First time telling this story. Not sure if it’s any good, but here goes…
When I was in college (for background, I attended a pretty well recognized party school that was also beach side so lots of college hotties), I got hired to work at some after school program. However, this program was unique in that it served only girls (so like Boys and Girls Club, except the boys). What was really surprising though is that on my first day, I would learn that out of the entire staff of 11, there was only two guys and I was one of them.
I’ve always been a nice guy. That is to say, I’m really mindful about how I behave in front of women, I don’t joke around in inappropriate ways, and I look women in the eye when I speak with them. On one particular day, I had finished my assignment early and walked to our kitchen area to see if I can help with anything. I see one of the other instructors, Sam, furiously preparing snack while the other guy that worked there just sat by reading the paper. I walked in not really thinking much about it and asked if I could help. She desperately said “yes! thank you!” and I proceeded to help. That moment, that genuine act of kindness, would be a turning point. I was trustworthy and reliable and people love coworkers they can trust. Many of the women began hanging out in my classroom or asking me for help. Eventually many of those friendships evolved to FWB and in what would ultimately become an amazing fuck fest that included even banging one of the kid’s moms.
For the sake of keeping this story from getting too long, I’ll tell the story of when Sam and I slept together. When I first met her, she was dating someone, but just before the summer, she tells me that she broke up with him. So naturally, she wanted to party. She was also recently promoted to Assistant Director (meaning she became my boss) and was thrilled about making adult money. So we started hitting the downtown scene along with three other girls (two of which were so fucking hot). One night after being out, our friend dropped us off at her apartment. We were both pretty drunk and I definitely couldn’t drive home. She tells me, let’s go lie down. We go to her bedroom and jump into bed. She lies down next to me facing away and I instinctively roll towards her. She then screams out, “oh my fucking god i can’t take it anymore!”, turns around and jumps on top of me. I guess she’s being wanting to fuck me for some time.
Sam was a swimmer so she was pretty fit. She had nice rack on her too with shoulder length dirty blond hair and a cute face. So after she gets on top of me, she immediately starts making out with me. It was pretty hot. She sits up and takes off her shirt revealing a pretty sexy black bra. I sit up to start playing with them, unhook her bra, and start sucking on these beautiful tits. She’s moaning hard and yells at me “take off your fucking clothes!” I flip her off of me and start taking off my clothes. Once I’m done, I lean over her, pull her jeans off of her, and start running my fingers up and down her thighs. I tried to slow and gentle about it, but Sam just tells me “please fuck me already! I’m so wet!” So I pull her panties off and run my finger over her pussy lips and man was she WET! I grab my dick, rubbed it against her clit, before fully going in. I went in so easy and started pounding away. I start off laying against her, but got into a pushup position and start really going hard. Sam wraps her legs around and is basically screaming in pleasure. It’s really turning me on. I do this for several minutes before I sit up to continue fucking her. From this angle, I get a really good look at her tits bouncing up and down — my favorite position. I grab her legs and throw them over my shoulders as I continue fucking her as hard as I can watching her tits bounce. I then open her legs wide and take a moment to see my dick go in and out. I go slowly at first before building up rhythm again. At this point, Sam starts to rub her clit while I fuck her holding her legs at her ankles. After about a minute, she says “oh my god, i’m about to cum!”. She then turns and screams into a pillow. (I stopped for a moment to pat myself in the back haha!). Sam is breathing pretty hard and says, “that was fucking amazing!”
After she caught her breath, we switch into cowgirl position. She grabs my dick and slowly sits on top of it. She was super tight from having just had an intense orgasm, but after a moment I slide right in. She lets out a long moan as her pussy completely takes my dick and starts to ride. I’m really enjoying the view so I put my hands behind my head and just watch her ride away. Her eyes are closed as she finds a good rhythm letting out soft moans. I then grab her hips and start speeding up a bit. Her tits continue to bounce and I want them bouncing on my face so I lean her over so she slightly lays on top me and start motorboating them. With my hands on her hips, I start to fuck her getting her moaning louder and louder. She starts to ride me harder and faster indicating to me that she’s getting close so I rub her clit with my thumb while my other hand pays with one of her nipples. She has her hand over my hand and playing with her tit with her other hand. I’m fucking loving it. She let’s out a loooong moan, convulges, and collapses onto me. I keep my dick inside and rub her ass.
At this point, I’m surprised that I still have gas in the tank and I ask her if she wanted to keep going. She asked me how much longer I can go. I responded that I wasn’t sure since I had been drinking. She tells me she’s not sure how much longer she can go so I said I’ll try to finish. I stand up on the side of the bed bringing her towards the edge. She feels even tighter know as I slide my dick in. Sam moans a bit so I ask her if it still feels good; she says “yes, keep going.” I start fucking her, slowly at first, then speed up. She’s still moaning but I don’t think she’s enjoying it as much as before. Fortunately, I’m getting really close so I speed it up which gets her to moan even louder. As soon as I’m close, I pull my cock out and send ropes across her stomach and tits. I think I may have gotten her face too cuz I saw her wipe her cheek. Sam continues to lie there breathing hard so I collapse next to her not realizing how sweaty we had gotten. After she catches her breath, she jumps in the shower. I walk in a couple of minutes later and ask if I can join her. She says yes, so I do and we help clean each other off. She tells me that she hadn’t sex that good in a while, an obvious diss to her exbf. I laugh it off. I’m pretty sober at this point so after I’m clean, I drive home.
We fucked one other time after that and messed around at a sleepaway summer camp we coordinated together before she got serious with her now husband and moved to Portland. My wife and I actually visited her and her husband several years later and hit the brewery scene pretty hard. On the way to dinner, where we were pretty buzzed, our partners were talking to one another about 10 yards in front us while Sam and I caught up behind them. Sam grabs my arm and quietly says remember that summer when all we did was fuck. I shush her cuz I never told my wife that Sam and I slept together and even she had told her husband, I’m sure he wouldn’t want to hear her talking like that. Fortunately, it didn’t sound like either heard her, but she just laughed and said that was a lot of fun.
Like I alluded to earlier, Sam was just one of the several coworkers (or their roommates) that I slept with during my time working at that program. All of which began from just being a nice guy. Happy to share more of those stories if you liked this one. It was fun writing this — definitely took me down memory lane.
Source: reddit.com/r/gonewildstories/comments/ien7u5/the_time_i_m_slept_with_my_boss_f
And they say nice guys finish last.