The Club's Back 9
By Jeffanie
As I made my way off the 13th green with guys, we headed over to the
snack shack for a drink and a burger.
We drove over in our golf carts and waited to be served. "Well look
who's still working the shack!"
"Shut the Fuck up Jeff!"
"Awe, come on Olivia the fresh air will do you some good."
"Well it just pisses me off that I have to come out here and work the
shack because we can't keep any of those college girls we hire to
work."
"Well, what happened to Kris and Kelly, they were doing great?"
"They both called Ms. Prescott and just quit, and didn't even give a
reason. So now I have to work out here til 5pm and then work in the
dinning hall tonight til 11pm, I'm so pissed and tired of all the long
hours!"
"How about a burger to go with that Shake you got goin on there,Honey?"
I watched Olivia's sexy ass and legs walk away from me to get my order.
The other guys were waiting to tee off as i got my food and drink.
"Here you go dear." I gave her a $10 tip and a wink of the eye. "Whats
the big tip for hot stuff." She looked at me with a smile and waited
for my reply. "Maybe some day we can hook up and have a little fun?"
Then her smile turned to a pissed off look! "Your just like all the
other guys around here, you think a girl is that dumb!"
"Take it easy Olivia, I meant it, why don't we get something to eat one
night?" I heard the guys yelling for me from the tee box, but I was
trying to score with Olivia. She crossed her arms and popped out her
hooters at me."Well, if you are truely serious, I guess we could try it
sometime, but it will be on my terms only." I gave her my number and
told her to give me a call. I walked over to the tee box with a big
smile!
"Well it's about time, come on and hit your damn drive." We teed off,
and when we got out in the fairway the guys wanted to know if I scored.
"I think I'm in guys, I gave her my number."
"Wow, so it looks like you got your foot in the door with Olivia the
goddess."
"Come on guys she may never call."
"Well I'll go $5000 and say you won't get her on her knees."
"You got a bet Fred."
"How about you Jerry, you want a piece of the action."
"I would love to have her suck me off, if you can fix it, I will go the
same $5000."
"I don't know how you are gonna trick Olivia into your sting operation
you got goin here, she aint like those college brats you've been
tricking over the past year. If you can pull this one off, you will be
my Idol!"
"OK, if she sets a date up with me early this week I'll have her on her
knees for you guys by the weekend." We shook hands and went on to
finish up our round.
Over the past year I have been blackmailing the dumb college girls who
come to work at the snack shack. I would promise them the world, and
after I got plenty of nude photos of them, I would then turn around and
have them on their knees sucking off all the members of the club who
would put up the $500. Of course after they suck the guys off, they
quit and never come back. I always tell them never to call the cops or
I would post all the photos around campus and their hometown.
Naturally, I would bang them from both ends and make a couple bucks on
the side. Being 25 years old and small in size, I never had much luck
with girls so this was my only way to get the hot ones I wanted.
Besides, who are the people gonna believe anyway, a college tramp, or a
fine upstanding Country Club member!
Monday and Tuesday came without any word from Olivia. On Wednesday I
finally got a message on my machine at home. "Hi Jeffy dear, Why don't
you come and pick me up at my place tonight and we'll get that dinner
you want so badly." I called her back right away and set up the time
and got directions to her place. Later that day at the club I told the
guys that we have a date set and our bet was now live. I told them with
any luck I will have Olivia ready by Saturday or Sunday night!
I picked up Olivia around 6:00 and we headed to her favorite restaurant
for a steak. "I want to thank you for giving me a chance Olivia, you'll
see i'm not like all the other guys."
"Well, I'll be the judge of that dear." She was dressed to kill with
super shiny nylons, a short Black skirt and sky high heels. She was
actually taller than me in her heels by at least 3" since I only stood
5' 8". "So tell me Jeffy dear, what is it about me you like so much!"
"Olivia, you are true Femininity, and your beauty is cover girl
material, I just can't believe you're not married. I wanted to ask you
out the first time I seen you when you started working at the club, but
Ms. Prescott told me you were dating someone at the time."
"That's not true, I've been single and free for the last year or so,
you should've asked me then. To be honest, I was hoping you would ask
me out sometime." I could'nt believe what I was hearing, this girl is
gonna be so easy to get in bed.
We had our meal and headed back to her place, hopefully for a drink or
two. "Thanks for the dinner Jeffy dear, say why don't we have a drink
before you go and talk a little."
"You don't have to ask me twice Olivia." She grabbed my hand and I
walked behind her following that super tight ass hiding under her
leather skirt. "Have a seat I'll get us some wine." I took a seat on
her leather sofa and waited for those Black nylon covered legs to join
me. With her red hair and beautifully tanned complexion this was going
to be the best girl ever for me, and I knew the guys would pay plenty
to have her on her knees for them."Here you go dear." We rasied our
glasses for a toast. "To a new begining." Our glasses touched and she
sat down next to me, crossed her legs and siped her wine. "So how do
you like my little skirt and legs?" I almost chocked on my wine when
she asked me. "Why,I, I think they're beautiful Olivia, I stammered
out!"
"Just beautiful, don't you think my legs are sexy?" I was starting to
get a little nervous as she kicked off her shoes and laid her feet on
my lap! "Why yes Olivia, your legs are very sexy" I can tell you like
them dear, because you can't keep your eyes off of them!" She was right
I was in total awe of her legs and who I was with. Her Black Nylons and
red painted toenaills were so sexy and they were now on my lap! "Maybe
you could massage my feet sweetie?" I quickly gulped down my wine and
began to massage her feet. "OHHH that feels so good dear, your a pro at
this. Very nice Jeffy you have a great touch. I bet your little dick is
getting harder and harder!" I quick looked up at her and made eye
contact as her foot went right to my groin.! "Boy you sure are getting
all stiff and hard!" Olivia's nylon covered pretty feet were now
massaging my hard on and I was about to loose it. "Olivia, maybe we
should check out your bedroom now that I'm so hot for you?"
"Not so fast sweetie, this is just a little taste of how I will blow
you away when we make love. First you have to do some things for me to
show your not like all the other guys, and then when I'm satisfied of
your loyalty, we will make love." My hard on was getting harder and
harder as Olivia's Black nylon covered feet massaged my groin. "What do
you want me to do Olivia?"
"Meet me here tomorrow morning at 8am and we will see if you're ready
to take the challenges I have for you."
"OK, I'll be here bright and early." She put on her heels, pulled me
from the sofa, and escorted me to the door. As quick as it started, it
was over, and I was on my way home. I got very little sleep and when
morning came I phoned the guys and informed them of how things were
progressing.
I arrived at Olivia's place at about 7:50am. "Good morning sweetie, she
grabbed my hand, pulled me inside and gave me a morning hug. "So are
you ready for a litle fun this morning dear?"
"Yes, Olivia I'm ready to please you and do what you desire."
"That's great dear. Now, here is what I have in store for you today.
Since I have no help at the snack shack, I have been trying to cook and
serve all by myself. Today you will help me do the cooking and I will
do the serving."
"WO, WO, WO, You want me to work with you at the shack, are you crazy?
Do you have any idea how humiliating this will be when the other
members see me?" She crossed her arms and walked over to me. "Look, you
either help me out, or you can find someone else to take to dinner in
the future!" She towered over me in her Heels as I decided what to do.
I then thought about the $10,000 I bet with the guys and new I was kind
of in a spot. "OK, you win, I'll help you today." She smiled and gave
me another hug. "Great, now lets get you in your little snack shack
outfit." She pulled me into her bedroom and on her bed was a skirt and
a girls top along with some low heeled shoes. "What is wrong with you
Olivia, I can't be seen wearing this stuff!"
"Will you stop your complaining, you will be working in the back, so no
one is gonna see you. I even have a wig for you to wear and some sun
glasses."
"NO, NO, NO, I can't do this Olivia, this is fuckin crazy. I will be
the laughing stock of the club if someone spots me wearing a skirt."
"Fine, then you can just leave, and don't ever ask me out again!" I
stood there and looked at the feminine clothes as Olivia gave me
another hug and began massaging my groin and whispered in my ear! "Your
gonna look so cute in your uniform, maybe we can make out a couple of
times when it's slow this afternoon?" It wasn't long before my dick was
hard. and Olivia's hands were in my pockets stroking me off! "Come on
sweetie you can do it for me, all you have to do is cook and I will do
the rest."
"OK, OK,
you win." Great you can start undressing." I took off my clothes and
Olivia handed me a pair of white shiny panties. "Can't I wear my
underwear!"
"Absolutely not, your gonna work as a girl today so you will dress like
one to." Olivia then strapped me into a padded bra and began to lace me
into a mini corset! "What is all this stuff?"
"I have to give you the proper figure so you can fit in your skirt."
She then threw me a pair of tights! "Here, you have to wear Black
tights so no one sees your leg hair. I could'nt argue with her so I
pulled the shiny tights up all the way to my waist. "Very good sweetie,
now put on your Blouse and skirt for me." It wasn't long before I was
totaly dressed as a girl. Olivia put on my shoes and then had me sit on
her bed. "Now lets get your wig on and we will be off to work. She
placed the wig on, and then handed me my sun glasses. She pulled me off
the bed and then to a mirror. "My god, I look pretty good, I think this
might work?" She gave me another hug, gigled a little, grabbed my hand
and pulled me out the front door. There was no changing my mind now!
We arrived at the shack around 9:00 and had to work until 6:00. All day
I was dreading that someone would recognize me. I cooked hot dogs and
burgers while Olivia ran the register and served everyone. All in all,
the day went very smoothly. Many of the club members were asking who
the new girl was, and Olivia told them I was the new snack shack girl.
When we got back to Olivia's I was pretty beat and sat on her couch.
"You were awesome today dear, let me get some drinks for us." Olivia
got us another bottle of wine and sat right beside me on the couch. "I
can't believe you let me dress you up as a snack shack girl and made
you work a full day as well! It looks like you may score with me big
boy, I am truely impressed!" She gave me a big hug and then rubbed her
legs with mine. "Maybe you are different than the rest of the other men
i've known." She held my hand and stared into my eyes. "So what's next
for me Olivia, do you want to do something tomorow?" Well tomorrow I'll
let you think about what you've accomplished today, but Friday morning
I want you here at 9:00am so we can have some more fun." Her foot
started to massage my rock hard Pantied dick as I was falling more and
more into her feminine grip, and it was supossed to be the other way
around. We drank the bottle of wine and exchanged another hug or two
and then I headed back to my place.
On Thursday I played golf with the guys and told them that things were
looking great for Saturday night at the usual time and place. The word
around the clubhouse was that Olivia would be serving on Saturday night
and now all the guys were getting their cash ready, because everyone
wanted her. I told Fred I wanted $1000 per member for this one. I knew
there was no way to back out now, and I had to get Olivia's confidence
in me.
I showed up on Friday at Olivia's at the 9:00 am starting time she
requested. "Come on in dear, we have a big morning ahead of us." She
pulled me in and sat me down on her sofa. "So are you ready for your
2nd. challenge dear?"
"Yes I am Olivia, what are we doing today, working at the shack again?"
"No, No, No dear, I've got bigger plans for us today. Since you were
such a good girl on Wednesday, I thought we would do a little shopping
today, if you're up to it?"
"I'm ready for you Olivia."
"That's great honey, why don't you start undressing while I wait for
you in my bedroom. I knew she was now planning on me to be her girl
again for the day. "Come in sweetie look at the pretty things i have
for you to wear today." On the bed was a pile of white and Pink
garments. "You want me to wear that stuff?"
"Of course dear, your gonna look so cute in this pink skirt and
sweater. I even got you some White silky tights for your legs." I
couldn't believe I was about to get dressed in this stuff. "Olivia can
we do something else where I can be a guy?"
"If you don't want to be my girlfriend for the day I'll understand.
Just remember when you leave, your chance of making it with me goes out
the door as well!" Once again I now stared at all the feminine clothes
as Olivia towered over me in her high heels and miniskirt. It wasn't
long before I was being strapped into a padded bra and Panties. I
pulled the White Opaque tights up my legs and Olivia tied me into the
mini corset like yesterday. "Today I want you to wear a pair of low
heels dear." She handed me a pair of 2" Pink wedge pumps and like
everything else, they fit perfectly. I pulled the seweater over my head
and slipped on the skirt. Olivia straightened out my skirt and it fell
just below my knees. "Very very nice Jeffy dear, you look great. Now
smile for me." I looked up and she started taking pictures of me with
her camera! "Olivia, give me that camera!"
"Shut up and stand there like a good girl while I add to the pictures I
took yesterday at the shack."
"What, you have pictures of me in the shack?"
"Of course sweetie I have a lot of good ones of you in your little
skirt flippin burgers."
"Please Olivia, give me those pictures!" She smiled at me and laughed
as she put her camera in her purse.She put the same wig and glasses on
me and once again I was now dressed as a woman for her pleasure and
fun. She tied a scarf around my neck and handed me a purse as we went
out the door.
"Where are we going Olivia?"
"We are going to a couple stores and into the mall to buy a dress or
two."
"What are talking about? I'm not gonna be fooling anyone in a dress
shop!"
"Will you relax, you'll be perfect, and you really have no choice since
we are 3 miles from home. Of course, if want me to let you out I will
stop the car and you can walk back home." I was screwed and she new it.
We pulled up to a drug store and she handed me a list. "OK dear get
your ass in there and buy everything on this list."
"Please Olivia, I can't do this!"
"Of course you can dear, you'll be just fine. By the way give me your
wallet."
"What for?"
"Just give it here!" I handed her my wallet from my purse and she gave
me back one of my credit cards. "Now get your ass in there and fill
that list." I opened the car door and walked into the store. I looked
at the list of things to buy and they were all feminine items. Nail
polish,Hair color,perfume,lotions,Pantyhose and about 6 other items.
For 20 minutes I shopped up and down every isle until I filled my
basket. When I went to check out I noticed the check out girl was a
girl from the college I tricked and blackmailed last year! With my
heart beating rapidly I set my items on the counter. "Good morning Ms.,
did you find everything you were looking for?" I nodded my head and
kept it hung low hoping she would not recognize me in my feminie
outfit. "Your total is $85.45." I handed her my credit card and she
swiped it through the machine. She looked me over while we waited for
the card to be accepted. She handed me the slip and I quickly signed
it. "Thanx for shopping with us Ms.." I grabbed the bag and quickly
went out to the car. "Well how did it go for you sweetie, let me see if
you got everything." As she inspected the bags contents I was trying to
regain my composuer after the close call Ii just had. "Very good Jeffy
dear, now lets hit another store or two!" She smiled wickedly at me and
we drove into the mall. Over the next 2 hours we shopped and shopped
and not one person ever questioned my appearance. Every store we
shopped at I ended up buying girls clothes, make up, underwear even
jewelry. My credit card was getting a real workout too. I must have
bought over $2000 worth of stuff. Olivia's camera was also flashing all
morning, she must have taken 100 pictures of me in all the stores.
"OK dear lets make one more stop at the dress factory before we head
home. "I hope you are enjoying this Olivia, I'm not sure how much more
of this I can take?"
"Your doing great Jeffy, I am truely impressed with your feminine
side."
"Stop that Olivia, I want to show you my masculine side."
"Actually you would make a nice girl with some more work. Besides, I
think you like the little outfits I put you in."
"I'm only doing this to prove to you I am not like the other guys
you've been with and that's all. I never wore womens panties and skirts
before!"
"Well you look good in em, so why don't we go try a couple more on at
the dress shop?"
We pulled into the dress shop and went inside. "Come along sweetie,
lets see how you look in some of these outfits." Over the next hour I
tried on several skirts and even a couple dresses as Olivia checked the
fit and took plenty of pictures as well. "Please, Olivia I have had
enough, can we go now?"
"Sit your ass down and let me try on a few things." I sat down and
waited for Olivia to try on some outfits. I loved looking at her
perfect figure and long nylon encased legs. Everything she wore was
beautiful. We headed to the sales desk to check out and finally leave
the store. As usual, I paid for the items and the sales girl didn't
even blink an eye at me, I guess I looked like girl after all. When we
got out to the car Olivia gave me a big hug and a kiss on the cheek.
"You were fantastic today Jeffy, let's go home and get a bite to eat."
"Yea, I'm starving."
We unloaded the car and put all the bags in Olivia's Bedroom. I took
off my wig, scarf and glasses and Oliva shouted out! "Hold on dear I
want you dressed like that til we finish lunch."
"Please Olivia can't I change into my clothes?"
"Absolutely not, we are having lunch and then we will have a nother
drink before you go." As Olivia made some soup and sandwiches I sat on
the sofa still wearing my feminine outfit. We finished our lunch and
Olivia brought over another bottle of wine. "Here you go sweetie." I
took the glass from her and drank down some.
"So Jeffy, where would you like to go tomorrow night?"
"I'm not sure, what are you in the mood for?" With aplayfull smile she
kicked off her shoes and slid her foot up under my skirt! "Well I think
I'm in the mood for some wild fun, do you think you're up to it?" Her
toes reached my panties and slowly masagged me. "I could feel myself
hardening up as her other foot slid up to my panties. "God Olivia, I'm
so hot for you!" Her feet then began to pull my knit skirt down off my
legs. "Come on sweetie, reach in those panties and pull out that Pee
Pee for me!" My mind was on overload as I pulled down my tights and
Panties. "That's a good girl, now lets see how you can stroke it!" I
quickly grabbed my rock hard penis and closed my eyes. "Oh, Olivia
Please suck me off!"
"Keep going dear I want to see how large you can get, and don't you
dare shoot your load all over your skirt.!" I stroked myself for
several minutes as her nylon covered feet massaged my shaft and groin
area! "Please Olivia I can't hold it anymore!"
"Ok sweetie you can stop now I've seen everything I need to see." She
came over to me and planted me with a deep kiss! "Tomorrow night I will
give you the hottest sex you ever had wherever you want to do it. All
you have to do is one more thing for me and I will be yours."
"Yes Olivia I want you so bad!"
"Go put your clothes on and I will see you out. I picked up my skirt
and went to change as Olivia cleaned up the dishes and glasses. She
gave me one more Kiss as I left. "I'll call you tomorrow morning so be
ready." I kissed her one more time as she closed the door and I headed
home.
As soon as I got home I called Jerry and told him everything was on
schedule. I told him I would have Olivia at the shack around 8:00 after
she finishes her evening work. Like in the past I would text him to let
him know when everything was ready. I also told him to bring the 5
grand so he could pay his part of the bet he was about to lose. I
drove back over to the snack shack and secretly put the handcuffs and
phone in my secret spot so I would have them ready for tomorrow night.
All night I was thinking of how much I was gonna bang Olivia, and then
I somehow have to trick her into all the other stuff I had planned for
her. I knew now I had to do what ever she wanted tomorrow or I was
gonna lose a lot of cash to the guys.
Saturday morning arrived and around 9:00 Olivia called me. "Good
morning Jeffy dear, get your butt over here by 10:00, we have a little
issue to deal with." She wouldn't tell me over the phone so I quickly
went over to find out what was up. I knocked on her door and she left
me in. "Oh my god Jeffy we have a little problem."
"Calm down Olivia what are you talking about?" "This morning I got a
call from Ms. Prescott and she wanted to know who was working in the
shack with me the other day."
"So what's the big deal, just tell her it was one of your girlfriends."
"Well I did, and then she told me it was against club policy to work
without signing the proper forms. She then asked me if I would get her
to help work at the club today since two girls called off."
"Well what did you tell her."
"I told her I would get her to help today."
"Oh my god Olivia, I can't work in the shack today, all the guys are
playing a tournament, they will see me."
"It's not working the shack dear, it's woking the dinning hall inside
the club."
"Now how the hell am I gonna fool anyone in the club? I may fool some
people at a store, but this is way over the top!"
"Come on dear, I will get you ready for everything, I have told Ms.
Prescott that your shy and don't say much and she'll buy it, she's not
that smart." I was a basket case as everthing was starting to go down
the drain. Olivia then came over and embraced me. "Come on dear all you
have to do is fill some water pichers and take away some dishes and it
will only be for about 4 hours. We will be done by 7:00 and then we can
spend the rest of night together." I looked at her as she nailed me
with her best Kiss yet. I knew I had no other choice if I was to win my
bet.
"Ok Olivia, how are we gonna pull this off." She hugged me again and
then went over to the phone and started dialing. "HI Shelia, its me
Olivia, do you think you can give me a couple hours today say around
12:30 to 2:30? Great I'll be over with her this morning."
"Who was that Olivia, That was Shelia, she has a shop in town and I
need her expert skills to pull this off. Now lets get undressed and
head to the bathroom. I undressed and she pulled me into her shower.
"Now the first thing we have to do is bleach your body hair so you look
more feminine. The bottles are on the shower ledge. Just wipe the cream
all over including your face and wait about 15 minutes. I grabbed the
bottles and began to smooth the cream all over my legs, arms and body.
"Here, let me get your back." Olivia squirted more cream all over my
back and ass cheeks and then waited for the cream to work. Her smile
had more of a deviliish and playfull look as she looked on. "Yes you
are gonna look so good when I'm done with you dear." The time went by
and Olivia handed me a wash cloth and turned on the shower. "Get busy
sweetie, I'll go set out some clothes for you to wear. I wiped the
cream off and to my horror all my leg hair went with it! My arm and
body hair were also dissolved as I wiped them clean!. "Olivia, get in
here, I shouted!"
"What's the matter dear?"
"My hair is gone, this stuff isn't bleach!" She grabbed the bottles and
looked at them closely. "I'm sorry dear, but it looks like you bought
hair remover instead of bleach when you were at the drug store
yesterday. Don't worry it will grow back in 6 weeks."
"This isn't fair Olivia, now I can't wear shorts around the club"
"Well don't blame me, you bought the wrong stuff, now stop your crying
and rinse off." My body was now totaly hairless and smooth like a
girls, all soft and silky. After rinsing off and drying myself I went
into Olivia's bedroom.
She then began to cover my skin with baby oil. "Hold still sissy let me
massage this stuff in.""Please Olivia can you call something else, I
don't think this is gonna work?" She grabbed my earlobe and pulled it
hard! "Now look sweetie, your gonna help me today and your gonna like
it, understand?"
" Her tone had changed and I could tell she was getting pissed. She
then began to spray me all over with a feminine body spray. "I smell
like a woman Olivia!"
"No shit, your gonna look like one soon so shut up!" She quickly
wrapped a padded white bra around my chest and handed me a pair of
white silky Panties. "Here you go Jeffy dear, no more tights for you,
you are ready for Pantyhose."
"Are you crazy, I'm not wearing pantyhose!"
"Stop arguing with me and put your pantyhose on, now!" I sat on her bed
with her nylons in my hands as she stood over me waiting for me to put
them on! "Lets go sweetie!" I slowly worked the suntan nylons up my now
hairless legs. "Very nice, very nice, you have great legs dear." She
then gave my ass a good smack and pulled my earlobe again!"
"You better not argue with me anymore dear or I will be looking for
another man tonight, do you understand me!"
"Yes Olivia, I'm Sorry." Olivia then wrapped the white mini corset
around my waist and pulled the laces tight to give me the proper
figure. "Here, pull up this slip and put on this camisole while I get
you your dress and Heels. My mind was going out of control as she
feminized me, but I knew in the end I would be the big winner. Olivia
pulled a white dress over my head and then zipped up the back. The
dress was a very feminine silky dress and it was one I bought yesterday
at the dress shop. "Here put on these Heels. I placed my nylon covered
feet inside the white pumps and at the urging of Olivia I walked around
the room for her. "NO, NO, NO, your not walking right. Pop out your
chest and swing your hips!"
"I'm trying Olivia, give me a break." Over the next 30 minutes I
strutted back and forth until she was satisfied. Once again a scarf was
tied around my neck my wig and glasses were in place and we were
heading for the door. "Here take these garment bags and put them in the
car, I want to stop at the dry cleaners while your getting worked on."
I grabbed my clothes and started to take them out to the car with me as
well. "Whet are you doing? I didn't tell you to take those with now put
them down dear."
"Please let me take my clothes so I can change for our date tonight."
She took my clothes from my hands and threw them in her bedroom! "Now
lets go sweetie you can get your clothes later when we get back. We
walked out the door and into the fall morning sunshine.
My legs were shiny and silky and my dress flowed beautifully with every
step I took. We got in the car and headed into town. When we got into
town we ended up at Sheila's salon. "What are we doing here Olivia?"
"Well you can't be a girl with that hair style and your nails need work
as well." Before I could argue I was being pulled in through the front
door. "Hi Olivia, is this the sissy you told me about?"
"Yes, he needs a great new hair style along with nails and makeup and I
need her done in 2 hours!" I didn't like the sounds they were making
and I definatly did not like being refered to as a sissy! "Come on
sweetie lets get you all dolled up." I looked back at Olivia as Sheila
pulled me across the tiled floor. "Have fun Jeffy, I'll be back to pick
you up in a couple hours."
"Ok sweetie the first thing you need to do is take off that lovely
dress so you don't get it messed up." Sheila unzipped my dress and then
instructed me to take off my nylons so the girls could work on my
toenails. I sat down wearing just my feminine undewear in the padded
chair and Sheila went to work washing my hair. "This is gonna be a
great challenge, we don't get many sissy boys in here." I wanted to
reach out and punch her, but I had to keep the big picture in mind for
tonight. After Sheila washed my hair she covered my hair with a smelly
lotion. "My god, what is that stuff?"
"Oh it's a little of this and a little of that, don't worry dear."
After about 30 minutes she began to tightly wrap my shoulder length
hair in curlers!" The other girls who were working with other customers
were snickering and giggling while Sheila took care of me. "There you
go sweetie, now lets get you under the dryer fror a while. "Here is a
little stress reliever mask you can wear while my girls do your nails."
I put on the little mask and sat back in the chair in total darkness as
Sheila placed my head up under the dryer and turned it on.
Over the next hour the girls began to file and shape my fingernails and
work on my toenails, all I could think about was how I was gonna spend
all the cash tomorrow. I never knew how much a girl had to go through
just to look good. I was almost dozing off when Sheila returned and
turned off the dryer.
"Hi dear how is it going?" I took off the mask and saw Olivia and then
I noticed that my nails were now extended 1/2" long and covered in
shiny red nail polish! "Oh my god Olivia! look at my nails, how do I
get this stuff off?"
"Just relax sweetie, your glamour look is needed to fool everyone at
the club later." My toenails were also femininelypainted bright red.
Panic was starting to set in on how feminine my appearance was
becoming. Sheila was laughing at me as she uncoiled my hair from the
rollers. "Come on sissy, don't tell me you never painted your nails
before." Olivia's smile was full of eagerness and I think she was
getting turned on by the way I was looking. "Yes dear, tonight I am
gonna rock your world!" Sheila finished combing out my hair and then
started to apply my makeup. Over the next 30 minutes my face was
covered with liquids and powders. "Now hold still dear while I get
these false eyelashes on you." I kept my eyes shut as she applied them.
She then coated them with endless amounts of Mascara! "Very nice
Shelia, very nice!" Olivia was sitting seductively in front of me as
she watched my trasformation. "Pucker up sissy boy." Shelia cupped my
chin and rolled a good amount of Sultry red lipstick across my lips
again and again. Both women stood towering over me and gave each other
a hug. "Absolutely perfect Shelia, you have out done yourself this
time." Olivia Pulled me from the chair and gave me a big hug and kiss
on my forehead. "Lets get you dressed dear we have to be at the club
soon."
We walked to the changing room and I noticed one of the garment bags I
put in the car was hanging on a hook and my dress I wore to the salon
was no where to be found. "Olivia, where is the dress I wore?"
"Your not wearing that to the club dear, you will need a special
serving dress for this evening." I looked at her puzzled as she took
the garment bag from the hook and unzipped the bag. "This will be your
dress for tonight dear." I looked in awe of the shiny Golden club
serving dress that hung from her finger. "No way, I can't wear that
Olivia, I'll never fit in that!"
"Oh yes you will, now start undressing, I have other sexy foundation
garments for you wear." She snapped her fingers and Sheila gave my ass
a sound smack! Olivia watched me closely as I undressed down to my
birthday suite. Sheila walked in with a box of black feminine underwear
and sat it beside me. This situation was getting way out of hand as I
had no other options but to keep going. Somehow I had to get out of
this mess, and I still had to get Olivia to her destination for the
guys tonight.
I stood naked in front of both women and Olivia began to spray me with
perfume all over. "You're gonna be the talk of the club sashaying
around in your little dress sweetie."
"Please Olivia, lets talk about this for a minute." She threw me a pair
of Black satin panties as Sheila walked out of the room with all the
clothes I wore to the shop. I now had no other choice but to wear what
they gave me! "Those panties fit you nicely honey.Now hold still while
I give you some realistic breasts. "No Olivia, Don't you dare!" I
watched in horror as Olivia sprayed my chest with adhesive and then
pressed jiggily breast forms with nipples on to my chest! "You're
fucked up Olivia, get these off of me!"
"its too late dear, that glue has allready set and your stuck with em."
Both women laughed as I sank deeper and deeper into there clutches.
Sheila then wrapped a Black satin bra around my newly formed breasts
and tightend the straps for a perfect fit. "You have such beatiful
lingerie sweetie."
"Yea, and he bought it all when we went shopping yesterday." I wanted
to run but where could I go without any clothes. "Here you go dear you
can put on some more Pantyhose for us." Olivia handed me a pair of
Suntan pantyhose and like before I pulled the silky nylon material up
my legs and all the way to my waist. "Very nice sweetie, let me see how
smooth you ass is now." Olivia grabbed my nylon covered ass and slid
her hands all the way down my nylon covered legs. "Yes Jessie dear,
dear this is exactly how I pictured you would look and feel all covered
in shiny Pantyhose."With great excitement Olivia pulled another Shiny
Black garment from the box. "Come on Sheila lets get her into her
corset for tonight." Olivia wrapped a shiny Jet Black corset around my
waist and seconds later the women were lacing me in it!' "Such a good
girl you are letting us dress you up like this."
"Please Olivia stop this now I can't wear this thing, I want out of
this deal!" I was almost breaking down as she ran the laces through the
eyelets and began to tighten them. "Arms up sissy boy, we need every
inch so you can fit in that dress!' Sheila gave my ass another sound
smack and then another as I lifetd my arms way above my head! "Olivia
tightened me up with one final pull and snaped it shut with a tiny
lock! I put down my arms and sat on the chair trying to get my breath
back, all the while I stared at the shiny golden metalic dress I was
about to wear.
"Here, you can roll these stockings up your legs while your sitting
down, and make sure your seams are straight." I took the Jet Black
back seamed stockings and rolled each one up to my thighs. The women
then lined up my seams and attatched them to the 4 garters dangling
from the corset I was wearing. "it's now dress time sweetie!" Olivia
unzipped the back of the Gold metalic dress and invited me to step into
it. With no way out, I stepped into the dress and Olivia eagerly pulled
it up and over my feminine hips. "Now put your arms through sweetie." I
put my arms in the long golden sleeves and with great satisfaction
Olivia pulled the zipper all the way up past my neck, the collar
covered my neck completely all the way up to my chin! Sheila then
closed all 6 buttons of the sleeves and Olivia clipped a pair of shiny
gold hoop earings to each earlobe, now there was no way of getting out
of this mess, I couldn't believe this was happening to me! "Sit your
ass down dear, we have some lovely heels for you!" From another box
Sheila began to put my nylon covered feet into a pair of 4" Shiny
golden open toe sandals. She strapped them on high around my ankles.
"Lets see you can walk in those dear." I stood up and walked around for
the two of them!"
"Beautiful Jeffy dear, just beautiful! Come on lets get her to a
mirror." I was taken out into the shop in front of a dozen other
women!" My heart was racing so fast as my high heels clicked along the
salon floor. I Looked in the mirror and I was in toatl shock! "My god
what did you do to my hair?"
"Why it's called a perm and color sweetie!" I pulled at my curly hair
to make sure it was me and not a trick.All the women were laughing
histericaly as I stared at the lovely creature in the mirror. My shiny
dress ended above my knees and flared out with the built in Black
crinoline Petticaot. My girlish figure was perfect and my legs were so
sexy and shiny. I could even see my red toenails shinning through both
layers of nylon I was wearing! My makeup was flawless with deep red
lips and slutty Black mascara filled eyelashes, I truely was a
knockout! I was an emotional wreck as panic was setting in, and then it
hit me, I had to go to the club in this outfit and work!
Olivia pulled me over to the register and handed Sheila my credit card.
"That will be $550 sweetie." My jaw dropped as she zipped it through
the machine. "Sign here dear and you hurry back for some more fun when
that color fades out." All the women laughed at me as I signed the
receipt and Olivia quickly pulled me out of the salon and over to the
car. "Just let me look at you glamour girl, my god you are so HOT in
that dress!" Olivia gave me a big hug and another kiss as we pulled out
and headed for the club. There I was totaly feminized and looking as
hot as Olivia!
"When are you gonna change into your dress Olivia?"
"When we get to the club dear, It was sent out for cleaning earlier
this week." When we got to the club Olivia took us around back to Ms.
Prescott's Office. "Now look dear, I told Ms. Prescott your name is
Jessie, just nod to her and don't talk to anyone. I told her you had a
sore throat and you couldn't talk much. I know you can pull this off
Jessie dear, just remember, chest out and swing those hips baby!" She
gave me one last hug and then pulled me inside. "Well good afternoon
girls, you must be Jessie. How nice it is to meet you dear. You look
smashing in that serving dress, I wish I had a figure like yours."
"Now Jessie, before you start your shift you must sign some paperwork
to work here at the club, so I need you to sign these 3 forms and then
we will get you out on the floor. Olivia has given me your address,
phone number and some other minor information so all I need is for you
to sign at the X's." I quickly signed all the forms and watched Ms.
Prescott put them in the filing cabinet. "Now Olivia, I have changed my
mind on what I want you girls to do tonight. Olivia, I want you to go
down to the shack and clean it up, I had two complaints from members
today and I don't want anymore! When you finish down there you can come
back and help out with Jessie here." I looked at Olivia in disbelief at
was happening! I need you girls here until 7:00, so get going and I
will give jessie a little tour and instruction on what is to be
expected from her tonight."
I watched Olivia wink at me with a smile and walk out the door, Ms.
Prescott then guided me out into the dinning area. I now was on my own,
dressed like one of the club's serving girls! "First thing young lady,
put your name tag on and tie this apron around your waist." My name tag
said Jessie and I pinned it to my dress, I then tied the matching
metlic gold apron around my corseted waist. "Now you can start setting
up all the tables with silverware, napkins and drinking glasses. I have
one table here all set up the way I like it, you can do the rest." Over
the next 45 minutes I set up all the tables per Ms. Prescott's
instructions. My Dress was so shiny in the bright lights and no one
ever thought I was I guy, my confidence was growing with every high
heeled step I took. "Very nice Jessie, I think you may have a long term
career here. Now tonight, all you have to do is keep the water glasses
full and give the patrons another knife or fork if they ask for one,
Ok." I nodded to her and she gave me a tour of the Kitchen and the rest
of the dining area as well as the bar. "When we got back to the
dinning area the tables were filling up and Olivia was still not back.
Ms. Prescott then asked me to start filling up all the glasses. I
teetered around in my tightly fitted dress and high heels filling glass
after glass. All the women in the club's auxilliary were here for their
once a month gathering and they all made a fuss over me and how much
they liked my appearance and manner! I looked at the clock and it was
now 5:30.
"Oh Jessie dear." I walked over to the hostess desk where Ms. Prescott
was seated. "Look dear, your gonna have to help serve since Olivia is
not back yet." Ms. Prescott sent me to the kitchen and I now was forced
into serving meals to everyone and there was no other girls helping me
for the 20 tables! Over the next hour Ms. Prescott pushed me hard to
deliver the meals and do everything else as well! The women were not
shy in their demands as I was litteraly running at times in my heels to
get what they wanted. My legs and feet were killing me and my waistline
was getting femininely crushed by the corset Olivia tied me in! I was
running out of gas and trying to keep up with everything. By 6:30
Olivia was still was a no show as I was the only one prancing around in
a serving uniform clearing all the tables along with serving coffee and
tea! I was also running out of time as 8:00 was almost near and I still
had to get Olivia ready for the guys. I finished removing the last of
the dishes at about 7:00 when Olivia walked through the door. I was so
pissed off yet relieved to see her. I was exausted but I was now done
with everything and ready to get the hell out of there!
"Well done Jessie, you were fabulous this evening. I think I will have
you back tomorrow afternoon if your not busy?" I looked at Ms. Prescott
as she waited for my reply. "Why don't we see how the rest of the
evening goes Ms. Prescott, Jessie and I got some things to do and I
think she may be wore out for tomorrow."
"Ok Olivia, give me a call tomorrow morning, I would love to have her
for another party."
Olivia pulled me out into the dark parking lot and gave me a hug and
planted the best Kiss I ever got on my lips! "I knew you were different
than all the rest. Any guy that can do you what you did for me over the
last week deserves my affection and love!" She embraced me and rubbed
her nylon coivered legs with mine as I teetered on my high heels. The
cool night air whistled around our nylon covered legs and I started to
get hard! "Please Olivia, I want to do it with you right now on the
back nine, I'm so hot for you!' "Just listen to you, you want to fuck
me dressed as a woman?"
"Yes, I don't care I need you now, please do it for me!" She slid her
hand up to my panties and stroked my throbbing hard on! "OK sweetie if
that's what you want, hop in the golf cart and I'll take you for a
ride!" We both got in and took off into the darkness! She steered the
cart with one hand and steered my pantied hard on with her other hand.
"How does this spot suit you Jessie dear?"
"This is perfect Olivia!" Over 3/4 of a mile away from the cluhouse we
pulled up aside of the snack shack and got out of the cart. I now could
finish off the night in a big way as things were looking up. She held
me close as we made out in the dim moonlight. "I'm gonna mess your up
makeup with all this lip service I'm giving you Jessie."
"Give me your key to the shack Olivia, I want to get us a bottle of
wine for this special moment."
"Sure dear, here you go, I could go for a glass myself."
I took the key from her and walked over behind the shack to get the
cuffs. I pulled the bag from under the shack and quickly texted Jerry
to be here in 30 minutes, I then inserted the key in the lock and
opened the door to the shack. As I opened the door a bunch of women
came storming out! "Grab him girls!" I said nothing as three women
grabbed my arms and pulled me over to Olivia. "We got him girls, we got
the bastard now!" I was totaly shocked at what was going on as my
wrists were put behind my back and cuffed with my own handcuffs. One of
the other women then slapped my face and grabbed my newly permed hair!
"You fuckin bastard, you are gonna wish you were never born after we
get done with you!"
"Who the hell are you, and what are you doing here? Olivia please help
me! I cried out" I stood there in my serving dress and heels surrounded
by a dozen women!
"Well Jessie dear I want you to meet some of the women who came out to
see you tonight. This is Mrs. Sanders and this is Mrs. Baker, this is
Mrs. Cooley and of course you already know Sheila from the salon." The
other 8 women are also from the area. "I don't understand Olivia
what's going on, let me out of these handcuffs!' "Shut up dear, I will
do the talking and you will do the listening." Two women griped my arms
tightly and dug their nails deep into them. Another women had a good
hold of my hair as I stood there helplessly. "You see, Ms. Pescott and
I were fed up with all the girls who quit working out here at the shack
over the past year, and we were determined to find out why. Finally we
got a break when one of the girls told us how you tricked her into your
little sex game and how you humiliated her with everything you did to
her."
"No, that's a lie, you can't prove a thing Olivia."
"Your so wrong dear, I want you to meet her mother." A woman came out
of the crowd of women and slapped my face hard. "You bastard, my little
girl will never be the same after what you made her do. She may never
recover. I hope you rot in hell for what you did!" She slapped my face
again as a tear rolled down my cheek from the pain. "Please Olivia let
me go, this is all wrong, I never did any of this!" I was completely
terrified and I was totaly screwed. "No Jessie dear, you're caught and
you must pay for what you did."
"No one will believe you, no one, now let me go!"
"Two can play the blackmail game sweetie, just look how nicely dressed
you are for us tonight. Your wearing a club serving dress, Pantyhose,
High Heels and Makeup. I bet all the other club members would love to
hear about your little hobby."
"No, no, its a lie you made me do this." Come on sweetie, you begged me
to dress you up and take you shopping, at least that's what I'll say to
everyone. Why, Mrs. Baker here owns the dress shop that you bought your
dresses in. Mrs Cooley owns the drug store where you bought all your
makeup and Pantyhose. Mrs. Sanders owns the lingerie store where you
bought all your feminine underwear yesterday and of couse you had
Sheila do your hair and two of the girls you blackmailed did your nails
today while you were wearing that mask at the salon this afternoon so
you would be beautiful for your waitressing debute here at the club
tonight." All the women laughed at me as Olivia went on and on, and I
was losing all hope. "The best thing is this dear, we got it all on
tape with the stores security cameras, and we have all the receipts
from your credit card with your signature on them as well. That's why I
wanted you to use your credit card instead of cash, so we had a nice
little paper trail if we needed it, and since you were in such a hurry
to sign the receipts, you didn't notice the women cleverly moved the
decimal point to the right and added one extra zero to the total so you
ended up paying 10 times than what the actual costs were. Your little
shopping spree yesterday cost you more than $20,000 instead of the
$2000 you thought."
" You hoars let me go and give me my money back, this isn't fair I'm
not gay I don't enjoy dressing as a woman!"
"Don't forget about all those pictures I took of you this week dear,
including this gem I got of you when you weren't looking." I looked at
the print that Olivia held in front of me and there I was dressed in a
skirt, blouse and tights Jerking off my stiff rod on her couch with my
eyes closed. "I think this picture will show everyone how much dressing
as woman turns you on." I was now totaly screwed and they had me! "Ok
you win, let me go now, you have all you need to get even."
The night is young Jessie dear, and we didn't set all this up just to
get even. We all think you should learn the finer points of being a
woman." The women pulled me along up aside of the shack to an awaiting
blanket. "On your knees girl!' I was pushed to my knees and my ankles
were quickly cuffed and then tied behind me to the light pole along
with my cuffed wrists!"
"What are you doing, let me go!"
"Now Jessie, it is your turn to do a little lip sevice."
"What are talking about? I cried out!" Olivia came over and put her
hands on my shoulders. "It's like this sweetie, earlier this week Ms.
Prescott bugged your golf cart to find out what you were up to, when
she uncovered your little plot, she thought it would be a nice treat
for you to take my place in that trap you were setting and now here you
are on your knees all dressed up for the guys!"
"No Olivia, don't do this to me, let me go I'm Sorry for what I did,
Please!" I was shaking and just about ready to cry at the situation I
was now in. "Tough luck dear, the women came out here to see you
perform and get their revenge. We will be collecting all your money and
watching you from the shack, just like you did to all those innocent
girls."
"This will never work Olivia, the guys will see it's not you sitting
here and leave."
"Remember today when I left the salon for those 2 hours dear?' "Yea,
so."
"I actualy came over to the club and wore that same dress your wearing
now and did a little waitressing for the guys at the bar so they could
see me all decked out in Gold. Ms Prescott gave all the other girls the
day off today so I was the only one the guys had a chance to see today
in a serving dress. Since I snuck you into Ms. Prescott's office today
you had no contact with any of the guys, so in their eyes I was the
only one here today. Now here you are in the same dress, red permed
hair, with red lips and nails just like me earlier today. I think your
appearance is close enough to fool em in all the darkness out here." My
heart started to race as reality of what she said was starting to take
hold! "I won't do it, you can't make me do it, I'm not sucking anyone's
cock!"
"You have no choice dear and I'll tell you why. Those forms you signed
in Ms. Prescott's office this afternoon were admission of guilt papers
that were pre-notorized by Mrs. Blake over here. By signing those
forms, you were admitting your guilt to all the sex traps and blackmail
you put those girls through, in other words, your fucked!"
"Tears began to roll down my cheeks as they played their final card.
"You will be on your knees until all the guys are done with you, and
the first time you cause any discomfort or cause any problem, Mrs.
Muncy will take you down to the police station in her squad car and you
can spend the next 10 years in jail all dolled up for the inmates."
"Please Olivia, I can't do this!" I cired and begged as the tears
rolled down my cheeks. "Oh, I almost forgot!" I watched as Olivia
removed my name tag and attatched hers to my dress. "There you go girl
now your ready for some action and you better no spill a drop!" I was
sprayed with a good amount of perfume and I watched her unscrew the
outside security lightbulb and enter the shack with all the women. She
then opened the widow slightly so the guys could slide the money under
it just as I had done many times before. Panic was about to turn into
reality as the dim moonlight was just bright enough to show my feminine
silhouette!
I sat on my nylon covered knees as the cool fall night air breeze blew
through my permed hair. It wasn't long before a golf cart pulled up and
a man went over to the window and slid his money under it. He walked
over to me and began to unzip his fly. With his big hands he grabbed my
Fire Red hair and pulled me up to his awaiting hard on that was bobbing
in front of me. "Come on bitch open up." I new it was Mr. Randall who I
had golfed with many times before. "Lets go Olivia, I aint got all
night." I just couldn't open my mouth as his dick pushed against my
lips. I then felt a shock around my neck, and then another and finally
a third that joted me enough to open my mouth! He waisted no time in
driving all his manhood down my throat! I mumbled and choked on the
size of his dick and I couldn't stop him now that he was all the way
in. "Ooooh yes Olivia, You looked so hot today in that outfit I just
couldn't wait for this moment tonight!" He rammed me back and forth, I
even hit my head against the metal pole I was bound to. "Here comes
your dinner slut!" I felt his cock twitch, and then again as his motion
quickened. I was balling like a baby as he moned out, Olivia, Olivia,
Yes,Yes!!!! Seconds later mountains of cum filled my mouth as he
pounded me again and again. "Oooooh God that was great slut!" I
swallowed every drop as per Olivia's demand and sat there sobbing. Mr
Randall left go of my hair, walked over to the shack and tapped the
window. "Thanx Jeff, I don't know how you do it, but keep doin it
buddy, I'll see you later." The golf cart sped off and I knew when he
got back to the clubhouse someone else would be comming out for me!"
"Very nice Jessie, Mr Randall sure got his money's worth. Next time
don't take so long to start or we'll have Ms. Presscott give you
another shock. I looked up at her as she smiled down at me. "That
collar in your dress is fitted with a little shock device and Ms.
Prescott is back in her office watching this with her night vision
camera. You will be shocked harder if you keep fucking around!"
"Please let me go Olivia, Please!"
"You got along way to go, so pucker up sweetie. Looks like your mascara
and make up is ruined from all your crying dear, now I'm sure the guys
will never know its not me!" Over the next hour I sucked off 7 more
members and was emotionaly crushed. The women all enjoyed me servicing
the men who their daughters serviced over the past year. I knew the
worst was to come when Jerry pulled up. He slid his envelope of cash
under the window and then approached me. "Well bitch you just cost me 5
grand so you better give me your best blow job ever!" Now dressed as a
club service girl wearing Pantyhose,High Heels and a dress, I had to
suck off my golfing buddy!" With two fist fulls of my Red permed hair
he pushed his dick way down my cum stained throat!" I pulled as he
pushed and his shaft engulfed all of my mouth! "That's it Olivia, suck
it all in my slut!" The sound of my handcuffs rattling once again
filled the air as he pushed and pulled and pushed! Tears continued to
roll down my cheeks from the humiliation and servicing of my friend.
For 5 long minutes he face fucked me again and again until he couldn't
hold it any more! His moans of pleasure now filled the night air.The
familiar twitch of his rock hard dick gave away the inevitable as he
shot his load 5 times down my throat! "How was that Olivia dear?" His
dick went limp and then he pulled my hair one last time."Lets do this
again sometime bitch!" I hung my head low and contiued to cry as he
drove off back to clubhouse. The next hour was filled with me sucking
off member after member including Freddy who was my last to serve.
I sat crying my eyes out and my body was shaking and trembling when all
the women came out of the shack. The women removed my handcuffs and I
was pulled up to my feet. "What a night Jessie dear, you serviced 20
club members in a little over 3 hours. I have about $30, 000 here from
your excellent service you provided. Add that to the $20,000 from your
credit card and we have a nice 50 grand! All this money is going to
these women to help pay for all the damages you caused to their girls."
The women all came over and gave my pantied bottom a sound smack as I
stood there shaking and totaly whipped. Olivia then put her hands
around my corseted waist and stared into my eyes. "Your punishment is
not quite over dear. Unfortunatly the women want you to work as a
waitrees in the club for 2 more years to help pay for more therapy for
the girls you fucked!"
"Please Olivia, I can't, don't make me do this I'm sorry for what I
did, let me go." She wiped my tears with her fingers. "There are two
more things we have to take care of tonight dear." All the women
surrounded me and then I was pushed on my stomach face down on the golf
cart seat! "Cuff her wrists to the seat ladies."
"At the suggestion of Ms. Presscott, we are now gonna give your first
round of female hormones to help fill out your breasts and hips, you
don't want to be wearing a corset all the time do you?"
"My god Olivia, please don't do this to me, I don't want to be a woman!
I looked back and watched as the women pushed up my skirt exposing my
pantied bottom. I kicked and kicked to try and stop them but is was no
use, I was out numbered and exhausted, all I could do was cry! "That's
it ladies pull her pantyhose down and her panties. Dr.Tally you may
have the honors." A woman walked up behind me, slapped my ass hard and
then stuck me in my ass cheek with a needle. Moments later she repeated
the same in my other cheek. "There you go you fuckin bastard, my little
girl at home won't even talk to another boy after what you did to her!"
She smacked my ass again and then stepped back. I laid ther sobbing and
shaking from all the humiliation, sucking off and now I had female
hormones running through my body! Olivia then stepped up to the cart.
"Jessie dear I have to tell you, the first time I saw you, I wanted to
make love to you like no one before! But first I wanted everything to
be perfect for the 2 of us. Now here you are wearing your gold dress,
sexy high heels and pantyhose. Your even wearing Black seamed stockings
as well. I could not ask for anything more to turn me on!"
I heard her skirt fall to the ground and then she grabbed my corseted
waist. "There's just one more thing you should know dear, my name is
not Olivia. it's Oliver!" I looked back and watched as she shoved her
rock hard dick deep into my virgin ass!"
"Nooooo! please stop!!!! I cried out." Again she pushed and then one
more time!"
"Oooh yes Jessie, now I'm all inside you sweetie, how I longed for this
moment! I wanted to fuck you in the shower today so bad, but this was
well worth the wait." I pulled at my binds as tears continued to roll
down my cheeks and Olivia's Motion rocked the golf cart and my world as
she promissed she would. "Please stop this, please!!!"
"Shut up you bastard you deserve everything your getting, no one can
here you beg out here but us, keep going Olivia!" My cries and Olivia's
sexual moans of pleasure filled the night air as the women watched
their revenge unfold before their very eyes. "How are you liking losing
your virginity to me jessie? You were turning me on so much this week
letting me dress you up as my girlfriend. Don't worry dear, this will
not be the last time we do this! With my 9" in your back side, I think
we are giving new meaning to the Club's Back 9!" I was perspireing and
sobbing and Olivia was panting heavily! I could feel her motion was
quickening as her shaft slid effortlessly in and out of my ass! "Get
ready dear, I can't hold it anymore, here I cum!" I was totaly out of
breath as I meakly cried out one more time."Noooo Olivia, please pull
out, please!" Her grip tightened around my waist as she screamed out!"
Jessie, Jessie, Ooooh Yes!, Yes!, Yes! It felt like an earthquake with
the golf cart shaking as she climaxed deep inside me again and again
and again! Ooooh, Oooh, Oooh, jessie dear! Her motion slowed and the
golf cart stopped rocking and she pulled her dick out of my ass! She
fell to the ground shaking all over from her orgasmic overload. The
women all applauded her performance as I laid there beaten and whipped.
My panties and Pantyhose were pulled back up and my hands were freed
from my binds. I was in total shock as I sat in the golf cart trembling
and terified. Olivia put on her skirt and pulled me from the cart. "You
are now mine and don't ever forget it!" I never came like that before!
My life has been missing something for the last 2 years, and now I have
found it!" She kissed me deeply and gave me a bear hug as my trembling
body tried to recover. All the women gave each other hugs and cried a
little as they got their long awaited revenge.
Everyone got into their golf carts and we drove back to the clubhouse.
Ms. Prescott was waiting to greet us as we pulled in. "Well ladies how
about a night cap?" All the women walked into the dinning area and Ms.
Prescott walked me into the bathroom. "What a performance Jessie, I
hope you understand your punishment is not over dear. After what
happened tonight Olivia will not be able to show her face around here
again so your ass will be in here working parties and the snack shack
every day for the next 2 years, and if you're a bad girl, we may just
keep you around sucking cocks for another year, so don't piss me off!"
You will be living with Olivia from now on. Some of your victims have
already cleaned out your house and will be setting fire to it
tonight."So what ever Olivia wants, you better give it to her or it's
off to prison in your little dress and Heels." Now wash your face off,
I'll send Olivia in to fix your makeup so you can serve us properly my
dear." I stared at my mascara ruined reflection in the mirror as Olivia
walked in and hugged me from behind. "How's it going dear? I hope you
can forgive me for some of the things they made me do to you. I myself
have 2 more months of Blackmail to finish before they let me go, I
hope!"
"What, their blackmailing you to?' "Yea, I use to be a good looking guy
just like you, and then one day they forced me into a dress, and I have
been dressing like a woman ever since. Tonight was the first time they
let me have sex with someone since this all started. I must say, I
loved banging you Jessie!"
"But you look so hot Olivia?"
"It's the hormones sweetie, just like the ones they shot in your ass
tonight. You'll be thinking just like woman and looking as hot as me in
about 8 months, so get ready for your bra size to be a C or D real
soon.!" I hung my head low as Olivia consoled me. "Come on sweetie,
lets fix your makeup and serve these bitches so we can get out of here
tonight. The night is young, and there is still one more thing I want
to get straightened out between us before the night is over." Her hands
slid up under my dress and into my panties and she whispered into my
ear. "I'm gonna get you so good and stiff for me when we get back home
dear, my ass is screaming for your 9 inches!"
Email me:
[email protected]