by Rocco

Gender: Male
Age: 48
Race/ethnicity: White
Current location: California
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Manager
Relationship status: Single
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)? 77
How many hookup stories have you here posted before? 2

The Threesome

How long ago did this hookup happen? 8 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…)? Short fling

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 met J when I posted an ad seeking a threesome and this lead to us becoming fuck buddies while we both continued searching for a third to make the threesome fantasy come true. J was a blonde woman in her late thirties with a cute face and fabulous tits. She was interested in exploring her bisexual side. After a few weeks she connected with K a slender brunette and the three of us agreed to meet for dinner and see if we were attracted all around.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The actual hookup began at J’s place. We all were excited but a bit unclear of how to begin. I suggested that we head into the bedroom and take our clothes off, J and K agreed and so the fun began.

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? K began by immediately giving me head. She was actually kind of aggressive in a way, and this got me quite turned on. J meanwhile started kissing me, which was actually really fun while being blown. K suggested I fuck J but since I had already fucked J on several prior occasions we exchanged looks that communicated that K should have the first go. From here we proceeded to try out all sorts of fun three way combos. I fucked them each twice, but had held back on coming. Eventually we started to figure out how to wrap up. J commented how she really liked the way it felt when I orgasmed when fucking her doggy style, saying she could feel my cock pulsating when I came. K liked the sound of this and wanted to try so we got repositioned with I lying back while K ate her pussy and I fucked I from behind. I fucked her long and deep for quite a long time, maybe ten minutes in this position. Eventually I reached the point of no return, I grabbed her hips and thrust deep deep inside and then pumped her full of cum. She loved it. We all hugged and cuddled and basked in the glow of having shared something special.

Did you have an orgasm? Did your partner(s)? I did. The partners did too at various times.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We used condoms, a whole bunch of them, switching to a fresh one each time we switched between partners.

What were your REASONS for having this hookup? Feeling horny and curious about a threesome.

Were alcohol or drugs involved? If so, how much? We had a couple drinks at dinner but not much.

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? We hung out, got dressed, and went our separate ways. I contacted J a few days later to see if she fancied a fuck and she indicated that I ought to contact K instead. She had complained that my cock was too large for her while K really liked it. I liked them both, actually but was more attracted to J perhaps because we had done it more times. I could have contacted K but didn’t. Somehow that never happened so we all went our separate ways after that one memorable night.

To whom did you talk about the hookup? How did they react? I told nobody.

Was this a consensual and/or wanted experience for you? For your partner? Absolutely consensual.

Do you regret this hookup? If so, why? No regrets.

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? The sex was fun. I believe a repeat performance would have been even better because we would have been familiar with one another, but alas this was not to be.

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 or anything else? Having a threesome as a single was great! Had this happened in the context of a relationship where a third party joined in I could imagine this getting really complicated.

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