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What’s your gender? Man
How old are you? 54
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Boston
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Hi
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
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)? 6-8
How many hookup stories have you here posted before? 1

The Next Time

How long ago did this hookup happen? 4 years ago

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

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

How long did you know the person before this hookup? For more than 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? My wife, L was 49. Long black hair, green eyes and about 150lbs. at the time. The other was my best friend, B, who is 5’11” and about 240. We’ve all been friends a long time. I had submitted a previous story about them hooking up the first time. This was the second, that I was aware of, time they hooked up.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The first time they had hooked up I had drank too much and went to lay down. After they thought I was sleeping they ended up having sex. I instigated it this time by pretending to drink too much and going to bed leaving them alone.

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 knew my best friend was coming over to watch the game so I pretended to drink more alcohol before he got there. Last time I had had to lay down and my wife had hooked up with him. This time, shortly after he arrived, I pretended to drink too much, too fast. I had purposely done it early to give them plenty of time to see if anything would happen.
After drinking some I told them that I had drunk too much, too quickly, and was going to lay down for “a few”. I went into the living room, right next to our tv room, and laid down on the couch. I pretended to fall asleep with 5 or 10 minutes.
As before I heard them whisper awhile and really didn’t know what was happening but I was still excited. After a while, my wife came in to check on me. She went back to the tv room, partly closed the door, and I heard her say that I was out like a light. B just said good.
In a few minutes, I heard them both start to moan a little. I heard him say, “you are so fucking good at that!” She told him she loved his cock so I imagined he was getting a blowjob. This went on for a while and I heard him say I wish you could teach my wife to suck like that. She stopped and I heard her ask him if she really wanted her to call her and give her pointers because she had been doing her husband? He said, somewhat louder, God no! and they both laughed.
After some more time I heard her say, “I want you in me.” He asked, “What if we get caught?” She left the room, came in again to check on me, I had begun to act like I was lightly snoring, and she went in and told him, “You know how he is — once he’s passed out nothing can wake him.”
She led him to our bedroom and I gave them some time before I heard my wife moaning. I went to try and peek but they had partially shut the door so it was harder to see.
When I was finally able to look my friend had my wife bent over our bed and he was pounding her hard from the rear.
Though I wanted to watch more, I snuck back down the hall and waited. In a while I heard her trying to lower her voice and she was saying, “fuck me,” over again and again and then muffled her cries as she came.
At that point, I went back to the couch and pretended to again be asleep. They didn’t come out of the room for a while and when I again heard moaning I started to go watch again but ran back to the couch when everything got completely quiet.
Shortly they came back downstairs and went into the kitchen. That talked in low voices for a while. I heard him tell her that he had wanted to fuck her for years and she seemed surprised at that. Like last time I heard him ask, jokingly, when could he make another appointment and she asked him, “What about tomorrow?” He asked if she was serious and she said I was working but she was serious. He said, “Oh my god!” and I heard them kiss. In a few minutes I heard him moan again. I quietly got up and was able to peek around the corner to see her on her knees blowing him in the kitchen. I went back to the couch, made noise like I was waking up, and started to get up. I heard them stop and I went into the bathroom.
When I came out they were both sitting in the couch in the tv room watching the game as if nothing happened.
After the game, my friend left, and we went to bed. My wife was incredibly horny and was all over me. We started to have sex and I didn’t last long as I was already worked up and was even more excited fucking my wife knowing she had fucked my friend earlier and she had no idea I knew.

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? This was all very new and exciting to me and I had a lot of mixed emotions. I really wanted to tell them I knew and had no problem with it but didn’t know if that might actually stop it, so I said nothing. The next day, while at work, I was incredibly excited knowing my friend intended to go over and fuck her. When I got home she was, again, wicked horny and we ended up skipping dinner and had a marathon session of sex. It was obvious, to me, that he had got her all hot.

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

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Intoxication, It had been so exciting the first time I wanted to repeat the experience.

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

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I instigated it but they didn’t know I knew.

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’ve never told anyone about this.

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? Very exciting. Seems to enhance our live life.

What was the WORST thing about this hookup? Not telling them that I knew what was going on. I wanted it to lead to more but wasn’t sure how to do that.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’m surprised at my own reactions but has made sex even better.

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? I feel, between two consenting adults, that as long as no one gets hurt there is no problem with it.

What do you think about the Casual Sex Project? I think it’s great to learn so many people feel similar or have similar experiences.

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