First Time Rimming A Guy

by Doe

What’s your gender? Man
How old are you? 38
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? UK
Highest education received: Some college (not currently in college)
What’s your occupation? Self employed
What’s your current relationship status? In a serious relationship (open)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Switch
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? 1

First Time Rimming A Guy

How long ago did this hookup happen? 22 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For more than 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? I will call him Jack(not real name). We were both 16 at the time, known each other for several years. He would stay at his grandparents next door to me often. We had our first gay experiences together (see previous story), we were wank and suck buddies. I was also fooling around with his twin sister at the same time.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It happened at my house when he stayed over. We had already been wanking together for over a year and that had progressed into sucking each other off every time he stayed over. I had managed to get hold of a proper porn VHS tape from mail order, mostly guy/girl scenes but a bit on girl on girl thrown in.
We would watch the tape together, in particular, the anal and rimming scenes. My bedroom was the opposite side of the house to my parents and above the garage so, we could be quite loud, especially with the TV on most of the night.

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? It was late at night in my room, we were chilling naked in my bed together watching MTV(when MTV was good). Jack suggested putting the porn tape on again because he wanted to wank off before sleeping. I instead suggested we skip the tape and act it out together. He wasn’t sure what I meant so I just started kissing him and squeezing his ass. I pushed him over on his front and mounted him. I pressed my hard cock against his ass and began grinding it up and down. I pressed hard to make sure my length was rubbing up against his hole. Then I slid down his body and buried my face into his ass, I had already rimmed his sister a few times so I just did the same to him and he really enjoyed it. After about 10 minutes we swapped and he rimmed me, oh boy what a feeling, instantly hooked. We both wanted to cum so we laid face to face on our sides and started rubbing our cocks against each other until we both shot our loads, we were covered in each others cum. Not long after we still ended up putting the porn on and I sucked him off because I was desperate to taste his 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 carried on fooling around with rimming and grinding becoming a normal routine. We both loved the experience and couldn’t wait to repeat it.

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? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection

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? Told no one

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Realizing how much I enjoyed rimming with guys.

What was the WORST thing about this hookup? Nothing.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It played its part in my developing sexuality.

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? It felt more degrading to rim a guy compared to a girl.

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? It’s not for everyone but it’s great if you want to explore sex.

What do you think about the Casual Sex Project? It’s great for sharing experiences.

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