First Time With A Guy

by Sam

What’s your gender? Man
How old are you? 46
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Engaged/Married (monogamous)
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 20
How many hookup stories have you here posted before? 0

First Time With A Guy

How long ago did this hookup happen? 26 years ago

What was your relationship status at the time? Dating casually

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? I was dating a girl named Karen a the time and she had a friend named Dave. We would all hang out.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She was working on a Friday night and then she was going home to bed because she worked early in the morning. He and I were hitting a party and then went back to his place for some more drinks and watched tv. We were hammered so he said I should crash there. Then we switched on some porn.

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? After a few scenes, we were both getting into the porn and rubbing ourselves. Soon our cocks were out and I noticed that he could be in a porno with the size of his cock. We were stroking and talking about the blowjob scene. I started talking about how good my girlfriend was at blowjobs. He then confessed that he was a virgin and had never even had a blowjob before. I couldn’t keep my eyes off his cock even though I wasn’t even curious. It wasn’t helping that he kept asking questions about how a blowjob feels. Then he noticed I was staring at his cock and he made a comment about my girlfriend’s oral skills and winked at me. I made him swear to never tell a soul and I would show him how a blowjob felt. He was cool and I lowered my head to his crotch. I bobbed on him slowly but hardly had him in my mouth. He started pumping my mouth and grabbed my head and slammed into me and shot a huge load of cum in my mouth. I had to swallow just to breath. When he let me go, he smiled and said that was awesome. I couldn’t believe I just sucked my first cock and swallowed his load. I went to the kitchen for some water. When I came back he was hard again and the porno was now on anal. I went back in the kitchen and grabbed some oil dropped my clothes and walked back into the room nude with only the bottle of oil. He looked at me and said, “I swear I won’t tell a soul about this either.” I bent over the couch, rubbed the oil on my ass and his cock, and he got behind me gripping my hips. He slowly entered my ass and waited until I adjusted to his monster in me. He slowly inched his way in and then he fucked me. He couldn’t resist and started pounding me, which hurt. Finally, I got used to it as he was hitting my prostrate. He mentioned that I was hard the whole time he was in me and that’s when I reached down to grab my penis as I came all over my hand and he shot off inside me. I felt his every twitch and that felt great. He then brought my hand to my mouth and had me lick my own cum. He fucked me a few more times that night. Now we fuck every Friday when my girlfriend has to work.

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? He fucked me every Friday when my gf worked

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, Learning new things, experimenting, Just happened, I don’t know why, just went along with it

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Somewhat

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

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? Getting used

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

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