By Carol Collins, 1998:
Leon thinks he has to sew his own dress and wear it to school to get a passing grade. Does he pass the class?
Leon Jenkins was fifteen years old. Admittedly, he was small, maybe even scrawny, for his age. Some of the bigger boys picked on him at school. He had learned to do whatever it took to prevent the physical abuse that the larger, and usually dumber, boys inflicted on him. He avoided them whenever he could. Most of the time, that meant that he was leaving to go to school earlier than the school bullies in the mornings and leaving later in the afternoons. The study hall that he was sent to in the mornings and afternoons also doubled as the Home Economics classroom. Some of the bullies kidded him about taking the cooking and sewing classes. The fact that he had long brown hair that hung below his shoulders didn't help, but he wore his hair long as he tried to look like his favorite rock star. This year, starting the ninth grade, the kidding had come home to roost. He had a choice between taking another Physical Education class, meaning he would be alone and naked in the locker room with the very bullies he had tried to avoid, or, he could take Home Economics. He chose Home Economics as the lesser of the two evils.
His next door neighbor and a classmate, Joy Daniels, was a pretty redhead that exhibited a wild streak that some times got her, but usually Leon, into trouble. She was medium sized for a girl. At five foot five, she was the same height as Leon. She was proud of the two firm breasts that she had grown over the last couple of years and wore blouses and sweaters to emphasis them. Her legs were nicely shaped and she usually wore skirts, dresses or shorts to show them off. Her bedroom window was directly across from Leon's and, occasionally, he would get a glimpse of her as she changed her clothes. He had masturbated several times as he watched her slowly removing her clothing as she prepared for bed.
Debbie Williams was the wildest girl at the school. She was also Leon's height, general size and weight. Her long brunette hair and doe brown eyes, firm but small breasts and adventuresome attitude resulted in her being best friends with Joy. Since both were taking Home EC at the same time as Leon, they teamed up together on their projects. Debbie wore very short mini skirts that rode up her legs to reveal that she usually wore thigh high stockings instead of conventional pantyhose. It was rumored that she had been felt up by over half the boys in school. Unfortunately for Leon, he was not one of the fortunate boys who had been able to sample Debbie's charms. He wanted to, but he was just to shy and bashful to ask.
The cooking projects were successfully completed and the new class assignment was to sew a dress and wear it to school in order to get a passing grade. One day, the Home EC teacher, Mrs. Brown, jokingly told Leon that since he had signed up for Home EC, he also would have to wear a dress the following week. She had even said this in front of the entire class. Before she could tell everyone that she was only joking, the intercom interrupted her, her young daughter had been injured on the elementary school playground and she needed to take her to the emergency room. She left without telling Leon that she was joking and that he did not have to wear a dress to school. Since it was Friday, and there was to be no classes on Monday, Mrs. Brown would not be back to school until next Tuesday. Poor Leon sat at his desk in silence as the girls giggled and laughed about him wearing a dress to school.
"What have I gotten myself into?" He thought to himself as he sat quietly. If he came to school wearing a dress, the bullies would really give him a hard time! Joy and Debbie took pity on Leon and tried to cheer him up by telling him that they would still be his friends even if he were wearing a dress. Leon resigned himself to his fate. He decided that he would have to go to the fabric store and purchase a dress pattern and the material this weekend with Joy and Debbie as they bought their patterns. His plan to lessen the possibility of having the school bullies give him trouble by taking Home Economics instead of Physical Education, had backfired.
Saturday morning, Leon went over to Joy's house. Joy's mother, Millicent Daniels, a beautiful redhead, drove them over to pick up Debbie on the way to the fabric store. Mrs. Daniels thought that it was funny that Leon had to sew a dress and wear it to school. She had always thought that Leon was small and delicate looking and probably would have made a better girl than he did a boy. She was even interested in seeing how much like a girl he would look when he wore a dress. She listened as Joy told her about what Mrs. Brown had said and commented, "Don't worry, Leon, I'm sure you will make a real cute little girl." Her comment did not boost Leon's male ego.
Three different dress patterns were picked out. Mrs. Daniels picked out Leon's pattern for him. He was practically repulsed by the lace and silk decorations in the picture of the dress on the package. When she picked out pink thread, pink lace and matching pink silk material, he was sure that she was kidding. He found out differently when she paid for his material at the same time she paid for Joy's and Debbie's. She was enjoying the ordeal that she knew she was putting young Leon through as she smilingly led the embarrassed boy out of the store. Joy and Debbie were upset because Mrs. Daniel had found the prettiest pattern for Leon instead of them.
The rest of the day was spent measuring, cutting fabric and sewing. Millicent had borrowed an extra sewing machine to speed things along. Still, she had to supervise as she instructed her daughter, Debbie and Leon in the finer points of dress making. When she was showing Leon how to attach the pretty pink lace to the pink silk fabric of his dress, he hung his head because he was too embarrassed to look up and see the smiles on Joy and Debbie's faces. Finally, things had progressed far enough for the final fittings. Debbie was so excited, she peeled out of her pull over top and mini skirt to try on her dress. She was wearing a pink silk set of brassiere, skimpy panties and tan thigh high nylons. Her young breasts were a little small, but a pair of large nipples could be seen poking out the thin pink lace of the bra cups. Leon's eyes practically fell out of his head as he saw his beautiful friend in such a state of undress. When Debbie glanced in his direction and smiled as she slipped her new dress down over her head, he felt his little penis stiffen in his pants.
Leon's reaction to Debbie's near nudity was not lost on Millicent Daniels. She had Debbie stand on a stool and Leon help her as she pinned the hem of Debbie's dress. Debbie insisted on it being even shorter than she normally wore. The tops of her thigh high stockings were almost visible. Millicent had Leon place some of the pins in the hem. She occasionally flipped the hem up to check the straightness, thereby exposing Debbie's smooth white thigh above the lacey tops of the stockings. She could see that Leon's hands were actually shaking. Mrs. Daniels and Leon assisted Debbie as she removed her dress. Debbie sat down at one of the sewing machines and began to sew the hem without putting her top and skirt back on.
Now, it was Joy's turn to try on her dress. She was a little shy about removing her top and shorts until her mother told her to not worry about Leon. She was told, "Just think of Leon as another girl while we are sewing dresses." Leon's face turned red as Joy removed her outer clothing. He had sneaked a peek at his cute redheaded neighbor as she had changed clothes in her room, but had never seen her this close up as she exposed her white brassiere and panties to him. Millicent and Leon helped Joy try on her dress so that the pins would not stick her. Then, she was helped up onto the stool. She said she wanted her hem a little longer than Debbie's. Millicent couldn't stop herself from exposing most of her own daughter's naked thighs to the young embarrassed boy as she flipped up the hem to check its straightness. When the hem was pinned all the way around and Joy was helped down from the stool, her mother told her to just leave her blouse and shorts off, too. Joy shrugged her shoulders and sat at the other sewing machine and sewed the hem on her dress.
Now was the time that Millicent was looking forward to and Leon was dreading. First, she instructed him to remove his clothing. He wore a tee shirt, jeans, athletic shoes, socks, and jockey shorts. When the older next door neighbor insisted that he remove his shirt, jeans, shoes and socks, he, at first, refused. But, with her insistence, plus Joy and Debbie's encouragement, he stood before them in nothing but his white under shorts. He automatically crossed his arms across the front of his body to hide the small bulge of his little penis. Millicent was enjoying herself as she handed him his dress, forcing him to remove his hands from the front of his shorts as he slipped it over his head.
Leon felt the cool silk fabric caressing his body as it slid down around him. It made his penis even harder. Millicent was truly impressed by how much Leon looked like a girl. "You really could have made a pretty little girl, Leon. Of course, a girl your age should have developed some boobies by now. The darts in the sides of the bodice are going to waste without something up top." She stared at the loose top of Leon's dress for a moment, then seemed to think of something. "Leon, step up on the stool. Joy, you and Debbie pin the hem of Leon's dress for him while I search for something." Millicent left the room as Leon climbed up on the stool.
Joy and Debbie seemed to enjoy themselves a great deal as they worked on the hem of Leon's pink silk and lace dress. Of course, the first thing they did was to get into an argument over the length of the hemline. Joy wanted it to be just below the center of the thigh, just like hers. Debbie wanted it to be well above the center of the thigh, just like hers. Finally, they compromised. The hemline was pined at just above the center of Leon's thighs. When he had tried to tell them that he wanted it below his knees, the two girls simply ignored him.
As Debbie flipped the hem of Leon's dress up to check it, she could not resist the impulse to raise it all the way up until Leon's cotton jockey shorts were exposed. Leon's face turned red as he tried to pull down the hemline of his dress. Debbie exclaimed, "Watch it! You'll make one of us get stuck with a pin if you wiggle around too much." Leon stood still even as Debbie flipped up his dress, exposing his cute little bottom. Joy's eyes got big and round when she saw her best friend's hand move up Leon's thigh and grope Leon's left buttock. Debbie grinned as she whispered to the embarrassed boy, "Nice ass." Leon frantically pulled his dress down just as Mrs. Daniels walked back into the room.
Millicent had seen the way that Debbie had fondled the derriere of the cross-dressed little neighbor boy. It had brought a smile to her lips as she saw him pulling his dress down and the way his face had turned red. She lay the articles of clothing on the table, picked out one of the pieces and turned toward the three teenagers. "I noticed that the dress just didn't hang correctly. The reason being that a girl of fourteen should have some breasts. So, I went up to the attic and went through the clothes that Joy had outgrown. I found just the thing for Leon." Millicent held up a small but well padded white brassiere. "Joy was not happy because her breasts had not developed as much as her friend Trina had, so I bought this for her last year. Of course, Joy's breasts grew quickly and she didn't need the padded bra anymore. However, I think this is just what Leon needs to make his dress hang correctly."
Leon began to shake his head. He mumbled something about not wearing any brassieres. He almost jumped off the stool and run from the house. He changed his mind when he thought about the fact that his other neighbors would see him as he ran home. Plus, he had not told his mother or father about how his teacher had required that he sews and wears a dress to school the following week. He didn't know how his parents would react to his appearing in public in a dress. To be seen running into the house in a pink silk and lace dress just might give his father a heart attack.
Leon meekly stood still as Mrs. Daniels approached him with the padded brassiere in her out stretched hands. He even let the dress slide down off his upper torso, exposing his bare chest and back to the three grinning females. Millicent slid the bra straps up his arms and pulled the back strap around his flat chest and hooked it in back. The bra was more than a simple padded brassiere. It actually had falsies built into the cups. They were just about a B cup. He was now the equal of Debbie in the size of his breasts. Debbie felt a little jealous of the boy with boobs at least as big as her own.
Leon was quiet as he pulled the top of the pink dress back up. He was too ashamed to say anything as he stood up on the stool in a bra and silk dress. Millicent stepped back a little and admired the visual effect that putting the brassiere on the fourteen year old boy had made. From the neck down, he really did look like a girl. From the neck up, he looked almost like a girl. As Joy and Debbie looked at Leon with smiles on their pretty faces, Millicent walked over to the pile of other things she had brought down from the attic and fished out a tiny pair of pink panties.
Millicent Daniels walked over to where Leon stood on the stool and held out the pink panties. He shook his head and said, "No way!" Joy and Debbie laughed at the idea of their friend wearing a pair of little girl's panties. Their laughter only made Leon's face turn redder.
Millicent told the protesting boy, "You have to put these on. The silk material of your dress hugs your body so well that the course seams of your cotton briefs can be seen. Besides, after you put these on, even you will agree that they are so much more comfortable than boys jockey shorts." Leon saw that Mrs. Daniels was not going to change her mind. When he finally agreed to change, he wanted to go to the bathroom to do it. Millicent, however, insisted that he change while still standing on the stool. "Just reach up under your dress and pull down your cotton panties. Step out of them and step into your silk panties. Your dress will cover you and we won't be able to see a thing as you pull the new panties up."
Leon saw that the older woman was serious. He had already submitted to her demands and this was but an escalation of her dominance over him. Joy and Debbie watched in fascination as he reached under his skirt, and his cotton jockey shorts fell down his smooth trim legs to land around his ankles. His face was beet red as Debbie giggled. Millicent grabbed his shorts and told him to step out of them. She tossed them onto the table where the pile of other things sat. Leon discovered just how small the pink silk panties were as Mrs. Daniels handed them to him. He bent over slightly as he stepped into them and pulled them up over his calves and thighs. The panties were bikini cut and only covered the bottom halves of his small rounded buttocks in back and just over the top of his penis in front. The silk was so cool and flimsy feeling, he almost felt as if he were still naked under his skirt.
Millicent's hands smoothed the dress down over Leon's round bottom. It made her become a little excited as she felt the power over such a youthful boy. Feeling of his cute derriere as her hands rubbed the silk dress material over his silk panties made her crotch tingle. She was amazed at the sensations she was getting from the fourteen-year-old boy in a pink silk dress. She was shocked at her own actions, but could not bring herself to quit. Only the fact that her teenage daughter was watching kept her hands from wandering around to the front of Leon's dress. She looked up into the embarrassed boy's eyes and wanted to push him even farther into the world of femininity.
The dress now hung on Leon as well as it would have on any girl. His body was small and thin and even looked feminine. The dress was fitted the rest of the way by Millicent, Joy and Debbie, as Leon sheepishly stood still as final alterations were made. When Leon stepped down from the stool, Mrs. Daniels insisted that he remove the dress and finish the alterations wearing nothing but his feminine undies. Joy and Debbie were surprised at the feminine figure that he possessed as they helped Leon sew the final seams in the pink silk dress.
Millicent went to another room and phoned Leon's home. Leon's mother, Janet Jenkins, answered. Millicent carried on a conversation for a few minutes. Leon's parents were aware of the Home Economics teacher's requirements that Leon sews and wears to school a dress that he had made. His mother had been a little shocked at first, but had decided that, since all the other students in the class had to do the same thing, it was only right that her son did, too. She thanked Millicent for helping her son with his school project since she did not have a sewing machine. Millicent asked if it would be okay for Leon to spend the night with them since he needed to finish his project. She smiled as Leon's mother told her it would be perfectly okay. "In fact," Leon's mother told her, "We'll take advantage of the occasion. Jules and I will have sort of a second honeymoon."
Millicent hung up the phone and went to see how things were progressing with the sewing. "How is it going, girls?" She asked as she entered the room. She had purposely said "girls" and not "girls and Leon." She thought that he was so adorable as he sat at a sewing machine dressed in his padded brassiere and tiny pink silk bikini panties. If his long hair was only styled the same way as Debbie's, she figured that he could be mistaken for Debbie's sister. That's when she had the idea about how to accelerate the boy's feminization. She could not explain why she felt such a compulsion to see Leon looking even more feminine that he already did, but she decided to follow through with her plan.
Millicent had returned to the sewing room to find that each dress was almost finished. She helped the three teenagers into their dresses. When each dress was zipped up, she had to admit that the dresses looked quite good. She was especially impressed with the pink silk and lace dress that Leon wore. The padded brassiere had made a tremendous difference in the appearance of his dress. She decided that if his hair was fixed differently, he could pass for a girl without anyone being able to guess his true gender. Millicent told the youngsters, "You all look beautiful! I can't tell you how excited I am to see three young girls turning into three young ladies. Leon, stand up straight. If you are going to school in a dress, you'd better work on your posture. Your movements need to be a little more graceful, as well. Why don't we spend the rest of the day working on that."
Leon had planned to finish the dress, go back to his house and play some video games. He was shocked to hear that his mother had given permission for him to stay the night with the Daniels. With Mr. Daniels out of town, he would be the only male in the house. Of course, you could not tell that by looking at him. In his pink dress, he looked more like an attractive girl. He heard Mrs. Daniels add, "Everyone's dresses look perfect. To keep from messing them up, let's take them off and hang them up. Joy and Debbie, you can put your other clothing back on. Leon, you need to work on developing some charm and feminine mannerisms. So, keep on the undies and I'll give you something else to wear over them."
Leon was now very worried. He had signed up for the Home Economics class to keep the school bullies from beating him up in the Physical Education class. If he had to wear girls' clothes all weekend, which was what he was beginning to suspect, perhaps it would have been preferable to have taken his chances with the bullies. Leon hung his pink dress on a wooden clothes hanger and placed it in the closet next to Joy and Debbie's dresses. He saw that Mrs. Daniels was watching with something of a gleam in her eye. He did not realize just how feminine he looked as he shyly looked down at the floor. The white padded bra and the pink panties were pure female, but the small bulge in the front of the lace panties was male. Millicent shifted her weight around so that she could squeeze her thighs together.
Leon looked up to see Mrs. Daniels coming toward him with a white pull over top and a red skirt in her hands. In the pit of his stomach, he knew that the clothes were for him. He did not resist as the top was pulled over his head. He even raised his arms so that the top could be pulled down over his upper torso. Leon heard Debbie giggling as he stepped into the red skirt that Mrs. Daniels held for him to step into. She went behind him and zipped it up and buttoned the button. When Leon looked down at his body, he found that the padded brassiere's bulges looked even bigger than he knew they really were. Still, he could not get over the idea that he had tits!
Millicent held out a pair of girl's shoes with a one-inch heel. As he slipped them on his feet, he heard Debbie say, "Leon looks good enough to get a date. In fact, I know several guys that would go out with Leon." Leon's face turned a bright red. Joy thought that Leon did make a pretty girl, even if he was wearing her old clothes. Millicent had to squeeze her thighs together very tightly as she felt a slight tremor pass through her body.
For the rest of the afternoon, Leon was tutored in the finer points of feminine behavior. He was taught how to sit, how to stand, how to walk and how to gesture with his hands. Saturday evening, Millicent showed the teenagers how to apply cosmetics for different occasions. She, naturally, demonstrated these techniques on Leon. Leon sat quietly, looking at the transformations taking place in the mirror as he was made up to look like, in succession, an innocent school girl, a debutante and a hooker. He only objected when Mrs. Daniels plucked some hairs from his eyebrows. Debbie had told him, "Stop acting like a baby! All women have to pluck their eyebrows." He tried to say that he was a boy, but Mrs. Daniels told him to not move until she was finished with the tweezers.
Finally, it was time for everyone to take a bath and get ready for bed. The Daniels' home had two bathrooms. It was decided that Joy and Debbie would share one bathroom, while Mrs. Daniels and Leon used the master bath. Leon had thought that Mrs. Daniels would go first, but found out that she had other plans. She led him into the bathroom and began filling the bathtub with warm water. She sprinkled bath oils and bubble bath powder into the filling tub. She smiled at his as she went about getting the bathroom ready for them.
Millicent Daniels moved in close to the young boy in girl's clothing. "Let's get you into the bath, shall we?" Leon stood in shock as his next door neighbor began to strip his female clothing from his nervous body. "You look so cute in girl's clothes. I just know you were meant to be a girl. You are much too nice to be a boy. You even have a pretty face. You body is small and shaped almost like a girl's. Your skin is so smooth and clear; most girls would love to have skin like yours. I think you make a very sexy little girl."
By this time, Millicent had the young boy stripped to his brassiere and panties. Her hands lightly touched Leon's smooth shoulders, moving across his bra shoulder straps. Her fingers teasingly moved down to the white padded brassiere cups. Her crotch was tingling as she cupped the padded bra with her hands. She remembered the intimate times she had spent with Sharon, her best friend and lesbian lover, in high school, as she slowly fondled the cups of Leon's brassiere. Still facing Leon, she moved her hands around him, hugging his body to hers in the process, as she unhooked the snaps of his bra. She could not stop herself from nuzzling Leon's neck and nibbling on his earlobe as her arms were wrapped around his young body.
Millicent lay the little white brassiere with the rest of Leon's clothes as she stepped back to look at him. She noticed that there was an erect penis in Leon's panties. She felt her own panties getting moist as she stared at the tented pink bikini panties. She realized that what she was doing was actually wrong, but she could not stop now. Millicent slowly dropped to her knees, reached up to the waistband of Leon's panties, and very slowly pulled them down. Leon tried to stop her but let his hands drop to his sides when she told him, "Move your hands out of the way, Leon. Just pretend that we are a couple of girls getting ready to take a bath. Pretend that we are lovers." Girls that are lovers? Leon had heard that there were such people, but he had never known of any.
Millicent smiled as Leon's triangle of pubic hair, relatively small penis and under-sized ball sack came into view. It was stiff, but it could certainly be said that Leon was not overly endowed with a huge cock. It looked to be only about three and a half inches long. With such a small cock, he would have to be very proficient at giving head to a girl in order to keep her satisfied. Millicent decided to start his education in eating pussy, tonight.
Leon meekly stepped out of his panties when instructed to do so. He glanced down to see that Mrs. Daniels was starring intently at his hard penis. He felt even more blood flow to his erection as the older woman's breath blew across the sensitive head. Leon's eyes almost bulged from their sockets as he saw the grown woman lean forward and wrap her red lips around his penis. The sensation of a warm soft mouth sucking on his penis for the first time prevented him from pulling away. Leon was frozen to the spot as he experienced his first blow job in his short life.
Millicent had only played around with a few women before she had gotten married. Her husband was the only other male that she had had sex with. Perhaps, it was the fact that she now thought of Leon as almost a girl, that she was attracted to him. Millicent's hands massaged Leon's small rounded buttocks as she blew him. Her lips moved up and down on the short hard cock in her mouth until, a couple of minutes later, Leon shot his sticky cum into her suctioning mouth. Millicent didn't stop sucking on the boy cock in her mouth. Instead, she only sucked harder as her fingers moved into the crease between his bottom cheeks. Leon's penis went immediately back to full erection when he felt a finger penetrate his small virginal anus.
Millicent reluctantly pulled her mouth off from the small cock as she turned off the water before the tub overflowed. She stood up, took Leon's hand in hers and led him into her bedroom. Her lips met his and he tasted a sweet, thick flavor on her tongue as it penetrated into his mouth. He realized that she was feeding him his own cum, but, at this time, did not care. He only knew that Mrs. Daniels had made him feel better that he had ever felt when he played with himself. When Millicent lowered her creamy lips to Leon's nipples and began to suck on them until they were wet and swollen, he felt his knees weaken. She positioned Leon in the center of her marriage bed and climbed on top of him in a classic sixty-nine position. Leon was surprised when as he saw Mrs. Daniels' wet red haired vagina moving down onto his face. He had never seen one before. And, now, he had one smearing juices all over his young face.
Millicent began giving instructions to Leon on the best ways to eat pussy. He licked the protruding flesh in the top of her wet slit and heard her moan. He continued to eat her as she began to shift around on his mouth and nose. He could barely hear her moans as her thighs held his head locked between them. He continued on instinct as he finished the older woman off. He heard her squeals of delight as her climax swept through her body. Even, Joy and Debbie, who had come to investigate the loud noises were shocked to see Joy's mother sitting on Leon's head as she shuddered and shook during her orgasm.
Debbie had already taken a shower and wore only a towel wrapped around her pretty body. Joy had just been getting ready to get in the shower and was wearing her panties and bra. The door to the master bedroom was standing partly open and the two inquisitive girls easily saw the activities on the bed. Joy was in a state of shock. Debbie, on the other hand, was becoming excited. After Joy's mother had her orgasm, she lowered her mouth to Leon's small erect cock. She swirled her tongue around it a few times before she swallowed it whole.
Debbie moved directly behind Joy to get a better view over her redheaded friend's shoulder. Joy was so engrossed by the scene on the bed, she hardly noticed that Debbie had dropped her towel and was pressing her nude body into Joy's back. Joy did notice when her best friend moved her hands up to cup her breasts through her brassiere. Joy had played with her own breasts as she had masturbated in the privacy of her bedroom. But, that was after everyone else was asleep, her light was turned off and her door was locked. Now, she was standing in the hallway, just outside her parent's bedroom, where her mother, was sitting on the face of her next door neighbor's son. And, just as if she needed things to be more interesting, her best friend's fingers had just moved over the top and had slid underneath the cups of her brassiere and were playing with her erect nipples. Joy knew she should make Debbie stop toying with her swollen nipples. She knew she should walk into her mother's bedroom and stop what she was doing with Leon. But, Joy's knees were trembling so much, she couldn't move.
Debbie began to kiss her redheaded friend's neck as they watched Joy's mother and Leon writhing on the bed together. Since Joy had not objected to her advances, Debbie slid one of her hands down over the front of Joy's body, slipped it inside the waistband of her white silk panties, and dipped her middle finger into her girlfriend's moist cleft to massage her clitoris. A couple of minutes later, Millicent raised her head from Leon's wet penis just in time to see her daughter reaching her own climax on Debbie's wiggling fingers. Millicent had never felt closer to her daughter than she did as she watched her only child experiencing sex with another girl.
Debbie saw Mrs. Daniels waving them to come over to the bed and join Leon and her. Millicent demonstrated to each of them the art of pleasing another woman. Debbie had been giving blowjobs for a couple of years, so, she and Mrs. Daniels gave Joy lessons on how to suck cock. By the time that everyone finally fell asleep, poor Leon's penis and balls felt as if a milking machine had pulled over a gallon of sperm out of him. What had bothered him the most was that Mrs. Daniels had insisted that each time one of them had sucked his cock until he came, that he be fed some of his own cum to eat. Of course, Leon considered it to be a small price to pay for the best night of his life.
The next morning, everyone had to take a bath, even if they had taken one the night before. Leon was further embarrassed by the fact that Mrs. Daniels shaved his legs and underarms while he was in the tub. Afterwards, Millicent insisted that Leon put on one of Joy's baby doll nightgowns before breakfast. Joy was upset that her mother had chosen her best nighty to give to Leon. It was made of thin, almost a gauze type of material, pink nylon with matching pink panties. Leon felt foolish wearing the sexy garment as he looked at his reflection in the full-length mirror. Mrs. Daniels also made him wear a pair of high heel shoes for practice. He wobbled a great deal on the three-inch heels as he slowly walked to the kitchen. Joy and Debbie were fixing breakfast as he and Millicent entered the room. Debbie clapped her hands as she saw how cute Leon looked. Joy gave him a warning not to mess up her best nighty.
Leon was instructed in the etiquette of eating like a young lady. The gauzy material of his baby doll nighty continuously rubbed against his sensitive nipples as he moved. After the way they had sucked on his nipples last night, they were tender and swollen this morning. Leon helped Joy and Debbie wash dishes and clean the kitchen after they had finished their meal. Leon still wobbled a bit in his high heels, but he was becoming more at home in them.
Millicent called to Leon from her bedroom. Leon's shoulder length hair swayed slightly as he moved down the hallway to the master bedroom. He sat down on the stool in front of Mrs. Daniel's make up table when she told him to. She kissed him on the cheek as she said, "You were wonderful last night. I really enjoyed what we did together. I had never thought of involving my own daughter in my fun before last night, but she learned quickly." She picked up a hairbrush and began to brush Leon's long brown hair. "You know, I just had a great idea!" She reached over and turned on her hot rollers. "A little curl in your hair will make all the difference in the world in your appearance."
Leon thought of protesting as the hot rollers were wound onto his long hair. But, the way that the three females had drained the semen from his body the night before, had sapped his strength to argue. He meekly sat and watched in the mirror as all of his hair was rolled up on top of his head. He figured that he could always wash his hair and the curl would come back out, so he relaxed. Millicent went to the bathroom closet after she had set all of Leon's hair. She found the bottle she was looking for and returned to her bedroom. Millicent shook the bottle, used the spray nozzle to coat the hair coiled around the rollers and smiled at the shocked expression on Leon's face.
"Don't worry. This is just a new type of hair lightener and permanent wave compound. I just bought it and wanted to try it out. You can be the guinea pig before I put it on my own hair." Millicent sprayed on the reagent compound to complete the process. Leon's hair changed from a brown to a blonde before her eyes! She had never seen such a sight. She clapped her hands in glee and called Joy and Debbie to come and see what had happened. The two younger girls were impressed by the transformation. Even with his hair up on rollers, Leon looked like a young girl with blonde hair. Debbie was even a little jealous.
Millicent showed Leon how to apply his facial powder, eye shadow, eyeliner, mascara and lipstick. She even had him doing part of it himself as she applied a coating of red fingernail polish. Debbie and Millicent sat side by side on the bed as Joy removed the hot rollers from Leon's blonde hair. Joy brushed the curly locks of hair into a very feminine hairstyle. Even to his own eyes, the reflection in the mirror appeared to be a very pretty girl with wavy blonde hair gently caressing the tops of her shoulders. The pink baby doll nighty, makeup and red nails, only added to the illusion. Leon was entranced with the image of the beautiful girl in the mirror. The ironic fact was that he, as his own wimpy self, would never have a chance of scoring with a girl as beautiful as he now appeared to be.
Millicent whispered into her daughter's ear and Joy went to her room to fetch some more clothing. Leon was awoken from his reverie by Millicent, "Leon, you are entirely to pretty to be called Leon anymore. Perhaps, we should call you Linda. What do you think, girls. Does she look like a Linda?" Both nodded their heads as they looked at the "boy next door" who sat in a pink nighty with blonde hair and cosmetics on his face. "Good, then. Linda, Joy has brought you some more clothes to wear today. Let's everyone get dressed."
Leon removed his nighty and pink panties. After last night, there was little need for modesty between these four people. He slipped a pair of tiny red panties up his legs, but had to have help hooking his padded red brassiere in place. Millicent held the red mini dress for him to slip over his head so that she could make sure that he did not muss his hair. She zipped up the back of his dress and handed him a pair of red two-inch high heel shoes to put on his feet. He was told to practice walking in the new shoes as Millicent got ready. Leon walked back and forth as he learned to balance himself in the high heel shoes. After the three inch heels he had worn this morning, he adapted quickly.
Leon was so enthralled with his reflection in the full length mirror as he walked toward it, and walked away, while looking over his shoulder, he had not noticed that not only had the three real females gotten dressed, but that they had their purses in their hands. Millicent enjoyed watching "Linda" move about the room, but had decided that it was time for them to go. "Linda, Honey, Joy and I need to go to the mall to do a little shopping. Debbie and you are going with us." Leon's pretty face screwed up in a mask of horror. He would die if anyone saw him made up like a girl. "Come on, Linda, don't be shy. You are just as pretty as any other girl your age. You can blend in with Joy and Debbie. In fact, I'll probably be the only woman there who is accompanied by a beautiful brunette, a beautiful redhead and a beautiful blonde."
Leon tried to talk Mrs. Daniels into letting him stay at her home while they went shopping without him. She wouldn't agree. "All girls belong at the mall. You have just never experienced shopping from a female perspective. I know you will have a great time there." Leon did not have very many options. He certainly could not run home to the safety of his own room. What would his mother and father say if he came home dressed as a girl? With the three females talking him into going, Leon resigned himself to his fate. He was told that everything would work out perfectly as long as he remembered to act as if he were a normal fifteen-year-old girl. He glanced at his reflection in the mirror for a moment and decided that at least he looked the part.
Joy rode in the front passenger seat while Leon and Debbie sat in the back of Millicent Daniels' Honda sedan. The ride to the mall was uneventful except for the time that they stopped at a traffic light and another car pulled alongside. In the other car were some of the bullies from school that Leon had gone through so much to avoid. Leon glanced over at the car and saw that the older teenage boys were waving at them. He slunk his head as Debbie cried out, "Oh look! There's Carl, Bob and Ted." Debbie and Joy waved at the bullies who had made Leon's life miserable at school. He remembered very well the time that they had caught him in the boys' restroom, had grabbed him, picked him up in the air, turned him upside down and was about to put his head in a toilet. Only the arrival of a male teacher had saved him from what he was sure would have been a watery death. He had not done anything to the bullies to cause them to pick on him. To them, he was just an underclassman wimp who deserved no better treatment. Debbie droned on and on about how dreamy Carl was. Joy said that she thought Bob was a hunk. Leon thought that they were all three turkeys.
When Millicent parked in the lot at the mall, they practically had to pull Leon out of the car. Even with everyone's assurances that he looked like a pretty girl, and with the blonde hair, could fool even his own mother, he was nervous. Leon was led into a woman's clothing store, where, for the next hour and a half, Millicent picked out clothing for Joy, Debbie and him to try on in the changing room. At first, he was frightened, but, after the first half-hour, he began to relax. By the time they left the store, he was as eagerly trying on new dresses as Joy and Debbie were. Of all the people to run into, they practically bumped into the three large bullies. Hellos were said. Debbie introduced Leon as, "Linda, my cousin visiting from out of town." Leon was surprised by the cordiality that the bullies showed to him and the other girls. That's when Mrs. Daniels said she had to run an errand and left the six teenagers to talk. Ted moved to stand close to Leon. At over six feet, Ted towered over Leon. He looked into Leon's eyes when he looked up into his handsome face. Leon noticed that he had sparkling blue eyes. Ted was about to speak when Carl stated, "There is a great movie showing in the Mall Theater. How would you ladies like to see it? Our treat, of course." Debbie said "yes" immediately. Joy took only a moment to think about it before agreeing to go. Leon held out for several minutes, until he felt the intimidation of the older, and larger, bullies as they kept asking him to go. When Mrs. Daniels returned, she was asked if they could go to the movies with the three guys. Leon was shaking my head "no". She ignored him and told them it would be okay except that she needed to go to a hair appointment and would not be able to take the girls home if they went to see the movie. Carl offered to drive them home since he had his father's car. Leon's heart sank when Mrs. Daniels said that they could go and have fun.
Carl paid for his and Debbie's tickets. Bob paid for his and Joy's. That meant that, for all practical purposes, Leon was Ted's date since he had paid for them. He followed along with them simply because he did not think that he had any other choices. The inside of the theater was already dark as the previews were playing. Ted was very considerate as he let Leon sit down first. Leon was afraid that Ted would recognize him at any minute and begin beating him up. Leon flinched as Ted raised his arm and placed it around his shoulders. Leon looked to his left to see that Joy was snuggled up to Bob as he placed his arm around her. Debbie and Carl were actually kissing!
Leon looked back at the screen as he thought about his predicament. The one thing that he had noticed was that bigger boys certainly treated younger and smaller girls differently than they treated younger and smaller boys. Leon felt Ted's hand moving down his arm, over his shoulder and onto the padded cup of his brassiere. That's when Leon made the mistake of looking up into Ted's eyes. His head lowered toward Leon's red lips before Leon could even think about pulling away. Last night was the first time that Leon had been kissed by a girl. Now, a guy big enough to beat him up, if he made Ted mad at him, was kissing him and when Leon tried to pull his head back, he found that Ted's arm was wrapped around his neck. Leon thought to himself, "Don't panic! The kiss will be over soon." That's when Leon felt a large tongue penetrate his lips and enter his mouth. That's when Leon panicked.
Leon struggled in Ted's strong arms as he tried to break free. It was like wrestling with a gorilla. When Ted finally let him go, he leapt to his feet and jumped past Ted to run up the theater aisle as fast as his high heel shoes would let him. He reached the relative safety of the lighted lobby and looked around for the nearest escape route. Just when he had decided that he would go home, Debbie grabbed one of his arms and Joy grabbed the other one. Before he could tell them that he was going home, they had whisked him through the door of the Ladies' Restroom.
Debbie pushed Leon up against the tile-covered wall as Joy checked to make sure that they were alone. Debbie had a nasty expression on her face as she said, "We have been flirting with those guys for weeks and now you are trying to spoil our chances of having a good time. Those guys are hunks! Joy and I want Carl and Bob for boyfriends. What you do with Ted is your business, but we will not let you ruin our chances." I told her how Ted had kissed me. "So? Don't you realize that half the girls in our class would trade places with you if you gave them a choice? More girls in Home EC masturbate while thinking of one of these three guys than all the movie stars combined. You should feel flattered that Ted has taken an interest in you."
For the first time since this had all started, Leon decided to show that he had a backbone. "You listen to me. I am a guy. Guys don't kiss guys. And, I will most certainly not kiss Ted. Nor, will I let him kiss me. I'm going to call mom and have her come and pick me up. And another thing, I don't care how badly you want to date those guys, I am not going to let Ted paw me." Leon felt good. He had grown a backbone and had asserted himself.
Debbie had a hard look on her face as she spoke softly, "Okay. Do what you want. However, Joy and I are going back in there and we are going to tell the guys how you have pulled a fast one over on them. We'll tell them that you dressed yourself up like a girl just to play a prank on them. I'll tell them that you got Ted to kiss you so that you could go to school next week and make fun of them. What do you think that they will do to you when they catch you?" The backbone that Leon had developed only moments earlier, crumbled to dust. He felt tears coming to his eyes. Joy grabbed some toilet tissue and told him to dab at his eyes so that he would not ruin his eye makeup.
Debbie hugged Leon and whispered, "You really are more girl than boy aren't you? Don't worry, Linda, we'll tell Ted that it is your time of the month. He'll understand. And it won't mess up Joy's and my dates with Carl and Bob. Ted is such a dreamboat, too. Just relax a little. Forget that he's a guy. Pretend that you really are a girl. A little kissy kissy never hurt anyone. Okay?" Leon saw no way out of his situation. After all, he had enrolled in the Home Economics course so that the bullies would not beat him up. His plan had backfired. He reluctantly nodded his head. "That's a good girl. The next time we spend the night together, I'll make it up to you." Debbie smiled and lightly kissed his lips just as the door opened and two older women came into the restroom. They had shocked looks on their faces. Debbie, Joy and Leon returned to the relative safety of the darkened theater.
Debbie leaned down and whispered something into Ted's ear as she passed him on the way to her seat. He nodded. He stood up as Leon sat down. Leon would have never suspected that Ted had any idea what manners were. Ted didn't try to put his arm around Leon or kiss him in the theater. Debbie and Joy wasted no time with their dates, though. Their lips were locked together, and they were visibly groping each other all during the movie. About half way through the movie, Ted reached into Leon's lap and took his right hand in his. Ted spent the rest of the movie with his huge hand engulfing Leon's much smaller and more delicate hand.
Finally, the movie ended. Debbie and Joy came up for air. They had to re-arrange their clothing as the lights came up. They joined the throng filing out of the theater. Bob said something about going for a pizza. Everyone, except Leon, enthusiastically agreed. The Pizza Place was a favored teen hangout in the mall. As they entered the restaurant, Carl had his arm around Debbie, Bob had his arm around Joy and Ted slipped his arm around Leon's waist. Ted bent down and whispered in Leon's ear, "I'm afraid that one of the other guys will try to steal you away unless I have my arm around you. You don't mind, do you, Linda?" Leon looked up into Ted's blue eyes. The pizza restaurant was a place where an underclassman student had to be brave to enter because the upper classmen sometimes ran them off. And yet, here he was with one of the very guys that might have beaten him up if he had violated the upper classman territory as a male. Ted had his arm around him and would be willing to fight for him to protect him. Leon decided that girls were treated far differently than boys.
Ted held the chair for Leon as he sat down at a large table. A conversation was started where Leon was asked about where he lived and what school he went to. Debbie answered most of the questions for him. Under the table, Ted held his hand the entire time that they waited on the pizza order to arrive. A couple of times, when Leon looked at Ted and Ted smiled at him, he returned a friendly smile. Leon was not flirting with the much larger guy, it was just reflexive. What really did surprise Leon was the fact that he was starting to have a good time. He was also beginning to think that Ted was a nice guy, when you got to know him.
The pizza was ready. As Leon ate a slice of pepperoni pizza, he found himself talking more as Ted carried on a conversation with him. Ted was handsome, in a hulking kind of way. He certainly did have the bluest eyes that Leon had ever seen. By the end of the meal, Leon had become relaxed and was enjoying the company. The guys paid for the meal and escorted the girls out of the restaurant and to Carl's dad's car. It was a four-door sedan so it wasn't too crowded in the back seat. Debbie sat up front with Carl and the other four were sitting in the back. Joy and Leon were in the middle while Ted and Bob put their arms up around them to make a little more room.
Leon could not help but see that Bob and Joy were kissing again. Bob had even laid his hand on Joy's bare thigh and had moved it up her leg. Joy pressed her thigh against Leon's as she opened her legs for Bob's hand to move farther. Leon could see that Bob's hand was far enough under Joy's skirt that he had to be playing with her crotch. Leon looked away only to be face to face with Ted. Ted had also noticed the amorous activities of the couple sharing the back seat with them. Ted slowly moved his lips closer to Leon's. Thoughts raced through Leon's head. He remembered the threat that Debbie had made. He did not want Ted and the other much larger boys to beat him up and toss him out on the side of the street. He did not have many options. He felt Ted's lips tenderly touching his.
The kiss that Ted gave Leon was gentle. Ted had been told that Linda was an inexperienced virgin that was having her period. He thought that Linda was one of the cutest blondes that he had seen outside of professional models. There was something about this girl that really turned him on and he did not want to offend her again like he had done in the Movie Theater. He moved more slowly this time. He slowly placed his free hand around Linda's tiny waist and held her small delicate body in his arms.
After the initial revulsion that Leon felt from being kissed by another boy, he resigned himself to the fact that Ted had bought him a ticket to see a movie and a pizza. Leon had never been out on a date with a girl, but he knew that a guy expected at least a few kisses from a girl when they were on a date. He tried to relax as Ted kissed his lips several times. After all, he had actually begun to like Ted. He decided that the situation could have been much worse. That's when Ted pushed his tongue into Leon's mouth.
When Leon managed to gently push Ted away, he saw that they were not on the proper street to their homes. They were actually on a narrow wooded road that was used as a Lover's Lane by the high school students. Carl parked the car in a secluded spot and turned to the back seat. "Okay, Ladies and Gentlemen. It is fun time. The last one out of their clothes has to pull clean up duties." Instantly, Carl, Debbie, Bob and Joy began removing their clothing. Leon knew that if the bigger guys saw him nude, he might not survive the night. He was surprised when Ted opened the door and pulled him from the car. They stood beside the rear fender.
Leon looked up into Ted's face as he heard Ted whispering, "I know you aren't like Joy and Debbie." Leon's heart stopped for a moment! Did Ted know that he wasn't really a girl? Had everyone lied to him when they told him that he could fool anyone into believing that he was a female? Was Ted about to beat him up? "You are not a slut like they are and I respect you for it." Leon began to breathe again. When Ted put his arms around Leon's waist, Leon was almost happy to let Ted kiss him again. Even when Ted probed Leon's mouth with his huge tongue, Leon did not try to pull away. After a few minutes of being kissed by the much larger young man, Leon noticed that his knees were getting weak.
When their lips parted, Ted looked into the car. In the back seat, Joy was naked and laying on her back as Bob moved up and down between her spread legs. In the front seat, Carl sat up in the middle of the seat while Debbie sat facing him, straddled across his lap, and moved up and down while Carl sucked on her small but pointed breasts. Leon felt Ted's huge penis as it became erect and was pressed against him. Ted took Leon's arms and wrapped them around his neck as he lowered his lips to Leon's. Leon had decided to go with the situation, no matter how strange it got. Leon parted his lips to allow Ted's tongue to enter his mouth, and then, he began to suck on the invading tongue.
When their lips parted, Ted whispered to him, "Oh, Linda! You are the sexiest girl that I have been out with. You are so pretty! I love the way you look. At the Pizza Place, the other guys were jealous of me because I had you." This time, when he kissed Leon, Leon actively kissed him back. Leon had never had anyone make him feel so wanted before. He did not resist even when Ted took one of his hands in his and guided it to the front of Ted's jeans. Leon was simply amazed at the size of Ted's tool. His fingers gripped the long fabric covered shaft on their own after Ted moved his hands away.
"Linda, you are the sweetest girl, but I am in pain. I think my balls will explode if you don't help me. I know you are a virgin and can't do anything right now, but could you please take it out and play with it for me?" Leon gazed up into the big blue eyes and slowly unzipped the front of Ted's pants. Perhaps, it was the full moon? Perhaps, it was the moans and other sounds coming from inside the car? Leon reached into Ted's blue jeans and pulled out the largest cock that he had ever seen.
Leon was not very well endowed. Ted's penis was twice the size, both in length and width, of Leon's. Ted closed his hand around Leon's fingers and guided his much smaller hand in a stroking motion up and down the long thick shaft. Leon couldn't understand why he was breathing so heavily as he handled another guy's penis. Ted brought his mouth back to his and kissed his passionately as Leon continued to stroke the huge cock. When their lips parted, Ted whispered, "I know you aren't a slut, Linda, but would you please kiss the head of my cock? You don't have to give me a real blowjob. Just kiss it and maybe lick on it a little."
Leon's mind was screaming, "NO!" even as Ted used his hand on Leon's shoulder to guide his blonde head down towards the huge purple penis. The almost baseball bat sized head was pressed against Leon's closed lipstick coated lips. Part of Leon's mind told him to run. A few drops of pre- cum were smeared onto Leon's red lips. Leon knew he should not be doing this. The smell was not unpleasant, nor was the taste when Leon's tongue automatically came out and licked his lips. Leon remembered, once again, the threat that Debbie had made as he swallowed his pride and opened his lips to accept Ted's huge member into his warm moist mouth.
Leon blocked out all thoughts of this being wrong as he began to bob his head up and down on Ted's huge cock. His own little penis was standing at attention in his silky panties as he went down on another guy's cock. Leon could not explain why he wanted to please the older and much larger boy. He just knew that he had developed a new type of relationship with Ted, and he wanted to make Ted happy. To make Ted happy, he would let him cum in his mouth. Ted being a teenager himself, he did not last long with Linda's warm sucking mouth working on the sensitive head of his cock. He blasted his thick gooey semen into Linda's mouth as he held her head in his hands to prevent her from pulling away. Leon was swallowing his cum.
Leon almost choked as the first spurt of boy juice rocketed from the tip of Ted's cock. By the time that the second pulse of cum was shot into his mouth, he had to swallow just to make room for it. Six or seven spurts later, Ted released his tight grip on Leon's head as he fell back against the fender of the car. There was applause as Leon gulped down the last drops of cum. Carl, Debbie, Bob and Joy were hanging out the windows of the car as they applauded Leon's cock sucking abilities. Carl said something about letting Linda suck his cock, too. Leon stood up and hid his reddened face in his hands in embarrassment. Ted put his arms around him protectively and said, "Carl, get Debbie to suck your cock. Linda is my girl." Leon gratefully hugged Ted and laid his head on the bigger boy's shoulder. The others said something about "True Love" as they pulled their heads back inside the car windows. Debbie and Joy wasted little time trying to prove to Carl and Bob that they could give as good of a blowjob as Linda had given Ted. Both Carl and Bob closed their eyes and pretended that it was the pretty blonde that was sucking their cocks as they fired their semen into the suctioning mouths of their girlfriends.
Leon had a sperm coating on his tongue as he was lovingly held in Ted's strong arms. He knew that tonight had been as big of a turning point in his life as last night had been. No matter what happened in the future, he would always remember the last two days. When Ted's fingers gently tilted his head up, Leon eagerly kissed him. An hour later, they were dropped off at Joy's house.
As they entered the front door of the Daniels' home, Leon almost turned around and ran back out the door. His mother sat on the living room sofa with Mrs. Daniels and another woman. Mrs. Daniels told Debbie and Joy to go upstairs and for him to come into the living room. Leon walked into the room on leaden legs. What would his mother think of him? He was wearing a red mini dress and red high heel shoes. He had makeup on his face, his lipstick was smeared from the kissing and sucking Ted's cock, and his mouth still tasted of sperm.
Leon's face was red and his head hung down as he approached the sofa where his mother sat. He heard his mother speaking, "When Millicent told me that they had made you wear a dress and that they had fixed your hair, I had no idea that you would be so beautiful!" Leon realized that his mother was not mad at him. He glanced up to see her smiling. "Come over here and let me look at you." You certainly know how to move in high heels. And, I like your hair blonde. It suits your complexion. Millicent, you did an excellent job on my little girl." Janet Jenkins stood up and hugged her new daughter. She had always wanted a daughter, but had given birth to a son. Now, the situation was corrected.
Millicent Daniels spoke up, "Linda, I want you to meet a very special woman. May I present Julie Jenkins." The third woman in the room stood up. She was about the same height as Leon, very attractive, but was older. When she told Leon hello, Leon almost fainted. Julie Jenkins was his father!
Leon's mother explained that his father had been a cross dresser all his life and that he enjoyed getting dressed up when Leon was not at home. She laughed when she told him that he had almost caught his father on several occasions when he had come home early. Janet told her son, "Julie enjoys what we do together and I hope to see more of Linda around our house from now on, too. You make such a beautiful young lady, it seems a shame to waste your life as a boy." Leon hugged his mother and Julie.
The next week, Leon wore the pink silk dress that he had sewn to school. He also wore makeup, panties, a padded brassiere, pantyhose and high heel shoes. His hair was still curly and blonde. The girls in his Home Economics class accepted him as one of them almost immediately. The rest of the school, he knew, would take a little longer. Mrs. Brown didn't have the heart to tell Leon that she had only been joking when she had told him that he had to wear a dress like everyone else.