Ok, this is probably not the kind of "wild" story that skibum requested, but it is a fucking wild coincidence.
WARNING There is some disgusting content to follow, so if you're easily grossed out or offended you might want to scroll down to the next story, and possibly put me on ignore. But I swear on my eyes this is a true story.
It was the spring of 1998, immediately following a divorce from my first wife. I was glad to be rid of her but exhausted from the process. My buddy decided to take me on a long weekend trip to Ocean City Maryland to celebrate.
Before we even got inside the hotel, we met a couple of hot sluts in the parking lot, struck up a conversation, and made plans to meet them for drinks. Later on at the hotel bar I had an eye for, let's call her Slut #1, and he immediately hit it off with Slut #2. End result, it turns out #1 and I did not get along, not at all, and she got pissed off when #2 took my buddy back to the girls' room, leaving #1 alone with me at the bar. Being the gentleman that I am, I offered to put aside our disdain for each other, and let her spend the night in my room which, for lack of a better option, she reluctantly accepted. We did manage to have a few laughs and slept in separate beds.
In the morning, I made us a couple of bloody marys to cure our hangovers and sent her on her way. My buddy showed up shortly afterwards and gave me the details. Slut 2 was not only the best fuck he ever had, but she gave him his first-ever rim job. Now I was glad to hear that, because having had several myself, I'm a fan of it, especially from a total smoke show like Slut 2. But then he shared something else. He'd been suffering with hemorrhoids since before we left on this trip, and the long drive down there didn't help his condition.
He was hesitant to meet up with this girl again because, pleasurable as it was, he was apprehensive about the hemorrhoid thing. I asked him how long she was licking his butt and he said about 10 minutes or so. Bam... case closed. Obviously IF there was a problem, she'd have quit long before that, right? He agreed.
So the second night, the four of us went out, my buddy and #2 were like a couple in love, and #1 and I both hooked up with others. She went off with some guy, I took a girl back to my room and had a pretty good time. My buddy went back to the same place to get his hemorrhoid-ridden ass licked again. The next and final night, #1 and I went our separate ways early on, and my buddy and #2 never even went out. They just stayed in the room.
So it turns out we were all leaving the next morning. These girls were from southern NJ and we were from northern NJ, so we ended up on the ferry together from Delaware to Cape May. Other than a few sarcastic digs at each other, #1 and I were basically civil. My buddy and #2 looked like they were on their honeymoon. It was pathetic.
Well obviously, I never spoke to #1 again, but he met up with #2 several more times, even though it was a long drive. She did the ass thing every time. He said he enjoyed it even more after the hemorrhoids had healed. After a few meet-ups, they lost touch with each other.
You might think this story's over, but not quite yet.
Fast-forward about 5 years... We have a friend who we like a lot but don't see him that often, maybe a couple times a year. He was coming off a messy divorce, and instead of taking some time to breathe he jumped right into another engagement with some other girl he had just met. He shows up to my buddy's house for the annual Christmas Eve party with his new fiancé. By now you can guess where this is going, right?
Yes ass-licking Slut #2, who we had almost forgotten about, was now our friend's bride-to-be. She had no idea whose house she was visiting. We had no idea who our friend's new fiancé was. When they walked in the door I was there to greet them. I shook hands and hugged my friend. Looking over his shoulder I saw her behind him. I recognized her immediately, but I don't think she recognized me. I wished her Merry Christmas and went to find my buddy. He was out in the backyard, smoking a joint and having a drink by the fire pit. I got a drink for myself and a fresh one for him before letting him know who just walked in.
By the end of the night, the three of us all knew who was who, but none of us let on that we knew each other. Our friend, her fiancé, was in the dark. To her, it had been just a weekend tryst with a couple follow-ups, which was in the past and need not be mentioned. To us, it was a hysterical story that we would love to expose, but we just couldn’t tell our friend that his fiancé, who he kisses every day, had once sucked on our buddy’s asshole. He married her and several years later divorced, but to this day we haven’t told him about it. Pretty sure there’s no need for that, funny as it would be.