Betty Pearl's Sissy Stories 20.1
Sissy Story Archives (older stories) => Pre-2011 Sissy Stories => Topic started by: littlebetsy on January 15, 2007, 10:02:34 AM
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“Show and Tell”
a new story by the author of
“Mandy’s Little Plaything”
and “Little Miss Pink Bows”
(The following story was inspired by a drawing sent to me by one of my readers. I am in his debt for the idea of Howard, Mary Jane and the most unusual morning they spent together.)
SHOW AND TELL, PT. 1
“Howard, please come here! We have a visitor who wants a word with you.”
Mr. Loomis, Howard’s algebra teacher, stood at the front of the room, speaking to someone just outside the door. Howard, who sat in the very last row of desks, was startled to be summoned to the front. The timid boy would have to rise and walk to the door where he could be seen by 30 or so other members of the class. Worse, he would have to parade down a long aisle with six students on either side of him.
That action, which would seem easy enough to any other youth, was for Howard an unimaginable task. For unlike the rest of the class, he was not wearing the regulation school uniform of blue blazer, white shirt, burgundy tie and gray trousers (for boys) or gray skirt (for girls).
Howard was dressed in the shame clothing that his mother had made him wear both at home and at school for the past two years.
On his head was a pink baby bonnet with a wide, lacy brim. It was tied at the chin with an enormous pink satin bow. Howard’s body was barely covered by a short, pink and white print dress, fashioned with an extra large lace-edged collar, puffy short sleeves, and multiple rows of ruffles across the chest and at the hem. Peeking out from beneath the hem was a pair of matching panties, embellished with lacy leg openings and a pink bow on either side. More pink bows could be found on the toes of his black Mary Jane shoes and the lacy cuffs of his anklet socks. A pair of dainty white gloves completed the ludicrous picture.
Howard was dressed not like a three-year old girl but the way a three-year old girl might have been dressed in a long-ago age of folderol, frippery, frills, furbelows and foolishness.
“Howard, did you hear me? To the door now!”
It was bad enough to appear in front of any crowd of this size. (Howard was usually the last to leave and the first to arrive in a room so that he drew as small an audience as possible.) But now the feminized lad was going to have to traverse a gauntlet of malevolent classmates along the aisle. He would be the near-naked prey for their hateful words and molesting hands.
In particular, he dreaded passing Sabrina Duncan, the raven-haired beauty who had brought glory to the school as an Olympic-class fencer. Ever since Howard began wearing his little girl’s clothing to school, Sabrina’s taste for abuse and persecution had been sharply aroused. She, above all others, loved to follow him down the halls, taunting, teasing and twitting him. It was the clever-cruel Sabrina who had invented such delicious quips as “Does sissy need her panties changed?” “Does sissy need her bottom spanked?” “Does sissy have a date tonight with her boyfriend?”
Sometimes Sabrina would simply breathe, "Oooooooh! Aaaaaaaah! Oooooooh! Aaaaaaaah!" to the beat of Howard’s patent leather shoes clicking down the hall.
Her malice had been particularly painful to Howard because, prior to his forced-infantilism, he had been the most devoted of Sabrina’s fans, appearing at all of her matches with posters reading “Touché, Sabrina!” Flowers, greeting cards, balloons and little teddy bears were frequently placed at the altar of Sabrina’s locker by this ardent but foolish worshipper.
“Howard,” Mr. Loomis boomed. “Do I have to come get you?” The class tittered in amusement.
Howard stood and forced himself forward, one little pink-bow toe after the other. As he moved, he heard the all-too-familiar kissing sounds. Why they chose to mock him this way, Howard did not know. But wherever he walked at school, in the halls, in the lunchroom, in the library, he was trailed like a pestilence by those squeaky, cartoonish kissing effects.
He was now passing Sabrina’s long, straight, dark-brown hair. Unlike the others with their leering faces, her back was turned to him. Was she ignoring Howard? He kept his pretty pink-bow toes moving.
Then it came. A sudden, brutally sharp pinch of tapered fingernails on the tender flesh of his upper thigh. A quick, precise thrust by an expert swordswoman. Poor Howard howled in pain – and the room roared with laughter.
Oh, how he hated crying in front of them, but, despite his best efforts, tears of pain and humiliation flooded his eyes.
He looked back over his frilly shoulder at his tormentor. Unlike the others, Sabrina was not laughing out loud. Her beautiful face was a study in cool, ironic amusement. Her wide eyes and slightly parted lips seemed to say, “Is this all it takes to wound you? Then you make easy sport, my pet!”
Howard rushed out of the room and into the relative safety of the corridor. He found himself in the company of Mr. Loomis, a woman, and a girl wearing the academy’s uniform but of middle school age.
“Howard,” said Mr. Loomis in his usual pompous, stagy voice, “I believe you know Miss Dean. She was your teacher two years ago.”
“Y-yes,” said the miserable youth, trying to control his sobbing. “Hello, Miss Dean.”
“Good morning, Howard,” said the beautiful woman with the helmet of platinum blond hair. “You know, I thought you would have grown up somewhat over the years. But you look quite the same as you did in middle school – perhaps even more childish.”
Howard blushed at having these demeaning words said about him and at having to appear in his babyish clothes in front of this strange girl.
“Say, ‘thank you,’ Howard,” blared Mr. Loomis.
“T-thanks, Miss Dean.”
The scornful blond exhaled and shook her head at this hopeless case of a boy. “Howard, this is my star student, Mary-Jane Linklater.”
“Hello, Mary-Jane.”
The girl looked back at him in a way that disturbed poor Howard. Although younger and six inches shorter than the high school youth, Mary-Jane studied him as if he were a tiny bug in a display case. She was a petite thing with skinny legs and arms. Her long red hair was neatly combed and parted but seemed too voluminous for her rather small pale face. The black-rimmed glasses that sat on her short, freckled nose also seemed too big for her.
“Hello, sissy,” she said with a sneer.
Howard blushed with anger and humiliation. But instead of correcting the girl’s manners, the two teachers exchanged a glance and chuckled.
Miss Dean explained, “Howard, Mary-Jane and I are here because this week our class is studying doctors and medical practices. This morning Mary-Jane is going to give a presentation and she needs a subject to practice on. It occurred to me that someone soft and submissive like you would be ideal.”
The girl looked up at her teacher and said, “Yes, I think he’ll do. I wouldn’t want anyone much bigger.”
Mr. Loomis said, “Howard, Miss Dean called your mother earlier today and received her enthusiastic permission. The presentation should take only thirty minutes or so. I’ll hold your books for you until you get back.”
“Thank you, Mr. Loomis,” said the lovely woman with a knowing smile. “We won’t occupy any more of your valuable time. Mary-Jane, take Howie by the hand and lead the way across the school yard to our classroom.”
“Oh, Miss Dean,” brayed Mr. Loomis. “I almost forgot.” The man darted into his classroom, and came back with an object in his hand.
“What is it?”
“You may want this. If Howie ever gets surly or unruly, his mother gave me this to use on him. Take it with you and apply as often as needed."
With that, he handed the woman a very large wooden hairbrush.
(To be continued.)
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SHOW AND TELL, PT. 2
As Mary-Jane led Howard by the hand down the hallway of classrooms, she looked sidelong at him and said, “You look perfectly silly, you know.”
Howard gazed at her, searching for a sign of geniality or sympathy. But the little face that stared back revealed nothing but amused contempt. In her eyes he was an implausible freak of nature. She had happened upon a bizarre specimen in the wilds and was hurrying home to display her discovery to the world.
“I sure would be ashamed to be dressed in a baby girl’s bonnet, dress and panties,” the child chirped as she eyed him head to toe. “And I’m a girl!” she added.
“Don’t think I can’t see those frilly baby panties sticking out from under your short dress,” she said derisively. “Everybody can. Everybody can see a big boy wearing baby-girl panties decorated with little pink bows and rows and rows of ruffles. Even when I was a baby I was never dressed in anything so ridiculous!
“But maybe you don’t know any better. Maybe you’re too stupid to realize that boys aren’t supposed to dress that way. Especially a high school boy who should be old enough to drive a car and take girls out on dates! Not that any girl would ever go out with a pathetic sissy like you!
“Or perhaps you dress that way for fun, Howie,” she said as her tone shifted to sugary condescension. “Do you feel nice and snug in your precious baby bonnet? Do you like the way the ruffles on your dress tickle your bare legs? Are you in love with making those pink bows on your shoes dance across the floor, sissy?
“Tell me, is it fun pretending to be a widdle baby girl wiff lacethy pantiesths? Do you have a widdle dolly to pway wiff? Does your mommy spoon-feed you and wipe your pretty mouth after meals? And wipe your little bottom after a visit to the potty? Does she bathe you and towel you dry and hold the lacy panties out for you to step into? Do you sleep in a crib with a teddy bear and wet your pink diapers at night? Huh?
“Answer me, boy!” she yelled, turning suddenly angry. “Why do you go prancing around in silly girlie clothes? How dumb can you get?
“Oh, look, you’re crying now! Crying in your pretty pink outfit! You really are a baby, aren’t you?”
Miss Dean, who was walking behind the boy and girl, had been keeping her silence. She knew that the purpose of Howard’s clothing was to plunge him into excruciating shame. And if the humiliation came from a girl, smaller and younger than Howard, so much the better. But now she assumed her duty as an educator and began to explain Howard’s ludicrous attire.
As the trio left the high school building and crossed the academy’s beautifully landscaped grounds, the teacher interjected, “Mary-Jane, Howard is not a sissy by choice. He has been dressed in lace and frills by his mother, who is punishing him for past misdeeds.”
“What kind of misdeeds?” asked the curious youngster.
“Well, it all began when Howie was your age and in my class. He was in the throes of puberty and had just discovered the joys of masturbation. Normally, boys can control these urges, or, if they do give into them, relieve themselves in a dark, private place. Not poor Howie. His moments of arousal were very intense and occurred several times a day. Perhaps it was because there were a number of very pretty girls in our class just blossoming into young womanhood, or maybe something in his psychological or physical development went off-track.
“Whatever the case, Howard sought ways to release his sperm and make his painful erections go away during school hours. Mind you, this was especially difficult for our boy, because by nature he is very quiet and timid. He would not masturbate in the lavatory, apparently, because there was not enough privacy. Nor would he wait until he got home. The little sneak looked for ways to do it in plain sight.
“One method was to sit at his desk with a book resting on his lap. Then as he politely watched me conducting class, he would press the volume against the erect p-nis inside his trousers. It seems that with just enough pressure and only a slight degree of movement, he was able to achieve orgasm without calling any attention to himself.”
“That’s disgusting!” said the prim girl in glasses.
“Quite so. Later, he refined the technique to the point that he was able to pleasure himself without use of the book and while keeping both hands on top of his desk.”
“So he was making sperm in his little boy’s underpants?”
“Umm-hmm. And this was happening several times a day. One day in the spring, I counted a total of six climaxes, three in the morning, three more in the afternoon.”
“How revolting! But one thing I don’t understand, Miss Dean. You said this boy was able to pleasure himself without anyone noticing. So how do you know how many times a day he did the naughty thing in his pants?”
“Well, the fact is, Howie’s little secret escaped everyone but me. Call it a hunch or woman’s intuition, I could tell something was going on. Perhaps it was the way the boy’s eyes went totally vacant or the way his face became quite flushed only to turn sickly pale a moment later. I decided the only thing to do was confront him with my suspicion. Do you remember that day, Howard?”
With his white gloved hand held tightly by the little redhead, the pathetic sissy had been a helpless audience to this mortifying discussion. Tears were forming in his eyes again.
“Y-yes, ma’am.”
“Well, tell Mary-Jane what happened, princess.”
Howard could not make eye contact with the fiercely judgmental child. He looked down at the little pink bows on his shoes. “M-miss Dean called me to her desk after school and . . . and . . . asked me a question.”
“Well?” demanded the skinny girl as she gave the sissy’s hand a severe squeeze. “What did she ask you?”
“If . . . if . . . I-I had been ejaculating in my p-p-pants!”
Mary-Jane giggled with delight to see the babyfied boy forced to make such a loathsome admission.
“And what did you tell her?” asked Mary-Jane beaming with glee.
“Y-y-yes, I had.”
Mary-Jane threw her head back and laughed with abandon. “Oh how embarrassing to be caught being naughty in your pants by a pretty teacher like Miss Dean!”
“Well,” continued the pretty teacher, “That day I drove little Howie home myself. I marched him into his house and had a very frank discussion with his mother. Poor Howie sobbed all the way through it. Then his mom slapped Howard’s face several times and made him take down his trousers in front of me. I’ve never seen a face turn so red. When she examined little Howie’s briefs there was no question as to what he’d been up to. Then while I sat watching, Howie was made to bend over and reach for his toes while his mother beat his bare b-ttocks over and over until the boy screamed in pain. This is the very hairbrush she used,” said Miss Dean holding up the object in question.
“And is that when the brat started wearing girlie clothes?”
“Yes! Howie arrived at school the very next day in an adorable butter yellow bonnet and dress, which made no attempt to hide the sweet little rumba panties underneath! His mom told me that she chose a material that would darken when wet. That way, his teacher and all of Howie’s classmates would know whenever precious had made a little sissy mess!”
(To be continued.)
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SHOW AND TELL, PT. 3
"Sounds to me like a perfect solution!” said little Mary-Jane, taking on the airs of sophistication. “I imagine a boy would do anything to make that humiliation stop.”
“You would think so,” sighed Miss Dean with a smile. “His pretty clothes brought out the cruelty in all his classmates. The boys did the predictable roughhouse such as trip him, lift up his dress, or shoot his panties with a squirt-gun to make it appear that he’d wet himself.
“But the girls were worse. They killed him with kindness. They were
always complimenting his darling shoes, fussing with his bonnet or the puffy sleeves on his dress, powdering his nose or spraying him with cheap perfume. They cautioned him to cross his legs when sitting so boys couldn’t peek at his crotch. They demanded to know his color preference in lipstick and nail polish. They would show him photographs in magazines and ask which little nightie he preferred or which male movie star he thought was cutest. They pestered him for his phone number so a handsome guy they knew could ask him out. Howard could endure the boys. But the mean girls reduced him to tears. They really knew how to get to him. And they basked in his suffering.”
“Yet I see that the sissy is still in his shame clothing,” said the young girl with a sneer.
“Yes, well, Howard’s mother has demanded that the little wanker prove himself by remaining chaste for at least 60 days. Only then will she allow him back in boys’ clothes.”
“And he hasn’t been able to last that long?”
“No! Isn’t it pathetic? But when I spoke to her this morning, Howie’s mom said her son was at Day 59. If he can hold out until tomorrow night, he will at long last wear trousers again.”
The girl peered through her glasses at the babyfied teenager. “I wouldn’t be surprised if this silly boy gave into his weakness before then,” she said disdainfully. “After all, he’s been in dresses for two years now and keeps slipping back into his nasty habit.”
“Yes, Mary-Jane, he allows his p-nis to do his thinking for him.”
“And another thing occurred to me, Miss. Dean. You said that Howard is not a sissy by choice. But if he keeps making stiffies and messes in his little girl panties, he must actually want to stay in sissy clothes.”
“Why, Mary-Jane,” said the sexy woman as she stroked the girl’s shiny red hair. “I can see why you consistently make the highest grades in my class!”
The teacher and two students finally arrived at the middle school. On their way to Miss Dean’s classroom sissy Howard caught the eye of many girls and boys who passed him in the hall or spotted him through open doors. Mary-Jane felt his hand trembling with dread.
“Don’t worry, little girl,” she said with stinging cynicism. “Everyone in our class will be delighted to see you. They’ve been looking forward to my presentation all week. After we finish today you’re going to be a celebrity!”
Miss Dean opened her classroom door and found her students quietly attending to the writing assignment she had left them. However, when Mary-Jane entered with Howard in tow, the children began to stir. First with whispers, then with muffled titters, then with hurled insults and unrestrained laughter.
Miss Dean kept her calm demeanor and restored order with one word:
“Silence!”
All students sat up straight, closed their mouths and made obedient eye contact with their teacher.
“Class,” she said in a voice brimming with confidence and dramatic allurement, “as part of our study of medical practices we’ve been treated to a fascinating series of demonstrations. So far, we’ve seen how a stethoscope works, how a blood pressure meter operates, and how to examine a blood sample under a microscope. Today, Mary-Jane Linklater will show you a procedure that cannot fail to hold your interest. I will now turn the floor over to her.”
The teacher then walked to the other side of the room, sat down and crossed her beautiful legs.
The precocious redhead squeezed Howard’s gloved hand and brought the girlish thing center stage.
“Hi, class,” she said with a smile that showed off her dimples. “Miss Dean and I went over to the high school to get this sis—umm, this boy. His name is Howard, and he’s going to be the subject for my demonstration.”
The girl then released Howard’s hand, took one step away and looked him in the eye.
“Okay, Howie,” she said matter-of-factly. “I need you to pull down your panties and lie face down on top of Miss Dean’s desk.”
The sissy stared at her in disbelief. “W-what?”
But Mary-Jane would brook no hesitation. “Take off your little-girl undies and get on top of that desk, stupid!”
“No-o-o! I won’t! I c-c-can’t!”
Frowning and placing her hands on her narrow hips in frustration, the girl looked to her teacher. “Miss Dean, will you please make this stubborn sissy cooperate?”
The teacher stood up and approached the boy in the pink bonnet. She was lightly slapping her palm with the back of the big hairbrush.
“Howie,” she said with infinite calm, “You must do what Mary-Jane says. Otherwise, I shall have to apply hard wood to your seat.”
“Oh, but Miss Dean,” begged the boy in lace and ruffles as he fought back the gathering flood of tears, “why? . . . Why?”
“Because, dear Howie,” she said with excited eyes as she gently caressed his cheek, “Mary-Jane is going to show the class how to give an enema.”
(To be continued.)
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SHOW AND TELL, PT. 4
Poor, foolish Howard thought he could make a break for the door. But Miss Dean, despite her four-inch heels and tight black skirt was far too quick, far too strong.
Howard’s pretty shoes had run only a few feet when the tall, athletic woman caught his left wrist and twisted it cruelly behind his back. As the teen boy cried out in pain and fear, Miss Dean bent his torso downward over her left hip. Then she made liberal use of the extra-large hairbrush.
Boys and girls of all ages like nothing better than to see a sissy soundly thrashed. And Miss Dean’s bright-eyed pupils were no exception. They laughed, cheered and applauded as their beautiful teacher assailed Howie’s lace-covered fanny and bare thighs. These were no mere love taps. She intended to reduce the rebellious fairy to a mass of pain, tears and disgrace. And she knew she had complete carte-blanche from sissy’s mother.
Each stroke started with her arm arced high above her head. Then, bringing her shoulder muscles into full play, she slammed the hairbrush down with ruthless violence. A quick, forward flick of her wrist a split-second before impact super-charged each blow.
Smack! Smack! Smack! Smack! Smack!
“Owwww! Owwww! Owwww! Owwww! Owwww!”
As she administered the spanking, the strict teacher shifted her position so that pupils on both the left and right sides of her classroom would enjoy a nice view of the boy’s pantied bottom and the upper thighs that were soon glowing red from the impact of the hairbrush. After 20 blows, Miss Dean felt the boy’s resistance fade. A few more strokes and she released her lock-hold on his wrist. The pathetic creature slumped into a sobbing, squealing, shuddering pile of pink ruffles.
Miss Dean straightened her posture and pushed a lock of blond hair away from her beautiful face, now flushed with the excitement and exercise of chastisement. She smiled as she observed her handiwork.
“Very well then,” she said, breathing heavily. “Mary-Jane, you may continue.”
The bossy little redhead stood over the weeping lad and repeated her earlier command. “Sissy, pull down your baby-girl panties and lie face down on teacher’s desk!”
Wracked by pain, fear and abject humiliation, the boy meekly rose and reached into the waistband of his preposterously frilly panties. He hesitated, but only briefly. He bent forward and pushed the garment down to cover his equally frilly anklet socks.
When he stood up, the classroom exploded in laughter.
For while Howie had deservedly acquired a reputation as a compulsive, incorrigible wanker, his hairless genitals seemed too tiny to serve that or any other purpose. The shrunken dic-kie must have been considerably smaller than that of every other boy in the room, all younger. It was indeed as dinky as a toddler’s: a pencil stub resting on two little acorns.
But size did not provoke the riotous laughter so much as style. For encircling miserable, red-faced Howard's dainty c-ck and balls, was a pretty red ribbon tied into a bow.
Mary-Jane’s hand flew up to her laughing mouth. “Why, Howie,” she said in a voice sweet with merriment, “even your little peeny has been sissified! I do not understand. Why dress up a part of your body that no one but your dear mommy would ever see?”
The humbled youth was too distraught to reply.
“Well, Mary-Jane,” said Miss Dean, “perhaps Howie’s mother has tied the lovely ribbon on as a forget-me-not. It is attached to the boy’s most tender and private part, so that he will feel it all day long. It is like a string around one’s little finger. It will constantly remind the brat of his baby-girl status. It will be like a whisper repeating in his ear to be giddy and giggly and girlish – both inside and out. I think it’s just adorable. Well, enough distractions. Mary-Jane, do proceed.”
The girl looked at the sissy through her big spectacles and simply pointed at Miss Dean’s desk. Head hanging in shame, Howie climbed hand and knee onto the desk top, which was covered with a protective plastic sheet, and lay face down. The bright red cheeks of his fanny glared like beacons before the hungry eyes of the young students.
Howard was facing away from Mary-Jane. In front of him sat the beautiful Miss Dean with her crossed legs a mere foot away from his hot, wet face. The sexy teacher watched her star student but occasionally gave the humiliated boy a smile and a wink. Behind him Howard heard the squeaky sound of latex gloves being pulled on and snapped into place. Then something was wheeled over to the desk.
“Class,” said Mary-Jane, mimicking the speech of an experienced practitioner, “today we will be using a standard ‘IV stand.’ And hanging from that hook at the top you see a half-gallon ‘enema bag.’ Earlier this morning I filled it with hot, soapy water, but I’ll bet it’s cold by now. However, since this is only a demonstration, it probably doesn’t matter.”
Howard then heard the sound of something clanging against the metal stand.
“Now,” continued the girl in her snotty, pretentious little voice, “some people refer to this part as the ‘hose.’ But the proper name is ‘flow-line.’ One end is screwed into the bottom of the ‘enema bag.’ Further down the line is this device, which is called the ‘shut-off valve.’ I’ve listed these parts and others on the blackboard for those who are wise enough to take notes. Right now our ‘shut-off valve’ is in the ‘off’ position. That means the water in the bag has only traveled this far down the ‘flow-line.’”
Howard felt Mary-Jane’s skirt brush against his bare leg. She was now next to him, behind teacher’s desk.
“However, when the ‘shut-off valve’ is in the ‘on’ position, the water will continue all the way to the end of the ‘flow-line.’”
Perhaps it was the least of his problems, but Howard simply detested the way this swaggering little girl overstressed the syllables in each of her specialty ‘terms.’ This ostentatious dress-parading of her wisdom smarted on his ears almost as much as the hairbrush had on his b-ttocks.
“And when the water reaches the end of the ‘flow-line,’ it will enter a device that those of us familiar with this procedure call the ‘nozzle.’”
The girl paused to pick up a box from the floor and place it on the desk, upstage of Howard’s bare buttocks. Howard saw a quickening of interest in the student audience and began to dread what lay in store.
“As you can see, ‘nozzles’ come in a variety of shapes, sizes and textures. For example, this one is short, smooth and straight and no bigger than my pinky finger. It would be ideal for a baby or very small child. However, today, we are dealing with a big baby brat. And so I will be using this one.”
Howard could not see the device in question, but the children gasped and gaped in awe.
“Class, this is called a ‘p-nis nozzle’ because of its shape. As you can see it has a nice long shaft, which ends in a hemispherical tip. The widest part is one and a half inches across. I have chosen this model because once it is inserted into the subject, his bowels will not be able to eject it. The head will lodge above the ‘sphincter’ muscle. Can everyone say, ‘sphincter’?”
“Sphincter!” the kids cried in unison.
“It will have to be manually extracted by me, the technician,” Mary-Jane said proudly. “Observe the realistic contours and veining on the shaft. I also like the fact that this ‘nozzle’ has a nice weight and feel to it. It’s quite comfortable in my hand. I have an extra one that I will pass around the room. Renée, while I’m attaching this one to the end of the ‘flow line,’ will you share the second one with the rest of the class?”
A cute girl with a light brown ponytail rose from her desk on the front row to take the object from Mary-Jane. As it was passed from one curious child to another, Howard was at last able to see it. The instrument was black, shiny and . . . huge! Worse, it was designed with a sinister upward curve. Howard groaned in terror.
“Hush, little girl,” Mary-Jane admonished, as she patted the boy’s recently spanked rump. “I know you’re anxious to get started, but first we have to prepare your bottom for entry.”
(To be continued.)
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SHOW AND TELL, PT. 5
Howard watched as the children passed around the spare enema nozzle. Some girls wrinkled their noses at the large p-nis replica and refused to handle it. Other girls displayed a healthy curiosity and playfulness. A little blond in a pixie cut held it with both hands and thrust it at her neighbors as if it were a saber. She handed it over to a pretty Asian girl who lay the rubber pen-is on her desk top and then raised her hand and delivered a karate chop to the juncture of the shaft and head. These hijinks provoked uncontrollable snickering among the children.
To end the disruption, Miss Dean collected the nozzle and held it in her lap for the remainder of the demonstration.
“The final item needed for an enema is ‘lubricant,’” said Mary-Jane as she continued to pat Howard’s naked rear end. “We’ll be using this tube of ‘petroleum jelly.’ It will make penetration of the subject’s ‘anus’ a bit easier. Now that we are familiar with the equipment, the demonstration can begin.
“First, we apply a small amount of ‘lubricant’ to the tip and shaft of the ‘p-nis nozzle.’ Yes, you have to get it nice and slick. But don’t use too much. You don’t want to waste any or make a big mess. Then I will squeeze a thin line of ‘jelly’ onto my index finger. Can everybody see?
“Next I’ll use my other hand to part Howie’s b-tt cheeks. And then I’ll just insert my greased finger right up his little hole!”
“Ummmmmmmph!” Howard cried, to the great delight of the giggling audience.
The skinny girl’s finger wormed its way into Howard’s body and began rudely feeling around. Howard tried kicking his feet, but they were hobbled by his lacy baby panties. He tightened his buttocks and tried to squeeze out the unwanted wiggling guest, but the muscles in his anal canal were no match for the little girl’s insolent forefinger.
“It’s really no trouble,” said Mary-Jane breezily, “Just like spreading shortening on a cupcake pan before you add the batter. Round and round, back and forth, and . . . there! That should be enough of that.” Howard felt her impertinent finger slither out.
The girl put away the lubricant and picked up the nozzle. The fearful Howard could feel the tip of the evil device resting gently against the jittery cleft of his buttocks.
“Here comes the exciting part,” said Mary-Jane in a theatrical whisper. “My finger was like a little scouting party sneaking into enemy territory. Now we will attack with our main force. Again, I part the cheeks. Then I place the point of the ‘nozzle’ directly in front of the ‘anus.’ And now I push it in. Hmmm, let’s try that again. One, two, three, push! No? Okay, let me use both hands. One, two, three, push! Darn! Miss Dean! I need your help! Sissy Howie is being stubborn and not letting me enter his ‘rectum’!”
The lovely blond teacher walked over to the desk, the alternate rubber pen-is in one hand, the extra large hairbrush in the other. “Howard,” she said with a note of diminishing patience. “It is most inconsiderate of you to obstruct Mary-Jane’s demonstration. She has gone to a great deal of trouble today on our behalf. You have no right to spoil what she had planned. I order you to relax your orifice and permit her to penetrate you this instant. Do you hear me?”
To underline her command, Miss Dean raised the hairbrush and delivered three more scalding spanks to his red rear end.
“Owwwww! Owwwww! Owwwww! B-b-but, Miss Dean, I can’t. The nozzle’s too big!”
“Nonsense! I don’t want to hear any ‘but’s.’ What I want to see is a b-tt – your b-tt – with a large rubber p-nis stuck inside it!”
The class roared at their beautiful teacher’s cruel witticism.
The woman returned to her chair and let the little redhead continue. Again, the girl applied the forward tip of the nozzle to the miserable boy’s fundament. Then, taking a breath she put all her upper body strength into pushing the probe forward. The sissy groaned in pain. The girl grunted as she labored. The class held their collective breath.
At last Howard’s reluctant rosebud surrendered to Mary-Jane’s willpower. The puckering mouth between his rear cheeks shyly parted its lips, s-cked in the tip of the nozzle head, next gulped the whole head, and then swallowed almost the entire shaft.
“Mary-Jane, you’ve done it!” cried Miss Dean. “You’re inside him now! He’s at your mercy!”
The class cheered and gave the little redhead a standing ovation. She put on her dimpled smile and bowed before her fans.
“Thank you, Miss Dean,” she said. “And thank you, fellow students. I’m so grateful for your support. We have overcome a great hurdle and are now in a position to deliver the goods. Our subject lies before us, naked, prostrate and unprotected. Now with just a flick of my finger, I have the power to unleash a flood into his helpless body. Behold, the mighty waters of the enema!”
The next fifteen minutes were the worst in Howard’s short, unhappy life. The fat rubber p-nis inside him was a brutal, unyielding intruder. It stretched his tender flesh in ways that Howard did not imagine possible. It refused to be ignored, refused to be accommodated, refused to release its grip on the boy’s consciousness. But then came another invader sent by the snooty, officious little girl. A rushing stream of ice water coursed through every twist and turn of his entrails, inflating his abdomen and exerting pressure points of pain throughout his lower torso. He felt like a balloon ready to be popped by any mischievous child with a pin.
An unexpected and devious twist to this torture was that once the contents of the enema bag had drained into him, Howard was forced to remain in position for a quarter of an hour while the waters, in Mary-Jane’s neat phrase, “do their work.” He lay there moaning in pain, the object of ridicule and entertainment for a roomful of happy, fully dressed boys and girls.
But the greatest indignity was that his little beribboned member had been prodigiously aroused by Mary-Jane’s lively little hands and their intimate contact with his rear end. Hidden from the crowd of onlookers, Howard’s tiny sex organ had lengthened and stiffened between his bloated stomach and the plastic-covered top of Miss Dean’s desk. Despite the pain elsewhere in his body, his little p-nis had decided it was party time. And it didn’t help that only inches from his face were Miss Dean’s soft, elegant hands, which held and absent-mindedly fondled the second rubber pen-is.
Poor Howard needed release in more ways than one.
When the fifteen minutes had at last ended, Mary-Jane took hold of the back end of the nozzle to extract it. Because of the tight fit, she had to make several attempts. She would pull, but the rubber pen-is remained in the grip of Howie’s tight rosebud. Mary-Jane then made a series of quick back and forth movements, trying to dislodge the pen-is head from its resting place. But this action only caused Howard’s pelvis to rock to and fro, exerting an exquisite friction on his tumescent wee-wee. And at precisely this moment, the beautiful Miss Dean, who was sitting directly in front of Howard, uncrossed her legs, giving the poor lad a brief but inflaming view of a dark stocking top and white garter strap.
The teacher saw Howard’s face flush and then go sickly pale.
The nozzle finally came out with a loud “pop.”
“All done, Howie!” announced Mary-Jane. “You may get up and tip-toe down the hall to the little boy’s room.”
However, the petticoated figure seemed quite unwilling to rise from the desk.
Miss Dean smiled and said, “Mary-Jane, grab the sissy’s shoulder, I’ll take his leg and we’ll turn him over. No point in struggling, Howie. You know I can use the hairbrush again.”
“Oh, my goodness,” said the prissy little girl. “There’s a milky liquid all over Howie’s wiener and your desk top, Miss Dean. Look, his pretty dic-kie ribbon is soaking in it. Did the sissy ej-c-late while I was working on him?”
“There’s no doubt about it, my dear. It seems he finds you quite irresistible.”
The girl giggled deliriously. “Well, that means . . . ”
“Yes, poor, sweet baby Howie is going to be wearing fancy baby bonnets, frilly dresses and lacy panties to school for another two months!”
The End
----------------------------------
But Wait! There’s More!
Coming Soon to This Website!
A new story by the author of
“Little Miss Pink Bows”
and “Show and Tell”:
HOLLYWOOD SISSY
What really goes on behind the walls
of America’s movie star royalty?
Betsy Danker gives us a rare peek at
a beautiful starlet’s depraved lifestyle.
Excerpts:
“So instead of marrying a real man, someone who thinks for himself and pursues his own ambitions, Allison got herself a submissive weakling, a pet who worships the ground she walks on.”
“As silly as the baby doll nightie was, the oddest thing was the boy’s head. It had been completely shaved, except for a small, wispy topknot at the crown. This little lock of hair was gathered and tied together by a pink ribbon.”
“And Samantha, may I present my sissy son-in-law, whose legal name is now Sissy Betsy Baby Girl McKenzie. My daughter named him after one of the dolls from her childhood and he took her last name, of course. His former name is forbidden to be spoken in this house.”
“The sissy bit his pretty lower lip and then said, ‘My wee-wee bewongs to my missthwess. Itsth not for me to pway wiff.’”
“’You see, Samantha,’ said Ginny as she placed the cane back in the vase, ‘with a good disciplinary program, rewards – sexual or otherwise – are not really necessary. Well, that bit of exercise has given me an appetite. Shall we have lunch now, darling?’”