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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
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? In a serious relationship (open)
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
How many hookup stories have you here posted before? 0

First Threesome

How would you best classify this hookup? Group sex

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? I’ve been in an open relationship with my girlfriend for ~6 years. We’ve slept with a number of other people during that time, mostly separately. We’ve had group sex together before, but only involving other girls, no guys. She’s a cute curvy girl with the softest hair ever, and a sharp wit. She’s a real firecracker in the bedroom. I’m lucky to be with her.

On a month-long trip, we met a guy (let’s call him The Philosopher) who we both enjoyed spending time with. He was a nice, considerate guy who made me feel welcome, like a friend amongst a group of people I didn’t know well. We started hanging out during our free time and he began inviting us to join him for dinners. As the trip progressed, my girlfriend said she was developing an attraction for him. One day we arrived at a beautiful long white sandy beach. My girlfriend and I went for a walk. At the far end of the beach, there was a set of creaky wooden stairs leading to a viewpoint. From the top, we could see people in the distance but no one near enough to really notice us. I pulled down my pants and she started to blow me. After I came, I asked her if she’d like to do the same to The Philosopher and she admitted she was thinking about it. I started to fantasize about this as well. I wanted to watch them fuck.

This seemed like a great opportunity for a threesome, something we’ve really wanted to do but were waiting to find just the right guy. The problem was that we didn’t really know if Philosopher would be into this sort of thing. I was quite certain that he liked my girlfriend and would probably sleep with her if she were single and available, but the couple-dynamic complicates things. We liked him not just in a sexual sense but as a new friend and as someone I really respected. We didn’t want to ruin that with an awkward proposal that might make him feel uncomfortable or like sex was our motivation in spending time with him. As the days went by, I made sure to create the opportunity for them to get a bit closer, having her walk between us or beside him while I hung back a bit. One evening after dinner I returned before them, leaving them to walk back together in the near pitch black night.

Toward the end of the tour, Philosopher asked if we’d like to join him for a nice dinner. We had a growing sense that he was open to new experiences and willing to take risks. This invitation seemed like he was creating an opportunity for something to happen. Was he thinking about this too? Perhaps the more intimate setting, good food, some wine, and being away from the big group would break the ice?

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? To some people, delicious food is almost sexual and I think that’s true of all three of us. Dinner was, of course, delectable. After three bottles of wine, my girlfriend really wanted to take The Philosopher home. We didn’t really have a game plan, though. I don’t function particularly well when drunk, but I thought if we made him comfortable coming back to our hotel room, that would tell us he was interested and also get the sparks flying. At the end of dinner, I asked if they’d like to get dessert, knowing a good place was near our hotel. Instead, Philosopher suggested a quiet bar where we had a few more drinks. He had some unbelievable stories and he captivated us, making us lose track of time. All too quickly, though, the lighting went up and the bar closed.

Perfect – enough spending time in bars, anyway. I had my girlfriend suggest we grab a bottle of wine and go back to our place. Philosopher agreed. Game on. Problem – search as we might, we couldn’t find anywhere selling booze other than crowded bars. Nothing. We settled on another quiet bar. Not more than halfway through our new drinks they also stopped the music, raised the lights, and kicked us out.

Out on the street and nowhere to go, I resorted to reciprocating Philosopher’s captivating stories with our own great tale, one of a near-death experience, while walking in the direction of our hotel. I opened the front door and Philosopher seemed willing to come up. I was getting really eager. Inside, I motioned for Philosopher to sit on the couch, my girlfriend joining at the opposite end. I then sat where she had put herself, requiring her to move right next to him, creating physical contact.

By this time, my girlfriend was quite drunk, and while she continued the story in a very entertaining way, she went on forever and ever, as drunk people do. Philosopher took a washroom break and I started to kiss my girlfriend. She got very turned on. When Philosopher came back my girlfriend wrapped up the story and as she did so I started to give her some more kisses while Philosopher looked on, appearing somewhat unsure. I asked if he’d like to join us for some fun. “Depends on what kind of fun”. “What do you mean what kind of fun?” responded my girlfriend. “What?” responded The Philosopher. Fucking drunk people. This went on for a few more turns and I knew I had to do something. I put my hand behind my girlfriend’s neck and kissed her passionately, putting an end to the drunken miscommunication. As I felt her get turned on, I pulled back and immediately pushed her to Philosopher. They began to kiss deeply and sensually. I could tell right away that he was a great kisser and she moved to straddle him.

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 didn’t take too long for clothes to come off. Philosopher was very hard and massive. He has the kind of cock you’re sure you’ve seen somewhere in porn. My girlfriend was the center of attention with hands and tongues all over her and a huge cock in her mouth. After thoroughly enjoying herself on the couch, she said: “I want to fuck Philosopher now”. We moved to the bedroom where I witnessed some of the best sex I’ve ever seen in person.

How sexually satisfying was this hookup? Very

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 all met up the following day for lunch and shared our memories and feelings. It was a very nice way to reconnect and to know that we all felt good about the experience. For our first MFM threesome, I don’t think we could have chosen a better partner. The comfort and sexual tension that had built up over the previous weeks grew very strong, and the connection ran all three ways. Philosopher was respectful, sensual, attentive, and a much more skilled lover than I’ve ever been. The satisfaction I felt from watching my girlfriend receive pleasure was as fulfilling as any sex I’ve had. I’ll never forget witnessing the intense physical and emotional connection between them. I’m so grateful to have found such a good partner for this experience.

We live in different countries and are unlikely to see each other again anytime soon. At the moment, I feel that if we were to meet again, I’d just be friends with Philosopher while letting him and my girlfriend enjoy one-on-one sex together.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Thought it was an important experience to have

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? 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

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

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