Sissy School

Copyright 2018 by Zeta

All rights reserved

This story may be freely distributed in electronic form but must include this copyright.

Sissy School

is a work for pure fiction and all locales, names, characters, places, and incidents are the products of the author's imagination. Any resemblance to actual events, locales, or living persons is entirely coincidental

A very

special thanks

to

bbwgalpresent

whose sharp eyes and exemplarily editing skills greatly improved the readability of this story.

Contents

Chapter 1

Jennifer Kay looked away from the 60-inch flat-screen monitor, her face pale and grim. "So, it's true" she said, the resignation in her voice unmistakable.

"I'm afraid so" said Dr. Rosemary Goodman, sympathetically. "Seeing

is

believing, I'm afraid."

Jennifer sighed looking away saying, "Yes, all too true."

What she had just seen was her 26-year old son, Len, strip naked and then dress in her panties, bra, stockings, and one of her finer dresses. His penis had been so hard and erect that she could see it poking the front of her dress through her panties as he proceeded to parade though her house, sashaying like a girl, and admiring himself in every mirror he encountered. And if this hadn't been enough, he had ended this 'stroll' by pulling up the dress, rubbing himself through her panties until he had cum, semen extruding though the front of

her

panties and running through his fingers and dripping onto the floor. All this in crystal-clear, life-sized high definition imagery.

Looking back at Dr. Goodman, Jennifer said angrily "I knew something was up with him, but...but nothing so...so disgusting! And in my panties, no less!"

"I know how troubling this can be to see" said Dr. Goodman, her tone still sympathetic. "However, we now know exactly what Len has been doing so we can now start helping him."

"Helping him!" said Jennifer, still angry and becoming frustrated. "He's a pervert, a dirty little pervert and he should be spanked till he can't walk. How can you possibly 'help' him?"

'He's not a pervert" said Dr. Goodman, her voice firm but reassuring. "In fact, your son is quite normal; he just needs some guidance and training".

"Normal! You call that normal?" said Jennifer pointing at the blank TV screen.

"Yes" replied Dr. Goodman calmly. "It's typical male behavior, nothing to be alarmed about."

"How can you call what we just saw 'normal'?" said Jennifer, still angry but also starting to become curious. "Surely, you're not implying that all males dress in their mother's clothes and...and...well, you know."

Dr. Goodman suppressed a smile, took off her glasses and placed them on her desk. "No, of course not. But it's not exactly uncommon either."

"Not uncommon" echoed Jennifer, her anger fading and her curiosity growing.

"For all their bluster and macho behavior most males have feminine fantasies, of one sort or another. Most would never admit to them of course, and fewer still would dare to act them out, however, it's not uncommon for some males to privately exercise their fantasies especially if they feel confident that they won't be found out. It may seem odd, but it actually happens more than one might think."

"Really?" said Jennifer, becoming intrigued.

"Yes, quite so. Len is just one of those males that have taken the first step from fantasy into reality. In a way, it's quite brave of him."

Jennifer thought about this for a moment and then said skeptically, "Even if what you say is true, I can't have him dressing up in my clothes, and...and, well you saw what he did."

"Yes, I quite agree with that" said Dr. Goodman.

"Well, what's to be done then? Even if you could somehow stop him from dressing up in my clothes, he still would have all the other idiosyncrasies we talked about earlier. I don't see how you can help him."

"I understand your frustration and concern" said Dr. Goodman. "But really, Len is going to be just fine. Remember what we discussed during our first meeting?"

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

Jennifer sighed and sat back in her chair, remembering her first visit with Dr. Goodman. She had come to see Dr. Goodman about three months ago on the recommendation for her life-long and best friend Ellenore Daniels. Ellenore had known Len since he was a baby and treated him like a nephew. Len loved Ellenore, or Elle, as he and everyone else called her, and sometimes Jennifer thought he had a better relationship with her best-friend than he did with her or his older sister Melanie whom he seemed to hate. In any event, Jennifer had discussed her growing concerns with Elle, and she had recommended a visit with Dr. Goodman, a psychiatrist and close personal friend. Jennifer had been reluctant, but her motherly concerns had eventually outweighed her trepidation and she had finally gone to see the good doctor.

Dr. Rosemary Goodman had not been anything like what Jennifer had been expecting. First of all, her 'office' was actually a mansion-size house in one of the best neighborhoods in town. "This is going to be expensive" she thought as she approached the house. She couldn't have been more wrong. Dr. Goodman had not seemed to care about money at all, a fact Jennifer had found surprising. "I work on a sliding scale which you will find quite affordable", she had said, when Jennifer had broached the subject straight away. Secondly, Dr. Goodman was not at all like Jennifer's idea of a psychiatrist. Tall, blond, buxom, and shapely, she looked more like a model than a doctor. Her dress was elegant but casual, as was her manner. Finally, there was none of usual Freudian nonsense of answering questions with questions. Dr. Goodman was straight forward and always answered all her questions in a matter-of-fact manner.

"How long have you suspected this has been going on?" she had asked.

Jennifer had pulled at her necklace and said, "About a year, perhaps a little longer."

"And you have done nothing, until now?"

"No" replied Jennifer, still pulling on her necklace.

"Alright. Tell me about your son, Ms. Kay."

Jennifer stopped pulling on her necklace and said "Well for the most part, Len's been a good boy. He never really got along with his older sister Melanie, but besides that and he's never really given me any trouble, at least not until now. Even so, I am not sure 'trouble' is really the right word for it."

"Oh" said Dr. Goodman matter-of-factly, "then how would you characterize Len's behavior?'

"I don't know exactly" replied Jennifer, pulling on her necklace again. "Odd. Yes odd, I would say."

"In which way?"

"Not in a crazy way or anything like that" said Jennifer. "It's just that Len has never behaved like you would expect a boy to behave, if you know what I mean. I blame myself a lot for this, since I was forced to raise him by myself".

"You mean he's always been around women" said Dr. Goodman.

"Yes, exactly" replied Jennifer. "All my friends are women, and Len is always surrounded by females. I think it's why he's the way he is."

"And how's that?" asked Dr. Goodman.

"I don't know exactly...shy, not withdrawn, but he stays to himself a lot" answered Jennifer. "He does like hanging around my girlfriends however, especially Elle" added Jennifer quickly.

"I see" said Dr. Goodman. "How does he get along with your girlfriends?"

"That's just it" said Jennifer, moving her hand away from her necklace and waving it, "he gets along great with them. He chit-chats and carries on like he's one of the girls. In fact, it's too bad he wasn't born a girl, like his sister."

"You said that he does not get along with his sister" commented Dr. Goodman. "Can you tell me about that?"

"I'm not sure there is much to tell. His sister Melanie is quite a bit older, ten years to be exact. They never interacted much, probably because of the age difference. When Len turned 13, Melanie was already out of college and living on her own. Before Melanie left for college they used to fight a lot. Len would tease her about her clothes, appearance, and boyfriends and so on. Typical brother-sister stuff. Used to drive her crazy. Nowadays they see each other on weekends, but there is little interaction."

"I see" said Dr. Goodman. "But otherwise he gets along well with your friends".

"Yes" said Jennifer.

"Hmm" said Dr. Goodman. "So, what are your concerns?"

"Well when he's not with the girls or me, he just stays to himself. He also doesn't have any male interests like sports or cars or even girls own his age. He's basically a grown man, and he's never had a girlfriend. I thought he might be gay, and I even asked him, but he claims he is not, and I believe him."

"Perhaps he just enjoys the company of older women then" said Dr. Goodman.

"Yes, that's what I thought too" said Jennifer, starting to pull at her necklace again.

"But?" said Dr. Goodman.

"Well..." began Jennifer, but she stopped, a blush spreading over her face.

Dr. Goodman waited a moment then said, "When did you first suspect?"

Jennifer looked down and said "About a year ago. Len is home most of the time and pretty much has the place to himself while I'm at work. I started to get the impression that my things have been moved around, that they were not quite how I had remembered leaving them."

"By 'things' you mean articles of your personal clothing" said Dr. Goodman.

"Yes" said Jennifer. "Very personal articles" she added after a few moments, and then blushed again.

"Of course," said Dr. Goodman.

"It was all very odd and nothing that I could place my finger on exactly, continued Jennifer. "It seemed to start with my panty drawer. It's hard to describe since nothing was missing, but it seemed to me as if someone had been in there, perhaps looking for something. Later, I noticed the same thing with my bras and stockings, and finally my dresses. At first, I thought it was just me being absent minded or just plain forgetful. However, my intuition kept gnawing on me, telling me that something was not quite right."

"I see" said Dr. Goodman. "And so, you decided to find out."

"Yes, exactly" replied Jennifer impressed at how perceptive Dr. Goodman was. "I arranged my panties in a particular way so I could tell for sure it they had been moved. Sure, enough when I came home, nine times out of ten they had."

"But you still were not that concerned" commented Dr. Goodman.

"Yes" answered Jennifer. "I thought that perhaps Len was curious or maybe looking for money (although he never seems to spend any and I always give him what he asks for without any hassles)".

"And?"

"And then I noticed that some of my panties seemed to have been worn" continued Jennifer, her voice almost a whisper.

Dr. Goodman remained silent but nodded encouraging her to continue.

Jennifer looked up and her eyes were full of tears. She was not sad, but frustrated and worried. "I found some panties in the laundry that should have been in my drawer and they looked...used."

"Did you confront Len?" asked Dr. Goodman.

"No" said Jennifer drying her eyes. "I couldn't be absolutely certain it was Len and even if I was, I had no proof. If I confronted him and he denied it, then what was I supposed to do?"

"It's a delicate situation" agreed Dr. Goodman.

"Yes" agreed Jennifer. "However, I did decide to discuss it with my best-friend Elle; you know Elle Daniels? She's the one that recommend that I come and see you."

"Yes" said Dr. Goodman tersely, smiling slightly.

"So here I am" said Jennifer. "Do you think you can help me, or more importantly, Len?"

"What your son is doing is not uncommon" said Dr. Goodman reassuringly. "I understand your concern that he might be wearing your intimate garments and, that given some of his other behavior that you described, that this might indicate a more serious problem".

"Yes, exactly" agreed Jennifer.

"Well first off, let me reassure you that Len's behavior, although not conventional, is not uncommon either, or for that matter all that unusual."

"What?" said Jennifer, not sure that she had heard Dr. Goodman correctly. "Come again."

"Many, many males have fantasies that involve dressing up, or even acting like, women. It's quite common" explained Dr. Goodman.

"Sexual fantasies?" asked Jennifer.

"Yes" said Dr. Goodman.

Jennifer looked at her skeptically and then said, "You mean that most males dress-up like my son?"

"No" said Dr. Goodman. "In fact, most don't."

"I don't understand" said Jennifer, looking confused.

"Most males have sexual fantasies of being a woman or dressing up like one" explained Dr. Goodman. "At the most basic level, it's a matter of curiosity. Women have similar fantasies about being male."

Jennifer, nodded, blushing slightly.

"For most males these sexual fantasies are kept private and never acted upon. In essence, they never rise above the level or idle curiosity. For other males, this curiosity is taken a step further into experimentation, and in some cases, it can become a significant part of their lives."

"You mean they become...women?" asked Jennifer

"If you mean, have hormone treatments followed by sex reassignment surgery, then no" said Dr. Goodman. "That's entirely different, and from what you have described about Len, I would have to say, he does not appear to fall into this category. At best, he might be a transvestite, but that is far from certain at this point."

Jennifer flinched at the word 'transvestite' but was relieved to hear that Dr. Goodman did not think her son wanted to have surgery and become a woman. "Then what do you think is wrong with him?"

"Perhaps nothing" said Dr. Goodman. "Len could merely be one of those males that occasionally enjoys acting out his fantasies in private."

"But you don't think so" commented Jennifer.

"It's hard to say" said Dr. Goodman. "There is an entire spectrum of behavior involved and this is a controversial area of psychology with many different schools of thought, most in conflict with each other."

"So, there is nothing that can be done?" said Jennifer, worriedly.

"No" said Dr. Goodman. "It's more a matter of what you feel comfortable with. What approach you feel will work the best for yourself and your son."

"You mean there is no right answer here" said Jennifer, becoming frustrated again.

"Correct" said Dr. Goodman. "That's the bad news, so to speak."

"And the good?" asked Jennifer.

"There's a wide range of treatment options available" answered Dr. Goodman.

"You mean I can choose the one I like best?" said Jennifer, her voice tentatively hopeful.

"It's not a matter of choice

per se

, but rather the one you are most comfortable with, and also one that works best for Len" said Dr. Goodman.

"I see" said Jennifer not really understanding. "And what exactly are my choices?"

"That's impossible to say at this point" said Dr. Goodman. "First, we need to determine if Len is wearing your clothes, and if so, what he is doing when so attired. After that we can decide on the course of treatment."

Jennifer frowned, but said "OK. And how do we go about finding out for certain?"

"Oh, that's simple enough" said Dr. Goodman. "I have a superb technical staff and they can wire your house in a few hours."

"Wire?" said Jennifer.

"Place cameras and recording equipment in your bedroom and the other living areas. The actual devices are small and essentially invisible unless you know precisely where they are hidden. Within a week we will know exactly what Len is doing when you are away."

Jennifer was shocked. "You mean spy on him?"

"I wouldn't use that term" said Dr. Goodman, "observe is the term we prefer. It's the only way to know for certain. Of course, if you object to such direct methods, I fully understand and we can try an indirect approach like individual therapy. It will take longer, but..."

Jennifer cut her off, "No, no. I need to know now, for better or worse."

"OK then, I'll have my technical staff contact you and make the necessary arrangements" said Dr. Goodman.

Jennifer nodded and said "And if we do find out that he is dressing in my clothes, what then?"

"We will sit down and discuss your options. Just remember, no matter what we find, there will be a variety of choices. There is nothing 'wrong' with Len, it really just a matter of making the right choices for him."

"You mean like choosing a career or a major in college?" said Jennifer.

"Essentially. It won't be quite that simple but, that's a good analogy" said Dr. Goodman.

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

"We talked about making the right choice" said Jennifer, returning from her reflection.

"Yes" agreed Dr. Goodman.

"So, what are our choices?" asked Jennifer.

"Before discussing that, let's consider Len, first and what we have just seen and what it tells us about him" answered Dr. Goodman.

"Alright" said Jennifer, uncertain exactly where Dr. Goodman was going. The thought of discussing the horrible video she had just watched, repulsed her, and Jennifer's eyes flicked towards and away from the TV screen.

"I know you found the video disturbing" said Dr. Goodman, noticing the quick movement of Jennifer's eyes, "however it tells us a lot about Len, and as such it's worth discussing. I'll try not to dwell on the details, more than necessary."

"Thank you" said Jennifer, her eyes avoiding the TV.

"First, I would have to say that Len is definitely not transgendered nor is he a transvestite" began Dr. Goodman.

"That's a relief!" said Jennifer.

"I'm sure it is" said Dr. Goodman. "Len's behavior suggests something entirely different. For one thing, he is not a simple cross-dresser. Although he does not appear to need or want to publicly disclose his cross-dressing like a transvestite, he is not entirely private about his feminine behavior either or his female tendencies."

"I don't follow" said Jennifer. "He only dresses up in private and only when no one is at home."

"Yes" said Dr. Goodman, "however, if you look closely at the video you can see that he is not as careful as he could be about taking and using your clothes."

"I am not sure I follow" said Jennifer.

"Well, consider this" said Dr. Goodman, "he uses your clothes regularly, yet he makes obvious mistakes about returning them to their proper places. This is what made you suspicious in the first place. In addition, he seems to have become more and more careless in his handling of your clothes. For example, in the week that we recorded him, Len starts out by washing your panties after ejaculating in them and ends up later in the week just tossing them soiled into the laundry. This pattern is consistent with your own observations. Initially Len started out handling your clothes very carefully but has become increasingly more casual with them over time."

"Perhaps, he is becoming overconfident and therefore careless" said Jennifer.

"Perhaps" said Dr. Goodman, "but I think not. If you watch Len, he is very meticulous in selecting various garments, dressing, and with his overall appearance. He is not just grabbing panties, bras, at random and dressing in them for a quick thrill. On the contrary, he takes his time and is thoughtful and deliberate in his selections. In short, his actions are carefully planned and well thought-out. It is therefore surprising that he appears to give little or no thought to cleaning-up, so to speak. His behavior is suspiciously inconsistent."

Jennifer thought about what she had seen in the video. Len had taken his time selecting which items of her clothing to wear. Panties and bras matched, as did the dresses he chose. Even what he did while dressed-up seemed planned-out. She had to admit that Dr. Goodman had a point. Still..." I see what you are saying, but he could just be getting careless, uh...cleaning up."