Next | Part 1, 2, 3, 4, 5, 6, 7

The story of the sleepover is perhaps one of the more unusual, impromptu, and awkward sexual situations I’ve ever found myself. I often wonder if it had been planned ahead of time or if it was simply the result of being drunk and horny. Either way, it’s a story that I don’t tend to recall very often.

It’s a story that I usually don’t talk about or even think about. And it’s a story that I definitely don’t bring up with my friends, as you will see, for very obvious reasons.

It begins at a house party.

The party itself is pretty standard. People do shots, we play games. People chug beers and make inappropriate jokes. Other people get involved in very philosophical debates, while girls in the other room compare boob sizes.

Like I said, the party itself is pretty standard. But this isn’t the story of the party, it’s the story of the sleepover afterwards.

There were three of us sleeping over: Brent, Carol, and myself. Brent and Carol had been dating for over a year. I’d known them both since before they started dating. In fact, I think I may have been the one that introduced them.

They were the typical couple in terms of almost everything. And I’d known them both for so long that they felt like siblings. Carol was cute, but I never thought of her as anything more than a friend.

Little did I know that was about to change.

After the party ends, we set up some air mattresses in the basement. Our hosts leave us with blankets and bottled water and head upstairs for bed. Carol and I are setting up our beds as Brent brushes his teeth a floor above us.

Carol’s wearing pink pyjama pants and a rather low cut tank top.

Normally I wouldn’t pay her any more attention than I would to a guy friend, but she kind of keeps yawning and stretching in my direction. Guy friends don’t have boobs that become more visible in tank tops when they stretch. She catches my eye a few times.

I shake it off though.

We’re all drunk. She’s just tired. Her boyfriend is upstairs. She’s my friend, just my friend. Friends don’t ogle friends’ boobs, so just ignore it and stop looking.

We finish putting our beds together and collapse.

She’s lying directly beside me.

We make small talk about the party, about being drunk, about funny things that happened. All pretty normal stuff for us.
Then, she turns to me. “You’re so far,” she tells me.

“Sorry…?” I reply, unsure of whether she was fishing for an apology or not.

“Come here,” she says, as she pats the bed beside her.

It seems like an innocent enough request.

I scoot over and she does the same.

I’d like to point out now, before I go any further, that it’s not common practice for me to steal my friends’ girlfriends, or to hit on them behind their boyfriends’ backs. It’s certainly not my style to sleep with them.

Just thought I’d throw that out there.

Our legs are now touching. Our faces are inches away. She pulls one of my arms over her and lays one of hers over me.

She smiles.

I don’t know what to think. I don’t know if this is innocent or not. But I’m not a cheater, so I bring up her boyfriend.

“Brent is taking a while eh?” I say.

She nods, “He always does.”

“Yeah…” I reply, unsure of what else to say.

She giggles.

We continue our idle chit chat. We chat about pretty much nothing. I’m still drunk, and all I can think about is her hand grazing down my back. I keep telling myself that this is innocent. I tell myself that it doesn’t mean anything. Her boyfriend is right upstairs for Christ’s sake! How could this mean anything?

“Cuddling is nice,” she tells me.

“Yeah,” I reply.

It’s still innocent. Right?

Then the moment breaks.

“Hey guys,” Brent says drunkenly as he stumbles downstairs. “Trying to steal my girl, JD?!”

I look up immediately and stutter, “Brent I uh…”

Carol laughs.

So does Brent.

I realize he’s joking.

“Obviously!” I say sarcastically, hiding my panic. I feel like I’ve just been smacked with a defibrillator.

Carol reaches up and Brent hugs her as he rolls into bed on the other side of her. Carol turns over, her back now to me and starts to cuddle with Brent.

My heart rate returns to normal. I guess it was innocent after all.

I’m relieved. Although, a small part of me which actually thought sex might be on the horizon—probably the penis—is disappointed. But mostly, I’m relieved.

Next | Part 1, 2, 3, 4, 5, 6, 7

This particular embarrassing tale has been dedicated to Shay.

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