What’s your gender? Man
How old are you? 47
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? OC, CA
Highest education received: Some college (not currently in college)
What’s your occupation? Super spy, but not really
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Hedonistically flexible
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? 5 or 6

Sex With An Ex(‘s Best Friend)

How long ago did this hookup happen? 16 years 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 1 to 3 years

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? Jen. She was petite, barely 5′, 100lb. Very short brown hair, blue eyes, an appealing smile, but otherwise very average. She was my ex-wife’s best friend, so I’d met her a number of times. We had never hooked up before this, and I wasn’t particularly sexually attracted to her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My ex confessed that she cheated on me. A lot. I decided I’d fuck her best friend, but I had no actual plans. Looking back at it, I think she instigated it.

I’m at a party, and Jen was there. She was always super friendly, flirty, and genuinely seemed fun. She knew we’d separated, and gave her condolences, along with giving me a shot. And another. We had too many drinks together, to the point where neither of us is going to be driving anywhere. I was flirting heavily with Jen, who kept looking better and better as the liquor flowed. She wasn’t at all bad looking, just not really my type. Petite, not really much shape, kinda pixie-like, but not as cute as a pixie would be. She was also kinda young.

Jen and I were having fun together, to the point where we stopped noticing much of the party around us. She was totally enamored, and I was eating it up. Anytime I’d compliment her, she’d blush. I was getting off on that, and the feeling that she was really genuine. Also, I was drunk.

She had to pee, but the bathroom was taken and had a line. She just said ‘come with me’ and went to the backyard. ‘Make sure nobody is coming’ and she pulled down her jeans, squatted, and pissed. She just went up another notch. Not necessarily the pissing itself, but her attitude about it, complete lack of shyness… and she had a rad landing strip.

Jeans on, standing up again, she took my hand to go back in, but I pulled her to me and kissed her. There was a moment of shock or surprise, then she kissed back. We sloppily made out for a couple minutes, hands starting to explore, then she stops dead. “Oh shit, what about [your cheating separated wife]?”

“My ex is not part of this, but I understand if it makes you feel uncomfortable,” was my response. As much as I wanted to fuck Jen to piss off my ex, I also liked her, and I’m not about to just use someone. We talked for a minute, the whole time she was looking at my eyes, then lips, then eyes, then lips… then started kissing me 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? We move back inside the house, the party still going, and find ourselves in a bedroom. Making out continues, and I took her shirt off, revealing a tiny red see-through bra. She took my t-shirt off and started kissing my chest (about her head height- I’m a good 9-10″ taller than her). We stumbled to the bed, where she laid on her back and I pulled her jeans off, she scrambled to get to my belt while I asked if she was ok with this. “Yessss” and my pants were getting pulled down by a very enthusiastic young lady.

One of us is naked, one is wearing a tiny bra and itty-bitty panties. They barely covered her landing strip. I pulled her panties off, pulled her bra off, and I looked at her for a moment; some of those concerns of her looking super young were gone. Her little titties were perky, hips looked feminine, and her pussy was pretty. And- she was aggressive.

I pulled her towards me to kiss her, she wrapped her hand around my cock and grabbed my ass with her other hand. I don’t think we kissed long, before my dick was in her mouth. She sucked in a very porn-like manner. Lots of saliva, lots of hand, lots of… ahh… noises. Whatever, my dick was in her mouth and she spent plenty of time with the balls before I pushed her back onto the bed, knelt beside it, and pulled her pussy to my mouth. I ate away like it was my last meal, while she moaned, bucked, shook, and apparently came a few times.

Jen sat up, pulling me up to kiss her, and she said two things I’ll never forget: “I love the taste of my cunt” as she kissed.. and “*I* take it in the ass” with a long emphasis on “I” which I took as she knew my ex hated anal, as she turned and bent over in front of me. She also said something about not being on birth control, ovulating, and I heard it when my cock had just bottomed out in her pussy. I slowly pumped a few times, while rubbing her ass. From what I remember, it was the pinkest hole I’d ever seen. Cock out of her pussy and sliding into her ass, she went wild again. Just as the tip was getting in, she pushed back *hard*, slamming her ass into my pelvis, cock all the way in, and wanted fucked *really* hard. I legitimately fucked her asshole as hard as I could. Not fast, but hard. Coming out until my cock was at the rim, then slam back in as hard as possible. We kept this up for a while, Jen bucking and at some point doing most all of the work while I just met her pushing.

Sometime in here is when the door opened. We were fucking on the bed that had a lot of people’s coats on it. Some coats still on the bed, some on the floor, some that, ahh… may need to go to the cleaners.

Here we are, my cock in Jen’s ass, her still bucking back and forth but slowly now, and some chick looking for her jacket. As drunk as I was, that chick was sloppy shitfaced drunk. I’m not sure she even knew what was happening.

The door closes, I keep fucking and Jen absolutely screams that she’s cumming. Loud. Loud enough for plenty of people to hear. She shook and collapsed forward, rolling onto her back as she did. She grabbed my cock and started sucking. It only took a moment before I came in her mouth. I think she swallowed, but really fuck if I can remember for sure.

Jen pushed the jackets off the bed, and we got under the covers. We cuddled for a while, kissed a lot (and yes, I realize my cock was in her ass, then she sucked it, then I made out with her… and no, it doesn’t bother me in the least), and fell asleep.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

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 woke up super early the next morning but realized it wasn’t actually super early. Or early at all. It was around 10 am. I woke Jen up, who was totally hung over. We dressed and kinda snuck out of the house. Jen hadn’t driven there, so I offered to drive her home. We had breakfast, then drove to her place.

Jen was pretty damn cool. She was really big on “no strings attached” because she didn’t want a relationship at all, but we ended up casually seeing each other for a year or so. To this day I still don’t know if my ex ever found out. I completely stopped caring about doing anything to piss her off by the time Jen’s panties were off.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Not the greatest method, but anal

What were your motives for this hookup? Fun, pleasure, horniness, Intoxication, Revenge / Getting even, It was easy / convenient

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol, Marijuana, hashish

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol, Marijuana, hashish

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 close friend, who wasn’t surprised in the least.

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

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? Being surprised at how aggressive and enthusiastic of a lover she was

What was the WORST thing about this hookup? The hangover

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not a change, but more a continuation on the path that I’ve followed for decades.

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? Casual sex has been both a large part of my life and other times, not a part of my life at all. I’ve been in open relationships, closed relationships, single, etc.

What do you think about the Casual Sex Project? It’s great. I’m glad to see it’s doing well.

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