A story I started a long time ago  

neednewfriend57 60M
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2/28/2021 9:18 pm
A story I started a long time ago


My name is Steve; 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 . 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 , to make a modest living, and the rest of the is mine. This is what basically led to my present problem. Being shy, lack of sex, too much free time home alone, and a computer 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 the control of a wicked woman. I knew I was far to shy to seek a dominatrix and live my fantasies, so I just continued to fantasize and play with myself.

One 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 to serve a mistress, without actually having to 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. least to it was a big plunge. I had made up my mind, the way that this could be satisfying to , was to MAKE myself follow every order my online mistress gave . With trembling fingers I signed up the website, filled the questionnaires, and gave her all the information she asked for.

When I checked my e- the next , 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 way I would be granted permission was if I carried her orders. She asked if I had a digital camera, explaining that visual proof of her orders being carried would be far more convincing than just a written of it, thus allowing her to grant permission to 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 outlet for living my domination fantasies.

The next I received an e- from my online mistress. She was delighted 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, , 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.

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 of the question, I was to shy to even ask women , there was no way I could go pink women's underwear and stand in front of the clerk to for them. I decided the 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 to female size charts. So I picked 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, for it with my , and for priority overnight shipping. The shipping 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 that , and arrived late the next morning. As I opened the box and looked at my purchase, it occurred to that mistress had ordered to obtain sexy underwear, she hadn't told to wear it or anything else. So I immediately e-mailed her and told her of my purchase. Shit, another of no cumming.

The next morning I went about my work as usual, it took to almost noon to finish transcribing the doctor's notes. After I was done for the , I stripped naked and checked my e-, 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- them to her. 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 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-, with the attached pictures, I again thought about quitting. But, once again I reminded myself of my promise and clicked send.

The next I checked my e- for a response from Mistress Jenny, but there was none. Again the next , but once again, still no response from her. Finally on the third I received an e- from her. She told I had done well and that I had waited long enough to , 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 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 , and the video had to clearly show doing it. Each and every one of these stipulations had to be met, or I couldn't jerk off and . 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 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 to do it right then; I knew I had to wait till tomorrow. Damn it, another of no orgasm.

The next 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 , but not extremely . It was nearly noon, so the sun was and bright. first I was nervous as I stepped outside, but I kept telling myself, it was the middle of the week, middle of the , most people weren't even home, those that were, were housewives busy cleaning or taking care of their . 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 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!

As I was floating through my fantasy world, back in the world of reality I heard a female's voice right behind me. "Well what do we have here?" My heart stopped, my eyes snapped open. Standing above and behind me was my neighbor , Sara. She had apparently quietly slipped through the gate, and right up to where I was lying in the chaise lounger, undetected.

Sara and her husband Mark had moved in next door almost a year ago. They were an early twenties couple, with no , Mark worked as a lab tech the hospital, Sara stayed home. They were an attractive couple, physically fit, with both spending lots of time by their pool working on their tans. I had been cordial to them, saying in passing and such, but I had never gotten to know them very well. Now, looking up Sara, I was stunned, I couldn't speak; all I could do was to try using my hand to cover my, now rapidly deflating, cock. Though I was able to cover my cock, I knew there was absolutely no way to cover the way I was dressed. "Looks to like what we have here is a homosexual transvestite playing with himself." I couldn't believe what she had just said, I wasn't a transvestite, I wasn't homosexual, and I didn't want my neighbors thinking I was. I stammered "this isn't what it looks like." She cocked an eyebrow and said "it looks rather obvious to me, you are a sissy cocksucker faggot video taping yourself, beating your meat outside in the sunshine, if this isn't the case maybe you should explain, and maybe you can convince me otherwise." I was mortified at being caught, and even more mortified at what my neighbor thought of me, and might tell everyone else in the neighborhood. I was trapped, and I knew it. On one hand, if I explained she would think I was a freak, but on the other, if I didn't explain, she would think I was an even bigger freak. As she pulled a chair up beside me I knew what I had to do, like it or not.

I stopped the camera from recording, and began to explain how I had been curious about female domination, and had signed up with Mistress Jenny, and this was her task she had given me. She asked me all sorts of questions about the tasks I had been ordered to perform and Mistress Jenny's domination of me. I decided it was best to answer each question honestly; otherwise I would never convince her that it was the truth. After a long question and answer session with my neighbor, she leaned back in her chair, crossed her legs, smiled, and told me "I believe you have a video to finish." As I was starting to get up out of the lounger, I told her I would finish it later, she quickly leaned forward and pushed me back down, "No, you will finish it now!" "I am sure your mistress will be quite amused at you being caught and watched." I knew she was right about Mistress Jenny being amused, and it is really hard to argue with anyone when you are outside, dressed in pink frilly lingerie. So, I gave in and sat back, pressed the record button on the remote, and began to try and get my cock hard again. I didn't think I would be able to with Sara watching. But, as I closed my eyes and thought about my situation, I was surprised at how fast it did come back up, and how fast I came. The first couple of shots of shot into the air and landed on my stomach, the rest oozed and over my hand. It was by far one of the best orgasms I had ever had by hand. As I lay there in post orgasmic bliss, it suddenly occurred to , I hadn't mentioned the fifth and final stipulation of my reward. Oh Gawd, I was going to have to lick my with her watching. I waited, hoping she would leave, but she just continued to sit there watching. I knew I had no choice, the way to finish the video, was to clean everything up, with her watching or not. I sat up without ever looking at her, looked straight into the camera and began to lick the off my hand. Having not in almost a week, I had shot a very huge load. Sara began hysterically laughing, asking if cleaning up my by licking it up was part of my assignment. When I answered yes, she laughed even more, telling me looks like I forgot to tell her about that part. She watched as I scooped the from my<b> stomach </font></b>and licked it up too. I had never licked up my own before, and having Sara watch made it even more embarrassing. Once I was done, Sara stood up and told it was time to for her to leave, she had things she needed to get done, but before leaving to she told me "Have a good evening slaveboy." The entire scene with Sara was so embarrassing that I went inside as soon as she left. I knew if I didn't download the video and send it right away, I would chicken . So I immediately downloaded the video and sent it to Mistress Jenny.

I thought about what happened with Sara all night long. Though it was erotic and stimulating, I just couldn't risk the embarrassment of getting caught again. So, I made up my mind to e- Mistress Jenny the next , to thank her and tell her I couldn't continue any further. The next morning I started my as normal, I got dressed and headed the door, get my days work from the doctors, but when I opened the door, there was a package lying in front of it. It was a plain white gift box with the word Surprise written on it. I brought in and opened it to see what it was. Inside, to my horror, I found pictures, digital pictures printed from a computer printer, pictures of in my backyard, dressed in my pink frilly women's underwear. They were pictures of me setting up the camera, chair and such. From the pictures it was obvious they were taken through a knot hole in the fence. Suddenly I remembered the medium sized knot hole in the fence between mine and Sara's yard. I had peeked through it a couple of times last summer to admire Sara lying by her pool, but over the winter I had forgotten about it. Obviously Sara had seen me through it, taken the pictures, then came over. Also inside was a cassette tape, labeled "Copy of Confession." I took the tape over to the tape player; I used for work, popped it in and began to listen. To my horror it was my entire conversation with Sara. Apparently she had a pocket recorder concealed on her the entire time I was spilling my guts to her, now she had my entire confession on tape. How could I have been so ? How could I let myself get caught like that?

I looked at the clock; I didn't have time listen to see just how much was on the tape, although I was pretty sure all of it was, including the part about me licking off my hand. I was already late; I needed to meet with the doctors to get my work for the . As I left the house to get in my car, Mark was leaving the same time. He gave me a friendly wave and said . I also heard Sara tell good morning. She was standing on the front porch seeing her husband off for the . My blood ran cold, what was good about it. I muttered a good morning to them both, not too friendly, but yet not cold enough to piss off Sara. I quickly got my work and returned home. When I sat down to type, I remembered the words of Mistress Jenny; you must always wear your pink panties when you are home alone. Screw it, I thought, I am ending it today anyway, besides those damn things have got me in enough trouble already. So I remained dressed in the street clothes I had worn to pick up my work. Work was frustrating, I was irritable, and I kept thinking, why can't these damn doctors speak more clearly? But by lunch time I had stumbled through most of it, and what I hadn't finished wasn't due back for two days, so I knew I could do it later. So I grabbed so lunch and relaxed a bit. As I was signing on to e- Mistress Jenny, I heard Mark's car leave, he had obviously came home for lunch. Within minutes the doorbell rang. When I answered it, it was Sara.

Sara was all smiles, "Afternoon Stevie, how are you today," she said as she stepped right past me, as if she owned the place.

"And how are you Sara?" I said with just a hint of sarcasm, which Sara chose to ignore.

"Did you like your little surprise package today?"

"Not really, where did you get those pictures?"

Sara proceeded to explain how she had been in her backyard taking pictures of a robin, when she heard me knock over the tripod and curse it. She peeked through the knot hole intending to say hi, but when she saw how I was dressed; she couldn't help but a few pictures through the knot hole. She explained how when she saw start jerking off she couldn't resist the temptation to come tease and torment me, and how she had grabbed her pocket recorder to tape my stammering about being caught. She told me she didn't realize at the time just how useful both, the pictures and tape could be. After explaining just how I had gotten myself in this mess, Sara got a disappointed on her and asked:

"Hmm, isn't Stevie supposed to be dressed in his pink panty set when he is home alone?"

"I decided not to today, I decided to tell Mistress Jenny I quit!"

"Why not, you looked so cute in them, as a matter of fact I think we need to go online and order you a couple of more sets, maybe different colors even."

"I don't think so!"

"Oh you don't, well I do, and in case you have forgotten, I have you at a slight disadvantage here, I have your pictures and taped confession."

"I haven't forgotten that Sara."

"Also, in case you have forgotten, Mark works as a lab tech at the hospital, the same hospital where all your doctors practice, and I am quite friendly with most of the women in the neighborhood, sure would be very incriminating if those pictures and tape started getting passed around at the hospital and our girls afternoon socials, now wouldn't it?"

I couldn't believe what she was saying, she was blackmailing me, and if I didn't go along with it, she would make me into the laughing stock of the neighborhood and the medical professionals. I was trapped, with no way , and she knew it! I was dumbfounded, I didn't know what to do; my fantasy was becoming a nightmare!

As I stood there, Sara put her hands on her hips and told ;

"Stevie, you got two choices, you can get your ass in there and put on your pink frilly panty set and start doing what I tell you, or you can stand there, and I can go visit Sharon down the street and show her my little discovery, which is it going to be?" I was beaten, I knew it, and so did she. So I went to my room to change. I came back into the living, room wearing nothing but the pink panty set I had bought, to whatever consequences Sara had in store for .

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