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Hey, got two more done so I'm at 5/10 which I'd say isn't too bad. This friday I had a date cancel on me last minute, I was already all dressed up and ready to go so that kinda sucked. Even put on my one fancy set of lingerie, black, lacey, belt and stockings and all, just under a cute little black dress. I had planed to let the guy fuck me, so I was also pretty horny looking forward to that. Boredom led to scrolling through reddit, remembered my card and then I got stuck thinking about the 'Run up a tab, sex your way out of paying it' challenge. The way it turned out I also completed 'Let a stranger take you to a secondary location'.
I've mostly been to bars or clubs with guys so far and they can usually get me in. But since I was already good to go, I thought why not just go out alone and try to get in by myself. The bar I picked is a pretty small place and I got in no problem. Could barely even order my first drink before the first guy started hitting on me. Pretty much the reason I almost never go out alone, also never really feels that safe but this time that kinda turned me on a bit. Since I wanted to at least have a something on that tab, I got a small water with my second drink and waited till the third guy, which maybe took like ten minutes or so. He was kinda cute but pretty average, middle aged guy in a suit doing something in finance. He came in pretty aggressive, just sat down next to me and ordered me another drink without asking, then smiled. Usually the kind of guy I would just pass on with a mean comment, but I just went along with it and made sure it got put on my tab. We then just chatted a bit and got very flirty pretty quickly. You could tell he was doing this a lot, or at least trying to, the whole kind of flirting, picking up women, being a fuckboy thing haha. I bet not with a lot of success usually, never felt actually smooth and he also got kinda excited when I showed more interest. I just had a bit of fun playing it super naive, pretend falling for his 'game'. This took maybe around 45min or so, probably less. And the rest is not really that memorable, to be honest. I let it slip that this place is kinda lame and want to get going, he asks if he can take me some place else. When the barkeeper comes with the tab, I put my hand on his thigh and give it a little stroke, then ask if he would mind getting it. Which he did immediately, then went to his car. He took me to his place, went through some more of his little pick up strateg things, which I kinda still pretended to fall for, and then it just progressed from there. I could tell that the further we got, the less experience he must have had with these things. Made out a bit on the couch, kinda awkwardly let him finger me for a bit. Then he tried going down on me, which was super bad and I had to cut short. Sucked his dick a bit, which also was average but alright, had to be careful not to make him cum too quick. Which he kinda did anyways, cause from there he just put on a condom, bent me over the couch and pulled up my dress, fucked me doggy for probably only a minute or so and came.
After that I just quickly got home, not the most exciting story, I know. And honestly, for me the fun of it was mostly just trying to complete the challenges. Thanks if you read it anyways :P
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