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What’s your gender? Man
How old are you? 58
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 60
How many hookup stories have you here posted before? 1

Incredible Threesome (MFF, Cheating)

How long ago did this hookup happen? 1 week

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? Group Sex

How long did you know the person before this hookup? For less than a month

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 am a 58-year-old professional with a 53-year-old girlfriend who I love and may marry at some point. We have a great sex life. I also sometimes keep a younger sugar baby on the side because it is super fun to have a secret younger lover. My current sugar baby is 20, latina, and we have been together for about 3 months. We get together 3-4 times a month, sometimes for sex, sometimes for normal activities (visiting a bookstore, or fine dining, etc). She is 98 lbs, petite, incredibly cute, and small B breasts. I had never had a threesome and (DUH) always wanted to, so a couple of months in I asked her how she felt about it. It turns out that she’d never been with a girl, but she was super interested in it. So she was actually quite eager.

The search was a little tedious but we eventually met a 24-year-old Asian girl who is bi with a preference for women. She is 5’7″, average physique, also small B breasts, a super cute smile, and short black hair. The first night we met, we sat in a coffee shop for about two hours and basically all fell in love with each other. You can never, of course, predict the future, but it felt like we would all get along. We had another dinner together a week later before we decided we were ready to move to a hotel. We scheduled a late afternoon hotel check in one week later. We discussed all of our preferences / phobias about sex (e.g., one of us has been assaulted and there are some behaviors that can trigger those feelings, so we reviewed that; one of us only does oral after they have known someone for at least a little while, etc. etc). We also laid out clearly that there were no expectations, that if at any time any one of us felt uncomfortable, that any one of us could call off the whole party if they felt they needed to. We discussed being attentive to each others’ needs and making sure nobody was ‘left out.’ We all really clicked and had a similar sense of humor so these conversations went really smoothly.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met in the late afternoon and went out to walk around and shop; I bought them both earrings and we picked up some scented candles etc. Then we checked into the hotel – we had a nice suite. We ordered room service and ate supper while we chatted. Then we watched a comedy movie – nothing like laughter (IMO) for breaking down interpersonal boundaries. We only got about half way through the movie before we started kissing and snuggling.

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? Over the course of about 15 minutes the girls’ tops came off and they started in with some serious kissing, boob caressing, and kissing each others’ boobs. For the first 10-15 minutes, I just watched. I was going to insert myself into the group if I wasn’t invited at some point, but I figured I would just watch and give them the chance to bring me in at some point. About 10-15 minutes in, the Asian girl started reaching for my cock through my pajama pants. I undressed and she caressed me. Then I knelt on the bed above her head (she on her back) and started kissing her lips, face, and breasts from an ‘upside down’ position. Meanwhile, the Latina girl was taking off her pants and panties and started caressing and fingering her pussy. Things melded and I cannot remember each step, but I ended up on my back with each of them on my side, we were kissing and fondling each other. I asked my original sugar baby if I could ask the new (Asian) girl to ride me and she said sure. So I put on a condom and the new (asian) girl got on me in cowgirl. I caressed her clit with my fingers while she rode me. My original (Latina) sugar baby knelt behind the Asian girl riding me, and wrapped her arms around her, caressing her chest, breasts, tummy, and face. This was an absolutely incredible visual – one of the high points. After 5-10 minutes, I invited them to trade places and they did – the Latina girl on me in cowgirl, the Asian girl kneeling behind her and holding her, caressing her while she rode me up and down.
We took little breaks throughout after we would be in a position for 5 minutes or so -nothing ‘scheduled’, but if one of us got stiff or uncomfortable we’d stop and sit and kiss for a couple of minutes and then initiate some other position. Somewhere in here my Latina (original) SB got on top of the Asian girl (essentially missionary position without penetration!) With the two of them face to face, they began kissing each other, caressing and kissing each other’s breasts, and then fingering each other. As they did this, I knelt behind them and entered my original Latina’s pussy, essentially doggy style. After a couple of minutes, I pulled out and entered the Asian girl as she lay on her back under the Latina girl. I would stroke within each of them for about 1-2 minutes, then pull out and immediately enter the others. I spent about 5-7 minutes just going back and forth from one beautiful, clean and tight pussy to the other. This was heaven and probably the high point for me. Later we did an Eiffel tower with my original latina SB on me in cowboy and the new (Asian) SB riding my face. She rode my face/mouth so hard that I literally could only breathe when she was on an upstroke, and she was practically dislocating my jaw. It was really uncomfortable, but also sexy as hell. I was gasping for breaths on each upswing until she came which was intense. After that, I was pretty much done but the girls kept going for another 10 minutes or so before collapsing and we add cuddled.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, but I was close

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 lay in bed and cuddled, finished our movie (which was incredible). I got to watch them get in and out of bed and walk around naked to go to the bathroom or minibar etc. This was amazingly sexy. The Asian girl had to go into the living room to study for a final exam the next day. Around midnight the Latina girl had to go home so she left us. The Asian girl and I slept together and in the morning we did a few minutes of kissing and naked caressing, but not really making love. Then I took her home and we made plans to get together again this Thursday. Everyone was on cloud 9 at how well it had gone, how comfortable we all were, how great the communication was, how much we enjoyed each others’ company.

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, Making new friends

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol, Marijuana, hashish

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? Two former Sugar babies I keep in touch with. They were very supportive.

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? Just how well we all got along together, followed by the incredible sensation of being physically connected to two people at once.

What was the WORST thing about this hookup? That the Latina girl had to leave at midnight, and that theAsiann girl had to study a couple during the evening. Otherwise, it was utterly fabulous.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’ve never really had a problem with casual sex or the *idea* of threesomes. But this was my first threesome experience and it went better than I would have expected – just because 3 people are involved.

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? I am so looking forward to rounds 2, 3, 4 ….

What do you think about the Casual Sex Project? It’s a good place to share secrets lol

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