First Gay Date



What’s your gender? Man
How old are you? 28
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Enginneer
What’s your current relationship status? Single
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? 16
How many hookup stories have you here posted before? 0

First Gay Date

How long ago did this hookup happen? 4 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? Just met that day

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’s white, 38, 6’2, perhaps 200 pounds, 7 inch cock, nice body, and a soft face. We met while having coffee. I thought he was good looking.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met while having coffee and we chatted for a bit. He asked if we could have drinks later that night. I said yes (not knowing if it was friends or a date). A couple of hours later, we met for drinks. He was already seated in this wrap-around booth and he invited me to sit beside him. When nobody was really around, he wrapped his arm around my waist and pulled me closer. I realized it was a date at this time. He was looking at me so intently. I turned my head towards him and closed my eyes. He leaned in and kissed me. We were in a bar close to where I live and I didn’t want to be outed, so I smiled and backed away. I put my hand under the table and onto his lap. I felt his cock getting hard under his pants, so we paid the bill and I invited him to continue the night at my place.

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? On the walk back to my place he was asking me what I would like to do and I told him that I am more submissive and like the idea of sucking cock and doing anal. He told me he was a total top and had seen me around and wanted to fuck me for a while. We got back to my place and I took him to my bedroom right away, shedding our clothes as soon as we got in the front door. He pushed me onto the bed and we made out with him on top of me. He put his tongue down my throat and I was gasping for air. I tapped him a few times and started making my way down his body, kissing his neck, nipples, and stomach before settling on his cock. It was hard and he had trimmed his pubes. I engulfed his whole cock with one swift plunge. He breathed a little heavy as he asked me to not do anything I am not comfortable with. I said it’s fine, I wanted to suck his cock. I continued for a few minutes, but my neck was getting sore and I didn’t think he was close to cumming, so I turned my body over and reached for the lube on my night stand and handed it to him.

I laid flat on my stomach and I felt a plop of lube on my asshole. I felt all his weight on me and his cock right pushed up against my ass. He asked if he should use a condom and I said I didn’t have any. He told me he was clean so I backed my ass against his cock and it started to penetrate me. I told him to go slow and he did. As he was thrusting slowly into me I started kind of holding my breath and taking it better. He started pushing deeper with each thrust. It felt really good. I was just really getting into it when I felt him cumming in me. He got off me and his face was a little red. he was apologizing for cumming so quickly. I told him it was fine and that I really enjoyed it. I gave him some wet wipes for his cock and put a towel down under me and we laid on the bed kissing. His cum and lube were leaking out of me. He asked me to get on all fours and try to push some of the cum out. I did. Some came out and he used his finger to scoop it up and asked me if I would like to swallow it. I was a bit repulsed by the idea of eating something that came out of my ass, but did it anyway. It actually wasn’t bad. I went to kiss him after, but he wasn’t into the idea of kissing me with his cum or my ass juices in my mouth so we didn’t.

We took separate showers.

We had a couple of martini’s over the next two hours and cuddled on my couch, naked. My ass still felt gooey from the cum. I was a bit bored and asked him if he could get his cock hard again. He told me yes, a blowjob would probably do the trick, so I blew his rather limp cock and it soon became hard again. As it grew, I asked him where he wanted to cum. He said he just usually cums in the moment, so I stroked his cock with my hands and periodically sucked it with my mouth. I asked him to tell me when he was close to cumming. After what seemed like 20 minutes I could feel his breathing increase and he told me he was close. I wrapped my lips around his cock and his cum shot straight up against the back of my throat. I kept me lips sealed around his cock, and pulled off with a pop. I opened my mouth to show him his cum. He was gasping for air, smiling a little. I swallowed. We went to bed and had sex again in the morning, all anal. It was great!

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, not even close

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 kept in touch as friend with benefits.

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

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, Submission / Relinquishing power, Didn’t want to disappoint my partner

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

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? Nobody

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? The sex was quite intimate and I liked that he came in me.

What was the WORST thing about this hookup? The first round of anal intercourse was actually quite short. It was a little painful to get him in me for such a short, yet pleasureable fuck.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I started dating men on top of dating women.

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? I loved it.

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 wish people would be more open to it.

What do you think about the Casual Sex Project? Its awesome. I love a good story to get me in the mood.

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