by J. Slim

Gender: Male
Age: 31
Race/ethnicity: Caucasian
Current location: Belgium
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Musician
Relationship status: Married
Religious affiliation: Jewish
How religious are you? Not at all
Sexual orientation: Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 3
How many hookup stories have you here posted before? None

First Time With a Man

How long ago did this hookup happen? 2 years

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? One-night stand

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? Some context is required here:
I consider myself to be pretty straight, got married to my first girlfriend and only sexual partner. I always fantasized about women, fell in love with girls and so on, but over the years I developed a vast sexual fantasy world and was exposed to a lot of internet porn, testing the boundaries of what and who I could be turned on by.
I found myself at some point looking more and more at pictures and videos of other guy’s cocks and getting turned on. I eventually started going into chatroulette and having cyber-sex type interactions with both men and women. Mostly men. It became a sort of addiction. By the time I came clean and told my wife, we had to take a break and I had to sort this out, find out if I want to be with her, and if I want to be with men or women. We separated for a few months and agreed that if we ever want to truly be together again, I have to check things out. So I set out to live out the fantasies and virtual interactions I was having online.
I put an ad on Craigslist “casual encounters” and after weeding out some guys and going on 2 “dates” to meet the guys and feeling I couldn’t go through with it, I finally found one guy I felt I could do it with.
He was a Spanish guy, in Belgium on business. He was married, in the closet and cheating on his wife while on the road (which I felt kind of iffy about..). I didn’t ask his name until after we were done so I guess it didn’t really matter to me. I think that I actually replied to his ad, I liked it because he advertised: “Hudje Cock and horny” which I found funny. He did have a nice thick cock, though it wasn’t “Hudje”… When we met for beers at a pub nearby his hotel I thought he wasn’t very attractive or repulsive. Just a guy, in his early 40’s that seemed as excited and nervous as I was.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We exchanged nude photos, not sure if we sent pictures of our faces or not, and decided to meet. We discussed what we’d like to do and what was off limits. I was more precise as it was my first time and my attraction to men was ambiguous and confusing. I wanted to try mutual masturbation, frotting (rubbing our cocks together) receiving and possibly giving oral. No kissing, no penetration. That was it. He was cool with it, he wasn’t into penetrative sex either but he was more experienced.
We arranged to meet at pub close to his hotel, I was late and tried to send him emails to tell him I’m running late but he didn’t see any of them and when I got there he was just about to give up and leave.
We had a few beers (I ordered a couple of very strong Belgian beers trying to gather up my courage). We spoke for a while and I barely remember what he was talking about (I think he was in high-tech, he was married with kids and his wife didn’t know he was gay/bi), all I could think about was “I think I’m actually going through with this tonight!” At some point we ran out of stuff to talk about, we each had about 3 beers, and I think I suggested that we move on to his hotel. My heart was beating like mad, I was super excited! It felt like I was playing a character, like I was in a movie of my own fantasy but I had no idea how it was going to develop and how I’d feel.

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 got to his hotel room and the plan was to watch porn together and start jerking off together and see where it leads. But the internet didn’t work and he fumbled with it trying to get a connection.
He finally gave up and came to sit next to me on the sofa and we started to masturbate next to each other. I asked him if he’s hard yet and he said he is. I asked to see it and he pulled out this gorgeous 7.5 inch, thick uncut penis. I asked if I could touch it and he of course said “go ahead”. The moment I touched it still feels like one of the most electrifying sexual moments of my life. It was warm and swollen with a thick head. He was uncut which was a big turn on and great fun to touch and jerk off.
It’s strange it’s just touching another person’s body part, but it turned me on immensely.
He then started to suck my dick while I jerked him off. He was really turned on as well and had to stop me a few times because he was about to cum. He got down between my legs and gave me some pretty good head, deepthroat and ball licking, the whole package. It felt good but I was slightly turned off by seeing a man sucking on my penis. I focused instead on his dick which was a huge turn-on so I reached down and jerked him off as he blew me.
We then jumped on the bed and started rubbing our cocks together in a kind of “non-penetrative” missionary positions with me on top. At one point I told him I wanted to try to put it in my mouth. I went all the way down to his cock, puy my tongue on it and the taste and acidity of it startled me and I jerked backwards. It was like putting your tongue on one of those square batteries that give you a jolt. I figured that I just wasn’t ready and I better just focus on what was turning me on and what I felt comfortable with.
I told him I want him to cum first and I jerked him off. He came a big load all over himself after about 1 minute. I then climbed over and fucked his mouth until I was ready to cum and though he said I could cum on his face and mouth, he changed his mind and asked me to cum on his chest, and sure enough I did. He was covered in both our loads by the end of it.

Did you have an orgasm? Did your partner(s)? We both came once.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None, but only oral and mutual masturbation was involved. My wife insisted that I get tested once we got back together (another story for another website…) and I tested totally clean.

What were your REASONS for having this hookup? I was going through a roller coaster at the time. An identity crisis and a relationship crisis. I was acting out in ways that I never imagined I would or could when I started going in these internet chat-rooms while my wife was next door, sleeping. I had to bring everything in my life under question and I had to come up with some answers. The process leading up to the hookup was agonizing but the actual event was pretty exhilarating.

Were alcohol or drugs involved? If so, how much? I had about 3 strong Belgian beers (8.9%). I wasn’t drunk but I definitely had a buzz going. I’m not sure how much he drank, probably the same.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? After the hookup I walked around on cloud 9. Super proud that I went through with it and had a good experience, being that I was agonizing and brooding about trying to get with a man for a few months beforehand. I often fantasize about this experience though I am ambivalent about it since it came through me cheating on my wife and almost losing her forever. I have no feelings for this guy I hooked up with. He was only a means to fulfill a fantasy of mine. I don’t think he expected anything more from me. He didn’t even ask my name when we were leaving his hotel room. I’m now back together with my wife, we’re doing great though I sometimes feel guilty about thinking about this hookup as much as I do.

To whom did you talk about the hookup? How did they react? I told my wife of course and few of my close friends. They were sympathetic, though the way I present it is more like I went through a really hard crisis and had to figure things out. I still haven’t really had the courage to tell people how much I enjoyed the experience. I guess it’s all the guilt that’s tied into it.

Was this a consensual and/or wanted experience for you? For your partner? Absolutely. For both of us.

Do you regret this hookup? If so, why? I don’t regret it, I think it gave me a taste of something wild and exciting and different. I do however feel bad for hurting my wife and putting through 4 very intense months of uncertainty and it create wounds in both of us and in our relationship that are only now starting to heal. But the hookup came after a period that it was already clear that we have to stop and reconsider everything, so my guilt is less about the encounter itself than what led up to it.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing was living out a fantasy that I had for so long. The build up to the actual event was so big that the payoff was huge for me. Though I had another encounter with a man a few weeks later that wasn’t nearly as fun and was acutally kind of a turn off.
And touching his big uncut penis was pretty awesome.
The worst part was that it came late in life when I was already deep into a committed relationship and I had to hurt someone I love deeply in order to have this experience.

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup or anything else? I’m grateful to have stumbled on this website. I think I need to tell this story in the most honest way I can and it’s hard for me to do in my personal life with the people around me. Maybe I’m afraid of being judged or I’m still a bit ashamed. I have shared this story but always with a kind of regretful spin, like it’s something bad that happened to me, even though writing it here I see how much I enjoyed that night and how important it is to me.

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