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The Whiz Kid Belladonna Angelica Park sat alone in the living room of her spacious colonial style home. She caressed the sleeveless, dark colored dress decorated with a bright sakura pattern that was resting in her hands as a number of thoughts went through her mind. She looked down at the above the knee dress with an elastic waist and wide black belt and admired its design. She felt that it would look nice on most young women, but she was not a young woman. Angelica was in her early fifties and knew that the dress was not purchased for her. That was something that her cleaning lady missed when she excitedly brought the hidden dress to Angelica's attention. Angelica did not let on that she was certain the dress was not for her. She thanked Rosa and sent her back to her tasks around the household. Rosa had left the home hours earlier to go clean another house, leaving Angelica to contemplate why her son had the dress in his room. Angelica was fully aware that her son had not been involved in a relationship since he moved back into her house. She knew that his self-confidence had been destroyed by the collapse of his professional career. While Billy Park built a successful internet company out of college, his meteoric rise was matched by a swift fall. In the course of three years, Billy went from a college student to a multimillionaire living on his own to broke and living with his mother. Billy realized far too late that he should have disinvested some of his shares of the company as his mother repeatedly advised him to. While Angelica was an accomplished businesswoman who owned her own boutique firm, Billy felt that her financial ideas were more inline with a small business model and not the sort of national brand he wanted to build. Accordingly, Billy never gave his mother's advice much thought. Billy's failure to heed her advice made his decision to return home to her hat-in-hand all the more humiliating. He knew that she would scold him for failing to listen to her. It was something that he heard his father withstand when his companies invariably went belly up. There would be no words of wisdom from his father on how to weather the brunt of his mother's criticisms though since he passed away while Billy was in his last year in college. It was a devastating personal loss for both Billy and his mother, but between the life insurance payment and the lack of the inevitable financial drain of his old man's businesses, Angelica's business was more successful than ever as she was able to reinvest more money into the firm than she had been able to since before she married. Billy's success also meant that Angelica would not have to carry his living costs either, which served to further enhance her financial position even as the market continued to drag. Billy's independence, however, was a thing of the past now. His paper only wealth was gone, and he was living back in her ward. It had been three months since he moved back home. Angelica welcomed him back with open arms even as she berated him for thinking that he was somehow smarter than her and for failing to heed her advice. Billy withstood her words in silence, knowing that he had no real defense. Angelica noted it too and realized how shattered the experience left her son. She spent the following weeks trying to build him up, but his efforts to obtain employment were floundering as much as his confidence was. Her son's despondency greatly concerned her. She was also concerned by his behavior as he began to keep to himself and take long walks alone because it was something that he did not need any money to do. Angelica heard the front door open and knew that her son had returned from one of those walks. She took a deep breath before she asked, "Billy, can you please come in here?" Billy followed the sound of his mother's voice into the living room. He paused as he turned the corner in the hallway that led to the room and saw the dress in his mother's lap. With hesitant steps, Billy approached her and inquired, "What's up?" "Would you like to explain why Rosa found this in your room?" Angelica asked her son in response. "It was an ex-girlfriend's. She just left it at my place." "Really? So why did you bring it here when you moved back home then?" "I couldn't bring myself to throw it out." "Or return it?" "We're not on speaking terms; you know how it gets sometimes." "I sure do, and that's why you either give the stuff back or throw it out, unless you have some other use for it." Billy blushed as he shook his head and said, "It's not like that." "It's not?" Angelica asked with raised eyebrows. Billy shook his head in silence. Angelica smiled for a second as she reached behind the couch and pulled out a bag. Billy grimaced as she dumped his feminine belongings out of the bag and onto the coffee table. "I suppose all this was her stuff too, right?" Angelica asked. Billy put his head down and closed his eyes so he would not have to look at the collection of panties, bras, hosiery, blouses, breast forms, dresses and two pairs of pumps. Billy cursed himself for sneaking the clothes and shoes back into the home. Billy thought that he would be able to hide them where his mother would never find them, but Rosa discovered the dress while she was cleaning and informed Angelica about where she had found it. After Rosa left the home, Angelica went to that spot and continued to prod around until she uncovered the rest of Billy's feminine stash. Billy knew that he had been found out, but he could not bring himself to admit the humiliating truth. "Yes, that's right those were hers too," Billy lied after a long pause. Angelica leaned back on the couch. Billy could see the incredulous look on her face and knew that he was not fooling her. She coughed and said, "I know you're lying to me." "I'm not. I mean, who else's would they be?" "I think they're yours, dear," Angelica replied as she stared into his eyes. Billy turned away from her gaze as he lied, "No, no! Why would you think that?" "First off, they're all in your size." "How do you figure that?" "I can do size conversions between men and women's sizes. I've been buying clothes for us for decades, so it isn't really hard for me to figure out that these clothes fit you." "It's not what you think....," Billy began to respond. "Then what is it?" Angelica interjected as she stood up and moved next to her son. While Billy was four inches taller than his 5'3" mother, he was intimidated by her as she looked up at him with a steely look in her eyes. "I'm going to give you one last chance to tell me the truth or I'm throwing you out of here. I don't care what you do with this stuff, but I won't have you lying to me." Billy clenched his fist and closed his eyes as he replied, "They're mine." "Thanks for confirming what I already know. Now, could you explain why you wear them?" "I like how they feel." "How they feel. They feel girly. You like to feel girly?" Angelica asked, slightly taken aback before she quickly realized that she should not have been surprised by his response. Billy blushed and turned away from her. Angelica closed her eyes as she knew that he had answered her in the affirmative without saying a word. "So, you're gay," Angelica said as she began to rub her arm. "No. I'm not gay, I just like to...." "Feel like a girl?" Angelica asked. "Yes, but that..." "Doesn't make you gay?" Angelica interjected again as she raised her eyebrows. "No, it doesn't." Angelica rolled her eyes and sighed. She was certain that Billy was lying to her about his sexuality. She could not imagine that a straight boy would ever wear women's clothing. While Angelica was angry about her son lying to her about the clothes, she believed that he was lying to himself about being straight, so she decided to not push the issue. Angelica stared at her distraught son and hugged him as she said with a forced smile, "I don't care if you like to do this, Billy. Just as long as you're happy." Billy was startled by his mother's seeming acceptance of his cross- dressing. He hugged her back and thanked her as tears formed in his eyes. Billy quickly batted them away before they released each other. After they stood in awkward silence for a few moments, Billy cracked a smile and asked, "Well, were do we go from here?" Angelica grinned as she said, "I suppose I should meet that daughter I always wanted." Billy felt slightly offended by her statement and inquired, "What's that supposed to mean?" Angelica shook her head as she answered, "Nothing. I'm happy I had you Billy. I wanted a son, but I also wanted a daughter. You know the issues that I had, so I only had a son." Billy nodded as he did not want to discuss the reproductive issues that his mother had that had prevented her from carrying other children to term. Billy knew that his mother loved him and considered it a miracle and a blessing that he was a born a healthy male child. Billy turned the conversation back towards his cross-dressing as he replied, "I don't know if I'm ready to let you see that. It might be too weird for the both of us." "It wouldn't be that weird. It might be kind of nice for us to have a mother-daughter moment," Angelica replied with a laugh. Billy squirmed as he processed her comment and responded, "I'd still be your son, mom, just in a dress." "I know that, but let's just pretend that you're my precious little girl." Billy blushed and laughed at her remark before he politely refused her request again. Angelica shook her head as she said, "Oh, come on. It'll be fun for both of us. You enjoy dressing up. I'd enjoy giving you a few pointers. It'd be like having a mother-daughter relationship, except we skipped over that whole bitchy teenager that I'm worried about getting pregnant phase." "I don't know about that, mom..." "Well, you're right. You were a bitchy teenager, but I didn't have to worry about you getting pregnant," Angelica interjected. Billy cocked his head as he blushed and replied, "No, mom, I was talking about it being fun for the both of us..." "Well, my fun is the only fun that matters since I pay all the bills. I think, when you were on your own, it was you who told me that since you were paying your own way, I shouldn't tell you what to do. I guess it's the opposite now, right?" Billy sighed as he remembered telling his mother the very words she was repeating to justify him acceding to her request. "You're not going to back off this until you see me dressed up, are you?" Billy asked. "Oh, you can read me like a book," Angelica replied with a grin before she told Billy to collect his female clothing and bring them back up to his room. Billy complied with her request and walked up to his room with his bag full of feminine clothing. He hurried up the stairs and headed for his room where his mother was waiting for him. She took the bag from his hand and laid out the outfit she wanted him to wear on his bed. Billy looked at the outfit consisting of a black and white, tweed pencil skirt with vertical piping detail, a black turtleneck with a ribbed collar, cuffs and neckline, black sheer pantyhose and his black slingback, peep toe pumps with a buckle on the vamp and asked, "Why did you chose this?" "I think it's the perfect little secretaries' outfit." "Why not go glamorous instead?" Billy countered with a smile while he held up the dress his mother had confronted him with. "That's not quite as useful in the office place," Angelica replied in a matter of fact tone. "Why does that matter?" Billy inquired. "If I want to see if you can pass for a normal girl, then it matters a lot." "Why would you want..." "There's an opening at work, Billy," Angelica interjected. "An opening, but your office is...," Billy began to reply before he realized what she telling him. In haste, Billy continued, "Oh, no! No! No! No! Not a chance, mom" "What else have you been doing? What else is there for you to do? You haven't been able to get a job. Why not come to work for me?" "Doing what?" "Working for me," Angelica answered. "Again, doing what?" "It's nothing glamorous, but it's a job." "Doing what?" Billy inquired once more. "Well, the job that's opening up is for my personal assistant..." "Personal assistant, you mean your personal secretary," Billy interjected. "Secretary is such an antiquated term." "You just used it to describe the outfit," Billy said as he pointed to the clothes his mother had selected for him to wear. "Force of habit." "You can't be serious about this, mom." "Well, I'm not sure if I'm serious yet, Billy. I don't know if you can really pass yourself off as a woman. I think you can, but I don't know." "This is crazy!" "There's only one way to confirm that, dear." Billy blushed as replied, "Why can't I just come to work for you as a man?" "There's just less of a chance of you embarrassing the both of us this way." "How do you figure that, mom? You don't think I'd be more likely to slip up in heels?" "Well, maybe, but you know as well as I do that I don't employ any men in the office." "So, because you discriminate against men, I have to come to work for you as a girl?" "Honey, I don't discriminate against men. Men just can't handle taking direction from a woman." "Yes, that doesn't sound discriminatory, mom." "It's not discriminatory, it's a fact." "Based on what?" "Personal experience." Billy rolled his eyes as he knew that his mother never hired a single man to work for her and was basing her claim on the experiences of other businesswomen she knew. Billy threw up his hands as he said, "This is all moot, mom. I could never pass..." "How do you know that?" "Personal experience," Billy replied, using his mother's words. "I'd like to give you a second opinion," Angelica countered. "What's wrong with my own?" "We often have the wrong idea about how we look, Billy. It's all a matter of perception." "So you think you'll be a better judge on whether I can pass myself off as your secretary?" "I'm sure I could. I'm pretty good at judgment calls, and not just big ideas." Billy knew that her comment was a dig at his own judgment. He wanted to retort something, but he held his tongue. As he stood in silence, Angelica reached towards the bed, picked up the skirt and tossed it at him and said, "Let's see if you got this one right." Billy stared at her in silence for a second as he clutched his tweed above the knee skirt. He knew it was pointless to fight her on it. Billy understood that he was not getting out of the situation he found himself in unless he dressed up for his mother. Angelica smiled at him as she noticed that he was capitulating. She stepped out of the room and told him to come see her in her room when he finished dressing. After his mother stepped out of the room, Billy closed his bedroom door. Billy stripped out of his clothes and put on his sheer pantyhose first before he placed on his bra, which he stuffed with his breast forms. Billy covered up the bra with the turtleneck his mother selected for him before he placed his legs through the pencil skirt. He pulled it up to his waist and zipped the rear zipper before he slipped his feet into his slingbacks and adjusted the straps around the back of his ankles. After he finished dressing, Billy checked to make sure his fake bust was straight beneath his turtleneck in the mirror behind his closed bedroom door prior to opening it. Billy peered out the door and heard the television in his mother's room on. Billy stepped off his carpeted floor and onto the wood floor of the upstairs hallway. He heard his heels clicking on the floor as he slowly strode to his mother's door. Billy hesitated before he knocked upon it and peered into her room. Angelica turned towards the door and smiled as she saw how her son looked from the neck down. Angelica complimented his appearance as she stood up to inspect him. Billy blushed at her compliments regarding his feminine figure as she walked around him. Angelica smirked as she noticed that nothing below his neck was giving away his gender. Angelica shook her head as she laughed and said, "Do you know what I would have given to have legs like that at your age?" Billy only blushed and shook his head in response. Angelica smiled as she giggled a little while she added, "You're so lean, and just the right padding, makes you seem so girly." "You seem to be enjoying this," Billy said with a blank expression on his face. "How could I not? I'm almost sure that I've got Dorothy's replacement standing right in front of me." Billy rolled his eyes before he inquired, "Why is Dorothy leaving anyway?" "Her husband is a business man. He's being relocated by his company for a promotion, and she's got to follow him with the kids." "Oh," Billy replied as his mother walked behind him. Billy felt her fingers running through his long hair as she said, "Billy, I hate to tell you this, but no one would have a clue that you're a man from your neck down." "You're kidding me?" "Well, you're right. I don't hate to tell you it. I love to, actually. It's so wonderful, really." "Okay, maybe you're right, but look at my face, mom. I'm not a girl." "Not with that attitude you're not, but with a smile and a little makeup, I'll bet you'll look cute as a button." "What's cute about a button?" Billy replied, his voice dripping with sarcasm as he bemoaned how serious his mother seemed to be about taking him on as her secretary. "It's a figure of speech. I suppose it doesn't have to make sense, like you being a boy with the pretty figure of a girl." Billy blushed at his mother's words as she peered around his shoulders to stare at his face. While Billy was embarrassed by her praise, he was somewhat proud of it since he had dieted and worked out to maintain a girlish figure that he had never shown off to anyone besides himself before. Angelica walked away from Billy and returned with a brush. Angelica sat Billy down on her bed and began to brush his long straight hair. Billy cringed as Angelica brushed out the knots in his hair, but he tried to maintain a tough and manly expression as his mother told him about her office. Billy listened as she described the various employees, whose names he had all heard before. Billy listened carefully and asked questions about them, trying to humor his mother while she brushed his hair. When Angelica finished with hair, she turned her attention to his face. She grabbed him by the hand and led him into the master bathroom where she took out her makeup bag. Billy caught his reflection in the mirror and marveled at how nice his brushed out, long hair looked as it framed his thin face. Angelica broke his concentration on his appearance when she told him to sit down. Billy sat on the closed toilet lid and watched in the mirror while his mother put on his lipstick, lip liner, blush, eyeliner and mascara. When she finished, Billy stood up to take an unobstructed look at his appearance. Billy's jaw dropped as he stared at himself. He looked much better than he usually did en femme. He figured that it was probably because his mother, unlike him, knew how to properly apply makeup. Billy shook his head as he looked at himself and thought about his mother's words. He knew that there was no way that she was going to let him back out of going to her office for an interview to be her personal secretary. "Still think you judged yourself correctly?" Angelica asked with a smile. Billy began to shake his head in disbelief before he caught himself and said, "Yes." Angelica glared at her son and said, "What did I say about you lying to me?" "I'm not lying, mom!" Billy countered weakly. "Well, my house, my rules, so you'd better get ready for your new job. You'll be coming in for an interview on Tuesday." "Mom, can we talk about this?" "Why? What were you planning to do on Tuesday?" "I was...I was..." "Going to keep looking for a job? I know, but there's no point looking when there's one open and employer ready to take you on." "I can't be your secretary!" "Oh, you underestimate yourself." "That's not what I meant, and you know it!" Billy exclaimed with a huff. "Don't take that tone with me, young lady. I'm your mother and I expect to be treated by you with respect." Billy slumped before he apologized. Angelica smiled at him and said, "Apology accepted, but I don't want to hear another word about you coming to work for me." "But...," Billy began to respond, trying to get a word in edgewise. "I said not another word," Angelica interjected. "What if I get another job?" Billy asked as his mother turned away from him. Angelica turned to face him and answered, "If you get another job, you're free to leave my company. That's your call. I wouldn't stand between you and a new career, but I won't stand for you staying at home idle when I can put your pretty face to work either." Billy nodded before his mother led him out of her room. ----------------------------------------------------------------------- With the terms of his employment set, Billy spent the rest of his Saturday redoubling his efforts to find a job. He continued to send his resume that evening, Sunday and Monday, but he continued to receive no responses. The lack of responses was not unexpected for Billy. He had been dealing with it for months, but he kept hoping against hope that some job would save him from the humiliation he was sure he was going to suffer when he went to his mother's office for his 'interview.' Tuesday came quicker than Billy imagined it would. He woke up to the sound of his mother knocking on his door, telling to him to get up. Billy forced himself out of bed and headed towards the stairs. He had a quick breakfast with his mother before he showered and made sure that his body was clean of body hair before he joined his mother in the master bathroom after putting on his panties, breast forms, bra and turtleneck. Angelica smiled at her son as he entered in his robe that covered his feminine undergarments and turtleneck. She had Billy blow-dry his hair while brushing it under her direction while she continued to get ready beside him. Billy felt uneasy as his mother walked around him in her bathroom dressed in her pink robe with only her nude pantyhose covered feet giving any indication that she was wearing anything underneath it. He breathed a sigh of relief as she stepped out of the bathroom to put her clothes on while he continued to blow-dry his hair. Angelica reentered the bathroom dressed in a pinstriped navy blue pantsuit and navy blue pumps not long after. "How do I look?" Angelica asked her son as he put down the blow-dryer. "You look very pretty, mom," Billy replied. Angelica smiled back at him as she remembered how he used to compliment her appearance when he was a child. She was sure her husband had convinced him to do it, but she liked to hear the compliments from her son anyway. Now, that he was doing it without any external guidance, Angelica could not help but feel good about it. Angelica clapped her hands and said, "Let's get you ready for your interview okay?" "Sure, mom," Billy said as the smile left his face. Angelica took out her makeup and took to applying it as she had that Saturday afternoon. Billy watched in the mirror as his face became increasingly girlish as more cosmetics were added. Finally, Angelica finished and said, "Okay, there you go. I've got to go, now, baby. Just remember, I've scheduled your of an interview at 10:30. Don't be late!" "I won't, mom," Billy countered before his mother walked out of the room. Billy sighed as he got to his feet and walked to his bedroom. He drew open the closet doors and stared at his feminine wardrobe that he no longer hid. Angelica had even increased the wardrobe by bringing home a few more outfits after work the day before. Billy loved the skirts, tops and dresses she bought for him, but he hoped that they would be unnecessary. Billy stared at his phone for a moment, hoping an employer would call and prevent him from going forward with his interview, but the phone remained silent. Billy turned away from it and untied his robe. He hung it up before he took out a pair of nude pantyhose. He rolled them down and rolled them up his legs as he had done hundreds of times when he was by himself. Billy smiled as he curled his toes in the pantyhose and felt the familiar silky feeling on his legs and feet. Billy stood up and tucked himself away in his panties and pantyhose before he took hold of the skirt he had worn on Saturday. Angelica was insisting that Billy wear the same outfit to her office for his interview. Billy did not object to it as he knew that it was no more potentially humiliating than any other feminine outfit he would wear out of the house. Billy stepped into skirt and pulled it up his body before he pulled up the rear zipper. Billy felt the pencil skirts familiar feminine restrictions on his legs that so often delighted him as he walked back over to the closet. He bent from the knees, as the tight skirt practically required, picking up the pair of heels Angelica had chosen for him to pair with the outfit. Billy stood back up with the heels in his hand and walked towards the bed. He rested on the edge of his bed and was about to his put his feet into the left shoe when he heard the phone rang. Billy dropped the shoe and lunged towards the phone hopeful to hear a stranger's voice offering him an interview. Billy's hopes were dashed as he heard his mother advise him that the highway she had taken was experiencing severe delays. A feeling of disappointment overwhelmed Billy for a moment before he thanked his mother for the call. After he hung up the phone, Billy hung his head for a moment. He moved back towards the bed and put on his heels. He then walked over to the dresser where the modest bangle, rings and necklace that his mother had bought for him were resting. Billy looked over the jewelry with unease. He had never worn jewelry in his life, even when he was en femme, because he did not like the way it felt on him. Billy put the silver necklace on first before he pulled up the sleeves of his sweater and placed on the crystal embellished, silver tone bangle. After he worked his hand through the bangle, Billy felt awkward as he moved his arm and felt the bangle slide a few inches and up and down his forearm and wrist as he did so. "How am I supposed to get used to this?" Billy asked himself. Once he finished shaking his head, Billy put on the heart-shaped silver ring. Billy was instantly bothered by the pressure it applied to his finger, but he knew that his mother would have a conniption if he did not wear it to the interview. Consequently, Billy walked out of his bedroom, knowing that there was nothing he could do about the ring. Billy strolled towards the stairs with his cell phone in his hand. He carefully descended the steps at angle, remembering his mother's advice. Once he reached the bottom of the stairs, Billy put his cell phone in the pocketbook his mother had provided for him. Billy reached inside it and saw his license and keys amidst a sea of feminine sundries. Billy reached into the bag and took out his keys before he headed for the door. Billy took a deep breath as he stared around the neighborhood and hoped no one would see him getting into the car en femme. Billy knew, however, that his hopes were unrealistic, especially if he would be doing it on a regular basis. Billy got into the car and turned the key in the ignition. He felt nervous as he pressed the brake to shift the car into drive since he was going to be driving in heels for the first time. As Billy approached his first stop sign, his foot slipped out from under him. Billy breathed a sigh of relief that no one was coming. He resituated his feet and more carefully pressed the ball of his right foot down onto the pedal. Billy paid close attention to his footwork as he drove down the streets that lead to the highway entrance. While Billy was nervous about being seen en femme, getting to his mother's office safely was his paramount concern as he drove that morning. Billy felt a wave of relief wash over him as he parked in the parking lot of his mother's office building. Billy looked at the clock and knew that he did not have much time to dawdle. As Billy had arrived at the office after 10, he had to park along the edges of the parking lot and make the long walk to the building. Billy clutched at the pocketbook that hung from his shoulder as he looked at the uneven pavement to make sure that he would land his feet properly to avoid taking an embarrassing spill. Billy walked into the building and headed for the elevator. He pressed the button and went up to his mother's floor without encountering anyone in the building. As the elevator doors opened to his mother's office's floor, Billy felt a growing sense of dread. He walked towards his mother's office and pushed his way through the door. A young girl, who appeared to be his age stared up at him and asked, "Can I help you, Miss?" Billy was silent for a moment as he processed the girl's simple question. While Billy instinctively wanted to flirt with the girl, his appearance made that idea a non-starter. Being aware of this, Billy answered, "Yes. I have an appointment with Miss Park?" "Oh, okay, I'll tell Angelica you're here." "Thank you," Billy replied before he sat down on one of the chairs in the lobby. Billy picked up one of the sports magazines off the table before he realized that he was supposed to be a woman. He pushed the magazine aside and took hold of a People magazine instead. Billy thumbed through the pages as he thought about how the young girl in the office did not indicate that she felt that there was anything strange about him. Billy felt a familiar sense of pride over his feminine appearance even as he was ashamed of himself for feeling that way. After ten minutes, his mother opened the door. She smiled as she saw her son sitting cross legged with a People magazine in his hands with his ringed finger on the outside of the magazine cover. "You must be Elissa?" Angelica said. Surprised by the name his mother called him, Billy forced a smile to his face as he put down the magazine and responded, "Yes, and you're Miss Park?" "Please, call me Angelica," Angelica responded as she shook Billy's hand and continued the ruse. Angelica showed Billy into the office he had not been in over ten years. He followed her to her remodeled office and took a seat in front of her desk. Angelica complimented Billy's appearance, prompting Billy to blush. She then explained the job to him for a few minutes before she said that she was going to bring Dorothy in to greet him as she was going to train him to be her replacement. Billy sat back in the guest chair as he mother picked up her phone and called Dorothy to ask her to come into her office. Dorothy walked in and smiled down at Billy. Billy had never met Dorothy before, even though Dorothy had been working for his mother for eight years. He had, however, heard a good deal about her. Angelica smiled as she introduced Billy and Dorothy and said that Billy had been brought onto the company. Dorothy congratulated him before Angelica asked Dorothy to show Billy around to get him acquainted with the office and the staff. Dorothy nodded and led Billy out of Angelica's office. Billy followed behind Dorothy as she showed him where the copier, fax machine and supplies were. As they walked through the office, Dorothy paused to introduce Billy to each member of the all female staff they met along the way. Billy tried to memorize their names as he walked away from each of them. While Dorothy introduced Billy to each of the office workers, Billy felt nervous that they would realize that he was not really a woman. He wondered if his mother, at one time, had a picture of him in her office and they would connect his face to that picture, but no one in the office was giving any indications of doing so. Billy felt relieved that no one could tell that he was really a man or the son of their boss. While still sensing that relief, Billy was brought over to Dorothy's desk. She then showed him some of the basic tasks he would be required to learn under her tutelage. Billy wanted to roll his eyes at the ease of the tasks that seemed so meager as he contrasted them with the responsibilities he held at his own business, but he knew that he was in no position to complain about that. Billy smiled and listened to Dorothy as he sat next to her at her desk, which would soon be his. The location of the desk was one desk over from Anna Burke's. Anna was the only girl in the office that was under 35. Billy was sure that she was the only one he might be able relate to so he was happy to be in close proximity to her. While Billy was attracted to Anna, he knew that she saw him as nothing more than another girl. Billy was prepared to accept that to form a cordial relationship with her as he knew it would make his time in the office more palatable. Billy felt that the groundwork for a friendship was there as Anna seemed genuinely happy to finally have another 'girl' of her age group in the office. After Dorothy finished showing Billy around, she brought him back to Angelica's office. Angelica smiled at Billy and asked him what he thought. Billy replied that he was excited by the prospect of working in her office, since he was sure that that was the answer his mother wanted. Angelica nodded her head and said, "That's great! Can you start tomorrow?" Knowing that his mother would not take no for answer, Billy replied, "Yes, I'd love to." Angelica smiled and nodded as she walked over to him to show him out the door. Billy said goodbye to a few people on his way out and made a show of thanking Angelica for the job again, as he was certain a real girl in his position would. Angelica replied in a magnanimous tone, "You're welcome, dear," before she winked at him. Billy walked out of her office and headed for the elevator. He pressed the button to go down and took it to the lobby. As Billy walked towards the door of the building, he felt conflicting emotions pulling him apart. While part of him was more than intrigued with the idea of being one of the girls in the office, he was also scared that he would slip up and show his true gender. Billy wondered what he would do if that situation presented itself or, worse, what the other girls or his mother do. Billy felt a bit uneasy as he walked out the door and wondered what he was going to get himself into when he walked back through it the next morning. ----------------------------------------------------------------------- The next morning, Billy strolled through the door to the office dressed in a russet colored, knife pleated, knee length skirt, cream colored blouse with a rounded neckline and pleated front overlay, black floral patterned, lace tights and two-inch patent leather high heels with a rounded toe. His mother had purchased him the outfit and insisted that he wear it for his first full day at the office. As he walked towards the desk he would be sharing with Dorothy, he took off his coat and stared down at his skirt and heels and thought to himself in a sarcastic tone, 'Yes, this is how I wanted to reenter the workforce.' Most of the office workers were not in the building yet as he continued to walk around the office. He noticed that only Dorothy and his mother had arrived prior to him that morning as he went to hang his coat up in the supply closet where the girls hung their coats. After he finished hanging up his coat, Billy sat beside Dorothy to begin his week and a half of training to become her replacement as his mother's personal assistant. Dorothy gave Billy an office account under his assumed name, Elissa Loy, to log onto the company's computers before she began to show him how to use the functions on the computer. Dorothy continued to show Billy the various programs on the computer that he was expected to master, and many of which he already had, while his mother's other employees filed into the office. They all said good morning to Billy and Dorothy as they made their way to their desks, cubicles and offices. While Dorothy was showing Billy how to use the computer programs, she was also fielding phone calls for Angelica. Billy listened closely to how he was supposed to answer the phone for her and how he was supposed to take messages to relay to his mother about who the caller was. As Dorothy went on to discuss another program that Billy was familiar with, but felt as if he had to feign unfamiliarity, he became distracted by Anna. Anna was sitting cross legged with her shapely, black sheer pantyhose covered legs sticking out from beneath of the hem of the miniskirt of her dark grey skirt suit. Billy had to fight to prevent himself from unambiguously leering at her. As Dorothy went to take a smoking break and left him to test out what she had taught him about a particular program, Anna smiled and wheeled her chair towards Billy's desk. Billy smiled back at her and asked, "Can I help you?" "I suppose so. I couldn't help noticing that you were noticing me." Billy blushed and said, "That's just such a great skirt." "I know, right." "I love the design," Billy lied again regarding the reason for his leering at her as he tried to get the erection that was warming his seat to abate. "I can tell you where I got it. If you'd like," Anna said. Billy nodded and took down the information that Anna provided him before Anna said that the store had a lot of good work clothes for 'girls' their age. Billy thanked her as Dorothy walked back into the office to continue their training. A few minutes after Dorothy returned to her desk, Angelica called over to her to ask her for a cup of coffee. Dorothy got to her feet and told Billy to follow her into the kitchen. Billy did so and watched as she took his mother's cup from the drying rack. She identified the cup to him, which had a specific design that was unique, as was every other cup in the rack. Dorothy explained to Billy how his mother liked her coffee as the coffee brewed in the Keurig. Billy took mental notes and thought that making coffee for his mother would be the simplest task, but Dorothy then noted, "It's been a slow day so far, but when it's busy, here, just realize that you're going to be making coffee for everyone." "I thought you were my...Angelica's personal assistant," Billy replied, catching himself. "I am, but I'm supposed to help out Anna and Karen. They're everyone else's secretaries and receptionists." Billy nodded and accepted that he would find himself eventually making coffee for the higher ranking girls in the office. Billy felt aroused by the fact even though he knew that it was strange reaction to being humbled yet again. When Dorothy finished making the cup of coffee, she told Billy to bring it into his mother. Billy took the cup from her and carried it towards his mother's office, careful not to spill the contents. He knocked upon her door as he came to a stop. Angelica smiled as she looked up at her skirted son carrying a cup of coffee for her. Angelica told Billy he could enter. She thanked him for bringing her the coffee as she said, "You're so helpful, Elissa." "Just trying my best," Billy responded, uneasily. "Let's hope you're this helpful at home." "What's that?" Billy asked. "Well, I hope you're this helpful with your mother at home. You know you should always be kind and helpful towards your mother, you only get one," Angelica lectured with a smile. "She's so right," Dorothy said she walked in to give Angelica a fax that had just come in. "I know that," Billy replied as he blushed and turned to walk out of the room. He understood the point his mother was making. She was making clear that his adolescent lackadaisical manner around the home would no longer be tolerated. Billy knew then that he was expected to be a productive assistant for his mother at work and at home. Billy sat back down at Dorothy's desk and continued to receive instructions from her. They also made small talk with Anna and Karen, the office manager, who was also seated close to them. Billy felt out of place as the girls talked about various Real Housewife shows with the higher ranking women who came by to make small talk, which they built around their discussion about work related things. Billy blushed as he heard Karen's complaints about her husband's sloth and lack of interest in the kids. 'Do I really need to hear this?' Billy thought to himself before Karen and Dorothy started to discuss their kids. Billy and Anna looked at each other and rolled their eyes. As the day went on, Billy realized that Anna was really going to be his lifeline to help him maintain his sanity as he was adrift in a sea of estrogen. While the older women prattled on about things he did not understand, and was sometimes happy he did not, Anna was willing to make small talk to him about music and celebrities he was familiar with. While celebrity gossip was not something he was particular keen on, he was aware of it and could discuss it. He was also not as big of a fan of Pop music as Anna was, but he knew the songs she was talking about and could bluff his way through it as if he were a fan of the various acts she mentioned. Shortly after 1, Billy's mother left the office for a meeting. As Billy stood up to grab lunch with Anna, he asked if Anna knew who his mother was meeting with. Anna nodded and gave the name of the firm's accountant. Billy nodded in response before Anna added with a smile, "He's so weird. Like wears women's clothing weird!" "Aren't you wearing women's clothing?" Billy asked, after a pause, wondering if she was insinuating something about him. Anna laughed before she replied, "Yes, but I think being a woman makes that a little more normal of a thing to do. Don't you think?" Billy rolled his eyes before Anna grabbed his forearm and said, "Let's go." While Billy found Anna's domineering behavior a bit disagreeable, it was tolerable for him. Billy went along with Anna to the luncheonette next door to their office building. They walked through the parking lot and across the median that separated the parking lots of the two premises. Billy felt a burst of hot air as he walked into the crowded building and went to stand on the line with Anna. They chatted about how he was enjoying his first day before they placed their orders at the counter and waited for their lunches to be prepared. As they waited, Billy asked, "How is it working for Angelica?" "You'll find out," Anna replied with a smile. "No. I mean, seriously?" "She's not bad. She's a bit headstrong, but if you look at Dorothy, she lasted with her for years. She wouldn't even be leaving if her husband hadn't taken a promotion." "I suppose you're right," Billy said as he picked up his lunch and waited for Anna's to be finished before they carried their food to the cash register. They paid for their meals and took a seat at an open table. Billy felt relieved to take a seat and get off his heeled feet for a moment. He snuck his feet out of the shoes to give them a rest while he ate across from Anna, who was talking about a chick flick he knew nothing about. He bluffed his way through the conversation before they brought their trays to the garbage bin and headed back to the office. After they returned from lunch, Billy continued to work beside Dorothy and began to do some of her tasks under her supervision. A little after 4, Karen asked Dorothy and Billy to clean the cups that had been left in the sink by his mother's higher ranking employees who felt that it was an unproductive use of their time to clean up after themselves. Dorothy nodded and said, "Elissa, you've got this, right?" Billy felt that as the new 'girl' he had no option other than to nod his head and go and clean the cups in the sink. He walked into the kitchen and took hold of the sponge and the dish soap and began to clean the cups. As he continued to do so, Angelica walked into the kitchen and stared at her son with a smile. She said hello to him as she reached into the refrigerator. Billy blushed as he said hello back to her, embarrassed to find that his mother was seeing just how low his position really was, even though she had put him there. Angelica inspected her son's work as she said, "You're doing a good job, dear." "Thanks," Billy replied in a deliberately emotionless tone. Angelica smiled as she whispered into her ear, "You should consider putting those skills to good work at home." Billy nodded in responses to his mother's words. Billy knew that he only placed his plate and cups in the sink when he was at home, leaving his mother to rinse them off and place them in the dishwasher. Based upon his mother's words and tone, Billy understood that she expected that situation to change. Billy accepted that it was a fair arrangement given that his mother was paying for his housing. Billy nodded to himself about it as he finished cleaning the glasses and cups and put them in the rack to dry before he walked back over to his desk. Billy settled back in at the desk beside Dorothy and continued to listen to her as she instructed him on another task. Billy nodded as he realized how his life was going to be for the foreseeable future. As he accepted his current situation, Billy settled into a routine. He decided he would go to work as Elissa each day and spend his weeknights looking for a new job so that he could resume his male life as soon as possible. Once the week and a half passed and Dorothy departed, Billy was left as Angelica's personal assistant or secretary as Billy and Anna referred to themselves, seeing no point in dressing up their positions. While Billy sometimes felt demeaned being ordered about by his mother at work, he knew that no one found it odd since they were all under her thumb as well there. Billy decided that it was pointless to fight his role at the bottom of the office hierarchy. While he was not happy to be spending time copying papers for others, filing documents away, drafting correspondence, fetching coffee and cleaning up for his mother and her higher ranking employees, he accepted that it was his role for the foreseeable future. Accepting that made Billy's situation seem less humiliating to him. While he still wanted to do more with his life and not have to wear heels to work every day, he was happy enough, for the time being, to be working, even if his new position did not command the respect of his old one. His home life was similarly changed. While he was expected to maintain a separation of Angelica from his 'mom', while he was at work, Angelica took her son's knew found willingness to listen to her and please her to her full advantage. She made a list of chores she expected him to do around the home and Billy took to completing them. After a lifetime of having his mother rinse off his plates and glasses, Billy was now cleaning hers. He cleaned up after their every meal and was expected to help his mother cook. At first, Angelica asked for his help, but after a few days, it was an unstated fact that he had no choice but to do so. Billy also began to do his own laundry and most of his mother's. The only thing his mother kept him from washing was her intimates since she felt that they would both find that situation too awkward. Billy was also expected to get his mother's laundry from the drycleaner. That, however, was part of his formal job description. Much like at work, none of the tasks at home were more than he could handle. Conversely, Billy found that they were easy for him to do and they made his mother's life easier as well. With her increased time to herself, Angelica was able to get some much needed rest and time to formulate new ideas to expand her company even further. Billy noticed the effect of his mother's new ideas on the workplace as his mother instituted measures that increased productivity. Not all of the changes were popular, but Billy, like her other employees, had to accept them. At the same time, however, Billy was growing more comfortable with the girls at work. He researched many of their frequent topics of discussion on the internet so that he could bluff his way through conversations about various television shows and movies. As Billy grew more accustomed to his feminine persona, he also found himself more at ease making small talk about his morning beauty routine and how long it took him. He became more willing to compliment the other girls clothing, shoes and bags, much in the same way they freely complimented him. As the third workweek after he started came to a close, Billy also discovered that Anna wanted to take their office friendship into the outside world. While Billy was hesitant to agree to Anna's plans to go to a salon on Saturday morning and then to a club that night, Billy found that Anna was not willing to take no for an answer. It did not help that his mother overheard their conversation, and decided to encourage it as a way of building a level of camaraderie between the two of them. Billy felt cornered by his mother and Anna and relented to Anna's request to go along with her. ----------------------------------------------------------------------- That Saturday, Billy followed Anna into the salon, wearing the flip flops he borrowed from Anna, which Anna insisted he wear. He felt out of place there, even as he knew that he looked just like any of the other girls in the place. He took a seat beside Anna after she gave their names to the receptionist. They chatted for a few minutes before the stylists they had reservations with were ready for them. They were then seated next to each other. As Billy sat down, the stylist asked what he wanted done. Billy replied, "Just a trim." The stylist looked at him oddly before Anna laughed and said, "Don't listen to her. She's just not used to getting her done at a real salon." "I'll say! Look at these split ends, and no layering, ughh..." The stylist said as she ran her fingers through Billy's hair. Billy blushed before Anna told the stylist what to do to his hair. Billy did not quite understand what she told the stylist, but he said, "Whatever you think is best," and shrugged. The stylist nodded and got to work. Billy noticed that the same work that was being done to him was being done to Anna's hair. He liked Anna's hair, but he wondered why they were putting tinfoil on both of their heads. "Is the government trying to read our thoughts," Billy asked as he looked at Anna. Anna laughed as the stylist continued to work on them as she replied, "If they did, I think you'd be in real trouble." Billy blushed and wondered what she meant while she started to laugh again. Billy zoned out for a bit after that, but the girls kept working on their hair before Anna got up and led Billy over to the manicure/pedicure station. Billy shook his head at Anna and said, "I was just going in for the haircut." "Oh, don't be a spoilsport," Anna replied as she pushed him down onto the seat. "This isn't really necessary," Billy said as Anna sat next to him. "When these girls get through with your nails, you'll see how wrong you were." Not wanting to make a scene, Billy replied, "Okay, but lets keep it something muted. I don't want to look to garish." "So no red," the manicurist said to Anna and Billy. "NO RED!" Billy replied reflexively. "Okay, what color then?" The manicurist asked. "Something muted like maybe a peach." "Nothing solid," Anna chided him. "Why not?" "You could paint your own nails a solid color. If you're going to pay to have someone else to do your nails, there has to be at least a little intricacy to it." Billy shrugged and told the manicurist, "Just give me whatever you're going to give her," as he pointed at Anna. The manicurist nodded and began to work on their nails, taking turns working on each of them. Billy watched with a sense of unease as he noticed that his fingernails were being given a French manicure despite the fact that his fingernails barely covered the tips of his fingers. Billy wanted to object, but he felt that it was already too late, and he knew that he could get nail polish remover if he wanted to get rid of it for an interview in the event that the opportunity arose. After their toenails were painted to match their fingernails, Anna and Billy were taken back over to finish their haircuts. Billy waddled over to the station, careful to keep the separators between his toes as he walked towards it. His ungainly steps made Billy feel foolish even as he saw girls in salon, including Anna, walking the same way. He sighed while he sat down on the chair. He then watched with a slack jaw as the tin foil was removed. He looked at the red highlights that had been added his chestnut colored hair and cursed himself in his head. Billy knew then that he would have to dye his hair if he got an interview. Billy tried to put his hair color out of his mind as the stylist began to layer his hair. As she portioned off parts of his hair, Billy worried about the final results in silence. As she finished cutting his hair and began to style it with a curling iron, Billy realized that he was familiar with the style of the haircut that Anna mentioned to the stylist for him. If he had known the name of it, Billy would have objected to the hyper feminine style that would likely necessitate the removal of most of his hair to look even ambiguously masculine. The long layered, multi-toned haircut with side swept bangs that he admired on Anna was not something that he had wanted for himself. Despite his unhappiness about his haircut's potential affect on what was left of his male life, he had to admit to himself that he looked much better as girl with the layered hair cut. With their hair and nails done, Billy followed Anna's lead and carefully took his money out of his pocketbook. Billy paid the salon and tipped the stylist and manicurist before he walked out of the salon with the separators still between his toes and the flip flops slapping against his feet. Billy walked to the passenger's side of Anna's car and got into. Anna smiled and asked, "There, was that so bad?" Billy wanted to tell her the truth, but he was sure that doing so would have made for an awkward drive if she did not kick him out of the car then and there. Consequently, he nodded and said, "You were so right." "I usually so am," Anna replied with a smile and a wink. The wink turned Billy on as he felt his member stirring beneath the skirt of his dress and three layers of panties. Billy struggled to think about anything other than Anna as she drove them back towards her home. When Anna pulled up in front of her home, she invited Billy inside. While Billy had left his car in front of Anna's house, he had not gone inside when had arrived earlier. Billy saw no problem with following her in, so he took her up on her offer. As they walked through the door, Billy heard two young men talking to each other. Billy instantly felt knots in his stomach. "Is your boyfriend home?" "Boyfriend? No. I live with my parents. That's my brother and his loser friend." "Oh. Okay," Billy replied, still feeling worried about what the boys would think about his appearance if they saw him. Billy sat down at a table as Anna reached into the refrigerator to take out three slices of a hero. She asked Billy, "Do you want a piece?" "Why not?" "I don't know. I thought maybe you were watching figure," Anna replied. "What are you insinuating?" "Nothing. I was just asking a question." "Are you saying I'm fat?" Billy exclaimed. "Who said that?" Billy heard a boy say. "Nothing, Nat. Don't worry about it," Anna responded to her brother. "I'll decide who's fat," Nat retorted as he walked into the room with his friend in toe. "You called her fat?" Nat said in disbelief as he looked Billy over. "No. I didn't call her fat. I was just asking a question. I could have, and was, insinuating that she probably diets to look that good. That takes work." "I can see that," Nat's friend Skip said while he leered at Billy. Billy squirmed as he sat in the boy's gaze. "So how old are you?" Skip asked as he leaned over Billy. "You shouldn't ask a lady her age, don't you know that boy," Billy replied. "Well, you look too young to really be a lady." "I try," Billy replied as Anna smiled and tried to unwrap the hero slices, but she did not want to touch the plastic wrap with her freshly painted nails. "Do you need help?" Skip asked her. "We need a boy," Anna replied with a smile. Billy laughed at Anna's partially feigned helplessness before Skip unwrapped the hero slices for them. As Billy took a bite, the boys continued to hang around him despite Anna's attempts to shoe them away. After Billy finished eating, he had enough of the two of them leering at him and trying to get him to fall for their lines. Billy excused himself and said goodbye to Anna as they stepped out of her house. Anna apologized to Billy for her brother and his friend, but Billy told her that he was not upset by them. Anna looked relieved by his statement before she asked, "So you're still coming over tonight for our night out?" "I wouldn't miss it," Billy replied. Billy walked to his car and waived goodbye to Anna before he started to drive down the street. As he turned the wheel of his car, his eyes were caught by his French manicured nails. While he had been distracted most of the time since he had gotten them done, Billy was finally able to bemoan the fact that his male life outside of his home was finished until he removed the nail polish from his nails. Billy also felt that if he did it too soon, Anna would find it out and might discover his secret. Billy sighed as he decided to keep them until his nails got damaged. Once Billy pulled up in front of his mother's home, he headed inside. Angelica was sitting in the kitchen when he walked in and asked to see what he had done at the salon. Billy started to rub his elbow as he walked into the kitchen. As he walked through the doorway that led into the kitchen, Angelica gave him a startled look. "What?" Billy asked. "Wow," was the only response that Angelica could muster as she marveled at his appearance. "Is it that bad?" "That depends on what you consider bad," Angelica said while she got to her feet. "What's that mean?" Billy asked nervously. "I mean you just went up a whole point as a girl." "What?" "Honey, I'd say you went from cute to hot." "Oh, don't be ridiculous." "I'm not. I think you got a lot more from me than I ever realized. You don't look like your father at all. You almost look my mom." "Grandma?" "Oh, not when you knew her, dear. I mean when she was young. You look a lot like her. You two could almost be twins." "Well, that's just what I was going for. Now, if you'll excuse me...," Billy began to say. "You should take it as a compliment," Angelica, sensing her son's sarcasm. "That's a compliment? Mom, I'm not a girl!" "I'd be more willing to hear you out on that if you hadn't just flashed your manicured nails when you tossed your hands to the side." Billy blushed as he crossed his arms to hide his fingernails even as his toenails were visible in the baby blue flip-flops that Anna had leant him. Angelica laughed at the pout on Billy's blushing face as she said, "And with that look, you're going to tell me that you're not my little girl." Billy gave his mother an enraged glare, but he knew better than to come up with a retort. Billy stewed for a moment before he told her he was going up to his room. Billy walked up the stairs and settled in his room. He laid down on his bed and tried to put thoughts about being treated as a girl out of his mind. It was a futile effort though as the feminine clothing he was still wearing, his manicure and the open closet exposing his feminine wardrobe all provided him with reminders of how the world was seeing him. Tears started to stream down as his face as he thought to himself, 'I was a rich entrepreneur and guy. Now, look at me! I'm crying in my mom's house in a dress and working as her damn secretary. What kind of man am I? Jesus, how can I even think I'm a man when I dress like this? No! I never wanted to be a girl, I just liked the way it feels.' Billy wiped the tears away from his eyes and saw the black mascara that had run down his cheek. He sighed as he stood up and went into the bathroom to remove his makeup. Billy rested around the home that afternoon in his male clothing, even as his fingernails and feminine hair were unambiguous reminders that he was not an ordinary guy. After having dinner with his mother, Billy decided to get ready to go out with Anna. After spending the whole afternoon reflecting on his situation, Billy figured that if everyone thought that he was a girl, he may as well see what life was like for the other side. With that decision made, Billy dressed in a beige, form fitting dress made of tiers of lace with a rounded neckline, black ribbed, control top tights and a pair of beige, platform pumps with a 4? inch heel and crisscross vamp straps. Billy did his own makeup, following the instructions his mother had given him in writing. Billy smiled at his reflection and stared at the girl in the mirror that he felt was attractive. Billy started to laugh as he realized that he was lusting after himself and could never seduce the girl in the mirror. He was also certain that no one he would meet when he was out with Anna would do so either. After applying a little of the perfume his mother had purchased for him, Billy said goodnight to his mother and headed out the door. He then drove to Anna's and knocked upon her door. Anna's brother greeted Billy with wide eyes and said, "Are you sure you wouldn't be happier staying in tonight? It's a little cold for that dress." "I'll survive," Billy replied as he walked inside, feeling Nat's eyes upon his legs. Anna's parents came out to greet Billy. Billy shook their hands and said it was nice to meet them. He felt strange meeting the older couple, and he could sense that they were not happy that their daughter was going out to a club, even though she was in her mid-twenties. As Anna came down the stairs, Billy was enthralled by her appearance. The lust he felt for her returned as the aspects about her that turned him off dissipated momentarily as he stared at her thin, black stocking covered legs, which were poking out from beneath her silver dress with a cowl neckline, a woven top with rhinestone embellishments on the bodice and a jersey skirt. Once she reached the bottom of the stairs, Billy listened as her parents told Anna to behave and act like a responsible young woman. Billy was momentarily shocked by the way they talked down to Anna, but he figured it was no different than the way his mother treated him. After Anna's parents finished talking to her, they waited outside for a cab to come. Billy was a little intrigued as to why they called a cab and Anna admitted to having a prior driving while intoxicated conviction on her record. "I can't risk a second one. If I get caught again, Angelica's going to can me, and I'm afraid that she would do the same to both us if you were caught drunk driving," Anna replied. Billy nodded and agreed with her assessment. Billy then asked, "Is that what that how spiel they gave you was about?" "Yes and no. I was a party girl in college, and they don't think I've ever outgrew my sorority girl days." "Have