Date: Fri, 25 Apr 2008 00:52:24 -0400
From: story1963writer (at) aim (dot) com
Subject: My Descent (TG)

My Descent

by story1963writer

This is the first time I've told my story publicly. I wrote this maybe 3
years ago, and have shared it with one person.

I used to cross dress in my hotel room while away on business trips. I'm a
fat bald 46 year-old who looks ridiculous dressed up in ladies underwear.
When you're obsessed, though, appearances don't necessarily stop you from
doing something.  I'm married, but my wife doesn't know about my hobby.  I
never do it at home.  It was something I only did when traveling.
Fortunately, as a sales manager, I spent a lot of time on the road.  But
with airport security these days, it has become way too risky to carry a
suitcase full of ladies undies and a dildo for pleasuring myself.

Even as a nine or ten-year old, I was the one who volunteered to play the
girl role when we played games.  Thinking back, it's funny how sexual some
of our play was even though we did nothing overt, and didn't really know
what we were actually doing.

I don't know how I got the idea to do it, but in high school, I began to
dress up in my sister's or my mom's underwear and walk around in front of
an open window.  Then I would jack off.  I don't think anyone ever noticed
me.  If anyone did, I never found out about it.  My sister had a garter
belt and my mom had this fabulous pink and black lace highly boned corset
that I liked to wear.  This was at the end of the girdle era.  I carried on
with this even into college, when visiting home for the summer.  I stopped
cross-dressing when I was caught by my father.  I pleaded mental illness
and he didn't punish me but he didn't try to do anything to help me either.

I saw my first picture of a transsexual sometime while in college.  There
was a spread in Hustler of a shemale.  That wasn't revealed until the last
photo of the spread, of course.  I was absolutely fascinated.  Yet men held
no attraction for me whatsoever.

I had a roommate for the first year of college, during which my sex life
revolved around masturbating to girlie magazines.  Then I got my own
apartment, and I made one of the great discoveries of my life.  My anus.
It welcomed many interesting objects ranging from vegetables to tools to
furniture legs.  My favorite was a hammer because the head was so heavy
that I could squat over it and it would move in and out as I bounced up and
down.  At some point, the cross-dressing urge returned.  I stole a few
things from the washing machines in my apartment building.  I went to
clothing stores in run down areas of town where they would have big bins of
panties on display and I would pick a few pairs and buy them.  The
anticipation, the planning, the actual selection of the panties, and
bringing them to the counter to pay for them was painfully exciting, yet
tainted by humiliation.  In retrospect, maybe it was the humiliation that
was the most exciting part of it.

I remember that I would walk past lingerie stores and admire the expensive
satin and lace panties.  They were so much nicer than the 99 cent, plain
polyester panties I was buying.  I had to own some. I staked out a store
and went in as soon as the doors opened on some miserable Saturday morning,
because I thought that was the time I was least likely to be seen.  The
owner greeted me nicely, and I asked her to show me some nice panties.  She
asked me what size my girlfriend wore, and I replied that they were for me.
I shivered with delight as these words came out of my mouth.  But the
counter lady was appalled and she began to scream that I was a pervert, and
I quickly ran out into the relative anonymity of the rainy street.  It was
many years before I went back to a lingerie shop.

I started traveling regularly for business in about 1998.  I realized that
I was totally anonymous in the cities I visited.  I didn't know a soul.  My
hotel room gave me a place to be alone and uninterrupted.  I started off
traveling with one pair of panties.  As the urge to dress became greater, I
became more brazen and began to take more risks.  I would go to Sears and
buy nylons.  I would go to the Maidenform outlet and buy panties.  I was
happy to learn that older sales help were respectful and served you without
complaint.  Younger sales girls are another story entirely.  They laugh at
you and sometimes make faces. I had no clue how to buy bras, so that was
always interesting.  They never fit.  I would go to "Avenue" which is a
"big woman's" store that sold lovely satin panties.  I eventually acquired
a garter belt and a Rado garter brief.  I think I reached a point where I
was carrying more lingerie in my suitcase than stuff for my business needs.

Upon arrival at a hotel, I would hang out the "Do not disturb" sign, lock
the door, and strip down.  I would open the curtains, pull out my lingerie,
and dress up.  I'd parade around the room, look at myself in the mirror,
pinch my nipples, and begin jerking off. When I became aroused enough, I
would lay down on the bed, keep pulling on myself, and begin speaking
loudly saying things like "Oh, your cock is so big.  Stick it in my ass.
Fuck my ass.  Ram it in me," in hope that someone in an adjoining room or
in the hallway would hear me.  This is how I would ultimately orgasm.

On one trip, while visiting the porn district, I just gave in and bought
myself an 8" dildos with the rubber suction cup attached to the scrotum on
the bottom.  I was set.  I fucked myself silly that night.  I was afraid
that I would become incontinent, I had stretched myself out so much.  But
ass muscles have a memory, and by morning all was right with the world.

Eventually, I was ready for the next step.  It's not too hard to find ads
for shemale or tranny prostitutes in most big cities.  My first experience
was Vancouver.  The hooker had little tits, really smooth skin and was
hairless from the neck down.  I didn't know exactly what to do.  I had
never visited a hetero escort, let alone a transsexual, and I was scared
out of my wits. Basically, I just lay there stroking this girl's thigh,
looking at her uncut cock from a relatively close vantage point, but not
daring to touch it.  Eventually she asked if I wanted her to blow me.
Her's was the first blow job that ever ended in my coming, even though I
was covered.  She gave much better head than my wife ever did.

Well, once you put your toe in the water, it's inevitable that you'll want
to get fully immersed.  I started visiting t-girl hookers wearing panties
and stockings underneath my business suits.  Eventually touching thighs
went on to be touching tits and gentle carresses of the organ.  Then the
grip my obsession had on me began to strengthen.  On maybe my sixth visit I
finally took a cock in my mouth.  It was one of the most exciting moments
of my life.  It was so much more fun than eating pussy, because you were
able to see the effect of your work as that cock became hard in your mouth.

Then 9/11 happened, and travel with a suitcase full of stuff you didn't
want to have revealed by the security agent wasn't so easy anymore.  First
I ditched the dildo.  Eventually, I threw all my lingerie out.  Since I
never dressed at home, keeping it there just increased the risk of being
found out.  This didn't stop me from being obsessed with shemales, however,
and I eventually knew that I was ready to lose my "virginity."  It was with
this ugly transvestite, again in Vancouver.  She looked nice in the
pictures on the web; a true testimonial to the skills of some glamour
photographers.  Well, despite her appearance, this creature had an
incredibly seductive way of talking, and she suggested that we do all kinds
of things, and the next thing I knew, we were naked and enmeshed.  Her cock
was small, and really wasn't all that sastisfying compared to that dildo I
used to fuck, but my cock is pretty small, so I wsa not in a position to be
that critical.  In any case, it was nice to have something sliding in and
out of my ass without having to provide the motion.  I came.

Since then I have been with two more shemales.  Once it was nothing
special, but the other had fabulous natural-appearing tits and a huge thick
uncut cock, maybe 18-19 cm long.  I saw that thing and I immediately had to
have it in my mouth.  It was the first and only BBBJ I ever gave.  She was
a little rough, and she sometimes forced my head down on her shaft until I
was beyond gagging.  It gave me much greater respect for chicks and guys
that can deep throat huge cocks in porno films.  Well, I succeeded in my
mission of making that tool hard, and she flipped me over, put on a rubber,
greased me up, and plunged that monster into my ass.  I thought I would
die.  I can't really describe the feeling but I'll try.  It's like having
to go to the bathroom for about an hour, but you keep holding it in and you
feel that tremendous pressure building inside you waiting to be expelled,
but kind of in reverse, and with rhythm.  She did me for what seemed like
30 minutes, before flipping me over so that we were face to face, and
finishing me with her hand simultaneous with her own orgasm.  I came so
hard I accidentlly squirted into my own mouth.

That was about 4 years ago.  I finally understood why some men risk their
life for the sake of a good hard cock in the ass.  Common sense said quit,
this is a dangerous game. I wish I could say that common sense was the
reason why I stopped, but the real reason was that I didn't think I could
ever have that intense a sexual experience again.  Instead I began surfing
internet porn sites of every imaginable sort looking for my thrills that
way.  I am a bit ashamed by what I have found turns me on, but then again,
humiliation seems to be part of my sexual persona since childhood.

Prologue

On a recent business trip, I could no longer resist the old urge.  I had to
get fucked.  I Googled "transsexual escorts" for the city I was visiting.
The first escort I called sounded like a totally stoned junkie, with a deep
man's voice.  Not at all in keeping with the stunning picture provided.  I
found another ad for a shemale who looked pretty nice in the photo.  You
could tell the pic was real because she wasn't perfect.  I could see that
her boobs were silicon, and she had sort of a big ass, like a Brazilian,
but her face was nice.  I called her.  She had a very feminine voice.  I
asked her if she was a "top."  She replied "Versatile."  After a few
seconds she asked me "Do you want to get fucked?"  I answered excitedly,
"Yes."  Then she asked if I liked to suck dick too.  Again, I answered
"Yes."

She said "Good."  My cock was awakening and my heart began to beat faster.
She said that she had a 7" long, very thick cock, and that some found it to
be too big.  I said that very big sounded very good, that I was ready to
take all she could provide.  We went through the usual negotiations, she
agreed to come to my hotel, and I hung up.  Maybe 5 minutes later, I called
her back to call it off; I had chickened out.  She made like she was very
understanding and said "OK sweetie, maybe next time."

She may know me better than I know myself, because I'm already having
fantasies of my next visit to that city, and of calling her again.  But I
think that next time, to help overcome last minute fears, I'll tell myself
that I'll ask her to wear a condom when I suck her off.

If you like my story, please write me
story1963writer at aim.com