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I Have Had Sex With a Transexual

Personal Stories, Advice, and Support 216 People

    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 36-40, M 2 Responses Jun 13, 2013

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    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

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    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 26-30 13 Responses Jul 15, 2012

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    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 26-30 3 Responses Apr 5, 2012

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    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

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    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 22-25, M 1 Response Oct 3, 2013

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    Aapje

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

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    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 36-40, M 1 Response Dec 11, 2013

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    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 46-50, M Jun 13, 2013

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    Amanda

    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 2 Responses Jan 16, 2013

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    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 2 Responses Dec 6, 2013

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    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 1 Response May 9, 2012

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    Azura

    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

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    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 26-30 1 Response May 26, 2013

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    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 3 Responses May 28, 2012

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    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

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    Second Time With A BBC Tranny

    I prepared my self anally with a huge warm cleansing enema, took a long hot shower with old spice body wash and put on a pair of lucky boxer briefs. After getting dressed I headed out on the 1 hour long drive. Upon arriving I was greeted at the door by Candy with a deep sloppy...
    Ilcitlsh Ilcitlsh 26-30, M 2 Responses Sep 4, 2013

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    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 6 Responses Jun 23, 2013

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    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 12 Responses Feb 1

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    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 4 Responses Aug 10, 2010

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    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 26-30 2 Responses Mar 28, 2011

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    Not Yet !

    but I want to. Really want to.
    Terri67 Terri67 66-70, M 1 Response May 30, 2013

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    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 51-55, M 3 Responses Jul 19, 2013

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    Lisa

    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

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    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

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    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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    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

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    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

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    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 18-21 Aug 26, 2013

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    First Time With Bbc Tranny Part 1

    Her voice sounded just like a slutty sweet black freak over the phone line . Name was candy she loved sucking white **** and wanted a man to cream pie her ***. So we agreed to meet at the mall parking lot , I arrived early and shopped for a new outfit . She arrived and picked me...
    Ilcitlsh Ilcitlsh 26-30, M Jul 24, 2013

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    Let's hear some stories?

    I'll tell you mine if you tell me yours
    VenusIncarnate VenusIncarnate 26-30, F 4 Responses May 22

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    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 26-30 May 24, 2013

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    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

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    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 4 Responses Jan 1

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    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

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    Related Experiences

    I had sec with my uncle ;) and i loved it! Msg me for the story !
    Vannnessaaaaa Vannnessaaaaa 18-21, F 8 Responses Oct 9

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    One time me and him were so loud he had me handcuffed and the neighbors thought something was wrong so they called te cops and we lost the keys to the cuffs so I had to awnser the...
    oilchick1488 oilchick1488 18-21, F 6 Responses Oct 12

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    A few years back I ran into a third cousin of mine and I knew that she was a bit slutty, specially after her divorce. We had gone partying before and we were each other's 'wingmen...
    dazedandconfuzelled dazedandconfuzelled 31-35, M 1 Response Oct 6

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    He had me up his big window in his room and was ******* me so hard that we cracked the window
    oilchick1488 oilchick1488 18-21, F 5 Responses Oct 12

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    I have always had a thing for older woman and I do not regret the things that have happened between us.
    bradlydc bradlydc 18-21, M 1 day ago

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    When I was 10 my cousin who was 13 came into my shower, and she kissed me, told me i was hot and made me **** her. It was so amazing after we got past the weird, after that day we...
    Carsonisthedawg1025 Carsonisthedawg1025 18-21, M 1 Response Oct 5

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    Forty-seven, to be exact. That's not counting the two I've been married to, and countless prostitutes.
    Nakeddave61 Nakeddave61 51-55, M 1 Response Oct 8

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    I've had sex with some 16yo's. I've done it with my cousin. And i've done it with my friends brother & his friends. (Mostly 14 & 15)
    WhiteGirl702 WhiteGirl702 22-25, F 13 Responses Sep 30

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    I would probably go for sex with my close friends as part of friendships..i do not say it casual as it's with my friends and with whom I like to do everything I like feel like ...
    Ravidesai Ravidesai 41-45, M 1 Response Sep 22

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    Back in high school I baby sat for this couple, they were in their early thirties with a seven and four year old. Now let's talk about the sexiest man I've ever met. This dad had...
    SteelNettt SteelNettt 18-21, M 2 Responses Oct 3

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    I was chatting to this guy on Grindr a few weeks ago, he didn't have a profile pic or any kind of profile, but he was 2 streets over and wanted to suck c**k, nothing else. So I...
    crake101 crake101 31-35, M 2 Responses Sep 23

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    He's escaping. He doesn't meet her when he sees her now. He stands with others & looks at her. If she texts him, he doesn't show up, or it's more like a one word thing. Has she...
    Xyanii Xyanii 22-25, F 2 Responses 4 days ago

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    When I was a sophomore in highschool I was staying after school one day finishing up a test. She was sitting at her desk texting her boyfriend now husband. She was getting horny...
    Carsonisthedawg1025 Carsonisthedawg1025 18-21, M 2 Responses Oct 5

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    In the parking lot at the mall and it was great
    mbac mbac 41-45, M 4 days ago

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    Say hi if you want to talk.
    TwoBrains TwoBrains 41-45, M 2 Responses 3 days ago

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    Write about your experience
    bumble2bumble bumble2bumble 26-30, M 6 hrs ago