Back when I was 21, I was working as an intern at an engineering firm. My boss (I’ll call her Kathy) was one of the toughest ladies I’ve ever met, and she didn’t mess around when she needed something to get done. She wasn’t mean or anything like that, but she was firm and demanding. I worked my ass off for her, and I definitely credit my work ethic to her high expectations and refusal to settle for any sub-par results.
After I graduated from college I got a job out of state. When I was hired, my new boss told me that my reference from Kathy was one of the most impressive he had ever heard.
Fast forward to now, I am 25 and applying for a new job in light of COVID. I reached out to Kathy to see if I could put her down as a reference again. This was the first time I had ever talked to her while she wasn’t my boss and I was kind of caught off guard by her casualness. It turned out she was going to be in town the next week to check in on a relative and asked if she could buy me lunch. The girlish excitement in her voice when I said I would love to join her for lunch was a little uncomfortable since I had never experienced this side of her.
The day came and we were sitting outside under a tent while the server with a mask on took our order. I cannot stress how strange it was seeing Kathy outside of work. I was used to seeing her in tasteful professional attire but today she was wearing a red sleeveless turtleneck with these high waisted jeans and my brain was so confused. I had never had an unprofessional thought about this woman in my life and in this moment I could not tear my eyes away from her curves.
Kathy ordered bottomless mimosas for both of us and shot me down when I protested. As the lunch progressed and the mimosas kept coming, it suddenly occurred to me that Kathy was flirting with me. I, being a bit buzzed at this point, started laughing uncontrollably while she just smiled and looked at me. I finally caught my breath and with the biggest smile on my face, I asked “what is happening right now??”
Kathy gave me a knowing smile but changed the subject as the server brought our check. She told me that I was going to walk her back to her hotel before taking my arm and leading the way. We were bantering and laughing like idiots when we arrived at her place. She told me I needed to join her for a cup of coffee to sober up. Since there weren’t any coffee places to sit down in (pesky COVID), we were gonna have to take them up to her room.
It was after leaving Starbucks but before we got back to the hotel that she kissed me on the cheek. At this point we were laughing with our arms around each other all buddy buddy so it didn’t seem that weird, but then when I turned to look at her she went in for the kiss on the lips.
I must have still been a bit buzzed because without even thinking, I kissed her back, and slowly parted my lips as her tongue glided into my mouth. We composed ourselves, took a deep breath, and started walking a bit faster back to her hotel. We were giggling like idiots the whole way.
We made out in the elevator for the first few floors before I pulled away for a second and asked “ok wait, what the fuck??” She laughed and said, “I’ve had my eyes on you since the moment you were my intern. But I’m not a man so I keep shit professional in my workplace. But we’re not in the workplace anymore and I’m not your boss so as far as I’m concerned, you’re fair game now.”
With that, she kissed me again, and there was something sooo fucking hot about the way the smell of coffee around us was giving me flashbacks to the office break room when I worked for her.
I don’t even know how to describe what happened when we got to her room. She had clearly been wanting this for some time because once she got me on her bed she fucked my brains out. I did not do a thing. Honestly it was the most surreal moment of my life, having her straddling me with her tits in my face while she whispered the filthiest things in my ear. I have never felt so desired in my life.
Afterwords, Kathy held me in her arms and played with my hair for a while. She started brushing her fingers along my bare chest and it got me hard again. Before I could say anything, her arm tightened around me and she was jerking me off while whispering in my ear again. I came in her hand and she cleaned me up with her mouth. I could not believe what was happening. She was so sweet and affectionate.
That was last weekend and I still feel like it was a dream. When I told her I was going to post about it on reddit, she sent me a video of her masturbating naked in bed while moaning my name. She wanted to “get me in the right mindset.” Kathy, I don’t think you have reddit, but if you do, know that you are a professional powerhouse and the coolest woman I have ever met?
Source: reddit.com/r/gonewildstories/comments/izs9n9/my_25_exboss_43_from_out_of_town
Pesky COVID lol. Are you sharing the video too? :)
Hot as fuck ? story
That’s what it feels like when a sexually frustrated cougar attacks a young, tender morsel like you. She probably felt super-naughty with a dude half her age. You should have called her “Mrs. Robinson,”…you might be too young to get that joke but your cougar would laugh hysterically. What middle age corporate executive DOESN’T want to bang the intern? Too irresistible. Thanks for a salacious and entertaining story about your practically non-consensual tryst with a middle aged woman. You are well on your way to becoming a sugar baby… she did offer to PAY for lunch. Coincidence? What say you? I’m joking by the way ?
Super hot, will you see her again?
This is a delicious story!