Kelly Lingerie
I had just split up with a few of the boys I hang out with after school
at the burger shop. They made their way down Main Street while I took a
route to the more elaborate store fronts of the city. After walking 6
blocks I made my way down Rainbow Avenue and I could see the bright
street light illuminating the storefront windows of Kelly Lingerie. This
was the highlight of my week because I got to see all kinds of womanly
items I would never see anywhere else except in catalogs. My pulse
quickened as the store front window was just about 20 yards away. I began
to slow my steps and peered over my shoulders to see if anyone else was
walking behind me. With the coast clear, I stepped right up to the window
and took notice of a manequine decked out with a Black lacey Bra, garter
belt and stockings. To the right of that manequine was another one
modeling a satin shaper with sheer control top pantyhose. Hanging in the
corners of the windows were bright white, Pink and Blue fluffy
petticoats. For what ever reason I was drawn to this store and admired
the shiny silky lingerie. Every couple of weeks there were different
items to look at and I made sure I got to see the new items for sale
every week. After about 2 minutes of eyeing up the lingerie I continued
my way home in the darkness. It was around 6:00 and Mom was still working
at the knitting factory til 11:00. When I got home I continued thinking
about how great it was to see the lingerie in the display windows at
Kelly Lingerie. I made myself some pizza and then made my way to the
computer to see what else Miss Kelly had for sale this week. As soon as
the web page popped up I got a second dose of more fantastic lingerie
items including some old time girdles with side zippers on them! The
shiny satiny tight fitting garments looked awesome on Miss Kelly's models
and it made it impossible not to stare. A tight fitting white figure
hugging garment and shiny suntan nylons attached to the garters was a
great way to end the day. Also today Miss Kelly had some of her young
store helpers in some of the photos promoting stockings, pantyhose,
shapers and other feminine items. An upper East side girl I've been
admiring for months now was also in one of the photos. There stood the
proud and beautiful Diana holding two frilly petticoats by her side. The
sale price was $99 or 2 for $149. Her beautiful smile, long hair and
polished appearance made me melt! She was one of the most beautiful girls
I had ever seen and I would give anything to get close to her. After
downloading a few pictures from the site I sent out some emails and began
doing my homework before Mom got home. Over the next hour I tried to
focus on my homework but couldn't get the Diana images out of my head. I
found myself back online again trying to absorb every single inch of
Diana's stunning beauty. Shoulder length auburn hair, polished
fingernails, perfect makeup with Black outlined eyes. She looked like she
was 25 but she was just 16 or 17 years old. Even though I was only 14, I
still had eyes for her compared to the other girls in my school.
As the weeks continued on I found myself in front of the huge glass
windows of Kelly Lingerie again and again. I was now stopping by 3 or 4
times a week and also staying longer than my usual 2 minutes. The sheer
fabrics and vibrant feminine colors continued to take a hold of me for
some reason. I know I was a boy but in the back of my mind I wondered
about things that young boys shouldn't think about. My fascination with
pretty colorful underwear and figure enhancing womanly foundation
garments were stuck in my brain. For a while I would daydream about these
feminine things once or twice a week. But after discovering the Kelly
Lingerie store earlier this year my fascination with shiny feminine
underwear became the highlight of my day and I couldn't get enough of it.
Late one September evening after leaving the Malt shop with the guys, I
made my way back down Rainbow avenue. Like so many times before the
Street lights were illuminating the store front windows of Kelly
Lingerie. When I got a look at the manequines modeling a pair of old time
all in one open front girdles with sheer tan stockings attached to a pair
of extended garters I felt a strange sensation rush through my body like
never before. The shapers were light Pink and another was in light blue.
I stood there eyeing both of them up and got my nose as close to the
glass as possible. I was just inches away from them as the glass
separated my desires and the lingerie. Without realizing what I was doing
I slowly reached my hand up to the glass to try and touch the feminine
finery. I was lost in another world as my eyes looked at the Blue and
then the Pink. My eyes darted back and forth again and again and again as
I tried to make up my mind which one was prettier. As I gave in to the
Blue shaper and tan stockings a voice opened up from the side of the
building. "Can I help you with something young man?" I quickly snapped my
head to the right and noticed Miss Kelly stepping out of the darkness. I
quickly lowered my hand to my side and took in a deep breath as she
clicked her heels towards me. After about 10 steps she got to within two
feet of me. I was busted, she caught me red handed as she placed her hand
on my trembling shoulder. "So sweetie, which do you prefer, the Blue or
Pink?" I was frozen as she eyed me up some 2 feet taller than me. "I...
I... I... I'm not really sure Mam?" I quickly lowered my head as she
began tapping her high heeled clad foot just inches from my sneakers.
"You know what I think little boy? I think you were doing more than just
window shopping sweetie?" I Once again quickly snapped my head up to her
with my mouth wide open. "N... N.... No, no Mam. I wasn't window sho...
sho... shopping!" I then noticed the small 'Help Wanted' sign taped in
the lower left hand corner of the big window. Without even thinking I
blurted out to her. "I... I.. Was wondering about the help wanted sign."
Miss Kelly placed her hand on her slender waistline and began to grin.
"Really, you want to work in MY lingerie shop? I swallowed hard as she
tossed her long hair over her shoulders. As our eyes met she could sense
my embarrassment by the way I was fidgiting and trembling. After a long
stare she opened up her purse and pulled out her keys. "Follow me
sweetie." We walked back around the side of the shop and she stuck her
key into the lock on a side door off the main street. After disarming the
alarm and turning on a few lights she walked me to her office. There were
boxes, satin hangers and lingerie hanging everywhere. I once again
swallowed hard as she guided me into her office. "Have a seat sweetie
while I dig out an application." While Miss Kelly rummaged through her
drawer, I noticed boxes of stockings, tights, and pantyhose in fancy
retail packs. I could tell these were high end sheers because of the ones
I noticed selling on eBay for $50-$80 per pair. Miss Kelly took her seat
and handed me the application. "Now before we get to far, I need you to
fill this application out and have one of your parents sign it at the
bottom. You obviously are a minor so I need parental approval before you
can start." I took the form from her hand as she continued to eye me up
while spinning her gold bangel on her dainty wrist. As I began looking
over the application she crossed her jet black nyloned legs making a
fantastic staticy sound. "So what's your name sweetie and why do wish to
work in my shop?" I folded the application in half and looked up into her
eyes. "My name is Gary and I want to work for someone close to home." Her
smile grew bigger as she took her tiny perfume bottle and began spritzing
her wrists. "Well to be honest Gary, I could use a strong boy to help
unload delivery trucks along with helping out with my inventory problems
right now. You see, most of my girls that work for me hate breaking nails
and getting runs in their stockings from handling the boxes. "Do you have
a problem with chipping your nails or getting runs in your hose?" My
mouth dropped open wide as she let out a soft giggle. Before I could
respond she stood up and walked out from her desk. "I'm sorry Gary, I
just want you to understand that the girls you'll be working with are
much older and will pick on you a little for amusement. I just want to
make sure you can take a joke?" As she inspected my hand her index finger
slowly brushed over my longer than average nails. I don't know who was
more aroused as she eyed up my hands. I could see her smile growing just
as mine was. Her soft touch and stunning beauty made it impossible to
think straight as I fidgited in the chair. I tried to slowly pull my
hnads away but she made it clear she wasn't finished inspecting them.
"This should be very amusing, a boy working in a lingeire shop? I sure
hope you know what you're signing up for sweetie?" She pulled me from the
chair with both of her hands gripping mine. I stuck the application in my
pocket as we made our way back outside. "Miss Kelly, how much an hour
does the job pay?" "Well, I usually pay my girls $12 an hour plus
commissions. However your situation will be a little different so I'm
gonna have to think about it? You get your application signed first and
then we'll figure out the pay scale." She clicked her heels down the
alley and I litterally ran home to get busy filling out the application.
What an amazing stroke of good luck came my way tonight. Not only did I
get a close up of Miss Kelly's stunning beauty but I now had a chance to
get even closer to Diana and all those wonderful femmy items in the
store.
When I got home I tossed my books on the kitchen table and took out a
pen. Over the next 30 minutes I filled out the employment application
making sure everything was in order. After filling out every line I
cracked open a coke and headed up to the computer. I had Miss Kelly's
website bookmarked so it only took a few seconds to pop up. Today a few
of the other girls were posing with longline shapers, garter belts and
hosiery. Miss Kelly was running her Buy 2 get one free on sheer
stockings, tights and support pantyhose specials. She had all the
greatest brands, 9 to 5, Peavey, Victoria's Secret, Donna Karan, Evan
Picone, Miss Priss, Sheer Delights along with plenty of fine Italian
brands. The two girls posing with the feminine items were about 17 or 18
and getting ready to step into womanhood. They were just as feminine as
Diana, with their long hair, perfect makeup and nails along with their
soft Pink short skirted uniforms all Miss Kelly's assistants wore. The
one thing I didn't like seeing today was the 'HELP WANTED' banner at the
top of the webpage. It was clear I was going to have competition in
getting a job there but nothing in life is easy.
When Mom got home I immediately ran downstairs to help with the grocery
bags. "Hi MOM!" I took the bags from her hands and she set her purse on
the kitchen table. "Ok Gary, what do want this time? You only help with
the bags when you really want something." I pulled the application from
under the shopping bags and unfolded it. "Well Mom, you were the one who
insisted I get a part time job to make a few extra bucks and today I
stumbled into a potentail opportunity. I handed her the application and
she took out her glasses from her purse. "All you have to do is sign it
at the bottom and I can return it tomorrow." Mom's mouth dropped wide
open as soon as she began reading it. "Have you lost your mind Gary? This
is an application to work for Kelly Lingerie and that overbearing
Caroline Kelly who charges 3 to 4 times more for lingerie than what they
sell for in other stores!" "Mom, please calm down. I believe it is the
object for a business to make, not lose money?" "Ha, Ha, very funny Gary.
What I'm trying to say is Miss Kelly Rapes her customers with her high
priced items." "Well if her prices are so high, how has she managed to
stay in business for all these years?" "I don't know Gary, I don't shop
there and neither do any of the other women I work with." "Well maybe her
prices are too high for you? She seems to have a very large following of
customers?" "Gary, Gary, Gary, one of the big things that draws customers
in is her daughter Diana." "DIANA! She's Miss Kelly's daughter? I thought
she just worked there?" Mom cracked a thin smile as she quickly noticed
my dissapointment. "So It's Diana hmmm? You ain't interested in the money
you want to get a little closer to her." "Ok, Ok, Mom, that's part of it
but I still could use the money." "Well, I wish you luck sweetie, I
believe Miss Kelly's daughter is a little out of your league and she has
to be at least 3 years older than you?" "Don't worry about the age
difference Mom, no one has seen her with a date yet and maybe I can
sliiiiiiide my way into one with her?" Mom shook her head from side to
side and continued reading the application. "So what kind of hours will
you be working if you get the job?" I hesitated with my response as I
watched Mom pull her pen from her purse. "I'm not really sure? Maybe
after school or Saturday's I guess. Me and Miss Kelly didn't really talk
about hours or pay yet." As Mom signed the application she shook her head
from side to side. "Not sure why Miss Kelly would want a teenage boy
working in her lingerie shop when she has plenty of young girls to employ
as helpers? Mom handed me the application back and then went on to
unpacking the groceries. My heart was beating fast as I hurried my steps
up to my room. With great pride I placed the application in my binder
with high expectations of getting the job to work for Miss Kelly and her
daughter.
The following day after school I skipped the visit to the Milky Way Kid
hang out and made my way down to Miss Kelly's shop. The whole day at
school I daydreamed about finally seeing Diana in the flesh and hopes of
getting the job. When I got to the huge window I noticed that the
manequines were still covered with the same lingerie as yesterday when
Miss Kelly caught me eyeing them up. The 'Help Wanted' sign was still
posted in the window which was a good sign, Miss Kelly still had the job
opening available. I went around to the side entrance of the store and
pressed the ringer. After a few minutes I pressed it again and again with
no response. I waited another 5 minutes before making my way to the
storefront door that all of Miss Kelly's customers used. The inside of
the door was layered with pink chiffon drapes and it was impossible to
see inside. With one deep breath my sweaty hand turned the doorknob and I
pushed the door open. The loud bell that rung out made it impossible to
enter the store quietly. After shutting the door 6 sets of black outlined
eyes quickly peered down at me. There were 3 women standing 6 feet in
front of me along with 3 of Miss Kelly's helpers with big grins on their
faces. I noticed the girls from the website and it only took a few
seconds for one of them to greet me. Her name was Constance and she was
so pretty! Her long blonde hair and blue eyes were to die for. Not to
mention her long shiny nyloned encased legs extending from her short
uniform skirt. "Well, we don't get many boys in here sweetie! Are you
here for the hosiery sale or are you here for a fitting?" All the girls
and women began giggling as my cheeks turned 3 shades of red. "I.. I..
I'm here to see Miss Kelly." She got a disappointed look on her face as
she wrapped her arm around my waist. "Miss Kelly went to pick up her
daughter from school but she'll be back any minute now. Why don't you let
me show you around til she gets back?" Constance's firm grip around my
waistline felt real nice and I just loved the way she took hold of me.
Over the next 10 minutes I got a tour of the whole shop from the first
floor to the second floor. Bras, Girdles, Petticoats, slips, Pettipants
Tights, Nightgowns, Pantyhose, Camisoles, Panties and Garterbelts. You
name it, they sold it, and I was loving it! All the pretty things I was
looking at from the sidewalk for months were now just inches from my
fingers. When we got back downstairs the other store helpers encircled
me. As they towered over me in their 3 inch high heeled shoes Victoria
placed her hand on her hip and stroked my long hair. "So what do you want
to see Miss Kelly about if I may ask?" I hesitated with my response as I
was cleary outmatched and intimidated by the girls confidence and
appearance. The smell of their sexy perfume filled the air and the store
was now empty except for the 4 of us. Just as I was about to respond to
Victoria, Brittany cut me off. "I think he's here to buy some pretty
things for himself? I've only ever seen 3 guys in here and they were all
Xdressers." Constance stroked my long hair while Brittany went on. Yea, I
bet you'd just love to get your hands on some of these silks and satins
wouldn't you baby?" From the hosiery display Brittany pulled a pair of
tan stockings and stuck her hand into one of them. As the girls tightened
the screws on me, Brittany rubbed her nyloned hand all over my cheeks.
"How does that feel sweetie, have you graduated to pantyhose and
stockings yet or are you still wearing your Sisters tights?" I was about
to fall over as she continued slowly stroking my face with her nyloned
hand. I was speechless and under Brittany's powerful spell. Constance
then broke the silence and pinched the top of my zipper. "$20 says he's
wearing panties." "No way, he's wearing tights!" As the girls blurted out
bets I felt myself losing their feminine battle. Then out of no where we
heard a loud clap of hands, 'CLAP CLAP CLAP'! "Allright girls! That will
be quite enough!" We all looked over to see Miss Kelly and her daughter
Diana stepping into the room. Miss Kelly walked over and took the
stocking off Brittany's hand. After inspecting it for runs she lifted up
Brittany's short skirt and swatted her pantied ass. 'CRACK! CRACK!
CRACK!' Stockings are for legs not arms or hands my dear, make sure
remember that the next time you grab one!" "But Miss Kelly we were only
having a little fun with pretty boy here." "That will be enough Brittany!
I don't pay you girls to screw off while I'm out, now get your asses back
to work! Come Gary you can join me and Diana in my office so we can go
over your application." Victoria's mouth dropped wide open as she placed
her hand on her shapely hip. "Application! Boys don't work in Lingerie
shops they work at lumberyards or McDonalads." "Not now Victoria, we'll
discuss it later. Diana darling take our guest back to the office and get
him a cold drink while I help the girls with the tomorrow's specials."
Diana grabbed my sweaty hand and I quickly closed my fingers around her
hand. "This way sweetie." She called me sweetie! What better way to start
a possible working relationship. As her heels clicked along the tiled
floor her tight clad legs rubbed together under her short preppy plaid
school skirt. I was so in awe of her as she quickly whilst me out of
sight of her Mother and her mean store helpers. With every low heeled
step she took I had to take an extra half step. She was so elegant in her
feminine footwear and I couldn't keep my eyes off her shiny white legs or
her tight skirted ass.
After getting me a Coke she sat beside me and once agian grabbed a hold
of my hand. "I have to apologize for the girls out there. You see we
don't get many boys in here and I just want to say you handled their
humility extremely well." As I sipped my Coked she eyed me up and down
with her black outlined eyes. We shared a few smiles between us as she
rocked her tight clad leg in front of me. "You know Gary, Mom was right
about your hair and nails being more feminine than masculine." I began
choking on my Coke at her observation and tried to get a word out in my
defenmse but couldn't get one out between coughs. It was then that Miss
Kelly joined us and closed the door. "Now Gary, may I have your
application for employment please." After one last cough I pulled the
application from my pocket and handed it to her. After a few minutes of
silence she began nodding making her earings jingle. "Well, everything
seems to be in order. Diana do you have any questions for Gary here?"
Once again her smile and eyes got the best of me as I nervously began to
fidget. "Do you promise to work hard and show up on time?" I nodded
without saying a word as Diana went on. "You must be able to work some
Saturdays and Sundays. You won't work every weekend but we may need you
to fill in when we're short handed. Are you ok with this schedule?" "I
will do my best for the company and work when ever you need me." Miss
Kelly looked at her daughter and took off her glasses. "I don't know
about this Diana. Having a young boy working in a crowded Lingerie shop
could bring some unwanted solicitation from the town council? They might
not see this as good and proper employment practices?" Diana rolled her
eyes to the ceiling and hopped to her heels. "Look Mom, you said last
night we need a strong back around here to help with deliveries and Gary
here is willing to work weekends. We may interview 25 more girls and not
one of them will work weekends like the 12 girls we interviewed last
week." "I know Diana, but maybe we should..." "Mom, we could really use
Gary no matter what the city council thinks. He's willing to work, he
lives close by and the best part of all you won't have to worry about him
stealing panties and Bras out of here like you did with other girls in
the past." Miss Kelly sat back in her chair and let out a defeated sigh.
"Ok, ok we'll give him a chance. Gary, I want you here after school
Monday, Tuesday and Wednesday of each week. I'll start you out at $11 an
hour for 3 weeks. After the 3 weeks is up we will reevaluate the
situation. "Lets go introduce our new helper to the girls my dear. Once
again Diana grabbed a hold of my hand and began walking me back out to
the storefront. Miss Kelly followed behind us and once again clapped her
hands loudly. 'CLAP CLAP CLAP'! "Gather round girls." As Miss Kelly's
girls drew closer Miss Kelly pointed the storefront window. "Diana then
pulled me right up to the window. For a change of scenery, I was now
looking out onto the bare sidewalk where I stood for so many months
admiring the fancy lingerie on display. "Go ahead Gary, it's tradition
around here for every girl to take down the help wanted sign after being
hired." With a reach of my hand I pinched the help wanted sign with my
fingertips and pulled it off the glass. Diana began clapping and we made
our way back to everyone. "Well girls, Gary will be joining the team on
Monday. Please give him help when ever he asks for it but do it back in
the storeroom. I don't want him on the sales floor unless it's absolutely
neccessary. Now if any of you have anything negative to say you better
say it now." As Diana's hand gripped mine, Constance stepped up to me
with a grin and stroked my hair. "Miss Kelly, Does he get the 15%
employee discount on his Bras and panties he buys?" There was a slience
for about 5 seconds as eevryone took in her comment. It was then I felt
Diana's hand grip mine tighter for some reason as her smile grew and
grew. She then opened up to Constance. "Actually he's gonna get 20% off
his panties and bras you little witch!" I couldn't believe what I was
hearing from Diana's mouth. I know it wasn't my place to try and correct
her but I really wanted to say something to defend my masculinity. Miss
Kelly then broke up the war of words and I was once again taken back to
the office. Both Miss Kelly and Diana gave me soft welcoming hugs and a
round of enthusiastic smiles. "Ok Gary we'll see you on Monday, here's
the security code for the back door. I don't want you coming in the front
door at any time is that understood?" "Yes Mam, I understand." She handed
me the code and Diana handed me another Coke. "See you next week
sweetie." She gave me a wink of her eye and I all but melted as I made my
way back out to the side alley.
When I got back home Mom was in early and I erupted with the news. "I got
the jonb Mom! I start Monday after school." She immediately took off her
glasses and stood up from the chair. "Is this some sort of joke Gary? I
heard from Mrs Baker that there was a list of applications a mile long
that were handed in over the past 2 weeks. How is it that Miss Kelly made
a hasty quick decision to hire you?" "Mom knock it off and don't be
suspicious. Miss Kelly needs someone to put deliveries away so the sales
girls don't break their nails or get runs in their stockings. She was
also impressed at my willingness to work weekends when the other girls
can't make it." Mom shook her head from side to side as I beamed with
confidence.
"Ok Gary, I'll play along and let you work. I will tell you this, as soon
as I see a decline in your grades or any other abnormalities I will be
putting an end to your part time job. Do we understand each other?"
"Don't worry Mom, my grades won't be slipping. Can we go down to the bank
before it closes so I can open up a savings account?" "Just hold your
horses, you haven't even got one paycheck yet. We'll go down the day
after you get your first check. Now get yourself washed up before
supper." The remainder of the evening was spent eyeing up the Kelly
Lingerie website trying to see what all was for sale and where it was
located in the store. Even though I wasn't gonna be out on the sales
floor with the sales girls I still needed to know as much about the store
as possible.
The weekend was long and I was so excited to get to work for my first
day. I shrugged off the little games the girls were playing on me last
week but I couldn't get the feel of that silky nylon Brittany rubbed
against my cheeks. Her peircing Blue eyes and the smirk she had on her
face while she toyed with me was something I'm never gonna forget. Deep
down I really wanted her to do it again for as crazy is sounds. When I
got to the store on Monday Miss Kelly greeted me after I walked in and
showed me where to punch in at the time clock. After punching in she led
me to her office and had me fill out a few more teenage labor forms to
make everything legal. As I filled out the forms her daughter Diana came
in to join us. "Hi Gary, it's so nice to see you're on time for your
first day." She gave me a playful nudge with her elbow and I immediately
got red faced. Our eyes met and for about 5 seconds she had me in a
transe. Her long hair, pink lipstick covered lips and rosy cheeks were to
die for. Miss Kelly took the forms from my hand put them in her file
cabinet. "Allright Gary you can follow me and Diana to the back." Miss
Kelly stood almost 2 feet taller than me in her 4 inch high heels and
Diana was clearly over 10 inches taller than me in her low heels. Being
sandwiched between them was a great way to start my first day.
When we got the back storage area Miss Kelly flicked on the light and the
room illuminated with 100's of opened and broken boxes of underwear and
foundation garments. I stood there eyeing up everything and really didn't
know what to say. After a long silence Diana gave me another nudge with
elbow. "Weeeell, what do you think Gary?" After scanning the flor and
shelves I spoke up. "Miss Kelly I'm not rying to be rude but, this is a
disaster area!" She wrapped her arm around my waist and began walking me
down the cluttered aisles. "Well put Gary, and let me be a little more
clear about what you're looking at. This is YOUR disaster area! Starting
today you and Diana will be straightening out and organizing this Atomic
Nylon/Lycra Mess." "Miss Kelly you must be joking? It will take months to
reorganize and restock everything." "Take it easy sweetie, Diana will
help you organize, rebox and get all these items with pricetags so I can
start selling them. What you're seeing here is a product of having too
many young girls working for me. They come back here looking for
something and never put things back the way they were. That's why we have
the problem we have." As we walked down more of the cluttered aisle Miss
Kelly picked up a box filled with Vintage all in one shapers. "You see
Gary, I could use all these shapers for my larger customers but I can
never find them when I need them." Without warning she pushed 5 or 6
satiny shapers into my tummy. "Hang on to these while I get this box off
the floor." My small hands immediately grasped the satiny foundation
garments while Miss Kelly picked up the box. As soon as she had the box
off the floor the bottom opened up and the rest of the shapers fell into
the asile. "Damn it! Diana get me some of that 3" clear shipping tape so
I can fix this box." While Diana clicked her heels over to the table Miss
Kelly bagan draping more satiny shapers over my shoulders! "Miss Kelly! I
don't think I should be touching...." "Hush Gary! You don't want to start
your first day off on the wrong foot with me do you?" By the time she was
done I was holding and covered with over a dozen shapers in various
feminine colors. When Diana came back with the tape she wrapped her arm
around my waistline pressing the lingerie even tighter to my tummy! "Here
you go Mom." Miss Kelly took the tape while Me and Diana watched. Rather
than take some of the shapers from my hands she straightened out her
skirt and let her long hair brush against my neck. Talk about a turn on!
My trembling hands held the shapers as tight as possible as my tiny body
pimpled up and softly fidgited. It took Miss Kelly a few minutes to fix
the box while Diana peered down on me and smiled with great enthusiasm.
"Ok Gary, give me those shapers." She took the shapers from my hands and
laid them in the box. "Thank you for holding them for me Gary I'm glad to
see you're not afraid of a little lingerie. Now lets continue with the
tour shall we?" Once again I was sandwiched between Miss Kelly and her
daughter as she slowly led me up and down the cluttered aisles. Panties,
Nylons, Bras, satin hangers, nitegowns, petticoats, you name it, she had
it in her messy storage area.
When the tour was over Miss Kelly handed Diana the blank inventory list
and then made her way back to her office. I once again looked all over
the room and began shaking my head. Diana put the inventory list on one
of the boxes and looked down to me. She said nothing as she smiled. Her
gold necklace, earing and bangels only enhanced her stunning beauty and
she clearly had me under her spell. "You know Gary, you looked so
adorable holding all those shapers. You clearly passed Mom's first test
with a A+." With a confused look I shyly looked away from her. "Test,
what test was that?" She began running her fingers through my long hair
and giggling. "Well, most boys would've dropped those shapers in a split
second, but you seemed to be enjoying it if you ask me?" I quickly
snapped my head up with mouth wide open! "Di... DI... Diana! How could
you say such a thing?" She began laughing and clapped her hands together
making a loud CRACK! "Take it easy Gary, I was just pickin on you. I know
by now what boys like and don't like. You just kinda suprised me with
your willingness to handle such feminine things. After seeing that, I can
clearly see that we're gonna make a great team. Now lets try and figure
out a strategy on getting this place back in order." She gave me another
hug and I instantly began smiling. I just loved everything about her and
if I wasn't in love, I knew I soon would be.
By Wednesday evening Miss Kelly came back to inspect our 3 days of
progress. As she stepped her high heeled clad feet down the now non
cluttered asiles she nodded with approval. Even though we wern't even a
quarter of the way through with our project she could clearly see things
were moving in the right direction. When she got back to me and Diana she
placed her hand on her shapely hip and began running her fingers through
my long hair. "Well Gary, it appears Diana has made a wise choice in
bullying me into giving you the job last week. The two of you have done
quite well in your first few days." Diana's smile couldn't have been
bigger as Miss Kelly continued looking around. "Mom, do you think it
would be ok if me and Gary continued working on this project on
Saturday?" Miss Kelly let out a sigh and looked over to her daughter.
"How quickly we forget Diana. You know I have the ladies auxillary for
lunch on Saturday and I need you and Constance to help me." "Well, what
if I get one of the other girls to fill in for me?" "Diana darling, the
reason you're helping out is because Victoria will be out of town and
Brittany's going to take her SAT's. No, the two of you will have to
continue with this on Monday next week." I could see Diana was upset but
I really couldn't object to Miss Kelly because she was the boss.
When I got home I went to do my homework. I had been doing just enough to
get by the past few days so I now had plenty of time to get caught up.
Even though I was doing my best to concentrate on my work, thoughts of
the last 3 days working with Diana at the Lingerie shop was not easy to
turn off. Her beauty and charm was exactly what I liked about her. She
was always nice to me and in her own way played her little games without
me trying to notice. Like earlier today when she tried to softly tie a
pink ribbon in my hair without me noticing. I was lifting a big box with
my back turned to her but I could feel her softly touching my hair.
Without saying one word I let her quickly tie the ribbon before I put
down the box on the shelf. A few minutes later I noticed the ribbon and
softly complained to her about it. She had the biggest smile on her face
and to be honest so did I. I knew deep down she really liked me for some
reason, but I just couldn't put the pieces together? Perhaps next week
more clues would surface about her and why she was being so nice to me?
The following Monday at 3:00 I punched in and made my way to the back
room. Diana and her Mother were going over the inventory list and
pointing at boxes at the other end of the room. I broke the ice as I got
closer. Hi Girls! How was your weekend?" Both of them had disappointing
looks on their faces and Miss Kelly quickly handed me the list. "It was
not the best weekend Gary, hopefully yours was better?" She stormed out
of the room back to her office while Diana tapped her low heeled foot on
the floor. Her mood was vary bad and it looked like she was ready to
kill! I softly gave her a nugde of my elbow breaking her concentration.
"Hey, it's me, Gary, remember?" After a long pause she cracked a smile
and nudged me back. "Sorry Gary, I had a bad weekend." "Yea, that's quite
obvious from the way your Mother was acting. Did the two of you have a
fight or something?" She slammed the inventory sheet on the table and
placed her hand on her hip as her temper reappeared." "That witch
Constance didn't show up on Saturday to help me and Mom so I had to work
my ass off twice as much to help with Mom's luncheon. I don't mind
helping out but it was Victoria's and Constance's turn to work and I
ended up doing it all by myself!" "Ok, Diana, take it easy, I can't
believe your still upset 48 hours later?" "I'm sorry for venting Gary, I
guess I really don't have anyone else to vent to?" She began stroking my
hair as her eyes met mine. Another long 10 second stare down began and it
was clear something was brewing between us.
After a long exhale she picked up her list again and we began calming
down. Today we were working a little later than usual because of some
deliveries that were made. When Diana opened up the new boxes and pulled
out several longline girdles with garters attached to the bottoms she got
a huge smile on her face. My heart began beating faster as she held out
one of the garments in front of me. "Just look at these girdles Gary!
They have to be 30-40 years old. I wonder where Mom got these at? She's a
whiz at finding this stuff online." She pulled out Pink ones, Blue ones,
Yellow ones along with Bright white ones in several different sizes. I
was mezmorized by what laid in front of me with the most beautiful girl
fondling them. When Diana stood up and laid one of the white ones over
her chest I watched in awe at the shiny satiny legs drop to the hem of
her skirt. "I wonder what it's like to wear one of these under a dress
all day?" As she motioned herself in front of a mirror I began to think
how great she'd look in one of those girdles and tan stockings. As she
twirled in front of the mirror my wandering hands reached over to grab
one of the girdles. Just as I picked it up she turned back and caught me
with it in my hands. I instantly froze as she began to giggle. "What are
you doing Gary?" I began breathing heavier as the silky smooth feel of
the girldle got the best of me. "I... I.. I'm not sure Diana? These
satiny girdles look so interesting to me. For some reason I find them
alluring?" She slowly clicked her heels over to me and took the girdle
from my hands. She then took a nylon stocking from the floor and stood
behind me. With a grip of my hair she slowly began tying up my hair with
the stocking. "You know what I think Gary? I think you knew all along I
was tying that Pink ribbon in your hair last week?" My mouth dropped wide
open as she continued tying up my hair. "Take a good look at all those
lovely tight fitting girldles sweetie. Maybe it's you who really wants to
know how nice they fit instead of me, Hmmmm?" I could feel myself getting
weak in the knees as she finished tying off my hair with the girly pink
stocking. Before I could dig myself out of the hole I was in she pulled a
light Blue girdle from the box and pressed it against my chest. "I bet
this Petite one would fit you real nice?" As I looked down to see the
dangling short legs at my crotch Diana looked deep into my eyes. "You're
not trying to get away sweetie, perhaps we could get you some stockings
to attach to those garters as well? It's only the two of us back here,
why don't we have a little fun to start the week?" I began shaking my
head as my confused brain tried to process what was happening. Before I
could get one word out I stepped away from Diana and took the girdle from
her hand. "Diana, this is crazy, boys don't wear girdles or... or...
stockings!" "Ohh come on Gary, I noticed the way you fondled the nylons,
scrafs and slips last week. You may be kidding yourself but you're not
kidding me." Once again she pressed the shiny Blue longline girdle to my
chest and eyed me up. "Just think how much fun it would be to slip into a
pair of support stockings and this dreamy longline shaper. I'd bet you'd
look great in it!" For a brief second I was about to crumble but after a
long exhale I once again took the girdle from her hands. "Diana, please!
We have lots of work to do. What is your fasciantion with seeing me in
thi... thi... this Girdle thingy?" She placed her hand on her hip and
cupped my chin. "Ok sweetie, maybe we'll play another day. You're not
quite ready to take that big feminine step yet?" She tossed the blue
girdle back in the box and I quickly grabbed her hand. Her fingers
interlocked with mine and once again we looked deep into each others
eyes. "May... Maybe we could go to a movie or... or.. have a milkshake
sometime?" She began giggling and tossed her hair over her shoulders. "So
the truth comes out, you want to go out on a date. Maybe I read you the
wrong way Gary? I thought for sure you had a thing for silks and satins?
It looks like you're just like all those other boys who chase me around
in my heels trying to get in my panties. This clearly puts our working
relationship on a different level. Now lets get back to work shall we?"
She untied the stocking from my hair and the Girdle box was put on the
shelf. Her great smile and charm were now replaced with a more military
work ethic. We worked the rest of the night and it was all business. I
thought for sure my days at the shop were numbered now that she knew how
I felt about her.
The next few weeks I found myself working in the storage room by myself.
Diana was no where to be found and I was as depressed as could be.
touching and caressing all the beautiful items I was looking at through
the big store window over the past few months were no where near as
exciting as when I would see Diana handling them. I missed her smile and
touches so much and I have no else to blame but myself for asking her
out. On Fiday I was unloading some fantastic new hosiery that came in
when Constance and Brittany came back to visit. I had all the nylons on
the table and was just about to put them on the shelves when Brittany
grabbed a pair. "So stocking boy, what happened betwen you and Diana?
Haven't seen her for weeks and we want to know what happened?" I took the
nylons from Brittany and set them on the shelf. "Well Brittany I guess we
had a little falling out? Either I did the wrong thing or said the wrong
thing to her?" Constnace then took a seat and crossed her tan stockinged
legs. "Well the only time she clams up and dissapears is after a boy asks
her out on a date." I looked to the ceiling and then let out a sigh. "Yes
Constance, you're exactly right. I asked her out to a movie and she got
all pissy about it. She flirted with me every day and held my hand
several times so I kinda figured she was interested in maybe going out? I
guess I just don't understand what makes her tick?" Both girls began
giggling and then opened up. "Well We know for a fact she's never been
kissed and has a huge problem with getting close to any boy. That's why
we were so shocked to see her grab your hand the day you took the Help
Wanted sign out of the window." "I know exactly what you mean Brittany!
You know, Miss Kelly was kinda against hiring me but Diana insisted on it
for some reason?" "Well there must be something about you she liked? Are
you sure you didn't piss her off in any way?" My mind drifted off for a
few seconds as I replayed Diana pressing the longline girdle to my chest.
I then let out a sigh and folded my arms. "Well, maybe I did the wrong
thing by not doing something she wanted me to do? That's all I'm gonna
say about it because I really don't know? She was gone the next day and I
didn't even get a chance to apollogize to her." Brittany then set down
her drink, smiled and eyed me up. "Well stocking boy, what if I was to
tell we might be able to get you back on Diana's good side, if we wanted
to?" I looked at them both with wide open mouth and eagerly listened. "We
know Diana is gonna need help tomorrow, a lot of help. You see, me,
Victoria and Constance will be out of town all weekend and Miss Kelly has
a few buyers coming in to schmooze over." I looked at the two of them
with a puzzled look on my face as I tried to figure out what it was they
proposing. "Ok, so she's gonna need help what's that got to do with me?"
Constnace and Brittany began pulling several pairs of satin panties from
one of my inventory boxes and placed them in front of me. "Right now Miss
Kelly is fretting in her office trying to figure out how Diana will
manage to keep up this weekend by herself. If you really wanted to get a
second chance with her and move up in the company now would be a great
time to march yourself into her office and vollunteer to help Diana
tomorrow." As I began thinking about what was just said Brittany began
counting out the panties she pulled from the box while Constance wrapped
her arm around my waist. "In return for this valuable information, we
want you to pay for our darling panties with that big 20% employee
discount you get." "My god Constance, the two of you picked out over 20
pairs! Even with the 20% discount the cost is over $400." There was a
long silence as I stared at the colorful satin panties that laid in front
of me. I knew this deal would wipe out my whole months pay but I just had
to see Diana again to try and work things out. "Ok, ok, it's a deal, I'll
go see Miss Kelly right now. But the deals off if she decides not to let
me help." Just as I was about to step away from the girls Constance
grabbed my arm. "Hold it stocking boy, you forgot our panties!" The girls
pushed the pile of panties to my hands while I looked up to them. "What's
going on girls?" "Listen stocking boy, you need to take those panties
with you and tell Miss Kelly your buying them. We want to make sure
you're not stealing them from the store. Get a receipt with your discount
like the rest of us get when we buy something." "Constance please! I
can't walk in there with $500 worth of panties in my hands asking for a
discount, she'll laugh at me!" "Last chance stocking boy, you either do
it our way or forget about the deal." As I stood there trying to figure
out what to do. In walked Miss Kelly from one of the back doors. She was
only 15 feet away from us and the girls immediately started giggling. I
swallowed hard as her high heels clicked over to the table. "Well Gary,
that's a real nice collection of satin panties you're holding. Her hand
ran through my long hair and I was once again caught with womens
underwear in my hands.
"So what's going on back here girls? Victoria's out front trying to help
4 customers all at once. Why aren't you girls out there helping her?"
Brittany wasted no time in filling in the blanks for Miss Kelly. "Well
Miss Kelly you're not gonna believe this but when we came back looking
for those slips you wanted this morning we found stocking boy here with
his hands full of satins." My mouth dropped open wide as I began to feel
Miss Kelly wrap her arm around my waist. "Go on Brittany, it seems Gary
here is at a loss for words?" "Well, he was wondering if it would be
allright to use his 20% discount on some new underwear. I closed my eyes
hoping the ground would swallow me up as Miss Kelly began to pull a few
pairs from my hands. "Of course Gary, it's quite allright to use your
discount for these darling panties. Maybe we could throw in some tights
and pantyhose for you as well?" "Mi... Mi... Miss Kelly I really
don't..." "Hush Gary and let me help you with those." I swallowed hard as
Miss Kelly took the panties from my hands. "You girls get your asses back
out front while I get these panties rung up for Gary." The giggling girls
clicked their heels passed me and we began walking right behind them to
her office.
When I got seated Miss Kelly closed the door and sat up on her desk with
nyloned legs crossed. She eyed me up for a long 10 seconds before
grabbing the box of satin panties. "So Gary, what was really going on
back there. I know you really don't want to blow a whole months salary on
panties do you?" I realized I was over a barell and had no way out if I
was ever gonna hook up with Diana again. "Miss Kelly I have to be honest
about the panties. Constance and Brittany were trying to get them at a
better price by using my discount. You see, they did me a little favor
and me buying them the panties was my end of the deal." "$500 in panties!
That must have been one hell of a deal you made with them?" As she began
zapping the barcodes with her price gun I fidgeted in the chair as she
went on. "No Gary, I don't believe this story. There has to be something
else going on with the three of you? I sat there silent while she
finished zapping all the barcodes on the tags. "It's not my business to
pry into what ever the 3 of you are doing, so for now you can have your
24 pairs of darling satin panties for $423.00. I'll deduct your pay
accordingly over the next month. You can help yourself to a few pairs of
pantyhose or tights as a bonus when you get back to the storeroom. Now,
is there anything else I can do for you to finish out the week?" It was
now or never so I cleared my throat and stood up. "Well Miss Kelly
there's one more thing. I overheard the girls talking this afternoon
about not being able to help you with your social function tomorrow." I
can tell I struck a nerve as she uncrossed her nyloned legs and hopped
off her desk onto her heels. "Yes Gary, it appears that all my girls will
be out of town tomorrow leaving me in a bind. May I ask why you're so
interested in this dilema?" I took in a deep breath and set my box of
panties on her desk. "Well, I'm not really busy tomorrow so if You wanted
and extra pair of hands maybe I might be able to give you and Diana a
hand?" Miss Kelly lowered her head and placed her opened palm over her
eyes. "This is some sort of joke right? You can't be serious about this?"
Miss Kelly eyed me up as I tried to make my case. "This is no joke Miss
Kelly I really want to help you and Diana if I can?" "Obviously the girls
didn't mention all the details of the weekend duties? You'll be on your
feet all morning and constantly be walking around until the last dish is
rinsed off." "Look Miss Kelly, I know how to wash dishes, I wash them
every day at home." "Yes But Gary, you don't understand what all goes on
and I'm not sure you would last more than a few hours?" There was a long
silence between us as she thought about what to do. I then made a bold
statement not knowing how it would change my life forever. "Why don't you
give your daughter a call and see if she would like me to help her
tomorrow? If she says no then we can both go our separate ways this
weekend." After another long pause she picked up her phone and called her
daughter. As I sat in the chair I heard the 5 minute conversation that
finally ended with a Miss Kelly grin. "Ok Gary, Diana's looking forward
to your company tomorrow. Be at my place at 9:00am and do not be late!" I
jumped from the chair and clenched my fists tightly. "Thank you Miss
Kelly, I won't let you or Diana down tomorrow." I turned to grab the
doorknob and Miss Kelly opened up to me once more. "Gary Darling!" I
quickly turned to see her with the box of satins in her hands. "Don't
forget your pretty panties." I took the box from her hands and quickly
went back to the storeroom. A few minutes later Constance and Brittany
joined me. "Well Stocking boy are you in for tomorrow?" I handed the box
of panties with the long reciept to the girls and grabbed my inventory
sheet. "Looks like I'll be seeing Diana one more time tomorrow. I sure
hope she can put the past behind and move on?" The girls didn't even hear
a word I said as they began fighting over the panties which I just paid
over $400 for!" Before I left for the day Miss Kelly informed me that I
would be getting overtime pay for my Saturday hours along with
complimentary lunch, snacks and drinks.
The whole night I kept wondering how to talk to Diana when I see her in
the morning. On one side I want to tell her how great it is to see her
again and on the other hand I wanted to try and apologize for asking her
out the way I did. I tossed and turned most of the night but managed to
doze off around 2:00am. After eating a light breakfast Mom drove me down
to Miss Kelly's House in the ritzy part of town. As she pulled up to the
driveway I grabbed my phone and unlocked the door. 'What time should I be
by to pick you up?" "Ohh don't worry about that, Miss Kelly said we were
going back to the store after everything wrapped up. I can walk home once
we finish up." "Well have fun sweetie, maybe tomorrow or Monday we'll
stop down at the bank to open up that savings account." "Yea, there's no
rush on that right now Mom, I kinda spent a lot of my pay already." I
shut the door and began the 100 foot climb up Miss Kelly's paved
driveway. I knew deep down the first 5 minutes with Diana would be tough
ones but somehow I had get through it calmly with some sort of maturity.
When I pressed the doorbell a series of chimes began echoing from inside.
After a quick look at my phone I noticed I was 10 minutes early.
Hopefully this wasn't gonna be a problem?" With the sound of high heels
clicking closer and closer to the door I took in a deep breath and
watched the door crack open. As soon as Diana's eyes gazed down on me I
was once again under her spell. There was a long stare with flirty smiles
between us. Finally I had to break the ice. "Well are you gonna invite me
in or what?" Her long arm quickly grabbed my wrist and she slowly walked
me in. After about 5 steps her hand slid down to my nervous hand and our
fingers interlocked. "It's so nice to see you again Diana, the shop just
isn't the same without you there every day." She gave me a nudge with her
shoulder and then gave me a big smile. "I can't believe you volunteered
to help me out today Gary. When Mother called me yesterday and told me
you wanted to help I almost fell off my chair." "Look Diana, I'm sorry
for asking you out the way I did a few weeks ago. I guess I'm just not
that good with girls yet?" "Don't blame yourself Gary, I was kinda hard
and acted very childlishly that day. I had a lot of time to think about
what I tried to get you to do and I sorry about that. Now give me a hug
before Mother gets downstairs." Our bodies embraced for a nice soft hug.
I could tell she was enjoying on the level because of how friendly she
was treating me. When I tried to break off the hug she squeezed me
tighter and tighter. "10 more seconds sweetie, it's been so long since
I've seen you." The smell of her girly perfume and makeup filled me up
with a morning overdose of her femininity. By the time we broke off our
embrace both our hands connected and I was under her spell once more.
When we got into the kitchen she quickly pulled out several trays of
fruit and vegetables from the fridge. On the stove was a pot of simmering
spagetti sauce along with bread baking in the oven. "Ok Gary, you can
start by peeling those oranges and grapefruit while I work on the
vegetables." I began pressing my fingernails in the rhines of the oranges
while Diana began washing off the carrots and lettuce. "So what is it
that's happening here today Diana?" "Ohh this is a tough day sweetie. We
have to get all this food ready by 11:00 when Mom's other franchisees
stop over to discuss their declining sales." "Franchisees? But Constance
told me that there were out of town buyers coming in for lunch." "No no
no Gary, that's two weeks from now. Constanace has her weekends mixed up.
Now today we have 10 other women stopping by for lunch so Mom can start
cracking the whip on them. Needless to say it may get a little hostile
this morning?" I continued peeling the fruit while Diana stirred the
sauce and prepared the salad. Around 9:30 Miss Kelly came strutting in
in a bright white Leather Mini skirt with matching 4 inch white pumps.
Her log tanned stockinged legs were to die for as she grabbed a piece of
celery from the tray and crunched down on it. Her tight fitting electric
blue metallic sweater showed off her busty chest and really went well
with her miniskirt. "Good morning Gary, nice to see you and Diana working
hard." I was in awe of her feminine look and hesitated with my response.
She could tell she was intimidating me as she gave me a wink of her black
outlined eye while crunching down on her celery. After Diana gave me a
nudge I snapped out of my transe. "Ohhhh, uhhhh, nice to see Miss Kelly!"
After stiring the sauce Miss Kelly took Diana's apron off and grabbed a
glass of Orange Juice. "Diana, why don't you take Gary upstairs and get
ready. I can handle the kitchen duties for a while til you get back." "Ok
Mom! Gary put down that knife and wipe your hands off." Before I could
get my hands clean she grabbed my hand and quickly walked me out of the
kitchen. Her fast walk had purpose as I tried to keep up with high heeled
steps. "Diana! What's the rush?" As she hummed away we made our way
upstairs and down the long hall to one of the back bedrooms. After
opening the door she pulled me into the darkness and shut the door. Once
again she held me close and began whispering in my ear. "So are you ever
gonna ask me out again?" As I hesitated with my answer her wandering hand
began stroking my long hair. "You know I'm kinda jealous on how great
your hair looks. With a little shampoo and conditioner it might be
prettier than mine." I slowly broke off our embrace but our fingers
stayed interlocked. "Diana, I'm so confused about you!" I'm afraid to ask
you out again because you might get mad at me again?" "Calm down Gary and
take a deep breath." After I exhaled I heard a soft click and a lamp on
the table illuminated the room. Diana then wrapped her arm around my
waist and turned me to the bed. On the bed laid two long sleeved Pink
dresses, and white aprons. Along with the feminine clothes were shiny
opaque white tights, bras, satin panties, camisoles, white gloves and
very feminine Pink patent low heeled shoes. As she pulled me closer and
picked at my hair I began to put the pieces together. "So what do you
think Gary, You ready to continue or do you want to run from me again?" I
nervously picked up the shoes and then looked back at her. "Constance
never said anything about dresses or or or girly shoes! She took the
shoes from my hands and tossed them back on the bed. "I guess it must
have slipped her mind? Let me explain it to you sweetie. You'll never be
my boyfriend until you become my girlfiends! Now we don't have a lot of
time to fish or cut bait this morning. Our guests will be here shortly
and we don't have much time." I got down on my knees and looked up at
her. As she stood with hands on her hips she enjoyed my struggles that I
was enduring. "Please Diana, I didn't sign up for dresses an... an.. and
tights!" "Maybe next time you should read the fine print before you
decide to step up to the plate?" "But you don't understand! I'm doing
this all for you! I just wnated to be with you today and help out." She
got down on her knees and looked deep into my eyes as our fingers
interlocked. "If you're doing this all for me today, then I suggest you
get out of your clothes and get your panties on." "But what if one of
those women recognize me? Do you have any idea how embarrassing this will
be for me?" "Calm down Gary, you'll be back in the kitchen the whole
time except when we're serving the meal. You'll be in and out of the
dining room in 5 quick minutes. Surely I'm worth 5 minutes to you?"
"Diana you're not hearing me! They'll know I'm a boy in a dress as soon
as they see me." "Enough Gary! You either start undressing now or you can
forget about being my boyfriend and going out on a date." She pulled me
to my feet and folded her arms up under her breasts. I once again looked
at the pile of feminine clothes that laid on the bed as Diana grabbed her
dress, panties bra and tights. "I'm going to the bathroom to change. I
hope you will make the right decision by the time I get back?" I knew
this was not going to be easy because half of me wanted to play dressup
and my other half was slamming on the brakes as hard as possible. I
closed my eyes, exhaled and then began to take off my shirt and pants. It
only took me a few minutes to pull the pink satin panties up to my ass.
The matching Pink bra fit me a really nice across my flat chest and the
begining of my crossdressing had finally begun. As I pulled the shiny
white opaque tights up my legs I watched my leg hair completely
dissapear. Even though I had rougher edges than Diana you would never
know I had boy legs in my tights. After snapping the tights around my
waist. Diana came back into the room. I quickly looked away while she
came over and hugged me. "I knew you wouldn't let me down girlfriend!"
She wiped a single tear from my cheek and I then went to give her a kiss.
For a brief second her lips separated and I saw her warm tounge! I was
inches away from her lips when she stopped me. "What do you think you're
doing sweetie? You're gonna have to do a lot more to earn that first
kiss! Now let me look at your pretty underwear." After inspecting me all
over she stepped over to a dresser drawer and opened it up. She pulled
out a few pairs of pantyhose and began filling my bra cups until they
were stuffed! "Ohh that looks so much better love! Come now, lets get
your dress on and see how it fits." After unzipping the polyester dress
she threw it over my head and I stuck my arms into the sleeves. She
snapped a few buttons shut at the cuffs and then began adjusting the
dress to my boyish frame. "You know, this looks to be a nice fit for you.
If your ass was a little plumper you'd look much better." As the zipper
teeth began clicking up my spine I felt the dress tighten up around my
tummy area. The skirt of the dress came to mid thigh and showed off
plenty of my tight clad legs. "Get your shoes on sweetie while I get you
some earings to wear. "Earings! Come on Diana, this is asking just way
too much from me." "Stop whining Gary, we're almost finished. I stepped
into the girly Pink shoes and tied the white apron around my waistline as
tight as possible to try and give me a girlish figure. After Diana
clipped on my gold dangly earings to my pierced ears she walked me over
to her vanity. "Now look Gary, You have to wear some blush and lipstick
to hide your boyish apperance. A little eyeliner wouldn't hurt either."
"Please Diana, I can't take much more of this." Over the next 15 minutes
she began applying makeup on my face. Lipstick, blush, eyeshadow and
other beauty items were picked from the vanity until she was satisfied.
After my makeup job was complete she sprayed us both with girly perfume
and brushed out my hair into a more feminine looking dew. I was then led
to a mirror where I got a good look at myself and her big smile. "You see
baby, no one's gonna recognize you in that outfit!" I was speechless as I
stared at the two young girls reflections in the mirror. I was looking
real good but there were hints of my boyishness all over including my
unpolished nails and the fine hair on my fingers. When I raised my hands
to hers she handed me the white gloves and I quickly put them on. "You
see Love, all is now hidden. Just keep your trap shut for the next 3
hours and everything will be fine. Come on, lets get back downstairs so
Mom can get a good look at you."
With every silky step we took together Diana continued to make a fuss
over me. She was totally enthralled with my new feminine look and wasn't
shy in telling me about it. The skirt of my dress fluttering over my
tight clad legs and the silky feel of my long sleves felt so nice. Maybe
there was hope I could pull this off for the next 3 hours?" When Miss
Kelly got a good look at me she uncrossed her nyloned legs and high
heeled it over to me and her daughter. "Not bad Diana, not bad at all!
She looks so sweet and innocent in her tights and dress." She wrapped her
arm around my waist while Diana picked at my hair. The two of them
fondling me was the spark that began the fire in my panties. I could feel
an erection beginning to blossom with every silky step I took and
feminine touch they gave me! "Remember Diana, I want Gary back here until
it's time to start serving." "Yes Mom we've been over it 100 times."
"Gary darling, don't say a word even if you're spoken to. Just smile,
politely nod and walk back to the kitchen if you get pinned down.
Understood?" I nodded making my earing jingle to the delight of Diana.
She gave me one last hug and then we began setting the table for Miss
Kelly's guests.
Over the next hour my semi hard pantied cock grew into a very strong
erection. The perfume, lipstick and being femininely dressed by my dream
girl had opened my feminine floodgates. Diana could clearly see that
something was wrong with me as I nervously tried to block out the
sensations I was feeling. After everything was set to go she grabbed my
gloved hand and yelled to her Mother. "Mom I want to freshen up our
makeup before everyone shows up." "Good idea dear just don't take too
long." Before we hit the first step with our feminine feet she whispered
softly to me. "What's the matter sweetie, you seem to be lost in space
the last half hour or so." I tightly grabbed her hand and she rushed me
back up to the changing room. After sitting me on the bed she gazed deep
into my eyes. After a few sniffs her mouth dropped wide open. "OH MY GOD
GARY! Don't tell me you have a...?" Her hand slid up under my skirt and
softly touched my pantied hard on! Her smile grew as big as ever while
her opened palm slid effortlessly over my stiff nyloned cock. "Di...
Di... Diana, what's happening to me?" I was nervously shaking and rubbing
my silky arms trying to make sense of everything that was happening.
Diana on the other hand was as cool as could be. "You know Gary, this is
very unladylike and we can't have you downstairs smelling like boy
butter!" She pulled me from the bed and took me into one of the
bathrooms. She lifted up my skirt and pulled down my tights and panties.
My rock hard cock sprang out in front of the sink and she immediately
turned on the cold water. Over the next 5 minutes she filled cup after
cup of cold water and poured it on my throbbing cock. I let out soft
moans and tried to pull on it several times to her disappointment. By the
time she got my erection under control we had made a nice mess in the
bathroom. Just as I was about to pull up my panties and tights she
stopped me and handed me a pantyliner. "Here put this in your panties..
Maybe this will keep you from feeling all girly!" "I... I'm sorry Diana,
I don't know what had come over me?" She cupped my chin and once again
gazed into my eyes. "Don't worry sweetie, some boys have feminine
tendancies and don't even realize they have them. You just might be one
of those special boys?" We shared another hug just as the doorbell rang
out. "Remember sweetie, keep your mouth shut and try not to make eye
contact with Mom's guests."
After sneaking back to the kitchen Diana began filling glasses of water.
I began filling the salad bowls and friut cups just like Miss Kelly
instructed me. I was slowly getting my senses back but the feel of my
clothes and watching Miss Kelly sashay around in her tight fitting
miniskirt made it impossible to get control of my emotions. As the guests
piled in my nervousness grew. Many of the women were laughing it up and
having a good time before the meal was served. My nervousness only grew
when I heard one of the women and Miss Kelly getting closer and closer to
the kitchen. I looked over at Diana with my terrified outlined eyes and
she motioined me to turn my back and check the spagetti sauce. I had just
taken off the lid when Miss Kelly and her guest entered the kitchen. "Ohh
Caroline that sauce smells so good. You and your daughter have once again
out done yourselves." "Well Thank you Melissa, I know we aim to please
when it comes to entertaining our franchisees." There was a pause for a
few seconds as it felt like 20 sets of eyes were staring at me. "And
who's the new girl if I may ask?" Miss Kelly cleared her throat but
before she could answer Melissa opened up again. "By the way, I heard a
rumor that you had hired a stocking boy or was it a boy in stockings to
help out with your store." I could've fainted right there as Miss Kelly
began choking on her wine. "Mel... Mel... Melissa where on earth did you
here about that?" I overheard a few of the highschool girls gossiping
about him when they were in my store last week. They said you hired a
stocking boy and had him working part time. Many of the girls were pissed
off because you hired him over them. Any truth to this Caroline?" "Ohhh
Melissa, why do you listen to those gossiping girls. All I can say is
that those girls wern't willing to work weekends, that's why they were
turned down for the job." "Well, they seemed very convincing. I can tell
when they really mean it by how emotional they get." "Well, lets talk
about it later and get this luncheon going. Girls you can start serving
the spagetti now that everyone's here." Miss Kelly and Melissa walked out
to the dining area and I took in several deep breaths. Diana gave me a
hug and a few comforting words. "Hang in there girlfriend, you still have
over 2 hours to go." I gave her a hug and began babbling in her ear.
"Please don't make me go out there Diana. I don't think I have the
courage to have them all look at me especially after what Melissa just
said." "Calm down Gary! You're getting your panties in a bind. Just keep
your head down while you wheel the cart out. I'll place the plates in
front of everyone and we'll be back here to hide out in 5 minutes. Now
come on, start filling up the plates."
After the cart was loaded up with the entrees Me and Diana began walking
out to everyone. Diana placed the plates in front of the women who really
didn't pay any attention to us. By the time the last plate was on the
table Miss Kelly gave me and Diana high praise. "Thank you girls, find
some way to amuse yourselves for the next half hour. Just as I was about
to push the cart away from the table I felt one of the women grab the
edge of my skirt making me abruptly turn around. "And what is your name
sweetie, I don't think I've seen you here before?" I shyly looked away
like Miss Kelly told me and she quickly dived in to rescue me. "Ohh where
are my manners. Everyone say hello to my newest girl Ga..... Ga... Gabby!
I could've cried as Miss Kelly addressed me with a girls name! I was
frozen stiff and Diana came back to help push the cart. "Come Gabby, we
have pots and dishes to wash." Miss Kelly ran her hand through my long
hair as she saw the terror in my eyes. "Don't mind Gabby ladies, she's
just a little shy." As the women began eating I hurried my steps back
into the kitchen and immediately hugged Diana. "Ohhh Diana, I'm so
ashamed at what happened out there! I don't think this was such a great
idea dressing me up as a girl?" She held me close for over two minutes
before nervous tears began filling my eyes. "Easy now Gabby, you'll ruin
your makeup. I took in a few deep breaths while she dabbed my tears with
a tissue. It took me several minutes to calm down as I tried to make
sense of what was going on inside my head. Here I was dressed as a girl,
having hard on issues while the girl I want to kiss so bad continued to
fill my head with more and more feminine theories and thoughts. All I
knew that when this day was over I'm never coming back to help out again
at one of Miss Kelly's gatherings. The store girls can have my place from
now on.
By 1:00 everyone was out of the house and I found myslef in the middle of
a Miss Kelly and Diana sandwich. "You did wonderful Gabby! You fooled
everyone out there. Even Mrs Valentia was complimenting how nice the two
of you looked in your dresses." Miss Kelly gave me a kiss on the cheek
while Diana interlocked her fingers with mine and stared deep into my
eyes. "You girls finish up down here while I change and take care of a
few things upstairs. Then we'll head back to the store to finish out the
day." Miss Kelly Clicked her heels out of the kitchen while Diana
wrapped her arm around my waist. "Well Gabby it looks like I owe you one.
I know it doesn't seem like we did a lot today but you were a big help."
"Please Diana, lets finish up so I can get out of this dress and wash off
my makeup." She got a real pouty look on her face as she put her lipstick
covered lips just a few inches from mine. "Come on Gabby, why do you want
to change so quickly? I thought you might want to head into the shop in
one of my skirts and tops since you're looking so good right now." I
began shaking my head from side to side and stood my ground. "No way
Diana! It's bad enough I had to wear a dress, tights and makeup for half
the day. No, I think I want to change back into my pants and shirt before
we head out." "Ohhh Gabby, waht's a couple more hours of dressing up? We
can work together on our storage project and maybe we can find you some
more panties to buy while we're there?" "Very funny Diana! You just wait
til I see those bitches Brittany and Constance on Monday. They suckered
me into this dress thing and then got $400 in panties out of me as well."
"You seem upset Gabby? I thought since we worked so well together today
that you would be helping me and Mom out on a regualr basis when we need
you." "Ohhh no you don't Diana! I have to draw the line somewhere. I'm
not saying I won't help out anymore but the next time I show up I'll be
reading the fine print before signing up." She began giggling and stroked
my long hair. "Don't worry Gabby, one of these days that little head of
yours will be reminding you how much fun it is to play dress up and wear
makeup. By the end of the month you'll be begging Mom for more Saturday
overtime work." She gave me a kiss on the forhead and then we headed back
up to her room to clean up and change.
When I showed up for work on Monday I found myself alone once again. My
hopes of seeing Diana working by my side again turned into one of lifes
many disappointments. After about an hour of reorganizing some bras and
dreamy camisoles Brittany came strutting back to my desk. She put down
her Starbucks Coffee cup and smiled. "So, how'd it go sweetie? Did you
and Princess Di patch things up?" I set my pen down and rather than blow
up on her I took the more relaxed route. "Well it wasn't what I was
expecting but everything worked out fine for the luncheon." "So I guess
it wasn't worth $400 in panties hmmm?" "Don't worry Brittany, me and
Diana are on the road to recovery. I still have to think about a few
things she wants me to do, but well get through it." "well there must
have been some headaches cause I don't see Diana here today." I took a
sip of my Coke and picked up my clipboard. "Yea well, she must be busy
today or something? I'm sure she'll be here on Wednesday to help." "I
guess time will tell stocking boy!" She turned and took about 15 steps to
head back out in the main shop before turning back to me. "Ohhhh by the
way, you sure looked great in your Pink dress and tights!" I quickly
turned to her and yelled. "What did you say? What Dress! What Tights!"
"Take a look at the website and you'll see what I'm talking about
sweetie." I quickly went over to the storeroom computer and clicked on
our webpage. True to her word there was a posting about the weekend
Franchisee luncheon with several pictures of me and Diana in our Pink
dresses! Even though I had my back turned in all the photos you could
still make out 2 young girls with long hair wearing pink dresses and
girly shiny white tights!
After catching my breath I raced into Miss Kelly's office. She was just
finishing up a call when I closed the door behind me. "Yes Gabby, what is
it?" "MISS KELLY! Please don't call me that in here." She took off her
glasses and gave me a wink of her black outlined eye. "Settle down Gary I
was only kidding, now what's on your mind?" "Miss Kelly please take those
luncheon images off our webpage. Everyone can see I'm wearing a dress in
those pictures!" "Gary will you calm down! The images have been up since
Sunday morning and I haven't had one person come and tell me that it was
a young boy in one of those dresses. You're secret's safe with me and
Diana." "Miss Kelly it's not that simple, Brittany and Constnace know it
was me in those photos." "Don't mind the girls having a little fun with
you. I told you when I hired you that you would have to deal with a few
pranks and lots of kidding around." "I don't care Miss Kelly just take
those pictures down before someone puts two and two together." "Well,
you'll have to take that up with the webpage admistrator who took the
pictures, I don't have the skills to remove the images." "Well how can I
contact the administrator?" "Ohhh that will be very easy, you can discuss
it with her this weekend at my Halloween social on Saturday. I'm sure
Diana would love for you to join us? She just loves being sneaky with her
hidden cameras and she hasn't stopped talking about how great you looked
on Saturday!" Now I knew I was screwed! Diana was using the pictures to
twist me into another one of her Mother's Saturday functions to help out
again.
"This is such crap Miss Kelly! I don't want to wear tights and pink shoes
again! Can't I just be a regular boy?" Miss Kelly came over and gave me a
hug. "I promise you won't be wearing tights or girly pink shoes for the
party." Her fingers worked through my long hair as I thought about
returning for another one of her gatherings. After a long look at the
pictures on the website I gave in. "Ok, if the pictures are removed
quickly and I don't have to wear tights or girly shoes I'll show up for
Saturday." Miss Kelly picked up her phone and began pressing buttons.
After several rings she opened up. "Diana darling I have great news!
Gabby has decided to help us on Saturday for the party but you need to
take the Luncheon images of her off our webpage immediately. Gabby's a
little nervous about how she looks on the website." After a few nods of
her head she set down her phone and began walking me out of her office
back to the storage room.
"You know Gary, my daughter has eyes for you in some very unique way. I
know your real close to winning her over but you have to keep an open
mind when you're with her." "Miss Kelly I'm so confused about how I felt
this weekend working in those clothes? I loved being with your daughter
but why does she get so turned on by dressing me up to look and act like
a girl?" "Ohhh Gary, she's just experimenting a little that's all. I will
admit she tends to eye feminine boys up rather then the bad boys or jocks
who constantly try and get dates with her." "I'm not feminine am I?" She
began to giggle a little and then slid her hand down to my waist. "You
may not realize this Gabby, but I've seen you drueling over several items
in the store over the past few weeks. You seem to be confused at what
your doing at times but I can clearly see what's going on." I swallowed
hard as we entered the back room with her locking the door behind us. Her
hand slid down to mine and she interlocked our fingers together. I was
starting to get warm all over as she walked me back to one of the dark
dressing rooms that never gets used. "Miss Kelly why are we going back
here?" Her high heels clicked away and her short leather skirt continued
to slide over her suntaned nyloned thighs. Now way out of sight from the
sales girls and customers she pushed open a door and clicked on the light
switch. Hanging on the hook was a Kelly Lingerie sales girls dress, low
heeled shoes and several pairs of feminine undewear. Miss Kelly began
playing with my long hair as I nervously looked at everything. After a
few seconds she took the dress from the hook and I almost passed out when
I saw the name 'GABBY' sewn on the uniform. The short skirted silky Pink
chiffon dress was clearly made for me but I couldn't understand why?
"Miss Kelly, why does that dress have my name on it?" "Ohh come now
Gabby, it's quite obvious I want you to start working up front soon.
You're knowledge of my inventory will be a huge asset to my customers and
they can't tap that knowledge with you hiding back here in the
storeroom." She laid the dress over my chest and the skirt came right to
mid thigh like all the other sales girls dresses did. "Miss Kelly I think
you've been hanging around your daughter too long? Why do the two of you
continue to try and dress me up as a girl?" She let out a sigh and hung
the dress back on the hook. "Questions, questions, questions! That's all
I get from you Gabby! Victoria gave her notice today and she's only gonna
be with us til the end of the week. I don't have time for interviews so
Diana suggested that you could fill in nicely if we need you until I find
a suitable girl to replace her. Now start getting undressed so we can see
how it fits you." Miss Kelly wasn't in the mood for any BS as she began
unsnapping my jeans. Before I could lodge one protest she had my shirt
off. "Miss Kelly I don't want to be a up front sales girl!" "Calm down
Gabby, with a little polishing you'll be perfect for the job." By the
time I was completely naked Miss Kelly had a handful of girly lingerie in
her hands. "Get your panties on sweetie!" I quickly pulled up the Pink
panties to cover my cock and balls while Miss Kelly quickly wrapped a
padded pink bra around my chest. Once again I began to feel my cock begin
to stiffen up from the feel of the shiny satiny underwear. After a good
looking over Miss Kelly wrapped a bright white waist cincher around my
waist and began pinching it shut with the fabric coated buttons that
lined the front of it. My beathing began to soften up as the tight
fitting cincher began to squeeze my waistline into a more feminine shape.
"Miss Kelly this cincher is really tight on me! Maybe one of those
Longline girdles would work better?" "Nonsense Gabby, the short legs of
those longline girdles would be noticable because the skirt of your dress
is so short. This is just a quick trial run for fit. We'll polish you up
real nice if you make it out front in the coming weeks? Here, get your
support hose on while I unzip this dress." Miss Kelly handed me the beige
control top pantyhose and I began bunching them up. "You know Gabby, you
should have your toenails polished at all times if you want to fit in
around here." "Please Miss Kelly you're pushing me too far!" After
tucking the waistband of my pantyhose up under my cincher, Miss Kelly
unzipped the dress and threw it over my head. After fitting it around my
cinched waist she began to zip me up. The dress quickly began to fit
around my feminine frame to the delight of Miss Kelly. "This is really
fitting you nice Gabby! Kudos to Diana for getting your measurements
exactly right this past weekend." Miss Kelly pulled my hair up and let it
fall onto my shoulders. She then spun me around in my stockinged feet
making the skirt of my dress flare out. "Ohhh Gabby, I'm loving what I'm
seeing. To bad Diana isn't here to see you in your salesgirl dress." Miss
Kelly's soft long nailed tipped fingers fondled my tight waistline,
padded breasts and nyloned legs to the point where I grew a massive
hardon in my panties! I was a mess to say the least. Every soft touch of
my skirt on my nyloned legs and Miss Kelly's fingers were turning me on
in a big way. "Ohh my god! You need shoes and a ribbon for your hair."
Miss Kelly grabbed my sweaty hand and began walking me back to the main
storeroom away from the dimly lit secluded dressing rooms.
As we inched closer and closer to the locked door I could hear the sales
girls chatting about the pictures on the website. Miss Kelly had 3 pairs
of low heeled Pink shoes well hidden in the storage racks and pulled out
a size 7 for me. "Step into these pumps sweeite and lets see how they
fit." My nyloned feet entered the tight fitting shoes and I quickly began
to complain. "Miss Kelly these are really tight, an...an.. and the heel
height is too high for me!" "Nonsense Gabby, now lets walk around a bit
and see if we can break em in. As Miss Kelly held my arm I slowly began
taking small steps around the room. My stiff cock in my panties couldn't
have been stronger and I couldn't have been more humiliated by my
feminine apperance. Then when I heard Constance's voice from the sales
floor I almost passed out. "Yea, in an another month or so sweet Gary
will be a regular working girl around here. I can't wait to see how she
looks in one of our cute pink dresses." Miss Kelly heard it as well and
wasn't shy about voicing her opinon. "Sounds like Constance has it all
figured out Gabby! Maybe we should make our way out to the sales floor
for a few minutes hmmmm?" My throat was dry as could be as I continued to
accustomed to my new feminine fotwear. "Pl... Pl... Please Miss Kelly let
me change back into my boy clothes." She showed no sings of stopping her
feminization of me as she placed a pink headband in my hair and clipped
on a pair of pink earings to my ears. After a good looking over she
handed me my clipboard and pen. We stared at each other for about 10
seconds before she snapped her fingers loudly. 'SNAP! SNAP! SNAP!' "You
can get back to work now Gabby and try not to put a run in your hose."
Miss Kelly walked back to the dressing room and locked it real good
before walking back over to me. "I'll keep the girls out of here for the
next few hours, now get your pretty ass moving!" She gave my pantied ass
a nice swat which only turned me on even more for some reason. She
slipped out the side door back to her office as I stood there trembling
with nervousness. After a few deep breaths I accepted my feminine fate
for the day and went back to organizing the storage room.
Over the next 2 hours I dealt with my feminine demons that were slowly
winning the battle inside me. Not only was I wearing pretty lingerie, I
was also touching and caressing all those lovely panties, stockings, and
satins from the beat up boxes that littered the floor. My cock never lost
its erection and several times I had to stop and try to understand what
was happening to me. The strong support hose on my legs and tight fitting
waist cincher made me melt with every low heeled step I took. The
laughter of the sales girls on the other side of the locked door only
made things worse as my fragile mental state continued to crack with
every one of their girly comments and giggles. "I'll bet you $50 he's
back there trying on some of those panties right now Constance." "No, no,
no, Miss Kelly has him in some sort of tight fitting girdle and
stockings! You know how much she loves to be in control of her shop."
"Yea, I wish we could see what was going on back there before we leave."
At 5:00 Constance rapped on the door as the girls were closing up. "Bye
Gary, see you on Wednesday!" More girlish giggles came from the other
side of the door as I stood there in my dress terrified. About a half
hour later I heard Miss Kelly's heels clicking from her hallway that
connected her office and the storeroom. I quickly put a smile on my face
and tried to look busy before she arrived. To my surprize it was Diana's
heels I was hearing. She was holding her purse and two large garment
bags in her hands when she got a good look at me. "Well Gabby, looks like
you're ready for the slaes floor to be a runner?" I set down my
clipboard just as she set down her purse and garment bags. Our eyes met
once more and she held me close. "You look so awesome in your sales girl
uniform. I can't wait til Mom gives you your big chance one day." Our
nyloned legs were zapping each other with electrically charged static
jolts with evry subtle move. I then quickly commented to Diana about the
sales girl dress. "Diana please let me change before I lose my mind. Your
Mom locked my boy clothes in the dressing room and I can't get them."
"Shhhh Gabby, let me hold you for a few minutes before you change. I had
to come over to see you after Mom told me how great everything fit." I
tried to break off our embrace but her firm grip on me was even more
powerful than before. When her nyloned thigh brushed against my stiff
pantied cock she began whispering in my ear. "Looks like you're enjoying
your dress and heels sweetie. That little pantied cock of yours is so
stiff!" I trembled with orgasmic satisfaction as she slowly slid her
silky thighs against my crotch. I let out a few soft gasps as her lips
pressed to my neck. Her warm waxy lips felt so nice and my erotic
excitement grew and grew. "Mom tells me you hardly put up a fight this
afternoon when she was dressing you. I sure hope this is a sign of things
to come?" With my earings jingling with every soft touch I placed my chin
on her shoulder. "Ohhh Diana, I'm so in love with you!" She softly
stroked my long hair and then snuck her hand up my skirt. As I waited for
her to grab my stiff nyloned cock her hand went to my ass and she began
massaging it. "Such a good girl you are Gabby letting Mom dress you up.
Maybe one of these days we'll have the same kind of fun again?" With her
soft hand massaging my ass and her nyloned thighs sliding across my stiff
pantied cock I closed my eyes and waited for and explosion of cum in my
panties. Over the next minute I felt my cock tense up and jolt a few
times! "That's a good girl get all that nasty boy butter out of you so
can think straight again." I was panting heavily and was a feminine mess
with everything she was doing ot me. As things slowed down Diana lifted
up my skirt and peeked at my panties and pantyhose. "Aaawe would you look
at that. There's no cum stains. Looks like you're not quite ready yet for
your first climax." She lowered my skirt and then picked up the garment
bags and keys to the locked dressing room. Our fingers interlocked once
more as we clicked our heels down the tiled floor.
When she unlocked the door she hung the garment bags on the hooks and
began unzipping my sales girl dress. it only took a few minutes to get
the dress and waist cincher off. When I went to take off my panties and
nylons she quickly stopped me. "Hold it Gabby, You'll be needing those
for Wednesday and Friday." She handed me my pants and made it very clear
I was wearing my feminine underwear home. "Please Diana, I don't want to
be paraded around in that sales girl dress for the rest of the week. Let
me dress normally. You have no idea how difficult it is to wear the
opposite sexes clothes." "That will be enough girlfriend! Now finish
dressing." I reluctantly pulled my pants up over my nyloned legs and
Diana helped me pull my shirt over my bra. At least she took out the
padding so no one would see bumps on my chest.
After I was completely dressed again she wrapped her arm around my waist.
"Now sweetie, Mom tells me you're gonna be joing us for the Halloween
party on Saturday. After giving it plenty of thought I decided on some
great costumes for you and me to wear. Diana unzipped both bags and
pulled out Batman and Robin costumes for us. "OHHH MY GOD Diana! I love
them." "Since you were dressed as a girl last weekend I decided to show
you how much I appreciated it. I can endure a little humility as well and
wear a boys costume for a few hours. I have to tell you though I really
wanted to get the Supergirl costume." I gave her a big hug and she once
again pressed her lips to my neck. "Thank you for letting me be a boy
agian Diana! I was so nervous about what was in those bags. I thought for
sure I was gonna be feminized again!" "Well the deal is this, you're
wearing the sales girl dress for the rest of the week and then it's my
turn for you to have some fun with me as Robin." Without even thinking
about it I nodded and agreed. She zipped up the bags and left them hang
on the hooks. "We'll pick them up at the end of the week before the party
on Saturday. Mom want's you at the house around 10:00 to help with
getting all the food ready like before and then in the afternoon we can
hang out together before the party." We walked hand in hand from the
dressing room and right into Miss Kelly's office. "Everything's set for
Saturday Mom. Gabby loved the costume idea I had." Miss Kelly picked up
her purse and put on her glasses. "Splendid girls, It will be great to
see Gabby in her sales girl uniform for the rest of week and the two of
you will be the talk of the party I'm sure."
After we locked up Diana gave me one more kiss on the cheek before I
watched them drive off. My steps were quick back to the house as the cool
fall air filled my lungs. When I got inside around 6:00 Mom was waiting
for me in the kitchen cooking dinner. I set my bag on the table and
greated her. "Hi Mom how soon til we eat?" She was frying up some
hamburger and just got done wiping off her spoon when she turned to me.
Her hand immediately was raised to cover up her wide open mouth. "My god
Gary!" I looked at her funny as she slowly walked over to me. I could
tell she was in shock as she slowly began raising her hands to me. "What
is it Mom?" While shaking her head her extended fingers pinched my
earlobes. Just that quick she pulled and held out the pink earings Miss
Kelly clipped on my ears earlier this afternoon. I let out a gasp because
I didn't even realize I was still wearing them. I couldn't beilieve Miss
kelly and Diana let me out of the shop wearing them! "Mo... Mo... Mom I
can explain this!" Before I could get one out her fingers pulled off the
girly Pink headband from my head and set them aside of the earings on the
table. "Gary, Gary Gary! What the hell is going on in that lingerie shop?
Earings and headbandson a boy!" I quickly tried to difuse the situation
as I noticed plumes of steam coming from the stove. "Mom your hamburger's
burning!" She stepped over to the stove and moved the frying pan to a
clod burner. She then sat me down in front of my feminine earings and
headband. "I take it this is some sort of joke or something? What are you
doing wearing Pink earings and headbands?" I took in a deep breath and
then sarted lying like never before. "Mom it's ok, Diana and I made a
little bet over the weekend and I lost. Because I lost I had to wear the
headband and earings all day at the shop. I just forgot to take them off
before coming home." She sat back in the chair while firmly holding the
headband and earings. "I think there's more to this by the nervous way
you keep fidgiting in the chair. Give me you phone right now." I opened
up my bookbag and took out my phone. "Wha.. wha.. what do you want my
phone for?" I'm calling Miss Kelly to get to the bottom of this earing
story of yours." I nervously sat in the chair as Mom paged through my
contact list. "Here we go, Miss Kelly. I'll put this on speakerphone so
we can both hear. You keep quiet unless you're spoken to." As soon as
Miss Kelly picked up my heart began beating faster. "Yes Gabby what is
it!" I could've fainted as she refered to me as GABBY!" Mom didn't pick
up on the 'Gabby' intro and went right into the conversation. "Miss
Kelly, this is Gary's Mother how are you doing this evening?" "Just fine
mam thank you for asking. What's on your mind at this late hour?" "Well,
I was wondering if you could help me with clarifying something Gary and I
were talking about? You see, he came home a litle different than usual
tonight." "Different Mam? In what way?" "Well, I was wondering if you or
your lovely daughter could fill in the blanks for me?" "Hold on while I
get Diana over here so she can be of some help because I'm not sure what
you're referring to." After a long pause the sweet feminine voice of
Diana came through the speaker. "Hi Mrs. Hollister, Mom said you need
some help or something?" "Hello Diana, I'm sorry to bother you with this
tonight but it can't wait. Can you tell me if you noticed anything
strange about Gary today when he left the shop. Diana started giggling
and then her Mother chimed in. "Diana, get control of yourself and tell
her." "I.. I.. I'm sorry Miss Hollister but if you're referring to the
earings and headband I guess I'm to blame for that." "So it's true then,
Gary lost some sort of a bet with you?" "Well there's more to it than
that but I really don't want to get into details. I'm sorry about sending
him home wearing the earings and headband I guess I was just so amazed by
how comfortable he was wearing them all afternoon." Mom's eyes opened
wide as I reached for the phone to stop the call. "Comfortable Diana, you
did say comfortable?" "Yes Mam, he never once asked me to take them off
while we were working." Thank you my dear for clearing that up. Have a
nice evening." "Good bye Miss Hollister tell Gabby I'll be thinking about
him!" "Gab.. Gabby! Did you say Gabby? Hello...! hello....! She must have
hung up? Now why would she call you Gabby?" I tried to get my composure
back as Mom turned off my phone, smiled and handed it back to me. "You
know if I was a boy and I was wearing earings I would make damn sure I
took them off before I went home. You must be under Diana's love spell or
something?" "Mom it's not like that, we haven't even gone out on one date
yet." "Well you better start thinking a little clearer than you are now.
The next time you bring your work home with you I might not let you off
the hook so easy. Go get ready for dinner, we'll be eating in 20
minutes." I raced up to my room and set the earings and headband on my
dresser. I quickly took off the bra, panties and nylons Miss Kelly put me
in and threw them in the box I kept under my bed. The whole crossdressing
thing I had going on was almost exposed tonight thanks to Miss Kelly and
Diana's big ideas for me. There was no way they were ever gonna get me
out in the shop to help with customers in one of those pink dresses. Some
how I had to get Diana and her Mother to postpone their big feminine
plans for me?"
Wednesday at the shop Miss Kelly once again assisted me into my feminine
underwear dress and shoes. Today she made me press a headband in my hair
and clip on my Pink earings. She also insisted that I polish my nails
with glossy clear nail polish just to be more official, whatever that
meant?" After my polish dried my longer than average nails gleamed with
feminine shine from the bright overhead lights. Once again for 3 long
hours I rummaged around the storeroom organizing every type of feminine
undergarment. Several times I felt my cock begin to tense up but for some
reason I never got hard toady. On my 10 minute break I went back to the
changing room to once again look at me and Diana's costumes for Saturday
nights party. I unzipped the bright Pink plastic protetctive covering and
peeked inside. It was so nice to see the Batman and Robin costumes again.
I just couldn't believe that Diana was gonna let down her femininity and
allow herself to dress up as Boy wonder. Saturday couldn't come soon
enough for me." After zipping the bags back up I went back out to the
store room where Miss Kelly was waiting for me. It was now almost 5:00
and the sales girls were punching out and setting the alarm for the front
door. After the girls left out the back Miss Kelly unlocked the store
room door and asked me to follow her. I froze in my tracks which only
seemed to upset her. "Lets go Gabby! The girls are gone and it's just us
in here." "Miss Kelly please! Someone might see me through one of the
windows?" "I have the curtains pulled back so no one can see inside now
get your pretty ass moving before I polish those nails with Pink polish!"
I reluctantly lowered my head and walked over to her. "That's a good
girl." She grabbed my hand and we both began stepping out into the main
part of the shop. "Now Gabby, I think it's best for you to know that I
have big plans for you. I think you'll be a valuable asset to my shop the
sooner I get you out of the store room. I figure you might have another 2
weeks or so back there before your work is finished." As Miss Kelly
encircled me I looked up at her in disbelief. "Don't look so frightened
my dear. After all, you owe me a big favor after Monday nights surprize
phone call from your Mother." "Big favor Miss Kelly? You and Diana told
her the truth except for the part of us making a bet." "Her hand patted
my skirted ass and she cupped my chin. "Me and Diana could've sunk your
ship but we didn't. I wonder what your Mother would've said if we told
her you were wearing panties, pantyhose and a bra along with your earings
and headband?" My mouth opened wide at her feminine threats but there was
nothing I could really say. "Yes Gabby, I think next month will work out
fine in getting you properly polished up for your big debute. Who knows,
maybe you'll make it to lead girl if my sales girls continue to resign. I
was feeling weak in the knees while Miss Kelly continued telling me about
her BIG plans for me. But then there was some sort of comotion out on the
sidewalk in front of one of the display windows. Miss Kelly grabbed my
hand and we both carefully inched our way over to the big window. To my
horror I noticed all my buddies from school standing in front of the
window. They all looked confused and at a loss for direction. I went to
step back but Miss Kelly kept me in front of her as we watched the boys.
"Friends of yours Gabby?" "Please Miss Kelly get me away from this window
before they see us! I'll be a laughing stock at school if the guys see me
in this dress!" "Calm down Gabby, they've been here 3 times last week and
twice this week now lets listen in on what they're talking about." I
watched Miss Kelly slide a small picture to the left exposing a small
speaker. After she turned the switch on we could hear everything they
were saying. "I don't know Bobby, I followed him down this road 4 times
this month and he just dissapears into thin air. I have no clue where he
goes but it's gotta be around here somewhere?" "Well he just can't
dissapear. Danny where did he go when you followed hime on Monday?" "Same
thing Bobby, it was right around here when I lost track of him. He didn't
even know I was following him and when I turned the corner he was gone."
I was getting more and more nervous as my buddies went on. "Well sooner
or later we'll find out where he's going. Lets get back to the malt shop
for a burger and come up with a new strategy for Friday."
They began walking away and I began breathing again as Miss Kelly covered
up her secret speaker set up. "I just love this little speaker thing
Diana put in about 3 years ago. Now I can tell what my customers are
saying and what kind of price they're willing to pay for my overpriced
lingeie before I put anything on sale. Come Gabby, lets continue with
what I have planned for you before we lock up for the day." If my menntal
state wasn't fragile enough now I had a pack of wolves trying to track me
down. Unlike yesterday I remebered to take off my earings and headband in
the dimly lit dressing room. Just like Monday Miss Kelly insisted that I
wear my panties and nylons home under my jeans. She told me it would help
get me in the right frame of mind in becoming a 'Kelly Girl' as she put
it.
When I got home Mom was once agian in the kitchen preparing supper.
Before I could make my way up to my room she yelled out to me. "In here
Gary!" I walked into the kitchen and set my bookbag on the table. "What's
up Mom?" "Gary your friends stopped by to see you this afternoon and they
were wondering what had gotten into you the past month. You don't stay
long at the burger shop, play cards or go to movies with them anymore."
"It's quite obvious Mom, I don't have time for those things now that Miss
Kelly has me working 4 days a week." "Well I told the boys you got a part
time job and they knew nothing about it." "Mom please. if they knew I
was working at the shop they laugh and tell everyone. That's why I left
them out of the loop." "Well they know about where you work because Danny
asked me if you worked near the underwear store." "Mom! you didn't tell
them did you?" "Relax sweetie, I told them nothing but you better watch
your back because they seem determined to find out what's going on." I
sat there with my mind racing as Mom placed my plate in front of me.
"Well which bet did you lose today sweetie?" I heard the words but
couldn't put the sentace together becasue I was deep in thought. I looked
up at Mom and she repeated herself. "I said, which bet did youlose
today?" I immediately reached up to my ears and head but there were no
earings or headband to take off today. "Very funny Mom! ha Ha! She set
her plate down and grabbed my hand from the table. With one twist of my
wrist a shiny reflection bounced off my polished nails. "Earing on
Monday, Clear nail polish today. what's it gonna be for Friday Gabby?
LIPSTICK!" "Mom please don't call me Gabby! It's bad enough Miss Kelly
and Diana call me that all day." I pulled my hand from her grip and
turned 3 shades of red. "There's some nail polish remover and clippers on
my dresser. I'm sure you don't want to be the talk at school tomorrow
with those girly nails. Dinner wil be ready at 6:00 so you have plenty of
time to get that polish off." I picked up my bag and hurried myself to my
room. After shutting the door behind me I began to really worry about all
these little feminization tricks Miss Kelly was playing on me and the
fact that I never see them coming until it's way too late do anything
about it.
On Friday afternoon I skipped my last class and snuck out the gym exit to
get to the shop before my buddies could follow me today. I got in about
2:00 to the surprize of Miss Kelly. "Well Gabby, starting early today are
we?" "Miss Kelly I guess I felt like working a little extra today if you
don't mind?" "Not at all sweetie, Diana had a day off from school and
she'll be working with you today so punch in and join her." I wasted no
time in getting back to the storeroom where Diana was waiting for me.
When our eyes met it was instant smiles for both of us. "Gabby!" After a
long hug Diana interlocked our fingers together. "You still comin
tomorrow Batman?" "You bet I am Robin! I've been counting down the hours
til party time!" "Well before we get to the party lets get you properly
dressed for this afternoon's work. Mom was kind enough to wash your
uniform so it's nice and fresh for you." "Diana couldn't we skip the
dress and heels for today? My feet are still sore form Monday and
Wednesday's workouts." "Ohh no you don't Gabby! We made a deal to take
down those luncheon images and we're not going back on it now." When we
got back to the dressing room I could see the pink plastic costume bags
that our costumes were in. Before I took off my pants I unzipped the
Robin costume Bag and pulled out the costume. "Come on Diana, try it on
I'm dying to see you in it!" She took the costume from my hand and hung
it back on the hook. "You get undressed immediately while I put this
back. You can wait another day before you see me in it." I watched her
place it back into the bag and rezip it back up. She then unzipped the
batman bag and pulled out the costume. "Hmmm, maybe I'll be Batman and
you can be Robin instead?" I had just slid on my hose and turned back to
her. "NO WAY! I'm Batman and you're Robin we already decided that on
Monday." With a disappointed look she put it back in the bag and zipped
it back up. She then began zipping me up into my Pink Kelly Girl sales
dress. I stepped my nyloned feet into the low heeled shoes and Diana
completed my look with a Pink scrunchie and earings. Today however the
clear nail polish was gone and a bottle of Pink polish sat by a tube of
lipstick. "I'm so glad you got here early, now we can do your nails and
get some light makeup on your face." Diana sat down and crossed her
lovely tan stockinged legs. She polished each of my nails with quick
drying Pink polish that matched the color of my Kelly Girl dress. While
my polish dried she waxed up my lips with Pink lipstick and brushed my
cheeks with some pink blush. I never protested once and she knew I was
hooked on what she was doing to me. She gave me wink of her eye and her
feminine excitement began to build as I got prettier and prettier. When
she walked me to the full legth mirror I could see two pretty girls in
the mirrors reflection. Even though you could pick out my boyish features
the feminine web I was caught in made it impossible for me to accept I
wasn't enjoying myslef. "Come Gabby, lets get busy."
For 4 long hours I pranced around in my short skirted dress and heels to
the delight of Diana. She was really impressed how well I was handling
myself in my feminine footwear. I caught her eyeing me up several times
and spotted some frustrating and disappointing looks on her face as well.
Despite her emotional setbacks she made sure she brushed herself against
me every chance she could. She pinched my nylon ass so many times that it
began to sting! Her feminine charm and beauty was so great to be around
so when it was time to leave and take off the dress she could tell I was
kinda bumbed out about it.
After changing back into my clothes and cleaning up my polished nails and
makeup Diana handed me the costumes while she picked up her purse. "Now
Gabby, be at my place tomorrow at 10:00 sharp. If you want to come
earlier that's fine just don't be late!" "So how long is this party gonna
last?" "Who knows, Midnight, 2 am? Ask your Mom if you can spend the
night with us then she won't have to stay up late to come pick you up."
"Hey that's a great Idea Robin! "You bet it is Batman, come on, lets get
out of here." I carried our costumes out to Miss Kelly's office where she
was just finishing up her invoices. "10:00 tomorrow Gabby, please don't
be late." "I won't forget Miss Kelly, I'll be there before 10:00." I made
my way out the door carrying my bookbag and our costumes. By the time I
got home my arm was killing me. The costumes weighed alot and my frail
arms had all they could handle for the 6 block walk back to my house. I
took the costumes up to my room and hung them on my door hook. I was so
looking forward to tomorrow with great expectations. After taking off my
feminine underwear I got inot a pair of sweats and a tshirt. I then
started on my weekend homework to get it out of the way before tomorrows
big day with Diana and Miss Kelly. Mom was working late tonight so I left
her a note that I needed a ride to Miss Kelly's for 9:00am. I could eat
a quick breakfast and then get over there early so I could be with Diana
longer.
At the breakfast table the next morning Mom was not keen on the sleep
over idea but she went along with it when she saw important it was to
spend as much time with Diana as possible. After showing her the costumes
she immediately shook her head. "Well that must have been one big bet you
won with Diana to get her to put on a Robin costume in front of all her
friends and Miss Kelly's guests tonight?" "Here's Miss Kelly's email
address, I want you to send her a message tonight sometime and I'll have
her snap a few pictures of us together to prove I won the BIG bet with
her. I may have lost a few battles this week but I surely won the war on
Friday." "Ok, ok, I'll send her a message around 8:00 to see the two of
you. Now finish up so I can drop you off before head into town to do some
shopping." After finishing up my cereal I grabbed my overnight bag and
the costumes while Mom locked up. I proudly walked down to the car where
my good friends Bobby and Danny just happened to be passing bye. "Well,
well, well if it isn't Houdini! You're not gonna get away from us this
time Gary. Now where the hell do you work at and how come we can never
find you?" "I got myself a girlfriend and I've been preoccupied keeping
her happy, if you know what I mean?" "Ohhhh yeeeea, we know what it's
like to have the fresh smell of snatch! So what's in the bags?" "Ohhh
these are our costumes for tonight's costume party." "well where is it?
Maybe we'll stop by?" "Ohhh it's by invitation only so you can't get
inside. I'll tell you what though, you go to 1004 Panasonic drive tonight
around 9:00 and ring the bell. Whoever answers the door, tell them you
want to see Gary and Diana. "You'll flip when you see us in our
costumes!" "Ok Gary, 1004 Panasonic drive, got it!" By now Mom was
running late and tried to chase the boys from the car. "Come back another
time boys we're on a tight schedule this morning." I laid the costumes on
the back seat and jumped in the front with Mom. After a honk of the horn
we made our way over to Miss Kelly's house.
When Mom pulled up to the driveway I hopped out with my bag and costumes.
"Have fun tonight dear." After another honk of the horn she drove off and
I began my trek up the driveway. When I got to the top of the hill I
noticed a fancy foreign red sportscar parked by the sidewalk. It must
have had 10 coats of paint on it the way it shined. The custom license
plate read 'JET POWER' and the chrome embelishments shined as bright as
could be. After ringing the doorbell Miss Kelly greeted me at the door.
"Well good Morning Gabby! You look so drab in those jeans and
sweatshirt." "Well if you don't mind Miss Kelly lets go with GARY when
the party gets going since I forgot my pink dress and heels back at the
shop." After a chuckle she walked me in and right to the stairs. "Go
ahead up to Diana's room, she's with two of her friends from school. You
can set your bag and costumes in the spare bedroom." I made my way up the
stairs and hung a right into the spare bedroom. On the bed were two
leather coats, purses and kick ass leather boots. I laid the costumes on
the bed along with my overnight bag and then took the short walk to
Diana's room. I could hear the girls giggling loudly as I approached and
took in a deep breath before knocking on the door. 'Knock! Knock!' Diana,
it's me, are you decent inthere." I then heard one her friends softly
whisper. "She's here, she's here!" After some more giggling Diana's sweet
voice rang out. "Come in Gabby! Come in!" I pushed the door open and
there sat two stunning long haired french girls eyeing me up! The two of
them were undressing me as I inched closer to Diana who hopped off the
bed and gave me a hug. "Good morning Gabby, I want you to say hello to
Jeannette and Julliette AKA the JETS." I was speachless as both girls
were identical twins with long brunette hair, black polished nails and
perfect makeup! Both of them were dressed identical with short Black
leather skirts and shiny black nyloned legs. After a good stare Diana
gave me an elbow in the ribs. "Don't be rude Gabby, say hello to the
girls." I quickly put a smile on my face and acknowledged them. "Nice to
meet you girls. Are you coming to the party tonight?" Before one of them
could answer Diana walked me over to the bed and sat me in betwen them.
"Actually Gabby, they stopped by to show me their costumes for another
party they're going to tonight." "Aaawe too bad you won't be here to see
me and Diana in costume?" One of the girls then nudged a little closer
and crossed her nyloned legs in front of me. "Yea, we have a 4 hour drive
to get to our party in New Jersey this afternoon so we can't hang around.
Too bad you and Robin can't join us, I think we'd have a lot of fun
together, isn't that right Julliette?" "It sure is Jeannette, Diana's
told us all about you and how flexible you are when it comes to certain
female things." She gave me a wink of her eye as she also crossed her
nyloned legs and twirled her shiny nyloned foot in front of me. My eyes
were all over the two of them and I wanted so bad to interlock my fingers
with them. Diana looked on with a huge smile and could see I was at a
loss for words as the girls twirled their hair with their black tipped
fingers.
We made small talk about their outfits and car for a few minutes then
Miss Kelly yelled up from downstairs. "DIANA! Get down here and help for
a second!" "OHHH Mom, can't it wait a few minutes?" "No it can't, get
down here right now please!" "Sorry guys I have to run I'll be back in a
few." Diana raced out the room and shut the door behind her. It only took
the girls a few seconds to start up with me. "So tell us Gabby, are you
wearing panties right now? Diana told us how much you love crossdressing
and playing dress up at the lingerie shop." Jeannette's nyloned toes
began inching up my pantleg and she got a disapponted look on her face
when she saw my leg. "Gabby, where's your nylons sweetie. Diana tells us
you love support hose and tight fitting girdles. We thought for sure you
would be wearing them for her this morning?" "Girls! Girls! please get
control of yourselves. Diana was just kidding about the nylons and
panties." "Ohh I don't think so Gabby!" Julliette then took out her phone
and proceeded to show me countless pictures of me in my Kelly Girl Pink
dress from the shop. "You see sweetie, we know all about you and your
hidden femininity that Diana talks about at school all the time. She's so
frustrated because she can't seem to break you out of your shell." Both
girls interlocked their fingers with mine and my cock began to stir. "You
know Gabby, I bet if we played dress up with you we'd get you to crack in
one afternoon. Maybe one day when Diana loses interest in you, you can
stop by our place for a few feminine rounds with us? We'd love to put the
moves on you down in our basement wouldn't we Julliette?" I tried to get
up but they held me firmly in place. "You see how weak and feminine you
are Gabby?" You have no idea how to process our moves because of how much
you like it. Most boys your age would have had their hands in our panties
by now but you seemed to be preoccupied with other thoughts?" I began
breathing heavier and heavier as they began licking my neck. "We just
love feminine boys sweetie. Now be a good girl and let us see your pretty
panties!" Jeannette's hand slid into my jeans and right on top of my hard
cock. "That's a real nice boner you got going on in there Gabby. Diana
tells us you haven't even cummed yet. You're still shooting blanks in
your panties." Both girls began giggling as I was on the verge of passing
out. Both of their hands were pulling on my cock as they continued
filling my head with feminization stories they wanted to play out with
me.
It took Diana a good 5 minutes to get back to put an end to the French
connection. She could see me and the girls were having fun while she was
gone and wasted no time in blasting them. "Damn it girls, leave Gabby
alone. She's a very delicate flower and the two of you play too rough
with feminine boys!" Both girls got off the bed and straightened out
their skirts. "Take it easy Diana, Gabby was just telling us about how
much she's looking forward to becoming a Kelly Girl and working with the
other sales girls next month." Jeannette gave me a wink and Julliete ran
her fingers through my long hair. "I just love her hair Diana! I sure
would like to see what she looks like on her first day." "Don't wory
Julliette, there will be plenty of pictures on the website when Gabby
makes her debut. You girls better get going if you want to be in Jersey
at 2:00." "Yea we have to get going. It sure was nice meeting you Gabby!
I hope our paths cross again soon?" "Come on Gabby, get down to the
kitchen and help Mom with the crock pot while I say goodbye to the
girls." I hurried myself out of Diana's room and made my way into the
kitchen to a waiting Miss Kelly. "Well Gabby grab your apron and start
cutting up the vegetables." "But what about the crockpot?" "I took care
of that, we're now moving on to bigger and better things." Miss Kelly
tied a white apron around my waist and I began cutting up carrots and
celery. As the teenage girls walked out through the livingroom they
continued to make a fuss over me. "Ohhh he's to die for Diana! You're so
lucky he showed up and applied for the 'stocking boy' job." "Yea,
sometimes things just go your way I guess? You two have a safe trip to
Jersey and we'll talk again at school on Monday." I felt more relaxed
after hearing the sportscar fire up and peel off down the driveway. The
last thing I needed in my life were two more crazed girls who wanted to
feminize me to the bone!
By 1:00 everything had been diced and chopped up. The beverages were
chilled and all that was left to do was get our costumes on. When Miss
Kelly showed us her Wonder Woman costume me and Diana began ooohing and
aaahing. "Looks like you signed up with me and Diana for the Superhero
theme?" "You bet I did Gabby, when Diana and I picked up the costumes at
the store on Monday I decided to come back for the WW costume." "Well
you'll look awesome in that skimpy thing Mom." "Thank you my dear! Now
why don't we all head upstairs and get dressed?" "Mom it's only 1:00, the
party doesn't start for 3 more hours." "Well it never hurts to be ready
in case we have some early guests or possibly some trick or treaters." We
followed Miss Kelly up to the spare bedroom and I picked up the Bright
Pink costume bags that held our costumes. I handed Diana one bag and then
began unzipping another bag. After the zipper was pulled down I reached
inside and grabbed the hanger. "Ohh Diana this is gonna be so much fun
tonight. I pulled the costume from the bag and Miss Kelly let out a gasp.
"What the hell is that!" My trembling hand held out a Black satin short
sleeve dress with a built in white fluffy petticoat and satin apron! I
stared at the frilly feminine costume for 15 long seconds and began
shaking my head. "I don't understand where's my Batman costume!" Diana
quickly unzipped her costume bag and pulled out an identical black satin
dress with a built in white petticoat. She then let out a big sigh. "OH
MY GOD! Julliette must have grabbed the wrong bags when the girls left!
They're gonna be so pissed off when they find out we have their french
maid costumes." "Well that's not a problem Diana, call them up and have
them bring the costumes back and we'll switch them." "It's not that easy
Mom, the girls left over 4 hours ago and they're probably in Jersey by
now!" I fell to my knees clutching the black satin dress and frilly
white satin apron. A single tear rolled down from eye as the three of us
thought about what was next. After a long pause Miss Kelly pulled me and
the dress from the floor. "Well I guess we really have no other choice
but to have the two of you wear the girls costumes?" Miss Kelly began to
pick at my long hair while Diana pressed the dress to my chest. "I don't
know Mom, Jeannette's dress would probably fit Gabby better but I really
can't be sure?" "Well the two of you better decide quick because my
guests will be arriving shortly. Make sure you do something with Gabby's
hair if she decides to wear the maid costume." Miss Kelly left the room
and closed the door. Diana came over and hugged me with the two dresses
between us. "I'm so sorry about this Gabby! I was so looking forward to
being Robin tonight." "Yea, it sure looks like the dress gods just won't
let me catch a break will they?" She held me close for 5 long minutes and
stroked my long hair. All the while I continued eyeing up the Black
dresses. "You know Gabby, I can't really force you wear the maid dress
but I was hoping you would do it for me and my Mom. She's really counting
on us tonight." I stood there silent with my body softly trembling.
Diana's soft touches and begging made it tough to walk away from her.
"Gabby, if you do this for me tonight I promise we'll go out on a date
and you'll have your girlfriend!" Her hand slid down my thigh and a small
smile appeared on my face. As soon as she saw it she began unbuttoning my
jeans. Her eyes gazed down to me as my pants fell to my knees. "Your turn
Girlfriend, step out of those pants and I'll blow your mind tonight!" Her
hand slid inside my white underwear and right on top of my semi hard
cock. With soft silky pulls I quickly stepped out of my pants and took
off my shirt. Her lips met mine and we shared a 15 second kiss. I was now
over the edge of the feminine cliff with no parachute! I would do
anything she asked to get another taste! After our kiss was over she
interlocked our fingers and she began walking me out of her room. She
hurried me down the hall to the bathroom and locked the door behind us.
Now lets get those socks off and start working on your hair like Mom
said." I began shaking a little as I kinda knew what Diana was up to. I
tossed my socks on the floor and Diana took a white bottle from the
cabinet. "Hop in the shower for me sweetie while I get this conditioner
mixed." "Diana I think this asking way too much of me. Please don't mess
around with my hair. I like it the way it is." She showed me the bottle
of conditioner and then began to wet my hair with a squirt bottle.
"You're gonna love this conditioner Gabby! Just give it a few minutes and
then we'll shampoo your hair as well." After squirting the white cream
all over my hair she worked it in with her fingers. "Doesn't that feel so
nice sweetie?" I stood there totally shocked at her being unfazed by my
nakedness. After my hair was totally drenched with conditioner she placed
my hair up into a ball and then snapped on a tight pink rubber cap.
"Really Diana, what the hell is going on here and what are those other
pink bottles you have?" Just as I was about to step out of the shower she
picked up one of the pink plastic bottles and began filling her palms up
with a thick Pink cream. "You're gonna love this stuff Gabby and I've
been waiting so long to do this!" "DO WHAT!" With a confident smile she
began to smear the cream all over my arms. "Uhhhhh Diana, what are doing?
Is this more conditioner or shampoo?" She turned my palms right side up
and then began filling them. After the bottle was empty she quickly
grabbed another one from the marble top vanity. "Start creaming your
thighs and shins sweetie while I work on your backside." She turned me
around and her soft creamy hand began to touch my shoulders. The cream
felt so nice and the sensual way she applied it made my cock stiffen up
once more! "Diana, I'm starting to get hard again! Maybe we better finish
this later?" She hurried herself and quickly coated my ass and legs until
there were three empty bottles laying on the floor of the shower. Even my
balls were coated with the pink cream. "Now you stay still until I get
back and don't wipe off that cream until I tell you to. I'm gonna try and
get hold of those two French Fried Fashionistas of mine to see if they
noticed the mixup yet?" She gave me a wink of her eye and then pulled the
shower curtain all the way towards the spikets. While I stood there
covered in Pink cream my stiff cock stood straight out at attention. It
was very clear that Diana knew how to press my buttons and did what ever
she wanted to keep me walking a fine feminine line for her. I just hoped
tonight's party wouldn't be to crowded or crazy.
When Diana made her way back to the bathroom she had changed into a
casual pair of sweats and sport bra to hide her budding feminitity. My
creamy Pink skin was tingling all over and I wanted to get the cream off
as quick as possible. "Ok Gabby lets get that hair rinsed out and cream
off of you!" She pulled the tight fitting shower cap off my head and
turned on the shower. As I rinsed my hair out I noticed tiny brown specs
of hair on the bottom of the shower. After shaking my head real good I
came to realize that my long hair was fine and wet. However when I wiped
the cream from my arms I noticed all my thin arm hairs were gone! My legs
and tummy area were also hair free as the warm water cascaded down my
hairless body. "DIANA! What's going on here! All my arm and leg hair is
going down the drain." She pulled back the curtain with a smile and could
clearly see I was on the verge of tears. "Here, get the rest of that
cream off while I get you some baby oil for our bath." I wiped every inch
of me clean of the cream while Diana watched with a confident smile. My
skin was soft, sliky smooth and pink all over just like a young girls. I
now wondered what I got myself into and what else Diana had planned for
me.
After I was toweled dried off Diana began polishing my toenails bright
red. With my cock still stiff as could be there was no way I could tell
her I wasn't enjoying myself even though I was quite confused on what was
happening. Several times Diana would give my buldging head a lick or pull
which only made me harder! While my toenails dried she ran a disposible
pink razor across my neck and face to remove every last bit of boyish
fuzz. Now that I was smooth all over her enthusiasm continued to grow.
Her smiles were bigger and her fondling of my sensitive skin was turning
her on just as much as me. when my nails had dried she began to draw a
steamy bath. She stepped out of her sweats, panties and sport bra before
collecting me in her arms once more. "Ohh Gabby, you feel so nce now!" I
could feel her body softly trembling as her budding breasts touched my
silky smooth skin. "Diana, why did you put hair remover on me? What am I
gonna do when the guys in gym class see my hairless legs and arms?" "Take
it easy Gabby, It will grow back in a month or so. Besides, Mom insisted
that you be Naired good and proper since our sexy dresses have short
sleeves and shorter skirts. You can't wear girly opaque tights with the
formal dresses we'll be wearing. Sheer pantyhose won't hide leg hair so
we had to Nair you." "I understand that Diana, but you should've asked me
first before doing something like this." "Well, I have to tell you Gabby
I always wanted to secretly Nair my boyfriend and put him in a dress one
day. Thank you for being so special and letting me fulfill one of my
teenage fantasies!" Diana turned off the water to the tub and then
squirted a liberal amount of baby oil all over herself and me before we
stepped in. We sat face to face and massaged the steamy oily bath water
all over our tender skin. My cock was still as hard as could be and she
took good care of it with little oily pulls with her soft hands. "I got a
hold of Julliette to figure out what happened. Apparently you set our
costumes by the girls purses and coats in the bedroom and Jeannette
picked them up by mistake not knowing that Julliette hung their costumes
on the back of the door. Mom then came up and moved everything around a
few hours later not knowing who put what costumes where. The girls will
be on their way back from Jersey in a few hours and will try and stop in
later tonight to apologize." I let out a sigh as I gazed down to my soft
feminine skin and bright red polished toenails. "I understand Diana, you
have no idea how depressed I am right now. I wanted to have fun being a
real boy tonight in my Batman costume. Now I have to wear another dress
in front of bunches of people. I'm getting so nervous just thinking about
it!" She gave my rock hard cock a few soft pulls to try and calm me down.
"Take it easy Gabby, it's just some of Mom's business partners and
friends. We have a lot of work to do but I think we can pull off this
feminine miracle Girlfriend? And who knows, you might just fall in love
with your new look?" A few times I could feel myself getting ready to cum
when the base of my hairless cock tensed up but once again nothing
happened. "By the way Gabby, who flirted with you more while I was gone,
Jeannette or Julliette?" I lifted my head up with a big smile and eyed
her up. "Jeannette was by far the flirtier one. They both wanted to see
if I was wearing panties but I stopped her just short of pulling my
zipper down." "Hmmmm, Interesting? I thought for sure Julliette would've
tried a stunt like that before Jeannette. Did they get you hard while
they played with you?" I quickly looked down at my red toenails and Diana
cupped my chin. "Gabby, I asked you a serious question. Did they get you
hard?" I let out a sigh and confessed. "Yes girlfriend, they got me nice
and hard just like when we're touching each other and having girly fun."
'Thank you for being so honest Girlfriend. One thing we must have is
TRUST! Now we have a few things to go over so listen up." We sat in the
tub talking for over an hour massaging the oily bathwater all over us. We
made out a few more times to try and soften the feminine blow I just took
with the costume mixup.
By 2:30 we were out of the tub and Diana began working on my makeup and
hair. For 30 long minutes she masterfully coated my face with makeup,
eyeliner, lipstick and pink blush. My long soft hair was brushed out felt
so nice on my hairless shoulders compared to before. That conditioner and
shampoo really feminized it good and proper! My longer than average nails
were filed into a girly oval shape and polished real nice with Bright Red
polish. Diana even plucked a few hairs from eyebrows to help hide some of
my boyish features I still had remaining. After she finished up with her
makeup it was time to get dressed. I stepped into my darling Black satin
panties while Diana strapped me into my bra. On the table was a small box
and after opening it she pulled out 2 life sized silicone breast that
looked as real as hers. "Mom was saving these for your debut as a Kelly
Girl at the shop but I think this as a good time as any to start breaking
them in." After placing them in the cups of my bra she tightened up the
bra straps to give me a awesome looking bustline. "Get your nylons on
while I get your waistcincher ready." With pantyhose in hand I sat my ass
down and began bunching up the nylons. "Carefull Gabby, those French
Silks go for $40 per pair." After stepping my red toenailed tipped toes
in the black nylon I slowly pulled the silky hose up my legs. "Ohhh
Diana, these feel so wonderful!" "You may never go back to boy underwear
again sweetie?" Diana helped smooth out some of the uneven areas before
snapping the waistband around my thin waist. "Looking real good
girlfriend!" I was falling in love with the new silky feel against my
hairless skin. Everything was happening so fast as Diana continued with
my feminization. Her soft hand sliding over my nyloned thighs and ass
made my cock as stiff as ever! She now wrapped the Bright white waist
cincher araound my waist and began to snap it shut. "Ok Gabby, this is
gonna be a little uncomfortable at first because it's a size smaller than
the one you wore at work all week. Take in a deep breath for me so I can
get this thing on properly." WIth each snap of the buttons I sucked in
more and more air until I couldn't get any more in. "Tha.. tha.. that's
all I can take in Di... Di... Diana!" The last two buttons snapped shut
and I slowly exhaled my filled lungs. After a quick inspection she pulled
my dress from the padded hanger. "I sure hope you can fit in this or
we're totally screwed!" The dress was tossed over my head and she
immediately pushed my hairless arms into the short poofy sleeves. "Well
that's a good start, it doesn't seem to tight yet?" While I held my hair
up she swished the stiff white petticoat over my nyloned legs making me
weak in the knees. "Diana that petti feels so soft and I love the noisy
sound it makes against my nylons." "Take it easy Gabby, don't start
drifting off on me. I need your full concentration tonight." She began
zipping me up the back and I watched the Black satin began to tighten up
against my feminine frame. Half way up my back she ran into a little snag
but after pulling the zipper back down and up the teeth began clicking
together again. The zipper was pulled all the way up to the back of my
neck and was clasped shut for a wonderful fit. I let my long silky hair
fall to my satin shoulders and marveled at how great I looked in my
dress. "My god Diana, it really fits me! Just look how great everything
is coming together." She wrapped a crisp white satin apron araound my
waist and tied it off in a bow. "Sit your ass down so I can get your
heels on." I twirled around in a circle and watched my poofy underskirt
twirl under the skirt of my dress that only came to midthigh. Everything
was turning me on! My buttery soft skin and silky fabrics were something
I wanted more and more of. Diana had me step into a pair of shiny Black
low heeled strappy shoes that clearly showed off my red nyloned toenails.
The heel height was about 2 inches which was just a bit higher than what
I was wearing at the shop all week. A pair of diamond earings were
secured through my piereced ears and a few sprays of perfume from a heart
shaped bottle completed my look.
After helping Diana into her dress and heels we looked each other over
and fine tuned our feminine look. She then walked me to her Mom's full
length mirror for a peek. The reflection and transformation was
incredible. Shine beamed from us like two stars in the night! Our satin
dresses, long hair, shoes and nyloned legs had a feminine chic shine to
them that couldn't be missed. When Miss Kelly joined us in her Wonder
Woman costume she had to stop in her tracks before entering her bedroom.
"My God Gabby, you two look stunning in those maid cotumes!" Miss Kelly
stroked my long hair and slid her long red nailed tipped fingers up and
down my nyloned legs. My cock instantly jolted in my panties and my skin
pimpled up with goose bumps. She nodded with approval and raised her
phone to us. "Ok girls, squeeze in tight and give me some great smiles. I
have to have a few pictures of the two of you." As soon as we wrapped our
arms around each other, our petticoats touched and sparked with a staticy
charge! ZAAAAAP! "WOOOOW! Did you see that Gabby?" After getting my
senses back I nervously began twitching. "Not only did I see it, I felt
it all over my dress and nyloned legs!" Miss Kelly riased her camera and
the two us puckered our ruby lips for her. "Ohhh that's perfect girls!"
We posed for 10 or so pictures and then went back to Diana's room while
Miss Kelly made her way downstairs. With fingers interlocked and our
black outlined eyes staring at each other, Diana pulled me closer. "So
girlfriend, any regrets yet?" I gave her hug and as soon as our satiny
breasts touched I felt her twitch violently. She immediatley let out a
soft gasp as our petticoats sparked again and again with every subtle
move we made. "You know Gabby, there's no turning back now for you? If I
know my Mother, you'll be out front at the shop on Monday as her new
Kelly Girl." The sound of our dresses rustling together and the feel of
our satiny bodies touching pushed me to the point of no return. Whatever
was happening to me today was now locked in my brain with no combination
in sight to unlock it! But the bigger problem was what was going on in my
panties. My cock was so stiff and I was so turned on that I couldn't
think straight. I was rubbing my nyloned legs together as she held me and
she knew something wasn't quite right. "Gabby, are you feeling ok?" When
I didn't respond I felt her hand slide up under my petticoat and onto the
control top of my pantyhose. "Boy this might be your strongest one yet
sweetie?" I left out a soft moan when her fingers began fondling my
nyloned cock. "Ohhhhh Diana, I feel so feminine right now!" "Well why
don't we try something a little different this time sweetie?" She locked
the door behind her and pulled the blinds aside of her bed. The room was
now quite dark but I could still what was going on. I watched in
amazement when she knelt down on her nyloned knees. Her hands and head
then disappeared under my snowy soft petticoat. As I teetered in my heels
I stedied myself as she rolled down my pantyhose and panties. Her mouth
quickly engulfed my stiff cock and she began sucking me off! I watched my
petticoat bounce around as she feverishly licked and sucked. Her warm
tounge and waxy lips provided just the right amount of lubrication and
friction to get the base of my cock jolting. Unlike before my cock began
spewing gobs of boy butter deep down her throat with every silky sucking
motion she had. I was a complete feminine mess as my dreamgirl who I had
admired for months pleased me in a way I never thought would ever happen.
After she sucked me dry she kissed the head of my cock and tucked it back
into my satin panties. The control top on my pantyhose was pulled back up
and her head slid out from under my skirt and petticoat. She gave me the
best hug and began giggling. "Looks like that was a first for both of us
Gabby? I sure hope you enjoyed it as much as I did." I gave her kiss on
the lips and she immediately stuck her cum coated toung on mine! The
sticky boy butter tasted salty and she made sure to lick the inside of my
cheeks all over before breaking off our kiss. She then began giggling as
I tried to make sense of just what happened. "Don't look so confused
Gabby, maybe someday you'll be on YOUR knees pleasing your boyfriend the
way I just pleased you. I'm just priming you up with a little taste
before that day comes. Lets get ourselves cleaned up and fix our lipstick
before we head downstairs." Over the next 15 minutes or so we fixed our
makeup, dresses and brushed out our hair one last time before heading
downstairs to join up with Miss Kelly.
With very feminine strides me and Diana waltzed into the kitchen where
Miss Kelly had bowls of chips, drinks and snack trays all set to go. I
was still getting use to my dress and petticoat bouncing up and down with
every step I took. I also couldn't get my first orgasm out of my head or
the thought of Diana sucking me off so nicely. By 4:00 costumed guests
were arriving, me and Diana hung out in the kitchen as long as possible
before Miss Kelly came in and grabbed our hairless arms. "The party isn't
here girls it's out there." With a firm grip both of us were pulled out
of the kitchen to the awaiting crowd of guests. As soon as her guests
laid eyes on us flashes filled the room along with oooohs and aaaaaaahs.
"Ladies, if you need anything tonight my maids will continue to fill your
wine glasses or plates with snacks. I swallowed hard as several costumed
women walked over to greet us. "Well Diana I must say you and Gabby look
stunning in your costumes, especailly Gabby here. Just look at him Grace,
long girly hair and nails with a proper bust and waistline. "I just can't
believe what I'm seeing Ruth! To think that this is Miss Kelly's Stocking
boy from the shop she's been telling us about for the past few weeks. The
women fondled my skirt, petticoat and hair for what seemed like an hour.
The comotion drew more women over to admire my look and all I could do
was smile and nod. "How about that Leslie, he even shaved his arms and
legs so his sheers would look awesome with her dress." "Yea, I see what
you mean. I wonder what his boyfriend would do to her if he saw her in
that sexy outfit?" The girls all laughed including Miss Kelly who
continued to hold me in place so I couldn't sneak back in the kitchen.
The fuss over me continued for over a half hour. At the request of Miss
Kelly I walked as femininely as I could down the hall and back to show
the women that Miss Kelly wore the pants around here. "She really handles
herself nicely in those heels Caroline. Do you have him practicing at the
shop or something?" "Ohh most certainly Janet! Gabby loves wearing her
Pink Kelly Girl dress and heels when she's working with me after school."
The women's glasses were all empty and Miss Kelly instructed me and Diana
to get busy refilling them.
By 8:00 all the women were getting a litle tipsy. Me and Diana mingled
with almost all of the them in between filling glasses and walking around
with silver serving trays full of snacks. Even though I was still quite
nervous I continued to do the best I could without tripping in my heels
and spilling wine all over the place. After a refill me and Diana went
back to the kitchen for a 10 minute break and to open more wine bottles.
"Gabby, you're the talk of the party! Everyone loves you and your new
look. Mom is really impressed with how well you're taking this wardrobe
malfunction the Jets put us in." "Diana, I'm really having a good time
but this waist cincher is killing me! Can't we losen it up a bit before
we go back out?" "Gabby we can't do that now. I would have to completely
undress you to possibly losen it and we don't have 20 minutes to do that.
You're just gonna have to tough it out for another few hours til everyone
leaves." I continued trying to twist my waistline for a better fit but my
hairless skin made it impossible to slide the cincher in any direction.
Just as we were about to head back out with the wine and trays. Leslie
and Janet came walking in the kitchen. "Hey girls, you got company and
you're wanted out front." Diana's eyes opened up wide and she grabbed my
hand. "I thought I heard Julliette's sportscar outside! Lets go Gabby, I
can't wait to hear this great apollogy from Jeannette and Julliette!"
"Yea, it better be a damn good one for what they put me through!" Diana
and I briskly walked passed everyone with petticoats bouncing under our
short skirts out to the front door. "Fix your skirt and apron Gabby!" I
twisted my apron while Diana fluffed out my petti and the skirt of my
dress. She then wrapped her arm around my waist and gave me a wink. "You
may have the honors Gabby. Give it to them good!" My feminine hand
grabbed the doorknob and I began raising my voice as I pulled the door
wide open. "I'm wearing this damn dress becauase of you gi...!" There was
a long silence as I looked out at the 5 boys I hung around with from
school! I began biting my lipstick covered lip with Bobby stepping a
little closer. "GARY! Is that you in the dress?" I could've cried as the
boys encircled me and Diana. "You boys leave Gabby alone!" "OHH MY GOD!
She called him Gabby!" The boys began laughing it up and I began to get
very emotional as I teetered in my heels in front of the boys. "What
happened to Batman and Robin?" The two of you look more like that maid in
the Clue movie except she was a real girl not a boy in a dress!" Danny
then lifted up my petticoat and skirt exposing my pantied ass to the
boys. "Just look at that guys, girls panties and pantyhose!" I femininely
swatted at Danny's hand but he quickly pulled it away before I could slap
it. "Let go of my dress and leave my panties and pantyhose alone Danny!"
The boys erupted with laughter and were quickly getting out of control.
Diana consoled me as my eyes began filling up with tears. Miss Kelly came
over to see what was going on and pulled me and Diana back inside. "You
unruly boys get out of here, Gabby has plenty of work to do and she can't
hang around with you tonight." The door slammed shut and I was in tears.
Diana rushed me by everyone and marched me upstairs to her room.
Once inside her room she held me close as I balled my eyes out. "There
there Gabby, you knew this day would come when your secret would get away
from you." "This is all your fault Diana! If your friends wouldn't have
taken our costumes my friends would've never seen me dressed like a girl!
How am I ever gonna have the strength go to school on Monday or any day
for that matter? Once the boys tell everyone I was dressed as a french
maid for Halloween my life will be over!" Makeup stained tears fell to my
ruby lips as I cried in Diana's arms. Miss Kelly came up to see if there
was anything she could do but the dam had already burst. With all the
comotion the party broke up around 8:30 and I never left Diana's room.
After my tears were dried up she washed my face, reapplied my makeup and
brushed out my hair. By 9:00 I was back in one piece but I had a million
butterflies in my cinched tummy making me as nervous as possible. We
helped Miss Kelly clean up the last of the dishes and glasses. She was
heading to another party in her kick ass Wonder Woman costume and made it
a point to tell us she wouldn't be home til dawn.
Just as we were getting ready to head upstairs. We heard the fancy
sportscar buzz up the driveway. This time Diana opened the door while I
stayed a step back. When Jeannette and Julliette came in carrying the
costume bags I flipped out on them. "You bitches! Do you have any idea
how my life is screwed thanks to you!" Jeannette set down the garment
bags she took by mistake and walked over to me. She looked me over from
head to toe and then wrapped her arms around my cinched waistline. "You
look so freakin hot in my dress pretty boy! Now let me show you how sorry
I am for all the trouble I caused you." Before I knew it her lips were
burning mine and her hand was up under my petticoat! I tried to wiggle
out of her grip but the long day in heels and humiliation had zapped all
my strength. For 2 long minutes we shared a very long passionate kiss.
Finally Diana stepped in and broke off our kiss. "Come on Jeannette, let
her come up for air for heavan sakes. Her fingers interlocked with mine
after the kiss and I could see Diana and Julliette were quite amazed at
Jeannette's bold move on me. "Diana, I just love your new Girlfriend!"
Diana placed her hand on her hip and and began stroking my long hair.
"Yea, it seems Gabby's everyone's favorite new girl. Come on, lets hang
out up in my room for a while. Mom's gone til sun up so we have the house
to ourselves." The four of us began walking back up to Diana's room but I
was in no mood for anymore fun. I was tired and so confused on what to do
next when Monday arrived.
For the next half hour we sat on Diana's huge bed. Me and Diana were
still dressed in our maid uniforms despite my cries to take it off. We
had music playing and all of us talked about makeup, clothes and school.
Jeannette was right by my side but I tried to sit as close to Diana as
possible. "So Gabby, any idea on what's gonna happen at school on
Monday?" I looked over to Julliette who had a big smile on her face. "I
have no clue at this point? I may just skip Monday and work at the shop
all day if Miss Kelly lets me?" Diana gave me a shoulder nudge and I lost
my balance on the bed. My hand slid over to Jeannette and she immeidately
grabbed it. "Maybe you could spend a day at our school on Monday Gabby? I
know the high priestess would love to have you as an honorary student for
one day." "Jeannette, how am I gonna fit in at an all girls school?"
"It's easy sweetie, you wear a proper uniform and get yourself dolled up
like you are now. I know Mrs Wetherford would be thrilled to see you
especially after all the class conversations we've been having about you
the past few weeks." My mouth dropped open wide and I wiggled my fingers
from her grip. "You were talking about me!' "We sure were, how bout it
girls?" Diana began giggling and rubbing my satiny back as she filled me
in. "Yea Gabby, when I told Mrs Wetherford we had a boy working in the
Lingerie shop the whole class erupted with curious questions." "My God
Diana, you didn't tell them my name did you?" "Relax Gabby, no one knows
your real name except Jeannette and Julliette." I sat there in a daze as
the girls began cackling about how great it would be for me to show up at
their school on Monday.
At Midnight we were still going strong with music playing and talking
about everything girly. Then Julliette hopped off the bed and pulled
Diana with her. "You got anything good to drink around here Diana?" "Ohhh
I'm sure we have a few bottles of wine left over from the party." "Well
lead the way because I'm thirsty." The two of them began walking to the
door with Diana leading the way. When I saw Julliette's hand slide down
onto Diana's poofy skirted ass I blinked my thick lashed eyes for a
second look. Diana began giggling and showed no opposition to Julliette's
touching. "You two have fun until we get back!" Julliette flicked off the
light switch leaving me and Jeannette in the dark. After the door shut I
felt Jeannette's hand on my nyloned legs. "Did you see that Jeannette?
Your Sister put her hand on Diana's ass!" She inched closer to me and
pulled me close. "Take it easy Gabby, the 3 of us have been experimenting
with each other for months now." Her lips pressed against my neck and she
began sucking it. "S... S... Sooooo the two of you are like dating
Diana?" As her tounge slid up my neck she pulled me even closer. "One of
the hazzards of being in an all girls school, there are no boys to date.
Now settle your pretty ass down and hold me closer." I sat there in
another cloudy thought pattern as some of the feminine pieces to Diana's
puzzle began to click together. No wonder Diana's been dressing me up
like a girl and treating me so nice the past few weeks?" After another
long kiss I felt Jeannette's hand up under my skirt again. "So do I fit
into your experimenting game in some way?" "You're already in it Gabby,
and by now you'll never forget how great your clothes feel or when you
have your first orgasm dressed as a girl. No crossdresser can ever put
those things out his mind after he's had a little feminine taste of the
other side." All her touching and fondling had once again made my pantied
cock rock hard. Her soft hand massaged it perfectly just like Diana's did
earlier today. "Jeannette, please stop this before they come back."
"Realax Gabby, by now my Sister's on top of your girlfriend devouring her
tounge and lips. It wouldn't hurt to get a little excitement out of you
during our makeout session you know, now pucker up girlfriend!"
Jeannette's comments through me for a loop to think that Diana was into
Girls and Boys that dress like girls.
While me and Jeannette made out her soft hand began to work it's magic on
my stiff cock. My feminized body was shaking all over as my massive
erection filled my panties and pantyhose. Jeannete was softly stroking my
hair while her nyloned legs intertwined with mine on the satiny bed
sheets. She knew I was close to climax and pulled me from the bed. "Now
Gabby, I've been dying to this with you ever since I saw you on those
secret survalance tapes Diana showed me months ago." Her head went up
under my poofy petticoat and skirt just like Diana's did earlier today.
As my nylons and panties were pulled down her warm mouth engulfed my
stiff cock! I let out a few feminine moans and placed my hands on her
shoulders while she sucked me off. The base of my cock began to twitch
and my body began to quiver all over once more. I let out a few orgasmic
cries and my stiff cock opened up squirting cum into her mouth. Once,
twice and then a third time I creamed her mouth while I shook with
pleasure. This was by far a stronger orgasm than the one I had with
Diana. I was so turned on and thrilled with everything she was doing to
me. The excitement of the moment got to me though and I fell back on to
the bed trying to catch my breath as my feminized body quivered and
shook. She immediately pulled up my panties and pantyhose as I laid there
catching my breath in the darkness. She then laid on top of me and
pressed her cum stained lips to mine! As soon as she forced my lips open
she spit my cum into my mouth! As I mumbled and tried to open up I began
choking and swallowing it. I could feel her facial expression turn to a
smile as I swallowed down every last drop. "That's a good girl Gabby!
Just a little taste of what's to come for you if you ever get yourself a
real boyfriend?" I closed my eyes for a breif second and then slowly
began to pass out just as Diana and Julliette came back to the room.
"Well Jeannette did you get her to cum again?" "Not only did she shoot it
for me, she also swallowed it as well." "Great job girlfriend, we now
have a boy toy that can give us everything we were missing as our sexual
desires mature." "Lets drink to the great day we had and what's to come
Girls!"
When I woke up the next morning Diana's head laid just a few inches from
mine on the satin pillows. Our hair was entangled together and I was
still dressed in my maid uniform. She however was dressed in a pair of
Pink pajamas from what I could see of her. I laid there for about half an
hour trying to remember the last thing that happened before I passed out.
My pillow and my side of the bedspread were stained with makeup that I
slept in. I could see my heels were on the floor next to Diana's dresser
and her uniform that laid over the back of her vanity chair. The sun was
bright beaming through the Pink drapes and I could here Miss Kelly
walking up and down the hall past Diana's room. After giving Diana a
nudge with my elbow she slowly began to stir. "Come on Mom, just 10 more
minutes." She pulled the bedspread over her head and tried to go back to
sleep. I in turn yanked the bedspread from her hand and the bright
sunshine beamed down onto her pretty face. "Diana please get up and help
me out of my maid uniform." She slowly interlocked her fingers with mine
as we laid face to face on the pillows. Her eyes were shut but she wasn't
even close to getting back to sleep. "Just let me lay her for 15 more
minutes Gabby, then I'll let you out of your dress." "Diana Please, we
have things to talk about. Now please wake up." After a yawn her eyes
barely opened up and she began smiling. "Gabby, why did you sleep in your
dress last night?" "Very funny Diana, I passed out last night after
Jeannette wore me out. At least I think that's what happened?" After
another yawn she opened her eyes up to about halfway and reached up under
my skirt. "Jeannette tells me she got you to cum. Is that true sweetie?"
"She sure did! It was an orgasmic fealing I'll never forget." "Was she
better than me, Gabby?" I hesitated with my answer for about 5 seconds
before interlocking our fingers together. "Diana, the two of you pressed
my buttons perfectly to induce me to cum. But for some reason my Cum
stream was stronger with Jeannette than when you got me to cum." Her free
hand began massaging my limp nyloned cock as she shut her eyes all the
way again. "Hmmmm, interesting! So what did she do differently? Did she
jerk you off first or maybe give you a nice nylon foot job to get so
excited?" Diana's soft hand massaging my cock and all this cum talk once
again began making me hard. "Diana please! She sucked me off just like
you did, I'm not sure why I cummed so much better in her mouth? This is
all kinda new to me." As she stroked, my cock continued to get aroused.
"You know Gabby, they say you never forget your first time. But in your
case you may not forget your second time?" I let out a soft moan as my
cock began to grow inside my Black satin panty and pantyhose. The sound
of Miss Kelly prancing up and down the hall in her heels added more
nervousness to my fragile psyche knowing full well she could walk in on
us at any time! "So tell me Gabby, did Jeannette swallow your cum like a
good girl or did she spit it out on the floor. I know for a fact she was
saving her first time to be with you so I kinda figured she swallowed
every drop." I began biting my lower lip as my cock stiffened up even
more. After a long hesitation Diana increased the tightness of our
interlocked fingers. "Well Gabby, I have to know, did she swallow your
boy butter?" In total frustration I laid my head back down on the pillow
next to her head and closed my eyes. "Well, after I shot my load in her
mouth I fell back on the bed trying to catch my breath. That's when she
pressed her lips to mine and squirted my cum back in my mouth!" Diana's
massaging now had me fully erect and her smile grew and grew. "How about
that! A girl giving a boy a cum job with his own boy butter. And here I
thought I was being shrewd by just giving you a taste from my tounge when
we kissed. So did she let you up to spit it out or did she make you
swallow it?" "Ohhhhh Diana, this is so embarrassing! I swallowed it all
because I had no strength left in me to get up and spit it out." Diana's
hand snuck inside my panties and pulled my stiff cock out. She then
wrapped my soft petticoat around the shaft and began pulling faster. "Now
be a good girl Gabby and give me a morning cumming before we get out of
bed." She was turning me on just like Jeannette did the night before.
Even though her Mother was sashaying right past the door my stiff
erection began to climax. My feminine body began to quiver and my cock
came to life with every silky pull. "Di... Di... Diana! I'm gonna cum!"
"Shhhh, keep your voice down Gabby! Mom's right down the hall." Her head
slipped under the bedspread and once again under my petticoat. Her lips
wrapped around my cock and after three jolts from the base of my cock I
began moaning and cumming! Three more powerful cum shots filled her mouth
as she sucked me dry. My breathing was heavy and my quivering body shook
with excitement for the third time in 18 hours! Then I shot a fourth and
fifth load into her mouth to complete my morning cumming.
When her head popped up from under the covers her half shut eyes met mine
and she moved in for a morning kiss. I could tell her mouth was still
full of cum as I tried to twist from her grasp. "Diana, what do you think
you're doing!" Her hair was messed up and her breasts were quite visable
to me. I tried to twist away once more as her lips inched closer. I knew
she was about to let me have it and there was no stopping her! When her
lips pressed to mine she began to refill my mouth with my own cum like
Jeannette did last night! "You better swallow every drop and lick me real
good Girlfriend!" Her power rush and our cum breakfast was now turning me
on for some reason but I couldn't understand why? I swallowed down every
drop and began licking her tounge and the inside of her cheeks to try and
get every last bit of it. She knew what was going on and humped my semi
hard cock with her thigh to try and get me to cum again. Unfortunately
her Mother began knocking on the door just as we finished kissing. "You
girls get your asses up and shower! You have to eat breakfast and get
dressed before head into the shop for 12:00." We both held each other
close and when She went to get up I pulled her back into my hairless
arms. "Diana will you be honest with me?" She began stroking my long hair
and pulling on my semi hard cock once more. "What is it Gabby?" "Well,
last night Jeannette let it slip that you had some secret tapes of me or
something? What is she talking about?" Diana gave me a wink and hopped
off the bed. She rolled her tv right up next to the edge of the bed and
popped in a 6 inch wide black tape into a machine on top of the tv. After
hopping back into bed with me she turned on the picture. "Now Gabby, take
a good look at the images I'm about to show you." After a few seconds an
image of the outside of the store came into view. A few seconds later I
walked up looking into the store windows. Diana's fingers interlocked
with mine and she skipped to the next scene on the tape. Again and again
she showed me peeking in the windows eyeing up the lingerie clad
manequins. "You see Gabby, we've been watching you for 6 months now
hoping some day you would find the courage to walk into the store so we
could put our feminine moves on you. Unfortunately you wouldn't step
inside. So then my Mother suggested the 'Help Wanted' sign when we showed
her how many times we recorded you sneaking peeks at our manequins. After
she busted you snooping around a few weeks ago you fell right into her
lap when you nervously asked her about the job." Diana turned off the
recorder and cupped my chin. "There's no going back Gabby. Gary has set
sail on another ship, from now on it's gonna be silks and satins!" She
gave me one more powerful kiss on the lips as I sat there completely lost
at how this all played out on me. "So I guess Julliete and Jeannette
never had another party to go to last night did they? The three of you
had the costume switch all planned out in advance?" Diana gave me a wink
of her eye and cupped my chin once more. "It's about time you figure a
few things out Girlfriend. Did you really think I would wear a boys
costume?" I lowered my head and began shaking it making my earings
jingle. "Don't take it so hard Girlfriend, sooner or later we were gonna
get you the way we want you for our fun. Now lets get you cleaned up
before we join Mom at the breakfast table."
After finally getting out of my maid costume I got to shower and take my
messed up makeup off I was ready for a relaxing bath. The steamy bath
water felt so different on my hiarless skin and seeing my bright Red
nails in the water took a little getting use to. I shampooed my hair and
lathered up with a girly shower soap Diana gave me to use. After towel
drying myself off and moisturizing my smooth skin I wrapped my towel
around my waist and walked back to Diana's room to change. When I got
inside she was already dressed in her Kelly Girl Pink uniform complete
with shiny tan hose and pink low heeled shoes. hanging from the bed
canopy was another Pink Kelly Girl uniform with the name 'GABBY' sewn on
it in bright White letters. "Diana, what's going on? Where are my clothes
I wore yesterday?" "We don't have time for that right now Gabby. Get your
panties and nylons on so I can do your makeup before you get your dress
on." Diana pulled off my towel and handed me the panties and pantyhose.
"Diana I have to get home this morning I can't work in the storeroom
today." She began snapping her fingers while checking her look in the
mirror. 'SNAP SNAP SNAP!' "Now Gabby! Lets get moving! I allready talked
to your Mom and she said it would be ok for you to work today." I slid on
my panties and began bunching up my pantyhose with my fingers. "But I
don't want to work in the storeroom today." "You're not working inthe
storeroom, you're gonna be helping me out front today since the other
girls are out of town." I snapped the waistband of my control top
pantyhose around my bellybutton and Diana quickly wrapped my Pink bra
around my chest. My silcone breasts were jiggled into the cups of my bra
and Diana began wrapping the waist cincher around my sore waistline.
"Please Diana, I can't take another day in that thing!" She gave my
pantied ass two nice swats. 'CRACK! CRACK!' "Knock it off Gabby, I'm in
no mood for fun and games. We have to be down at the breakfast table in
30 minutes or I'll get my ass swatted. Now suck that sissy gut of yours
in so I can snap this thing shut. I wasn't on my nyloned knees yesterday
sucking you off for free?" I lowered my head and pouted as I sucked in as
much air as I could. Once it was in place Diana threw a light pink nylon
slip over my head and the hem of the slip came to mid thigh. She then had
me step into my dress and zipped me up. Without saying a word she pulled
me over to her vanity and began removing the Red polish on my nails. She
worked very fast and repolished my nails in bubble gum pink polish. The
same color that matched my heels and dress. It only took her 15 minutes
to make up my face and brush out my hair the way SHE liked it! A few
spritzes of perfume, earings and bangles on wrists completed my feminine
Kelly Girl look.
When we got to the breakfast table Miss Kelly was rushing around packing
up drinks and papers in her bag. "You girls can grab a graola bar for the
ride in. We just don't have the time for cereal today." Diana grabbed her
purse and two granola bars for us. Just that quick we were outside in the
morning sun walking to the car. The feel of the cool morning air on my
hairless and nyloned skin felt so nice and the sound of three girls
clicking their heels on the sidewalk was a real wakeup call of what I was
becoming.
The ride to the shop was uneventful as we ate our Granola bars and drank
some juice. Miss Kelly and Diana talked about the days specials and
wasn't expecting to much business for a Sunday afternoon. After opening
the shop I went to punch in and Miss Kelly immediatley grabbed my
timecard before I could punch in. "You don't have to punch in anymore
Gabby, you're now salary and family after what you did for Diana
yesterday." Diana wrapped her arm around my waist and began walking me to
the large front of the store. "Now just be yourself today Gabby. I'll
greet the customers as they come in and you can head to the back to fill
the orders for me." The sound of our nyloned legs rubbing together
reminded me of the first day Brittany and Constnace showed me around the
shop. Now here I was the one wearing nylons and wearing a Kelly Girl
dress doing the same thing.
The first hour of the day was quiet with only 2 women browsing. However
at 2:00 several girls I go to high school with showed up to do some
shopping. I recognized Tina, Ashlee, Melanie and Sara as soon as they
giggled their way into the shop. I lowered my head in the stocking racks
as Diana went over to greet them. "Morning girls, are you looking for
anything particular today?" Tina quickly opened up while the other girls
began separating themselves from Diana. "Well, to be honest were looking
for someone not something. You see, we heard a rumor that Gary Hollister
was working here and we just wanted to find out if it was true?" Diana
hesitated with her response as Melanie and Ashlee inched closer to me and
the stockings racks. I began to get a little jittery as they walked right
behind me. With my back turned they couldn't see my face and continued to
browse the girdles that were dangling from padded hangers. "Hey Tina,
check these out! Ashlee pulled down a longline All in one girdle in
bright pink with attched garters. "Can you imagine a woman wearing this
under a dress all day." Tina then took the girdle and waved it in front
of Diana. "Do you have anyone here that can model this for us by chance?"
Diana quickly took the garment from her and put it back on the rack. "I'm
sorry Miss but we don't have anyone available to model foundation
garments today. Tomorrow would be a better day when I have a full
compliment of sales girls in the store." Tina being as brash as could be
pulled it back down and pointed over to the stocking racks where I stood.
"What about her? She's not doing anything and looks quite capable of
modeling this for us." I began to tremble in my heels as they all inched
a little closer dragging Diana with them. "Listen girls, you don't look
like the girdle type to me and Monday would be a much better day if you
really want to see it modeled in person." Once again Diana took the
shaper from Tina who wasn't taking no for an answer. Over the next few
minutes a small cat fight insued bringing Miss Kelly out from her office.
"Diana what's going on out here!" "Ohhh Mom, it's nothing I can't
handle!" "Well obviously there seems to be something going on." Tina then
took the shaper from one pissed off Diana and placed her hand on her hip.
"We were asking to see this modeled but we were told that we had to come
back Momday for that to happen." Miss Kelly took the Girdle and began
smiling. "This runs $149.99, do you have the cash for such a purchase?"
Tina opened up her Chanel purse and pulled out two crisp $100 bills and
placed them on the table next to Mis Kelly. Miss Kelly handed the shaper
back to Diana with a pissed off look on her face. "These are paying
customers with cash Diana and you know how much I love Cash transactions.
You should treat them with a little more respect. Have Gabby slip into
this so they can see how it looks and be quick about it!" I could've
cried as the girls stood their ground and waited. Diana took the Pink
shaper from her Mother's hand with an even more pissed off look. She then
grabbed my hand and began walking me back to the changing room. "Lets go
Gabby!" As soon as we got out of ear range I began fretting. "Diana, I
can't wear that thing in front of them! They only came in here to
humiliate me! Can't you see what they're trying to do?" "Calm down Gabby
and get your dress off while I try and come up with a way out of this
mess." "I have a better idea Diana, you take your dress off while I
figure a way out of this mess!"
Over the next 10 minutes I was stripped of my pretty pink underwear and
Diana had me step my nyloned feet and legs into the dreamy longline
Girdle. It took her almost 5 minutes to wiggle my pantyhosed legs and ass
into the tight fitting long line girdle and get it to the point where she
was satisfied with the fit. My silicone breasts were dropped into the
cups and she began tightening up the straps behind me. Once it was
finally on Diana attached Tan support stockings to the hidden garters
that rested a few inches above the short legs of the shaper. I was now
wearing stockings over my pantyhosed legs for an ultimate nylon overdose!
She then put me back in my dress and heels before walking me back out to
the girls. Miss Kelly was chatting with the girls when Diana and I walked
back out. As I stood in front them they eyed me up all over and Diana
started her sales pitch. "As you can see girls, that shaper Gabby's
modeling has redefined her bustline and trimed her waist a few inches.
Her dress is now a little loose on her comapred to before." Diana slowly
spun me around in my heels so everyone could get a good look at me. "You
can also see the attached hidden garters holding up Gabby's stockings are
perfect for girls who want to stay a little old fashoned and skip the
pantyhose aisles." Diana lifted up my short skirt and my gartered
stockinged tops came into view. After lowering my skirt Miss Kelly opened
up to the girls. "So what size can we get you today for one of these
dynamite figure enhancers?" Tina with hand on her hip began shaking her
head and stepped right in front of me. "This isn't really what I had in
mind. I wanted to see how it looks on her without the dress, if you know
what I mean?" Miss Kelly then stepped right aside of my nervous nyloned
and girdled body. "Well Miss, this isn't a Victoria's Secret catalog
where you can see everything! We are limited on what we can show you
legally." I continued nervously trembling as the tough Tina pressed Miss
Kelly once more. "Weeeeeell the store's kinda empty, and I really don't
understand why tomorrow would be any less 'LEGAL' than today to see Gabby
here model this for us without her dress on?" Miss Kelly was in a pinch
as Tina Check Mated her. After peering down to me with her black outlined
eyes. She stepped behind me and pinched the zipper of my dress! "Very
well then, Miss Kelly unzipped my dress right in front of everyone and it
fell to the floor. My boyish frame and fake breasts now had no where to
hide. Diana lowered her head with embarrassment as I nevously looked at
the smirking girls.
"Aaaawe just look at him girls! All silky smooth and wearing things he
shouldn't be wearing! Looks like the boys wern't lying about seeing him
in a maid costume last night." When I went to pick up my dress Tina
quickly stepped on it with her low heeled foot. "Let go of my dress
Tina!" "Not so fast Gabby, we don't get to see boys modeling girdles and
stockings every day. I must admit, she sure looks great even for a
sissy!" With the girls moving in for a closer look, Tina ran her hand all
over my girdled frame and stockinged legs to the delight of the other
girls. "WOW! I never seen a boy wear stockings before!" "Hell Sara, he's
wearing pantyhose and stockings at the same time! Just look at the
'SissySwirl' pattern on her legs." Ashlee ran her hand over my nyloned
legs as Miss Kelly held me in place. "We can get you the stockings and
pantyhose Gabby's wearing to complete your feminine look as well for
about $40." Over the next 5 minutes the girls fondled me all over and
gave me disgusted looks. Tina then put her $100 bills back in her purse
and closed it up. "You're right Mam, this is just way too much girdle
action for me to handle." Once again I was totally humiliated in front
of more high school students I went to school with. To make matters
worse, Miss Kelly allowed Malanie and Ashlee to snap a few pictures of
me adding to my humiliation. As the girls began heading out the front
door they all blew me a kiss and in perfect synchronitity they waved and
cried out "Bye Gabby, see you in school tomorrow!" It took a while for me
to get my composure back but Miss Kelly's kind words and soft touches
softened the hard knocks I continued to take. She told me this was part
of the job and I would have to live with a little humiliation now and
then. I stayed in my long line shaper and stockings for the rest of the
afternoon per Miss Kelly's instructions and to teh delight of Diana.
As the day wound down we were just about to close when an older woman
came in. Diana immediately walked over and greeted her. "Thanks for
coming Mrs Wetherford! Come and meet Gabby, she's right over here." The
older woman and Diana clicked their heels over to me as I was holding
another Longline girdle just like the one I was wearing. "Gabby, say
hello to the high priestess of our school Mrs Wetherford." I swalloed
hard as the two of them peered down to me and my tightly gripped girdle.
"Good afternoon Mam." She said nothing as she eyed me up and encircled me
a few times. "Ohhhh she's adorable Diana! Just like you described her.
She looks perfect for an up and coming boy/girl. "Polished nails, long
hair, nylons, heels and I see Miss Kelly has her in a one of her Kelly
Girl dresses today! Clearly her feminine side is taking over her." While
Diana and Mrs Wetherford contiuned to compliment my feminine look Mrs
Wetherford snapped a few pictures of me and gave me one of her business
cards. "Gabby, the student body and myself would love for you to stop in
next week and be an honorary student for the day. I can give you a tour
of our charming school and you can sit in a few classes with the girls
for fun. Maybe you might even want to transfer from that public school
that you go to? I know I wouldn't want to be going back there tomorrow
after your friends seen you in those cute maid costumes last night." I
took the card from her and Diana wrapped her arm around my girdled
waistline. "You know Gabby, the girls would love to have you in class
with us. They have been so fascinated with all the stories I've been
telling them over the past month. You would definately fit in better with
us."
Mrs Wetherford didn't buy one thing in the store. She only stopped by to
see me to try and intice me to visit the prestegious Saint Teressa's all
girl school that she overlooked. At 4:00 I was stripped of everything I
was wearing and my makeup was washed off. My nails were cleaned of my
polish and for the first time in 36 hours I was back in my dungy jeans
and sweatshirt. Miss Kelly dropped me off at home around 5:00 where Mom
was just about to start cooking supper. "Well look who's finally home! I
can't wait to see that paycheck of yours with all this weekend overtime!"
Before I could even get my overnight bag on the table Mom took it from my
hand and began unzipping it. She pulled out several pairs of pantyhose,
panties, bras and a longline girlde Miss Kelly let me have today. "Well
Gabby, I guess now's a good time to talk about all those things you have
in those boxes under your bed?" "Mom can't we discuss this later, I've
had a long past few days." "Sit you pretty ass down and start being
honest with me. Now what's with all this lingerie in your bag? Are you
taking your work home with you now or do we need to start making some
changes around here?" I took the nylons and panties from her hands and
put them back in my bag. "Mom this is just a prank Diana played on me. I
don't have any use for these things." "So you don't wear any of this
stuff when your with Diana or Miss Kelly then is that it?" "Yes Mom, how
could you think I wear panties and pantyhose?" Mom then pulled out her
phone and began tapping the screen. "So how was the Halloween party last
night?" I swallowed hard and then lowered my head a little. "It went well
and Miss Ke....!" Before I could finish she turned her phone screen to me
with a picture of me and Diana in our Black satin maid costumes. I was
speachelss as I stared at the pretty girls on the screen. "Miss Kelly was
kind enough to send me a few pictures of the two of you last night after
I emailed her to see the two of you in your Batman and Robin costumes.
You sure look great in that maid uniform and the smile on your face tells
me that you were enjoying yourself. "Heels, stockings, makeup and and it
looks like you even shaved all over to look the part better?" "NAIR MOM!
Diana naired me without telling me." "Aaaawe poor baby, looks like Diana
won another bet that you didn't tell me about and the Batman and Robin
costumes were just a smokescreen for what was really going on." "Mom, you
saw the costumes before we left yesterday! Two of Diana's friends took
our costumes by mistake and me and Diana had to wear the maid costumes."
"Ohhh Gabby, will you just come out and tell me the truth so we can move
on. It's quite obvious you have a strong feminine side that's now
emerging trying to show itself. All the fashion catalogs and girl
magazines hidden under your bed proves beyond a doubt I have a girly son
who wants to be more feminine. How on earth are you gonna deal with this
tomorrow at school? Four of your friends stopped by and aked me if you
were gonna wear a dress to school tomorrow and I've had many of the women
I work with email pictures of you in your Kelly Girl Pink store uniform
today." "Mom Please! Enough already! I'm not planning to go to school
tomorrow. Miss Kelly said I could work all day with her until I figure
out what I'm gonna do?" "Ohhh really! I hate to tell you this Gabby, but
Miss Kelly isn't your Mother and she's not making decisions for you.
"You're going to school to get an education and that's that. Unless of
course you have a better idea?" In desperation I opened up my bag and
pulled out Mrs Wetherford's school card and handed it to Mom. "Well if I
have to go to school tomorrow I want to go to school with Diana and her
friends at Saint Teressa's." Mom looked at the card and tossed it on the
table. "Gabby, that's an all girl school for the cities Elite. First of
all you can't get in because you're a boy. Second, we don't have the
yearly $12,000 for your tuition." "Mom, I'm just gonna be an honanry
student for the day. Mrs Wetherford told me today that she would love to
have me stop by and attend classes for a day." Mom began shaking her head
as she eyed me up. "I know this is some sort of prank and I'm gonna teach
you a lesson young man!" Mom picked the card back up and began calling
Mrs Wetherford. After a few rings Mrs Wetherford picked up. "Yes, good
afternoon Mrs Wetherford, this is Gabby's Mother how are you doing
today?" Over the next few minutes Mom talked to Mrs Wetherford. Her mouth
dropped open several times with her head nodding up and down as well.
After 5 minutes Mom began finishing up the call. "Yes, Mrs Wetherford,
I'll have her there tomorrow morning around 8:00." Mom set the phone down
and began tapping her long fingernails on the table. "It appears Mrs
Wetherford's quite interested in having you swing by? I'm not seeing how
one day will change anything for you because eventually you'll have to go
back to your regular school. But for tomorrow you'll be going to Saint
Teressa's for the day. I have no idea what you'll be wearing? She
insisted on a dress or skirt so maybe you better get a hold of Diana and
see if she has something you can wear for tomorrow? I've gotta let this
sink in while I'm cooking dinner so you get moving?" I picked up my bag
and began making my up to my room. I called Diana up and told her what
was going on. By coincidence she said she had some thigns that might fit
me and was going to bring them over after supper. I got out of my clothes
and took a long shower to try and figure out what had happened to me the
past few days. Things were clearly spiraling out of control with no way
of stopping it.
The next morning Mom got me up around 6:00 and informed me to shower
while she laid picked out my clothes from the stuff Diana brought over
last night. After a shower and good rub down with moisturizer I made my
back to bedroom. On the bed laid Pink panties, bra and Beige pantyhose
along with my waistcincher and silicone breasts. After getting into my
pretty underwear and filling my bra cups with my silicones, Mom began
fitting me into my waistcincher. "This is so wrong Gabby, I can't believe
I'm doing this to my son?" "Relax Mom, I wore this cincher for 36 hours
the past few days. I need this to pull off my feminine illusion to the
girls at school today." As she struggled snapping the cincher shut I
looked at the bright white blouse and Pink denim miniskirt that laid on
the bed along side a full length pink slip. After getting my cincher on
properly Mom tossed the silky slip over my head and let it dangle down to
my nyloned thighs. The silky nylon slip caressed my curves and almost
looked normal to the disbelief of Mom. "This slip fits you really well
sweetie. I'm amazed how feminine you look in your underwear. Perhaps I
should start shopping at Miss Kelly's shop? Get your blouse and skirt on
while I get your makeup and nail polish ready." After clipping on a pair
of dangly Pink earings I put on my long sleeve white blouse and pulled up
my miniskirt. The front button and zipper closure on the front of the
skirt made it very easy to close up and fit around my cinched waist. Once
again I was in sheer hosiery and pink underwear which I was falling in
love with. My above the knee skirt showed off plenty of my shiny beige
nyloned legs. After stepping into a pair of 2" pumps Mom began polishing
my nails in bubble gum pink polish. It only took a few minutes for the
quick drying polish to dry. 2 coats of glossy clear polish followed
giving me very feminine looking hands.
"Now, Mrs Wetherford said light makeup and light colored lipstick.
Apparantly she doesn't wnat her girls wearing Black polishes or heavy
makeup at their ages?" "Just make me look good Mom. I don't want the
girls giving me second looks all day." She just shook her head from side
to side and began working on me. Over the next 15 minutes Mom put eye
shadow, mascarra and blush on my cheeks. She finished me off with Pink
lipstick and a few spritzes of Girly perfume to give me a feminine
scented smell. While she brushed out my hair she gazed in the mirrors
reflection. "You know Gabby, you're gonna have some big decisions to make
in the next month or so. You can't keep playing for both teams. I'm not
rushing you, but you're gonna have to choose between being a boy or a
girl?" "Just give me time Mom, I'm not sure what I want right now? Maybe
something will click soon and I'll be able to make better decisions on
these new feelings I continue to like?" She placed a Pink headband into
my hair with the Word 'PRINCESS' embroidered on it and pressed it into
place a few inches above my forhead. I was now ready for school and we
made our way downstairs to the breakfast table. The sound of my nyloned
legs brushing against my nylon slip sounded so wonderful and I just loved
when my rubbery breasts would bounce around in my bra cups just like a
real girls would.
After breakfast we made our way to Saint Teressa's all girl school. The
school sat high up on side of a mountain away from everything else. As we
got closer and closer to the main gate Mom gave me one last chance to
pull out. "It's now or never Gabby, do you still want to go to school
here today?" It only took me 2 seconds to sigh and respond to her. "Mom,
I can't go back to Jefferson High. Mrs Wetherford is expecting us at 8:00
and right now it's 7:55 so we better hurry." After stopping at the
security gate the guard pointed to the direction for Mrs Wetherford's
office. Unlike mornings at Jefferson high, there were no groups of
students fooling around, no student parking or yellow busses anywhere to
be seen. The front of the school was completely empty except for a few of
the maintenance crews working on the hedges. After parking near the front
entrance Mom and I began the walk to the door. "Straighten your skirt
Gabby and look up when you're walking!" My feminine fingers pinched the
hem of my pink skirt and I pulled it down back in place. When we got
inside we made our way over to the adminstation offices. Mrs Wetherford
was waiting for us when we stepped inside. "Well good morning ladies! So
nice to see you're on time." Mrs Wetherford came over and immediately
pinned a nametag to my blouse while she eyed me up with great enthusiasm.
"It's so nice to see you this morning Gabby. If the two of you will
follow me, we'll begin the tour of our prestegious school." The three of
us began walking down the halls of the school while Mrs Wetherford talked
about the history of the school.
"The Saint Teressa's school for girls was founded back in 1929 to help
educate young girls during the depression era when most public schools
were closed. We have a long heritage that dates back almost 100 years now
and our graduation rate is 99%." As my heels clicked on the tiled floor I
could see the Pink lockers that lined the hall we were in. "As you can
see every girl has her own book locker and she also gets her own gym
locker as well." Mom then began grilling Mrs Wetherford. "So how on earth
will you be able to permit a boy to enter the girls gym locker area for
changing? Surely the other parents of these young girls would never
permit it?" "Excellent question Mrs Hollister and one I really don't have
an answer for right now. If Gabby does enroll in the school I would have
to discuss the situation with my board of directors. Now here we have the
cafeteria. Mrs Wetherford quickly changed the subject and steered us
through the doors leading to the cafeteria.
"Here the girls can order breakfast before classes and stop by for snacks
between classes if they choose to." "How much does the lunches and snacks
cost per week if I may ask?" "Absolutely nothing Mrs Hollinger! All the
meals, drinks and snacks are included in the yearly tuition fee. If Gabby
chooses to bring her own lunch rather than having a prepared lunch,
that's also fine." Now if you'll follow me we'll head to the biology lab,
gymnasium and Library before we head back to my office to complete the
orientation process." We made our way through several empty classrooms
along with the huge gym, auditorium and labs the school had. We didn't
see many students except for a few classrooms where teachers were giving
lectures to the girls.
When we got back into Mrs Wetherford's office Mom and I sat in her cushy
chairs while she sat behind her large old fashioned desk. "So what do you
think Gabby? Does this look like a better place to get your education
than Jefferson high?" Before I could respond Mom opened up to the
question. "Mrs Wetherford I just don't understand why you would want my
Son to enroll here? Are you sure the school board and parents would go
for this?" "Mrs Hollister you have nothing to worry about. I'm sure I can
sway the board into accepting Gabby's enrollment with a little smooth
talking. As far as the parents go, well, that me be another situation
we'll deal with later. Right now, I think getting Gabby accustomed to the
school is more important. You really don't want to send him back to
Jefferson High after what happened this weekend. Those Senior girls would
eat him alive and the boys might get physical with him?" Mom thought
about Mrs Wetherford's observations while I nervously sat there rocking
my nyloned clad leg. "Hmmmm, you might have a good point there. I never
thought how cruel they might get with Gabby?" Mrs Wetherford stepped out
from behind her desk and handed Mom an indoctrination folder. "Take this
home with you and read it over. It explains everything we do here and
gives you a bio on the fine teaching staff I've hand picked to teach our
girls. Come back for Gabby around 3:00 this afternoon and if the two of
you have any doubts you can leave and head back to the public school
system." Mom began paging through the folder and pointed to one of the
pages. "Mrs Wetherford, even if Gabby does like it here, I could never
afford the yearly $12,000 enrollment fee. We struggle as it is with my
factory job pay." "Don't worry about it Mrs Hollister, there are grants
and other options that Gabby might be able to receive because of your low
household income. Let her spend the day with us and we'll talk again this
afternoon." Mom picked up the folder and her purse as Mrs Wetherford
helped me out of my chair. "Well have fun today Gabby, I'll see you later
this afternoon." Mom stroked my long hair and put on her sunglasses
before walking out. Mrs Wetherford once again began eyeing me up from
head to toe. "Yes Gabby, you're gonna love being a student here. My staff
and I will help you blossom into a fine respectable young lady like we
have with so many other girls that clicked their heels down these
hallways. Come now, lets take a walk to one of the classrooms and we'll
get you introduced to your classmates for the day." While I straightened
out my skirt once more Mrs Wetherford went ot her phone and began
dialing. After a pause she began talking. "Hi Gwen, I'm bringing our
honorary student for the day up in a few minutes so wrap up what you're
doing and get ready to greet us." She put her phone back down and wrapped
he arm around my cinched waistline. "This way my dear, we don't want to
keep Miss Sanderson's class waiting."
It took us about 5 minutes to make the walk upstairs to Miss Sanderson's
classroom. The door was wide open and the girls could clearly hear me
coming as my heels clcicked on the floor. A few feet from the door the
girls went silent except for a few "She's here" comments. I swallowed
hard as Mrs Wetherford walked me right into the classroom. As soon as the
20 or so girls saw me they began smiling, giggling and whispering. "Well
you must be Gabby?" The tall leggy teacher clicked her 4 inch heeled feet
over to me and took me from Mrs Wetherford's grasp. As I nervously looked
to the sea of smiling girls sitting at their desks I shyly looked away
trying to settle myself down. "Thank you Mrs Wetherford, I'll take it
from here. Mrs Sanderson turned me to face her class and then placed her
hands on my trembling shoulders. "Everyone say hello to our honorary
student for the day, Gabby." The class opened up with a winded reply
"Hiiiiiiiii Gabbyyyyyyyy!" Followed by snickering and giggling to the
dismay of Mrs Sanderson. "Allright girls settle down and get control of
yourselves!" As the girls chatted between themselves Mrs Sanderson walked
me over to my chair in front of her desk and handed me a pad and pencil.
I was amazed at how they all looked alike in their preppy momogramed
school sweaters, short plaid skirts and shiny bright white tights. I
clearly stuck out like a sore thumb in my blouse, pink skirt and sheer
beige stockinged legs.
After everyone settled down Mrs Sanderson had the girls open up their
books and began talking about important dates in history. Her lecture
lasted until about 9:30 and then decided to get me invovled in the
classroom discussions. "Gabby dear, would you kindly turn your desk and
face the class for this next discussion." I stood up and straightened out
my skirt while tossing my long hair over my shoulders to the delight of
the girls. "Gretchen! Did you see him fix his skirt and toss his hair" "I
sure did Sophia, and he did it so femininely." More whispers filled the
room from the enthusiastic girls which made Mrs Sanderson crack her
poniter on her desk to get the girls attention. 'CRACK! CRACK! CRACK!'
'Ok girls since you're all so fascinated with Gabby you can now begin to
ask her questions about clothes, makeup, and whatever else you want. Just
keep your questions sincere and proper or the next crack of my pointer
will be swatting your skirted asses! Now who wishes to go first?" I
watched a dozen arms get raised in just one second. Mrs Sanderson hopped
up on her desk, crossed her Tan stockinged legs and pointed into the
crowd of girls with her pointer. "Lets see, Sophia, since your so
talkative this morning you may go first." "Thank you Mrs Sanderson.
Gabby, when did you first realize you liked girly things and wern't like
regular boys?" Sophia's million dollar smile was so beautiful and the way
she twirled her tight clad ankle and shoe made me feel I was in way over
my head with these girls. "uhhhh, well I guess when I was 6 or 7 I began
looking at my Moms Montgomery Wards and Sears Catalogs. I just loved how
the bright colors, satins and nylon shined on the girls modeling the
dresses and lingerie." Several girls mouths dropped wide open as I
fidgited in my chair. "I see, did you ever tell your Mom or Dad how you
felt about these 'different' feelings you were experiencing?" I began
rocking my nylon clad leg and nervously responded to her. "My dad left us
when I was about 5 and to be honest I really didn't know why I was
looking at satins and silks the way I was? It's not something you talk
about when you're playing hockey or baseball with the guys." Sophia was
just about to ask another question when Mrs Sanderson stopped her. "Hold
it Sophia, lets get a few of the other girls involved. Uhhhhh Gretchen,
what do you wish to ask Gabby?" With a big smile she twirled her hair
with her fingers and spoke up. "So how does a boy hang around with other
boys if he desires to be a girl?" Mrs Sanderson nodded and pointed back
at Gretchen with her pointer. "Excellent question Gretchen!" All eyes
were on me once more as I nervously fidgited in my chair. "Well it's
kinda difficult to explain. Even though I played baseball and football,
my mind was always distracted with my love for feminine things. I guess I
just went through the motions when I was with the guys?" "WOW! It must be
very tough to turn on Guy emotions and then flip flop to feminine
desires? I take it you're now going to want to be a girl from now on?" I
cracked a smile and femininely rocked my leg as I hesitated with my
answer. Miss Sanderson pressed the tip of her pointer to my wrist and I
looked up to her. "Well Gabby, Gretchen asked you a sincere question. Are
you planning on joining 'TEAM GIRL'?" "Well, I really haven't made up my
mind yet. There's still a few things I'm not understanding?" "Sensible
answer my dear. Perhaps those pieces to your feminine puzzle will fall in
place for you in the near futrure? Now let me seeee, Ummmmmm, Shasta,
what would you like to ask Gabby this morning?" Shasta was a knockout!
Bright Red hair and she was built like a brick house from her hips to her
busty chest. "Not to get too personal but do prefer to be kissed by girls
or boys?" The classroom began oooohing and aaaahing as I turned 3 shades
of red with embarrassment. "Girls! Girls! Hush and let Gabby answer."
"Shasta, I've only ever kissed girls." Mrs Sanderson then pointed her
pointer to me again. "That's not what she asked you Gabby! She asked you
which you prefer being kissed by Boys or Girls?" For some reason my mind
began getting confused as I sat there without replying trying to process
the question. Then the classroom of preppy girls began whispering to
themselves "BOYS! No its GIRLS! Noooo she likes BOYS! BOYS! BOYS!"
Finally I got my senses back and was about to answer when Mrs Sanderson
cut me off. "Well, obviously Gabby has a taste for boys and girls if I'm
reading here shy body language correctly. This might be one of those
things she's trying to figure out on her jouney through feminitity? A few
more questions and then you girls will head to the gymnasium for some
field hockey."
The class broke up around 10:00 and I stayed behind with Mrs Sanderson.
"You handled those personal questions very well my dear, I'm impressed.
For the next hour or so I want you fill out this form for me. Every girl
must fill this form out before being officially enrolled here at Saint
Terassa's" I took the form from her hand and looked it over real good.
The top of the form read 'FEMININE IQ' and I began paging through it. Mrs
Sanderson picked up my pencil and handed it to me as I eyed up the 100
question form filled with multiple choice questions and pictures. "Now if
you're not sure about a question and don't know the answer, it's better
to leave it blank rather than taking wild guesses. Ok Gabby?" I noded and
began working on the form. Some questions were real easy like 'What do
girls wear with a formal dress? (A) Sneakers (B) Heels (C) Boots or (D)
Flip Flops. Some other questions had pictures to matchup with the
answers. There were 4 pictures of hosiery and I had to match up the
pictures with following answers. (A) Tights (B) Stockings (C) Pantyhose
(D) Knee Highs. When I got to makeup questions I left more answers blank
than I filled out the same was true with a few other parts of the test.
By the time I was done at 11:30 I was through the form but only answered
about half the questions. Mrs Sanderson then walked me down to the
cafeteria for lunch. The girls I was with earlier were through playing
hockey and stood in line waiting for lunch to be served. "You girls take
good care of Gabby and see that she gets a good lunch before her
afternoon classes begin with the older girls." I Grabbed my tray and
stood in line with the other 40+ girls. Gretchen then began rubbing her
shoulders with me. "Hey girlfriend, Jeannette's telling everyone you two
had a great makeout session on Saturday." My mouth dropped wide open and
I felt a little twitch in my panties for some strange reason. "Yea
Gretchen, she's also telling everyone she got him to cum! I sure wish I
could've been there for that!" The girls all began ooohing and ahhhing as
I stood there fidgiting and completely embarrassed. "How about it Gabby,
were you Jeannette's 'Maid of Dreams' girlfriend on Saturday night?"
Without answering her the line started moving and we slowly stepped our
way inside. "Yea I bet you looked great in that maid costume she made for
you?" We were now in front of the cafeteria crew with trays in hand as
the line slowly moved. Today they were serving tossed salad with a
chicken breast and fruit cocktail. We filled our trays and then went out
to the dining area with the rest of the student body. I walked with head
held high and could see all the curious girls eying me up. Just as I was
about to sit down Diana came rushing over to me. "Ohh no you don't Gabby!
You're sitting with me and Julliette." Diana guided me to the front table
where the older girls sat. All of them were queens wearing the finest
uniforms compared to the younger girls. Silky white tights, shorter pink
plaid skirts with cashmere like sweaters. I was now way in over my head
as I set my tray down aside of Julliette and a Diana.
"Girls say hello to Gabby." Everyone waved, smiled and greeted me as if I
was just another girl. "With any luck Gabby will be a new attendee here
in a few days. I know she would love schooling with us rather than that
rabble down at Jefferson high." As I began eating Diana began to fill me
in on all the gossip that lurked around every corner of the school. Who
was dating who, who got caught drinking and who's on Mrs Wetherford's
shit list. She also informed me that Mrs Wetherford and her team of
teachers were going to do everything they could for me and get me
enrolled as quick as possible. Things were clearly happening for the
better and at a fast pace to boot! For the next half hour Diana's
classmates encouraged me to be myself and show off my feminitity. They
all loved how great I looked in my Halloween costume but Diana and the
Jets made sure it was them who made it all possible with their sneaky
costume switch.
At the end of Lunch Mrs Wetherford walked me back to her office and had
me fill out another form or two. She then walked me up to Diana and her
classmates. After knocking on the door another tall leggy blonde teacher
came walking to greet us. "Miss Everhart please have your class show the
upmost courtesy to our honorary student of the day Gabby. I'll be back at
the end of the day to complete her orientation." Miss Everhart grabbed me
by the hand and began walking me into the classroom. Unlike the younger
girls cackling and gigling, the maturer crowd just eyed me up and made it
perfecly clear who had confidence and stature in the room. "Allright
girls, books closed, and say hello to Gabby here." Miss Everhart wrapped
her arm around my waist and then began walking me up and down the aisles
to meet everyone. "This is Melanie our class president and this is Holly
our class Princess. Over here is Wendy and that's Julliette and of course
you know all about Diana." After meeting all 28 girls Miss Everhart sat
me in front of the class and stood proudly in her 4 inch spike heels and
tight sweater dress. "So Gabby, which girl do you think is the prettiest
in my class?" She really caught me off guard and I quickly blurted our
'DIANA'! "Sensible answer my dear, especially since you work with her at
the lingerie shop most days. My class and I have been waiting 6 long
months to see the boy who Diana was telling us about. I sure hope you
come up to our expectations? After all, it isn't every day a boy gets to
sit in one of these chairs for an education."
Over the next hour Miss Everhart began lecturing to her class of preppy
girls. You never heard one peep out of them while Miss Everhart elegantly
clicked her heels around her desk, chair and blackbord. Her hot body was
so beautiful and I was smitten with her beauty and grace. After her
lecture I was walked around to everyone once more to get a more personal
experience. Every single girl admired me for what I was doing and made it
a point to come join them and enroll at the school. My fears of going
back to Jefferson high were becoming a distant memory with every smile,
wink of an eye and flirty foot twirl the girls gave me. I had a smile on
my face evey second of the afternoon as the girls excepted me and my
feminine choice to join them today.
At 2:45 Mrs Wetherford came up to collect me as the girls got their final
instructions on homework from Miss Everhart. On the way back to her
office I straightened ourt my skirt and continued smiling from ear to
ear. "So Gabby, how did you like your orientation today? I can tell by
that smile that you must have liked it?" "Mrs Wetherford, everything was
great! The girls, the lunch and the teachers were so nice to me."
"Splendid my dear splendid! Now I want you tell your Mother that when we
join her in a few minutes. She seems to be on the fence to start the
enrollment process so we have to win her over somehow?"
When we got back to Mrs Wetherford's office Mom clearly saw the joy
beaming from me. "Well Gabby, I haven't seen a smile that big since you
got the job at Miss Kelly's lingerie shop. I take it you had a fun day?"
I enthusiastically crossed my nyloned legs and grabbed her hand. "Mom
everything is PERFECT here! I love the girls, the classrooms and the
teachers Mrs Wetherford has on to continue my education." "Take it easy
Gabby! It was only one day. Are you sure you want to make this big
decisison in one day?" I said nothing but nodded my head making my
earings shake. Mrs Wetherford then added her opinion as Mom eyed me up.
"I think it's quite clear that Gabby would love it here Mrs Hollinger.
Just look how happy she is." Mom then fired back at Mrs Wetherford with
an unsure voice. "I'm sure the school is lovely but I think my son needs
professional help rather than to join an all girl school for the cities
elite?" My smile quickly dissapeared from my face as my ship was begining
to take on water. "Mom how can you say soemthing like that? Can't you see
what would be best for me right now?" "That's just it Gabby, I don't know
what's best for you, I really think a few sessions with a psychologist
would be best before we decide on your schooling?" I let out a sigh and
sat back in my chair. Mrs Wetherford then pressed her intercom and spoke
up. "Gladys dear, would you kindly step into my office for a few
minutes." While Mrs Wetherford and Mom continued chatting another tall
middle aged woman entered the office. "Gladys this is Mrs Hollinger and
her son Gabby. The tall woman arched her eye as soon as she heard the
word 'SON'. She then stood proudly and sophistactly in her spike heels
and silk dress. "Mrs Hollinger, I'm willing to have our Medical person
here examine Gabby at no charge to you if you wish to proceed to a
psychologist. You see, Miss Baker here is a fully licensed psychological
professional and a graduate of the school herself. She's more than
capable to examine Gabby. She could begin tomorrow and it wouldn't cost
you a dime!" Mom began nodding her head and then grabbed my hand. Why are
you being so nice to us Mrs Wetherford? It seems to me your team is
jumping through a lot of hoops to enroll my son here?" Mrs Wetherford
tapped her pen on her desk and then took off her glasses. "Very well Mrs
Hollinger, I'll be up front with you. I need a minimum of 50 students in
my classes to meet my funding requirements. Right now we only have 49
girls and I need one more before the end of the fall semester or our
funding will be pulled and the school could eventually close next year if
we can't raise the capital to cover our costs?" Mom then sat back in her
chair the way she always does when she's about to negotaiate. "Yes I was
wondering why there were so many classrooms empty when you were giving us
our tour this morning?" "At one time I had 150+ girls here with 12
teachers but now a days with the economy being so bad many of our girls
have gone to public schools for their education." Mom then began to nod
and clear her throat. "Well then, perhaps we can strike a deal by the
end of the week on Gabby's enrollment in the school now that we have a
little leverage?" Mrs Wetherford cracked a smile and took out her pen.
"I'm listening Mrs hollinger." Mom confidently began rocking her crossed
leg and folded her arms up under her breasts. "Why don't we have Gabby
spend another day or two with you so she can get a real idea of what
she's signing up for. I'll also take you up on your offer to have Miss
Baker examine my son without any medications to see if his mind is right
to take on such a drastic change in his life! Why don't we talk again on
Wednesday and see how things go? Maybe we can reach an agreement that
works for all of us?" Mrs Wetherford put down her pen and quickly swung
herself out from behind her desk. "Thank you so much Mrs Hollinger, I'm
sure we can work something out this week." Mrs Wetherford then pulled me
from my chair while Miss Baker continued to smile at me. "And you young
lady, I'll see you tomorrow in a nice dress and heels. We never wear
denim in my school and the only skirts I allow are the official school
uniform skirts." I nodded with acceptance to the dress code and we were
walked to the front door. "I'll notify my contact at Jefferson High on
what's going on with Gabby so we don't have any interferance with the
truant officer. Take care ladies." Mom and I walked out and once again I
was smiling from ear to ear as I clicked my heels over to the car. Mom
was now on a power rush and briming with confidence after putting Mrs
Wetherford in her place.
Mom dropped me off at the Lingerie shop a little later than usual but
Miss Kelly wasn't to disappointed considereing where I was all day. I was
put into my Pink Kelly Girl Dress with freshened makeup and was out front
helping Constance and Brittany for the rest of the afternoon. All I could
think about was going to school with all those beautiful high society
girls and the possibile feminine fun that awaited me if Mom would enroll
me. Later in the day I was back in the storeroom with Diana who had
brought several dresses for me to try on now that Mrs Wetherford fine
tuned her dress code for me. Miss Kelly supervised the whole fashion show
and gave me subtle pointers on how to act, walk and gesture in a more
feminie manner. She wasn't shy in telling me I was more unlady like than
lady like in some of my boyish steps and turns. I got 5 dresses from
Diana and Miss Kelly threw in several pairs of designer hosiery, panties
and shapewear to help me prepare for my few days at the school. Diana
also informed me that the girls were melting over me in the gymnasium
making so many compliments on how great it would be to have me in school
on a daily basis. Several of them wanted to go out on dates, dress me up
in their clothes, do my makeup, hair, nails and they all wanted me to be
their partners on school projects. When Mom and I discussed the days
events at the dinner table she slowly began to acknowledge that Saint
Teressa's might not be a bad idea after all.
The next morning I was smartly dressed in a very chic Red dress with
Black flowers on it. The skirt of my dress came to my knees and the long
sleeves added a more feminine look than yesterdays denim skirt. Today Mom
put more makeup on me than yesterday and outlined my eyes with Black
eyeliner for a more mature look. My nails we were repolished in Red and
glossed over with high gloss finisher to make em shine. Red Lipstick,
earings and 2 1/2" red open toed ankle strap heels completed my look.
Under my dress I was wearing Shiny Suntan control top Pantyhose and A
wonderfull Red bra & panty set Miss Kelly gave me last night. Ny waist
cincher was the only thing that continued to be uncomfortable for me. For
10 long hors I had to endure another day with my tummy and sides being
squeezed into a feminine hourglass shape. After a few brushes of my hair
and spritzes of perfume we were heading to the breakfast table. A quick
bowl of cereal and a glass of Orange Juice was all I had before heading
out the door.
After about 10 steps Mom let out a sigh after looking in her purse. "Damn
it! I left my sunglasses on the table." While Mom headed back inside I
made my way down the sidewalk. I got about 20 feet from the car and then
noticed my school buddied pointing in my direction. Bobbie's voice then
rang out. "Hey guys check it out, that might be Gary?" I seen them
approaching quickly and began clicking my heels to the car. In
desperation I tried to open the car door several times to get in but it
was locked. Mom was still inside getting her sunglasses when my buddies
surrounded me. "Well well well, if it isn't GABBY! Where were you
yesterday pretty boy? The cheerleaders did a nice number on your locker
filling it with panties, nylons and perfume you little sissy!" Danny then
picked at my hair while Jimmy began inching up my skirt. "Check it out
guys, Gabby got her hair done at the salon and got her nails polished as
well!" "Let me go you assholes!" Danny had my skirt lifted all the way up
exposing my pantyhosed ass while two other boys held me firmly in place.
"Just look at what he's wearing guys! Shiny Girly panties, pantyhose and
he's silky smooth all over with no leg hair!" "You better never step foot
in Jefferson High again Gary or you're ass is gonna get beat! Wearing
girls clothes, makeup and working in a lingerie shop pretty much disolves
your chances of being 'one of the guys' anymore!" My hair, dress and
tightly bound body were being pulled in different directions as I
teetered in my sexy heels. While I tried to pull from their grasp the
boys twirled me around in a circle messing up my dress and hair. "Let me
go! Let me Go! MOOOOOOOM! MOOOOOM!" "Aaaawe what's the matter Gary, don't
like playing with the boys anymore you little sissy? No wonder you
couldn't throw a football more than 15 yards or hit a baseball out of the
infield! Now let me give that pantied ass of yours a working over!' I
peered behind my shoulders to see Danny lifting up my skirt again. "Let
go of my skirt Danny!" With my skirt flared up Bobbie gave my pantied ass
three sound smacks with his hand! 'CRACK! CRACK! CRACK!' I then
femininely whined out to the boys delight. "OUUUUUCH! That hurts Bobbie!
You better not put a run in my pantyhose!" The guys erupted in laughter
as I once again cried out for my Mother. A few seconds later Mom finally
stepped out of the house and clearly saw the boys mistreating me. She
pressed her Fob and the car horn filled the air along with the sound of
the engine starting. "You boys leave Gabby alone and get to school!"
Bobbie gave my ass one more good swat before lowering my skirt. "See ya
around Gary! Maybe someday I'll let you suck my cock!" They quickly began
walking away before turning to face me one last time before yelling out
to me. "HE'S GOOOOT L'EEEEEGGS!" Totally humiliated I sat my sore pantied
ass in the car with Mom right behind me. "Did they hurt you Gabby?" I sat
there in a daze for a few seconds before answering her. "No Mom, they
just wanted to beat me up! Now you see why I can never go back to
Jefferson High!" "Allright dear calm down, the excitement's over." I
tried to rub the sting from my ass as Mom pulled away from the curb.
By the time we got to Saint Teressa's I had calmed down. Mom fixed my
hair and dress before we made our way back to Mrs Wetherford's office.
While Mom and Mrs Wetherford started negotiating over coffee, Miss Baker
in her bright Aqua dress walked me down to her office. With Our heels
clicking on the tiled floor and our nyloned legs sliding and rubbing
under the skirts of our dresses I took in a few deep breaths with my
confrontation still rattling me a bit. Over the next hour Miss Baker
asked me all kinds of questions and jotted down my responses on her pad.
Questions about makeup, clothes, boys, shoes, girlfriends, boyfriends
were the main subjects that we talked about. We then got to some delicate
and very personal questions. "Now Gabby, have you ever kissed or touched
a boy you had a crush on?" Without wasting any time I responded in a very
certain tone. "Ohhh No Miss Baker, I like girls, not boys!" "I see, well
then have you ever kissed or touched a girl you had a crush on?" "Yes
Mam, I've kissed a couple girls in the past week." "How did you feel
after your first kiss Gabby?" "At first I really didn't have any emotions
but after a 10 minute makeout session I began to get more interested."
Miss Baker nodded her head and jotted more scribbling on her pad. "Now I
want you to be completely honest with me Gabby. Were you femininely
dressed or in your boy clothes when this happened?" I began getting red
faced as I hesitated with my answer. "Well Miss Baker, I was wearing a
french maid costume for Halloween and the girls I were with kinda tricked
me into the dress. You see they..." She quickly cut me off and uncrossed
her nyloned legs. "I'm not interested in how you got in the dress dear,
just tell me what the girls did to you?" "Miss Baker this is kinda tough
to explain, you see the girl I had a crush on put the moves on me after
she felt my...." "Your what Gabby? What did she touch?" After a long
silence I giggled like a little girl and opened up. "She touched my
panties and the hard thing inside them." Miss Baker never flinched and
quickly continued with me. "Did she fondle or pull on your hard thing
sweetie?" "Ohh she did more than that Miss Baker. Her mouth and tounge
worked me over real good." "Go on Gabby." Miss Baker's head began to
shake from side to side as I began describing what Diana did to me. "I
never experienced anything like that before as she licked and sucked my
hard thingy." "Did she get you to cum sweetie?" "She sure did! In fact I
came 3 times with her the next morning in bed." While I began feeling a
stiring in my panties Miss Baker took off her glasses and eyed me up. "At
any time while she was taking care of you, did you ever think of yourself
being in her position and doing what she was doing with a boy?" As I
tried to process her question a strange feeling raced through my body.
For a split second I thought about the cum taste that Diana and Jeannette
gave me after they sucked me off while I pictured myself on my nyloned
knees. She could clearly see I was having difficulty with her question
and after a few seconds she grabbed my hand. "You're smiling and
fidgiting in the chair Gabby, I guess that means you might be into those
things, hmmmm? It's ok sweetie, I'm not shocked by your thinking process
considering how femininely you're dressed." As I tried to hide my smile
the thought of being on my nyloned knees began to contaminate my brain
with unthinkable feminine thoughts.
My meeting with Miss Baker ended around 9:30 and I was once again walked
up to Mrs Sanderson's classroom to join the girls I had class with
yesterday morning. Today it was all business and I was given a notebook
and pen to take notes and join in with the class discssuing all sorts of
things. The girls continued smiling and winking at me making me feel so
wanted and in demand. A few of the girls gave me their email addresses to
keep in touch when I wasn't in their class. At luchtime I sat with Diana
and her elite classmates. We laughed, joked around and they all made it a
point to tell me I would be sitting with them, not the firstand second
year girls when it came for lunches and other school projects or field
trips.
By Wednesday afternoon I had clearly fell in love with all the staff and
the beautiful girls I had classes with the past few days. When I got back
to Mrs Wetherford's office Mom and her were yuckin it up over coffee and
my enrollment form was in her hand. "Well Gabby, Mrs Wetherford and I
have come up with a solution in getting you enrolled here at Saint
Teressa's. All you have to do is say the word and we'll get the ball
rolling for next week." My eyes opeend up real wide and I quickly hopped
to my heels. "YES! YES! YES! Sign me up!" Mom stood up and gave me a hug
while Mrs Wetherford and Miss Baker joined in. "Welcome to Saint
Teressa's Gabby. You're acceptance in the school has helped us all in a
big way my dear." I then looked up at Mom who was briming with
confidence. "Mom how on earth did you come up with the money for the
tuition?" Mom stroked my long hair and smiled. "Ohhh don't worry about
that sweetie, Mrs Wetherford's taken care of that little problem for us.
All you have to do is meet with a few of the funding officers next week
and everything will be fine." I gave Mom another hug and almost began
crying because of how overjoyed I was knowing I wasn't going back to
Jefferson High anymore. "Mrs Hollinger, bring Gabby back tomorrow morning
so we can fit her for her school uniforms and fine tune her enrollment
form. I want to go over it one more time to make sure it isn't rejected
by my board of directors on Friday when I present it to them." "I'll have
her here tomorrow at 10:00am for her fitting. In the mean time we've got
shopping to do and closets to rearange for my teenage girl here." Mom
walked me out of Mrs Wetherford's office leaving Miss Baker, Miss
Everhart with her.
"Well done ladies, I'm so glad we were able to hook Mrs Hollinger and
Gabby to our fine establishment." "Yea well this is just the first hurdle
Mrs Wetherford. He still has to make it through the funding officer next
week and she ain't gonna be as friendly as we are." "Take it easy Miss
Baker. I'm sure your doctored up phycological profile of Gabby will be
satisfactory for them? After all, convincing Jeannette to do her part was
quite a masterpiece. I still can't believe you were able to twist her
mind in just 3 short months?" "My pshyco analysis was one thing Mrs
Wetherford, but I think the thought of the school potentionaly closing
and her ass back in pulic schooling was more of a motivator for her. I
wish I could've been there when she gave that boy a mouthfull of his own
cum! I always wanted to do that to a boy." "Well it doesn't matter how it
worked out, her part's over and Gabby's here. Miss Everhart, make sure
Jeannette gets the votes needed for class President next year." "Yes Mrs
Wetherford I'll do what's necessary. By the way, how are the parents you
contacted so far accepting Gabby's enrollment?" "Well they understand the
dire consequences that the school is in. Rather than lose their $12,000
tution they're willing to look the other way on having a pretty boy join
them for class everyday. Lets keep in mind that Gabby isn't just our 50th
student, he's a multimillion winning lottery ticket this school
desperately needs! All of us here will benefit greatly when the funding
officer secures our 3 million dollar grant for having a 'Tranz Girl'
getting her education here. Hundreds of other all girl schools across the
country have opted out of the 'Tranz Girl' funding potential which opens
up the door for us to be the first to get our hands on all that money,
and Gabby's gonna help us get it." "Mrs Wetherford, how much have you
told Mrs Hollinger about the funding?" "Miss Baker she knows nothing! I
told her the tuition for Gabby would be picked up by other parents who
have daughters here and that they would be reimbursed after Gabby's
enrollment goes through and our funding check arrives in October. I also
gave her $5000 to help insure Gabby has a wonderful feminine wardrobe to
keep her in the right frame of mind we need her in for the next 8 months.
All of you here just make sure those stuck up brats you teach everyday
keep being nice to him until further notice. I don't want him having
second thoughts about his big decision to enroll here. Now if there any
other questions?" "Mrs Wetherford." "Yes Miss Everhart?" "So what are we
gonna do about the Kelly's? They're kinda in the middle of all of this
and are gonna be pissed as hell if this thing blows up on us?" "I'm not
sure Miss Everhart? For now, Caroline and Diana know absolutely nothing
about what's going on here with the funding requirements and lets keep it
that way. We didn't ask for their help but they did set the table for us
after showing Jeannette and Juliette those video clips of Gabby eyeing up
the lingerie from the sidewalk. Maybe when we're finished with Gabby
we'll do something nice for Diana when she graduates next year? We'll
talk more tomorrow so get back your classrooms."
When Mom and I got done shopping we cleaned out my closets and dresser.
All my old clothes were bagged up and tossed in the attic while my cute
dresses and pretty underwear began filling my drawers and closet. After
years of hiding under my bed, I pulled out my box of Victoria's Secret,
Sears, JC Penney and Montgomery Ward catalogs. I could now look at them
freely to admire these beutiful girls and get some great ideas on how to
look more feminine. I didn't work at the lingerie shop today for obvious
reasons. Diana stopped by for diner with me and Mom after they closed up
to chit chat and inform me once again how great it was gonna be to see me
at school as a student. After supper Diana and I retired to my room and I
showed her all the great things Mom and I bought this afetrnoon at the
shopping center. After freshening up my makeup and getting me dressed in
a dress she wanted to see me in we enjoyed a more intense makeout session
on my bed. Her long nails pinched my skin as her feminine hormones began
to mature. Deep passionate kisses, soft moans and her quivering convinced
me that we were now definately a couple. My pantied cock was enjoying
everything that was going on and Diana knew how to take care of me. Soft
touches and pulls on my pantied cock made me twitch with excitement again
and again. This time however before she could get her head under my
skirt. I began shooting gobs of cum in my control tops and panties.
Diana's smile couldn't have been bigger as her hand slid inside my wet
panties. With her extended index finger she wiped off the head of my cock
and pulled it out in front of my lips. As her eyes began to get the best
of me she pressed her cum tipped finger past my pink lipstick covered
lips and into my mouth. "Make like a straw sweetie, I know you're dying
for another creamy taste." I closed my eyes and she slowly slid her
finger in and out of my mouth! Alarm bells went off in my head as the
taste of cum once again invaded my tastbuds! For some reason I began
sucking her finger which made her giggle. "That's a good girl! Nothin
like a little practice before you take on the real thing some day?" My
trembling feminized body began telling me that what she was doing to me
was erotic and ok. I think if she had offered me cyanide I would've taken
it!" As I continued sucking I felt her slide her other hand into my wet
panties making twitch even more. "Settle down Gabby, you're virginity is
showing!" It wasn't long before she switched fingers giving me another
fresh taste of creamy Boy Butter! Her 3" extended stiff finger I was
sucking on made it perfectly clear my feminine tendancies were now taking
over. I was hot and turned on by what she was doing to me. She left me
makeout with her cummy fingers for 5 long minutes before letting me catch
my breath and calm down. She then let out a sigh as she realized that I
had sucked some her nail polish off her nails! Diana left around 9:00 and
I was so messed up from our makeout session. I went to bed around 10:30
after redoing my own nails and picking out a nice dress for tomorrow's
uniform fitting at Saint Teressa's.
The next morning after breakfast I made sure Mom was in the car before I
stepped out of the house. I didn't want another confrontation to start my
day with my exbuddies from Jefferson High. Unlike the days before, Mom
dropped me off at Saint Teressa's before heading back to the shopping
Center for some more things I would be needing. I entered the school on
my own carrying my purse and a small Pink school bag for books and
tablets I may be given later today. When I got to Mrs Wetherford's office
I was greeted by her and a tall unfamiliar woman. AS soon as I entered
the main office Mrs Wetherford pointed to me and the tall woman
immediately took off her glasses and placed her hand on her hip. "My god
Leslie! She's beautiful!" The two of them walked over to me and Mrs
Wetherford wrapped her arm around my waist. "Gabby, I want you to meet
Miss Lacey from the state funding board. She's gonna be interviewing you
this morning." With a confused look on my face I meekly replied. "But I
thought I was getting fitted for my uniforms today?" "Well we can do that
this afternoon after lunch. Miss Lacey's not gonna be available next week
so she decided to make the 4 hour trip today to make sure your
application gets completed." Miss Lacey encircled me a few times and
picked at my short skirted dress and long hair. "Something wrong Leslie?"
The tall woman knelt down and then inspected my nyloned legs and pretty
polished toenails peeking out of the front of my shoes. "Just look how
feminine she is! Sheer pantyhose, open toed sandals and that chic teenage
Pink dress is to die for! She's obviously been dressing for years now
hasn't she?" "Why don't you and Gabby head to the conference room and do
your interview. I'm sure she can fill you in better on how long she's
been dressing." Miss Wetherford took my purse and bag while Miss Lacey
took my hand and began walking me to the conference room. Her perfume
mixing with mine made a very sexy smell together and I loved it! Our high
heeled steps on the tiled floor were in perfect synch as she slowed her
steps just enough so I could keep up.
When we got to the conference room she sat me down and opened up her tan
briefcase. "Now Gabrielle, I have a bunch of questions for you and I need
honest and up to date answers for them. Do you understand sweetie?"
"Gabrielle Mam, you called me Gabrielle." She arched her thin feminine
eyebrow and then flipped over her folder and showed it to me. On the
folder there was the name 'Gabrielle Hollister'. "I know everyone has
been calling you 'Gabby' for fun but what we're about to talk about is
very serious. So for the next few hours, lets go with Gabrielle, ok?" I
crossed my tanned nyloned legs for her and pulled the hem o fmy skirt
over the top of my knee. She instantly smiled and began with her
questioning. 'Now Gabrielle, why do you wish to enroll here at Saint
Teressa's?" "Well Mam, I think I would fit in better here with me wearing
girls clothes rather than my old High School." "Yes, I see you were at
Jefferson High for 2 years before your application was accepted earlier
this week. Tell me sweetie, did the boys and girls pick on you or beat
you up because of your feminine look?" "I wouldn't say I got beat up but
there have been some intimidating situations with a few of my
classmates." Miss Lacey jotted down my information as I told her about
yesterday's issue with the guys and also about the time Tina made a fool
out of me in the lingerie shop last week. "Now Gabrielle, have you ever
kissed a boy or a girl yet? And if so, how would you describe it?" I
immediately began smiling and blurted out to her. "I've had lots of fun
with a few girls here at the school Miss Lacey and Kissing them is a
great experience." "So you never had any romantic intentions or contacts
with boys yet?" "Uhhhh I really haven't had any boyfriends yet." She
continued jotting down notes and flipped over another page in the folder.
"Tell me Gabrielle, have you ever made a mess in your panties?" I got a
confused look on my face as her eyes focused on me real close. "I never
peed in my panties Mam." She took off her glasses and pointed down to my
crotch area. "That's not what I mean dear, I need to know if you ever
cummed in your pretty underwear?" I began turning red with embarrassment
as she knew the answer before I could even give it. "Well Mam, I guess
so, you see me and Di...." She quickly cut me off and eyed me up. "How
many times a week are you playing with yourself Gabrielle?" My mouth
dropped wide open as her friendly tone was quickly changing. "I... I... I
don't need to pull on my thingy! My girlfriend takes care of that for
me." Miss Lacey let out a sigh and sat back in her cushy chair. She began
shaking her head from side to side and I was begining to wonder if I just
blew my chances of entering the scool?
For the next hour I answered more questions on, fashion, makeup, the
female body and what was going on in my pretty little head. Miss Lacey
also asked me if at any time did Miss Wetherford or her staff promised me
any speicial treatment, favors or cash payments for items in return for
my application to the school. When I told her NO, she began nodding her
head for the first time in an hour.
When we got back to Mrs Wetherford's office to go over the interview, we
were joined by Miss Sanderson and Miss Baker. After we were handed drinks
Miss Lacey opened up her folder and put on her glasses. "Gabrielle's
interview went very well ladies. I felt she was honest and quite feminine
in the way she presented herself to me today. She clearly deserves a
chance to get her education here. But, I must emphasize that I'm not 100%
convinced I'm getting the full story here." Smiles quickly turned to
concerned looks as Miss Lacey crossed her nyloned legs and went on.
"Although Gabrielle is beautiful and very feminine, she still has a very
long way to go to womanhood. By her own admission, she's been making
messes in her panties, not showing much interest in dating boys and when
I pressed her on her goals in life she just shrugged her shoulders." Mrs
Wetherford quickly rose to her heels and placed her hands on her hips.
"Really Miss Lacey! I think your questioning of our student here is quite
out of line!" Miss Lacey took off her glasses and pointed them to Mrs
Wetherford. "Correction Leslie, 'Potential Student' without my
recommendation for Gabrielle you'll have to find another suitable girl to
fill that 50th spot to secure your funding." After a long silence Mrs
Wetherford cracked a smile. "Tell me Miss Lacey, what would it take to
help you be convinced of Gabrielle's abillities to get her education
here?" Miss Lacey began rocking her nyloned leg and tossed her long hair
over her shoulders before putting on her glasses again. "Well, if you
ladies can provide me with a little more proof of Gabrielle's feminine
intelligence I might be persuaded to give her the adequate score she
needs. Right now I think I'm just looking at a very pretty crossdressed
boy who makes messes in his panties and has no desire to continue with
life as a young girl!" I rolled my eyes to the ceiling and let out a
sigh. But just as things looked the bleakest, Miss Sanderson uncrossed
her nyloned legs and stood up. "Leslie, do you still have that 'feminine
IQ' test I gave Gabby earlier this week by chance?" Mrs Wetherford looked
at Miss Sanderson with a puzzeled look. "I.... I... IQ test?" Miss
Sanderson gave her wink of her eye and Mrs Wetherford began rummaging
through papers on her desk. "Ohhhhh yes, yes, the 'Feminine IQ' test.
Give me a second, now where is Gabby's test score?" It took her a few
seconds before finding it and handing it Miss Sanderson while Miss Lacey
watched. She then walked over to me and showed it to me. "Gabrielle, is
this the test you took on Monday?" Her long red nailed fingertip pointed
to my name and the date on the test. "Yes Miss Sanderson, that't the one
you gave me." Her hand was covering up my test score as I glanced at it
one last time before she handed it over to Miss Lacey. "I think
Gabrielle's score on the 'Feminine IQ' test may make you think twice
about not pushing her enrollment though Miss Lacey?" Over the next few
minutes Miss Lacey checked out my answers to the test and compared my
handwriting to prove I was the one who filled out the answers.
"Well, Gabrielle's score of 98% does sort of change my views on her
current state of mind. Perhaps if she could correct some of those unlady
like things she's doing and keeps her grades up we can push her
enrollment through? Miss Sanderson gave me a wink knowing full well I
only answered half the questions on the test she gave me Monday morning.
My smile began to grow as I watched Miss Lacey take her pen from her pad.
"A boyfriend or two for Gabrielle would really solidify the situation
here ladies." Miss Lacey smiled at me and gave me a wink while everyone
watched in anticipation. She began signing the necessary documents to
complete the enrollment process and the schools funding for the next
fiscal year. "You'll have your funds deposited into your account by the
end of the month. Get Gabrielle her uniforms and see that she's analyzed
by Miss Baker here on a weekly basis to keep her panties clean with
severe discipline for future messes! I'll stop by in 2 months to see how
her grades are progressing along with checking her attendance record. I
want to make sure this isn't a one week thing to try and get the funding.
My congratulations ladies on being the first private girls school to
allow a boy into their classroom." Everyone gave me hugs and I couldn't
have been happier. Mrs Wetherford was so happy now that she had secured
her funding along with the other confident teachers she had on her staff.
I was still a little confused on why Miss Sanderson enhanced my 'Feminine
IQ' score but at this point I wasn't gonna question it!
After lunch I was fitted for my school uniforms. Soft Pink monogramed
sweaters, short plaid skirts, crisp white long sleeve blouses and many
packages of shiny white tights that all the girls wore every day. Miss
Baker fitted me with some cute white and pink patent leather shoes with
low and no heels to make sure I was in compliance with the schools
uniform policy. When we got back to the office area the teachers were
sipping champagne and smiling from ear to ear. Miss Sanderson wrapped her
arm around my waist and set down her half full glass. "Welcome to Saint
Terssa's sweetie, I hope you understand it's skirts, panties and 24/7
feminitity until further notice? Starting on Monday you will report here
for your first day to start your education at Saint Teressa's all girl
school." Miss Sanderson looked deep into my eyes and began stroking my
long curly hair. Her smile and enthusiasm made me crack a smile. "Why are
you looking at me like that miss Sanderson?" She swallowed down her
champagne and then eyed me up with a more womanly look. "You better keep
your hand out of your panties young lady! That type of behavior will not
be tollerated. Proper spankings and detention will be in your future if
continue to do these unlady like things. We don't want to disappoint Miss
Lacey when she comes back for a follow up in two months. Do we understand
each other?" She gave my long hair a nice little pull to get her message
accross. "Oooouch! Miss Sanderson that stings!" "Your pantied ass will be
in worse shape the first time I catch you messin up your panties sweetie!
So keep that in mind! Your nails, hair and makeup will be in perfect
order every day like the rest of the girls! Demerits will be handed out
if you don't meet up to my expectations in the classroom, is that
understood Gabrielle?" I was in a dazed frame of mind as she towered over
me with her intmidating stare. "Well Gabrielle, I'm waiting!" I softly
spoke up as she sensed my uneasyness. "Ye.. ye.. yes Miss Sanderson." She
stared deep into my eyes for 5 long seconds as I slowly tried to step
away from her. This wasn't what I had signed up for to say the least!
Gone was her friendly smile and her words of encouragement had been
replaced with an ultimatum to follow her rules or get my pantied ass
spanked!
After talking with a few other teachers Mom and Mrs Weatherford emerged
from her office. Mom was stuffing a large envelope into her purse and had
one of the biggest smiles on her face I had ever seen. She quickly
grabbed my trembling hand and pulled me away. "Lets go Gabrielle, you'll
get your uniforms delivered to the house on Friday. Now lets get some
lunch before you head to Miss Kelly's for your afternoon shift at the
lingerie shop." Everyone waved to me as Mom pulled me from the office. I
began getting a lot of butterflies in my cinched tummy as Mom pulled me
out into the hall. The sound of my low heeled shoes clicking on the tiled
floor filled the air as we made our way to the door. "Mom, I think we
should talk about this girls school thing one more time. You see, Miss
Snaders...." "Hush Gabrielle! There's no turning back now, the contracts
have been signed and the school is now compatible with a the minimal
amount of students to stay open." "Contracts? What contracts?" Mom put on
her sunglasses and whilst me out the door into the bright sunshine. "Head
up and keep your skirt down sweetie. Make sure the world sees you coming
Gabby because you're about to make history over the next 8 months here at
Saint Teressa's!" Mom, please slow down and listen to me!" "Not now
Gabby, first we have to stop at the bank to make a large deposit before
lunch and then we'll buy you some more dresses and shoes at the mall."
With long strides my nyloned legs rubbed together under my skirt and the
soft wind blew up my skirt and made my long hair flutter into the wind. I
now wondered what kind of feminine deal Mom made for me with the historic
all girls school?