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?"
