My Gay Exploration


This post is sponsored by The T Bar.


What’s your gender? Man
How old are you? 22
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
Highest education received: Some college (currently in college)
What’s your current relationship status? Single
Religious affiliation: Atheist
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Sexually Bi, emotionally Heterosexual
How many sexual partners have you had in your life (including oral sex)? 5
How many hookup stories have you here posted before? 0

My Gay Exploration

How long ago did this hookup happen? 1 year ago

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

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

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 decided to actually materialize my bisexuality and went on a gay dating site to explore the “market”. At some point I met this boy, one year older than me, seemed gentle, nice. We messaged for two days and planned to meet on that Friday night to go at a gay club. He was an average height, chubby and was at it seemed, gentle and shy. We went to the club, made small talk, engaged in dancing, had a soda, then a drink, both of us. We mostly tried to talk in that chaos.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Later on that club night we went at the back of the club, found some sofas and privacy as it was big enough of a club and not fully loaded. We stayed there for a while, then I decided to have some guts and went on his lap. I started kissing him for a while, he liked it, we did that a bit more and I was getting horny. I reached for his penis in his jeans and rubbed it to get it hard. He seemed surprised but Ok with what I was doing, so I continued until he cummed after a short while. I took what I could from there, put some in my mouth and frenched him. At this point, I must be clear, I was wanting just some sexual gains to fulfill my night, rather egoistically. From there, we danced a bit more, he only grabbed my penis a bit while doing so, remaining shy and maybe a bit shocked from my sudden escalation from before. We leaved the club and I offered to meet him tomorrow, at a cheap hotel. He agreed.

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? The next morning I rushed to that hotel to rent a room. I told him the I had and to come at around 1 PM, after explaining the night before the location. I decided to make a bit of a fuss and went to buy a bottle of red whine, then went to the room at around 12 PM and waited. He knocked at some point, entered and I offered him a seat on the room’s sofa.We opened the wine and drank it from the plastic cups I had with me, talking and trying to get comfy. The wine kicked in a bit and I made a move, continuing with another round of kissing. Now, he was a bad kisser, but at least this time he seemed to try more. I took his tshirt off, unbutton his pants and let him finish undressing while I went on the bed. His penis was already up, he came near me, we kissed a bit more and then I went for a gentle blowjob to enjoy myself. He came in, maybe, less than too minutes; Like a reflex, I swallowed. That was unpleasant for my grand scheme of having sex. I also stripped down, lay on the bed and let him blow me. Worst BJ of my life, but I tried to enjoy it. I asked to go 69. His dick seemed to get hard again as I was sucking and I stopped him from our 69 as I was reaching my ejaculation. Stopping that, I went for the condoms and lube that I had with me. Rather bossy, I told him to stay doggy style and proceeded with anal that lasted shortly as I came soon after entering. The rest of the time was spend cuddling and sucking each other, as I lost hope to try anal again that day. He didn’t mind. The mutual sucking/masturbation was pleasant, but not so exciting as I hoped my day to be. We parted ways after 3 hours or so, but I stayed in that room until the next day since I rented it and didn’t wanted to waste my money.

How sexually satisfying was this hookup? Somewhat

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? We entered a week of messaging and I discovered his true annoying personality that made me cut him loose from my contacts and interests, ending any future flings.

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, Learning new things, experimenting, Thought it was an important experience to have, To feel more confident, To cheer myself up

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? I don’t know

What substances did your partner(s) consume? Alcohol

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? One close friend. She was happy for me from what details I told.

How would you best summarize people’s reactions about this hookup? Relatively positive

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Exploring my homosexual interests regarding sex.

What was the WORST thing about this hookup? Partner wasn’t capable to deliver much of a sexual moment and enthusiasm.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Neah.

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

All things considered, how NEGATIVE was this experience? Not at all 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? Loving it. Healthy. Fun. Exciting. Trying to get more withing my limits and conditions.

What do you think about the Casual Sex Project? A great initiative.

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