Sissy School

"So, when does all this happen?" asked Jennifer.

"In a couple of days" answered Pam. "I want to monitor Len for another day or two, just to make sure of his routine. After that, a day to set everything up, and then we go. I'll call you a day ahead of time, but let's tentatively say three days from now."

"OK", said Jennifer, "the sooner the better!"

******************************************************

Now three days later here they were, sneaking up house to surprise Len. Pam had described in detail what was going to happen. "I must warn you, it's going to be quite embarrassing for you, as well as Len", Pam had cautioned her that morning.

"It can't be any worse than what I've seen on the video" Jennifer had replied.

"Seeing it in person, can often be unsettling" said Pam. "Remember you are going to have to watch while he masturbates and comes right in front of you. This is something most mothers never see their son's do."

Jennifer blushed but said, "I'll manage. I just want this disgusting nonsense with my panties and clothes to end."

Pam nodded and said "OK, then I guess we're ready."

As they approached the door, Elle joined them. She had been waiting in her car down the block for Pam and Jennifer to start walking towards the house. Behind Elle were the two large women in grey who had rung the doorbell a few minutes earlier.

Elle put her hand on Jennifer's shoulder and whispered in her ear "It's going to be fine."

Jennifer smiled grimly back at her and mouthed the word 'Thanks'. She was very happy to have Elle along. It's was comforting to have her best-friend with her during this ordeal. Jennifer and Elle had talked almost continuously about this moment for the last three days and now it was finally here. It was Pam however who suggested brining Elle along. "Ellenore is going to be an integral part of this from now on" she had said. "She needs to be there. Plus, the more women Len sees, the more humiliating it will be for him."

They had even discussed bringing Melanie along as well. Pam had suggested this and Jennifer and Elle were not opposed to the idea. However, when Jennifer discussed the matter with her daughter, explaining what she discovered and what she planned to do, Melanie had demurred. "I always knew something was up with him, so I can't say I'm surprised" she said. "It's about time you did something with him. Much as I'd like to see his face when you confront him, I have a project due at work and I can't afford to take any time off. However, keep me informed. I'd be happy to help out in any way I can."

Jennifer had been disappointed at Melanie's decision not to come, but she was very relieved that Elle was with her. 'I can't wait till this is over' she thought.

Pam took the door key out of her pocket and silently slid it into the lock. Noiselessly twisting the lock, she silently swung open the front door. The five women quietly entered the house and ascended the stairs, Pam leading the way followed by Jennifer and Elle with Pam's two large assistants bringing up the rear. Once at the top of the stairs the group moved silently in single-file down the hallway to Jennifer's bedroom door. The bedroom door was open and Pam held up her right hand, signaling them to stop, just short of the doorway. Pam took out her iPhone and brought up her camera app. Holding it up, so Jennifer and Elle could see, the three women looked at the image on the small screen.

Jennifer had to place her hand over her mouth to stifle a small cry of outrage. Elle, suppressing a smile, put her hand on her friend's shoulder as they watched Len just a few feet away from them around the corner of the open doorway. Len stood with his knees bent about two feet in front of the bed dressed in one of Jennifer's pleated skirts and a white blouse. With his left hand he was holding up the front of the skirt, the pleated material bunched in his forearm, which was pressed against his stomach. His right hand was inside a pair of white cotton panties, pumping away at an unseen, but obviously very erect penis. After watching Len for about 30 seconds, Pam put her iPhone away and holding up her right arm, pointed her index finger at the open door, signaling the group to move forward into the bedroom.

As they went through the doorway, Jennifer thought 'Len was going to finally get what he deserves!'

As for Elle, her heart was beating fast with anticipation and excitement. She had to admit that she was enjoying this, despite poor Jennifer's obvious discomfort. Not that she wasn't sympathetic towards her best friend's plight; Elle did not have any children, but she could still empathize with Jennifer. However, the idea of catching Len in such a comprising and shameful act made her excited and she could feel the wetness in her panties. He was going to make such a delightful slave! For the last couple of years, she had been watching him with increasing interest. She had known Len since he was a baby and loved him like an aunt. As time went on, she found herself flirting with him and then hugging and kissing him (in a very aunt-like way, of course). If only he wasn't her best friend's son, and off-limits she had thought. When Rosemary Goodman had approached her with a possible match and she had discovered it was Len, she was secretly thrilled. Thanks goodness Jennifer had not been upset with her and had quickly and surprisingly agreed to the match. Now they were closer than ever before, and soon, Len would be hers!

Pam had arranged everything down to the last detail. The assistants, as Pam called them, had posed as saleswomen to distract Len and lower his guard. "Subconsciously Len knows that it's extremely unlikely that he will be surprised twice in one day. In addition, it will make him slightly anxious so he will likely hurry things along. We don't want to have to wait around in the hallway all day while he fumbles around."

And she had been right. Now as the five of them stepped through the bedroom door, Pam said in a very stern voice, "And what exactly do you think you are doing?"

******************************************************

After the annoying saleswomen had left, Len immediately went back upstairs, and after tossing his robe on his mother's bed, fetched a Kotex pad and placed it inside the panties he was wearing. Walking over to the closet, he opened the door and selected a simple white blouse and a pleated skirt. He liked this skirt because it was loose and open, with its A-line cut. Normally he would have put on stockings and shoes, but time was running short and besides the damn saleswomen had spooked him. He needed to get moving. Once dressed, he admired himself in the full-length dressing mirror. The delicate material of the panties felt fantastic against his buttocks and contrasted nicely with the stick pad caressing his penis and balls. The pad felt incredible and his penis had grown hard as soon as it made contact with the Kotex pad. Closing his eyes, Len tried to savor the moment. His penis was hard, erect, and throbbing and his spine tingled with excitement. He could feel the silky soft material of his mother's clothes caressing his skin everywhere. So many pleasurable sensations all at once; it felt so sensual and Len felt very sexy and girlish, despite the ridiculous image that stared back at him from the mirror.

After a few minutes all these wonderful and sensuous sensations overwhelmed him, and closing his eyes, Len pulled up the front of the skirt and put his right hand into the panties and started stroking his penis. Later he would blame himself for closing his eyes, but for now he let himself go, enjoying all the fantastic sensations.

"And exactly what do you think you are doing?" said a woman's voice from behind him.

Startled, Len's eyes flew open and he jerked his hand out of the panties as he reflexively turned around to face the unknown female voice. Len's mouth fell open, speechless as he saw the owner of the voice. She was a beautiful woman in her mid to late thirties with a voluptuous figure. Her hands were on her hips and unbelievably she was flanked by his mother and Elle and the two large women dressed in grey whom he had seen though the peephole only minutes earlier. All the women stood looking at him with angry and unhappy expressions on their faces. Elle was the only exception; her mouth curved upward in a slight, amused smile.

Len's eyes widened in horror, seeing his mother and Elle, and the other strange women standing next to them. Petrified, all he could do was manage a soft groan.

"Well, answer me, young man" demanded the woman sternly. Len's eyes flicked from his mother to Elle, and back to the woman again. Dumbfounded he stared at her. Smoldering brown eyes stared back at him, searched his face, and sparkled with disapproval as she eyed him up and down, her gaze pausing momentarily on the panties he wore. Embarrassingly, the skirt had caught in the waistband of the panties, leaving them exposed for everyone to see.

"I...I..." Len finally managed to stammer, unable to articulate further. Thoughts and questions raced through his head faster than his mind could process them. Where had this woman come from? What were his mother and Elle doing here? How had they gotten into the house? Why hadn't he heard them come in?

"You what?" demanded the voluptuous woman.

"I was... I was just trying..." began Len, struggling to find his tongue and recovering a little from the shock that held him paralyzed in front of his mother, Elle, and their stern companions. How can this be happening? He thought. I must be hallucinating.

"Trying what?" asked the woman, tapping her right foot impatiently on the carpet and continuing to eye Len.

"I wanted to...I was just seeing if..." Len stammered again.

"Seeing what?" The woman questioned, her tone harsh and skeptical.

"If they would...fit" said Len, finally able to complete a sentence.

"How dare you!" said his mother angrily.

Pam loudly exhaled and pointing at the panties she said "You're doing more than seeing if they fit."

Len looked down and saw his penis tenting the panties. It stuck straight out, throbbing against the Kotex pad. Blushing bright red, he fumbled with the skirt, trying to pull it out of the panties. This can't be happening he thought. It was his worst nightmare come true! I must be dreaming. That's it, I am asleep, in my bed. I'll wake up soon, alone, and this will all be over, just a bad dream.

Jennifer also looked to where Pam was pointing. 'Oh, god!' she said silently to herself. Len's erection was visible to even the most casual observer. This made her even angrier (if that was possible). Len was going to get what he deserved once and for all!

Elle standing beside her fought to keeping from chuckling. Len looked so ridiculous, yet adorable in his mother's clothes. But the best thing was the expression of shock and surprise and disbelief on his face. 'God! He's going to make such a good slut!' she thought. Under her dress, her panties were soaked. She had not been this excited in a very, very long time.

"That's disgusting!" Pam said harshly "and in your mother's panties no less. You should be ashamed of yourself young man!"

Len blush turned a deep red as his shame and embarrassment increased. His penis however took on a life of its own and Len felt it throbbing uncontrollably. Why won't it get soft? He asked himself. The darn thing was hard as a rock and pulsating. Things were bad enough, without having a hard-on in front of his mother and Elle and their demanding companion. But the more embarrassed Len became, the harder his penis got. He couldn't control it, try as he might. It was like some weird nightmare. "Oh god, groaned" Len. Why hadn't he woken up yet?

"God has nothing to do with this!" said Pam emphatically. "Don't make excuses to me! I've been watching you for several days now and I know exactly what's going on here!"

Len's mouth fell open in shock. This woman had been watching all week! How could that possibly be?"

"I've known what you've been up to from the beginning" said Jennifer fiercely, yet quietly to her son. "I also know that you think that you've been fooling me. A few weeks ago, I consulted with Dr. Berkshire here and she agreed that it was time to put an end to your disgusting and disrespectful behavior."

Len looked at his mother and his eyes widened with fear. Her quiet voice frightened him more than if she had shouted at him. Beneath the quiet he could sense her barely contained furry. Len knew he was in big trouble. What bothered him even more was his mother's statement that she was here with this Dr. Berkshire to 'put an end' to what he was doing. Reluctantly, Len realized that what was happening was not a bad dream. It was instead his worst nightmare come true. He was in big, big, serious trouble!

"Mom, I'm sorry" said Len, his words sounding hollow in the crowded room.

"Not as sorry as you're going to be" replied Jennifer.

"Please, mom, I beg you" pleaded Len "I'm sorry, please it won't happen ever again." But even as these last words left his mouth, Len knew that a simple apology was not going to get him out of this awful mess. How could he have let this happen?

"Yes, it will" said Dr. Berkshire, pointing at the panties Len wore.

Len's mouth opened again, and he looked from his mother to Dr. Berkshire to Elle, and down to the panties. His penis was harder than ever and visibly throbbed against the Kotex pad. Len groaned and fought to control himself. He couldn't get the damn thing to relax! A shiver went through his body as it tingled and quivered with desire, just like before a spanking. What's happening to me? Len thought.

"It's clear that you can't control yourself" said Dr. Berkshire. "That's why we're here. You're a sissy who can't control himself"

"No!" said Len, but even to his own ears, the denial did not sound convincing.

"Yes, you are" said Dr. Berkshire, stepping closer to him. "And I'm going to prove it to you."

"No please!" pleaded Len. "Mom, please I am sorry. Please it won't happen again! You've got to believe me!"

But Jennifer just shook her head and Dr. Berkshire took another step towards him.

In desperation Len looked at Elle and said, "Aunt Elle, please tell them, please!"

But Elle just looked at him with the same amused half-smile on her face.

Nodding at the two large women in grey, Pam motioned them from where they had been waiting by the door. The two women walked swiftly towards Len and, taking positions on either side of him, grabbed his arms.

Len, gasped in surprise and began to struggle, however the two Amazons were surprisingly strong and his efforts were completely ineffectual. "Let me go!" he protested in desperation.

Dr. Berkshire sighed and said "There is no point in struggling. My assistants are well trained and you will only hurt yourself if you persist in trying to break free."

Len continued to struggle but soon realized that Dr. Berkshire was correct. Both the women holding onto his arms were bigger than he was, and judging by their iron grips, much stronger also. After another minute Len gave up, unable to move his arms.

"That's better" said Dr. Berkshire.

"What are you going to do?" asked Len.

"Exactly what I said" replied the doctor.

"And how are you going to do that?" said Len starting to regain some of his composure. "I don't believe you."

"I know" Dr. Berkshire said matter-of-factly. "But you will."

"Never" protested Len.

"I have a very simple test" continued Dr. Berkshire, "and a proposition. If you past the test, then I (and the two women holding you), will leave and never bother you again. If you fail, then you will come with me, and willing do whatever I say."

This is insane thought Len, but he could see that Dr. Berkshire was quite serious and with the two Amazons holding him like a vice, there was little he could do but acquiesce. Summoning his courage, he cautiously asked, "What's the test?"

"Simple" said Dr. Berkshire, stepping right next to him, her soft brown eyes searching is face, "I am going to pull down the panties you are wearing and expose you to everyone in this room, including your mother and Elle. I'm then going to rub your penis. If you cum, you fail. Only a true sissy could remain hard in front of his mother and cum."

Len gulped, not believing what he had heard. "No" he said finally.

"Well then" said Dr. Berkshire your refusal to take the test shows clearly that you are a sissy." Nodding to the restrainers she said "take him away."

The two Amazons started to pull Len towards the door, but he said "No, wait." Len's mind was racing. He was caught in a Catch-22 situation he realized. The idea of being exposed in front of five women, one his mother (no less) horrified him. Inside the panties however his penis throbbed uncontrollably. How did I ever get into this mess? He thought. But there was no escape. The two women held him tightly and Len could barely move. Even if he did somehow manage to break free, what was he going to do? Run out of the house, dressed in his mother's panties and clothes? He would be arrested for sure and taken to jail. Then he'd really be in for it. Len knew he wouldn't last two minutes in a jail cell dressed in his mother's clothes, not to mention trying to explain himself to the police or a judge. This Dr. Berkshire was going to drag him off either way to god only knew where. What awaited him, Len could only guess. One thing was certain, he was almost sure that he wasn't going to like it. His only chance was in passing this ridiculous test. If he failed, then he would be no worse off. The only problem was that the idea of being 'tested' excited him (as well as being taken away). And in front of Elle, no less! His penis was harder than ever and still throbbing like crazy. Still some chance, no matter how ridiculous or desperate was better than none. However, in the back of his mind Len thought, what's wrong with me?

"Well?" said Dr. Berkshire.

"OK" said Len quietly.

"OK, what?" demanded Dr. Berkshire.

Len gulped, took a deep breath and said softly "I'll take the test."

"Good" said Dr. Berkshire.

Standing directly in front of Len, Dr. Berkshire pulled down the panties he was wearing, exposing his erect penis and the Kotex pad to everyone in the room.

Len blushed and groaned. Although it wasn't accurate, he felt as if everyone in the room was staring at his erection. He could feel his penis throbbing and embarrassment pulsated through is mind. This is so humiliating thought Len. Still part of him was secretly thrilled. He had often fantasized about exposing himself to Elle, perhaps even playing 'doctor' with her. Now here he was, standing in front of her, his penis erect and full exposed to her gaze. Elle smiled at him wryly and Len blushed, his entire body tingling. 'Oh god!' he thought. Even if he managed to pass this test, Len knew that he would never be able to look Elle in the eye again, not to mention his mother!

"Aren't we excited? Dr. Berkshire commented. "Wearing panties makes you hard, doesn't it sissy boy? And what's this?"

Dr. Berkshire pulled the Kotex pad from the crotch of the panties and held it up for everyone in the room to see. Smiling slyly, she said "Thick pads excite you too? Or perhaps you would like to have a period?"

Len groaned again and closed his eyes in shame. He was not sure what a period was, but he dared not look at Dr. Berkshire and he was too embarrassed to even glance at his mother or Elle. This had better be a dream he thought in desperation.

As if reading his mind, Dr. Berkshire said "You can't just close your eyes and pretend this is a dream. You've been caught and how I am going to expose you, in front of your mother and Ellenore, for the sissy that you are."

With that, Dr. Berkshire reached into her pocket and produced a small bottle of lubricant. Opening the top, she held the bottle over Len's erect penis and squeezed. Lubricant flowed out of the bottle and onto Len's throbbing organ. Len winced as the cold lubricant touched his hot penis. Closing the top of the bottle and placing it back into her pocket Dr. Berkshire took Len's penis in her right hand and said "nice and hard. This won't take long." With that, she started stroking his penis.