filed in Man Stories on May.29, 1987
Things are better when they’re forbidden. It’s just a fact of life.
They say that people want what they can’t have.
Drinking is more fun when you’re underage. Girls love bad boys. Actors want to be rock stars and rock stars want to be actors. Teenage boys want MILFs and men want barely legal coeds. And of course, there’s just something about having sex with someone you’re not supposed to, in a place you’re not supposed to, in front of people you’re not supposed to.
A friend once told me that he had sex with his girlfriend at a sleepover, when all his friends were sleeping around him in sleeping bags.
I told him I could do better.
In the summer, the unit of time is not minutes, or hours, or days, or weeks, or even months. The unit of time is parties. Life becomes judged based on parties.
The McDonalds run where Sarah puked on the drive-thru speaker: that was the 4th party of the Summer. The time that Josh and his girlfriend got into an awful fight in the living room at a house party, and everyone else ended up huddled on the patio to wait it out: 7th party. The party where everyone got sick from eating marijuana brownies because my friends cooked actual marijuana leaves into the brownies: 3rd party. And the time of Truth or Dare and the sneaky, naughty sex: 8th party of the summer.
It’s funny how so many innocent childhood activities can suddenly become highly sexually charged when you’re an adult: wrestling, tickling, Twister, piggybacks, and of course, Truth or Dare.
There were five of us for this particular party. Besides myself, there was Greg and Scott, two of my friends from work; Sarah, a friend of mine from school with a sarcastic but cute demeanour; and of course, the girl without whom, this story would not exist: Jill.
Jill was the type of girl that would never let you be bored. She was spontaneous and easy going. She had a smile and a laugh that could just light up a room. And try as you might, it was almost impossible to have an awkward moment with her, no matter what you ever said or did.
She was also one of the cutest and quirkiest friends I had at the time.
Jill was a tall, slender brunette. She wore her hair in a pony tail all the time, and somehow that just made her sexier. Being slender, she had naturally small breasts, but they were always perky, which somehow fit with her personality. And her ass was a little bigger than you might expect for her physique, but big in a good way, if you know what I mean.
Jill was a sexy cutie. And she was just a friend.
Jill and I had always casually flirted, but nothing really ever came of it. I guess it was the kind of flirting that was borderline brotherly-sisterly rivalry. It was subtly sexual, but usually more friendly and fun focused.
If you asked me now why I never really looked at Jill as anything more than a friend, I couldn’t tell you. Maybe I’d just known her for too long. For most of the time that I’d known her, I had a girlfriend in some way, shape, or form, so maybe that was an issue too. But even after I became single, it just never clicked in my head that our flirting meant anything more to either of us than friendly banter.
Whatever the reasons for our asexual relationship, everything changed the night we all played Truth or Dare.