by

What’s your gender? Man
How old are you? 45
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Engineer
What’s your current relationship status? Single
Religious affiliation:
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 40-ish
How many hookup stories have you here posted before? 0

Anal To CIM

How long ago did this hookup happen? 10 years ago

What was your relationship status at the time? Same as current status

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? Back in the days of the rare, real casual sex interested female on Craigslist, one day paid off for me. Browsing the casual sex personals, I found a local female in her 30s who wanted to have some fun. We met up at her place across town. I was skeptical after numerous fails on CL, but when I arrived and she opened the door, I was blown away.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Email exchanges off CL got us hooked up within hours. By mid-day, I was standing at her door with very little planning. I’d say she instigated it by posting an ad and I was the lucky chump browsing that day who found 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? We went upstairs to her bedroom right from the front door. She had on some sexy undergarments, had blonde hair, and big, lovely tits showing lots of cleavage in a halter top. She was casual and laid back with a smoldering sexuality. I still think she may have been a retired porn star, but that’s probably me embellishing. She laid on the bed and spread her legs to reveal a beautiful trimmed pussy that was pink, and tight. I went to work with my tongue and the taste was amazing. She came quickly with her pussy clenching and unclenching and a lot of hair grabbing. In no time she was sucking my cock bareback, which I enjoyed. She didn’t suck long and wanted me inside her soon after. I asked about a condom, but she wasn’t interested and I was so horny that I just went for it. What an amazing pussy she had. She quickly had me on the edge of cumming and I had to pull out to prolong the experience. To my surprise she flipped over and said, “Want to fuck my ass?” I became school-boy eager and she had to slow me down and guide me inside – yes, still bareback. Damn if felt good, and she seemed to be enjoying it too as I plunged in slowly and fairly deeply, though not balls deep as she was clenching up. It was so nice. If I hadn’t just gotten so close to the edge, I might have cum quickly. Before long she asked, “Want to cum in my ass?” I did not, and in hindsight I should have, as I have never given an anal creampie to this day. Instead, I was fixated on cumming in her mouth. “Can I cum in your mouth?” I asked. “Sure,” she said, somewhat reluctantly. I pulled out and stood by the bed while she got on her knees. She gave my cock a look, and a light suck, but pulled back a bit and opened up her mouth, tongue out. I think she didn’t like the taste of her ass, so I stroked just a little and in no time, I was cumming. I have a powerful cumshot and it went to the back of her throat and gagged her. She was committed though, and kept her mouth open, gagging and clearly struggling while I finished off. My cum was dripping and drooling out of her mouth as she swallowed and spit at the same time. She sat back on the bed and actually apologized for gagging. Here I was feeling bad for gagging her (and also a little turned on). That was about it. There was no small talk. We got dressed and I left. We never met up again.

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? After the hookup I thought about her a lot. It was a very satisfying sexual encounter. I felt like I had enjoyed a guilty pleasure with a bareback experience with a stranger like that. A huge risk, I know, but man I just couldn’t resist. It was always just going to be that one time. We both knew it, and I still lust after her.

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, Learning new things, experimenting

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? 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? No one.

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? The absolute indulgence of it, and her sexual nature giving me a fantastic orgasm.

What was the WORST thing about this hookup? I maybe should have taken her up on that anal creampie. Seems unlikely to ever happened now.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I know it is possible now.

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? Sometimes you just take a risk and go with it. I got lucky and I know that.

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? It should be more socially accepted.

What do you think about the Casual Sex Project? Fun.

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