Bad First Dates: The Silk Boxer Shorts
My last post discussed my first ever date with a guy I’d met online. Today, I’d like to talk to you about the second man I met online, once again on Plenty of Fish, on The Other Side of the World, during a Big Love breakup. It was every bit as disappointing as the first one was, except this time around I got laid and a couple of free dinners out of it.
I must’ve been going through a phase or something because my second online date was with yet another bald guy. We actually went past the stage of the awkward first date, even venturing into the second, third, and fourth date. It was on the third date and fourth date that we slept together, and it was as we were sleeping together that I realised I just wasn’t that into him. In fact, I wasn’t into him at all. Not in the slightest. I didn’t even think I was attracted to him. He wasn’t a bad-looking chap … he just wasn’t what I was looking for.
The sex was … well, it wasn’t good. I don’t want to say that he was bad, but we definitely weren’t compatible with each other. On the first occasion, he waddled across the living room to me, his silky (and cheesy) boxer shorts still around both ankles, cock pointing at me, condom in place. It took everything I had not to laugh. It was just so weird. Not sexy at all. It was all just so … weird.
Everything felt a little robotic from that moment onwards, from the way he climbed on top of me on the couch to the way he pulled my underwear off. And we didn’t account for the height difference: his six-foot-something versus my five-foot-two-and-a-half. I couldn’t breathe with his chest smothering my face, and there was no comfortable way for us to be with him on top. I tried to move us so that I was riding him but he was having none of it. He just kept pounding into me, his heavy body basically crushing my chest and restricting my breathing, jack-hammering away like his life depended on it. And the kisses, once so soft and actually quite enjoyable, turned into sloppy, slobbering licks. At one point, his tongue was actually in my nostril, though that was partly down to the height difference, I think.
Despite it being really quite terrible we decided to give it another shot.
“I was nervous,” he said. “Please give me the chance to show you I’m not a mess of a man.”
And because he was actually a nice man, I gave him another chance. It was against my better judgement but still, the second chance was given.
“We could smoke a joint if you like?” he suggested. “It might relax us both?”
After my first almost-arrested experience it felt like I was having deja-vu, but we did as he suggested and had a great date. He took me out for dinner, refused to let me pay, and invited me back to his for the night. We sparked up, had a beer or two, laughed and talked a lot, and when it came to getting into bed I genuinely thought we’d have a better run of things this time around. The joint had worked; we were relaxed.
It was every bit as awkward and uncomfortable as it was the first time around. I didn’t orgasm. Again. I faked it. Again. And I’m also fairly certain that he didn’t cum either. It was an absolute disaster. We both tried really hard but there was no sexual chemistry at all. We’d probably have become great friends if we’d met under different circumstances, but great lovers? Nope. We definitely weren’t destined for that.
The worst thing about this guy is that I kinda knew we weren’t compatible when we met for our first date. It was dinner and a couple of drinks, nothing too flashy or spectacular, but although we had fun, the sizzle that I’m looking for just wasn’t there. I didn’t feel it when I kissed him for the first time, nor did he give me butterflies. I wasn’t nervous around him, not in a way that I have been with other men. Big Love gave me hella butterflies, but this guy? Not even the tiniest of flutters.
But, you know, I tried not to be a bitch and give the nice guy a chance. And I really did give him a chance. Four dates. Three dinners. Countless drinks. One joint. Two fucks. Whatever needs to be there just wasn’t there.
I shoulda listened to my gut on the first date and he wouldn’t have become just another awkward notch on my bedpost.
Thanks so much for reading my blog today! 🖤
If you’re in the market for something a lil’ spicier, why not check out one of my smutty favourites:
