First Time Anal



What’s your gender? Man
How old are you? 57
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Post-graduate degree (currently pursuing)
What’s your occupation? Financial Services
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Adventuresome
How many sexual partners have you had in your life (including oral sex)? 80 +
How many hookup stories have you here posted before? 2 or 3

First Time Anal

How long ago did this hookup happen? 40 some years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Fuck-buddies / Booty call

How long did you know the person before this hookup? For 1 to 3 years

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 around my age at the time maybe a year younger, around 16. He was tall thin with dark blonde hair and green eyes with a big cock.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Tommy and his brother were childhood friends. My family and theirs had large farms in the same area. I had been closer with his brother Greg who was my age. We would hang out together, fishing, drinking, talking about girls and sex. Typical teenage stuff for that time period. Greg, Tommy and I would often camp out or have sleepovers on the weekends. One night we started talking about sex and Greg was laying next to me and reached out under the cover and grabbed my cock. I was hard and I reached over and grabbed his and we jerked each other off while talking about girls. Over time we gradually started playing together, giving each other blowjobs, sometimes doing 69.

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’m not sure if the brothers talked about this, but eventually when Greg was gone somewhere Tommy and I started hanging out together and one night he grabbed my cock as his brother had done under similar circumstances. Both guys had similar builds with big cocks. One night Tommy and I were alone camping out, drinking beer. We had previously been giving each other blow jobs. This night we started playing and soon we were naked and sucking each other off when he asked me to lay on my back. I thought he was going to slide his dick between my thighs like we had done before, sometimes looking at a playboy magazine. We didn’t have girlfriends yet so we would improvise ????. I layed on my stomach and instead of going between my thighs I felt his big cock at the entrance to my asshole! I was pretty buzzed so I kind of went with it. He slowly pushed the head in and at first it hurt like hell, but after a few minutes the pain went away and he pushed more of his big cock in. He started fucking my ass and it started to feel good and I came without even touching myself. He cried out and shot his cum in my ass. He finally got off of me and said it was my turn but he didn’t think he could take my cock in his ass, so he would suck me off. He didn’t know I had already cum.

How sexually satisfying was this hookup? Very

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? We remained friends and he and I would play together, but we never did anal again. We eventually got girlfriends and we grew apart.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)

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

How wanted was this hookup for you at the time? Very

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? No one, but one time he and I hooked up in front of his cousin so I guess he knew about it.

How would you best summarize people’s reactions about this hookup? I didn’t tell 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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Getting fucked in the ass! New experience. I later would fuck some other guys in the ass, but I never was the bottom.

What was the WORST thing about this hookup? Eventually, we grew apart, we might have crossed a line we didn’t plan to.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? At the time I was a worried I might be gay, this was before people discussed sexuality on a spectrum. Over the years I have been with far more women then men, so I realized I mainly prefer women.

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

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

Anything else you want to add about this hookup? If this had happened today and I was the same age, I think I might have had more experiences with guys and have been more comfortable with same sex encounters. It took me many years to realize it was ok and healthy. Not everyone is the same

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? Having had many threesomes, some bi experiences it has to lead me to accept who I am and enjoy thinking about the hot experiences I have had.

What do you think about the Casual Sex Project? Great!

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