Panties For Men

Caught on Camera—Punished in Panties! By Sissy Helga

Ian’s heart pounded as he waited nervously outside the office of Ms. Evans, the headmistress of the coed school Ian attended. She was a formidable woman, tall and with dark-hair and startlingly deep brown eyes that could transmit benevolence or cruelty according to her mood. Her pupils all came from the surrounding district, some from a relatively wealthy area and some from the rough part of town.

Ian had a pretty good idea why he had been called to her office. He had a thing about girls’ panties, and nothing gave him more pleasure than creeping up behind an unsuspecting girl and yanking up her dress to get a good look at her panties. He loved making the prissy little girls shriek as their panties were exposed. He also loved to hang around playgrounds hoping to see girls on the swings or, even better, the monkey bars when they'd hang upside down from their knees, their dresses cascading down to cover their faces as their panties were completely exposed. It was a time when even little girls often wore panties made of silky nylon with lace just like their Mommy’s.

Just the sight of a girl’s panties made Ian’s **** all stiff and tingle with pleasure. He had yet to have his first proper orgasm, but, unbeknown to him, itt would soon happen, and in a very humiliating way!

Ian nervously knocked on the headmistress’s door. Ms. Evans called him in to her study. Two girls were standing by her desk, Cynthia Bailey, the head girl, and her deputy, Marlene. Ian stood in front of Ms Evans’ desk.

“You’ve been pulling up girls’ dresses again, haven’t you, Ian?” said Ms. Evans. Ian blushed bright red! The girls s******ed, knowing this was going to be fun! “You, naughty boy! Well, young man, I’ve got something here to show you!”

She walked over to a home movie projector and switched it on. A dazzling light shone on to a white screen on the wall. The film started. To Ian’s horror, he was the star! He had been filmed lifting up girls’ dresses in the playground. There was also a clip of him standing by the monkey bars in a nearby park, his hands fiddling deep in his trouser pockets as he watched the little girls hanging upside down, their cute silky panties fully displayed. Watching girls showing off their panties was this boy’s favorite sport! As he watched the film, he felt his face burning up even more.

“Now, Ian,” Ms. Evans said, “we could send this to your parents, and possibly show it to the whole school as a lesson for other randy little boys like you, or you can agree to a punishment tailor-made for you. Which is it to be?”

Ian gulped. He had no choice. His parents would kill him!

“Please don’t show it to anyone else, Ms. Evans. I’ll do anything, but, please, don’t let my parents know!”

Muriel Evans smiled to herself. She was going to enjoy this!
“You realize if you agree to our punishment, there’ll be no going back?” Ian nodded.
“Right, young man, take off your clothes!”

Ian gulped with shock! But, when Ms. Evans gave an order, you obeyed! Slowly, Ian took off his jacket, then his school tie, then his shoes and socks. Then, he removed his shirt.

“Come along! We haven’t got all day! Get your trousers off!”

This was terrible. With the headmistress and the two girls leering at him, he dropped his trousers, stepped out of them, and stood in his underpants, his hands folded in front to cover himself.

“Get the stool, Cynthia!”

The head girl pulled a stool across the floor in front of Ian.

“Up you get!” she giggled.

Ian did as he was told.

“Put your hands on your head! There’s nothing there that we all haven’t seen before!” Ms. Evans ordered.

Ian did so, very aware of the girls ogling the front of his underpants.

“Get his underwear off, Marlene. And, Ian, keep your hands on your head or you’ll feel this!” Ms. Evans wielded a strappy vicious looking cane.

Ian’s heart lurched in his chest. They were going to strip him naked, and there was nothing he could do about it. He was by nature a shy boy, and hated stripping off in front of other boys, let alone women and girls. Ms. Evans swished the cane through the air. Marlene walked up to the poor boy and pulled his underpants down round his ankles.

Marlene pulled Ian’s pants down!

Ian felt the cool air of the room circulate around his genitals. He wanted to hide them behind his hands, but the fear of the cane stopped him.

Marlene steadied him, and told him to step out of his underpants. Ian’s pubescent **** and balls were now on display, and were the subject of amused jeers from Ms. Evans and the two girls.

“Not very impressive, Ian. Marlene, see if you can do something about it before we dress him!”

Dress him? Ian’s mind whirled. What were they going to do? His thoughts were cut short as Marlene began to slowly hitch up her school uniform skirt. Up higher and higher! Her stocking tops and garter straps came into view, and then her white panties! White full-cut nylon panties. Semi-see-through panties with girly lace edges! Ian’s eyes were transfixed by the beautiful vision. Helplessly, he felt his **** stirring! Marlene toyed with her taut suspenders, making her panties ripple sexily. Ian’s **** engorged in spite of his utter embarrassment, and soon it was sticking out like a tent pole (but a small one!) as Marlene continued to give him teasing glimpses of her panties!

“That’s better!” murmured Ms. Evans. “Now, Cynthia, get his panties! You see, Ian, as you seem fascinated by girls’ clothes, you’re going to wear them!”

“Oh, no, ma’am! Please! Not that!” pleaded Ian, tears beginning to fall down his cheeks. “Please don’t make me wear girls’ panties!”

“Oh, yes, Ian! Or, the film gets distributed!”

Ms. Evans said, “It’s fortunate that we put on that nursery rhyme show last year for the kindergarteners because we now have such a nice supply of pretty little girl outfits in sizes that should fit Ian very nicely. I picked out some of them from the wardrobe room, so go to it girls, pick out some things from that box on my desk.”

Cynthia rushed over to the box, rummaged around inside and pulled out a pair of girls’ pink nylon panties! She waved them in the air, and then walked up to Ian and held them by the waistband in front of his horrified eyes!

“I chose these specially for you, Ian! They’re very girly, aren’t they? Pink, of course, and very silky! What a lucky boy, being able to wear such gorgeous panties! Come along! Step into them! Do the honors, Marlene!”

Ian gulped! He was going to be dressed in girls’ panties! By a girl! By Marlene! Oh, no!

Marlene kneeled down and held the panties open by Ian’s feet. Ian looked down into the garment with which they were going to humiliate him. Ms. Evans stood behind Ian and held his waist to steady him. It also meant she would have an excellent view as this boy was put into girls’ panties for the first time! Ian lifted his left foot and threaded it through the elastic legholes of the panties. Then, he did the same with his right foot. Then, agonizingly slowly, Marlene began to slither the silky panties up the boy’s legs. Up over his knees.

Marlene pulled the pink panties up Ian’s legs!

Ian looked down as the silky pink prison approached his stiff ****. Marlene bunched the panties around the top of Ian’s thighs, then held the waist-band right out in front of the boy’s ****. Ms. Evans seized the rear of the waistband and stretched it out. Ian was now looking down into what looked like a pink silky bag.

“Let’s do it, girl!” said Ms. Evans, “let’s get him into girls’ panties!”

Marlene and Muriel pulled the waist elastic up. The double nylon gusset of the panties pressed between Ian’s legs. Then, SNAP! The waist elastic snapped round the boy’s waist. The silky pink nylon enfolded his excited **** in a prison of forbidden femininity! Ian’s shame was total, but mixed with the shame was a frisson of sexual excitement!

The silky pink nylon caressed Ian’s ****!

The silky pink nylon caressed his ****! He would never forget the first time he was put in girls’ panties, and his whole sexuality would be perverted in the future by what was happening to him now!

Ms. Evans and the two girls stepped back, admiring their victim. Ian’s genitals made a most interesting bulge in the front of the panties!

The shiny pink nylon radiated out from his jutting penis, giving a whole new slant to the term

‘panty lines’! The boy’s **** was so excited by the silken caress of the panties that it began to visibly twitch! And, with each twitch, the most sensitive part of his penis brushed against the nylon, the slithering material setting up a vicious circle of bizarre pleasure. Ian felt totally humiliated as his excited **** tented out the panties in a most bizarre way!

“Now for his bra!” murmured Ms. Evans.

She picked up a tape measure, and slipped it round Ian’s chest, feeling his nipples as she did so!

“Mmm! A 32B should do!” she said.

Marlene smoothed down her skirt, and delved in the bag, her hand emerging with a pink nylon girls’ bra. Eagerly, she held it in front of the boy.

“Put your arms through here!” she ordered, holding the straps open invitingly.

Poor Ian’s mind was in a whirl, and he did as he was told. Sally adjusted the straps round his shoulders, and then moved behind him, and fastened the bra, snapping the elastic as she did so. She then put her hands round his chest and began to caress his nipples through the silky nylon. Waves of pleasure swept through Ian’s body. His little nipples erected immediately, much to Marlene’s delight.

“Not much of a punishment, this!” she said. “The sissy loves it!”

Ian stood there helplessly, as Ms Evans, Cynthia and Marlene ogled his bra and bulging panties!

Marlene began to snap the elastics in the waist and legs of his panties!
“Girls’ panties! Girls’ pink panties!” she began to chant in time with the snaps, “Ian’s wearing girls’ pink pan-ties!”

Ms. Evans and Cynthia soon joined in, taking it in turns to snap the bra and panties they had dressed the boy in. Ian squirmed with embarrassment, but there was nothing he could do to stop this. The contrast between the tension of the elastics and the smoothness of the nylon of the panties and bra emphasized the erotic nature of the garments.

“Now for his other clothes!” said Ms. Evans.

Ian’s feet were placed in little white ankle socks, and then white leather buckled shoes with low, but definitely feminine, heels. Then, Cynthia walked over to the bag again, and pulled out a full-skirted pink satin party frock, which rustled as she shook it out. Under the pink satin, a frilly nylon petticoat complimented the frock. It was every little girl’s dream, and every little boy’s nightmare!

She walked up to Ian, bunching the frock up in her hands, and slipped it over his head. With the assistance of the other two females, she slipped the boy’s arms through the armholes. The frills cascaded round the boy’s thighs. Cynthia smoothed it over his body. Fortunately, the full skirt hid the bulge in his panties made by his ****, which was still twitching with forbidden pleasures, although the boy himself was overwhelmed by his humiliation.

Ms. Evans stood back. The young boy looked vulnerable and quite beautiful!

“What else, do you think, girls? He looks very cute, and I want it to be quite clear that he is a boy wearing girls’ clothes, but he’s look so good in a nice long wig.”

The girls cheered to put a wig on him with comments that he’d still look like a weepy faced boy. Ms. Evans agreed but said the girls should make up a sissy sign of some sort to hang around his neck as she went to the costume department for their stage shows to find a wig. When she returned the girls had made a sign that read “Sissy Panty Peeker” and hung it around his neck.

“So! That should do! Now, girls, take his hands and we’ll take him to his classroom!”

So saying, Ian was dragged out into the corridor and along the passageway to his classroom.

“Please don’t show me to the class like this! Please don’t!”

Tears were beginning to roll down Ian’s cheeks.

“But we want everyone to know what happens to little boys who pull girls’ dresses up to see their panties, Ian! Come along!”

A buzz of excitement was emerging from the room as they approached it. Ms. Evans swept in and the two girls followed, pulling Ian in to the room in front of the whole class. The gasp was audible!

“Wow! Look at that! That’s a boy in a dress! Yuk!”

“It’s Ian! He’s wearing a dress!”

“What a sissy!”

“He looks a complete pantywaist!” shouted Ian’s arch rival, Terry. “I wonder what he’s wearing underneath?”

Ms. Evans addressed the class.

“Children. You all know how Ian likes to go round trying to see what girls are wearing under their dresses. Well, now the shoe is on the other foot. Tell the class what you’re wearing under your dress, Ian!”

“P-p-panties, ma’am.”

“What sort of panties are you wearing, Ian? And speak louder and tell us in detail or you’ll be in even bigger trouble.”

“Pink panties, ma’am. Girls’ pink panties! Pretty girls’ panties with lace and ribbons and stuff!”

“Yes, children! Ian’s wearing girls’ pink panties under his pretty dress, very pretty ones I might add! He likes to watch girls playing, hoping to peek at their panties, so now he can join them! Tell the class what you are, Ian!” she ordered.

As tears streamed down his face, Ian forced the words out. “I’m a panty boy, Ma’am!”
“Louder!”
“I’m a panty boy!”

And panty boys like to show off the panties they’re wearing, don’t they Ian?” “Yes, Miss!”

“Right, boys and girls,” she said, “from your comments, I can tell you like the ‘Sissy Panty Peeker’ sign the girls hung around Ian’s around his neck. So now it’s your turn; I’ll hand out some cards and you can write messages and we’ll hand them round his neck and Lucy will make a video and Marlene will take photos so that we can post them on the notice board!”

The class hooted with laughter and giggles, as they wrote on the cards.

Ms Evans took the first one, and with it, replaced the card which she had previously put on the poor boy. The new card read, “Yes. I am wearing girls’ panties too!”

The class s******ed with glee. As Marlene got busy with the camera, he was directed, “Tell the class what it says, Ian! And speak up so you voice is captured on the video.”

Ian swallowed hard, and forced the words out. “I am wearing girls’ panties too!” The class erupted with laughter. Tears began to run down his cheeks.
“Ah! How sweet!” said Cynthia. “Our sissy is crying. What a baby!”

Ian’s discomfiture seemed to arouse the other kids; the boy’s humiliation was strangely sexually exciting -- most of the boys now had hard-ons in their trousers and most of the girls had damp panties!

“Terry. Would you like to put your card on Ian now?”
“Yes, Miss,” he answered, smirking, and changed the card.
“Well, say it!” ordered Marlene.
“Would you like to see my panties, boys?”
“Yes!” shouted the boys. “Show us your panties, Ian!” they shouted.
“Well, come on then, Ian!” said Ms. Evans, “don’t keep the boys waiting! Show them!”

Ian blushed beet red. Tears continued to stream down his face as he reached down and grasped the hem of his frock and pull it up.

“Higher! Higher!” the boys and girls began to shout. “Let’s see your panties, Ian!” “Let’s see your panties, Ian!”
Gradually, Ian’s panties came into view!
“Right up, Ian! Pull your dress right up!” ordered Ms Evans.

Ian hoisted his frock all the way up to expose his bare tummy above his saucy, high-waisted panties.

“Pink ones!” someone shouted.

“He’s wearing pink girls’ panties! Look!”

“What a sissy. Only a fag would let someone make them wear pink panties.”

Poor Ian was aware that the eyes of the whole class were staring at his humiliating panties.

“Those panties are really girly! What a sissy! What’s that little bulge at the front of those nice panties, little girl?”

And sure enough, Ian’s small **** was thrusting against the front of the pink panties; he didn’t want it to be hard and couldn’t understand why his body was betraying him; how could he have a surging erection while suffering such intense shame?

“Right! We’re all going into the playground now to give him a dose of his own medicine! This way!”

With that, Cynthia and Marlene took Ian’s hands again. Ms. Evans led the way out of the classroom. The girls giggled as they pulled him down the corridor, and through a door into the playground.

“He’s all yours, boys and girls!” Ms. Evans called out, and went back into the school leaving Ian at the mercy of his classmates!

But, they were not in the mood for mercy! In a flash, Ian was surrounded by screaming and giggling boys and girls, all of them trying to pull his dress up! There was nothing he could do to stop them as his dress was yanked up, exposing his pink panties!

“Look at his pretty panties, everybody!” an excited little girl squealed.

The children started chanting. “We can see your pant-ies! We can see your pant-ies! We can see Ian’s pant-ies! Ian’s wearing pant-ies!”

“We can see your pant-ies!”

The more Ian resisted, the more excited his attackers became. Suddenly, a hand grabbed the bulge in the front of Ian’s panties. It was Terry! As his fingers squeezed and tickled Ian’s ****, another boy had his hand up the back of Ian’s frock, tickling his ass through the silky nylon.

“No, no!” screamed Ian, “get off! Don’t!”

He was totally shocked by the sexual assault as the little boys enthusiastically played with his private parts through the slithery nylon! But, his hands were pinned behind him, rendering him helpless as Terry’s fingers grabbed and fondled his **** and his balls through the silky material!

“Anyone else want a go?” shouted Terry. “Yes! Me! Me!”

Ian struggled, but in vain as other eager hands, girls’ and boys’, had a feel of his panties and the contents!

“Now, leave him to me!” said Terry. “Hold him still, boys!”

Terry looked into Ian’s eyes. He slithered his hands over Ian’s breasts, and then down over the silky panties, cupping Ian’s balls in his left hand as he fondled Ian’s **** through the silky nylon with his right hand.

Terry fondled Ian’s **** through the silky nylon!

“You really like this, girly-boy, don’t you?” Terry sneered.

“No, no! Please stop Terry.”

“But you’re a panty-loving sissy-boy, Ian! And sissies like it when boys play with their little ****s!”

And, to Ian’s chagrin, his **** was now fully erect in the silky panties as Terry squeezed and tickled it.

Eventually, Terry stopped.
“Let’s get him to the monkey frame!!” someone screamed.

Ian was hauled across the playground to an adjacent field in which was situated the very monkey frame on which he had ogled little girls!

Ian was dragged to the frame and forced to climb up and sit on the top rung. Someone held his feet and he was forced back over the top bar until he was suspended upside down from the backs of his knees. Ian’s frock cascaded down over his head. His pink silky panties were totally exposed to the ogling children.

Ian’s pink silky panties were totally exposed to the ogling children!

His struggles made the scene even more exciting. As his legs kicked ineffectively, the pink nylon of his panties rippled in the sunlight, emphasizing the incongruous bulge made by his genitals. Terry walked forward, his eyes only inches from the bulge of Ian’s **** in the panties.

Cynthia and Marlene realized that things were going too far, but the juices flooding into their own panties were indicative of how sexually exciting the whole scenario was, and they did not want to put a stop to it. Particularly as Marlene was filming the whole thing with her video cam, and this particular film needed a fitting climax!

Terry was aware of Ian sobbing under the inverted frock. He was in control, and he wanted to maximize his rival’s humiliation. He slowly and deliberately placed his left hand on Ian’s panty-clad buttocks, fondling them obscenely as he poked at his victim’s ******* through the stretchy pink nylon. With the fingers of his right hand, he seized Ian’s **** through the front of the pink panties, and squeezed as he laughed in Ian’s face. Terry held Ian’s **** through the nylon panties and squeezed and pumped it, making the sissy boy shutter! “What’s this then?” he sneered, and with that he began to trace his fingers up and down the length of Ian’s nylon- enclosed ****, slithering the silky material over the most sensitive parts of the boy’s penis!

“No! NO! Stop him, somebody!” screamed Ian, acutely aware of the intense humiliation of being wanked in public by a boy while he was wearing girls’ panties!

Ian’s pleas were muffled under the voluminous frills of his petticoat, upturned and held out of the way so everyone could see. The big petticoats trapped against his face by the kid’s hands determined to keep his skirts and slips up for an unobstructed view. All Ian could see through his tearful eyes were the feet of his classmates as they crowded around to get a good view!

He was helpless as he felt Terry’s fingers playing with his **** and balls through the silky material of those awful girls’ panties he was wearing. But then, to his horror, he began to experience waves of illicit pleasure. His excited **** betrayed him as Terry slithered the pink nylon over it! He mustn’t cum! He mustn’t! But, he couldn’t stop! He was going to be forced to cum in the panties!

Everyone stared as Terry’s fingers closed round the bulge in Ian’s pink panties and began to deliberately masturbate him! Suddenly, Ian’s cries turned to moans. Terry felt Ian’s body arch, and then Ian was thrusting his **** back and forth in Terry’s fingers.

Ian moaned helplessly. “No-o-o-o!”

“Yes!” shouted Terry, his fingers encircling Ian’s **** and squeezing.

“Gotcha!”

Ian’s **** throbbed, and then was spurting into the panties!

Ian’s **** throbbed and then was spurting into the panties!

He was having his first sexual climax—at the hands of another boy, and while wearing girls’ silky things, and in front of a giggling and cheering crowd of boys and girls!

He was well and truly hooked! Hooked helplessly on the monkey frame, hooked on girls’ panties, hooked on shame and humiliation, and hooked on being masturbated by another boy!

Tears streamed down his face as he was led back into the classroom.

“I think we’d better get him changed!” sneered Marlene.

She and Cynthia pulled Ian up the corridor and back into the head mistress’s study. They stripped off the pink satin dress, and his saturated panties, and gave him a towel to clean himself up. When the poor boy had finished, they dressed him in a girls’ petticoat and, over that, a schoolgirls’ uniform!

Marlene held a pair of beige nylon panties in front of his face.

“More panties for you, panty-boy!” she sneered, “but this time, you’re going to put them on in front of the whole class!”

Ian’s protests were in vain as the girls dragged him back into the classroom. Marlene addressed the class.

“Right, boys and girls! Naughty boys like Ian have to be taught a lesson! So, watch! He is going to put on girls’ panties in front of you all!”

The boys and girls gasped! They were going to see Ian’s ultimate humiliation!

Marlene held the girly beige panties up for the whole class to see, waved them in front of Ian’s face, and then handed them to the boy!

“The class wants to see you put your girly panties on, Ian! Don’t disappoint them! Do it! Put your panties on, now!”

Ian’s will was broken! Slowly, he stepped into the panties, and began to pull them up. Slowly, Ian stepped into the panties!
The boys and girls watched excitedly. This was fun!
Eventually, he managed to get them up round his thighs and under the petticoat. “Wait!” Marlene called out. “Would anyone like to help?”

Every hand in the classroom shot up!

“Right, Tommy,” Marlene said to the youngest boy in the class, “you can help panty-boy Ian put his panties on!”

Tommy was the youngest boy in the class. He had full lips and long eye-lashes like a girl, and was the only boy Ian had ever fancied! But now, the pretty boy was going to humiliate Ian further! He stood behind Ian, grinning, and slipped his hands up Ian’s dress to seize the waist-band of the panties!

“Right, Tommy. Finish the job!”

Tommy could have pulled Ian’s panties up under the dress, but as he pulled the girly garment up, he also pulled up the front of Ian’s dress and petticoat, so everyone had a clear view as

Ian’s balls and **** as they disappeared into their silky prison! Ian’s **** and balls disappeared into their silky prison!

Somehow, being dressed in girls’ panties by this boy was the most humiliating thing Ian could imagine! He began to cry as the silky panties entrapped his male genitals!

“How sweet!” someone shouted, “he even cries like a girl!”

“Now, Ian,” Marlene said, “hold the front of your dress up so Tommy can adjust the fit of those panties!”

Tommy knew exactly what Marlene had in mind! As Ian held the dress up, exposing his panties to the class, Tommy began to play with the waist and leg elastics of the panties, snapping them and jiggling the panties about over Ian’s ****. In spite of, or because of his humiliation, Ian felt his **** swelling again, becoming erect and stiff, tenting out the front of the panties!

Tommy was quick to realize that Ian was in a state of sexual excitement. The younger boy began to pretend to reposition Ian’s **** in the panties, but all the time, he was tickling the end of Ian’s ****, or cupping Ian’s balls and jiggling them up and down, so that the beige nylon brushed over Ian’s **** with a silken caress! The whole class gazed in excitement as Ian’s panties rippled in constant movement.

As Tommy “played” with Ian’s **** in the panties, it became fully erect!

“Marlene, I can’t make his **** go down! What should I do now?” asked little Tommy, knowing full well what the answer would be.

Marlene grinned.
“Well, Tommy. We were always taught that to make a swelling go down, you have to rub it!”

So, Tommy rubbed Ian’s ****! Gently and slowly at first, but then fast and vigorously. Ian could not resist the result of this forced masturbation. He felt an irresistible climax begin to overwhelm him. Ian’s knees buckled. Tommy’s little fingers grabbed Ian’s **** through the nylon of the panties, and squeezed!

He felt Ian’s **** begin to throb, and then it was spurting into the panties like a fountain! Ian’s shame was complete. The whole class had seen him being wanked by a younger boy! Wanked while wearing GIRL’S clothes! Wanked through a pair of silky panties! Yet another boy had made him cum!

Marlene pulled Ian out of the classroom and made him take the wet panties off. She then reached under her skirt and pulled down her panties, and gave them to the hapless boy.

“Your lucky day, sissy! Put my panties on!”

Ian’s will was broken. He took the panties. They were totally transparent! He stepped into them and pulled them up. They settled round his little **** which immediately began to swell again! Marlene grinned at the sight of the boy’s penis growing in her panties, easily visible