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I Want To Experience Sex With A Shemale

Personal Stories, Advice, and Support 1,218 People

    Something New

    I'm a bisexual guy, I came out around 4 years ago, I was 16...I've had sex with guys and women...I've had **********...but I want to try something new...recently I've realized that I get really horny when I see pictures of TGs and I've started watching shemale ****...I'd love to...
    jonjon93 jonjon93 18-21 2 Responses Sep 30, 2013

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    Sharing The Dream

    Yes I do. I want to be with an asian shemale. I want to experience that totally sexy sensual feeling of being with a sex that is between two sexes. To feel her, taste her, kiss her and hold her. To look into her eyes and let her know I want her and appreciate and desire her. To...
    crisean crisean 46-50, M 2 Responses Dec 15, 2011

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    Shemales

    being a sissybitch love going to thailand and meeting ladyboys who are so hot and sexy!!love them whether they have big **** or not so hot!!first time with shemale was when i was in another city on business and had tried to stop being a sissy and ended up in a tranny club and...
    mandiejune mandiejune 51-55, M 1 Response Jun 24, 2011

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    Making Out In A Bar

    There is a bar in Phoenix that I went to one night around Halloween last year. I didn't realize it was a tranny bar until I went inside. I was so excited and turned on. I went to the bar and ordered a drink. A girl came up to me and we started talking. I knew she had a little...
    jessicahartts jessicahartts 26-30 8 Responses Aug 17, 2011

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    I Need Sex With A Shemale

    Maybe someday I will get to know the person. I want to have sex with a shemale. Reading your experience on this EP do not have to be afraid - I can just have fun :)
    viki19 viki19 18-21, F 8 Responses Jun 6, 2012

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    My Wife And I Are Wanting The Experience

    this is what we really wish for. we have had long talks. talk is over now we want experience it with you, game night? lets become friends and get to know each other
    daywane daywane 46-50, M Aug 29, 2011

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    ...with My Girlfriend Watching

    I have a fantasy involving a ********* with my gf and a well-endowed She-male. I could watch as my gf is ****** then she can watch as the she-male buggers me with her superior ****. We can then both take turns sucking her penis. My girlfriend has tiny little ******* and I have a...
    litlebigman2 litlebigman2 51-55, M Jun 17, 2012

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    My Confusion

    Im gonna try to summarize my life in a few lines: When I was a little kid aroun 4 - 6 years old I used to play "the doctor" (getting naked and touching) with some of my male friends My mom caught me several times and just looked at me in a really dissapointed way I tried once...
    nesnes876 nesnes876 22-25 2 Responses Apr 24, 2011

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    Wondering

    I had sex with a man when I was young. I have had sex with women since. Watching shemale **** absolutely turns me on and I think the sexual experience would be sensual and uplifting. I wonder if there are any that would be interested
    loffe9 loffe9 66-70, M 10 Responses Apr 6, 2011

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    If She Would

    i know this girl, absolutly loves shemales, she addors funinary and all sorts of things in the lines of she males, and im sorta on the scope myself, i wear panties and crossdress daily throughout my streets and home town, but non one ever trys to pick me up, (wish a girl would...
    meryl007 meryl007 22-25, M 3 Responses Nov 15, 2011

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    Making Out In The Changing Room.

    One late night as i was doing my window shopping, i came across a shop that sells sexy ladies clothing & i spot a very short miniskirt, which measure only about 20cm long. It was a black jeans miniskirt ! It was my love at first sight on this skirt. As i was looking at this skirt...
    cdson cdson 26-30 1 Response Jun 21, 2013

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    Hungry

    I have always been curious about shemales. I have always wondered what it would be like to be with one.
    natenrw77 natenrw77 36-40, M 1 Response Oct 18, 2013

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    My First Time

    I had sex with a shemale on New years of 2013. It was the hottest thing ever. It was with this babe: www . babynikkitrans . blogspot . com Sexy as ****!!!! She had a perfect body. The yummiest ***, and a delicious large **** shoved in both my mouth and *******. The funny part is...
    lsweety999 lsweety999 22-25 Jan 5, 2013

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    Meet

    I would love to meet a shemale and have an experience of a life time....any takers?
    TheJames1 TheJames1 22-25, M Jul 16, 2013

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    Cathy

    ive only ever had one sex session with a she male her name was cathy please feel free to read about it in my blog under 'Cathy'
    gina999 gina999 41-45, M Jul 3, 2011

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    I Want To Be Shemal

    I have always wanted to have a female body and a couple of years ago I started taking female hormones, things happened fast for me my chest started to tingle and feel sensitive and sore, I kept my doses really low so the guys at work would not notice. I took this low dose for 2...
    iloveladyboyscock iloveladyboyscock 26-30 4 Responses Oct 5, 2013

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    Shemales

    being a sissybitch love going to thailand and meeting ladyboys who are so hot and sexy!!love them whether they have big **** or not so hot!!first time with shemale was when i was in another city on business and had tried to stop being a sissy and ended up in a tranny club and...
    mandiejune mandiejune 51-55, M 2 Responses Jun 24, 2011

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    I Have Had Sex With A Shemale

    When I was much younger and living in the big city, I got nearly blacked-out drunk one night and picked up a pretty feminine shemale. She gave me great head, and I ****** her most of the night before finally passing out. I didn't realize what had happened untill the next morning...
    luvtoswallowblkcum luvtoswallowblkcum 51-55, M Oct 18, 2012

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    Shemale Sex

    I have for the longest time wanted to have sex with shemales. I am a bisexual married man (wife does NOT know). I love eating *****, sucking ****, giving rim jobs, sucking ****, and having my **** *** ****** by men/ women ith strapons. The ultimate sex experience though would be...
    will1956 will1956 51-55, M 2 Responses Apr 3, 2012

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    This Has Been On My Mind For So Long

    I want to **** her and suck her and then have her do the same to me
    deleted deleted 26-30 Jun 17, 2011

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    Hi I'm Deaf I'm George

    I need shemale **** my *** I can't look shemale
    Cooldeag64 Cooldeag64 22-25 Aug 7, 2012

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    A Few Ideas

    This is a relatively new fantasy for me. I can just imagine the soft feel of a woman, her soft breasts against mine, gentle kisses, long hair, and her hard **** ******* in and out of me. The quiet moans we make as we embrace while she's inside of me. Mmmm. Then her pretty...
    AmyLloyd AmyLloyd 31-35 5 Responses Jul 13, 2011

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    Wants To Pleasure A Shemale

    Several years ago in New Orleans, I had a date with a shemale prostitute. At that time my only interest was in being pleasured by her. She sucked my **** until I came several times. I have since had sex with males, but, again, I was the one receiving the pleasure...
    CuriousBottom69 CuriousBottom69 41-45, M 1 Response Oct 6, 2013

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    Sexual Fantasy

    I've always considered myself to be straight because I'm a genetic female and I've only had sex with men. However, I've always wanted to have sex with a TS woman. I imagine it to be the best of both worlds. It seems so difficult to be able to fulfill this fantasy.
    brownsugarluv88 brownsugarluv88 26-30, F 8 Responses Jul 12, 2013

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    Fantasy With A T

    I fantasize about a much better hung she-male ******* my *** while teasing me about my tiny ****. It would be fantastic if my girlfriend or any other girl was to watch my humiliation.
    litlebigman2 litlebigman2 51-55, M Jan 5, 2013

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    If You're A TS Girl Looking For A GG This Is For You

    Hello ladies. So as you may or may not know I'm a genetic woman. My fantasy has been to get laid by a TS woman. I'm always up to chat on yahoo. There's an app called yahoo messenger or it can be done on the computer. Web cam can also be done from yahoo messenger even on your...
    brownsugarluv88 brownsugarluv88 26-30, F 1 Response Jul 12, 2013

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    I Want To ...

    Well I think I want to . I've often fantasied . But , lately , it feels like I want to . Really want to . But I don't know how to start . or if I should .I could use your adviice .
    deleted deleted 26-30 1 Response Sep 26, 2011

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    Fantasy!

    I have always wanted to be with a women and find a nice hard ****. I have always liked surprises!  
    hotcoyote hotcoyote 56-60, M 2 Responses Oct 12, 2012

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    While I'm Tied Up

    I love being tied up during sex. I love to be controlled by a woman. I want to experience being truly submissive to my captor. To have a beautiful sexy woman be able to **** me hard while I am at her mercy. To have a **** shoved in my mouth but be looking at a beautiful woman...
    pmikey pmikey 46-50, M Aug 17, 2011

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    I want to suck a shemale's ****

    I would love to have sex with a she male, playing with her **** and her **** and kissing her lovely lips. I want her to **** me in the *** and suck my ****. I want to suck her **** and **** her ***, caressing her stockings and stroking her soft long hair. I want to...
    deleted deleted 26-30 May 19, 2012

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    New Experience

    Hello All, I'm a 34 Year Old experienced Dom. While I consider myself a lesbian I am very intersted in being with a shemale. By that I mean someone who is actually a T-girl, not a guy dressed in womans clothing. I would love to take an actual T-girl as my slave. Your Queen...
    MistressTiffany12 MistressTiffany12 31-35, F 1 Response Oct 17, 2013

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    Possible Bucket List Item

    I've had lots of sex with all different types of men and a few women. I know several TVs and TSs and find them very sexy and erotic. I would love to have sex with one or all of them (wink). Somthing about the softness of a woman with the **** of a man at the same time...
    AmyLloyd AmyLloyd 31-35 6 Responses Jun 30, 2011

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    I had sex After I Found My Hubby's secrets

    I am a bi female. I never paid attention at crossdressing and shemale things until 2 years ago, some clues that my hubby might be a cd, were caught randomly. I got frustrated but started getting into those m2f things such as cd, tranny, shemale, sub. Once, when I was in my...
    cindymwf cindymwf 41-45, F 18 Responses Feb 11, 2012

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    Related Experiences

    Well I owe my father something because he took the blame for something I did once! I think he wants me to blow him but I am not sure! I am bi but he doesn't know! How can I get him...
    jackbx jackbx 13-15, M 1 Response Aug 15

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    My father is fat and hairy!
    Bulkver Bulkver 36-40, M Aug 13

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    I want to talk with anyone about... I dunno, stuff. The new boots I just bought, or the guy at work I like or whatever, I dunno. I DON'T want to talk about your penis, sex...
    CaseyGirl97 CaseyGirl97 16-17, F 12 hrs ago

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    I Havnt actually had an experience yet . My fwb and I have sext with couples and I find it Hott sexting with other females . It's fun when I'm at work and well my bf def gets the...
    Noismkr Noismkr 31-35, F 2 Responses Aug 13

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    I've wanted to experience making love to a virgin all my life and be the one to make it happen, but wasn't able to find someone to experience it with.. Just being that person that...
    kidswiss kidswiss 22-25, M 1 Response a week ago

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    I want to talk with anyone about... I dunno, stuff. The new boots I just bought, or the guy at work I like or whatever, I dunno. I just DON'T want to talk about dirty or pervy...
    CaseyGirl97 CaseyGirl97 16-17, F 1 Response 12 hrs ago

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    I really want to have great mind blowing sex with someone I love.
    Skywalker1979 Skywalker1979 31-35, M 1 Response Jul 31

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    I think i would be great to have sex with a trans women. They are really gorgeous but also independent in a sense. I'm not gay but I definitely want to go for a transvestite woman...
    lolzmeplz lolzmeplz 16-17, M 4 Responses Aug 4

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    This is something I want to try I have never even dated a black man much less had sex with one but there is a first time of every thing right ??
    1Miserablemind 1Miserablemind 18-21, F 8 Responses Aug 5

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    Do you think anyone apart from your partner would want sex with a pregnant woman??
    HanEK HanEK 31-35, F 26 Responses Aug 9

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    I want to have sex with woman while my boyfriend partipates however he wouldn't **** her or lick her. She would lick me while my boyfriend ***** me and I would return the favour to...
    Readingaddict Readingaddict 18-21, F Aug 9

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    I have never had sex with a condom simply because me and my man wants to start a family. We haven't had sex in 3 years due to log distance but hoping he comes soon from South...
    roselani2005 roselani2005 26-30, F 6 Responses Aug 17

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    I miss having sex.... But I want to have meaningful sex with someone I love. I don't have anyone like that in my life yet. :(
    Grapemonster Grapemonster 22-25, F Aug 19

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    I really want to have crazy sex with my sister
    Harryharry123 Harryharry123 22-25, M 5 Responses Jul 30

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    I have always had sex without condoms. It feels better and is natural. This year it finally all caught up to me and now I'm 5 months pregnant. However that won't stop me and I'm...
    wanting1992 wanting1992 18-21, F 12 Responses Aug 18

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    I had sex with my teacher in year 9 in the school pool. It was great.
    zacisbest45 zacisbest45 16-17, M Aug 16

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    Numerous times started when I was 16 they were in their 30's was having sex with 3 of them stopped after I turned 22
    Ant35 Ant35 31-35, M 3 Responses 4 days ago

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    I love sex without protection! Love to feel every ridge and vein. Ask me more in the comments and I'll answer... Gotta avoid those that watch since they are blocking my stuff now...
    catiemae87 catiemae87 26-30, F 27 Responses 3 days ago

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    Please re