by Chuck

What’s your gender? Man
How old are you? 22
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Some college (currently in college)
What’s your occupation? Student
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Kinky
How many sexual partners have you had in your life (including oral sex)? 17
How many hookup stories have you here posted before? First!

First Time Making an Older Woman Submit

How long ago did this hookup happen? 2 Months Ago

What was your relationship status at the time? Single

How would you best classify this hookup? Fuck-buddies / Booty call

How long did you know the person before this hookup? For less than a month

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? Very cute in shape white woman who was a decade older than me. Short haircut, nice little breasts, perky butt. Talked thru an online site for about a week, went on a date to make sure neither of us were (totally) crazy. Heavy making out, sucking on her breast outside when no one was around, but no sex that day. Nothing but positive feelings before the hookup. She has a great personality and is very attractive.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Hookup began in a hotel room after she picked me. Planning was involved in regards to the date, time, and what we both consented to. I instigated as I like to take charge and she likes to submit.

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? Her nude body grinding on me while I was still fully clothed and she wasn’t allowed to use her hands to touch me. Her trying to get my penis in her mouth before I could even take my boxers off. Shoving my penis down her throat until she gagged. Repeat. Slapping her in the face with my penis. Spanking her bare handed. Much gusto. Brushing my penis against her back, butt, and breasts until she was begging me to stick it in her. Doggystyle with my hand clutching her hair. Missionary with me choking her out. Slapping her across the face with my hand. Throwing her around. Rim jobs both ways. Her playing with my balls (my favorite). Handcuffing her to the coat rack, and spanking her. Much gusto again. Anal for my first time ever. Not really a fan. I much prefer the vagina. Cowgirl. She was a great lover and we both really enjoyed ourselves. Ended with her masturbating on top of me after I had finished for the second time.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

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? Just hang out for a bit after. She’s easy to talk to. Felt great about it the next day. We keep trying to make plans to see each other again but its not working with our schedules. We talk once a week, if that. She’s cool but not like I really have a sense of her day to day life.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Withdrawal, Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Thought it was an important experience to have, To feel better about myself, To feel more confident, To cheer myself up, Power / Dominance

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? Two friends. “Nice bro.”

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you 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? Finally getting to do anal.

What was the WORST thing about this hookup? Not really digging anal.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Hasn’t.

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

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

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? Everybody should be free to make their own choices. We’re adults.

What do you think about the Casual Sex Project? Great. Keep it up.

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

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