by Jake

Gender: male
Age: 16
Race/ethnicity: white
Highest education received: Not graduated from high-school
How religious are you? Not at all
Sexual orientation: Bisexual
Any other term(s) that describe your sexual orientation/sexuality better/best? More into guys
How many sexual partners have you had in your life (including oral sex)? 17
How many hookup stories have you here posted before? none

“Just Experimenting”

How long ago did this hookup happen? August 2013

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…)? one-night stand

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 a little less taller than me (I’m tall), had straight dirty blonde hair and Grey eyes. He had the perfect body for a tank top in my opinion. He always had nice clothes on and smelled nice.
He was my best friend for two years. We knew everything about each other and met up at least one time a week. Me, him and another friend of mine were kind of a best friend group at the time. Slowly I felt I have feelings for him and for some time I didn’t even know it’s sexual feelings. One time our other best friends in the group told me he told her he doesn’t know what it means but he may have some feelings for me.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After some time we forgot about our feelings and for some reason stopped being friends at all. Not in a bad way we just drifted apart. Some time after that we talked again and decided to meet up. We met about once a week for some time and got a little closer. One time we met up at a park next to his house and in a moment of silence I asked him “Tell me something I don’t know about you.” After 20 seconds of thinking he started repeating the words “I’m not gay” and threw in “I may be bisexual” one time in the middle. I understood he has some problems with his sexuality. That night we were really close to a kiss. Not in a romantic way just sexual but it didn’t happen in the end. After that we decided to meet up at my house a week later when my parents are not there and he said he’ll bring alcohol. I was convinced that’s when something was going to happen.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? When he got to my place we saw there’s not enough alcohol for the both of us so we decided that only one will drink and he volunteered. After drinking what’s left of the bottle he quickly got kinda drunk and casually took off his clothes till he was left with boxers. After some time we just talked he tried to take off my pants just as a joke so I did and then he pushed me on a long bean bag I had. We were just lying there with him on top of me looking at me for a while and then he started talking about thinking about experimenting. I told him I’ve experimented with guys and girls and that it doesn’t really say anything about you so he will calm down about it. Suddenly he started kissing me and we made out. Slowly I put my hands on his perfectly shaped ass and rubbed them around. Then we went to my room where we did exactly the same thing just every couple of minutes we switched places so we will both be on top and beneath. If I can say one thing that he’s the best at its grabbing my ass. It felt so good I loved every second of it. It was crazy cause I wanted it to happen for so long and it finally did. With me on top I started rubbing his dick over his boxers and it felt bigger than I thought it would be. I stopped kissing him and went down to give him oral. I took his dick out of his boxes and it looked even bigger than it felt. I sucked his dick and his balls when he told me to get over next to him. He took off my boxers and started sucking my dick. He was way better than I thought. I held his head pushed it in and out and he managed to deep throat. He told me to suck his dick again this time he was holding my face from both sides and he fucked my face. For some reason, maybe the alcohol, I enjoyed it but I wasn’t caught up in the moment on the other hand he was. He pulled me roughly to his face again sucked my dick fast while grabing my bare ass. I told him I’m going to cum but all he did was shove my dick deeper and I came in his mouth. 
After that we stopped. I guess me being satisfied satisfied him. I loved the way he treated me. I never saw that in part of him. He was rough but caring and fun.
We decided to go to sleep and he asked me if he can come sleep with me and for some reason I don’t know till today I said no. I just didn’t want to sleep with him. Now when I think about it I would do anything to go back and let him sleep with me. It bothers me that much.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I was only 15 and he was not even 15. We didn’t think about that kind of stuff even though I knew I won’t go any further in case I did catch something from other people I’v been with.

What were your REASONS for having this hookup? Being a horny teen.

Were alcohol or drugs involved? If so, how much? Third a bottle of vodka for him.

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? We didn’t talk for about six months and then we started meeting up again. We didn’t do anything or talk about it. He will still acting totally straight. He was afraid of being anything else then heterosexual. For a month we met up about 4 times and I started thinking it may lead to something more between us, maybe even a relationship. It’s not that I was in love with him or even had a crush I just considered it have a good idea. I could see me being serious with him. The last time we met we talked about what happened and he told me it was fun and he liked it but he wanted being with guys to be different. I thought he meant being in a relationship and not just a one time things which made me kind of happy but his next sentence disappointed me when he said he wants stuff like that to happen only rarely if he’s drunk at some party, he doesn’t want it to be a casual thing.

To whom did you talk about the hookup? How did they react? I told my friend from the group we three had and she really laughed. Telling my girl and guy friends about my one time things is casual for me. Lately I told two of my guy friends who know him and they were very surprised but amused.

Do you regret this hookup? If so, why? I would do anything to go back and let them sleep with me. My only regret.

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? Physically the best thing was him grabbing my ass. He just knew how to do it. They weren’t any bad things but I guess the whole level of it could be better if I was a little drunk.

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

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