by Holo

Gender: Male
Age: 32
Race/ethnicity: White
Current location: TX
Highest education received: College degree (eg., BA, BS)
Occupation: Law
Relationship status: Married
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 40
How many hookup stories have you here posted before? 1

First Casual

How long ago did this hookup happen? 5 years

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…)? Stranger

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? Thin, young guy, maybe late 20s. We met on CL (Craigslist), m seeking m casual encounters.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I went to his apartment and knocked on the door. We arranged over CL

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 walked in and he led me to a bedroom.
It was my first CL encounter. Maybe his too. We stood there for a sec. He was wearing shorts and no shirt.
I had on jeans with nothing underneath. I said “maybe you should start sucking my cock”.
He knelt down, unzipped me, and started vigorously sucking on my cock, and I got very hard in his mouth.
After a few minutes he suggested we get on the bed.
I lay down and he sucked on me more, and I pulled his shorts and boxers off. I rolled over – he was still standing – and started sucking his cock. It was my first time, and I loved it. He said things like “oh god, that’s magical, that’s beautiful” and so I just took my time and enjoyed myself.
Eventually he got on the bed and I said “I want to fuck you in the ass”.
I’d brought condoms and lube, and he eagerly knelt on the bed.
I regarded his beautiful ass while I put on the condom and lubed up.
With no warning I penetrated his ass – he cried out loudly.
I grabbed his cock and stroked it while I pumped away on his ass. He moaned and leaned back into me. I stroked him and fucked him until we both came. I loved it.

I quickly left. He thanked me and that was that.

Did you have an orgasm? Did your partner(s)? Yes, and yes.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Condom.

What were your REASONS for having this hookup? I was horny and curious to be with a man.

Were alcohol or drugs involved? If so, how much? i was pretty tipsy.

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 left, he thanked me.
I felt pretty weird for a few days, but then got over it. It was so anonymous he could have come to my door and I’ve not have recognized him.

To whom did you talk about the hookup? How did they react? No one.

Was this a consensual and/or wanted experience for you? For your partner? Yes, totally consensual on both ends.

Do you regret this hookup? If so, why? Nope.

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? It was intense, very hot, safe, consensual and completely nsa.

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 or anything else? This was the first of what has been about 25 CL anon hookups.

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

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