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I Have Had Sex With a Transexual

Personal Stories, Advice, and Support 210 People

    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 Oct 3, 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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    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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    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 2 Responses Jan 1

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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 1 Response Jul 19, 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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    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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    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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    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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    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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    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 3 Responses Jun 23, 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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    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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    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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    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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    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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    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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    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 5 Responses Feb 1

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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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    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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    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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    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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    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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    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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    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 1 Response Jun 13, 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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    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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    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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    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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    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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    Aapje

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

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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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    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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    Not Yet !

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

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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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    Related Experiences

    Okay I live in Michigan I was 17 now 18 at the time and the age to consent to sex is 16 I'm guessing that's with any age but below 16. Anyways this 42 year old police officer who...
    cupcakes38 cupcakes38 18-21, F 3 Responses Jul 19

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    Kinda family: when i was 12 we went abroad to visit family and i had sex with 4 of my male cousins (distant cousins) at the same time, in a field near their house.
    Julieloli13 Julieloli13 13-15, F 19 Responses Jul 1

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    I had sex with over 200 girls before my 18th Birthday...
    Raddaddy Raddaddy 41-45, M a week ago

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    I've only had sex with one girl. And it was amazing!!!! I like boys and I'm sure one day I'll find the right one
    Randi97 Randi97 18-21, F 4 Responses 6 days ago

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    I want to have sex with a big women so I could sexually pleasure her hit me up
    Dloveski Dloveski 36-40, M Jul 4

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    I had to stay late after school and my teacher had get megan tightly crossed i asked get if she was ok and i saw her run to the toilet. I heard a plop plop and accidently opened...
    reddeath11122 reddeath11122 18-21 1 Response Jul 19

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    I hugged my aunt and couldn't resist grabbing her butt so I did and it was so juicy and soft and nice. After she smiled and winked at me. I wish I could play with it all day.
    RacerXX2 RacerXX2 13-15, M 3 Responses Jul 9

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    with my niece and cousin. But not at the the same time
    mrmarine mrmarine 46-50, M 7 Responses Jul 20

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    My aunt has a wonderful butt I wish I can hump it and haver her sit on my face.
    RacerXX2 RacerXX2 13-15, M 2 Responses Jul 11

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    I finally caught my aunt bent over I have a pic ;)
    RacerXX2 RacerXX2 13-15, M 10 Responses Jul 11

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    Mom and I have been together for about two years now. I am so happy and thankful and hope it never ends, and Mom's told me that she's never felt more loved and wanted - and I sure...
    BMart BMart 18-21, M 5 Responses 2 days ago

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    Did it with my best male friend. We were both waaaaasted. He got it in the wrong hole and it hurt for a week, blood and all. Ouchhh! So we are mutually not into each other but...
    amandapanda88 amandapanda88 26-30, F 4 Responses Jul 4

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    I want to have sx with a beautiful BBQ women I'll go to you if your in the bronx
    Dloveski Dloveski 36-40, M Jul 4

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    My cousin who is also a girl and is 4 years younger than me keeps wanting to play 'lesbians' when nobody is watching. I'm so confused and don't know whether I am straight or bi!
    irwinslaugh irwinslaugh 16-17, F 4 Responses Jul 7

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    I really want to F*** my aunt. I want her to bounce on my co**
    RacerXX2 RacerXX2 13-15, M 2 Responses Jul 9

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    I remember when I hugged my aunt and she put my face in her boobs. I loved it
    RacerXX2 RacerXX2 13-15, M Jul 9

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