One of my most vivid memories of youth was in early high school. I was fooling around with a girl named Maria, who lived a few blocks away from me. She was a very soft-spoken and sweet girl. We were the same age, but she went to Catholic school, whereas I went to public school.
We had that strange type of childhood friendship where you are intense friends for a few weeks and then don’t speak for a month and then run into each other again and become intense best friends for another isolated time, over and over again. We ran in different circles, but it seemed like we came back to each other when we got tired of our other friends.
The intense memory was going over her house one day when her parents weren’t home. She was in a very particular mood. She was flirty and sort of bratty, and she was picking on me and sort of sitting close and touching me and teasing me all afternoon.
Well, teenage Jack didn’t know what to do there. I was nervous and confused by her strange behavior. I wanted to make some kind of move, but I didn’t want to do anything wrong.
I had messed around with a few girls, and I’d had one strange sexual encounter, and eventually, I realized Maria was coming on to me, so I did what any red-blooded boy would do. I suggested we play Truth or Dare. She was very enthusiastic about that idea.
The chess game began, a truth to start off like the game isn’t just an excuse to make out. Giggles, flirting, testing boundaries. In ten minutes, she had her dress off, and I got to see a surprisingly grown-up lingerie set. We were kissing. We were touching. Then I got up the courage and asked if I could take off her bra. She was red-faced and bright eyes as she nodded and said, “yes.”
I somewhat awkwardly reached around her, and she let out a little laugh and pushed me away. Then she smiled and said, “oh, sorry, this one is different.”
Then she put her hands on her breasts for a moment and just sort of held them, which I found mesmerizing. She then reached for the clasp that was in the front, between her breasts, and she opened it and then pulled her bra apart, and there were her tits, and I swear angels sang, and golden light haloed them.
It’s not that I hadn’t seen tits before, it was just at that age it was always in the half-dark or sneaking around somewhere, or they were half-covered, or we were in a super rush.
This time, there they were, displayed proudly, happily, gloriously. She smiled at me, and with a little blush, said sweetly, “you can touch them if you want.”
And reader, I did. And it was really neat.