Logo

Has anyone been tricked into having sex with a shemale? How was the experience?

11.06.2025 00:18

Has anyone been tricked into having sex with a shemale? How was the experience?

Anyway, we were chatting to them on and off and throughout the evening. As we got more drunk I got closer to this girl, she had long black hair, her name was Adriana, she was Brazilian and very beautiful. I couldn't believe she was interested in me, and at the end of the night when she asked me to go back to hers I jumped at the chance. It was just a short cab ride there, we didn't kiss in the cab but she just rested her hand on my leg during it. That alone had me aroused as I anticipated a fun night.

I wouldn't say I was tricked, but my very first time with a trans woman (please don't call them shemales) was back in 1998 when i was 22. I was in London visiting a friend. We were out having a few drinks. There were two lovely looking ladies sat at the table next to us, at least I thought they were ladies.

As soon as we entered her flat and shut the door we were all over each other. Lots of very passionate kissing and groping. It was then I felt it, a hardness in her panties. I'm not ashamed to say I freaked out and froze. She knew what the issue was obviously and asked me not to leave, but to sit down on her couch and talk about it. I was still freaking a bit and quite bewildered by it all so was in a kind of autopilot mode when I sat down. After a few minutes of drinking some vodka to calm myself and talking to her I relaxed and realised I was curious and incredibly turned on by the fact she had a cock. I admitted this to her and we began kissing again. This time there was no stopping me and I immediately reached for her cock, feeling it grow in my hand as i played with it. I pulled it out of her panties and knelt down on front of her, it was around 18cm so a good size. I put it in my mouth and started to suck her cock. I realised I really enjoyed it, with Adriana was telling what to do. I was so turned on by this that as cane as I wanked my own cock while sucking her. A few minutes later, she blew a hot load in my mouth and I swallowed every drop. We sucked and fucked all night long, it was truly awesome. We became fwb for a few years, with me visiting whenever I was in London until she sadly returned to Brazil in 2002 and we lost touch. I have been hooked on trans women ever since, and even though my opportunities are severely limited these days due to being married to a beautiful cis woman, it is an itch I simply have to scratch every now and then. It is without a doubt the hottest sex a man can ever experience

Hello,hope y'all doin good, i came to Quora to share my strange story , a very weird one , a story when luck smiled at me ,maybe u will enjoy it , let's begin,have fun... A year ago ,I was a real porn addicted(btw I was 18) ,but never had sex before, I don't have a gf I didn't try to find one even ,always thinking to go to find a sex worker but then I just don't , everyday watching different bodies getting fucked and everyday enjoying. One day, I was watching porn, a big ass lady with big boobs ,just after seeing her the image of my female cousin poped in my mind, (let's introduce her : she's 35 years old , very big ass , nice boobs ,not very big but nice,always wearing tight clothes , she's divorced ) and I thought of me fucking her ,I never had sexual desires for her but now I do days went by and when I met her I was so horny ,I couldn't stay with the family cz my penis was clearly erected , I realized this is my first time I get horny for one of my family ,it not illegal in my country.well to make a long story short( if u want details just text me I will tell u 😊),I decided to give her signs that I want to fuck her,finally I decided to have sex and with my cousin , I thought it is the best beggining for me, i started touching her when I came across her in a narrow place , make her feel my hard cock when we hug , I thought it will hard and I will be ashamed but no , I felt nothing and she said nothing , probably she thought it was by mistake,anyways, I decided then to talk with her about sex, waited for her to be alone in a room and talk with her, I confessed everything about me watching porn and addicted..etc,she said it's normal and u are growing up and u must have sex,well at that time I was like whaaat????? Well I didn't control myself and asked her for sex ( horny like I Ve never been before) she said that she will think Abt it ,2 weeka went by then she called me ,telling that she reserved a room in a hotel and we meet tonight ,we met,and bruuhh, sex is great , I mean, I had to find a pirstitue ,what I was waiting for to have such a feeling ????, I will never forget that night, I started kissing her she was kissing hard ,she misses sex so bad , she sucked my dick and swallowed my semen ,I felt I'm in a dream , then when fucked ,her ass was very big and the anus was open ,didn't struggle to get my hard cock inside it , she was obviously missing sex , she was shouting ,fuck me yh fuck me , I go fast after every word until I cum , we did that 3 times , then we went to her pussy , using condoms I fucked her so hard the moans were higher , everything was perfect ,in the end I asked her to lick her body , licked pussy ,ass, boobs,then she sucked my cock until we sleeped ,all I know that she was dirty ,well before even having sex with her I knew she is an open minded woman , and a woman that looks that she donesnt know anything , but she knows everything, but never expected having sex with her ,well she was horny and that helped...but no one of us regretted that sex ever.. We still have sex from time to time ,and I started having sex with sex workers , joining threesomes..etc If u want pics of her text me.