Stories

Oops! I Slept with My Best Girlfriend

Couple in Disagreement

Welcome to a shameful and embarrassing page of my journal. And let it be said, here and now, from the guy who never needs a good reason to have sex, that sometimes it’s just not worth it.

Out with it: I’m gay, my best girlfriend is straight, and we kinda-sorta-accidentally had sex.

I wish I could say we were experimenting. Alas, we simply found ourselves together one night after she’d just been dumped. We had some red wine, “Why can’t I find a guy like you?”, “Because I’m gay.”, “We should get married.”, and on and on – it was ridiculous. Then we’re in bed naked. I wouldn’t even describe it as sex, as I know it. It was more like a penetrative cuddle. Argh.

I wouldn’t go so far as to say I closed my eyes and thought of England, but I did start regretting it shortly after we started. It wasn’t good; it was weird. And incomplete. There were things that neither of us were into, though we couldn’t say so directly. I couldn’t go down on her. That would have been just too gross. And her rimming me was out of the question. Although it turns out my best girlfriend gives awesome head. Too bad I’m so uncomfortable knowing that about her.

It hasn’t hurt our relationship, but we’d take it back if we could. It will never go away. It will shadow over us like the ghost of Hamlet’s father, forever. I hope one day we’ll remember it as nothing more than a blip compared to everything else our friendship has endured, or perhaps we won’t remember it at all.

Mark my words: friends, work colleagues, etc., should not be fucked with. I swear, in my early sex life I wanted to fuck anyone I could, regardless of appropriateness. Clearly I hadn’t made enough mistakes before shagging my B(G)FF to learn that it’s easier to see the lines after you’ve crossed them.

Besides, I’m a gaylord. What was I thinking?! Eeeew. All you guys out there who’ve never has sex with a woman – stay away! It’s so…so… complicated! And unsettling.

Follow the lines.

Be safe!

Any sex with straight women stories you want to share?

Tell us what you think!

Tell us what you think!

Meet Men Looking for Fun in Ashburn at DiscreetGayDating.com
To Top