Flirting taken to the next level.
I've got a co-worker, Maryann, who's a lot younger than I-I'm in my mid-40s and she's in her mid-20's-and very inexperienced. Our relationship has progressed from being friends to close friends to even closer friends. She's very shy about sex, even though she's evidently very interested in it, too.
We often talk about sex, about masturbation-she claims she never has-and about my activities with my wife, with myself, and with third parties; my wife and I have very progressive views on sex. I'm also a bit of an exhibitionist, a fact that I've disclosed to Maryann over the past couple of years slowly but surely. We have an interesting agreement. We toy around with sexual behavior, but only so much as we don't acknowledge it and only so long as it's deniable, at least on the face of it. It's led to some interesting encounters.
It started when I noticed that Maryann was more than a little interested in checking me out. (This is something she flat-out denies, which is funny, but it's so obvious. But I let it slide because I do so enjoy it and don't want it to stop.) One day I was wearing a pair of khakis that were pretty tight. When paired with my usual boxers under them, my outfit revealed a good deal of information for anyone who cared to spend much time looking. Maryann was one of those people. At first, I was a little surprised because she always seemed so shy. In fact, other people think of her as being a prude, which, once you get to know her, is way off base.
Anyway, once I realized there was some level of interest there, I began to give her opportunities to see a bit more. At first, I'd just get my cock a little hard on the sly in my office before popping into hers for a quick question. Once she realized that there was more substance to my package than before, she had a difficult time paying attention to the conversation. Her eyes would wander down to below waist level and linger. I'd stand so as to maximize the effect. Her breathing would get shallower, but, amazingly, she'd keep up with the conversation. It was great fun.
Eventually, she began stopping by my office to check me out, which I loved. It got to the point where I would stroke myself slyly in her presence, neither one of us ever letting on that anything other than a chat was going on. Occaisionally, I'd get so hard that my nearly fully erect cock would be outlined in my pants, with the swollen head clearly visible there. Occasionally, she'd sit in a chair next to me, watching me do my thing and clearly getting into it. A couple of times after such an encounter, I've had to go to the restroom, take out my cock, and masturbate while thinking of her, of course.
I've taken it a step futher, as I've touched her on several occasions, always maintaining the pretense that nothing was going on. I'd stand next to her as we were looking at a document and let my elbow 'accidentally' rub against the side of her breast. I don't let on that what I'd really like to do is pull up her shirt and bra and suck and lick her nipples until she screamed for mercy. But she knows. We just don't say.
One evening Maryann called me at home-our friendship goes beyond the workplace-while my wife and I were in the middle of sex. My wife continued fucking me while masturbating herself while I spoke on the phone with Maryann, who, I should point out, took many opportunities to pause, presumably so she could listen to the proceedings. I did little to hide my arousal, even after my wife had come and had continued to work me with her hand. God, I'm getting hard again writing this.
I'm not sure where my friendship with Maryann will go. My wife would be fine with me bringing her home so that both of us could do her, and I'd love that too. Maybe one of these days I'll whip it out for Maryann to see firsthand. Maybe she'll take matters into her own hands. All I know is that we're all having fun now.