I’ve told a version of this story before, about five or six years ago in a series that I ended up having to take down. I’d been a little careless with some people’s privacy, and it caused problems for them in real life.
Since then, I’ve focused on fictional stories that have been more stylized, but a few people have reached out and asked if I’d ever return to my confessional style of writing. I’ve thought about it a lot, but I’ve been avoiding it until now.
Earlier this week, I reconnected with an old friend, someone I hadn’t spoken to in about twenty-five years. He knows all of the people in this story, at least the ones I named. He’d heard bits and pieces of it before, but never the whole thing from the person who knows it the best.
I ended up telling him everything, and I figured if I could tell him, I could tell everyone here too.
When I first published it, I called it a “fictionalized version of the truth.” This isn’t that. This is what actually happened. Only the names have been changed. I’m not making that mistake again.
This was sometime around 1994 or 95.
I was in a cuckolding relationship with my girlfriend, Alyssa. We didn’t call it that. I don’t even think the word was around at the time. I’m sure it was in dictionaries, but no one used it – not as an insult, or as a lifestyle choice. I didn’t hear that word until years later. At the time, we called what we were doing “partying.”
If Alyssa said someone was coming over to party, I knew that didn’t mean they were going to have a few drinks and listen to music. She was going to get fucked, and I was expected to be there when it happened.
That’s just the way it was. And it wasn’t at all like what you see in porn now, or the way most people write about it. She was my girlfriend, not my mistress or dominatrix. She wasn’t cruel or abusive. She loved me. But she also loved fucking black guys, and she wasn’t going to give that up for anything.
In the beginning, she saw a lot of different guys. No doubt she had her fun, but I think she did it to test me, just to make sure I was really on board with everything. Once she realized that I was, she started spending most of her time with a Jamaican guy named Devon, who was a few years older than us. We were nineteen or twenty. I think he was about twenty-five.
Devon had a twin brother named Marlon, and he was dating an older woman named Dee. She was in her mid-forties and married. Her husband was loaded and came from a very well-known family. There’s a theatre and the wing of a library in Toronto named after members of his family. Parts of his personal collection are on display at the Art Gallery of Ontario. He was that kind of rich.
Alyssa and I didn’t just fall into a cuckolding relationship. Dee influenced everything. Alyssa really looked up to her, and she thought Dee had it all. Her husband was reliable, loving and caring. He looked after her and was a great guy to be around. Then on the side, she had Marlon, a young stud with a massive cock who could do things to her that her husband couldn’t. That’s how Alyssa saw it, and she wanted the same for herself.
The problem was getting me to go along with it, and that’s something Dee solved for her. I was young, and she knew exactly how to get me to buy in. She didn’t just make it sound normal, she made it sound sophisticated. She had me convinced that accepting an arrangement like that meant that I was more open-minded and cultured than other guys, and that I belonged in her circle.
“Jealousy is for lesser men,” she told me. “You’re above that.”
When you’re that age and someone with that kind of sway tells you that, you want to live up to their expectations. It’s really hard to turn around and say “no, actually I’m not,” even if it’s true.
Dee made it all make sense to me, so I went along with it. She called it a modern relationship, and I didn’t feel hard done by. I felt like I was ahead of the curve, on the cutting edge of something new and exciting. Dee did such a job on me that any time I was having doubts or wasn’t happy with my situation, I felt guilty – like I was letting her down for not being the man she thought I was.
The fact that she was living the lifestyle herself and seemed to have the perfect life didn’t just make it easier to believe, it made it easier to want.
Anyway, that’s the background. This is the story.
Dee invited Alyssa and me up to her cottage, which was about two hours north of Toronto. Calling it a cottage doesn’t do it justice. It was a luxury summer home on Lake Muskoka, at least twice the size of any house I’d ever been in before.
Her neighbours were all people you’d know. Saturday Night Live’s Lorne Michaels owned the place right next to hers. Kurt Russell and Goldie Hawn were less than a 5-minute walk away. The future captain of the Toronto Maple Leafs, Mats Sundin, was nearby too. That was right before that area really took off. Soon afterwards, Tom Hanks, James Cameron, and Prince all had places on that same lake.
When she said she was having a party for modern couples at her cottage, we knew exactly what that meant. The women were there to get fucked by a stable of experienced guys that Dee had on call. The husbands and boyfriends were there to take a back seat and let it happen.
When we got there, everyone was outside. The women were on a huge deck that lined the side of a pool behind the house. The men Dee had invited were there too. All of them were black.
I recognized one of them right away. I was a fan of his. I won’t say his name, but at the time he was one of the biggest rappers in Toronto. I’d seen him live and owned a couple of his CDs. I wasn’t into sports, but I later found out that the guy he brought with him was an NFLer who played for the Buffalo Bills.
All the husbands and boyfriends had their own spot by the lake, maybe a hundred metres away. There was a canopy tent, some picnic tables, a barbecue, and coolers full of drinks. That’s where I ended up.
Alyssa went up to the deck. Dee and Marlon were there to greet her. Devon was there too, but I think he was trying to play it cool by not running over to her as soon as she showed up. Or maybe he thought he could fuck her whenever he wanted, and this was his chance to be with someone else.
Down by the lake, I remember thinking that I was about to join a select group of modern men, and that maybe one of them would take me under his wing and mentor me. The reality hit a lot differently.
The first thing I noticed was the tension. It wasn’t a bonding session of forward-thinking men that I hoped it would be. It was a support group for guys whose wives were getting plowed by strangers.
None of that registered with me at the time. I thought being the new guy and younger than the rest of them, I was the cause of the unease.
They tried to cover it up by distracting themselves with hands of poker and doing their best to share a few laughs over beers. To an extent, that worked. But every so often, someone’s wife or girlfriend would disappear into the house with one of the guys from the deck, and everyone went quiet until the guy she came with said something. Once he did, it was like the rest of us could too. We just had to give him that little moment.
Looking back on it now, I don’t know how I didn’t realize how fucked up that whole situation was. I just remember thinking that some of those guys couldn’t handle it, like even though I was the youngest guy there, they weren’t on my level. I almost pitied them because they didn’t have what it took to be in a modern relationship.
When Alyssa went inside, I didn’t go silent. I was proud. She was with two guys, one of them picked her up and threw her over his shoulder. The other guy smacked her ass as they walked and he was already pulling at the strings on her bikini. She laughed the whole time.
And I sat there watching it happen, and instead of thinking what the fuck, I remember thinking this is it, this is how the elites live, and I wanted more of it.
Alyssa and the guys were gone for a long time, over an hour, maybe two.
The whole time we were down by the lake, the same thing kept happening with the other women. One after another, they’d get led into the house, then came back a while later looking a little flushed, usually hanging off whoever took her inside.
When Alyssa came back, she was different. Her hair was a mess, and her makeup was smeared. She wasn’t even walking right. Even from where I was, I could see a wobble in her steps. She looked like she’d been fucked hard and had no shame about it at all.
Devon saw it too. For the first time since I’d known him, I caught what I thought might be jealousy on his face. I think that was confirmed when he grabbed another girl and pulled her inside, staring down Alyssa the whole time. I don’t even think she noticed.
Alyssa made eye contact with me. It was her way of checking in. I smiled back at her, and she dove into the pool. Seconds later, a new guy swam up to her, and they started talking. I knew what would happen next.
Not long after that, Dee came down to the lake to talk to one of the guys. His name was Mark, and he was one of the older guys there, probably 35. She asked him to go inside and change the sheets on the bed his wife had just been fucked in.
I feel so stupid admitting this now, but I had no idea that this element of humiliation was part of the dynamic between him and his wife. Dee wasn’t asking him to do a routine chore, she was twisting the knife. All of that went right over my head, and I jumped in and told him I would help.
We didn’t dare go up onto the deck, even I knew not to do that. Instead, we went in through a side door that opened into the kitchen. For a few seconds, everything was normal, beyond it being the kind of house I’d only ever seen in movies. Then we walked past the living room, and I heard it before I saw anything.
When I looked in, one of the guys’ wives was on top of some guy, riding his cock hard, right there in the open. Another woman was on the couch beside them, legs spread wide, fingering her pussy as she watched them fuck. Alyssa was the only girl I’d ever seen naked before, so all of this was shocking to me.
Across the room, another guy was sitting in a leather chair with one of the girlfriends on her knees in front of him. He had a fist in her hair and was moving her head up and down. It didn’t look like she was giving him a blowjob. It looked like he was fucking her face, practically choking her with his dick. She seemed to be loving it though.
Her mascara was running down her cheeks, and it instantly made me think of the way Alyssa looked when she came back outside.
Mark didn’t look at any of it. He just kept his head forward and walked straight to the stairs.
We went upstairs and down a long hallway. Most of the doors were closed, but you could hear what was going on behind some of them. Lots of grunting and moaning, coupled with the sound of bodies slapping together. It was weird knowing that Devon was in one of those rooms fucking some girl to prove to himself that he wasn’t bothered by seeing what those other guys did to Alyssa. I’m not sure if a cuck is ever supposed to feel sorry for a bull while he was fucking some beautiful woman, but there I was.
At the end of the hall, the door to the room we were going to was open. When we stepped inside, you didn’t have to guess what had happened in there. The bed was wrecked. The sheets were half pulled off, the comforter was on the floor, and the top sheet was still damp from sweat and who knows what else.
Not far from the bed, there was a chair with a folded set of clean sheets on it. We changed the bed without Mark saying a word, but the look on his face said everything.
On the way back, I saw something that’s still stuck in my head, and this is the part that my friend wanted to know the most about. One of the bedroom doors was wide open, and I couldn’t help but look in.
There were three women, two blondes and an Asian girl, all completely naked on the bed. The three of them were on their hands and knees, lined up side by side. The rapper was fucking one of the blondes from behind, while the other two waited for their turn. The thing that still makes me laugh is that he was totally naked, but still had his shoes and socks on.
I stopped for a few seconds and watched as he fucked the first blonde, then pulled out, stepped to his right and pushed his cock into the other blonde.
The Asian girl dropped onto the bed and rolled onto her back. When she saw me standing there, she smiled and waved at me like there was nothing strange about any of this. The first girl slid down between her legs and started eating her out.
The rapper saw her wave and looked over his shoulder at me. He nodded toward the hallway. The message was clear, move along. So I did.
Something like twenty years later, he starred in a TV show. My girlfriend at the time loved it and never missed an episode. I didn’t tell her about any of this. But she’d be sitting there watching him on TV, and all I could see was that room—him fucking the blonde, still wearing his shoes and socks, and the Asian girl smiling and waving at me.
