Caught, Blackmailed & Forced to Become Tonya

Let me tell you a little about myself. I am a nice looking 34-year-old male who has always had a very varied interest when it came to the sex department. In my younger days I had played around with many different aspects including BDSM, cross-dressing, bi curious times and the like. So needless to say, by the time I was 30 I had little interest in plain vanilla sex. With the ease of access to all these and other kinky themes via the Internet, I was now in hog heaven. I could see as many pictures as I wanted, place personals in order to meet people or have hot e-mail exchanges as well as a host of other activities.

Well like any sexual need, it became more and more part of my daily life, I would find myself continually checking my secret e-mail address to see if anyone had made contact with me, I would ogle over pictures covering all sorts of kinky themes that usually included cross-dressing, BDSM and some gay and bi postings. I was fortunate that I was able to check these things out at home in the evenings and mornings, but also while I was at work on my laptop. I would spend most of my lunch break checking out my usual sites. As I traveled a good amount, I would take my laptop with me so I could continue these activities while on the road. I was always very careful to clear out my temp. files when I was done in case Mike our IT Manager or his assistant Amy ever needed to load something onto my computer and came across my deepest secret life.

So on Friday morning I didn’t think anything of it when Mike sent me an inter-office e-mail asking me to stop by his cubicle, we had been talking about getting new laptops and I figured he just needed to go over the options. I grabbed a cup of coffee and headed off to his cubicle where he sat at his PC. He told me to come in and take a seat. He leaned over towards me so he was only a few inches away and started to speak in a low voice. He told me how he had been checking our server for web site access information and said that he had discovered a number of strange sites that had been visited by employees, I could feel my face turning a little red with guilt still thinking that he can’t have anything on me, after all I was always so careful. I saw a slight smirk on his face when he saw my face turn red. He proceeded to tell me that he had a list of some VERY interesting sites that I had visited, I tried to deny it and tell him he must be mistaken when he offered to show me the list, I said sure show it to me, trying to hide my trails and be a little cocky about it. Just then Amy showed her head around the cubicle to ask Mike a question just as Mike was about to upload the list, I quickly told him it wouldn’t be necessary and again turned a brighter shade of red with the thought of also being caught by Amy.

After Amy left I said to Mike what should we do about this situation then. Mike started to smile an evil grin and said, well you know this kind of thing is against company policy and I have this memo prepared to send to your boss. I was horrified and asked him if there was some way we could keep this under wraps and that I could probably find someway to pay him back in return. He said he had thought about the same thing and had some ideas and told me to go around to his house at 7pm that evening so we could talk about it easier away from his cubicle, I agreed and said I would see him then.

I arrived at Mike’s house that is out in the country, not real big but neat and secluded. I knocked at his door which he opened and invited me in, I noticed that he was dressed in a pair of spandex type jogging shorts and a muscle type t-shirt, the type with no arms. Although I say it myself, Mike was a good-looking guy in his mid 30’s who appeared to work out on a regular basis. He caught me quickly checking out his body including what I could see was a large bulge developing in his spandex shorts, I quickly diverted my eyes but not before he gave me a knowing grin. I asked him what he thought we should do about the web site info. He said that he had been watching me for some time and knew that I lived alone in a small apartment. He continued to tell me how he was getting too busy to look after his country house and in return for not turning me in, he wanted me to come over on a regular basis and help him look after it. He even suggested that if I didn’t like my apartment, I could pay him the rent I was paying and share his place that was much nicer than my apartment. He said I would be expected to do many chores for him including preparing some meals, cleaning his house, doing his laundry etc. I can’t say I liked the sounds of it too much, but had little choice.

After I agreed, he said that he drawn up a little contract that would hold me to what he had just suggested. I read it to myself “ I Tony Green willfully submit to any demands made to me by the Master of the estate, I will further agree to perform any duties he requests of me however personal in nature without question. Should I at anytime disobey one of Master’s order I will be subject to a punishment of Master liking” I thought it was a little strange how he kept referring to himself as Master, I figured he fancied himself as a Master of his country estate. I figure I may as well sign it; nothing too much can come of it.

After I had done so, Mike told me that if I was going to be his housemaid that I needed to dress more appropriately, I said in what and also asked him why he called me his maid, he just smiled and said you will find out Tonya. Tonya, I thought to myself, this is getting a little to weird. I said to Mike, look I think this is going a little off track and that I should leave and we would discuss some other sort of payback. He got real mad and punched me real hard, it hurt like hell, while I was recovering he said listen here honey, you aren’t going anywhere, you have signed a binding contract, I also have a memo ready to send if you don’t start doing as you are told. With that he told me to take off all my clothes so I can start to get ready. I reluctantly took off my clothes down to my boxer shorts which for some reason were sporting a hard on, he told me to take them off which I did. As I was straightening up I saw a flash as Mike took a photo of me with his digital camera. I asked him what he was doing and he just said “a little insurance that’s all”.

He pushed me ahead of him and told me to go upstairs to the first bedroom on the right. As I entered the room I got the shock of my life, there stood Amy in a short black leather skirt, red silk blouse, black hose and high heels, I turned to try and leave but Mike grabbed me and said you’re not going anywhere honey. He said Amy was going to give me a bath and clean me up ready for the next phase of my transformation.

Amy was in her late twenty’s and was great looking, many of the guys at work lusted after her enjoying the sexy outfits she would wear to work. She told me to get into the bathroom and then proceeded to smother me in a thick cream that smelt pretty bad. She told me to stand there for five minutes while she ran a bath. After five minutes she had me get into the bath and rinse off, as I did all of my body hair just started to wash away, I thought shit, what are they doing to me, but at the same time I was getting pretty aroused. She sat down on the toilet with me standing in front of her with my cock more or less at eye level; she then proceeded to shave the thicker hair from under my armpits and then shaved any hair that was left on my cock and balls. This got me real hard, Amy took hold of my hard cock in her hand with lovely long nails painted in a bright red and started to laugh at it, is this all you have, I was only about 4” fully erect and even then it was small in diameter. My face turned red again with the humiliation.

Amy then lower her head and placed the tip of my now fully erect cock on her thickly painted lips. She gradually opened her mouth and my cock slipped in the full length, I felt kind of humiliated, I had read on the porn sites about all the ladies who often gagged the first time the full length of a cock went in their mouth, here I was in her mouth in one full plunge and it barely reached the back of her tongue. So did I care, I was about to get blown by one of the hottest chicks at work, my co-workers would be so jealous to know what I was about to get. As she started to work back and forth on my cock I thought to myself, this is not half bad considering I was the one who was supposed be getting punished here. I placed my hands around her head and started to push her head onto my cock so I was face-fucking her, boy did it make her mad. Amy instantly withdrew from my cock, reached up and slapped me real hard across my face and told me that she was the one in control here and that a worthless slut like me should not even think about trying to get the upper hand. I said I was sorry, and she slapped me again but this time on the other cheek and said that it is sorry Mistress and that I needed to learn some manners.

I had never been much of a lover and started to cum very quickly, she sensed the pressure building up in my balls and just as I was about to blow my wad into the back of her throat, she quickly pulled my cock out of her mouth and finished me off by jacking me off into a glass. Amy then instructed me to go into the bedroom and lay down on the edge of the bed facing up; I quickly complied so not to get another slap, which still stung both of my cheeks. She then instructed me to open my mouth good and wide and to stick my tongue out. Amy got onto the main part of the bed and proceeded to poor the contents of the glass onto my tongue making sure she spilled some onto my chin, top lip and cheeks and told me not to move. Just then I saw another flash of the digital camera and heard Mike start to laugh. I turned my face to look over the edge of the bed to see Mike standing there with his fully erect cock only inches away from my mouth. His long cock, which must have been at least 10” long and as thick as my wrist, was glistening from what smelt like baby oil. I started to protest as Amy turned the LCD screen of the camera to show the picture she had just taken. I was shocked to see my face and tongue covered in cum with Mike’s cock just above my open mouth looking like I had just given him a blowjob to completion. Mike told Amy how that would be a great picture to e-mail around the office if their new slut decided to try and back out of the contract and not obey their every command. My heart sank as I realized I was basically screwed, whatever Mike had on me with the web sites was nothing compared to the picture they now had. Mike turned to Amy and told her to finish getting me ready and to bring his new slut to him when she was finished. Amy told me to scoop up the cum off my face and to lick my hand clean of all my cum and then swallow it. I did as instructed and I must say, I savored the sweet taste of my cum. Amy then handed me a face cloth to clean up my face for the next part of my transformation. I asked her if she could tell me what was going to happen to me. She sat on the bed next to me and started to explain that she was going to transform me into a she-male slut for Master Mike’s personal use and that if I knew what was best for me I would go along with them without any argument. She asked if I was going to put up a fight, and I said no, she quickly scolded me and said NO what, sorry Mistress, I meant to say No Mistress, “that’s better” she said.

Amy took me by the hand and told me to stand up, she then told me that she had been out shopping for me and had bought me some wonderful things to wear. Just then she reached over and picked up several shopping bags and placed them on the bed. Out of the first bag she pulled out a black corset that had lacing all the way up the back and heavy boning. She told me to turn around with my back to her while she started to put the corset on me, I was surprised at how well it fit even though I was not very well built and probably had what could be described as a feminine shape to me. Amy proceeded to lace the corset up very tightly, or so I thought. She then told me to lay face down on the bed while she planted her knee in the small of my back and tightened it even more. I started to complain that I could not breath easily, she told me to start to breath with my upper chest, which I did and it felt better. Next she helped me pull up black stockings and attach them to the garters on the corset. I was starting to get very aroused again at this point, Amy noticed and started to laugh, I think Tonya is rather enjoying this; I just blushed a very deep red, deep down though I was. A nice pair of black silk panties finished off my attire for the evening.

Amy pushed some false breasts into the top of the corset and said “they will have to do for now until we can get something more permanent”, more permanent I shouted, boy was I sorry. After another hard slap across my face Amy continued to tell me what an ungrateful piece of shit I was, that she and Mike could have turned me in and I would have been out of work and disgraced in front of everyone, except she felt sorry for me and convinced Mike I would be fun to blackmail. I started to cry, Amy gave me a hug and said, “it will be alright Tonya, and you will make such a nice little girl and will enjoy life so much more”. She then led me over to a makeup table, wiped away my tears with a tissue and started to apply some make-up.

First she put on a base foundation that smoothed out the look of my face and covered any signs of a beard shadow. Next she outlined my eyes with black eyeliner and had me close my eyes while she was doing so. I thought I could see a flash through my eyelids, and sure enough I did, when I opened my eyes, Mike was taking some more insurance photos! After about twenty more minutes I had on nice eye shadow, rouge on my cheeks, bright red lipstick and thick mascara that made my eyelashes very long in appearance. When Amy was done, she had me look in the mirror and I saw a very good-looking young lady looking back at me, even with my long boyish hair, which I kept in a pigtail. Amy took a hot curling iron and started to style my hair; in no time at all she had my long hair in a flowing feminine style with bangs hanging down over my forehead. I was then given a nice pair of patent black strap 5” high heels to put on. I was a little shaky at first, but Amy helped teach me how to swing my hips and soon I was walking like a pro. With my small 5’ 4” frame, even with the heels on I could pass for a real nice looking chick and was really starting to get into it.

Amy gave me a glass of white wine to celebrate my new look; I was walking back and forth swinging my hips, putting one foot in front of the other in true catwalk fashion. Amy was capturing me on video that I was so happy to pose for, I guess not really realizing it was even more insurance and dirt on me. I was half way through the glass of wine, when I started to feel a little light headed and very turned on, I could feel my heart starting to race and just before I slipped further into a sexual frenzy, thought to myself that maybe the drink was d**gged.

Just then I felt a strong pair of hands come from behind me and start to caress my now shapely waist working further up to my false breasts, I could also feel a large bulge pushing against my butt as I was being man-handled. I spun around to be greeted by Mike with a big smile on his face, he turned to Amy and said, nice job honey, she looks terrific. Next Mike’s lips came up to mine and he started to kiss me full on the lips, forcing his tongue into my mouth. Feeling rather loose from whatever was in my drink, I responded and started to push my tongue into his mouth, all the time being videotaped by Amy. Mike’s hands grabbed hold of my ass and he started to feel me through my black silk panties, rubbing and caressing my ass cheeks. I then felt him pull the panties to one side and start to dart a finger in and around the opening to my virgin ass.

Mike starts to tell me how happy I am going to be being his own personal slut and how he is going to teach me how to pleasure a Master and anyone else he chooses for me to be used by. He takes one of my hands and guides it down to his crotch. I start to play with his bulge through his pants with my long deep red false fingernails, he groans with approval and instructs me to pull his shorts down. As I do I feel his huge cock springs straight out, I instinctively grab hold of it with my hand and start to play with it.

Mike places his strong hands on my shoulders and pushes me down to my knees; I know what is expected of me. I kiss the end of his big shaft, which has to be almost 10” long and so thick. I open my mouth as he starts to guide his long shaft into my mouth, my mouth is stretched wide open to take up the diameter as he starts to pump and face fuck my mouth. He starts off slowly until I get used to it in my mouth, he then puts his hands behind my head and starts to increase the pace fucking my mouth harder and harder. I almost gag when it gets to the back of my throat, I hear Amy laugh as she brings the video camera in for a close-up. Mike continues to fuck my mouth, telling me to play with his shaved balls, he then has me lick and suck on each of his heavy balls then use my tongue to lick back up the length of his shaft until I am at the end where he once more berries it into my mouth. This goes on for what must have been half an hour until I feel his balls start to tighten up, I try to pull away from his cock, but he puts his hands behind my head once more to keep me in place. Next I feel the first long spurt of cum hit the back of my throat, then the next and the next, I start to gag as he pulls away giving me a chance to quickly swallow to stop from gagging, he continues to cum spurt after spurt over my chin, cheeks, eyes and nose, he then pushes his cock back into my mouth for the last couple of spurts. I lick down the shaft cleaning it and making sure that I get every last drop of his cum. I have never known anyone cum as much as Mike did as I scoop up the cum off my face with my long painted fingers and put it in my mouth putting on a great show for the video camera.

Amy comments to Mike how I am one hell of a cocksucker, so good she wouldn’t be surprised if I have done it before. Mike agrees saying that I am one horny slut that he is going to enjoy having me as his personal fuck slut and that he can’t wait to try out my pussyass!!!

Now they not only had evidence from my internet activities, but they also had photographic evidence. Photos that may have started out being innocent in the making, but told a far different story to anyone looking at them. To anyone looking at them I was gay, a pervert, a sick bastard that liked to dress up in women’s clothes and suck on men’s cocks until they explode in my mouth, basically I was screwed, I had now way out other than do as they wanted.

Mike sporting a huge grin on his face told me to “sit down slut Tonya, I want to tell you about your new life”. As you have no doubt figured out we now own you, to do with as we please. You will dress the way we tell you to, act the way we expect, service us both domestically and sexually whenever and however we wish. You will be used and abused sexually in ways you never even fantasized about when you were surfing your favorite transgendered sites. Not only will you serve us sexually, but you will also serve whomever we choose, from friends of ours to perfect strangers. You will become a cum slut, forever wanting hot fresh cum in your mouth, on your face and up your pretty tight pussyass. Your only mission in life from this day forward is to provide pleasure to others. Some of these pleasures you will enjoy providing, like the times you will act like the pretty young cock slut you so much long to be. Other times you will not enjoy so much, like when you are the centerpiece of one of our sex parties, restrained in the center of the room with your pussyass at perfect fucking level and your head held out at waist level. You will be used as a cum dump, a mere object for anyone’s sexual relief. On bondage nights not only will your ass be sore from being fucked repeatedly, but your ass cheeks will be bright red and welted from some pissed off Mistress or Master who decides your ass is going to be the means to take out their frustration on. Oh yes Tonya my sweet little cum slut, your life is going to be very different from now on, very different.

At the end of my lecture I could see that Mike was getting very turned on again and was sporting a huge hard on. You like the look of that don’t you Tonya, well let’s see just how good you are at being used my little cum slut. With that Mike got on the bed and just pointed towards the area of the bed in front of him as my indication that I should know what is expected of me. I positioned myself on my hands and knees with my virgin pussyass sticking up in the air only inches away from Mike’s cock which at this point was fully erect again.

Amy came over and squirted some lube over my pussyass and then proceeded to push first one finger and then two and finally three fingers into my pussyass. It hurt a little at first but once she told me to push back and relax it started to hurt less and took on a pleasurable feeling. I couldn’t believe what position I now found myself in only a couple of hours after arriving here…what had I got myself into. Moments later Amy withdrew her fingers which were quickly replace by the pressure of Mike’s huge cock pressing against my pussyass, he told me to relax and that soon I would be all his, his personal little fuck slut.

Gently at first he pushed until I opened up and the head of his cock slipped in, gradually he pushed more and more of his length into me until I felt his balls up against my ass cheeks. He just sat there for a while letting me get used to his huge cock….another flash went off in the corner of my eye. Mike then started to pull back and then push back in, slowly increasing the speed. After a short time I hate to admit it but I was really starting to enjoy the feeling. Amy now had the video camera recording catching first hand Mike taking my virginity. I couldn’t help starting to moan with pleasure telling Mike to fuck me harder and deeper. Oh yes he said, you are going to be one hot fucking slut, just ehn he pulled completely out of me leaving me feel empty and sad. I started to beg for him to put it back in and fuck me hard like the slut I am, his slut. He rammed his cock back into me in one hard thrust, I let out a yelp of pleasure.

He continued to fuck me for what felt like an hour, all the time I was pushing back to meet his forward thrusts. Just then he started to grunt and tell me he was about to cum, he was going to let me have his hot seed deep in my hot and well fucked pussyass. Just then I felt him stiffen up and could feel the first of his enormous spurts of hot cum deep within my pussyass. Spurt after spurt he let loose deep inside me. When he was done he pulled out of me and told me to stand up and bend over slightly at the waist. Amy was right behind my ass with the camera filming away as Mike’s fresh and still hot cum started to run out of my enlarge pussyass hole and down my legs. Mike ordered me to scoop up the cum and eat it off my hands in fro not the camera. I was no well and truly his slut, and more to the point I wanted to be too.