First Sexual Experience with Another Boy



What’s your gender? Man
How old are you? 27
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? Scotland
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Arts
What’s your current relationship status? Single
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? With prefernece to women
How many sexual partners have you had in your life (including oral sex)? 35 (I think)
How many hookup stories have you here posted before? 0

First Sexual Expereince with another boy

How long ago did this hookup happen? 16 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Boys fooling around at sleepover

How long did you know the person before this hookup? For less than a year

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? Another 11-year-old boy like me name L. We were friends as we lived close together and spent a lot of time together. I was a very reserved and anxious child while he was quite opposite and in a way rougher than me (family wise). We had become good friends in the meantime and regulalrly had sleepovers.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I bloomed sexually very early (though didn’t lose my virginity until I was 19), and had discovered masturbation sometime around the age of seven or eight (although there was nothing to produce at that time so to speak, but I could still orgasm, though I didn’t really start masturbating properly until about 12). Anyway, it happened during a sleepover at my house when we had stayed up late watching horror films. We had talked about how we both looked forward to having sex with girls and talked about practicing. L. was definitely the one who instigated it.

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 basically compared penises, which we were able to get erect and got naked with me on top. We started grinding them together (frotting) which I won’t deny felt good and I still like to this day. However, I ended up getting uncomfortable and stopped although L. didn’t want to. That was really it. I’m keeping it vague as well on account of our ages in case anyone considers the story inappropriate (apologies if you do but it did happen, and technically it counts as sexual contact). It did stick with me for years and was a part of my repressed bisexuality until I was much older.

How sexually satisfying was this hookup? A little

Did you have an orgasm? No, not even close

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? We remained friends until our families had a falling out. After that, I ended up moving to another town and we lost contact. I did run into him when I was 19 at a job center once. It was really just a quick acknowledgment as I was in a hurry.

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

What were your motives for this hookup? Learning new things, experimenting, Just happened, I don’t know why, just went along with it

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? A little bit

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, even to this day.

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? I discovered at a very early I do like guys as well as girls.

What was the WORST thing about this hookup? I felt awkward about it and like I said it was part of my repressed bisexuality for many years.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really, I was just a kid.

All things considered, how POSITIVE was this experience? A little positive

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

Anything else you want to add about this hookup? I hope no one finds this story inappropriate, it is really just a tale of two boys discovering sexuality. This story isn’t meant to arouse or titillate in any way whatsoever, but I guess it feels kind of good to get it out there finally. The rest of my stories are much more age appropriate and will have more detail.

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 like casual sex, and think it can be a healthy part of anyone’s life at least at some point. I’d like to see attitudes change towards it in the future, as I think a lot of people deny themselves it and can lead repressed lives, but that isn’t really relevant to the story.

What do you think about the Casual Sex Project? I’ve been reading the stories here for a long time and find them to be very educational not only in why we do it but also our behaviour. Not to mention it can be helpful reading other firsthand encounters when thinking about my own.

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