What’s your gender? Trans woman
How old are you? 28
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? US
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Medical
What’s your current relationship status? In a serious relationship (open)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Mostly gay/lesbian
Any other term(s) that describe your sexuality or sexual identity? I’m a transgender person that lives as a female full time.
How many hookup stories have you here posted before? none
His Wife Wanted to Watch
What was your relationship status at the time? In a relationship (open)
How would you best classify this hookup? Fuck-buddies / Booty call
How long did you know the person before this hookup? For 1 to 3 years
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? I met him several years ago on an online hookup/cruising site for gay men. He was thirty years or so older than me but we were both into the same things and he was looking for a trans. We hooked up then and a couple of times since. I knew he was married which made it even naughtier in my mind, which I enjoy.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? He messaged me on the website which I just happened to visit that day out of boredom. I don’t go there a lot. He asked if I was looking for some cock, and since I was in the mood for some strange and I felt comfortable with him in the past, I told him I was. We arranged to meet at his house in a few hours and I drove over at the appointed time. He only lives 10 minutes away.
I didn’t dress up at all because he is older and a little fat as I said, and I don’t find him that attractive. I was just wearing some skimpy daisy duke shorts, a white tank with no bra, and some wedge sandals. I didn’t have much makeup on and my hair was just pulled back in a ponytail. I was very casual.
When I arrived, I walked to his front door and he met me there. As soon as I was inside, he kissed me really passionately with a lot of tongue. I could tell he was worked up. He led me by the hand towards the bedroom and then he told me his wife was there. I stopped in my tracks! The whole point of hooking up with a married man is the fact that they are hiding it from their wives. I told him I wasn’t comfortable with that and he said she was just there to watch and wouldn’t say or participate in any of it.
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? I let him lead me on, and once we got in the bedroom, I saw a glimpse of his wife sitting in a chair in the corner covered with what looked like a sheet. I only saw her face for a second before he spun me around by my hand and started kissing me again. I was really nervous at this point but he is a really good kisser, so I closed my eyes and started to get into it. He held me really close to him by the small of my back and I could feel his cock through his trousers on my bare thigh.
After a bit of this, he started pawing at my shorts, so I broke our embrace and dropped my shorts and tank. He told me to keep my heels on and so I went to my knees with nothing but a lavender lace thong and wedge heels on. I unbuckled his belt and unbuttoned his trousers and fished his cock out which I began licking and sucking. He had a good bit of precum. At this point, I think I had forgotten about his wife behind me. He was removing his shirt and stuff while I sucked him.
After a lot of this, he pulled me to my feet and kissed me more, led me to the bed, the whole time keeping me with my back to where his wife was sitting. I got on the bed in sort of a child’s pose with my ass at the edge. I could hear him finishing to undress and it was then that I thought about his wife again and I was starting to enjoy performing for someone. I heard him behind me and felt him pull my thong to the side when he started tonguing my ass really good. I got into to this really quick and it wasn’t long before he was stroking my cock, tonguing my ass, while I was squeezing my breasts and pinching my nipples. I started moaning like a bitch.
After a while, he stood and I could feel his cock at my anus. I splayed my hips down so he could enter me and he started slowly, squirting some lube as he entered me. I was ready for a good one at this point. We fucked like this for a bit then he wanted me on my back. I had my ankles over his shoulders when he entered me again. He kept trying to lean down and kiss me more so I pulled my legs behind my shoulders. I am very flexible and lithe but even I can’t do that for too long. He really started pounding me then and I was moaning and whimpering. The entire time he was fucking me he kept calling me a “fucking cunt” and ” filthy whore.” All that had me turned on and with the pressure in my ass and on my prostate and the friction on my cock from his body, I was building towards a huge orgasm.
Several of my lovers in the past, both male and female, have told me I cum like a girl. This was one of those orgasms. It started as a pressure in my tummy spreading and radiating outwards. I felt myself building and building almost painfully until it felt as though I was going over a cliff. I was thrashing and I could hear myself moaning some primal language. By then my legs were around his waist. I felt, at one point, as if I was leaving my body. It wasn’t a sudden end like an ejaculatory orgasm. It just sort of tapered off slowly. My ass was rhythmically contracting on his cock and it wasn’t very long before he grunted several times with hard thrusts. I could feel his moist semen in my ass as he laid all his weight on me. His flabby, sweaty, hairy chest and stomach were on top of me and I just wanted to lay there and cuddle. When his cock slid out of me, I could feel the emptiness in my ass as it gripped on nothingness and I whimpered a little.
My lover didn’t want to cuddle. He rolled off of me and told me I could shower if I wanted. I had tons of my own precum smeared all over my tummy. As I sat up, I got my first good look at his wife. Her sheet was on the floor and she was squatting almost on the chair furiously working a vibrator on her vagina. She was not very attractive in the face and her body looked flabby like her husband. But, I tried not to stare as I didn’t want to disturb her as I dressed and said goodbye to him. I didn’t shower and I drove home with the smell of his sex and sweat all over me and the feel of his cum running down my thighs and on my thong.
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 sort of felt bad about the wife not joining in. I’m not really into girls but I’m sure we could have come up with something.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None
What were your motives for this hookup? Fun, pleasure, horniness, Submission / Relinquishing power, Boredom, It was easy / convenient
How intoxicated were you? Not at all (no alcohol or drugs)
How intoxicated was your partner? Not at all (no alcohol or drugs)
How wanted was this hookup for you at the time? A little bit
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? I shared this with a really good friend that is also transgendered. They thought it was hot.
How would you best summarize people’s reactions about this hookup? Relatively positive
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? My orgasm. Those kind are harder to come by and everything has to be just right. I can have a regular orgasm anytime I want by masturbating.
What was the WORST thing about this hookup? I would have liked some cuddle time afterwards and maybe assisted with getting his wife off.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really.
All things considered, how POSITIVE was this experience? Fairly positive
All things considered, how NEGATIVE was this experience? Not at all negative
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 think it has its place. All sorts of people need sexual release. Oftentimes relationships get in the way of that.
What do you think about the Casual Sex Project? I find writing this has been rather cathartic.
You have a hookup story to share? Submit it here!