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I Have Had Sex With a Transexual

Personal Stories, Advice, and Support 236 People

    Well I Am One

    Im a full time trans. Ive also had a trans gf once, and did casual with another. had another lover who eventually became trans. I like playing with them, but end of the day... i still need that man to **** the hell outta me hahahaha
    WhiteMushroom WhiteMushroom
    26-30, F
    2 Responses Mar 26, 2013

    Different Tgirl Strokes

    I love the different ways each of my favourite tgirls penetrate me when they **** me. They all have different styles when they initially enter me and how they slide their tgirl 'clitty' in and out of me. One of them is 'rough' with me and likes to just thrust straight in...
    anykey anykey
    46-50, M
    1 Response Nov 20, 2013

    My First Time

    Well my first time was when I was 20 years old. I was so nerves, I had been searching on craigslist for weeks and looking at all of the different shemales/cds that would post on there. I myself like to dress up in female clothes from time to time. Finally one night I was at...
    wellimga wellimga
    26-30, M
    1 Response Oct 3, 2013

    The Best Ever.

    I have been with several transsexuals and it is by far the best sex ever. When they say the best of both worlds it is the truth. I can't wait to do it again.
    AustinButtMan AustinButtMan
    41-45, M
    3 Responses Aug 10, 2010

    Christmas stuffing Yesterday I went to visit

    one of my favourite pre-op tgirls I have been dying for a suck a **** all week and she did not disappoint me We met at her door, she was already just in her bra and panties, lacy and black, she looked really good in them and I could see her small 'mound' of her reasonable size...
    anykey anykey
    46-50, M
    1 Response Dec 6, 2013

    I have a few favourite tgirls

    and they all have their own style when I see them :) With A, she kisses me on the lips when I walk through the door, I hug and kiss her and when we get to her bed we just wrap our bodies around each other as we kiss, I love kissing her beautiful breasts With K, she always make...
    anykey anykey
    46-50, M
    Jan 25, 2016

    I Want To Have Sex With A Transsexual

    I've never had sex with one or even met one, but I'd really want to! So if you are one, contact me, I'd love that! And if you live in Belgium, that's even better, because I live there too :)
    TomDrum TomDrum
    Aug 26, 2013

    My First

    I've always benn interested inTS's, it was hard when I was younger because I thought there was something wrong with me. But I just couldnt stop looking at shemale ****. It turned me on so much more and I always imagined what it would be like. In my fantasies I would always be the...
    Uhtred2008 Uhtred2008
    26-30, M
    2 Responses May 28, 2012

    Still Have Fantasies

    I have had sex with many TS women and loved every moment. I am versatile when it comes to TS women, not sure if that makes me bi or bi-curious since I do not have the same desires for men. I would usually search CL and after a few emails, meet for late night passion filled...
    deleted deleted
    3 Responses Mar 28, 2011


    Here is another story about an experience with a t-girl named Lisa. I have been seeing Lisa for casual sex over the past few years. I first met her in a bar and we hit it off. I had not seen her in a while as she had moved flats and decided to contact her. She gave me her new...
    anykey anykey
    46-50, M
    3 Responses Jan 16, 2013

    Playing With ****

    She showed up fashionably late. I met her on the porch and was immediately excited by the slender young blonde that gave me a warm embrace hello. She was sweet and social while getting to know me and my boyfriend over a drink. She excused herself to the bathroom and came out in a...
    Dgirl5 Dgirl5
    31-35, F
    5 Responses Jun 23, 2013

    Duo With Two Transexuals

    One of my most memorable transexual experiences was engaging in a duo with two really cute transexuals while traveling in England. I've never sucked or been sucked so much in my entire life - it was amazing and I hope to have the chance to do it again. Unfortunately penetration...
    desiderio desiderio
    46-50, M
    3 Responses Jan 10, 2012

    Azura Just Gets Better

    This is a follow up to my last story about this lovely t-girl lady - EP Link My experience started as usual with Azura meeting me at the door and we started kissing and caressing straight away and she undressed me before I went to have a shower. When I got back from the shower...
    anykey anykey
    46-50, M
    2 Responses Jul 26, 2013

    Online Hookup

    I was away on a business trip for a few days. One evening in the hotel I was idling some time away on the internet prior to going out for the evening to meet with customers and the boss. Got chatting to a 'lady' called Michelle (name changed to protect her identity) - got...
    deleted deleted
    10 Responses Jul 15, 2012

    It was fun and mind-opening

    for me. I had no problem seeing and loving her as a woman. I was impressed with her belief in herself and truth to what she felt. Sexually, she was a big turn on for me. Starts as vanilla; than switches gears and ends up habanero. In addition to being a mix of M and F roles...
    deleted deleted
    Feb 9, 2016

    Trans At A Sex Club

    Thought of sharing this here, i posted it elsewhere but whatever. This is a trans sex club, where everyone is free to come and play with us i guess sorry its long --- Some guys have asked for what happened so here it is SHORT VERSION Everything went perfect LONG VERSION Before we...
    WhiteMushroom WhiteMushroom
    26-30, F
    3 Responses Mar 26, 2013

    I had a wonderful experience with a tgirl

    friend of mine the other day, after some passionate kissing she pushed me on to my back and started to massage my prostate with two fingers slipped inside me I raised my legs to give her better access as it was a wonderful feeling and I wanted more Then she slipped on a condom...
    anykey anykey
    46-50, M
    10 Responses Feb 1, 2014

    Twice And Both Super Exciting

    Once in San Diego with a not so attractive but very sweet TS. I LOVED sucking her off and making her come. She had the prettiest little breasts, fake of course, but very cute. Her penis was on the small side but she had a good load. Another time in SF. She/he was gorgeous...
    Sexualism Sexualism
    51-55, M
    Jun 13, 2013

    The other day I had a bit of a disappointing

    **** by a tgirl - if there is such a thing? It all started when I decided to go visit one of my favourite tgirls. I was feeling like a bit of mutual ******* so I decided to visit Lisa, a pre op tgirl with a nice tgirl 'clitty', about 6-7" and uncut. Lisa also likes to be...
    anykey anykey
    46-50, M
    3 Responses Jan 1, 2014


    I have seen Azura many times and I must say she is my absolute favourite t-girls and she just seems to get better and better As usual, Azura met me at the door and we started kissing and caressing straight away, she started to undress me right there and I could tell it was going...
    anykey anykey
    46-50, M
    1 Response Mar 22, 2013

    Use To Wonder..

    I'm a straight male(at least I thought I was) who was never really attracted to another man, but somewhere along the line I started getting turned on by pics of transsexuals. eventually I decided to take it another step farther and went to a Trans bar in Sin City to check out the...
    wax59 wax59
    56-60, M
    2 Responses Jul 19, 2013

    This experience is more of a montage of a

    number of experiences over a number of years with a number of tgirls Its far and away my favourite type of sexual experience and it all stems back to my first experience My first experience happened quite by chance. I was at a brothel and the girls were being introduced one...
    anykey anykey
    46-50, M
    3 Responses Jan 20, 2016

    1st Time

    I was approached by a woman in a bar in Sydney an we hit it off so decided to head to her place. As we were walking she disclosed her secret, I have always been a little curious about transsexuals and was about to find out. Needless to say we had a great time that night and...
    Chrisking12345 Chrisking12345
    41-45, M
    1 Response Jun 13, 2013

    I met a transexual and had sex with her

    yesterday and today. Today with her was probably the hottest sexual experience I've ever had in my life. I've been with some cute girls before, but she was stunningly gorgeous. We 69'd, took turns ******* eachother and I came hard, deep in her ***. If you have any questions or...
    Sicko69 Sicko69
    41-45, M
    1 Response Dec 11, 2013

    Taken In By A Transexual

    Years ago I had a relation with a TS. She had a really perfect figure with about 108 cm of hips. Breast were large C maybe. First time I had her shave me from neck to toes, and I dressed in some of her jeans and a blouse and flats. We went out to a bar and had a great time...
    deleted deleted
    3 Responses Apr 5, 2012

    A Great Start To The New Year...

    I had no plans for new years eve this past year so I figured "what the hell" and posted an ad on CL for a strictly platonic female to come join me for dinner and some smoke. Within minutes I received a response from a very attractive and slender African American female that was...
    kinkymale40165 kinkymale40165
    36-40, M
    2 Responses Jul 7, 2013

    Finally The Experience I've Been Looking For

    I've been interested in meeting a transgendered woman for some time now. I've always been turned on by shemale **** and fantasized about one day having the opportunity to have sex with a t-girl. I'd tried twice previously but my first attempt the girl was very passive, not into...
    subgent subgent
    41-45, M
    2 Responses May 9, 2012

    Good Times

    I've hooked up with a few tgirls now about 8 I think! At first I was real nervous but since I've relaxed I love it the feel of there **** in my mouth that ill suck as long as they want until the want to take me from behind and **** my *** until they can't hold on anymore.
    Mulligans Mulligans
    26-30, M
    1 Response Feb 17, 2013

    Its the holiday season now

    and its a time to put your feet up Lucky for me I had the chance to put my feet up the other day, over the shoulders of one of my favourite tgirls, Amanda, and I just lay on my back and enjoyed it as she sank into me and &^%ed my brains out :D
    anykey anykey
    46-50, M
    3 Responses Dec 24, 2014

    A Little Surprised

    I can't say I have had sex with a Tranny so this may not be the appropriate place to post but I did have a Tranny experience. One night after leaving a ***** club I was horny and wanted to go to a bar and try to pick up a lady. Across the street, was a rundown bar and thought...
    deleted deleted
    May 24, 2013


    I have a story about an experience I had with a t-girl named Amanda. I first met Amanda at a transexual brothel and she was my first real t-girl experience. Since then I have been seeing her on and off over a couple of years. This story is from one of my encounters with Amanda...
    anykey anykey
    46-50, M
    1 Response Jan 16, 2013

    First But Certainly Not Last

    I have been fascinated by transsexuals since my early teens. I remember an episode of "Hill Street Blues" where one of the cops dated a woman who ended up being a transsexual. Just the thought of a man transitioning into a woman aroused me even then. By my twenties, I had...
    deleted deleted
    1 Response May 26, 2013

    Let's hear some stories?

    I'll tell you mine if you tell me yours
    VenusIncarnate VenusIncarnate
    31-35, F
    4 Responses May 22, 2014

    Post-Op T-Girl *****

    A few days ago, I went to visit my favourite post op t-girl named Krysta In the past, my favourite experience with Krysta was to have her **** me with her strap on, 8", purple, thick, soft, flexible jelly *****. This time I thought I would try something different When Krysta...
    anykey anykey
    46-50, M
    Sep 11, 2013


    ik ben aapje uit turnhout ik ben46j
    aapje aapje
    36-40, M
    Jul 30, 2012

    Post-Op Transexuals Are A Lot Of Fun Too

    Here is another story about an experience with a post op t-girl named Krysta. I have had quite a few experiences with her, here are some of the best. The first time I visited her, Krysta gave me a prostate massage, something I had never really tried before. I was sold on her...
    anykey anykey
    46-50, M
    Feb 13, 2013
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