I'd love to say that it started out innocently enough, but there really wasn't anything innocent about it. I had been working as a software trainer for a small computer consulting company in Georgia, and my job was to train the clients on the computer systems that we sold them.
One of those clients was a group of people from an industrial machinery company. Among the people in this group was a secretary who was undeniably cute. Lisa was short in stature, but amazingly upbeat and good-humored -- especially at 8 am, when the sessions began. There are times when two people who happen to be roughly the same age are in a room filled with older people and they tend to gravitate toward each other. This is precisely what happened with us.
After the first training session, Lisa asked me if I helped people with their computers at home. I told her that I could, but for some reason she didn't want me to come over to her house to help her set it up. Instead she suggested that she come over to my house so that I could show her using my own computer equipment.
Now, essentially I'm a very lazy person, and I figured that if she came over, I wouldn't have to worry about driving anywhere. Sometimes I amaze myself at my own cluelessness. In fact it really wasn't cluelessness – I honestly didn't think that she would have anything else on her mind other than what we were talking about. After all, I'm usually not that lucky. Usually.
Lisa came over that evening, but we never got around to working on the computer. She and I sat down on the sofa and began talking, and she told me that she had a confession to make. It turned out that she hadn't wanted me to go to her apartment because she was living with her boyfriend. She said that she found me attractive and wanted desperately to have sex with me. To say the least, I was a little struck by her candor.
She asked me if she could kiss me, and while the ethics of my response should have taken over, they didn't. We began to kiss on the sofa with increasing passion. At some point she leaned back, and I began to kiss along her neck, ultimately taking her earlobe in my mouth. I knew that some women respond enthusiastically to this, but Lisa went one step further. As I sucked her earlobe, she began to writhe and press her body against mine. We were still clothed, but there was no escaping the damp heat pressing against my groin. Her hands were running up and down my back as her fingers pressed into me. Her breathing was coming hard and fast, her breasts crushed against my chest, but her moans were becoming loud and ragged.
Her hands grabbed my hips as she pulled me into the space between her legs. I felt her stiffen as she cried out in a long wail. She came against me as I slowly eased off on my sucking. In my life, she was the first and only person who has ever come simply by me sucking on her earlobe.
She pushed me back, trying to get air. I was a little stunned at her response, but excited beyond belief. There was no doubt that she had felt my erection pressing into her as she held me, and I was hoping that she and I could move to the next level, and soon.
It was not to be. "I'm sorry," she said. "But my boyfriend will wonder why I'm gone so long." The look on my face must have revealed all, because she quickly followed up with, "let's meet here during my lunch hour tomorrow."
Lunch couldn't come fast enough for me. We began seeing each other during her lunch hour, sometimes simply talking and eating, and sometimes fucking ourselves silly. The next day she came over and took complete control, which is unusual for me. She sat on my bed, undressed herself, and then unzipped me. She took me in her mouth for a little while, and then told me that she wanted me to come inside her pussy. All her talk was keeping me on a very wonderful brink.
She turned around and pointed her gorgeous ass at me. She had a little ying-yang tattoo on her right cheek. Off my raised eyebrow, she said that it was something for me to look at as I fucked her. I loved her language.
I eased into her, and felt an amazing contradiction. Her pussy was soft, smooth, warm and inviting, and I didn't want to leave it. She was on a time limit, though, so she was doing everything she could to make me come fast.
"Do you like my ass?" she asked. Silly girl; she had an amazing ass. "How about my pussy? You like sliding your cock in and out of my pussy? How about when I do this?" And with that she actually managed to make the muscles in her pussy ripple. I don't know how she did it, but it felt as if there was a wave of pressure riding along my shaft. I held on to her ass and fucked her until I came hard inside her.
She got off me and off the bed at that point, and went into the bathroom. When she came out, she put on her clothes and told me to email her. Since the training that I had been doing for her company involved the use of secure email, I knew what type of content she would be expecting.
At work we wrote each other about what we liked to do, what we fantasized about doing, and how much. At our lunches, it seemed like we were never able to do what we talked about thanks to the limited time. Our emails grew more and more raunchy, though, and our imaginations were running at a high sexual simmer.
It didn't take long for her to tell me that she had a standing fantasy to do it with a woman. She also told me that she wanted to watch me have sex with another woman. She was, she said, an exhibitionist at heart, and I apparently made incredible facial expressions and noises when we were having sex, but she couldn't appreciate it properly because she was too close.
My mind grew aflame with the possibilities. Who could there be to provide this extra added element?
At the same time as I was "seeing" Lisa, there was another girl who was helping me out at the house. Effectively, I was finishing up my doctoral work, and I desperately needed help. I needed someone to help do research at the library, organize things in the house, run errands, and I had an arrangement with her where I would pay her for her help. She was a true administrative assistant. Jenn was a very different person than Lisa, however, in that she had not one assertive bone in her body. I had to tell her everything to do, because she was far too timid to risk doing something wrong.
Jenn and I started sleeping together around the same time as Lisa. It happened more by accident, actually, in that we were sitting around talking over dinner one night about relationships. I had just gotten out of one and wasn't looking for one, and she told me that she never really had one. She also told me that she had never even had sex, but it wasn't because she didn't want to. No one would apparently take her up on it.
This surprised me, since Jenn was not unattractive. She worked out, she took care of her appearance, but she could best be described as 'plain.' She had dark red hair, full lips, and a fair complexion and yet despite this, was easily invisible in a group of people.
She asked me that night over dinner to help her lose her virginity. I can't say I was taken aback by the request, because I had thought that perhaps she might have had a crush on me anyway. What surprised me was the way she asked me, almost trying to sell me on the idea, persuade me that there would be no strings attached. I told her that I wasn't sure about it, because I knew what kind of emotional attachments lay ahead. She promised repeatedly that she understood what the risks were, that she was a big girl, and didn't want to remain a virgin any longer. Twenty-five years was too long, she said.
I acquiesced, thinking I was going against my better judgment. We went into her bedroom, and she put on some music. Not slow, romantic music, as one might guess for someone's first time, but Nine-Inch Nails, the tune that goes "I want to fuck you like an animal!"
As the heavy techno synth bass began pumping out a rhythm, she began to sway to the music. It seemed that this shy, demure, 25-year-old virgin harbored some intense sexual fantasies, and this strip tease would only be the first to come through.
She stripped awkwardly, and at one point in time I asked her if she really truly wanted to do this. She had only taken off her shirt and her pants and was standing there in a mere bra and panties. I had figured that if she needed an out, this would be the time to do it. She looked at me in a desperate panic, afraid that I would call the whole thing off. Assuring me that she really did want to continue she explained that she couldn't believe she was finally going to get laid. Her nervousness, she said, was excitement.
Not entirely convinced, I sat back down on her futon bed, and watched her as she continued her stripping. She removed her bra, revealing small, cone-shaped breasts. Her skin was almost bleach-white, she was so fair. As she removed her panties, I could see a small tuft of hair emerge, then two pink distended lips that glistened in the room's light. She was telling the truth, apparently, she was very turned on.
With her clothes off, she returned the NIN CD to the beginning of the track, and threw herself at me. Her sudden energy nearly frightened me, since I wasn't used to this type of behavior from her – ever. She pulled my shirt out of my pants, fumbled with my pants, and took my cock out.
"Oh wow," she said. "I've never seen one in real life before. Can I try putting it in my mouth?"
I nodded. She was a bit rough with her hands at first but her full pouty lips wrapped around the cockhead carefully enough. She may have never done it before, but she was careful to avoid her teeth. She sat up almost as quickly with a huge smile on her face. "I've never done that before!"
She was leaning over me so it was quite easy for her to push me back down on the futon and straddle me. She took me in her hand and began to sit on my cock. As the cockhead entered her body, she struggled for a moment. As tight as she was, I was not going to enter her quickly.
She began to move up and down, almost trying to force my cock all the way up her pussy, as if she could bounce her way down my shaft. Her approach left a little to be desired in terms of gentleness, but she was enthusiastic enough to make up for her inexperience.
We fucked long and hard, and with a vigor that I never would have placed a virgin to embrace. When I finally came, she actually thanked me, that she felt like she wasn't so much of a loser. I was stunned to hear her say such things, because I'd never equated being a virgin with a loser. Regardless, she seemed content to the degree where she felt better about herself, so I didn't want to argue.
I told Lisa about it the next day. She told me that she wished she could have watched.
Jenn came over in the evenings to help me out, and at some point I got the idea to put two and two together. I had told Jenn about Lisa long before that night where she asked me to take her virginity, and described some of Lisa's fantasies about watching and being with another woman.
"Please understand that I'm not asking you to do anything you don't want to do," I told Jenn. "She just has a fantasy about watching me with another woman, and you know about her fantasy about being with another woman, but there wouldn't have to be any of that if you didn't want to. I was wondering if you might be interested in letting her watch."
She told me that she wanted to think about it. The next day, she told me that she had thought about it and the idea actually turned her on.
"Which idea?" I asked.
"Both," she grinned.
I told Lisa. Lisa had never met Jenn, but knew about my activities with her. She loved to hear me recount the stories of Jenn going down on me while I worked, screwing on the dining room table, or having her take me out and suck me while I was driving somewhere. The idea was turning her on as well.
One night Jenn was over and we had started fooling around. We were on my bed, and I decided to call Lisa. My cock was deep inside Jenn's pussy, and when Lisa answered the phone, I told her so. Placing Lisa on speakerphone so she could hear both of us, I introduced her to Jenn.
Lisa wanted to know all the details. Jenn was flat on her back watching my cock fuck her slowly. We weren't in any hurry, so it was just a slow screw. Jenn told her everything that was going on.
We could hear Lisa sigh. "If I hang up quickly," she said suddenly, "it's because my boyfriend came home." We told her we understood.
Lisa became a director. She began to tell us what to do, and how to do it. She told Jenn to go to the freezer and get some ice cubes and put them in a bowl. Jenn did that, and returned. Lisa told her to put an ice cube in her mouth and soften the hard edges, which Jenn did. Then Lisa told me to put my cock in her mouth when the ice cube had melted.
