- Boss and Assistant
- Published: Oct 22, 2012
- Author: SassynSexy
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- Category: Spanking stories
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"Boss gives his assistant a good spanking and fingering which results in great sex as well as anal"
I accepted a position as a personal assistant to the Owner and CEO of a large privately held corporation. Mr. Ryan is demanding, controlling and downright hot! He is about 7 years my senior and from the moment I laid eyes on him I was hooked. He is 6’4, brown hair, piercing blue eyes, strong features and in amazing shape for his age. I am 5’4, petite with curves in all the right places. Like Mr. Ryan I work out a lot and I am certain this was one of the reasons he hired me. I’ve never done this type of work before, however with my age and business experience Mr. Ryan felt I deserved a chance.
About Mr. Ryan: He is 57 years old and built his consulting firm from the ground up. His net profits are in the millions because of the affluent clientele he has managed to keep. He is powerful in his industry, controlling with his staff and runs a VERY tight ship. He divorced his wife about 2 years prior to me joining the company and had no one new in his life since. I wondered why, why a man who is successful and handsome could possibly be single, but he is.
He and I began to work closely on various projects from day one. It was very evident there was amazing chemistry between us but I know it’s not a good idea to get my meat where I get my milk. Mr. Ryan paid me very well and expected a lot out of me in return. Mr. Ryan came into my office one afternoon and asked if I could stay late the following evening. He had a big presentation with one of his biggest clients and wanted my assistance. He went onto to say it would be best to work after hours so there are no distractions. I agreed this was a great idea. He asked me to have dinner delivered as we could possibly be working late into the night.
The following morning all I could think about was being alone with him, after hours in his sprawling office. I fantasized about making mad passionate love to him on his desk, the large table and in front of the window that overlooks Lake Michigan.
“Stop it” I said to myself. “This is not going to happen.” “He is your boss and you’re not going to go there!” Needless to say, I slipped on my sexiest lingerie, a tight fitting skirt, a button down blouse that could either show my cleavage or not. Feeling sexy was important to me regardless of the outcome.
I arrived at the office and there was a different air between us. Mr. Ryan rarely smiled at the staff; he is a very serious man. This morning however he was and I wondered if he was thinking the same thing as I was. He was usually careful with his compliments, however this morning he said
“You look beautiful this morning Ms. Grace.” “Thank you” Mr. Ryan I said. Grace is my first name and he has never refereed to me in that manner, it was a huge turn on. I felt so sexy and sensual.
The last of the staff left and our dinner was delivered. I set everything up at the table in his office and he surprised me with a nice bottle of red wine. Yes we were working, however it was after hours and a couple of glasses wouldn’t hurt. During dinner we made small talk. Mr. Ryan drilled me about my life and why a beautiful girl like me is still single. I really didn’t want to go there so I changed the subject to him and his life. I learned he was taken to the cleaners by his ex-wife and was the reason he doesn’t date.
I suggested that we get started on our work and he agreed. I set up the lap top and went to work while he dictated to me what he needed/wanted. It took us about an hour, he was pacing and I was typing away. Without him noticing, I had unbuttoned a couple of my top buttons exposing my cleavage and beautiful bra. I asked him to have a seat and review where we were at. I navigated him through the presentation making sure he could see down my blouse. I could tell he was distracted but wasn’t sure if it was me or the wine.
Suddenly he turned to me and said:
“Ms. Grace, you know that you are distracting me with that beautiful cleavage.” “And you’re out of dress code Ms. Grace. He said.
I said “I am sorry Mr. Ryan sir.”
“Don’t be, I like it.” He said “I have liked you since you walked into my office Ms. Grace.” He said
“Oh Mr. Ryan sir, I am flattered but, you’re my boss and well I don’t think that is a good idea.” I said
“What’s not a good idea Ms. Grace?” “This?” as he ripped open my blouse exposing my tits and toned body.
“Mr. Ryan, yes this, I don’t think this is a good idea” I said
“Ms. Grace, I think it’s a fantastic idea!” he said
“But Mr. Ryan you’re my boss and I don’t dip my pen in company ink.” I said
“Ms Grace, I want you, I have wanted you since I laid eyes on you and I get what I want.” He said
He removed my bra and started sucking my tits like no man has. I threw my head back and yelled out “OH MY GOD that feels so good.” Hi hands moved to the hem of my skirt, I could feel him pulling it higher and higher. I though oh know he will know I didn’t wear panties to work. My skirt is now around my waist, his hands are on my tight ass, his lips working my nipples.
“Ms. Grace, you don’t have any panties on what a naughty girl.” He said
“No Mr. Ryan, I was in such a hurry this morning that I forgot them.” I said
“Well Ms. Grace, you know what happens to naughty girls don’t you.” He said
“No sir Mr. Ryan I don’t. I said
“Bend over Ms. Grace you need a spanking.” He said
“Oh Mr. Ryan please, no, please don’t spank me, I promise to be a good girl.” I said
“Ms. Grace, bend over you’re getting a spanking.” He said
Bent over his desk I was in heaven, I wanted it so badly and hoped he wasn’t too rough with me. As his hands landed on my tight ass I felt my pussy pulsating. With every slap I wanted more and he was gentle in nature. With each slap on my ass his finger was working on my pussy which was dripping wet!
“Ms. Grace, get on your knees and suck my cock.” He said “Yes Sir Mr. Ryan” I said.
His cock was big and beautiful and I couldn’t wait to have it in my mouth. I love sucking cock I said to him. He placed his hand on the back of my head almost forcing his cock into my mouth. He loved it; he loved how I sucked his cock and said
“Ms. Grace, you suck cock well, now let’s see how you fuck.” I couldn’t believe what I was hearing. Mr. Ryan is so conservative and reserved I wondered where this was coming from.
“Mr. Ryan sir, please fuck me, fuck me good.” I said.
I bent over his desk exposing my tight ass again. He spanked me again before inserting his BIG cock into my TIGHT pussy.
“Oh Ms. Princess Grace, “Now you’re going to get fucked like never before.” He said.
He started slowly, inch by inch until all nine inches was inside of me. “Oh yes Ms. Grace, you’re going to get a good fucking.” He said. We fucked faster and faster, harder and harder both of us yelling out in ecstasy. He slowed his moves and inserted a finger in my ass.
“Ms. Princess Grace naughty girl, do you like anal?” he asked.
“Yes Mr. Ryan sir, I do.” Please fuck my ass Mr. Ryan” I said.
Slow and easy he put his cock into my tight ass…spanking me with every inch. “Sir, spank me and fuck my ass.” I said.
“You’re so naughty, I love you my Princess Grace.” He said
I wasn’t sure if I heard him right but stayed in the moment. I loved his cock in my ass and worked every inch. We fucked passionately for over an hour before we both came. We fell into a passionate kiss after we both came hard. He held my face in his hands and said:
“Ms. Grace, I fell in love with you the moment I saw you. These past six months have been a challenge working so closing and not being able to caress you. Will you please do me the honor of being my girlfriend?” He said.
“Mr. Ryan, it would be my honor to be your girlfriend if you promise me one thing, promises me that you will always spank me and fuck me like a naughty girl” I said.
“Yes Ms. Grace, I promise” he said “But I have one more assignment for you Ms. Grace” he said.
“What is that Mr. Ryan?” I asked
“Your next assignment is to pleasure our biggest client and I at the same time.” “Are you up for the task Ms. Grace?” He asked
“Yes Mr. Ryan I am” I said
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