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Intervention

by Gingerfred Man

 

Chapter One – Vigilance

Dr. Howard Turner had been headmaster at Spermley Academy for ten years as of August 8.

Howard had been vigilant in his efforts to stamp out some of the disgusting practices he knew existed at other elite boys’ preparatory schools, and had been largely successful. But lately, he felt the challenge growing almost too great.

Spermley parents were confident that entrusting their lads to the gentle care of Dr. Turner and his staff ensured that their little heirs would not be wanking each other’s little willies in the woods. No senior boys would be found in the showers kissing a freshman as the senior’s boyish cock slid in and out of the younger boy’s pouting pooper.

Oh, no. Spermley Academy was a "gay-free zone" because Howard saw himself as a public servant dedicated to removing and eliminating gay thoughts from the minds of the fine young men under his care.

Howard had read the stories and heard the rumors about other boarding schools, particularly in England, where you had to throw the "pleasures" of whipping and being whipped into the sordid mix. Boys sucking each others cocks until they sprayed each other’s faces with sticky goo. Boys sodomizing each other! Staff sodomizing boys, for heaven’s sake.

Howard’s methods were severe. He knew that. Some might call them harsh. He could endure that criticism. But it was worth the potential criticism to have the happy, healthy environment Spermley was famous for.

Parents supported him enthusiastically. Even when he explained his methodology to them. And when they made their sons submit to Howard’s methodology.

It was, after all, for their own good.

 

Chapter Two – A Developing Situation

Desmond Robbins had only been at Spermley Academy for three months, but he was desperately unhappy there.

Desmond was 14 and a small lad who had been subject to a lot of teasing from the older, crueler boys. What was worse was the fact that Desmond was quite pretty. Not cute or boyishly handsome. Pretty.

Desmond knew he wasn’t gay. He liked looking at girls and often thought about being naked with them. It made Desmond’s little three-inch charmer all stiff when he thought about pretty girls. Why, then did so many boys, even at Spermley Academy, tease him about being a sissy? Some even made horrible suggestions about things they wanted to do with him. And to him. YUCK!

His mother had sent Desmond to Spermley because of the gay-free reputation of the place. She feared, and rightly so, that boys at other schools would soon be undressing Desmond and enjoying the soft pleasures that his warm, delicious body offered. But there would be none of that at Spermley. Fiona Robbins was sure of it.

A summons from Dr. Turner in early December of Desmond’s freshman year was not totally unexpected, nor unwelcome. If anyone could help Desmond, it would be that dedicated public servant.

Fiona met Desmond and accompanied him to Howard’s office for what could be the most important meeting of the young boy’s life.

"Good morning, Mrs. Robbins, young Robbins," Howard said. In the English style adopted by many American boarding schools, the boys at Spermley Academy were always called by their last names.

"Good morning Dr. Turner," Fiona said. Desmond was silent. He was too scared to speak, since he was certain that whatever was about to happen to him would be bad.

Howard understood. But rather than set the boy’s mind at ease, he pressed his advantage.

"I’ve been getting reports I don’t like, Robbins. I’m hearing that you’re being teased as a sissy. Is this true?" Howard demanded.

Desmond flushed. "Yes sir. But it’s not….."

"Hah," Howard said loudly. "Of course you would deny being a sissy. No one ever admits it. Especially in front of his mother. And no sissy ever admits his own culpability in arousing other boys. Have you ever been tested?"

Desmond looked puzzled. What test? "No sir"

"Then we must test you. And quickly." Howard looked at Fiona, who appeared worried, but confident in Howard’s competence and good will. She nodded her assent.

Howard continued. "Testing takes time and therapy can take longer. But I highly recommend it. I’ll see to it personally. But I’ll need your full support and complete obedience. Both of you."

Poor Desmond blanched. What would he be required to do? He was terrified.

But Mrs. Robbins enthusiastically promised not only her full support, but also that of her son. If there was to be pain before erasing sissiness from Desmond, she was totally prepared to subject her son to that pain.

"Very well. Robbins, you will report to me for a full evaluation at 3 p.m. Friday. Be prepared. The first session will probably last the entire weekend."

The entire weekend! What was the headmaster going to do? Desmond began to cry and whimper.

Howard said, "You see, Mrs. Robbins? This sissiness is what we need to rub out. Have no fear. My methods are solid."

Fiona looked at Howard as if he were an avenging angel, committed to her cause. Then she looked at her whimpering little pussyboy of a son. Well, that would be corrected soon enough.

Howard bade them goodbye, hurrying them a little, since he had another de-sissifying appointment in a few moments.

He was looking forward to that appointment very much. Because it presented a challenge. Only because of that.

Robert Wimpley had been coming to Dr. Turner for counseling for more than two years. And very little progress had been made. Still, Howard was hopeful of a breakthrough. He had to keep pushing.

Robert was getting ready for their appointment in Howard’s small apartment that adjoined his office. Robert had had his own key to the private, outside entrance for over a year now. Because he often came by for emergency counseling.

Howard was eager to see Robert. To judge his progress. And to see if his sissiness had declined as a result of Howard’s intensive, repeated treatment.

Howard entered the door to his apartment and walked to the bedroom. Wimpley was there, acting as sissified as ever.

Howard sighed. It appeared he would have to "counsel" Wimpley yet again.

Robert was sitting at a vanity table that Howard had graciously provided for the poor, sissy wretches that fate sent him for salvation. A truckload of cosmetics were provided for their therapy. The intent was that the "possessed" sissies were to be presented with temptation and then exorcised by rejecting it.

Temptation appeared to be winning its tussle with Robert. He had applied a soft foundation that accented his lovely features perfectly. His eyes he had enhanced exquisitely and his red, puffy, glossed lips ached for kisses.

Howard felt a stirring in his trousers as he looked into Robert’s gorgeous eyes. That was good, because he would need to be erect to present Robert with even greater temptations.

Howard’s soldier stood fully at attention when he gazed at Robert’s silky, sexy, girlish body. Howard kept a full closet of therapeutic lingerie for the pathetic sissy wimps he was treating. Robert had chosen to slide silky, black, seamed hose over his long legs and complemented his perfect, painted toes with strappy, six-inch-stiletto mules. To complete the disgusting ensemble, Robert had adorned himself with a lacy garter belt and a tiny camisole that only reached the top of his hairy pubic region. The little tart had omitted panties and his miniscule penis was stiff, red and throbbing. It also appeared to be leaking something sticky.

How do boys allow this to happen to themselves, Howard pondered for the millionth time. He began to remove his tie, then his shirt, preparing for the therapy that he hoped would, that time, offer the breakthrough he needed and prayed for. But never really achieved.

Howard removed his trousers and noticed with disgust that the little sissy was licking his lips at the sight of Howard's cock. Oh, if only this burden could only be lifted from him.

Howard was actually a very attractive man. Tall, broad and muscular. Very handsome, with sandy-blond hair. And a wonderful, world-class cock. Fat and long with a thick, dark foreskin concealing a pink head. Ridged, blue veins. Heavy, cum-saturated ball bag.

People often wondered why Howard had never dated women. The answer was simple. His mission took too much time to allow it.

"Does the sight of my naked body excite you less than last time, Wimpley?" Howard asked hopefully.

"Oh, yessir. Lots less. But I’m still drawn to it."

And Robert sprang into Howard’s manly arms.

Howard embraced Robert. For some reason, Howard’s cock was throbbing and leaking very badly.

Howard said, "What about kissing?"

"Let me see," the patient asked. "Mmmmmm." Robert loved being in Howard’s arms and being kissed by him. Howard was a beautiful man, even if he was a dense, self-righteous putz. Robert had learned to get exactly what he wanted and needed from Howard by telling him what he wanted to hear.

"I’m sorry, sir" the little creampuff said. "I liked that as much as ever. Maybe we should try other things."

Howard was discouraged, but not crushed.

He had to admit that the next test felt rather good.

Robert was on his knees slurping and sucking Howard’s delicious cock. Howard moaned in…..shame. But the sissy persisted.

Robert had sucked a lot of cocks. He was very popular in the dorms and with other faculty members. But he liked Howard’s cock best. He loved dressing up to make love and had built quite a lovely girlie wardrobe, which he wore frequently for the delight of many in the Spermley community.

He wasn’t alone. There were dozens of girlyboys in Spermley who learned their inclination and capabilities because of Howard’s efforts to rehabilitate them and remove their sissiness.

Spermley Academy was a nest of rampant, cum-drenched sissiness, proving yet again that "do-gooders" often achieve the direct opposite of their objective.

But Howard was unaware of this, as were the students’ parents. The boys and faculty were fully aware. And delighted, since they had their pick of eager, pretty sissies whenever their cocks got hard.

Howard was unaware because he never really checked what was going on in the dorms. He always seemed to be "counseling" a sissy or potential sissy in his private apartment.

All Howard was aware of were the lips and tongue caressing his tender parts. It was a shame, really. Young Wimpley didn’t seem to be getting any better. So few did, actually. But that didn’t mean Howard would give up.

Wimpley did seem to be constantly improving at that foul business he was doing with his lips and tongue. Why did it always make Howard’s guts wrench and balls drain?

Oh. There it was again. Howard prayed for Wimpley’s redemption as he blasted sticky globs of mannish cream into the boy’s eager mouth.

Robert loved making Howard cum. The headmaster seemed to adore it and detest it at the same time – a conflict of the type that made life interesting enough to go on.

And Robert wasn’t through with Howard yet.

"Dr. Turner, you promised you would do the nipple test this time."

Oh, right, Howard thought. Robert lay on his back and lifted his cami to expose two lovely, boyish nipples. Red and puffy and begging for kisses.

Could Howard be getting hard again already? Whatever for?

Robert’s peeny was vibrating as Howard touched his gentle lips to the right nipple. To make it a full test, Howard began to gently milk the little pantywaist. Robert squealed in delight, signaling that the test would fail, but for science’s sake, it had to be completed anyway.

Howard kissed, licked and sucked Robert’s left nipple as he changed tactics by entering the boy’s tight anus with his middle finger.

"Unnnnhhhh," the little sissy said. Then he began to spurt his cream in thick little globs.

Howard stopped licking the boobie and kissed Robert’s pretty lips as the sissy shivered through his intense orgasm. They kissed for quite a while as Howard found the ladyboy’s prostate and massaged it mercilessly. The poor lad gasped, panted and made another big cummy mess.

This was becoming one of his worst failures, Howard said. Then he tried for one last success. The boy’s tummy was deluged with cum. Howard used his fingers to gather it and carefully slather it on the inside of Robert’s anal opening.

That made Robert scream and cum yet again. It was a losing battle for Howard.

The headmaster mounted the little panty boy, who placed his calves on Howard's shoulders and wiggled in a way that would make him look extra-fuckable.

The headmaster’s horn was up (regrettably) and he plunged it into the little panty pussy’s honeypot. Oh, that felt good, Howard thought. In a bad way.

Robert’s eyes opened in helpless lust. The big man had him skewered and was on top of him. He was a turtle on his back. Helpless. Fucked. Mmmmmm.

Fearing yet another failure, but pressing on, Howard made the sissyboy cum twice before Howard winced, moaned and poured out his life’s essence into the young fellow’s bowels.

Howard was exhausted. Robert was fully fucked.

Thinking quickly, Robert cuddled up to Howard and said, "I think we’re getting somewhere, Dr. Turner. I didn’t enjoy that as much as the last time." That was a lie, of course, since it would make the top ten fucks list in Robert’s diary.

But a pleasing lie. Howard beamed. "Do you really think so, Wimpley?"

"Oh, yes, sir. In fact, let me clean you up. I’ll probably really hate that."

Progress, Howard thought, as Robert licked all the spunk and poop from Howard’s beautiful cock. Then kept it up until he got yet another "girl’s big reward" to swallow.

Progress!

 

Chapter Three – Desmond’s Evaluation

That Friday afternoon, Howard allowed himself the smallest sliver of hope as he prepared for his evaluation of Desmond Robbins. Perhaps this lovely young boy with the sweet, blue eyes, tinkling laugh and delicious lips would turn out to be straight as an A-K-Q-J-10. Howard would have to test Robbins thoroughly, but perhaps Howard could save just one lad from the horrors of sissy debauchery.

Debauchery was high on the weekend agenda at Spermley Academy, since the students and faculty knew that their pure-hearted, but dotty headmaster was going to be far off-campus, fucking some poor lad’s pretty bottom in a misguided effort to keep him straight.

Desmond’s mother had threatened him with every weapon in her massive arsenal to ensure that he would give Dr. Turner his full and enthusiastic cooperation for the "test."

Desmond was terrified when Howard's secretary waved Desmond into the headmaster’s big office. Desmond closed the massive oak door, then turned to face a smiling, friendly Howard.

That was a surprise.

Howard welcomed Desmond, then said, "This could be very easy and over very quickly, or it could take most of the weekend. It all depends on you really."

Desmond desperately wanted it to be over. He relaxed a tiny bit at Howard's soothing manner.

Then things took a bad turn.

"Off with your clothes, Robbins! All of them. Now."

This wasn’t going well at all. Desmond froze.

Howard became firmer. "I said NOW, young man. Do you want me to call your mother? Do you want a whipping?"

Desmond couldn’t decide which was worse. Whippings were rare at Spermley. The boys were on the whole very happy and well-behaved. Although Desmond did notice a lot of strange noises from some of the other rooms at night. And there were those strange looks from Desmond’s roommate Harry Stevens, a big, muscular, handsome chap who sometimes looked at Desmond as if he were sizing him up for something. Especially when they were getting dressed for bed.

Desmond had no choice. He took off his school blazer. Then his shirt, trousers and shoes, standing before his headmaster in only underwear and socks. Surely Dr. Turner didn’t really mean everything.

But he did. "Off with it ALL, I said, Robbins."

Oh, my. Tears formed in the sweet, young boy’s eyes as he removed his undershirt and socks. When he slid down his underpants, he began to sob softly.

Howard looked him over carefully. He's lovely, he thought to himself. Those homosexual-leaning boys won’t leave him alone. I must prepare him. But that sobbing!

"Enough of that sissy weeping, Robbins. And please remove your hands from your privates. I must see them to make a full evaluation."

The little angel sobbed again, but dutifully held his hands to his sides, revealing a beautiful sight to his concerned headmaster.

Howard was the first, except for Desmond’s mother, to view Desmond’s perfect, pink package. A three-inch, girlish cock drooping dejectedly, but prettily, over a tiny, pink, wrinkled bag of two hard grapes. Desmond's cock was even uncut, with a long, tight foreskin of kissable flesh. Howard looked at Desmond's gorgeous cock, then at his pretty face and empathized with the young boy. He’s a perfect doll, Howard thought. If I don’t stamp out all his potential sissiness, he’ll be on his back ten times a day, taking cocks into his angelic body, screaming and creaming in sinful ecstasy.

The public-spirited headmaster continued his examination. "Turn around, Robbins," he instructed.

Reluctantly, Desmond complied.

Oh, that bottom! Pink and plump and perfect! Howard felt his cock stir. If he, who was pure of heart, felt such stirrings, Howard reasoned, imagine how the lustful would react to Robbins’ perfect body.

Howard made a thorough visual inspection of the whimpering Desmond’s bottom, then asked him to spread his cheeks. Desmond’s eyes got wider and it looked as if he would bolt, naked, from the room.

Howard said, "Do as I say, Robbins, unless you want me to do it for you."

Desmond did NOT want Howard touching him. He saw that Howard had the look. The look that his roommate Harry had when Desmond was getting undressed. Desmond always turned away from Harry to hide his privates, but Harry still seemed very interested in the view of his bottom.

So Desmond gently gripped his cheeks and parted them, exposing his perfect, little, wrinkled, pink-brown tulip for Howard’s examination.

Howard gasped audibly. This was bad. This was very bad. If Desmond kept his sissy tendencies, countries would be going to war over possession of that incredibly beautiful anus. The joys it promised (to the evil, of course) were intense and immense.

This was an emergency. The testing had to begin immediately.

"Release your cheeks, Robbins, and face me."

Desmond did so, but quivered in anticipation of what was next.

Howard looked down. Even Desmond’s feet were girlish and pretty, with cute toes that would take polish and entice men to kiss and suck them.

Then Howard got his first thorough look at Desmond’s chest. My goodness, Howard said to himself. The boy’s nipples are even puffy and pouty. Men will kill for the opportunity to kiss and adore them.

There was only one defense for the poor, blighted boy. Howard had to bring all of Desmond’s girlish tendencies out, then crush them one-by-one through demonstration of the disgusting consequences.

It was Howard's own technique. Developed solely by him. And while he had been field-testing it for eight years at that point, it hadn’t actually, sort of, exactly worked. But Howard, as a PhD, knew that he was intelligent enough to do anything. The fact that his PhD was in 16th Century Lithuanian literature was inconsequential.

Howard instructed a naked, frightened Desmond to sit on a stool in the middle of Howard’s office. Howard then produced a shopping bag and withdrew a pair of seamed, tan stockings from the bag.

He rolled them into donuts and, instructing young Robbins how to roll them on, ordered him to do so.

Reluctantly, Desmond rolled the silky treasures on. They felt VERY good going up his nearly hairless legs. He blushed to think that he was wearing something a lady would wear. Then Howard produced a lacy, white garter belt, which he put on Desmond, then attached it to his stockings.

Having a man, especially his headmaster do such an intimate task, was humiliating to Desmond. But it was only the beginning. The educator then drew out a pair of black, patent-leather pumps, with three-inch stiletto heels. He slipped them onto Desmond’s feet and ordered him to stand.

Desmond did so. Whoa! It was hard to get his balance, but Howard talked him through the technique and in a few minutes, Desmond was walking around the office with relative ease. Howard’s cock was betraying him again. He looked at the cherubic student and could not take his eyes off the way the heels made Desmond’s bottom jut out invitingly. Or the way Desmond’s limp little cock and balls swayed as he walked. It was most disheartening.

Howard then took Desmond to a full-length mirror and extracted a pair of pink panties from the bottomless bag. Desmond didn’t want to look at himself, but he did. He was disgusted at how girlish he looked in stockings, garter belt and heels. But for some reason, his little peener was at full stand.

Howard's heart sank when he saw that. Robbins had failed the first test.

"What’s the matter with you, Robbins? You have an erection from looking at yourself in that disgusting outfit."

Desmond's eyes filled with tears once again. "I’m sorry, sir. I can’t help it"

Howard harrumphed. "Put these panties on to cover up that disgusting display."

Desmond sat and eased on his first panties. They felt wonderful! Smooth and silky. And they rubbed so sweetly against his poor, hard doodle. He got even harder and even began to gasp a little.

Howard noticed. "I’d better get you away from that mirror or something disgusting will happen. Follow me."

Howard led Desmond into the apartment that adjoined his office and sat him at the vanity table. Then he instructed him in the use of cosmetics, which were difficult to apply with the boy whimpering and crying. But he finally made the lad up. Really up. Desmond was ready for the cover of "Glamour" or "Cosmopolitan." Or even "Panty Boy" magazine.

Desmond was astounded at the results. Even he realized at that point that he had something special going for him.

Howard asked the boy to stand. Desmond wasn’t completely used to walking in heels, but he got to his feet. Howard slipped a lacy white training bra on Desmond and the effect was even more electric.

Howard's cock was rampant and pushing against his underpants and trousers. He was very ashamed at his reaction, but realized that such things were inevitable. Even he, Howard Turner, PhD, was affected by the sight of this boy-girl masterpiece, this sweet confection.

But duty above all. He would not allow his feelings to deter him from duty’s swift completion.

Well, not totally swift.

Howard stood Desmond facing another full-length mirror, then Howard silently dropped his pants and underpants.

Desmond was fascinated by the delicate feminine beauty that he saw in the mirror. He had no idea that he was capable of appearing that way. Beautiful. Sexy. Desirable.

Unfortunately, Desmond's cock noticed too. It was sticking straight up and turning dark colors. And the veins were pounding.

That was the moment Howard chose to begin his tests.

"I’m ashamed of you, Robbins," a naked Howard said from behind Desmond. "An erection from looking at your sissified self!"

Desmond was so enchanted by his reflection that he hardly heard Howard. He managed to reply on autopilot, "Sorry, sir. I can’t help it."

"Well, I’m duty bound to show you the kinds of degradation sissiness can lead you to."

"Uh huh," Desmond said. He was falling in love with his feminine self.

Suddenly, for the first time in his life, a hand other than his own or his mother’s was on Desmond’s little, sissyish wee. Dr. Turner’s hand was in Desmond’s panties, skinning Desmond’s peener up and down. He had never even done that himself, and it felt wonderful!

Desmond felt Howard’s hot breath on the back of his neck and then – Howard’s erect cock rubbing against the small of Desmond’s back, right above the separation of his bottom cheeks.

Desmond did not like that. Another male rubbing his dripping cock over his tender skin was too much of an indignity. Desmond knew that it was "gay," therefore, wrong and evil. He began to twist away from Howard, but Howard was too strong.

Howard kept rubbing his cock against Desmond, while lecturing him on the sins of a sissy lifestyle and the necessity for Desmond to avoid it. All the while, Howard had his hand in Desmond’s panties, stroking his little cock, making him feel things he had never dreamed possible.

Desmond had never had an orgasm. Didn’t even know what one was. But he was about to find out. In a big way.

Howard kept lecturing and rubbing. Lecturing and rubbing. Desmond felt sweet rumbles in his tiny ball bag. He groaned with carnal pleasure as he felt a pang he had never felt before. Then he stopped resisting Howard and surrendered to feelings beyond his imagination.

Desmond’s tummy clutched. His eyes watered. He felt every whit of control leave his body. He gasped to Howard, "Something’s happening to me." And he began to spurt his sissy cream for the first time.

Desmond was in sexual agony, seized by equal parts of ecstasy and humiliation. It was so wrong to cum in the arms of his headmaster, but it felt so good. He wanted to go home to his Mama. And he wanted another one of those things he just had.

Howard’s hand was drenched with the sweet boy’s virginal cum and he was millimeters away from cumming himself as he felt the sweet friction of his thick cock against sissy flesh.

Howard was very "Unnnhhhh" discouraged at the pretty boy’s "Ohhhhh" reaction to the "Ahhhhhhhh" frigging he received, but it didn’t prevent Howard from spurting manly cream all over the boy's soft back.

If only Robbins had resisted more. If only he had punched me or run from my office, Howard thought. Why do they all get rock hard when they see their sissy selves in the mirror? Are there no boyish boys?

The answer to that last question was yes and his name was Harry Stevens, Desmond's roommate.

As Howard and Desmond were cumming all over each other in Howard’s apartment, Harry had positioned himself by a window where he could see the inevitable moment when Dr. Turner would hustle Harry’s roommate out Howard's back door for a weekend of "testing."

Of course, Harry was making good use of the time as he waited. A lovely little sophomore sissy named Leslie Spunker was wearing the prettiest pink negligee as he knelt between Harry’s legs and feasted on Harry’s substantial cock.

Harry patted Leslie’s head lovingly and encouragingly, but his interest shifted from Leslie’s pretty, voracious lips to the scene playing out at Dr. Turner’s back door.

Desmond, whose already girlish face had been cosmetized to feminine perfection, was wearing a large, boy's, winter coat over what Harry was sure was silky lingerie. Desmond was balancing in very high heels as he tried to resist Dr. Turner’s efforts to install him in the passenger seat of the headmaster’s car.

Desmond’s face was beauty itself and Desmond’s legs….in those high heels……Oh. Harry clutched and began to spurt his boy’s cream into Leslie’s wet, eager mouth.

Leslie was quite proud that he had excited Harry so. Little did he know who and what were really on Harry’s mind.

 

Chapter Four – Off to the Stabbin’ Cabin

Desmond was silent and miserable as he sat in the front passenger seat of Howard’s moving car.

Neither had said a word for an hour and a half, but their minds were racing.

Desmond was thinking how wonderful that feeling was that had possessed his body and made his cock spurt goo. He was also thinking about how uncomfortable it was to be sitting in panties that still held that goo. And how he had made that goo for all the wrong reasons. He was terrified of Dr. Turner, who, Desmond had decided, was a few fries short of a Happy Meal.

Howard was thinking about how he would have to give young Robbins the full treatment, something he rarely did with possible sissies. But Robbins was so girlishly, exquisitely beautiful that a life of sin awaited the boy if Howard did not intervene. For some strange reason, Howard’s cock had been stiff during the entire ride. Thinking about simulating lovemaking with the boys often did that to him.

Desmond would have jumped out of the car and run away at any of the stoplights they came upon. But where would he go? Especially dressed in lingerie under his coat. If a truck driver picked him up to offer him a ride…… That was too horrible to imagine.

Howard’s Volvo entered a woodsy road and five minutes later, the teacher and student pulled up to a very nice looking cabin in the woods.

Howard got out, then held the door for Desmond, who reluctantly stepped out. Picking his way carefully in his big heels, Desmond followed Howard inside the cabin.

Much to Desmond’s surprise, the cabin was warm, spacious and luxurious. The living room, kitchen and bedroom were all one large space, with what appeared to be a massive bathroom behind a door.

Dr. Turner obviously came from old money, another possible explanation for his dottiness, Desmond thought.

Howard suddenly turned solicitous, which scared Desmond even more.

"Let me draw you a bath, young Robbins. You must be feeling messy. We’ll get you cleaned up and dressed, then have some dinner."

What did he mean, "we’ll get you cleaned up," Desmond thought. Desmond was old enough to bathe himself.

Howard disappeared into the bathroom and Desmond could hear water running. Desmond’s eyes fell on a set of butcher knives in the kitchen. Desmond could defend himself if need be. But who would believe what was happening to him? He hardly believed it himself.

A few minutes later, Desmond heard Howard summon him to the bath. Reluctantly, Desmond entered the bathroom. It was huge! And richly appointed, with a deep, double-wide tub filled with sudsy water. It did look inviting, but Desmond did not trust Howard, to the point that he had not yet removed his overcoat.

Howard smiled, "Not going to take a bath in your overcoat, are you, Robbins?"

Desmond sighed and accepted a piece of the inevitable. He removed his coat, turned his back to Howard, slipped out of his messy panties, stockings, heels, garter belt and bra and, covering his privates with his hands, got into the bubbly tub.

It felt wonderful. Warm and comforting. And cleansing. But Desmond’s ease was short-lived.

Desmond felt the water ripple and looked over to see that he had been joined by a naked Howard, who was brandishing a washcloth, which he started to use to clean the make-up from Desmond’s face.

Desmond didn’t like the naked male companion in the tub part, but the make-up removal was a good step.

Howard used the washcloth firmly yet gently and then returned to cleaning himself, leaving Desmond alone to clean his own body.

Desmond wondered, was the worst over?

What do you think, Dear Reader?

When Howard was done with his bath, he got out of the tub, dried off with big fluffy towel and told Desmond he was going to fix dinner. Warily, Desmond got out of the tub, and peeked out the bathroom door. Howard was clattering about in the kitchen. That was a good sign. He was also buck-naked. That was a bad sign.

Desmond dried completely, then realized that he had no clothes. Howard showed up at that moment carrying a very skimpy, pink nightie that would barely cover Desmond’s privates. He offered it to Desmond, then watched as Desmond hesitated, but without choices, put it on.

Desmond wasn’t sure how he looked in the girly outfit, but when he saw Howard’s cock reach full growth, he had a general idea.

Howard, who would remain naked all weekend as part of Robbins’ therapy, was shaken by Desmond’s beauty. Even without make-up, Desmond was a world-class cock-stiffener. Even he had succumbed.

Howard cleared his throat and said, We have time for some testing before the casserole is ready; let’s go in the bathroom."

Desmond realized his respite was over. What would Howard do?

"You’re not completely clean, Robbins," Howard said as he mounted an enema bag and filled it with sudsy water. "Did your mother ever give you one of these?"

Desmond began to quake and tremble. He shook his head and said, "Not since I was little, sir."

"Well, it’s a cleanliness requirement for testing here at the headmaster’s teaching cabin."

Resigned to that portion of his fate, Desmond watched in fascinated horror as Howard greased the nozzle with Vaseline.

Howard left the room for a moment and returned with four-inch stiletto bedroom-slipper mules for Desmond’s pretty feet. Desmond put them on, caught his balance and noted, dejectedly, that Howard’s cock twitched at the sight of Desmond in big heels.

Howard stood behind Desmond and noted how sweetly Desmond’s girlish bottom pushed back. It was almost begging to be entered with an enema nozzle. And perhaps later, something else.

Howard lubed his finger with Vaseline and very gently entered the boy’s tight, angelic anus.

Desmond panicked! What was happening? Howard said, "I’m only preparing you for the enema. I won’t hurt you."

Being hurt was not what Desmond worried about. Inexplicably, his little cock was engorged with hot blood and was stiff and throbbing. Howard touched something back there that no man, except a proctologist, should ever touch on another man. Desmond was in a frenzy. Howard kept moving his finger and suddenly, that feeling came back and Desmond was cumming! Hard! Ropes of sissyish cream spewing from his poor, sore balls and out the tube of his cock.

Unnnhhhhh. It was agony and ecstasy, shame and joy, humiliation and delight!

Howard sighed in disgust. Only a sissy would react like that, he thought, as he continued to rub the boy’s prostate throughout his prolonged, gut-wrenching orgasm.

The boy looked exhausted already. And they hadn’t even had dinner yet.

Howard took his finger out and replaced it with the enema nozzle. The boy docilely accepted the enema’s contents, failing to notice that Howard was licking clean the finger that had entered the sissyboy’s virgin anus.

Howard told himself he was making a study of the tastes and smells of sissies in comparison to real boys. Nevertheless, he enjoyed it immensely and was very stiff and rampant when Desmond’s guts began to tell him he had to evacuate.

Desmond told Howard he had to "go," hoping that Howard would be gracious enough to leave the room. No such luck.

"I’m seeing this through, young Robbins," the brave educator said.

Desperate to poop, Desmond sat on the toilet. Knowing that Desmond was rooted to the toilet, Howard conducted another test.

Howard stood in front of the grunting, evacuating boy and placed his cock near Desmond’s face. Desmond pushed it away with his hand, which Howard thought was a good sign. Then Howard stepped back and manipulated himself almost to the point of cumming. How easy that seemed to be in Desmond’s presence. He watched Desmond’s eyes and noted sadly that Desmond was watching with some disgusted (?) fascination as Howard stroked himself to near ecstasy. When Howard was ready to cum, really ready to cum, he stepped forward and blasted his goo directly into a startled young Robbins’ face. Desmond winced and turned his head. He would have run, but he still needed to be on the toilet.

What kind of a lunatic is this guy, Desmond thought. And how could Mother fall for his baloney?

Howard was quivering from the force of his cum. The little sissy seemed to be affecting even him.

He would record a C- for this test for Desmond, who resisted, but still allowed it to happen. Someone like Harry Stevens, Howard was sure, would have punched Howard in the mouth, stolen the Volvo to escape and set the cabin on fire, for an A+.

Howard cleaned Desmond’s face, explaining that it was only a test and to not get ruffled or offended. Even Desmond knew that it’s offensive when another guy cums, uninvited, in your face.

Then, Desmond being fully evacuated, Howard stood him up, cleaned his bottom thoroughly, which Desmond almost enjoyed, then scrubbed his cum from Desmond’s face.

Expecting a further horror, Desmond instead received quite a good dinner. A homemade pork chop and rice casserole, salad, and apple pie for dessert.

Dinner conversation was all from Howard. He prattled on about his boyhood and how a man who lived in the mansion next door (three miles away) to his family spent many hours with Howard desissifying him, much as Howard would do for Desmond.

Many of Howard’s techniques were drawn from those encounters with the man, who would often fuck young Howard’s pretty little pantied bottom four or five times a day, with lots of kissing, tonguing and cocksucking thrown in for dessert.

The new generation of sissies needed the fruits of that legacy for their salvation.

When dinner was finished, Howard sent Desmond to watch TV while he cleaned up. Would it be a normal moment at last?

No. The only thing on television was movies of older men having their way with pretty, young, pantied, powdered and perfumed sissies.

Desmond didn’t like it, really, but he watched. Everyone seemed to be having a good time and the men were very nice to the sissies. The sissies made that gooey stuff a lot and they were even <blush> sucking the men’s big cocks and making them gooey too.

Desmond watched the action in fascinated horror. Young boys with made-up faces and girlish lingerie were performing unspeakable acts with older men. And enjoying them immensely. He watched wide-eyed as a pretty young thing giggled as his glossed lips kissed up and down a man’s thick cock, then took the head into his mouth and sucked the man to a gooey blast.

Despite himself, the movie made Desmond’s cock vertical. He almost didn’t mind when a naked Howard joined him on the couch and began to stroke Desmond’s cock very nicely as they watched a sissyboy on the screen get some incredible attention from an older man.

Desmond watched the lad lie on his stomach, pull down his pretty panties and spread his bottom cheeks open for his man. The man knelt behind the lovely sissy and licked his bottomhole deeply. The sissy was moaning and seemed to be enjoying everything tremendously. Desmond couldn’t tell, but he thought the sissy made a big, messy cum just from the man eating his little sissy pussy. But the most amazing thing was that man appeared to be preparing to put his enormous schwannstucker into the tiny tulip of the sissy’s soft, pink bottom! It would split the poor boy in half! But the sissy was eager for it! Panting and gasping and begging for a good fucking! It was horrifying! Desmond could never allow that to happen to him! But the man put his peach-sized cockhead at the entrance to the sissy’s "pussy" and pushed the entire head in! Oh my goodness, Desmond thought. He’s killing that poor boy! But the sissy only appeared to be dying with pleasure. He squealed happily and pushed back for more cock as the man stroked his huge schlong in and out of the lovely boy’s bottom. How?

Desmond could never do anything like that. He was sure of it. But the movie was making him very excited. Howard really knew how to do that stroking stuff, Desmond thought. It felt really good. But he knew Howard would spoil things and he was right.

Still reaching under Desmond’s nightie skirts and stroking Desmond’s cock so sweetly, Howard began to kiss Desmond’s neck. It wasn’t totally awful, but then Howard kissed Desmond’s cheek as he brought him closer to one of those things Desmond had to admit he liked. Then Howard’s lips met Desmond’s and Desmond was about to protest when he was interrupted by a tidal-wave force orgasm that almost ripped his guts out. Howard kept kissing Desmond through the gooiness and Desmond didn’t even mind when Howard slipped his tongue into Desmond’s pretty mouth.

Somehow they seemed to keep kissing for another 15 minutes or so and oddly, Desmond’s hand found Howard’s cock, imparting similar pleasures to Howard and ending in manly, gooey spurts, and soft caresses and kisses.

Desmond was miserable. He had enjoyed that way too much.

Howard was miserable. Desmond had enjoyed that way too much.

Maybe if they had just, well, you know, enjoyed themselves without all that crap.

But then we wouldn’t have a story, would we?

Both were a bit cummy when they arose from the couch, flipped off the TV and moved toward the bed. For sleep. Of course.

Howard got a washcloth and a towel and cleaned the cum from Desmond and himself. Then he got a clean nightie out of a drawer for Desmond. The new nightie was white and diaphanous. And it opened at a spot between Desmond’s nipples. Desmond blushed when he put it on and suddenly both he and Howard were hard and randy again.

Desmond was struggling to keep what was left of his male self. He vowed that he was not sucking cock or letting Howard put his whopper into Desmond’s tushie. And that was final. Even though the sissy in the movie seemed to REALLY enjoy that. Not for Desmond. Uh uh.

He kind of liked the kissing, though and really liked cumming. Very much. He even enjoyed making Howard cum. It was as if Desmond had some power in the relationship.

But no fucking or cocksucking. If he had to steal the Volvo and burn down the cabin, he would.

He had to admit that he liked the perfume Howard was dabbing on his neck and between his nipples and behind his knees. And he liked how Howard laid Desmond down in the bed and was kissing him as he tickled Desmond’s balls. The balls are very sensitive and love a good tickle. With kissing. Oh, was that thing happening again? It was.

Aaaahhhh. Ohhhh. Desmond was once again in heaven, floating on a cum-filled cloud, sucking on his headmaster’s tongue and spurting his boyish cream.

Exhausted, Desmond fell asleep in his headmaster’s naked arms. Howard rubbed his stiff rammer against Desmond’s perfect bottom, but resisted the evil urges that threatened to consume him, and joined Desmond in slumber.

 

Chapter Five – A Saturday to Remember

Desmond’s sleep was filled with dreams. He was a beautiful princess and all his subjects were approaching his throne to tell him how lovely he was.

One of his subjects was a handsome young man who looked exactly like his roommate Harry Stevens.

But Harry was very fresh. Not content to just adore Princess Desmond, Harry lifted the beauty’s skirts and began to suck Desmond’s sissy prick. If Desmond was a princess, why did he have a prick? And why was he fantasizing about Harry? And why did the dream seem so real?

Then he awakened to a room filled with daylight and a very busy Dr. Turner, who was on his knees on the bed and very lovingly and enthusiastically sucking Desmond’s sissy wee. Desmond’s eyes were wide in amazement. And his mind was processing the first-time joy of having his cock sucked. Even if it happened to be by his headmaster.

Howard, who knew that breakfast was the most important meal of the day, was about to get an RDA of protein. Just to make things extra nice for his research subject, Howard entered Desmond’s bottom with his lubricated finger.

The sucking felt fantastic to Desmond, but the finger in the tushie! Oh, baby! The poor sissy was overmatched and he began to spurt his cream. It felt wonderful!

Glob after glob of heavenly liquid was transferred from Desmond to Howard, who was trying to make the weekend as challenging to Desmond as possible and succeeding wonderfully.

Despite himself, Desmond was half in love with his headmaster. Like a baby bird whose first sight is a cat and for his very short life considers Tabby his mother.

Should he suck Dr. Turner’s cock in return? The sissy in the movie did. And loved it. And took the man’s cock <blush> "back there" as well.

NO!!! Desmond was no faggot. Although he didn’t mind that Howard had not removed his finger from Desmond’s bottom and had even reinforced the lone digit.

Dr. Turner continued to frig Desmond’s bottom as he moved up to kiss Desmond. The lad loved the kissing, but suspected that some of the saliva he was licking inside Howard’s mouth was actually his own cum.

Surprisingly, he was not repulsed.

Desmond slipped a warm soft hand to Howard’s pubic area and hefted Howard’s balls for the first time. They were enormous! For a second he wondered if Harry’s balls were that big. Why was he thinking that?

Desmond’s hand seemed to drive Howard wild with lust. He wriggled and kissed Desmond harder, moaning loudly when Desmond began to skin Howard’s big monster. Howard was fighting evil thoughts of love for this beautiful sissy (evil, gay thoughts) but his attention was diverted by a four-alarm cumstorm. Howard winced and cringed at the sweet agony of his release.

Desmond was frightened and insanely excited at the same time. The two kissed for a long time until Howard broke it up.

Howard went into the bathroom and drew a warm bath. Desmond got up and joined him in the bathroom, since he had to pee. For some reason, Desmond sat to do so.

Howard noted this with interest. The boy was sinking into sissiness. He would have to intensify his efforts.

Howard got into the huge tub and beckoned Desmond to join him. The boy was less wary than he had been. He removed his nightie and got into the lovely, cleansing water.

The two co-habitants stayed apart for a while. Then Desmond dropped the soap into the tub and it floated over by Howard. The boy reached for the soap, but grabbed Howard’s cock by "mistake."

Howard’s heart sank. The lad was taking the initiative! This was terrible.

Still, he didn’t resist when the boy began to wank his wiener with his growing expertise. In fact, Howard moved toward the little cherub and began to use his soapy hand to stimulate the boy’s nipples.

That surprised Desmond! He was discovering one erogenous zone after another and this was a very good one indeed.

Desmond began to whimper a little as Howard teased his nipples manually, then released Howard’s cock to allow Howard to suck and lick the little nubs. That was an eye-opener! And a ball-drainer. Poor Desmond experienced his first sub-surface orgasm, spurting his goo into the frothy tub and holding on to his love partner as he quivered out his sissy cream.

Howard seized the initiative back by picking Desmond up and carrying him from the tub. The boy was so light and soft and girlish. Howard had to protect him.

Desmond was accepting his fate a little more each minute, though it was the fate Howard wanted Desmond to avoid.

It was happening to him again, Howard thought. I try to help these boys and all they do is get worse. And am I lying to myself? Do I really love fucking these little angels?

I believe we know the answer to that.

Howard experienced a bit of a catharsis at that moment. He decided that he could stop fighting the idea of who he was and start enjoying it.

How many of us ever do that?

He had 24 more hours with this perfect princess. A princess who seemed to like being a sissy in a man’s arms. Maybe if they dropped the pretense…..

Howard sat on the toilet seat and began to dry Desmond with big, fluffy towels. For the first time since they had been together, he gave Desmond a choice.

"Would you like an enema, Robbins? I promise you’ll like what happens after."

Desmond noticed. He felt the power shift to him and he liked it a lot.

"Yes, please, sir," the little sissy said.

Howard dried himself, then put the cutest little blue nightie on Desmond. He administered the enema then, unlike the last time, stood away from Desmond as all the "dirties" left his body.

Desmond looked at Howard and asked, "Aren’t you going to stand in front of me and tease me with your penis, sir?"

Howard felt a little ashamed of himself for doing that the previous night. But then he heard Desmond say, "I wish you would."

Oh my.

Howard stepped toward the seated, pooping Desmond. He was very hard and erect. The sissy beckoned him closer.

Then Desmond did something he never believed he would do.

He held Howard’s cock in his sweet hand and kissed the tip lightly. Then he gave Howard’s balls a good licking. That was all Howard needed. Howard had the biggest cum of the weekend and what he believed was the biggest cum of his life. He sprayed the poor boy’s face with manly goo. And the boy giggled all the way through it.

So that was what consensual sex was like. Nice. Very nice.

Howard held Desmond to his chest and thanked the boy profusely.

When Desmond was finished with his business, Howard gently scrubbed him clean, then adoringly took him into the living room to instruct him in make-up once again. When Desmond’s face was sissy perfection, Howard helped Desmond put on white stockings, garter belt, bra and four-inch stiletto heels.

Panties, which would have been quickly removed, were omitted.

Howard made good on his post-enema promise. He carried the willing little doll to his bed. Howard lay on his back and coached Desmond into a position where Howard could eat the little sweetheart’s delicious, squeaky-clean bottomhole.

The poor little sissy was once again unprepared for the intensity of feelings associated with a good pootie-licking.

The heavenly sweetheart screamed in release as the first of three cums left his over- challenged balls. After the third spermstorm, Howard gave Desmond’s exhausted balls a delicious sucking and licking, causing yet again a goo-a-thon to occur.

The boy was frantic with lust and wanted to suck Howard’s cock in humble gratitude. But Howard had bigger plans for that particular erection.

He positioned his seraphic companion on his sissy back, then threw Desmond’s calves over his shoulders.

Desmond knew his moment was at hand. He was about to be fucked like a helpless little girl. Like that sissy in the movie. He knew now that he would enjoy it every bit as much as that sissy did.

Desmond gritted his teeth as he waited for the pain of insertion. But Howard had prepared Desmond so well that the boy felt only intense, searing, sissy pleasure. An ass full of cock. A heart full of joy.

Howard was enjoying the first non-bullshit fuck of his life and he had never been happier. This wasn’t therapy. It was fucking. Hot and dirty. With cum and saliva and grunting and gasping and messiness.

Yessss!!!

The two lovers went at it hammer and tongs for three rounds and in the end, it was a draw. They spent the day and night together and in a narrow sense, fell in love. Not married-with-a-white-picket-fence-and-2.3-children love. Love from mutual understanding and satisfaction of a shared need.

 

Chapter Six – The Beginning

It took Howard and Desmond a long time to get home to Spermley Academy that Sunday. They kept stopping every 20 minutes or so to kiss and fondle. Desmond had asked that Howard, when they were alone, call Desmond "Madeline" or "Maddy" and use feminine pronouns when referring to her.

Maddy wore stockings and heels with a tight miniskirt and pretty blouse on the trip back. She would have worn panties but her "Howie" wouldn’t hear of it. He played with her little sissycock all the way home. And she had the spermy skirt stains to prove it.

Howard had never been happier. Now he could enjoy Maddy and her sissy sisters without guilt. In fact, he wouldn’t worry anymore about "gay" things happening at Spermley. He was pretty sure that very few of the boys would actually be sissies and he was certain that almost no boys would want to have sex with sissies.

When the lovers got back to Howard’s apartment, they fucked.

What did you expect?

And planned for future fuckings. Lots of them.

Maddy was getting very good at sucking Howie’s cock, but she wanted a lot more practice.

They were both very sad when Maddy had to get into those awful boy clothes and be Desmond again. But they made a date for the following afternoon.

Desmond insisted on wearing his "Maddy lingerie" under his boy clothes.

As Howard kissed his sweetheart farewell, he asked, "Aren’t you afraid that your roommate, young Harry Stevens, will catch you in your lingerie and tease you?"

Desmond smiled. "Not at all, Howie darling. Not at all."

 

 

 

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2002 by Gingerfred Man. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.