by: Rob

Gender: Male
Age: 30
Race/ethnicity: White
Current location: New York
Highest education received: College degree (eg., BA, BS)
Occupation: Self-employed
Relationship status: Married
Religious affiliation: none
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 30
How many hookup stories have you here posted before? 1

The Sweet & Bitter Affair

How long ago did this hookup happen? 6 years ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? 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? They were a couple of friends of mine. I’ll call them R and S. R and me hung out a lot as friends in the same small town we were living in at the time. It had developed into a day to day friendship. After some bad dates and hearing her endlessly complain about not being wanted despite being a very lovely girl I offered to have sex with her and we had a brief fingering make out on the beach. It was always just friends. Nothing more. S was another friend who I knew a little bit. She was flirty with me and we never properly went on any dates, but was good company. She and R had developed into good friends over the course of a year. Both very lovely and lively girls.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was invited for a night cap at S’s apartment by R. I didn’t think much of it as I went and thought we would just hang out. They had been to dinner earlier in the night and were a little bit tipsy. We talked for around an hour and S went to the bathroom. R said to me that they had been thinking about playing with each other and wanted to know if I wanted to join in. I said yes and R passed me a condom. S returned and we said we’d like to see what happens with us playing. She agreed.

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? We all started to make out and get undressed. R had a thin body and large breasts that were very perky and a clean shaven pussy. S had smaller breasts and a similar body. She had a small amount of bush and to my surprise a small clit ring. I went down on both of them as they made out. Both had incredibly tasty pussies. I wanted to get my cock sucked, but R said she didn’t do it on guys she wasn’t in a relationship with. S said she would and she started to blow me while R sat on my face. After a while R wanted to get fucked, and said she hadn’t had sex for a while. I laid her down and began fucking her missionary as S laid next to us kissing me and playing with R’s boobs. I eventually started fingering S to an orgasm and had put a finger in her ass at the same time. I tried to play with R’s asshole at the same time, but she wasn’t into it. I went to fuck S and asked her if she wanted it in her pussy or ass. She said both, so I fucked her in her pussy for a bit and then switched to her ass. She said to R that’s it’s different but a lot of fun. We switched back and forth between fingering each other while I kept going down on each of the girls to orgasms. I wanted to cum and while I was fingering R shot my load onto S’s stomach. We took a short break. Just cuddling and kissing. We got started again with me going down on S while R watched us. I eventually licked S’s ass for a bit and stuck my fingers in her pussy. I also used my other hands and played with R’s as she leaned against the wall watching. S got on top of me and we got into a great rhythm while R played with herself. I laid them both down and alternate between fingering one and licking the other’s pussy. Both of them made out and sucked on each other’s tits. I laid down between them and wanted to cum. I teased R about not wanting to help out, but she gave a grin and slowly started jerking me off while I made out with S. I shot another load onto S’s stomach and we all relaxed after a night of very hot sex.

Did you have an orgasm? Did your partner(s)? I had two. They had several at least.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Condoms

What were your REASONS for having this hookup? I had always liked S and heard she wanted to make out with me. R was an odd bird in wanting to be provoking and say she was perfectly bi-sexual, even though that was not the case. They both wanted me for different reasons. Pleasure, potential relationship or both. I liked them both, too.

Were alcohol or drugs involved? If so, how much? Mild intoxication from all.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? I left after we were done. I was invited to stay the night, but had to work and wanted to get up early and workout beforehand. I had a good time and thought everything was okay and saw them both again in different social settings. S seemed to want to date me and I offered, but was given mixed messages over the invitation. R wanted to do something similar to that with another friend, but she soon found a boyfriend who disliked me and thought we were still fucking. Distance and mixed messages from all sides lead to friction and S feeling used. I saw S briefly sometime later, but the distance and awkardness grew too large. I still think well of them, but it was a situation I should have passed on and saved the friendships. I patched things up with S after she had moved away and told her I was sorry for how she felt she was used. We left on friendly terms and no longer speak.

To whom did you talk about the hookup? How did they react? I told a friend who was not connected. He was amused. R told her future boyfriend which lead to friction between us and then we stopped talking. We eventually spoke and had coffee a couple years later. She told me her boyfriend and her had entered an open relationship and was offered sex again, but I decided to decline. We never spoke again.

Was this a consensual and/or wanted experience for you? For your partner? It was consensual from everybody. We just shouldn’t have done it.

Do you regret this hookup? If so, why? I do, for all the reasons listed above. It was very hot and a wonderful sexual experience, but the fallout from that was too large and not worth the several hours of pleasure. Don’t do these things with friends. It only hurts people if everyone isn’t on the same page.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I was a hot experience. I loved fucking, smelling, and being with both of them. I wish they had done more direct oral sex with each other, but that’s a minor complaint. The worst was the loss of the friendships. It simply wasn’t worth it and I regret it to this day.

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

All things considered, how NEGATIVE was this experience? Very negative

Anything else you want to add about this hookup or anything else? A mixed bag of a hot experience with terrible fallout. I would do it again, but I would make sure that the participants would be completely NSA and we would not know each other. Threesomes are hot, but not with your friends.

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