Assistant with Benefits
This is a true story. It is my first attempt at writing so please give me suggestions to improve.
I love being self-employed!! I have a small successful consulting practice, just me and my assistant, Anne. We have a busy season for 4 months of the year which basically pays our wages for the whole year. The other 8 months of the year we work shortened hours just to deal with client questions.
My assistant, Anne, is hot. When I hired her she was a 22 year old college graduate who had excellent administrative skills and customer service skills. She has worked for me for 5 years. In those 5 years she has lost weight and unknown to me had a breast enhancement. So, now she is this hot 27 year old. Anne is 6 feet tall and has legs that go on forever. And she knows it, most days she wears short skirts to show off her wonderful legs. I love when she comes into my office and seductively crosses those legs. Her skirts highlight her tight perfect ass which has been toned by many, many hot yoga classes. Anne is also proud of her perfectly enhanced breasts and usually wears a nice silk semi-transparent blouse with a pretty bra under neath. The girl makes it hard (pun intended) for me to concentrate on my work.
Anne and I flirt back and forth. She will come in for a signature and "mistakenly" brush her breast against my shoulder. Or if we are bantering back and forth and she is being difficult I will give her a quick spank on the ass. She always rewards me with a sexy smile when I slap her ass so it has encouraged me to be bolder and sometimes I will let my hand linger on her ass after the slap.
This playful flirting was fun, but we never crossed the line and kept things in the office on a professional basis. One quiet day at the office that all changed….
That day Anne wore her usual office attire - a short black mini skirt and a low scoop white top which highlighted her hot pink bra underneath. Today's tax was to review our client files and send out progress reports. We were in the meeting room reviewing client files and Anne was writing stuff on the white board. I was trying to concentrate on the conversation but all I could think of was her perfect ass. I always wondered if Anne wore underwear under the skirt. After years of checking out her ass as she walked away I could never discern a panty line. Today, she caught me checking out her ass!!
She turned around quickly and caught me. She said, “Paul are you listening?” I said, “Ahh, sorry … I have a headache today and having trouble concentrating.”
She said, “Ok, I have just the thing for you, wait here”. She left the meeting room and returned a moment later with a bottle of Tequila one of our clients had given us and two shot glasses. She pulled up a chair and sat across from me. She filled the shot glasses and we each downed a shot. We repeated and then she sat back in her chair across from me and did one of her seductive crossing of the legs. In my mind, this was always in slow motion. The alcohol was starting to hit me and my stare was drawn to her sexy legs. She said, "Are you enjoying the show?"
I snapped out of it and said, "What, no, just enjoying the alcohol, hit me again." We had a few more shots and we were getting drunk and laughing at everything.
All of a sudden, Anne blurted out, "Earlier when I was writing on the white board, were you checking out my ass?”
I said, “No, err, well yes….”
Anne said, “Well good it is about friggin time, what does a girl have to do to get some attention around here? I don't wear these mini skirts because they are comfortable, you know!”
We were still seated facing each other, almost knee to knee. I moved my chair closer and put my hand on her knee. Her legs weren't crossed and when I put my hand on her knee she widened her legs (as much as the mini skirt would allow).
I said, “Was this the kind of attention you were looking for?" As I said that I moved my hand up the inside of her leg and just inside her skirt.
She exhaled and said "Un-huh"
I couldn't move my hand any further up her skirt and said, "I see what you mean by these skirts not being comfortable!!" She was in a breathless trance and just nodded and looked at me with those "Fuck Me Eyes" that she has.
I asked her,"Let's see if we can make you a bit more comfortable, shall we? Stand up for me will you?"
She stood up and I turned her around and undid the button and zipper at the back of the dress and let the skirt fall to the floor. This time I gasped. Indeed she was commando underneath the skirt and what was displayed before me was her perfect bare ass.
She bent over and put her hands on the arms of her chair and spread her legs wide for me. From my seated position this gave me a perfect view of her shaved pussy.
I moved my hand slowly up the inside of her leg and took my time approaching her pussy. I had fantasized about this for years and I wasn't going to rush things. When my hand made contact with her wet pussy she moaned and pushed into my hand. I had her right where I had always wanted her.
I lightly rubbed the outside of her pussy and got her pussy juices flowing.
I inserted one finger in her hot pussy and started slowly going in and out. I was still seated and she was bent over in front of me. I enjoyed watching my finger go in and out of her tight, wet pussy.
She was soaking wet and I inserted two fingers and went as deep as I could. She pushed back against my hand do get me deeper. I started going a bit faster and she started moaning and rocking back and forth on my hand. I took my other hand and slapped her bare ass. Not too hard, but hard enough. Her juices were dripping down the inside of her leg. I started moving my hand faster and faster and probing her pussy as deep as I could. She was moaning loudly and let out a loud scream. She came all over my hand and her knees buckled slightly. I slowly removed my hand to let her recover.
In her dazed afterglow I gently stood her up and turned her around to face me. I undid her blouse and removed it. Then I unsnapped her bra and her perfect breasts came bouncing out. They were even better than I had imagined. They were perfectly symmetrical and she had large erect nipples just begging to be sucked. I moved my mouth to her right breast and gently licked her nipple with my tongue. She shuddered and I took her nipple into my mouth and started gently sucking. As I was doing this she started running her hands through my hair and grinding her tits harder into my face. I sucked harder and moved my hand down to her pussy and started lightly fingering her clit. Within seconds she came again.
She cradled my face in her hands and passionately kissed me on the lips. Now it was my time to melt. Her kiss was full of passion and I don't think I had ever enjoyed a kiss so much in my life. While I was mesmerized by the kiss, Anne was quickly undoing my belt and removing my pants and underwear.
She broke free from our kiss and got down on her knees and gently held my rock hard penis with both her hands. She gently flicked her tongue over the head of my cock and licked up the pre-cum from its tip. Then she took my full cock into he mouth and started sucking and bobbing on my cock. Both her hands were on my butt cheeks and she was pulling my cock deep into her mouth. I could feel my cock hit the back of her throat but she was determined to take the full length of my cock.
Just as I was getting close to the edge Anne looked up at me mischievously and said, "Boss, will you please fuck me on the board room table?" With that comment, she playfully laid down on the table and spread her legs inviting me to join her. I pulled her to the edge of the table and gently rubbed the tip of my cock against her clit. I needed the time to regain my composure because Anne's incredible blow job had almost made me cum in her mouth. Now I was ready. I slowly entered her pussy. My cock is average length but quite thick. I gently eased my thick cock into her tight, wet pussy and let her juices coat my cock. She looked so beautiful laying naked on her back with her legs wrapped around me and my cock embedded deep in her steamy pussy. She gave me her "Fuck Me Please" look and I started moving in and out slowly. I had fantasized about this for years and was not going to rush. I began thrusting faster and faster. We both started making a lot of noise. I fucked my beautiful assistant as hard, as fast and as deep as humanly possible. We both came explosively together. I collapsed on top of her and nuzzled my face in her breasts while we both caught our breath.
After a while, we came back to reality. We got up and got dressed rather awkwardly.
“This isn’t going to be awkward is it?” I said
“Not unless you make it awkward!” she said.
She was right, it was not awkward at all. We have had, hot, steamy office sex many, many times since.........