The New Show Ch. 02

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A man is trained by his mistress.
2.2k words
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Part 2 of the 3 part series

Updated 11/02/2022
Created 10/24/2013
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My new interest in wearing ladies panties has become more time consuming than I ever thought that it would. It seems that each time I try something new it just pushers me to move up to the next level. What started out as me wearing them on my occasion trip to the mall quickly lead to backyard strolls wearing only the panties and a short tee shirt, the occasion nature walk but it was never enough.

I decided that since i spent half of my live at the office that this would be a good place to wear them. Whoever designed our office building must have love sun light, it was shaped in a "U" with each office having at least one window. I worked late most nights and often would find myself watching as the lights on the opposite side turned off one at a time, these lucky people were heading home. Eventually the only time I would see a light was when Rita the cleaning lady would turn it on to clean the office. Rita was a nice lady about mid to late thirties I would guess, I had never really talked to her other than a casual hello as we passed in the hall.

After a few days of wearing my panties to work it was time for something new. It was after normal working hours and the other side of the building was dark. First I slipped off my shoes then my pants while still sitting at my desk I removed my socks then my shirt leaving only my new lacy black thongs on. I sat there for a while nervously scanning out the window for any movement. As time passed I became much more comfortable with my attire and even began walking around the office, this felt so good and bad at the same time. This became my nightly routine as soon as the building went dark my clothes disappeared except for my panties.

One night just as I had finished getting dressed I heard a key in my door, the door opened and in walked Rita, a couple of minutes earlier and she would have caught me. I said hello and she replied with a good evening I see that you have put your clothes back on. I almost fell off of my chair. I pretended to not know what she was talking about and she explained that she knew what goes on in this office after dark. I denied everything, Rita said that she was going to have to report it but I told her that it was her word against mine. She pulled out her phone and showed me pictures of me prancing around my office wearing only a pair of ladies panties. My face dropped into my hands in shame as I began begging her not to report it, I will do whatever you ask. In hindsight I probably just should have let her report me and taken my lumps.

Obviously she had planned what she was going to say. She told me to strip everything except for the panties. Rita started snapping more pictures of me as I undressed, after a few minutes she told me to take my cock out and start stroking it, I hesitated at first but she gave me a challenging look. Reluctantly I began jerking my cock while Rita snapped many more pictures. She moved over to my desk and a started doing something with her phone and my computer. She later explained that she had sent the pictures to a web address and downloaded my mailing list from my computer. If I resist her she will send the address to everyone on my list.

The constant stroking of my cock combined with Rita staring at me and taking pictures was getting me to a familiar point, I was going to cum soon. As I looked around for something to catch it, Rita took my coffee cup and approached me, she removed my hand and replaced it with hers, after a few quick strokes I could feel my cock was about to explode. Rita aimed the end of it at my cup and I was soon pumping a load of warm cum into my cup. When I was finished Rita handed me the cup and instructed me to drink up. I refused and she gave that look again and picked up her phone, she told me that this was the absolute last time that she was going to take any more resistance from me and began pushing buttons on her phone. I begged her to stop, said that I was sorry and raised the cup to my lips. Opening my mouth I tipped the cup up and allowed the it to slide out into my mouth. Rita ordered me not to swallow but instead stick my cum coated tongue out for her to see it. She smiled and took a picture then told me to swallow.

Rita appeared to be pleased with me and sat at my desk, she told me to sit on the desk in front of her with my legs spread. She began explaining some of her rules to me, I was never to hesitate when she gave me a command, from now on she would be visiting me every night and I was to be wearing only woman's panties when she arrived. While talking she had been glancing down at my cock and then she took it in her hand and gave it a few stokes, there was still the odd drop of cum oozing out of it the first couple landed on my desk then she took the next one on her finger and placed it between my lips. I sucked on her finger and licked it clean. She got up to leave and began to leave but told me to lick the cum off of my desk, she didn't like a dirty office. I didn't hesitate and bent over to lick it clean she grabbed my ass and commented that this was going to be fun, then left the room.

I quickly got dressed and headed home all the way there my mind was racing. As much as I tried I knew that there was no way for me to break Rita's hold on me and I was terrified to think what she might have in mind for the future.

The next day went by a way too quickly, I had to rush to get my work completed before Rita arrived, secretly I was hoping that she might not but I couldn't take the chance so as soon as the office lights began to go out, off came my clothes. Rita arrived a little earlier than the previous night and was pleased to see that i was as she put it in my uniform. She had a small bag with her and said that she had been shopping for me. The first thing that she removed was a small camcorder which she quickly set up and began filming me, she smiled and said that she couldn't wait to post these videos on the website. Her hand went back into the bag and removed a dildo it actually looked just like a real cock.

Rita held the dildo in front of her groin and instructed me that this was the same as a command anytime I see this I was to drop to my knees and take it in my mouth. I have watched some porn movies so I knew what she expected me to do. I sucked and licked her dildo just like it was real but choked when she put it in too far, she told me that I would bet used to it and become a good little cock sucker

She reached back into her bag and removed some kind of jell. She made me stand up and remove my panties after getting me back down on my hands and knees she began lubricating my ass with the jell, occasionally inserting a finger . It hurt a little she was the only person other than my doctor to ever touch me there. Rita moved behind me spread my knees and began to slowly insert the dildo into my ass. It hurt each time she progressed but felt so good as she eased of the pressure. I could see my cock hanging between my legs, it was getting harder the more she fucked me. The cock, i mean dildo, was sliding in and out much easier now and Rita would gain a little with each inward stoke.

Once she had had enough for now she removed the dildo. It had been painful but also very erotic getting fucked by a woman. My cock was harder than it had been years, Rita smile and handed me my coffee cup which I soon made a deposit into then without hesitation drank the cum and licked out every last drop. When I was finished she smiled and held the dildo to he groin. I knew what she wanted but I also knew where it had just been. She gave me that look and I dropped to my knees, closing my eyes as I took the dirty dildo into my mouth. She patted me on the head and told me that I have to keep my toys clean. Just before she left she reached back into her bag and removed a small butt plug and instructed me to put it in my ass each morning when I first get to work and she will remove it in the evening. She said that this would help my ass to get ready to be fucked.

After Rita had left I got dressed then sat there for a few minutes thinking about what had just happened. I had never expected to get raped and enjoy it.

This carried on for the next few evenings, Rita had given me a name she calls me "slut". Every now and then she will change things a little and have me lie on my back while she lowers her pussy or ass onto my face or once in a while onto my cock. I was never much for eating pussy but I knew that I had to give it my best I could not disappoint Rita.

The beginning of the second week Rita surprised me with a couple of new toys, another dildo and butt plug both a little larger than my original ones, like before they were tight but she said that I would soon get used to them and I did.

Midway through the week Rita shocked me when she entered my office with another woman. There I was standing there in my black lacy panties and a hard on, I felt so embarrassed. She introduced me to Sandy as "slut". Sandy was a medium height woman in her early thirties with a slim build and red hair, like Rita she wasn't exactly what I would call gorgeous but they both had a certain sex appeal that was unmistakable.

Rita soon began demonstrating to Sandy how well my training was going, before long they had me on the floor Rita with my new dildo in my mouth and Sandy reaming my ass with my original one. When they were done and after I cleaned the toys orally, Sandy told Rita that she was horny. With Rita's blessing Sandy laid me on my back and planted her cunt directly over my mouth. I went right to work servicing her by now I was getting pretty good at eating pussy and Sandy did have a nice fresh cunt. The biggest difference with Sandy was that while I was licking her she bent forward and took my cock in her mouth, I wasn't used to anyone caring about my satisfaction.

Sandy truly was horny and it wasn't long before she began to have an orgasm, with her juices flowing onto my eager tongue. Soon afterwards I could feel my cock about to explode into her mouth, she pull my cock most of the way out and held it there so that my cum was deposited onto her tongue. She quickly spun around and gave me a big open mouthed kiss, depositing my cum onto my tongue then she told me to swallow. The girls took turns that evening pleasuring themselves with me, I must admit it was great.

For the next while it was just Rita and me, she was always trying new things with me seeing just how far she could push me. Each week there would be new toys always a little larger than the previous ones. I must admit that the butt plugs were making it much easier to take the dildo up the ass. I thought that Rita was beginning to take it easier on me but soon realized that I was just getting used to her abuse and actually enjoying it.

With the vast picture and video library that Rita had posted of my training I know that she will own me for as long as I amuse her. I am a little nervous of what she will do when she does tire of me.

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AnonymousAnonymousover 10 years ago
nice :-)

Not really into the pantie thing but the rest was excellent :-)

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