by Red and Gray
What’s your gender? Man
How old are you? 40s
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? Manager
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Atheist
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? Insatiable
How many sexual partners have you had in your life (including oral sex)? Around 40
How many hookup stories have you here posted before? 2
Wife Set Me Up On A Date
How long ago did this hookup happen? Last night
What was your relationship status at the time? Same as current status
How would you best classify this hookup? Fuck-buddies / Booty call
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 and I have known this couple for a number of years and we go out together occasionally. Their marriage and sex life is a disaster and I can’t figure out how they’re still together. They’re both incredibly good looking people and ‘Jenna’ is quite a diva which makes it difficult to be around her at times. She and my wife are both bisexual and very attracted to each other but have never hooked up for a long and complicated set of reasons I don’t pretend to understand. They are very close and I know way too much about this couple’s sex life, or lack thereof.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I’ve been working out of town for almost 3 weeks and decided that I was going to get tickets for a show and book a hotel so my wife and I could have a night alone and away from her teenage kids that live with us. Private time is rare so this seemed like a great idea. I got home and could immediately tell that my wife wasn’t feeling well so I started to cancel our reservations and she told me that Jenna wanted to see the show if I didn’t mind taking her instead. I was a little resistant at first but decided to go. My wife then talked me out of canceling the hotel so that I could drink and walk to the hotel then sleep in. This made sense to me and I headed out to pick up Jenna. Jenna is already incredibly attractive but that night she had put a lot of effort into looking good. She was wearing a short skirt and midriff top that showed off her very toned figure. I should have known something was up but I’m admittedly slow on picking up on subtle cues. Jenna was overtly flirty, holding my hand, and taking my arm as we walked. As I mentioned earlier she is a diva and I didn’t think anything of it as she was enjoying the attention she was getting from me and the guys admiring her as we walked past.
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? Jenna was snuggled up to me for most of the show which was really nice and I was very aroused but still hadn’t put the pieces together about what my wife and she had planned. Near the end of the show, I received a text from my wife that she hoped I was having fun and added a winking emoji. Jenna and I were still holding hands and just before the show ended she took my hand and placed it on her inner thigh. I was a little shocked but began to realize what was going on. I rubbed the inside of her thigh for a moment then leaned over to kiss her as I ran my hand up her leg and over her panties. We kissed passionately and I felt her gasp as I slipped my finger inside of her. She was very wet and squeezed her legs together to keep my hand in place as she started to grind on it. I broke off from the kiss and told her we should go to the hotel. Once in the hotel room, we continued to kiss as we undressed each other. I picked her up and tossed her onto the bed. For years my wife has been telling me the details of their conversations about all the things she wished her husband would do or would like to try so I have a mental list of cheat codes to pleasure her. I went down on her for a very long time and worked my fingers over her g spot (something I know she doesn’t get at home) making her cum multiple times. I flipped her over and entered her from behind while pulling her hair with one hand and controlling her hips with the other. We both came hard and collapsed on the bed holding each other and laughed about what had just happened.
We spent the next few hours fucking, sucking, and licking each other until we both passed out.
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? We had sex again in the morning and agreed that we should get together again. My wife was eager to hear all of the details when I got home and got very turned on as I recounted what happened in far greater detail than I did here. My wife stopped me at one point and asked if I had showered before leaving the hotel, which I did with Jenna and ended up back in bed with her. My wife very turned on, said she needed to taste Jenna on me and proceeded to give me an amazing blow job…still can’t understand why these two haven’t hooked up.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None
What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Thought it was an important experience to have, It was easy / convenient
How intoxicated were you? A little tipsy/high
What substances did you consume? Alcohol, Marijuana, hashish
How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it
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? Just my wife
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? Surprise sex with a very hot woman.
What was the WORST thing about this hookup? Needing to keep this secret from her husband. Might be a little awkward next time we go out as a couple.
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? Not at all negative
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