The Tennis Instructor

Did I ever tell you about how I lost my virginity? Ha... lost. I threw off my virginity when I was 19 with a woman who was 36.

Back in Burlington, my whole family belonged to this country club. I took tennis lessons there growing up. I got pretty good, and when I turned 18, they let me work as an instructor. It was an easy gig and I got to know some of the really wealthy clientele. Lots of horny housewives in Burlington—more than you would think.

There was this one woman I knew—5’11”, blonde, a little older but she was still real hot. I would always see her there and I’d say hello when I had the chance—oh hey, how are you, how’s your game… you know, the usual. I later found out she was divorced, and she actually lived right around the corner from my parents’ house. So this one time she came up to me and said, “we should go kayaking some time.” I was like, “Yeah, sure.” We never actually did, but from then on things were a little more friendly between us.

Then this one Friday night, I’m walking out of the locker room, and she invites me over for pizza with her kids. They were like 10, 8, and 6 at the time. So I go over, we have some pizza, watch TV, the kids go to bed… and she just keeps bringing me more and more beers. She must have brought me five or something, and that was a lot for me at the time. We ended up on her couch… I think she blew me the first night. The next time I saw her was a couple weeks later, and we got it on. Let me tell you, from there on in, I would drop by her house any old time. I would be out with my friends, or on the way home from the bars… I’d just drop in unannounced. She showed me where she kept her key and I would just let myself in.

She was cool! Really cool… and she lived in this awesome, old Victorian house, but it was real creaky, so when I let myself in, I would go up the side of the stairs super careful, then walk down the edge of the hallway trying not to make too much noise. I was petrified of waking up the kids, but once I was in her room, I figured I was safe. I’d take off my clothes, jump in bed, and it was sexy time. I would just sleep over and go home early the next morning.

The next year, I went to college, but whenever I would come home, I would go over and have sex with her. She was totally cool like that. But this one night, I think it was the summer of my sophomore year, I came home from the bars at like 2am. I was really hammered. I crept up the stairs like usual, really quiet, went into her room, took off all my clothes, and as I was tip toeing into her bed, totally nude, I look down between my legs. A shaft of light from outside came through her window, and right beneath my balls I see her daughter, asleep on the floor. I was confused at first, but then I looked around, and as my eyes adjusted to the dark I saw that all her kids were sleeping in the room. It was like a freaking slumber party. I was like, “oh shit…” For a minute, it seemed inevitable that they would all wake up and see me standing there with nothing on. I was bugging. But I somehow managed to sneak back out with all my clothes and took off…

I never went back to see her after that. I don’t think she even knew I was there that night. My mom randomly started gardening with her a few years ago. I used wonder if they ever talked about it. “Hey, it’s funny we’re gardening buddies now, because I used to sleep with your son.”

Weird.