by DJ

Gender: Male
Age: 31
Race/ethnicity: White
Current location: Connecticut
Highest education received: Some college (not currently in college)
Relationship status: Married
How religious are you? Not at all
Sexual orientation: Bisexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Bisexual recovering sex addict
How many sexual partners have you had in your life (including oral sex)? 50
How many hookup stories have you here posted before? Too many

First Time Top

How long ago did this hookup happen? A week ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Booty call

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? K was a younger black man whom I met on Grindr. He was very feminine and was definitely a bottom.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I’m also typically a bottom with men, but I saw him at Walmart one night and was surprised how attractive I found him to be. I messaged him the next day and he invited me over during my lunch break.

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? I got off work for my lunch break and he lived about two minutes away so I just drove over. I walked in and we sized each other up as men do when they’re hooking up. We went up to his room and began kissing.  I don’t usually like kissing men at all, but his big lips and smooth skin felt good on mine. I was surprised at how frantically I kissed him and how much it turned me on. He took control and began to grind all over my body. This was a bit weird. He kind of dry humped me for a few minutes. I didn’t get much pleasure from this and ended it quick because I had limited time. So I told him to suck my cock and he obliged. It felt very good. Then I stood up and we kissed some more. I took my pants off and removed all his clothes. I noticed he had a very small cock and wasn’t hard. I didn’t take it personally because I think he might be transgender (obviously pre-op) and I’ve heard that transgender guys don’t get hard ons easily. I didn’t care much though. I just needed to get off. So I bent him over, slid on a condom, and slid my cock inside his willing ass. His ass felt great on my cock, and he had a nice bubble butt that looked great bouncing on me. As I pounded him, I realized that the condom had broke. So I pulled out and came on his ass. I couldn’t believe how much I came. It was a massive load and it looked great on his black ass. I

Did you have an orgasm? Did your partner(s)? I did. He did not.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Condoms. It broke at the end but I also just got tested.

What were your REASONS for having this hookup? I was very horny and wanted to try something new.

Were alcohol or drugs involved? If so, how much? No

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? I cleaned up and he hopped in the shower as I left and got a bite to eat, before returning to work.

To whom did you talk about the hookup? How did they react? My online friend. She was amused.

Was this a consensual and/or wanted experience for you? For your partner? Yes

Do you regret this hookup? If so, why? No

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Best was kissing him. Also, the amount of cum that I shot on his ass. Worst was that the condom broke, though I stopped immediately and I’m not worried anything could’ve transmitted in that time.

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

All things considered, how NEGATIVE was this experience? A little negative

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

What’s Your Fantasy? Click here to be part of the largest survey on sexual fantasies ever!