Couldn’t Get It In



What’s your gender? Man
How old are you? 61
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Seattle, WA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? software
What’s your current relationship status? Single
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Bicurious
How many sexual partners have you had in your life (including oral sex)? 30
How many hookup stories have you here posted before? 0

Couldn’t Get It In

How long ago did this hookup happen? 10 years ago

What was your relationship status at the time? Single

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? He was a nice looking guy, a little older than me.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was divorced and having difficulty meeting women. I had always wondered what it would be like to have sex with a man. In real life, I’m 6’4″, 230 lbs, strong and assertive. But I have always wondered what it would be like to be with a man and let him have his way with me.

I tried posting things on Craigslist but it seemed that every guy I contacted would flake out. So there was a guy who wanted someone to top him. I figured I could do that. So I went from being the bottom to being the top.

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 went to his place and he invited me in. I had condoms and lube with me. We sat on the sofa and made small talk for a while and I remembered that I was supposed to be the top so I started kissing him. It was okay, I guess, but I didn’t feel anything. I had hooked up with a woman at a film festival a couple of years earlier and was going down on her and realized how bored I was by it. This was shaping up to be boring also.

We moved into his bed room and we both got naked. We made out some more and moved into a 69. He liked my cock and wanted to get to the fucking. I had some condoms and so did he. He seemed to want me to use his, so I did. The lights were low and I couldn’t see if the condom was inverted or not. I had a hard time getting it on my cock. It seemed really small. Women have told me that I have a fat cock, and I never thought about it, but his condom was really tight.

I moved in to penetrate him and I couldn’t get my cock into him. I tried and tried, but there was just no way. He said he was gay and had been a bottom for years, but lube or no, I could not get my cock in.

He wanted me to finger him while he jacked off, which I did.

How sexually satisfying was this hookup? Not at all

Did you have an orgasm? No, not even close

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? He basically kicked me out after he finished and when I drove away, I thought, “I’m never doing this again.”

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? 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? Somewhat

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

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

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? Other

Did you get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? Somewhat

Why do you regret this hookup? I don’t know if I’m the kind of person who can do a hookup. I was supposed to go fuck this guy, and I just couldn’t get into it. I don’t think I was really attracted to him.

What was the WORST thing about this hookup? I wanted to like it and I was hoping that I would get over the hump about how to connect with men. It didn’t happen.

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? Not at all positive

All things considered, how NEGATIVE was this experience? Fairly 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? This was not the first time in my life that I had casual sex. The number of times it has been fulfilling is 1, unfulfilling 7.

What do you think about the Casual Sex Project? I wonder how accurate the stories are.

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