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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? USA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? District Manager
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
How many hookup stories have you here posted before? 0

Not Really Sleeping

How long ago did this hookup happen? 4 years or so

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

How would you best classify this hookup? Not planned

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, 5’4” about 150. Brown hair with 38c boobs. The other guy was my best friend, B who is about 5’11” and about 240 at the time. We’ve all been friends forever. L & B constantly flirted with each other. B was at our house often, usually watching whatever game was on t.v. and drinking our beer.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was at our house and we’d been drinking through a double header. I had been drinking vodka and coke and after drinking awhile it usually puts me out and everyone knows it but hadn’t tonight. When I got up to go to the bathroom I was super dizzy though and told my wife and friend I was going to lay down for a few. I laid down on the couch really thinking I’d probably fall asleep. As I laid there my wife and friend started talking in lower voices, but I could still hear them. My friend was trying to get my wife to flash her tits for him. At this point I pretended to deep breathe a little so they would think I was sleeping. They joked back and forth and my wife said if she did what would she get? My friend said anything she wanted and she said, “don’t tempt me.” They kidded back and forth a little more and he asked he to at least take off her bra. She told him to hold on a second and came in to check on me. Our living room is right next to our t.v. room. I pretended to be passed out. She went back and told him I was out of it and would be until morning. He said, “good take off your bra.” She laughed and I heard clothes rustle and her asked, “Better?” He said, “no, your top is still on.” She asked if she took her top off what was she going to see and he said, “I already told you, everything.” I was getting so excited listening to all this. I heard her say, “ta-da,” and I assumed her top was off when I her my friend say, “I always wanted to see your tits.” My wife giggled and said, “Your turn!” Again I heard clothes rustle and I heard my wife say, “I didn’t mean everything!” The idea that my best friend was naked with my wife in the very next room was one of the most exciting things I could never have thought of. I heard them move and whisper but couldn’t understand what they were saying now. A few minutes later I heard him moaning and had a pretty good idea what was going on. This was confirmed when I heard him say, “you really know how to suck cock,” and she told him to be quiet.
I was going crazy as this went on for awhile. Finally I heard him say, “I really need to fuck you.” She said, “wait a minute.” She must have put in her top because she had it in when she came in to check on me. I again pretended to be passed out and didn’t move a muscle when she put a blanket on me.
A minute later she was guiding my friend up the stairs to our bedroom. A few minutes later I heard her moaning. It took me forever to quietly go up the stairs, but when I did I peeked around the corner to see her on top of him. You’d think a guy would be angry or jealous, but to me it was exciting. Not wanting to get caught, I only get quick peeks but got to see many positions. As they started to finish, I made my way back to the couch.
A little while later they quietly snuck down the stairs. He went in, got dressed, and kissed her on his way out. He asked if he could make another appointment and she said definitely. He left. She cleaned a few things in the kitchen and then came to wake me up to go to bed. The next day when I ask what happened she said my friend left shortly after I laid down. To this day they don’t know what I know about that night and other hook ups.

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? This was a first and, surprisingly, very exciting for me. A few weeks later I pretended to drink too much, too fast and pretended to get sick. I told them I was going to bed. Shortly afterwards I again pretended to be asleep when my wife came to check on me. Within minutes I could hear them fucking for over an hour.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? They don’t know that I know.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Just happened, I don’t know why, just went along with it

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

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

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Not at all

Did you consent to this hookup at the time? I was too out of it / passed out / asleep and therefore unable to give consent

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’, but didn’t give a ‘no’

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? A little bit

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? It excited me in a way I wouldn’t have imagined.

What was the WORST thing about this hookup? That I didn’t get to watch. That I was afraid to tell them what I knew.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’ve never really thought casual sex was an issue.

All things considered, how POSITIVE was this experience? Fairly positive

All things considered, how NEGATIVE was this experience? Not at all negative

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