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Valentines By Cheryl Lynn This is a work of fiction and a follow up of my Eve stories. Please read them before this as it will make for a better story. I have resurrected and old character that I loved, Thelma Vitner from "A Christmas Story," which I thoroughly enjoyed. It may be downloaded for personal pleasure all other use prohibited unless approved by the author. If you do not enjoy forced feminization and humiliation, do not read. Again, this story is not for the squeamish and sensitive reader. You have been warned. Comments appreciated at [email protected]. Valentines Ever since Halloween Harold's life took a downward spiral. The holidays had seen his manhood devastated by a series of unwanted events. First he was tattooed then festooned into a fake vagina and artificial breasts. The tattoos would never come off and the prosthetics he was told would stay attached at least three months. Then for New Year's Eve he was abused by four boys. His only good break came the first week of the New Year, when his mother discovered that nail polish remover would dissolve the glue holding the prosthetics to his body. The relief he felt knowing that he wouldn't have to go to school with those awful attachments was palatable. Watching his mother remove them, however, had been traumatic. The fact that he could now masturbate was a great relief. His mother had also signed him up for therapy sessions after his ill fated Halloween experience. His mother, a single parent, worked as an assistant HR director in a small company. As such her benefits package was small and health care coverage limited. She could only afford to send her child to see his therapist once a month. She was shocked and appalled when he came home late Halloween night when she discovered what had happened. When that was followed up by his Christmas antics, she was beginning to wonder whether or not her son's adventures were actually forced upon him. If she had known what he did New Year's Eve, she would have had serious doubts. She had no delusions about her son. He was a wimp, had been all his life, and his few friends were definitely of questionable character. They were Goth's and in her mind, no man, no real man would wear lipstick and eye makeup even if it was black. So when her son showed up tattooed and reeking of alcohol and sex at Halloween, she wasn't altogether surprised. Hanging around a bunch of weird guys that wore makeup was bound to wear off on her wimpy son. She also knew that he had a habit of stretching the truth. It had been almost impossible to get a well qualified therapist to see him during the holidays but managed to find one who would see him. Her name was Thelma Vitner PhD. She was a tall severe looking black haired woman in her mid-to-late forties. She wore her hair in a tight bun fastened to the back of her head, a beak like nose and thin lips. Her eyes were a deep blue, cold and imposing like an iceberg. She dressed conservatively, usually in black, navy or grey business pants suits with starched white cotton blouses. She had a very commanding presents and Harold's mother was impressed upon meeting her. "This woman knew what she was doing," his mother thought as soon as they met. When Thelma told her that she had extensive experience with, as she put it, "delicate boys," and sponsored a summer camp for kids just like him, she was sold. "Harold, I want you to go with Doctor Vitner and tell her everything that happened. You can trust her and I expect you to tell her nothing but the truth," she instructed. Harold was intimidated by the doctor but reluctantly followed her into her therapy room. She told him that every thing he said to her would be held in the strictest of confidence and even a court order couldn't make her say anything. He felt better hearing that but still felt very small in her presents. He felt like a little kid being sent to see the principal. After the first session Dr. Vitner told his mother privately that Harold had some major issues to deal with and that he needed to see her every week after the holidays. When his mother said she couldn't afford to send him in weekly, Dr. Vitner replied that she would only charge what the insurance would pay. Greatly relieved, she happily agreed to put Harold under her care. As they left the office, his mother heaved a sigh of relief. "That woman is heaven sent. If anyone can help my Harold, she certainly can," she thought. Thelma sat back in her black leather chair with a big smile. "I haven't had a sissy to work on in ages. This one is going to be so much fun since most of the groundwork has already been laid. He obviously hates everything that happened and that's the challenge. Those tattoos were marvelous touches. I might have to consider doing the same to my future clients," she thought. Ooo Thelma sat in the shadows in a back corner of the room. The New Year's Eve party was getting into full swing. Mrs. Dalmatian and her precocious little boy, Delbert, had just left her table. Across the room Harold sat wearing his little girl costume looking miserable. Thelma was all smiles as she gathered up her things and left. "Oh what a wonderful way to bring in the New Year," she thought walking to her car. "That Mrs. Dalmatian is such a prude and so malleable. She'll see to it that Harold gets introduced to those young men. I can't wait until our next session to find out what he has to tell me. Not only that but I think it will only be a matter of time before I get my hands on little Delbert. With that curly brown hair of his, I bet he will make a lovely sissy dolly for his mother." Ooo Harold was in Thelma's office Thursday after New Year's Day. He was lying down on her leather couch crying as he described what had happened at the party. He denied wanting to participate in the party especially as a diapered little girl. He felt that his mother was humiliating him with her stupid costume ideas. Every one of her costumes wound up getting him into nothing but trouble he told her. "Harold you have to stop blaming your poor mother. She only wanted to have fun and putting on costume parties is a common event. Many families do that during the holidays. You should be happy that your mother wanted you to participate. What happened after you donned a costume was circumstantial. You only have yourself to blame for putting yourself in those situations. Like Christmas Eve, you knew as soon as you walked into that house that there would be nothing but trouble. Yet, knowing better, you aggravated the situation by not telling the truth about yourself. Just like on Halloween, if you had simply told that biker you were a guy before he took you off, nothing would have happened. You see dear, it's your own fault," Thelma lectured. "Bu....but....I...I didn't have time....I....I wasn't able to say anything," he sobbed in response. "Harold no matter what you say, deep down you know that's not true. If we are going to get anywhere with your therapy, you have to be honest with me and yourself. Now answer me either 'yes' or 'no' to the following questions. I don't want to hear any 'buts' or other response, understand," she said. "Good, the first question, did you tell that biker you were a boy when he accosted you at the store? No, okay, did you voluntarily drink booze at that bar? Yes, alright. Did you fight back or put up any real resistance to what they did? That was a 'no,' correct. At the Community Center or Christmas party, did you tell that young girl you were a boy? No. Didn't you think, once you were in that house, there might be trouble? Yes. When that girl put that prosthesis on, did you fight back? Again, a no. Didn't that cabbie suggest that you were a call girl? Yes. So if you knew he thought you to be a prostitute, wouldn't he want some kind of sexual favor for the ride? Again a yes. At the New Year's Eve party, weren't there a lot of people around? Yes. Do you think they would have stopped those boys if you had yelled out or even asked for help? Yes. Alright Harold that's enough for today. I'll see you next week. Please tell your mother I would like to see her for a minute, thank you," she said completing her test. Harold's mother left the office shaking her head. The good doctor told her that her son was in deep denial. To prove her point, she played back the recording of her 'yes' and 'no' test. "Every answer indicates that he knew what he was getting into Mrs. Jacobs. Harold as much as he may deny it, voluntarily put himself in the positions he found himself in. In every case, he didn't put up anything but a token resistance. It is my opinion that Harold is a transsexual and so bound by convention, cannot admit it, even to himself. How else can you explain his sexual activities with men or why he allowed himself to be put into those situations? Deep down, he wants to be the daughter you never had Mrs. Jacobs. To prove my theory, I want you to exchange all his male underwear for frilly nylon panties and camisoles, the lacier and beribboned the better. At first I'm sure he will complain and fight you but I guarantee by this time next week, you won't hear a peep of complaint. You need to be firm. Bring out his inner self and this will be the first step in curing your son. You must be firm dear. We need to bring him along slowly. Let him rant and rave but insist that he wear his panties and camisoles. You'll see, trust me," Thelma told her. Somewhat dazed by what the doctor had said, Harold's mother agreed to the treatment. She dropped him off at the house then left to do some shopping. She had doubts about her son becoming her daughter. The more she thought about it, the more she liked the idea. A daughter would be so much easier to get along with. "Well if my son wants to be a girl then who am I to argue? Doctor Vitner obviously knows what she's talking about. After all, she is the expert. If I were a boy, I think I would fight tooth and nail before I would wear girl's clothing. I'll know shortly what kind of son I really have according to the doctor. Come to think of it, Harold always bitterly complained when I gave him feminine costumes but after a bit, he seemed content," she thought as she pulled into the parking lot. While Mrs. Jacobs was shopping, Harold sat in his room. His mind was replaying what happened during his therapy visit. "I sounded like I volunteered to do that shit. Why wouldn't she let me explain what happened? You can't answer those questions with just a 'yes' or 'no.' It's like asking someone if they are still beating their spouse. I'm going to have to explain what happened at my next session. Oh well, she gave me a CD to listen to, so I might as well play it. She said it would ease my anxiety. Oh crud, it's one of those nature recordings. Let's see, the first track is 'Summer Thunderstorm,' then 'Coastal Waves.' Might as well listen to it, I don't have anything better to do." When Mrs. Jacobs arrived home, she found Harold in his pajamas asleep. The sound of a tropical rainstorm filled her ears. "That's strange. I don't remember him having that CD. He always listens to that horrible rap music," she thought. She decided to let him sleep while she emptied his draws of every stitch of underwear. Then she neatly folded his new lingerie, matching the panty with the coordinating camisole. As she left the room, she picked up his recently discarded boxers from the floor. Her next stop was the laundry hamper. Ooo The next morning Harold pitched the expected tantrum. When his mother walked into his room, panties and camisoles were scattered all over the floor. He was ranting, demanding to know where his underwear disappeared to. She let him carry on as she gathered up the scattered lingerie. She dumped the pile of panties and camisoles on the bed. "Harold that's enough! Now sit down and fold your underwear neatly and put it back into your dresser," she demanded pointing to the pile of clothing. "Tha....that's not my stuff!" he snapped back. "Oh yes it is and you will do as I say or I get my belt," she countered. His mother had always intimidated him. She was a big woman and when she took that attitude, he knew he couldn't win. Reluctantly he sat on the bed and picked up a pair of yellow nylon brief cut panties between his thumb and forefinger. He acted like the flimsy garment was going to bite him. Then, as if a switch was flipped, he spread the garment our before him. The nylon felt soft and smooth, semi-transparent with white rose floral lace inserts at each hip. The waist band was a white floral elasticized lace. "These aren't that bad. They look similar to my briefs except so much lighter and smoother. I don't wear briefs anymore but these look comfortable. Maybe I should wear them just to see what they feel like. No, I can't do that. These are for girls," he thought. Harold's mother sat down beside him and took the panties from his shaking hands. "Dear Doctor Vitner said you should wear these to help you. I don't understand it all but she is the doctor and you will wear these panties and camisoles until told otherwise. Now this pair is by Vanity Fair and the style is called a brief. It goes with this yellow camisole. Isn't it pretty? Notice the "V" lace insert at the bodice and delicate eyelet lace on the straps. Each of your panties has a matching camisole and it is important that you coordinate your lingerie. This is how you fold each pair and put them into your drawer. Now you fold this pair," she instructed handing him an emerald green camisole and panty. Harold wanted to protest but only managed to grunt and mumble as he neatly folded his lingerie. When he came to the last set, his mother told him to put those on then get dressed while she made breakfast. They were an iridescent purple with ivory lace detailing. The panties were a high cut style with a rose lace front panel. "Mother I don't want to wear these. They are for girls and I'm not a girl," he weakly protested. "It doesn't matter what you want Harold, its doctor's orders. I suggest you take it up with her during your next visit," his mother said ending any further argument. Ooo Over the next week Harold was very careful not to do anything that might reveal that he was wearing panties and camisoles to school. He was pretty much a loner at school but now he avoided his few friends whenever possible. Initially he was very uncomfortable wearing panties. Occasionally the crotch would slide and wedge between his balls and that was painful. More often than not, they would ride up into his ass crack. Those situations were not only uncomfortable but difficult to adjust in class or in the halls. He made sure to wear his husky cut blue jeans or cargo pants and sweatshirts to school. Towards the end of the week he stopped complaining to his mother just like the doctor had said he would. In Dr. Vitner's office she had him drop his pants and pull up his jersey. He was wearing a soft orange panty with white lace hemming and matching top. "Harold there is nothing to be embarrassed about showing me your pretty panties and camisole. I have seen your cute tattoos so this shouldn't be that bad. So how do they feel? Are they as soft and sensual as they look?" she said smiling. "Eeeerrrrrr, ye....yeah....I guess so bu....but I would like my boxers and tee back. These....this aint right," he stammered. "Not right dear? How could they not be right? They're just underwear. So what if they are pretty? You're not going around flashing your undies to anybody are you? No, so what's the problem? No, you keep wearing them. They will help you overcome your innate sexuality," she replied. "If you say so but....but I won't like it," he mumbled as he pulled his pants back up. "That brings me to another change I want you to make. Those bulky rough looking trousers and sweatshirts have got to go. They make you look like somebody asking for trouble. You don't want to get into any more trouble do you? No, I didn't think so. I'll talk to your mother in a bit and see what we can do about your options. Now tell me, have you been listening to your CD every night when you go to bed? Yes, that's a good boy. I have another one I want you to start listening to. It's like the other but the music is a little different. Okay, I think we are making headway. Try to keep an open mind about the changes I am asking you to make. In the long run you will thank me, no matter how strange they may seem at the moment. Now please get your mother for me," she said. "Mrs. Jacobs I have some good news. Harold is coming along better than I though he would. How has he been at home?" the doctor asked. "Doctor Vitner, you were right. When I brought home his new lingerie he put up a fight but just like you said by the end of the week, not one complaint. I'm still not sure what you are leading up to with his treatment but must admit that you have been right so far. I'm glad to hear that you think he is making progress," his mother replied. "Like I said in our last meeting, Harold is suffering from deep seated gender issues. To cure him we have to bring him along slowly, baby steps if you wish. First we have him adjust to wearing frilly panties and camisoles. If he doesn't rant and rave about having to wear such girlish attire, we move on to the next step. Which brings me to that next step; you need to replace all his bulky jeans, trousers and tops with more feminine ones. I suggest low-ride girl's jeans in blue, pink and white. He can wear the blue and white ones to classes. Save the pink for at home wear for the time being. Get him some nice women's slacks that he can wear anytime. For tops I would suggest some unisex sweaters and man cut blouses. I know this is a lot to ask but here, this is a card from a friend of mine. She has a lovely boutique and will give you a twenty percent discount on whatever you decide to purchase. Lara has a lovely range of clothing, lingerie and shoes. Speaking of shoes, get rid of those ugly trainers he's wearing. Lara will help you there. Well, it looks as if our time is up. Do you have any questions?" she stated. "Doctor, I'm not so sure about all this. I deeply care for my son and want what is best for him. Are you sure this will work? Are you sure he has a gender issue? I know he was never very masculine but this?" his mother asked. "Yes, Mrs. Jacobs, I'm sure. If he had absolutely refused to wear his panties and camisoles and gone commando, that would have proved me wrong. He will probably raise a stink about his new clothing but like last week, he'll stop complaining. Trust me, my methods work. You're stressed by all this. I have a CD here that will help. Put it on when you go to bed, it will help you sleep. See you next week," she declared. Mrs. Jacobs looked at the card as they were leaving the doctor's office. "Lara's Boutique, Everything the fashionable woman needs in one place," the card read. On the back of the card was the doctor's rubber stamped name. "Might as well give this place a try, I sure could use a twenty percent discount," she thought. "Lara honey, this is Thelma. I'm fine dear, just called to give you a heads up. I have two new clients coming your way, a mother and her son. Yes, the same deal as usual. This one, Harold, is older than my normal clients and will have to be handled with kid gloves for a bit. I only took him on because of unusual circumstances. He had a series of accidents, quite involuntarily, that make him a viable subject. I'll give you all the details later. Just be your doting adoring self for now. He's just getting the basic starter set. I already have him in panties and camisoles. No, it's a little too soon for bras and girdles, maybe in a week or so. Alright, you know what to do. Call me when they leave. Bye," she said. Ooo "What are we doing here?" Harold asked as they pulled into a space in front of the boutique. "Just stopping to get you some new pants and shirts like the doctor ordered dear," she replied. "Bu....but this is a girl's shop. I don't want to go in there!" he stated. "Harold Jacobs this is where we are going and you will behave yourself. Understand!" his mother snapped. When she used his full name, Harold knew that she meant business. Reluctantly he accompanied her into the shop. Seeing all the feminine finery spread all about unnerved him and he broke out in a cold sweat. "I so don't want to be in here much less anything they sell," he thought. "Hello, may I be of assistance? My name is Lara and this is my little establishment," Lara said as Mrs. Jacobs and Harold entered her boutique. Lara was a statuesque red head with sparkling green eyes. She was wearing a shimmering red satin peasant blouse and black wool pencil skirt and three inch black patent leather heels. She stood about five foot nine in her heels and had a very pretty face. Harold felt his penis stiffen as she approached them. Red heads with green eyes had always been a favorite fantasy of his. Lara was a dream come true. "Yes Lara, Dr. Vitner sent us to see you about...about getting some new pants and tops for my Harold here," Mrs. Jacobs said handing her the doctor's card. "Oh yes, the doctor and I are old friends. I have discreetly assisted many of her clients. Let me lock the door so we can have some privacy. What can I do for you today? Some nice jeans, slacks and tops, sure follow me," she replied leading them into the back. Harold stripped down to his panties and camisole. He was blushing, holding his hands over his groin and not daring to look up. As soon as he was told to strip, his erect penis immediately shriveled and he tried to object. "Mom, you can't expect me to take off my clothes. Not here, not in front of her," he said almost in tears. "Sweetie you don't have anything to be ashamed of. Not in here, not with me. I have seen this and much more in the past. Why I think it's wonderful of you to let your feminine side show. Not many men are that brave or as handsome as you. You have to try on these lovely new things your mother wants for you. I would be devastated if you left here with clothing that didn't fit properly and what would that say about my store? Here, try these lovely jeans on. Pretty please, do it for me. I think you will look fantastic in them," Lara purred. Harold hesitantly reached out and took the jeans from Lara. They were made of stretch denim, in a low-rider hip hugging style with a slight flare at the ankles. The four pockets were none functional and stitched in. It buttoned in the front and had a short zipper. They fit his thin frame like a second skin, smoothing out his crotch, separating and uplifting his backside. He thought they were at least a size too small but Lara said they were perfect. The blue and pink jeans were similar except the pink jeans had red and green floral embroidery covering the two back pockets. Harold protested loudly over having to wear the pink jeans. It took all of Lara's persuasion to get him to try them on. Even then he hesitated until his mother assured him that he would only have to wear them in the house. He was uncertain but tried them on. "There's no way a guy would wear these. All I'm doing is trying them on. It's not like we are actually going to buy them or me wear them," he thought. He had second thoughts after he had them on and Lara gently patted his ass and whispered in his ear that she thought he was very hot. He was fitted for three pairs of slacks in navy, grey and black. They were all a soft satin lined wool blend with a low waist and flared legs. Like the jeans, they had a button and short zipper front. The cuffed hems flared at the ankles and they had no pockets. Each pair hugged his crotch and ass in a tight embrace. He fussed but not nearly as strongly as he had with the jeans. Three sweaters with long sleeves and slightly scooped neckline were tried on next. The cream colored wool sweater had three thin horizontal black lines across the chest. The baby blue cotton sweater had a white star decoration and the lavender one was a soft fuzzy angora. He thought the last one was too feminine but Lara said he would look fabulous as she rubbed her hands across his chest. The feeling of the soft material moving across his chest as she rubbed made thoughts of rebellion disappear. He had only two problems with the three dress shirts. One was the fact that they buttoned funny. Instead of being left to right, they buttoned right to left. The other was the material. These were made of what Lara called micro-fiber and much nicer than the starched cotton style. He had to agree that they felt wonderful on his skin. The three shirts in ivory, baby blue and a soft pale pink were added to the pile. His trainers were replaced with a pair of cordovan square toed flats with a one inch block heel and a tassel on the vamp. Since his new slacks and jeans had no pockets, Lara sweet talked him into getting a cordovan leather "man" bag with leather strap. Several narrow leather belts were also purchased. After they checked out, Lara handed Harold a leather belt. It had blue turquoise cabochons in a floral silver setting spaced out along its length. The buckle and tip were in floral etched silver. "You were such a delight today Harold I want you to have this. It will look lovely with your pink jeans. Promise you'll wear it for me," she grinned. Ooo As Doctor Vitner predicted Harold raised a fuss for the first two days. After that he only objected when his mother asked him to wear his cute pink jeans. At school he caught a few derogatory comments but nothing more than the usual shit he always received. Some of the girls noticed that he was wearing girl's jeans, slacks and tops but just giggled. They also noted very visible panty lines. "That gay boy should really think about wearing thongs with those tight pants," they would say amongst themselves then giggle. Harold for his part thought his new clothing was androgynous or at least that is what Lara had told him. Other than his pink jeans, he actually believed her. Since none of the bullies said anything about his clothing in their taunts, he went about school thinking nothing of it. He still harbored misgivings about wearing panties and camisoles but the longer he wore them the more comfortable they became. In late January a pretty girl sat across from him in study hall. She was in some of his classes and he had a mild crush on her. She was about his size with long wavy chestnut colored hair. A little on the chubby side but otherwise had a nice figure. Her name was Gwendolyn. She had a reputation of being the school's "busy-body." She went out of her way to snoop into everybody's business and intrude whether or not they approved. They sat and talked the entire hour with her doing most of the talking. By the time they left study hall, she was convinced that the cute gay guy needed her help. She decided that she would talk to him again to get some more details but had already decided what she could do to help. After school she met up with one of her best friends, George. He was a tall muscular senior who played defensive end. What very few people knew was that he was gay. Gwendolyn knew because they had been next door neighbors for years and their families were close. She had tried to get him to come out of the closet but being a football player he couldn't afford to take the chance. All he ever wanted was to play in the NFL and he believed if it got out that he was gay, would never get that opportunity. She would date George off and on to keep up the pretense that he liked girls. When Harold said goodbye to Gwendolyn he was walking on air. It was the first time in his life that a pretty girl actually talked to him as if he were a real person. Not only that but when they parted, she kissed him on the cheek. He had been so happy afterwards that he didn't put up a fuss when his mother asked him to wear his pink jeans and lavender sweater for his therapy session. Thelma was more than happy to see him wearing the tight jeans and fluffy sweater. She complimented him repeatedly for how nice he looked. He was glad to get the compliment or at least he thought he was. He still was not totally comfortable dressing this way. He mentioned that he didn't like how tight they were in the crotch and she said she had a remedy for that. She also mentioned that his sweater didn't look quite right but she would take care of that as well. He was hoping that she would let him go back to his baggy cargos and sweat shirts. He also mentioned his meeting with Gwendolyn and how much he was looking forward being with her. "Oh dear, the last thing I need is for a girl to get interested in him. I've got to find out more about this Gwendolyn," she thought. As Mrs. Jacobs and Harold left their appointment, Thelma got on the phone. "Yes, may I speak to Gwendolyn please? Hello Gwendolyn I'm Doctor Vitner and I am Harold's therapist. He mentioned meeting you and seems very keen on you. So I was wondering......" she began. "Welcome back to my humble shop Mrs. Jacobs and oh, Harold that outfit is just precious on you. I see that you wore the belt I gave you too. How sweet. Come here dear and give Lara a great big hug," she greeted as they walked in. By the time she broke the hug, he was beet red. "So what can I do for you today?" she asked breaking the embrace and stepping back. "Harold is complaining about the tightness in the crotch of his new pants. We were hoping that you could recommend something," his mother responded. "Sure I can fix that. Here let me lock the door and let's go in the back," she said. This time she had him strip down to his panties. His embarrassment was even greater as his high-cut red panties revealed more than he wanted them to. Lara hushed his complaint even before he said it. "Harold those red panties are so cute and look marvelous. I wish more young men were brave enough to wear such flattering styles," she said giving him a peck on the cheek. He stood dumbfounded, holding a red panty girdle with a bright red satin diamond front panel embroidered with silver thread in a delicate fern pattern. Several others in different colors were stacked on a nearby table. "Wh....what a...am I suppose to do with these?" he stammered. He knew what they were and was confused as to why a boy would ever wear them. "Put them on of course silly. It's either wear a panty girdle or a gaff if you want to be comfortable in your new pants. If you would rather have the gaff I could get some for you but you'll have to take off your panties. I understand that dancer's gaffs can be painful. You will have to tuck your manly equipment back up inside your body to wear one. I wouldn't recommend them, that's why I brought the girdles. They will be more comfortable. With a girdle all you have to do is push your equipment back between your legs," she explained. The thought of sticking his balls back up inside sent a shutter of distaste running up his spine. It was very painful when that bull dyke shoved them up back inside and he didn't want to experience that pain again. Reluctantly he turned his back and stepped into the girdle. It was a tight fit and he struggled to pull it into place. "I....I think you...you got the wrong size. This thing is way too tight," he complained. "Oh no darling, it's a perfect fit," Lara admonished with a straight face. It was difficult not to laugh as she looked at him. The girdle had pulled his sex flat against his groin and the slightly padded bottom gave him a round butt. "Now that I've given you a nice girlish bottom, I need to get the top looking as good," she thought before saying, "Now doesn't that seem more comfortable than wearing a gaff? No, it's the right size. All you have to do is sprinkle some talcum powder on the inside before you put them on. They will slide up real easy then." "Errrrr, I guess so," he replied not understanding why he had them on in the first place. "Why am I doing this? I shouldn't even be here. This thing is so tight how can she say it's comfortable? The only choice I have is to wear this or a dancer's gaff. I don't want to wear that," he thought. When they left the store Harold had seven new girdles in almost every color of the rainbow plus white, black and beige. That night he played his new CD. It was a music montage of Celtic themes. Many of the songs were hauntingly sweet. He thought he heard a soft feminine voice in the background but dismissed the idea. In her room, his mother listened to her new CD. It was also a music montage but of 70's soft rock. She thought she heard a voice but paid no attention to it. Her day had been exhausting. Ooo As the doctor predicted, Harold bitched and moaned about having to wear the tight girdles. By the third day he didn't utter a single complaint. However, he did begin complaining about how his shirts and sweaters bunched up against his chest. Mrs. Jacobs took it all in stride. The more she looked at him, the more she thought about how he would look in a dress. When that thought passed through her mind, she shook her head and went back to doing whatever it was she had been doing. Now, she found herself really wondering what he'd look like with a better figure and in dresses. School started off wonderfully for Harold. Gwendolyn sat next to him in study hall. This time she did it deliberately unlike the last time when it had been the only seat available. The chatted the entire time and she made his day when she asked him if he was going to the school Valentine's Day dance. He never had the courage to ask a girl to any dance, much less, have a girl ask him. With his heart skipping in happiness, he said that he hadn't asked anyone yet. "Oh goodie, I am so glad to hear that. I was hoping you weren't already going with someone. Like, I mean, it's this Saturday night. Do you want to go? You do. That's wonderful. I have the perfect outfit. Be at my house no later than four so we can be at the dance by six," she said as the bell rang, handing a piece of paper with her address on it. He was a bit confused about having to meet her so early but didn't worry. "I have a real date for the dance," he thought as he picked up his things. During his Friday therapy session, he would have talked the entire time about Gwendolyn and his upcoming date. Dr. Vitner had to make him get back on topic on more than one occasion. She was trying to find out how he felt about his new girdles and if he was having any problems. "How could I have any problems when Gwendolyn asked me to the dance?" he replied. "Please Harold I am very happy for you but let's get back to how you feel about your new girdles. Don't they make your jeans and slacks fit so much better? You don't mind wearing panties and camisoles?" she asked. "Oh I forgot I'm even wearing lingerie and girdles but....oh my gosh! I can't wear that Saturday. I'm going to the Valentine's dance," he replied beginning to panic. "Settle down Harold. Don't upset yourself for no good reason. Are you planning to rape that poor girl?" she responded. "What! No! No, I would never do something like that! I'm not like that," he said raising his voice. "You don't have to shout Harold. I can hear you perfectly well. My point dear, is that, unless you take your clothes off, Gwendolyn will never know. Now that we settled that, are you having any other problems?" she stated. "No, not really except for maybe my shirts seem to be bunching up on my chest. It's a bit uncomfortable but I can live with it," he said visibly relaxing. "Have you given any thought to wearing a bra dear? It would make your shirts hang much more naturally," she said watching him closely to see his reaction. "A bra? Boy's don't wear bras," he automatically responded. "Are you sure you haven't given the idea some consideration? Tell me honestly now. I won't be judgmental," she asked. "Well, I have thought about wearing a bra for a couple of weeks but the idea is just plain stupid. Isn't it? I'm a boy and boys don't wear bras," he softly replied blushing. "Harold you have worn bras before. So the idea isn't stupid. There is nothing wrong in wearing a bra, millions of people do. If a bra makes your shirts and sweaters look so much better, what is wrong with wearing a bra? It's just another piece of clothing. I was talking to Lara the other day and she said she thought you would look right handsome in a bra," she replied. "Lara she's pretty....did she really say that about me?" he responded. "Harold I don't lie and if I said she said something, it's true. I think she likes you. She keeps telling me how courageous you are for letting your feminine side show through. Why don't you tell your mother to take you there after our session? Ask her to buy you a couple of bras. If she thinks the idea as stupid as you say, she won't do it. Just ask her and see if what I'm telling you is true or not," she answered. It wasn't until they were in the car that Harold asked her to take him to Lara's boutique. When she asked him why, he hemmed and hawed a bit. Finally, he admitted that he wanted to buy a bra to make his shirts fit better. She gave him a funny little smile but agreed. That wasn't the answer he was hoping for deep down in his gut but couldn't bring himself to say no. When Lara gave him a big hug and kiss on the cheek any further doubts were gone in the fluttering of his heart. They left the store an hour later with seven new bras. They were all underwire, slightly padded up-lift satin and lace confections in an "A" cup. Lara made sure that the colors matched the girdles he had purchased earlier. As he was leaving Lara made sure to give him another big hug, kiss on the cheek and pat to his round butt. Harold was very happy that they had stopped by. His penis was twitching in the tight confines of his yellow girdle. Lara's exquisite perfume lingered in his nostrils and he wasn't even thinking about the new yellow and white lace bra he was wearing. When he went to bed he put on his new CD and with a happy smile fell asleep. His last thought was, "This was one great week. I can't wait to take Gwendolyn to the dance." Ooo Harold sat in his room trying to decide what he was going to wear over to Gwendolyn's. On his bed were red nylon hip hugger panties, red girdle, matching camisole and new red bra. The bra's silver embroidered fern pattern on the cups matched that of the girdle's front panel. "I don't want to wear this, especially on my first date with Gwendolyn," his gut told him but his mind said otherwise. His mind was telling him that the lingerie would make him look sexy and appealing. With trembling fingers, he pulled the panties up his smooth legs. He had kept shaving them despite misgivings as after a few days, the stiff bristles would itch to the point of distraction. The new hair growth would also snag on the lining of his slacks. He had no trouble hooking the bra behind his back after having to do it so many times last month. With his lingerie on, he stepped into his charcoal slacks. The feeling of the champagne colored lining going up his legs sent a thrill of pleasure racing up his spine. He quickly buttoned the white micro-fiber dress shirt and tied a thin black tie around his neck. Sitting on the bed he pulled a pair of thin black socks on and stepped into his shoes. Grabbing his black sport's jacket and his man bag, he was ready to meet his date. "Great, you're here. Come on we have lots to do before we go," she greeted with an ear to ear smile. She grasped his hand and led him into the house where she introduced him to her mother. "Mom, this is that special boy I told you about, Harold. Harold, meet my mom, Joyce," she said. Joyce was an older version of Gwendolyn who greeted him with a bright smile. "It's so nice to finally meet you Harold. Gwen has told me so much about you. I can't begin to tell you how happy you are making our families." "Okay mom, we have a lot to do, do you mind?" Gwendolyn broke in. Not waiting for an answer, she grabbed his hand again and led him into her room. "Okay, strip," she ordered as she shut the door. "Errrrr....wha....what? Strip? Right here, right now?" he stuttered in confusion. "Sure how else are you going to wear the outfit I picked out for you? Don't worry you're going to look great when I finish with you," she stated. "Bu.....but I..." he started to say but she stopped him. "Harold you don't have to pretend with me. I know all about your little secret. I know you're shy and timid but I really want to help. Here let me unbutton that shirt for you," she said as she pushed his jacket off his shoulders. Harold stood frozen in place. "She knows my secrets!" his mind screamed. Before he could react, she had unbuttoned his shirt. "What a lovely camisole and your bra is so pretty. What lovely embroidery. I don't have anything nearly as nice. You're so lucky," she said as she pulled the camisole down. Harold began to hyperventilate as she began undoing his slacks. "N....n...no.....yo....you. Stop...please...what are....are you doing?" he gasped. "Calm down Harold. We have to do your hair and makeup first. Now, stop gasping and calm down. I'm not going to do anything to hurt you. Kick off those shoes and get out of those slacks," she firmly said. In a daze Harold complied. His head was reeling and to make matters worse, had no idea of what to do. A pretty girl had seen him in his lingerie and was talking about hair and makeup. He was extremely embarrassed but with his slacks around his ankles could do nothing. He felt faint and was happy to sit on the padded cushion of her vanity stool. He was getting his breath back as she was combing out a lock of his hair, coating it with setting gel and winding it on a hot roller. He started to raise a hand to stop her. She swatted it away with her rat tail comb. "Harold, sit still and let me finish this. I promise you will like it. Don't make me hit you again," she stated. Subdued for the moment, he let her roll his long hair onto the rollers. He could feel the heat from the rollers on his scalp and started to complain. "Harold, like I said, sit still and behave. I know your secret and I promise when I'm finished no one will recognize you. Promise, now behave and let me do my thing," she firmly said. With his hair in rollers, she began working on his face. His brows were still thin from his previous adventures but she plucked a few stray ones out. She worked on him steadily for an hour before she was satisfied with his makeup. Harold had watched in dismay as his face was transformed into that of a pretty young lady. She had done his eyes in an Egyptian motif using thick black eyeliner extending out form the corners, blending an iridescent blue into lavender into silver eye shadows to bring out his eyes. A heavy coating of black mascara extended the lashes. His lips were in a high gloss red plum color. "Yeah, the eyes are a bit over the top but you can get away with it for tonight. Here put these on," she said. She handed him a pair of sheer black hose with floral lace welts to put on. Seeing him stare blankly at them, she took one and rolled it into a donut. "It doesn't look you have worn stockings before so I'll show you how with this one. You can do the other by yourself. I'm so glad you keep your legs shaved. That's going to save us a lot of time. Just be careful not to put a run in them. They're expensive," she said as she began smoothing it up his leg. She folded up the edge of his girdle and quickly fastened the hose to the garter tabs. Harold couldn't believe what was happening and was powerless to stop her. He wanted to stop all this but his body didn't want to obey his wishes. When he felt the stocking going up his leg, the sensation was almost overwhelming. Her hands, as they kneaded the nylon up his leg, put goose bumps on his arms and a stiffy in his panties. "Here slip these heels on while I get your dress," she ordered handing him a pair of silver strappy three inch spike heeled shoes. He had a bit of trouble fastening the very tiny hook into the shoe buckle. Other than that he would have no trouble walking in them. After all, he had walked a mile in similar ones Christmas Eve. "Oh shoot, we have to do your nails before you can put on this dress. Good thing a bought a new set of artificial ones the other day. Put your hand up here on the vanity and let me get started," she said hooking the dress on the back of the closet door. Harold stared at the dress as she worked on his nails. The dress was cream colored silk with a mandarin collar and straight mid-calf length skirt. It was decorated at hem and bodice with brilliantly colored embroidered oriental stylized birds and flowers. She saw him looking at the dress, "I found that at the thrift store last month, can you believe it? I practically stole it for only $18.00. No telling how much that cost when new. It's a little big on me but I think it will fit you beautifully. We're going to have to fill out that bra of yours a bit though. Here give me your other hand, I'm finished with this one so don't smear it," she said. He looked down and saw that she had glued one inch oval extensions on his fingers. They were painted in the same bright shinning reddish- purple as his lipstick. He remembered to keep his fingers spread and wave his hand from the wrist. His actions didn't go unnoticed by Gwendolyn. "Did I have him pegged for the fairy that he is or what. George will fall head over heels in love with him. I just know it. They will make a wonderful couple. I'm so glad I sat down by him in study hall. Talking to his therapist made doing this so much easier. I still can't believe she thought I might want to date him. Like that would ever happen. I had some real doubts but after that talk, I couldn't wait," she thought as she glued and polished. With his nails dry, she slipped the dress over his head and zipped it up the back. It fit him like a glove and looked adorable on his slim figure. She removed the curlers and brushed out his hair into flowing waves. Then fluffing out his bangs set everything in place with hair spray. For a finishing touch, she pinned a black satin bow to the back of his head. "Okay you're done," she said as she sprayed him with a heady spice scent. A dazed and confused Harold sat on the bed as Gwendolyn got herself ready. She stood right in front of him and stripped off her sweat suit. He watched as she removed her green bra and bikini panties dumb struck. She didn't show the least bit of embarrassment or hesitation as she began to get ready. As far as she was concerned, he was just another girl. Gwendolyn was putting the finishing touches on him when Joyce called them down to meet their dates. She had given Harold a strand of pearls for his neck, pearl drop earrings and cabochon pearl ring. She also had him put the makeup she used in his man bag along with a bottle of clear nail polish in case he got a run, some tissues, a couple of tampons for realism and a small bottle of the spice perfume. When he heard her mother say their dates were there, he panicked again. "Wha....what date? You're my date. What's going on?" he gasped. "Oh get over it Harold! I fixed you up with my best friend George. You probably already know him, he plays defensive end for out team. Look, there is nothing to worry about, I swear. He's as gay as you are but is afraid to let anyone know. When you told me you weren't going with anybody, I decided to fix the two of you up. You make a beautiful girl and he can date you without anyone being the wiser. We can't call you Harold while you are dressed up like this. What's your fem name?" she said. He was so thunder struck by what she had told him that without thinking he said, "Heather." "That's a wonderful name, Heather, I really like it. Remember, it's important that you act like a real girl. When we go to the little girl's room, don't panic and sit to pee. If you can do that no one will know. Come on Heather, we don't want to keep our dates waiting," she said pulling him by the hand. When they entered the living room, Joyce did a double take when she saw Harold. "Oh my goodness, Har....errr..you look absolutely stunning, so much prettier than that tom boy that arrived here," she said. "Heather I want you to meet your date, George and this is my date Jeremy," she said giving him a little push toward where he was standing. George's hand completely engulfed Harold's much daintier one and his smile broadened from ear to ear. Despite the heels, George was a good head taller than Harold. His size and strength were intimidating. As they stood looking at one another, Joyce picked up her digital camera and began taking pictures. She had them all take several poses before she was satisfied. In the last pose, she had them kiss their dates on the cheek. Ooo The gym had been decorated in a pink and white motif. At the entrance was a heart shaped arch constructed of pink and white balloons. As each couple entered, the school year book photographer took their picture. They found a table in a back corner with a red heart frilled with lace as the center piece. Floating above it were several pink and white balloons suspended by multi-colored ribbons. Two other couples were already sitting there. Harold didn't know them but they were best friends of Gwendolyn, George, and Jeremy. Harold was nervous as the introductions were made. He was more nervous in this environment than he had been during Halloween, Christmas Eve or New Years. Then everybody involved knew that he was a boy in a dress. Here, he would have to convince everyone that he was a real girl. Talking and behaving like a girl was something he never had to do before. He decided his only choice was to watch the other girls and copy their actions as best he could. What he didn't know was that all the girls knew his and George's secrets. The girls all liked George and had decided to do everything possible to make them a real couple. Now that they had met the beautiful Heather, they were more determined than ever. Shortly after the introductions were made, the guys all got up and went to get them some punch and snacks. Once they were out of the way, the girls descended on Harold with a vengeance. He was initially horrified that they knew his secret. They assured him it was safe with them, safe as long as he didn't do anything to hurt George. If that happened, they would make sure the rest of his life was going to be pure hell. Once they were satisfied Harold understood the consequences, they worked together to give the "new" girl a cover story. After discussing it, the girls came up with what they thought a good cover. Heather just moved from the other side of town and lived with her aunt, Mrs. Jacobs. Her parents had died in a horrible car accident. She was going to the Catholic school, St. Thomas, and would transfer at the start of the next six weeks period. "So what do you think Heather? It's short, believable though a bit melodramatic. At least you won't have to answer any questions about your parents this way. If you have to, you can give out your real address and phone number," Gwendolyn asked. "I...I guess so. I don't want anyone to find out that I'm really a guy under all this makeup and clothing. It'll do for tonight," he answered. The band began playing as the boys came back. George asked Heather to dance but refused saying he didn't know how. "That's alright, I'll teach you. I'm a very good dancer," he said taking Harold's hand. It was a slow song and George, pulling Harold's hands over his shoulders, pressed his body in close. It wasn't long before Harold felt George's manhood pressing against his thigh as they rubbed their bellies together. He tried to back away but George only pulled him in tighter and kissed him softly on the neck. "Look Harold, you're not my idea of a perfect date. If I had my druthers, you'd be dressed like me. Since we can't do it that way, we'll have to do it this way. Now act like the adoring girlfriend or I'll get pissed. If I have to put up with you in panties and dresses, I want you to be super nice to me," he said giving him a firm pat on the bottom. About half way through the dance, Harold was fatigued from all the dancing and trying to keep up his feminine persona. The fast dances weren't so bad. All he had to do was copy the style of the girls around him, shaking his ass and shoulders. He was relieved when the girls all went to the lady's room. While standing in the cue, several other girls asked him who he was and where was he from. He replied, in as girlie a voice as he could muster, the cover his friends had developed for him. He wasn't use to standing in line just to use the bathroom and almost peed on himself as he entered the stall. Pulling up a tight skirt, pulling down a girdle and panties took time. When he finished his business, he had to pull everything back into order. Leaving the stall, Gwendolyn exited the one next to his. "Come on Heather, let's grab a spot by the mirror and fix our makeup," she said. Harold put his chunky man purse down on the counter and began searching for his makeup. As he pulled out his compact, a tampon fell out and rolled to the floor. He started to bend down and pick it up when Gwendolyn whispered, "Stoop, don't bend." His movement caught the eye of several girls waiting their turn at the counter. They just smiled knowingly back at him. They met the other two girls out in front of the bathroom. They all told Harold he was doing fine but really needed some help in his mannerisms. Several other girls joined them as they were about to go back to the table. They all wanted to know who the new girl was. When he repeated his cover story, they expressed their sympathies and said they couldn't wait until he joined them at school. Walking back to their table, Harold began to doubt the advisability of his cover. They expected Heather to register and begin classes with them in two weeks time. "Well it probably doesn't matter. After tonight, I don't ever plan on seeing Heather again much less George. I can't believe she got me into all this shit," he thought. As the dance progressed to its end, George was getting more and more intimate. He had his large hands squeezing Harold's round butt while grinding his groin into his, kissing him on his neck, ears and lips every chance he got during the slow songs. Harold didn't like it one bit but could do nothing to stop him. He wasn't doing anything that the other couples around him weren't doing. He was happy when the dance ended. He was more than ready to get back to Gwendolyn's and change back into his own clothing. Unfortunately, Jeremy drove to a deserted spot and parked the car. It didn't Gwendolyn and Jeremy to get into some serious petting. George didn't take much longer to get Heather into a tight embrace and serious lip lock. The windows were steamed opaque as the sound of zippers being undone filled the car. Harold caught a glimpse of Gwendolyn with the top of her dress pulled down, her "C" cups breasts revealed with her green bra shoved up above them. His attention was forced back down as George grabbed him behind the neck and pulled. Harold saw the large penis looming in front of his face. He tried to pull back but George was too strong. "Come on Heather, you been prick teasing me all night. Now it's time for you to show some appreciation," he said loudly for Jeremy's sake. Then more softly said, "Harold you had better do a good job or I'll be mad. You don't ever want to see me mad." It's not like Harold had never done this kind of thing before. He hated every bit of it but by now knew exactly what a boy wanted. Slowly he opened his lips and took the mushroom shaped head into his mouth. He ran his tongue over it the sucked before swallowing more of its length. He repeated that until he had every inch of that nine inch monster inside his throat. With his lips pressed into George's thick pubic hair, he gently pressed his teeth against the flesh and slowly drew back sucking as he went and breathing. George let out a loud, "Hot damn!" after the fifth time and erupted his seed into that delightful mouth. Harold swallowed glad that it was over. Instead of taking him back to Gwendolyn's, Harold was dropped off at his house. He wanted to protest that he needed his own clothing back but Gwendolyn said he could keep the dress as she looked meaningfully from him over to Jeremy. "Besides, George will be able to find your house again without having to get directions. Now, be a good girl and get out. Come over to my house after school Monday. You can pick up your things then. We're all tired and want to go home," she said stressing the word "girl". "OMG! How do I keep getting myself into these situations? How am I going to explain all this to mother? Damn, I hate Valentines Day," he thought as he walked up the drive to his front door.