What’s your gender? Man
How old are you? 55
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Chicago
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Attorney
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 30
How many hookup stories have you here posted before? 0
How long ago did this hookup happen? Three weeks ago
What was your relationship status at the time? Same as current status
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? I was on business and was horny for a man to man sexual encounter. He contacted me via Grindr, I had not met him before. He was a bear, about 6’ 3”, 280, with a bushy brown beard
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met via Grindr. He was staying at the same hotel. After exchanging pics and what we were into, he invited me up to his room.
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 room. There was not a whole lot of talking. We each got naked and then kissed deeply while standing next to the bed. We then lay down on the bed and kissed some more, his average size cock got hard and I sucked it for a while. He then had me lay on my back and touched and sucked my cock for a bit as well.
He then spread my legs wide and positioned himself so that his body was pressed up against me, his hard cock brushing the crack of my ass. He got some lube and spread it on his cock and on my ass. He raised my legs high and pushed the head of his cock against my hole. It popped in and I moaned as he began to thrust inside me—it felt good.
After a couple of minutes he pulled his cock out—I should add that he did not have a condom on, and direct me to turn over and lie on my stomach. I complied, placing a pillow underneath me and spreading my legs wide. He entered me from behind and began thrusting again, placing the weight of his body on mine as he fucked me.
As he continued, he began moaning and grunting and told me I had a hot ass several times. With the weight of his body on me, I could barely move but I was fine with it. I could feel his cock swell as he got closer to orgasm, it felt much fuller.
He then began thrusting faster and grunting. I could not feel him shoot his load in me, but shortly thereafter I felt the sensation of a lot of liquid in my ass as he continued to pump his cock inside me. Eventually, he slowed and continued to lay on me for a couple of minutes.
He pulled his cock out and I got out of bed and went to the bathroom to clean up. I could feel cum squishing in my ass as I walked. After I cleaned up, we said goodbye and I went back to my room
How sexually satisfying was this hookup? Very
Did you have an orgasm? No, but I was close
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? This was a one-time hookup. I felt good about it but did worry a bit about doing it bareback. He was married too but still…
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Discussed STI testing history
What were your motives for this hookup? Fun, pleasure, horniness
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
To whom did you talk about the hookup? How did they react? No one
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? Not at all
Do you regret this hookup? Not at all
What was the BEST thing about this hookup? The hot Anal sex, the intimacy of mutual oral and kissing
What was the WORST thing about this hookup? Nothing
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? Not at all negative
What do you think about the Casual Sex Project? I like the stories
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