Cheat Day - Sex Stories

Cheat Day

... didn’t match with a girl, I got sad, and when I did match with a girl and the conversations went nowhere because I didn’t know what to say, I got sad,

and

when we clicked, I got even more sad, since we couldn’t leave the house.

Katie was what people called “nerd cute.” She was a little thicker around the middle than she wanted to be, and had glasses and a brown-haired ponytail, and to top it off, had a liiiiittle bit of an annoying “um actually” habit, always wanting to one-up everyone in the room. Still, she more than made up for it by being a good friend, and at this point, nothing could drive a wedge between us. Jake only droves wedges once or twice, and even then, the wedges never stuck for long.

“That’s cool, but… is that it?” I asked.

He sighed. “Yeah, I know. Lindsay is out, as is Mike.”

“Wendy?”

“With her lung thing? Nah, she’s not taking any chances. Hell, she gave me this whole speech about how irresponsible we’re being.” He clicked his tongue. “This stuff is probably hitting her hard.”

“She’s probably jealous she can’t be there with you, dude,” I joked. Jake had a habit of ‘accidentally ending up’ sleeping with most of the girls, and a few of the boys, in our friend group. “Give Jake enough time,” we all used to joke. It was a bit of an open secret. Wendy happened to be his latest development, and even though both of them kept it under wraps, Jake’s sexual history was hard to hide for too long. With one exception, he was always pretty ...

... gracious and kind to them both before and after he slept with them, so it was never an actual issue, but it was still something fun to tease him about, especially since…

“Hey, c’mon, it wasn’t like that!”

…It was the one thing he was embarrassed about, as if he hated the idea of being seen as this slut or something. As far as I was concerned, good for him. I would have loved to get around as much as he did, but it kind of wasn’t my style to sleep with friends. If I was going to date or screw anyone, I didn’t want it to be someone I had history with.

I laughed. “Sorry,” I said with zero meaning.

“You in or out?” he barked. I could hear him blushing through the phone.

“I’m in, I’m in,” I laughed. “What’s the plan?”

***

Helpfully, all of Jake’s housemates terminated their leases and ran home at the first news of the pandemic, but Jake himself had no plans to return to his parents’ house no matter what, which meant he had a house all to himself. It helped that Jake’s house’s basement was the coolest living room a student could want, with shag carpeting and plush couches and even some kind of bar.

I was the first to arrive with plenty of time to spare, which meant the two of us got to spend some much-needed time lounging on the plush couches catching up with each others’ lives. Of course, thanks to the pandemic, there weren’t a lot of life events

to

talk about, but it was still cool. I at least had my parents to hang around – I had no idea how Jake kept his ...