Legally Bound free porn video

Legally Bound By: Cindy Renee' Anderson [email protected] Part 1 - The Date It had been a long time since I had a chance to dress in full female drag and I was desperately looking forward to a few well deserved days off. The last few weeks had been extremely busy at work and I needed some relaxation and fun. I had met another man named Steve using the local personals on the internet. I answered his ad that said he was a strong, handsome slightly bi- sexual man interested in making it with a sexy crossdresser. We talked for a few weeks then agreed to meet in person at a hotel bar. After the day's business was concluded on Friday, I checked into a hotel in Portland, Maine. I began by unpacking several of my favorite female outfits that I had brought along with me and hanging them on the bathroom door. Next, I retrieved my bathing and shaving bags placing the various products on the large bathroom vanity. I ran the water for a hot bath adding sweet scented bubble bath and assorted skin moisturizers. I quickly trimmed all my body hair from the neck down with an electric trimmer. Next, I gave my face and neck an ultra close shave removing all hints of stubble. I applied a skin softening facial mask to set while I soaked in my bath. When finished, I dimmed the lights and lit two scented candles to light my bath. The tub was large enough for me to sink in up to my neck when I laid back in the luxurious bubbles. I lit a long Virginia slims 120 and smoked indulgently holding my cigarette like a woman. I listened to some light woman's music as I soaked. A while later, I drained the tub and sat on the edge to shave with my ladies' razor and shave gel. First I shaved smooth my chest and stomach. Next came my hands, wrists, arms, and underarms. Soon I was stripping my ass and pubic area of all its hair also. Lastly, I worked my way up my legs from toes to hips. When finished, I couldn't get over the smooth sensation of the freshly shaven skin all over my body. I rubbed my entire body with scented moisturizers, creams, and slickening oils making it silky smooth to the touch. I even rubbed a few drops of KY jelly into my anus to keep it well lubricated. While the skin conditioners absorbed, I applied Secret Powderfresh anti-perspirant /deodorant and a few sprays of sweet body scents then peeled away my facial treatment. I began dressing by sitting on the bedside and slipping into a pair of black silk French cut panties. I loved the way the silk caressed my smooth cock and balls. I pulled on my favorite long white silk lounging robe which felt heavenly the way it flowed over my smooth skin. Next, a pair of white silk woman's' hair scrunchies for my wrists. I pulled a chair close and set my feet on a towel on the edge of the bed so I could paint my toenails bright pink. As they dried, I smoked a long cigarette and thumbed through the latest issues of Cosmo and Mode. Next, I moved to the vanity to apply a liberal coat of base foundation to my face using make-up wedges. I pulled my longish brown hair back and tucked it beneath a black silk headband to clear my hair from my face. I grabbed my ultra sheer nude pantyhose then sat on the edge of the bed and slipped my pink toenails of my left foot daintily into the soft material I had gathered. I slowly pulled the silky sheer material over my ankle and calf marveling how the hairless skin allowed the material to slide on as smooth as oil. With both sides of the pantyhose at my knees, I began a slow sensual wiggling routine that I had seen so many of my girlfriends go through as they struggle into the nylon encasement. Before I pulled the pantyhose all the way up, I unwrapped a Kotex regular maxi-pad, peeling off the paper to expose the sticky tape. I attached the maxi-pad to just the right spot in my panties, so it tickled and protected my asscunt hole and hid my fully covered cock and balls by squeezing them out of sight. I squatted a little to pull the tight gusset area over my ass and crotch and up to my waist. Again I squatted, making sure the shiny nylon had tightly bonded to my entire body. The tight seal caused the maxi-pad to make some crinkling sounds as it adjusted to the sheer nylon confinement. Lastly, I tugged on my tight black satin corset and adjusted it to smooth my waistline and give the illusion of feminine hips. The next step in my transformation was to remove my silk robe and to begin attaching my falsies to my chest. I opened a small box and retrieved a pair of life-like silicon breastforms with nipples in size 36D. I used a special adhesive on my bust area to keep the falsies snugly attached. Using special make-up, I lightly covered the breast forms and my chest and lower neck to make the color tones match and appear natural. I hooked my black silk-n'-lace unwire bra then pulled it into place, then made a few adjustments to give the appearance of a very natural large round bust. Over this I slipped on an elegant black silk thigh length slip with lace trim. The feel of the slippery silk rubbing against my nyloned thighs was an indescribable pleasure. It was time for me to pull a stool up to the mirrored vanity so I could apply my make-up and style my wig. I began by opening another small box that contained a long, very sexy, curly blonde wig. I set the wig on a styling form and began to meticulously curl and style the lovely blonde curls. After about 45 minutes of curling and spraying with sweet smelling hair spray, I was satisfied enough to pull on my hair net and fasten the wig tightly and securely to my natural hair with hairpins. I topped it off by clipping in a black silk bow for a feminine touch. Again, I used my headband to hold the hair away from my face so I could do my make-up. I started with my eyes, plucking and shaping my brows to give them a feminine shape, using a photo of a model from one of my magazines as a guide. Next, I colored my eyelids with a pinkish lavender shadow. I grabbed a dark black eye pencil and carefully traced and darkened around my lids, finishing up with black long-lash mascara to lengthen and thicken my eye lashes. A light, soft powder for my nose and cheeks came next. I used several brushes to layer on shades of blush and rouge to sculpt my cheekbone and give a healthy, sexy glow. Lastly, I began on my lips by starting with a creamy moisturizer, before applying a shiny pink gloss giving them a sensual wet appearance. I finished by using a small dab of thick brown make-up for a sexy beauty mark on the left above the corner of my lip. I studied the small collection of clothes that I had brought for a moment before selecting the ruffled black silk long-sleeved dress. I slid the slippery material over my head and then made a few adjustments to straighten my lovely dress out. I fit me perfect and felt great !! An opening below the neckline allowed a hint of busty cleavage to show, the lace trimmed bottom hung just above my knees, and the waist was drawn in enough to pull the material tight around my ass. I loved the bounce and sway of my life-like falsies as I walked to the bed and sat on the edge. I dug through my make-up bag to find my false nails. Soon I had carefully attached the 3/4-inch nails gluing them perfectly in place. Next, I used a nail file to give them a convincing shape. I took my time painting them my favorite bright pink and gently blew them dry as I read my woman's' magazines and smoked another Virginia slims, all the while sipping on a kiwi-strawberry wine cooler. Rummaging through my jewelry collection, I selected a pair of long dangling gold earrings with small hearts, a gold linked pearl necklace, several gold faux diamond rings, and a few bracelets. I grabbed my favorite 3-inch pointed heels that were black patent leather with open toes to showcase my pink toenails and fastened the tiny straps around my ankles. I had to prance around for a while in the heels to get my walk down pat. I finished with a few spritzes of my favorite perfume making me swell sweet and sexy. I filled my small black leather purse with the necessities such as make-up, cigarettes, and a spare maxi. Before leaving to meet my date, I gazed at myself in the full-length mirror. There I stood in all my glory; I appeared to be 160 pounds and standing 5 foot 10 inches in my heels, a big sexy bust and long curly blonde hair with perfect make-up. I was amazed at the beautiful sexy creature that was staring back at me, I certainly looked like a woman that any reasonable man would love to fuck. Cindy was dressed and ready to tease and please 'til she got her man. It was 9:00 PM as I casually strode into the dimly lit bar, subtly shaking my ass, past a small group of men at the bar until I reached an out of the way table in the corner which allowed me to survey the room. I had barely sat down and placed my purse on the table when a waitress had appeared. In my most soft and feminine voice I ordered a strawberry daiquiri and asked for an ashtray. As I waited for my drink, I glanced around the sparsely populated but cozy bar. God, it felt like every man in the place was stealing a look at me, obviously impressed and appreciative of my womanly appearance. I began to really enjoy the attention I was receiving for it greatly enhanced my self-confidence that I was passing perfectly as a genuine female. A short while later, the waitress returned with my drink and an ashtray. I lit one of my Virginia slims holding it like a woman while daintily sipping from the straw in my drink. After several minutes, a tall well-built handsome man left the bar and approached me. He introduced himself to me as Steve and asked if I was Cindy. My date had arrived, and he was cute! I told him that yes, I was indeed Cindy and to have a seat with me. He was about 6 feet 2 and probably a good 30 pounds heavier than I and several years older at 39. First, he told me that he was stunned with my appearance and couldn't believe that I was actually a man. We talked for over an hour getting to know one another. I found Steve to be very charming and handsome - a great catch for any woman, and we really hit it off great. He was a perfect gentleman and treated me just like a woman. Steve bought me several more drinks and kept complimenting me telling me how sexy I was. He told me that he was a lawyer and had a small practice in central Maine. He went on to detail his attraction to feminine crossdressers and so forth. I told him a brief history about how my dressing had progressed from the days of being a teen to the present. By 11:00 PM, I had decided that I had heard enough, I wanted this man in bed. My flirting had made Steve hot and horny and finally when he suggested that we go up to his room, I was all for it. We left the bar and headed for the elevator, I walked close to him with my hand on his arm. In the elevator, Steve wrapped his hand around my waist and onto my ass, another couple paid no attention to us. We stopped of my room so I could grab an overnight bag and some sexy lingerie. Once inside my room, Steve pulled me close for a long sensual kiss. Our tongues wrestled in a heated dance of passion. His hands roamed my body caressing me through the silk of my dress. My heartbeat raced for he was making me feel like such a woman. Steve commented about how he was impressed with the make-up and my feminine wardrobe scattered about the room. But enough was enough - I wanted this sexy man inside of me. Steve led me back to his room so we could get down to business. Once we had arrived safely inside, I pulled Steve's shirt off and gently kissed his chest leaving traces of my pink lipstick on his tender flesh. I unbuttoned and unzipped his pants then pulled them off from him. There, in front of me standing naked, was a perfect specimen of hunkish man. Steve helped me remove my silk dress telling me how sexy my perfume was, as I stood before him in my silken lingerie. We kissed again as we fell to the bed. I laid Steve onto his back and began kissing my way down his chest until I was face to face with my first cock. I really didn't know how to start so I decided to give him the type of blowjob that I've always loved. I grabbed his hardening shaft and began to softly stoke it, noticing how my pink nails contrasted nicely with the flesh of his cock. Next I parted my glossy lips and began to gently lick and nibble the head of his throbbing cock swirling my tongue around the head. I kept stroking his hard meat until he was fully erect. I sank my lips deep onto his shaft running my tongue across the full length as I gobbled and slurped his delicious cock. I delighted in his masculine aroma which mixed with my sexy perfume combining for the smell of sex. Steve grabbed the back of my head urging me to go deeper. I clamped my lips tight around his thick cock with glistened from my saliva and raised my eyes adoringly at my man. The room filled with my slutty sucking sounds and Steve's lusty moans of pleasure. I was thoroughly delighted by the taste, texture, and feel of his warm flesh running across my lips. Steve warned me that he was about to cum but I clamped my lips even harder as my head bobbed furiously up and down on his great cock. Suddenly Steve unleashed a torrent of warm creamy spunk down my throat. I swallowed hard then pulled back to get a good first taste of cum. "Mmmm..." It was even more delicious than I had dreamed. I savored my first taste of cock loving the though of bringing a man to pleasure just as a woman would. I excused myself momentarily so I could go and freshen up and change into something more comfortable. I grabbed my black silk teddie ensemble and brought it with me to the bathroom. I quickly brushed my teeth and gave my lips a touch-up of gloss. I stripped out of my bra, corset, and pantyhose and slipped into my silk teddie pulling on black seamed lace trimmed silk stockings and attaching theme to the garter straps from my teddie. I pulled my black satin panties up over the stockings as to allow easy removal and access to my mancunt by Steve. I smoked one of my long cigarettes indulgently and drank glass of wine Steve had prepared for me to soothe my nerves. We soon returned to the bed where again I began to slobber over Steve's wonderful cock. It was exciting to feel a man harden in my mouth. After a few minutes of this delicious assault, Steve was rock hard again. I changed positions to lay next to him on my knees giving him the hint that I wanted him in my ass. Steve pulled up behind me and began to pull down my panties exposing my smooth ass. I buried my face into the pillow and clenched my teeth waiting for the pain of being entered. I was nearly overwhelmed with excitement with the frission of knowing that I was going to get fucked in the way I had always dreamed off. I felt the tip of Steve's cock pressing against my puckered anal opening, and like any good woman would do, I reached back to guide his cock into my well-lubed asscunt. Slight shocks of pain hit me but quickly subsided leaving only glorious pleasure as he gently eased his throbbing cock further and further into my tight ass. Soon my man had established a slow sensual rhythm working his cock ever so deeper into my slickened depths. I moaned in an intense sexual pleasure that I had never felt within me. Instinctively, I rocked back on my knees to meet his hard thrusts as his silken cock worked its way in and out. "Deeper stud," I whimpered in my most feminine voice. I arched my back and tossed my head in pleasure as we established a comfortable pace in our fucking. I had never felt sexual pleasure this pure and fine, it felt so perfect laying there in my sexy outfit all dolled up like a real woman and getting fucked by a handsome sexy stud and loving every pulsating thrusting inch of his great cock. "So, this is what I've been missing," I thought to myself. I was lost in a world of pleasure feeling glamorous and sexy lying submissively beneath my man. He ran his hands across my chest rubbing and cupping my fake tits before grabbing tight onto my hips. After 10 minutes or so, Steve's pace began to increase and was soon fucking me fast and furious. I bucked with pleasure wanting my man to have a great orgasm. He stopped suddenly, tensing up, then buried his cock fully in my ass to let loose a warm slippery load of cum. I could feel the warm spurts streaming deep within my silken depths. Moaning lustfully, I soiled my panties with my own juices from my intense orgasm. I wasn't sure what had come over me but I felt myself surrender sweetly to the feminine thoughts and feelings that began to flood my mind. We lay there with my head resting on his chest, both exhausted from heated lovemaking. When I got up to grab one of my cigarettes and another glass of wine, I could feel the cum dripping from my now tender anus, but it made me feel so womanly, so complete. I was really starting to feel pretty tipsy from the drinks I had during the night. Later, I brought a warm towel to clean Steve's wonderful cock. When he had recovered, I gave him a long sensual blowjob to set him off to sleep with. I soon collapsed in fatigue and lay beside him as I drifted off to sleep. The February sun was shining brightly but was already beginning to set when I awoke and Steve was gone. Soon, I realized that I was back in my own room, lying naked in my own bed and I discovered that it was late afternoon. I had been out all day !! I got slowly and found my way to the shower. I took a long warm shower until I had come around enough to sit in a hot bubble bath. I laid back and smoked a long cigarette trying to piece together the events of the night before. Why had I slept all day?? I hadn't had more than 8 drinks all night. Where was Steve?? ...And why was I in my own room?? I thought that I had remembered everything - the night at the bar and the great sex afterwards. Something was odd but I couldn't quite put my finger on it. Buy the time I had finished my bath and toweled off, my stomach was groaning in hunger. I decided to get dressed and go out for some fast food for a quick fix. I dug through my make-up bag searching for my polish remover but couldn't find it. Next, I went to change into my jeans and tee shirt - but they were gone also!! And then, I noticed it... a large manila envelope next to my suitcase with CINDY printed on it in big bold writing. I grabbed and untied the string to open it. What was inside shocked me. There were 2 dozen photographs of me in close-ups at various times through out the night. Several shots were of me sipping drinks and smoking cigarettes at my table in the bar in all my glory. Another set showed me happily sucking Steve's cock, while another set was me getting my brains fucked out by Steve in my lingerie. There were also transcripts of our intimate Internet conversations and videotape, which I played, that captured our entire session of lovemaking in Steve's room. There was a small hand written note that I picked up and began to read. It was from Steve, it gave me directions to his house and told me to come fully dressed as Cindy. Lastly, it told me to be there by 8 PM sharp or copies of the material would be sent to the list of addresses he had assembled - they were my family's and several close friends!! I had little time to get prepared and pack my things to check out of the hotel. Why was he doing this to me?? While I shaved, dressed, and put on my make-up, I pieced together some of the pieces to the puzzle. Apparently, I had been drugged, and he must have had a private investigator photograph me and do research on the addresses. But why? I had told him that I secretly wished I was a woman, but it was only a rouse to gain his interest and make myself appear more feminine. Maybe, he took me seriously?? When I was dressed and packed, I foregoed the checkout and threw my room keys on the bureau and headed straight to my car. Part 2 - Trapped My mind flowed with a thousand thoughts as I drove north on the Maine Turnpike. The overwhelming questions of my predicament had made driving difficult at best. But first and foremost, I was famished; I needed some food to help regain my perspectives. I pulled of the highway exit and drove to the drive-thru at a fast food restaurant. I nervously placed a quick order then politely paid the cashier. I pulled to the curb to get down some much-needed nourishment. When finished, I pulled close to the rear-view mirror to re-apply my lipstick and to powder my nose. Beginning to feel better as I drove, I again focused on the lingering crisis I had gotten myself into. I had to admit, the fucking I had gotten from the night before was heavenly, but I was still a man, I had a life to think about and an image to protect. Perhaps I had revealed too much about my intimate fantasies during our long Internet conversations? I decided that I'd go along with Steve's little game and be back to work on Monday morning as usual. I smoked my long cigarettes and listened to chick music on the nearly 2 hour drive, catching occasional glances from men in passing vehicles. At 7:45 PM, with 15 minutes to spare, I finally pulled into Steve's semi-secluded driveway on the outskirts of Augusta, Maine. I surveyed the large chalet styled house in front of me. It was very nicely kept, with a modern design. With another quick check to my make-up, I was out of my car and headed across a short walkway to the front door. Arriving at the door, I noticed an envelope taped to it in plain view with "CINDY" written on it. I removed it then carefully tore it open. There was a short letter addressed to me from Steve inside along with another set of compromising photos taken of me from the night before. The letter told me to come inside and that he would be home in an hour or two after he had finished some business. I was to proceed to the upstairs bathroom and then to freshen up which meant adjusting my make- up and making sure that I was sweet smelling. In addition I was to change into the outfit that would be laid upon the bed in the master bedroom and be looking my best for when Steve arrived home. I opened the door to a lovely and expensively decorated household and had a look around. My heels clicked and echoed on the wooden floors as I crept about. I went back to the car to retrieve my make-up and overnight bags then made my way inside and up the stairs. I found the master bedroom, which was large with full-length mirrored closet doors and a canopied king sized waterbed. I noticed my outfit laid out on the large bed and picked the articles of clothing up to examine them: a long-sleeved white shiny satin blouse, a red leather mini skirt, and red 3 inch pointed heels - all in my sizes. How did he know? I moved to the large adjoining bathroom and spread my make-up out onto the counter in front of a large mirrored vanity. I quickly stripped out of my outfit then removed my make-up so I could cleanse my face. After freshening up a bit and restyling my curly blonde wig, I began to get dressed. First, I choose my white silk n' lace underwire bra and matching satin panties. I placed a fresh maxi in my panties to hide my bulging cock from being noticed and to catch any accidents. Next, I squeezed into a white satin waist cincher followed by shiny nude ultra- sheer pantyhose topped with a silky white half-slip. I returned to sit at the vanity and began to meticulously apply my cosmetics choosing subtle but sultry shades to complement my facial features. When satisfied, I slipped into the soft silky blouse and pulled on the leather mini. I choose my best gold jewelry and some accessories to complete the look. Lastly, I stepped into the red pointed pumps and walked around for several minutes to get my balance and walk straight. I paraded around in front of the mirrored doors infatuated with the sexy creature looking back at me. I was abruptly shaken from my reverie by a sexy whistle. I turned to realize that it was Steve watching me from the doorway. "What is this all about?" I pleaded. " I'll tell you what you need to know later, for now put on this coat, we're going out for drinks," he told me. Steve handed me an expensive silk lined long white leather biker chick style jacket telling me that I was to be his slut for the night or else. Moments later, we were on the highway headed 30 minutes north to Waterville. I smoked a cigarette and made polite conversation during the trip. Soon we had arrived at a cozy lounge inhabited by middle and upper class clientele. We settled into a table out of the way so we could talk openly. Steve, being the top, ordered us drinks before we got down to business. Steve began by telling me about some of his past failed relationships. The women in his life had been sluts like he preferred. However, they were also full of jealousy, gold diggers, cheaters, or just plain bitches. One bad relationship after another had made him grow increasingly weary and frustrated with the female persuasion. One day while chatting on his computer in a lawyers chat room, a man told him about his relationship with a TG (transgender) male to female and how he had transformed her into a lovely submissive female. Steve did some research on the subject and made a few contacts before deciding to give it a try. After he had talked with me for several weeks online, he decided that I was a perfect candidate for his new venture. Indeed, he had hired a PI to dig up some info on me, and indeed placed hidden cameras in his room, and then drugged me to remove my male clothing from my room. The carefully designed plan had schemed to ensure my submissiveness. "But, but... I can't... I don't," I stammered in shock from his revelations. "You can and you will," Steve said sternly. "Besides, tell me honestly that you live a fulfilling life." He was right, my life had been rather boring and unsatisfying thus far, and I had to admit that the previous night had been the best fuck I had ever had. On the other hand, I did enjoy some aspects of my masculinity - hunting, fishing, sports, and of course watching sexy women. Also, I had a life, a house, friends, family, and a decent job with a livable wage. I refused to give it all up. "God, how'd I get into this?" I thought to myself, my eyes began to fill with tears. As our evening progressed, Steve came to sit next to me so he could run his hands up my nyloned thighs. I tried to ignore him giving him the cold shoulder but he privately kicked me in the shin then grabbed my hand bringing it to his crotch for me to rub. Dissatisfied with my less than agreeable attitude, Steve yanked me by the wrist and led me out to his car. Steve glared at me and his voice became stern, "You have better straighten your ass out right now, you little sissy slut or I'll make things really difficult for you and that's a promise," he blasted. He looked like he certainly meant it, I was terrified. "I'm... I'm sorry, please don't show them, I'm so sorry," I pleaded. "I'm sorry Master," he corrected me. "Get in the car, sit down, and shut the fuck up, bitch," Steve scolded. On the way home, Steve's demeanor lightened. He began to tell me that he specialized in corporate issues and represented some of the larger local companies as a contract attorney. His secretary had recently quit and he was tired of dealing with hired help. That's when he had realized that it would be cheaper for him to change me into his ideal woman and have me working as his secretary and assistant than it was to pay the wages and insurance for a real woman who was eye pleasing. He figured that a $30,000 per year salary over three years would be put towards my sex re-assignment and various surgeries. In three years time, his initial investment would begin to pay off and he could pay me a substantially lower salary, which he called it an allowance. But not only would he be getting a secretary, he'd also be getting much more - a maid to clean his house, someone to make home cooked meals, a beautiful woman to please him in bed, and an escort to accompany him on business and social functions. Best of all, I would be someone who wouldn't and couldn't give him back talk or use and abuse him, I was to be his loyal and loving slave girl catering to his every whim and desire without question or hesitation. Arriving back home, Steve ordered me to go up to the bedroom and change into something more comfortable. He informed me that my training as his slave would now begin. I quickly undressed and slipped into my black satin teddie ensemble and matching black silk robe. In the meantime, Steve had sprawled out naked on the bed and ordered me to give him a good blowjob beneath the satin sheets. I started to half- heartedly give him oral when he grabbed me by the back of the head telling me to, "Like it bitch." I gave in to my situation and devoured his thick shaft like a cock- hungry slut. Instead of letting my swallow his load, Steve pulled out of my mouth and blew his creamy spunk over my nose and chin as to assert his authority. While he recovered, I was ordered to give him a nice back and foot massage. "Ahhh, I could really get used to this kind of treatment," he teased. Next, I was ordered to kneel on the bed while he tied my hands securely to the bedposts. He grabbed my panties and shoved them into my mouth to gag me. I felt a greased finger sliding into my puckered asscunt before Steve mounted me pushing his rock hard cock deep inside of me. I was helpless!! Steve ravaged me for a good 15 minutes with an intense assfuck before shooting off inside off me. I buried my face into the soft pillows and began to whimper about my predicament - while Steve took his time showering and preparing for bed. Eventually, I was released and allowed to clean myself up and smoke a long cigarette before returning to bed. When I was settled in, Steve grabbed a pair of handcuffs from his nightstand and shackled me to the bedpost to prevent me from bringing myself to orgasm. The following morning I was awoke to a sharp stinging slap to my ass cheeks. Steve informed me that he had a morning erection that craved satisfying. He unshackled me so I could move into position to please him. I nearly gagged on his massive hard-on. When his cock was fully covered in my saliva, Steve ordered me to crouch above him and lower myself onto his cock like a woman. I moved to a squatting position just above the tip of his raging cock and gently lowered down onto him. I laid my hands on his rugged chest to sturdy myself while I bounced up and down on his manhood. Steve made me do all the work while he lay back enjoying a good long tight fuck. My fake titties jiggled tugging on the flesh of my chest with each bounce. Eventually he orgasmed filling me full with a powerful jet of his warm cum. To Steve's displeasure, I accidentally came on his chest, though I was warned not to. He forced my face down and made me lick up every last drop. I was allowed to freshen up before being ordered to prepare breakfast for my master. While he ate his meal at the table, I had to kneel on the floor beside him and lick my portion from a plate. I spent the rest of the morning running around in my lingerie cleaning his house in between giving several more blowjobs. Finally in the afternoon, Steve summoned me to his study. I was made to write out a confession where I revealed that I was a gay transvestite who wished he was a woman and was in love with a man. He told me that I could return home. I was so happy, I wanted to kiss him. But that soon faded, for the next words from him shocked me. Monday morning I was to quit my job. I was to bring back the deed to my house so he could put it on the market for sale. I was to tell my friends and family that I was taking a job out west and leaving town immediately. All my possessions would be brought to an auction company and sold. If I did not return within 72 hours, copies of the photos, video, and confession would be mailed to my family, friends, and coworkers. Over the following three days, I reluctantly did exactly as my master had instructed. I headed back to Steve's place on Wednesday afternoon resigned to the fact that my life as I knew it was over. Gradually, I began to accept the finality of my situation, and even felt a part of myself begin to look forward to a new start. After all, the sex had been great, I did enjoy dressing as a woman, and Steve was a cute guy. Maybe this wouldn't be so bad after all. I was even starting to get turned on by the idea. But what about my masculine hobbies, interests and pursuits?? I arrived back at Steve's house finding another note with CINDI written on it lying on the kitchen table. The letter instructed me that I was immediately to go upstairs and re- feminize myself. I would find some clothes in my size in the closet. When finished, I was to set out tidying up the house and to prepare and evening candlelight dinner for two. When I looked into the bedroom closet, I was stunned. There, in front of me was at least a dozen different outfits and dresses, 3 drawers full of lingerie, 6 pairs of heels in different colors, a box of lovely jewelry, and several sexy wigs - a crossdressers paradise!! In the bathroom I found a box full of cosmetics, bathing products, skin care products, maxi pads, hairsprays, and a carton of Virginia slims 120's. I ran a warm scented bubble bath and soaked for a while contemplating my new life as Cindi. Later, I applied dilipatory lotion to my chest, arm, legs, and ass making then completely hairless. I used moisturizers and powder to soften my skin. I attached my breast forms then slid into my lingerie to paint my nails. I carefully applied my make-up and styled a long curly strawberry blonde wig then finished by pulling on a lavender silk blouse, nude ultra sheer hose, corset, and black silk skirt. Some jewelry, black heeled half boots, and sexy perfume completed my transformation. I began to clean the house and rummaged through the kitchen trying to piece together a meal that would please my master. God, I felt like a slutty housewife. Steve arrived just as I lit the candles for our dinner. His attitude was relaxed as we sat down to a cozy romantic dinner. He was obviously impressed with the effort I had put into preparing myself, cleaning the house, and a good meal. After dinner, he brought me a gift to reward my excellent behavior, a box with a dozen long stem roses. In my gratitude, I moved close to him for a passionate kiss. This wasn't so bad, I thought to myself. To celebrate my new beginning, Steve broke out a bottle if expensive looking champagne for a toast. After I had cleaned the table and finished the dishes, Steve called me into the living room. He handed me several pages of documents for me to review. The first page was a set of his rules for me that I was to closely follow. The second page were directions to The Glamour Boutique in a Boston suburb. The third was directions to a Mistress's house in Auburn, Maine. The fourth was a list of assignments dealing with feminization that I was to look up. Lastly, there was a contract for me to sign. The contract was drawn up very legal looking which basically stated that I willingly submitted to Steve as his personal property and agreed to do anything that he had in mind for me. I had no choice but to sign my life over to him. Hesitantly, I picked up the pen and scratched out my signature knowing full well that my life was about to take an abrupt change. Part 3 - In Training After I had studied the rules that my master had set out for me, I was instructed to go and change into something more suitable to begin my training in. I searched through my new collection of lingerie before selecting a white silk and lace teddie with a matching satin robe, white lace stockings, and 4 inch white heels. When I was finished dressing, Steve led me down into his basement. He gave me a mini tour starting with his entertainment room with bar. The other end of the basement had a laundry room. Another room to the side was fully set up as a gym with exercise equipment. Lastly, he led me into a room that he had converted for sexual purposes. A cabinet contained restraints and sex toys. There were hooks bolted into the ceilings and floors. In the middle of the dungeon was a padded leather reclining chair with a stainless steel frame. I'd read erotic stories about people having such places but I couldn't believe that Steve would actually have one. Steve sat on a puffy satin upholstered love seat while ordering me lean over against the half- reclined leather chair. Next, Steve told me to rub my fake tits and ass like a hot and horny woman. My master even let me remove my cock from its silken confinement and stroke it 'til I was begging him to let me cum. Steve's next move was to grab the centerfold of a PlayGirl mag and place it in front of me. Soon he was rubbing my ass like I was his slut. Steve pulled the back of my panties aside and started probing my puckered anal opening with the tip of his penis. He spread my ass cheeks wide and forced himself into me in a thunderous thrust. The scene was so intense that I released a jet of sticky seed all over my panties in a quivering climax. When Steve had finished ravaging my ass, he ordered me into the chair and then fastened the padded leather restraints securely around my wrists. Next, he removed my cum soaked panties and stuffed them into my mouth. Lastly, he tied a black silk blindfold around my eyes. I was completely trapped and helpless, unable to escape my confinement. I felt his fingers pinch some of the flesh on my side, then a sharp sting of a needle. I tried to scream but couldn't, I was terrified. I began to hyperventilate. Steve held my hand and removed my gag to calm me. "Relax sweetie, it's only a dose of estrogen," Steve said softly. He went on to explain that hormones would be necessary to re-shape my body into a more womanly figure. He told me that corset training would help my body redistribute fats to my ass and hips to give an hourglass shape. The hormones would help to develop breasts (along with implants), lengthen my hair, and soften my skin. "But I don't want to..." Steve held his hands to my mouth to prevent me from finishing. "But I do," Steve said forcefully. "Here, this will help you relax" Steve said as he popped two tranquilizers into my mouth giving me a sip of wine to wash them down. When the pills had started to kick in, Steve fastened a pair of headphones to my ears - using a silk scarf to tie them securely to my head. "And this will calm you down and help you to relax also," he reassured me. I lay back comfortably numb, as a woman's soothing voice began to speak while soft music played in the background. I listened as the sweet voice began to instruct me to breath in and out in certain rhythms. Within several minutes, I felt a state of total relaxation wash over me, probably brought on by the tranquilizers. I became mesmerized by the woman's voice as I drifted deeper into my relaxed state. The woman began to make suggestions about feminine and womanly dress, actions, and mannerisms. The voice reminded me of the joys of crossdressing - soft smooth skin, sweet scents, the caress of silk and satin lingerie against my skin, lovely feminine hair, sexy make-up, having large womanly breasts, and using woman's products and items marketed to women. The voice went on to suggest that I do my best at portraying a beautiful image of a woman, that I sit to pee, and suggested that I study the actions of other beautiful women to learn there actions and the way the moved and walked. The last I remembered the voice was describing the joys of pleasing your man and the virtues of being a good wife, lover, housekeeper, and slave. Two hours later when the session finished, I was awoken from the trance feeling more relaxed and refreshed than I had in years. Steve had released me from my confinement sometime during the session. I wasn't immediately aware of the suggestions in the later parts of the session but god, I had never felt more womanly when I saw my reflection in the large wall mirror in the chamber. I made my way upstairs to join Steve in bed. I didn't know what had come over me all of a sudden, but I wanted Steve in the deepest desire I had ever felt. The man inside of me screamed out that I shouldn't be feeling these longings for another man, I had a life with family and friends and masculine activities that I enjoyed. However, in the end, I was helpless to resist the sweet surrender to the compulsion to climb in bed with Steve and give him the best blowjob ever. We sucked and fucked until the wee hours of the morning. Never had I derived so much pleasure from sexual intercourse, this was better than any sex I'd ever had as a man did with a woman. In the morning, I awoke Steve for work with my lips wrapped around his morning hard-on. Later, while he showered and then dressed for work, I prepared a full breakfast for him as directed in the rules Steve had made for me. Later, after he'd left for work, I slipped on some exercise clothes and made my way to the gym in the basement. I hadn't exercised in years but strangely, I felt compelled to lose weight and get into shape. I peddled on the exercise bike for over 2 hours until my legs and buns were burning. During a rest break I found several aerobic workout tapes, popped one into the VCR, and played it on a large screen TV in the gym. I went through 4 complete workouts before I was over come with exhaustion. Later I relaxed in a long scented bubble bath before I shaved and sat for a long serious make-up application session. I dressed in a silk blouse and tight shiny spandex leggins and short heels to do the house work in. I scrubbed the floors, vacuumed the carpets, washed all the windows, and did all of Steve's laundry. By late afternoon, the house was in immaculate shape. I Knew Steve would be home in about an hour, so I began preparing a hearty meal for him though I hadn't been hungry all day. That evening after our dinner, again Steve led me to the basement room for more training and discipline. He had me take a tranquilizer and again, Steve bound me to give a hormone shot to my side and then fastened the earphones securely to my head for my feminization hypnosis session. And again we wound up having hot passionate sex later in the night. This routine went on for the next several weeks while Steve had been busy completing an important contract with his clients. I found myself immersing deeper and deeper into my new role as a female. One day Steve announced that he had to fly out West for a week of negotiations and that he wanted me to go to a Boutique in Mass. that catered to crossdressers and transgenders to get a glamour girl makeover. We would meet for a night on the town in Boston before he flew out. He had already made an appointment for me with a T-girl named Charlene at the Boutique/Salon for the following day - a Friday afternoon. The next morning, I packed a few things to bring with me and took special care in preparing for my trip. I dressed in a sexy shiny silk blouse and tight silk mini and styled my sexy blonde wig to look provocative. Before I pulled out of the driveway, I gave my lips another coat of wet red lipstick and pulled on a pair of chic sunglasses. During the 4- hour drive I became aroused by all the attention I was receiving from guys as they drove by me on the highway. I smoked my long cigarettes seductively and smiled back flirtatiously licking my lips. Soon I had arrived at the Glamour Boutique in Woburn, Mass. I approached a lovely woman sitting behind a counter and asked for Charlene. To my surprise, the lovely vixen in front of me was indeed Charlene. We exchanged some pleasantries, then Charlene started to explain the makeover package that I would be receiving. Charlene told me that Steve had paid a substantial amount of money for her to give me the ultimate look of femininity. First, I was led to a salon and changing room area. Charlene told me to strip naked and put on the nylon smock hanging in the large private changing room while she made a few selections for me. After several minutes, she joined me in the private room. She opened a small box to reveal a larger set of life-like silicon breast forms. She helped remove my set then applied a special adhesive to my breast area before attaching the new set firmly in place. The 38 D breasts fit snuggly but tugged my skin from their increased size and weight. She told me that it would take some time to get accustomed to the weight and bounce, but that the black silk bra she handed me would help. Next she handed me a matching silk g-string type panty that she explained was a penis gaff designed for crossdressers and female impersonators to smooth the bulge in my crotch area. She helped me put the gaff on having me insert my cock and balls into a specially built in pouch so it could be pulled between my legs and tucked securely out of sight. Now my crotch was smooth and featureless resembling an actual woman's. Charlene gave me a pair of soft silky French cut black panties to wear beneath my smock during my makeover. She brought me out to a beautician's chair and sat me down. First, she would start on my hair, she would die my hair to match the weave and extensions she would be adding to give me a more natural look until the hormones could grow thicker my thinning hair. While she worked her magic during the lengthy process, her assistant Lori (another sexy T-girl) gave me a moisturizing facial mask and a full manicure and pedicure before applying 3/4 inch acrylic nails to my fingers. When Charlene had finished, she began my cosmetic makeover by removing my facial and applying a layer of foundation. Soon both girls were working diligently helping to apply my cosmetics, explaining their methods and adding helpful hints as they went along. After 20- minutes the girls announced that they were done and rotated my chair so that I could face the mirror. I was in awe - there, in front of me was a reflection of a beautiful woman staring back at me from the mirror. As I gazed in disbelief at my reflection, Charlene retrieved a few of the outfits and dresses that she had selected for me. After trying on several different combinations, I settled for a dazzling vermilion pink satin blouse with modest sequins and a tight black silk mini skirt. Charlene handed me a pair of black strapped 3" spiked heeled pumps. It was amazing, I had never felt so much like a woman - I mean really felt like a woman. I noticed that it was getting late and decided that I'd have to hurry if I were going be on time to meet Steve in the hotel bar as he had instructed. I thanked the girls for their incredible services and exchanged pleasantries before bidding good-bye. Minutes later, I had joined Steve in the hotel bar which was trendy and upscale. He was genuinely impressed with my appearance to say the least. Steve whistled in approval of my convincing womanhood, sexy attire, blonde locks, and bigger bust. I loved the compliments he had for me. God, what was happening?? "I'm not a woman," I tried to remind myself, but it was all futile - I could not resist the urge to fall deeper and deeper into my new life. The hypnosis was altering my entire thought process and the way I viewed myself and the world I was living in. After a while, Steve's conversation turned to me taking an even more feminine role and having my breasts enlarged with implants and more hormones. He also told me that I would get some cosmetic touch-ups and a face-lift to make my face softer and rounder. He had me scheduled for a week of surgeries with two plastic surgeons had had been associated with. He had also enlisted me to be the servant of a professional domme who would put me through a month long finishing school to refine my personality and mannerisms to move more gracefully and feminine. With help from transsexuals online, he had designed a regimen to ensure that he could wipe out as much of my remaining masculinity as possible. Eventually, when I had progressed, he would see to it that I would have a complete sex-reassignment-surgery. He would have my identification legally changed to female. He also told me that soon I would become his wife and that I'd better learn properly to be a woman. I wanted to voice my resistance but it was hopeless, his decision was final!! Steve changed the subject with ease, but I was stuck on his words. It took several more drinks for me to be able to think about anything else, and after several more I had loosened up enough to begin to accept the inevitable. Soon, I was feeling not only acceptance of my situation, but to my amazement, I found that I was looking forward to becoming his woman. Goose bumps flooded over me in a rush of excitement as my resolve to become fully feminine strengthened. Finally, I caved in fully to sweet surrender to silken femininity. I began to experience a whole new range of emotions and feelings. I realized that I felt safe and secure when I was with him. I sensed that he had deep feelings for me and that he had come to need me and depend on me. We had an unspoken bond and trust in on another. I wanted to please him, I wanted to arouse him with my beautiful sexy looks, smooth womanly body, and feminine actions and thoughts. It all made sense to me now. The things I loved to do when dressing, shaving my legs, wearing sexy silk lingerie, sexy dressing, make-up, perfume, heels, and jewelry - all were so exciting because they we comforting me that I was a pretty woman in the eyes of my man. I truly wanted to be a total and complete woman in all aspects. My focus soon shifted to my feelings of friskiness and slutty thoughts. Steve was indeed a cute hunk of a man, financially secure, and was very charming beneath his dominating exterior. "God, I want him, I actually have the hots for him," I thought to myself. I pulled close to him and kissed him deeply and passionately as to seduce him. I actually found myself saying to him, "Thank-you for doing this to me." I told him that I loved him and wanted him to fuck me good, I'd do anything for him. Steve and I retired to his room at the stroke of midnight. I couldn't keep my hands off of him. I couldn't help myself - I wanted him, I wanted him in me, I was drunk and horny. I pulled Steve's shirt off and unbuttoned his pants as I kissed his chest and licked his nipples. Soon, I had pushed him onto the bed and I had wrapped my glossy lips around his hardening shaft. I sucked and slobbered over his shaft like a lust-crazed tramp. I slowed my assault when he was fully erect in my mouth so I could prolong his enjoyment of what must have been an incredible blowjob. Insatiably, I devoured his delicious cock, swallowing a warm creamy load of his savory spunk like an expert. Later, Steve banged my puckered asscunt like I was a porn star, while I moaned and whimpered in ecstasy. Never had I felt so satisfied and so complete. I was in total heaven rocking back and forth on my knees to meet his hard thrusts. The sensation of being filled deep with cock and the texture of his thick cock stretching my delicate oiled anus felt natural and absolutely marvelous! I remember happily thinking to myself as I drifted off to sleep - "So this is what it'll be like to be a woman, I Can't wait!! I really am Cindy now." THE END?? Steve's Rules for Cindi starting with a 3 month period. Print this out and keep it handy. Rules and Requirements 1.) Written assignments with pictures will be a requirement to keep your man informed of your progress. 2.) You will smoke 1/2 pack of Virginia Slims Luxury Lights 120's Regulars per day, thinking only feminine thoughts during. 3.) You are to start a feminization diet immediately and will lose 20 pounds during the next 3 months. 4.) You will sit to urinate making sure to wipe when finished. 5.) 3 times weekly you will soak 30 min. in scented bubblebaths lit by Glade scented candles while smoking your Virginia slims Luxury Lights 120's regs. 6.) After bathing, you will apply Neutrogena sesame oil to your body along with scented moisturizers. Excellent personal Hygiene will be a must. 7.) In addition to your maxi-pad, for one week each month you will wear a tampax tampon fully inserted in your girly hole. 8.) You will wear Secret Powderfresh Platinum Protection anti- perspirant/deodorant at all times. 9.) You will watch only television shows and channels that are of interest to women, soaps, talkshows, no news or sports. 10.) You will wear silk panties with maxi-pad; keep your toes painted pink, and be pleasantly sweet smelling at all times. 11.) You shall wear lingerie, nylons, and silk scrunchies on your wrists at all times when alone, 12.) When showering, you shall apply Caress or Dove neutrium to your pink bath puff and wash with it. 13.) You will practice make-up application for 1 hour each week. 14.) Twice a month you will take pictures of yourself fully dressed in femme at a public location. 15.) You will buy yourself a woman's razor and shave gel to keep your body smooth and freshly shaven at all times. These rules are meant to be simple, but will help to reinforce your femininity and submissiveness. You will keep me informed on your progress adhering to these foundations. Tasks 1.) You will buy Cosmo, Playgirl, and a feminine magazine of your choosing EACH month and choose 2 articles from each and write a short paragraph about how each pertains to you and benefits you in becoming better able to please a man. 2.) You will go to the health food store, get 1 bottle each of Black Cohash and Blessed Thistle, and take 4 capsules of each per day. 3.) You will find a full feminization hypnosis audio session and listen to it each night before going to sleep. (I recommend that to check the web for a feminization Mistress or Apronstrings.com) Get to work on this because this is very important !!! 4.) You are to post the above rules on your webpage as an annoucement to the world that you strive to be a complete woman. 5.) During the next three months, you will save enough money to buy a silk French maids full outfit, an ultra feminine bridesmaid/prom dress, and acquire a super feminine satin wedding gown (second hand will serfice). 6.) You will go to fictionmania.com and search for 3 REALISTIC stories using a keyword search with the following: hormones, breast implants, the operation, wedding dress, nails, salon, lingerie, heels and Frenchman. Each month you will read one then write a 1-page summary and how the story effected and pertains to you. 7.) You will search the internet for information about the entire sex- reassignment process from start to finish then write a 3 page report so I may use this information to help prepare you for the transition. 8.) You will post a message with pictures on ALL the New England yahoo TV clubs announcing that you are now considered a shemale pre-op transsexual and will seek advice on transitioning. 9.) You will find a post-op transsexual either locally or online and seek out her friendship and guidance during your transition. 10.) You will practice walking gracefully and naturally in 3" pointed heels and refining all your feminine mannerisms such as crossing your legs, softening your voice, and checking yourself in the mirror. 11.) You will purchase 1 BLACK and 1 WHITE Hanes-her-way silk-n'-lace underwire bra size 36D and matching silk panty for each. (You will fillout the cups with breast forms, enhancers, or padded quality water filled balloons) 12.) You will purchase at least 2 oversized, long sleeved satin or silk sleep shirts for you to sleep in every night. 13.) You will purchase at least 2 XL long-sleeved silk blouses, one solid shiny white the other a color of your choosing. 14.) You will purchase at least 1 pair of tight shiny Black spandex leggin's and 1 leather mini-skirt to wear with the above. 15.) You will make a complete and detailed inventory of your entire femme wardrobe and beauty supplies and submit it to me. (So, I can tell you what to wear) ** You will also be expected to regularly report to me on your progress in completing the assigned tasks, remember you have 3 months in which to accomplish these tasks that are designed to help you achieve true womanhood.