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Momma's Boy By Katherine Day (Story Idea by Kimber Anne) (Donald is a sweet, shy boy who gains a new life in a world of femininity.) Chapter One The boy lived in a world dominated by the sweet scent of perfume, the luscious pinks and whites of walls, woodwork, draperies, duvets and the daintiness of women's frocks. In his sixteen years, Donald Graves had always lived in a sea of femininity in the cramped two-bedroom bungalow he shared with his beautiful mother. Donald's father was long gone, having walked out when the boy was only five, leaving his mother with to raise the boy alone in the tiny home. He hardly remembered his father, and never again saw him, who had left his young bride and son without so much as a dime of child support. It was up to Donald's mother to pay the mortgage, taxes and up-keep of the house in the working class subdivision of a middle-sized city now in decline as its industrial base was lost in the exodus of its one thriving factories. Debbie Graves was a beautiful, talented woman, and was fortunate to have been spotted by an advertising executive while waiting tables at a posh restaurant when Donald was about seven years old. The executive, who handled a major account for a chain of women's clothing stores, thought the young woman had a warm, wholesome appearance that would appeal to the middle class clientele of the chain. "Debbie, let me give you my card," the man said when being presented the check, using her first name. Obviously, he had remembered it from her greeting earlier that she said routinely, "Hello, my name is Debbie, would you care for something to drink before you order?" "OK," she said warily, tucking it into the pocket of the skirt. "Seriously, miss, I want you to look at it. I'm George Harmon, with Cook's Fashions. You know the stores, I'm sure." "And what has that to do with me?" she replied, a bit sharply. She was used to getting invites due to her obvious good looks, always quickly rejecting them. Often she contemplated wearing a wedding ring just to ward off the constant flirts of man of all ages. "Debbie, please don't get me wrong," he said. "It's just that you might be just the person we're seeking to model a new line of clothes. We're holding auditions next week, and if you're interested, please call the number on the card. You'll talk to Sasha, my assistant, and she'll set up an appointment. No obligation, but I think you might be perfect for the job." Debbie Graves accepted the man's offer and was one of two women chosen for modeling a new line of clothes. Thus it was that the small Graves house became chock-full of women's clothes of all sorts, cosmetics and feminine garments; stockings and undies drying on the shower rod in the bathroom, young Donald was immersed into this world of lingerie and perfumes and lacy fineries. While Debbie's modeling assignments paid well, they couldn't supply enough income to support herself and her son, and she continued to waitress, restricting her work at the restaurant to the dinner hour, leaving the daytime hours open for modeling assignments. For Donald, it meant a series of baby-sitters until he reached the age of twelve and Debbie felt her son was old enough and responsible enough to care for himself. Usually he was placed in charge of a neighbor woman and her teenage daughters, who readily accepted the gentle, shy boy into their home, giving him space to do his homework, read or watch television where he went after school and stayed until his mother picked him up at about ten o'clock. Of the three daughters of Mrs. Campbell, Donald became especially close to Tanya, who was about fifteen when the ten-year-old Donald began staying with the family. All of the Campbell girls were intrigued that their next door neighbor had become a fashion model and they scoured the department store's advertisements for pictures of her in various outfits, ranging from outer coats to lingerie and bathing suits. Tanya had told Donald that she was the ugly sister in the family, being too fat and pimply, while her sisters (one younger and one older) were pretty enough to become models. "Maybe you can be like Cinderella, Tanya," Donald told her one day when Donald had turned eleven and Tanya was now sixteen. In the year, he had been staying in the Campbell household, the two had become inseparable friends as Tanya assumed the chore of watching Donald, freeing the other Campbell girls to do their own things. While Donald was free to be outside playing with the boys in the neighborhood as long as he stayed in the area, he found his time with Tanya to be special. The two had gotten into the routine of turning to television after school to watch one of those fashion shows in which poorly dressed women are turned into tasteful beauties. It had become the favorite show for the two lonely souls as they offered their own observations about the clothes the woman would choose to pretty herself. The other two sisters laughed at their sister, one of them saying nastily, "They could never make you pretty on that show Tanya." Donald was shocked as he saw Tanya begin to cry. "Don't say that to her," Donald challenged, his voice rising into girlish levels. "She's my friend and she is pretty." "Don't make me laugh, Donnie. In fact, they'd have a better chance of making you a pretty girl than Tanya," the older sister, who initiated the taunting, said. "I'm not pretty, Donnie. You are prettier than me," Tanya said, breaking into all out tears and getting up from the couch and running into her bedroom. "Now see what you've done. You made her cry," Donald said. He followed Tanya into her bedroom where he found her laying on her bed, sobbing noisily. "Don't cry, Tanya," he said, laying down next to her. Donald moved tightly against the girl, nestling into her softness. He felt warm and comforted. Soon Tanya quit sobbing and she moved to hold the boy tightly, her arms engulfing him. She smelled soapy and fresh, her skin was smooth over her mushy heavy arms. "You're such a sweet boy, Donnie," Tanya said. "You're my onliest and bestest friend, do you know that?" "I like being your friend," the boy said, his wonderment growing over the realization that this teenage girl would not have any other friends her own age. "It would be even better if you were a girl, Donnie. You really are pretty and I can imagine how you'd look in some of those outfits," she said. "I'd like being a girl with you, Tanya," he said, suddenly wondering why he said that. After all, he was a boy. "That'd be fun, but Donald, you must forget I said that," Tanya said, apparently realizing she may have gone too far. "You're a boy and soon you'll start getting a beard and you'll feel differently." "I suppose so," he responded simply. Little did he know that the seed that may have been planted inside him would start to spout and change his life forever. ***** "Did you mean it the other day when you said you'd like to be a girl with me, Donnie?" Donald blushed at the question from Tanya and didn't respond immediately. "Come on Donnie, did you mean it?" "I guess," he finally admitted. "But I'm not a girl." "No, you're not, but you could be such a cute girl," she said, her eyes bright with a sparkle. Tanya's eyes were in reality her only physic feature that could be termed beautiful; they were a dazzling blue and bespoke of the intelligence that the girl had. "I couldn't. I'm a boy." "That doesn't matter. Let's try putting some dresses and stuff on you and maybe fixing your hair and giving you a bit of makeup. Let's see how you'd look as a girl. What d'ya say?" "Oh, I'd be embarrassed," he protested. "But I like being your friend, Tanya." "We're like girlfriends now, aren't we?" Donald nodded. It was true, he realized, since the bulk of his activities at the Campbell household had involved watching fashion shows with Tanya and several teen girl sitcoms; the two also read a lot together and Tanya had introduced Donald to some current novels mainly focused on teen girls. "Let's do it then," Tanya said. "No one else will be home for several hours and I got just the clothes for you." Donald was intrigued by the idea of dressing up like a girl; since he was told several days earlier that he'd look cute as a girl, he had wondered if maybe that were true. He liked girly things, he knew, having watched his mother pretty herself up each day as she prepared for work either in the restaurant or on a modeling assignment. Several times when he was about seven or eight, she had invited him to sit on the bench in front of her vanity and she applied lip stick and eyeliner to him, finishing up the process of brushing his long light brown hair. "See mother and daughter together," Debbie said, laughing. "I'm pretty, mommy, aren't I?" Donald remembered he said. "Yes, you are my sweet," his mother said, hugging him and kissing him gently on the forehead. Donald loved those moments, the hugs and the admiration in his mother's eyes. Would she love him more, he wondered, if he was a girl? When Donald turned eight, Debbie Graves refused to let the boy sit next to her while she prepared her makeup; she also stopped putting makeup on him and ordered him never to do so on his own. "You're a boy, Donald, and you must grow up to be a man," she ordered him. "Yes, mother, I know, but it was just playing. It was fun," he said. "That may well be, but it is to be no more. Understand." ***** Even though Donald knew his mother would be mad and refuse to let him stay at the Campbells if she learned of him being put in a dress, the boy followed Tanya into her bedroom. It was not unusual for the two to spend time in the girl's room since it offered a refuge from the active household where loud music or television programs made it difficult to read. Donald normally curled up in an old easy chair while Tanya lay on her bed as the two would read. Tanya had a large doll collection as well, including several Barbies. When they got bored with reading, the two would bring out the dolls and begin dressing them with a large collection of doll clothes. "Don't you ever tell anyone I'm still playing with dolls at my age, Donnie," Tanya warned him. "Why not? It's fun, isn't it?" he said, teasing her. "If you do, I'll tell them that you play with them. What kind of boy does that?" This trip into the bedroom was not to dress dolls, but rather to dress up Donald as a girl. It was apparent that Tanya had planned ahead for the dress-up as Donald saw she already had clothes laid out upon her bed. "These should fit you fine, Donnie. I wore them when I was your age," she said. "I suppose so," the boy said, beginning to wonder whether this was such a good idea. She gave him a choice of two panties, one in pink satin with lots of lace and the other a plain satin in a peach color. "I'll leave the room while you take off all your clothes and change into the panties you like the best," she said. "Take everything off?" "Yes. Don't worry, with your panties on it'll be just like you're in your swimming trunks," she assured him. Donald never liked taking off his shirt since he hated to expose his chubby, soft body. His arms were mushy and he had developed a roll of fat at his waist. His flabby chest had developed small, girlish breasts, as well. It wasn't that he was particularly fat; he wasn't. He just didn't have the kind of body most boys had. With Tanya, however, he felt more comfortable because she, too, was fat and likely would not notice his sorry physique. Even though Donald was tempted to put on the lacy panty, he chose the other one, more to hide the fact that he was truly enthused about dressing up like a girl. He didn't want to appear to be too eager. "Good, I have just the bra that matches that panty," Tanya said when she re-entered. "A bra?" "Yes, Donnie, you're at an age when girls start wearing training bras. In fact, you could have been wearing one already. You have the cutest boobs." "I do not," he protested. "It's OK, Donnie," Tanya said in a comforting tone. "It's just your baby fat stage. As you get older you'll change, but for now let's just make you into a cute girl for a while. OK?" After the bra was fastened, she held out a light yellow summer dress and lowered it over his head, assisting him in putting his arms through the short, cap sleeves. It hung down to about mid-thigh and had a scooped neck that showed the top of his breasts and the cleavage. He liked the feel of the cloth around his legs. "Let me see," he asked Tanya. "Not yet. You're still not a complete girl," she said. She ordered Donald to sit on the desk chair, and began brushing out his hair; it was light brown and longish, reaching down to the back of his neck. "You have nice hair, Donnie, and I'll let it flow straight, but give you some bangs. That should make you a pretty girl." Donald sat still as she did her work, worried that he'd be unable to undo the girlish touches in time to revert into his male self. "There, now let's give you some lipstick and eye-liner," she said. "Not too much, Tanya. You'll just have to take it off." "Oh, you don't want to show my sisters how pretty you are?" she teased. "No," he said emphatically. Tanya giggled. "Really, I know you'll be just lovely." After she finished applying the make-up, Tanya said. "Here's a pair of my old Mary Janes you should be able to wear. Put them on and then you can go to the mirror and check yourself out, Donnie." Donald was afraid to look, convinced he'd look weird, like a boy trying to look like a girl. Instead, he saw a girl in the mirror; she was a soft, warm looking girl with a sweet face. "That's me?" "Yes, my dear. That's you. You have such a naturally pretty face, too." "I guess I could lose a little weight, though," he said. "You're not too fat, Donnie, and I know boys would like you just as you are." "But, I'm not a girl. I don't want boys liking me like that." Tanya laughed. "If you go to school wearing that, you'll get plenty of boys interested in you. I'm jealous." The girl taught Donald a few tips on how to act girlish, such as smoothing the dress as he sat down, keeping his legs together when he sat and walking with shorter steps. He took to it easily and the two acted as girlfriends for nearly two hours when it was time to return Donald to his boyhood. "Did you enjoy being a girl today, Donnie?" Tanya asked. "I don't know. It was kinda weird. I liked being pretty, but I'm a boy. I shouldn't be doing this. It must be wrong." "I know," Tanya said. "I shouldn't have suggested this. I could get in trouble." "It's fun being girlfriends," Donald said. ***** Tanya and Donald were unable to play dress-up again; there was always the expectation that others in the Campbell household would discover them. Both were horrified by that prospect, because Tanya knew that she'd be accused of corrupting the boy and that Donald felt he'd be forever shamed as a pathetic sissy boy. Yet, Donald relished the memory of those several hours as Donna -- the name the two children had chosen for him during the episode. Now that he was twelve, Donald's days of being watched by the Campbell's ended; he'd get home from school each day while his mother was still home, usually getting herself ready to head off for her waitress job. From about four-thirty every afternoon until about ten each night he'd be home alone, facing strict orders not to have anyone else in the house, except of course for anyone from the Campbell family, since they still maintained a loose supervision over the boy. At first, Tanya stopped over to see Donald during his hours alone on the ruse that she was checking up on him for her mother. She was still the lonely fat girl she had been, but she had begun to put more attention to her looks and to her eating habits in hope of losing weight. During their visits, she and Donald talked about what clothes she should wear to become more attractive and she was astounded by the good taste the boy had developed in feminine outfits. "Remember the day I dressed you up, Donnie?" she asked during one of those visits. "Yeah." "That was fun, wasn't it? she asked. "Yeah, I guess so." "You guess so? Donnie, you loved it, I know you did and you were so cute." Donald blushed. "Ever think of dressing up again?" "Ah . . . no," he answered hesitantly. "Never?" "Well, sometimes," he admitted, hiding the fact that he thought about it every day, usually when he was in bed, trying to get to sleep. It was then he became conscious of his girlish chest. Even though he was beginning to trim down and lose some of his adolescent fat his breasts seemed to be just as noticeable as ever. He found he loved playing with them and one night he had his first experience in masturbation. It was a magical mind-numbing happening and the creamy juices emitted while he was imagining himself as a girl. "I'm sorry I brought it up," Tanya said. "No, no, no. That's OK. We had fun then didn't we?" "Yes, we did, girlfriend," she said, giggling. He joined with a girlish giggle of his own. Tanya's visits quickly ended, however, since she got a job working from 4 to 8 p.m. most nights at a fast food place; then, too, she got her first boyfriend. ***** Thus it was that Donald was usually alone after school and into the evening; yet, he wasn't lonely. Since entering middle school, he had withdrawn from making friendships, feeling ill at ease among the rough- talking boys of his age. They all seemed to have discovered sex and the need to appear macho, constantly talking about "pussy" and "cunts" and using assorted four-letter words. Such talk bothered him, made him feel uncomfortable and he withdrew into himself. He learned to cook and bake, using his mother's cookbooks and watching shows on the food network. Each afternoon, he prepared a dinner for himself, with enough to be set aside for his mother to eat for her lunch the following day. "I feel so guilty, Donald, leaving you alone like this. Why don't you get out and make some friends?" his mother urged. "No, mother. You're busy, besides I like creating stuff," he replied. "Donald, that's not fair to you," Debbie said. "Mom, don't worry. Don't you like my cooking?" "Oh, my darling son, I love it. You're getting to be a real chef." It was hard for Donald to resist eating some of his own creations, particularly the apple pies he began preparing. He experimented with his own fillings, adding various spices and other fruit along with apples. He shared them often with the Campbell family; Mrs. Campbell was particularly impressed, telling him: "You ought to either market these pies or at least submit them in the County Fair for a blue ribbon." As a result, Donald continued to be somewhat overweight; he lamented his soft belly, bouncy breasts, mushy thighs and flabby arms. He knew he should begin exercising and occasionally tried to do pushups and leg lifts, but his spirit wasn't into to it. As she did every so often, Tanya stopped over one summer afternoon to talk. The two remained friends, sharing with each other all sorts of private thoughts neither would tell others. Theirs was a special bond. Donald by now was fifteen and Tanya was nineteen, a freshman at the local university studying English. While Donald continued to be chubby, Tanya had lost much of her weight and had become a quite lovely young lady. She would never be a thin woman, due to her naturally large frame, but with her sparkling eyes and warm disposition she was most attractive. "These oatmeal cookies are to die for," she told Donald on this visit. "If I don't watch out, I'll get to be fat again." The two were in the Graves kitchen drinking tea, giggling over the new Paris fashions pictured on the pages of a copy of Glamour magazine. "I can't see any woman wanting wear those things," Donald said. "Wouldn't you love to model them, Donnie?" she asked. "Me? I'm too fat." "You're not, really. Boys like girls with figures like yours." "Me? I'm not a girl." "I know, but I think back to that time when we dressed you up," Tanya said. "You looked so cute then." Donald blushed. "You should try it again, Donnie," she urged. "No, I can't do that." "You really do have a pretty face, you know." Donald quickly changed the subject, asking her about her relationship with her boyfriend, Brian. The idea of putting on a dress was ever- present, though he hadn't done it again. Maybe it was about time he did. Chapter Two The idea haunted him during the next day at school; it was a Friday and he knew his mother would be leaving for her waitress job about four o'clock and likely not be home until nearly eleven. He dreamed of giving himself a bubble bath, applying lotion across his body and becoming totally girly. For a while during U.S. history class, he looked across the aisle at Wendy McCord, who was one of the few girls who wore dresses to school, apparently due to her family's strict religious traditions. Wendy's dress was a relatively drab beige-colored affair that fell below her knees; it had a high neck and cap-sleeves that exposed her slender, soft white arms. She had a round face and wore no make-up. The girl's hair was brown, straight and hung down onto her back, restrained only be a dark brown hair band. He was enamored with the girl who even in her plainness exuded natural beauty and femininity. He considered the girl for a minute, musing that he had many of the same soft, white bodily features as Wendy McCord. He wondered for a minute about getting Wendy into a salon for a few hours, figuring that this plain, broad-faced girl could became quite pretty. Then Tanya's words of the previous night hit him: "You really have a pretty face." What if he were to be in a dress like that worn by Wendy? How would he look as girl? So often, he had looked at the girls in his school, thinking how much he would be just like them, gathering together in giggly gossiping or crying over the failure of some boy to notice them. He wanted to join them so often, but never did. He got home in time to see his mother - still in panties and bra - primping herself up before putting on her waitress outfit. Debbie Graves had never been shy about hiding her body from her son and since the boy had been young he had always hung around in her upstairs bedroom as she dressed. Often, he either complimented her about the makeup she wore or the way she fixed her hair; sometimes he'd offer criticisms. "You're always right, you know, Donald. I swear you're sometimes more like a daughter to me," his mother said more than once. "I want you to look nice, mother," he explained. "I know you do, honey, and that's so sweet," she would usually reply, following that with a brief hug. Donald Graves watched as his mother backed her car down the driveway and into the street. He looked out the window as her car continued west and out of sight. He bounded upstairs and into her bedroom, opening up her dresser drawers to pull out a hot pink thong, nude pantyhose, a denim skirt and a cute pink blouse with a scooped neck and cap sleeves. He smiled as he held the blouse up in front of him as he stood in front the mirror. "Wow, you're going to be hot, Donna," he said aloud, using the girl's name he had first chosen for himself during his youthful dress-up with Tanya. He followed that with a high-pitched giggle. The boy pranced into the bathroom and began to draw water for his bath. He took off all of his clothes, looking admiringly at his soft white body; he was not at all muscular and while that shamed him as a boy, he welcomed the look this day. He would look so convincingly as a girl, wouldn't he? He luxuriated in the warm, bubbly sweet smelling water, even beginning to sing in his faux female voice. Finally after some twenty minutes, the water cooled and he got out, drying himself off with a soft, pink towel. Sitting on the side the tub he shaved his legs and into his crotch, even though his body hair was thin and light and likely wouldn't be noticed. His smallish penis was erect and he pressed it between his chubby thighs, increasing the erotic sensation. He worried about getting so excited that he'd suddenly lose control and ejaculate, spoiling the moment. When done, he squirted a few spritzes of his mother's body spray and then applied her sweet smelling lotion to apply to his legs. Looking at the selection of containers of feminine cosmetics on the counter, he saw a small spray can of her feminine deodorant, and mused: "Why not? Girl's need that, don't they?" He picked up the can and sprayed its contents into his crotch and his anus. He looked at the large selection of cosmetics and smiled. He had watched his mother apply such makeup almost every day; since he had been a little boy, he had been enamored with the process and he knew how it should be done. He thought back to those early years when his mother had playfully applied makeup to his face; he so loved it when she did that and had been disappointed when she stopped the practice, telling him "little boys don't wear makeup. It's for girls." All alone and feeling adventurous, he began first with mascara, carefully wiping it on his face; he followed that with a bit of coloring to his cheeks, eyeliner and finally lip gloss. He enjoyed the process, particularly when he pursed his lips, as he'd watch his mother do many time. He felt so girlish as he did so. As he worked on his face, he saw the image of a smooth-faced girl in the mirror. He smiled at the image, who smiled back. "What a pretty girl," the boy said. "But I must do something about her hair." He began to brush his hair, which reached only down to the back of his neck; he wished it were longer. Nonetheless, he was able to create bangs that went across his forehead and helped to frame his face and enhance the femininity of the face he saw on the mirror. Finished in the bathroom, he wrapped the large towel around him, covering him from the chest down, as he'd seen his mother do many times. Now, feeling totally feminine, the sweet, smooth-bodied boy moved into the bedroom to put on the clothes he had selected earlier. He dropped the towel and stood naked in the room, glancing at the full-length mirror that his mother had affixed to a closet door. He was obsessed with the thought that his body was like that of a girl's, soft and tender and smooth. He put on the pink thong, stepping into it eagerly and almost lost his balance in the process. Then he realized that he forgot to find a bra in his mother's dresser, and carefully rummaged through a drawer, hoping to find one. He had watched his mother put on her bra many times, and had even assisted her in hooking it up at times. He found a pink bra with lace trim that seemed to match the thong. Fortunately, his mother was not a large-breasted woman. He looked at the tag on the bra; it was a 36-B. Since Donald's chest was fleshy, the boy felt that he might even fill the bra cups naturally. He fitted the bra, fastening it in the back without much difficulty, as if he's been doing this process for years. He smiled and he saw the result, again looking into the mirror and seeing a bit of cleavage. Next, he sat on the bed and put on the pantyhose, carefully rolling it up so as to not ladder it in the process - feeling as if he was a lovely teen girl. Donald put on the pink blouse, lowering it down over his head and finding it was quite tight; it took a bit of adjusting, but soon felt comfortable, feeling the satiny material against his skin. He felt pleased as the scooped neckline exposed the modest cleavage. Finally, he stepped into denim skirt, which also was tight around his tummy. The skirt was short, ending at mid-thigh, showing his legs in their nude-colored hose. He raided his mother's closet to find a pair of two-inch kitten heels with open toes. They fit him perfectly. "Hi, I'm Donna," the boy said in a high-pitched voice. He stood in front of the mirror, posing as he had seen models do during the many fashion shows he had begun watching on television. After doing several poses, one more feminine than the other, he walked out of the room in the heels, taking short steps, his feet pointing straight ahead, and his hips swaying naturally. Having watched the motions of the girls in his school, he found himself easily walking in what he thought were totally girlish mannerisms. He entered the living room, and sat on the couch, crossing his legs. He admired his pantyhose-encased legs, with his toes peeking out through the front of the open-toed shoes. Donald began giggling to himself; he'd never felt so good about himself in his life. The boy was so entranced into his life as Donna that he was unaware of the noise of a car entering the driveway next to the house. Suddenly there was a click and the sound of heels on the floor. "Mom can't be home?" he ask himself, frozen in fear. Yet, there his mother is, her eyes boring into him. "What are you doing, Donald? Or are you something else?" his mother said sternly. Donald grew flustered and stammered: "I . . . ah . . . ah . . . just . . . ah . . . mean . . ." "My dear," his mother interrupted him, moving over to sit down next to him. She put an arm about him and drew him close to her. Donald's face became buried into her modest bosom and he began to cry, his body rocking with emotion; his mother hugged him even more tightly as the scent of her faint sweet perfume filled his nostrils. Donald sobs subsided and his mother continued to pat his back slightly, her hand obviously feeling the straps of his bra. "Mother, you're home early?" Donald asked, his voice thick due to the crying. "It was quiet tonight at the restaurant and I asked to go home, and now I find that I have a lovely daughter," she said, her voice soft and gentle. "You know I always wanted a little girl." Debbie Graves released her son from the hug, and reached into her purse, pulling out a tissue and giving it to Donald. "Now wipe your face, my darling," she said, smiling. "You're not mad, mother?" he asked. "How long have you been doing this?" she demanded, not answering his question. Donald was confused; his mother seemed upset with him, but he couldn't tell whether she was mad and might ground him or discipline him in some way. "About two years, mother," he said. "I thought so. My clothes haven't been put back in the places I thought I left them." "I'm sorry, mommy. Let me go change back into my boy clothes," he said, beginning to stand. His mother held him down. "No, dear," she said. "Let's sit here and talk about this." "Yes, mommy, I'm sorry," he said bowing his head and feeling as if he was to begin crying again. "Now, do you like the feeling of being a girl dressed up pretty?" she asked. Donald didn't know what to say, fearing if he gave the wrong answer, his mother might become angry with him. "Well, do you?" she persisted. "Yes . . . ah . . . mommy. I love how it feels," he said, his voice quivering. "I thought so, and you know you are a very pretty girl," his mother said. She leaned over and gave him a sweet kiss on his cheek. "I feel like a real girl when I'm dressed," he said. "That's nice, Donald, but we can hardly call you Donald when you're in these clothes, can we?" The boy giggled. "What shall it be? Donna?" Debbie Graves asked. "Oh, mommy, that's a nice name." How weird was that, he wondered? Why had his mother chosen the exact same name that he has chosen? Had Tanya told her about his dressing episode? He doubted she would have. Still it was strange. His mother smiled at him, "Donna it is then, but let's make it Donna Jean." "Oh mommy, I love it," he said, putting his arms around his mother. "Yes, a pretty name for a pretty girl!" Donald was happy; he had been hiding his feelings from his mother for such a long time in fear of her rejection. If she would have dismissed his dressing up as either a childless happening or as something disgusting, he would have been devastated. He loved his mother dearly and wanted her complete acceptance and love. "Mother, you've made me feel so good. I was so afraid you'd make me take these clothes off and never dress like this again." "If it's how you feel about yourself, I guess we have to live with it and if you want to be a girl when you're at home you can, but I have conditions," she said, her voice growing a bit stern. "What are those mother?" he asked, affecting a soft, dismissive voice that he hoped sounded feminine. Debbie Graves smiled at the boy and said, "Well, Donna, we're first going to have to get you some clothes of your own." ***** "I see you already know how a girl is supposed to sit down, don't you Donna?" his mother said. The boy had entered the car, careful to smooth out the skirt he was wearing, as he sat down. He smiled, pleased to hear his mother address him as "Donna." He wondered whether he liked the girl's name better than being Donald. "I feel I should act like a girl, mommy," he said. "You must have been practicing," she smiled, as she turned on the ignition. Donald brushed back his long hair, using a dainty gesture that he hoped look appropriately girlish. He looked down at his nylon-clad legs, clearly exposed from mid-thigh as the short, print skirt had slid up. The boy smiled as he looked at his legs; while somewhat fleshy above the knees, his calves were slender and shapely. He mused to himself: "I have pretty legs, I think." He watched as his mother, turned right onto Grand Avenue, and headed in a direction that would take them to the outskirts of the city. "Where we going?" he asked. "You'll see, darling." She drove on for a while as they passed a string of fast food places, strip malls and gasoline stations. Donald fiddled with his hair, his imagination running rampant with the thought that he was a pretty teen girl on a mother-daughter shopping trip. "Now, Donna, why didn't you tell me you liked to dress up so pretty?" his mother asked. "We could have had so much fun together. I love having a daughter, too." "I was afraid, mommy, scared that you would think I'm a freak." "No, honey, mommy wants you to be happy and if you're happy to be Donna, that's fine." "I like being Donna," he said, feeling his face grow flushed. "My pretty one, if that's how you feel, there's nothing wrong with it," she said. "Lots of boys and men like to dress up and be pretty." "Mommy, I'm curious about something." "Oh?" "Yes, what does it feel like when you have sex? How do your boobs feel when you have sex?" "Don't worry, baby girl. You'll soon find out." His mother pulled the car into a strip mall and parked in front of the Horizon Medical Supplies store. "I have to run into the store for a minute. Just stay in the car, Donna." His mother soon returned to the car carrying a large green plastic bag, opened the back door of the car and put it inside. "One more stop before we go to the mall," Debbie Graves said once she had returned to the car. She turned the vehicle and continued the trek toward the outskirts. As they approached the Interstate, she turned into a parking lot filled with cars and several semi-trailer trucks. The store carried the name "Paradise City" framed in flashing lights. A smaller sign read, "Adult Toys and Books." Again she asked Donald to remain in the car, returning about fifteen minutes later with three large bags that she placed into the back seat. Donald tried to see what was in the bags but was able to only make out the word "STRAP" on one of the boxes. He wondered what kind of strap was in the box, but quickly determined it might be something a bit naughty. ***** "Nothing's too good for my lovely daughter," his mother said, when they reached the Westpoint Mall. "Is there anything special you'd like to wear, honey? The cost is not important. Anything. Anything at all to make you the prettiest girl in town." "Oh, mother, you know best, but I'd love more pantyhose and thongs, plus thigh highs and heels, too," Donald said, his eyes wide with excitement. "OK, darling. You wait here and I'll be back in a half hour, or maybe longer," she said, patting his hand gently before getting out of the car. He watched as he saw her enter the Fashion Bug store; he wished he could have gone into the store with his mother taking the role of being her daughter. Yet, he was glad he didn't have to face any possible embarrassment, since he feared that he still looked too much like a boy in spite of the skirt and top that he was wearing. His mother had warned him not to look in the shopping bags in the rear seat, and despite wanting to be mommy's good little girl, he couldn't resist the temptation to see what his mother had purchased at Paradise City Adult Toy Store and Horizon Medical Supplies. He flipped down the seat, giving him an opening to the back seat and the shopping bags. In the bag from the medical store, he saw a package that said "breast forms - size C." His penis hardened as he imagined himself weighted down in the chest by the faux breasts. His other discovery came from the Paradise City package and a box entitled: "Strap-on harness" with indication that it was "8 inches - standard." Suddenly the car seemed to grow hot and stuffy as Donald's imagination soared to make him a lovely teenaged girl. Fortunately, the Graves car was an older one without many gadgets, and Donald was able to lower the window a bit to let in the cold outdoor air. Spying his mother leave the Fashion Bug store, he quickly put the items back into their bags and restored the seat to its original position. His mother was lugging a bag in one hand and a garment bag over her shoulder; it obviously must have held a dress or perhaps a skirt and blouse. He got out of the car, opening the back door for his mother, and she placed the bag in the back and reached in to place the garment bag on a hook inside the left rear door. ***** The drive back to the house seemed to last forever. Donald was anxious to see all of the feminine niceties that his mother had bought for them. "Mother, I just know you must have found the loveliest of clothes for me," he said. "I just can't wait to put them on for you." "My darling, Donna, I think you'll be the prettiest girl around when you've put these on and we've made up your face and fixed your hair," she said, smiling at him. "You always have the greatest taste, mother." "Donna, honey, it takes more than pretty clothes to make you a truly pretty girl," Debbie Graves said. "I know, mother." For the next few minutes of the drive, his mother offered tips on how a girl walks, carries herself, sits down, holds her knees together, moves her arms and other mannerisms. Donald listened attentively, certain that he wanted to look and act in the most feminine of manners. "I feel I want to be a total girl, mother," he confessed as they drove into the driveway next to their home. "We'll see, dear," was all his mother said. ***** The idea of being "Donna" excited the boy and he eagerly assisted his mother in emptying the car and carrying the packages up to his mother's bedroom. "Don't look in the bags just yet, Donna," his mother warned. "Oh mother!" He was growing impatient to see all the clothes she had purchased. "Now, I want you to draw yourself a nice warm bath, and to use the bubble bath crystals; they're in the pink bottle in the cabinet. While in the tub you can shave your legs, your armpits and anywhere you have hair, except around your crotch. OK?" Donald found the warm, soft water stimulating and his penis grew hard as he heard his mother rustling the bags in his room. The scent of the bubbles added to his hardness. Putting first one leg than the other up on the side of the tub in order to run the razor, he was enamored with the smoothness and the softness of his calves and thighs. He hoped his mother would have nylons for him; he realized his legs would likely be pretty and most feminine. His penis continue to harden, almost to the point of unbearable pain; yet, he felt he needed to hold back. Finally he got out of the tub and as he was doing so, his mother entered the bathroom, holding a new, pink fluffy robe. "Are you excited, my darling?" she asked. "Oh, mother," he said, attempting to hide the erection from here. "Oh, honey, don't think I haven't seen that before, but my how the little thing of yours can grow and get so hard. That won't do. Let me take care of that for you." She told him to put the robe on and dry himself off. He did as instructed and before he could tie the robe closed, his mother reached down and took his small, but erect shaft into her hand, beginning to stroke it rhythmically. It pulsated within her hand, and Donald was surprised as she knelt before him, putting the shaft into her mouth, soon taking it all deep into her throat, and sucking on it, massaging it with her mouth. The pain was excruciating and soon he could resist no longer, shooting all of his cream into her mouth. "Oh my God," he exclaimed as his juices flowed into his mother's mouth, overflowing. When the flow stopped, his mother slowing slipped the shaft from her mouth and moved up, putting her lips against his, forcing him mouth open with her tongue, and releasing the juices into his mouth. "Swirl that around to taste, honey," she said. He loved the salty, unique taste of his own juices and wanted more. His mother then drew him tightly into a warm hug and he relaxed. He felt weak and spacey. After a few moments, his mother released him and used a damp washcloth to cleanse his pubic area. "You have such a sweet body, dear Donna," she said when she finished. His mother took him by his hand and led him into the bedroom. A sheet covered what Donald suspect were the clothes she had purchased for him and his imagination grew rampant, thinking of the feminine goodies that must be hidden under the sheet. ***** "Relax, Donna, we'll get to what's hiding under the sheet soon," his mother commanded, directing him to sit on an upholstered bench in front of her vanity. He noticed the vanity was covered with various cosmetics. "Are those for me, mother?" "Yes, dear, now turn around, so your back's to the mirror," she ordered. The chore of applying makeup seemed to take forever, but Donald enjoyed it. He was enamored with the sweet scents of most of the materials she used on his face; actually, he had watched his mother numerous times as she dressed and applied makeup and had wondered how it felt. So far in his occasional dressing episodes, he had only gone so far as to sneak into his mother's room and used lipstick. After working on his face, his mother brushed and styled his long blonde hair, creating bangs that went off to the right side of his forehead and small bob at the ends of the hair. Then, she painted both his fingernails and toenails a matching pink color. "Don't look yet, darling," his mother said when she finished. "I want you to see the complete Donna." "OK mother," he said, tempted nonetheless to see how he looked. "Now stand up and take off the robe," she said. "But, mother, I have no clothes on," he protested. "Just do it." He did as commanded, and felt totally exposed, ashamed of his soft, unmanly body. "You'll make a very realistic girl, I'm sure," his mother said, smiling. "Really, mother?" She didn't answer, but reached over and pulled the sheet off the bed, revealing a plethora of female garments, including a knee-length black cocktail dress, six pairs of heels of all styles (but all fashionable), nine packs of nude pantyhose, assorted nude thigh-highs along with two pairs of white pantyhose, and a set of black thigh highs. There were various pieces of lingerie, including dozens of panties in differing styles and colors, bras of both plain and lacy design, and several black and white slips. In addition, there was a two-piece swimsuit, girlish tee-shirts, about a half dozen skirts (mostly short) and an equal number of blouses. "What would you like to wear today, darling?" she asked. "Oh mother, all of it," he said excitedly. He felt his member beginning to grow hard again, as he looked at each of the items, picturing himself in various types of girlish dress. She reached down and picked up a short skater-style dress he hadn't seen before. It was pink, with lavender trim. "That's divine, mother," he said. "Let's start first with the undergarments," she said. She picked out a pair of pink, cotton panties. "Can't I wear the lacy panties, mother?" he asked. "None of them complement the dress, honey. It's such a short dress that if you lean over too far, your panties will show, so you need a pair that matches it." Before he could put on the panties, she handed him a thong-type garment. "Wear this first; it'll hold in your male part, and then put on the panties." She found a padded pink bra for him; he had a fleshy chest and already had the beginnings of girlish breasts and they fit perfectly into the bra, creating a cleavage. "Oh mother, just like a girl's boobs," he said. "Almost, but we'll add these to make you look more real," she said. She inserted breast forms into the bra cups. His mother lowered the pink skater dress over his head, being careful not to mess up his hair. When it was finally fitted to his body, he looked down, impressed by his bosom; the top of his natural cleavage was displayed by the scooped bodice. The dress was belted at the waist, and skirt flared out. "Now sit darling," his mother commanded. She assisted him in putting on the nude thigh highs, rolling them up his legs. He had watched his mother do this hundreds of time, and Debbie Graves was surprised how Donald - now Donna - was able to easily finish the process unaided. "I see you do it just the way any woman would. You're a natural girl, Donna Jean," Debbie Graves said to her erstwhile son. Finally, she put on a pair of sandals with a three-inch heel. "There you are now, Donna. You may look at yourself." She directed him to the full-length mirror on the closet door. "Oh, mother, I'm a girl." "Yes, and such a pretty one, too." "I feel just like Donna," he added. "What a lovely daughter I have," his mother said. She hugged him and soon both were crying. Donna Jean knew they were tears of happiness.