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What’s your gender? Man
How old are you? 40
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: High school diploma
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 20
How many hookup stories have you here posted before? 0

I Barebacked A Transsexual

How long ago did this hookup happen? 5

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? Just met that day

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? They were from a Latin Country in South America. Obviously had multiple plastic surgeries because they were total perfection with beautiful perky tits and plump ass. You would never know they were ever a guy.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was invited to a party at a friends house who owns a large business and a big party town down in south Florida. I was just taking it easy in his pool when she came up from behind me out of know where and began talking to me. She could speak english really well but had a latin accent. We talked in the pool for about 10 or 15 minutes and I had a hard time not looking at her body, because like I said, they were pornstar/beauty queen beautiful. We made our way out of the pool and on to a pair of lounge chairs for mayne another 45 minutes. By this time I had to use the bathroom so I told her I would be right back. Went into by buddies house because everyone else was going in and out of the pool house and it was crowded in there. I closed the door and the next thing I hear was a knock at the door. I open the door and there she is. She pushes me inside the bathroom and locks the door. She comes over and starts kissing me and rubbing my dick through my swim trunks. I become so hard it’s hurting. She is deep french kissing me, very sloppy but so very hot.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? She starts making her way down by body and pulls my trunks down and my cock springs out like a diving board. And when I say it was insanely hard is an understatement. So know I have this gorgeous girl on her knees looking at me then my cock and she starts to graze over it with her hand then looks up at me and slowly starts putting my cock in her mouth. She starts sucking it like and slobbering all over it. I end up having to put the seat down on the toilet from feeling almost dizzy from this amazing blow job. She tells me to move down to the floor of the bathroom so I do. She continues to suck and lick on my cock and the my balls. She pulls my legs up and makes her way back to my taint then she starts licking my ass which sent me to another realm it felt so amazing. And I couldn’t believe I had this beautiful woman doing all these things to me I just met. It truly felt like some kind of porno.

So anyway, we both make our way back to our knees and we’re back to making out and of course I want to reciprocate what she’s doing to me, and I start making my way down her body pulling her top away from her enormous tits and licking and sucking on her nipples. She stands up and starts taking her bottoms off and has her hand over her pussy which sort of confuses me but she slowly mover her hand and starts spreading her legs when all of a sudden a really large cock comes swinging from between her legs. It’s uncut and around 8 inches long and really thick. I’m really set back for a second but something in me got so turned on looking at her beautiful face huge tits and large beautiful cock that I just grab it and start sucking on the head.

I’ve never sucked a dick before but she seemed to like everything I was doing so it got me all excited. I lay down on the floor again and have her straddle me. I tell her to lower her ass over my face that I want to lick, suck and stick my tongue in her asshole. She does what I ask and is slowly storking her cock while I have my mouth on her asshole. She then raises up off me and moves down to my cock. Now remember, I’m at a friends house we were in the pool when we first met like maybe an hour and half ago so it’s not like I walk around with condoms on me just in case. Anyway she lowers herself down on to my cock and works it inside of her ass. She starts to slowly work my raw dick in her tight asshole. Once it’s stretched it out enough she starts picking up the pace and stroking her cock while she rides me. We’re about 2 or 3 minutes into it when she starts to shake and says she’s going to cum. Right then she starts shooting a huge thick load that shoots all the way up to my face and all over my chest. This sends me over the edge I finally shoot what felt like the biggest load of cum inside her ass that I’ve ever felt. I felt like it literally pulled my soul out. It felt like I was almost pissing inside of her. She got down from her feet to her knees and bent down and started kissing me and licking her own cum off my lips and chin. She then got back up on her feet and slowly lifting up pulling my dick from her ass. There was a huge amount inside of her, it just came oozing out of her ass. After we were both up, we both started pissing in the toilet and smiling and kissing each other. We got dressed and went back down to the party. It was a terrific day.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? I felt great. I thought at some point I would worry about an STD or something but it has never worried me. I got her number and we’ve hooked up 3 other times since then

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Just happened, I don’t know why, just went along with it

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? Nobody

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I’ve never been with a transsexual before and for my first time to be with one who was as gorgeous as she was was amazing and it sounds fucked up but I’m glad I did it bareback and cum inside them

What was the WORST thing about this hookup? Nothing I will fuck them for as long as they will let me

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes I love it. I loved fucking somebody who was a total stranger and loved doing it raw.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? Nothing other than I think I’m falling in love with her now which I guess that kind of sucks with the stigma that comes with being with a transsexual even though you would never in a million years know

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I’m glad it happened and if the occasion was to happen again I would do it without hesitation

What do you think about the Casual Sex Project? I like expressing my experience on here and letting the world know I fucked a total stranger transsexual bareback. Even though they’re not a stranger now.

You have a hookup story to share? Submit it here!