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What’s your gender? Man
How old are you? 44
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: College degree (eg., BA, BS)
What’s your occupation? Finance
What’s your current relationship status? In a lousy marriage and secretly dating
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 12
How many hookup stories have you here posted before? 0

First Time Anal

How long ago did this hookup happen? 1.5 years

What was your relationship status at the time? In a lousy marriage and secretly dating

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

How long did you know the person before this hookup? For less than 6 months

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? She is a super cool and sexy woman, late 30s, beautiful and has a great personality. I met her on seekingarrangment dot com. We had hooked up a few weeks prior in a hotel in the city where she lives and I travel to for business. First time was awesome as well but all we did was oral and “regular” sex.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was back in the city where she lives for an overnight business stay, this time I met her at her house and spent the night.

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? She had a massage table set up in the living room, she never went to school for it or anything but she gave me a full body massage as good as one could get in a spa. She started stroking my cock and balls and started going closer and closer to my ass. She could tell I was getting totally into it and then very casually asked: “Do you like anal?” I told her I had never done it but that it had been my number one fantasy for decades. She just scampered off and disappeared to another room and returned about 20 seconds later with a box of dildos and anal toys. I completely lost track of time so I really have no idea how long it went on, but she kept penetrating me with her toys and fingers, edging me and massaging me for a long time. I was so turned on and in that moment it was amazing. She finally let me have an orgasm and I just have this image burned into my memory of her watching these three or four huge arcs of cum sailing across her living room.

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? I felt amazing. I always knew it was just a fun seeking arrangement type hookup, but something about whatever the message, anal, and edging does to one’s brain chemistry, I never felt more deeply cared for by another person than that night.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)

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? Finally being with someone for trying anal sex.

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? How great it is to be in a consensual non-monogamous relationship. It seemed very “healthy”. Total honesty and no BS.

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? I still see her about once every 2 months. She seems to up her game every time. Some light bondage, blindfolds, strap-ons, etc.

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 think its good for us as a society to finally recognize that the secret is out in the open. We all like really good sex.

What do you think about the Casual Sex Project? Very interesting, I think it’s good to get these experiences out there.

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