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What’s your gender? Man
How old are you? 42
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Miami
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Process Engineer
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: RC
How religious are you? Somewhat
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 2
How many hookup stories have you here posted before? 0

My first Gay sexual encounter

How long ago did this hookup happen? 3 years

What was your relationship status at the time? Engaged/Married (monogamous)

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? James is 37 years old and shorter than I am. He is 5’6″ with a stocky build and outwardly gay. He is the life of any party and definitely a fun person.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? This was totally unplanned and unexpected. It was instigated by James while we were both staying at my brothers home in Long Island, NY after a night out on the town.

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 had never held any interest in men sexually, I am married and have several kids and overall a very happy and satisfying life. I travel for work and was staying in New York for work. One weekend my brother asked if I wanted to drive up to visit since I was not able to go home and we seldom get an opportunity to visit together. I rented a car and drove to his place. We had a great day and went out that night with several of his male friends. He suggested we all return to his house since most of us were too drunk to drive and five of us agreed. Back at his house we all sat around having a few more drinks and finally at about 4 that morning we started to go to bed finding places to sleep. I went into a spare guest room and laid on the bed with my head spinning and fully dressed in my jeans and a button down shirt. I closed my eyes and felt my head spin.

I faintly heard the room door open and opened my eyes to see one of my brothers friends, James, stumble into the room laughing from a conversation outside the hallway. He looked surprised to see me and said sorry and that he could not find a place to sleep and thought this room was empty. He sat on the edge of the bed as I lay there and asked if I was also gay. I told him no and he asked if I had ever had sex with a man and I again said no. This time he leaned in and kissed me squarely on the mouth before getting up and walking out the door to use the restroom saying he would be back if that was ok to which I replied “sure. “ I turned and was lying on my back half asleep when he returned a few minutes later.

I felt his weight on the bed beside me and then felt him begin to rub my back through my shirt like a deep muscle massage. It felt amazing and I took my shirt off with his help letting him rub my bare back. I felt my shoes and socks come off and then felt him reach underneath me and unsnap my jeans as my pants and underwear were pulled down. I had raised my hips giving him access and offered no resistance to his advances. I felt my ass cheeks being massaged and spread and then I felt his hot breath as his tongue began licking my anal opening. It felt amazing and I raised my hips to give him full access. My cock was hard as a rock and he reached around a few times and stroked me as I lay in complete ecstasy. I felt his tongue press inside my hole and thought I would cum. I heard him whisper in my ear that he wanted to fuck me but he didn’t fuck drunk boys but maybe some other time he would take my ass and fuck me good.

He turned me over onto my back and began sucking my cock and jacking me off as I lay on the bed with my pants down around my ankles. He remained fully dressed and continued giving me one of the best blowjobs I had ever experienced. He moved down and sucked my balls as he jerked me off with his hand until I shot a huge load of cum all over my chest and face in an orgasm that seemed to last for minutes. Once my cock was drained he kissed me softly and got up leaving the room. I was too tired to move and fell asleep in the position he left me covered in my own cum.

I woke up the next day and dressed and walked out with matted cum in my hair that I could not wash out in the sink. Several of the guys were sitting at the table drinking coffee. I got a lot of stares and finally one of the guys remarked that it sounded like I was having a lot of fun last night and they all laughed. James walked in and said his goodbyes and invited me to come visit him anytime I was in the Boston area where he lived. He gave me his cell and address and then left.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

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? The next day my head re-lived the experience over and over. I enjoyed it immensely and did not know what or where it would go. James had given me his address and number and I traveled to the Boston area frequently. Since this time we have become very close friends and friends with benefits when I am visiting his area.

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? Intoxication, Just happened, I don’t know why, just went along with it

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol, Marijuana, hashish, Poppers (Amyl Nitrate)

How wanted was this hookup for you at the time? I don’t know / I’m not sure

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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 have never talked about this to 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? It was an experience I never imagined or thought about. It forced me to reconsider my viewpoints on sex and my own sexuality.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I never thought of myself as being bi or thought it possible to have a relationship with a sexual component with another man. While my wife and James remain the only people I have had sex with or am currently sexually active with I would not say that a casual sexual encounter is outside the realm of future possibility. The sex with my wife is satisfying and different than what James and I share.

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? In life and in my marriage I have always been in a very dominant position. With James he is always the one to take full control and I fall into a very submissive role which I enjoy.

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 was raised with a very strict religious background and sex was not discussed. My wife and I have never really talked about sex or varied from what I would classify as being routine with no kink. This relationship has opened my eyes to a whole world of possibilities and enjoyment.

What do you think about the Casual Sex Project? I enjoy reading the experiences of other people.

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