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I Want to Have Sex With a Tranny

Personal Stories, Advice, and Support 1,480 People

    My Perfect Tranny

    I have had a thing for trannies for a long time. I am 45 years old and my fetish and desire to have sex with a tranny for about 15 years. I finally got up the nerve about three years ago to go on a transgender dating site. Within a few days I had met many sexy and willing t-girls...
    Globemaster001 Globemaster001 46-50, M 1 Response Oct 20, 2013

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    I'D Love To Make Love, In Wichita, KS

    I am a male to female transexual and would really love to find someone who would make love to me. I'm sure there is a nice person who is out there, that they would find me nice to play with. Stephanie
    StephanieShaw69 StephanieShaw69 56-60, T 1 Response May 8, 2013

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    Me To

    i want to soooooooooooooooooooooooooooooooooo bad!!!!
    pinedurby123456789 pinedurby123456789 22-25, M Jul 3, 2013

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    Having Sex With Tranny

    Best sex i had love it would keep doing againa and again they kno how suck and play with balls great ******* there tight hole mm if u tranny in fresno hmu got.my own pad 5594129789
    jakob559 jakob559 22-25, M Sep 8, 2013

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    indyheart indyheart 51-55, M Dec 19, 2013

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    I Want To Have Sex With A Tranny

    Having sex with trannies is a unique experience, they are so sweet and soft, and so understanding.I had have sex with women, this is really great, my favorite, with men, some times, I like that, but no so much as with women, but the first time I had sex with a tranny was really...
    Ed79 Ed79 31-35, M 2 Responses Feb 1, 2010

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    Best Of Both Worlds

    I love transexuals and transvestites. I have for a long time. I would not mind having one as a partner at all. And having breasts to play with and being penetrated too? Wow.
    deleted deleted 26-30 4 Responses May 29, 2010

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    Guy Looking

    Hey this is just a try i suppose lately i have kind of been ************ over trannies like alot its either feet or trannies. I really want to meet a tranny i have never been with a tranny but i want to im an anal virgin lol but honestly if you want to dominate you can or maybe...
    Stinkyfootlover Stinkyfootlover 18-21, M Jun 1, 2013

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    So Incredibly Horny!

    I adore sex with other TV's. Guys in feminine clothes are so sexy, I love a hard **** in a skirt, stockings and panties, love sliding my hand up a girl's skirt knowing there's a hot, hard **** waiting for me to touch and stroke and suck, and maybe a cute *** to ****.
    BiTvDeeUK BiTvDeeUK 56-60, T 2 Responses Jan 7, 2011

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    I Never Knew How Much I Would Love Sex With My Friend, The Tranny

    My wife had been very ill for a long time and sex with her was very painful so we just did not take the risk of causing her pain with sex. My friend knew that I was a man that very much enjoyed sex and just loved looking at someone in high heels and stockings. His wife would stop...
    hhstalegs hhstalegs 51-55, M 4 Responses Aug 19, 2011

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    I Want to Give It a Go

    The idea of a hot smooth body with a great pair of **** then a big throbbing **** between the legs always gets my **** hard. I want to start by sucking on her hard nipples and then moving down to take the hard **** in my mouth and start to suck. Then I want to feel hot...
    ClearSky99 ClearSky99 36-40 2 Responses Aug 23, 2009

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    Where Do I Find The TS Of My Dreams

    I fantasize about beautiful women with throbbing ***** on a daily basis. What is the beast way to meet a TS woman for sex? Has anyone had any luck?
    hodonjones hodonjones 26-30 Jul 17, 2013

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    Wanna **** A Tranny

    Have been so curious about ******* a hot tranny. One with a beautiful face and nice **** and a hard ****. I have always wanted to be dominated by a tranny. Would love a hard throbbing **** reaming me from behind. Her big **** down my throat as she blows a giant load has always...
    Nrana28 Nrana28 26-30, M Oct 19, 2013

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    Coworker Introduced Me To This Amazing World

    When I was 20 (I am 26 now) I worked as a security guard at a medical research clinic. One day we got a new employee (A nursing tech) named Lucy. Lucy was a forty-something year old redhead with a nice body, a cute smile and a strange "aura" about her. After a few days some of my...
    starlight575 starlight575 22-25, M 6 Responses Jan 6, 2012

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    Sex With A Tranny Would Rock

    I've been with other CD's before, some of which were actually relatively hot. BUT, never and actual transsexual. I'd like to treat them like a little ***** and **** the **** out of them! Also would like to dress up myself perhaps and be their ***** ;)
    chcgo25m chcgo25m 36-40 Oct 4, 2010

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    Looking Near Liverpool

    looking to have sex with a convincing young tranny living near liverpool england.
    janus4u2 janus4u2 46-50, T 6 Responses Nov 16, 2009

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    Seems So Long Ago

    My life has been up then down, now hopefully up again.  Before I got married I lived closer to NY City and could not stand the urge any longer.  My first exposure was as a young teen who accidentally picked up the "wrong" ***** mag in an airport magazine rack...
    kookycurious kookycurious 41-45, M 4 Responses Oct 28, 2009

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    I Want To Have Sex For The First Time With A Tranny

    Any body in Maryland close to Anne Arundel county
    bigsexy2034 bigsexy2034 18-21, M Mar 8, 2013

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    Younger

    Im an 18 yo. And i been ************ a lot to trannies. Ive been with girls like every other normal guy and its fun. But i wanna try something excitingly new. And trannies get me rock hard. The only thing that comes close is the time i spent a summer at my friends house. We...
    zanderps zanderps 18-21, M 1 Response Jun 25, 2013

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    I Want....

    to be made a little ***** for a tranny. Its a fantasy I have been longing to fulfill.
    nypennguy nypennguy 46-50, M Jul 31, 2013

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    I want to have sex with a transsexual girl,

    especially one with a smaller penis. I would like to give her oral as she does the same to me, and feel her inside me. I want her to have nice boobs but they don't have to be huge, just little A or B cups. Possibly C cups but I wouldn't kick her out of bed if she was bigger, LOL...
    iflash2 iflash2 66-70, M 2 Responses May 29

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    I Need Encouragement!

    It is my dream to sleep with a tranny! It would be the best of both worlds, beauty of a girl and acock. I want to feel her inside me! I'm just so afraid to actually do it. I have looked at many local ads. I'm afraid of catching something or even feel guilty afterwards. Any...
    LilShyCutie LilShyCutie 18-21, M 3 Responses Aug 2, 2013

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    Horizon Expansion

    It can't be so much different than having sex with any other person. I think it could be serious fun.
    troikabeauty troikabeauty 26-30, F Jul 5, 2013

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    Caught My Friend Crossdressing And What Happened Later

    I was on a bussness trip with coworkers and the hotel we where staying at shared a bathroom per two rooms. One of my coworkers is kind of afriend to me, he is no longer married and seems alittle on the Bi side but never really said anything to anyone. He sometimes acts alittle...
    hhstalegs hhstalegs 51-55, M 6 Responses Aug 22, 2011

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    I Want To **** A Tranny.

    I'm 20 looking for a tranny in Keller Texas are near by. Plz if any one is a tranny are a girl wanting to have sex are get into a relationship let me know.
    Mwreimer1993 Mwreimer1993 18-21, M Oct 15, 2013

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    Love It

    I have a friend who is say handsome and about 44. We had a few drinks one night at my house on the screened in deck while everyone was out for the night and well I just do not know what happend. we got to talking about sex and guys and he made the comment that he was BI. Wow...
    jimmyr51 jimmyr51 51-55, M 15 Responses Jul 7, 2009

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    Want To Try It.

    I'd love to try having sex with a tranny both ways giving and reciving. Anyone in Colorado know anyone like that?
    Ch3d3rbob Ch3d3rbob 18-21, M Oct 13, 2013

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    What To How Sex With A Tranny

    I been wounded for some time now about howing sex with a tranny any I'm Tampa fl that would help me with this
    Honduras1 Honduras1 31-35, M Jun 26, 2013

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    I Would Love To

    i would love to have sex with female ts. any female ts can message me. I would love to chat!
    pinedurby123456789 pinedurby123456789 22-25, M 2 Responses Jul 3, 2013

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    Tranny Topped

    I would love to be tranny topped. The breasts on my back...... The feel of soft skin. The best of all worlds!!
    ShaverII ShaverII 41-45 3 Responses Jan 3, 2011

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    Swallowing Tranny ***

    I love to kiss and worship the bulge in a tranny's panties, and then slowly kiss her thighs. It's so erotic to slowly pull her panties to the side and free her clitty ****. The moment when I first see that tranny **** is so amazing. Then I love to slowly suck on it and feel it...
    sissynikkicd sissynikkicd 41-45, M Sep 17, 2013

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    I Want It

    for years  pull my self thinkin of rooting a  tranny from behind playing with her **** and **** then have her **** me bareback
    thebigon thebigon 22-25, M 2 Responses Dec 1, 2009

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    My Neighbour

    I've had a few experiences with Tranny's in the past, mostly escorts. Some were good, some not so, but I've never lost interest in the occasional encounter. Recently I met a shemale online who as luck would have it lives in the same apartment complex as me. After chatting for a...
    BananaMeltdown BananaMeltdown 31-35, M 3 Responses Nov 15, 2011

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    Talk

    If any TVs wanna call me for some fun message me
    thecub1 thecub1 22-25, M May 16, 2013

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    I Guess I'm Being Selfish...

    I have a gorgeous t gurl FWB, but I'm looking for another one in the Louisville area. Safe play only... I'm very oral and love sucking and will bottom for the right ****.
    kinkymale40165 kinkymale40165 36-40, M Jul 6, 2013

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    Ftm Tranny

    Most people think that trannys are MTF (male to female). They imagine a woman with a ****. What people don't realize is that "tranny" goes the other way too. There are plenty of FTMs in the world (Female to male). I am one of them. I'm a dude with a ***** and a rape fantasy who...
    SJThornton SJThornton 18-21, M 5 Responses Feb 26, 2011

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    I Been With My Mom's T-girlfriend

    Since my mom was div, she became bi but she did not her girl friend was not a woman till in the bed. She dated with my mom over 2 years. We started our expereince since he caught me playing my moms lingerie in her room. then she knew I found her secrets too.
    20smale 20smale 18-21, M 3 Responses Dec 25, 2011

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    Highly Recommend It

    I've done it and must say some of these girls are hot!  **** and *** with a little twist!  It's an experience above all others!
    haileeTV haileeTV 41-45, T 1 Response Jan 14, 2010

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    A Little Shy..

    I'm a 17 year old girl that's turning 18 in 3 months and I really want to have sex with a TS. It just looks hot.
    mysteriousgurl23 mysteriousgurl23 18-21, F 1 Response Jul 3, 2012

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    Mind Blowing

    I'm here to say that the sex is mind blowing with the right girl. I had a girl when I visited Salt Lake City and we kept going for hours, and I mean hours. It took every bit of strengh I had not to *** right away. She was so clean and LOVELY. I licked her *** like it was a...
    Bill4756 Bill4756 56-60, M Oct 26, 2012

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    Would Love A Tranny Housewife

    Would love to find a trans housewife who's just as comfortable in shorts and keds as she is in heels and lingerie. Would live for her to be a stay at home girl, cooking and cleaning during the day, then letting me try to knock her up all night.
    deleted deleted 26-30 6 Responses Mar 8, 2013

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    Indiana Transexuals.

    Are there any from Indiana on here who would like to meet?
    Kingsludge Kingsludge 18-21 Jul 14, 2013

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    Once Was Not Enough

    I have only been with one tgirl. I would love to find another. I was in the food court at the mall just a few blocks from my office grabbing lunch when I saw her. She looked 18 or 19, 20 at the most. A cute emo type girl wearing a white blouse, a dark red skirt and thigh...
    live2sin live2sin 36-40, M 1 Response Jul 21, 2012

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    First Touch..

    i recently met a beautiful tranny.she touched me penis and instantly i was hard and dripping pre-***.ive fanasized about it for years.she had to go so we couldnt have sex and i dont know when ill see her again.this would be my first tranny.my only similar expierence was...
    maxxxpower maxxxpower 22-25 Oct 28, 2009

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    My Friends Wife Asked Me To **** Her Husband

    I have a friend that is bi sexual and a real sexy tranny. I had an interesting evening with both of them a while back where he was all dressed up as sexy as any hot woman. That night I found myself wanting to have sex with him again but did not want to go around his wife to get...
    hhstalegs hhstalegs 51-55, M 10 Responses Aug 25, 2011

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    On Hunt For Tgirl In Sa Tx

    I love trannys i wanna meet one in sa tx so bad i love everything about them
    twhahn twhahn 22-25, M 1 Response Oct 16, 2013

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    Ok Ok, I Am Curious!

    i'd love to try it.  the beautiful soft skin of a woman.  sweet gentle curves of breasts. and a ****.  i consider myself straight, but i would so LOVE to try this.
    georgesmith2008 georgesmith2008 36-40 1 Response Feb 18, 2010

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    I Had Sex With A Beautiful Tranny

    It was a Thursday about 9 years ago,and i'd decided to go out,i'd looked up a bar in West London called Ted's Place in Fulham,it looked ok,so i got my self made up,put on a little black dress,tights and heels jumped in my car and off i went.Got there about 9.45pm,parked the car...
    sheerdesire sheerdesire 46-50, T 14 Responses Sep 28, 2011

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    Just Curious

    I am hoping someone will satisfy my curiosity. I am new , and hoping someone wants to show me what i have been missing
    MJC67 MJC67 46-50, M Aug 8, 2013

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    It's been a really big fantasy of main

    for a very long time now. I would love to meet one so maybe we could act out some of my fantasy. if any takers hit me up and lets see if we hit it off.
    LeeIII LeeIII 36-40, M 1 Response Jun 17

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    Crossdressing Halloween Surprize

    I had been invited to a halloween party at some friends of mine home, I decided to just drop by for a minute then leave. When I got there I noted that one couple was crossdessed, she was dressed as a man and he was dressed as a slutty woman. I found myself drawn to him so I went...
    hhstalegs hhstalegs 51-55, M 5 Responses Nov 7, 2011

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    20yo Ts Looking For Friends

    Hi, I'm 20 yo TS who would love to meet some cool guys who are down with my lifestyle, or curious at least. I'm nice, fun smooth and very feminine. I have implants but everything else is real. Send me a message if you would like to chat...
    ladyboi20 ladyboi20 18-21, T 28 Responses Apr 30, 2012

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    Tranny ****

    i will admit that i do like to watch tranny **** (or shemale ****) which ever is the correct term for it. most of them are so damn hot, with their beautiful figure, massive boobs, slim figure and their sexy ****. i would love to bring home a tranny and bring her to my room. i...
    YoungFreeSingle1 YoungFreeSingle1 18-21, M Jul 6, 2013

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