Leaving Them Alone

by Scott

What’s your gender? Man
How old are you? 42
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? Paramedic
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Cuckold
How many sexual partners have you had in your life (including oral sex)? 6
How many hookup stories have you here posted before? 2

Leaving Them Alone

How long ago did this hookup happen? About 10 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, Amy, is 5’3,” 140lbs, and her bra size is 38C. She has black hair and green eyes. My best friend is 5’10,” 225 lbs, has brown hair, brown eyes, and a 7” cock.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My wife and best friend had been hooking up for some time now. I’ve written about a couple of incidents. Our friend is married but his wife has no idea what was going on. At this point, we had all gotten into the whole idea of my wife being shared. It had developed slowly over time but was happening all the time now. Our friend was looking for any excuse to come to the house and my wife was more than ready for him. If she knew he was coming over without his wife, she’d often dress in just a t-shirt or a button down shirt. She had told him a couple of times before to leave his pants at the door. They never stopped playing with each other the entire time.

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? It was no different on this night. Our friend was coming over to watch a Red Sox game. Amy was dressed in just a white t-shirt. He came in wearing gym shorts and a t-shirt. They kissed, he grabbed her tits, and she grabbed his cock. We made drinks and went to the living room. They sat together. She drew up her knees and spread her legs, and he started to play with her pussy as we carried on a conversation. This is how casual it had gotten. As they sat together watching the game, he pulled his cock out and she’d play with it.
Our friend got up for another drink, and when he came back, he stood in front of my wife. Amy knew what that meant and proceeded to start sucking his cock. Again, very casual, but still exciting to watch. As Amy was blowing him, he told me we were out of vodka. Amy stopped sucking him, started playing with his balls, and asked me to run to the store to get more. I knew they were looking for alone time, and if I went, it would take me at least 20 minutes but I said sure. As I started to leave, I said that I would get a pizza too, giving them more time.

I drove away but parked down the street and snuck back up to my house. It was dark enough. When I peeked in the window, my friend was already fucking my wife. He had her bent over the couch and was taken her from behind. It’s incredibly exciting to watch your wife getting fucked when she doesn’t know you’re watching. He fucked her hard, and I was surprised that he was also slapping her ass. This went on for a few minutes. Then, he stopped, pulled out, climbed onto the couch, laid on his back, and Amy climbed on top of him to ride him. Her expression said it all. She was moaning quite loudly and he was thrusting himself up as well. He moaned and came inside her. I was rock hard as she climbed off him and then licked all the cum off his shaft. I wanted to continue to watch, but I left to go get the pizza and vodka. When I got back to the house, Amy was sitting on the couch with her legs spread. Our friend was on the floor in front of her. He had lathered up her pussy and was shaving it bald, she had been trimmed before. He told me he liked it high and tight. When he was done, he washed her up and went down on her. For the rest of the game, they rotated between oral or masturbating each other. When the game was over, he said he’d better get home so his wife wouldn’t suspect anything. As soon as he left, my wife and I went to our bedroom. I went down on her bald pussy for the first time, and we fucked like crazy. We highly recommend sharing.

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? After we were done, we crashed. They had been hooking up for a while, so everyone was good with it all. My wife confessed she loved the variety, how often it happened, and that it enhanced our own sex life.

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, Attraction to partner(s), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, To cheer myself up

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 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? The next morning, I heard Amy on the phone telling her best friend everything. Her friend wanted every detail. Amy has been trying to get her to hook up with me, but so far she’s too nervous.

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

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? Excitement. Trust. How casual it is. Enhances our sex life.

What was the WORST thing about this hookup? My friend is married, and if his wife found out, or the word got out, it could be embarrassing.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes, we do believe that there’s nothing wrong with casual sex.

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? Highly recommended!

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? It’s too bad that casual sex is looked upon as taboo by some, especially just because you happened to be married.

What do you think about the Casual Sex Project? I think it’s great to learn that many people share the same feelings.

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