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What’s your gender? Man
How old are you? 35
What’s your race/ethnicity? Black
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? Higher Education
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? A little
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? No
How many sexual partners have you had in your life (including oral sex)? Too many to count
How many hookup stories have you here posted before? None

Strap-On Play

How long ago did this hookup happen? A couple of months ago

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Paid sex

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 don’t know why but I have strong urge sometimes to just be fucked but not by a man, I don’t consider myself gay and I’m not attracted to men in any way. But I’m incredibly turned on by dominant woman and especially dominant women with strap-ons. Because of this I regularly post on Craigslist and respond to ads about strap-on sex. Surprisingly there are a lot of women who post ads or who respond to my ads. This is how I meant this woman who called herself Tammy.

Tammy posted an ad about strap-on sex and I responded. It took her a few days to get back me and when she did she told me that she was very experienced in strap-on sex and that she charged a small amount but that she mainly did it to feed her ass fetish. Tammy sent me some pictures wearing a big strap-on that instantly made my dick rock hard. She was a very sexy black woman in her mid 30’s with a nice ass and fairly large tits. Once I saw the pictures I was excited to meet.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We emailed for a few days then exchanged numbers and texted to set up a time to meet. I decided to meet when my significant other was out of town and I invited Tammy over to my place. She came over in the middle of day, when she walked in she looked older than the pictures that she sent but still attractive. We sat on the couch and talked and she told me about herself and I did the same. I offered the money that agreed upon but she didn’t take it which threw me off. I think she wanted to earn it first, which I appreciated. Our conversation lead to strap-ons and she pulled out the dildos that she brought with her, she had about 4 different toys. They started out small and ranged to about 12 inches, which kind of scared me. Soon we both figured it was time to get to it and we headed up stairs to my guest 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? When we got to the guest room she ordered me to undress while layed out the various dildos that she brought. Once we were both naked she looked at my semi hard dick and smiled in amusement (I have a pretty nice sized dick). She then ordered me to place my hands in the dress and to stick my ass out so that she could examine me. I nervously placed my hands on the dresser and assumed the position while she kneeled behind me and started to caress my ass, lightly spanking it and licking my checks. Once she thought I was ready she lubed up her fingers and inserted her thumb in my ass, slowing stroking it and working my ass open. She played with my ass for a while and it felt amazing. After about 15 minutes she ordered me on my knees and made me eat her pussy, which I devoured like it was my first meal. She came over and over while she called me all kinds of dirty names. Once she was done with my tongue I picked out a dildo for her to use on me, I choose one that was about 6 inches and not too wide. She then strapped up and bent me over the bed and started to fuck me, and I loved every inch of her strap-on. I could feel her dick stroking my prostate and I felt like I was cumming every time. She fucked me for a good 20 minutes, changing from hard to slow and sensual. Then she laid on her back and I got on top of her and rode her. At first it felt weird to be in this position but I started to get comfortable and rode her harder and harder until my dick exploded with cum all over her chest, which she seemed to love as much as I did.

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? After the hookup we both cleaned up and either she’s an amazing actress or she really enjoyed herself. While we were both still naked she kissed my ass and complimented me on how nice it was and how that fuck was a great start to her weekend. We got dressed and she looked at the money that I left on the counter and asked, “Is that for me?” as if to say, “Have I earned that now?” and I graciously handed it to her.

I’m definitely going to get together with her again. Next time I want to try a bigger dildo and have her fuck me harder from behind.

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

What were your motives for this hookup? Fun, pleasure, horniness, Submission / Relinquishing power

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Marijuana, hashish

How intoxicated was your partner? I don’t know

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, I keep my desire to be fucked in the ass to myself. I can’t tell anyone about this side of me.

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Submitting to a woman with a strapon and being fucked. It felt amazing and I don’t know why society tells men that enjoying prostate stimulation makes you gay.

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, this wasn’t my first time with casual sex. I’ve done it many times, for regular sex and kinky sex.

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? No

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? While I love my significant other and find her beautiful both physically and mentally, I sometimes want things that she doesn’t want to do. So I look to causal sex to fill that void, and for the most part it has been a positive experience.

What do you think about the Casual Sex Project? I think it’s a good idea.

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

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