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  1. #1

    Has anyone had sex with a transsexual

    This is my thing I want to do.

  2. #2

    Re: Has anyone had sex with a transsexual

    Are you talking post surgery? I just met a trans that lived as a man but always frustrated. S(he) now dresses as a woman at home, has 80 outfits. I've been with her twice and its just like being with a chick. Very feminine, classy, and sexy.

  3. #3

    Re: Has anyone had sex with a transsexual

    That?s so hot?hopefully for me sooon

  4. #4

    Re: Has anyone had sex with a transsexual

    I would also love that to, but I am looking for one that has boobs and a cock.

  5. #5

    Re: Has anyone had sex with a transsexual

    i've had both, post surgery, and many pre, both were hot.

  6. #6

    Re: Has anyone had sex with a transsexual

    I've had the pleasure of being with the same trans girl a couple of times years ago. Saw her on Grindr, figured she was fake but chatted her up anyway. Trans porn is hot but tbh, kind of a turn off because the chances of meeting anyone close to porn quality is like unicorn hunting. After we exchanged pics, she invited me to her place over lunch. I drove over, still expecting to be catfished. WOW she opens the door and she's beautiful, I found a unicorn. Spent almost an hour admiring her beautiful body, she was petite, great fake rack, tiny clit that didn't work because of the hormones. She sucked like a champ and loved daddy/daughter play. Invited me back a couple months later, same scene. Lots of making out and sucking her tits and eating her ass before I fucked her. Wanted to be regular but guess it wasn't in the cards. She lived with her Daddy, guessing they were going through a dry spell and she wanted some strange. Lucky for me, I was in the right place at the right time.

  7. #7

    Re: Has anyone had sex with a transsexual

    I did a long time ago. I didn't realize it until after she was sucking my dick. By that time I was so aroused I played with it for a little bit. She danced at a trans club and sometimes I would go to her place late at night. We met because I was out outside bullshitting with some people outside a club. She stole my wallet and then someone told me where she was. So I went there, in a hotel room and got my wallet back, after she pulled a knife on me. But I called the bluff and we ended up having sex that night. She said she stole my wallet so I would looking for her.
    Last edited by darkale; Dec 2, 2023 at 6:39 PM.

  8. #8

    Re: Has anyone had sex with a transsexual

    i have with 6 or 7 over the years always had a good time

  9. #9

    Re: Has anyone had sex with a transsexual

    I have as a matter of fact lost my anal cherry to a Transexual

  10. #10

    Re: Has anyone had sex with a transsexual

    So those of you who have been here a while know of my journey through the sex trade as a tranny sex worker. I was a crossdresser for fun, and when I was roped into the business, that worked for extra income. I never had the surgery, either top or bottom, and it didn't seem to affect the clients who were interested in chicks with dicks.

    Fast forward 17 years and I am basically done with the crossdressing, happily bisexual and making a hell of a decent living in a non-sexually orientated job.

    Last Saturday, while enjoying a scotch in the VIP lounge of the airline I was flying I was approached by a rather handsome woman, quite tall in stiletto heels, black slacks and a grey silk blouse. She sits at my table and says, "Hello Mel". Mellissa was my "working"name. "Do I know you" I asked. Well to shorten a long story, she used to be one of my coworkers with the same specialty I had. But after I left the trade, she had gone all the way, getting her procedures done in Thailand and living life as a woman.

    We wound up sitting next to each other in first class and we agreed to meet at her hotel in Tampa the next day. And we did. Arriving at the door to her suite, I knocked, and when she opened the door she was wearing a rather attractive silk robe and I assumed little else. She opened her arms and asked, "Aren't you going to kiss me hello?" And when I did, she slipped her lips over mine and opened her mouth for a bit of tongue action. Disengaging, she said "I always wanted to fuck with you, and now I really can. Get undressed". And as I slipped out of my clothes she let the gown slip off her shoulders. She was magnificent.

    Before I could do anything she went down on me and I grew rock hard in seconds. I urged her back on her feet and told her lets go to bed, which we did. So here's the clinical stuff: Her breasts were natural, promoted by the hormone regimen she was on. When I went down on her, partly curious and partly because she needed to be wet (we used lube later) she was not shaved but was well groomed. The faint scars of the surgery were visible, but not objectionable. The complete assembly seems to be just a bit further forward than usual. But the feeling was no different from other woman I've had sex with. And later, when she gave herself to me anally, it was as good as it gets. Had we been strangers, it would have been a normal, pleasurable encounter. The memories we shared made it kind of special, and in the afterglow of some delightfully athletic sex, we shared a room service dinner and laughed about our time in Berlin, before going back to bed to play some more. She had business in Tampa the next day, and I was due in Los Angeles later in the week. But we'll meet again. She is a fine, fun woman. And everything else doesn't matter.
    Last edited by biguycancun; Dec 8, 2023 at 2:51 PM.

  11. #11

    Re: Has anyone had sex with a transsexual

    I'm glad it worked out

  12. #12

    Re: Has anyone had sex with a transsexual

    Quote Originally Posted by Spankme6969 View Post
    This is my thing I want to do.
    I so want too

  13. #13

    Re: Has anyone had sex with a transsexual

    I had been with several attractive cross dressers, but until one rainy afternoon in Orlando in 2018, I had never had never been with a tranny. Let me start by saying she was knock out gorgeous.

    I was just wrapping up after a long day of manning our trade show booth and had called for an Uber to take me back to my hotel, which was located on the other side of the city. When the driver arrived, he explained that it was really busy because of all of the conventions in town and asked if I would mind sharing the ride with another person. I told him no, not all. I was just happy to get a ride.

    As I climbed into the back seat, sitting there beside me was one of the most gorgeous women I'd ever seen. She was well dressed in a knee length skirt, silk blouse and high heels. She had long brown hair and the most beautiful brown eyes I'd ever seen. I politely introduced myself and she did the same, telling me her name was Patricia, but that she went by Patriz. While the driver slowly snaked us across town, I couldn't resist the opportunity to strike up some small talk. She explained that she was a pharmaceutical rep and that she was in town to attend a conference. Fortunately for me, her conference just happened to be booked into the same venue where my trade show was taking place.

    Just as the driver was nearing the entrance to her hotel, I quickly asked her if she didn't already have plans, would she be interested in having dinner with me later? You can imagine my disappointment when she politely thanked me for the offer, telling me that she did have dinner plans with a potential client. Then she added, "But maybe we could meet for cocktails later?" That had me smiling from ear to ear. At that point, we exchanged phone numbers. She said she would call me after they ended dinner.

    I didn't have a clue that she was trans. It was probably a good thing because it was hard enough to get through the dinner hour thinking about her as it was.

    At 9:30 on the dot, Patriz called. I could sense that she'd already had a glass of wine or two. We arranged to meet in the lobby of her hotel and soon we made our way to the bar and were sipping our first martini together. Over the next three hours or so, we exchanged stories about our jobs, what it's like to live on the road, etc. Eventually, we got around to talking about ourselves. She explained that she was born in Brazil and lived there until she was 14. That's when her uncle, who lived in Miami, sent for her and her brother to come to the states.

    The whole time we talked, I couldn't help but admire how beautiful she was. And I wasn't the only one. Just about everyone in the bar that evening was checking her out, including our waiter.

    For a non-native English speaker, she had a perfect command of the language. But as the night, and the drinks wore on, she told me that she had a big secret to tell me, and she would, if I promised to not get angry. I was thinking, oh shit, she's married or she has a boyfriend or girlfriend. Then she leaned over and whispered, "I haven't always been a lady, and most men still wouldn't consider me as one."

    It took me a few seconds to process what she was saying, and then it hit me. It was my turn to lean in whisper, "I'm okay with that. I find you extremely attractive, as does every man and woman in this bar. If you will kiss me, I'll know you are as turned on as me." She quickly turned her head and gave me one of the hardest and longest kisses I've ever had. The only thing left to do at that point was pay our tab and get up to her room.

    That night went by as if it were a dream. Starting with a make-out session while soaking in her jacuzzi tub, we kissed and fondled for at least an hour until I suggested we get our pruned bodies out and go to bed. She had the most amazing breasts and ass, and sported an impressive 6" "clitty" as she called it.

    We spent the rest of that night enjoying each other's bodies. We did everything from 69 to fucking in every position possible. She had the tightest ass and definitely knew how to use it. Without exaggerating, I came 5 times and I know she came at least twice if not more. I may have slept a total of a half an hour that morning. Unfortunately, I had to get up and catch a taxi back to my hotel before the sun came up, which made for one of the longest days of my life, but it was worth it.

    We kept in touch throughout the day via text messages and even managed to slip outside for a brief kiss and hug during lunch, that's when she gave me the bad news that she had to catch a flight out that evening back to Miami. Although we continued to call and text for several months afterward, she eventually settled down with a young man she had met at work. I wished her luck and told her that I would always cherish our brief time together. Unicorns do exist. You just have to get lucky enough to find one, and luckier still to keep it!

  14. #14

    Re: Has anyone had sex with a transsexual

    Quote Originally Posted by Spankme6969 View Post
    This is my thing I want to do.
    like everone else, this would be so f'ng H O T

  15. #15

    Re: Has anyone had sex with a transsexual

    I have need with 2. Both were more like booty calls but hung out from time to time.

  16. #16

    Re: Has anyone had sex with a transsexual

    I love transexuals. I was dating a trans lady up until recently. She is ultra feminine, fabulous hormone induced boobs and a delicious cock. Since then, I am also seeing another trans lady for some amazing sex. She gives great massages prior to the main course. Prior to covid, I was seeing another trans lady who love to fuck me and fill my mouth with delicious cum.

  17. #17

    Re: Has anyone had sex with a transsexual

    Yes I have it is a lot of fun if the two of you click

  18. #18

    Re: Has anyone had sex with a transsexual

    Yes Ladyboys a few times.

  19. #19

    Re: Has anyone had sex with a transsexual

    Yes I have. I met one on Craigs list a few years ago. I went to her place, she was a beautiful black woman with a great face, beautiful tits and a huge black cock. She sucked my cock very well then told me she wanted me to eat her pussy before I fucked her. I had never eaten ass that had a dick nearby but there's a first time for everything. I licked her pussy really good and wanted to suck her huge cock but she told me to leave her boy parts alone and fuck her pussy. She was a great fuck, I met up with her a couple times after.
    She has since had surgery and transformed into a woman. We talked on line, I wanted to fuck her new pussy but she told me she wanted to save it for a real relationship. I never hooked up with her again but should have.

  20. #20

    Re: Has anyone had sex with a transsexual

    this isn't exactly the same , but i had sex with a CD two days ago. it was at a porn theater near me. i sat on a couch next to her and pulled out my 7 inch cock. she liked what she saw , and got down on her knees and sucked me with a lot of guys watching. after a while i asked her to go to a booth with me for more privacy. once there, i kissed her and then got on my knees and sucked her cock. she wanted me to kiss her ass too , which i gladly did. after a while of sucking , she finally came in my mouth , which i swallowed like a fag whore. i loved this experience , it was so fucking hot. there were two men watching from the curtain, as i debauched myself sucking cock and eating cum . it was wonderful .

  21. #21

    Re: Has anyone had sex with a transsexual

    The ultimate for me!!!! Pure bliss!!!!

  22. #22

    Re: Has anyone had sex with a transsexual

    As you may remember from my previous post, I recently met a now woman I had worked with when we were both working as chicks with dicks at a rather posh whorehouse that will go un-named. I spent over two years there. Since my departure and return to a more "normal" life she had gone on to have the surgical procedures to become a woman. She bumped into me at an airport and we had a wild and satisfactory night and day of sex, only having to go our separate ways, but agreeing to meet again, soon.

    I spent the last 3 days with her again, this time at her apartment in Miami, and the sex was even better and more interesting. After our first excited fuck on Christmas Eve, we settled to some less frantic, exploratory sex. She had said to me that when we worked together she always wanted to have sex with me and now we had fulfilled that wish, with extras, because after I fucked her in the traditional, missionary position, she then turned over and begged for it in the ass. I asked which she preferred and she said it was 50/50. Then later, while she was sucking my she slid first one and then two perfectly manicured fingers inside me. I began humping her fingers while she encouraged me to cum, and then I did, with lots of noise that I didn't know I was capable of. She told me that if she still had her penis, she could fuck me forever.

    Sometime later the talk went to remembering the good old days when we ere both working together. She asked about what my real preferences were and I confessed that while no longer playing at trans, I still preferred to bottom, to which she said she would like to top me. Her strapon wasn't huge, and the feeling of her holding my hips while she fucked me was intense, and I shot a fountain of cum as I lost control.

    The last game we played was a quasi-Lesbian night. She dressed me in panties and nylons, like the good old days, and she made very slow and deliberate love to me, never touching my dick, but massaging my over-stimulated prostate until I came again. She wants to spend a weekend with me totally en femme, which means for me shaving and makeup and all the tedium I used to do to make myself pretty or at least attractive to clients that liked that sort of thing. I am tempted. It's been years, but the memories are flooding back and although I had not been with a woman back then, the idea is tantalizing. We will meet again in the new year. I'll let you know what happens

  23. #23

    Re: Has anyone had sex with a transsexual

    I've already recounted my first experience with my transexual former coworker. It has continued, on and off and we keep in touch. Last week she texted me, asking when I'd be in Florida again. I texted back "whenever you want me" and she texted a date, time and that she'd pick me up when I arrived. The date arrived and she picked me up at the Miami airport. She rushed into my arms for a hello kiss and she did this girly thing of lifting one leg behind her as we hugged. In white slacks, and a white shirt offset by her dark tan she was a beautiful sight to behold. The 4 inch white patent heels were the perfect compliment.

    It turns out that she lives in one of the older high rise condos on Collins Avenue, and I was impressed that after her car, a 330i convertible, was driven away by the garage attendant, the elevator, which she called with a key, took us to the top floor, which she shared with one other apartment. The furnishings were contemporary, white, with white carpeting. I got the grand tour, the ocean view and a blow job before my shoes came off.

    We finished undressing each other and went to bed. We took it very slow, with lots of kissing and rubbing and after a few minutes she whispered "finger me, please" and I asked where she kept the lube, it being a forgone conclusion that we would need it for her to have sex. She told me she'd get it later, but to please finger her, which I did.And when I did, she was wet, something that I thought was impossible for a trans girl. She was so happy that I noticed it and so proud of her accomplishment.

    As she explained to me, there are four methods commonly used to create the new vagina for a trans woman. Listening to her explanations, I gained new respect for what she had gone through to become a woman. The details made me lose my erection. From the laser hair removal to the actual slicing and sewing, it is a horrible ordeal. But in essence the procedure used to construct her vagina left nerves and their connections intact plus the mini-glands that create pre-cum in place. For some trans women this procedure and some others allow for sufficient lubrication to facilitate intercourse. After this lesson in trans surgery I tried to get back in the grove by going down on her. And it was pre-cum, but I increased the lubrication and gave her what appeared to be sufficient pleasure with my tongue until she pulled my face away and said "fuck me". And fuck her I did, first in her vagina, then in her ass. She came, making the right noises both times.

    I rolled off her, thinking that for a self proclaimed 100% bottom, I was doing a lot of topping, and when she took me in her mouth again, she knew, probably from our past working history that I was making an effort to please her that was not in my usual preference set, and sliding a finger into my ass was her way of thanking me as she skillfully extracted a gigantic orgasm from me, vigorously massaging my prostate until I ran dry.

    We had slept for several hours when I was awakened by her sobbing. When I asked what she was crying about she told me it was happiness. It seems that I am the first and only man to fuck her since her surgery. When we worked together, she always wanted me to fuck her, and now that wish had come true. To say that I am gratified but confused would be an understatement. But we fucked again before our morning coffee. After a very energetic Sunday, we already have our next weekend planned. So... to be continued.
    Last edited by biguycancun; Feb 20, 2024 at 4:11 AM.

  24. #24

    Re: Has anyone had sex with a transsexual

    ​I was a trans for 8.5 years and had lots of sex..

  25. #25

    Re: Has anyone had sex with a transsexual

    I had the pleasure of enjoy some time with a lovely Irish prop trans and she was more woman than many of the women I have know. She was a very passionate, attentive lover and came in a hands free anal orgasm every time I fucked her. Loved that and I really miss her now that she lost her visa and returned home.

 

 

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