An Office Affair

I had just turned 30 years of age when I was promoted to my new job. It felt great. A big bump in salary, nice title, a personal assistant as well as a secretary. A little overkill, I thought. A secretary and an assistant? Would I have to do any work myself? Even more than that was the office that went along with the rest. A big office, nicely furnished, a private bathroom, and a door that was kept locked at all times. The guy I replaced must have had issues. I wasn't sure, but the lock seemed to be over the top. Such privacy concerns that even my secretary had to be buzzed in. The only keycards that unlocked my door were mine and my assistant. I guessed that made her an assistant instead of a secretary.

But what an assistant. I had picked her out of a group of employees who asked for the promotion when I got mine. I swear I did not pick her because she was so young and pretty. Really. Honest. I think I really believe that, though it certainly didn't hurt her chances. I mean, I knew we would be spending a lot of time together. I had to pick someone who was not only capable, but someone whose personality suited mine. But the thought of looking at such a pretty 25 year old for so much of the day certainly did make me smile.

Karen was a striking brunette. Quite pretty. Long hair to match her long frame. She stood about 5 ft. 9, and it seemed that it was mostly legs. Long, thin, curvy legs - just like the rest of her. And nice, full breasts, noticeable even under her normally business-like attire.

It was only after she began working for me that she began to dress a little more sexily. And she began flirting. Just a little. I took her flirting to be just good natured

banter, and her wardrobe a reflection of my laid back style. Perhaps I misread it.

The story really began at a company-wide celebration just a few weeks after I started my new job. We had a party one Friday after work, complete with a buffet dinner and a good bit of (that is, too much) alcohol. I did not drink much. After all, as a new executive I had to set a good example.

Things had begun to wind down a little. That means the older folks began to drift out towards home. I was torn as to whether I should leave with them (as a boss) or 'let my hair down' with the under 40 crowd. So I stayed for a while, then decided I would leisurely go upstairs to my office, use the bathroom, get a few files to look at over the weekend, and then come back down for a final drink.

It felt good relieving myself in the toilet. I was thinking how the party would have been more fun a few weeks ago when I would have been just a lowly employee, instead of the newest 'boss'. I was still very aware of my image in the company as I exited the bathroom. Knowing I would be alone, I opened the door of my bathroom before I finished fastening my pants. I heard a woman giggle as I zipped up.

"I could help you with that," my assistant Karen said.

I just looked at her, surprised.

"But maybe I would pull that zipper down instead of up," she said, moving up close to me.

I realized that she must be more than a bit drunk, so I ignored her naughty comment. "I think I'm fine, thanks. Did you come in to use the bathroom?"

"Well, yes, I did. But it would be more fun to use you!" She was speaking slow, and with slight slurring. "You know, I have thought of this a lot of times."

I was confused. "This? What, uh, have you thought of?"

She was nearly touching me she was so close. I was getting nervous, mostly because I had been looking a lot down into her cleavage. She had put on a 'party outfit' after work, and her dress was pretty low cut, showing a lot of breast. It was impossible not to notice. I had tried all evening, but now that she was so close, and we were alone, and she was flirting...

Her voice sounded sultry as she said, "I have thought of us being in here, alone. You trying to get fresh with me. Me letting you. After all, I am your 'personal' assistant." She emphasized the word personal.

I opened my mouth to tell her to stop. This was not proper. I was her boss. We couldn't... OH! Her hand closed over my pants, right where my bulge had begun to form. That stopped me from saying anything.

She leaned in, pressing her breast against my arm. "It feels so good. But it will feel much better in a minute."

I swear that I was trying to speak. I honestly think I said, "No," but I admit it was not very loud. I'm not sure that even I heard it.

I felt her fingers slide down my bulge. I didn't realize right away that my zipper was going down as well. Her body slid down my body as she reached into my shorts. I gasped as her fingers found my naked shaft. She pulled it out just as her mouth came level with it and I could only moan as her lips touched the head.

"Shiiiit," I moaned as I felt her tongue run circles over my cock head.

She smiled up at me and said, "You like that?"

Really. I tried to tell her to stop. A moan was all I could get out, and she returned her attention to my dick.

She now had it pulled completely out of my pants, and began licking the entire shaft. She held it firmly by the base while sucking on the head. Firmly. While pumping her hand up and down rapidly.

I hadn't had a hand job or a blow job in quite a while. No sex of any kind in a long time. All I was capable of at this point was to close my eyes and let the feelings run through my body. I just stood there and let her suck, and lick, and pump for - How long? I don't know. It couldn't have been too long.

I felt my cock harden even more. I began straining. The cum started to boil up. Suddenly I groaned loudly and my dick shot a spurt of cum out. My knees nearly buckled, but Karen kept my dick in her mouth as shot after shot emptied into her mouth. She kept swallowing and sucking until I was spent.

She looked up at me, smiling, as a dribble of cum eased down over her chin. "Oh, that was nice. Did you think that was nice?"

"Yes," I managed to say. "Yes, I did." Now I could talk, but my mind could not think of what to say.

Karen stood, wiped her chin and lips, then gave me a little kiss on the lips.

"Thanks," she said, then turned and left the office.

Thanks? I should be thanking her. No, I should be reprimanding her for what she did. But I let her, so... Again I was at a loss for words. I was never like this, but the whole episode was overwhelming. I sat down in shock, taking several minutes before I could absorb what had just taken place.

The weekend was a little difficult for me. I was feeling extremely guilty. I felt like I had taken advantage of her, though logically I knew that she had done it all with no encouragement from me. But I was her boss. A position of authority. If I wasn't feeling guilty, I was feeling afraid. What if she was really drunk and changed her mind when she sobered up? Or had second thoughts for whatever reason. Or if this was a plan to use me? She could make a lot of trouble for me. I nervously waited for Monday morning. We had to have a talk.

When Monday came, I waited in my office for her to come in. Finally she did, same time, same attitude, same "Good morning, Mr. Green."

We had some small talk before she lept into the big issue of the day. "Mr. Green, about Friday. The party. Can we talk?"

I dreaded this. I Ieaned back on the front of my desk, as I often did. This time I really needed the support.

It was a bit of a relief to let Karen go first. See how she felt about things before I started talking.

"I was drinking at the party on Friday," she began.

"Uh oh," I thought. "Here it comes. I took advantage of her. Damn!"

"But I wasn't drunk," she continued as she stepped closer to me. "Actually I didn't have very much at all."

I was confused. That's not what I expected.

Karen was standing close now. "I hope you are okay with what happened. Maybe even enjoyed it a little?" she added, looking up in what seemed to me to be a sexy way.

She had completely surprised me again. What should I say now? The main thing was not to upset her. Make her happy.

"No, I'm fine. I mean, it was good." Not exactly what I wanted to say.

But it seemed to be good for her. "Oh, good. I wouldn't want anything to be strange between us."

"No, no," I said nervously. "Me neither."

"Then you're okay with what we did?" she asked, placing her hand on my chest and looking up out of her partially closed eyes.

"Well, yes," I said, still trying not commit myself. I loved the sex, but was uneasy with the boss/employe dynamic. "I mean, if you're okay..."

"Me?" she said. "Yes, I'm very good. I enjoyed myself immensely." Her hand ran down from my chest to my abdomen as she spoke.

My mind thought of the intense orgasm. She said she enjoyed herself? "I had a great time!"

"I'm so glad to hear that," she said.

My mind knew I should say something about her hand sliding down over my stomach, but the only thought I could really form was how happy I was that I have kept working out. Nice abs, hard stomach...

"Uhhh!" I was surprised to feel her palm pressing hard against my erection. I'm not sure when it got hard, but it certainly was. And while she pressed on it her fingers were undoing my belt. Her other hand helped on unfastening and unzipping my pants, and before I realized it my pants and shorts were on the floor. My hard cock was drooling in her hand.

"Well, hello, Lover," she said to my cock just before the head disappeared into her mouth.

I had never met a girl who was as fast at getting a dick into her mouth, but she felt even better. Her mouth and tongue made love to my dick, and her hand squeezed and pumped the shaft. Her other hand was cupping and squeezing my balls, while those fingers were tickling the skin behind my balls. I suddenly could not think at all. I was overcome with sensations.

Her hands went around me and gripped my ass hard, pulling me into her even further. I felt my cock slip into her throat and her finger slip into my asshole. I was gone. I yelped as my orgasm hit suddenly and I sprayed my cum deep into her. She swallowed every drop of it and licked it clean even before she let it out of her mouth.

I was leaning against my desk, as I had been the whole time. I seemed unable to move. Karen stood up, looked at me proudly, gave me a small kiss on the lips, and I never moved. Stunned. She took my limp dick and wiped off some moisture with her hands, then pushed it back inside my pants. As she pulled my zipper up she said. "Are you all right, Mr. Green?"

"Yes, yes," I said, without realizing it. then I finally regained my senses. I looked at her smiling, innocent face, so pleased with herself, and said, "Yes, I am," this time conciously speaking." I am fine. Great. But what in hell..." My voice trailed off as I found my chair and fell into it.

"Mr. Green, I... I don't mean to overstep my boundaries..."

She seemed suddenly nervous, not like the totally-in-control woman the last two times we met.

Then she gathered herself. "I was a little drunk at the party, but I didn't do anything I didn't want to. This morning I wanted to show you that. Prove that to you. In case you thought that you took advantage of me, or I didn't want to, or..."

She was starting to get too excited again. "Calm down, Karen. It's okay."

Before I could say anything else she began talking again. "Mr. Green, you are an attractive man, and I know sometimes that you notice me. My body."

I began to get nervous again as she continued. "Nothing bad, just normal. But I know sometimes there are office affairs, a boss and his assistant, for example. Anyway, in case you had thoughts like that, I want you to know that I wouldn't take it as sexual harassment."

"Our workshops." I began, referring to meetings on that topic.

Karen looked at me determinedly. "Those are for unwanted sexual advances."

"So you're saying that you want to?" I asked.

She looked surprised and confused for a moment. "No. sir, I'm not saying I want to have sex. Exactly. I mean, I'm not asking. Just that I thought you might be attracted to me, and if you were, you shouldn't worry that I would complain."

"Okay, I think that makes things pretty clear," I said.

Karen now looked scared. "Oh, I'm sorry. I said too much. Oh, and I certainly did too much. I am sorry, sir, if I offended you..."

This time I interrupted her. "No, Karen, you haven't done anything wrong. In fact you did things very well," I said with a look that tried to convey sexual pleasure. It probably didn't. "I feel fine about everything. You have no worries. How about we have lunch here. We can take a few hours to both calm down and be less nervous by then. Okay?"

We sometimes have lunch in my office. A working lunch, when needed. Perfectly normal, except today we wouldn't be working.

I didn't know about Karen, but my mind was a blur all morning. I got some work done, but my mind kept focusing on Karen. Her blow jobs, mostly, but also where do we go from here. What did she want? I felt so good that I had thought to record her when she came in this morning. For my own protection. Though now when I listened to it, it seemed more like a sex tape. But at least it showed she was willing. Really willing.

About noon she came in carrying lunch. Efficient as ever. But instead of eating we sat on the couch. We sat close, more casual and intimate.

I actually took her hand, looking into her eyes, and said, "So if I gave in to my attraction to you, you wouldn't object?"

"Oh, no, sir," she answered. I could hear a touch of excitement in her voice. "No objection at all."

"I don't believe you have a boyfriend." It was a statement, but really a question.

"No, sir. But I'm not looking for a boyfriend. I mean, well, we sometimes work long hours..."

"So how would this work, if we can be perfectly honest?" I asked. "Are you hoping for sex? A commitment? ..."

It was her turn to cut me off. "Not a commitment, sir. I'm not looking for anything, or expecting anything. It's just whatever you want. Sir."

That last word seemed purposely to be said all by itself. It was then that I realized she had been calling me 'Sir' a lot today. She didn't usually call me that very often. Was she trying to submit to me?

"I've had two blowjobs from you."

"Yes, sir," she said, not reacting to the word.

"And if I wanted you to do something else?"

She smiled. "What would that be, sir?"

"What if I said something strange? Something unusual? Like, 'Take off your panties.'"

I didn't know why I said that, and I didn't stop to think what kind of reaction to expect from Karen. But before I could think of what might happen, she had stood up and reached under her skirt. In just a moment she was pulling her panties off her legs.

"Would you like these. sir?" she asked.

"What I would like is some relief for this sudden pressure in my pants!"

I had meant this mostly as a joke, as I was actually getting a sudden pressure in my pants. But she was quick to help out, as she reached to my pants and unfastened them. She managed to get my erection out of my pants, and as she stroked it asked, "Is this better?"

I just moaned, and reached over, running my hand up her leg, under her skirt, brushing against her bare pussy lips. She moaned now, and her legs spread giving me more room. I slipped a finger into her split, which was not only hairless but surprisingly moist. As my finger slipped in her hole she rose up, moaning, pushing herself into me.

Somehow she ended up spread over my lap, one leg on each side of me. I withdrew my fingers from her pussy and lowered her down to my erection. I pushed my dick up into her as she lowered herself onto me. Soon our groins were grinding together, then I was bouncing her up and down. We were both moaning as my cock began expanding even more. I burst open, spraying my cum into her. Just a moment later her pussy began spasming and her body shook. When we both finished she collapsed on top of me.

"Is that what you had in mind, sir," she asked when she regained her breath.

"No, actually, not at all," I answered. "IN fact it was quite a surprise. But it certainly was wonderful."

We didn't have much more time to talk. At the end of the day, I asked if she was okay with the day.

"Yes, sir," she said with a smirk. "Best ever."

The next morning she had that same smirk on her face, After getting the day planned out, I suggested another lunch in my office.

"Yes, sir," she said.

"And don't bother with bringing lunch this time," I said.

"Yes, sir," she said, her smirk showing again.

When she arrived for 'lunch', I motioned her over to my desk. As she stood there in front of it I asked for her panties.

"Yes, sir," she answered. "I'll go get them from my purse."

It took a moment for that to sink in. "You're not wearing any?"

"I thought I wouldn't have any use for them," she said.

My dick had been a little stiff just thinking about 'lunch', but now it was getting hard. What do I do now?

"Would you get me a pencil?"

"From your desk drawer?" she asked, her eyes motioning to my center drawer, on the other side of the desk.

"Yes," I said.

"Shall I reach it from here?"

"Please."

She had to basically lay her upper body fully on the desk, as I had thought. As she did, her breasts smashed against it and pushed out, bulging nearly out of her clothes. She reached out awkwardly and pulled the drawer open, found a pen, and reached it up toward me. I had asked for a pencil, but neither of us cared.

"Thank you," I said. "You can just stay there."

"Yes, sir," she said, getting comfortable stretched across the desk.

I walked around behind her, her feet on the floor and her ass nicely presented. I brushed the back of her thigh as she lay there, and she didn't move. I did hear her breathe heavily, though. My hand roamed up to the outside of her hip with the same reaction. When I let it slide down over the cheek of her ass she let out a slight whimper.

"Do you like that?"

"Yes, sir," she said.

I reached down and began bunching up her skirt, raising it higher with no objection until i just reached down and pulled it up, laying it over her back. She did indeed leave her panties somewhere. I pushed her legs slightly which caused her to spread them. I now had a beautiful view of her ass and her pussy peeking out from under.

I slid my hand over her round globes and in between her cheeks. I kept going to her ass hole, then her slit, causing a long moan to escape her. My finger worked in her wet slit until I found her hole. It slipped in easily, and she moaned louder. I began working it in and out to more moaning. When I found her rough spot she squealed. I kept working it as she whimpered and squealed more, moving her hips against the desk, until she finally was hit with a strong orgasm, yelping as it hit.

While she was shaking I let my dick out of pants. I slid it into the same crack my fingers had found, and after a few trips back and forth I settled the head at her entrance. Her body was pushing back, as if to force my cock into her. I didn't hesitate long to help her by pushing my cock deep inside her, most of it plunging in on the first push. She gasped at the intrusion, then pushed back against me as I plunged deep inside her over and over. She had driven me crazy mentally and physically, and I let it all out as I drove my hips hard against her, driving my cock deep.

Karen held on the edge of the desk, her fingers gripping the side as her hips were shoved repeatedly against the other side. I reached underneath and found her hardened clit. Sensitive from her last orgasm, she went crazy from her clit stimulation and my cock driving deep inside her, plunging over and over. I couldn't hold on much longer when I felt her pussy tighten. Her pussy was working my cock, squeezing it, when she burst out, yelling, her body shaking.