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Office Rules


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Twenty-five year old tries his luck with a thirty year old MILF.

This is a true story about an experience I had three years ago. Names have been changed for privacy reasons. This is my first story, any feedback or suggestions on my writing style would be appreciated.

Her name was Jennifer. She was thirty years old and a mother of three children. She was in a long term relationship with the father of one of the children, the other two were from a past relationship. 

She had long dark hair that she wore up in a ponytail or clipped in a bunch while she was at work or at the gym but had it straight if she was going out for a drink or meal. She had a slimline figure, you'd be hard pressed to find any evidence of the three children on her figure. Regular outings to the gym kept her in great shape, she took pride in her ass and legs, especially in the summer when she could show them off properly. 

Jennifer joined the company I worked for in early 2016; she was a call agent while I was the administrator of the company. She seemed nice and definitely hot! I was young and inexperienced at the time, so I was often too obvious with being ‘too' nice to her. We always greeted each other with a smile and went about our day. All that changed on a Friday in June 2016 when we were having a conversation and she didn't know what to call me as she could call Mike, Michael, Mick and I said to her I'd think of what I want her to call me.

On Saturday I was having my breakfast and we had this text exchange over Facebook;

Me: "I finally realized what I want you to call me, although your reaction to what it is will tell me a lot." 

Jennifer: "Ok, I'm all ears, babes. What is it?? xx"

Me: "I might regret this like, but fuck it. I want you to call me Master but only when we're alone."

Jennifer: "Yes Master, I understand. xx"

Me: "You make Master very happy."

Jennifer: "I'm glad. xx"

Me: "You weren't expecting that, were you?"

Jennifer: "Not at all, no complaints though. xx"

Me: "Good, I like when one of my girls doesn't have any complaints."

Jennifer: "None from me. xx"

Me: "You won't like Master when he's mad (well, you might. Depends what you're into.) x"

Jennifer: "Mmmm I think I might!! xx"

Me: "I can be awfully demanding when I'm mad and not easily pleased, still think you'll like it?"

On Monday, when we were alone, I dropped a few simple commands to make sure she was playing along. Around 2:30 pm, I noticed that I was working alone in my office (management had gone somewhere) so I dialed upstairs to Jennifer's desk.

"Master wants to see you downstairs," I told her.

"Oh okay, I'll be downstairs in a second," she replied.

Immediately after I put the phone down I was getting hard. Jennifer made me wait three to five minutes before I heard the knock on my door. I let her in and closed it.

"I'm disappointed you took so long," I spoke firmly to her.

"I'm sorry, Master," she replied and looked at me like a sad dog with puppy eyes.

"I think Master needs to teach you a lesson," I said to which she flashed a smile.

"What do you have in mind, Master?" she said.

"I want you to brace yourself against the wall so Master can spank you," as I pointed to the wall of the office.

She complied with no resistance.

"Yes, Master," was the reply as she got into position.

To describe what she was wearing were thin tight leggings, a black tank top, and a clearly visible black bra. I walked up behind her and said; "You've been a bad girl haven't you?"

"Yes, Master," she replied. 

"You need to be punished," I said and I spanked her right ass cheek before grabbing it with my hand and squeezing it. 

I had never been so horny about Jennifer until that point when I got my hand on her ass. I continued spanking Jennifer, to her credit she stayed quiet but I swear I heard a few moans when contact was made on a few strikes. 

I laid both of my hands on her ass cheeks and started rubbing them before stepping into her. I simultaneously wrapped my hands around her waist and stepped into her further so my crotch was pushing into her ass cheeks. 

"Mmmmm," She audibly moaned.

"You like that?" I replied.

"Yes, Master," she said under her breath.

I started swaying us back and forth, our bodies in constant touch and I was getting rock solid in my pants as you can imagine! I pulled away and with a thrust pushed her forward as I started to dry hump her ass while holding her waist. I pounded her ass for two minutes, enjoying the sights and sounds she made making. I stopped and rested my now solid cock straining to be free of its constraints in my pants against her ass cheeks. I leaned forward and grabbed her tits and squeezed them, running my hands down her body, flicking her pants down a bit to see she was wearing black lacy knickers.

Before I could lower her pants any further or do anything else, I heard doors opening on the other side of the wall... someone is coming towards my office! I kept Jennifer in the same position and looked over my left shoulder towards a window that views into the corridor. To my extreme fright and somewhat delight I saw the young and very cute seventeen-year-old account apprentice looking at me and Jennifer in this position.

Fearing for my job in a split second I pulled away from Jennifer and said to her; "I think Rachel saw us," before letting out a nervous chuckle. 

"She probably doesn't understand it, she won't say anything," Jennifer said as she pulled herself up.

Rachel disappeared, myself and Jennifer were standing in front of each other, I sat down and told her to spread her legs a little, she complied. As my adrenaline was at an all-time high I placed my hand on her pussy and found it was very warm and wet to the touch even through her leggings.

"Good girl, you may go now," I said.

"Yes, Master," she replied, and I had to find a way to calm my thoughts down before continuing work.

As I got home from work that day, I thought to myself what else I could convince Jennifer to do...

 

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