by

What’s your gender? Man
How old are you? 35
What’s your race/ethnicity? White / Caucasian
What’s your current relationship status? In a serious relationship (monogamous)
How many sexual partners have you had in your life (including oral sex)? 22

First Time With A Man

How long ago did this hookup happen? 3 years ago

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? One-night stand

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 was a bit older than me, around 40. He was in good shape, was married, and told me he had been with a few men when he was younger. He stopped when he got married, but said he missed it.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I found myself getting curious about being with a man, so I posted an ad on Craigslist. After a few time wasters and men I wasn’t into, he contacted me and we set up the meeting at my apartment. He arrived later that day and I buzzed him up and greeted him at the door. He was smartly dressed as I think he came straight from work.

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? We went into the bedroom and both stripped completely naked. I was already hard in anticipation, but he wasn’t fully there. We started touching each other’s bodies and after rubbing his chest and ass a little, I took his cock in my hand and started stroking it. He continued to feel my ass and this was the first time I’d ever held someone else’s cock. The feeling of it getting hard in my hand was amazing. He was a bit smaller than me but was still a decent size, probably around 6 inches, which I was a bit happy about, not knowing if I could handle a monster the first time.

We both laid down on the bed together and he moved down and start giving me head. I couldn’t believe I’d finally given in and acted on my secret fantasy. He was sucking on me a few minutes then started working a finger inside my ass. It felt so good and I know right then I would go all the way, but before that, I wanted to try his cock in my mouth. I moved down and took the head into my mouth and started sucking it gently. I couldn’t believe I was doing this, but it also made me really horny. I kept sucking him as he started fingering my ass again, and that was when I told him I wanted him to try fucking me. He got up, put on a condom, and started rubbing lube into my ass and on his cock. I got on all fours and felt the head of his cock against my ass. He put his hands on my hips and shoved his cock in. I pulled away from him a bit as I was very sore. I reminded him I had never done this before and that he needed to go slower.

After a minute, to let the pain die down, he once again lined himself up and this time, he eased himself into me. It felt a lot better with him getting deeper each stroke until his hips were slapping my ass and I really started enjoying it. I started to moan and this was his signal to start fucking me harder, which felt really good, but I couldn’t go long as my ass was still a bit sore from his initial thrust. I then told him I wanted to fuck him now and he said okay. I put on a condom and lubed up as he laid on his back with his legs in the air. I moved in close to him and slowly pushed into his ass. He was really tight and it felt so good. I loved looking down at my cock going deeper and deeper into him before long I had my full length inside him and like I did before, he started moaning, so I steadily increased the pace until I was fucking him quite hard after a few minutes. I told him I was getting close and he asked me to cum onto his belly so just before I did, I pulled out, whipped the condom off, and shot onto his stomach. He then asked me to bring my cock back up to him and he started sucking me again, only now he could easily get two fingers into my used ass. As he sucked and fingered me, he was stroking his cock while I played with his balls until he came into what was now a puddle of both our cum, on his stomach.

How sexually satisfying was this hookup? Somewhat

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? After we were both done, he went to the bathroom to clean up. Then we both got dressed and said our goodbyes. I was so turned on by what had happened, I had a wank thinking about 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, Learning new things, experimenting

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

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? I don’t know / I’m not sure

Do you regret this hookup? A little bit

Why do you regret this hookup? I regretted cheating on my girlfriend.

What was the BEST thing about this hookup? Getting to experience something I’d fantasied about for a while.

What was the WORST thing about this hookup? That he wasn’t more gentle at the start so I couldn’t go very long.

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

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

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