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  1. #1
    Senior Member Veteran Poster FionaFortune's Avatar
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    Aug 2023
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    Post First Night as a Transvestite Whore in Las Vegas

    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.


    4 out of 4 members liked this post.
    Last edited by FionaFortune; 08-26-2023 at 06:45 AM.
    Fiona Fortune - Mature Tgurl for Hard Top Men and TGurls
    Find me on Twitter Fiona Fortune

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