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"You're missing the point, dear," said Helen. "Despite our age difference I'm not old. I've got many good years to look forward to, especially with the girls leaving soon."

The girls were Brynn and Nicole, Kelly's older sisters. Both had finished college a year or two ahead of Alana, and both had finished their postgraduate training and were ready to leave home as soon as their job offers came through, which was imminent. And Helen, of course was right. She was far from old, 60 or so standard years making her biologically around 30 give or take. With at least 200 standard years ahead of her, Helen could take a second spouse and be the matriarch of her next family. Except, of course for Kelly.

As a male, Kelly's life expectancy was much shorter than his mother's but not insignificant. At least 50 or 60 standard years, by which time Helen would be in her biological 40's or so. Not horrible but a long wait with little or nothing to show in-between. Alana could see her mentor's point and predicament.

"Perhaps", she mused half-jokingly, "you could hand him over to the Institute."

The Institute was officially The Institute for Gender Reassignment and Correction, North American Federation, but everyone just referred to it as the Institute. In principle it was the place to go for correction of physical problems and defects, and if one wished to change gender. Of course, no woman would even think of becoming a male and few males (if any) voluntarily submitted to the reverse procedure of becoming a woman, since such 'women' were legally still regarded as males even though they were biologically indistinguishable from females in every way. Originally the law had been more liberal granting full female legal status to any male who willingly submitted to gender reassignment, but too many women had protested against what they termed pseudo-females pretending to be real women. Intellectually Alana found such ravings ridiculous but on a visceral level having sex with a woman who used to be a male was emotionally repugnant. As such the law had been changed, the rights of such women repealed, and as a result, male patronage had plummeted to zero.

The Institute would have vanished becoming a historical footnote in the medical history texts if not for the fact that it was (for reasons that Alana still found obscure) taken over by the Federation Justice System where it quickly became part of the penal system. Wayward males accused of serious crimes found themselves sentenced to gender reassignment and a lifetime of sexual servitude at one of the Federation's brothels which served the remaining male population. The mere mention of the Institute was enough to sends shivers of fear and even panic through most males who regarded the place with horror and extreme trepidation.

Helen looked at Alana startled and then a look of contemplation came over her. "I was joking," said Alana not sure if she had offended her friend.

'Now that is not a bad idea," said Helen. "An excellent idea, in fact!"

Alana looked at her puzzled. "I wasn't serious, Helen. Besides Kelly would never volunteer to go there, and even with your guardianship powers you would still need him to agree."

"Who said anything about him volunteering," said Helen.

"But..."

Then the implications of Helen's words hit her. Alana was shocked that she would contemplate such action against her son. Yes, he was only a male but...still. "You can't really be serious," she said.

"Dead serious," said Helen, her face hard as stone.

"But wouldn't that be illegal," said Alana.

"Perhaps...probably," said Helen. "But I hear there is a shortage of femes at the brothels and that the Institute is not too particular or interested in investigating such matters."

Alana looked at her friend startled by her callousness. "Could you actually do something like that to...Kelly?"

"What does he have to look forward to?" replied Helen. "A life of pointless idleness, of being underfoot and in the way. The new laws are strict and getting stricter all the time. My guess is, that the Federation will eventually round up all the remaining males and do just what we are discussing. It's just a matter of time. Ten, maybe twenty or thirty standard years. Perhaps a bit longer. I am only proposing we speed things along, at least for him."

"We?" said Alana recovering from her initial shock.

"I know you are leaving soon," began Helen, "but I've seen the way you regard Kelly. It's not good my dear. Not good at all."

Alana blushed. There was more truth in Helen's words than Alana wished to admit, even to herself. Not that she would actually do anything. That was too absurd to contemplate. But still, she had to admit that she had a certain, well affection (for want of a better word) for Kelly. She had after all known him all her life, been in school with him, attended family events and so on. It was only natural that there would be some...feelings for him, however slight or insignificant.

"I see by the look on your face Alana that you understand what I am saying," said Helen.

"Yes...yes," stammered Alana. Perhaps Helen was right. Best to resolve this issue before something unfortunate happened. It would give her and Helen closure and besides, it would be best for Kelly in the long run. Helen was right, things would only get worse for him as the laws became ever more restrictive. The legal noose would eventually close around his neck and perhaps force him into even more unpleasant circumstances. Besides how terrible could working in a brothel be for him? At least he'd be doing something useful.

"Good!" said Helen. "The simplest plans are always best. It's no secret that Kelly likes you, so it should be a simple matter to lure him into the trap...."

So that was it. All Alana had to do now was call the Federation police and report Kelly. Federation law regarding male behavior had reached the point that if a male merely touched a female without her permission, a charge of assault could be brought and successfully prosecuted. The punishment, of course, would be gender reassignment followed by a life sentence of servitude, usually in one of the Federation's brothels. It would of course be Alana's word against Kelly's, but the word of a woman was more than enough to convict a male, even without other corroborating evidence. The rape scandals of the last decade had insured this. The outrage among the female population had been so loud and angry that legislation increasing male punishment for assault had passed both quickly and overwhelmingly. The definition of 'assault' had now become so broad that almost any physical contact by a male against a woman was considered as such. And the resulting penalties had also become commensurately harsher and more draconian.

"Poor Kelly," said Alana to herself. But sighing she added "it's for the best."

***

Kelly ran home, relieved and bewildered, as well as excited and frightened. Alana had never really paid him much attention before (although she had always been nice enough to him, certainly nicer than any of the other women he knew). And now suddenly, she was kissing him like...like...well Kelly was not sure exactly like what, but surely not like that! His penis had been so hard! If she had continued kissing him...well thankfully he had set the alarm. Not that Kelly had exactly wanted to stop. But he had heard enough stories and seen the news about males not keeping their proper place with women and it was enough to send shivers down his spine. He had no desire to be hauled away, sent to the Institute, perhaps worse, executed.

He could hear his mother's voice warning him "Never even think about touching a woman. The Institute is full of males who thought they could take advantage of a woman and get away with it!"

And Kelly knew she was right. In grade school and secondary school, talking back to an instructor or any woman, even another female student, would inevitably result in a trip to the principal's office followed by a bare bottom spanking witnessed by the victim. Now as an adult, punishment was much more severe. Permanent chastity and a public shaming for minor offenses like a lewd remark or an unwanted glance, gender reassignment for more serious offenses (like unwanted physical contact), and execution for crimes involving physical violence (rape or murder).

Kelly had heard of cases where a male had innocently and accidently had momentary physical contact with a woman and as a result, was severely punished. Just last year a male had tripped and bumped into a woman, his arm brushing her breast as he tried to regain his balance. After a public shaming in front of the victim it was off to gender reassignment and a life-time of servitude. Kelly shivered just thinking about it. No way was he going to let that happen to him!

But what had just happened? It was not like he had initiated anything. That morning his mother had told him Alana was coming by and that he was to go with her and help her. Though an unusual demand, it was not like Kelly had any choice in the matter either and he did not even dare to ask why or where. Questioning, refusing, or disobeying his mother would get him verbally chastised at a minimum and more likely severely punished. Kelly had suffered more than one bare bottom spanking in front of his taunting sisters to not want to repeat such punishment. Either way he would be forced to comply, so better to spare the humiliation and pain of a punishment and comply with his mother's orders.

That is not to say that Kelly was unhappy to spend time with Alana. She was perhaps the only female in his life that treated him with a minimum of decency. Unlike his demanding mother and haughty sisters who were always ordering him about, Alana at least asked nicely and then thanked him afterward. Truth be known, Kelly adored Alana and secretly had a crush on her (though he knew to hide his feelings).

Kelly was also not foolish enough to believe that his feelings could in any way be reciprocated by Alana. After all, she was a woman, and women did not have such feelings for males. Especially Alana, who was smart, beautiful, and popular. It was true that they had known each other forever and that she had always been nice to him, but anything more would be delusional on his part. Dangerously delusional. Still...what had all that...kissing been about?

The kissing on her couch troubled him greatly. Had it gone too far? Perhaps it had been a test and that frightened Kelly for if he failed his mother would surely punish him severely. He had been hard and Kelly hoped Alana had not noticed. It was so difficult to control himself when she brushed up against him and impossible when they were kissing. Kelly blushed at the memory of his erection. He was still excited and he knew he would have to cautiously and quietly relieve himself tonight after everyone was safely in bed (at least that is, if he escaped being punished for being late). Masturbation was of course strictly forbidden and the one time he had been caught his mother had beat his butt so hard and viciously that he literally could not sit for a week afterward. He could even feel the small scars left there as a permanent reminder.

Kelly trembled at the thought of relieving himself. If his mother or one of his two older sisters even suspected he was masturbating, he knew his mother would immediately place him into chastity most likely permanently. This had happened to a couple of Kelly's male friends who went about in a continual state of sexual frustration and discomfort. Kelly had no wish to join their ranks but his mother was continually warning him against 'improper thoughts' and the 'despicable and disgusting acts' that they engendered. To make matters worse, Nicole and Brynn, his older sisters, were constantly on the lookout hoping to catch him in some punishable offense. It had in fact, been Nicole, his oldest sister who had surprised and caught him that time. Kelly shuddered at the memory.

"Oh, my goodness!" Nicole had shouted after walking into his room unannounced. Kelly had been naked on his bed, pumping his penis, close to coming.

"How disgusting! Mom...."

His mother and his other sister, Brynn, had rushed into his room to see what was happening. Kelly who had been quite literally caught red-handed turned pale and was frozen with panic.

"Look mom!" said Brynn pointing "Look at his disgusting penis!"

Despite his embarrassment and shame Kelly's penis had remained rock hard. Kelly blushed and suddenly finding that he could move again, tried to roll off the bed and cover himself. However, his mother was too quick for him, and grabbing his ear, pulled him onto the floor at her feet.

"What exactly do you think you are doing?" she said harshly.

"I...I..." stammered Kelly.

"You were playing with yourself! We had our talk about this just last week and I warned you never to do this, didn't I?"

"Yes Ma'am," said Kelly.

"Whatever possessed you?" said his mother angrily.

"I...I..." said Kelly his mind blank and unable to come up with even the lamest of excuses.

Huffing, his mother sat down on his bed and pulling his ear again, tugged him to his feet and then over her lap.

Kelly remembered the spanking to this day; had occasional nightmares over it. Without even being told, Brynn had produced the whipping cane, a thin flexible staff whose mere appearance made Kelly quake with fear.

"Oh! Please no! Not that! Please I am sorry!" pleaded Kelly already in tears.

"Not as sorry as you are going to be in a few minutes," taunted Nicole.

"That's an understatement," added Brynn smiling maliciously.

Helen was a strong woman and in peak physical condition. Bigger and more muscular than Kelly she was both formidable and relentless when it came to punishment. She started with a bottom-reddening spanking using her thick, heavy hands. With in seconds Kelly's backside, including his upper thighs were bright red and stinging hot. And that was only the beginning.

"Please Ma'am I am sorry! Please!" wailed Kelly through a vale of tears.

"What a sissy!" said Nicole.

"Don't give sissies a bad name", said Brynn.

Helen pulled her son over her lap and shoving him into the punishment corner of the room, proceeded to cane is butt, one hissing stroke after another falling relentlessly on his tortured backside. When she finally stopped Kelly had been reduced to a quivering and sobbing mess, barely able to stand. His mother took him by the arm and leading him to his bed consoled him.

"I hate doing this Kelly, but it's for your own good. Impure thoughts lead to impure actions and those lead directly to the Institute. I am trying to spare you that awful fate. You need to be a good and respectful male, not a hooligan. Now go wash your face and get dressed."

Painful as the punishment had been, it was not the worst part. Nicole had smiled at him wickedly through the entire ordeal and later, when Brynn's girlfriends were over, they had thought fit to share the entire sordid episode in excruciating detail. At school, Kelly had blushed in embarrassment every time he encountered one of his sister's friends as they invariably asked him if he wanted to 'sit down'.

Nicole had even told Alana who had, fortunately, quickly changed the subject, dismissing the topic with seeming disinterest. For this Kelly had been grateful, but still she knew and even to this day he would occasionally wonder if she remembered, and if she did, what she was thinking.

Needless to say, that was the one and only time Kelly had been caught masturbating. There had been a couple of close calls, but luckily, he had managed to escape without incident. Brynn seemed especially keen on catching him and Kelly suspected she and Nicole had some sort of competition going on as to who would catch him next.

But Kelly had managed to keep his masturbations private and undetected, mostly by keeping them infrequent and late at night. However tonight he really, really needed release. Alana had filled him with lustful and (he knew) improper thoughts of desire and longing and he would not be able to sleep without getting some relief. Fortunately, Nicole was staying over at a girlfriend's and his mother usually went to bed early. Brynn also went to sleep early, so with luck he should not have any problems. That is, unless he was already in trouble.

When Kelly arrived at home, he announced his presence as his mother required "I'm home Ma'am!" he said.

"You're three minutes late!" said his mother.

But Kelly could tell from her tone that she was not angry. "How did it go?"

"Fine Ma'am" Kelly lied.

"Good" said his mother. "You better get to bed. I'm about ready to turn in myself. You can tell me all about it in the morning."

"Yes Ma'am," said Kelly. "Goodnight, Ma'am."

"Goodnight, Kelly."

That night after the house had settled down, Kelly pushed the covers aside and silently climbed out of bed. Opening the middle drawer of his dresser he pulled it out of the cabinet and laying it on the floor, detached the panties from the backside. There were three pairs, all white, silky, and smooth. One pair belonged to his mother, the other two to Brynn. Kelly had 'borrowed' them from the laundry one rare day when he had been alone at home. Well, borrowed was perhaps not quite accurate. He had taken and hidden them against the day when he might somehow obtain or buy a few pairs of his own. So technically borrowing was the right term, even if the exact return date remained somewhat vague. Besides, his sisters and mother had dozens of pairs and would hardly miss the three he had taken.

Kelly tried not to ponder too closely his motivations for taking these intimate feminine items. Perhaps because he dared not admit the deep desires and longings that drove his actions. He spent hours on the Net examining in great detail women's lingerie, panties, bras, stockings, dresses, shoes and every other conceivable item of female apparel. Panties were a particular obsession of his and Kelly knew every style and cut, every trim of lace and embroiderment, every fabric and texture available. One of the biggest surprises was how little women's intimate apparel had changed over the last one to two hundred years. Fabrics of course had changed dramatically but since the female body had essentially remained unchanged, cut, style, and embroidery had remained static. Dresses and outerwear, of course fluctuated widely from year to year but underwear remained the same. There was of course, only so much one could do with panties and bras, and most of this had been done long ago.

Looking at the various cuts and styles of panties, Kelly fantasized about wearing them, the feel of the satin-smooth fabric on his skin and penis, how feminine they would make him feel and look. Such thoughts and desires were taboo of course, and Kelly knew this all too well. In the current social climate any intrusion of male desires into female territory, no matter how innocuous or trivial was problematic at best and almost certain to lead to trouble. And trouble was not something that Kelly needed. It was difficult enough staying out of the way of his malicious sisters and his controlling disciplinarian mother. Additional problems he did not need or want. The mere thought of being sent to the Institute made him shudder with dread and fear.

Kelly took the pair of panties belonging to his mother and, putting them to his nose, inhaled deeply, taking in her female scent. Kelly loved wearing these flimsy, sexy garments and just touching them made him hard, although tonight that was not a problem. They were addicting as well as intoxicating and Kelly quickly slipped them on. The front of the panties bulged with his erection and Kelly felt a ripple of pleasure pulsate through his penis. After replacing the drawer, he climbed back into bed, covering himself. Reaching into the panties, Kelly rubbed his penis vigorously trying to prolong the release. Closing his eyes, he thought about Alana and how she had kissed him, her breasts rubbing against his chest. Half a minute later Kelly came, filling the panties with cum. After resting for ten minutes, he started stroking again, such was his excitement.