I 37 [F] slept with my boss’ 22 [M] son

This happened a few years back…I slept with my then-boss’ son. I wouldn’t actually say “slept with”, more accurately, it was some of the most dirty and passionate fucking I think I’ve ever experienced. Top marks.

At the time, I was in my late 20s/early 30s (I’m 37 now), and I worked for one of those companies where everyone not only knows everyone, but you are social outside of work, too. It was normal for us to go to an event, or casual meal, or late night beers around the fire pit at the boss’ house.

I was often at these events, and when I first started at the company, I knew my boss had some kids, but we didn’t really see them except in passing (some high school and college-age), though it was “known” that he wanted his son to join the family business. During an off-site, my boss wanted me to connect with one of our partners for an event we were putting on at a hotel, and oh my goodness. This guy was incredibly tall, fit, confident, well-dressed, sexy, and did he have a killer voice! He was so attractive that my normal professional and polite indifference went right out the window.

He seemed to pick up on my interest and shamelessly flirted with me during the entire meeting. After the work piece wrapped, he invited me to get some dinner, and asked where I was staying. Since I was staying in the hotel and had an early morning, he suggested we eat at the hotel restaurant, and boldness took over…I suggested room service instead. We’d been working hard after all!

As soon as we were in the room though, all that professionalism went out the window. Let’s call him Aaron for this. (Obviously not his name) He grabbed my ass, pushed me against the wall, pressed himself against me, kissing me hard. I was trapped, but completely electrified. I could feel (very hard) how excited he was too, as we made out and groped each other.

Finally, he all but dragged me to the bed and before I knew what was happening, he’d had my top off. I am very curvy, and when he saw my 36GG breasts, he said he’d been “dreaming of these since he met me”. I’m used to men being interested in my breasts, so didn’t think much more of it either than I wanted him all over them…kissing, licking, groping, biting…I also didn’t have to wait long before he was naked and I had his enormous (seriously, I was a bit scared) cock between my breasts. It was so intense, that he nearly cried when after he came all over them, I licked off some of the cum that landed on my lip.

We stripped and got into the large spa bath and after taking extra care to wash each other, (he also spent extra time licking my pussy while I hung over the edge of the tub) I found myself on the bed again, this time guiding that cock into my dripping pussy. Oh it hurt, too…and he was so energetic, so fucking deep, but I wanted it. I wanted him. I got up and turned around and he gripped my ass and drove himself in again. I think I may have even left my body it was so deliciously brutal, and when he came, I demanded that he do it in my mouth. I couldn’t get over how good he tasted, how he felt.

During the event in the morning, I didn’t see him, or anyone really. I was too busy supervising various groups to make sure everything ran smoothly over the next four days if the event. Each night though, he stayed in my room with me while we alternated between brutal fucking and slow passionate sex. I lived off coffee, and after the event was over, I think I slept for nearly a full day, I was so exhausted. I was fucked pink and bruised, and absolutely loved every moment of it.

A few months later, at another home event at the boss’ house, our team were all poolside enjoying the day, and who shows up, but the guy! He spotted me immediately and grinned. In a bathing suit (sarong on or no), there’s not much I could hide, but I got up and said hello. After small talk, we were inside having a drink, and it was getting dark. Most of the team were still out back around the boss’ fire pit, when Aaron grabbed my hand and marched me upstairs and I quickly found myself in a bedroom. Before I could speak, we were fucking wildly, but this time we had to be silent, and alternated covering each other’s mouths. He especially needed to keep me quiet when he started licking my asshole. Fuck, it was so intense!

After we’d collected ourselves, I told him we needed to get out of there, and he said he just wanted to relax a bit. I was confused because we were obviously in the room of someone who was a student. I knew my boss had kids, and I didn’t want to be in the way. I convinced him to relax downstairs, and as we were rounding the corner, my boss stops Aaron and after giving him a hug, (weird, I thought, even with how close the boss is with everyone) he proceeds to introduce his son to me! He told me (and the folks from outside who started filing back into the house) that his son Aaron was getting ready to graduate and had been picking up some work with our partners. He was excited for his 22 YEAR OLD son to join the team after graduation. As I was the top performer, my boss said he expected us to work closely. I blinked to clear my vision, introduced myself, and shook Aaron’s hand while under my sarong his cum was sliding down my thigh.

Source: reddit.com/r/gonewildstories/comments/uducza/i_37_f_slept_with_my_boss_22_m_son