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.
We pour some drinks and since I’m feeling ambitious I turn the conversation sexual pretty quick, once everyone else has left the restaurant and after some questions about her dating life. She ends up telling me that she’s only been laid once since the divorce, and not in the last 6 months. I see my window of opportunity and in more or less words I tell her I could help her out with that. I must have been pretty convincing because as I move closer she pulls me in and we start making out. I grab her ass as we kiss but soon she pulls away and kneels down and starts undoing my pants. “I’ve seen you showing this thing off,” she says. And of course she was totally right so with a grin I say, “I have no idea what you’re talking about.”
My cock springs out as she pulls my pants down and her eyes grow wide. “Holy shit, you’re fuckin’ huge!” she gasps. I love that kind of talk so it’s making me even harder, and I ask her for for me details. “Oh yeah?” I say. “I think you have the biggest dick I’ve ever seen!” she continues, grabbing ahold of it. I just smile and watch how she looks holding my cock, which is now rock hard and all 8 inches are looking massive as her small hands can’t even grip it all. I ask her to blow me and she starts fitting it into her mouth. She can only get a little bit past the head, but it’s ok because her tongue work was amazing.
Eventually we move to the back office where she lays back on the couch and spreads herself open for me. I eat her out briefly to get her juices flowing before sliding close and teasing her pussy with my cock a bit. I tease her for a few moments and lay my cock down on her stomach, letting her see how it passes her belly button and towards her chest. “Oh my god…” she says, “you’re going to wreck me…”
I took it easy though, and slowly pushed my cock in while she tilted her head back and gripped the cushions as her tight pussy swallowed me in almost as if it was begging for me. I continued loosening her up and going deeper with each stroke, and goddamn this woman could almost take it all. I start fucking her as deep as I can go and her moans turned into screams. “Oh fuck it’s so big! You’re soo deep!” before I lift her up a bit and change the angle. “Right there! Right there!” she starts yelling, and I start giving it to her hard as she quivers and soon the only sounds she can muster are whimpers of pleasure.
I pull out as she starts blowing me, letting me finish in her mouth. She swallows my cum and pulls her head away from my cock as is slides out of her mouth and flops down between my legs. She keeps staring at it, and eventually brings it closer with her hand to inspect it. “Wow…” is all she says. We’d end up hooking up many more times until eventually she started dating a more suitable life partner.
If you’d like to hear any more stories feel free to dm me, my willingness to flaunt my size has led to quite a few.
Source: reddit.com/r/gonewildstories/comments/12xr8li/fucking_the_manager_when_i_was_19_years_old_mf