My name is Steve; I'm a single guy, early thirties, average looking, decent build, nothing special, just your average guy you would meet most anyplace. I am very shy, basically an introvert, therefore I have never been married, seldom even date. It's not that I can't get a woman, just too damn shy to approach most and ask them out. So basically I am a homebody and keep to myself. I live in a quiet neighborhood, of smaller, but yet nice homes. Basically you would call them moderate priced starter homes. My job is great for someone like me, I work from home. I transcribe doctor's recorded voice notes to typed documents. Being a very good typist, it doesn't take but a few hours a day, to make a modest living, and the rest of the day is mine. This is what basically led me to my present problem. Being shy, lack of sex, too much free time at home alone, and a computer at home connected to the internet.
Basically my sex life consisted of masturbation while reading sex stories on the internet. Once my work was done I was free to strip naked, and sit jerking my cock all afternoon long, as I read sex stories. I read a variety of fantasy sex stories, but the stories about female domination were the ones I found most stimulating and erotic. I found myself having deep fantasies about being under the control of a wicked woman. I knew I was far to shy to seek out a dominatrix and live out my fantasies, so I just continued to fantasize and play with myself.
One day while I was surfing I ran across a website that did online domination. After reading what the site had to say and offer, I was completely intrigued. Here was a way for me to serve a mistress, without actually having to face her; it was a perfect plan for someone like me. I toyed with the idea for several days, before making up my mind to take the big plunge. At least to me it was a big plunge. I had made up my mind, the only way that this could be satisfying to me, was to MAKE myself follow every order my online mistress gave me. With trembling fingers I signed up at the website, filled out the questionnaires, and gave her all the information she asked for.
When I checked my e-mail the next day, I found a letter from my new online mistress. She took charge right away and informed me, my cock was now hers and I would no longer play with it unless she gave me permission, and the only way I would be granted permission was if I carried out her orders. She asked if I had a digital camera, explaining that visual proof of her orders being carried out would be far more convincing than just a written account of it, thus allowing her to grant me permission to cum more often. She also asked just how serious was I about becoming her submissive bitch, and following her orders. I responded back that I had both a digital camera, and a digital video camera, and that I was very serious, as this was my only outlet for living my domination fantasies.
The next day I received an e-mail from my online mistress. She was delighted at my seriousness, and the fact I had both, a digital camera, as well as a video camera. She told me that she planned to make good use of both of them, and me as well. She also gave me my first order to follow. I was obtain, a matching set of pink, lacey, frilly women's panties and bra, a pink garter belt, and pink thigh high stockings. She didn't care if I purchased them, if I got them from a female friend, sister, daughter, or even a stranger, as long as I got them. To make it even more difficult, she said they must fit properly, getting the correct size was my problem. She also informed me I was not to contact her, nor would she contact me, and I was not to play with my cock till I had completed this first task.
At first I didn't know what to do. I didn't know many females, and I was most certainly not going to ask the ones I did for their bra and panties. I knew going to the local stores and buying them was out of the question, I was to shy to even ask women out, there was no way I could go buy pink women's underwear and stand in front of the clerk to pay for them. I decided the only way was to use online shopping. After a little research I discovered a couple of online stores for cross dressers, and fortunately they even had male to female size charts. So I picked out the sexiest pink bra and panty set I could find, ordered a pink garter belt and stocking set, that matched the bra and panty set, paid for it with my credit card, and paid for priority overnight shipping. The shipping cost was a little steep, but I was horny and needing some relief and I figured quick compliance would earn me a few brownie points with my new mistress. My order went out that day, and arrived late the next morning. As I opened the box and looked at my purchase, it occurred to me that mistress had only ordered me to obtain sexy underwear, she hadn't told me to wear it or anything else. So I immediately e-mailed her and told her of my purchase. Shit, another day of no cumming.
The next morning I went about my work as usual, it took me to almost noon to finish transcribing the doctor's notes. After I was done for the day, I stripped naked and checked my e-mail, there I found mistress's next assignment. She had ordered me to shave my body completely smooth, except a small patch of pubic hair above my cock like the nude female models usually have. I was to use something like poster board and magic markers to make a sign saying Mistress Jenny's slut. I was then ordered to take several pictures of myself wearing my new outfit, holding the sign, and e-mail them to her. At first I thought I couldn't do it. I thought about just ending my subscription to the website and have no further contact with Mistress Jenny. Then I reminded myself that I had promised her, and myself, I would obey all orders. After all, it wasn't as if anyone ever saw me naked and would know I was completely hairless, except for the little landing strip above my cock. Soon I found myself standing before my digital camera, mounted on its tripod, body smooth and hairless, wearing pink lingerie, holding a sign, wondering if I would regret taking these pictures. I did half a dozen poses for mistress and downloaded them to my computer. As I composed my e-mail, with the attached pictures, I again thought about quitting. But, once again I reminded myself of my promise and clicked send.
The next day I checked my e-mail for a response from Mistress Jenny, but there was none. Again the next day, but once again, still no response from her. Finally on the third day I received an e-mail from her. She told me I had done well and that I had waited long enough to cum, but there were stipulations on my getting to play with my cock. One, I had to agree to always wear my new pink outfit, and only my pink outfit when I was home alone. Two, I had to be wearing my new pink clothes when I jerked off. Three, I had to video tape myself doing it, and send her a copy of it. Four, I had to be outside, in broad daylight, when I jerked off. Five, when I was finished, I had to lick up every drop of my cum, and the video had to clearly show me doing it. Each and every one of these stipulations had to be met, or I couldn't jerk off and cum. I couldn't believe her demands, it was embarrassing enough to have to jerk off dressed in women's underwear, and video tape it, but to do it outside, and lick up the mess afterwards. I knew it was the only way though, and I had come this far might as well go all the way. Besides, when the previous owners of the house next door had put in a pool and privacy fence, the previous owners of my house finished the other three sides, giving my own backyard complete privacy, so I could do it on the back patio and not be seen. But, it was too late in the day to do it right then; I knew I had to wait till tomorrow. Damn it, another day of no orgasm.
The next day I sat in my pink panty set, doing my transcribing work. I was very quick about it and finished early. The time was finally here, after days of no jerking off I was about to finally get much needed relief. I stepped out onto the patio, carrying my digital video camera and its tripod. It was late spring, so it was nice and warm, but not extremely hot. It was nearly noon, so the sun was high and bright. At first I was nervous as I stepped outside, but I kept telling myself, it was the middle of the week, middle of the day, most people weren't even home, those that were, were housewives busy cleaning or taking care of their kids. Besides, even if any of them were outside, I was surrounded by a privacy fence. I casually stood up my tripod, and moved a chaise lounge chair to the center of the patio. As I moved the chair, I knocked over the tripod, making a loud clattering noise. I quietly cursed and set it back up, hoping nobody heard it. I carefully set up the chair, the video camera, making sure the camera would catch all the action Mistress Jenny wanted to see. Once I was sure everything was in place, I sat down in the chaise lounger, pressed record on the camera remote. I pulled my already hard cock from pink panties, poured oil on my hand and began to slowly jerk off. The sun felt warm on my body, I was extremely horny from days of no jerking off, and the naughty wickedness of what I was doing. I leaned my head back, closed my eyes and was determined to give Mistress Jenny a long slow show of me jerking off. With my eyes closed I drifted off into a fantasy world of me submitting to Mistress Jenny. I was getting deeply involved in my fantasy, my hand stroking my cock felt great. It was at this point everything went to shit!
