Post
This experience may contain mature content, as flagged by the community. Please click away if you do not want to see this content, or if you are not of age. To report inappropriate content, please email us.

I Have Had Sex With a Transexual

Personal Stories, Advice, and Support 193 People

    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...
    Ilcitlsh Ilcitlsh 26-30, M 1 Response Sep 4, 2013

    Your Response

    Cancel
    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...
    deleted deleted 26-30 3 Responses Apr 5, 2012

    Your Response

    Cancel
    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...
    kinkymale40165 kinkymale40165 36-40, M 2 Responses Jul 7, 2013

    Your Response

    Cancel
    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...
    desiderio desiderio 46-50, M 3 Responses Jan 10, 2012

    Your Response

    Cancel
    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...
    anykey anykey 46-50, M 3 Responses Jul 26, 2013

    Your Response

    Cancel
    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...
    WhiteMushroom WhiteMushroom 26-30, F 2 Responses Mar 26, 2013

    Your Response

    Cancel
    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...
    Chrisking12345 Chrisking12345 36-40, M 1 Response Jun 13, 2013

    Your Response

    Cancel
    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...
    Uhtred2008 Uhtred2008 26-30, M 3 Responses May 28, 2012

    Your Response

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

    Your Response

    Cancel
    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...
    deleted deleted 26-30 May 24, 2013

    Your Response

    Cancel
    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...
    anykey anykey 46-50, M 2 Responses Nov 20, 2013

    Your Response

    Cancel
    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...
    Dgirl5 Dgirl5 31-35, F 3 Responses Jun 23, 2013

    Your Response

    Cancel
    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

    Your Response

    Cancel
    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...
    wax59 wax59 51-55, M 1 Response Jul 19, 2013

    Your Response

    Cancel
    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...
    subgent subgent 41-45, M 1 Response May 9, 2012

    Your Response

    Cancel
    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...
    anykey anykey 46-50, M 3 Responses Dec 6, 2013

    Your Response

    Cancel
    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...
    anykey anykey 46-50, M Sep 11, 2013

    Your Response

    Cancel
    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...
    deleted deleted 26-30 14 Responses Jul 15, 2012

    Your Response

    Cancel
    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...
    anykey anykey 46-50, M Feb 13, 2013

    Your Response

    Cancel
    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...
    deleted deleted 26-30 2 Responses Mar 28, 2011

    Your Response

    Cancel
    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...
    Sexualism Sexualism 46-50, M Jun 13, 2013

    Your Response

    Cancel
    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...
    Sicko69 Sicko69 36-40, M 1 Response Dec 11, 2013

    Your Response

    Cancel
    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...
    Mulligans Mulligans 26-30, M 1 Response Feb 17, 2013

    Your Response

    Cancel
    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...
    wellimga wellimga 22-25, M Oct 3, 2013

    Your Response

    Cancel
    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...
    Ilcitlsh Ilcitlsh 26-30, M Jul 24, 2013

    Your Response

    Cancel
    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...
    anykey anykey 46-50, M 2 Responses Jan 16, 2013

    Your Response

    Cancel
    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...
    WhiteMushroom WhiteMushroom 26-30, F 2 Responses Mar 26, 2013

    Your Response

    Cancel
    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...
    anykey anykey 46-50, M 2 Responses Jan 16, 2013

    Your Response

    Cancel
    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...
    deleted deleted 26-30 1 Response May 26, 2013

    Your Response

    Cancel
    Not Yet ! - but I want to. Really want to.
    Terri67 Terri67 66-70, M 1 Response May 30, 2013

    Your Response

    Cancel
    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...
    anykey anykey 46-50, M 1 Response Mar 22, 2013

    Your Response

    Cancel
    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...
    TomDrum TomDrum 18-21 Aug 26, 2013

    Your Response

    Cancel
    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...
    anykey anykey 46-50, M 2 Responses Jan 1

    Your Response

    Cancel
    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...
    anykey anykey 46-50, M 2 Responses Feb 1

    Your Response

    Cancel

    Related Experiences

    I am feeling this strong sexual affection towards my cousin and I wondered if someone could give me advise
    lumperjack18 lumperjack18 18-21, M 1 day ago

    Your Response

    Cancel
    I was 16 and the time and he married into my family. We were both different races i also have a strong belief for interracial relationships because of this. We still have a...
    RoseyRosalita RoseyRosalita 18-21, F 3 Responses Apr 5

    Your Response

    Cancel
    She just grabbed me an I didn't want to stop her an we ******
    brandoncox209 brandoncox209 13-15, M 1 Response 3 days ago

    Your Response

    Cancel
    Never had sex with a black woman but I want to.
    andykenny andykenny 26-30, M a week ago

    Your Response

    Cancel
    It was at lunch time. At that time I was cunfusde about him. We needed to finish our project for our school. He told me to go to his house. So after school I went to his house he...
    OscarMercardo OscarMercardo 16-17, M 1 Response 5 days ago

    Your Response

    Cancel
    I went to this party with my friend but i didn't know anyone there, so i was kind of shy. The more i drank the more out going i became (because that's what alcohol does to you) and...
    JordanElaine JordanElaine 18-21, F 8 Responses Mar 20

    Your Response

    Cancel
    I went to one of her fashion shows and I got invited backstage to meet her. When I got there I saw her she was wearing a bikini, anyway I said hi and she said hi back, I kept...
    Ladiesman93 Ladiesman93 22-25, M 2 Responses 19 hrs ago

    Your Response

    Cancel
    I married the man who took my virginity and have never been with anyone since. Both my husband and I fantasize about me being with someone else, but if it never becomes a reality...
    ShesAVeryKinkyGirl ShesAVeryKinkyGirl 26-30, F 4 Responses 4 days ago

    Your Response

    Cancel
    I was at her concert backstage and she walked past me when she finished and I grabbed her ***, she looked at me and pushed me behind a curtain and jumper on top of me. We started...
    Ladiesman93 Ladiesman93 22-25, M 2 hrs ago

    Your Response

    Cancel
    We have been married for 15 years and wanted to see how to have sex and watch sex via a web cam. You have to be sexy, we are! in good shape, and willing to show us how to do it...
    just4fun3 just4fun3 41-45, M 1 Response Mar 27

    Your Response

    Cancel
    I'm not gonna go into too much detail but he laid me onto his desk and ****** me. He has left a monkey bite on my arm that isn't going away, no matter how much I wash it with warm...
    Janslowjam Janslowjam 18-21, F 5 Responses Mar 28

    Your Response

    Cancel
    I didn't think I'd let it get that far cuss of what happened with my ex and with me wanting to wait till after i was finished with school.not only was he my crush but he's also my...
    CountryGirlinHell CountryGirlinHell 16-17, F 1 Response Mar 19

    Your Response

    Cancel
    I didn't but I think my brother might have. I think its hot.
    katysback katysback 22-25, F 8 Responses Mar 22

    Your Response

    Cancel
    Have ever *********** out in public I do it in public restrooms
    jdubvolt jdubvolt 26-30, M 3 Responses Apr 2

    Your Response

    Cancel
    It was one of the most weirdest thing ever. She's actually my step mom , my dad married her 4 years back . I noticed she always paid extra attention to me and one day when nobody...
    deleted deleted 26-30 4 Responses Mar 27

    Your Response

    Cancel
    My crush jokingly told me that if we were together, he would've banged me so hard if I would allow him. He would fantasize about me at night. Wait whut?? 😱 not sweet at all but...
    Pattsyy Pattsyy 22-25, F 2 Responses Apr 7

    Your Response

    Cancel
    and I loved it. everything's all ****** up now.
    MizThang MizThang 18-21, F 7 Responses 6 days ago

    Your Response

    Cancel
    Ladiesman93 Ladiesman93 22-25, M 1 Response 20 hrs ago