by James

Gender: Male
Age: 45
Race/ethnicity: Caucasian
Current location: London
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Teacher
Relationship status: Married
Religious affiliation: Catholic
How religious are you? Not at all
Sexual orientation: Bisexual
How many sexual partners have you had in your life (including oral sex)? Over 600
How many hookup stories have you here posted before? None

My First Time

How long ago did this hookup happen? 20 years ago.

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? He was a young guy. Were both cruising (by car) a well known gay cruising spot. It was my first time cruising and I was quite nervous.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We parked side by side and I went to his car. We started chatting. The only planning involved was that I wanted to get laid that night, hence the cruising.

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 was quite nervous and didn’t know what to do so I grabbed his crotch and began to pull out his cock right there. He suggested that we went to a more discreet place. I went back to my car and followed him. When we got there, we immediately started kissing. The first time I kissed a man. After some mutual oral action. He got pretty hard (he had a pretty big cock – around 7 inches, real 7 inches, not porn 7 inches). I guess he wanted to get fucked because he sat on my lap but I somehow persuaded him to be the top. We didn’t have any condoms so he penetrated bareback and fucked me for a long time. He was sweating and drops of sweat kept dropping on face.

Did you have an orgasm? Did your partner(s)? I didn’t have an orgasm but he came inside me.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None. As I said, he fucked bareback. It was the only time I ever had unprotected sex. He did ask me if he could cum inside me and told him to go ahead. I was lucky but… I still get hard just thinking about this dude cumming inside my ass.

What were your REASONS for having this hookup? I desperately wanted to get fucked. I had played with toys a lot. I even had an 8 inch dildo to play in bed at night. But I wanted the real deal.

Were alcohol or drugs involved? If so, how much? No.

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? Mixed feelings. On one side, I was happy and proud to have lose my virginity. But on the other side, I spend a few weeks worrying about STDs. That was a one time thing. From that one, I always wore condoms. It was my first time and one of the hottests fucks ever. I would love to meet that guy again. He was so gentle during and afterward.

To whom did you talk about the hookup? How did they react? No one. I’m still in closet.

Was this a consensual and/or wanted experience for you? For your partner? Definitely. And for him also. After all, we were both cruising a gay spot.

Do you regret this hookup? If so, why? Never. And I’m glad that my first time was with this guy. He was hot, gentle, and had a pretty big, thick dick. Wish I could meet him again.

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 adrenaline during the cruising part was awesome. But the best part was definitely the fuck he gave me. The worst part were the weeks after before I got the STDs test results. This hookup just confirmed what I already knew. I love sex with men. Today,  20 years and over 600 men later, I still love casual sex with anonymous men.

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 or anything else? Answering this survey sure made me go back in time

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

What’s Your Fantasy? Click here to be part of the largest survey on sexual fantasies ever!