I'm fascinated by cuckold origin stories. The one below is mine, and mostly true (a few minor timeline edits to make for better reading).
Louisville, KY 1992.
Becky and I met in spring of our senior year in high school, ushering at our city's stage theatre. I was a sexually confused kid who wasn't sure if I was into girls or boys, but happy with anyone if they paid me attention. Becky was tall and skinny, with long straight red hair and pale skin. Not beautiful exactly, she had a severe chiseled look and eyes that glittered from an inside joke no one else was included in. When she smiled at me, I felt warm and safe. We started dating three days after we met.
Our sex was frequent but very basic. Becky wanted to fuck every time we were together. I was a little overwhelmed by how much slickness her pussy created. I had no previous experience going down on a woman, and it all seemed more complex than a cock was. But entering her felt like velvet paradise. She was fine being on top, doing all the "work" as she called it, bringing herself to orgasm on my stiff cock with a soft sigh. I'd then close my eyes, let my brain drift away, and with a few more thrusts, cum into her warmth shortly after.
She was intrigued by me identifying as bisexual. She told me she was straight herself but found it fascinating someone could be attracted to more than one gender together. together.. I told her stories of my earlier exploits with guys and then we'd fuck after, it got her much more turned on than if I just started making out with her.
We both had scholarships to the same university, so our summer was mostly trying to find as much trouble as two honors kids could get into. It was her idea to find a guy to "share" between us. The idea had never occurred to me, but once she suggested it, my excitement grew rapidly. My parents' house was perfect for the hook-up: they went to sleep early and we had a hot tub.
The college section of our city had a late-night coffee house. It was one of the few places under 21s could hang out, so it became our spot. Becky decided this was where we should find our guy. We had a late dinner and showed up at the coffee bar around 10pm.
Becky was very comfortable radiating sexual energy, so it was almost comically easy to find a guy. His name was Frankie, twenty years old and a sophomore at our city college. He was sitting alone at a small table, charcoal sketching his coffee cup in a notebook. I thought he was cute if maybe a bit beefier than I'd prefer. With a mop of unruly black hair and a mouth a little too big for his face, he looked roguish.
Becky asked if we could join him with our drinks and she immediately brought up sex. She asked if he was "bi" and Frankie said "um, sure?" Becky then made the blunt proposal; we were going back to my house with a hot tub to fuck and he was invited to join us. Frankie, mostly looking at Becky and just glancing at me, agreed. We left our untouched drinks on the table and drove him back to my place in my car.
Becky sat with me in the front seat, Frankie in the back. Our conversation was bland stuff; where we went to school, where we were going next, what music we listened to. There was no talk about what we were about to do.
We got to my place and silently slunk through the dark house to the back patio. I got my clothes off first and removed the hot tub cover while they shucked off their clothes behind me. I imagined they were checking each other out.
Once we were all in, we all agreed how nice the water felt. Becky again wasted no time and started kissing me. Frankie then started rubbing Becky's small tits and shoulders. I was as little dizzy from excitement. How far was this really going to go? It was all up to Becky of course, but I wanted her to let Frankie go all the way.
After a few moments of Becky and me kissing, Frankie not-so-gently grabbed Becky's chin and turner her head to him. She seemed a little surprised and maybe nervous but after only a few moments of him kissing her, she shifted her body toward him. While watching his face, I reached across Becky under the water and gently felt between his leg, not sure what he'd do. His expression didn't change, but I felt his cock jump as I wrapped my fingers around its hardness. Becky was now fully turned toward him, deeply kissing him back, her own hands roaming his well-defined shoulders and chest.
The blue hot tub light made it kind of easy to see what was going on under the water, but Becky's gasp confirmed his hand was now between her legs, Frankie's forearm dipping in and out of the water as he played with her clit. Becky's hand, going for Frankie's cock found my hand already there. I heard her chuckle while Frankie was still trying to suck all the air out of her mouth with his own. We played with his cock and balls together.
Sadly, the middle of the summer isn't great hot tub weather, and with Frankie and I sandwiching her on both sides, Becky quickly over-heated. She stood up abruptly, and we both backed off, not sure what would happen next.