FionaFortune
08-26-2023, 06:40 AM
This is NOT an AD for escort services.
It's just a sexy story of one night of play.
Plus this happened over 20 years ago.
"I then gently rubbed around
his rosebud and slowly penetrated, back and forth gently until
I was in far enough to feel the prostate. I slowly pressed
around it. I then got into a pace of going down hard on the
cock with suction while at the same time penetrating to the
prostate and massaging."
I have always played with women's clothes since my
teens. It wasn't until my early twenties when I started playing
with guys while dressed, even though I had fantasized about
being a sexy gurl for men since my teens.
My kink is that I love to transform into a wanton slut for men.
I always felt shame about this desire, feeling like it made me
some pathetic freak. I would regularly purge all my girly stuff
and vow to be a strong straight man.
On one of those purges, I decided to enlist in military, feeling
that the discipline and masculine environment would be good for
me. The total experience was good for me. I got to travel to
Europe, got my college degree paid off, got into great shape
and made some great friends. The bad part of the experience
was putting my TV side deep in the closet. I was able to
honorably discharge after the first gulf war. At that point
I was hot to play as Fiona.
I got a job in Las Vegas and finally felt very free to to indulge
in my kink. I first hooked up with an older TV called Michelle
who would hold weekly parties at her place. Those were great
parties where we would hang out, get made up, dressed, sometimes
fuck and then go out to a bar called Gipsy and see if we could
pull guys.
One of the stark memories of that bar is when I saw a co-worker
from my finance job, he did not recognize me and I felt an
amazing thrill from that. It was like I became another person
free of all my hangups, a purely sexual being.
So, I was going out en-femme and hooking up with guys when I met
a tgirl hooker at the Gipsy. Fascinated, I asked her a ton of
questions, she said I was hot enough to do it too.
The idea of whoring was a tremendous turn on for me. Being a
dirty whore for any man with the cash, got me off. The problem
was the legal aspect, an arrest could destroy my career.
So I did a ton of research and actually talked to a criminal
lawyer. The plan I hit on was to advertise as a "Female Impersonator"
and charge per hour. Also, make it VERY clear that no sex was
promised or implied. Only paying for time with a "Female
Impersonator" entertainer. I actually got an entertainer license
and a pager (Phone #). Then I placed an ad in the old Las Vegas Sun
classifieds.
Holy Shit! The first day the ad ran, I left the pager and went
to work, when I got home I had 15 messages. I called them all back,
and was clear no sex was implied or promised, my rate was $70 per
hour and I was available in the evenings. Ended up with 5 dates over
the next 3 days. I was jerking it on every call thinking damn, I'm a
dirty TV whore now!
My first trick was at 7:30 pm the next day. I couldn't sleep and jacked
it probably 3 times thinking about how hot it would be to whore.
That work day dragged on, but finally it ended. I ran home, enemea-d,
and got dressed and made up, had an hour before the date. So I went
to a gay bar I used to hang at, "Snicks", which became "Bastille".
Had a drink, got some interest but killed time until my date. I went
to the address, rang the bell and it was a guy in a wheel chair.
Okay, I introduced myself, made it clear no sex implied and asked
for my fee. He paid, then I asked how he saw this going.
He said he could still get hard and he found Tgirls sexy. Cool, we went
to his bedroom. I helped him onto the bed, he presented his cock and I
got to sucking. Damn, this guy was hung, at full mast he was over 8
inches, a great cock. I just wanted to ride it and forgot my role.
I pulled a condom out, rolled it down and lubed it. I then positioned
myself to slowly lower my ass-pussy on to it. I always liked that position
for big cocks because I could control the insertion.
I impaled myself a bit too quickly, too far and it hurt.
I made a huge mistake in not putting a butt plug in before the trick.
I got off, lubed again, then slowly lowered myself on it. It hurt
less and that great feeling of fullness spread in my ass-pussy. That
was a great cock, 8 inches and thick, the head was a bit recessed into
the shaft, but the thickness was beefy. Once the pain abated, I really
got into banging my ass all the way down, balls deep and back up until
it almost slipped out. Then down again and up, feeling like true whore.
I changed position to classic cowgirl, keeping that meaty cock in
my twat the entire time. The look on my john's face was classic bliss
as his cock hardened. I fucking love that moment when the cock gets
it's hardest and that love muscle spurts it's load. Wish that moment
could last forever. The guy was sensitive after cumming so I reluctantly
climbed off. I asked him if could go again because I felt primed to fuck.
Sadly one erection was all he could muster. So I fixed my makeup and
left. That guy became one of my regulars. Once a week for next 3 years
he fucked me and I loved it.
My next trick was not until 9 pm, so I checked the pager. No
new calls. But I was in heat and dressed to fuck so I went to a
section of Industrial road with 2 dirty bookstores. Lion's Den and
the Love Boutique.
Lion's Den was the best with the most booths and best action but
Love boutique was okay sometimes too when the action died at the
Lion's Den. I parked and went into Lion's Den, back to the booths.
A little after 8pm so it was a bit dead. Got a center booth and
loaded a gay flic, was edging it when a nice BWC Big White Cock
came through. I dropped to my knees and began to wurk it. I
spit on it and tried to deep throat it all in one go. That pole
was thick. Both hands lightly scratching the ball, putting
great suction the crown while rolling my tongue around the ridge
and then sucking it all down to the balls. That cock got rock
hard and was about to blow when I pulled off it and invited
him over. I unlatched the door and he came in. I fell to my knees
and began wurking it again while digging my purse for lube and a
condom. I never ask guys if they want to fuck, I just put the
rubber on them and present my ass-pussy. They almost always just
go with it. This guy was no different. There I am bent over,
feeling him knocking on my back door, then Ungh! He rammed it
home balls deep in one go. Fuck that hurt! The cock was thick
over 7 inches with a banana curve. Luckily I had some poppers
in purse. After a few sniffs and some slower strokes. I got
into it and started pushing back.
"Thwap, Thwap Thwap" was sound as he bottomed out balls deep.
I was edging the whole time, but that point where he started
pounding it out, that was when the gorgeous electric feeling
of fullness pushed me over the edge. I started convulsing
and my rosebud started to grip that fuck pole in my tranny
twat. I was deep into a satisfying orgasm when his rock
hard cock stiffened and I felt that orgasmic spurting in my
ass-pussy. His orgasm lasted for nearly a minute after mine.
I was bathing in that temporary satiation of nice fuck
when he pulled out, ripped the rubber off and walked out.
After that I wiped up, fixed my clothes and makeup and left
to my next trick.
The guy had a big house in a nice neighborhood off East
Sahara near the golf course. I parked on the street, walked to
door and knocked. My john was early fifties, salt and pepper
hair, HWP and dressed in nice jacket. I was a bit surprised.
This was a good looking man with money, he could have a
host of women. I greeted him and he invited me in. I went
to the part about no sex promised or implied, he paid me, then
I asked how he wanted this to go. He wanted me to "serve" him.
I followed to his living room, where sat in nice big leather
chair. As he sat, down he snapped "Whisky, Neat". I went to
bar area and poured one from his crystal decanter. After I
handed him the drink, he ordered me to massage his feet.
Dutifully, I got down on my knees and took his shoes and socks
off, then began to massage his feet. I heard "Ahh, Yes", so
I just kept going. After about 10 minutes he said "Neck
and Shoulders". So I got up and started in there. After
a few minutes of massaging him I could visibly feel his tension
release. He then said "On Your Knees" and pointed to floor
next to the chair. I complied, he got up, walked to me and
undid his pants and dropped his shorts. "Suck" was what I heard
next. Not that I needed to be ordered to do that, I thought to
myself as suckled the flaccid member.
I started to lightly pull the skin and scratch the balls while
putting major suction around the crown, then going all the way
down. He really liked that and started to harden. The cock was
decent girth and a bit under six inches with a right ways bend.
I kept on sucking, varying things up a bit, but giving great
suction and taking the whole cock down for about 10 minutes.
I heard "Look at Me", he handed me a condom and lube. I thought
yes, I could use another fuck. He then said "put your index finger
in the condom lube it up and massage my prostate". Wow, I thought
this guy knows what he wants. I usually only need to finger
a guy when can't get off any other way. Even then, most guys
don't know about that or are too shy to ask. So I lubed it,
he spread wider to give me access. I then gently rubbed around
his rosebud and slowly penetrated, back and forth slowly until
I was in far enough to feel the prostate. I slowly pressed
around it. I then got into a pace of going down hard on the
cock with suction while at the same time penetrating to the
prostate and massaging. Damn that was this guy's button. Less
than a minute later, he grabbed my head and shoved it all the
way in while saying don't stop. Then he blasted a huge load
down my throat that I was choking to swallow. I did get a big
spurt though as he pulled out.
After that he was gushing my praises, saying it was one of the best
Blowjobs he ever had and he needed my info as there would
definitely be more sessions. The guy gave me extra $200 and
booked me for a party at his house the next Friday.
The party was a weird thing. A black tie dinner party for friends
and couples. He put me in a closet off the basement game room with
an open door and curtain just inside. All through the party a
string of male guests would come down to get "Serviced" by me.
He told them he found a hooker who gave amazing head. I was made
up behind the curtain, but I think most of them must have assumed
I was a genetic female. I know I saw several of the same cocks
twice so I must have a been a hit. After the party ended I
blew him again the same way. He never fucked me but I got to
be a paid regular at his parties going forward. I actually ran
into him once when I was in guy mode at a steakhouse bar. I was
too closeted about being Fiona at the time to even give him a wink.
After I left his place, I had one last trick for the night. An in-call,
the guy paid extra. He was late fifties with a gut and a wild beard.
I blew him to completion. The cock was average.
That was my first night as a transvestite whore in Las Vegas.
It's just a sexy story of one night of play.
Plus this happened over 20 years ago.
"I then gently rubbed around
his rosebud and slowly penetrated, back and forth gently until
I was in far enough to feel the prostate. I slowly pressed
around it. I then got into a pace of going down hard on the
cock with suction while at the same time penetrating to the
prostate and massaging."
I have always played with women's clothes since my
teens. It wasn't until my early twenties when I started playing
with guys while dressed, even though I had fantasized about
being a sexy gurl for men since my teens.
My kink is that I love to transform into a wanton slut for men.
I always felt shame about this desire, feeling like it made me
some pathetic freak. I would regularly purge all my girly stuff
and vow to be a strong straight man.
On one of those purges, I decided to enlist in military, feeling
that the discipline and masculine environment would be good for
me. The total experience was good for me. I got to travel to
Europe, got my college degree paid off, got into great shape
and made some great friends. The bad part of the experience
was putting my TV side deep in the closet. I was able to
honorably discharge after the first gulf war. At that point
I was hot to play as Fiona.
I got a job in Las Vegas and finally felt very free to to indulge
in my kink. I first hooked up with an older TV called Michelle
who would hold weekly parties at her place. Those were great
parties where we would hang out, get made up, dressed, sometimes
fuck and then go out to a bar called Gipsy and see if we could
pull guys.
One of the stark memories of that bar is when I saw a co-worker
from my finance job, he did not recognize me and I felt an
amazing thrill from that. It was like I became another person
free of all my hangups, a purely sexual being.
So, I was going out en-femme and hooking up with guys when I met
a tgirl hooker at the Gipsy. Fascinated, I asked her a ton of
questions, she said I was hot enough to do it too.
The idea of whoring was a tremendous turn on for me. Being a
dirty whore for any man with the cash, got me off. The problem
was the legal aspect, an arrest could destroy my career.
So I did a ton of research and actually talked to a criminal
lawyer. The plan I hit on was to advertise as a "Female Impersonator"
and charge per hour. Also, make it VERY clear that no sex was
promised or implied. Only paying for time with a "Female
Impersonator" entertainer. I actually got an entertainer license
and a pager (Phone #). Then I placed an ad in the old Las Vegas Sun
classifieds.
Holy Shit! The first day the ad ran, I left the pager and went
to work, when I got home I had 15 messages. I called them all back,
and was clear no sex was implied or promised, my rate was $70 per
hour and I was available in the evenings. Ended up with 5 dates over
the next 3 days. I was jerking it on every call thinking damn, I'm a
dirty TV whore now!
My first trick was at 7:30 pm the next day. I couldn't sleep and jacked
it probably 3 times thinking about how hot it would be to whore.
That work day dragged on, but finally it ended. I ran home, enemea-d,
and got dressed and made up, had an hour before the date. So I went
to a gay bar I used to hang at, "Snicks", which became "Bastille".
Had a drink, got some interest but killed time until my date. I went
to the address, rang the bell and it was a guy in a wheel chair.
Okay, I introduced myself, made it clear no sex implied and asked
for my fee. He paid, then I asked how he saw this going.
He said he could still get hard and he found Tgirls sexy. Cool, we went
to his bedroom. I helped him onto the bed, he presented his cock and I
got to sucking. Damn, this guy was hung, at full mast he was over 8
inches, a great cock. I just wanted to ride it and forgot my role.
I pulled a condom out, rolled it down and lubed it. I then positioned
myself to slowly lower my ass-pussy on to it. I always liked that position
for big cocks because I could control the insertion.
I impaled myself a bit too quickly, too far and it hurt.
I made a huge mistake in not putting a butt plug in before the trick.
I got off, lubed again, then slowly lowered myself on it. It hurt
less and that great feeling of fullness spread in my ass-pussy. That
was a great cock, 8 inches and thick, the head was a bit recessed into
the shaft, but the thickness was beefy. Once the pain abated, I really
got into banging my ass all the way down, balls deep and back up until
it almost slipped out. Then down again and up, feeling like true whore.
I changed position to classic cowgirl, keeping that meaty cock in
my twat the entire time. The look on my john's face was classic bliss
as his cock hardened. I fucking love that moment when the cock gets
it's hardest and that love muscle spurts it's load. Wish that moment
could last forever. The guy was sensitive after cumming so I reluctantly
climbed off. I asked him if could go again because I felt primed to fuck.
Sadly one erection was all he could muster. So I fixed my makeup and
left. That guy became one of my regulars. Once a week for next 3 years
he fucked me and I loved it.
My next trick was not until 9 pm, so I checked the pager. No
new calls. But I was in heat and dressed to fuck so I went to a
section of Industrial road with 2 dirty bookstores. Lion's Den and
the Love Boutique.
Lion's Den was the best with the most booths and best action but
Love boutique was okay sometimes too when the action died at the
Lion's Den. I parked and went into Lion's Den, back to the booths.
A little after 8pm so it was a bit dead. Got a center booth and
loaded a gay flic, was edging it when a nice BWC Big White Cock
came through. I dropped to my knees and began to wurk it. I
spit on it and tried to deep throat it all in one go. That pole
was thick. Both hands lightly scratching the ball, putting
great suction the crown while rolling my tongue around the ridge
and then sucking it all down to the balls. That cock got rock
hard and was about to blow when I pulled off it and invited
him over. I unlatched the door and he came in. I fell to my knees
and began wurking it again while digging my purse for lube and a
condom. I never ask guys if they want to fuck, I just put the
rubber on them and present my ass-pussy. They almost always just
go with it. This guy was no different. There I am bent over,
feeling him knocking on my back door, then Ungh! He rammed it
home balls deep in one go. Fuck that hurt! The cock was thick
over 7 inches with a banana curve. Luckily I had some poppers
in purse. After a few sniffs and some slower strokes. I got
into it and started pushing back.
"Thwap, Thwap Thwap" was sound as he bottomed out balls deep.
I was edging the whole time, but that point where he started
pounding it out, that was when the gorgeous electric feeling
of fullness pushed me over the edge. I started convulsing
and my rosebud started to grip that fuck pole in my tranny
twat. I was deep into a satisfying orgasm when his rock
hard cock stiffened and I felt that orgasmic spurting in my
ass-pussy. His orgasm lasted for nearly a minute after mine.
I was bathing in that temporary satiation of nice fuck
when he pulled out, ripped the rubber off and walked out.
After that I wiped up, fixed my clothes and makeup and left
to my next trick.
The guy had a big house in a nice neighborhood off East
Sahara near the golf course. I parked on the street, walked to
door and knocked. My john was early fifties, salt and pepper
hair, HWP and dressed in nice jacket. I was a bit surprised.
This was a good looking man with money, he could have a
host of women. I greeted him and he invited me in. I went
to the part about no sex promised or implied, he paid me, then
I asked how he wanted this to go. He wanted me to "serve" him.
I followed to his living room, where sat in nice big leather
chair. As he sat, down he snapped "Whisky, Neat". I went to
bar area and poured one from his crystal decanter. After I
handed him the drink, he ordered me to massage his feet.
Dutifully, I got down on my knees and took his shoes and socks
off, then began to massage his feet. I heard "Ahh, Yes", so
I just kept going. After about 10 minutes he said "Neck
and Shoulders". So I got up and started in there. After
a few minutes of massaging him I could visibly feel his tension
release. He then said "On Your Knees" and pointed to floor
next to the chair. I complied, he got up, walked to me and
undid his pants and dropped his shorts. "Suck" was what I heard
next. Not that I needed to be ordered to do that, I thought to
myself as suckled the flaccid member.
I started to lightly pull the skin and scratch the balls while
putting major suction around the crown, then going all the way
down. He really liked that and started to harden. The cock was
decent girth and a bit under six inches with a right ways bend.
I kept on sucking, varying things up a bit, but giving great
suction and taking the whole cock down for about 10 minutes.
I heard "Look at Me", he handed me a condom and lube. I thought
yes, I could use another fuck. He then said "put your index finger
in the condom lube it up and massage my prostate". Wow, I thought
this guy knows what he wants. I usually only need to finger
a guy when can't get off any other way. Even then, most guys
don't know about that or are too shy to ask. So I lubed it,
he spread wider to give me access. I then gently rubbed around
his rosebud and slowly penetrated, back and forth slowly until
I was in far enough to feel the prostate. I slowly pressed
around it. I then got into a pace of going down hard on the
cock with suction while at the same time penetrating to the
prostate and massaging. Damn that was this guy's button. Less
than a minute later, he grabbed my head and shoved it all the
way in while saying don't stop. Then he blasted a huge load
down my throat that I was choking to swallow. I did get a big
spurt though as he pulled out.
After that he was gushing my praises, saying it was one of the best
Blowjobs he ever had and he needed my info as there would
definitely be more sessions. The guy gave me extra $200 and
booked me for a party at his house the next Friday.
The party was a weird thing. A black tie dinner party for friends
and couples. He put me in a closet off the basement game room with
an open door and curtain just inside. All through the party a
string of male guests would come down to get "Serviced" by me.
He told them he found a hooker who gave amazing head. I was made
up behind the curtain, but I think most of them must have assumed
I was a genetic female. I know I saw several of the same cocks
twice so I must have a been a hit. After the party ended I
blew him again the same way. He never fucked me but I got to
be a paid regular at his parties going forward. I actually ran
into him once when I was in guy mode at a steakhouse bar. I was
too closeted about being Fiona at the time to even give him a wink.
After I left his place, I had one last trick for the night. An in-call,
the guy paid extra. He was late fifties with a gut and a wild beard.
I blew him to completion. The cock was average.
That was my first night as a transvestite whore in Las Vegas.