Awkward Times With Parents

When I was in high school I was dating this girl for a while, and became good buddies with her dad. He was a single dad, they lived in a nice house, and he was a very cool guy. I hung out at their place a lot because he was rich and heavily into gadgets so there'd always be cool things to play with. He'd even offer myself and the GF some light alcoholic drinks every once in a while even though we were both underage, his reasoning being we'd drink anyway and he'd rather have it happen in a controlled environment.

Anyway, the girlfriend (Karen) had a best friend, Maria. I hung out with both of them a lot and became pretty good friends with Maria as well. Maria was from a really shitty family, alcohol, drugs, daily fights, you name it. One fine day her father left them and her mom started bringing random men into the house, and stopped caring for Maria pretty much at all. So she started sleeping at Karen's almost every other night. I saw Maria run around in her underwear a couple of times late at night and started having really heavy threesome fantasies.

I was too chicken to ask Karen straight out, but I did have kind of a "theoretical" talk about threesomes with her one day and she wasn't exactly opposed, and then she told me she knew what I was thinking, and that they actually made out with Maria a couple of times already. The conversation kind of ended there, but later that night as we were going to Karen's place I kind of braved up to decide to ask the question later on, and was all excited about possibly having my threesome fantasy come true.

We walk up to their house and suddenly we can clearly see through the living room window Karen's dad giving it to Maria from behind, pulling her hair back. We kind of had a side view to it, and after a few seconds of stunned silence her father turned towards us and saw us through the window, and immediately ran out of the house towards us stark naked, still with a boner on, screaming something to Karen about how she shouldn't get the wrong idea or something incoherent like that. Karen started screaming at her dad, then Maria ran out wearing some old t-shirt and all of them were screaming at each other. Then the father said he needed to get dressed and ran inside, the girls followed him and Karen slammed the door, leaving me outside. I stood there for a little while and then walked off.

Yeah, so my fantasy never came true, and somehow my relationship with Karen ended pretty quickly after that. I never went back to their house after that.

One day when I was like 13 or 14 I think, my mom was in the kitchen reading or something. So I ask her an innocent question: “When’s your anniversary?” I asked because I knew it was the current month and I wanted to get her a gift. But instead of an innocent answer, she looks at me really seriously, almost afraid, and goes “Why do you want to know?” I look at her like she’s insane and just say “Umm . . . I’m just curious.” So she then has me sit down and proceeds to say something along the lines of “I guess you’re wondering why your birthday is in July . . .” And as I sit there, she proceeds to tell me how I was born in July when my parents were married the November before. To state it blatantly, my birthday would put conception the month before my parents got married. So great, I want to do something nice for my parents and I get the gift of knowing I was partially an accident. Gee, thanks Mom!

I have a very, um, 'straightforward' friend who once posed an interesting question to his father. At the dinner table. With his mom also at said table. Apparently, knowing that his father had had a vasectomy, and not being completely knowledgeable about the difference between semen production and sperm production within the male body, he asked, rather blatantly,

"So, dad, what happens when you come?"

His dad, being insanely cool/laid back just pauses for a moment, perhaps to look at his wife, who was nearly choking on some beverage, then says, "It just stops the swimmers. Stuff still comes out, you know." To which my friend cheerily replies, "Oh!" and continues with his meal.

When I was about 14, it was about 2pm, my parents were out and I was sitting in the living room in a chair right next to a big window. I was busy fapping away like an evil dervish. Anyway, I stood up and came on the floor, before rubbing it into the carpet with my socks - as was my style at the time. I pull up my trousers and sit down. Suddenly there's a tap-tap-tap on the window, and my fucking next door neighbor is there. Crouching down, looking through the window, smiling. He points to the front door. I tell him my parents aren't home and he goes away.

To this day, a full 10 years later, I can't look him in the eye. He was probably standing there, waiting for me to finish.