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Part 2 I was born Kelly Stark. I grew up in a town of about 60,000 people. It was big enough that people minded their own business but small enough to allow kids to be able to breathe. Looking back, something was wrong for as long as I can remember. I'm not going to bore you with details about my family or any of that. Let's just leave it that as a kid I sometimes wore my sister's clothes. I would put on her clothes and jack off and pretend I was her with some boyfriend of the moment. Mom caught me once. She asked if I wanted to be a girl. I lied and said no. I quit cross dressing at home though right then. I grew up to be 6' tall with blonde hair and blue eyes. I had a fair skin coloring and I am considered a good looking guy even though I'm not like some lantern jawed cartoon character. I have "fine" features as my mom says. I have a degree and I'm a successful businessman. Let me go back and tell you where my life started going out of control. Chapter 1 I was 18 years old. I was leaving for college to a state university almost 200 miles from home. I had been a popular kid in high school. My girlfriend, Debbie, had been Homecoming Queen and a cheerleader and a gymnast. She was a petite girl of about 5'1" and she weighed 110 lbs. She had a smokin' bod and was a lot of fun to be around. She wasn't the sharpest pencil in the box and college wasn't in her future. I thought I loved her and she felt the same. Our sex life was like most teenagers; grab-n-grope, countless hours with me begging, hand jobs...pretty much like almost everyone I suppose. I was the slightly above average kid who never really took life seriously. I was on the sports teams but never really played much. I went away to school and I loved it. My mom and dad had been pretty strict while I lived at home. When I got away to school it was "party time". I went to parties and drank beer and smoked pot. I managed to go to class but studying wasn't a part of the program. I went from being an A & B type of student in high school to straight C's my first semester. Debbie had even come up and visited a couple of times but I was a "load" and she saw the handwriting on the wall. She ended it over semester break which was fine. I had already started dating other girls anyway. My parents sat me down after semester though and we had "the talk". Their message to me was that they weren't paying for C's. If I wanted to be a C student then I was on my own dime for school. So I added the occasional study session to my repertoire of attending class and managed to bring everything up to at least a B for spring semester. But weekends were filled with parties and chasing girls. My roommate pledged a fraternity and moved out. This allowed me to have the occasional "sleepover" and I got a bit of a reputation. This made it harder to pick up girls but WTF. Chapter 2 Life pretty much stayed the same for the next couple of years. I went to school and partied. I worked in the summer delivering furniture from a store in town but I partied then as well. Then my junior year, I met Jillian. She was 5'6", blonde and blue eyed. She had a gorgeous face and a smoking bod. I was totally in love. She was smart and funny. At the end of our junior years, I asked her to marry me and she said yes. We didn't set a date but we did move in together. It started out awesome. We were 'in love' and we did things together and we had fun and we studied and I partied. I'm not sure what happened but after about 6 months, she started "going to the library" and "working late" at her part time job. At about 7 months she came home and asked me to move out. She had been seeing someone else and it was over between us. I moved in with some friends and went in to a tailspin. I was devastated. I barely finished spring semester but I held it together with mostly B's and one C. My parents were understanding but they made it clear that I needed to move on and that my senior year would have the same expectations as before. My sister, Jamie, was in Europe for the summer. She was in grad school and majoring in Art History. My parents always held her up as an example. She was a straight A student and Valedictorian of her high school class. She was engaged to a guy by the name of Wyatt that she had met at college. He had been president of his fraternity and was now at Harvard Law School. I started sneaking back into her room that summer and wearing her panties. I was ashamed of what I was doing. She was this shining example and was going to have a wonderful life and I was a partyboycollegeguy who fantasized about sucking cocks while wearing my sister's panties. Chapter 3 I finished college with a degree in communications. I started interviewing for jobs. I interviewed and interviewed and sent out resume after resume. I was 21, living at home, and I was back in my "summer job" of delivering furniture. One day, I saw an ad online and it was for a researcher at an Executive Search Firm. I posted my resume and then got a call to come for an interview. When I got there I had to fill out a lot of paperwork and then I had to do a bunch of psycho logical testing which scared me. Then they sent me home without really talking to me. They called the very next day and asked me to come in and meet one of their "Executive Recruiters". I did and we hit it off. His name was Bob and they offered me the job which I accepted. I wasn't going to get rich overnight but I had a base salary and then I could make bonus if the projects that Bob assigned to me came together. So I quit my furniture job and went to work with Bob. He had 4 researchers including me. We worked well together and after 6 months, we had the number 1 team in the firm. I had moved out to an apartment and life was awesome. I was partying on the weekends and working my ass off during the week. I was learning the business from a guy I thought was the best. When I had my first performance review, the only criticisms Bob had of me were that I needed to be more assertive and that I needed to project on the phone. I was kind of soft spoken and sometimes people called me "miss" or "ma'am" because of my name and being so soft spoken. I also know that for some reason, I didn't have to push as hard as my other male colleagues to get through to people. I also didn't get as many questions about why I was calling. But I also was starting to accumulate my own female wardrobe. I was cross dressing sometimes on weekends, mostly for my own enjoyment. I occasionally played in the chat rooms but never agreed to meet. I wasn't doing it all the time but once or twice a month, I would spend the weekend at home. Then I met Joni. Chapter 4 Joni was a successful career woman that worked in the communications industry. She was 6 years older than me. Joni was 5'10" and wore a size 10 dress. (Why did I know that?) She was a brunette with brown eyes and a pretty face. She was ambitious and hard working. We had met at a party by mutual friends. Despite our age difference we hit it off and I asked her to meet me for a drink. Joni was a very well built woman. She had been a swimmer and still swam for fitness purposes. She never seemed to have a hair out of place and I could see her perfectionism right away. So we met for a drink and decided to see each other again. She worked long hours and traveled a lot but I liked her and I was willing to accommodate her schedule. After all, I worked pretty long hours myself so we had to make an effort. We liked each other and only dated for 3 months before we married. I never told Joni about my cross dressing and I purged my female clothes. Our sex life was never "rock your world" but it was adequate and when we were on vacations together was always better because we could both pay attention. I know that sounds strange but in many ways we were alike, driven and ambitious and hard working. The major sources of conflicts between us were her perfectionism and my lack of maturity. From the outside we had a good marriage. But as with many things, all was not as it seemed. Chapter 5 I was 22 when we got married and Joni was 28. She was already successful and I was trying to be. She made more money than I did. She was a perfectionist and sometimes kinda bossy. I was immature. She didn't want kids and I was uncertain but thought maybe I did. We kept separate finances and she sometimes complained that I didn't make enough because she could afford to do things that I couldn't but it was her idea to keep things separate rather than pool our resources. See how it went in circles? So like a lot of couples early in their marriage, we fought some. But unlike many, rather than work it out, we both withdrew to our work. She was traveling a lot and many times left without resolution. One night, I got home from work and I made myself a sandwich and, instead of my usual glass of wine, I had a scotch and water. I ate my sandwich and then decided to have another drink. Feeling a little sorry for myself for being married to such a bitch, I had a third drink but this one had no ice and no water. I was "feeling it" by this time and I went back to our bedroom to watch TV. I walked in took off my clothes and put my normal sweat pants for bed. As I was laying there I looked at my wife's dresser. The drawers on the right side were all hers and mine were on the left. I got up and walked over and opened the top drawer on the right side. It was her bra and panty drawer. The scent of her sachet hit my nostrils and sent me into overdrive. I took off my tee shirt and sweatpants and briefs. I took out a matching pair of panties and bra. They were a wine color with black lace. I sat on the bed and pulled the panties up my legs until they settled gently in to place. They fit. She was the same size as me. Then I took the bra and turned it around and fastened it in front. Then I turned it back around and pulled it up, putting my arms thru the shoulder straps. It was a little tight but not awful. Joni was a "B" cup. I didn't have breast forms so I grabbed a pair of socks which filled in the cups of her bra. Then I looked in the mirror. God I was so turned on. I went out and got another drink and then went back in and got on my computer and went in to the chat rooms. I had "cyber" with two different guys without the cam on. The second time I was touching myself the whole time. I must have cum for a full 2 minutes. I cleaned myself up and then went to bed. The alarm went off the next morning and after two cups of coffee and some Advil, I was able to get ready and go to work. I felt guilty and ashamed but I did the same thing that night without the alcohol. Only this time I tried on some of the clothes in her closet. Almost everything fit. Chapter 6 This began a pattern. Joni would travel on business and I would come home and dress up. I got a post office box and began to order some other things like a good wig (shoulder length, ash blonde, human hair), breast forms, my own make up (My coloring was fairly close to Joni and so I started with her brands and tones. A few years later I learned that I had chosen wisely), a few pairs of shoes that would go with some of my favorite outfits, and a dildo (I liked to put in my mouth and pretend I was sucking a cock when I was dressed). I kept all of these things in a locked suitcase that lived in a dusty old corner of our attic. I knew she would never find them since whenever she needed something from the attic she always asked me to go up there. I was ashamed of what I was doing but sometimes when I was completely dressed with makeup, I felt a sense of almost euphoria that I never felt before. It was almost as if it was somehow "right". This went on for the next 3 years. Joni would travel and I would dress. I never went anywhere because I was afraid of getting caught or seeing someone I knew. But sometimes I would go for a drive. I don't know what I would have done if I had car problems but I didn't think of that. During this time my maternal grandmother had passed away. She was very sweet and I had spent a lot of time with her when I was little. She always watched my sister and me when mom and dad had a date night. She was modestly wealthy and left both my sister and I about $250,000. I put most of mine in the market, companies like GE and Microsoft and Berkshire Hathaway. I also put about $30,000 in an "emergency fund where I could get my hands on it. It was just a passbook saving account. By this time, Joni and I were in separate bedrooms. We never had sex and most of the time we were pretty much in to our own stuff. Even on weekends, she did her deal and I did mine. I enjoyed yard work and being outdoors with my shirt off and she would read and work from home. I didn't have a great body for a guy. I wasn't overweight but I wasn't a muscle head either. I weighed about 155 lbs and I had inherited my dad's muscular thick legs. I ate like a horse and always had trouble keeping my weight up. My skin "tanned" well and sometimes my hair would bleach out a little in the summer sun. Sometimes I would lie in the sun on our deck in my briefs. We lived on acreage in the country and there was nothing behind us but a big open field. At work, I had been promoted. I was now the manager of all the research assistants at the firm (12 people, 10 of whom were women). I was making almost as much as Joni. Bob was no longer my boss and I reported to the owner of the firm. My title was Office Manager. It was August 1. Chapter 7 The union at the company where Joni worked was going on strike. This meant that many of the managers would have to go to other cities in order to staff those positions. They were going to be put up in apartments and they had to stay for the duration. She could be gone a day or she could be gone for 6 months. Nobody knew and the union had already staked out a hard line position. So Joni packed two suitcases this time. (Fortunately not taking most of my favorite things.)The union was threatening to walk on Saturday at midnight. I took her to the airport on Saturday morning where the company had rented a 747. If they settled at the last minute, then she would be back home Sunday. If not, then I didn't know when I would see her again. We promised to talk every day. I had decided to throw caution to the wind. I wasn't going to try to get caught but I was going to start to let my fem side live. On the way home I stopped and got a pedicure. It's not unusual anymore for men to do that but it was my first time. Then I stopped at three drug stores where I bought several bottles of depilatory lotion. I went home and drew myself a nice hot bubble bath. I soaked for a good half hour then stood up and covered every square inch of my body below the eyebrows with the depilatory. With blonde hair, I wasn't profusely hairy but I wanted to get rid of all of it. I waited the required amount of time and got in the shower. The drain plugged twice but by the time I was finished, I was smooth like a newborn. I couldn't believe how it felt. Just walking through the house with my smooth hairless legs was incredible. I sat and crossed my legs and then recrossed them just reveling in the way it felt. I then proceeded to paint my toe nails a bright red and watched TV while I waited for them to dry. A few weeks before when Joni was out of town, I had decided to go out to an adult novelty store that I used to go to once in a while before I met her. It was late afternoon on a Saturday and I had applied some foundation and face powder along with some eye liner and mascara. I was wearing sunglasses but I'm sure it was obvious that I was wearing makeup. I was the only one in the store and I had decided to purchase a very sexy pair of black panties "for my wife". I walked up to the counter and I had had a few friendly chats with the clerk before. His name was Don. He was a biker type. He was showing me a naughty book he was reading. I couldn't quite see and so I took off my sunglasses. He got a big grin on his face. I was puzzled and then remembered the eye makeup. I'm sure I blushed bright red. I gave him my credit card and he reached out and tweaked my nipple through my tee shirt. I looked at Don and he said, "You should come out to the 'The Backdoor' some Saturday night, Kelly girl. It's drag night." I smiled. "Maybe I will." I left and went home and fantasized about sucking a biker cock. So tonight, I was going to get dressed and go down to The Backdoor. The show started at 10:00 so I wanted to be there at 9:30. I went out and lay in the sun for a couple of hours. It was so wonderful with my hairless legs and body and sun tan oil. About 5:30 I came in and drank a Gatorade and had a salad. Then I hopped in the shower and luxuriated in the water running over me. After I patted myself dry, I used Joni's Victoria's Secret Strawberries & Champagne body lotion. I so wanted to smell pretty. It was about 6:30 and I was good on time. I put on a sexy pair of lacey black bikini panties and a short cover up and went and made myself a scotch on the rocks. I sat with my legs crossed and watched the news. It was about 99% that the union would strike. At 7:00, I turned off the TV, made another scotch, and went back and sat at Joni's vanity with my makeup kit. I decided on a more dramatic evening look that I had studied on youtube. Forty five minutes later, an attractive blonde woman with short hair looked back. I stood and removed the cover up and applied the adhesive for my breast forms. They were a "B" cup and almost unbelievably realistic down to the cleavage. I attached the breast forms and waited for the adhesive to dry. Then I applied makeup around the edges and looked in the mirror. Unless knew, you couldn't tell. I had an instant erection which I took care of and then I "tucked" my boy parts back between my legs and pulled my sexy panties back up. I put on the matching demi bra and the effect was so very real. The dress I selected was a black dress with short sleeves and V-neck. It had lots of lace and the pleated skirt came to about 4 inches above my knees. It had a black belt which I tightened enough to accentuate my trim waist. My hips were boy hips but I had a cute butt and I loved the way my dress swirled around my hairless legs and panty clad bottom. I was going bare legged tonight because I had an awesome tan and it was still summer. I reached over beside the bed for my shoes. I had selected the strappy sandals with a two inch heel. I was after all 6' tall and I wanted to show off my pretty pedicure. I was almost finished. I put on my wig and brushed it out. Since it was human hair I could style it a bit and I put a few loose waves in it with my curling iron. I anchored the wig with a few pins. I added a delicate chain bracelet and a pair of clip on hoop earrings. Then I attached some bright red glue on nails. I looked in the mirror. I found it very exciting and erotic but I also felt a sense of being myself. I sat and peed one last time then pulled my panties back up and 'tucked" again. It was 9:00. I finished my drink, grabbed my keys and my wallet and put my wallet in one of Joni's purses. I also grabbed my lipstick, my compact, a travel size KY, nail file, tampon, and a condom. Hearing my heels click on the concrete even as I walked in to our garage was very exciting. I got in my wife's VW Bug, hit the garage door opener and turned the key. I headed for The Backdoor. Chapter 8 I had to park 4 blocks from the bar. So I grabbed my purse and swung my legs together out of the car and stood making sure everything was in place. I stepped away from the car and hit the lock button and put the keys in my purse. I turned and started toward the bar. I had practiced walking in a feminine manner with my elbows out and with a certain sway. I also knew that most "queens" overdo so I tried to be as realistic as I could. I caught a few people looking at me as I passed but nobody stared. One single guy who apparently was already a little drunk whistled. I was on cloud nine. I got to the bar and had to show my ID. The bouncer looked at it and then at me. He smiled and winked. "Have fun." He said. The place was already crowded but I found a place at the bar and ordered a Cosmopolitan. I looked around a little and noticed that a few men were looking at me. I turned back around and my drink was already there. I opened my purse and took out a $20.00 and when he brought the change back I left a couple of dollars on the bar. So I sipped on my Cosmo and watched things. I finished my drink and the bartender brought me another. I was getting a little buzzed at this point. I felt a hand on my hairless arm and I turned. It was Don, the biker guy from the adult novelty store. I smiled and we started talking. He bought me another drink and I had to pee again. I asked him if I should use the men's or women's and he told me men's. So I went and sat down. I finished and washed my hands and re did my lipstick. As I left, I heard another whistle. I got back and Don was still there and the show had started. He invited me to join him and his friends at a table. I sat and I talked to him. There was another girl there and we talked too. Suddenly I felt Don nudge me. I turned and he handed me a coke vial with a little spoon attached to the top. He looked at me and I looked around the table. It appeared that everyone was "sniffing" more than they should. So I discreetly did some like I had seen on TV. Holy shit! I suddenly became the "sexiest bitch in the bar." I was kissing Don and we danced between shows. He gave me another 'hit' of coke and then he leaned over. "Hey Kelly girl? Wanna go out to my car and fool around?" I smiled and nodded. His car was in the alley behind the building and we got in and he started kissing me and feeling up my breast forms. I was so hot and I was moaning and with my soft voice I know I sounded like a girl. Then he reached under my dress and started to caress my inner thigh. I spread my legs like a girl and he rubbed my crotch. Then he took my hand and put it on his pants and I felt his rock hard cock and I started rubbing it. He moved his hips and said, "Take it out Kelly girl." So I undid his belt and unzipped his zipper and took a hard 6 inch cock in my hand that didn't belong to me. We were kissing and he was rubbing me and I was jacking him off. Suddenly he looked me in the eyes and said, "I want you to suck my cock, Kelly girl." God I was so hot and so I did. It didn't take long until he tensed up and grabbed my head and forced it down my throat. All I could do was swallow and I had to swallow 3 times. I sat back and so did Don. I burped and giggled. "Excuse me," I said. He laughed. "Sissy slut and her cum burps." I liked it when he said "sissy slut". He buckled his pants. I was too embarrassed to admit it but I had cum when he did as I was sucking his cock. I had on messy panties. He said, "Well Kelly girl. Can I drive you to your car?" I smiled and said, "Not sure I can walk." So he did and I made it home. I looked in the mirror and I had dried cum all over my chin. I pulled my panties down and jacked off in the mirror because I was a sissy cocksucker. Chapter 9 I woke up the next morning and after coffee and Advil. I turned on the Sunday news. The union had gone on strike. They said it would probably be a long one. It could last over 3 months and maybe even 6 months. I had a little breakfast and then got online for a while. I was still horny about last night. About noon, I got in the shower and removed the breast forms. I shaved very closely and my legs were still smooth. I put on a pair of pastel pink silk panties and a pair of jeans and sneakers with no socks. I wore a t-shirt and I did a light day makeup on my face with mascara and just a little eyeliner. I had a double scotch no ice and watched a couple innings of baseball. I called the adult novelty store and Don was working. I didn't say anything and hung up. I grabbed my wallet out of Joni's purse and my keys and I went and got in my VW Passat and drove down to the store. When I walked in there was one other person in the store. Don saw me and smiled. I pretended to browse and finally the other person left. I put my sunglasses up on my head so Don would know I had on eye makeup. He smiled. "Hey Kelly girl! How's my little sissy slut today?" Now I was turned on. "I just wanted to tell you how much fun I had last night Don." He smiled. "Well come around here bitch. I got more where that came from." And with that he put a mirror on the counter with two lines and a rolled up dollar bill. I took the dollar bill and did both lines. Fuck I was so hot. I went around the counter and he kissed me and I started rubbing his cock. "Kelly girl...Be a good little sissy slut and get down under the counter and suck Don's cock?" I got down on my knees under the counter and he unzipped his fly and took his cock out. In minutes I was sucking his cock. He was standing there. Then I heard the bell on the door ring and someone else was in the store, "Hi Roger!" Don said. So he apparently knew this person. They talked for a minute or two and you could tell Don was distracted and his balls were beginning to tense up. I heard Roger say, "You alright, man?" Don said. "Ya I got my sissy bitch under the counter here sucking my cock, as soon as I cum, I'll let you fuck her mouth." And with that he grunted and threw his head back. I swallowed and swallowed. Then he stepped away and his friend Roger stepped up with his cock already hard and in his hand. So I took him in my mouth. "Shit, Don. This fuckin' whore sucks cock like a pro!" In 5 minutes he was finished and I swallowed his cum too. Roger patted me on my head, "Fuckin' cum dump." Then Roger left and I stood up. I had cum in my panties when Roger had cum in my mouth. Don looked at me and said, "You better scoot, Kelly girl. Someone else might walk in and you'll have another cock to take care of." With that he smacked me on my ass and I put my sunglasses back on and headed out the back entrance. I got to my car and I looked in the visor mirror. I had little droplets of cum all over my face. I drove home that way. Just as I walked in the phone rang. It was Joni. We talked for a few minutes and she gave me her room number at the hotel. Chapter 10 It was a very busy week at work. I was tired Friday night but I came home and used my depilatory lotion so that my body and legs would be hair free all weekend. I made myself a salad and had a glass of wine. I got on the bathroom scale and I had lost 3 lbs. I was down to 152 lbs. Joni called but we only talked for a minute or two. She suggested that we only talk every other night which was fine by me. I got online to play in a chat room for trans girls and I flirted back and forth with this guy. He said his name was Gerard. I told him my name was Kelly. We chatted for a while and he was very nice and he wanted my number. I declined and then he gave me his number which was from the same area code. I went to bed and got up the next morning. After taking care of some basic tasks I grabbed a cup of coffee and got back online. Gerard was there when I entered the chat room and we continued while I gave myself a pedi and painted my toe nails a hot pink. Pretty soon, I looked at the clock and almost 2 hours had gone by. So I said good bye and he gave me his number again. I went in and put on a pair of peach colored silk panties and some jeans and a tee shirt and I went to one of the local tattoo and piercing shops. I wanted my navel pierced and I left with a belly button ring. I ran home and started getting dressed. I was going out again to The Backdoor. I started getting ready around 7:00. I made myself a half a pitcher of vodka martinis. I poured one and went back to my bedroom where I applied the adhesive for my breast forms. I then attached them and did the makeup around the edges to hide them. I spent a few minutes on my eyebrows and they were soon pencil thin. I planned to tell my coworkers they had been singed when I lit the grill. I then did my face in an evening style with smokey eyes and some very red lipstick. I also wore false eyelashes for the first time that night. For the evening I selected a pair of salmon colored panties with a ribbon on the front. I wore a salmon colored silk halter dress with a v-neck that was backless down to nearly my waist. The skirt came to about 3 inches above the knee. I also had a pair of salmon colored sling back open toed mules with a 3 inch heel. I had my wig styled during the week and I loved the look. The sides were swept back revealing more of my face. I put on my clip on gold hoops and a small gold pendant that drew attention to my cleavage. Even though my own nails weren't very long I had filed them to a feminine shape that afternoon and so I applied matching hot pink polish. During the week that week, I had bought a women's wallet and so I switched all my identification and cash and then placed it in my purse. I grabbed another martini and I had a few minutes so I got back on line and there was Gerard. We chatted for a bit while I drank my martini. He asked what I was doing and I told him I was going out. He asked if I was dressed and I described my attire to him. He said I sounded hot. I finished my drink and logged off and headed out. I found a parking place about 2 blocks closer this time and was disappointed in a way. I loved hearing my heels on the pavement while the night air swirled around my legs and up my pretty dress. I got to the bar and Don was already there. I joined his table and we had an almost repeat of the prior week. Don and I flirted and then he gave me a third "toot". I was so horny. He leaned over and asked if I ever "played rough" I smiled and shrugged. He grabbed my hand and made it clear we were leaving. It was midnight and I thought we were headed to his car. He wanted to take a short cut down an alley. We were maybe 20 feet into the alley when he roughly grabbed me by the wrist and pushed me up against the wall. He said, "Does Kelly girl like it in the ass?" I was so fucked up that it made me hot and I told him about the condom and KY in my purse. He took my purse and opened it and took out the KY. "Fuck the condom bitch. I'm gonna fill you with cum." He unzipped his pants, took out his cock. He took the KY and put a lot on his cock head. "Turn around and bend over sissy slut." I did as he told me and he pulled down my panties and put some KY on my little hole. Then he stepped forward and I felt him at the entrance to my ass pussy. He pushed forward and I felt him enter me. I don't know if it was the alcohol or the coke but after some initial pain, he started pounding into me. He was grunting and I was moaning. He kept hitting this one spot that made me see stars it felt so good. He finally started to pump even harder and said, "Gonna cum bitch!" and he did, I felt his moistness inside me. Just as he was catching his breath I heard a familiar voice come around the corner. It was Roger. "Don! I think this fuckin' whore needs more cock. She's all lubed up." I had stood up and cum was running down my leg. "Bend back over bitch." I did as I was told. Roger stepped behind me and he entered my ass pussy and he must have been drunk because he fucked me for 20 minutes but he must have cum a quart because his cum was leaking before he pulled out of me. After he finished, I stood and turned around. I pulled up my panties. Don was gone and Roger was waiting. I picked up my purse and opened it. I took out the tampon, pulled my panties back down, and I inserted the tampon in my ass to keep their cum from running down my legs as I walked to my car. I drove home and when I got there I went in my bedroom. I stood in front of my mirror, pulled down my panties, removed the tampon so their cum ran down my legs. I jacked off because I was now a sissy cocksucker who liked it in the ass. Chapter 11 I woke the next morning and got a cup of coffee and got online. Gerard was there and we chatted. It seemed like only a couple of minutes but I looked at the clock and more than an hour had passed. So I logged off and hopped in the shower. I removed the pink polish from my fingers and replaced it with clear polish. I did my now usual Sunday make up and got dressed. I wore a Pastel tank top that was bare midriff to reveal my navel ring. I wore a pair of denim shorts and some flip flops and the whole world could see my hot pink toes. I headed for the store to see Don. I parked in the lot and walked in Don looked up and said, "Shit! Shake it but don't break it Kelly girl!" I must have looked puzzled because he explained that I walked like a girl. I shrugged and put my purse on the counter. Why was I still carrying a purse in boy mode? Any way we chatted and then Don said he had something for me in the office so I grabbed my purse and we went back there. He said, "Here are three pill bottles. Take one white one from this bottle, another white one from this bottle and two blue ones from this bottle every day. They're vitamins and you'll be amazed at how much better you feel in 6 months." I took the four pills he handed me with a swallow of water. Then he said, "Okay, every week you also need to come by here on Sunday afternoon for your shot, okay?" I nodded and I turned around and pulled down my shorts and panties just enough to offer my hip. He pulled a syringe and needle out of his drawer. The syringe was already full with an amber colored liquid. He wiped my skin with an alcohol swab and then gave me the injection. I headed home and it was still early afternoon. I put on a bikini and lay in the sun for a few hours. I came in and made myself a salad and weighed myself. I was down to 148 lbs. I watched TV and then Joni called. We chatted about nothing for a while and then suggested that she was getting swamped with work so maybe we should just talk once a week on Monday. I agreed because we really didn't seem to have much in common. I got online and Gerard was there. We chatted for a few minutes and then I looked at the clock. It was 11:00 already. So I logged off and went to bed. The next morning I woke up and spent the first half hour nauseous and throwing up. I was finally able to drink some coffee and eat half a slice of dry toast with my 4 pills. I got dressed and looked in the mirror. My hair was a little longer than I normally kept it. Oh fuck it; I'm going to grow it out. I just loved how my thin arching eyebrows opened up my face. I had left a bit of stubble as I had made an appointment for today to have a session of laser hair removal. I had set up 8 sessions with each session 4 weeks apart. Work was a total bitch today. One of the other girls that worked there asked me about my eyebrows. I told her that the grill had flared when I lit it. She nodded and mentioned that the grill had "done a good job". I noticed a few people whispering. One of the guys asked me if I hurt myself. I looked at him with a puzzled look and he just said something about I was walking differently. I left the office at 5:30. I made my appoint for the laser session and she sent me home with a skin cream. I took off my suit and hung it up. I pulled a pair of gym shorts on over my panties and had some broccoli and carrots for supper. I logged on and chatted with Gerard. We were on again for 2 hours tonight. Where did the time go? The last thing he typed was "Good night, Jessica." Three weeks went by and I was in a routine. The last three Saturdays, I had gone out to another bar in town called "Pink Pants" that also catered to the trans community. I was starting to make some new friends as Jessica Johnson. I didn't want to be Kelly anymore. Over the 3 weeks, I only went home with a guy twice. The first week I was having too much fun getting to know new people who all told me how hot I was. Chapter 12 It was Sunday Sept. 15th. My ass was sore but it was a pleasant sore. The guy I went with last night had an 8 inch cock that was almost as big around as my wrist. I was on my second cup of coffee and had already taken my pills. I hopped in the shower and did my makeup, grabbed my purse and headed out to meet up with Don. He gave me my shot and asked me how things were going. I told him I was down to 138 lbs. He smiled, "What's your goal?" I told him 135 lbs. he asked if anyone had noticed my changing appearance. I said, "Ya a few people at work. They gave me shit about getting my ears pierced for a week. But I bought this new pant suit that I'm going to wear tomorrow. It's black with a side zipper and I bought this purple lavender silk blouse that looks awesome." He smiled. "Good girl." On the way home I stopped at the Tattoo Emporium. I told them I wanted a "tramp stamp" and they started to hand me the book. I told I knew what I wanted and I handed piece of paper to the guy. He smiled and took me back. Three hours later I walked out with my new ink on my lower back right above my butt. It was two words stacked, in a cursive script. It said "Sissy Slut." I also had a brand new piercing with the tiniest crystal stud in my left nostril. I drove home and looked myself in the mirror. I was a tall skinny blonde with long legs and a cute butt. I had bikini tan lines. I had a navel piercing, a nostril piercing, and both ears pierced and now I had a "tat". My own hair was down to past my collar in back and over my ears on the side. My stylist had recommended a very feminine short style the last time I was in and I was at least three shades lighter in color. I kept my legs and body hair free, my toes painted bright red or hot pink, my fingers now sported four fairly fem rings and I no longer wore my wedding ring, and my nails were not boy nails even though I wore clear polish. Monday I walked in to work in my new pant suit with purple silk blouse. I was total day makeup with light powder, peach colored lipstick, and mascara only. I wore simple black pointy toe flats. I wore some new .5 carat diamond stud earrings and a simple diamond pendant. I set my purse on my desk and my boss walked out and said, "Kelly. My office now." I sat down and crossed my legs. "Kelly, I don't know what the fuck is going on with you and frankly, I don't care. You're a disruption to our office and I'm letting you go. Here is a document I want you to sign that is a non-litigation agreement and if you sign it today before you leave, I'll pay your salary for a year." I asked a few questions and he didn't answer any on advice of counsel. I signed the papers and when I got back to my desk, there was an empty box. I packed my personal items and left. When I got home, I put on my new hot pink bikini and made myself a half pitcher of martinis. I went out on the deck and called a few of my girl friends who told me I should just "go for it." After about 3 hours in the sun, I had polished off the martinis and I went inside and put on the matching cover up. I got online and chatted with Gerard. It felt like only a couple of minutes but it was an hour later when I logged off. I went in to my room. I took every stitch of boy Kelly clothes, (pants, jeans, underwear, socks shoes, shirts, everything.) I put it all in two boxes and took it to the Salvation Army which was closed. I left the boxes on their loading dock. They were really heavy and I remember thinking that I was really getting to a weak little sissy. Then I giggled..YEAH! Chapter 13 I headed home and I called a plastic surgeon that had been recommended to me. I made an appointment for a consult but he couldn't see me for another month. It was getting a little cooler and I went to the tanning salon and bought a package of 20 sessions. I was chatting with Gerard almost every day. For the last month or so, I had been sending him a battery of pics of me almost every day. They were whole body shots from several angles naked. He also occasionally requested something dressed in a pretty outfit or sometimes sexy lingerie. I was now a size 8 and by the time I was finished losing weight I was hoping to be a size 6. Gerard thought I was pretty. I was pretty well behaved most of the time. While I was waiting to see the plastic surgeon, I partied like every Friday and Saturday night. The strike drug on. Joni said something about me coming to see her and I begged off as I was "impossibly busy at work". I had another laser treatment. I also started electrolysis 2 times a week. Owwwwwww!. But I was starting to see results. I was still taking my four pills and getting my once a week shot from Don. My skin was sooooo soft. Even though I was dieting and losing weight, I didn't seem to be as defined, especially my legs. They seemed softer and rounder. My face seemed a little fuller. Don thought I looked younger. Two days before I was scheduled to meet the plastic surgeon, I was out and it was a Saturday night. I was no longer wearing my breast form because most of my friends knew I was TS and those that didn't just thought I was a flat chested girl. I never wore a bra because it allowed me to wear revealing clothes. Tonight, I had on a denim mini skirt, a pair of white silk thong panties, with a pair of powder blue 3 inch pumps. I had on a white halter top that was backless and a denim jacket. It was fall and a slight chill in the air but I still was the "Hot blonde with the summer tan" (thank you tanning bed). My hair was still short but my stylist did wonders and it was cute and fem and another shade blonder. I was more than a little drunk and I had gone home with Don and a couple of guys I knew pretty well. We got to their place and smoked some pot and then one sat on my left and one sat on my right. Don was in the chair across from us. They both started kissing me and I started making out with both of them. At about the same time they both started playing with my nipples and it was like an electric shock. I moaned very loudly which encouraged them. Soon they had my jacket off and they had untied the tie around my neck. Each was sucking on a nipple and I was moaning and writhing like a cat in heat. I had unzipped both of them and was jacking their cocks, one in each hand. They were both 6 or 7 inches and thick. I looked over and Don had his phone out and was doing a video. I didn't care. Eventually they took off my skirt and panties and my now semi- hard 7 inch cock came into view. All I had one was my powder blue pumps. One of the guys helped me up on all fours while the other stood up and sat on the arm of the sofa. I looked up and he took his cock and slapped my face with it playfully. I took him in my mouth and started sucking his cock. The other guy got behind me and spit on his cock a couple of times and then took a finger of KY and lubed my ass up even though by this time I didn't need a lot. Then he looked down and he grinned and looked over at Don. "Hey Don! Your fuckin' whore has a new tat on her ass. It says 'Sissy Slut'" Then he pushed forward roughly and said "You fuckin' dig it in the ass, don't ya whore?" All I did was moan a little loader because his friend had both hands holding my head raping my mouth. Plus I was experiencing a new sensation. I had little boobies and each time one of them pounded into me, they jiggled. I was in total bliss. Each guy eventually deposited their load. I swallowed and wiggled my tight butt. Then Don handed his phone to one of the guys and then he got on and deposited another load of cum in my ass. While the guys caught their breath, I grabbed my clothes and purse and went in to the bathroom. I fixed my makeup and got dressed. I inserted my tampon to keep cum from leaking then put on my thong panties and the rest of my clothes. I went out and kissed each one on the cheek. Then I leaned back down and let out a little cum burp in the face of the one who fucked me in the face. "Bitch," he said. Sunday was tanning bed, hormone shot, and run errands. I wore black yoga pants, black sports bra, pink hoodie and a pair of flowered pink, green, black and yellow kicks. I got home and weighed myself. I was 135 lbs. I made my appointment for my consult with the surgeon the next day at 2:00. He and his nurse examined me and as we were going through the numbers I was struck. He said that I was 5'10". I said "Doctor I'm 6'." He had me get back on the scale again and adjusted the height measure. "Yes. 5'10" on the button." I saw it with my own eyes. "But how...?" I started. The Doctor looked at me, "Jessica, when were you last measured and by whom?" I told him that me and my sister used to get measured every year on our birthday by our dad. "I see. Well sometimes dad's 'fudge' a little." We discussed what I wanted. I told him I wanted "full facial feminization" surgery. He looked puzzled. "But you're very pretty now?" he said. "Thank you Doctor. But as I get older, I will become more masculine, even if I maintain my current hormone regimen." He smiled because that was the right answer. Surgery was scheduled for one month from that day. Chapter 14 I partied on the weekends and occasionally during the week. I was chatting with Gerard every day. I remember one of our chats started out with "You a very naughty girl Jessica." Then he said something about a video. Our chats just flew by and sometimes they seemed like 10 minutes and a couple of hours would pass. The fateful day arrived. I packed an overnight bag and Don drove me to the clinic. I got checked in and I thought it was weird that Don seemed to know the Doctor. I had almost "A" cup boobs now. I was still 135 lbs but I felt like my thighs and butt were a little plumper. They took me back to the surgery prep area and the nurse gave me a shot that relaxed me a lot. Then they gave me like 9 forms to sign and when I was finished, the shot had taken full effect so I took off my clothes and put on the little clinic gown. I looked around for Don but he was gone. They turned on the TV but I was too spacey to follow. They came in and wheeled me down to surgery where the Doctor was waiting. The nurse inserted my IV and I was out in seconds. When I came around I felt like I had been hit by a train. I was in and out and the when I woke up the nurses gave me more pain meds and I fell back asleep. My face was covered in bandages. But why did I have bandages on my chest? My throat hurt so bad I thought they must still have some tubes in there. I even had sore spots on my tummy, my butt and legs. God why all of this? I have no idea how many days had passed but one day the Doctor came in and checked me out. He asked how I was feeling. I pointed to my throat and the rest of my body. He smiled and nodded. "You will be beautiful my dear. My best work yet." After I don't know how many days, he came in and removed some bandages. "Ah you are healing well my dear." I asked for a mirror and he said, "Not yet. Give it a few more days." Slowly I came around. My chest hurt and my throat hurt but I was under strict orders not to talk. I had to write notes to my care givers. Finally the Doctor came in and said that he was removing my bandages today. First he removed all my facial bandages. He gave me a mirror. I was still swollen and bruised but unless I was mistaken, I was going to look identical to my sister, Jamie. I was happy about that. I looked at my throat and my Adam's apple was gone. I smiled. "Do you like so far" he asked. I nodded. He said, "Its okay you can speak. I said, "Yes..." and I stopped. Who the fuck was the girl with the bimbo voice? I tried again. "Yes..." Fuck! It was me! Then he removed my bandages from my chest. I now had a beautiful pair of at least "C" cup boobs. I smiled. I said, "What else was done to me and how much more do I owe you?" God my voice was kinda hot! He replied, "Well we did some liposuction to even further reduce your waist and we then redistributed some fat to your buttocks and thighs. You also know about the trachea shave and while we were there we shortened your vocal cords. You're all paid up courtesy of Gerard." I spent another night at the clinic and then Don picked me up. I have no idea what my measurements were before but I was now 38C-25-35. It took almost a month for all the swelling and bruising to go away. Joni called and I let it go to voice mail. She wouldn't have believed it was me anyway. The message she left gave me a laugh. Apparently she wanted a divorce. She had fallen in love with one of the guys she worked with and was pregnant from him. I was going to be served with papers tomorrow. Finally I met Gerard. We chatted online and he gave me instructions to dress casually. I wore a white cotton strapless tube top, a yellow cotton mini skirt with a lace hem, pastel yellow silk panties and yellow 4 inch pumps. I was picked up at my home and driven to an estate in the country where I was shown into his study and I sat and crossed my legs to wait. A few minutes later a very distinguished looking man of about 50 years old walked in. He was close to 6'6" with salt and pepper hair and deep brown eyes. He was in excellent shape and he walked up and offered me his hand. I stood and we began to walk around his estate. I came to learn that Don worked for him at the novelty store. He also owned several websites. Don had shown him the video and he had seen my pics from early stages of transition. Our chats had been hypnosis sessions. He offered me the opportunity to work for him. I would live at the estate and have an unlimited clothing budget and expense account and he would pay me $200,000 a year. Of course I would be at his disposal in all ways at his request. I asked if this included sex and he smiled and nodded. "What else would I have to do?" I asked. He smiled. "Well, I have seen you act on video. Maybe you would like to audition in person?" We were by his pool and he turned and looked at me and unzipped his pants. He pulled his semi-hard cock out and it had to be 8 inches long and as big as my wrist. I knelt before him and looked up in his eyes. He began to rub his cock over my face as our eyes remained locked. I took each of his balls in my mouth and sucked. They were as big as golf balls. His cock was hard now and fully erect he was 10 inches. I took his cock in my hands and licked and kissed it up and down the entire length. I finally reached the head and I licked the drops of precum and then took the head in my mouth and swirled my tongue around it. He was so big in girth that I was only able to take about half of his hard cock in my mouth. I was so hot because it was the biggest cock I ever played with. He rolled his head back and moaned, "Mmmmm Sissy Slut....Suck that cock whore." and he grabbed my now shoulder length hair and began to bob my head on his cock. "Play with your tits, bitch." I pulled my top down and began tweaking my hard nipples which sent me over the top. I was moaning like the horny bitch I was when he began to help me to my feet. "I want to fuck that gorgeous girlie ass Sissy Slut." We walked to a table a few feet away where I removed my panties and hiked up my skirt as I bent over. He took some lube and put some on the entrance of my ass pussy and began to fuck me with his fingers. I was in heaven when he took his hand away and I felt his cock as it began to enter me. I had ridden and fucked so many different cocks over the last several months but this the biggest. I finally took it all and we began to build a rhythm. After a few minutes he grabbed my hair and pulled my head back as he pounded into my hole. "You like that you fucking whore?" "Yes daddy I love it. Fuck my hot ass daddy." And it got so hot with dirty talk that when he deposited his load I blew my wad on the concrete by the table. We stood with his dick in my ass as he softened and we caught our breath. Eventually he fell out of me, and he put his cock away as I grabbed my panties. We walked to his study where I grabbed my purse and went to the bathroom where I inserted a tampon and put my panties back on and repaired my makeup. I walked back in his study where he was seated behind his desk looking at his computer monitor. He motioned for me to come around his desk where he offered me his lap to sit on. I looked at the monitor, "What is it?" I asked. "It's a test site called www.sissyslut.com. Let me show you." It showed all the pics of me that I had sent him and the video that Don took with his phone. Gerard went on to explain to me that if I came to work for him, he would get my legal name changed to Jessica Johnson. Then I would debut the website with my stage name of "Sissy Slut". If things went well, we would do more photo shoots with professionals and for sure more videos. We would sell memberships to the site and all I had to do was be pretty and sexy. Then he put the contract in front of me. "All you have to do is sign here.".....