Sissy School

His mother had looked at him and said, "That's because girls don't play around down there like some boys I know do."

Len had blushed and Elle curious and half amused, had said, "What's this all about?"

"Nothing" Len said quickly, now even more embarrassed.

His mother had glanced at Elle and the two women traded knowing looks and a slight smile appeared on Elle's lips. Fortunately, his mother let the matter drop there, but the message was clear. After that, Len was much more careful about what he said and more importantly, he stopped trying to get (what he now referred to as) forbidden information from his mother's girlfriends.

In desperation, Len had even tried talking with his sister, but their relationship had never been good, and broaching such a delicate subject with her was both difficult and awkward. Opportunity was another problem. Since Melanie no longer lived at home, Len only saw her only on weekends, and not every weekend at that. One Sunday when they were alone (their mother had run to the grocery store) Len had made an attempt at discussing the taboo subject of sex with his sister. "So, do you have a boyfriend now that you are living alone?" he inquired casually.

"Why do you ask?" replied Melanie suspiciously.

"Just curious" said Len, adding "it must be lonely living alone". The last remark was a mistake and Len realized this as soon as the words were out of his mouth.

"Such a male comment!" said Melanie angrily. "Just because a woman lives alone does not mean that she is lonely. I don't need a man in my life to be happy! Besides when did you ever care about how I felt?"

Len had apologized but that had ended the conversation and with it Len's attempts at gleaning any information from his sister. All this was very frustrating of course, but nonetheless it had not prevented Len from experimenting on his own. Fortunately, his mother's job kept her out of the house most of the day. This left Len plenty of time to explore and to play, which was essentially the only avenue open to him. Still, there was only so much he could do by himself. Discovering his mother's panty and bra drawer had been a big leap-forward.

During the day, while his mother was at work, Len had found himself inexplicitly drawn to his mother's bedroom as if by some unidentifiable invisible force. He would walk by it, stop at the door, and without going inside, stare at the dresser and the drawer containing the panties. Sometimes, Len would find himself just standing there and staring without any recollection of why or how he had come into his mother's bedroom. However, Len did notice that the frequency of these visits was increasing with each passing day and that the time he was devoting to staring at the closed drawer was getting longer and longer. Worse still, were the erections these visits always seemed to produce. At first this disturbed Len but soon he relaxed and accepted what he was unable to control. After all, although being naughty and playing with his penis was always satisfying, it was also horribly monotonous. Eventually he worked up the courage and took the plunge.

Going to his mother's bedroom, Len opened the drawer and took a single white cotton panty from it. He chose white because there were more of these in the drawer than any other color. Closing the drawer Len had quickly undressed. Holding the panties, he saw that his hands were shaking with excitement. Lifting his right leg, and then his left, he stepped into the panties and pulled them up, around his waist. They were a little tight, but overall, not a bad fit. They also felt wonderful! The soft material caressed his skin and incased his penis in a white seamless cloud of delight. Almost immediately Len felt his penis stiffen with an erection. As if by magic, he saw the front of the panties inflating and stretching until they resembled a small tent around his groin, with his penis acting as the tent-pole.

Len's penis throbbed inside the soft material sent a shiver of excitement down his spine. He could not control himself; pushing the panties down, he exposed his erect penis and rubbed it. Within a few seconds, he came, cum shooting onto the carpet. Fortunately, and by some miracle, none managed to get on his mother's panties. Len hopped over to the bathroom, the panties between his knees, and cleaned up. Taking off the panties he returned them to the bottom of his mother's panty drawer and cleaned up the carpet.

For the next few days, Len kept trying on his mother's panties, with the same results. The small white garment was remarkable. It was unbelievable that something so insubstantial could produce such intense and overwhelming sensations. Len had never experienced such powerful orgasms in his life. However, he also realized that he now had a problem. Although his mother had not yet discovered anything amiss with her panties, there was a very real possibility that sooner or later she might. That's when Len had started experimenting, rearranging his mother's panties in the drawer. To his surprise she never said or even hinted that something might be amiss. This pleased Len greatly, since he knew that his mother would not hesitate to speak up if she even had the slightest suspicion that something was out of place.

After several weeks of experimenting with panties of different colors, styles, and materials, Len decided to explore more the contents of the dresser. The next drawer down contained panty hose, and the drawer above, bras. There was so much stuff, that Len was at first overwhelmed with the choices all the feminine clothing presented. The panty hose looked interesting, but difficult to put on. It also looked as if it might be tight and uncomfortable. Len therefore decided to try on the bras. Like the panties there were several different styles and colors to choose from. Len decided to start off simply and chose a plain beige one with soft comfortable looking cups. Putting it on turned out to be harder than he had imagined. It took him almost fifteen minutes before he managed to adjust the straps and fasten the awkwardly placed clips in the back. However, when he finally did get it on, it felt superb. Choosing a matching pair of beige panties, he quickly pulled them on, and then went to the mirror to examine the result. He looked stilly and stupid, but the female garments felt great, and of course, they were so exciting to wear. Anyhow, how they made him feel was the important thing, and he felt wonderful!

And so, it went, day after day, week after week. As time went by, Len explored more and more of the delights contained in his mother's bedroom. After the bras came the pantyhose, then dresses and shoes. Next was the attached bathroom. There Len found makeup (which he tried but abandoned as being too messy and unrewarding) and Kotex. The Kotex was a real find: the thick soft pads fit in front of the panties had felt fantastic against his penis and balls. He was not exactly sure about their purpose, but the instructions on the box were clear enough as to their usage. More perplexing were the tampons; the diagram on the box was crude and confusing. Were they really intended to go up his ass? Unsure, Len decided against trying them. Perhaps in the future, if he could somehow get more information about them.

Now, well over a year later, Len felt very comfortable inside his mother's bedroom and with its contents, which he regarded as belonging, at least partially, to him. He had even learned some degree of control over his body. In the beginning he would get hard, stroke himself a few times, and cum within minutes or even seconds. Now he could go an hour or more before giving into temptation and coming. Best of all was the way the clothes made him feel: so feminine and girlish! Oh! How he wished that he could be a girl! Or at least feel like one! Today, however Len was a bit pressed for time, due to a late start and all the reminiscing he had been doing. Time to get going; the clock said 2:30PM, only 30 minutes before he had to start cleaning up!

Suddenly from down stairs Len heard the noise of a car pulling up in front of the house, and doors slamming. Len froze, his heart in this throat. Next, came the sound of female voices talking outside. Rushing with hands shaking, Len closed the dresser drawers, and ran to his room. There he put on his robe. A knock on the front door, followed by the doorbell chime (which echoed like a church bell), disrupted the peace of the quiet house. Len tiptoed silently to the front door and looked through the peephole. On the porch two large women dressed in identical gray pantsuits stood, holding pamphlets. Len relaxed slightly. Damn saleswomen canvassing the neighborhood! This had happened to him before. The doorbell chimed again followed by another knock. All he had to do was remain silent for a minute or so and they would go away. Len heard one of the women through the door say "No one home." Still looking through the peephole Len saw the two women turn and walk away, continuing next door to bother the neighbors no doubt.

Len let out a slow breath and said "Damn" out loud and to himself. This sort of thing happened once a month or so, but it never ceased to alarm him. Well at least they hadn't shown up while he was in the middle of playing with himself; that was really annoying! Turning around, Len hurried back upstairs taking his robe off has he climbed the stairs. "Got to get going" he said out loud again.

Chapter 3

Jennifer sat next to Pam Berkshire in the back of the van and stared at the large flat screen TV, watching Len as he moved about the house. The scene was much like the one she had witnessed a week earlier in Dr. Goodman's office, except what she was seeing now was not recorded but happening live as she watched. Jennifer watched as Len strolled into her room, stripped naked and went into her bathroom to shower and then slather her expensive body lotion on this arms and legs. Next came the powder followed by Len rummaging and pawing through her intimate apparel. Jennifer shook her head and tried to control her disgust and anger. "Damn him!" she said to Pam. "Just look at him!"

Pam nodded and said "It won't be much longer now."

A few minutes later a car pulled up to the cub and two large women, dressed in identical grey pantsuits, got out and knocked on the door. On the monitor Pam saw her son, freeze and then rush to his room to put on a robe.

"Probably worried it's you" said Pam.

"Yes, most likely" said Jennifer as she watched Len creep to the front door and silently cower in his robe as the grey-suited women knocked. When the women left, Len hurried upstairs, taking off his robe as he went.

"That's it" said Pam, time to go.

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

Three days earlier, Dr. Goodman had introduced Jennifer to Dr. Pamela Berkshire. "Pam is my assistant and will be taking care of Len" she said by way of introduction.

"Pleased to meet you Doctor Berkshire", said Jennifer.

"Same" said Pam, "but please call me Pam. May I call you Jennifer?"

"Sure" said Jennifer.

Pam was a woman of average height in her late 30's, with a voluptuous figure, which was further enhanced by her very large and full breasts. She had shoulder length light-brown hair and large brown eyes which could appear soft and sympathetic (as they did now) or hard and fierce. Full pouty lips lent her face a pleasant and empathetic expression, which Jennifer found instantly appealing.

"I am very glad to meet you at last" said Pam with a sincerity that seemed both genuine and true. "Dr. Goodman has told me so much about you and Len and I have been looking forward to working with both of you."

"Same here" said Jennifer.

"Please", Pam said, pointing to a small sofa in front of her desk, "be seated and make yourself comfortable. Can my secretary, Grace, bring you anything? Coffee perhaps or maybe some tea?"

"No, I'm fine, thanks" said Jennifer sitting on the sofa, which was remarkably comfortable.

"Well let me know if you would like something later" said Pam, sitting down in a large leather armchair opposite the sofa where Jennifer sat.

Dr. Goodman looked at Jennifer and said, "You are in very good hands. Pam is fabulous, as you will soon find out for yourself. I'll leave you in her capable care. If you have any questions or concerns you can always call me, at any time, night or day."

Jennifer said "Thank you doctor" and Dr. Goodman turned and left the room, closing the door behind her.

"Well, let's see" began Pam. "I talked with Dr. Goodman extensively about your son Len and your conversations. I have also seen the video. I want to reassure you that I am very confident that Len will make a wonderful partner for Ellenore. I am here to feminize and train Len and get him ready for a committed female-led relationship."

The word 'training' struck Jennifer as odd. She had heard Dr. Goodman use it during their conversation and now here it was again. "Yes, I would like you to treat Len so he can marry Elle and make her happy" said Jennifer.

Pam smiled slightly and said "We don't treat patients here Jennifer, we train sissies. Your son cannot be treated, since technically there is really nothing the matter with him. Rather we can help him, through feminization and training to discover his hidden desires and realize his full potential as a devoted companion to Ellenore. In the end, this will leave him feeling fulfilled and happy. In short, we can help him discover who he really is."

"I'm not sure I understand" said Jennifer.

"Of course," said Pam, her tone understanding and confidential. "Most women in your situation are usually confused and more than a little embarrassed. This is quite understandable, as well as normal. It's our job, no my job, to explain everything so you will feel confident in your decision and comfortable with your choice."

Jennifer sighed, relief easing some of the tension she felt. "I am confused, I must admit" she said. "This is all so new and bewildering."

"Yes, and your feelings are quite normal" said Pam. "I know Dr. Goodman only explained briefly what we do here. Let me provide you with more detail. After that I am sure you will have a better idea of what is happening with your son, and what will happen to him, once he is here."

"Yes, please do" said Jennifer, trying to keep some of the anxiety out of her voice.

"Len is typical of many if not most males" began Pam. "I am sure Dr. Goodman explained that all males have fantasies of being women at some point in their lives. The ancient Greek myth of Tiresias, for example, illustrates both the antiquity and durability of this fantasy. Some men never act out their feminization fantasies, either because they are too frightening or because they fear discovery. Others, will do some exploring, and like Len, engage in cross-dressing, and the like. For many, this is where it stops. Perhaps their curiosity is satisfied or they fear reprisal if they are discovered. Whatever the reason, the exploration stops. For others, however the exploration continues. It eventually begins to take on an almost addictive quality. Such males can't stop; what started out as touching leads to trying on and then wearing. The more they do it, the more they need to continue. You can see where this is leading, I'm sure."

"Yes!" said Jennifer sitting forward on the sofa. "It's like an obsession."

"Exactly" said Pam. "But compulsion is a more accurate description. Such males are compelled to wear female clothing so they can fulfill their deep longing and desire to feel like women. Unfortunately, for most males this must be done is secret, least their feelings become known, and they suffer the inevitable shame and humiliation."

"I know" said Jennifer. "That's why Len only puts on my clothes when he is alone in the house."

"Yes" said Pam, "but there is more to it. For some males, shame and humiliation is terrifying and they will do anything to avoid it. Such males go to great lengths to avoid discovery, even to the point of giving up their 'habit', so to speak, for long periods. For others however, shame and humiliation are both fearful and exciting."

"Yes, Dr. Goodman called this the Loop", asked Jennifer.

"Yes, exactly" said Pam. "Such males become sexually excited when they are actually being shamed or humiliated by women. Worse, they are ashamed that they are sexually excited and that their excitement can be seen. This in turn makes them even more excited. It becomes a vicious circle or loop, so to speak, and hence the name."

Jennifer blushed. "So, you believe Len experiences this Loop?"

"Yes," said Pam. "It's quite obvious from the video. There are various technical terms for this such as 'positive feedback' and the like, but calling it the Loop, is clear and straight-forward."

"So, what does all this have to do with training?" asked Jennifer.

"It makes Len an ideal candidate" answered Pam. "As such, psychologically he is predisposed to serve and satisfy his partner, Ellenore. This is what he wants, even if he does not realize it yet. Forced feminization and training will give him the realization of who he is and what he truly wants. In addition, it will give him the means and knowledge to achieve this goal within a healthy and loving relationship. This in turn will make him happy and complete."

"So, what's involved in this training?" asked Jennifer.

"There are essentially two parts to his training. This first is what I like to call boot camp. This is where Len will be feminized and learn the basics of being a sissy and how to serve and please a woman. The second part is customized and is different for each candidate. For this, you, Ellenore, and I will sit down and work out a program. The idea is to customize Len's training to Ellenore's specific needs and desires. Of course, your opinions and ideas are also welcome (as well your daughter's), so that's why all of us will work together to plan this phase of Len's training."

"I see" said Jennifer, not really sure that she understood what Pam was telling her.

"I know it's all very vague and confusing at this point, but soon everything will be clear. In the end, it will all seem very natural and simple."

"So, when do we start Len's training?" said Jennifer, anxious to begin.

"Well first we need to get Len over here and have him sign the necessary agreements."

"Yes, of course" said Jennifer, blushing as she remembered what Dr. Goodman said about getting Len to 'agree'. "So how do we go about getting Len here?"

"I've been watching Len now for about a week" said Pam "and he has a pretty regular routine: he gets up around noon, has a quick breakfast, then showers and shaves. Next, he goes through the ritual of putting on lotion and powder and finally he selects panties, bra, and a dress. Once he's dressed, he spends about 20 minutes or so enjoying your clothes and feeling feminine until he cannot control himself any longer. The ritual ends with Len masturbating and ejaculating into your panties. After that he spends about 20 minutes cleaning up, and he is done for the day. All and all he's done by 3:30 or so."

Jennifer blushed when Pam mentioned Len's masturbation, but she was also angry at her son and she said, "It seems you could set your watch by what he does."

Pam smiled slightly and said "Yes, it does seem that way. But this makes things much easier for us."

Jennifer's eyebrows went up, but she remained silent.

Pam continued, "We want to catch him in the act. Essentially this is what he wants. After that, we will bring him back here and go from there."

"What if he resists?" said Jennifer.

"That's never happened" said Pam. "However, I have a couple of assistants, just in case he needs some...persuading."