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Life at Ann Taylor Belladonna As the Christmas season approached, I was your normal 21 year old college student. I hung out with my friends and complemented their fashion. I would watch Gossip Girl and One Tree Hill, my favorite shows, with my best friend, Clarissa. Okay, I'll admit that I wasn't quite your normal 21 year old guy. I was somewhat happy about that to be honest. I knew how guys my age acted. They're all a bunch of dicks obsessed with sports, rap music or metal and fucking every easy girl they could find, but the girls like them anyway. So, I guess I can't blame them for acting that way. If it works for you, I guess you keep doing it. It was not for me though. I was all about fashion, pop music and girl talk. All of my friends were girls since I was a teen. That was when my male friends peeled away from me as rumors spread about my sexuality. I never cared too much about it though. My parents were sort of oblivious to what I was. They divorced when I was ten. Despite living with each of them at various times, neither one of them ever picked up on my cross-dressing. However, they did know about my unusually girlish interests. Despite that, neither one ever asked about my sexuality. They knew I only dated girls, but that did not quell their suspicions. If they only knew about my drag exploits, I bet my mom or sister would try to set me up with some guy. I was blessed to have an older sister growing up named Constance. My only sibling was two years older than me, and she followed trends closely. We were about the same build growing up so I saw her room as sort of a candy store once my urge to cross-dress became apparent to me. I was so jealous of her stuff. I always felt that she was the lucky one. I badly wanted to be her. I wanted to be able to dress like her. I wanted to be one of the girls she hung out with. Dressing in her clothes gave me an escape from my boring male life. I started doing it when I was 6. I was lucky enough to remain smaller than her until I was 15. Even when that passed, I only ended up being three inches taller than her, so her skirts, shorts and dresses still fit me kind of well. My calves were too big for her pants though. I tried dieting to get them slimmer, but I couldn't get them slender enough to fit her pants. That was an outwardly odd part of me to my fellow classmates. A lot of the guys in my school were obsessed with adding bulk, but I never seemed interested. I put up with a lot of put downs for it, but I gave back insults as good as I took them. Anyway, no one knew the real reason I tried to keep my weight down except for Clarissa, my best friend. Clarissa and I had been friends since we were 10. She picked up on my girlish leanings early on. Her parents knew of them too. I was only the boy allowed in her room. I knew that was because her parents thought I was gay. I wasn't gay, but I didn't feel any need to correct them. I wanted to be able to hangout with her, and my cover was not likely to be blown. I knew I came off gay around her parents. I liked what Clarissa liked. We were both into women's fashion and watched the same shows on the WB and then the CW. Clarissa knew that I was attracted to the girls as much as I was attracted to their clothing, but she never let that come between us. Clarissa has kidded with me that I should have been born a girl for years. As I got older, I admitted to her that I felt the same. I even told her about my cross-dressing when we were in high school. Clarissa was understanding about it. She helped me come to terms with the fact that it was a part of me that I could not deny. I in turn provided her with a shoulder to cry on when she had a fight with one of her many boyfriends. I tried to help her with them, but I could never put myself in her boyfriend's mindset. Outside of attraction to women, I simply could never understand the way men think. I had a string of open-minded girlfriends over the years. None of them knew about my cross-dressing, but I'm sure they all had their suspicions. They all knew my girly interests. The relationships all followed the same course. They were fun at first because I shared so many interests with the girls. Then I would get bored with them. That's when we'd break up. I guess I wanted the relationship I had with Clarissa plus sex. That's what I was looking for in a girl. I knew I'd never have that with Clarissa. My attraction was not reciprocated. She always went for the bad boy type, not the good 'girl.' I was trapped in the dreaded friends category with her. I resigned myself to being her closest friend. There was no doubt about that. All of her other friends were girls, and they all competed with her. I was friendly with the five of them. I hung out in a group with them playing the part of the den mother. I was comfortable around the girls. I knew I had no chance with them because they did not go for guys like me. They were girls who wanted men, which they often reminded me I was not. The girls would joke around that I was 'one of the girls' and a 'girly girl.' I did not mind the labels so I did not fight them. They were friendly with my girlfriends over the years, but I knew I had to keep my distance from some of their boyfriends. Most of their guys were cool with me because they thought I wasn't interested in their girls. Others were a bit more homophobic and did not like their girls hanging out with me. That didn't stop the girls, but I knew which guys I had to avoid over the years. I hung out with the girls throughout high school and when they came home from college during the holidays. Clarissa did not go away to school and neither did I. We both went to the same commuter school. Things with her stayed the same except it took me longer to get to her house after high school when I moved. When I started my college career, I went to live with my dad. He lived two towns over and closer to the school I was planning to attend, but I really went to get away from my mother. She was smothering me after Constance went away to college. Besides the increased distance from Clarissa, the only downer about my father's was that I did not have my sister's closet to sneak into anymore. Clarissa helped me build up my own stash at the local thrift store to deal with that. Over time, I built up a nice collection of pants, skirts, tops, dresses and shoes from there. Clarissa would give me her opinion on every piece, the way I always did when I went shopping with her. Clarissa even helped me come up with the perfect hiding place for my clothes within the box spring of my bed. Clarissa would later play a big role in my public debut as a woman. That whole thing came about when I wanted to get a job to earn some money for Christmas presents. There were a fair amount of jobs out there for me in retail. I looked for places to apply before Clarissa suggested Ann Taylor. She had been working there for over a year and said it was the perfect job to make use of my interests. I asked, "Do they even have employees that are guys?" "Who said anything about guys?" she countered. "Well, how could I....Oh, wait? I think I've got it. You want me to apply as a girl," I responded stupidly to Clarissa's amusement. "Why not?" Clarissa answered with a grin. "Well, I wouldn't be able to pull it off." "I've seen you in drag so many times, Ashley. You know I can't believe that." I smiled at her response. I like to think of myself as a decent looking girl. That's what I see when I check myself in the mirror after I've dressed in my girly best. It was always pleasing to me when Clarissa seconded my opinion of myself. I wanted to do it. It sounded like fun. I didn't think I could pull it off though. I shrugged and said, "Even if I'm willing to do it, they won't hire me." "Why not?" "They'll find about my masculinity from my application or work history." "Why? You've only worked retail, you've got a girls name, all you got to do is check the box that's says female and no one will ever know." "They'll call my old bosses..." "They don't bother. I know my boss. She's lazy like that. If I vouch for you she won't call. She won't even do anything with your social security number." "Are you sure?" I asked. "I'm positive. You've just got to trust me. Okay?" I nodded and said, "Get me the application." "I already did," Clarissa replied. She pulled the application from her pocketbook as she sat on the edge of my bed. She handed it to me and told me to fill it out. She stood over me as I answered the inquiries. When I finished, I handed it back to her. She told me that she would hand it to her boss personally to get me preferential consideration. Clarissa then told me to take out my girls clothes. She wanted to pick out the best interview outfit she could find for me if her boss gave me a call. She told me I'd have to dress up everyday for work. Clarissa explained that had to wear dress pants and a blouse or a dress. The only time I'd have to wear Ann Taylor was if I wanted to wear jeans. Then I'd also need to wear a blouse and a blazer to look presentable. Clarissa took out one of my black dresses and said it would do. She then took out one of my pairs of black heels to go with it. I thought I'd look out of place wearing them to a store, but I trusted Clarissa's judgment. Clarissa then left to go to work. I stayed home and did my reading for class. The next day at school, I got a call from Clarissa's supervisor. She told me that she was interested in interviewing me. I thanked her and made arrangements to be interviewed after class that day. On the way to the mall, I stopped at a deserted parcel of commercial property and changed into the dress and heels I had left in the car. I put on my makeup in the car and pulled my long hair back neatly before I pulled out of the abandoned lot and back onto the street. I pulled into the malls parking lot and stared at the building as I began to have second thoughts about going in. I wondered if I could really pull it off. Could I really keep people thinking I was girl? It seemed like a difficult thing to do even though I had years of practice under my belt. The thought about how fun it would be to work with Clarissa while pulling off the ruse was enough to overcome my doubts. I got out of my car and headed into the mall. I walked around unnoticed. No one seemed to care that I was walking around in a dress and heels. No one gave me a stare that said that I looked out of place in them. I even caught an ugly guy leering at me which gave me a strange sense of pride. I continued to walk through the mall and towards the store and looked inside. There was only one customer in the store, and she was being attended to by an older woman. I stepped through the doorway and made my way towards the counter. "There's my debutante," Clarissa said with a smile as she saw me. We hugged, and she showed me into the backroom where I was going to be interviewed. Clarissa's boss came in. She introduced herself as Sue to me. We exchanged pleasantries before she got down to interviewing me. She asked me a few questions before she hired me. She told me I could start the next day. I was elated. I thanked her and went and thanked Clarissa. Sue saw us and called another two clerks over to introduce me to them. One was an older woman named Dawn, while the other was a younger girl named Denise. I was struck by Denise's beauty, but I tried hard to conceal that. After saying hello, I went back to my car. I drove to another deserted spot and changed back into my male clothes. The next day I went to work at Ann Taylor. I again dressed in a vacant lot before I headed to my job. I clocked in and met the staff working with me that day. One of the workers was Denise and the other was Clarissa. We were three of the four youngest employees at the store, and we knew we'd frequently work with each other. I found out quickly that Clarissa was friendly with Denise. I could see why. She was a great girl. If I had met her under different circumstances, I may have asked her out. As customers came in, I approached them and asked if they needed help. The few that said they weren't just looking used me to help them pick out outfits. I enjoyed that part of the job. I would check inventory to see if we had things in certain sizes that weren't on the floor. I really had a zest for helping women look there best. I found an odd satisfaction in helping dress the women that came through the store. I liked looking a woman over and being able to say what I felt would look good on them. Now that I looked like a girl, I felt free to give my opinion to strangers about skirts, dresses, tops, suits and shoes. These were things I talked about with Clarissa and our friends over the years, but not with those I was unacquainted with. The women usually agreed with my recommendations. Sue noted this and told me that I was a natural at determining what would look good on a person. When I wasn't helping the customers, I helped keep the inventory in order. I made sure everything was in its right place on the racks and made sure folded items were folded correctly. I also brought some inventory out and put it on display. I managed to talk to Clarissa from time to time. She often brought Denise into the conversation, and I got acquainted with her. Denise made me a little nervous though. She gave me knowing looks and often examined me as I worked. During one conversation with Clarissa, she said with a smile, "I'm sure you know what it feels like for a boy." Denise was standing next to her and smirked. She then whispered into my ear, "Don't worry, I won't tell. Clarissa explained it all to me, and I really like what you're doing." I blushed as she pulled away from me. I knew any chance with Denise as a man was gone. I had to put it behind me and go on playing the salesgirl. The next day was the day before Thanksgiving. I was scheduled to work, but Clarissa wasn't. However, I was happy to see that Denise was working the same shift as me. I got to work helping customers find what they wanted. Sue was very impressed with me and said that it was rare for a girl my age to have such good sales instincts. I thanked her for the compliments and went back to helping customers. When there weren't any customers. I helped keep the racks in order like the day before. I also fitted in as much time to talk to Denise as I could. She was receptive. I got to know her a little better. I found out that she worked at Ann Taylor full time. She didn't go to college because she wasn't a very good student. I tried to talk her into going to community college, but she kind of brushed aside that talk. She asked me how I liked working at the store. I gave her my honest opinion. I liked helping women dress and find clothing that really works on them. After work, Denise invited me out to dinner with her. I was ecstatic about the invite. I went with her to the T.G.I. Friday's on the other side of the mall. We talked a little about our relationships with Clarissa before she asked, "Do you have any romantic feelings about her? I replied that I didn't. Denise seemed kind of happy about that. I wasn't sure how to take that. Denise was kind to me, but I still wasn't sure whether she thought I was some kind of freak or something. That concern was gone by the end of our meal. As we ate, Denise asked about my family. She asked why I dressed. She then inquired, "Do you have a girlfriend?" "Why do you ask?" "I'm just curious about what a girl would say if she was dating someone like you." "I'm not dating. I've dated in the past, but no one recently." "Really?" Denise answered with a smile. I smiled back and said, "Yes. Though I am looking." "For a girl or boy?" I was taken aback. She didn't know what my orientation was. I wondered if Clarissa hadn't told her that I was straight, but part of me knew she did. I didn't know if Denise really believed her. "A girl of course," I answered after a pause. Denise nodded and said, "I've got a girl for you then." I looked her in the eyes and said, "I'd love to meet her." Denise smirked, and we made arrangements to go out dancing that night after we finished eating. We went and danced late into the night at the club. My feet felt like they were being stung by a thousand bees by the end after so many hours in heels, but I put on a happy face. I even got a good night kiss out of it before Denise and I parted ways. The next day, I went to Thanksgiving dinner at my aunt's with my father and sister who came into town the night before. I sat and watched the football games with my male family members while the women worked and talked. I kind of wanted to be with them, but I knew my place in the family was with the men. I knew I had to fight my urges to be one of the girls. The next day, Ann Taylor was swamped with the Black Friday crowd. There were so many girls working that day, and we rarely had time to say more than two words to each other. So despite having both Denise and Clarissa working with me, I didn't do much talking about anything other than women's apparel. As I gave a customer my opinion of the dress she tried on, I felt an arm around my shoulder. I looked over at Clarissa who was giving me a shocked look. I turned slowly towards the person and saw my mother's smirking face. "How's my baby girl doing?" She said. I went white. I must have looked like death at that moment. She sized me up and said, "You look very pretty today." "Thanks," I managed to say after a brief pause. The customer looked at me strangely as I started to sweat. I thought I was going to faint. Mom put her hand on my shoulder. She looked into my eyes and said, "I let you get back to what you were doing, but I need you to call me on my cell during your next break. Is that clear, young lady?" "Yes," I struggled to say as I swallowed the vomit that had crept up into my throat. She turned and waved as she went back into the mall. I froze as I watched her leave. I was in shock. The customer broke my stupor. She asked what was wrong. I came up with something I can't even remember. I went back to helping her, trying to put my mother out of mind. It was futile. She was all I could think about as I waited for my break. When it came, I walked out to my car. I sat in the driver's seat and locked the doors. I then dialed my mother's number. I wanted to get the whole thing over with as quickly as possible. I didn't want to have to wait to hear what she was going to come at me with. "Ashley, darling, how are you?" Mom said as she answered. "Good," I replied with a stutter. "Good? You don't sound it dear. Have the other girls been teasing you?" "No," I said as my voice started to shake as well as my hand. "That's good. I wouldn't want my baby girl being made fun of because mommy came by her job." I couldn't believe how my mother was screwing with me. She kept referring to me in female terms like I had always been her daughter. I couldn't take it anymore so I snapped, "What the hell's going on?" I heard silence on the other end. My mother then spoke in a clear stern voice, "Ashley, I won't have you talking to me that way. I'm your mother. Secondly, I think I have the right to ask you the same question. So tell me, Ashley. Why is my only son working at Ann Taylor as a salesgirl?" I hated to say it, but I saw her point. I explained what happened and my past as best I could within three minutes. When I finished, my mom said, "Well, Ashley if this is what you want, then I'm not going to stop you. Of course, I can't have you doing this around your father, he'll have a fit. You know that. So, you'll have to move back in with me." "What?" "You're moving back in with me. It's the only way to make sure that this doesn't get out to your father." I knew what she meant. She was going to tell him if I didn't agree to move back in with her. She had never wanted me to leave. Constance told me I was breaking mom's heart. I kind of felt like she was right at that time too. I just felt that I needed a little freedom. I didn't want to be checking with her before I did anything. Dad didn't give me a curfew like mom did. I just got tired of having to account to someone else for my behavior. I was not surprised by how my mother played her hand. She was a successful business woman because of her killer instincts. When my mom saw a way to get what she wanted, she used it. She wanted me back home, and, now, she had the perfect weapon to get me back. I said, "You're right mom. I'll have to move back in." "I'm glad you saw it my way. Don't worry, it won't be like before. There's going to be big changes, now." I managed to reply after some delay, "Great." "I'll see you soon, Ashley. Love you." "See you, love you," I replied using poor grammar. I collected myself before I headed back into the mall. I went back to work and put clothes on the racks and folded them whenever I wasn't assisting a customer. Clarissa came over to me when she could to try and talk about it with me. I explained what had happened. She said she'd be there for me. I thanked her for that, but I wasn't in the mood to talk about it at the time. After work I changed back into my men's clothing and went home. I told my dad I was moving back in with mom. He was not hurt by it. He was a little confused, so I made up some bullshit about mom hating living alone. He bought that because he knew that the part about my mother was true. The next day, before I even moved in, Mom gave me the rundown on the terms of my new life. She started off by saying that I no longer had to call her wherever I went and I didn't have a curfew. I was ecstatic about those terms. I basically had been given what I wanted from her from the start. However, my joy was short lived as I heard the rest of it. Mom told me that I was not allowed to wear men's clothes anywhere but my father's and school. Outside of those two places, my male life was over. The impact that would have on me was something that gave me some concern. Mom continued. She said that I had to do the chores that my sister used to do before she moved out. I knew that this meant that I had to vacuum the house and do the laundry weekly. My sister also used to wash the pots and pans whenever they were used for dinner. I had never done a chore in that house. My sister was quite upset about that fact. She used to mock me that I was, "Mommy's little prince." I reveled in it around her. Now, my mother was making it clear that I lost that status. I had gone from Mommy's little prince to another serving wench. I was now going to be her little helper just as my sister had once been. That caused me even greater concern. I felt that I wasn't just going back home to mom's. I was replacing my sister. I wasn't going to be the little prince; I was going to be her baby girl. She also told me I had to make up for lost time with her. She didn't elaborate, but I was sure I wasn't going to like it. About the only thing I liked about the thought of going back was moving a little closer to Denise. Denise went to private school her whole life so I never got to know her growing up even though she lived only 5 minutes away from my mother's. After talking with mom, I called up Clarissa to help me move on Monday after school since I knew she wasn't working that day either. I moved my stuff out with Clarissa and mom while Dad was at work. Clarissa would try to lift my spirits as we cleaned out my room, but she knew it was futile. I could tell. She knew how I felt. I was torn about the whole thing. I wanted to spend more time as a woman, but I didn't know if I really wanted to spend all my time outside of school as one. I wanted a healthy mix, but Mom was titling the scale towards the female side after years of being dressed like a man. I was a bit unnerved about losing control of the direction of part of my life to her, but it was out of my hands. I knew I had to live with it for at least a little while. I locked up Dad's house and headed back to my loaded up car. I drove to my mother's house. I unloaded my car, my mom's and Clarissa's. We then set the stuff up in my old room. When we were done, I hugged Clarissa and thanked her. I politely asked her to go at that time. She understood. She knew I had to settle in with my mother for the day. After Clarissa left, mom called me into the kitchen to have a talk. I was kind of nervous about what she was going to say. My mother picked up on it given how my feet tapped the floor and how I was fiddling with my fingers. Mom told me to calm down before she said that she wanted to make up for the time she lost with me when I moved in with dad. I was not particularly sure what she meant seeing as I was a guy when I left and, now, I was dressed like a girl. So I wasn't certain which me she really wanted to hangout with. I figured it was the new me given her house rules. Mom then told me that she expected me to go food shopping with her like my sister had done. I figured it wasn't the worst thing in the world so I didn't put up a fight. Mom continued and said that I had to eat dinner with her every night I wasn't working. I was not happy about that, but I felt that I was not in a position to complain. Mom then told me to get ready to go to the store with her. I grabbed my pocketbook and said I was ready to go. We then headed to the store in her car. She pulled up in front of the grocery store and made me get a cart for her. I wheeled it behind her through the store as she picked up the groceries that she had on her list. She had me pick up the stuff on the low shelves and the high ones to save her stress on her back. After we paid for our groceries and went back home, mom got me started on my chores. She told me it was a vacuuming day. I took out my mother's vacuum and went to work upstairs first. I vacuumed all three bedrooms before I went down the stairs and vacuumed the living room rug. The longer I vacuumed, the more I thought about my sister. I felt that mom was making me into her. I had gone from being my own person into being my sister's replacement. After I finished, it was close to dinner time so Mom made me go into the kitchen and help her make our meal. I had never cooked before so I followed my mother's directions closely as she worked beside me. I found it a little interesting. It was a lot better than vacuuming. There was a little creativity to cooking that cleaning didn't provide. I wondered if my sister ever kind of enjoyed cooking with mom. When we finished, I carried the meal over to the dinner table that I had set. We ate together and mom asked about school and my job. She was particularly interested when I started to talk about Denise. I knew she realized that I was infatuated with her. I couldn't conceal that so it was probably obvious to my mother After dinner that night, I wanted to go see Denise after she got off work. She called and asked me how everything went. She wanted to see me too, but Mom was keeping me sequestered in the house for the night. Denise was bummed, but we were both working the next day so we knew we'd get to spend sometime together the next day. Since mom made me stay home that night, I knew she wanted us to spend time together. She put on the television and made me watch her favorite programming with her. She went to her TiVo and put on Desperate Housewives first. I had never seen the show before. I followed its Soap plotlines and music to try to figure out its appeal. I enjoyed the show. I thought it was kind of funny here and there. Mom then put on some other show we watched together, before I told her that I needed to get some sleep for school the next day. She told me goodnight, and I went to bed. I got up the next morning and dressed in jeans and a t-shirt. I put on my sneakers and headed out to school as Ashley the boy for the third to last class day before finals. I took my familiar seat in one class beside Clarissa. After that class, we had a break in our schedules. We headed to a fairly secluded part of the campus to talk about what had happened. Clarissa asked how I was handling my new living arrangements. I said it was okay. She asked specifically, "How are you dealing with the dress- code?" I smirked and said, "That's the best of it at home. I just miss being able to go out looking like this. There's so much less involved when I just want to step out." Clarissa smiled and said, "I wouldn't know, but I have to believe you." "Yes. I used to take that for granted back when I dressed only when I wanted to." "Well, I take comfort in you knowing what we have to put up with. At least one of you guys should have to know." "Yes, being one of the we will do that to you." "I think all guys should have to go through it once." "That wouldn't go over well." "No. I wouldn't think so. People are too uptight about that kind of stuff. They're really quick to take offense and make judgments." "I'm well aware," I answered as I felt a small grin come onto my face. Clarissa put her arm around my shoulder and said, "Just keep your head held high and your chest out when you walk, and you'll make it through these times just fine." I thanked her, and we hugged. We then headed back to our classrooms. We didn't have the same second class so we parted ways. We met up for lunch before we finished our day off in a class together. After school, I went home and changed into my work clothes. I came out in my dress and heels. Mom gave me a look and said, "You know it's pretty cold today?" "So?" I replied. "Don't you want to dress in something warmer?" "This is all I got to work with," I replied as I checked the contents of my pocketbook. I said goodbye to mom and headed out the door. I drove down to the mall and went back to work that late afternoon. Whenever I could get the chance, I would talk to Denise. In the various little conversations we could muster, I managed to tell her about everything that was happening. Denise told me she was happy to have me living closer to her. After work, I talked with Denise in the cold parking lot before I headed home. After that, my life fell into a predictable pattern. When I wasn't finishing up at school, I was doing 1 of 4 things. Sometimes I would be studying for my exams or working. If I wasn't doing either of those things I was helping Mom around the house and hanging out with her. Beyond Mom, school and work, in my free time I managed to spend some time with Denise. Given mom's directive, I had to do it dressed as the girl Denise met me as. I was sometimes troubled by that. Denise never met the Ashley I had grown up as. She only knew me as the increasingly feminine coworker. That was something that gave me pause. The more time I spent as a girl, the more girly I seemed to act even when I was dressed in my male clothes. I knew that I seemed less out of place when I dressed a girl. I could blend in as a girl. When I went around dressed up like a boy, I caught people snickering about my effeminacy. I found it increasingly harder to pass myself off as a straight guy than a lesbian. It was a problem that Clarissa found amusing. I think mom did too. Mom began to give me more girly perks too as I settled in as her new daughter. As I finished vacuuming the living room on the first Saturday in December, Mom called me into the kitchen. Mom told me she was taking me to Ann Taylor to buy me some pants for work. She said she wanted to see some diversity in my clothing. I explained to her the company policy regarding jeans and she said she could make that work for her. She told me to get ready so I went up to my room. I was actually kind of excited about it. It was one of the few real benefits I had received after moving back in with mom. I had forcibly traded my free time for my sister's old chores, but it was also accompanied by the freedom to walk around my house as a girl and my mothers desire to indulge my urges. It was making me less bitter about being blackmailed into moving back in. I slipped off my dress and put on my gaff plus two thongs to really make sure that I was tucked away properly. When I was satisfied, I put on one of my blouses plus a pair of black pants I got at the thrift store. I put on a pair of black pumps so I could get the right read on the pant length before I headed down the stairs. I picked up my purse and waited for mom to grab her keys. Mom drove us down to the mall, and I followed her into Ann Taylor. We headed right to a jeans rack. I pulled out a pair of five pocket, skinny jeans. It had a straight leg cut. My mother gave me a pair of denim leggings to try on. I took them with a little hesitation. I was a bit concerned about being exposed wearing them. I knew it was unlikely, but it was still in the forefront of my mind. The only thing that even got me to try them on was how cute I thought the zippers running up the back of each calf were. That I had that thought also concerned me on some level. I tried them on and came out and showed mom each. She gave me an approving look to the one I picked out. I then changed into the pair she picked out. She inspected the one she selected closely as I wore it. She was careful to make sure that it did not show off anything but my figure. She told me they were good to go. After we picked out the jeans, we headed over to the jackets. I picked out a black stretch, cloque zipper jacket. It had an overlapping front with an asymmetrical zipper. It also had a crinkled chiffon trim at collar. I tried it on and it fit perfectly. I then put on another jacket. It was black wool in a military style. There was tonal trim at the collar and tonal buttons. Mom gave it her seal of approval, and I decided to go with it. I figured that was all she'd get me, but she pulled me towards a pants rack. She selected some grey, black and beige pants and handed them to me. I tried them on and showed them off to mom who approved of them all. I redressed in my pants and carried out the ones I had just tried on. I took hold of the jeans I was buying and carried them around the store as mom showed me other stuff. She ended up buying me a few blouses and sweaters in various styles and colors too. I was really elated as I watched her hand over the money to Kristen, the clerk working the register for us. Kristen was a nice woman who I didn't work with often because she had poor sales so she got few hours. She said a few words to me about business that day as she rang my stuff up. Mom and I carried my new stuff to the car, and then we headed home. I went home and hit the books. I crammed for my test that coming Monday. After taking that test, I went home and dressed up in girls clothing as mom required me to. I wasn't working that day and neither was Denise. I gave her a call and asked if she'd like to go shopping with me. She took me up on my offer, and I picked her up at her house. We drove to the mall and headed for a store that she liked. We went into the shop and headed for the racks. Denise asked my opinions on some pieces, and I told her I liked a skirt she picked out. She tried it on, and I said I liked it again. She helped me pick out a blouse before we headed to the shoe store two stores down. I wanted a new pair of heels to go out in because I didn't like wearing my work shoes out. I looked at a number of pairs before I found a pair I adored. Denise smiled at them and said, "You have to try them on." I looked at the shoeboxes and found my size. I put on the baby pink and white, peep toed, 4 inch pumps. They had a concealed platform and white bow at the vamp. I put them on and tested how they felt walking them. They were pretty comfortable for heels. I showed them off to Denise who said that I had to buy them. She complemented the design as I got a feel for them. As I finished walking around in the shoes, I took them off. I brought them to the register and paid in cash before we headed for the door. After we left the shoe store, we headed for the ladies room. Denise gave me a grin as we walked into it together. We sat in adjacent stalls and talked as went. We finished up and headed towards the sink. As we checked our makeup in the mirror, I told Denise that, "Men don't realize how easy they have it." Denise smiled at me and nodded before she reapplied her lipstick. I freshened up my own as well before we headed back out into the mall. Denise pulled me into Victoria's secret. She walked over to the babydolls and started to peruse them. Finally, she stopped and smiled at one as she pulled it out. Denise held the black, lace trimmed babydoll with a pair of matching black panties up in front of me and said, "I think my boyfriend will like this. Don't you?" She winked as she said boyfriend so I knew she was referring to me. I said, "I know he'll love it. It will really flatter your curves." Denise smacked my arm lightly and said, "I know. Do you think he can handle seeing something like that?" "Sure. Why not?" "I don't want any jealousy." "There's no jealousy there. Just lust," I replied. "I think you're right. Let me try it on." Denise went into the dressing room and got changed. I waited patiently for her to come back out as she took her time getting dressed. I believe she was trying to build suspense to screw with me. "What do you think?" She said as she opened the dressing room door. I almost fainted. She was that good looking in it. I tried to speak, but I was unintelligible. Denise laughed and said, "Sometimes, you're just like a man." I blushed and said, "You look great." "You think?" Denise retorted. "I, um...he'll love it." "I could have guessed as much," Denise answered with a smile before she closed the door behind her to change back into her clothes. After Denise bought her babydoll, we headed back to my car. I drove her home and gave her a kiss goodbye before I went back to my place. Mom was waiting there for me and asked to see what I bought. I showed off my blouse and heels. She really liked the heels. We talked about the design, and I realized how girly I sounded. I really couldn't deny it, even in part. The more I lived as a girl in that house, the more I increasingly realized that mom was starting to consider me her other daughter. I was quickly conforming to what she thought a daughter should be too. Ashley the girl was becoming the dominant part of my personality. She wasn't just a part of it that I reveled in when I choose. My male self really had fallen into the background given my mom's rules. Even though I dressed as one four days a week, I still never really got the chance to really enjoy the parts of being a man I liked. I felt that I had become more a girl than a man given all the time I spent in a woman's shoes. It really hadn't hit me at that time just how much my self-image had shifted, but I really felt not long after that afternoon with Denise. After work one day later that week, Clarissa and I went out into the mall after an afternoon shift. We headed down to the food court and got online for a burger. As we talked as waited, I heard three guys behind us. One of them was clearly referring to me. I heard him make a crack at my disproportionably thick calves. I blushed, and my shame was instant. Clarissa picked up on it and said, "Forget those idiots. You look good." I nodded, and we gave our orders. I barely touched mine. I did not feel much like having fast-food at that moment. Clarissa realized it and tried to console me. I knew that my calves weren't really that big. By I was so otherwise thin that they stuck out. I mean I wasn't rail thin like an anorexic model, but I was medically the right weight for a girl my height. I was 5'8" and 135 pounds. I wondered how much thinner I would have to be to not have to deal with those comments. I really rededicated myself to my appearance after that. I kept myself on a strict 1200 calorie diet and worked out whenever I could find the time using mom's Pilates workout DVD. By the time finals started, I had dropped five pounds. I wasn't quite where I wanted to be yet, but I felt I was getting there. My body was the only thing I was feeling good about besides my relationship with the girls as I took my first final. I knew the subject matter, but I always worried with tests. I always did well, but for some reason I stressed myself out every time. To make matters worse, the tests were the easiest part of college at that point to me. I felt increasingly out of place as I dressed up like a guy to go to take the tests. I tried to carry on like one as I made my way around the school, but I would find myself inevitably behaving like the girl I was primarily living as. I was also having a hard time reconciling the male face I saw on the way to school in my rear view mirror with the person I felt I was. My unease at the time helped my weight loss. I didn't feel much like eating as my stomach was always in knots. Clarissa and Denise both tried to relax me, but nothing seemed to help. Carrying on at school as a guy proved too much. I had heard the rumors about me going around among my classmates. I knew I was coming across as increasingly effeminate despite my attempts to disguise it. In addition to rumors about my sexuality, there were people saying that I was going to get a sex-change. I had no interest in one, but I understood where they were coming from with it. Going to the bathroom there became a real chore too. I wore panties in addition to an unpadded bra to college everyday I had to be there so I could feel normal. The panties complicated matters when it came to peeing. Of course, the dirty looks I got from men when I tried to use the urinal next to them didn't matter. I felt threatened by them so I used the toilet. I heard whispers about me as I was peeing sitting down. I knew the rumors, but I didn't deny them. I didn't see much point it. Who would ever believe the truth anyway? All the stresses in my life were adding up. I was at wits end by the time finals finished. I felt I did well on the tests and started to feel better. However, my greatest relief was knowing that I was going to be drastically reducing the amount of time I spent dressed as a man. My hours picked up at Ann Taylor after the semester ended. I was among the best performing salesgirls so Sue was happy to give me more hours. Either Clarissa or Denise usually worked with me, so I never really had a moment alone there. I loved that. If I wasn't talking with Clarissa or Denise I was with a customer. I loved talking fashion with those women that came through the store. I found that I really enjoyed helping women look their best. A lot of them appreciated my opinions. I would spend my time away from Ann Taylor hanging out with Clarissa and Denise, sometimes together and sometimes just one on one. Me and Clarissa watched shows, went to the movies and just talked at times like we had always done before. However, Denise provided me the same plus a little more. Everything I did with Clarissa I did with her, but being alone with Denise also meant that a physical connection was in reach. I had never been with a woman like her. Well, I might have actually. I would never know because none of the others knew my secret. That secret was now my life and Denise was a big part of it. She became my girlfriend in two senses. I had been a pseudo girlfriend to my exs, but this was different. Denise only knew as Ashley the girl when we weren't under the covers. My ex girlfriends thought of me as a strange man, but Denise made clear she thought of me as a woman with a little twist. Life outside of that was normal. I finished up my Christmas shopping and kept doing my chores for mom. Mom bought me clothes and shoes instead of giving me a weekly allowance like she used to give Constance. I didn't complain because I knew I was getting stuff that was worth a lot more than she used to pay Constance. I thought more about Constance as the month drew on. As Christmas day approached, I knew that the day Constance was coming home for the holiday was imminent. After college, she took a job across the state. I had talked to her since I started to live primarily as a girl, but I hadn't told her about it and neither had my mother. She wanted to leave it as a surprise. I was really nervous about what she would think about the way I was living. Constance was supposed to drive home on December 23, and I was off that day. We expected her sometime after lunch. Mom made me wait around for her. She wanted to get my surprise out of the way early. Mom made me dress in a pair of black leggings, a long light gray, off the shoulder tunic and a pair of golden thong sandal. She said that the outfit was good around the house clothing for a girl my age. The whole outfit was outrageously girly to me. I knew that's why mom picked the stuff out for me. It's not that I didn't like the outfit; it's just that I didn't want to introduce my sister to this side of me dressed like that. The tunic gave me the most pause. Since it hung off one of my shoulders, it showed off the straps of my pink bra my mother purchased me. I was sitting on the couch in the living room reading the latest issue of Vogue when I heard a car pull up in front of the house. I paused for a moment as I figured it was Constance. I knew that there was no escape from her finding out so I just sat there and continued to read. Constance came through the door carrying a suitcase a minute or two later. I heard my mom as she ran over to her and kissed her on the cheek. Mom made Constance put down her suitcase and dragged her over to me. Constance looked at me strangely before Mom said, "Constance, I want you to meet your little sister Ashley." I saw a look of surprise on Constance's face before it turned into a look that told me that she understood me a lot better than she had before. Still a part of her did not quite believe what she was seeing. Mom left us to get acquainted for a moment. "Ashley, blink twice for torture," Constance whispered into my ear as our mother turned away from us. I smiled and said, "It's consensual. I like this. I like the way it makes me feel. It makes me happy in a strange way." Constance nodded slowly with a vacant look in her eyes. She suddenly stopped and said, "So none of this is mom's doing?" "Well, the part with me living here is. She caught me at my job at Ann Taylor..." "Wait, you work for Ann Taylor?" "Yes, I'm clerk there. I get a nice employee discount if you want anything." "Uh, huh." "Anyway, I was helping this lady pick out a dress when I felt her arm around me. I looked up at Clarissa, she works there too, and I knew I was screwed." "So Mom made you come home?" "Yes, I have to live with her in exchange for her not telling dad and his family. It's really not that bad here. I get to dress full time now, except when I'm at school." Constance smiled and said, "That's great for you. It really is. I love your shoes too." "Oh, thanks. Mom bought them for me." "Mom bought those?" "Yes." "You're lucky. You should have seen the crap she used to buy for me, hideous." I titled my head to the side and nodded. Constance then sat beside me. She grabbed my hand and said, "Are you really happy doing this?" I nodded and said, "I've never been happier. The only drawback is that mom's got me doing all your old chores." "Really?" Constance said with a laugh and a smile. "Yup." Constance smirked at me. She always used to get on moms case about how I didn't have to do as much as she did around the house. I think I made her day by telling her that. She made my day shortly thereafter when she asked, "Did you lose weight?" I smiled and said, "Yes, I dropped 10 pounds. I'm down to 125." "I weigh 128," she responded with some concern. I changed the subject and complemented her lavender, leather purse. She accepted the complement and asked me how long I had cross-dressed for. I told her the truth and told her about what I used to do. She wasn't happy that I used to wear her clothes, but she wasn't angry either since I didn't destroy any of them back in the day. Mom then came into the room and started to talk to Constance. A few minutes later, we started to decorate the tree. We ate dinner together and watched the TV after that before we went to bed. The next afternoon, I was back to work at Anne Taylor. Constance came by my job and looked into the store as I was changing the clothes on a mannequin. She grinned and laughed at me before she continued on her way through the mall. Clarissa came by later and picked me up because we were going out together after work. I had worked the closing shift that Christmas Eve with Denise. We helped the few last minute shoppers that came in. They were mostly young women shopping for their mothers at the last second. We had a few desperate men come in and ask us about our opinion of certain clothes they picked out somewhat blindly. You could tell that some of them did not have a clue what size their girls were, but they bought them clothes instead of gift certificates anyway. I helped them out as I best I could because I wanted to make the sale even though I wasn't on commission. After work, Clarissa, Denise and I went out to a local bar that failed to card young women in the ordinary course of their business. We walked towards the bar and saw a group of single young men glancing at us. Clarissa made eye contact with one of them. Three of the men then came over. Kurt seemed really interested in Clarissa as he started to talk with us. Brian seemed interested in Denise. I got stuck with Chris who seemed like the wingman. He was not interested in me, but he was taking one for the team. They tried their best to charm us and bought us drinks. I disliked the whole thing. I kept close to Denise as she flirted with this man in front of me. Finally, I pulled her away from them and into the ladies room. I asked her, "What's going on?" She smiled and said, "Calm down." "Calm down! I thought we were...." "We are, silly. I just don't want to pay for drinks." "Seriously?" "Yes, babe. It's what we do. We're women. How do you not know that?" "I'm not quite sure." "You've got a long way to go before you've mastered this," Denise said with a smile. I accepted her explanation and headed back out into the bar. We continued drinking and talking with the guys all night. Clarissa ended up giving Kurt her number while Denise and I snuck out to her car. We then headed back to the mall to pick up Denise's car. As we separated for the night, I gave Denise a goodnight kiss before I got back into Clarissa's car. Clarissa then drove me towards my house. When I got home, I brought the gifts I bought for my mom and sister down from my room and placed them under the tree. I then headed in for the night. The next morning, I awoke and I put on my make up. I then came down the stairs dressed in one of the pajama sets mom had gotten for me right after Thanksgiving. They were my favorite pair with purple paisley print cotton pants and a simple v-necked cotton tee-shirt. My mother was already up when I got down the stairs. We wished each other a Merry Christmas and I helped her cook a pancake breakfast. Constance came down almost as soon as we finished. I wondered if she waited for us to be done so she wouldn't have to help out. After breakfast, we headed for the tree to exchange gifts. Mom loved the purse and blouse I got her. Constance said she liked the dress I got for her, but I think she was being kind. She did like the new I-Pod I got her though so my efforts with her weren't a total waste. Constance got me a new I-Pod as well. It further supported my belief that we thought alike more so than either of us liked to admit at times. Constance and I then opened our gifts from mom. My gifts were like the ones that Constance had received in years past. There were a lot of clothes, three pairs of shoes and two purses. She bought me skirts, dresses, pants, blouses and jackets. There were a few DVDs too. As I got to the final boxes towards the wall I realized that they were all in identical wrapping paper. Mom seemed especially eager for me to open them. I opened the largest box first and saw the simple red dress with a back zipper, scoop neckline and cap sleeves. The hemline was well above the knee. I thanked my mother and opened the next box. It contained a pair of 4 inch high red pumps. They were patent leather and had rounded toe. I then opened the third box. It contained a white belt. It was leather and its silvertone buckle was decorated with crystals. I began to realize that the colors all went together. I stared at the fourth and last box knowing that it too was part of the outfit mom wanted me to wear for Christmas dinner. I unwrapped the last box and saw the simple pair of white tights. I pictured the outfit that these clothes would make together and laughed at how girly it would look. I knew mom was hoping I'd be her doll for the day the way my sister once was on holidays. I thanked mom before she confirmed to me that the last four things I opened was what she wanted me to wear when our guests arrived. I said I would and helped her clean up the shredded wrapping paper. After that, I carried my gifts to my room before I went back downstairs to help mom get the house ready for our guests. When I finished up with her, I went upstairs to get ready to go to my father's house. I closed my bedroom door and started to take off my pajamas. I felt a familiar disgust as I stood naked and saw the painfully male body that was beneath my pretty clothes. I put my panties back on instead of my old boxers just to have part of me feel normal. I then put on a shirt and a pair of dingy jeans. I put on the one pair of male socks I had left and put on my black skateboarding sneakers. I looked in the mirror. I looked like a chimera. I had a woman's head and a man's body. I hesitated before I removed my makeup. I took a good look at my face as I did it. The more I saw of my true face, the more disgusted I came by how I looked. I stared into the mirror as I finished. The only girlish feature left was my long straight hair. I looked plain. I felt like the face I was looking at was alien to me now. I had avoided looking at myself without makeup since the end of the semester. I had only been living as a woman full time for a week, but I already felt the face I had grown up with was not my own. I realized that I might never be able to go back to living as a man. Dejected, I headed down the stairs and saw my sister waiting for me. She looked at my familiar face and said, "I almost forgot what you looked like under all that stuff, Ashley." I didn't answer her statement. I changed the subject and said, "Are you ready to go?" "I was waiting for you," she retorted. Constance and I then headed over to our dads. He greeted us with hugs and we exchanged gifts with him. I opened my gifts from dad and saw the pair of men's jeans in one of the boxes and cringed. Dad asked what was wrong. I lied and said that I was just having a little stomach pain from what I ate the night before. He offered me some medicine, but I turned him down. After we finished with our gifts, we had a cup of coffee with him. We had polite conversation with him, but I felt out of place. I did not feel like myself. I remembered all my conversations with him over the years, but they felt like they weren't mine anymore. My dad noticed my apparent discomfort. He broached the subject, but I blew it off as girl trouble. He apparently did not know how to take that. My mannerisms in his home were effeminate. They were that way since I was 10, but they were really getting worse. They had gone from noticeable to glaring. From the way I sat to the way to the way I talked, it was all girly and causing him some consternation. He was as uncomfortable watching me as I was sitting their dressed as his son. Constance picked up on it too. She later told me that I looked like a fish out of water, and Dad looked like he had seen a ghost. We finished up there and I packed up my car with Constance after we said goodbye to Dad. I then drove home from my father's with my sister. She noticed my intensity as I drove. I felt so wrong at that moment. I'd see myself in the mirror, and I'd cringe. I needed to put on my face. I pulled up in front of my house and hurried into it. I looked back and saw Constance looked at me with an astonished look. She was realizing what I really had become. I rushed into my room and slammed the door so that my mother would not see me. I felt hideous and wanted to hide as I put on my makeup. I began to relax and slowdown as I put more of it on. Each application calmed my nerves. I brushed out my hair and felt sedate as I stared back at the girly face in the mirror. That was my face, not the one I showed my father. The Ashley he had seen was gone. This pretty one was all that was left of that boyish thing. I then disrobed and put on my Christmas clothes. I put on my white tights, breast forms and bra before I slipped into my red dress. I then left my room and called out for Constance. She came over and zipped me up before I went back into my room and put the white belt around my waist. Constance came in a little later and examined me as I stood before her dressed like either a Christmas tramp or the biggest sissy in the world, depending on your point of view. The red dress hugged my body. I looked in the mirror as I clasped my fingers together in front of my chest. I looked so pretty in it. I even looked down at my legs and they seemed to be thinner. I still felt I needed to drop another 5 pounds before I'd be comfortable despite what Clarissa and mom had to say, but I still felt pretty. I turned to Constance and asked with a smile, "How do I look?" Constance smirked and said, "Like Santa's little slut." I walked towards my heels before I paused. I knew that it was weeks until I had to go back to school, so I felt I had to ask if she had any nail polish on her. Constance paused and said she had more of the red nail polish she was wearing. I asked her if I could use some. She nodded and said, "I'll do it for you." I jumped a little and clapped my hands before I hugged her. She paused to look me in the eyes after our embrace ended before she left to get the polish. I was so happy. Nail polish was just what I needed. It would make sure that I wouldn't be going out in my hideous old clothes until I had to. Constance came back in and did my nails in this lovely crimson red color. I walked around the house as they dried. I would periodically stare down at them and smile. I felt as if my hands looked right for the first time. My mom complemented the way they looked when I showed them to her. When they were dry, I finished helping mom set up for our Christmas dinner guests. They were my widowed Aunt Katie and her two kids. Aunt Katie had a daughter my age named Devin and a son two years younger than me named Dave. Devin was 5'2" and had weight problems her whole life. She was overweight and then she thinned down in high school. Once she went away to college, she put the pounds back on. She was not obese, but she was chubby. I know it embarrassed her. She was the only heavyset person in our family. It didn't help her that she had Dave in her family. Dave was your stereotypical guy. He was into sports even though he wasn't big enough to play any of them at the top level. He was my height and weighed about 160 pounds. He hit the weights pretty hard in high school and liked to tell us that he was bulky, but I sometimes felt he didn't understand what bulky men looked like. I thought he looked fit and not like a weight lifter. Aunt Katie was 5'5" and almost eternally thin. The woman was a twig. She was also the sweetest person in my family. Mom had already told the three of them all about me so they weren't in for a surprise. Mom told me they were accepting of it, but I really didn't know what they would think once they saw me. I heard them come to the door so I put on the red heels I had carried into the kitchen. Constance let them in, and I walked behind my mother when we went to greet them. I saw three dumbfounded faces staring at me. Now, if this was the first time I was seen in women's clothing I would be concerned that I looked some sort of freak. I knew that they were actually impressed or surprised by how passable I was. Aunt Katie came over and hugged me and said, "You look darling." I thanked her and looked at my cousins. Devin stared vapidly at me, shaking her head a slight bit as her eyes ran over my body from head to toe. I saw her lips moving a little. She was as silent as her more amused looking brother smirked at me. Finally she blurted out, "That's not fair." I was one of five faces that stared at her with confused looks. "What's not fair?" Aunt Katie asked. "How the hell does he end up with a figure like that, and I get this?" She declared as she clutched her waist. "Probably doesn't eat as much cake..." "David," Aunt Katie shrieked. For the first time, I felt uncomfortable in a dress. I didn't like being refer to as 'he' when I wore one. I felt the word didn't fit me. Devin's exclamation made us all uncomfortable. Aunt Katie and mom tried to calm her down. They told her she wasn't that overweight. Dave had to walk out of the room to not snicker in front of them. I walked into the kitchen with Constance to check on the turkey mom was cooking. Constance had been doing that for her for years. She did it every alternating Thanksgiving and Christmas since she was 12. She kind of schooled me in what the thermometer readings meant. Mom and Aunt Katie came in a few minutes later. They took over in the kitchen and dismissed Constance and I, telling us to go talk to our cousins. We followed their orders. I walked in hesitant steps that Constance noticed. She knew that I was concerned over what they would say. I was never close with Dave and Devin, and they apparently had issues with the new me. Constance tried to reassure me about what I was doing as we walked into the living room where Dave was watching a basketball game. Devin looked at me and said, "There's my two cousins looking all pretty." We walked in and looked at her. Devin continued, "Ashley, I'm sorry about before. I just wasn't expecting you to be so dainty." Dave smiled at his sister's remark. I sat down and smoothed out the skirt of my dress before I heard Constance respond for me, "That's what you get when you take care of yourself. Ashley's giving you something to aspire to." "You're still a bitch, Constance," Devin responded. "I'm the bitch?" Constance rejoined. I tried to stay out of the verbal cat fight that ensued until I was dragged into it. Devin yelled at my sister, "At least my brother's not a little fag going around town dressed like Katy Perry." I was satisfied that she at least said I dressed like a fashionable girl. I was ready for the abuse that came with living the way I was living, but Constance was not. She shot back, "My brother may be a cross-dresser but he's got more heart and is more of a lady than you'll ever have." "More of a lady? He's got a dick. Just because he's parading around Ann Taylor doesn't make him ladylike or even stylish." "Ann Taylor?," Dave interjected. "I work there," I answered. Dave shook his head as he looked at me and said, "You've got to be kidding me, Ashley. I thought mom was joking. What could you possibly be doing going around like that?" I responded, "I'm being myself. It's really helped me." Dave retorted, "What can dressing like that possibly give you?" "It has its benefits," I answered. Dave went to respond, but Devin cut him off by saying, "I'm just curious, Ashley. Do you attract gay men or straight men dressed like that?" "Devin, come on," Constance interj