Giving my manager her first huge cock when I was 21 [MF]
Here's a quick story because I don't feel like working at the moment...
I've posted a few stories about how I gained a reputation for being hung in college and by the time I was a junior I had learned how to use it to my advantage pretty well. When I was 21 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′ 8″ and a body that would please both ass and tits guys. I'll be honest I was trying my hardest to fuck her.
Being 21 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 semi springs out as I help her pull down my pants she wasted no time wrapping her lips around it. She starts blowing me and using her hand to jerk me off at the same time. I'm rock hard in no time and she stops to take a breath. "God you're big!" she exhales, before going back for more.
Eventually we move to the back office where she takes off her clothes, lays back on the couch and spreads herself open for me. I begin eating her out and it's apparent that she's already very aroused. Soon though she lets me know that she needs me to fuck her. She stays on her back, legs spread as I tease her a bit with my cock. I do the thing where I lay my cock on her stomach so she can see how deep I'm about to go. "Oh my god, I don't think I've ever had a dick this big," she says wide-eyed. I slowly push the tip in as she grips the cushions, bracing herself. I start loosening her up, going a little deeper each time I push into her. Her pussy is like a vice grip. "Ohhh fuck, oh fuck" she keeps moaning, clinging as I explore deeper inside of her.
Her body adjusted quickly though and soon I'm giving her every inch with long, hard strokes. This makes her lose control, and with her head tilted back she starts asking me to choke her. Now it becomes primal, animalistic sex as I grip her throat and start pounding her hard and deep. All she can do is moan and gasp as I continue fucking her, until she wraps her legs around me and pulls me in tight as she tenses up and shivers in bliss. I loosen my grip, get in close and ask her if she likes it. "So good.." she sighs while directing her gaze to my cock as it's now slowly thrusting in and out of her.
She wasn't done though, and neither was I. Quickly I flip her over and start fucking her from behind, and now the moans get louder. As I watch her bounce on my cock I decide to keep playing the alpha and ask her how much better I am than her ex-husband. "So much better. Much much bigger." And almost as if she was waiting for permission, or maybe she could tell that it turned me on, my cock was all she could talk about from then on. It might be immature but watching my cock spread this woman out while she talks about how much bigger I am than her ex husband, or anyone she's fucked for that matter, was the ultimate ego-boost imaginable. Especially for a 21yr-old in college, I mean come on.
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 relaxed for a bit, had another drink and then it was time for round 2.
We ended up fucking 3-4 times that night, and suddenly I was looking forward to work every weekend because this turned into a routine for some time until she eventually found a more suitable life partner.