Should I [M] fuck my boss [F]

Well I did.

This all started with a happy hour. Charity happy hour actually.

I had convinced her to loosen up and to order whatever drink sounded good to her. I believe it involved a rum, orange liquor and some sort of cream. My intention was for her to have a good time as I had no idea what her private life was like. She’s a woman in her early thirties out with coworkers for some drinks. I’d describe her as very petite, maybe 110 lbs, but with defined hips, pale and with reddish, brown hair. It’s an open bar occasion so she’s getting comfortable and trashed. Honestly, to this point, I’ve thought nothing more than the occasional “would not be mad if she was naked” type thought, because she seems like the most innocent person you’ve ever met.

This night, she proceeds to spill beans of her sex life. She definitely loosened up and she got to talking with my coworker. In jaw dropping fashion, she tells him she’s had an orgy relatively recently. Fuck. I’m convinced she 100% regrets telling him this. Regardless, the rumor makes its way to me because he can’t keep his mouth shut. Well my mind is flowing with fantasies now. As the night progresses, we kind of all act like it hadn’t been mentioned and make our way home. I’m so horny though, so I text her as I’m leaving and make sure she doesn’t need a ride. I’ve never crossed my fingers so hard. [Unfortunately she gets an Uber and that ends the night.]

Over the next few weeks, we avoid blatant conversations about this but it’s definitely lingering. At this point, all I know is her exploits and based on all interactions, there’s no attraction coming my way.

A month later we have another outing to where it involved a lot of alcohol. Throughout the night, everyone was very cordial, not to disturb the norm and also not to drop the bomb of what she does in her free time. By the end of the night only a few were left standing. Those few ended up at a bar where she apparently felt very comfortable and push and pulled about mine and another coworkers sex life. I don’t truly know what was going through her head that night but I have a good idea.

The night I fucked her for the first time is one I’ll never forget. It was pouring and I was trashed. She had driven 30 minutes to meet up. She got in the passenger side door wearing a t-shirt and some short ass shorts. I’ll never forget those shorts because i can vividly see them coming off. 

I felt like I was the one in charge considering she’s my boss, perhaps it was because she came to me, but man, when I told her to suck my dick, she fucking sucked my dick. It was incredible. She got naked and wanted my dick.

She had a sexy body and wanted my cock. It was so easy for her to convince me to give it to her. This went on for a long time, and honestly, if I controlled time, we’d still be there, making out, her sucking dick, me sucking tits, preparing to fuck. God it was bliss.
After a while we made our way to the backseat. I know it was a tight space but we were so turned on. I had a 11/10 babe in my truck naked who’d been sucking my cock on demand. Imagine not wanting to fuck her.

I had her willingly pinned against the seat. Dick was hard as it’s ever been. I was rubbing my cock in her wet lips and I’m pretty sure I was convincing myself to not do it but I couldn’t control it. When I first entered. God fucking damn. It was so wet and warm. I’ll never forget that first feeling. We fucked with the pouring rain outside and I pulled out and came all over her sexy toned body. Since then, I think about it every hour.

This continued on for several other hot meet ups, some in office, but she recently moved on to another job. That hasn’t stopped some very great meetups.

Source: reddit.com/r/gonewildstories/comments/fv6k9y/should_i_m_fuck_my_boss_f