The Boss

I was so excited about my first real job since I got out of college. The company was big and I knew that if I did my job well I could retire from here very well off financially. For the first couple of months everything was going great. My coworkers were nice, my bosses praised my work, and I had never been happier. But, as with all things in life, there were going to be some bumps in the road. And, as it turned out, my bump was going to be Mrs. Taylor. 

Mr. Taylor was the CEO of my company and his wife also held a very high position in the company. From what I heard they started this company fresh out of college and built it into a solid company by the time they were in their mid forties. As luck would have it a bigger kid on the block wanted to buy up the competition and the Taylor’s company was the one they targeted first. Rumors had it that the buyout made them both very wealthy and the new management wanted to keep them around for at least ten more years.

The Taylors were a great set of bosses. They treated the employees very well and everyone had a lot of respect for them and what they had done, including yours truly. I almost viewed them as sort of surrogate parents. The only problem was I was starting to develop a huge crush on Mrs. Taylor. She was a very beautiful older woman. She had a body that was curved by the years, but very sexy curves. I would guess her to be about 145 lbs, dark brown hair, big tits, and a sexy set of green eyes that seemed to burn to your very soul. 

At first I didn’t notice how sexy she really was, but as I started to take note of her through the months I became more and more attracted to her. She wore business suits to work that were pretty conservative. I loved the times when she would have me work on an assignment that caused me to report directly to her. The day she finally had me wrapped around her finger was on one such occasion. I was working on a very high profile report and she had called me into her office to review what I had done so far. I gazed at her while she reviewed it and took time to notice every aspect of her beauty. I was thinking to myself that this had to be the sexiest older woman I had ever seen. Until Mrs. Taylor I had never really thought about women that much older than me. 

I must have been daydreaming about her when she said, “Brian did you hear what I just said?”

“Uh, I’m sorry Mrs. Taylor what was that again?”

“Brian I need you focused on this assignment. Is that going to be a problem for you?”

“No ma’am not at all.”

She walked around the desk with the report in her hand. She leaned over to show me something in the report when I noticed that her blouse was open and I had a full view of her magnificent tit right in my face. She wore a pink satin bra with lace trim. I also noticed that her nipples were straining against the material. Oh how I would love to release them and suck them into my mouth. I tried as hard as I could to stop staring, but I had grown to be so fond of her I just couldn’t make myself to look away. The words coming from her mouth we just blah, blah, blah. All I was doing was admiring her tits. I realized that I was starting to get hard which made me nervous. What would I say if I tented my pants right there in front of her? I had to look away. But my gaze just kept coming back to her tits. I looked down and I could see the outline of my cock straining against the leg of my pants. I hoped Mrs. Taylor hadn’t noticed it as well. How embarrassing.

I was in trouble. I almost sported a full on hard on in front of my boss whose husband is also my boss. What if she saw it? Would they fire me for that? And what am I going to do about the report we just reviewed. I didn’t pay a damn bit of attention as to what she wanted me to work on. All I could do right now is rush to the bathroom and release my aching cock from the confines of my pants. I sat the report on the edge my cubicle and went straight there. I just needed to stroke it a couple of times and think about Mrs. Taylor’ sexy breasts. Oh god it felt so good, but it was so bad.

I was about to lose my load when I heard the door open to the restroom. Oddly when the person walked into the room it sounded like the clicking of a woman’s heels. I was frozen like a deer in headlights. Who was that? No woman would be in here. This is the men’s restroom.

I felt my heart drop into my stomach when I heard, “Brian are you in there?” shit it was Mrs. Taylor. She must have followed me in here. What the hell is she doing in here?

“Um…um. Yes Mrs. Taylor.”

“Well what are you doing in there? I don’t hear anything.”

“I …I just haven’t been able to start yet. That’s all.”

“Brian are you lying to me? I think you are. I think you’re in there stroking your cock.” 

What the hell. How in the world did she guess or think that?

“What?” I asked surprised.

“Come on Brian I noticed you looking down my shirt. Staring at my tits, and I also noticed you getting hard in your pants.” She said with a giggle.

“No I swear Mrs. Taylor I was just going to the bathroom. Honest.”

“Brian you don’t have to lie about it. As a matter of fact, I don’t like employees who lie to me. Now open the door.”

I was so busted. What the hell is she going to do to me? I tried to stuff my cock back into my pants, but that was like trying to put a square peg into a round hole. Reluctantly I slowly opened the door to the bathroom stall. She stood there with her hands on her hips and just looked down at my crotch.

“I knew it! You dirty little man. I want to see you in my office at the end of the day. Do you understand?”

I lowered my head in shame and weakly said, “Yes Mrs. Taylor.”

I was absolutely worthless the rest of the day. I even packed up some of my things because I just knew that I was walking into a firing that afternoon. My dick always seems to get me into trouble somehow. And it really fucked up big this time. I guess that is the curse of being well hung and horny all of the time. I just can’t believe I screwed up the best job I have ever had. How would that look on my resume? Fired from last job because the boss caught me jerking off? Who would ever hire me? Washed up at thirty.

About five minutes before five Mrs. Taylor’ AA came to my desk and said, “Mrs. Taylor would like to see you now.”

Shit here it comes.

I followed the AA down the hall and into Mrs. Taylor’ office. She was sitting at her desk talking on the phone and doing paperwork. She waved for me to take a seat and told me she’d be with me shortly. I was like a kid in the principles office just waiting for my punishment. 

Once she hung up the phone she buzzed the AA and said, “Becky that will be all for today. I do not want to be disturbed for the rest of the day. Is that understood?”

“Yes ma’am”

“Thank you.”

Her gazed then turned to me and those beautiful green eyes that I had always admired were now burning a hole in me.

“Well Brian it seems we have a sticky situation here. You are one of our best employees and we had big plans for you. However, in light of what happened today I’m not so sure we had the right idea about you.”

“Mrs. Taylor I’m so sorry for what happened today. I don’t know what I was thinking. I can assure you…”

“Just stop Brian. I can assure you of one thing for sure. And if it leaves this office I will swear you are making it up and fire you on the spot. You will have no grounds for any type of lawsuit when I tell them what you did today. Do you understand?”

“Yes ma’am.”

“I can assure you Brian that what happened today made me very wet.”

What did she just say?

“Excuse me Mrs. Taylor?”

“You heard me Brian. It made me very wet. My husband and I have spent so much time building this company up that he has forgotten that I have needs. Needs that he has ignored for far too long. So while what you did today was very unprofessional, I’m willing to let it slide. But I want you to do something for me first.”

“Anything Mrs. Taylor. ANYTHING!”

“I want to watch you stroke your cock for me. Will you do that? And remember that none of this happened. I never asked you to do that, and I will swear that you made advances towards me that made me uncomfortable so I had to fire you. Understood?”

“Does this mean I get to keep my job too?”

“Of course you get to keep your job, and if you keep your mouth shut and keep what happens between us between us then you might just go farther with this company than you ever imagined.”

“Now take that beautiful cock out that I saw earlier. I’m curious to see what it looks like again.”

I could not believe this was happening. I mean I jerked off thinking about her all of the time anyway, but now I was going to get to do it with her watching. This was going to be so hot.

“Come on Brian sit on the couch over here and get comfortable and give me a good show.”

She sat across from me in an arm chair and her eyes were transfixed on my crotch as I slowly unzipped my pants. I slowly pulled out my semi hard cock. I heard her gasp as I took it all the way out. She also licked her lips like she liked what she saw. I thought I would be embarrassed stroking my cock in front of my boss, but I must admit that it was a very hot scene. It wasn’t long before I had it stroked to the full eight inches. The head was purple it was so hard. I continued to stroke it slowly at first. Rubbing the precum all over it to slick it up. 

“You have such a beautiful cock Brian. I don’t think I have ever seen one quite that big before. And the head is so perfect. Just an absolutely lovely cock.” She now had one leg over the side of the arm on the chair. Her skirt was hiked up and she was slowly rubbing her pussy through her matching pink panties. I could see that the crotch was getting very wet and that made me stroke faster. She was moaning softly and had opened up her blouse and was caressing her breast.

“God Brian I am so wet. My husband and I work too much and he has not fucked me in over a year. He just doesn’t seem interested in me anymore.”

“Well I know he’s my boss, but I think he is and idiot for not wanting to sleep with you Mrs. Taylor. I think you are still very hot.”

“Brian will you just rub that big thing against my wet pussy please?”

She didn’t have to ask twice. I picked her up and sat her ass on the edge of the desk. Hiked her skirt all the way up to her waist and dropped my pants to the floor. I began humping my hard cock against her slick mound. Only her panties kept my cock from rubbing directly against her hot little pussy. She seemed to love it. She just kept rocking her wet cunt against my hard cock. I couldn’t take this much longer. She was moaning uncontrollably now. I wonder if her AA could hear us or if anyone could hear us. What would her husband think if he walked in right now? I’m sure I would be fired right away.

“Mrs. Taylor?”

“Yes Brian?”

“I want to pull your panties to the side and rub it directly against your pussy. Do you want that?”

“Oh god yes Brian”

I pulled them to the side with my thumb and continued humping her slick pussy. It helped too that she was completely shaved. It felt so good against her wet slit. I wanted to put it inside of her so bad. And it was only a couple of minutes before I did just that. Her head was leaned back. Her mouth was wide open, and she was furiously stoking her clit. I couldn’t stand it any longer. 

I aimed the head at her opening and slide it right in. She jerked her head up and said, “What are you doing Brian. No we shouldn’t be doing that.”

“You know you want it Mrs. Taylor or you wouldn’t have called me in here to watch me jerk off. Tell the truth this is what you wanted all along. You want to be fucked and fucked good.”

I kept inching my hard cock into her tight little snatch. God she was so tight it was like fucking a virgin again. Oh god she felt so good. Her mind was telling her no, but her pussy started talking through her mouth overriding the mind. 

“Oh Brian noooooo. Oooooh yessssss! Oooooh god that feels so good. Fuck me. Fuck me harder. Fill me with that fat cock of yours.”

I pumped her as hard as I could. I was afraid I’d fuck her right off the desk. Her legs were wrap-locked around my back and she was now humping back trying to get as much of my cock as she could. Mr. Taylor was a fool. This lady is still one hot fucking number. 

“You like that don’t you slut? You like getting fucked don’t you. Tell me whose pussy this is. Tell me slut!”

“Oh Brian, oh yes, fuck my pussy, oh yes. Oh, oh, oh. God that feels so good.”

I felt her body shudder and knew that she had just had one of the best orgasms she had had in a long time. How could her husband neglect such a fine trophy wife? His loss. My gain. 

I knew I wasn’t going to last much longer either. So I just pumped for all I was worth and was soon filling her sweet pussy with my hot seed. She screamed and came again just as I released my load.

We stayed crumpled on her desk for a few minutes. Lying there breathing hard and she was rubbing my back.

“My god I almost forgot how wonderful that felt. You are so good Brian. I haven’t cum like that since…since…hell I don’t remember ever cumming like that.”

I laughed and said, “Well it was definitely my pleasure. Hell I thought you called me in here to fire me.”

“Fire you? Please. I knew when I saw you staring down my shirt today that I was going to tease you until I could get you into a situation where I could use you. Then when I saw you big cock outlined in your pants I knew I had to have you. It got me so horny my dumbass walked into the men’s restroom. And luckily for me no one saw me and you were doing exactly what I thought you were going to do in there. I could see it in your eyes.”

“Now get dressed before my husband or someone barges in here on us. We need to meet somewhere besides my office from now on.”

“How about my cube?” I said laughing.

“Yeah that’s a good idea. No get out of here, and act like I just wrote you up.”

“I hope I can pull that off. I doubt I’ll be able to wipe this smile off of my face for a few weeks. You are so hot. You don’t know how many times I jerked off fantasizing about you. And now that I had you the fantasies didn’t even come close to the real thing. You are so hot.”

“Well thank you. I wish my husband felt the same. I know he loves me, and I him. But I need sex and he just doesn’t seem interested.”

“He’s a fool.”

Updated: March 23, 2019 — 5:25 am