School Days

Petti Pulp Fiction

ON PETTICOAT POND

BE BE AWARE THAT IF YOU ARE UNDER NINETEEN YEARS OF AGE OR OFFENDED BY SEXUAL DEPICTIONS, DO NOT STAY. ALL SUCH STORIES ARE DEPICTED BY A BLUE PETTICOAT. THIS IS A BLUE-PETTI AREA. Return to Petticoat Pond's Main Page

Author unknown: If you would like to take credit for this work, please contact us--credit is given where credit is due. No copyright notice was posted.

Edited by Paige S.


SCHOOL DAYS

Author possibly a "Daisy", according to a reader. If you would like to take credit for this work, please contact us--credit is given where credit is due.
No copyright notice was posted. Re-printed as found.


Reilly woke up early that morning and quickly showered and dressed in his school uniform. He was a freshman at St. Mark's Academy for Boys, and, although his studies were progressing nicely, he was still homesick. It was November, and he had been away from home for over two months. He had always been an excellent student in grammar school and, from his earliest years, had been something of a teacher's pet to the nuns at St. Stephen's.  Boarding school was a new experience, however; he missed his mom and sisters and, although he never would have dreamed it before, even the nuns. St. Mark's was a small school run by an order of cloistered priests. There were no females at the academy at all; the teachers as well as the support staff were all members of the religious order.

This morning promised to be interesting at least. A small group of ladies from the local parish had been invited to share breakfast with some of the students and their teachers. This was to be something of a “get-acquainted” session, in that rarely had the academy grounds been open to outsiders, especially women.  As a reward for doing especially well in his classes, Christopher had been selected as one of the half dozen students invited to take part.

The breakfast was held off the main dining hall in a separate room.  The boys helped serve the breakfast, bringing each of the ladies food before taking their seats which alternated around the table, one of the ladies, one of the students, and one of the priests. Chris served Father Tom and then brought a plate of bacon, eggs, and pancakes to the woman he would be seated next to.  He guessed she was nearly forty and although on the heavy side, had a very kind and even pretty face.

She thanked him as he took his seat and introduced herself as Mary. Her perfume filled Chris's senses and after being separated for months now from any female company at all, Chris delighted in the conversation and seldom let his sight off her. He spoke of his studies and his participation in intramural sporting events, and she in turn spoke of her life in the small community just down the road from the academy gates. Mary explained that she was a widow with one daughter away at college on the West Coast. Chris listened attentively and impressed Mary as a perfect little gentleman.

The breakfast over, the boys cleared the dishes and the Fathers expressed their gratitude to the ladies for attending. A suggestion was made to continue this interaction, perhaps by permitting the students to visit off-campus periodically.

Chris returned from the kitchen and moved to take his seat, but Mary motioned him to her lap where, although a little embarrassed, he felt very comfortable. With her arm around the young freshman, she cradled him affectionately against her massive bosom and ran her fingers thru his curly hair. She told Father Tom how Chris was such a cute little child welcome to visit her home at any time, and as the priest agreed to allow the boys off grounds and thanked her for the kind offer, Chris was lost in a flood of senses. He let his head rest against her wondrous breast and let the smell of her heavenly fragrance fill him.

The Thanksgiving holidays were now upon them and this presented something of a problem. While most all the other students were from the region, Chris' family lived almost 1000 miles distant. Although this was unusual, Chris' father was a member of the alumni and hence the selection of St. Mark's for the boy's education.  While his family wasn't poor, flying home for Thanksgiving and then again in a few weeks for Christmas was more than they could afford. It was assumed Chris could remain on campus, and while that was possible, it would cause the staff inconvenience in that repairs to the dormitory had been planned while the students were away. A solution was quickly found.

The subject came up on Sunday as Mary was chatting with Father Tom after Mass at the local parish where he assisted.  Mary offered to open her home to the boy for the long weekend and the priest agreed subsequent to approval from Chris and his parents. Of course, after a week of dreams filled with visions of the older woman's breasts and the heady aroma of her perfume still in his mind, Chris' answer was guaranteed. His mom and dad also thought it an excellent idea after a recommendation from Father Tom.

Wednesday, after the other boys had already been picked up by their parents or taken to the bus depot, Chris anxiously awaited his ride. His small suitcase was packed and ready to go. Just as he realized he was the last still waiting, Mary pulled up in the driveway. He sat his suitcase behind the car near the trunk as Mary came around the car and motioned him to her. She lovingly wrapped him in her arms and gave him a kiss on the forehead, explaining how pleased she was to have him for the holiday. As she enveloped him in a warm hug and drew his head against her bosom, Chris once again seemed lost in her warmth.  She opened the passenger door and the boy, almost in a trance, took his seat beside her and off they drove. (Did you notice that? Where's the suitcase?)

As they pulled in the circular drive to Mary's house, Chris looked out in awe. Obviously Mary was wealthy, the house appeared almost a mansion and the grounds leading up to it were nearly as large as the entire campus. To his surprise, they were greeted as they pulled up by a tall young woman dressed in a maid's uniform. Mary introduced the woman as Carolyn, her personal assistant and maid. The boy, his eyes glued to the woman in her short black satin dress and dark stockings and heels, blushed as Carolyn curtseyed and, taking the lad by the hand, led him into the house.

Dinner was about to be served, and after being shown the powder room where he could wash up, Carolyn ushered the boy into the formal dining room and seated him next to Mary at the large table. The table seemed almost too empty, but then Chris remembered that Mary had been recently widowed, and Mary explained that, like him, her daughter Susan had decided to stay on the West Coast with friends for the holiday.

Everything about the house was beautiful; it was huge and decorated with ornate lace curtains and fresh flowers on every table. Never had he been in such a wondrous place. As the two of them chatted, Carolyn served the meal. At such an impressionable age, his body and thoughts affected by the rush of hormonal change, Chris couldn't help but steal glances at the maid as she scurried about, her brief uniform showing off frothy white petticoats as she bent to place the various dishes on the table. Mary smiled knowingly at Carolyn as she took note of the boy's distraction.

“You've had a long day, hon. Why don't you draw a bath for our little guest, Carolyn, and he can get what I'm sure is some needed sleep. You'll be sleeping in Susan's room, Chrissy”

Mary went on to explain.

The boy noticed the affectionate manner in which she had addressed him, and while blushing slightly, liked the sound of it.

“Thank you, Ma'am. You've been so kind to me.”

With that, Mary excused herself and Carolyn led the youngster up a long curving stairway to make an early night of it.  Following the young woman a step of two behind, Chris couldn't help but notice how her long shapely legs disappeared beneath the froth of petticoats. From this new vantage point, Carolyn also displayed the frilled garter tabs that held her stockings taut. Glancing over her shoulder, she smiled as she noticed the boy's stare and gave her hips a more pronounced wiggle to tease him further. She led the boy into his room for the weekend, and while he was too polite to say anything, he couldn't help but feel strange.

Susan's room was far different from any he had been in before. It was definitely a girl's room; the walls papered in a delicate pink floral pattern and the bed which dominated the whole room looking as if it belonged to a princess. It was covered in a canopy hung with wispy lace as were the curtains and the vanity.  “I'm sure you'll be  comfortable here, ”Carolyn said with a gleam in her eye as she entered the bath just off the room and began filling the tub.

Chris stole a peek into the bath and saw that it too was definitely that of a young lady: everything in pink, from the towels down to the thick carpeting. Chris waited sheepishly, anxious for the woman to leave him in privacy.

Carolyn re-entered the room and noticing the boy being ill-at-ease brought him relief. “I'll leave you to your bath, sweetie; you'll find everything you need in the bath. I'll be back later with your  things.”

With that she left the room and Chris quickly removed his clothes, and, leaving them folded on the bed, hurried into the bath. For as long as he could remember, he had only taken showers, and this bath was not just a bath. The large tub was near overflowing with a froth of fragrant bubbles. Being alone, there was no need to feel embarrassed, so he slowly slid into the warm luxuriant suds. Just as the boy settled into total relaxation, he was startled by the door opening and Mary entering, Carolyn at her heels.

“I'm afraid we have a slight problem, dear,” spoke Mary.  Somehow your suitcase didn't make it into the car when we left the academy. I've called the school, but there's no answer"

”Oh, that's right, I don't remember putting it in the trunk; it must be still there in the driveway, said Chris as he tried to slide deeper beneath the bubbles.  I guess I will just have to wear what I came in; it's no problem.

"I'm afraid I already sent your clothes to the laundry," Carolyn volunteered.

“I'm sure we can find something for you to wear, dear. Here, Carolyn will shampoo your hair and I'll look for something. You needn't worry your little head.”

The boy, although embarrassed by the presence of the two ladies in the bath, being in such unfamiliar surroundings, didn't dare refuse the kindness of his host.  Covering himself beneath the suds, he sat quietly while Carolyn soaped his back and scrubbed him with a soft brush. He hadn't been “given” a bath since early childhood. Despite his confused state, Carolyn's efforts were pleasurable. As she knelt at the side of the tub and began lathering his scalp, Chris' eyes were drawn again and again to the bodice of her uniform. Carolyn was obviously well endowed in that department, and peeking through the sudsy lather, Chris watched intently as her cleavage shook so closely to his face. Taking the handsprayer, she rinsed the soap from his hair, running her beautifully manicured fingers thru his curls. Retrieving a fluffy pink towel from the cabinet, she held it out and motioned Chris out of the tub.

“Don't be embarrassed, dear,” she said with a grin. I do have brothers, you know.”

The boy quickly grabbed the towel and wrapped it tightly around himself as he stepped from the tub.  Carolyn had already taken another and began to vigorously dry his hair. She then wrapped the towel about his head and, giving it a twist, left it bound as he had seen his mother do so many times before with her hair after shampooing. She surprised him further,  however, when while he looked away, she had begun to douse his hairless upper body with body powder. His face turned bright red as this was certainly not for men. She had used a feathery puff and the powder had a decidedly feminine fragrance.

She giggled.  “There. You'll smell so sweet for bed now,”; she said as she turned and left the room.  “Let's see if the mistress has found you something nice to wear.”

At last he was alone again. Just as he finished drying himself, he  heard the two women return to the room.

“It seems you'll have to borrow something from Susan's wardrobe, Chrissy,”  Mary said from the bedroom.  “I know these are hardly suitable for a nice young boy, but they'll have to do under the circumstances.”

Carolyn entered the bath, and what she carried in her hands caused the boy's jaw to drop. Carolyn offered the frilly pink nightie and matching panties to the stunned adolescent. The little babydoll had a lacy bodice and silken spaghetti straps.  The panties were equally brief and, like the top, were trimmed in lace.

“Oh God! I can't wear that! said Chris loudly.

Hearing that, Mary joined them in the bath and put her arm around the boy. “Oh, don't be silly!  It's only till tomorrow and we'll get your things from the school.”

“But I'll look so funny in a girl's nightgown,” whimpered Chris.

"Now, now, you put them on and I'll find you a robe to wear. That'll be better then, won't it?” asked his host.

“Well, I guess so,” replied Chris, his face still beet red. Mary and  Carolyn left the room and closed the door behind them.  Chris lifted the dainty little panties and resigned himself to a night in girl's frillies. He stepped into them carefully and pulled them up his legs. To his surprise, they felt wonderful, so soft and silky.  Then raising his arms, he slipped the short nightie over his head and let it float down over his slim body. It too felt delicious, but that that was something that would forever remain his secret.  He turned to look in the full length mirror on the back of the door. The sight that met him gave him a shudder. Standing there on the fluffy carpet, he could have been mistaken for a girl, his hair bundled up beneath a thick pink towel and his body sheathed in such a sexy little babydoll of the same hue. His body gave away what his mind was thinking. As he gazed at the reflection in the mirror, his penis began to grow and thicken.  How could he think this way, he thought. I'm a boy! Just then the door opened and Carolyn inched thru. Chris just about jumped out of his skin with embarrassment. He turned away to hide the source of his shame as Carolyn let out a giggle. 

"You look darling,” she said, grinning inside as she caught a peek of the boy in the vanity mirror, his attempt to hide his erection failing. “Here, let's put this on,” she said as she held a diaphanous pink robe out for the boy to slip into. This was almost as bad, but it was, at least, somewhat longer and offered a degree of modesty. It too, was trimmed in lace at the shoulders, hem, and sleeves. With that, she took the boy's hand and led him back into the bedroom.

Mary was there waiting, a glass of warm milk in her hand.  “You look so precious,” she said as she handed the glass to the boy and kissed him on the cheek.  “Drink this now; you'll sleep better, dear.  Carolyn will stay and dry your hair for you and tuck you in; I'll be up later to kiss you good-night, Turning away, she winked at the pretty maid and left the room, closing the door behind her.

“Sit up on the bed here, Chrissy,” said Carolyn. Finish your nice warm milk and I'll take care of your hair.”

Despite his embarrassment, the boy felt a delicious warmth sweep over him. He had never been pampered as he had since his arrival. He sat on the bed, his frilly robe spread out around him, as Carolyn removed the damp towel and began to brush his curly blond hair. Whether it was the result of such a long and exciting day, or warmth of his milk, his whole body seemed to relax. As the beautiful servant girl drew her soft hands over his scalp again and again, he seemed to float away into another world.”

“Isn't this nice?” asked Carolyn, as the boy could only nod.  “You're as pretty as a little girl in your nightie. You smell so sweet and lovely, dear.”

Chris felt lovely, too. He had never felt anything like this. He couldn't explain it. One part of him wanted to scream and run, but another part of him, held captive by the light caress of the silky lingerie, the gentle attentions of the maid, and the warmth of his bedtime drink refused to leave.

"So soft, so pretty,” he could hear Carolyn whisper in his ear.  He could feel her fingers gently trace along his neck and down the bodice of the nightgown.  “My beautiful little Christine,” she whispered as he laid back against her bosom, his mind lost in a trance.

 “He felt her red-tipped finger draw across his lips and his body seemed to shiver to her touch. He hardly took note as she lay him back on the silken sheets, running one hand thru his hair and the other down and under his frilly babydoll.  She pulled the lacy little panties down a bit and freed his penis, now hard and throbbing. He shuddered in delight as she took a frilly hankie from her bodice and wrapping it around his shaft, began milking him. His senses were  overloaded; the touch of the silky nightgown on his body, the  fragrance of the room, the sight of Carolyn bending as she ministered to him, and the feather-like stroking of his genitals controlling his mind. Finally, as she caressed his lips with her own and he tasted the creamy red gloss that covered them, his whole body shuddered in spasm. His boyish juice exploded into the silken handkerchief.

Carolyn smiled down at their guest and gently cleaned him.  He had never in his life felt so wondrous. Lifting his back from the cool sheets, she removed his robe, and now, dressed only in his babydoll with their matching panties, she pulled the coverlet over him. Kissing him on the forehead, she whispered, “Good-night, Chrissy; sleep tight.”  She turned off the light and closed the door behind her, leaving the boy asleep and dreaming.

The boy's sleep was filled with dreams that would have disturbed him had they remained in his memory more than a fleeting moment.  In his dream, Christopher had found himself back at St. Mark's Academy for Boys in the room he shared with two other students. What surprised him, however, was that while the other two wore their pajamas as they climbed into bed, Christopher found himself dressed in a blue satin gown. The dream was hardly surprising for that night, visiting the home of Mary, a local woman who had befriended him, he had, indeed, gone to bed dressed in a frilly nightie borrowed from her daughter's wardrobe.

 *****

He awoke from his slumber suddenly, light streaming into the girlishly decorated bedroom as Carolyn, the beautiful housekeeper, flung the curtains wide.

“Wake up, sleepyhead,” whispered the maid in his ear.  “Breakfast will be ready in just a few minutes.”

 As the cobwebs cleared from his brain, the activities of the previous  evening flooded back into his consciousness. As if somehow disbelieving, he quickly peeked beneath the satin sheet, blushing as his feminine attire was confirmed.

“Come on, sweetheart - we'll have to hurry,” Carolyn said as she threw back the covers.

The teenage boy, startled, tried to cover himself, but the maid just grinned and, taking his hand, pulled him from the bed. 

“Here, hon, slip on your robe and let's wash your face,” she said, holding the diaphanous, lace-trimmed bed jacket.  As the boy slipped his arms through the flowing sleeves, she smoothed it over his  shoulders, letting it settle lightly over the much shorter pink babydoll.

Leading the youngster into the bathroom, she draped a fluffy towel around his shoulders and then, lathering a soft facecloth with fragrant soap, began to wash the sleep from his eyes. After rinsing the lather from his smooth skin, Carolyn gently patted his face dry with a soft absorbent towel. Just as the night before, Christopher stood passively, unsure of his feelings but somehow almost under a spell as everything was being done for him. Unused to such pampering, he found it quite pleasurable. Taking a toothbrush and even squeezing the paste on it for him, she said, “You finish brushing now, Chrissy; I'll find your slippers.”

Newly refreshed, he sheepishly returned to the bedroom where Carolyn motioned him to the small seat facing the mirrored vanity. Seated before the mirror, his eyes were drawn to the lace trimmed bodice of his dressing gown.  As the maid stood at his back, slowly brushing his longish blonde hair with an ornate silver brush, his mind reeled.  “This is crazy,” he thought, “she's treating me just like a little girl or something.”  Despite his embarrassment, however, the more overpowering emotion was guilt, guilt that, beneath the blush, he actually delighted in her ministrations. He felt he should put a stop to all this, but the gentle stroking of the brush and the silky touch of his gown and panties on his skin seemed excuse enough to postpone any rebellion. His mind was brought back from his reverie as Carolyn knelt and slipped a pair of pink satin slippers over his feet.

The image of a princess being attended by her ladies-in-waiting rushed through Chris' brain as the maid took his hand and brought him to his feet. 

“Oh dear, we'll have to hurry; we can't leave Mistress waiting.”

Though the backless slippers had but short wedge heels, the boy took hesitant steps. “Let me help you, sweetheart.” Reaching her hand around his smoothly covered waist, Carolyn assisted the femininely gowned boy from the room and down the wide stairs to the brightly decorated dining room.

Again the input from the boy's senses seemed almost overwhelming. Here he was, being supported by a beautiful woman dressed in the briefest of costumes and smelling of the most wonderful perfume, her arm encircling his waist and pulling him close, all the while his own skin sheathed in the silkiest of fabrics; and more, not only was his attire softly arousing as it brushed his thighs, it was exquisitely feminine.

“Good Morning, Chrissy,” greeted Mary, his host as they entered the room. “Did you sleep well, darling?” she queried as Carolyn led the boy to her waiting arms. “I know a big boy like you doesn't want to hear it, but you look very pretty in Susan's nightie,” she cooed as she enveloped the boy in her arms. “I'm sorry about your lost luggage but it wasn't so bad, was it, dear?”  Blushing deeply as she gently brushed a stray hair from her young guest's forehead, he could only nod.  “It's a shame boys never have the chance to wear such pretty things and look so nice,” she continued. “It's just not the same around the house with Susan being away at school; she loved playing dress-up with all her pretty clothes.” As the boy took his seat at the table, he noticed what must certainly be loneliness and heartache in his host's eyes.

“Oh Carolyn, you'd better try calling the school again and see if they've found Chris' suitcase,” Mary called to the maid as they finished their breakfast of melon and toast.  Unsure of his emotions, Chris looked forward to finally getting back into jeans and shirt.

"I just tried again, Ma'am; there's still no answer at the school,” said Carolyn as she returned to the room.

Noting the distress in the boy's expression, Mary motioned him to her, and cradling the still nightgowned lad in her lap, she hugged him close.  “Don't worry, sweetheart; we can't have you spending the  whole week in Susan's nightie, now can we?”

Again, a sense of guilt and shame came over the boy, for that very thought seemed somehow appealing. 

“I suppose we'd better drive over to the school; perhaps your suitcase is still in the driveway where we left it,” comforted Mary.  “In any case, it's time you were out of your nightie and dressed.  Carolyn, take Chrissy upstairs,” the maid was directed. “ We'll have to find something else for him to wear in the car.”

Taking her charge in hand, Carolyn led him from the room and back up the long curved stairway.  Knowing that he would soon be out of the silky gown, Chris seemed to take special note of its whisper-like softness. As he climbed each step, he secretly delighted as the lace hem caressed his thighs and panty-covered rear. Before they were halfway up the long staircase, he couldn't help but notice another sensation. The sensuous touch of the filmy fabric had had a dramatic effect on his adolescent member as well. Growing more tumescent with each caress, seemingly out of his control, it strained against the lacy confines of his silky panties. This new “problem” did not pass the notice of the sexily clad maid. Smiling, she let her hand glide around the boy's waist and teasingly slowed their pace a bit. Her proximity made matters worse as the added sensation of her touch roused the now flush boy even further. At last reaching the bedroom, the boy, now almost quivering, broke free and rushed into the bathroom to hide his embarrassment.

“What is it, sweetheart?” responded Carolyn, hurriedly following the boy into the bath.  There she found the boy, his cheeks ablaze, covering himself with his hands as best he could.

“Darling, don't be embarrassed,” the maid said softly.  “Did your lacy little nightie do this?” she asked.

Moving his hands from their position, she let her fingertips side over the front of his gown, her nails barely brushing his now engorged penis.  Her eyes noting the tent-like bulge, she teased, “It seems our little Christine enjoys being a precious little girl, doesn't it?”

Near fainting as she reached beneath the hem of the babydoll and caressed his throbbing malehood, the boy had to grab the edge of the sink to keep from falling.

“Oh Chrissy, look what you're doing to your frilly little panties; if it wasn't for this, I'd think you were a sweet young girl.”

Moaning softly, the boy, now a captive to the maid's intoxicating caress, surrendered to the rush of pleasure. His body sheathed in delicate silk, his feet shod in pom-pomed satin slippers, and his pantied and swollen penis gently milked by Carolyn's enveloping fingers seemed ready to explode.

“You like your little panties, don't you, sweetheart?” cooed Carolyn. “You want to be a sweet little girl, don't you?”

At that, the young boy's penis shuddered and released its pent up excitement into his pink panties.  Christopher stood quivering, for the second time since his arrival, Carolyn had excited him to the point of sexual climax; this time, however, he had erupted into the silky pink panties he had been forced to wear after forgetting his own clothes back at the academy.  On the verge of collapse, the scantily dressed maid helped the embarrassed boy to the padded bench opposite the tub.

“You do look precious, Chrissy, but you really needn't blush.  It's plain you love your pretty nightgown and panties; I'd find it even more unusual if you didn't.” 

The teenager looked up into the maid's eyes quizzically. “What do you mean?” he asked.

 "It's just as Mistress said,” she went on. “Boys are so deprived, never able to dress up in pretty dresses and nighties like girls. Forgetting our suitcase has given you an chance to see just how nice wearing silky frillies can be.”

“But I'm a boy! I shouldn't feel this way,” he answered ashamedly.

“Don't be silly, honey,” she said, slowly lowering the now stained panties down his legs. “There's no reason boys shouldn't be able to feel pretty like their sisters.” Taking a soft washcloth, she carefully washed the boy.

Not since early childhood had anyone seen him so intimately, though considering the occurrences of the last day, there was little left to feel embarrassed about. Both Carolyn and her mistress had treated him with a kindness and love he'd been without since leaving for school at summer's end.

“Come along now, Chrissy; let's find something especially pretty for you to wear in the car.”

“You want me to wear a dress when we drive over to school?” he questioned, his voice almost faltering.

“Don't worry darling; before I'm finished, your own mother would swear you were her daughter rather than her son,” Carolyn joked. “And I don't want to hear any excuses; I know you're just dying to wear a cute little dress and have your hair curled.”

Though he didn't answer, Chris knew she was right. Yesterday he wouldn't have imagined it, but like so much that had transpired since his arrival, he was certain the day ahead would prove most exciting.

Just then, Mary entered the room.  “And just what are you two scheming in here?” she said with a smile.

“Why, Christine was just telling me how much she was looking forward to going for a little drive,” the maid answered, her eyes twinkling.

“Oh, I see....didn't I tell you wearing Susan's things wouldn't be so bad, sweetheart?” she asked as she hugged the boy to her.

“It'll be just like having Susan home again, won't it, Ma'am?”  volunteered Carolyn.

“Indeed it will; come along now Christine, we'll have to pick out something especially pretty,” Mary said, leading their guest back into the bedroom.

Remembering his now lack of panties, the boy clutched the lace-trimmed robe tightly around the nightgown, and sheepishly followed, the anticipation of actually leaving the mansion while dressed as a young girl building with each tick of the clock.

"Let's see now,” Mary thought aloud, throwing open the sliding mirrored doors lining the wall of the bedroom.  The boy's eyes widened as row upon row of delightfully colorful dresses, skirts, and blouses were revealed.

"What do you think, Carolyn?” Mary queried as she removed an exquisitely feminine pink dress from the rack. Their guest couldn't take his eyes off the airy creation. The dress was a beautiful pastel satin, its bodice and skirt highlighted with a wide band of white lace.  “I think our little girl will look adorable in this, don't you agree, Carolyn?”

“Oh Yes, Ma'am,” the maid replied, her beautifully manicured hand caressing the boy's cheek as he blushed deeply.

“Isn't it pretty, Christine?” she asked excitedly, winking at her  employer.  “Well?  Christine, what do you think?”

“Yes, it's very nice,” he finally answered, both women smiling at his obvious embarrassment.

“Nice?...judging from the look in your eyes, I would have thought something more than just nice,” giggled the satin and petticoat clad maid.  I'd almost forgotten; we'd better find you a new pair of panties, hadn't we sweetheart?”

Opening the top drawer of the large chest near the bed, Carolyn searched for a moment, then returned to display a darling pair of white satin panties. They were trimmed in frilly lace at both the waist and leg openings, and even more elaborately across the seat with several rows of lace running from one side to the other.

“My goodness! Those are precious, just perfect for my new niece's first day out and about,” gushed Mary.

Stooping low, he maid held the panties open, and steadying himself with a hand on her shoulder, the boy, one foot at a time, gingerly stepped into them. Trying to remain modest in the presence of the two ladies, Chris attempted to hold the hem of the babydoll nightie down as Carolyn slowly raised the wondrously smooth panties up over his knees. Smiling up at the red-faced youngster, she continued on, tugging the panties up all the way and her hands hidden beneath his gown, smoothed them over his recently drained member.

“There now...that's better, isn't it Hon?” she asked the boy. Not waiting for a reply, she stood and began removing his filmy robe.

“Let's not waste any time, Chrissy dear,” Mary said, taking the hem of the babydoll in her hands and lifting it over the boy's head.

Standing before them in only his girlish new panties and slippers, he tried again to cover himself.

“Don't be so shy, Chrissy; we'll have you all pretty again soon,” laughed his host. “I think our little girl should be properly powdered before donning her pretty dress” Mary directed the maid.

“Certainly, Ma'am,” she answered, taking a feathery puff from a wide-mouthed jar on the vanity. His eyes closed tightly, she dusted him generously with the sweet smelling body powder, coating his shoulders and ten moving down over his hairless chest and finally down over each thigh. Returning from the dresser, Carolyn held out a wispy white training bra.  Unsure of what was happening, the boy took a step back, but Mary promptly instructed him to raise his arms and quit tarrying. His arms outstretched before him, Carolyn slipped the lacy confection up over his elbows, and reaching behind, clasped the hooks which secured the silky garment. Though hardly needing any support for his non-existent breasts, he did feel somewhat more modest.  Any relief was short-lived however, as turning to Mary, he spotted what he knew to be a garter belt in her hand. In his mind at least, wearing panties and a dress was one thing, but being attired in something so totally feminine was somehow moving to an entirely different plane. Entirely at their mercy, however, he resigned himself to whatever they had in mind.

Circling his waist with the satin and lace belt, Mary motioned him to the vanity stool. Seated, he watched in apparent awe as Carolyn now approached, a pair of sheer white stockings flowing from her hand. Removing first one slipper then the other, the maid carefully gathered the sleek looking nylon and then slipped the stocking over his foot. "

“Raise your leg, sweetheart; a girl should always take care to keep her nylons straight.”  As she glided the wondrously silky stocking up Chris' leg, his breathing became more of a gasp.  It didn't help as she reached  beneath his little panties and guided the frilly garter tabs under and through before attaching each tautly to the lacy tops of the nylons.  Just as Carolyn fastened the last of the garters, Mary returned from the large walk-in closet with a pair of white patent leather low-heeled pumps. The front of each was decorated with a pink satin bow. Still kneeling, Carolyn took the shoes and slipped them on the boy's feet.

“Oh, those are darling, Christine,” she said as standing, she looked down at the pretty little shoes. “It's fortunate Christine and Susan are almost exactly the same size; our little girl will certainly have quite a wardrobe from which to choose,” beamed Mary.   Checking the length of the dress hanging from the closet door, Carolyn rummaged thru the back or the closet and shortly reappeared, a shiny petti-slip in her hand. Though somewhat short like the dress itself, the skirt was very full. Constructed of multiple layered taffeta and edged in delicate lace top and bottom, it rustled deliciously as she lowered it over the boy's up stretched arms.

Together, with the lad sandwiched between them, Carolyn and Mary adjusted the thin shoulder straps until it hung perfectly, the smooth bodice hugging his chest and the frothy skirt tickling his thighs. 

“Don't you just adore this wonderful petticoat, honey?” Mary asked, giving the skirt a shake. An almost imperceptible moan escaped from their charge's lips as the loud frou-frou and the silken touch of the lace brushing his nylon sheathed thighs seemed to envelope him in a kind of soft cloud.

Taking him by the hand, Carolyn again led the boy to the vanity where, after showing him how to sit properly in a skirt, she turned him away from the mirror. “It's time we fixed your face, dear,” the maid said taking a broad bib-like cape and tying it around the boy's neck and shoulders.  “Just wait till I'm thru with you, Christine; you won't even recognize yourself.” 

After a few minutes, the change was remarkable.  Eyeshadow, a bit of mascara, and blush had served to remove any hint of boyishness.

Lastly, lifting the youngster's chin gently, she brought a tube of lipstick close. “Purse your lips for me, sweetheart,” she asked, and after responding with a coquettish pout, she coated his lips with a pinkish gloss.

“Excellent,” complimented Mary; “a little touch up with the curling iron and our little Chrissy will be perfect”. 

Still facing away from the mirror, the boy sat quietly while Carolyn brushed and curled what had been longish hair for a boy.  After looking through a small drawer in the dresser, Mary approached with two matching satin ribbons, the exact color of the dress. After tying each into a pretty bow on either side of his head, both women smiled. Still beaming, they pulled their guest to his feet. “Don't look yet, Hon,” instructed Mary, “let's slip your lovely dress on first.” 

Taking the pink satin smock from its hanger, Carolyn directed the now petticoated boy to raise his arms carefully. Watchful of his makeup and new hairdo, the women lowered the beautiful garment over his head and outstretched arms. They fussed and primped, tugging it down gently until it settled over the fluffy petticoats. After fastening the row of buttons up the back, the maid removed a long sash from the hanger and wrapped it around the boy's waist, forming a large bow in the rear, giving the dress an almost bustle like appearance. The anticipation was excruciating, but when the two women at last spun the boy to face his reflection, he almost fainted in wonder. 

Looking back from the mirror was no teenage boy in a dress.  Instead was the most beautiful girl he had ever seen. His eyes moved from her delicately painted face, down over the bodice of her lace and ribbon trimmed dress, lower to where her legs seemed to escape from a bouffant cloud of frothy skirts, and finally down to the tiny pink bows which decorated her girlish slippers. Christopher, now Christine, seemed lost in a trance.

“How was this possible?” he thought to himself. As he turned to see the reflection from another angle, it hit him. As the layers of taffeta swished about his nylon-covered legs, there was no mistake. This was no dreamlike image - this was him!  He could have remained before the mirror for hours had the two women not awakened him from his reverie. 

“It's almost 10:30; if we're going, we'd better get along,” warned Mary. 

“Ooops, I almost forgot,” exclaimed Carolyn, rushing to the closet once more.  After briefly searching, she turned with a small white patent leather clutch and a pair of white glace gloves in her hands.  “We can't have you going and forgetting your purse, now can we Christine?” she grinned. The gloves, though snug, fit over his hands, ending just above the wrist in a ruffled lace cuff. 

“Now, come along, sweetheart,” said Mary, trying to rush things along.   With one last look in the mirror, the boy...er..the girl raised a gloved hand and lightly patted a stray curl back into place, then turning, was led from the room.  With the two women, one on either side, he was led down the wide stairwell. Each held one of Christine's gloved hands to steady the boy as he maneuvered slowly down the stairs, still a bit unsure of himself in the low heels. With every step, his frothy petticoats made a delightful frou-frou as they bounced and tickled his nylon-sheathed thighs. Once again, the youngster could feel the excitement build within the silky confines of his lace-trimmed panties.  Embarrassed by his own reaction to the soft touch of his exquisitely girlish attire, he tried to think of something else, but even the smallest movement seemed to defeat him and hold his mind captive to intoxicating caress of his borrowed frillies. 

Being  November, there was an autumn chill in the air, and as they stood in the entrance hall, Carolyn went to fetch her mistress' sable coat.  

“You'd better find something for our little girl, too,” Mary instructed. 

The maid quickly returned with a beautiful pink woolen double breasted coat.  Carefully she slipped it over the lovely dress and fastened the front. Lastly, Carolyn took a hatbox from the upper shelf and opening it, took out a wide brimmed straw skimmer. 

“Hold your head up, dear,” she asked as she tied a fancy bow under Christine's chin. “There now, you look just adorable, Honey,” she said, her hand straightening the flared skirt of the coat.  Bending, she gave the boy a little kiss on the cheek and opened the front door. 

“Come along, sweetheart,” beamed Mary, taking the delicately dressed boy's hand and,  with his skirts bobbing, walked together to the car.

Looking back as they drove down the avenue, he could see Carolyn smiling and waving. Just yesterday, he had sat in the same seat, but now, everything was so different.  Instead of jeans, his legs were now sheathed in smooth white stockings, and despite the weight of the woolen coat, the multi-layered petticoat made his skirt puff up all around him.  He felt he was sitting on a cushion of frills, his ornately trimmed panties only adding to the froth of his skirts.  Folding his gloved hands on his lap, he looked over to Mary, who smiled down at him. 

"Don't look so nervous, dear.  No one is going to recognize you now.”

They drove on, heading down the shaded boulevard toward the academy.  “I'm sure we'll find your suitcase, but it will be so much of a shame; you look so pretty as a girl.”

Blushing, the boy lowered his eyes in embarrassment.  “Really dear, you should have been born a girl; wearing pretty dresses is only half the fun.”  The gates of the school came into view.  “You'd better let me do all the talking, dear.  We wouldn't want you to give yourself away.”

Christopher froze in his seat.  “Oh God,” he thought to himself, wishing that he could somehow become invisible. The large iron gate was shut, so Mary pulled up and stopped just in front and got out. Seeing a lone priest working in the garden, she called to him.  The boy recognized him as Father Patrick, one of the older faculty members who was more or less retired now and spent most of his time tending the grounds. 

"Father, I'm Mrs. Alexander and one of your students is staying with me over the holiday. It seems we left without his suitcase.  Did you happen to come across it in the driveway last evening?” 

“I'm afraid not; I was just up that way a little bit ago.” 

“I brought my niece along with me in the car; would it be an inconvenience if we came in and looked for just a minute?” 

Looking out to the car, the old priest smiled and waved to what appeared to him a pretty young girl.  “Oh, I'm afraid that's not allowed; the academy is cloistered to women.” 

The boy couldn't overhear the conversation, but noted the look of surprise on Father Patrick's face. 

“Well, is it possible you could ask one of the other fathers if they might have come across it?” 

“I'm sorry, Mrs. Alexander, everyone else is away for the weekend now.” 

Mary interrupted,  “Oh, don't worry then Father; I'm sorry we bothered you.  I'm sure somehow we'll make do.  Happy Thanksgiving.”

Christopher noticed the woman smile as she turned and returned to the car, waving to the priest as he toddled away back to his  gardening.  

“Is something wrong?  Won't they let us look for it?” he asked her nervously.

“It seems it's definitely against the rules to allow ladies inside the grounds,” and with a gleam in her eyes added, “and as cute as you look, sweetheart, I'm afraid that applies to you, too.” 

“What are we going to do? It'll be four days till it opens now,” the boy wondered aloud, a tone of alarm in his voice. 

“Now, don't you worry your little head, dear; it seems you'll get to play dress-up a little longer is all.  It'll be wonderful having a sweet little girl in the house all weekend, you'll see.” 

The teenager's cheeks turned a bright red, but not out of  embarrassment from wearing such girlish clothes. Rather,  it was because deep within, he couldn't imagine anything nicer than  continuing this new and exciting experience for as long as he could.

The soft caress of the silky fabrics on his powdered skin and the way the two women (especially Carolyn) pampered him was drawing him in like a fly to a spider's web. There seemed no fight in this little fly either; despite arguments to the contrary, he inched toward their silken trap willingly. 

With his mind distracted with thoughts of panties and petticoats, Mary turned the car around and headed back home. After parking the car in the drive and leading her young charge back into the house, Mary explained what had transpired to the waiting maid. 

Though she tried not to giggle, it was obvious to the boy Carolyn took great delight in his misfortune. “Don't look so sad, Chrissy; there'll be time enough to try on all sorts of pretty things now. It'll be just like having a real live Barbie Doll to dress for a few days. Come Monday, I'll wager you'll feel terrible wearing nasty boy clothes.” 

Without her own family in the house (remember that Mary was recently widowed and her daughter was in college on the West Coast), Thanksgiving was to be celebrated at a local restaurant.

“It seems we'll have a young lady joining us for dinner today, Carolyn, and not the teenaged boy we were expecting,” the older woman quipped. 

“Shouldn't Miss Christine have a bath before we go, Ma'am?” the maid asked with a mockingly serious tone. 

“But of course, I'm sure she'll want to look and smell her best on her first time out to eat,” Mary responded, her voice equally serious in tone. 

The boy stood nervously by as the two women joked, and as he fidgeted, the rustling petticoats continued their unceasing caress. The thought of actually going to a public restaurant while dressed as a young prepubescent girl disturbed him momentarily, but he knew he was powerless to alter their plans for him.  In fact, the stirrings under the boy's fluffy skirts spoke more of his concurrence rather than any complaint.

“Go with Carolyn, darling; she'll get you all ready,” Mary whispered to the daintily dressed youngster, and gently pushed him toward the stairs.  Once again, taking him by the hand, the maid seemed to treat him more as a five-year old than the teenager he was.  Rushing up the stairs, pulling Chrissy behind her, the boy's skirts bounced and  rustled while below, Mary smiled up at the frothy vision as it disappeared into the bedroom.  Everything had gone according to plan.  In just one day, they had transformed the boy into a gaily and exquisitely delicate little miss.  And much to her delight, it was obvious in his eyes that he was beginning to love this new life. 

Carolyn closed the door and directed her charge to the satin ruffled vanity bench.  The boy plopped down, one leg bent back under him and looked back over his shoulder, the look in his eye as if waiting for her next instruction. 

“My goodness!  Christine! Is that how a young lady behaves? If that's the way you treat Susan's lovely dress, perhaps it's time to put you back into trousers!”

Startled, the boy didn't know what to think.  Had she really offered to end all of this?  And, more to the point, is this what he really wanted down deep?  Reflecting on all the events of the previous 24 hours, it didn't take long for him to stand, and spreading his petticoats and skirt carefully, more gracefully took his seat again. 

“I'm sorry, Ma'am, I'll be more careful,” he whispered, his eyes downcast in shame.

“Yes, that's much better, sweetheart,” answered Carolyn, a knowing smile crossing her lips.  “Sit here and I'll start your bath water,” she said, turning and entering the adjacent bathroom. 

The boy's eyes followed her across the room, drawn to her long stockinged legs and the brief skirt of her maid's dress.  As her hips swayed with each step, the youngster sat mesmerized.  The sound of water splashing in the tub filled the room as Carolyn re-entered the bedroom and stood behind the seated boy.

Lowering her head till her face was reflected in the mirror, framed by the pink ruffles highlighting the shoulders of the dress they had him wear, she wrapped her arms around him and gave him a squeeze. 

“You look so precious, Honey. You've made Mistress very happy.” 

His carefully made up eyes looked at her in the mirror, asking for explanation without a word.

“Madam misses her daughter so much since she left for college. Having you here dressed so prettily is just what the doctor ordered, I think,” Carolyn responded.  As the blush spread over his face, the maid began untying the satin ribbons from Chris' hair. Then, taking the silver hairbrush from the vanity, she started brushing the tangles gently.

"You don't know how happy it makes me to see Madam smiling  again,” she went on.  “I'm sure she'll really hate to see her little girl go once the weekend is over.” 

The boy rested his head back against her wondrously fragrant bosom as she slowly moved the brush through his longish curls. Closing his eyes, he seemed to melt into her encompassing warmth. 

“That's enough now, we have to move along,” Carolyn roused him. Taking his hand, she brought him to his feet and removed the matching sash which circled the waist of the pink satin smock.  As he stood before the mirror, she undid the buttons in the back and sliding the dress over his shoulders, let it fall to the floor.  After placing it on a scented hanger, she returned and did the same with the bouffant slip.  It collapsed into a mountain of froth around his knees, and, extending her hand for support, had him step gingerly from the lace cloud. No sooner had she returned from the large walk-in closet than he felt her hands at his hips, taking the frilled waistband of the silk and lace panties and drawing them down, careful not to snag the delicate fabric on the frilled tabs of his garter belt. 

As he tried to cover himself, she slipped the white panties down over his knees and then gently lifted one foot, then the other to leave him standing in only the matching training bra and garter belt.  He again looked in the mirror to see an image which now made him almost tremble. With his hair newly brushed and his face still made up, the sight of himself standing dressed as he was with the sexily clad maid at his back unclasping his brassiere seemed a dream.  She delicately took the each ribboned strap between her beautifully manicured fingertips and pushed them down over the curve of his shoulders. As she pressed her bosom against the now bare skin of his back, she glided her hands down around his neck and then lower till they covered the nipples of each breast. 

Cooing in his ear, she brought him to a state of complete distraction, “You have such lovely little breasts, Christine.”  Scraping the tip of her fingernails over the now stiffening flesh, she teased,  “See how your girlish little nipples stand up?” 

By this time, the excitement had spread far beyond just his non-existent bosom; his thickening member could no longer be hidden. Despite his efforts to hide it, his erection protruded almost straight out. 

With one hand continuing to caress his breasts, Carolyn reached around and took the discarded panties from the vanity, and, placing them over his throbbing shaft, began to milk the boy.

“Ummmm, nice soft panties,” she whispered in his ear.  She teased him unmercifully, “Does my darling little girl like her pretty panties?” Her perfume filled his nostrils, her soft lips caressed the nape of his neck. “You love your frilly new things, don't you, Christine.” 

As she slid the silky panties up and down along his member, he began to shudder,  “Yes! Yes! Make me your little girl!!”  With that, his shaft erupted into the delicate little panties and he collapsed down onto the vanity seat. 

Hugging the now exhausted boy against her, Carolyn ran her fingers through his hair and kissed his forehead.  "That's my girl, my precious little Christine.” Unsnapping the garters, she drew the long white stockings down his legs, and removed them. Drawing him to his feet, she unhooked the belt and laying it aside, led the  compliant boy into the bath.  Shutting the water off, the large tub was near overflowing with fragrant suds. She removed a silk scarf from the linen closet and wrapping it around his head, tied his hair up out of the way.  Helping Christine into the water, she knelt beside the tub and began to sponge the sweet smelling lather over his shoulders and back.  Lifting the yielding boy's arms, she swabbed under them and then moved lower over his chest and lathered his stomach. As Christine sat passively, the strikingly beautiful maid reached beneath the surface and no part of his anatomy was left unwashed. Taking a soft washcloth, she began to wash the makeup from his still beardless face.

“Close your eyes, dear” she warned as she gently cleaned the last vestiges of mascara and eyeshadow from his eyelids. Using the long hose sprayer, she rinsed the soap off him, and then holding a soft towel up, had the boy step from the tub. After Christine was properly powdered, Carolyn had him sit on the bed as she selected his wardrobe for the afternoon's excursion.   A little over an hour later, Carolyn came into the den where Mary was waiting. She no longer wore the brief maid's outfit, but instead showed off her stunning figure in a long blue silk gown.  Mary, too had changed for their dinner out. Though certainly not a beauty queen, the older woman still looked elegant in a stylish black suit. 

“Is our guest ready?” Mary asked.

“Yes, Ma'm, she'll be right down.”  With that, Carolyn called up the stairs, “Come down, Honey. We're ready to leave.” 

Christine appeared at the top of the stairs. She was a lovely vision in white. The maid had certainly chosen well for there wasn't a hint of masculinity left in the boy, rather he (now she) looked the perfect little princess. The dress was all white lace accented by delicate pink satin bows across the bodice and at the puffy sleeves and hem.  From their vantage point, the two women could easily view what must have been several layers of crinolines under the wide almost floating skirt.  Around his waist was a four inch wide pink satin sash tied at the hip with a huge bow.  He stepped carefully down the steps, his feet in white patent leather Mary Janes, highlighted by white anklets trimmed with a turned down pink lace cuff.  Short white gloves covered his hands, each tied at the wrist with matching pink satin bows.  His hair was styled exquisitely, his blond curls piled high and circled with a tiny little tiara. Though the dress gave the impression of girl no older than seven or eight, Christine's makeup appeared dramatically more grown up.  It was obvious that, in addition to lipgloss, blusher and shadow, Carolyn had also made use of false eyelashes. 

His eyes lowered, he stood at the bottom step and finally, his long lashes fluttering, looked up expectantly at his host. 

“Oh Christine, you look absolutely wonderful,” exclaimed Mary, thoroughly pleased at the latest transformation.  “I wish Susan could be here to see how darling you are.”  After donning their wraps, the two ladies led the daintily dressed girl to the car for the drive  downtown to the restaurant. 

*****

Though a small town, the eatery was crowded with those who had opted for Thanksgiving dinner out. The restaurant was the finest in the area, its oaken paneling and velvet draperies giving an impression of aged elegance.  The maitre-d' greeted the trio warmly and escorted them to a table on the slightly raised mezzanine.  All eyes were on the cute little girl as she made her way between the other tables.  Christina couldn't help but overhear the whispered admiration as the other diners paused and noted the precious darling accompanying Mrs. Alexander.  Self-consciously, Christine took his seat as the waiter held the chair for him, making sure to gracefully spread his skirt and petticoat.  It was with an almost audible sigh of relief that Mary ordered for him. 

While the two ladies ordered white wine, a Shirley Temple was suggested for the youngster. The meal itself was wonderful, though Christine felt on pins and needles throughout.

After the traditional turkey, cranberry sauce, and stuffing, Mary ordered pecan pie and coffee and another soft drink for her niece. 

Christine seemed to grow uncomfortable and Carolyn, taking notice asked, “Is there something wrong, sweetheart?” 

Despite the boy/girl's embarrassment, Christine couldn't wait any longer.  “I have to use the restroom,” he finally whispered. 

Smiling, the maid quickly summoned the waiter and asked, “Could you tell me where the powder room is? It seems our little guest had a bit too much to drink.”

After being shown the way, Carolyn took sheepish girl by the hand and led him down the hall to the door marked “Ladies.”  

Thankfully, the elegantly decorated room was otherwise unoccupied. Carolyn latched the door to provide some privacy, and to Christine's surprise, backed him into one of the stalls. Lifting the young boy's skirt and petticoat, Carolyn seemed to take charge.

Here, Honey, I'll help you. Hold your dress up now.”  As his cheeks turned a deep red, his lace trimmed panties were lowered to his knees and the maid inched him back until he was almost forced down on the seat. To his chagrin, Carolyn then gently took his soft penis in her hand and held it down, aiming it for him.  “Go ahead, dear; let me see my little girl tinkle.”

The boy felt totally mortified; never had he been treated like such a completely helpless child.  Despite his humiliation, Carolyn smiled as the sound of water splashing in the bowl echoed in the small stall. When he was finished, instead of replacing his panties to their former position, the maid had the boy stand, his petticoats still raised to waist level. She took a tissue and gently dried the tip of his penis, and with the frilly white panties still around his ankles, she opened her purse and removed a small container.  He looked down just as she opened it and watched as she removed a soft feather puff. After coating it with perfumed powder, she carefully dusted him, paying attention to cover not only his genitals, but also down along the length of his thighs. With one final caress, she patted his now silky penis, and then reaching down, slowly pulled his panties back to their original position.

“All finished, sweetheart,” she said, helping to straighten his petticoats as they floated down over his legs. 

After washing his hands, Carolyn had him face the mirror, and, taking a lipstick from the small white purse he carried, retouched the creamy gloss that coated his lips.  “Feel better now, Honey?” she asked,  opening the door and escorting the embarrassed youngster back to the table.

Still blushing, Christine took her seat, as Carolyn's eyes met Mary's and the two women shared a knowing smile.


 Return to Homepage