Caught Masturbating Twice

My office is filled with attractive women and my wife will tell you it doesn't bother her, but I can guarantee that it bothers her greatly. My assistant of three years recently got pregnant and put in her notice, she wouldn't be returning to work after the baby came. When I mentioned this to my wife, Kelly, she told me I should hire her Kelly, one of her friends who was recently laid off.

She arranged for Sally to come in for an interview and I wasn't surprised when I saw her. She was a forty-two year old, recently single mother of two with a more than a little extra pounds around her midsection. I could see that she had been an attractive woman, but the years hadn't been kind. Kelly thought she would be perfect -- someone to keep an eye on me that I wouldn't be the least bit interested in. I hired her on the spot.

Sally turned out to be an amazing employee, much more qualified and talented than my last assistant. Everything was going swimmingly for about six months and then it all went bad, very bad.

Sally and two other women from the office took a weekend trip to Vegas where they posed for a number of suggesting photos. The girls had emailed them around the office and I had one of the photos up on my computer. Margot, one of the other girls from the office, was standing next to Sally and another girl. She looked amazing. Thinking I was alone in the office I began masturbating while staring at her picture. She was so hot and I have had a crush on her for the past year. Just as I was about to ejaculate I heard something behind me, it was Sally standing in my doorway watching me. She immediately turned and scurried away before I could catch up to her.

On Thursday and Friday Sally called in sick. I started to worry. On Monday though she was back at work. It was awkward all day. Finally she sent me an instant message.

Sally: Sorry about missing work last week.

Me: If anyone should apologize it should be me, sorry.

Me: I am completely mortified. I am really sorry.

Sally: The hardest part for me is my relationship with Kelly.

Me: What do you mean?

Sally: It is just awkward?

Me: How so?

I was starting to get worried. This IMing was also strange. She was sitting just outside of my office, but instead of talking face to face here we were chatting on our computers.

Sally: Well... the next time I am talking to her I will feel guilty.

Me: Oh, you didn't do anything wrong, it was ALL me, sorry.

Sally: I can't help but be flattered that you think of me sexually. I have to admit it is a real turn on, but the fact that it turns me on is almost a betrayal of my friendship with Kelly. I know it is stupid, but it is true.

It was at this moment that I realized that Sally assumed I was masturbating while fantasying about her.

Sally: But you have no idea how depressed I have been. I saw a doctor just last week. It is embarrassing how important just knowing that at least one man in this world, even one married to my friend who is also my boss, is attracted to me. Thank you.

I didn't know how to respond. Did I tell her I was actually thinking of someone else? Would she tell my wife? Would she quit? Would she sue the company? I decided not to tell her.

Sally: I talked to Kelly on Friday.

Me: Oh, really? What did you say?

Sally: LOL, don't worry. The whole time we talked the only thing I could think of was the two of you making love.

Me: Really?

Sally: But you were thinking of me. Kelly had no idea. I guess that is why I felt guilty.

Sally: Have you ever thought about me when you were having sex with Kelly?

I didn't know how to tell her I wasn't the least bit attracted to her. I decided to say nothing at all. Ten minutes later Sally responded.

Sally: I thought so. ☺

Sally: Are you staying late tonight?

Me: I wasn't planning on it.

Sally: I thought if you were, you might let me watch.

Fuck, this was completely out of hand.

Sally: I didn't get to see you finish, I want to see you cum, just once. Please.

I didn't respond. I left at my normal time, but as I said goodnight to Sally she just glared at me. Sally glared at me all week, barely saying a word unrelated to work for the rest of the week. On Friday afternoon I tried to mend fences by sending her an IM.

Me: Are you mad at me? I am sorry if I upset you.

Sally: Yes.

Me: I am sorry.

Sally: I am not asking you to do something you haven't done before. We both know the truth. My request was simple and I don't know why you won't let me watch.

Me: I can't do that to Kelly.

Sally: Do what?

Me: I can't be involved with another woman.

Sally: Involved?

Sally: We aren't involved. Fantasies are normal. Let me watch.

I knew I couldn't go through another week like the last. I decided there wouldn't be any harm letting her watch once. Hell she had already seen me once before.

Me: Okay.

Sally: I'll be right in.

Sally stepped in my office and locked the door behind her. I sat on the couch and said, "This is one time thing, okay?"

Sally sat on the lounge chair smiling from ear to ear saying, "Okay."

I couldn't help but feel completely awkward at this point. I had never let ANYONE watch me masturbate, not even Kelly. I unzipped my pants and pulled out my penis. It wasn't erect at all. I held it in my hand and began to stroke it. Sally licked her lips and unbuttoned her blouse so I could see her bra. As I looked at Sally's face I couldn't help but realize she had been a beautiful woman years earlier. Her breasts were fairly large, but I assumed this might be more related to the thirty extra pounds she was carrying.

Sally noticed that I was getting aroused and said, "I have never told anyone, but I have always been jealous of Kelly. In college she always got the hot guys and in the end she got you. She would never believe you were attracted to me."

I didn't say anything, but I couldn't help but feel a little turned on. I was fully erect and jerking away when Sally unclasped her bra revealing her breasts to me. She arched her back and I couldn't help but be impressed. They were much larger than Kelly's. I began jerking off faster as I became more aroused.

Sally then got up and sat on the couch next to me. She put her hand on my leg, just under my crotch and whispered, "Promise me that the next time you cum inside of Kelly you will be thinking of me."

I didn't respond, but Sally wanted an answer. She grabbed my hand as I was jerking off. I stopped cold, feeling her finger touching the tip of my penis. Sally repeated, "Promise me."

I relented by say, "I promise."

Her hand lingered on over mine and she lightly rubbed the tip of my penis with her finger and asked, "Does that feel good."

I nodded in agreement.

She kept rubbing and asked, "Do you want me to stop?"

I didn't say anything. She slipped her other hand under her skirt and began fingering her own clit and said, "If you want me to keep going, just move your hand."

Almost involuntarily I let go of my penis and let Sally take it in her hand. She began rubbing it slowly. Then she said, "I don' think it is going to be hard for you to think about me the next time you fuck Kelly."

I didn't respond, I just sat there helplessly as she seduced me.

Suddenly Sally let go of my penis and threw her leg over my lap. We were face to face. She was straddling my lap, staring right into my eyes as she said, "Or maybe you need a little more help?"

She lifted her skirt over my penis, and pressed the tip against her vagina. She was wet and before I knew it she was lowering herself over my cock. Sally finally asked, "This is what you wanted, isn't it?"

This time I answered as she began fucking me, "Yes."

It only took a minute before I was cumming inside of her.