Nerdy friend and mom
Back in college I was big time into "Magic The Gathering" - both playing the game and collecting the cards. I joined a club at my university where the biggest nerds that were into the game would meet up once per week and play or trade cards. It was a big time weekly nerd convention, but it was actually pretty fun.
I became friends with a very nice, but very nerdy kid who seemed to know everything about the game and has an impressive collection. He would tell me all sorts of things about the game. We became friends because we were a bit different from each other and both wanted to branch out. He was short and skinny with glasses. And he was basically afraid to so much as look at girls. I would jokingly call him Milhouse (although not his real name).
After becoming genuine friends, I tried to get Milhouse to break out of his shell and meet more girls. I was single and also wanted to meet girls. So I was making an effort for us to go out to parties and meet girls with Milhouse.
Then at the end of the semester when school was out, I invited him to come hang out back home at my parents' house. My parents knew about my recent obsession with "Magic The Gathering" and they knew of my new friend Milhouse, but never met him before. So I had Milhouse come over for dinner and to play the game and meet my parents. I basically told my mom that he was extremely shy with girls and that my was plan to try to "get him laid." To which she just rolled her eyes to and told me to grow up.
After dinner we began playing the game. My dad had no interest, but my mom was interested in at least trying to understand this card game that we dedicate so much time to. So we set it up where she was partnering with Milhouse and they were playing against me. They were sitting together on the dining table bench across from me. My mom seemed to be having a fun time learning how to play. Milhouse seemed to be enjoying helping my mom play. She was drinking wine and we were drinking some of my dad's beers. They were even whispering moves and questions to each other for much of the game. We played for about 3 hours.
Milhouse ended up staying the night. We played video games after my parents went to bed. And he admitted to me that he had a major crush on my mom after playing the card game with her. He said that he was sitting so close to her that his leg and hip was touching her leg and hip during the game. He didn't say it in a crude way - but he basically said he had a hard-on for the entire time sitting next to her. And I could tell my mom was being intentionally friendly, almost flirty, towards him. And I was for whatever reason enjoying watching it. I'm not sure why. I wouldn't have liked that happening with any of my high school friends. But for whatever reason I didn't mind my Magic The Gathering friend simping for my mom.
So I told him to sleep on the main floor living room sofa. My bedroom was in the basement. My parents' room was upstairs. I thought that if anything would ever happen between Milhouse and my mom, it would be on the main floor when everyone else was sleeping. I had him spend the night at my parents' house 4 more times that summer. About once per month. My mom didn't actually play the card game again, but there were several more friendly interaction between my mom and Milhouse. I even told her once that he admitted to me to having a crush on her.
I'm 99% sure that nothing ever happened. But I always hold out hope for that 1% chance that my mom snuck downstairs one of those nights and gave Milhouse a blowjob for his first sexual encounter. And I have no idea why this was a turn on to me and I'm definitely ashamed of having this fantasy. And I was actually more so friends with him for the possibility of this fantasy playing out more so than Magic The Gathering or anything else.
He had no idea I had this fantasy. He only knew that I knew he had a crush on my mom. But I played it off in a "keep that to yourself" type of way. My mom seemed to be more aware that something was up. I would always try to make him sound really good - even making up stories that made him sound like a great guy and a shy nerd. And for an entire year I fantasized about them hooking up in my parents' living room. And I always wonder what that says about me and pretty much ashamed for even thinking it.
|