Subject: transsexual-heaven

I grew up in a small town, about an hour north of New York City.
I had spent lots of time with Playboy and Penthouse magazine, but
was not really active sexually through my teens or college years.
I mean, I had steady girlfriends, and had sex, but I wasn't a
Casanova type, chasing a different woman into bed every weekend.

When I graduated from college, I started going down to New York
City to visit friends, and just hang out. On one such trip, I
was checking out some hardcore pornography at a newspaper stand,
and noticed Screw Magazine. I opened it up, and thumbed through
it, and was startled to see the blatant advertisements for
prostitutes.

I purchased the magazine, and, upon arriving home, began reading,
and checking out the ads in more detail, slowly stroking my cock
as I read. When I got to the last few pages of ads, my eyes
popped out of my head.

Transsexuals. This was a first for me. I had never heard of
them, let alone seen one. Here, in black and white, were several
pages of them advertising their services. I spent many nights
checking out the pictures they each had in the paper along with
their ads. I started buying TS magazines, and as I got older,
renting TS movies. I spent lots of time in the Times Square
(before the city cleaned it up) bookstores, one of which had live
transsexuals in show booths downstairs. Twenty years have past,
and my minor distraction has become an active desire. The
Internet provides movie clips of whatever you desire, but I was
growing dissatisfied with merely viewing movies. I wanted to
have sex with one of these wonderful, mysterious, erotic
creatures.

I don't know if there are any transsexual escorts where I am
living now, but I had decided that the next time I was in a large
city, I would find one, and fulfill this long-lived fantasy.

As luck would have it, I had to spend a week in NYC for a
business trade show. As soon as I found out I would be going, my
heart started to pound. I could think of nothing else for the two
weeks prior to my trip.

The day arrived, and I drove down to the city. I checked in to
my hotel, and went wandering around the streets and avenues
surrounding Times Square. The peep shows weren't on 42nd street
anymore, but they were within a few blocks. I found a store with
T-Girls, and spent several hours going from booth to booth. I
was growing delirious with lust. I had to have one of them. I
settled on one particular woman, and tipped her so she would
slide a dildo up her ass while I watched. I jerked off while
watching this, and shot my load on the window between the booths.
I smiled at the object of my desire and left.

After dinner, I decided. That would give me time to recover so I
could enjoy this long-time fantasy coming to fulfillment. I
spent the rest of the day walking around the city. I didn't need
to be at the convention center until 9:00 the next morning, so I
was on my own for the day.

Finally, it was dinnertime. After eating, I returned to my
hotel room, showered and dressed. I went to a newsstand not far
from my hotel and picked up a copy of Screw. I returned to my
room, and started reading the current ads. I saw several who
looked good, and, believe it or not, several pictures which I
remembered from 20 years ago. I figured either they were not
photos of the girls, or they just didn't bother updating them.
Either way, I passed on those. Finally, I found one.

She was lovely, at least her picture was. She was an ebony
goddess. Her ad said she was 5'4, 115 pounds, 36c 26 36, 9"
uncut. She claimed to be of Brazilian, African American and
French ancestry. She went on to state that she was male to
female and was still able to cum.

This is it, I thought to myself, and picked up the phone. A
sultry, deep voice answered and we discussed my reason for
calling. She said she did out calls, and knew the hotel I was
in. An hour was $150, during which anything goes, with no limits
as to how many times I could cum. She would bring the condoms.
I asked it the picture I was looking at was really her. She told
me to look through the peephole when she arrived. If I wasn't
happy with how she looked, I should just not open the door and
she would leave.

I said ok, I would love to see her, and she said she would be
there in about an hour. I had a drink and tried to calm down, but
my heart was racing. I could still back out by not opening the
door, but I realized I would probably call another girl the next
day if I didn't do this one.

I was looking out the window when I heard a knock on my door. I
almost dropped the glass I was holding as I jumped. This was it.
I put the glass on the table, and looked through the peephole.
It was she all right, and she was a vision. I opened the door,
and smiled at her, not knowing what else to do. She smiled back,
and gave me a peck on the cheek. I stepped back so she could
enter the room and closed the door behind her.

She was wearing a white halter-top, with no bra, her nipples
plainly visible through the thin fabric. The halter left about
eight inches of smooth, firm stomach visible above the waist of a
red leather mini skirt, which was maybe 10 or 12 inches from
waist to bottom hem. Red garter straps ran down from underneath
her skirt to hold up her red, seamed thigh high stockings. Her
shoes matched the stockings, and the heels were about six inches.
I was taking in this vision of loveliness when she ran her finger
along my ear. I jumped and looked at her. She asked if I was
happy, or if she wanted me to leave. Not for at least an hour I
told her. I offered her a drink, which she accepted, and we
discussed what I would like to do. She said she was able to
provide me with whatever fantasy I desired, but payment was up
front. I handed her the cash, and asked if she would like to take
a shower with me. She said she would like that, that most guys
she ends up with haven't showered for hours, and don't smell all
that pleasant. I took her hand, and led her to the bathroom,
where I removed her clothes one piece at a time. When I had her
down to shoes, stockings, garter and panties, which were a red
thong, I stood back and looked at her. My cock was stiff as a
board, and I my breathing was ragged. I knelt before her, and
slowly pulled her thong down over her garter straps, watching as
inch after lovely inch of her wonderful cock became visible.
Once it was all exposed, I gasped. The ad said nine inches, but
had mentioned nothing about its girth. It was huge. I watched
with amazement as it slowly hardened, right before my eyes. When
she was fully erect, it must have been 5.5 or 6 inches around. I
moaned, and flicked the tip of my tongue up the bottom of this
wonderful, black cock. I had to have it, and moved to take it in
my mouth.

"Not so fast lover" she said, and pulled a condom out of her
purse. She put it on, and leaned back against the sink. 'Ok,
now, suck that cock".

I lost no time, taking her into my hot mouth. It took me three
or four passed up and down, but I finally succeeded in getting
the head of her cock lodged in my throat. I stayed down on her
shaft, using my hands to play with her balls, which were warm,
and hanging, loose and full. After a minute or so, I started
sliding up and down, sometimes all of it, sometimes just a few
inches. I was savoring my first cock sucking experience as well
as my first shemale experience. I was on my knees for about ten
minutes when she asked if this was how I wanted to spend my
entire hour. I got up, and took her condom off. We showered,
and then moved to the bed. I put another condom on her, and
sucked her until she was hard again. I was playing with her tits
and inhaling her freshly showered scent. I was intoxicated. My
cock was rigid, and rubbing between my belly and the bed as I ate
her cock.

She was running her hand through my hair, and pulled my face off
her cock. Smiling at me, she got on her knees, and rolled me on
my back. My cock was throbbing with my desire. She smiled at me
again, and I could see she had a condom in her mouth. She lay on
her stomach, and enveloped my cock, applying the condom as she
sucked her way down my shaft. She came off my cock, and looked
up at me.

"You're so excited, I want you to cum first so you can fuck me
good" she said.

I was in her control whether she realized it or not. I would
have done anything she wanted. She went back down on my cock,
slowly sliding her hand up and down my wet shaft behind her lips.
Very slowly she worked, flicking her tongue along the shaft as
she want, flicking it across my glans as she came to the top. I
started to squirm, and she sucked me all the way into her mouth,
her nose was buried in my pubic hair. She had her hands under my
ass, she was pulling me into her. I could not have been deeper
into her mouth. Then it happened. I exploded. I had an orgasm
the likes of which I had never experienced. She had inserted two
fingers into my ass and was actively massaging my prostate. It
felt like I came for ten minutes, pumping rope after rope of cum
into the condom. Once I was finished, she pulled her fingers out
of me, and slowly slid her lips off my condom-clad cock. I was
gasping for breath as she pulled it off, holding it tip down.
She had the tip, which contained my cum, in her mouth, and was
flicking her tongue and lips around it. She lay it on my face,
telling me she loves cum, but only from people she knows are
safe. I could relate to that, so I smiled. She then asked me it
I had ever eaten cum. I replied, telling her hers was the first
cock I had sucked.

"Well then, open up baby" and she poured my load out of the
condom into my surprised mouth. I was surprised, but found the
taste all right. In fact, I enjoyed it. I rolled it around my
mouth, savoring the bitter, salty taste. She watched me as I did
this, smirking behind half lidded eyes.

"I love to watch men eat their own cum" she said, rocking her
hips so her cock and balls rubbed on my chest. I reached across
my chest and took her cock in both hands, feeling it's satiny
hardness and warmth.

"You want to stick your cock up my ass now?" she asked, licking
her lips as she tossed the condom in the wastebasket.

I told her yes, but I wanted to suck her cock first, so I grabbed
a condom from the pile she had on the nightstand, and, copying
her example, put it in my mouth, and rolled it down her cock with
my wet lips.

"Very good, my little slut" she said, driving her hips slowly
back and forth.

I was now lying on my side, with her kneeling over me, on her
elbows and knees. My head was between her knees and elbows, on
my side. She was fucking my face as if she were doing someone
doggy style. I was motionless as her cock slid in and out of my
stretched lips, and down my throat. I could see her balls
swaying back and forth with her motion. I told her I wanted to
taste her; I wanted her to cum in my mouth. She sat back on her
heals, and told me for another $250, we could do the entire hour
bareback. I quickly handed her the cash, and pulled the condom
off her magnificent piece of meat. I engulfed it, making it a
part of my mouth. I could feel the smooth, hot skin sliding up
and down her shaft as she fucked my mouth. She used me like that
for about ten minutes, finally telling me she was going to cum
and asking if she should shoot right in my mouth, or pull out and
jerk off on my face. I replied by moving my hands to her
wonderful ass and pulling her deeper down my throat. I sucked
for all I was worth, using one hand to gently squeeze her balls.
I moved one finger to her tight rear hole and applied gentle
pressure. I felt something wet on my finger, and realized she
was squirting lubrication on it. I then slipped easily inside
her warm ass and pressed against her prostate this time. She
told me that was it, and grabbed the sides of my head, pulling
out until just the head of her cock was in my mouth. She slid
her hand up and down her cock. Her head was back and her mouth
open emitting a lustful moan. I felt the first splash hit the
roof of my mouth seconds later, to be quickly followed by three
more. She started fucking my mouth again, driving in and out the
full length of her meat. I pushed gently, and she backed off. I
sat up and swallowed, looking at her as I did so.

"Your pretty hot, for a first timer". She then pushed me down on
my back, took my cock in her hot mouth and sucked up and down
several times. She then squatted over me, with her hands on my
chest. She bent her thighs, and my cock penetrated her ass, with
her still hard cock standing proud against her stomach. I
switched my attention from my cock disappearing into her ass and
her cock jutting up from her patch of pubic hair. I could feel
the pressure build, and I guess she was able to see it on my
face, because she raised herself off my cock and said "oh no, not
yet, we still have time left.

"Roll over" she instructed, and once I was on my stomach, she
pulled my hips up so I was on my elbows and knees. I then felt
her tongue on my ass, and almost came as she stuck the tip into
my rose bud.

"I'm going to fuck you baby" she said, "let me know if it hurts".
I felt the cold lubricant hit my ass, then one, and then another
finger find it's way inside me. She moved them around and in and
out, loosening me up for her big cock. He fingers withdrew, to
be replaced with her mushroom shaped head. I felt gentle
pressure, and she told me to relax, then the pressure increased.
He grabbed my hips for leverage, and kept pushing. I was trying
to let myself stretch and admit her; I wanted to feel her inside
me. Finally, my sphincter let loose, and the head popped inside.
It felt like I was being torn apart. My rectum and anus were
screaming in pain.

"You have to relax, let it stretch. It should only take about
five or ten seconds."

I took deep breaths, and to my surprise, quickly stretched to
accommodate her. She then started slowly plowing deeper and
deeper. She would push in about two or three inches, stop for a
few seconds, and then pull out. She would then push in a few
more inches, and so on, until I felt her balls slapping my
thighs. Once she was all the way inside me, she pressed herself
to me, getting the last half-inch inside my stretched ass.

"You like that, don't you. You love cocks up your ass. I may be
the first, but I won't be the last, will I?"

I had to admit, I loved it, the feel of her cock head as it moved
inside my tight ass.

She began to saw in and out. Each time she pulled out, she
pulled all the way out, so I had to stretch to take her again.
After a few strokes, this was no longer an issue as my ass stayed
open long enough for her to bury it inside me again. She fucked
me for fifteen minutes, and then told me she was going to cum
again. I scrambled off her cock, turned, and took her in my
mouth, wanting to taste her again. This time, she drove her cock
down my throat, pumping her juice directly into my stomach. As
her final shudders rocked her, I pulled off, and gasped for
breath. She lay back, panting, out of breath from her second
orgasm. I put her legs over my shoulders, squirted some lube on
my cock, and put it at the entrance to her hot rectum. I slowly
pressed in, not sure how to do it.

"You have to push harder to get past my asshole baby," she
instructed.

I moved closer to her, and pressed my hips forward, hard. I felt
her ass give way and my cock entered her with a pop. I shouted.
I had never felt anything like it. Her ass was tighter than any
pussy I had ever fucked, and her rectum was hotter as well. I
could not control myself. I was plowing in and out of her as
fast as I could; driving my cock to the hilt each time I entered
her. Faster and faster I moved, striving towards the orgasm I
had to have. It only took about twenty strokes. I pulled out,
and jerked off between her legs, shooting cum on her stomach and
tits.

I lay back to catch my breath. Looking at the clock I saw we
only had a few minutes left. I asked her if she would like to
shower again before she left. She smiled, and said sure, that
would be nice to not have to travel dirty. We took a nice, hot
shower together, during which she got on her knees and first
sucked me for five minutes or so, then soaped up my cock and gave
me a long, slow, hot hand job that lasted fifteen minutes. We had
gone over the hour, but she said not to worry about it, she could
have gotten me off sooner if she wanted to. She went on to tell
me she actually enjoyed watching my face in the shower as she
slowly jerked me off. She kissed me goodbye, and left, walking
out of my dream as she had entered it.

I have since found attractive shemale closer to home, and
actually dated on for a year or so. I still love these beautiful
creatures, and have been with men several times. I consider
myself fully trisexual. I hope you enjoyed this actual piece of
my past. For all you who are wondering, go for it. I guess
going bareback was not all that wise, but I was caught up in my
lust at the time. I have been tested and am fine. Be safe, and
have fun.

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