Date: Wed, 15 May 2002 10:47:09 -0700 (PDT)
From: Stanley the Swinger <swingerstan@yahoo.com>
Subject: Being Passable

This is a story that deals with elements of crossdressing, as well as sex
between two males.  If you are too young to be reading this, please don't,
you have plenty of years ahead of you for it.  If this offends you, I think
you sure are deep into a website full of homoerotic porn for someone
offended by it.  Denial isn't just a river in egypt, is all I'm saying.
For those of you who are old enough, and honest with yourself enough to do
so, enjoy.  And send feedback to SwingerStan@yahoo.com

*****

I was never passable.  This was something I had accepted.  As much as I
would have liked it to be otherwise, I just never had the type of face that
could melt from male to female.  It didn't matter what makeup tricks I
used, or what type of wig I wore, I just couldn't pass.  It does kind of
suck sometimes, I would like to go shopping fully dressed, so that I could
try on outfits at the store without feeling like everyone was staring at
me, but it's also something I've dealt with, and I also have nothing
keeping me from growing facial hair.

Despite the fact that I couldn't go out in public dressed as a girl, I
still loved the clothes.  I loved women's clothes.  I loved everything
about women's clothes.  Guy's clothes are so boring.  I mean, yeah
sometimes it's cool to be tough and masculine, but come on, sometimes you
just need to be soft, and.. well, girlish.  And when you do that, you need
an outfit to go with it. I had the outfits.

But, due to my non-passability, I could only wear them in the comfort of my
own room.  I occasionally would venture out of my bedroom in a skirt and
pantyhose when my parents and brother were away, but I'd usually hurry back
into my room, fearing the front door would open and I would be trapped, a
damsel in distress so to speak.  But as hard as it was for me to hide my
dressing at home when I had my own bedroom, It was paradise compared to
when I first moved into a college dorm.

Suddenly, I had a roomate.  Someone who slept in the same room as me, in a
bed that sat at a right angle from mine.  Sure, I had found a place in my
room to hide a small stash of clothing, but I never seemed to get a long
enough stretch of privacy to actually put the stuff on.  Brent, my roomate,
was never guarenteed to be gone for any long period of time, and I was
terrified of him walking in on me just as I was buttoning my pleated skirt
around my waist.

So you can imagine how excited I was the night Brent got tickets to go see
a concert on campus, and I knew he would be gone at least 3 hours because
he wanted to see all the bands.  It would give me roughly 2 hours of
pure-crossdressed bliss, giving me enough of a window on both sides to get
everything put away before he came back.

20 minutes after Brent left, I pulled my little brown suitcase out from
between my bed and the wall.  I slowly looked through the items I had
brought to school with me to see what would have the honor of christening
the dorm room.  I decided against a pair of tight black clubbing pants
because I was sick of wearing pants for the last 3 weeks, as well as my
long black skirt, because I wasn't in the mood for a conservative look, I
wanted to be light and airy.

I instead settled on the aforementioned pleated skirt.  It was a blue skirt
with green plaid lines, I had a white, semi-sheer button up blouse that I
wore over a black midriff tank top.  Since the overall look had a somewhat
catholic schoolgirl look, I topped it off with a pair of knee-high
stockings, and a pair of black shiny men's strappy shoes that were the
closest things to Mary Janes I could find in men's 12 (another reason I
couldn't pass)

I could barely hold in the excitement by the time I pulled on the last
stocking and looked at myself in the mirror to button the middle buttons on
my shirt, leaving the bottom open to show off my bare midriff, and enough
on top to show off where my cleavage would be if I had breasts.  I took a
deep breath and looked at myself, head to toe.  I posed for a bit, smiling
at myself, in the clothes I belonged in.

I put on some Britney Spears music, which I only listened to when I was in
girly-mode, and sat down on the couch to relax.  I beleive being fully
dressed in women's clothes is the greatest stress-releif system in the
world.  I never feel more relaxed.  The problem here was, I got too
relaxed.

************

"Steve, what the hell?!?" I didn't even hear the door open when Brent got
back from the concert.  I was too busy sleeping on the couch.  I did hear
of course, when his shocked voice exclaimed the previously transcribed
quote.  I forgot what was going on for a second, but as I opened my eyes
and saw my outfit, I knew exactly what the issue was..

"Woah.. Brent.. I can explain.. um... you see.."  I tried to think of an
excuse.. I racked my brain trying to think of what possible explanation I
could give.  Halloween was too far off, Brent knew I hated Frats and so I
couldn't use rushing as an excuse.  I drew a blank. So I went with the
truth "I'm a crossdresser"

"Well no shit.. I can see that..."  He had a look on his face.. I was sort
of releaved by it, because it looked more like suprise than revulsion.
Suddenly I felt kind of bad for not just coming clean to him before.  "Why
didn't you tell me?" he asked, mirroring the same thoughts.

"I don't know.. I guess I was worried you'd freak out"

He went to the mini-fridge and handed me one of the beers we had managed to
sneak in, as well as popping one open for himself, before sitting down on
the couch.  "well, I guess I can understand that, I mean.. we've known each
other 3 weeks, and if I had freaked out, it would be a very uncomfortable
living space for the rest of the year. "

"Exactly.."

"But now that I know, and you know I'm not freaking out.. feel free to wear
whatever it is you want in here.. its ok with me."

"thanks.."

He smiled a bit, "well, why don't you model your outfit for me?" I looked
at him kind of oddly, but decided he was being pretty on the level, and
trying to understand this new aspect of my personality he discovered, so I
stood up and playfully teased the bottom of my skirt, and posed a bit for
him. I turned the Britney music up again and danced around to "baby one
more time" which seemed fitting based on my outfit.

When the song stopped, I did a little curtsey.  He eyeballed me up and down
and then said "Well now I know why you shave your legs...."  which, when
added to the sexy little dance I had just done for him, made me start
laughing, suddenly I lost my balance and fell towards the couch and right
into Brent's arms.

Both of us laughed for a second, and then it got very quiet.  We looked
into each other's eyes, and I think both of us were wondering not only why
didn't the other move, but why didn't we ourselves move.  then finally
Brent said to me.  "you know, I've always had a thing for schoolgirl
outfits."  It got quiet again, and I looked deep into his eyes, and I could
feel both our bodies leaning together, untill our lips pressed against each
oither's in a kiss.

We kissed for a few seconds and then Brent pulled away.  I didn't know what
to say, I think he was scared.  I know I was.  But we kissed again.  and
again.  It started out slow, but soon we were kissing each other over and
over, madly.  We moved up off the couch and were in each others arms.  I
felt myself wrap my stocking-clad legs around him as he pressed my back
against the wall for support.  It was then that I felt his stiff cock
pressed against mine. he started running his hands up under my skirt and
rubbing my ass.  He kissed my neck as I nibbled on his ear and the next
thing I knew we were on his bed, and he was pulling a condom out of his
sock drawer.

I unbuckled his pants and pulled his dick out.  I pulled off my white
cotton panties and continued to kiss his neck as unwrapped the condom, and
placed it into my hand, which I used to roll it over him.  He took two
fingers and got a bit of lotion from the same drawer, and began to finger
my asshole, spreading the lotion around my virgin hole, to prepare it for
what was next.

I slid my back against the wall and felt Brent pull my legs up onto his
shoulders.  He and I both took a deep breath, before he leaned down to kiss
me, and as he did, I felt him slowly enter my ass, gently and smoothly.  I
tightened at first, but finally loosened up as he eased into me.  The fact
that he continued to kiss me the whole time made it a lot more bearable.
Slowly he slid himself back and forth, and I thrusted my hips as well, the
tip of his penis rubbing against my prostate made my whole body quiver.

"I'm coming" Brent whispered as he continued to thrust.  I didn't get a
chance to say the same as the rubbing of his cock on my male g-spot made me
explode in ecstacy.  I had never had such a strong orgasm in all my life,
and it was all from the internal stimulation. I screamed loudly "I came
too" Brent said, before kissing me again and pulling out.  He rolled off of
me and we both stared at the ceiling, catching our breath.

I looked down at myself, Somewhere in our passion, my overshirt shirt had
come off. .  I could see that my blank tank would need replacing, and
Brent's chest was in need of a good shower.. but for now I was thankful to
see that my favorite skirt had not been soiled as a result of my orgasm, as
at some point Brent must have unbuttoned it, and it found it's place to the
floor.  Though we both needed to clean the aftermath off, for now we just
found each others arms.

"have you ever had made love to another boy before?" I asked Brent

"I still haven't" He said, as he spooned against me.  Those words still
mean something to me to this day.  when i thought about it, I understood.
We had not fucked as two boys, with one in a skirt.  When we made love that
night, I was making love as a girl.  It didn't matter that I didn't have
the right facial structutre, or that my feet were too big.  At that moment
when I fell into his arms, Brent saw into my soul, and saw the sexy girl
trying to get out.

And lying there, in Brent's arms that night, was when I finally felt
passable.