First Time with Another Man

by Anonymous

What’s your gender? Man
How old are you? 26
What’s your current relationship status? Single
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? I would consider myself bisexual, but not open to my family and friends
How many sexual partners have you had in your life (including oral sex)? Around 10

First Time with Another Man

How long ago did this hookup happen? A few 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? We met through Craigslist. I never was attracted to men until we actually met in person. He was a little older than me but not by much, maybe by like a couple years. He was about 6’1’’, athletic build and no piercings but with quite a few tattoos, short dark hair, no facial hair, and blue eyes.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I wanted to pursue being with another man after years of not being good with the ladies. I wasn’t really physically attracted to men but I thought it would change and it did. I was also interested in the idea of being the bottom when it came to sex with guys. I posted an ad on Craigslist with pictures, hoping there would be a man who’d be interested. I got a few responses but I was really picky and didn’t really like anyone or they lived far away. Eventually, I got a response from someone whom I was interested in and lived close by. We chatted for a bit and decided to meet up at his 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?

When I arrived at his place, I was very nervous. When he opened the door, he greeted me with a smile. I sat down on his couch and we talked for a bit. He asked if I wanted something to drink and I asked what he had. He told me he had an extensive liquor cabinet. I decide on some shots of Jack Daniels. We each had a few shots and I was getting pretty buzzed. He then made a compliment on my eyes and I made one about his as well. He then started leaning in for a kiss. I was so close to resist but I was hoping for the best. I was amazed that how good of a kisser he was. He was way better than any of my ex-girlfriends. I started getting really horny and was thinking, “I thought this would feel wrong but it feels so right.” He then told me to follow him to the bedroom. I got up to follow him and he started to hold my hand as we were walking to his room. When we got to his room, we continued to make out while undressing each other. I got down on my knees mesmerized by his cock and thinking that this was actually really happening. I was nervous about sucking a guy off but I had seen my exes do it enough that I would just follow how they did. He started to moan a little so I knew he was liking it. He then said he was ready to fuck me. I got up on his bed on all fours. He got a bottle of lube and started living up my ass. Before he put it in me, I was thinking it would hurt a lot. But when he did, it felt really good. He took it slow for the first minute and then started to speed up. “You like how that feels?“ he asked. “I love how it feels,” I said. We were both moaning in pleasure. He then wanted me on my back with my legs in the air. He would then started fucking me like this while I was stroking myself. After a while, I was about to cum. It was the most intense orgasm I had ever had. I came harder than I ever did either by myself or with my exes. I didn’t want him to stop because I was loving getting fucked. I knew he was getting closer to cumming as well. After a while he said he was gonna cum, so he pulled out and came a huge load on my face and in my mouth. I had always heard about the taste of cum and his tasted very sweet and was really warm. He asked me if I enjoyed myself and I said yes. It was getting late so I decided to spend the night so we spent the rest of the night making out in his bed until we fell asleep in each other’s arms.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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? When I woke up the next morning, he was still asleep. I quietly left, but I left him a note saying I had an incredible time and left him my number. He texted me later that day saying he’d like to get together again sometime. I wasn’t sure if I wanted to be in a relationship with a guy so I told him and he said he wasn’t really looking for one either but we could continue hooking up.

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Hoping or expecting it would lead to something more, Thought it was an important experience to have, To feel more confident

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

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? Somewhat

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 knows about this except the two of us

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Do you regret this hookup? Not at all

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? We continued to hook up occasionally and after a few months, we decided to pursue a romantic relationship. We would be together for a little over a year before we split up. He moved because he got a new job and it was best to go our separate ways.

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