INNOCENTLY
You never know how it'll will all start as it seems so innocent at the
time. Well, for starters it is the mid 90s and I'm returning to school to
begin my Junior year of college in Charleston, SC. At this time, I'm just
Tim a skinny kid from Maryland. I drove down with all my clothes, books and
everything else needed for the year packed in my beat up and tiny Ford
Escort. I was excited as this was going to be my first year living off
campus.
My summer had been pretty boring since my parents basically spent all of it
in Europe without me. My Mom is a teacher and so she has the summers off
and my Dad is a high-level executive who always took his time off in the
summer to travel with my Mom. Sure, they asked me to go but I figured they
basically wanted to be alone visiting places Paris, Rome, etc. and I
thought I would have plenty of fun hanging around town. My parents were the
type to just leave me to my own thing and do their own thing, they weren't
always the most involved. I was an only child and felt more in their way
than not. They paid for everything for me and anytime I'd ask for money
they'd usually provide it quickly. I think they felt guilty about not
overly wanting to be involved in my life. They preferred to just pay and
give me what I wanted so they could do their own thing.
Of course, as it turned out most of my High School friends had moved on to
live and hang out near their colleges and the ones still around either had
jobs, girlfriends or some combo of that taking up their time. So, I
basically did some running and calisthenics to stay in shape, played some
pick-up soccer occasionally and would play video games or watch movies the
rest of most days. As such by the time mid-August rolled around I was more
than ready to head back to school and have some fun with people my age. My
parents called and wished me well and off I went driving to South Carolina.
When I got there, I drove to the house my roommate Dan and I had rented. It
was a small Cape Cod type house but it was renovated kind of nicely. The
main floor had a bedroom, bathroom, the living room and the kitchen. While
upstairs also had a bathroom and bedroom. It also had separate entrances
which I guess was for when the house was rented to 2 different renters.
They could essentially keep the downstairs and upstairs divided. We figured
we probably wouldn't need them and would just use one. There was also a
basement with a washer and dryer and room to store some stuff. So
basically, we each got a room and a bathroom and would share the common
areas. We had chosen rooms when we rented the house and I took the
upstairs.
When I got there Dan was already there moving his stuff in. He was from the
East Coast of Florida so while the drive was still long it was a little
shorter than mine. We shuck hands welcoming each other back and then got to
the task at hand moving in. The place had the beds, a couch, some tables,
dressers and other furniture already there. Nothing fancy but good enough
for college students. We got everything from our cars into our rooms which
took a while. We figured if we like the place it would be our home the next
2 years so we each brought lots of stuff to make it feel that way. I
brought a TV that my parents had gotten me and we stuck it on the table in
the corner of the living room.
Once, we were finished we went downtown to grab food, a few beers and catch
up. Yes, both of us aren't quite 21 yet. I turn it in December right before
break and he turns it in November. But we each have fake IDs which in the
90s is something you could easily get away with. Most bartenders would be
shocked when it was really your 21st birthday and they'd served you for a
year or two. We hung out and talked about our summer breaks. Mine as I
mentioned was pretty boring while Dan's seemed exciting lifeguarding by day
on the beach, catching rays and beach parties by night. He sure beat my sit
around and play video games. He went on and on about awesome stories of his
summer.
Just as I was asking him about going to his house for spring break our
friends Kim and Dawn sat down at our booth. "Nice to see you guys," Dawn
said "how were your summers." Kim and Dawn were both from Georgia and had
met as roommates too. We all got along but there weren't any relationships
brewing it was all very plutonic and seemed to be clearly staying that way.
I went on to say "we were just catching up on our summers. Dan's was
apparently awesome and I was just about to ask him about joining him there
for spring break." "Oh no" Dan said "about that. My parents gave me strict
rules there Tim, no crazy parties there. They live in a quiet community now
since they moved. If I want to bring a girlfriend and chill out that's fine
but no dudes partying all hours." "Great" I said "my parents are going away
during spring break and I hoped to hang with you. I'll be bored out of my
mind." "Well there is still one way" said Dawn. "What is that?" I said
happily thinking that they had a place or something in Florida. "You could
become Dan's girlfriend!" Dawn exclaimed. I just giggled "yeah right." Kim
chimed in "you know you could probably do it you're pretty short and
skinny." Dan said "well your more than welcome try." Then rolling his eyes
"If you look good and I don't have a girlfriend by then I'll take you and
we can fool my parents during the day and then head out as guys at night.
You better look good though because my parents can't know" "Well we'll see
I guess." Meanwhile both Kim and Dawn were planning. "Our house tomorrow
night Tim!"
The next day came and as usually Dan and I went running in the morning. We
did this almost every morning. Dan was in ROTC and so he had to stay in
shape and I just went along to keep in shape and have something to do to
start my morning off right. Dan is tall like 6'4" or something and probably
200lbs or around there and muscular. He played all the sports in HS
football, basketball, baseball, swimming and surfed. He was the do it all
athletic type kid. I was much smaller only 5'6" and all of about 135lbs. I
played soccer in high school and was at best average. I loved baseball but
it became more of a sport I followed than one I played. I was in good shape
but initially still had trouble keeping up running with him. My legs would
have to take 2 steps to his one. But over time I figured it out and we'd
run close and do some sit-ups, push-ups and the like. Today he asked
giggling "so are you going to give this girl thing a shot with Kim and Dawn
tonight." I just shouted back "I'll give it a shot but I'll probably look
horrible." I ended it there because I figured this isn't probably going to
work out at all and I'll have to find something else to do on Spring Break.
That night I headed over to their house as they had asked. They chatted
with me about how I could do this since I was in fact not the biggest of
guys and had some girlish feature. They stripped me and then took some
measurements and basically asked me for 1000 dollars to get me everything I
would need. "Seems like a lot" I said. They both said back "it'll get you
started and if you like it you're going to too spend much more being a
girl." "Being a girl?" I said. "Yes, you can't just show up put on a wig
and some crappy makeup and fool his parents for 2 seconds and then hide in
a room. If you're his girlfriend they're going to want to get to know you
and talk to you maybe go out to dinner" Kim said. "So, you need to learn to
be one of us or fake being one of us all the time" Dawn said giggling. "The
only way to do that is to immerse yourself in it. You have plenty of time
before spring break but you're going to need to find out how to be a girl."
"I just figured it be change to girl then back to me once I get there."
"Yeah not that simple. Every weekend between now and then you need to be a
girl with us and by then we think you'll understand. If nothing else you'll
know what it's like." "Ok" I mumbled. I figured well it's my parent's money
and they'll give me more out of guilt if I need it. I gave them the $1000
and they said we'll get everything for you to initially be a girl and we'll
go from there. We'll see you on Friday night 5pm. They went on to say make
sure I shave everything and they were specific about where. I walked back
home and figured we'll see how it goes but I can't see myself wanting to be
a girl at all let alone every weekend.
The week flew by and classes started. It was a whole lot of meeting new
professors. I'm a communications major so it's lots of presentations now
that we're into the 2nd half of college. I got up to run and work out with
Dan every day this week so I feel energized after a somewhat lazy summer.
But each and every day Dan teased me about trying to become a girl.
Basically, he pulled out all the standard tropes that guys use. You know
like you want tits to touch them all the time or you're just in it for free
drinks. All the stuff along those lines and also along the lines of I won't
be enough for a stud like Dan. It's almost at the point where I want to be
so hot that I just get other guys to want me and make him jealous. I'm also
to the point where I just want to see how it turns out so I can either do
it or forget it and move on.
Friday came and since I was smart and planned ahead I scheduled no classes
this semester for Fridays. Yes, Monday through Thursday is loaded up all
day but I wanted the 3-day weekends. It's around noon and I decide I'll
take a shower and follow the checklist of shaving requirements the girls
gave me. It took a while but now I have pretty much no hair from my head
down. I had little to begin with on my chest so that was pretty easy. Legs
took a bit and now feel kind of strange with no hair. I made a mental note
to wear jeans to classes instead of shorts at this point. I don't want
anyone wondering what's going on. I've seen swimmers shave and if in
trouble I'll use a triathlon as my excuse. My face is a bit more normal to
shave but I have little there and I really only shave every week or so at
this point if that. Shaving my arm pits was weird and hard and while it's
nice not to have hair there does feel more than all the other areas. They
did have me shave around my privates but it wasn't extensive and more so
just keeping it contained within my underwear line. It felt weird
altogether to be so hairless but after 5 minutes it went out of my brain. I
got dressed in some jeans and a t-shirt and sat around until I left around
4:30 to head to the girls' house.
I had no idea what to expect when I got there but they sure did. They made
it clear that I was theirs for the weekend and not just tonight. They told
me I better learn quick because tomorrow night we're going out to dinner
and maybe the clubs. I just basically nod in agreement with whatever they
said at this point as I was at their mercy to help me. That and to not
expose me as a guy whenever we did go out. I was scared to death that that
would happen and every one would find this as a big joke. They took me
upstairs and we began to get started. It was going to be a crash course on
life as a girl.
First, they had me strip naked like zero clothes. It was along the lines as
we need to start you from being naked so you understand how to build out to
being a girl. Kim brought over a tan underwear thong type item. This is to
hide Mr. Willy. I looked baffled I guess. She said "you do know us girls
don't have a Mr. Willy, right?" That's when I got what she was saying. So,
I pulled up the thong which I later learned is called a gaffe and Kim
showed me how to pull back my penis and essentially make it and my balls
literally disappear. Well I guess I'm all in now. Dawn took some flesh
looking blobs out of a case and now I could tell these were going to be my
boobs. I'm going with boobs by the way. Tits sounds so slutty and trashy
and breasts just sound like a science teacher. So, boobs it is. Dawn sprays
my chest with a very sticky adhesive and then centers each blob on one of
my nipples. She holds them down for a while. After removing her hands
they're stuck to my chest and you can't even see the seam of where I end
and they start. They have me jump up and down which we all get a big laugh
out of and they make sure they stay on. Dawn said "They're C cups Tim, er,
we can't go with that. Did you pick out any names?" "Yeah, I did I'll go
with Heather. I figure it's way different than Tim and girly." "Ok then
Heather these are C so when you go to shop for more bras start there and
please go to Victoria Secret. It's the best." I'm thinking why do I need
more bras and why would I shop in Victoria Secret guys don't go there like
ever. They get out a bra and some matching panties in black. They explain
how to hook on a bra and then spin it around. My panties are now covering
my tan or apparently nude thong. My body does kind of look somewhat female
at this point with no hair, boobs and Mr. Willy hidden. They pulled out a
waist cincher and explained how to use it and what it's for. "With your
tiny waist the waist cincher will give you and hour glass figure right
away. After a few months you probably won't even need it. You're so
freaking skinny it makes me jealous. But it'll give you nice curves" Kim
said. Basically, I did look like a girl from the head down at this point. I
was surprised it wasn't overly difficult.
I did still look like a boy head on a girl body though but that was about
to change. They had me sit down and spun me away from the mirror. They
explained what makeup they were applying and assured me tomorrow we'll go
over it more. But tonight, was just to get me to believe I could be a girl.
After awhile they seemed please and both looked amazed. You're going to be
hot and guys are going to want you. "You mean like Dan who will know about
me" I said. "No, no Heather you're going to be like a 9 or 10 when we're
done. Like seriously superhot. You'll be batting guys away either that or
learning to enjoy being with them" Dawn said. "Why would I enjoy them?"
"Why would you not, is more the question?" Let's get a wig on her. They
placed a blonde wig on me first but didn't seem to like it much. "We
thought with your blue eyes that blonde hair would look great. It's ok but
let's try the black maybe her eyes will pop." As soon as they put the long
black wig on and styled it they just starred at me. I asked them "what was
wrong" a couple of times feeling panicked. After a while Dawn just
whispered "you, you are beautiful. You will definitely pass as a girl
physically. Once you learn how walk, talk, dress and act like one you'll
have guys dreaming about you." With that they spun me towards the mirror
and I was just as shocked. To the point that I thought it was all still a
joke and the way Dan thought of me being a girl when he was talking joking
to me. At this point I thought it was another girl was just pretending in
the mirror. I would move my hands and my mouth and turn and shake and the
half-dressed girl would do the same. I was waiting for the candy camera
moment. But a few minutes in to doing that, I too just sat there in shock
and disbelief. I had thought I would look horrible like a dude with a wig
and that would be that. But here I am looking better than almost any girl I
know and I'm not even dressed I'm basically sitting in my underwear. "Oh my
god, I can really do this!" I said. "Yes, yes you can!" said Kim. "Just
please let us teach you how to act, think and be a girl because I have a
feeling you're never going back." "Back to what?" I said. "Back to being a
scrawny, dorky and very much single guy!" Dawn said.
The rest of that night was mainly spent trying on outfit after outfit. They
had picked up every kind of item for me. From jeans and t-shirts to skirts
to sweater to a little black dress to sun dresses and on and on. Quite a
few pairs of shoes too. Sneaker, flats and what seemed like at the time
pretty high heels. They also provided all types of underwear or should I
say intimates now. There were bras and panties in various colors, thongs,
pantyhose and of course my biggest shock bikinis. "Why do I need a bathing
suit?" I said. "Again, Heather you're going to be a girl full time if you
do this Spring Break. That includes going to the beach as a girl. Unless
you want to go topless. Having a suit is a must." They would try stuff on
me and explain how it all should fit and where I could make changes. It was
a lot to take in really. I didn't know there was so much differences even
with things that would seem similar like jeans. They also discussed how to
move and act like a girl. Things from how to sit to how to walk and even
just standing. I did some walking in the heels and learn that it's hard and
is going to take some practice. I did get some things down but I probably
looked like a really awkward girl. I was surprised though how much I looked
like one each time I would catch a glimpse in a mirror. I was tired as it
was around midnight so we all agreed to end it for the night. Off came the
wig and both the girls and I decide in the future that should be one of the
last items removed. I was still all dressed in my LBD, with hose and heels
and makeup. But I had a guy's haircut. After that I removed the heels and
pantyhose and then took off the dress. I stood there half naked admiring
myself. The girls talked about how you like it don't you, you'll get used
to it and that I was going to be a great girl. I just shuck it off but I
had to admit I very much did look like a girl even with no hair. They
showed me how to take off the bra and waist cincher. Once that was done I
was given a robe, a box and a bottle of some kind of solvent. Dawn said,
"Off to the bathroom, you can take that solvent and rub it around your
boobs. Then they should peel off and you can place them in their spots in
their box. Then it's up to you to get Mr. Willy we don't need to see all
that. Afterwards put on the robe and come back out to take off the makeup."
I went into the bathroom and did as instructed after first eyeing myself up
and down. I was still really not believing it. I peeled of the boobs and
place them in the box. It already felt weird to not have them but the
weight being gone was nice. Peeling off the panties and then the gaffe was
a whole new experience. It felt good to be free again but it was kind of
little wet. Not soaked or anything but sweaty from being compressed. I was
turning back to Tim from Heather and while it felt ok I was dwelling on it.
I threw the robe on and stepped out of the bathroom. The girls showed me
how to remove the makeup and especially when they pulled off my eyelashes.
They explained that I could use my own eyelash but they were kind of short
or I could go from them to these simple ones in the normal daily girl range
or if I wanted to really vamp it up longer ones. So, I was back to being
Tim and strangely they kind of treated me that way. It was like Heather was
their girlfriend and Tim was like just some guy hanging around their house.
They did ask how I liked it and I just mumbled "So far so good." But in my
brain, I was like I can do this with practice. They said they see me
tomorrow around 4pm so we can get you ready to go out with us. I just said
"Ok I'll be here" and with that I was out to walk back to my house.
It was like a 5-minute walk but it seemed like forever. I had so many
thoughts going through my mind. I now knew I could look like a girl and a
rather good looking one at that. I wondered how long it would take to get
these simple girl moves down. I also thought about how is Dan going to deal
with this. I think he thinks I'll just be a clown and that will be that. I
kind of feel like I'm going to show him for busting on me about all this.
In that moment I decided I'm going to be such a perfect girl that he falls
for me without even knowing it.
The next morning, I was tired and didn't go for a run with Dan. I was up
when he returned and so he gave me the works. "How'd it go with all the
girly stuff..." he said laughing. "I guess being a girl wore you out or
should I say whore you out." He went on with these overtly male jokes for a
bit. I just said "It went well." In my head I was laughing to myself that
I'm so going to follow through on making him fall for me without his even
knowing. He asked what I was up too today. I just said heading to the
library and then over to the girls. I didn't mention heading out to dinner
or anything like that. He said "Well I'll be here watching college football
unless that's too manly for you." I just smiled and headed out.
At the library I looked for books on how to speak like women. I felt like I
had seen a book like that one time while doing research for a
communications report. After a while I finally found it and not to be
suspicious I checked out a few more communication type books. Just so I
could pass it off as research. It's funny looking back how I thought
everyone would notice that book and yet really no one even cared. I raced
home, I went past the TV and Dan watching college football and headed
upstairs. "Not watching the game?" Dan said. "Nah, I have to do some
studying." Little did he know on what. This would be the first time of many
that I read that book each time getting a little better and learning
something new. After barely practicing for a few hours it was time to head
to the girls. I could do the girl voice a little but mainly on scripted
lines and even then, not so greatly. I was walking out the door when Dan
asked where I was headed. "I'm going over the girls again tonight." "Oh,
more girly stuff I see or are you just trying to score with Dawn?" he said.
I just laughed and thought I'm scoring you and you won't even know it and
out I went.
Once over the girls it was fast paced since we were going out to eat.
"Don't worry we made plans for 7 so we have some time." With that I was
handed the box, the glue, the gaffe and a matching pair of bra and panties.
They basically point me to their downstairs bathroom and said get started.
First, I put on the gaffe and pulled back Mr. Willy. Then I put on the
panties which were pretty much a thong. I was beginning to love how it felt
to be tucked tightly. I would always get random hard-ons as a guy and hated
them. Now it would be important to be hidden away in case I did get a
random one. I glued on the boobs as I had seen yesterday and put on the bra
as shown. Took a second to admire myself and stepped back out. The girls
were in various stages of dress as they had to get ready and get me ready.
I could already tell it was going to be a more formal night. They worked on
my face explaining more and more about how to do it. I knew at some point
it was going to be left to me so I listened intently. I was then given what
looked to be pantyhose but it was so small. I was told it was a wig cap and
would keep my natural hair down so that the wig would look better. "It'll
be more important as your hair grows longer." said Kim. It took them a bit
to style it again explaining it to me the entire way. I looked like a girl
full out now and it secretly was feeling great. They put the waist cincher
back on telling me it would only be a few weeks. I hoped so because it
wasn't the easiest to breath with. I was then given black pantyhose and
watch as Dawn did hers and followed along. They went all the way up to my
bra basically. Dawn explained how that was to hide the lines. I was just
learning all this hide the lines under clothes game that women have. Once
done I was given the LBD again and slipped it on again. It kind of just
felt natural but I knew the tough part was coming, Heels! I knew that was
how it was going to be tonight. I was scared especially about walking
outside. Dawn just said "I know you're nervous especially in the heels. But
just go slowly, women aren't in a rush. We'll take care of you tonight
don't worry." They asked if I could talk like a girl. I explained about the
book and then said some of the practiced sentences. They were amazed. "You
sound just like one of us." I just went on to say "yeah only on specific
sentences." But even say that sounded like a woman. "Just practice Heather
and the more you talk the easier it'll be. If something sounds awkward or
manly just say something else quickly." We were finally all ready and
headed out.
It was on now and I felt it. It's one thing to be inside and with people
you know telling you, that you look great but now I was out in the wild and
nervous as could be. A first I just focused on walking and where my heels
would land even as the girls' chit chatted a way. I was a nervous wreck. We
headed down to the market which I had been too many times but never like
this. We were a few minutes early to the restaurant so Dawn went in a
checked us in while Kim and I stood outside. Never have I felt so exposed.
Kim talked to me and just reassured me it would be ok and that no one could
tell. Just then a group of guys from some of my classes were walking
towards us. I felt for sure they will notice me. Kim noticed and just said
"Smile." So, I did and I could see Tom from my class look right at me. I
knew for sure he'd be like Tim? I sat right next to him every class. But he
just smiled back and said "Good evening Ladies." I was shocked he didn't
even notice me as Tim at all. Kim just smiled and said "Great job Heather.
See it's going to fun and no one knows. Heck I can't even really and I
know. Just be one of us." Just then Dawn popped out and we walked to our
table. It's weird because walking I felt starred at but in a different kind
of way. Dawn whispered "they're checking you out as a woman not as a... you
know." It felt good to be starred at that way but it was going to take
getting used too.
We sat down and talked away. I then realized I had no ID. I whispered to
Dawn "I have no ID." "Oh" she said "yeah we took care of that." She handed
me a Georgia license with Heather Thompson on it and my picture. "But hey
no beer you're a woman right." We all ordered wine and I did so in my best
female voice. I also ordered a salad and a light meal. "Oh, she's getting
into it." exclaimed Kim. We talked while we waited and it was mostly about
guys but also a bit of reassurance if I was ok. I actually felt really good
and hadn't ever felt like this as a guy. It was nice to have conversations
about everything and not just sports and boobs. Every once in a while, I
would think about a movement or how I said something but I tried to just
let it happen naturally. It felt so right like I almost didn't have to try
much. It became comfortable to sit in a booth and talk, drink wine and just
be a girl out at dinner. The check came and the girls were ready to go.
"Now for the real fun" said Dawn with a smile and giggle. I knew we were
headed to a club but I had no idea what that would bring.
We paid and left and walked a few blocks to the club they liked. We got
carded but no one said a thing and in we went. This was certainly different
than the calm of a restaurant. "Just let it go a bit tonight Heather. We'll
keep an eye on you." Kim basically yelled to me because it was so loud. We
all headed to the dance floor. I just tried to mimic what they were doing
and how they were dancing. It's hard to dance in heels but I was getting
used to it. The 3 of us were pretty much dancing altogether but that change
when a group of a bit older guys came up and started to dance with us. We
all kind of got paired off as it was 3 and 3. Now I was really nervous.
What if this guy knows or finds out what I really am. Before I could even
get all those thoughts out his hands were on my waist. I was like I've only
done the guy thing where do my arms go. I looked quickly to Kim who
basically waived her fingers from the other guys neck. I quickly followed
suit doing the same. But now I could feel my body pressing up against this
guy. I quickly lost the worry that he thought I was anything but a woman.
We danced for a while mostly the music got louder and we moved faster and
faster. It was kind of intoxicating but the wine calmed me I guess. I just
tried to do things that girls had done to me in the past. After a bit a
slower song came on and now this guy pulled me in tight. I was shocked.
Were the girls right would guys really want me. We grinded closer and
closer together. I was finding it easier to just follow along instead of
leading. I started to find this guy more and more attractive. I guess maybe
because no one ever really made me feel wanted when I was a guy but now
here as a woman somebody finally wanted me. So, I guess naturally I wanted
him back. After the song he leaned in for a kiss and I just let it happen.
I felt so different I could feel everything from his facial stubble to his
hands pulling me tight to my boobs on his chest. I was blanking out from
the passion of it all. Just then I felt it and thought oh my god I came
untucked and he's going to know. I pulled apart quickly looking panicked
which I guess Dawn saw and she pulled me off towards the ladies' room. In
we went quickly. She pulled me into a stall together. I found out later
that women sometime do this. Smiling from ear to ear she said "so how did
it feel?" I said something along the lines of wonderful but I came untucked
and we were pressed so tight that he has to know I'm a guy now. "Hold on
Heather let's check this out." With that she whipped my dress nearly to my
face and then ran her hand flat from my stomach down through my crotch. "I
feel nothing" she said "it's all still tucked." "How? What?" I said.
"Heather um, you felt him." Just then I realized I had turned this guy on.
"See told you guys would want you. How's it feel to be wanted." We got
fixed up and went back out and danced a little longer. It felt so good to
dance especially with a guy. It was getting late and we all kind of wanted
to leave. I said "Bye" to the guy and he asked if we could meet up tomorrow
dinner as he was just in town for business till then. Knowing a one on one
date was a bad move at this point I quietly said "I have plans but maybe
next time." Out of the club we went and back to their house we went.
It was like nonstop talk on the way between the 3 of us. Mostly about how
it felt to be me and making a guy hard and did I want him. I went on and on
about the kissing and dancing just gushing about it. That and how I never
felt wanted like this before and how much I loved it. There were questions
about was I turned on too. I just said thing like I'm not sure and maybe
just into it all but not sure I was turned on. I did know that I was going
to be hard pressed to find something like this as a guy and I let them know
that. In my 2 days as a girl I felt better about myself and much more
desirable than I ever did as a guy. I still can't believe I let a guy kiss
me tonight and I said that many times. Dawn explained to Kim about the hard
on I had that wasn't mine and we all had a laugh. We finally got back to
the house.
Now it was time to get undressed and while the girls were looking forward
to it and being out of heels, bras, etc. But, I felt depressed and I'm not
sure but all of it got to me at once and I just cried. They asked why I was
so sad after such a great night. I went on to explain that they get to stay
girls and now I had to change back despite loving it so much. I had never
felt this much happiness and it was going to be erased in a few minutes.
Kim just said "you'll just have to be a girl more often. You can be a girl
whenever you're not in class and you have Fridays off right. So that
Thursday night through Sunday. Come over around 1 tomorrow and we'll go
shopping." I was happy to hear all that. It was time to start undressing
though because it was really late. I took the robe and stuff and headed to
the bathroom remembering to keep the wig on till the end. I spent some time
looking at myself in the mirror and could see how a guy would want me.
After a bit I took off the heels and dress. Stood there admiring my body
then peeled off the pantyhose and bra. Then let out the waist cincher and I
could breathe. I used the solvent to remove my boobs which felt great to
have off after a long night. I then peeled off the thong and gaffe together
and felt free and thought back to how I thought I was hard. My hand on my
penis stretching it back to normal was soaked. At first, I thought it was
just sweat but quickly realized that some of my juices leaked out to which
meant I was turned on a least a bit at some point. I pulled the robe on
headed back out of the bathroom and took all the makeup off as I was shown.
The last thing was to pull off my hair and place it on the Styrofoam head
and then pull off the wig cap. My hair was soaked which made sense given
all the dancing. There I was back to just Tim in a robe. The girls had
watched but kind of let me be. I think they knew that lots was going
through my head and it was. From eating out to being a girl to dancing with
a guy it was a lot to take in. I just grab my guy clothes changed quickly
and headed out saying see you tomorrow. I walked home quickly and quietly
and it felt weird to be moving fast and as a guy. Was Heather just me
playing a girl or was it going to be more? That kept spinning through my
head. I fell asleep quickly as I was so tired and confused.
Again, I slept through running with Dan and again he let me know about it.
More talk about being girly and on and on. When I turned him down to watch
the afternoon NFL games he really poured it on telling me I've abandoned
him and guys. He knew I was going over the girls again so he played on that
to bust more jokes on me. But he did ask if I looked good to which I
responded "I'm out of your league." "Yeah right I'm sure you just looked
like you in a wig." I grabbed my stuff said "Out of your league" with a
wink and left closing the door behind me with a thud. I walked over to the
girls almost giddy of what I was going to do to Dan. I now had a plan. I
was also looking forward to the adventures today would bring.
I got there and didn't even wait for them I just began the process of
getting ready. I was done quickly with my body and began doing make myself.
They had me tone it down since it was just going out to lunch and shopping
and not a night out. I was learning more about makeup and the do's and
don'ts. They had me dress in a skirt and a nice top. Flats were a nice
change from heels and were comfortable and much easier to walking. Off we
went with Dawn driving us to the mall. I was completely in girl mode now
and it felt way more natural minute by minute. I told them about Dan and
all the jokes and sarcastic talk and grief from him. Both agreed that my
statement of out of your league might just be right but it was nice either
way. They both agreed I was a 9 or 10 and once I learned female tactics
that I could be choosier on who I wanted. They agreed that they guy last
night was excited because I was probably a stretch for him. I then
explained my plan to come out to Dan. They both said let's wait a few weeks
until you have many things practiced then we can lay the trap.
The rest of the day we shopped and I like doubled the amount of clothes I
had. I spent another $1000 which I did eventually have my Dad call me about
but I just said I need clothes and off he went. Again, he mostly just
wanted to appease me and keep me out of the way. I've often wondered what
he thought of the Victoria Secret charge. Probably just figured I have a
girlfriend. I was loaded up with clothes much more panties bras, shoes you
name it. We did stop and return the blonde wig and the saleswoman convinced
me I should get another wig or two in case anything happened to one. The
girls went to another store and told me they pick me back up in a bit. The
saleswoman and I picked out about 5 wigs to try on. I asked if there was a
back area to try them on. "Of course," she said. We went to the back with
her to try on different wigs. "Ok take what you have on now off" she said.
I was a bit nervous and it showed but I took off the wig and was there in
my wig cap. "Oh my" she said "I would have never guessed that you're a boy.
You are beautiful even without the wig. It's our secret anytime you come in
to the back we'll go. I fix wigs too so don't be afraid to come in
whenever." That made me feel good and we tried on all the different ones. I
really like one that was also long but was black with a touch of dark red
so I went with that. I had plans for Dan and that one. Hahaha my evil
plans. The other I went with basically the same as now just in case. She
went on to explain how to clean them and maybe rotate especially after a
smoky night out. She explained how it's the worst to smell the smoke in
your wig on a Sunday after being out the night before. I also bought a
couple more wig caps because even now mine was still a little damp from
last night dancing. I also got Styrofoam heads at her request. She claimed
wigs were best stored that way. I was done and walked out and the girls
were ready to go. We stopped at my house knowing that Dan would be at the
bars watching the games. I snuck up my back entrance and dropped off all
the purchases. I would have to keep them all out of sight.
I spent the rest of Sunday just practicing with them and talking more and
more because that was my main issue at this point. I was feeling pretty
comfortable with being a girl at this point and to be honest Heather was
who the girls knew now and not Tim. Even though they knew it was the same
person. As Heather they treated as one of them where as soon as I was
changed back to Tim they treated my nice but stand offish. The night ended
early and I was back to Tim heading home only this time a week of classes
stood between me and being Heather again.
I got up this time and ran with Dan. I need to keep up my running to stay
in shape if not lose some weight. Dan was pretty quiet and doing his own
thing. I was day dreaming of being Heather and more so of practicing makeup
and voice skills at night. Dan opened with "you think you'll be out of my
league. You must look pretty good then." "I can hold my own. I think you'll
be surprised." We talked for a while and caught up. He explained what
happened in every game that weekend. I listened to that but mostly for the
Ravens which was our new local team. I asked him if could get privacy
upstairs to practice being a girl because I needed to practice more than
just on weekends. So, I told him I'd lock the joining door at the top of
the stairs and mainly use the back entrance unless I was using the kitchen
or living room. "You're really getting into this Tim." he said. "If I'm
going to spend a week or more on Spring Break with you I need to learn lots
and be good at it. You don't really want your parents and friends at home
to think you brought back a guy dressed as a girl, right?" "Well hopefully
you're out of my league as you say." he said basically giggling yeah right.
"But look I'm not take you unless you're good enough that I'd want to date
you. I could always find another date." I just smirked and we went on with
our day.
I saw Tom that day in school and we chatted about our class work and the
presentations that we're coming up. It's so funny that he has no idea he
looked dead at me and smiled on Saturday night. I was Tim now and Tim was
Tim and not a sexy girl named Heather. I felt like my brain was working
over time today. I kind of felt like I didn't know how I was going to keep
it up. Here I am in class checking out girls for what they're wearing and
what might look good on me. All the while asking myself what guy would I
like to hit on me. Apparently, I like the baseball players because they got
me going. It's weird to get hard without a gaffe to keep everything in
place. I have to remember that sitting in classes.
The week went by and every night I'd do my makeup and hair and sit and talk
as Heather over and over. I'd walk in the heels or stand and sit over and
over and over. I was the all-in type of person and so I was throwing
everything at this. I say that like I hate it but that's so far from the
truth. I love this and it's like I found a new. Boring scrawny Tim is
fading and Heather is here. Not to mention most night I would just think
back to Saturday night and dancing and kissing. My worry now is that at
some point I'm going to be Heather all the time and what does that mean.
Eventually things will move past kissing and dancing to more intimacy. I
figure take it as it comes but be careful. Other than Dan I'm not revealing
the Heather is a boy dressed up to anyone.
The weekend is finally here and I'm excited to be full on Heather again.
Even Dan knows to a degree. "I guess we'll run again Monday because you'll
be with the girls all weekend." he said. I told him I do the Ravens game
Sunday with him. His response was "As a guy or as a girl." I laughed "As a
guy. You're not ready for me a girl." "Sure whatever Tim." I spent the
early part of the weekend at the girls. I was Heather pretty much the whole
time. I fit right in and felt a part of the group. We went out again
Saturday night and I was looking hot. I wore a blue dress and it fit like a
glove. After the week practicing and now going our I was very used to being
in heels. We went out to eat and have wine. More girl-talk about the week
and which guys you found attractive. I told them about my baseball crushes
and they knew some and totally agreed. We went clubbing again this time it
wasn't as intimate a place and basically everyone danced together albeit
there were times when guys would grab me tighter. I loved grinding on one
guy's crotch. I knew it was making him harder and harder and it just made
me giggle inside. I left the girls house after changing back to Tim and
telling them tomorrow I'm watching the games with Dan. They were bummed but
understood I needed to hang with him too.
We went out that Sunday and enjoyed the games and a few beers. I got to be
honest after sipping wine beer just tastes blah. Not really into that much
anymore. I found myself starring at Dan and other guys a bit but not as
much as class. Dan caught me once and said "are you checking me out?" I
smile and said "Nope I'm still out of your league." I was a nice day out.
About half time of the 2nd games Kim and Dawn walked into the bar. "Hey
ladies" Dan said. They sat down with us for a few minutes. Dan asked them
questions along the lines of so is Tim a dork still as a girl. He keeps
telling me he I'm out of his league. I felt awkward with this talk because
I was on both sides of the fence of him and her in this conversation. Dawn
just said "He is in your league. She is way above your league." The girls
and I just looked at each other like yup. They left after a few minutes and
we watched the rest of the game with the Ravens blowing it late.
Dawn called me Monday night and told me to be ready for a trip come Friday.
They were heading to the University of Georgia for a football game but Kim
has to stay here for a class project and so I could use her ticket. Dawn
said we would stay at her parents. She asked if I wanted her to tell them
about me or just roll with it. I said just roll with it and if they find
out they find out. I spent the rest of the week practicing even more and I
was pretty confident now in my abilities as Heather. I packed everything
including an extra wig into my suitcase. I told Dan I was going away for
the weekend to Georgia with Dawn. He was bummed but understood. I met Dawn
over her house early Friday and changed quickly into Heather. I knew that I
was going to be Heather from now until late Sunday and that excited me. It
was a few hours' drive and we stopped for dinner and gas on the way. I was
wearing jeans and a t-shirt but it's funny how with boobs, makeup and long
hair and now a voice to boot that no one evens questions your sex they just
see you as you are. We got in late and I met her parents and brother.
Albeit I think I met her brothers tongue because he was all but drooling
looking at me. He is a High School senior so I guess I understood. Her Mom
was the southern host you'd expect and had everything out and beds made for
us. Her Dad said hi without really looking at me. It was an awkward hi I'm
not checking you out hi. I had my own room which was their guest room. That
was great because I could look the door and change and get ready in there.
It also had a large mirror which was needed. We kind of crashed quickly
knowing that tomorrow was a long day.
I got up early and dressed. Everything was in place as far as tucking and
boobs and hair and makeup. I pulled on a tight black skirt and some
pantyhose because it was going to be a cool day. I went with a white long
sleeve shirt and Dawn had given me a red Georgia Dawgs shirt to wear over
top. It was tight and my boobs looked huge in it. Her parents drove us over
to campus early and I guess got their normal tailgating spot. They knew
everyone and I was introduced to so many people I don't even remember any
of them. I got used to shaking hands and being hugged as a girl though.
It's interesting even though they're fake just how much you feel your boobs
when they're squished. We ate a bit drank some wine and threw the football
around. I could probably throw it better but I did the girl thing and
basically threw it like a shotput. Dawn and I talked to many, many guys
before the game. Each pretty much had a plan to have us at their parties.
But seemed Dawn had a place downtown on her mind for afterward especially
it they won.
The game was fun and it's interesting to play dumb and pretend like you
know nothing about football. The guys next to me explained it all even
though I probably knew way more than them. I just smiled and say things
like was that a first down or what does fumble mean again. On touchdowns by
Georgia I was basically groped by half the men near me including Dawn's
brother. I wasn't worried about it but you have wonder if it's excitement
about scoring or excitement about trying to score a feel. The game went on
and eventually Georgia won by an FG. Everyone was pretty happy and ready to
party.
We went out to the place Dawn wanted to go that night. I can see why
because it was more laid back than a club. You could dance and there would
be slow dances mixed in. We sat at the bar and had a drink and then some
other college guys bought us a round. That turned into talking about where
you from and where you go to school. The basic stuff I guess. After a bit
one guy named John asked me to dance. I just nodded yes and off we went.
Dawn and the other guy followed shortly after. I don't think I'll every go
back to dancing as a guy being a girl doing this is so much better. As a
girl you can pretty much move and dance however you want. I danced close at
points being grabbed by him and other times I just danced around with Dawn
together. I don't think I stopped smiling the entire time. It's a great
feeling to be wanted even if in my case you can't put out per say. We
danced for hours and eventually late in the evening some slow songs came
on. John pulled me close and I basically put my head on his shoulder and
let him kiss my neck. I felt so very turned on by that. I could feel myself
pulse but I knew I was still tucked tight. It was different kind of turn on
one that I never felt as a guy. My whole body was electrified not just my
penis. We went outside in the patio area and basically kissed for what
seemed like hours. If I had a vagina we'd have made our way home by this
point. But I had to be careful even drunk and in love. Dawn eventually
swung by and we all left together. Dawn claimed her Mom would be upset if
we didn't get home soon and she was probably right. So, we gave the guys
our numbers and of we went in a cab to her home. We spent a bit chatting in
her room about kissing and I told her how I felt turned on differently. It
was late so we turned in for the night. I decided to sleep without my wig
since it was so sweaty, smoky and hot. I figured the next morning I would
just use the other one.
The next morning, I was shocked to be woken up by Dawn's mom for breakfast.
I guess she figured we were all girls so she could come in and wake me. She
was baffled to where my hair was and why it was so short. Dawn came in
closed the door and explained everything to her. Her mom couldn't even
believe it. She said "I would have never in a million years even thought
you were" now whispering "a boy." "Not to mention you have our son and my
husband drooling over you. I'm just amazed?!?" Dawn assured her I was
pretty much a girl with boy parts well hidden. "She danced with and kissed
men last night mom. She's pretty much one of us at this point." "Well don't
tell your Dad or Brother because who knows and we all really want to have
Heather back up here. Heather do you have a place for Thanksgiving?" her
mom said. "No, my parents live in Maryland but they're head on vacation for
that week." "Well that settles it you're coming here for Thanksgiving. You
have the guest room all to yourself and I won't come in again promise. Now
girls get ready we're going to lunch before ya'll head back to Charleston."
I breathed a sigh of relief and never put my wig on faster. Dawn was like
guess you got to watch sleeping as a boy. We headed out to eat and then
left heading back to Charleston.
The weeks rolled by with me being Heather on most days each weekend. I
enjoyed all of it. From the girl talk to the dressing up and looking good
to be hit on and kissing guys. I was basically only Tim when I had to be in
class. I still ran in the mornings during the week with Dan but we usually
kept to ourselves in the house. Occasionally, he'd have other guys over to
watch the games. Here and there a girl would show up for a date. I usually
stuck to myself and practice. Dan would still chide me about him being out
of my league. I told him "I'm better looking than any of these tramps
you've had over the last few weeks." Dan's response "was ha doubtful."
Well I was final ready for my plan to be hatched on Dan. The girls agreed
that I was pretty much fully able to handle being girl when dressed at this
point. His birthday was coming up in a couple of weeks so my plan was to be
his date for it without him knowing. It was the weekend before his
birthday. I had the girls arrange a club to hang out with him at.
Meanwhile, I told him I would be out of town tonight visiting some friends
a few towns over. He left early to go meet Dawn and Kim. I bolted in to
action as soon as he left. I quickly transformed into Heather. I wore a
tight black dress with a skinny red belt. I did my makeup perfectly and I
put on that black with dark red highlights wig. I stepped into heels and
was ready to go get Dan and show him. I walked into the club and looked for
Dan. I spotted him and casually walked by flashing him a smile. Dawn and
Kim ignored me fully which was the plan. I couldn't be seen with them at
all or the plan might be ruined. I stood at the end of the bar pretending
to be looking for my date. I kept checking my watching. I walked back to
the bathroom passing right by Dan and smiling at him again. Really playing
it up like I noticed you. I spent a bit in the bathroom and then strutted
my ass right in front of Dan on my way to the other side of the bar. I
huffed and played with my watch again hoping that Dan would pick up on it.
Then I sat down all frustrated looking. I could tell Dan was looking at me
so I slowly looked up and shot yet another smile. Wow is he really this
dumb I thought. Sending me a f'ing drink I basically throwing myself at
you. Finally, after a few more watch looks and a few more playful smiles
and a few taps by Kim of hey that girl is checking you out, he sends a
drink. About time is going through my brain. I wave him over. Dan comes
over and I see he has no idea it's me like zero idea all he sees is a hot
chick. I tell him my name is Heather and a sad sap story of how I guess I
was stood up by this other guy. We chat for a while about nonsense really.
Most of which I made up. He asks if I want to dance. I laugh inside
thinking if you only knew but say sure and let him lead me. We danced the
rest of the night and it was actually quite nice. He is so tall that even
in heels I felt short. Lately I've been taking my heels off and holding
them to dance but I don't want Dan to realize my height because he might
compare it to Tim. So, the extra 3-4" of height changes where I come to on
him. I don't want him to figure it out not this way anyway. I could see
Dawn and Kim smirk and wink from time to time. He grabbed me tight from
time to time and while it felt exciting it felt different from my other
encounters with men. I guess I know him so it made it less mysterious.
Plus, I feel like once he knows it's me the thing is over. The night is
winding down and he finally kisses me. I let go and try to pretend is any
other guy than my best friend whom I'm kissing. He holds me tight and I
press up against him basically forcing my crotch into his to see if he is
hard. He is pretty hard and I feel it basically at my belly button. I swoon
thinking how much I would love a dick in me and dick really but that can't
happen yet. I look up and flutter my eyes him. "I got too go" I say. I
wanted to make it back home before Kim and Dawn take him. I'm waiting for
the date offer, still waiting, flutter my puppy dog eyes again and pull in
close. Finally, he says "Do you want to go on a date?" I respond with how
about "Hopkins restaurant at 7pm tomorrow. Obviously, my date tonight isn't
making that reservation." He says "It's a plan then. Sounds great see you
then." I give him a peck on the cheek and then stroll out rolling my eyes
as I pass Dawn and Kim.
I get home way before them and I lock all the doors and decompress. It's
hard sometimes to go back to being a guy. At this point only, I get to see
me change to or from Heather and even the girls know that at this point.
It's just so personal and I kind of don't want to be seen halfway. Either
you get Tim or you get Heather you don't get some combination of the two. I
take my heels off which always feels so great after dancing and spending
the night in them. It's weird to plop down 3-4" though, it makes me feel so
short. Being short is nice as a woman and the heels let you place yourself
right against a guy. Without the heels Dan's dick would have been up near
my boobs and that seem much less sexy dancing. I take of the sexy dress
hanging in back up in the closet. I peruse for what I'll where tomorrow and
try it on. It's a perfect dark green dress that hugs all my curves just
right. It also shows off my cleavage just right. Not too much and not too
little and it hugs my boobs showing their every curve. I take it back off
and place it back in the closet. I don't have dark green heel so I'll just
go with the black ones from tonight. I take my pantyhose off peeling them
all the way down slowly to not get any runs. I rub me feet after that and
remind myself to repaint my toe nails. I take off the bra which felt tight
tonight and scratch where it left lines. Feels great to do that after a
night out. I debate keeping on the boobs but figure I'll get redressed from
scratch tomorrow. I take the solvent and then off they come. I still place
them in the box because it hides them away and keeps them clean. Again, I
scratch all over my chest and it feels great. I note that I need to shave
my body tomorrow. It's not bad but short stubble on your chest and legs
feels so unsexy. I pull down the undies and I'm left with the gaffe. Still
amazes me how hidden it all is and that I look female there. I pull down
the gaffe and it's sweaty but there's no pre-cum in there. I wasn't really
turned on by Dan so that's my guess of why it's not there. I grab the robe
and wrap myself in it. It's weird to look at my hairless male body with a
sexy face and hair. Lately I've been taking the wig off at this point and I
do that here. I pull up the lace front and take out the crisscrossed bobby
pins holding it to my wig cap and I pull all the way back and off it comes.
I shake it out a bit and place it on the Styrofoam head to dry out and
brush. Feels weird now without my locks. There's nothing to move and play
with. I sit and comb out all the knots and tangles. Might as well do that
now so that I have more time tomorrow. I take off the wig cap and its damp
but not soaked. It was a mild night. I've been debating whether to grow my
hair longer in hopes to get rid of wigs or shave it all so it's less hot
and easier to manage. It's a toss-up but for now I've sided with growing
it. I take off the fake lashes placing them in the case they came in. I
then rub cold cream everywhere removing all the makeup. Takes a bit of
rubbing and water but off it all comes of and I'm back to Tim. I'm finding
it now takes a bit of me talking to get my voice back. So, I sit there and
read some sentence as male Tim. I don't know where this is all going but I
think about the future. I have a date tomorrow with Dan, I'm going to a
Thanksgiving dinner, what happens over Christmas break, do I do Spring
Break with Dan, etc. I'm getting to the point where Tim feels like the
person I change into and not Heather. Every time I change back it's harder
and I miss being her more and more. I don't know how dating Dan will go but
we'll see starting tomorrow. I faded off with so much on my mind. It's
easier to just dance and be me as a woman.
The next day comes and I go out running with Dan. I ask him how it was with
Dawn and Kim. He talks all about this Heather girl who he met at the club.
He's going on and on about her and how they have a date tonight. "Sounds
like that all worked out Dan," I said. "Here I thought you'd come home as a
girl." I said throwing the joke back at him. "Nah, I picked myself up and
hot chick who got stood up. She's hot like a 10!" he said. "A 10 like you
could get a 10," I said. "She smiled and flirted with me. She wanted me it
was easy," he said. Meanwhile I'm thinking yeah, I basically threw myself
at you repeatedly for you to take any kind of bait. "Still think I'm out of
your league Tim." "Yup, I do." "Well I'll have to bring her over at some
point to show you." "Good luck with that." Dan just shakes his head. He
goes on to tell me he'll be heading out earlier tonight to meet up with
some guys around 3pm and then he's heading over to Hopkins for his date and
don't wait up for him to watch the games. "Don't worry I say I'll be out
late tonight with the girls," I said. "Oh, that again. Well if it goes well
with this girl I might be skipping you on Spring Break. Just be ready to go
elsewhere or with the girls," he said using air quotes on girls. I'm like I
should dump you flat out tonight but that isn't the plan.
Dan leaves around 2:30 or 3pm. I hear him leave and drive off. I've already
taken a shower and shaved and did my toe nails and now I'm doing my finger
nails all in dark green. I start getting ready as this too will be my first
date as a woman. I'm excited but I laugh at the thought of it being with
Dan. That and Dan is freaking clueless to the whole thing. I build my body
as always starting with tucking and gluing on boobs. This time I decide to
change it up and I throw on my robe and wig cap and the begin to do my
makeup. I go with longer lashes not crazy but a bit longer. I check my face
over and over making sure there is no signs of Tim there. I think just the
eyeliner changes my looks so much that it would be hard to tell who I am
add in red glossy lipstick and thinking I'm a boy goes right out of
people's minds. I brush out the wig some more then place it on my head
pinning it down tight as you never know what tonight might bring. I brush
it out some more and spray it in place until it's perfect. I take off my
robe and I'm still naked. I look like any naked girl would so if my dress
comes off this is what your seeing. I take out a black bra and black thong
and put them on. I pull-on jet-black pantyhose and pull them all the way up
to my bra line. Nothing makes me feel more of a woman than pantyhose. I
feel like that is my woman armor and once it's on I've become a woman
fully. It just feels right and seeing the vent in my crotch lines up so
visually with no penis there to ruin it. This time I also wore pantyhose
with seams on them. I take a few minutes to straighten them. I hope they
turn Dan on. I pull the dark green dress over my head and slide it down. It
fits perfectly and I zip the back up and I'm fully dressed. I spray some
channel perfume and step through it letting it hit me all over. I pick up a
silver necklace with a horseshoe and put it on. I place my feminine watch
on and now all that's left is to step into the heels and grab my purse. I'm
Heather Thompson from Georgia tonight and I'm going out on a date. I call a
cab and wait. It picks me up and I said Hopkins please and the cabby knows
right where that is. We have some small talk about the weather and if I'm
going on a date. I answer all the questions and they're a good warm up for
me to get into my Heather voice. I pay the cabby and step into the
restaurant and figure here goes nothing.
I see Dan waiting at the bar and I walkup and give him a peck on the cheek.
"Hey Heather," he says "you look beautiful." I smile and say "You look
handsome yourself." We walk to our table with him following me and probably
checking out my ass or legs every step. It's so much more fun to be the
girl than the guy. I love the girl role so much. You get to play sexy and
flirt and basically the guys follow and watch you. I would say it's easier
but not sure that's fully the case. It's hard getting dressed up and
becoming a beautiful woman. The simple part is the act here in front of
Dan. That's the fun part. But maybe right now I guess in the end I can't
put out now so that holds things back girl-wise for me but it's nice that I
get to take it at my speed and not his. I go straight into girl mode
ordering wine and the salad. I'm not getting steak or anything like that.
Dan orders a beer and steak though and I'm like it figures. I'm also
wondering if he's planning to pay or split this meal. I don't overly think
it though. While we wait I sip on the wine and we talk. I tell him I'm from
Georgia which I am based on my driver's license. We talk about school and
since I know him I've heard most of the stories before but I smile and
laugh at all them. I tell him I'm a communications major. I was tired of
making up stories. He asks if I know his friend Tim who is also a
communications major. I pretend to think on it then ask him to describe the
guy. Then I say "Oh yes I know him. He stays kind of quiet in the classes
I've had with him. So, I don't really know him well." Meanwhile I'm
thinking well I'm him so yeah, I kind of know him. We talk about all sorts
of things school, sports (which I played dumb on besides Georgia football),
his plans after college. He told me all about ROTC and how he was headed to
the Navy. I keep trying to convince myself to be up for all this. Really,
I'm sure if this was any other guy I'd be hanging on his every word. Dinner
was good and Dan paid the full bill. I threw in the tip which is the least
I could do as a girl. We looked like any other couple in the restaurant
except only I knew this couple wasn't exactly what it seemed. I wondered if
the were any other woman in here that were really men. It really got me day
dreaming. Dan snapped me out it saying "you ready to leave?" I asked for a
minute to hit the ladies' room. I went in did my business and re-tucked
making sure it was tight since I knew we'd go dance or what not. I redid my
lips after eating and off I went. He stood up and was ready to go.
Since Hopkins was on the market we took a stroll. I held his arm like I've
seen many a woman do especially in heels. The market and cracked concrete
are such a challenge in heels. Dan found a park bench and asked if I wanted
to sit. I said sure and I sat cross legged dangling my shoe and bouncing my
top leg up and down. He put his arm around me and I snuggled in close
resting my head on his shoulder. We talked some more about life, etc. I
still was like this would be so romantic if it wasn't Dan. I was getting
cold so I asked if he want to go inside and dance. Really, I was in the
mood to dance. We walked back up the market and went to a quieter place. It
was nice to mainly slow dance. I liked playing that part. I loved to have
my hips held and be pulled in. I ran my nails on the back of his head
playfully and we'd kiss here and there. I was so used to being the girl and
dancing in heels and being led and pushing myself in tight that I'm not
sure I would even know what to do as a guy much anymore. Maybe not for
everyone but for me the girl side was so much better. We danced for a few
hours before it got quite late. "I better get going," I said. I asked for a
taxi and we sat on a bench waiting and making out the entire time. He'd try
to get further and further up my leg. A while it was a turn on I could have
that happen. I ran my hand over his crotch and I could feel how hard and
big it was. I never would have thought that I would want a guy inside me
but here I am desiring that. But I need to figure out how sooner than
later. The cab came and I gave Dan another kiss and then slide into the
cab. I knew I would be home way before he got his car so that was my plan.
I paid and raced up the backstairs before he got back. I knew I had him
now.
I undressed and it was for the first time it was weird while I felt I
looked hot my feelings for Dan just weren't overly there. I wondered if
they'd ever be. I sure knew what it felt like to want and be wanted and I
loved that. But this wasn't that. I had to let him know before he got stuck
on me. I stayed in my room all Sunday I didn't really want to go out. Here
I was wanting to be a girl but not wanting to be one with Dan. So around
3pm I called Dan and asked him to meet me in the sports bar downtown around
5pm. He got dressed and flew out. I took my time and got dressed too I
figured I could be late if needed. I put on the same tight skirt I wore at
the Georgia game and a tight long sleeve gray top. I looked good. I headed
downtown and met Dan who was happy to see me. We hung out and watched the
games together. I pretend to know nothing again like I did at Georgia and
Dan explained everything to me. We sat close in a booth and his arm would
slide up my shirt or up my legs. I was a bit more turned on by all this but
wasn't sure where it was going or where I even wanted it to go. After the
game I just asked if we could go home I was sad inside because this was
going to be hard. I asked if he could drive me. He said sure. I didn't give
an address but more or less gave directions and we got closer and closer to
our house. He said, "hey I live down this street too." I said quietly,
"just up here on the right." "Hey we might be neighbors," he said. I said,
"Ok stop here." He looked at me. "I live upstairs," I said. "Tim???," he
said. "It's Heather but yeah." After a long pause I just said, "Do you want
to go in and talk about it?" He just nodded.
Never had I felt so vulnerable in my life as we walked upstairs. We sat
down on my bed and he just starred at me. Like he was looking through me or
for any flaw that would say Tim. "It was you the whole time," he said.
"Like even the kissing?" I was perplexed by the question like he knew it
was me. I just sat there and tried not to cry feeling so exposed. Every
other guy had no idea I was a boy and even if they did I they wouldn't know
me as a boy. But here with Dan he knew me as Tim and I think that's why I
couldn't fall for him. Dan asked, "So do you like being a girl? I mean
you're right you are hot and maybe out of my league." I just said, "I love
being a girl Dan. I didn't think I would but it fits me. It's becoming
weird to be a guy during class." "I'm amazed it's you in there. You look so
feminine and your voice." "Well the Ravens sucked today," I said in a
clearly Tim voice. "Wow, yeah that is freaky don't do that again," he said.
"Am I really out of your league do you still want to date?" he said
awkwardly. I just teared up and shook my head no and just said, "It's
really just too weird Dan. Don't get me wrong you did everything a girl
would want to have. But, I found it hard to be passionate and into it with
you. I think it's because you know me as um." "As Tim?" he said. "Yeah and
hearing that you know that is why it really just can't happen. I would
never be able to think that you weren't thinking that," I said. "Tim er
Heather, I still can't believe it's you. How do you do it?"
I thought ok maybe if he saw it was all an illusion that it would be easier
for the both of us. "Ok look I'm doing this once Dan," I said. "Doing
what?," he said. "Getting undressed and turn back to Tim in front of you. I
do it be myself now and even the girls don't see the transformations
anymore. It's very private but I do think it'll help us both hopefully kind
of end the chances of dating." "Wait," he said "before you do that let's
make a deal." "Ok sure?," I said puzzled. He went on to say "If we're both
single around Spring Break, you come down to Florida as my date to meet my
parents and friends. It would score my points with both." Thinking nothing
of it "I just say sure deal but if you out me or stop me from dating then
it's off." I stand up and say "Kiss me!" He waits shocked then gets up and
kiss me. I basically ram my tongue down his throat and press my boobs and
crotch up against him. I then grab his balls hard and state directly to him
"And god help you if you ever out me to anyone! I would make your life
miserable."
We break apart and I think here goes nothing. I step out of the heels and
plop down 3-4." "I never realized how short you are Tim. Is it hard to walk
in those?" Dan said. "Whoa buddy, when I'm dressed as Heather you call me
Heather. It really shouldn't be that hard I don't think," I said. "Second,
yeah it's tiring to walk in heels. Not hard though and judging by how you
checked me out walking in them it's worth it." I take my necklace and watch
off and ask him to unzip me. As he does I peel of the straps of the dress
and let it fall to my ankles. I'm just there in bra and pantyhose. "My god
how the heck? How do you have tits? And no... you're hot even undressed"
Dan said. "Um, I prefer boobs," I said "Tits sound so slutty and hold your
horses mister." I pull down the pantyhose wiggling my ass at him to give
him a good look. I ask him to unhook my bra which he does and I cup my
boobs. I spin around letting my boobs fall and I jump and press up against
him again and throw my tongue into his mouth as he grabs my ass holding me
up kind of as I wrap my legs around him. After a bit I pushed myself away
and back to the floor and said "yup still feeling nothing with you. Sorry.
I know you want to grab a boob so go ahead. He does and I pretend to
wriggle in delight while over doing the girl actions. I lead him over to
where I have their box and solvent. I step away and spray the solvent all
over and said "go ahead peel one off." He does and is looking at it shaking
it and touching the nipple and the while I pretend like it's still attached
to me and giggle and laugh and say no. I pull the other one off and ask for
my boob back and place them in the box and close it. "Still want a flat
chested girl like me?" I said. "Look this next part is personal and really
I'm only doing it once." I grab the robe and throw it on. I open in up and
pull down the thong exposing the nude gaffe. Dan asks "What is that?" "It
keeps my privates hidden away and gives me the look of a girl," I said. I
quickly pull it down and pull out my penis stretching it out. I quickly
close my robe and tie it. "One time only show. Don't ask me again. Someday
it'll be gone," I said. "Look at some point here I'm going to change my
voice because I'll be more boy than girl." I sit down on my makeup chair
and I peel off my eyelashes just to have them out of the way. "Ok this will
usually end it," I say and with that I unpinned and peel back the wig and
just laid in on the table. I'll deal with it later. I don't even stop and I
take off the wig cap and then rub cold cream all over my face wiping off
the makeup. Once it's gone I run my hands through my hair and say to Dan in
my Tim voice "you want me now big boy." Dan just looked shocked and said
"yeah I can see why it would be awkward for us to work out. I now know
what's under everything. I would date Heather but agree it's weird that
it's you too." We talk a bit more then he heads downstairs. "I'll see you
tomorrow for our run," he said. "Sure," I said "and added I'll be dreaming
of you." "Yuck" was his response.
Part One to be continued!