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I Want To Experience Sex With A Shemale

Personal Stories, Advice, and Support 1,211 People

    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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    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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    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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    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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    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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    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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    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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    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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    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 17 Responses Feb 11, 2012

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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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    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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    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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    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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    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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    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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    ...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 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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    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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    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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    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 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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    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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    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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    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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    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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    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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    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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    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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    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 7 Responses Jun 6, 2012

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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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    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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    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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    Related Experiences

    I love my dad more than anything and wish I could have sex with him.
    JeremyCooper JeremyCooper 16-17, M 3 Responses 1 day ago

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    My dad is hot. I like it when he touches me.
    gayandproud13 gayandproud13 13-15, M 7 Responses Aug 31

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    I want to have sex with a female teacher in my school teaches maths,she's not attached and is only a mere 22 years old she has an a body like an hourglass,all the curves in the...
    TheGamechanger TheGamechanger 18-21, M 1 hr ago

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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 2 Responses Aug 21

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    hi i am from new delhi india i want to have sex with a sexy girl i will pay her gd bt i dnt hv ma prsnal place to **** plz help me out wht to do
    sexyboy034 sexyboy034 18-21, M 1 Response Sep 2

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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 hate how ppl who don't know me look at me and think I'm not a virgin...like wtf? And I hate how some people I know always tell me "just do it" "you're too pure" "gotta do it...
    Midnightangelx Midnightangelx 16-17, F 1 Response 5 days ago

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    I want to have sex with one so bad, like 14-15. (Im 16 btw, it wont let me change it)
    Gaywhore9 Gaywhore9 18-21, M 2 Responses 1 day ago

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    17 year old boy looking for a older man of any age to have sex with me! I'd do anything you want so message me?
    benw19 benw19 16-17, M 1 Response Sep 10

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    I love having sex with my boyfriend. We have the best sex ever!! I belief sex is very important in a relationship.
    Nathaly22 Nathaly22 18-21, F 4 Responses 5 days ago

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    Even though we don't have a label on our relationship, I still want to have sex with him and kiss him and hug him and cuddle . I like the way he feels inside of me . I don't know...
    neuroticgal neuroticgal 22-25, F 3 Responses 5 days ago

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    My girlfriend has been having sex with other guys, about 2 of them she had sex with multiple times
    jma13f jma13f 18-21, M 1 Response Sep 7

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    I have sex with my cousin all the time do you want to hear the stories ? ;)
    Vannnessaaaaa Vannnessaaaaa 18-21, F 24 Responses Sep 7

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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 Aug 25

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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 26 Responses Aug 25

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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 Aug 28

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    I love sex without protection, love being inside a women, and feeling every sensation....
    red1235 red1235 41-45, M Aug 31

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    I love having sex with strong young guys so they can hold me tight and never let go.
    Irishsunglasses Irishsunglasses 18-21, F 1 Response Sep 4

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