Anne & Scott Return to the Office

My name is Scott and it's been over six months since I took my assistant, Anne, on a business trip where we ended up fucking each other silly. For all the sordid details and a little more background on the two of us, I encourage you to read "What's Goes on out of Town Stays out of Town!"

I have thought about all of the ramifications that could develop from fucking your assistant, and trust me, very few of them are any good, but for some unknown reason I can't seem to get her out of my head. I know all too well that good pussy can cause you to do many things you wouldn't normally do, but there's more to it than that with her. I have as much fun if not more fun talking and hanging out with her as I do fucking her. Ok, definitely not more fun and maybe not as much fun, but still it's fun nevertheless. And I have no doubt that she feels the same way.

So what's the problem you might ask? Well the fact that she's my assistant is part of it. It's also the matter of my being 38 years old and she being 23. My being black and she being white. And I guess more importantly, my having a wife and 2 kids and she having a live-in boyfriend.

I love my wife. I truly do. We've been married for nearly ten years and have always had a great relationship. Our only problem (and it's really my problem) is our sex life. Prior to having kids our sex life was fantastic. Like most newlyweds we were doing it all the time until we finally leveled off to about 2-3 times per week around year five. Not an extraordinary amount but satisfying to us both.

Then after my son was born, the number of times dropped to about 1-2 times per week. It was right around this time that I started engaging in extracurricular activities while out of town with the guys or on business trips. A couple years ago my daughter was born and ever since then it's gone from once a week to about once every other week.

It's just been one thing after another that's caused the decline. The amazing thing is that we haven't allowed it to affect the rest of our relationship. When we do have sex, it's still great sex and each time we both talk about how we need to find time to do it more often. But then about two weeks later, we have sex again and say the same thing. So as you can see, the problem is not quality but quantity.

That brings me back to Anne. We've become very close friends since she started working for me nearly five years ago. It started off innocently enough and then became more and more flirtatious as the years went on until things came to a climax on our trip last September. Multiple climaxes I might add.

Like I've said Anne is not the first woman I've fucked since getting married, but she's been by far the best. She's also the first one that's lived in the same city as me. Everyone else was out of town hook-ups. Great fun, but easy to walk away from and avoid temptation. Also, far less chance of getting caught and fucking up everything in my life. That's why I was adamant in following my golden rule of what goes on out of town stays out of town.

After we got back from our trip, Anne and I agreed that it was a great experience but best not to let it happen again. We both had too much to lose. Things were cool the first couple of months. We were able to grow our close friendship as well as maintain professional decorum in the office. Everyone knows that Anne is my favorite, but she's an exceptional assistant and gets along with everyone in the office, so our working relationship has never been a problem.

The problem is that she is so fucking hot and I am so fucking horny. Erotic reading and jacking off helps, but that can only do so much. Let's face it; your hand is a poor substitute to good pussy. So what happened was that I noticed myself flirting more and more with Anne, who in turn started flirting with me again. Sort of like what was going on before we went on our trip. Again, nothing obvious to the rest of the office, but something definitely enjoyable to the two of us.

We were also comfortable enough to discuss our sex lives with each other. She knew all too well about my situation with my wife and I knew all about her relationship with her boyfriend. The cool thing was that neither one of us had the least bit of jealousy towards our significant others.

She and her boyfriend have been together for over four years. She moved in with him not longer after graduating college last summer. Being the good friend that I am, I advised her against it, but she didn't want to move back home and insisted that it was more of a roommate situation than living together. I think we both realized that wasn't really the case especially in a one bedroom apartment. I finally stopped giving her a hard time when she agreed to two conditions ... on the lease and on the pill. One to make sure she has legal rights to where she's living and the other to ensure her life doesn't forever change until she's ready.

Unlike me, she's having sex at least twice a week. She routinely describes it as good but not great. She says that she manages to cum about half the time, but too many times she feels that he's only in it for himself. She uses the same two examples that I've heard from many of my female friends, he wants in the pussy as soon as his dick is hard and then just as she's getting into it, he shoots his load and doesn't do anything else to get her off. I try to explain to her that unfortunately it's not uncommon for guys to be like that, especially at a younger age. Now of course that doesn't lessen her frustration but it damn sure makes me look good when she remembers our fun out of town.

Without a doubt her most frustrating sexual encounter with her boyfriend occurred last November on his 25th birthday. Being the good girlfriend, she planned a special night to celebrate the occasion. Fresh off of having the time of her life with me at a strip club on our business trip, she wanted to relive a similar experience with her boyfriend.

I tried telling her that many guys wouldn't feel comfortable going to a strip club with their girlfriend and not to expect it to be the same as when we went, but she was convinced he would love it and they would have so much fun. Well unfortunately for her things didn't go as planned. Her boyfriend was excited about going but never did relax while in the club. He tried drinking to help but all that did was get him drunk. She said they did get 2 lap dances but during both dances every part of him was stiff except the part she thought would get stiff.

I asked if she got a lap dance and she said she would have but could never really get into the mood. The night only got worse when they got home. Being his birthday, despite having drunk too much, he still wanted to have sex. Again being the good girlfriend, she went ahead and did it and sure enough it turned out how you might have expected. She said it was the worse fuck of her life. She wasn't horny in the least bit and in his condition he was clumsy, pawing after her, and more selfish than he's ever been. This time she was actually happy that he came so early.

As she was telling me I couldn't help but laugh and throw in a few well deserved I told you so's. I felt a little bad for doing so, but fortunately that's the type of relationship we have and I knew it would be cool. By the time she was done we were both laughing about it.

I told her I'd help make her feel a little better by taking her to lunch. Unfortunately I could never just take her to lunch. Although everyone on my staff knows that Anne is my favorite, hell she's everyone's favorite, I'm very careful not to show obvious favoritism or give anyone reason to suspect there's more to our relationship than meets the eye. So I took my entire staff out to lunch.

It was at this lunch that I realized I had to be honest with myself. My rule of only fucking around while out of town was in serious jeopardy. I was sitting beside Anne and she kept giving me these subtle looks that were really starting to turn me on. Her incredibly sexy brown eyes were doing a number on me and my dick had definitely responded accordingly.

In an effort to turn the tables I took a major risk by caressing her thigh under the table. My boldness in the company of the staff startled her but within seconds she turned and gave me an approving smile and slight nod. My actions were definitely affecting her but were having an even greater effect on me. My hard-on had grown increasingly more uncomfortable with no way to relieve the pressure.

When lunch was over, I quickly turned my back to the table to put my coat on and try to hide my obviously hard dick that everyone would have otherwise easily seen. Now it was Anne's time to laugh as she was thankfully the only one who noticed my predicament.

Back in the office I did something I had never done before at work. I closed my office door, immediately pulled out my still hard dick, and gave myself the relief I'd been craving. I blew a healthy load of cum into a tissue and was still reveling in the afterglow of a great orgasm when there was a knock on my door. Scrambling to get everything situated I just managed to zip up before my door opened.

"Oh it's you," I said as the object of my recent activity walked in.

"What do you mean, oh it's me," Anne replied.

"I should have known it was you. Everyone else waits until I say come in before opening my door."

"You know I always knock once and then walk in. You've never said anything about it before. What's going on with you?"

"Nothing, I was just busy." I said defensively.

"Busy? We just got back from lunch. How could you be busy so fast?"

"Never mind," I said as I threw the soiled napkin into the trash can. "You don't want to know."

She looked at me strangely for a moment before finally putting two and two together. Then as we always tend to do, we both burst out laughing.

"Oh my god Scott, you are so bad." she said in between giggles.

"It's all your fault." I responded. "You know I'm hardly getting any at home. You shouldn't tease me like you did at lunch. You saw what condition I was in when we left the restaurant"

"My fault! If I recall, you were the one stroking my leg. This is all on you."

"Don't play Miss innocent. You knew what you were doing. You damn near fucked me with your eyes right at the table."

"If I'd known it had affected you that much, I would have come in to your office earlier." she said seductively as we locked eyes.

"Oh really" I said "and what would you have done had you come in earlier?"

"Oh probably just watch you do whatever it was you were doing to cause you to need that tissue you just tossed away."

"In other words, continuing to tease and torture me."

"Not intentionally. I would have been more than willing to help you out, but I wouldn't want to violate your rule of what goes on out of town stays out of town."

"That's starting to sound like a dumb ass rule."

"Hey, it's your rule. But you know what they say; there are exceptions to every rule."

"Are you saying you'd like to be the exception to the rule?"

"Well," she said as she turned to leave, "Why don't you come up with a time and place that's safe for both of us and you'll find out exactly what I'm saying."

From the point on, I was determined to come up with the right scenario where I could fuck Anne again. But as horny as I was and as sweet as that pussy of hers is, I still had to be careful. This would not be easy. Outside of my trips, I had a daily routine and anything out of the norm would raise suspicions with my wife.

This may sound hypocritical but I do love my wife and I don't want to lose her or my family. Still, I knew there was no way I could work with Anne everyday knowing she's willing to hook up again and not do it. I'm a strong man, but not that strong. I have incredible will power when it comes to dieting and exercising and I can easily resist the temptation of drugs, gambling, smoking and other vices. But I'm a sucker for pussy. I've never been able to resist good pussy and god knows Anne has some good pussy.

So it was settled. To hell with my rule. No different fucking in town than out of town. The same rules apply ... enjoy the moment and don't get caught. Still I was having a hard time coming up with the perfect scenario until I remembered the company holiday party.

I told Anne about my plan for the holiday party and she agreed that it was perfect. More importantly, she seemed as excited as I was about the possibility of hooking up again.

The beauty of our holiday party is that it's for employees only. So, Anne and I had built in alibis with our significant others. They both knew about the party and assumed we would be coming home later than normal that day. What they didn't know was that the party started early in the day and truth be known, it really wouldn't be much of a party to make me or Anne want to stay late.

I had told everyone in the office that I wouldn't be able to attend the party for very long because I had a deadline to meet for a special project I was working on. Anne had told everyone that she wouldn't be able to stay very long because she had plans for later in the day.

The party was in our employee cafeteria located in an adjacent building to my office and started at 2pm. I stayed back in my office "working" on my special project as everyone in the office cleared out to the party. The plan was for me to head to the party a little after 3 and then leave by 4 to go finish my project. Anne was to leave a little before me and then we would meet up at a hotel on the outskirts of town. Well a little before 2:30; I hear a familiar knock on my office door and in walks Anne.

"Hey, we have a slight change of plans." she said as she closed my door.

"What's up?" I said in a concerned tone.

"Everyone sent me back here to tell you to stop working and come to the party now."

"Is that all? Hell, for a minute I was starting to worry. Let's go. The sooner we can get out of there the sooner we can get to our own party." I responded as I stood to leave.

"Not so fast." she responded. "Before we go there's something I have to do."

She then turned to lock my office door and proceeded to slowly unbutton her shirt, letting it fall off her shoulders and down to the floor.

"I don't know what you have to do, but whatever it is; don't let me get in your way." I managed to say as I stared at this incredibly beautiful woman undressing before me.

"Just shut the fuck up and sit back down." she ordered

Sitting back down the first thought that came to my mind was that I couldn't believe I've waited this long before hooking back up with this woman. I watched in awe as she removed her bra and her amazing tits came into view. No bigger than a b-cup, they were still quite exquisite with absolutely picture perfect nipples, whose hardness was a dead giveaway to her obvious arousal.

We never broke eye contact as she knelt down between my legs, unzipped my pants, and pulled out my rapidly hardening dick.

"Just so you'll know, this is what I would have been willing to do to help you out that day we came back from lunch."

"And just so you'll know, this is exactly what I was imaging you doing as I jacked off that day."

"Well, let's see if I can do a better job than you did with your hands." she said as she engulfed the head of my dick into her mouth.

"Ohh yeahhh" I moaned as she twirled her tongue around my dick and began bobbing up and down on my dick. How fucking great is this I thought. Here in my office in the middle of the day, one of the most beautiful women I know is topless and sucking my dick. Life just doesn't get much better than this.

Anne was no stranger to giving a blowjob. We had talked many times about how much she loved doing it, but this was far better than what I remember from our trip. I haven't gotten many blowjobs because it's not something my wife likes to do but this was without a doubt the best fucking blowjob I had ever gotten. She had one hand on my thigh, one hand in my pants massaging my balls, and her head bobbing away as her mouth made the sexiest slurping sound engulfing my rock hard dick.

I was tempted to close my eyes and enjoying the incredible feeling but I couldn't take my eyes off her. I wanted to engrave his picture in my mind forever and relive it in what I'm sure would be many future jack-off sessions. I started running my hand through her hair as she continued her masterful work on my dick. She began alternating rapid bobs up and down with a slow descent talking more and more of my dick down her throat. I found myself raising my hips to help her out until somehow someway she managed to fully engulf all seven inches of my manhood.

With her lips firmly planted on the base of my dick, she looked up at me with those sexy eyes and actually tried to smile. She wasn't moving but my dick was literally throbbing inside her mouth. My mouth was wide open but not a sound was coming out. I couldn't even exhale. Here she was, the one with a mouth full of dick, yet I was the one who could hardly breathe. She had sucked enough dicks to know when one was about to blow and right on cue she started bobbing up and down at an unbelievable pace.

I couldn't take it anymore and could only manage an inaudible grunt as I shot a wad of cum down her throat. While I was cumming I again started raising my hips thrusting my dick in her mouth. She tried to use her free hand to keep me in her mouth but she couldn't control it so she let me finish cumming on her tits.

"I take it you enjoyed that?" she said knowing full well the answer. "I know how long it's been since anyone has done that for you. I was going to wait until later but with everyone out of the office, I just couldn't resist. Consider it an earlier Christmas gift."

"Well turnabout's fair play. Let's say I show you just how much I appreciate the early gift."

"Slow your roll lover boy," she said as she began putting her clothes back on, "we have a party to go to. Everyone knows I came here to get you."

So off to the party we went. Anne told everyone that it took her awhile but she finally got me to come. She and I both chuckled as we thought of the double entendre of her getting me to come.

As expected the party was a dud. Anne & I didn't have to make any excuse to leave early because pretty much everyone was leaving early. As we were leaving the party, Anne whispered to me, "I don't want to go to the hotel."

"What ... what do you mean?" I stammered.

"Let's go back to your office. It'll be perfect. With the party the office is deserted, not even the night housekeeping staff will be there."

She had a point. The office would be empty and why risk being seen at a hotel. Plus that means it'll be that much sooner that I get into that incredible pussy.

"Deal" I said, "I'll meet you there in 10 minutes."

Back in my office I was as excited as a child on Christmas morning. Waiting for her watching the clock tick, my dick was already rock hard in anticipation. As soon as she got to my office it was like someone had unleashed a pressure can of passion. Without speaking a word, we started making out, frantically ripping at each other's clothes, with hands all over each other.

Fortunately I have the luxury of having a couch in my office and that's where we ended up, literally falling on it as we were kissing. Somehow we managed to get completely undressed with me lying on top of her. I paused for a moment to admire this incredibly beautiful and sexy woman and then I slowly worked my way kissing down her body. Savoring each body part, I progressed from her succulent lips to her inviting neck until I made my way down to her magnificent tits.

Her rock hard nipples were practically begging to be sucked and based on her moans starting with the moment I flicked my tongue over those nipples, she was thoroughly enjoying the feeling. With encouragement from her moaning and arching of her back I spent seemingly forever kissing, massaging, licking and sucking her tits.