Gay Again

by Juggler

What’s your gender? Man
How old are you? 23
What’s your race/ethnicity? White / Caucasian
What country and/or city do you live in? Germany
What’s your occupation? student
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Atheist
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? I am still not sure whether I am bi or actually gay. I am certainly not hetero.
How many sexual partners have you had in your life (including oral sex)? 4
How many hookup stories have you here posted before? 1

Gay Again

How long ago did this hookup happen? Last Weekend

What was your relationship status at the time? Same as current status

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

How long did you know the person before this hookup? For less than 6 months

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? N. is a 25 year old male. He is very slim and tall. He has long hair and looks a bit feminine. He is definitely gay. I had met him a while ago and he had introduced me to gay sex (see previous story).

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After my introduction to sex between men I was very conflicted. I had really enjoyed the contact with N. but I felt guilt towards my girlfriend. I kept on thinking about N. and having sex with men. My problems of getting aroused by my girlfriend got worse. I still have sex with her regularly, but I seriously wonder how much I enjoy it when I am honest with myself. On the other hand, I am scared of the social consequences it would have to declare myself gay. I am really conflicted.

So I kept on browsing the gay dating site that had put me in contact with N., but I didn’t meet up with anyone. Via this site, I had also chatted a bit more with N., but we did not meet up. I had been a good boyfriend. Last Friday I got horny and checked again. There was a message from N. asking whether I felt like visiting him that evening! His boyfriend was away and he wanted to hook up with me. That was so easy that I could not resist. I immediately messaged back that I was up for it. I then called my girlfriend and made up some story that a rock band she is not interested in would play I would go to the gig without her.

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? When I got to N’s apartment, we greeted each other with an intimate kiss as if we were true lovers. Yes, I did enjoy that. We went to the bedroom straight away and got undressed. N’s penis was very stiff right from the start. I was quite impressed that I had provoked such physical reaction in him. I also got stiff pretty soon. We touched, kissed, rubbed our penises against each other, and mutually gave blowjobs. At some point we in the 69 position.

I told N. that I was ready to be anally penetrated. I had fantasized about it and now I wanted to experience it. N. put a condom on, used a lot of lube, licked my anus, stuck a finger inside to put more lube in. I was impressed that he did not lose his erection during that process. He mounted me missionary style and told me how I should put my legs so it did not hurt that much. N.s penis is long and skinny but it still hurt more than I had hoped for. I still enjoyed the intercourse during which we kissed at times. It made me feel that now I have truly had sex with a man. N. ejaculated inside me. I wanked after he was done and N. helped me a bit by fondling and kissing my penis and testicles. He licked my butthole again which is a practice I am quite sure I don t want to do myself but I quite enjoyed N. doing it on me.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

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? After we had sex, we chatted and smoked weed together. We had a night out and N. showed me some gay clubs. The music was not to my taste, I have to say.
N. and I discussed our relationship on this night out as we were getting drunk together and smoking dope. I felt that we were developing a good friendship. N. told me that I have to understand that he would not be willing to hook up with me that often. He has a boyfriend. Yes, it is an open relationship, but if we met up this way often, N. feared that we would become lovers and he did not want this to happen. I have to say I was pretty moved by this, it was not just the alcohol and the dope.

N. was really friendly about this. He offered to help me hook up with someone that night, but I felt a bit shy about that. It was all a bit too much at once. I prefered to go home with N. N. at first refused, but later agreed, saying he would find me a boyfriend later. N. joked that once I had a proper boyfriend, we could fuck again.

I ended up sleeping in N’s bed. We had more oral sex and lovemaking, but no more anal. My butt still hurt a little bit from the first time. That actually felt good and i was really proud of the fact that N. had penetrated me.

I hope to see N. more often and also hope that he does not stick to his idea that we should not have sex to make sure we don t become lovers. He agreed to see me again, but next time with his boyfriend. The plan is to go out together and find me a boyfriend. I said all of this in a more complicated ways, but that is the bottom end of it.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Thought it was an important experience to have, Making new friends, It was easy / convenient

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? No one yet.

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? Somewhat

Did your partner get emotionally hurt as a result of this hookup? Somewhat

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The sex and the connection of friendship I have felt with N. N. really wants to help my in my journey to find my sexual identity.

What was the WORST thing about this hookup? That I felt a bit rejected by N., even though I do understand the reasons.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Homosexuality is something wonderful. Everybody who has any fantasies in that direction should try it. Honestly it was really as great as I had imagined it to be. Get over your fears, it is worth it.

If it does not work out with N., I will find more casual homesexual partners in secret until I am ready to break up with my girlfriend.

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

All things considered, how NEGATIVE was this experience? A little 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 does not work out with N., I will find more casual homesexual partners in secret until I am ready to break up with my girlfriend.

What do you think about the Casual Sex Project? I wish there were more gay stories.

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