Friday 16th April 2021,
Jack Gary

That Time I Had Sex With A Guys Wife While He Watched

I first learned about cuckoldry as a sexual fetish after reading a news story about a porn actor, who was known for playing president Barack Obama in many movies, went on a Samurai sword wielding spree and killed his co-star and injured two other people on a porno set in the San Fernando Valley. It was a gruesome and lurid tale, but the best part was yet to come. The murderous porn actor, who went by the stage name of Steve Driver, was eventually cornered at the edge of cliff and after being tasered by the cops fell 100 feet to his death – and it was all caught on camera.  Steve Driver, whose real name was Stephen Clancy Hill, was one of the preeminent actors in a niche porn sub-genre called cuckoldry. So was his victim, Tom Dong.

After reading this story I wanted to learn more about cuckoldry. It fascinated me that a man could get off on watching his wife fucking a much more dominate and much bigger male, while she teased and taunted him. The name itself of the fetish contradicts it’s own definition – in the fetish the cuckold is usually completely complicit in their partner’s sexual “infidelity” and takes masochistic sexual pleasure in it. This was a strange and dark part of human sexuality I hadn’t seen before and I want to be a part of it, at least once.

What I learned on my journey of finding the perfect couple that enjoyed this kind of fetish, and wanted me to be the third wheel, was that you couldn’t really take the usual flirting tips as your guide. This was the X-Games of looking for hook ups. This was the Iron Chef of trying to get your dick wet. My first stop was a cuckoldry group I strangely stumbled upon while looking through the local Chicago classifieds. We were to meet at a park bench in Oz Park – already a bad sign that I might be getting in over my head. When I went I realized immediately what it really was: an obvious scam. One of the women was an aging prostitute and this was just a way to fleece a bunch of freaks for money. I started yelling that they were all assholes and was immediately kicked out of the group. Good riddance.

About a week later I was still searching for the right couple. At this point I was in West Virginia for a work related event. I really wanted to know what it would be like to be in a cuckoldry situation. My curiosity had turned a bit into a full-blown obsession. One night I was out at this really podunk bar where a few guys were drinking a beer and the rest were picking their noses in what seemed like a somnambulant daze. The bar had that “I want to get drunk and screw” vibe written all over. I mean this place had vomit crust on the walls of the bathroom and creepy glory hole notes. Yet, I thought maybe I’d find a woman freakish enough who was into what I was after. I ended up talking to a cute girl at the bar. She drank milk out of an aluminum can and when I look back, the milk thing was probably a sign that I should have left immediately. However, I stayed and told her all about my quest to find the perfect couple that was into this cuckoldry fetish. After a good milk burp, her eyes got real wide and told me that her and her husband were totally into it.

I should have listened to my instincts. We went back to her place and it was a dump. I didn’t care, because I wanted to get my dick wet and I wanted to be in a cuckoldry situation. She started her dick sucking magic, which was more like a sloppy hillbilly slurp. After a while I heard the distinct sound of a shotgun being cocked. I immediately went limp when I felt the cold barrel against my neck. Apparently, the girl had lied to me and basically just wanted to get laid, because she was a hillbilly freak. After her husband, who might have been her brother too for all I know, escorted me out of the house with his rusty shotgun he told me that that this kind of thing happened weekly; then he showed me a skull. Either that was someone who was dumb enough to put up a fight or he was just trying to scare me. I didn’t want to stick around to find out.

I was out of luck…again. This time I was back in Chicago. I was at a little Italian restaurant bar. It was especially windy outside and I remember the roaring sound it made through the awnings. Perhaps that was a good omen, because I met a couple that was sitting right next to me and we all started to chat. The woman looked just like an ex-girlfriend of mine – it was slightly frightening. The guy was extremely short, bald and not very good looking. The woman was older, but sexy in a MILF kind of way. One of the first things the guy told me was that he liked watching his wife get fucked by black guys with giant dicks. Chi-ching! This was my couple…I knew it.

I told them that I was a sex journalist and that I was looking for a couple that I could “embed” myself with for the night for a story on cuckoldry. They said sure and we headed back to their flat. Keep in mind, night waking in Chicago is unbearably cold, so we had to get back before everyone lost the mood we developed in the restaurant. Alas, we get back to their enormous Chicago apartment and everyone was still ready to go. A few chapped lips, but not anything a good fire couldn’t cure. When we get inside we headed to the living room. Her husband made a fire. We talked for a while about this and that while we all warmed up. After about thirty minutes the husband walked about. I took this as my cue.

I started kissing reached in and started kissing the wife’s neck and she started moaning. I pulled off the top of her dress and her tits fell out. I started kissing her nipples and caressing them. They were firm and not showing much sag from age. Perfect areolas. Apparently her husband had watched her in a number of compromising cuckoldry situations, including a gang-bang with a college basket ball team while they all smoked cigars and drank Miller Light. Real classy I thought. As I started kissing her she started to moan louder and louder. Then she pulled out my cock. She sucked my dick like a real pro. Then she asked if I’d like to go upstairs to the bedroom. I sure did. My fantasy was definitely coming true.

When we got to the bedroom she took off her whole dress and jumped on top of the bed completely naked. The lights were dim and it was getting quite romantic. I started switching off between licking her clit and using a little pocket vibrator. She was getting so wet that an enormous wet spot started to grow under ass. She was literally dripping off the bed and onto the carpet, like after biting into a fresh peach. After she begged for it I starting fucking her and then she got on top of me and fucked me like she knew exactly what she was doing. It was incredible. That’s when her husband walked in and “caught us” in the act.

He looked mortified, but maybe that was part of the act – or maybe it wasn’t. Then something strange happened. He stripped down naked too. He had a pudgy, pale little body and a tiny dick. I definitely didn’t think of this happening in my fantasy. Here I am fucking this guy’s wife and her husband is five feet away, completely naked. As I was plowing into her and squeezing her tits she started to taunt him and call him names, like “small dick” and “fag.” She was really embarrassing him. He was beet red as she started telling him how much better I was at getting her off. Then she started flipping him off and getting really brutal.

In all my fantasies I didn’t think of how I would feel when I was in this situation. I just wanted to do it. Reality has a way of kicking in pretty hard when you are living out one of your fantasies – for better or for worse. Hopefully it leans more towards the former. However, I quickly realized that I wasn’t into cuckoldry. It wasn’t that I felt bad for the husband, but I just couldn’t get off watching his gross little red body and small dick while I was fucking his wife. I realized after an exhaustive search, and a good college try, that cuckoldry wasn’t for me.

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