Discipline fosters a fervent sissyboy
Nifty Stories can only continue with the generous support of its readers. Please donate at https://donate.nifty.org I laid my eyes on Braylen in his swimsuit and I was lovestruck. He couldn't have been with the other half dozen boys around him. They were all older teenagers.
What a strike of luck. Braylen was at the public swimming pool, the very one I am a member of, just around the corner from my house.
I was doing another swim routine after a rough week of work. As the principal of the Villa Ovatia Seconday School I have alot of responsibilities, so exercise is my therapy.
Braylen is just 12 years old, but seeing him in his black arena swim briefs defied his age. At school the mandatory uniform is a dull grey uniform. So, of all the boys at Villa, I never guessed Braylen would be hiding such a sublimely lithe bod.
Here, I could admire how beautifuly his tiny nipples adorned his supple chest framed by an upexpected broadness of his shoulders. And, the span of his boyhood basket made me salivate.
Plenty of boys were at the pool in various shorts, swim briefs, jammers. Some were fit and worth a passing fancy.
If they were my students, some would smile and wave and even say hello. Braylen was different, in his own world. Other students would probaby find him aloof, but I recognised the cool, calm sort of modesty behind the shadows of the introverted kid.
He wandered right near me, jumping in and out, splashing around. The softness of his graceful waist led my eyes down to his waistline via his prominently vee shaped line of his torso. The definition of his adominal muscles from hips to groin were spectacular.
The apitome of skinny. How could it be explained? Maybe from healthy diet and rapid metabolism, Braylen was not on any of the sports teams, yet he had such a trim bod coupled with the emergence of precocious muscle mass.
Truth became known to me later on that Braylen's Aunty, a Calisthenics Instructor, had introduced him to pull-up bars and parallel bars, box jumps and of course the regular jumping on his backyard trampoline could be partly the blame too.
All the frolicking around the pool complex had loosened his arena's. They'd dropped down revealing the paler skin of his bubble bum and were now barely sitting above his bulge as he jumped in the water.
Climbing out moments later the base of Braylen's dick came to view, right before me, below the smoothness of his pubic mound.
Under the soggy wet black elastane there appeared to be transformation into a substantial swell.
The breeze carressed his cool skin, as he clung to the handles atop the pool ladder and jumped onto the pool deck.
He looked down and realised how much of his modesty was laid bare. Swiftly the cord was drawn back and tied stretching his shaft sidewards tantilisingly.
This was the moment I discovered Braylen was more than the loner schoolboy, he was cute, adorable blonde with generously gifted genitalia.
I reflected on Braylen's bod, with all the faculties by which my mind stores could remember, as I opened my office filing cabinet. I flipped through the folders of student profiles.
I already knew Braylen was a decent student as he never was sent to my office. Now I wish he had been, and I was eager to learn more.
Despite not being popular, he wasn't a misfit but a good boy with good grades. His file revealed that he was the stepson of the school's Groundsman, whom I considered a friend.
How could I have not known. He certainly had never told me his boy was at the school.
His Mother was the school's Library Assistant, that much I did know. But, how perplexing. Why the big secret. I realised my behaviour was showing signs of infatuation. Heck, who am I kidding, I would pash him on sight if I could.
Braylen was eight when Andrei met the Mrs and Andrei began as groundsman at the school six months later.
Braylen spent most of his lunchbreaks in the library. His shy demeanour meant he had few friends but had a good buddy taught him to play checkers, mahjong and rummy. So the library was the place to be.
I was impressed with Andrei from the beginning. He was very adept at hedge pruning and he spent alot of time attending to the hedges around the perimeter of the school pool.
Curiously, it was always when the boys were training.
Andrei was popular with the boys though. I could see how keen he was with the fine array of fit boys when in his company.
The swim boys proudly hung around the pool area in their school issued swim briefs.
Stretchy royal blue spandex with white side panels and a pattern of small crimson red diamonds on the front that drew focus to their bulges.
The VO logo on the side hip denoted their school, their tribe, a symbol they valued for club dedication that kept them coming to every practice and meet.
Being an avid swimmer myself I regularly spent time with the Villa Ovatia coaching staff and involved myself with the swim club. The club had many potential champs and the staff ran a tight operation, which meant tight fit bods.
I could see that I had a common interest with Andrei, something that could be exploited!
I devised a plan. The first stage was creating a new position of Pool Supervisor and I directly offered it to Andrei. He would report directly to me working solely in the swimming area.
His duties were to maintain the pool, deck and changerooms and to oversee the procurement and supply of swim equipment and swimwear for the students.
Needless to say Andrei accepted immediately. It was a sure promotion from groundsman and he would constantly be around boys in speedos more than ever before.
At the end of his first week as pool supervisor I caught up with him and praised him for how spotless the pool was and especially the shower area and changeroom.
I subtly said that it must be rewarding to work in areas that would normally have a degree of privacy seeing that it is only accessible to swimming staff ...and the students.
The implication of any peverse desires was indirect but we both knew the meaning I was advocating. We both hung around the swim team much more than needed.
He knew I was a busy man and my time was valuable. We were on the same page and he came to understand that I was aware of the priviledge I had given him.
The swim staff appeciated my involvement and they felt that it was valuable to have the principal driving the sports agenda.
And they were being supported with another head in the department. The needs of their squad were met, and Andrei had needs of his own.
Andrei was appreciative and showed his gratitude by inviting me to join his family to the local theatre that they had intended to visit.
I made the counteroffer that his family join me as my guests to the new mega waterpark nearby. It would be more appealing to Braylen, I explained. Plus, I was desperately wanting to feast my eyes upon Braylen's precious body.
Andrei, ever the conversationalist, was great company so we got along well. As we entered through the gate that morning I gave for Braylen a pair of ice blue swim shorts that were lined with mesh eliminating the need to wear anything underneath. They were short and lightweight.
All day he wore them and every time they got wet they held tightly to his legs and clung stubbornly to his dick and balls.
Andrei scolded Braylen when he held his hands over his boyhood, visible in the see through material. His long prick was tenting enough for an obvious view of his glans peeking out of its foreskin.
'Braylen, hands to your side like a good boy, no wimping' Andrei clapped.
'And apologise to Mr Smith'
Braylen responded with hands on his hips, 'Sorry Mr Smith, Sir'
Braylen was so embarrassed, he overheard us men having a good chuckle about it all, and it didn't help his predicament.
Towards the end of the day Braylen wore a white singlet shirt. Even wet, the singlet still didn't fully cover up, the head of his prick could still be spotted.
I wondered why he persisted with the singlet, he could easily have put his black arenas on underneath. It was as though he actually enjoyed us observing his boyhood, but not the humiliation of an obvious display and certainly not the derisiveness.
My passion for photography was reason enough to shoot Braylen multiple times that day. His sweet smile was infectious and he felt free when at the pool.
He skipped around like a stray dog. I took a few shots when he climbed out of the pool and pulled the singlet off. His boyhood was clearly presented in the lens frame, the money shot ...or three.
The day was successfully documented in hi-res jpeg and I would be appreciating the images like a fine wine.
Importantly, I was now equipped with the knowledge that Andrei morbidly enjoyed embarrassing Braylen.
I joked to Andrei that Braylen's so shy and effeminate he would suit being dressed up as a femboy. Andrei's interest piqued, he knew where I was going.
Braylen could easily lend himself to being a femboy too. Whilst not vain, he did have a high regard for his own physical appearance. Well groomed and he already had a sharp sense of style.
We laughed about it at first, but then we began exchanging ideas of seeing Braylen in girly undies and one piece outfits.
I suggested it could be a great punishment plan. Make him wear girls underwear when he's naughty.
Andrei explained he was not the disciplinary one, the Mrs was the real authoritarian in the household. Nevertheless, I felt comfortable in divulging a very hidden secret to Andrei.
As I had been an educator for many decades I had collected, by means of covert stealth and happenstance, to acquire a large array of girls underwear.
A collection full of tops and bottoms for preteens right through to mature teens. I'd acquired leotards and teenie clothes from countless school trips and camps.
I also collect lingerie but that's another story.
The ultimate pleasure is watching instances when the girl with the missing underwear, I pinched, has no option but to go pantiless.
They get so disconcerted and slightly ashamed, baffled as to how they lost them. Girls tend to wear very short shorts and when they are pantiless it is priceless.
So I selected some of my earliest old fashioned cotton knickers, the immature type with dainty trims.
A weeks worth, ranging in white and pastel colours. I also picked some adorable soft cotton training bras and small crop tops.
Andrei dutifully took them home and considered how to explain it all to the Mrs. He opted to just wait until Andrei had done something serious enough to warrant punishment.
Thankfully, not long later, Braylen forgot to do one of his most vital chores.
Poor Braylen was preoccupied by his gaming and neglected to take out the bin for the collection truck.
Apparently when the Mrs found out she was furious. She scolded Braylen for being so immersed in his game and ignoring her reminders.
The rubbish was surely going to overflow before the next collection.
Braylen was in trouble. Andrei took the oppertunity to pull the Mrs aside and sell my idea.
He highlighted that Braylen didn't seem to be getting too upset anymore when she smacked on his bare backside. He even submissively dropped his clothes and parted his legs without any prompting.
The Mrs had a think about it and was right on board the tactical switch.
Braylen had slipped up bad and inevitably was to discover the new discipline regime. The Mrs replaced all of his undies for my lot. He was forced to comply.
'Noooo ...I don't really have to wear these Dad, surely, it's sooo weird, I can't please' Braylen had said sheepishly to Andrei.
'You know the rules, what Mum says goes and you don't want to upset Mum, do you. You've been very disobedient, unfortunately there's consequences and that's going to be your underwear, at home and at school, for the next 7 days. No exceptions'.
Braylen scowled, as could be expected, when given the bag of girls underwear which he was to sort and fold neatly into his emptied drawer.
Seated on his bed he sulked gloomily as he took each item out and inspected it thoroughly and added it to a flat lay in front of him.
As he took out the last pieces, a set of training bra and pink knickers with lemon lace trim, Braylen sunk forward burying his head in his pillow.
I had chosen well for size, four fit best. One was fairly tight and two fairly loose.
I was given notice to check on Braylen at school to make sure he was wearing his girly undies. If he ever looked too comfortable I would pull him aside. He never knew when he was going to be sent to my office too, so he dare not cheat.
I demanded he undress to his undies every time he attended my office. It was absolute bliss. He looked beautiful, his awkwardness made him ever so cuter.
This wasn't the worst of it. I also photographed a full body picture of Braylen standing with his boyhood curled tightly in his panties each and every time. Oh, how his package lifted out the fabric exposing his genitals so alluringly.
The proof was sent in low-res to the Mrs, as well as filed to a new folder on my computer (named Braylen).
The pouting from Braylen was pitiful but the sullen brooding was negated by the glorious view of Braylen's pretty bod, somewhat humiliated into the making of a obedient little femboy.
Incredibly this re-occurred many times. After so many months my "Braylen" folder grew with the additions of more and more of my clothing collection Braylen was forced to wear.
One of my favourite photos included Braylen in a pink, shiny, ribbed leotard.
Was Braylen getting into mischief on purpose? It seemed to become more and more commonplace. And this time his mother had asked for extra discipline from me, and I did not question it.
I set to punishing my femboy standing before me, his dick already erect. He looked restful and obviously didn't know what he was in for.
'Do you think it's acceptable to have an erection in my office Braylen', I began.
'Ahhum ... I am sorry Sir but this leotard...' Braylen went silent.
Embarrassed, Braylen lowered his head 'It really turns me on Sir' he admitted, feeling culpable of wrongdoing.
The leotard really did look attractive on Braylen. He had been growing his hair for some time and he was fitting the androgynous identity he had been developing.
'Well it is a fine looking outfit Braylen and it suits you very much and it's okay to like it. It was meant to be punishment though, and as seeing how much it is pleasing you, given the tent you have there, I will have to provide additional discipline'.
First I tested the spanking for myself. Surely enough, he voluntarily stripped naked and faced the wall and gobbled up every open handed whack, as I stood pressed up to him looking over his shoulder admiring his hard dick wobble.
'There is no tolerence for being erect in my office, imagine what your mother would think if I sent her the photo with your boner in it', I whispered into his ear.
I hastened to dispel any doubt of his deserving of peach patches on his bubbly tush whilst also acknowleging his poorly hidden enjoyment of the second round of punishment with a softer tone in my voice'.
It comforted any anxiety Braylen had and seeing as though we were both enjoying the firm handed training, and his little rod getting stiffer than ever, I directed him to walk to my desk and bend over with hands horizontal to my desk.
'Hold on to that desk Braylen', I almost gushed as I sat and rolled my chair over to him observing his soft balls haging in front of my face.
I started with gentle smack of a leather paddle. He was silent, I held a hand under his belly finding the tip of his penis.
My other hand slid tenderly over his bum. A harder slap elicited a slight murmur. Each spank was followed by a gentle stroke of his butt all the while the fingers of my other hand lightly touched his shaft and glans head.
Another whack closer to his boy hole drew out a little moan. Perfect, I see Braylen loved the humming sensation surrounding his undiscovered boi pussy.
Whacking of my paddle became more rapid drawing him into a steady panting motion. Drumming his bum hole he whimpered and let out final helpless groans.
Ejaculate pumped to the slow tempo of my paddle, legs twitching from the orgasmic pleasure, his breathing receded and his penis wilted back to its flaccid state.
It was proving difficult to find a reasonable punishment to discpline Braylen without his enjoying it.
So, on the very next occassion I had to discipline him I took it to the next level.
Braylen presented himself to my office and upon stripping I witnessed him undress to his baby blue knicker set, semi transparent, in a floral and striped pattern.
Braylen had loads of precum stains all over the very skimpy briefs. This was a huge infraction.
Yes, new levels of discipline was required. I administered a silk blind fold and slid my fingers down Braylen's chest down to the raging prick poking out.
Cupping his balls I brushed my palm up his shaft and gripped the panties open with my thumb and tugged them down to his knees.
Braylen gushed in arousal, he was primed for his ejaculate to be released. Sticky cum stained panties!
Braylen was getting worked up in anticipation. His hard cock swaying up and down with his heavy breathes. He shifted his knees about, to help drop the undies to the floor.
I revealed my cock and pressed it on his. He smiled in amazement as I introduced my manhood with his boi cock. We stroked together, Braylen finding his hand on my cock and me reciprocating on his boyhood.
His touch was so soft, loving and unrelenting. I moved the mask away, Braylen looked down and watched intently at his cock squirming as it rolled around in my hand. When I saw him fire away I couldn't hold my sperm load any longer, we spurt together into a splattered pool.
To his dismay I collected and mixed it together with a special erectile liquid supplement. Braylen didn't know when I fed him the sperm soup that he was going to be hornier than ever.
What's more, for the next 48 hours Braylen's flacid dick were to be locked into a chastity cage. His erectile tendencies were in a new world of denial.
Braylen was now plunged into a dimension of sexual discipline. The cage restricting his penis from erection and frustratingly preventing fullness of arousal.
I was the lone keyholder. Braylen was given a tiny pair of old fashioned navy nylon girls bum hugging briefs with a high waist. He protested against the whole thing but this was punishment after all.
He left my office in what was yet the most dowdy of all the underwear he'd worn, his dick totally devoided of obtaining pleasure, entirely governed by my permission.
My loins were stirring when he returned after that 48 hours of denial. He displayed himself in a daggy pair of knickers baggy enough to cover the cage.
Braylen stepped toward me with a pleading look on his face. I revealed the key and I could be mistaken but Braylen could have had a tear in his eye.
Piece by piece I reduced him to bare naked. His prick rose to a very gradual but admirable full erection. I stepped away and returned with a flogger whip.
'It's not over yet', I warned menacingly.
Braylen's eyes grew wide as he absorbed his next predicament.
I neatly tethered each ankle with cuffs and tickled his chest teasingly with the slithery whip strands. My mouth sporadically kissed each section of skin with warm brushes of my lips on his tender skin.
Braylen's abdominals were subjected to lashes from the whip, more slaps crossed his nipples before sliding tantalisingly down to his aching cock.
Moans of pleasure and pain ensued as the whipping began on his cock, the torture of the leather strands lashed randomly across his shaft and sensitive crown head.
Tears were undoubtedly evident on Braylen's cheeks. I took that as a cue to smother his cock with my hot mouth. His moans were replaced by steady panting and sobbing. This time his tears were of euphoric happiness.
His large load of jizz escaped in rapid streams as I stroked it into my hands as lubricant and relentlessly extracted each last drop from his boyhood.
As the semesters passed Braylen's outerwear style began changing with body hugging outfits, vintage in style.
My femboy pierced both his ears and wore beaded and braided string bracelets, blouse like tops and Corduroy pants.
He made a reputation for himself with unrestrained style of outfits. Vintage jackets and quirky hats, always adorned in his girly attire being the good femboy.
I even had to correct myself when the name changed to Braelyn. This was the point where he became she.
Braelyn matched the new identity that she was springing forth. There was a graceful swing of the hip to Braelyn's walk, effeminate gesturing of the hands and an acquired higher tone of voice.
Months had passed transforming Braelyn. Quirky outfits were now the signature look that easily set Braelyn apart from others.
There were some detractors but Braelyn actually began to flourish which attracted more friends. And she looked sexier than ever.
I still insisted she had to attend my office when called upon, generally this was after school. And when Braelyn entered my office smelling sweet and juicy scented with perfume it lifted my mood as well as arousing my loins.
When she stripped for her photos she was confident in her femininity and it showed in her posture and attitude.
When she was well behaved, or got good praise from teachers, I rewarded her with specially designed femmeboy erotic lingerie. Her first set were stockings adorned with bows and pearls, held up by elastic garters and exciting lacey bottoms that comfortably housed her dick.
It was funny, Braelyn posed really well in her lingerie, happily dishing out her own model poses of supermodel fame.
Braelyn was now an all together femboy, especially at home where she totally embraced her inner femininity without limits. She dabbled with makeup and entirely shaved her arms and legs. A fine silver anklet slinked nicely atop her pretty feet.
The next stage was for Braelyn to model herself in her femininity, as well as expand into experimental artistic endeavours.
Now was time for a promotion. Mrs Smith became Head Librarian and rewarded with an all expenses paid weekend away with Andrei.
The arrangement being that they have a dirty weekend away whilst I look after Braelyn. Braelyn would be looked after, I planned to spend an intimate weekend of my own with my little femboy.
The first day we spent on an outdoor adventure. We drove to a remote forest and hiked a short trail in to a pristine stream.
I took the chance for us to rest and have snacks I had packed. Next we stripped off completely nude and I grabbed some supplies from my backpack. Bodypaint and brushes.
Braelyn's bod was pumped from the trail walk in and looked so delectible as I started to apply paint to skin.
I painted pink, purple, white, and blue fine lovehearts and elegant flowers to her chest all the way to the base of her dick shaft. I snapped as Braelyn wandered around stark naked exploring her new habitation.
The dappled light highlighted new growth of more whispy pubes that had began around her prick.
We left the clothes behind and rock hopped ahead naked upstream over rocks and through streams till we arrived at a sparkling waterhole.
We lay in the clear cool water for a while splashing around and jumping in from a higher boulder. Braelyn hopped out to warmth, sunning on a bare boulder.
I lay in the water and admired her wet glistening body warm up. Her penis plumping as the rays of sun set its vigour upon her flaccid member.
We headed from our respite, back to civilisation, our adventure in the outdoors complete.
At home we washed up and freshly dressed and cuddled up together for hot chocolate reviewing the pictures of the day. Braelyn sat in my lap and felt my growing hard on as I fondled her inner thigh.
Braelyn looked up at me hungrily. I took her hand and led her to my bedroom. Placing her limp body onto the bed, she lay on her side lifting a leg to my direction.
I climbed over and we embraced in a warm kiss. I carressed her butt as she brushed my chest.
Pulling her to the edge of the bed I opened her pants and kissed around her thighs, she giggled as I worked my way closer to her prick only to continue kissing her belly.
Braelyn arched her arms back fervently. I directed my kisses up to her nipples and slid my tongue teasing on the pointy nubs. Kissing her neck she gushed before I returned back to her dick.
I held her penis in my fingertips as I began a slow massaging of my tongue on her dick glans before embracing it into my lips slurping up and down accross her frenulum and crown ridges.
Plunging her whole member in my mouth sent Braelyn's hips twisting beneath me as I worked away on her boyhood in a long loving suck in expectation to guzzle from her rigid rod.
A build up of simply too much pleasure was about to tip her over. Braelyn gained toward break point, puffing loud symphonic breathes.
Unable to withhold any more slopping on her femboy dick she passed the border to climax spurting her cum in my mouth.
As my mouth siphoned her forceful blows she arched her head with a grimace on her face until she had no more to unload.
We lay together as she regained breath together in a moment without equal.
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