Teased Into Crossdressing                by: Kresha Matay

 

Mary caught her stepson, David, looking up her skirt as they sat watching TV. He was lying on the floor, at an angle to her crossed knees. Casually, in an effort to be subtle, she adjusted the drape of her misplaced skirt, at the same time re-assuring herself she hadn't exposed all that much. The most David could've seen was the welt of her nylons, possibly the garter straps and maybe some bare thigh. This wasn't the first time she had caught her stepson trying to see up her skirts. In addition, she had caught him staring down her blouse when he held a chair for her, or down her robe when she bent to kiss him goodnight. She suspected he was also guilty of peeking through the old-fashioned keyholes in both her bedroom and bathroom doors. While this adolescent voyeurism had initially made her quite uncomfortable, Mary had recently become aware that she secretly enjoyed being spied upon. Knowing her stepson found her attractive boosted her ego. In the last few months she had accepted his peeking and at times, was even guilty of provoking it.

David was sixteen, her only child by marriage. Ron, David's real father had been her husband for three years, then vanished one night without a trace. His first wife, David's mother, had left both of them, for a traveling salesman. Mary, who had dated Ron before he married David's mother, got him on the rebound after the uncontested divorce. Everything had gone well for awhile, even David's acceptance of her as a surrogate mother. Then the two adults began having problems. Ron went out for cigarettes one night and never returned. A missing person's report had been filed and the local police had investigated, but no clues to his disappearance had ever been found. The court awarded David to Mary's care after his real mother had refused to take him into her new household.

At first, Mary thought her husband had met with foul play, but as the years went by and no new evidence of his whereabouts was ever discovered, she changed her mind. She accepted the fact he had just left them to manage on their own. It was just recently that he had been declared legally dead and the insurance company had reluctantly paid Mary the settlement check.

During those seven years, Mary had taken an assortment of menial jobs to support the two of them. None of which paid much, just enough to get by. This left Mary little time for a social life of her own. She eventually convinced herself it didn't really matter; it was better to be without a man then to be hurt again. All she had was her jobs and David. Performing the duties of both parents wasn't easy, but Mary did it well and a warm and cohesive bond developed between stepmother and stepson.

The settlement Mary received meant she would never have to work again. These last six months had been wonderful for both Mary and David! A new home, a new car, new clothes for both of them and most importantly for Mary...time. The time to spend on herself and David. She had never allowed herself to become "frumpy" or even "mousy", but also had never had the spare cash to really take care of her appearance. Now she did! She transformed herself into an extremely attractive woman of thirty-three, a woman who drew attention from both sexes, wherever she went. Fortunately the basic bone structure, body features and feminine symmetry had been hers from adolescence.

Mary was glad that David was finally showing an interest in the female gender. David had been much slower than normal in reaching puberty. At first Mary had merely ignored the fact he paid little if any attention to girls. But when he reached the age of fifteen and still exhibited no interest, nor developed any of the physical signs of puberty, she became quite concerned. Taking him to a Urologist, for a complete physical examination, while embarrassing for both of them, had relieved her concerns. The doctor, after a thorough exam, had assured her David was quite normal and it would be just a matter of time before the changes occurred. The doctor's diagnoses had proven correct. Just before his sixteenth birthday the changes had begun. She was so pleased that she allowed him certain liberties that she would have never considered proper if she hadn't been so concerned.

David began to show interest in feminine clothing, most especially women's undergarments. This she considered a good sign of his "growing up". She remembered how curious her brothers had been when she started wearing bras and nylons. In an effort to help David she decided to "inadvertently" leave her lingerie piled on top of the dryer instead of immediately putting it away, as was her usual practice. After a day or so, she noticed the garments had been examined. In addition, she began to notice unexplained runs in her nylons and pantyhose. Mary accepted this as the price of David's curiosity, assuming David’s mishandling of the sheer and delicate materials inadvertently caused the snags and runs.

Mary also found that she was beginning to enjoy the tricks he employed in his efforts to spy on her. She rationalized that since it only involved the two of them...it couldn't hurt. She was getting an "erotic charge" whenever she became aware of his attempts. The feelings became so enjoyable; she began to find ways to create them!

She would carelessly position herself so David could see up under her skirts just past the welts of her hose. She would bend to the waist in order to pick up a piece of imaginary lint when he was standing behind her. She knew the effect the tightly drawn skirt would have on the youth. She began wearing garterbelts and nylons instead of pantyhose thereby upgrading her stepson's level of excitement.

Mary would quickly "dart" between the hall bath and her bedroom, wrapped in only a towel. Later she would claim to have forgotten" her robe. She would leave her bedroom door slightly ajar so David could observe her in her nightgown as he passed her doorway. The only thing Mary refused to do was allow David to see her naked. At times, she would inadvertently "forget" a button or maybe even two on her blouse, allowing him a peek at the upper rise of her breasts. Once, in a playful mood, she even spilled some water on the kitchen floor as she stood before the sink doing the dishes. Tossing David a roll of paper towels, she asked?

"Honey, would you please wipe up the floor for mom so I don't have to bend in this tight skirt?"

Mary leaned against the sink, her legs spread taut against the skirt material. Looking back under her left arm...she saw David, on his hands and knees, his head at her ankles, his face turned upwards, staring up her taut skirt, paying absolutely no attention to the spill. Mary smiled to herself as she recognized the excitement on her stepson features. He had the best view of her nylon-clad thighs and panty covered ass she had ever allowed him. She could feel his warm breath on her ankles and calfs as he moved to get an even better look. When she felt her leg muscles begin to tremble, from her own excitement, she decided he had seen enough. Calling down to him, she asked?

"How are you coming with getting it wiped up?"

"Almost finished, mom!" He hurriedly answered.

Quickly he wiped up the spill and adjusted his erection so his stepmother wouldn't discover what he had actually been doing as he knelt at her feet.

That was the most exposure she had ever allowed. She never let him actually see anything more than if she was lying on the beach in her bathing suit, it was the act of teasing that excited her and brought David back for more. She took erotic pleasure in the bulges that formed in his pants and the actions he took to hide them from her. In her mind, these were more signs he was growing up normally. Mary actually rationalized she was helping her stepson "catch up". She explained away her actions and any possible guilt, reasoning it was better he experienced these "lessons" at home than with some unknown teenage girl which he might get pregnant and thereby ruin both their lives.

Some of David's actions, she didn't quite understand. Those she couldn't explain, she ignored, even though they preyed on her mind whenever she was alone. The one that bothered her most was not being able to discover what he did when he hid out in his locked room. She suspected her stepson withdrew into a fantasy world, plotting his next attempt to see her naked.

What David really did in his room was...masturbate! Within the last seven months he had discovered the female of the species and the effect these discoveries had on his penis. Puberty, long delayed, had attacked with a real vengeance.

At first, not understanding what was happening to him, he sought advice. Since he was too embarrassed to talk to his stepmother, he asked an older boy at school. This was at first greeted with laughter and then with the advice to "steal" a pair of his mother's panties from the hamper and rub them over his dick and balls whenever he got the urge.

Unsure of the advice, he nonetheless did as instructed and obtained the obvious result...orgasm. Everyday for the next week he performed the same act until the panties were no longer smooth and silky, but caked with his emissions. Assuming his stepmother would never miss one pair of panties, he stuffed them into the garbage can, behind the house. Realizing he couldn't continue throwing away his stepmother's panties without eventually being discovered, he stole two pair off a neighbor's clothesline. These he hid in the back of his closet.

One day, when he was left alone in the house, he decided, "If the panties feel so good against my dick, I wonder how they'd feel if I wore them?" Quickly undressing, he stepped into the pale blue pair he had stolen, pulled them up his legs and snuggled them around his ass. The coolness and silkiness of the material created an instant hard-on. He had a difficult time getting the panties to "sit" right, like the way they fit those models in the Penny's catalog, until he discovered that bending his dick backwards between his legs helped. Standing before a mirror, he posed his lower torso mimicking how he remembered the models in the catalogs stood. It was definitely an exaggerated but fun experience for the youth. He enjoyed the silky feelings of the material against his skin and spent long minutes rubbing his hands over his panty covered ass, while fantasizing it was a woman's buns he was stroking.

Pleased with himself he nervously snuck into Mary's room. There he found a discarded pair of his stepmother's nylons. They were still attached to a garterbelt. Cautious to the extreme, David worked at the unfamiliar garment until through trial and error he discovered how to roll the silky hose up his trembling legs and re-attach the garters. By this time his hard-on was raging, no longer held back between his legs. Sitting on the edge of his stepmother's bed, he crossed and re-crossed his legs, reveling in the feel and texture of the hose. Running his hands over his silken legs was so exciting...he was losing control. In fear, he quickly removed the garments, rushed to the john and orgasmed into some tissues.

This was his first step into crossdressing, but only the first. The experience had been far too satisfying not to repeat. From that first exciting moment, whenever he was alone, he would sneak into Mary's room, carefully open her lingerie drawers and borrow a bra, panties and nylons. His stepmother always kept her lingerie drawers disorganized so she never discovered her pretties had been disturbed.

David quickly progressed to wearing his stepmother's dresses, blouses, skirts, slips, nightgowns and high heels. Make-up, a wig and earrings became the next step in his adventures. Each new adventure increased his obsession with feminine clothing and the sensuous pleasure he derived from crossdressing and acting feminine. He continued to practice his gender switching, experimenting like any other teenage girl would and actually became adept at wearing feminine attire. As he became more and more comfortable with each new advancement. He began to fantasize what his life could have been if he was a pretty and sensuous female instead of a male. More and more his daydreams and desires revolved around ways he could change his gender. Like other young boys who have had the same fantasies he created dreams in which he utilized various methods to become female. They didn't have to be based in reality. One gender change came about due to a witch's magic spell, another, finding a bottle with a genie inside, a third, from a mysterious combination of chemicals. It didn't matter how outrageous the method his mind created to explain his change, it only mattered that he had found a means to become female...if only in his mind.

Now he began to "study" females, as a different gender. Whenever he discovered a disparity in male vs. female mannerisms, he went home and practiced until satisfied he had copied it perfectly. Whenever he crossdressed, he would stand before the mirror and create fantasy conversations speaking in a girlish voice. With enough practice he managed to develop this feminine voice, also to perfection. David initiated an alter ego. One, which made him, feel more attractive.

Once tempted, his young mind became obsessed with women, their clothes their mannerisms and their bodies. Under the pretense of looking at sporting goods, toys and tools, he "memorized" the women's clothing and lingerie sections of every catalog he found around the house. He became an expert on lingerie and foundation garments. He ascertained the purpose each item fulfilled towards enhancing a woman's figure. He was disappointed his stepmother didn't own many of the foundation garments, but realized she had no real need for some of them. Matching Mary's lingerie labels against the catalog descriptions, he learned to distinguish the subtle differences of each material. Using this same method, he studied the labels of the dresses, skirts and blouses he found in Mary's closet. Diligently applying himself, he soon became expert enough to determine what any woman was wearing, the material from which her skirt, blouse or dress was made and in many cases the fashion designer who offered it for sale.

For every time his stepmother caught him trying to see up her skirt, or down her blouse, there were twenty more times he got away with it. When he wasn't fantasizing about being dressed in women's clothes, he dreamed of going out with Mary...as her daughter. He knew he couldn't tell his stepmother about his crossdressing, but almost wished she would catch him, thereby, finally bringing it out in the open.

The desire to actually see a naked woman's body grew so strong he no longer could control his emotions. Finally he decided to take a bold step...hiding out in Mary's bedroom and watching as she undressed. If he got caught spying on her, he reasoned, he would be forced to admit his fantasies about seeing her nude and might even be brave enough to admit to his crossdressing. Telling Mary he was going out for awhile, he slipped back into the house, into her bedroom, and hid under her bed. David knew she was going dress shopping shortly and hoped she would change her outfit. He wasn't sure he would see her naked, but at least he would see her in just a bra and panties.

After about twenty minutes (it seemed like an eternity), Mary entered her bedroom. Stripping to her "undies" she sat before the dressing table and did her make-up and hair. Mary had no idea she was being "spied" upon. She went through all the normal motions of getting ready.

To David lying under the bed, each step in her preparations was exciting and educational. He was able to barely glimpse the crack of her ass through the sheer white panties she wore, but no more. As his stepmother would reach for something, she would turn slightly. This afforded him a partial view of her bra-covered breasts. While he had previously "caught" sight of her in a bra, for some reason this time was more exciting since she didn't know he was there. His hard-on pushed up against his stomach, forcing David to adjust his position. He wanted to play with himself, but was afraid he might ejaculate in his pants. While David lay there, holding his breath, Mary reached into her drawers, select a garterbelt, sheer black hose and a matching bra and panty set, the same set he had worn just the day before.

Totally unaware of her stepson's presence, Mary reached behind her back, unhooked her bra and slipped her arms out from the straps. Then, as every woman does after removing her bra, she massaged "life" back into her sensitive breasts, squeezing, kneading and rubbing the firm mounds of flesh. David realized what his stepmother was doing even though her back mostly blocked his view. Picturing the scene, in his mind and seeing her nude back, his mind raced.

"Oh how I wish I had breasts like Mary's!"

With a start, he came to the realization that he no longer thought of her in a sexual sense. His earlier fantasies about Mary had including touching her breasts, etc. Now he wanted to have breasts like hers! He no longer felt desire for her, but instead wanted to be like his stepmother...a female! His goal had changed.

David missed his big chance when Mary inserted her thumbs into the elastic waist of her panties and slid them down off her legs, tossing them to the floor. It had happened so fast the hidden youth wasn't able to see anything other than the quick flash of the crack separating the moons of Mary's asscheeks.

Now her "tan lines" were visible. Straining to see more, he adjusted his position, and in doing so, he lightly bumped his head against the bedframe. The pain, not serious, made him wince. He didn't realize the sound his contact with the frame made was so loud. He assumed his stepmother hadn't heard it.

He was mistaken! Mary had definitely heard the bump. She also had seen the movement of the dust ruffle, reflected in her vanity mirror. Mary controlled her natural reaction to cover herself. She immediately realized it had to be David under the bed. This was more than just peeking...he had actually seen her naked breasts and ass! Looking at her image in the mirror she held a silent discourse with her reflection.

"I can do one of two things, I can continue as if I didn't know he was there, or I can start a yelling, screaming fit. If I throw a fit, it won't change the fact that he's already seen me naked, besides maybe I'm partially to blame. I've teased the poor boy to the point he probably couldn't control his desire to see a naked woman and who else is there for him to spy on?"

Smiling into the mirror and recognizing the mischievous twinkle in the eyes of her reflected image, she continued her silent discourse.

"Afterall, what actual damage has been done? I'm sure every young boy tries to see his mother naked and most, I imagine, succeed. I tried to see my father and my brothers naked when I was a young girl! It's better if I don't let on, that way nether one of us needs to be embarrassed."

Pausing a moment, she mused. "Besides I bet I can have some fun with this situation."

The longer she contemplated her decision, the more thrilled she became. Mary's rising emotional state overcame her natural inclination towards modesty and therefore she decided to "give" her stepson a "show" he would long remember. Deciding how much she would permit him to see, she put her verdict into action. Turning sideways on the stool, she swung her legs parallel to the dressing table and David's view. Mary's legs now faced away from David thereby affording her stepson a most generous view of her nakedness but at the same time she avoided exposing her womanhood to the hidden youth. As he watched, Mary went through a series of exaggerated motions as she attached her garterbelt.

David was forced to bite his clenched knuckle in order to muffle his excited moan! There sat his stepmother...naked, her breasts exposed. To her stepson's excited stare the full, round mounds gently swaying and bobbing before him were perfect. Mary's pert reddish brown nipples, because of her own excitement, stood out from her equally large brown aureoles. The breasts showed just the faintest hint of a muscle sag, but for her age and David's lack of experience, they were outstanding. As she moved, they bounced, jiggled or swayed. Having never seen an adult woman's breasts, he lay there mesmerized by their beauty. Mary allowed him a generous examination, delaying her normal method of dressing to insure he would remember every rounded curve of her sensuous orbs.

David's concentration was snapped to attention when his stepmother bent down to roll her sheer black nylons up her legs, past her knees and over her thighs. Mary spent a long moment adjusting the proper fit of each nylon. She sat, raising and extending one leg after the other, just like Mrs. Robinson, running her fingerpads along the sheer material and stretching it taut against her smooth leg muscles. Finding imaginary fault with each leg, Mary removed each nylon and repeated the operation. David, meanwhile, thought he might have seen the merest hint of her hairy mound when Mary alternately raised each extended leg into the air, to run her hands up and down her legs...but he wasn't sure.

After attaching the garters, she inserted both feet into her panties and "squiggled" herself into the red silk material. Slipping her arms into her matching Demi-bra, she teasingly adjusted how her breasts fit with-in the cups. Then caught the hook in front. Raising her arms, she did an exaggerated and sensuous stretch. This caused her breasts to push up and out and bent her back into a cat-like pose. A pose every woman has performed since the beginning of time to entice members of the male gender. Momentarily maintaining the stretch, Mary examined herself in the mirror. She smiled.

Finally letting her arms drop, she rose to her feet. Bending over, knees locked, she made a final adjustment to her nylons thereby offering David an excellent view of her pantied ass. The angle was perfect; he saw the triangle of her crotch as the silken material bunched around the pouting lips of her womanhood. As Mary turned and walked to the closet, David was fleetingly rewarded with an eyeful of her panty covered muff. This was too much for the feverishly excited minor. Biting his knuckle, he came in his pants!

Mary, realizing how excited she herself was getting and also aware there would be no opportunity to relieve herself, had chosen to cut the "show" short. Deciding to give her stepson one last thrilling glimpse, she took a few steps, stopped, paused a moment as if in contemplation of what to do next, then, with determination, strode to her closet, gone from David's view. Within two minutes she returned carrying a dress in her outstretched arms. Stepping into the lined dress, she then slipped on some heels and left the room and the house.

David continued to lie hidden...till he was certain Mary had driven away. Slithering out from under the bed, he picked up his stepmother's discarded panties and rushed to the bathroom, where he proceeded to liberate his throbbing manhood from the gooey mess inside his pants. It took but a few quick strokes...and he came a second time, more profusely than before. To David's utter amazement his organ remained rigid. David's final orgasm came more slowly, but as potent. Barely able to stand, he replaced Mary's panties where she had dropped them, retired to his room and fell asleep dreaming of what had occurred.

Mary, as she drove away, decided she had taken the correct tack. The image of her stepson masturbating after she left brought a smile to her face.

"I wonder if I should teach him a lesson and spy on him. Maybe I will, afterall, turnabout is fair play!"

Other things were happening in David's life. As his desire to be female grew, David no longer hung out with the guys, but took every opportunity to spend time with girls his own age. They at first were naturally suspicious of his motives, but soon came to realize he wasn't a threat and eventually even welcomed his membership in their close-knit group. They "felt" he "understood" them, and treated them as equals, not like his counterparts. The girls, Karen, Kathy, Joyce, Susan and Tammi were just as sexually naive as David was. Within a brief period, they recognized the value of having a non-threatening male as a member of their clique and accepted him. This opened a new world to David! Now, comfortable in his presence they began to openly discuss all the topics that young girls talk about, namely boys, clothes, their looks, their bodies and of course sex as if he either wasn't there or was female like them.

David joined in the conversations as their male authority. He offered constructive observations without the usual hidden male agendas and made practical suggestions as to what made guys notice girls. His astute proposals were tested and found helpful in their attempts to catch the attention of boys. The girls became so comfortable with his presence, they never became anxious over their stance, dress or the possible disclosure of their budding bodies to his view. In David they quickly recognized his fashion expertise and always sought his opinions on different styles and selection of clothing. It started with skirts, tops and shoes, then naturally progressed to lace on a slip, then bras and panties...till that one pivotal day.

It was over Christmas vacation and happened at Karen's house. Her parents both worked and wouldn't return till much later in the day. The girls were in an especially playful and fun-loving holiday mood. They decided to "dress-up" in the clothes, shoes, and hairpieces of Karen's mother. They took turns playing the mistress of the house, while David was expected to act the part of the husband. They had played this game many times before, but today it would be different. Instead of leaving the room to change, the girls decided to see if they could shame David by changing in front of him. When he didn't react as they had expected, they confronted David.

"We don't think it's proper that you see us in our bras and panties while you sit there fully clothed. How do we know you won't tell everyone? We think you should strip down to your shorts just like us. If you don't, you'll have to leave and never be with us again."

David, realizing he had no option if he wanted to remain...agreed to their demand. Afterall, he silently mused, for a boy...it was just like being on the beach in a pair of trunks. The problem was...he wasn't wearing shorts! That morning he had worn the pink lacy panties he had stolen from his neighbor! David had become so accustomed to wearing panties, he had forgotten. When he dropped his pants the girls saw his groin was covered in pink panties with delicate lace at the waist and legholes. The girls, stunned for a moment, quickly recovered, then began to laugh uproariously. Catching her breath, Karen giggled.

"Now we know why you like to be with us! You really want to be a girl!"

David made a grab for his clothes, but before he could cover-up, he was seized by five pairs of arms, wrestled to the floor and pinned to the carpet. When he realized he couldn't overpower his assailants, he stopped struggling. The girls allowed him to sit up, but still firmly held his arms and legs. Each girl, in turn, investigated how David looked in panties. He was "forced" to stand, twist, turn and twirl around so all could see how the ultra-feminine panties fit his male frame. Now instead of being embarrassed, he was secretly enjoying their interest. After all five girls had their fun, he was allowed to sit back down on the floor. Kathy, silently surveying the other four, made a gesture to which the others nodded agreement, then stated.

"If you don't want us to tell everyone you’re a sissy who wears girl's panties, you better stay seated while we go and talk about what to do with you."

Searching their faces, he knew the threat was real. Nodding his head in acceptance, he remained seated as the girls went into the next room to discuss his fate. They weren't gone but 10 minutes, but to David, fearful of what they might decide, it seemed like hours. When they returned, the girls sat around him and then made their demands.

Kathy spoke first, "David, we really like you and we'd like you to stay a member of our little group. We trust you! You've really been a big help to all of us! If you want to dress as a girl, we don't care. It's OK with us...but you'll have to do it our way. Afterall, what would people think if it got out what we were doing? Our reputations would surely be ruined! You must agree to everything we demand of you and always without protest. If you do what we ask, we promise never to speak of this outside of the group. Since you like to dress like a girl...we'll dress you like one of us. We think it'll be a lot of fun! Some of the things you'll have to learn won't come easily and may even be embarrassing. But that's the price you'll have to pay if you want to be one of us. We can't be discovered playing with a boy dressed up as a girl. No matter what excuse, nobody would accept it!"

Now Tammi spoke, "We're going to change your name to Darla. That's short for darling and that's what we want you to become...OUR DARLING! Whenever we get together we'll transform you into Darla. If you "pass", and we think you'll make a very pretty girl, we'll reward your hard work by inviting you to a "slumber party". You'll get to sleep between us in the same bed. At the slumber party, we'll play girl games, like teasing each other's hair, applying new make-up, tickling and other things we'll tell you about later. If you’re nice to us, we may even take you clothes shopping! I'll bet you'd like that. Just imagine yourself in the women's department trying on new skirts, blouses and dresses with us there to help you. Think how much fun it'll be to "fool" the shoppers and saleswoman."

Karen interrupted, "Since you'll be one of us, we'll show you what we look like...naked. That way you'll know what a "real" girl looks like. Of course, we expect to see you naked also. I'm going to take Polaroid pictures of you dressed as Darla. We'll be in the pictures with you. That way we'll all be protected. We think it'll be lots of fun. Well, those are our terms, do you agree?"

As the reader can imagine, David couldn't have been more delighted. The girls were providing most of the features of which his fantasies were comprised. He would be seeing his girlfriends naked. He would be assisted in crossdressing, taught to "pass", attend slumber parties and enjoy all the girl things he so wished to be a part of his life. He would go shopping and really "be one of the girls". Without even a moments hesitation, he quickly agreed to their terms.

The girls were just as pleased and squealed in glee. None of them had ever seen a naked male body and looked forward to seeing David's. Also, they had not fully outgrown their childhood game of playing with dolls, dressing them in different outfits, etc. David would become their life-size doll and plaything.

It was quickly decided that Joyce and Susan, who lived nearby, would run home and bring back additional clothing for David to try on. Susan, since no one was home at her household, also wisely thought to borrow some "sexier" clothes that belonged to her mother. These included a garterbelt, nylons and a pair of high heels. If questioned later, she planned to explain the girls were playing "adult dress-up". Since they had done this before, she knew her mother would be pacified. After they returned, the fun really began.

When he removed his pink panties, you could have shot off a canon and nobody would have noticed. Letting his legs fall open he exposed his cock and balls. If he finally hadn't stepped away, they would have spent hours playing with his maleness. Afterall he defended...the real purpose of the afternoon was to transform him into their Darla doll.

Even though David had reached puberty, he was still quite hairless and what he did have was light in color, so there was no need to shave his legs or chest. As they laid out the different feminine outfits, David began to search the pile of lingerie Susan had brought back. Selecting the black lace garterbelt, he fastened the hook and twisted it into position. Susan noticed and got the attention of the others. Without comment, they all took seats and watched...fascinated by his actions. Meanwhile David picked a pair of taupe colored nylons, inserted his toe into one and rolled it up his outstretched leg. Fastening the garters to the welt, he stroked the hose into place. When he had completed the process with the other nylon, he stood. Then deciding he needed a bra, he said with an impish grin.

"Kathy, why don't you hand me your bra, I can't get dressed without one."

This suggestion was met with gales of laughter and pressure from the other girls to comply. Kathy, who had the largest tits, the reason David had selected her, was reluctant unless the other girls also removed their bras. When Susan, the least bashful, moved to unhook the front of hers, the others followed suit. One by one, they, shyly at first and then more sensually, exposed their firm youthful breasts. Each girl’s breasts were of different size and shape, but all were beautiful.

David was in all his glory! Before his stunned eyes were five sets of young breasts, ranging from Joyce's budding "nubbins" through Kathy's 36/C cups. Susan reached up her hands and cupped hers. Teasing him by bouncing her hands, she questioned provocatively.

"Darla Sweetie, wouldn't you like to own a pair like these?"

David smiled his agreement and commented, "They're all soooo very beautiful, I would be truly satisfied if I had breasts as sexy looking as any of you."

If the girls had any remaining reservations about their actions, his comment eliminated their doubts and further endeared Darla to them.

Taking the still warm bra from Kathy's outstretched hand...he proceeded to put it on. Then using his and Karen's socks, he filled it. Picking up a long blond wig, which Karen had laid in front of him, he placed it atop his head. As he stroked the tresses into place he looked around until he saw them. They were partially hidden under a beautiful, white silk nighty. Reaching under the nighty, he extracted a pair of black leather 3" high heels. Inserting his toes, he casually slipped the shoes onto his nylon-encased feet and "pranced" across the room. Extremely proud of his ability to walk in heels he "minced" his way to where the girls sat. Back and forth he swished, from one end of the room to the other. Throwing a look back over his shoulder, he enjoyed the stunned look on their faces. He had the feminine mannerisms and walk down perfectly. When one of the girls commented.

"His legs look better in nylons and heels than mine!"...he threw her a kiss.

Turning his back to them, he bent forward at the waist. Running his fingers from his ankle to the welt of his nylon, he again adjusted the hose. Tammi began to clap, followed quickly by the others. All five girls had seen their mothers perform the same motion to straighten their hose. Again turning and covering his pantied crotch with both hands, in the classic "September Morn" pose, he asked in his feminine voice.

"Isn't anyone going to give the new girl a hug and kiss to welcome her into the group?"

For the rest of his life, David would consider this his "Coming-out Day"!

During the next five months all six "girls" had a wonderful time learning about the opposite gender. They played "Show Me Yours and We'll Show You Ours".

The girls were correct...he was able to easily "pass" as Darla. After a couple of "test" situations (short trips around the block), David gained sufficient confidence to join the girl's at a local Teen-Club dance. He had absolutely no problem convincing everyone he was a visiting cousin of Karen's. Darla tried to refuse all the boys who asked her to dance, but after so many requests and pressure from the girls, he finally accepted. He soon realized it was easier to follow then to lead. A couple of the boys tried to hold Darla too tight and/or "cop a feel" of his panty clad ass as they danced Darla around the room. Gently, but firmly, she corrected the way she was being held and warned her partner, "If you try that again, I'll slap you!" After a few similar warnings, the word got around and Darla was only asked to dance by the polite ones.

Going to the ladies room was also quite an experience. Tammi and Susan went with him. After relieving themselves, they loitered a bit, listening to the conversations around them. David was surprised how openly the girls exposed their partially clad bodies and also how intimately they helped their girlfriends adjust their clothing. Some of the conversations he overheard were absolutely shocking! He had never imagined young girls were as sexually open or "hungry" as these endorsed.

After the dance, the six compared notes. Teasing Darla about the numerous requests they received for information about her and the times she was asked for her phone number. Darla admitted she was thrilled by the attention and found it nicer being asked to dance without the fear of rejection.

Kathy asked, "Did the boys turn you on?"

"No", she responded. "I felt no physical attraction towards them. It certainly was a pleasant experience dancing with them, but mostly because of the satisfaction I derived from convincing them I was female and pretty."

Kathy wouldn't let up.

"How about the kiss I saw you get from Jimmy, Joyce's brother?" She giggled, "It sure looked like you were enjoying yourself!"

Darla blushed a bright red, "He surprised me! Before I knew what he was doing, Jimmy had me in a 'bear hug' and planted his lips against mine. I was afraid to make a scene, so I let him kiss me. It wasn't unpleasant, but it didn't excite me. Thank God, he didn't try to 'French' me, I don't know how I would have reacted to that! I think it was just the realization of fooling him that was so nice. Besides if you all hadn't done such a good job with my transformation, he wouldn't have wanted to kiss me! For that, I guess, I should thank all of you!"

"Gee, I sure wish I could tell that smart-ass brother of mine how you fooled him and how he was kissing a guy in girl's clothing. I could 'black-mail' him into doing anything I wanted!" Joyce giggled. "I won't, but it sure would be great to hold over him."

After Darla's success at the dance, she was invited to more than one slumber party, meeting the parents without anyone being the wiser. It was at these parties she learned to apply her own make-up and style the wig they had chipped in and bought her. Any day off from school, but which their parent's worked, became a "special" holiday. They would meet, assist their Darla in getting dressed and take a bus to a mall on the other side of town. There the six girls would spend the day as any other group of teenage girls would...shopping for clothes and cosmetics. The only drawback was the need to "dress-up" in skirts and such in order to make Darla's "passing" easier. They taught Darla the nuances of shopping, how to tease an attractive shoe salesman and how to reject "come-ons" from teenage boys "stalking" the mall. After each new experience they would return and compare notes on Darla's level of performance. Suggestions were offered and practiced, so that by summer, Darla had mastered her role-playing to everyone's total satisfaction.

While David's transformation was happening, Mary was again becoming concerned about David. She didn't understand the lack of attention he paid her. He very seldom tried to look up her skirt or down her blouse anymore. David, of course, was getting to see "the real thing" and no longer felt the need to spy on her. But Mary didn't know this. She was naturally concerned. He still didn't date. He would disappear for hours and offer no explanations as to where he went. He supposedly slept overnight at his buddies’ houses, but she had never met any of them. He had also developed some strange mannerism. Mannerisms, Mary viewed as feminine or maybe "gay" in nature. He walked differently, he speech was more dramatic, and he was gentler, better behaved and more soft-spoken. Her continued attempts to tease him were only partially successful. In the hidden reaches of her mind a question began to grow, "Was David becoming gay? I think it's time for me to find out!"

What Mary wasn't ready to admit was...she missed the sensual excitement whenever David "peeked" at her. She had spent many a night remembering the scene in her bedroom the afternoon he hid under her bed. Driven by her concerns, Mary decided she must know why her stepson was no longer interested in peeking at her. She remembered her thoughts, in the car, after he had spied on her. "Turnabout is fair play." A plan began to form. She would tell him he was going to be home alone Friday night. She was going to visit her brother Phil in Detroit and return late Saturday night. In reality, she would sneak back into the house and hide herself. Knowing his stepmother was gone, she felt David would relax and expose what he was doing on the sly. Her only concern was David might invite his "gay" friend(s) over. She was that sure he was turning from girls in favor of boys. Putting her plan in motion, she informed David of her proposed trip at breakfast Friday morning.

David was ecstatic. His first thought was to invite the girls over for a slumber party. They could have the house to themselves. As his stepmother went upstairs to pack, he went for the phone. Calling Kathy, he was informed that she had a date and couldn't make it. Call after call was made, all with the same negative results. Each girl had to do something either with dates or family and wouldn't be available. David, somewhat despondently, said to each of his young friends that he understood. To himself, he mused. "Well, I guess I'll just have to have my fun alone tonight. I'll still have a good time! I've wanted to try mom's new black dress, anyway. It will be Darla's house tonight!"

Mary moved her time of departure up as she observed David's excitement grow with each passing minute. She loaded her car and drove away about 3:00 PM. She had skipped lunch, deciding to grab a bite before she returned giving David the time to become relaxed with his stepmother's absence. She didn't think she'd have to remain hidden too long, but was prepared to spend the night hidden in the closet...if necessary. At the restaurant, after her meal, she called home. When no one answered, she smiled at how well her plan was working.

"David must have taken my suggestion and gone to Wendy's."

Parking the car around the block, she hurriedly "snuck" back inside and hid herself in the hallway closet. Mary had checked it out already. If David didn't bother closing his bedroom door, she could observe everything he did through the adjustable slats in the closet door. What she didn't take in to account, was that David would use her bedroom. Therefore she wouldn't have the unobstructed view she expected. She didn't have long to wait.

Mary heard David enter the house, close and then lock the door behind him. Surprised, she watched as he went around the house, tightly closing all the curtains and shades. When he finished, he went to her room. This again surprised her. From her oblique angle, she could see only the area at the foot of her bed. Disappointed, she nonetheless waited until she was sure that's where he would remain. Then taking a chance, she silently positioned herself in the hall at the doorway to her bedroom.

Sneaking a peek inside, she saw David standing naked before her dresser. She watched in utter amazement as her stepson began selecting and then putting on the different pieces of feminine clothing taken from her drawers. Nylons, a garterbelt, a matching bra and a pair of panties soon covered his nakedness. Mary was no longer interested in her stepson's nudity, this was more interesting. Double shoulderpads were inserted in the cups of the bra and filled them out nicely. This brought a smile to her face.

"Obviously, he done this before!" she silently giggled.

Meanwhile David had moved to his stepmother's dressing table. There he proceeded to work magic with her make-up and a longhaired wig he produced from a bag he had carried in with him. Earrings, jewelry, perfume, false eyelashes and false nails soon followed.

Mary watched in stunned silence, as David rose, walked to her closet, selected her new black crepe and chiffon dinner dress and stepped into it. Her best black leather 3" high heels soon followed. Expecting him to have trouble with the heels, she was again pleasantly amazed at the ease and grace he showed as he walked across the bedroom to the full-length mirror next to her dresser. By now, David had transformed himself into a perfectly lovely young woman. If Mary hadn't seen the change herself, she wouldn't have had a clue as to David's true gender.

Mary decided to wait a little longer before she stepped out to challenge him. She hadn't reached a decision as to how to handle the situation. She hoped he would say something to help her better understand his actions. She was somewhat confused, but also thoroughly amused. Her stepson was a crossdresser and a good one at that! She had heard of them, but had never quite understood the whys or the reasons. Was he gay? Did he crossdress to entice boys or men? Or was there some other reason? The next few sentences helped dispel the gay concern. An even bigger surprise came when he began to speak. The voice was perfect, just like the rest of him.

"I wish Mary could see me now!" he said. "Maybe if she saw me this way she'd realize how much I want to be her daughter...instead of her stepson! Wouldn't it be wonderful if she accepted me! I could dress this way every day! We could share all the wonderful things a mother and daughter do together. She could help me much more than the girls. It's fun to be Darla for them, but it would be so much better if Mary could accept me as her daughter. Besides, I know the girls are losing interest in my gender transformation. They're more interested in boys and going out on dates, while I'm only interested in being Mary's daughter."

That was all Mary had to hear. Her stepson wasn't gay! She was however, shocked to hear him admit his girlfriends knew about his gender switching and that they had helped him with it. She realized he must have received help from someone. He couldn't have become so adept at "passing" if some female(s) hadn't taught him not only how to dress, but also the nuances of being feminine. The important thing, as far as she was concerned...he desired women...he wasn't gay. The relief she felt almost caused her to sigh aloud, thereby exposing her presence. Her mind raced. David wanted to be her daughter! It was more than just the desire to wear women's clothing. There was no question he was more than adequate at crossdressing. The more she stared, the easier it became to believe there was a young woman standing in her bedroom and wearing her clothes. A beautiful one at that!

Mary had always wanted a daughter...this just might be the chance. Besides if it didn't work, they could move away and start all over again, nobody the wiser. If that's what her stepson truly wanted, she decided, it was her responsibility to help him in any way that she could. Her course of action decided upon, she stepped into the room and said.

"Darla, you look wonderful in my new dress! In fact, I think you should keep it. It looks nicer on you than on me. I'm so glad I have a lovely young daughter who can wear such attractive clothes. You remind me of myself at your age. I think you could use a little help with your make-up, but I'll be more than willing to show you! Why don't we go downstairs, fix ourselves something to drink and talk about your desire to become my daughter. There's so much we need to discuss. If you’re going to become my full-time daughter, then we will need to change our entire lifestyle. Before we do, however, I'd like a hug and kiss from my pretty girl!"

David had heard the sound of his stepmother entering the room even before she spoke. Whipping around in fear, the chiffon skirt "twirling" out from his nyloned knees, he was preparing to offer an explanation, even though he knew it was fruitless. When he realized what his stepmother was saying, he couldn't believe his fortune. She was accepting him as Darla! This was really happening just as he had dreamed it might. Rushing to her open arms, he threw himself into them, hugging her tightly. Cheek to cheek, they whispered words of love, understanding and gratitude. As David became more and more convinced of Mary's acceptance, he began to cry. Tears of joy ran down his face. When he was finally able to speak, he stated?

"You’re the best mother a girl could have!"

Then realizing what he had just said, he began to giggle.

"Oh mom, you don't know how much this means to me! I don't really like being a boy. I remember even when I was younger thinking how wonderful it would have been to be born a female so I could grow up to look just like you! Maybe that's why it took so long for me to start puberty. Maybe I wasn't supposed to be a boy. I don't really know! What I do know is the only time I feel good about myself is when I'm Darla."

Darla's new mom spoke, "Honey, you might be right. Maybe you should have been born a girl. With my help, maybe we can fix that. We'll look into getting your identity legally changed when you get older. From what I understand, it's not that uncommon or that difficult. We'll worry about that later. Right now, I want to hear the whole story. I want you to explain how you know so much about wearing women's clothes and don't you dare leave anything out. I want the whole story, everything about your crossdressing. How you got started, grew into your femininity and all about these girlfriends who helped you."

David explained in detail. He revealed how he started with his crossdressing, how he had progressed and how the girls had discovered him one day wearing pink lace panties. This brought gales of laughter from Mary and also David.

"I can just imagine that sight. You're face must've been at least the color of your panties. What happened next?" she asked.

David continued his story, explaining what the girls had offered him, how he had accepted and how they had helped him grow into the role. Then, when he had become proficient at passing, they had taken him to a Teen Club dance. Deciding to admit everything, he told her about "The Kiss", his being asked to dance and how much he had enjoyed the attention. David revealed how he had flirted with the boys and the numerous requests for his phone number.

Mary interrupted, asking the obvious questions, received the answers she hoped, and then Darla continued. She explained how the girls took their Darla on shopping trips to the mall and the fun they had fooling the various saleswomen as they tried on dresses, skirts, slips, blouses and shoes. Once, Darla explained, she accepted assistance from a woman who David knew was Mary's favorite salesgirl. The woman never suspected a thing. Mary giggled as she imagined the scene.

David continued. Pajama parties, he explained, were the most fun. The girls would introduce Darla to their parents and "she" fooled them every time. None of the parents ever caught on. He got to wear their nighties, had his hair put up in rollers and wrestled around the beds together, all with the permission of the parents. Then when they finally went to sleep, the girls would fight to see who would lie next to him. Semi-nude teen-age girls, who would "snake" their hands inside his silken panties and play with his penis, surrounded him! Of course, he would use his hands inside their panties at the same time. In explaining the rest of his story, he skipped around a bit, revealing incidents about the other games the girls played and the fondling they performed between themselves as he watched.

Then David went into his desires. He told Mary how he had come to believe he had been born in the wrong gender. He wanted to grow up a woman. He knew that's what he should be! He said he realized this the day he saw her naked. When he started to explain his hiding under her bed and how excited he had become, Mary let him finish. Then she admitted she had known he was under the bed. She also admitted her teasing games. David was stunned!

He asked, "Mom, why did you let me peek at you?"

"Honey, all those years, without a man around, made me feel less than desirable. When you started to sneak peeks up my skirt and down my blouse it made me feel attractive. I liked feeling that way and decided as long as it was only the two of us...what could it hurt? All women tease. Don't you think we know when a man is staring up our skirts? We certainly wouldn't wear the clothes we do if we didn't want men to stare at us. Real women enjoy the power we get when we casually expose our bodies. Think about it. We women can't bend over without our breasts being partially seen and how about our short skirts. Think about how tight we wear our clothes...so every curve is outlined for men to fantasize over. Everytime we sit, we "show" at least our thighs and usually more than that. Do you think we cross our legs just to cover up? No, we do it to give men another chance to see! In this male dominated society it's one of the ways women have of controlling men. Now some women are too shy to admit it, but we do it to attract the attention of the men and get them to do what we want. When I saw the bulges in your pants I decided to have some fun with you, not to have power over you, just to see how you were maturing."

Now that they had been honest with each other, their relationship had changed. It wasn't as much stepmother to stepson, but one of equals. Mary suggested they refresh their drinks, return to the couch and continue their talk about David's desire to become Mary's daughter. They spent the next two hours covering the topic.

Mary admitted how much she had always wanted a daughter. While she had always loved her stepson, she explained, she had felt "cheated" that she would never have a daughter to share and teach the joys of being feminine. Darla would be the answer to her prayers. "Oh, how I look forward to these changes!" she announced a number of times as they talked.

Numerous issues were left to be decided at a later date. The things they needed to resolve immediately...they did. They decided that David would have to tell the girls his stepmother had discovered his crossdressing, forced him to explain, forced him to expose their involvement and forced him to break off his relationship with them. He was told to explain to the girls that his stepmother had also found the pictures. If the girls didn't want Mary to call their parents, they were to forget it ever happened. David was certain they would accept the terms and while he hated to threaten them (and lie to them), he understood the need.

Since Mary was not tied to a job, she decided she would sell their house and would move to another city. There, David would become Darla, Mary's daughter, on a full-time basis. They'd investigate legally changing the gender statement on his birth certificate and possibly a partial sex change operation (breast implants), after they moved and he became of legal age. Mary planned to take Darla, to her own gynecologist as soon as possible. The doctor had been her friend since high school and Mary was sure she would help. She hoped her friend would prescribe female hormones. These she explained would help David's skin grow softer and minimize facial and chest hair. They might even make his hips wider and his breasts larger and more sensitive. Since he had been so late in reaching puberty, he might still be able to change his frame. If nothing else the doctor could give them direction. Plans were discussed for them to drive over to Indianapolis that weekend and go clothes shopping. They could act as any other mother and daughter and nobody would be the wiser.

Mary also informed David that her regular hairdresser had once told her a story where she had done a female impersonator's hair. Mary felt the woman would do David's hair in a feminine style if the price were right. The woman offered cosmetic assistance training and so they planned to avail themselves of her skills. Mary suggested a trip to the local medical supply store to purchase prosthetic breast sacks. These would give Darla the realistic look, feel and weight of a woman's breasts. They would also "move" more naturally under Darla's clothing. Various other topics were discussed, decided upon or cataloged for future discussion.

Finally, both mother and newfound daughter began to show signs of exhaustion and decided to call it a day. After both had removed their make-up, Mary ran a tub, not for herself, but for Darla. As the water began to flow she added bath oil beads.

David was aglow as he stepped into the deliciously warm, scented water of his first "female" bath. While in the tub, Mary had him shave the "peach-fuzz" from his legs and also his underarms. When the water began to lose its warmth she handed him a towel and instructed him in the manner of patting himself dry.

Mary presented her new daughter a white satin nighty with spaghetti straps to sleep in. Then kissing Darla goodnight she said. "This has been quite an exciting day for the both of us. Beginning tomorrow we'll be able to share all the wonderful feelings of being female and being mother and daughter. Now get some rest, there's always tomorrow!"

Mary and Scarlet O'Hara were both right...there was always tomorrow, but that's another story.

 

The End

 

© 1995
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