Sissy School

But Dr. Goodman cut her off saying "No, she did not. Please don't jump to conclusions prematurely. Ellenore had no idea who she was selecting."

"What?" Jennifer said, incredulous. "I told her that I went to see you, so she knew..."

Dr. Goodman cut her off again saying "Yes, but she did not know that Len was a possible candidate or even that he was the candidate I proposing she sponsor. When I did finally reveal who he was, she immediately declined to sponsor him, saying that your friendship was more important to her than her own potential happiness. We had quite a long discussion and it took me some time to convince her to remain open to the idea. Finally, and very reluctantly she agreed, subject to the condition that you and your daughter Melanie approved of the match."

Jennifer became shamefaced and said "I'm sorry it's just that I thought..."

"Yes, it's quite a natural conclusion to make under the circumstances. However, let's put that behind us. I want you to think carefully about such a match and what it would mean for Len and for Ellenore. In a sense, both their future happiness, as well as your own, rests upon your decision."

Jennifer was disappointed in herself. She had jumped to conclusions about Elle and she felt embarrassed that she could think such awful thoughts about her dearest and best friend. However, Dr. Goodman was right, she needed to think carefully about a match between Len and Elle, since the happiness of both was in her hands. Elle was in her mid-forties and about 20 years older than Len. Their age difference was considerable, but Elle was still very youthful in her appearance and seemed very vibrant. On the other hand, she and Len had known each other forever, and more importantly they seemed to get along very well together. Len adored her and she loved Len. She also got along well with Melanie. In addition, Elle owned her own business and was very well-to-do. She could easily support Len and take care of him, so finances would not be a problem. Jennifer was very close to Elle, so having her as Len's spouse would be just one more thing they had in common. As Jennifer continued to think about it, the pluses kept adding up. In fact, the only negative she could come up with was the age difference and even that was not completely without its positive side. Len needed a mature woman who could guide him, and yes, even control him. Elle could be very forceful and even controlling, so handling Len would not be a problem for her.

After a while Jennifer said, "Now that my initial surprise has worn off and I've had time to think about it, I see your point. I am pleased by the idea and I think they would make a good match."

"Excellent" said Dr. Goodman, "I thought you might."

"However," said Jennifer, "aren't we forgetting about Len? Although he loves Elle, he may not want to marry her. After all, she is quite a bit older than he, and it would essentially be like marrying an aunt."

"Don't worry about that" said Dr. Goodman, "I understand your concern, but it's pretty rare for a candidate to reject a sponsor."

Jennifer's eyebrows shot up in surprise. "Really? I find that pretty surprising."

"It's not, if you think about it for a moment" said Dr. Goodman. "Remember that what Len really wants is to be disciplined and controlled and told what to do, even if he does not realize it yet."

"But..." began Jennifer.

Dr. Goodman held up her hand and said "Please hear me out."

Jennifer nodded and she continued. "I know that you were going to say: that Len can be stubborn and difficult to convince even when he knows you are right."

"Yes, exactly" said Jennifer.

"But in reality, this is just his male ego getting in his way. In Len's particular case he is almost certainly too ashamed to admit that this is what's best for him and even more importantly that this is what he really wants and desires. It's essentially a self-defense mechanism to avoid embarrassment (and we know what that does to him). However, any objections or denials on his part are easily circumvented by direct intervention."

"And how to you propose to intervene?" asked Jennifer.

"Oh, that quite simple" by comforting him face-to-face" answered Dr. Goodman.

"But he would just deny it" counted Jennifer.

"Not if he is masturbating in your panties at the time" said Dr. Goodman.

Chapter 2

Len stood in his mother's bedroom, naked, and looked around, checking his surroundings one last time. He had gotten up late, as usual, showered, shaved, and then fixed himself. The' fixing', as he liked to call it, consisted of putting body lotion on his legs and arms, and baby powder on his butt, penis and balls. Len enjoyed the soft feel and fresh scent of the powder on his private parts, and how silky it made him feel inside the panties he would soon put on. Unlike the lotion, the powder was not absorbed by his skin, and as a result, it left a residue on the clothes he wore. It also had a distinctive, if not pleasant, odor which unfortunately seemed to linger for quite a while. Len knew that he had to be careful least his mother sees or smell it on her panties and become suspicious. That would never do, of course.

Len both smiled and shuddered at the thought of his mother finding out how he spent his afternoons. The idea of her seeing him dressed in her clothes was simultaneously amusing and frightening. Len could picture the absurd expression of shock on her face, the cheek muscles tightening as if she were going to sneeze, her mouth gaping wide, revealing a speechless tongue unable to articulate thoughts overwhelmed by confusion and disbelief. This brief bit of amusement however quickly vanished as he thought about his own shock and embarrassment at being suddenly discovered by his mother. Involuntarily Len shuddered, his spine tingling, the hairs on his arms rising as he remembered.

Up to now, Len had taken pains to be careful and he intended to continue doing so. Still, careful as he was, he had experienced a few close calls and, one in particular, that had left him shaken for days. Even now, a year later, its memory, was enough to sober his thoughts and set his body tingling with fear. That day had been like any other, and Len had just finished and was undressing, putting everything away, when his mother had unexpectedly come home from work early. Len remembered how he had been momentarily paralyzed with fear, frozen in place in the middle of this mother's large bedroom, trapped and corned, naked as the day he was born, with no avenue of escape. Fortunately, his mother had immediately gone back outside for something, possibly an item forgotten in the car or for the mail. In any event he had been extremely lucky, for this had given him just enough time to run to his room and frantically put on his clothes, before his mother returned to the house.

Worse than the fear of being caught however, was the sexual tingling that had passed involuntarily through his body and had left his penis erect and throbbing even as the terror of potential discovery gripped his mind. When his mother had walked into his room moments later to say her customary 'hello' upon returning home from work, Len had been forced to sit down at his desk and keep his back to her in order to hide his throbbing erection which was noticeably visible even through his clothes. However, his luck had continued and his mother failing to notice anything amiss, had pecked his cheek and asked "what's for dinner tonight?"

The close-call had left him shaken and it had taken him several days to recover sufficiently to resume his afternoon affair with his mother's clothes and the naughty solo sex that inevitably followed. However, the sexual tingling that had accompanied the near-disaster continued to haunt him and Len found it difficult to put out of his mind completely, even a year later.

Len had learned two contradictory lessons from this episode. First, he needed to give himself a time-allowance and a safety margin to account for the unexpected. His mother usually returned from work around 5:30PM, so to be safe Len decided that he needed to be done by 3:30PM. Since it usually took him about two hours to 'play', this meant he could start no later than 1:30PM and must 'cut things off' after 90 minutes to allow sufficient time for clean-up and double-check that everything was in its place. The second thing Len had learned was that, despite obvious mistakes on his part (such as leaving soiled panties in the wash), his mother was quite clueless about his afternoon activities with her intimate apparel. He had even experimented, to test her, by rearranging some of her bras and panties in her chest of drawers. Never once had she mentioned anything to him or displayed the slightest suspicion. This, he concluded, left him a sort of safety-margin, or error-tolerance, in case he made a mistake (like perhaps using too much powder or lotion).

Still Len knew there was always some risk of being caught. However, as time passed and his mother stuck to her routine and continued to miss the few mistakes he made, Len worried less and less about being caught. Whatever risk remained, whether real or imagined, it lent a certain thrill to his afternoon play that Len would have missed had it been completely absent. Still, he needed to be careful. His mother might be clueless but she was definitely not stupid.

Ironically Len could not remember when or why he became interested in his mother's clothing. Possibly it was because of his sexual fantasies. These had always involved, and been centered around, women (usually older than himself), punishing and humiliating him. Why this was so, Len could not say, nor did he dwell on it, for he lacked both the psychological awareness and mental alacrity for such self-analysis. A more thoughtful and knowledgeable person might have surmised that, perhaps, it was all deeply rooted in his subconscious, manifestations of indelible impressions from bare-bottom spankings administered by his mother in front of his sister for assorted acts of childhood misbehavior. And indeed, Len could remember the various sensations associated with such discipline: having his arm roughly grabbed as his mother pulled him towards her; his pants being summarily pulled down, the feeling of nakedness as he stood exposed before his angry mother and smiling sister; the feel of his tingling penis against his mother's bare thighs as she pulled him over her lap; the anticipation of waiting for the stinging pain to come; the hot tears; the taunting of his sister as he was spanked; the consoling voice of his mother afterward as she told him it was for his own good. But none of this rationale occupied Len's thoughts. He simply focused on the task at hand and the pleasure it brought him. Len did not need a reason to do what he was doing nor did it occur to him that he should have one.

However, thoughts of dominating women, like his mother, did excite him and Len found himself drawn to all things feminine. He loved talking with his mother's girlfriends, especially Elle for whom he felt a longing affection. Elle seemed to feel the same way too. During the last couple of years their relationship had evolved to the point where they now regularly flirted during their frequent conversations. There was even some innocent physical intimacy as they hugged and kissed (on the check) whenever they parted or greeted each other. This happened quite often too, as Elle was always coming over, typically on weekends, to hang out with Len and his mother (and unfortunately, sometimes, his sister). The three of them got along famously and went shopping together, to movies, out to lunch or dinner, or just lingered around the house, talking or watching TV. Surprisingly, Len thought, his mother either did not notice the increasing mutual affection and light flirting between himself and her best girlfriend, or did not care, or both. Given how oblivious his mother was towards his usage of her panties and bras, Len leaned toward the former when he thought about the matter, which was not too often.

His mother's cluelessness could be annoying at times, especially when she tried to fix him up with girls his own age. She had done this several times in the past, introducing him to various members of the junior staff from her office or to the daughters of some her girlfriends, such as Madison Reynolds. Len could not relate to these young women whom he found immature, even though in some cases they were a year or two older than him. There was a certain tension and awkwardness between him and the young women in question that he could not quite identify. The conversation always seemed artificial with the girl asking him questions about his goals, career, education, etc. When Len asked similar questions, they were either causally avoided or the subject was changed with the introduction of a new set of questions. Len recalled his one and only 'date' with Madison as a typical example of this behavior.

"So, Len, I heard that you might be moving out soon and getting a place of your own?"

Where had she heard that, Len wondered? He and no such plans and had not even hinted to Madison that he might even be considering such a thing. Annoyed, he had decided to counter with a question of his own. "How about you? Are you still living with your mother?"

Madison frowned and changed the subject immediately. "Have you ever been to Paris? I was there last year as part of an art class I was taking at the JC." Len sighed. He found such talk tedious and boring and none of it enjoyable. And so, it went.

In contrast, talking with older women like Elle was effortless and always natural and pleasant. He could talk for hours with Elle and his mother's other girlfriends (like Madison's mother, Lori) about anything: movies, clothes, shopping, food, and so on. These women always had something interesting to say and they never peppered him with personal, trivial or dull questions. Len thought some more about Elle and how easily they got along. Now there was a real woman, he thought. If only...oh well, it was time to stop fooling around and get going.

Len glanced at the small digital clock on his mother's night stand. Two PM, time was passing; he was going to have to make today's play session quick if he was going to meet his self-imposed 3:30 deadline. Walking over to his mother's chest of drawers, Len pulled the middle drawer open and looked at the selection of panties inside. His mother tended to favor beige and white cotton panties and these dominated the available choices. To the right, was a small selection of lacy and sexier panties in black with a few silky white ones thrown in presumably for variety. Len selected one of these, a lacy white pair with small bows. Just touching the silky garment made him excited and Len's penis visibly stiffened. Stepping into the panties he quickly pulled them up, but he had to tuck in his now erect penis least it bent uncomfortably upward.

The panties felt wonderful and Len stroked the front of them enjoying the sensation of the soft silky material against his powered balls and penis. The latter, stuck straight out, tenting the panties and distorting the skimpy garment unnaturally. Len sighed. If just once, he could control him and not get hard until the panties had been on for a minute or so. How incredible it would be to feel his soft penis get hard inside this most sexy of garments!

Time however was short, and he could not afford to linger on such minor points. Opening the drawer above, Len quickly selected a plain beige bra and expertly put it on. His mother's bra selection was fairly limited and mainly consisted of plain but comfortable everyday bras with two lacy black bras reserved for dressier occasions. Len had tried one of the later on, but since he lacked the necessary anatomy and hence the need for the garment, he chose a plain one, preferring comfort over the stiffness that came with style. After all, it was the effect he was after, not the support. His mother was not particularly large breasted (she was a B-cup), but nonetheless, the bra was ill fitting and Len stuffed a couple of wads of Kleenex into each cup to improve both the fit and appearance. That done, he walked over to the closet and admired himself in the full-length mirror.

Objectively, Len knew he looked ridiculous, but the sensation of the soft, delicate feminine garments was incredible! By comparison his own underwear seemed thick, heavy, and clumsy. Len rubbed the crotch of the panties again, enjoying the sensation of the silky material against his balls and penis, intrigued by the lack of any opening in the front of the panties. Of course, Len was aware that girls were built different from boys, but the truth of the matter was, that even though he was well out of his teens, he was still a virgin. Len had never seen a woman naked, in the flesh. Not even his sister, Melanie (although this was not for lack of trying). His sister always seemed to have a sixth sense in this regard, and try as he might, Len could never seem to catch a peak of her unclothed. All such attempts were further complicated by his mother, who took a very dim view of such activities. If caught, Len knew a bare bottomed spanking would be his only reward, and to make matters worse, it would be in front of his sister who would be the one getting a 'peek'. A few such spankings had quickly dampened his efforts of glimpsing Melanie naked.

After Melanie moved out, Len had tried looking at porn on the old computer his sister had left behind. This had been equally fruitless as his mother (unsurprisingly) hated what she called 'filth', and Len, despite his best efforts, had only seen a few (not too revealing) pictures of naked women before his mother took control of this, their only computer. Hiring a specialist, his mother had effectively blocked all the relevant web-sites, much to Len's frustration and dismay. Worse, the one or two times he had managed to circumvent the blocking of these sites, his mother had somehow found out and they had, had long, uncomfortable and embarrassing discussions about respect for women and his inappropriate behavior. In the end, Len had given up further attempts at trying to find out more. However, with Melanie out of the house and his mother gone all day, Len had turned his attention to more immediate and rewarding activities.

What Len little had found out about the female anatomy was intensely exciting and he was able to make further inferences from his mother's undergarments. Clearly girls were different and whatever they did or did not have down there, required no opening in the front of their panties, at least to pee. Len had tried to find out more by obliquely joking and hinting around with Elle and some of his mother's other girlfriends, but to no avail. He also had to be careful, as his mother was quite puritanical in regards to these matters.

Len blushed involuntarily as he recalled the time his mother had caught him playing with himself. Despite that fact that he was in his early teens at the time, she had still spanked him bare-bottomed, and over her knee and in front of Melanie. His embarrassment and humiliation (as well as the tingling in his penis) had been intense and long lasting. With Melanie smiling smugly at him, she had scolded "Never, ever touch yourself like that again!" That is something for when you get married. If I ever catch you doing that again, this spanking will seem like a light pat, in comparison!" As a result, Len had learned to be more careful, waiting until he was sure she was gone before doing anything.

However, the matter had not completely ended there. His mother refused to answer even the most basic questions about sex or even the human anatomy. Worse, if she even caught him hinting about these subjects with her girlfriends she would act immediately to embarrass him. He had tried as much with Elle one time, causally commenting how women's panties were so much lighter and thinner then men's underwear (they had been talking about clothes in general).