Date: Wed, 5 May 2004 20:57:18 -0700 (PDT)
From: Dan R <vtcarfanatic@yahoo.com>
Subject: My first time crossdressing: the college years

The College Years

	After my week of dressing, my mother noticed that things were not
quite as she had left them, and became suspicious.  She asked me if I had
been in her things that I of course denied, but I think she knew what I had
been doing.  Because of this I quickly put a stop to my dressing, but
continued reading stories of other crossdresers, looking at pictures, and
of course masturbating to them.

	Many years later I graduated from high school and moved on to
college.  In college I was lucky enough to get a single dorm room, and
immediately saw the opportunity for a previously unknown privacy.  After a
few months of getting used to the college lifestyle and classes, I decided
it was time to renew my interest in dressing, and the next weekend I jumped
in the car and headed to the store.

	Deciding that Wal-mart was the best store for me at the time, I
went inside and headed for the lingerie department.  I didn't want to
arouse any suspicion, so I quickly bought a black garter belt, a pair of
black thigh-high stockings, and a powder blue thong.  I told the checkout
woman they were for my girlfriend and asked if they were returnable if she
didn't like them, and then headed two towns over to the next closest
Wal-mart.  There I bought a pair of purple bikini-cut panties, a purple
thong and 3 pairs of nude stockings.  Knowing I would never be back to this
store I hurried through the checkout lane and drove back to the dorms.

	For the rest of my freshman year, when the urge hit me I would slip
on the panties, garter belt and hose and masturbate, but when the semester
ended I hid these fanciful items at the bottom of a box and went back home
for the summer.

	Heading back for my sophomore year, I met a girl named Jill.  She
had fiery red hair and we quickly became great friends.  She had an off
campus apartment all to herself, and quite a few nights I fell asleep on
her couch, we became close very quickly.  She was 6' 2" tall so we saw eye
to eye, but wasn't skinny in the traditional sense, in fact the two of us
shared basically the same body except for the fact that she had large DD
breasts.  We talked about everything from sex to movies to classes, but I
was reluctant to share the secret of my crossdressing with her for fear of
alienating her.

	After several months though, she was looking for laundry detergent
in my closet (she spent a lot of time in my room so I thought nothing of
it) she ran across my panty stash.  I didn't know about it at the time and
she didn't say anything, and for several days I heard nothing about it.

	About a week later we were chatting AIM about things and we got on
the subject of fetishes somehow, and she asked if I had a panty fetish.  At
first I denied it but when she explained that she had found my stash and
wasn't upset or anything just curious and wouldn't think any different of
me, and after some prodding from her I let it slip that I enjoy wearing
them.  To my surprise she said she thought it was interesting and wanted to
know more.

	After a long talk that went far into the night, I had told her all
about my week alone, my Internet activities, and my desire to dress more.
Towards the end of the conversation, she asked me if I would ever consider
dressing with someone, and I told her if it was someone I trusted, which
she replied to asking if I would like to come over to her apartment and
dress, and she would help.  At first I was reluctant but she finally talked
me into it, and we decided on Friday as the day.

	Thursday night I didn't sleep much at all, and Friday I sat through
my morning classes in anticipation.  My penis was already mostly hard, and
concentrating on the boring material was tough.  Finally my classes were
done and I jumped in my car and raced to her apartment.  After the short
drive, I arrived at her apartment around 12, and knocked on the door.

	She opened the door in a short black skirt, white tank top, and
platform sandals that made her slightly taller than me.  Her red hair was
pulled back and she smiled at me as she stepped aside and invited me in.  I
followed her up the stairs to her apartment (she lived on the top floor of
a house that was divided into several apartments), and after a few moments
of awkward silence she asked if I wanted to get started.  Not knowing what
else to say, I said sure and she handed me a bottle of Nair (at this point
in my life I had a fair amount of body hair).  She told me to apply it to
everything from my neck down and pointed me towards the bathroom.

	In the bathroom, I stripped off my clothes and quickly applied the
bottle to my body.  Through the door I asked her what to do next, and she
told me to wait 5 minutes than get in the shower, which I did.  While I was
in the shower rinsing off the foam and watching my hair run down the drain,
I heard the door open and close again, and I heard Jill on the other side
of the curtain.  She scooped up my clothing, then told me to towel off,
wrap the towel around myself and come on to her bedroom.  Climbing out of
the shower, I wrapped a towel around my chest and walked to the bedroom.

	She sat me down in front of her Vanity mirror, and told me to close
my eyes.  She immediately started plucking my eyebrows to give them a more
feminine shape, and then I felt her tug a wig down over my hair.  After
ensuring my eyes were still closed, she went to work on my face and I could
feel her applying concealer, mascara, eyeliner, and lipstick.  Finally she
announced that she was done and I opened my eyes.  In the mirror was a
young blonde woman that could easily have been mistaken for Jill's sister,
and I beamed as I saw myself.  She giggled as she saw my reaction and told
me to get dressed.

	As she left the room and closed the door behind her, I turned in
the chair to see the clothes she picked for me on the bed.  We were almost
exactly the same size so I wasn't worried about anything not fitting.

	Dropping the towel, I picked the blue Victoria's Secret thong and
slipped my smooth legs through the holes.  I settled the back comfortably
between my cheeks and realized that the thin material would do nothing if I
became any harder than I already was, but I did my best to make my
semi-hard member smooth behind the front.  I picked up the matching lacy
bra and clipped it around my check, then spun it around and pulled my arms
through the straps.  I noticed for the first time the two water balloons on
the bed, and I placed them in the cups giving myself DD breasts.  I cupped
my hands around them and bounced them, feeling the weight and smiling at my
new breasts.

	Next I grabbed the jean skirt that was laying on the bed, and
slipped it up my legs.  As I zipped the back, I realized how short it
actually was; it ended just about my mid-thigh and I could see it would
take constant attention to ensure my panties wouldn't be visible if I bent
over or sat down.  A white top, sleeveless and low cut in the front,
followed the skirt and I quickly buttoned it.

	Finally on the floor was a pair of stiletto heels.  They were black
with thin ankle straps and a 3-inch heel, and I picked them up and sat on
the bed.  I felt the skirt ride up and felt the comforter on my smooth
upper thigh.

	Slipping my feet into the shoes, I wrapped the ankle strap around
and buckled it.  The shoes were a little tight but still fit, and as I
stood I felt my thighs stretch and tighten, and I teetered on the heels
before I regained my balance.  I took several laps of the room to get used
to walking in the heels, and then opened the door and walked out into the
living room.

	Jill whistled from the couch where she was sitting as I walked into
the room.  I strutted to the middle of the room and spun around.  I felt
the skirt lift as I twirled and knew that she was getting a good look at my
thong and I felt my cock grow at the thought.

"Come here" she said after I had finished twirling, and I strutted myself
towards the couch.  Stopping just in front of her, I stood there with my
legs spread shoulder width apart, I was surprised when she leaned forward
and ran her fingers up my smooth thighs.

	My cock instantly sprang to attention as he fingers ran up and down
my thighs, and as her hands slipped under the hem of my skirt my lips
parted and I let out a low moan.  She smiled at and ran her hands up
farther, then slid them back down.  I bit my lip and looked down at her,
and she grinned back with a sly look in her eye.

"You look incredibly sexy right now, you know that?" she asked me.

"I feel incredibly sexy too" was the only reply I could muster.

	She stood and pressed her lips into mine.  At first I was surprised
but quickly closed my eyes and reciprocated the kiss, our tongues
intertwining with each other.  I could taste our lipsticks and that turned
me on even more.  My hands wrapped around her back and caressed her hair,
while hers moved down my back.

	After what seemed like an eternity kissing, she broke it by turning
me towards the couch and pushing me backwards.  I teetered on my heels for
a brief moment then fell backwards onto the couch.  Jill dropped to her
knees in between my legs and leaned forward to kiss me again.  As we
continued to kiss, I felt her hands running up my thighs, pushing my skirt
higher and higher, till I felt cool air in my hairless crotch.  I knew my
thong was doing almost nothing to hold my hard cock in place, and the
thought of what it must look like made it twitch.  I felt her hand tug at
the thong, and it slipped to the side as my cock sprung into the air.

	I felt her smile as we kissed and she pulled back and looked down.

"Mmmm, I like what I see here." She murmured before she pushed my legs
further apart with hands and dropped her mouth towards my crotch.

	I could feel her warm breath on my skin as she began to lick and
kiss my shaft and head.  She worked her way down till she kissed my sack,
then back up towards the head.  I threw my head back and moaned as she did
that, which made her giggle and lick my head harder.  She kissed her way
down my right thigh, then back up and down the left one, driving me insane.
Finally she settled back on my crotch, and slowly took my throbbing member
between her soft lips.

	I didn't last long as she gave the most exquisite blowjob ever, and
after what seemed like too short a time I found myself moaning that I was
about to cum.  She pushed her head further down on my shaft till I felt the
back of her throat tough my head, and she let out a soft moan that shook
the muscle against my penis, and I exploded into her mouth.

	I clutched the edges of the couch as my whole body tightened with
my orgasm, and I involuntarily lifted my bottom from the couch and
half-stood as it took over.  I felt her suck it all down as I shot inside
her mouth, then I collapsed back down as she finished me off.

	She gave the tip of my dick a flick of her tongue as she removed it
from her mouth, and after cleaning a few spot of cum from my shaft, she
tucked it back into my panties and smoothed out my skirt.  I looked down at
her with a smile, and told her it was time to return the favor.

	We quickly swapped positions, and after a few more passion-filled
kisses I lowered my head and began to kiss my way up her thighs.  I was
anxious to return the awesome orgasm she had just given me, and I quickly
pushed her skirt up around her waist as I continued kissing.  I immediately
noticed that she wasn't wearing panties and knew she had been planning this
from the moment I first told her about my dressing.

	She moaned out as my kisses found her clit, and I sucked it into my
mouth and bit down gently.  Her body shook as her first orgasm hit her, and
I grabbed her hips and pulled her crotch towards my face as I sucked harder
on her clitoris.

	After her first orgasm passed, I began to work my tongue lower, and
quickly it slipped inside her.  She moaned even louder, and with my right
thumb I began to rub and massage her clit as my tongue worked in and out of
her wet folds and hole.  Quickly she had a second and third orgasm before
she begged me to stop and let her breathe.

	I smoothed the skirt back down and sat on the couch next to her.
As she caught her breathe, her hand began to caress my thigh again and my
cock again began to harden.  As we sat there side by side continued to
kiss, until suddenly she threw her leg over me, and straddled me with a leg
on each side.  She broke out kiss just long enough to tell me she wanted to
feel me inside her, and with her free hand pushed my skirt up around my
waist and again pulled my thong to the side.

	She hiked up her own skirt, and quickly lowered herself down to my
crotch.  I felt my cock at the entrance to her hole, and then it slipped
inside.  The feeling was incredible as she bobbed up and down on my erect
member.  We continued to kiss, and our hands intertwined as we fucked each
other.

	After what again seemed like too short of a time, I moaned through
our kiss that I was going to cum, and she replied that she was too.  As her
body pushed down on my cock, I felt my shaft swell and my hot cum began to
shoot inside of her.  As she felt my cock swell and begin to unload, her
own orgasm washed over her and she collapsed onto me.  Our kiss broke as
her head fell to the side and she moaned out.

	As we sat there together, my now softening cock still inside her,
she began to nuzzle and kiss my neck.  After a bit of this she rolled off
and told me to go clean myself up, and I looked down to see dried cum from
both of us all over my crotch.  I strutted to the bathroom and quickly used
a wet washcloth to clean the cum from my skin, then tucked my now
completely flaccid penis away.  Settling my skirt back into place, I
emerged from the bathroom and followed Jill into her bedroom again.

	She quickly fixed her make-up in the mirror, then turned to me and
redid mine just as quickly.  Handing me a small purse, she said we were
going out and to grab my wallet.  A little apprehensive about going out, I
hesitated briefly, but she reassured me and I grabbed my wallet off the bed
(my male clothing was no where around) and followed her out the door.

Part 2, in public coming soon

I would appreciate anything you would like to send me, feedback, stories,
pictures, anything at all.  My email is Vtcarfanatic@yahoo.com.  Danielle