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I’ve been dating my boyfriend around six months now but before that I was single for several years after a long-term relationship. In that time, I was far from a celibate saint and boy, did I have some weird encounters.
Presented here are the final five of top ten of my odd, crazy or otherwise insane hook-ups. Names have been changed to protect the creepy.
5-I met Calvin on a camping trip. He was a sexy bear, and I ignored a few personal tics of his. We didn’t talk much until the night before we left so when he asked me to go to the coast a few weeks later I accepted. He claimed he worked in Estate Management. Turns out, he worked for wealthy people cleaning their houses and running errands once or twice weekly. I was on deadline and told him I had to write, but the dude couldn’t stay silent for more than fifteen seconds. Calvin also claimed to be the first self-lubricating bottom.
4-Dexter was an older man, a bit out of the range I liked to stick with (15 years older than myself) but his pictures looked good, so I met him. The pictures ended up being at least five years old, but that didn’t stop me. Dexter needed either a huge ass dildo or a fist to get off. I’d never fisted a guy before, so I thought ‘what the hell.’ My first time ended up being the last time. Not my thing at all. The best part of this experience was when we were done he started talking shit about his ex-boyfriend, who happened to be a guy I’d already hooked up with.
3-Generally, I had bad experiences with the younger generation, but I’d talked to Matthew on and off for months so we got together once or twice for a little fun. The first time wasn’t great, but it wasn’t bad either, so I was fine with a second time. However, while I was performing oral sex on him, he texted his mother. His fucking mom! I may not have the best fellatio skills, but I know I’m not horrible. Then he had the balls to ask me why I wasn’t hard. Gee, I wonder.
2-When I was still in Nevada, the choices were pretty slim, so I hooked up with guys I might not have otherwise. While George and I were kissing and groping, he suddenly buried his face in a pillow and brought a hand to his mouth. He was removing his dentures, but apparently didn’t want me to know what he was doing.
1-This is actually two different men, but they fit in the same category–Topped by dudes who shouldn’t be tops.
Many years ago I had a threesome with a friend and a buddy of his named Eric. I’m not a size queen or anything, but Eric wasn’t sporting much below the belt. However, my buddy wanted Eric to fuck me, and I figured why not, it’s not like he could hurt me, right? I was on my hands and knees, and Eric positioned himself behind me. I kept wondering why he wasn’t pushing in, then my buddy asked if it felt good. I DIDN’T FEEL ANYTHING! What could I say? It was a no win situation for me. What if I said yes, and Eric said he wasn’t in yet? Or what if I announced that he wasn’t in and Eric said he was?
The other time something similar happened was when a guy named Claude said he wanted to fuck me on my stomach. He apparently didn’t have much experience because his cock slid up my ass cheeks instead of penetrating me, but he didn’t realize it. Instead, he went on about how good it felt and how tight I was.
And that is my top ten weirdest hook-ups. Hope you all had a good laugh at my expense.
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