by Generous

Gender: Male
Age: 22
Race/ethnicity: Mixed (Indian/White)
Current location: London, UK
Highest education received: Post-graduate degree (currently pursuing)
Occupation: Student
Relationship status: It’s Complicated
Religious affiliation: Hindu
How religious are you? A little
Any other term(s) that describe your sexual orientation/sexuality better/best? Sexually fluid
How many sexual partners have you had in your life (including oral sex)? 20-30
How many hookup stories have you here posted before? 1

Being a Good Friend

How long ago did this hookup happen? 5 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…)? Long fling

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? My friend, let’s call him James, was a good friend of mine in school. We got on well and we’d known each other practically our whole lives. James is about 5’9, thin but toned with defined abs, brown hair and blue eyed.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were 17 at the time. James hadn’t been coming to school for a few days I went over to his place to give him his missed work. When I went into his room, I was expecting him to be sick or something, but he was just lying in bed playing his nintendo. We got to talking and he told me that he had been feeling really miserable of late because he told his mum that he thought he was gay and she wasn’t taking it so well. So he’d been holed up at home ever since as they worked their stuff out.

I felt bad for him. It came as no surprise to me that James is gay, it’s pretty obvious if you know the guy at all. I sat there and listened to him and tried to be supportive, made a few jokes to lighten the mood and make him feel better.

He then confessed to me that he’s never kissed a guy. He’s kissed a few girls but always wondered what a guy would be like. He was really torn up about it and felt like he was stuck. I felt really bad for him, so I told him that if it mattered to him that much, he could kiss me.

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? James was very surprised by my offer and I didn’t think he’d go for it. But he immediately said, “Are you sure?” I was cool with it and kind of curious myself, so I said, “Yeah”. He leaned in and kissed me then.

All cards on the table, I didn’t mind being kissed by a guy, but in that moment, I knew I preferred women beyond any doubt. But since this was something so important to him, I kissed him back and faked a bit of passion in it. I made out with him for 5-7 minutes and felt like I had had enough and pulled away.

We were quiet after that, it got awkward and I could see that he had gotten hard. He wasn’t even trying to hide it.

He then slowly asked me if he could see my cock. I was a little uncomfortable at that point, but I know I’d seen guys’ cocks before at school and it didn’t seem like too bad a request. In all honesty, the fact that he wanted to see my cock was a bit of a confidence builder since I had just been dumped by my then-girlfriend a few days ago. So I said, okay, and undid my trousers and pulled out my cock. It was completely soft.

He sort of just stared at it for a minute. Then he asked if he could suck it.

I was about to say no, that that was taking things too far, when he interrupted me. He said that I could watch porn on his computer while he blew me and I could pretend it was a girl. He just seemed so desperate and hopeful, I figured, what the hell?

So I pulled off my trousers and boxers and lay down on the bed and put on some porn on his computer while jacking my cock. He kept his clothes on the whole time. I started responding to the porn and getting harder. He then bent down and took my cock in his mouth. No prep leading up to it, no teasing, he just went for it.

It was really good! A mouth is a mouth, after all. He sucked my cock like a man possessed and eventually I stopped watching the porn and just wrapped my fingers in his hair and fucked his mouth.

About 15 minutes of him blowing me, and I told him I was about to come. It was supposed to be a warning. He then paused and told me to come in his mouth. I thought that was incredibly hot. So I came in his mouth. He choked a lot because it was quite a big load, but he sucked it all.

I then pulled up my trousers and left. We didn’t talk about it.

Did you have an orgasm? Did your partner(s)? Yes, I did. One. He didn’t.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Nothing. We were both 17 and it was his first time getting any action.

What were your REASONS for having this hookup? Pity for my friend and a bit of bi-curiosity.

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? Afterwards, I didn’t really think about it much. I knew I preferred women and I would rather be with one, but I was certainly not opposed to being pleasured by a guy. It was an odd realisation to come to.

James and I, from then onwards, established a routine of sorts. He would blow me pretty much every day, including weekends. Most of the time at his house, a few times in my car, once at the cinema and a few times in school. We kept this going for until we finished school and went to different unis, excluding the 4-5 months that I was in a relationship with another girl in-between.

To whom did you talk about the hookup? How did they react? I told a few friends about it years later. They thought it was cool.

Was this a consensual and/or wanted experience for you? For your partner? Yes, for both.

Do you regret this hookup? If so, why? Not really. I do feel though that James always hoped that I wanted more. For that, I feel bad because I knew I could never truly give him what he wanted. I told him that on many occasions, but I don’t think he fully accepted it.

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 best thing was probably the fact that I received daily, enthusiastic blowjobs. The worst about how I’m sure James felt led on in a way.

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

All things considered, how NEGATIVE was this experience? Somewhat negative

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