It’s been awhile since I wrote about my boss Rachel so here’s another one for old time’s sake. If you haven’t read the first 2 parts I suggest at least the first part for context and the 2nd if you’re a degenerate like me who just likes to hear about people fucking. Enjoy!
At this part of the FWB relationship with Rachel, I did in fact receive the job role I wanted with higher pay thanks to Rachel. I was her direct report now so at work I did whatever she told me to but outside of work and in the bedroom she did whatever I told her to.
A couple of weeks after I was transferred to Rachel’s team, I was working when she called my register and said she needed to schedule a meeting with me to discuss my training progress and sales numbers. It was late in the evening (for business hours) and I told her there were only 2 of us in that area for the rest of the night and she said to let my coworker know I had to meet with her and that she asked them to cover the floor until I returned. Once I passed on the message, I walked upstairs to her office to meet with her. I walked in, while her back was towards the door. She told me to shut the door while continuing to type away on the computer. I did as instructed, and soon as the door closed she turned to face me.
She was wearing a black skirt with a red button shirt that would have been appropriate for the office had she not undone 2 buttons before I walked in. I immediately started to get hard and said “I’m not really here for a performance eval am I?” She kept a straight face and said, “oh you are most certainly are Mr. _______. As a matter of fact I’ve been looking forward to evaluating your performance all day long.” She said that last part very coyly. As much as I was enjoying the foreplay at work, I couldn’t help but say “are you sure this is a good idea? I thought we agreed to keep this stuff on the DL while working?” Rachel stared at me before saying, “Mr. _______ your performance eval is very important to your new position and will be crucial when it comes time to offer you a raise. Do you really want to turn down this great opportunity when it is right in front of you?”
——————sex starts here——————————
I knew she was enjoying the back and forth and even though what she said really didn’t make a lot of sense, once again I did not have enough blood in my brain to make the smart decision. I pulled the blinds down to her office door window and said, “What do you need me to do?” Rachel smiled and walked around her desk to sit on the edge of it in front of me. She gave me some forms to fill out and at this point I was super confused about what was actually about to happen. However no sooner did I start filling the forms out then she unbuttoned her shirt all the way and removed it completely before kneeling in front of me. She knelt there in her black skirt and sheer black bra before undoing my belt. She pulled my pants and underwear down before running her tongue up and down my shaft. She did this a few times before taking all of it in her mouth. I expected her to try to be quiet but she moaned as she bobbed her head up and down, maintaining eye contact all the while.
Soon she stood up and hiked her skirt up, revealing absolutely no underwear underneath. She lowered herself onto me and began sliding back and forth, undoing my tie so she could kiss my neck and collarbone. I moaned softly and grabbed her by the hips. She was so tight and wet that I almost came after a few minutes except soon there was a knock on her office door. She quickly placed her hand over my mouth and said loudly “Who is it? I’m in a performance evaluation”. A female voice that I recognized as being one of our LP detectives answered back and said, “Sorry give me a call when you’re done please.” We waited there absolutely still until we heard her walk away before Rachel began grinding on me again. Rachel laughed quietly and said, “oh my god that was hot. Did you feel me cum a little as she was talking to me?”
I answered back, “oh that was funny to you?” Before she had the chance to answer, I picked her up and took a few steps to get to the edge of her desk. I laid her down on her back and began rubbing my dick up and down between her pussy lips. She moaned before covering her own mouth out of fear of being heard. As I pushed myself into her again, I reached over and yanked her bra down, letting her large tits jump free. Both of her hands went to her mouth while I grabbed her by the hips and pushed into her again and again. Her tits bounced up and down with each thrust and before long her face got really red which told me she was close to cumming. Sure enough about a minute later her eyes got so wide they looked like they might pop out. She began shaking and moaned quietly into her own hands.
I pulled out of her slowly and she stood up, legs shaking. She turned around to fix her bra and that’s when I pushed her facedown onto her desk. “I’m not done yet.” I said quietly to her. Her ass looked so good from the back and we had talked about doing anal soon so throwing caution to the wind I rubbed my dick up and down her ass, using our various body fluids for lubricant before very slowly pushing myself into her asshole. She gripped the sides of the desk with both hands so hard I heard her knuckles pop so I reached around and covered her mouth with my other hand. By now I was about halfway in her ass and her legs were shaking more than ever. I began pushing very slowly in and out of her ass, grabbing one cheek with my free hand. Unfortunately I was still only halfway in, as she bucked in pain if I tried to go any deeper. Her ass was so tight I could tell she hadn’t done anal too often if at all. I was now at a point where I was thrusting a little faster and she winced a little with the pain.
From my angle I had a very good view of her tits against the desk and watched as they jumped with my more forceful thrusts. Finally I could feel myself getting close to finishing so with one hand still over her mouth and the other on her hip, I pushed one last time and felt myself cum inside her ass. She whimpered softly and continued squeezing the edges of her desk. I stayed inside her until I could feel myself finish pumping everything I had into her. Once I felt myself completely empty, I pulled out very slowly. By that time she was limp against the desk breathing hard. Her hair was disheveled and her mascara was also messed up a bit but she winced a little bit as I pulled myself out. I was genuinely surprised there wasn’t anything on my dick (if you’ve done anal you know what I mean) but figured it was due to not having been in all the way. As I bent over to pull up my pants, I could see my cum dripping very slowly from her asshole.
I asked if she was okay and she nodded, still breathing too hard to say anything. She finally stood up and grabbed some paper towels under her desk to wipe herself with. She fixed her skirt and bra. While she rebuttoned her shirt, her legs shook like leaves and she said, “thank you for your hard work today Mr. ________. I think I made the right choice in bringing you to my team.” I checked my watch and saw that our meeting had been about 30 minutes so I needed to get back to the floor. She nodded and waved at me to go. The last thing i thought when I left was that her office smelled like sex.
I got back to the floor and my coworker asked how my eval went. I told him she rode me pretty hard on her expectations but I felt it went well. About 15 minutes later it was closing time. I saw her once more before I left. She came into my area and when my coworker walked away to clean up she told me quietly, “I can still feel your cum in my ass.” I smiled and said “I hope my eval went well.” She laughed and walked away.
P.S. I found out later that the LP detective who knocked on the door was a friend of hers who found out that same night what we were doing that night before closing. While she never participated, she did go on to help us have more workplace escapades by covering for our occasional disappearances.
Source: reddit.com/r/gonewildstories/comments/m8zgav/how_i_21m_became_fuck_buddies_with_my_boss_30f