by Baby

Gender: M
Age: 40
Race/ethnicity: Caucasian
Current location: Colorado
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: lawyer
Relationship status: domestic partner
Religious affiliation: none
How religious are you? A little
Sexual orientation: Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 50
How many hookup stories have you here posted before? 5

Took It in the Ass

How long ago did this hookup happen? 3 weeks

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…)? one night stand

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 not very attractive, flabby fit guy, hairy, in his late 20s.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Craigslist. I wanted to get fucked in the ass. He was the responder I chose. He was ok with anon and would pound me in the ass with a condom.

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 went to his apartment and knocked. He let me in. It was dim, but not dark.
He showed me the bedroom. I asked to use the restroom. I peed and cleaned up a bit more. I went back to his bedroom.
He was in boxers and a t-shirt. I massaged his cock while he unbottoned my shirt.
I dropped my shirt and he unzipped my jeans and felt up my cock.
Then I got to my knees and pulled off his boxers. I sucked on his 5″ cock a bit. It was small and easy to deep throat and he groaned and moaned.

I stood up and said “lay down.”

He did and I got naked and knelt next to him. I kissed him and stroked him. He was enthusiastic so I pulled his head up and he sucked my cock a bit.

Then I said “fuck me, baby”.

He flipped me on my back, stood up and reached for some lube.
He put my legs on his shoulders then fingered some lube into my ass. I was so nervous and tight. He laughed and said “it’s just my fingers”.

Then he showed me his condom, put it on, I felt for it, and he put lube on it.
I guided his cock into my ass, pulled his bed covers over my face, and dug my heels into his shoulders.

He pounded my ass. His 5″ cock felt nice, sexy. After a minute I said “stroke my cock” and he did.
He stroked me with him and as he came he stroked me hard and I came too.

He pulled out, and I rolled up and grabbed my clothes.

In the bathroom I cleaned up and got dressed. As the bathroom was near the door, I exited, said “thanks” and left.

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 for anal, none for oral.

What were your REASONS for having this hookup? I wanted to be fucked in the ass.

Were alcohol or drugs involved? If so, how much?: none

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.

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? Wanted, yes

Do you regret this hookup? If so, why? Nope, except he was not very attractive and I regret that.

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

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

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