Captain Squish

There are a few things I’ve done in my dating career that I really regret. But at least I try to learn from my mistakes.

One night I was out at my local watering hole drinking solo. I do that sometimes, especially when I’m single. It’s the best way to meet men.

So this sweet young thing starts talking to me, and he’s just adorable. He’s in a local band I’ve heard of, but never seen. I even know some of the people in the band, so we have tons to talk about. He’s very sweet, and five years younger than me.

The night turns toward the morning, and we’re still chatting. His friends, including his ride, come and ask him if he’s ready to go, I can tell he’s hesitating, so I offer to give him a ride home if he wants to finish his beer. He eagerly accepts my offer.

But here’s the thing: I’m having fun, but I’m really not DTF that night. Some nights you’re in it to win it, and some nights, not so much. This was not my night.

So by the time the bar closes, when we get into my car, I tell him, “Look, I’m enjoying your company, and if you want to come to my place for a beer, that’s cool, but I’m not going to sleep with you.”

He says he wants to come over, and he’s OK with the deal.

So we go to my place, drink some beers, and make out a bit. It’s getting late, very late, and I’m getting drunk. Somehow, and I honestly don’t remember the details, we decide to go to bed. Again, I tell him he’s welcome to stay, but I’m not going to sleep with him. Oh, yes, fine, fine.

I fall asleep.

Some time later, I wake up, and I realize my hand is on his dick. He’s got my wrist, and he’s pushing my hand into his dick. His flaccid dick.

“What the fuck?” I say, sitting up, “was that your dick?”

“Well,” he said, “I mean, I was kind of expecting more.”

I got up and turned on the light.

“No. Fuck no. You need to leave. Now.”

He pouted while he got his shit together.

“Can you give me a ride?”

“You’ve got to be fucking kidding me. You can walk.” I lived miles from his house, and I didn’t care.

But you know what? I realized right away what an idiot I had been. I mean, seriously? Don’t let a 22-year-old boy sleep in your bed if you don’t plan on fucking him.

But also, boys, don’t press a sleeping girl’s hand into your fleshy, soft penis. That’s just gross.