What’s your gender? Man
How old are you? 32
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Musician
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Jewish
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? Straight with a bit of a penis fetish
How many sexual partners have you had in your life (including oral sex)? 3
How many hookup stories have you here posted before? 1

Ambivalent Encounter

How long ago did this hookup happen? 4 years

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? At the time I was on a break from my relationship with my wife. I was secretly going on Chatroulette and jerking off my both men and women. It was going on for a while and became a kind of addiction and I finally came clean and told my wife. We agreed that if we’re ever gonna end back together again I’m gonna have to figure out if I we ever want to be together I have to figure some stuff out. So we broke up for a few months and I set out to live out these experiences I’ve been having in the virtual world. After a long and quite agonizing period of trying to gather the courage and going on a few “dates” that went nowhere I finally gathered the courage and went through with one hook-up that went really well (which I wrote about here beofre). This hook-up was the second one I had with a guy.
He was a gay guy that contacted me through my Craigslist ad. He seemed intelligent and sane and lived close by. We met at a cafe near my apartment and I was a bit disappointed that I felt no attraction to him. He was slightly effeminate which I don’t find very attractive and he talked a lot and quite frankly I was barely listening to what he said, but emboldened by my previous encounter that was a huge success I decided to go through with it anyway.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After I had a few beers to gather up my courage and he ran out of stuff to say, there was an awkward silence and we decided to go to his place which was in walking distance. On the way over the conversation turned a bit more towards what we were about to do. We got to his flat and I saw his tennant (he rents the first 2 floors as a B&B) which was slightly awkward and we went up to his room. There was no real sexual tension or flirtation going on beforehand and the whole thing felt quite awkward though exciting as well…

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? In our email exchange I specified what I was interested in doing (mutual masturbation, receiving head, watching porn together, possibly giving head). He was obviously much more experienced but he was fine to follow my lead and didn’t try to force anything on me or push my boundaries beyond what I said I was comfortable with. I suggested he put on some porn to get us started and he offered me to choose some straight porn but I told him to put on whatever he likes these days so he put on a gay porn video. At this point I still wasn’t hard and was feeling quite awkward. We both started to undress and I remained with my shirt on but nothing else. He then started to give me head and he was quite good at it, deepthroating my cock (which my wife never was able to) and licking my balls. One of the biggest turn-ons for me about being with a guy is if he has a nice cock. I find a thick hard dick, dripping pre-cum, with heavy, manly balls to be incredibly hot but this guy had a really weird dick… I couldn’t tell from the nude pics he sent because they were shot from below in black and white and were quite artsy but it looked to be normal.
Up close, his dick was just strange and unappealing. It was very short, like maybe 4 inches but it was quite thick. The head of his penis was much thinner than the shaft and was a totally different color, like a dark red. He also had a long foreskin which I’ve never seen in person. It looked almost like a stump of a bigger dick that was cut in half. So between his weird dick and the gay porn I just wasn’t really feeling it. He sensed that and stopped at one point and asked if I’m having some trouble staying hard, to which I replied “yeah a bit”. He said “is this better?” and spat on his hand and started jerking me off really hard which just felt amazing and got me hard quickly. After a minute or so of this I came a big load all over his sheets which he didn’t seem to mind. After I came I said I wanted to make him cum as well and he seemed really surprised and said he wasn’t expecting anything in return. He laid down and I started jerking him off but his dick was so short that I didn’t know how to work it. I was apparently focusing too much on the head of his dick (I’m circumcised so I don’t know much about jerking off uncut cocks) and he showed where and how to touch him. He came soon after and was quite vocal though it seemed slightly theatrical, like he was trying to make me feel better or something.

How sexually satisfying was this hookup? A little

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 went to wash up in the sink as he was was taking off the sheets. A strange thing happened which also happened in my previous hookup with a guy: I felt a lot of phlegm building up in my throat during the hookup and after as I was washing up I tried to cough it up and spit (without making too much gross noises) and it got stuck in my throat and I started to gag/choke on it. I was afraid I was gonna barf in the sink. The weird thing is that I happened both times right after the hookup as I was washing up…
I said goodbye and thanks and went home. He sent me a text the next day asking if I want to hang out and I replied that I just want to get back to building my relatioship with my wife back again and that it was just a one time thing for me. He was very sweet and understanding and wrote back best of luck and said that I have a great cock and a great body and thanks for the fun experience. That was nice to hear and I felt ready move on. Having had a few experiences with men, I felt confident that I fall somewhere on the Kinsey scale but closer to the heterosexual side. I felt ambivalent about the hookup but happy to start getting back together with my wife (if she’d still want me back…)

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Thought it was an important experience to have, I was trying to figure out if I’m bi and what it’s like for me to be with a guy

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? I don’t know

What substances did your partner(s) consume? Alcohol

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? 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 spoke about it to some close friends but not in any detail. Just mentioned that I experimented with men while my wife and I broke up for a few months.

How would you best summarize people’s reactions about this hookup? Relatively positive

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? Not at all

Do you regret this hookup? A little bit

Why do you regret this hookup? I wish that I hadn’t gone through with it since I didn’t really feel attracted to him. The whole thing of going through and cumming while feeling very ambivalent was a bit unpleasant. I wish looking back that would have followed my instincts but at the time I wanted to get another experience “under my belt” and move on.

What was the BEST thing about this hookup? The fact that I went through with it, after a long period of not having the courage to do anything with men outside of sex chat-rooms online. Also the fact that I wasn’t really attracted to him and remained ambivalent throughout reinforced the feeling of where my sexual orientation really is focused.

What was the WORST thing about this hookup? His weird dick. His saliva smelled bad on my dick and his breath kind of smelled bad too.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really. I have no problem with casual sex and I suppose if I wasn’t in a committed relationship I could get into it but I’m married to my first girlfriend and I love her to death and we’re in a monogamous relationship. I have no judgement for people who enjoy casual and/or don’t believe in monogamy but I feel I figured this out and I’m ok now where I am and my wife and I are doing really well.

All things considered, how POSITIVE was this experience? A little positive

All things considered, how NEGATIVE was this experience? Somewhat negative

What do you think about the Casual Sex Project? I love it. The stories are fascinating and often sexy and arousing! I visit often and enjoy reading realistic, honest accounts of people’s sexual encounters.

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