Shtupping a 22-Year-Old Straight Boy

by Ray

What’s your gender? Genderqueer / Nonbinary
How old are you? 34
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: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Professor
What’s your current relationship status? Dating casually
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Pansexual
How many sexual partners have you had in your life (including oral sex)? 7
How many hookup stories have you here posted before? 1

Shtupping a 22-year-old straight boy

How long ago did this hookup happen? 1 month

What was your relationship status at the time? Single

How would you best classify this hookup? Friends-with-benefits

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

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 met this nice young man at a flogging workshop; we exchanged some banter, and went off to flog other people. He left before we could exchange contact details, but I found him on Fet and added him.

He’s a nerdy programmer boy with beautiful dark eyes and a deep voice. He dresses badly, but undresses well.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? He asked if I wanted to practice flogging and other sorts of play together, and I said sure. We messaged each other discussing what we liked, and I discovered that he was great at listening and at dirty talk. We met up at a cafe, planning to wander around the city together in the daytime and then go to a play party in the evening, but I felt really attracted to him, so at my suggestion, we went back to his place and made out. Then we watched a movie and went to the play party and made out again.

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? At his place: we kissed a bunch, he hurt me with various kinky toys, I gave him a blowjob, and we both masturbated. We talked dirty about how he was hurting me and I was loving it. (That was true.) I told him some stories about stuff I had done with other lovers.

At the play party: he hit me with a bunch of kinky toys again, I gave him another blowjob, and we rolled around cuddling and scratching each other for a while. We did more dirty talk on the theme of how I like it when he hurts me. A couple of times he hit me really hard and I swore/ insulted him, which is part of the fun for me.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? We both went home to our respective houses and I went to sleep very happy. We wrote each other messages afterwards, and he said a careless thing that hurt my feelings, and I told him so. His response was thoughtful and apologetic. We kept talking, and we have hooked up again, and I’m going to jump him tonight. He’s great, and I have a crush on him, though neither of us wants a committed relationship. I’m just enjoying the feelings of novelty and sexiness and excitement.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, IUD (Intrauterine device), Discussed STI testing history, Exchanged recent STI test results

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Submission / Relinquishing power

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? I told a few friends, who congratulated me on the sexy fun I am having.

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

Did you get emotionally hurt as a result of this hookup? Somewhat

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? He is a great communicator, and it’s so sexy. He listens to me, he seeks out information about what I want and how I feel, and he tells me what he wants and how he feels.

What was the WORST thing about this hookup? Getting my feelings hurt by the careless thing he said.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I feel better about sex with men, better about casual sex, and more confident of myself.

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

All things considered, how NEGATIVE was this experience? Not at all 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? When I was a teenager, everybody told me that people who have casual sex with each other don’t care about each other as humans, or value themselves. Based on my most recent experience, this is a lie. I am divorced, and the casual sex I’ve been having is so much more respectful and more fulfilling than the married sex I had for years.

I also feel much more positive about sex with straight men after this experience. (I’m still making myself invisible to straight people on OKCupid, though.)

What do you think about the Casual Sex Project? It’s so great to get people’s story out there.

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