Twice the Fun

 

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What’s your gender? Woman
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? United States
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Attorney
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Bi—leanings
How many sexual partners have you had in your life (including oral sex)? 25-30
How many hookup stories have you here posted before? Zero

Twice the Fun

How long ago did this hookup happen? One month 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 am married to a woman, but I enjoy having sex with a man on occasion when I am out of town on business. I had two separate hookups on this occasion and met both on Grindr.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was out of town. My first hook-up contacted me on Grindr, he was also middle-aged and a cross-dresser and wanted mainly to have oral sex. He invited me to his hotel room and said he would leave the door ajar and be wearing panties, lingerie etc.

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 arrived—it was dark and he was in full cross-dress except no wig. I got naked and into bed and we ground and I touched him and rubbed him through his panties and fishnet stocking. He was not particularly attractive, but I was very sexually aroused by his feminine attire. He started sucking my cock and I began fingering his ass and he asked if I wanted to fuck his “pussy.” We had not discussed anal before, but I said yes, and I slipped on a condom, lubed up his ass and slid my cock inside him and started fucking him doggy-style. He began moaning very loud and began bucking hard, which brought me close to coming right away. I tried to slow down, but he kept bucking and I quickly came. He expressed a little disappointed that I did not last longer, but expressed satisfaction I was willing to fuck him. I cleaned up and left.

After a few hours, I was still horny, and I really wanted to bottom. I went on Grindr again and made contact with a middle-aged black man who claimed to have a really huge cock that would satisfy any man. After texting a bit, I felt that he and I were compatible and I invited him up to my room. When he first arrived, we began to undress and he then stated he had forgotten his lube in his car. I told him I would need lube. He left to go get it and I thought perhaps that he would not return—but he did. We both got naked and into bed. He was tall like me—which I like. I began caressing his body and then began sucking his cock. It was huge—I mean huge. It was extremely thick and I could only take 2/3 of it into my mouth. He was clearly enjoying being sucked and began rubbing my head and playing with my ass. I was a little scared to have anal because of his size but eventually, I asked him if he wanted to fuck me and he said yes. I told him to go slow and that I would need lots of lube. He positioned me at the side of the bed on my hands and knees. He was standing and fingered me for a while to loosen me up. Finally, I could feel the head of his cock pushing into my ass—I gasped as he continued to push in. It was definitely painful at first, but he was fucking me very slowly and it eventually started to feel really, really good. After about 5 minutes, he asked me to lie on my stomach and climbed on top of me and started to fuck with his body pressed on top of mine. I really enjoyed it, and eventually, he started moaning and grunting and thrusting harder as he came. He stayed on top of me with his cock still inside of me for a couple of minutes and then pulled out. He cleaned up and we had a nice conversation before he left.

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? Being married, I felt some guilt, but at the same time felt satisfied with the sex I had. These were one-time hookups and I do not expect to see either again.

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

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 did not talk to anyone

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? A little bit

Why do you regret this hookup? Some guilt over cheating on my wife.

What was the BEST thing about this hookup? The intense pleasure when fucking—and being fucked.

What was the WORST thing about this hookup? There was no kissing during either encounter, which I like.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really. This was the first time I ever had sex with two separate people though, so perhaps I may be inclined to experiment more.

All things considered, how POSITIVE was this experience? A little positive

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

Anything else you want to add about this hookup? I especially enjoyed my second encounter—even though I did not cum.

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? I wish I did not feel as guilty.

What do you think about the Casual Sex Project? I really like the stories.

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