First Time Ass Pounding

by Biguy

What’s your gender? Man
How old are you? 47
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 (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? Not sure maybe 75
How many hookup stories have you here posted before? 0

First Time Ass Pounding

How long ago did this hookup happen? 9 years

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

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

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? He was in his late 20s and an athletic African-American man with an 8 inch cut thick cock. I met him on craigslist, having placed an ad looking for a top. I didn’t know him at all but he had a nice body, he smelled good. He didn’t say much.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We exchanged a few emails, a few photos, and arranged for him to come to my house.

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 went upstairs to the bedroom. The first thing we did was I got on my knees, lowered his pants and took his soft cock into my mouth. I licked his balls and as far back as I could reach towards his ass crack. I had cleaned myself out before he came, and I had been using a dildo in my fingers on a regular basis to prepare for getting fucked the first time. After he became hard, I put a condom on his cock, lubricated, and squatted over his dick and took it slowly into my ass. Once that became comfortable, I suggested that I put a condom on his cock, lubricated and squatted over his dick and took it slowly into my ass. Once that became comfortable, I suggested that I lie on my back. He was getting into it at this point. He put my legs up over his shoulders, pushed his cock into me and begin to pump in and out. We started kissing. I put my hands on his ass and felt his pelvis thrusting into me. After a while, the sensations became intense and uncomfortable. I asked to stop fucking. I got on my knees again, took the condom off and started deep throating his cock. He seemed frustrated not to be able to come while fucking me. Ultimately he jerked off a few times and came in my mouth. He had a huge load of come. He spurted multiple times, filled my mouth with cum, almost like he was peeing. I came in my hand at the same time. To this day I regret not swallowing his load down.

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 agreed to meet again. Ultimately we met probably four or five times. We never really said much to each other. On subsequent encounters, he mostly fucked me with condoms and came inside of me. I would jerk off while I was fucking me and come with him. The last time we met before I moved out of state, I asked him to pull out and come all over me. He sprayed a big load all over my belly. It was a good thing while it lasted. I always wished he could have fucked me with no condom, fill my ass with his seed. It really didn’t seem worth the risk of the time and I’m glad it didn’t happen apart from the fantasy.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Submission / Relinquishing power

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

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? My wife at the time. I guess she was okay with it.

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

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? His beautiful cock, his huge load of cum in my mouth

What was the WORST thing about this hookup? Discomfort from getting fucked the first time

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It was fun to get fucked after years of fucking women, taking the more submissive role. Ultimately the feeling of sex is similar whether it’s a man or a woman, the same release,

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

All things considered, how NEGATIVE was this experience? Not at all negative

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? If it were not for STDs, I would be way more slutty

What do you think about the Casual Sex Project? Fun to read stories

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