Wow. Where to even begin? The other day I posted an ad about wanting to gamble on an upcoming Rangers game. I received a lot of messages, but mostly from people who aren’t super familiar with hockey or a few fans of competing teams who unfortunately were outside of NYC.

But finally, someone good reached out. He was concise in his first message, noting his life-long fandom of the Rangers might not be exactly what I’m looking for, but that he’d still like to make a wager.

The bet was simple. He would give me two of his season ticket seats if the Rangers won. If the team lost, him and I would go back to his place and make the loss sting a little less - he just wanted some head. There was a twist though. He wanted me to wear some gear for the Islanders (the New York Rangers’ biggest rival).

I immediately knew where his head was at. It would embarrass me and massively turn him on. After all, who wouldn’t want to see a “fan” of the other team literally sucking your dick.

We figured out that both of us would be going to the game yesterday against LA. Different sections, but still a game we could watch in person. We met up at the first intermission and he got me a beer. “Cheers to a good game” he said. He was a little older than I imagined - about a decade older than me. Handsome and fit, clearly established in life and well off. Right as we confirmed the bet in person, I remember thinking how he wouldn’t even miss the tickets. So, at least I could feel better about my hopefully soon-to-be win. But just as quickly as the devious thought entered my head, he made me recite the bet out loud. I could have sworn everyone else around us heard us talking, their eyes starring daggers at me as I sulked back to my seat.

Can you guess what happened? I’ll let you Google the score, if you want. For everyone else, the Rangers lost. And it wasn’t even close. I can barely start getting my things together and leave my seat before I get the text to meet him by the exit.

We got on the subway and made our way to his apartment. A few jokes were made about where the night was headed, but we mostly talked about the game. Things changed right when we got to his place. He opened the door and instructed me to take off my Rangers jersey and wait for him to get back with my punishment.

He throws a practically pristine Islanders shirt at me. A gag gift he received from a friend a few years back, he said. The second I got the cheap, rough fabric over my head, he ordered me to kneel in front of him. What followed was some of the worst (and most fun) degradation of my life. He leaned into the hockey angle hard, and I would have been laughing along with him at his quips about the how he “finally found an islanders fan worth spending time with,” but he was getting more and more rough on me.

He spent the next hour alternating between fucking me face and getting me to beg for his cock. By the end, I was an absolute mess both mentally and physically. The shirt was covered in spit and cum and he practically threw me to the side once he finished. I eventually collected myself, asked to use the restroom and washed up before making my way out. As I left, he thanked me for turning his night around and joked about how he hopes to see me at another game. “If you do, ask me about another wager,” he said.

I spent all of last night and most of today recovering. I wish I could say I learned my lesson, but I’m definitely more inclined to want to accept some bets. I haven’t had someone treat me like that in ages and it was just so fun.