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I Love Shemales

Personal Stories, Advice, and Support 1,710 People

    My First Experience..

    ..it was in Hamburg that i tried the first time a shemale...i chatted with her at adultfriendfinder and we made an apointment..i was very nervous and excited, so i went of from where i lived towards the "reeperbahn", the well known redlight-district of hamburg...i had a map...
    scatlover1969 scatlover1969 36-40, M 1 Response Oct 4, 2011

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    peteadams peteadams 31-35 1 Response Apr 14

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    My Story

    Well I deep in my heart I want so,so much to be shemale.I for yrs have been in the closet.I SECRETLY DRESS,I am not that good at dressing/make up,I want to be pretty. Honestly as a child I secretly dressed in moms cloths,I loved it,well I dare not let know one find out,my first...
    1sheila 1sheila 41-45, M May 23, 2013

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    My Ultimate Fantasy

     I am a straight male but for some reason i love to see a beautiful women with a throbbing hard coc*. I have no idea why it turns me on so much something about having an elegant beautiful shapely women with a huge penis gets wheels turning. I would love to meet a beautiful...
    shemaleboner30 shemaleboner30 18-21 3 Responses Oct 6, 2009

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    I Married Her!

    I started dating a trans woman almost three years ago, and this April we got married in Puerto Vallarta. On my birthday, which was ******* awesome! It was actually a little weird. My parents are Mexican and really conservative, but they didn't say anything even though I could...
    jojokarel jojokarel 26-30, F 9 Responses Sep 1, 2013

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    I Love Tgirls

    I have been with several tgirls, nothing can beat a hot girl with a big ****.
    deleted deleted 26-30 5 Responses Jun 4, 2012

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    Shemales - Love Em

    I have always loved shemales. A woman with a coc* is so arousing. I love it when they still can get hard and like showing it off. I even like hermaphrodites. They are nmore arousing because you can have best of both worlds, a coc*, a pus*y, a*s, and ti*s all in one. Ummmm ...
    BarbieB BarbieB 56-60, M 24 Responses Aug 1, 2008

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    I Have.

    I have and I loved it. I only go for the girls that bottom because I feel like most women want to be treated and made love to as women. The thought of a girl topping me is not a turn on!
    odiscordia odiscordia 36-40, M 1 Response Jan 20, 2013

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    Ladyboy Shemale

    I meet a lovely kind and fun girl who tuned out to be a ladyboy. Is it wrong to date and be sexually attracted to the same sex?
    abrogerh abrogerh 51-55, M 1 Response Jul 28, 2013

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    The Best There Is

    I have been with a number of transgendered girls and I must say they have all been a slice of heaven.I was as nervous as a jackedoff house cat my first time,but Brooke put me at ease right away.After chatting awhile we started hugging and kissing.She was in lingerie and it left...
    daldav daldav 61-65, M 4 Responses Nov 11, 2010

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    My Wife Is One....

    Simple as that. The most wonderful girl in the world, designated male at birth, and lived lived less than half of her 20 years as a boy. The best of both worlds. So loveable! :-XPXP
    TGLove TGLove 18-21, T 1 Response Apr 24, 2013

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    My Shemale Experience

    A straight married male friend of mine dared me to dress in drag with him, and go out for Halloween. We were to have a contest to see who could come the closest to passing as a female. I prepared in advance, collecting the necessary garb, make-up, wig and heels; the whole nine...
    deleted deleted 26-30 4 Responses Jun 1, 2012

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    Shemales Are Hot!

    I been out with several shemales. What a great combination-A beautiful fem body with a hard hot ****. I've enjoyed having hot sex with them. I can be both the top and bottom-give and recieve with the same person. A great turn-on.
    TamponPanzee TamponPanzee 51-55, M Sep 19, 2012

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    Anyone?

    Shemales are so hot. My friends say: "Wow. Your so stupid for liking shemales." Or something close to that. I've always wanted a shemale girlfriend/boyfriend. If there are any that want to idk maybe have a relationship comment below? :D
    Shark411 Shark411 18-21, M Feb 21, 2012

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    The Latest

    I recently met a t-gurl in Craiglist. Josie (short for Joselyn) a nice slender Mexican gurl. A lot of the Latina Gurls where I live in CA do not usually go out with AA men, so I was sure to let her know my ethnicity, and she was cool with it. I'm experienced with T Gurls and I...
    odiscordia odiscordia 36-40, M 1 Response Jun 23, 2013

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    Want To Try One

    I have never been with a shemale but have looked at them in books and online. Most of them are beautiful looking woman with very nice breasts. But under their panties is a big ****. Being able to play with their boobs and suck their nipples and them go down to find a big...
    davis36a davis36a 61-65 17 Responses Oct 7, 2010

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    Beyond Erotic...

    Any shemales reading this I must say I have never seen anything on this Earth as erotic and sexy as you. I'm unable to truly express my thoughts except to say WOW! What a fantastic world we live in.
    hertoy hertoy 61-65, M 8 Responses Dec 7, 2010

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    She Was Taller Than Me and Her Eyes Were Magical

    I love shemales. It’s almost … well it is actually obvious … that this statement is a fantasy rather than an experience for everyone else here. There is nothing wrong with that. But, perhaps a dose of reality could lend a little more credence and seriousness...
    CherrySissy CherrySissy 46-50, T 6 Responses Sep 17, 2008

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    Shemale Date

    i have been out with a few shemales and love it ,the best of both , a nice **** and soft breasts
    aliciasuks aliciasuks 51-55, T 4 Responses Feb 16, 2010

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    I Need A Shemale

    I need a shemale to serve and work for
    Bigdick699 Bigdick699 22-25 Oct 1, 2012

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    I Really Want To Meet A Transsexual Women!

    I have always wanted to lose my virginity to a transsexual women from the moment I watch a **** with a "shemale" in it and from then on thats i can think about see i live in Fl and i cant seem to met any transsexual women.I have tryed many websites but I can never seem to find...
    BrEnTtHeMan4 BrEnTtHeMan4 22-25, M 1 Response Aug 5, 2013

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    Shemale *********

    Shemales without question are some of the most erotic creations in this world. If you are a straight man, you have the option of staying that way with the ****, mouth, and ***. But if you want to experiment, the **** is right there. And if y ou are a woman, you have grand...
    Quest75 Quest75 31-35, M 2 Responses Apr 4, 2010

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    Shemales

    It is nice to see that there are people that love us. Believe me, there are a ton that hate us like no tomorrow. I really do not understand why people cannot understand that there are many gender blends...trans, cis, dualed. And more. And all my sisters are lovely gentle...
    Danielle60 Danielle60 51-55, M Oct 29, 2013

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    The Bus Ride

    It was getting late. The sun went down. The tiny Southwest town was nothing more than a bus stop with a  general store gas station combo with a trailer for house on the other side of the street. I got on the bus just before the driver was about to leave. Lucky for me my last...
    Bootydude Bootydude 56-60, M 4 Responses Mar 27, 2012

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    Thresome At The Marriot.

    a couple of months ago, i responded to bp ad for 2 asian tgirls. when i got to thier room, a young petite asian girl answered the door. she was friendly and sexy. she asked if she liked what i saw, and them showed her perfect c cup breasts and said suck my nipple while my gf is...
    cockadmirer cockadmirer 31-35, M 2 Responses Oct 28, 2012

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    I know most shemales are gay

    but I would love to have sex with one. I think I'm starting to gain a thing for them. Like I love boobs and I love **** give me both in one and a pretty "girl" what more can I ask for.
    BiRacialGoddess BiRacialGoddess 22-25, F 5 Responses Jul 24

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    First Time With A Tgirl

    Hi i would like to write about my first time with a TGirl .I arrived at her house around 9:30 pm , i remember when i pulled up to her house and before i knocked on the door i was really nervous and shy yet very intrigued . I meet her a few weeks ago at a gay trans friendly night...
    cam2088 cam2088 22-25, M 2 Responses Mar 9, 2013

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    Need A Shemale **** To Play With!!

    Wanna experiment my bisexual side with a shemale who has a nice **** and breats ;) I wanna taste sucking a ****, making it big on my mouth and taste it as it **** into my mouth.. Makes me horny and hard as i dream of it.. My *** craves for that **** now..
    Ladyboyy30 Ladyboyy30 31-35, M 2 Responses Jun 6, 2012

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    I Love Shemales

    I find them a lot on LA back page. I love then so much. I'm such a straight guy. But I love them, I'm obsessed. In LA they look like models and aren't cheap, but it's worth it. I love to get a very pretty one with big implants. First I like to make out. I like or tounge a to be...
    hideme66 hideme66 26-30 Jun 16, 2013

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    Not Yet, But...

      Another huge fantasy I have is related to a woman f**cking me with a strap-on. It's to have sex with a true transsexual. I want to see her ******* bounce arund as she strokes in and out of my behind until she shoots hot **** up my ***!
    dab37863 dab37863 56-60 4 Responses Oct 24, 2008

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    I Need Help Someone Please Help

    I need to speak with either a shemale or someone who's been with one so I can better know what to expect I'm new to this and I would love to get some advice
    Bigdick699 Bigdick699 22-25 Oct 1, 2012

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    My First Time With A Shemale, Part 1

    In the mid 90’s, I used to live in a border city and would go across to Mexico to party. When I was not able to close the deal with one of the local girls, I would head down to Boys Town and look for a pro to take care of my business. At some point, I was “warned” by a...
    amantelatino03 amantelatino03 51-55, M 2 Responses Jun 14, 2013

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    I Want A Shemale

    i love shemale i love shemale ***** and *** i wanna become a **** to one
    Poo1000 Poo1000 18-21, M 3 Responses Oct 23, 2013

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    Sex With Shemales

    I'm a str8 guy but I've been ducking shemales for many years now. Usually ill meet them off Craigslist or the Chatlines. Once in awhile ill meet one who loves raw **** and she becomes my regular. I jus love 2 suck a nick hard she **** til it squirts its sweet juice in my eager...
    iluvshecumwet iluvshecumwet 31-35 2 Responses Jul 27, 2013

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    Thugish

    Hi everybody, I'm Katrina. Majority of my life, I've been crossdressing. Its been a tough road. I've never been a sissy, because my mother was a strong lady of the house. I guess, I take after her. I use to get pick on till I fought back. There's times, I went thru racism...
    Jedimindtrick39 Jedimindtrick39 36-40 6 Responses Jul 26, 2013

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    I Find It Funny ( As In Ha Ha & Odd )

    I will begin by telling you I 'am a Shemale Dominatrix. I have an extreme fetish for black kidskin leather gloves & a black leather everything I can wear fetish also. I presently have 7 slaves that I see on a regular basis. I have such a love of torture. Therefore you can bet My...
    evaevil evaevil 41-45 6 Responses Mar 13, 2012

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    15 Years Ago

    Well about 15 years ago in my party days I was out drinking one night I had been drinking heavy and started driving home and got stopped well needless to say I got taken in.It was the weekend so I couldn't post bail until Monday morning,so I had to stay in the drunk tank. Well...
    johw johw 51-55, M 4 Responses Nov 28, 2010

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    Lactating Shemale

    Hi, Rachel Here, I am a lactating Shemale, ,I get so horny when I do manual nipple and breast stimulation ( 4 or 5 times a day) or use my breast pump. I got into lactation because as a Shemale I wanted real breasts, I took a course of natural hormones which worked superbly to...
    femi9 femi9 46-50, T 1 Response Mar 7, 2010

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    If There Weren't So Many Of You ...i Wouldn't Believe It.

    Although I should note that I am a young man just a few months out of my teens ...I guess it is more appropriate for this group to know that I have been raised and lived most of my life as a daughter and a sister.  The causes and reasons why are lengthy at best and still of...
    kayleew2000 kayleew2000 18-21 9 Responses Sep 4, 2012

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    Omg, I Get Turned On Sooo Much By A Girl With A ****!

    Im a young girl, I enjoy both men and women. However, whenever i ********** i find that not matter what i start watching or reading it always leads me to watching T/S ****, like ******* every time. I cant explain specifically why i get so hot, i just do. Some of the things that...
    thatgurl52 thatgurl52 22-25, F 4 Responses Apr 6, 2012

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    Heyy (:

    If anyone wants to **** my tight virgin *** msg me u have to live in fl srry!! (;
    BrEnTtHeMan4 BrEnTtHeMan4 22-25, M 1 Response Aug 26, 2013

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    My Experience With Cassie

    My experience with Cassie, the big black transsexual girl I had decided to visit, was nerve-wrecking at first, but a wonderful experience in the end. I drove 35 minutes to see her...nervous about what neighborhood she might be in and what attitude she might have. I was excited...
    frank23198 frank23198 46-50, M May 28, 2013

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    My First Time With A Tranny

    Yes, like so many other shemales lovers I consider myself straight. Lol. I've spent my whole life having gorgeous girlfriends and sexy women over for one night stands. I was in the military, I love hunting and fishing. But a tranny is the most sexy thing in the world to me. It...
    hideme66 hideme66 26-30 1 Response Jun 12, 2013

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    I Am From Algeria And I Wanna Have Experiance Weth Shemal

    just i wanna going to USA for live wth shemal because i can't in my contry
    deleted deleted 26-30 2 Responses Jun 6, 2013

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    No Story

    Just wondering were in the north Florida area can you find shemales that would like to show me the wonder of all there sexual gifts.
    slapstic slapstic 56-60, M Aug 30, 2012

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    F#cked By A Shemale

    I am a straight acting guy, 33yo, married, kids, ect.... I have had bi experences in the past (closet bi lifestyle). When I was in my early twenties, I had a handful of encounters with shemales. Three different girls, one of them and I hooked up often for a stretch. Of these...
    jcks1979 jcks1979 31-35, M Sep 4, 2012

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    I Love Shemales

    i love the **** with the pretty ones with titts.  i am a women and i would love to have sex with a shemale.  some of them are so beautiful.  my goodness are they sexy.  not the ones that just wear bras but the ones that take the time to shave and look like a...
    ldylace ldylace 46-50, F 5 Responses Jan 26, 2010

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    In Love With Shemales

    Im in love with shemales I don't know how to handle this my biggest fantasy is to be with a shemale I wanna feel what its like to feed this craving I been in love with shemales since the first time I seen one on the internet. I just want to meet some transexuals any shemales hit...
    eflo4811 eflo4811 26-30, M Nov 17, 2012

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    Tried It And Liked It

    I've been with one shemale, i have to say it was a great experience. She got me to try things that i never considered before and to this day i wish i could have more play time with her. But we fell out of contact, so now i'm looking for a new shemale to play with.
    isdintrepid isdintrepid 26-30, M 4 Responses Dec 16, 2011

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    I Have Fantasies....

    i have fantasies about my husband bringing home a beautiful woman and asking me to have sex with her, only to find out that she has a ****..... omg i can picture him/her asking me gently to get on my knees the pulling out his(her **** and asking me to open my mouth...... then he...
    ladybijou ladybijou 36-40, F 15 Responses Jul 26, 2011

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    Related Experiences

    I'm extremely attracted to tgirls and shemales with big c*cks if you are one of those message me
    Thatoneguy72826 Thatoneguy72826 18-21, M 1 Response Sep 26

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    So my guy is not gay.. Far from it, but he's very very curious about tgirls and gets real turned on by movies or pictures even the though of a woman's body with still male parts...
    megansunshine megansunshine 18-21, F 4 Responses Oct 8

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    I love them sexy ladies but too bad I can't find any :( #sadmoment
    JimmyDlove JimmyDlove 26-30, M 1 Response Oct 6