Author: tollsie

Meeting my new roommate [MF]

A lot of you wanted to hear more stories after my last one and I have some time to kill while I wait for my car in the shop…

This story happened my junior year of college (yes another college story but it was a crazy time in my life) … Myself and two of my close friends needed to find a place to live for the upcoming year and we had a friend who recommended a place to us. She ran track and knew a handful of girls who lived in a duplex and the bottom unit just opened up. They were fine letting us three dudes move in downstairs, and so we did.

One of the first weekends there we all decided to go up to one of the guy’s parent’s lake house to party and get to know each other better. We’re playing some games before heading to the bar and started getting pretty loose. At one point one of the girls, Jen, as a joke (at least framed as one) asks which one of us dudes has the biggest dick. My two friends both immediately point to me and burst out laughing. I acted embarrassed but certainly didn’t deny it either. Read more »

Fucking the manager when I was 19 years old [MF]

I knew I had a big dick early on, and by the time I was a sophomore in college I had learned how to use it to my advantage pretty well. When I was 19 I was working as a server at a restaurant on the nights and weekends, and our manager was a woman in her early thirties. She had been divorced about a year prior and was a single mom. Whoever divorced her was an idiot because she was absolutely gorgeous. About 5′ 6″, slim-thick with a big ass and perky B-cups.

Being 19 and full of vigor I flirted with her early and often, and I made no attempt to hide it. One night she’s stocking some cupboards beneath the bar after close and I walk over to talk to her. I lean up against the bar and since I’m a big shower I stood in such a way that you could see it, and know that I was packing. I ask her if she has any plans for the weekend. She turns to me and says she has no plans, but her son is with her dad so she’s hoping something comes up. I respond by saying that I don’t have any plans either, but maybe we should have a drink before we head home. As I’m responding I notice her sneak a couple glances at my crotch, which is all I was hoping to achieve really, and I did not expect the next part to work out like it did. Read more »