A young looking and slight 18-year-old boy sits outside the Headmistress’s room, obviously feeling anxious. His legs kick back and forth under the chair and he keeps looking up at the door. His uniform looks unkempt, like he has just thrown it on after Games. After some long, countless minutes elapse, he hears a loud, slow “Come!” from a female voice behind the door. He knows his fate is about to be decided and hangs his head before slowly standing up and shuffling his feet toward the door. The door opens easily and quietly and he moves slowly in, hoping to prolong the time until She notices him. A gentle push and the door clicks quietly back into place.
“Jeremy! Good. Stand there.”
The Headmistress indicates a spot on the floor directly in front of her desk. He quickly moves forward, not wanting to risk any further rebuke.
“I have a report here on my desk, Jeremy. It regards your behaviour, or rather your recently discovered activities. This is very unfortunate as your school history has been exemplary until now, excellent grades, no misdemeanours. And then there is this. Discovered in a gym storage room, spying on the ballet class. But what is this here? Not just watching, not just filming, not just playing with yourself, but all this while dressed in a school uniform. Or should I say, a schoolgirl uniform. Oh dear. Found by the poor ballet teacher too, Madame Jenoix.”
Jeremy stared at the floor, remembering being caught by Madame Jenoix. It wasn’t yesterday, as it said in the report, it was actually around 4 weeks ago. But it was pointless saying anything, the evidence was damning enough and trying to implicate Madame Jenoix would just make it worse.
It had all started several months ago, just before another dreaded Games lesson. Desperate to avoid another humiliating, painful and unpleasant ordeal, Jeremy had slipped quietly behind the gym in hope of finding somewhere quiet to hide. There was just some bare ground next to a fence, and nobody would come down here, he thought. It was quiet at first and Jeremy happily daydreamed next to the large waste bin, one of those big ones that could fit a huge amount of rubbish. Sitting on a crate next to it, all was peace and quiet until some voices penetrated his reverie.
“Shit,” Jeremy thought, “now what?”
He couldn’t go back the way he came, and the other way led out to the playing fields where he’d be spotted. Hoping to hide behind the big bin, he quickly moved the crate away and tucked in behind. But inside of finding bare wall, instead there was a hole! It seemed to lead inside the building, and he could hear some voices somewhere far inside. Not hesitating, he quickly dived in and pulled the crate back in place. Finding it quite spacious inside, but very dark, Jeremy slowly moved forwards towards where some light was filtering through. It looked like wooden slats and he could hear chanting on the other side.
“I know that song! That’s the football cheerleaders song!” thought Jeremy.
Looking around, he noticed that some of the slats weren’t placed properly and had gaps in, allowing him to look through. Getting used to the light again brought the extremely pleasant sight of the entire senior cheerleader team practicing in full kit. They must have just been getting warmed up and a few were still doing their stretches. Standing up straight, then bending full over to touch their toes gave an unbelievable view of their pretty, frilly knickers. They would then straighten, stretch one leg out to the side and run their hands, lovingly in Jeremy’s mind, along their entire hose-covered leg down to their trainers. They would then start over again and do the other leg. Jeremy couldn’t believe his luck! Guessing his position from what he could see, he must be in the old gym storage room. It had been disused for years after a new, modern gym had been built next door. Now this gym hall was only used by a couple of classes that didn’t need any equipment. Barely used at all now, Jeremy thought, he only knew of the ballet class that came here to be left alone by the boys. The cheerleaders probably came here for the same reason. Watching the warming up was a lot of fun, and an erection soon made itself known. Figuring he was probably safely hidden here, he pulled it out and started stroking his cock in time with the practice music.
Watching the couple dozen best-looking girls in his school, all in pretty, sexy, tiny uniforms as they danced and joked around was just perfect. Jeremy had had plenty of fantasies involving these girls and their uniforms, although not all at the same time. Checking his watch he saw there was still 45 minutes of the lesson to go and slowed down his self-pleasuring so he could enjoy the full show.
After warm up finished they had a few minutes to catch their breath and spent the time hugging, slapping the occasional ass and jumping around. This all seemed to involve a huge amount of pantie material being flashed, and Jeremy loved every moment. They were all wearing the same uniform of course, but each one had a different colour and style of panties. He saw thongs, g-strings, plain white panties, blue gym knickers and one pair of fire red lacey French knickers that really caught his attention. They then went into their main practice routine, shaking their pompoms, dancing and singing the cheerleaders songs.
Never having been up this close before, Jeremy realised why the school governors attended every game. They had a box right by the cheerleader stand, and must get this beautiful view every single game, while showing support for the school. Many had wondered why they insisted on that box, which had a ground level view of the field instead of the usual high up one, but this must be it. Nobody could turn down a regular view of that years crop of the schools finest cheerleaders flashing their panties at you. And flashing panties seemed to happen a lot, even now they were doing regular routine instead of a warm up. The skirts seemed designed to flip up and get caught on the back of their tight tops, causing their pretty panties to stick it out when they bent over. Jeremy wondered if the uniforms were also kept the same because of tradition or their tendency to show everything. The cheerleader tops weren’t much different. All the girls were quite buxom anyway, but after squeezing into a top a couple sizes too small made them appear busting out.
One part of the routine had them spin round and bend over, giving Jeremy a view straight down their tops causing Jeremy to start panting. This went on for some time, but the lack of air-con in the old gym hall was starting to show on some of the girls. A few of them stripped their tops off, revealing tiny sports bras small enough to hide under their uniforms but so small they revealed pretty much everything. Doing little more than pushing those glistening, sweaty mounds up and together gave thoughts of sliding your cock between them, fucking those gorgeous tits and shooting your load over their pretty, panting faces. The music was skipped forward to the next track, which Jeremy recognised as the end of song game. Realising they would be leaving soon, Jeremy sped up his hand ready to finish. Before he could, the song finished and he felt a keen disappointment, before the girls started hugging and kissing each other, congratulating on a good practice. The girl in the red knickers hugged a tall blonde, who accidentally flicked up her skirt and grabbed a handful of French knickers and tight ass. The other girl didn’t seem to notice or mind, and Jeremy shot his load watching those delicious red knickers getting groped by another beauty.
Checking the time again, Jeremy realised the lesson would be over soon. He watched the girls file, some hand in hand, out to the changing rooms before edging himself back towards the hole in the wall. Checking that all was clear, he let himself out, covered the hole again and then rejoined the crowd heading to the next lesson. Feeling giddy all afternoon, he kept drifting into a daydream of girls knickers and cheerleader uniforms.
The next day Jeremy had an idea. He found the gym schedule on the school computer system and checked all the lessons booked in the old gym. Sure enough, there were the cheerleader practice and ballet lessons he had thought of. There were some boring things like PE for the younger classes in there, but most of interest were the after school classes. Apparently they held 18 year old girl ballet classes in there 3 nights a week! Turns out the school was the only place in the area with a proper ballet teacher, Madame Jenoix. All the local dance colleges sent their ballet classes here once a week for extra practice. Living nearby, Jeremy knew it would be easy to be back here each night in time to watch, starting from tonight.
More prepared this time, Jeremy brought his camcorder and a small stool with him, and snuck in to the gym well before the girls were due to arrive. He got set up in front of the door, and pointed the camera through one of the holes he felt would get an overall good view. According to the clock on the camera he still had over an hour to wait and realised he’d been over eager. Never mind, he thought, let’s have a look round.
Pushing the door gently, he was thankful that it swung open easily and slipped out before pushing the door closed. He took a little walk around, looking for somewhere else he could hide, or could put his camera but couldn’t spot anywhere obvious. Checking some of the other rooms, he found the girls changing rooms and showers. Now this would make a fine place to observe, Jeremy thought and began looking carefully for a place a camera could go here. He found a small cupboard that contained the old fuse box. Not big enough to fit much, and covered in dust for disuse. Perfect. All he would have to do is make a small hole for the lens, start the camera before the lesson and then hurry out before the girls arrived. Just as he was thinking this, he heard a door slam shut!
Voices came down the corridor, and Jeremy realised he’d spent far too long in here! Panicking, he dashed through the first door he found and ended up in the towel room.
“Should be safe for the moment” Jeremy thought.
The towel room had long been disused. Pupils were expected to bring their own towels to cut costs, leaving the towel room a handy hiding place. Looking around further just in case, Jeremy spotted the air vent in the ceiling was not placed correctly and could probably be moved. Quickly scaling the empty shelves, Jeremy pushed the vent further and pulled himself through the gap, replacing the vent again after. Being a very old building, there wasn’t a proper suspended ceiling. Instead, when an air-con system had been installed back in the 60s they had simply created a false ceiling. In a bid to bring in more revenue the air-con had been used to make the building useful in the evenings and summer. It was also perfect for Jeremy, now able to hide so long as he was careful.
Enough light filtered up through gaps in the false ceiling for Jeremy to take a look around. This floor stretched the whole width of the building, but lengthways there was a wall that Jeremy guessed must be the wall for the main hall. Plenty of space too here though so long as he didn’t want to stand. Around 10 metres away was a whole network of pipes, heading down into the main floor.
“Water pipes. Oh! The showers of course.” Jeremy thought after spotting them.
He shuffled over in that direction and sure enough could see through a gap straight into the girl’s showers.
“This is too good to be true…”
Jeremy shuffled sideways a bit and found the changing rooms, knowing the showers wouldn’t get used til later. Reaching carefully into his pocket, he carefully removed his other, smaller camera that he’d been intending to hide earlier. Finding a nice vantage point, he poked the lens through a gap and settled back to wait, and watch.
Another twenty minutes passed, until eventually the girls started streaming in from the coach outside. All very attractive, slim athletic girls with extremely pleasing figures, they filed in to the room and found a bench. Slowly peeling off their uniforms, they began to change clothes. They were all wearing the uniform of a local dance college, which was designed to be tight and flexible for dancing. A close fitting, tailored white blouse under a burgundy woollen blazer started the uniform, with a standard grey, pleated skirt below. Being older, these girls had stretched the rules and the skirts hung barely down to their smooth, well-defined thighs. Over-knee white stockings and heeled Mary Janes completed the outfits. Under was a different matter of course and Jeremy had a perfect view of more types of underwear than he thought existed.
These girls obviously enjoyed dressing up, and were wearing everything from cami-knickers to the tiniest of G-strings. Jeremy particularly loved the girls in French knickers, all beautiful lace and frills lovingly encasing those perfect bodies. The same situation was true on top. Basques, bodies, babydolls, bras, camisoles, silk and lace was all over.
Jeremy was in heaven; it was like his own perfect temple of bows and frilly undies. The girls stripped down further, leaving a room filled with completely naked hot, nubile teens rubbing moisturiser and talcum powder into their perfect, glowing skin. They then slipped into their leotards, all in identical burgundy before trotting off to practice. Jeremy switched off the camera and wondered what to do now. The girls wouldn’t be back for an hour, and it was quite cramped up here. He shuffled back to the towel room vent and let himself back down. He was now on the other side of a door leading to a room filled with some of his most perfect fantasies… Hot girl’s underwear.
Jeremy had pilfered a few items in the past to play with, but these were on a whole different scale. His hormones leading the way, Jeremy slipped through the door and into the chamber of wonders. Not knowing where to begin, he put his hand in the nearest bag and pulled out a silk camisole and matching pink cami-knickers. Running his hands through the material, he closed his eyes and dreamed of wearing them, and the rest of the school uniform, and playing with the cheerleaders in the shower.
Dropping the underwear back in the bag, he continued on going through all the bags. Knowing he wouldn’t be able to take any of the underwear they had brought with them in case he got caught, he got the idea to have a look for clean underwear ready to wear after their showers. They would just assume they’d forgotten it, and hopefully not think too much of it. Searching the bags more thoroughly he found lots of interesting items including some vibrators! There were a few dildos, and even a little pile of love eggs in one bag. Jeremy made a mental note of those to check out the girl when she came back.
As for underwear, Jeremy picked out a pair of pink silk French knickers. He didn’t want to take too much in case it was obvious, and was feeling conspicuous. Before he disappeared back up into the ceiling, on a whim he reached into a bag a pulled out the vibrator he had found earlier. It was the biggest of the three and looked well used. Bringing it up to his face, he breathed in deeply and could faintly smell the girl who had been using it. Pulling out her little thong too, he smelled the still damp crotch and got a strong scent of the girl. He then slipped the vibrator inside the knickers and took it in his mouth, sucking it down as far as he could. Closing his eyes again he dreamed the ballet dancer was fucking his mouth with a strap on, and he was one of the other girls. Licking the vibrator clean, he replaced them back in the bag and decided to leave.
Thanking his lucky stars he’d left the camera in the main hall running, he climbed back up in to the ceiling, shuffled over to his camera and waited for the girls to finish. He took the opportunity to slide off his trousers and underwear and pulled the beautiful silky, pretty and very frilly knickers he had purloined up over his cock. He then put his trousers back on so he didn’t damage them, and contented himself by playing with his penis through the silky material.
Eventually the girls returned, and were eager to strip off their sweaty leotards and jump in the shower. No shyness from these gorgeous babes as they pulled their tight, shiny leotards off, grabbed a towel and headed to the showers. Jeremy followed, taking his camera with him, and continued to film the girls that had now started showering. He watched the water running down between their perfect breasts, down their tight torsos and between their legs. Girls facing the other way showed him their pert backsides as they bent down to pick up their shower gel. A few girls were messing around squirting each with their shower gel, long white streaks running down their perfect bodies like a bukkake party before being rubbed in and covering their smooth, silky wet skin in bubbles.
The girls spent a while in the showers cooling down from their practice, slippery hands stroking breasts, thighs, backsides, and ass, between their legs… Jeremy thought he was wrong earlier. This here must be heaven. Eventually the girls grabbed their towels and left, drying themselves off. Moving back to the changing rooms before the last shower was turned off, Jeremy got the camera ready again. He found the girl with the big vibrator, and also the one whose underwear he’d stolen. Making sure he got some close ups of them, he checked them out more closely.
The girl whose panties he was now wearing was a short, Japanese looking girl with black hair pulled into a ponytail. She was very pretty, but looked annoyed at not being able to find her clean knickers.
“Fuck,” she said, “I forgot my clean pants.”
“Or your boyfriend is wearing them!” another girl shouts back.
“Yeah yeah, at least my boyfriend could fit in my underwear!” she shouted, before pulling on her school knickers instead.
The girl with the big vibrator was a tall redhead, with a gym work out physique. She looked like she took her physical exercise seriously, and quite probably her sex too hence the thick, long vibrator. You certainly wouldn’t argue with her in bed, she looked more than capable of putting you in your place and taking what she wanted.
The girls dried off and began pulling on their evening clothes. Even more frilly, pretty panties selected carefully to tease their boyfriends with lacy, push-up bras to tease everybody else. A few girls pulled on full basques, and got their friends to help tie them up, and then fasten their stockings. The sight of these fantastic angels pulling on black stockings, rolling them gently up their perfectly smooth legs before fastening the silk stocking tops to their beautifully embroidered and detailed basques was enough to send Jeremy almost over the edge.
The final moment came for him, literally, when he caught sight of a girl pulling a pair of knee-length black leather boots up her legs, 4″ heels poking out from below. Jeremy came as she took hold of the heel in her fingers and stroked along it, like she was giving her boyfriend a handjob, before pushing the boot the rest of the way on to her foot.
The girls left soon after, and waiting a few minutes for safety, Jeremy let himself back down, picked up his camcorder and then disappeared back home.
Reviewing the tapes, Jeremy was extremely pleased. He had a good view of the changing room and shower video, but the main hall was just as good. A whole room full of pretty little 18-year-olds in leotards and over-knee socks was an amazing sight. The amount they could stretch their legs up was remarkable; their boyfriends were very lucky. Although knowing the way of the world, their boyfriends were also jock assholes who would happily cheat on these bounteous angels. Jeremy was happy to be this close to the girls, and spent much of the night reviewing the tapes over and over. He took a particular interest in the tall redhead, who had one of the most incredibly pert and round backsides he’d ever seen. Tightly hugged in her leotard and then bent over, she became his desktop wallpaper.
This continued for quite a while. Jeremy continued to film the ballet and cheerleader groups and slowly built up a little collection of clothes that he kept in the gym. Each time he went now, he would dress up in a pair of blue, slightly too tight, gym knickers and a silk blouse, before pulling on a school blazer and skirt. These two he had been lucky enough to obtain after one of the girls had an accident, and wet herself in the bathroom. Nobody but the girl knew, she thought, not counting on the camera Jeremy had hidden there to watch the girls peeing and sometimes playing with themselves. She had hidden the sodden skirt, blazer and blouse behind some pipes and then left, presumably intending to pick them up the following week. They were removed far sooner though, with Jeremy enjoying her still piss-wet clothes that evening.
He also wore a pair of old over knee socks that had a run in and been thrown away. He loved all the clothes he had procured, only still wanting a leotard but these were always being worn or too many people were present.
One day however, Jeremy was watching the ballet as per normal during games. Fully dressed in his mismatched uniform, he was jerking off looking through the gap in the cupboard door when a shadow fell over it. Leaning back a little, he realised somebody was stood on the other side! Before he had a chance to move anywhere, the door opened and he was revealed, cock still in hand and a pair of knickers in his mouth to Madame Jenoix. His mouth fell open, causing the knickers to fall out. Madame looked slightly startled, and then amused.
She didn’t say a word, but closed the door slightly, checking nobody else had noticed and then said “Don’t go anywhere, stay exactly as you are, and I will deal with you after the lesson. Don’t forget those panties in your mouth.” she smiled and then left, closing the door behind her.
What to do? Madame Jenoix knew Jeremy and would have recognised him. He had spent a lot of time staring at her legs, stiletto shoes and dresses in the past, and frequently caught by her eagle eyes. She had never said anything, merely smiled and teased him, often letting her shoe dangle off her toes and swinging it back and forth towards him. She would then take her time sliding it on and off her foot before finally inserting her foot fully in.
There was no doubt she had recognised him. No point leaving then. Should he get changed? She had specifically stated he shouldn’t, and should put the dirty panties back in his mouth. He did so, although his mouth had now gone dry, and tried to play with himself unsuccessfully. Can’t even get an erection now, he thought, thinking back to all the times around Madame he’d be desperate to lose one.
Twenty minutes later the lesson ended and the girls left. It was the last lesson of the day, so there wouldn’t be anyone in here anymore today. After a while Madame Jenoix walked back in, now wearing what looked like her regular school teaching uniform instead of the ballet leotard she had been wearing earlier.
She was much taller than Jeremy anyway, but with her ponytail flowing high out of her head and the eye wateringly sexy Jimmy Choo’s she was wearing she towered over him as she opened the cupboard door again.
Her long, tight skirt did nothing to hide her slender and ballet toned body, and she had left off her normal blazer in favour of her body-hugging leotard. Her nipples could be seen quite clearly through the top, and it showed off her breasts as though the leotard wasn’t there.
“Well well. Jeremy isn’t it. I knew you had a crush on me, but this is silly. Why don’t you come on out of there?”
She opened both doors wide to let him out and noticed the camcorder.
“And recording the memories for posterity, how touching. I think I’ll borrow this and see what you like so much later.”
Jeremy went to stand, causing Madame Jenoix to rebuke him, “No no, on your knees is quite acceptable. Crawl to me.”
Dropping back on to his knees, he shuffled forwards towards Madame, panties still in his mouth.
“Well aren’t you a pretty little thing Jeremy, or should I call you Jenny? Yes I think I should. But oh dear Jenny, that uniform you are wearing is a disgrace. I shall have to punish you for that, but for now let us get you dressed properly. Follow me to my office, and stay on your knees. Eyes on my heels, but I probably don’t know to tell you that, do I, you little pervert?”
Madame walked slowly toward her office, and Jeremy followed behind on his hands and knees, watching Madame’s tall, stiletto thin heels tapping along along the wooden floor. He hadn’t managed to get a pair of shoes yet, and was still dreaming of Madame’s shoes when suddenly she stopped dead, and he bumped straight into her! His face, still stuffed with panties, pushed up against her long, taught legs and he felt her stockings rub against him. The feeling was electric, and he was suddenly reminded of his predicament.
“Now now Jenny, plenty of time for that later. We have to punish you first. You can walk the rest of the way, but keep your eyes down. Focus only on my shoes, legs and ass. I’m sure you can manage that.”
She ran her hands over her tight skirt and down her stockinged legs causing Jenny’s breath to stop until she reached her ankles and stopped, ass pushed up in the air with her legs spread. Giggling while she straightened up, Madame walked forwards again into her office and sat down on the edge of her desk facing Jenny.
“Kneel.” Madame stated, and Jenny quickly complied, kneeling in front of her legs. Keeping to the earlier rule he kept his eyes on her legs, which were now less than a foot away from his face. She lifted up one foot, popped her stiletto off so it was just hanging on her toes and held it up in front of Jenny’s face. The heel was barely an inch from his face, and he whimpered slightly, aroused and ashamed beyond belief. The object of his desire, right here in front of him, teasing him in the most cruel way, and she knew his humiliating crossdressing secret.
“You like shoes, don’t you Jenny? And stockings too I imagine. Do you like it when I run my fingernails down them, does that make your little peepee get hard? I’m sure it does, you can’t take your eyes off me in class, how sweet you want to come to my other classes too. Especially my ballet class.”
Madame lowered her foot again, pushing the shoe back on to her feet. She then lifted her other foot, and placed the heel and sole of the shoe on Jenny’s chest, pushing lightly.
“Do you like my ballet outfit or my teachers outfit more I wonder. A tight little leotard and over knee socks versus my stockings, heels and tight, stern dress. Such a difficult choice for a horny little girl like you. But as I said earlier, I can’t have you in that disgraceful, ruined uniform. What would people think? One of our prettiest girls dressed like that. Why don’t you take off all those clothes for me, and drop them on my desk next to me here.”
She patted a space next to her, “Oh but I don’t want you talking so keep those panties in your mouth.”
Jenny quickly stripped down to her knickers, and folded the clothes neatly into a pile on the desk.
“Now now, when I tell one of my pretty, sexy little girls to strip I expect her to strip all the way. I want to see your hot, wet little pussy too. Shame about your lack of cleavage, maybe I can help with that later.”
Jenny, face down and burning red, lowered his knickers as well and dropped them on the pile.
“That’s better Jenny, be a good girl for me and this could be enjoyable for both of us. Now, what are these clothes you’ve been wearing? These knickers belong to Samantha in my senior class. And this uniform label says that they are Wendy’s from another class. What’s that smell? Did you piss in these sissy? Did you wet yourself?”
Jenny shakes her head vigorously. “Oh dear oh dear, wetting yourself in uniform. What a pathetic creature you are. These socks… Look familiar. Yes, they’re mine. I threw them out a few weeks ago. How precious, you found my cast offs and wanted to wear them and be just like me. I guess that means the other girls didn’t give you their clothes either did they? Not surprising, you are far too girly for them to be interested in you. Luckily for you though, I am interested in girls, even ones with no breasts and an oversized clit like you. Why don’t you stroke your little clit for me? I want to watch you stroke your pussy.”
Jenny reached down to what Madame had called her clitty and took hold of it, slowly stroking whilst still staring at Madame’s legs. She lifted her foot again, and slid the toe under Jenny’s balls, pushing back and forth gently against her as she played with herself.
The soft leather of Madame’s high heels felt wonderful, and the sight of her long, slender stocking-clad legs quickly brought Jenny to excitement, panting and tugging on her clit quickly. Waiting for her to almost finish, Madame said “Stop!”, swinging her foot back before kicking Jenny squarely between the legs.
Jenny squealed loudly, stars in her eyes, and rolled over clutching herself.
“I said you were to be punished, not pleasured little slut. Now back up on your feet and let’s get you dressed properly.”
Jenny struggled back up and stood once more in front of Madame Jenoix.
“Good, well behaved girl.” she said to Jenny.
“I don’t often get to watch my girls play with themselves, rubbing their little clitties hard until they orgasm for me. I do so love watching my ballet girls fingering themselves, all the time with their eyes on me. Sometimes I use my shoes on them too, I love their slick juices on my toes as I slide them in and out of their tight little pussies. I’ve never been able to work out if I prefer the girls that willingly come to me, or the ones that I force into it. Both are fun in their own way, and the forced ones will do so much more for me.”
Madame’s nipples had grown large and dark under her tight blouse, and she gently played with herself, looking at my slender body.
“Practically no hair, that’s convenient. But still a little too much for my liking, especially here.”
She ran her leg, from knee to ankle up between Jenny’s legs causing her to shiver with pleasure once again.
“Shower time I think, come along.”
Madame fished something out of her desk, and then left the office with Jenny following behind, hands over her privates. She was gently rebuked.
“Hands at your sides, sissy. I like my girls on display at all times. And are you looking at my backside like I told you? Imagining what 25 years of ballet would do to my 30-year-old backside? Good. Here we are, step inside.”
They had reached the shower room, where Jenny had hidden his camera in the ceiling. He had gone shopping a couple weeks ago and bought some new video cameras, security type ones which activated on movement. He’d been able to get much more footage now he didn’t have to be there in person. Of course, it also meant his current predicament was being caught on camera.
“Now then, you’ll probably enjoy this Jenny. Face the wall, hands above your head, and spread those legs for me. I bet you’ve wanted me to spread your legs for some time. That’s a good girl.”
Jenny did as she was told, feeling a little chilly up against the cold wall. Her nipples perked up as she accidentally rubbed them up against the wall.
“Now hold still, this might be a little cold.” Madame said, pulling on a pair of latex gloves before squeezing a hand full of gel out in to them. She then reached between her legs and rubbed into her privates, covering her little scrotum in cream and causing her to moan in pleasure again.
“See, that isn’t so bad is it? Be a good girl and we can have so much fun together.”
Pulling her fingers back a bit she covered Jenny’s ass crack as well before heading down and ran her creamy hands over Jenny’s legs. That done, she pumped out some more gel and then put her hands around Jenny’s waist causing her to take a deep breath at the sudden contact. Madame lovingly stroked her hands up over Jenny’s chest rubbing her cream and latex covered hands all over, and spending a lot of time playing with her nipples. Jenny was in ecstasy now, feeling her nipples being pulled and stroked was so much pleasure. Madame smiled, knowing Jenny wouldn’t be able to resist anything else that she demanded.
Finishing with the cream, Jenny was now covered in the white goo everywhere that might have hidden hair.
“Good girl Jenny, now wait there for me. I’ll go and find you something to wear.”
Still stood facing the wall, Jenny felt like a naughty girl with her hands still on her head. Her clitty was now fully engorged and her nipples still tingled with excitement from Madame Jenoix’s touch. After five or so minutes, Madame returned to find Jenny still stood in the same place.
“You are a well behaved sissy aren’t you? You make me so happy. Now let’s take care of all that ugly boy hair so you can be a lovely pretty girl like me.”
Turning on the shower above Jenny, Madame quickly washed all the cream off, ordering Jenny around as she went.
It never hurts to get your girls used to following orders, as she knew from her teaching.
Finished with the shower, she stood back to take a better look at her new toy.
“Mmm, what a lovely, perfectly smooth girly body you have now. So much better. You are going to be such a perfect little girl for me aren’t you? I’ll make sure you get lots of playtime with me and I’ll turn you into a lovely little sissy girl. Do you only like girls, or do you like boys too? I wonder. Well we can find out about that later. Dry yourself off with this towel and we’ll put some clothes on you before you catch a chill.”
Jenny followed after Madame, towelling herself dry and revelling in the soft towel against her smooth, hairless body. It felt wonderful, and she thought about what it might feel like to have silky underwear or a pair of stockings against her skin now. Finishing with the towel before she got back to the office, Jenny adjusted the panties that were still in her mouth.
“Oops, naughty miss I am, I’d forgotten all about those panties in your mouth. Let’s take those out shall we? Now you are a girl I have to treat you like a girl, not a naughty boy who needs punishing and humiliating.”
Madame pushed her red painted nails and fingers deep into Jenny’s mouth, forcing the panties further in, before whipping them out quickly, leaving Jenny dry mouthed and running her tongue round her mouth.
Madame Jenoix reached over her desk bending fully down and wiggling her backside toward Jenny, who got a tiny glimpse of Madame’s stocking tops as she stretched. She opened a drawer, and fished about in it, then said “Make me happy and turn around like a good sissy, I want your eyes closed as well.”
Jenny did as she was told, turning about to face the door again before closing her eyes. She felt Madame approach from behind and felt Madame press her body up against Jenny’s smooth, super sensitive body. She gasped slightly, feeling Madame take Jenny’s nipples between her long painted fingernails and pinching them lightly, just enough to cause a whimper before running her nails down Jenny’s naked body. The sissy writhed around under Madame’s touch, panting at the pleasure as she was teased.
Whispering quietly, letting her breath play down Jenny’s neck, Madame said “Open your mouth for me, nice and wide. I’ve got a present for you, for being such a well behaved, pretty little girl.”
Jenny quickly did what she was told and opened her mouth wide for Madame.
“Thank you Jenny, such sweet surrender makes me very pleased. And very wet.”
Running her hand back up Jenny’s body, flicking her nipple as she went, she stroked up the little girls neck before moving her hand away.
“Hold still.” Madame whispered, letting her tongue slide between her red lips to touch Jenny’s neck, causing a shudder and another whimper.
Knowing this was a vital moment of submission for Jenny, Madame wanted to make sure she was as sensitive and aroused as could be. Stroking up the inside of Jenny’s leg with her foot, she felt the girl’s sissy clit throbbing hard through her stockinged knee and knew the time was right.
She brought her hands together in front of Jenny, slid the penis gag sharply into her mouth, then sliding her hands quickly along the leather straps to the fastening. Pulling it tight and forcing the long, very hard dildo into Jenny’s mouth, Madame quickly buckled the straps and adjusted the positioning to make it more comfortable.
Jenny looked startled, but managed to keep her arms by her side even as the big black cock invaded her mouth. Her eyes flickered open, but she closed them again quickly, not wanting to upset Madame.
“You make me so happy; I love well-behaved little sluts. I have so much I’d like to do with you. And if you work hard enough for me, I won’t have to tell the Headmistress about your little perverted peeping. Now that I know you’ll be nice and quiet for me, let’s get you dressed shall we?”
Turning Jenny round by the shoulders, Madame smiled warmly at her before planting a big kiss on Jenny’s cheek.
“Aren’t you delightful? No wonder the girls laugh at you and the boys pick on you. The girls are probably jealous of your lovely feminine body. And the boys probably fancy you, with your lovely long hair and pretty face. I bet you’ve imagined what it would be like with a boy, you dressed like a tramp and him with his cock in your mouth like that gag.”
Jenny blushed again; it was one of her favourite fantasies when wearing her stolen panties.
“I thought so. Well let’s get you dressed and then you can enjoy that big dick in your mouth even more. Lift your foot and I’ll pull these up on to you.”
Jenny did as instructed, and Madame took a pair of really pretty, frilly pink French knickers from her desk. They had bows all along the hem and frilly lace around the legs and were quite the most delightful panties she’d ever seen.
Bending down to pull the frillies up Jenny’s leg, Madame brought her face level with the sissy’s boy bits. Seeing how turned on Jenny was made Madame moisten in her own, very pretty panties. She made a point of blowing warm air across Jenny’s sissy clit, before sliding the silken drawers up her smooth, super sensitive legs.
Jenny squirmed and wiggled at the feeling, making Madame smile. Nestling the frillies up around Jenny’s waist, the teacher had to tuck the little penis quite firmly inside, where it still insisted on poking out happily. Unable to resist giving it one more stroke through the silk, Madame heard Jenny make a little, high-pitched whinny like squeal. Madame smirked at her near complete control over her new charge, and reached for the next item of clothing.
“Now this is lovely isn’t it Jenny?” Madame asked, holding up a pale, soft pink basque. It was obviously quite expensive and possibly designer. The lace work and embroidery was exquisite, and Jenny felt it belonged on a beautiful model, not her plain frame. Small red hearts, tastefully sewn along the edges, framed an inner partition with dozens of frills sewn down it. It is, if anything, even more pretty and girly than the panties.
Jenny eagerly helped Madame to dress her, and then lifted up each leg in turn to allow her to slowly roll a pair of pink stockings up Jenny’s legs. The feeling was just as Jenny had imagined, she closed her eyes and enjoyed every moment of pleasure from the smooth nylons.
“You might be wondering where these clothes came from, sissy.” Madame remarked as she ran her fingers and hands up and down Jenny’s legs, ostensibly straightening the stockings.
“The panties are a spare pair of mine, I keep a spare pair here just in case the sight of all those delicious young girls dancing around and playing with each other makes my knickers too wet to wear any more that day. So I come back here, play with myself til I cum and then get changed. The stockings are just a spare of ballet stockings in case a girl forgets hers. Those were worn just today by one of the girls you had been spying on. The basque, well that was a present that I bought for a girl a couple years ago. She had been my lover for a little while, and I bought her that to wear for me while she gently lapped at my pussy for hour after wonderful hour. But now you get to wear it today, a privilege I don’t offer lightly.”
Now the underwear was in place, Madame Jenoix picked up a skirt from the desk. It was a standard school uniform skirt, grey and pleated. Jenny stepped in to the offered garment and soon her panties were covered up. Next were the uniform top, tight lacy blouse, tie and blazer.
Madame Jenoix stood back to appreciate the view, and made a fuss of straightening Jenny’s clothes. “So pretty. You really are a delight. But let’s give you a little make up before we go any further, and I intend to go much further with you. Come and sit down for me.”
Jenny followed Madame around the desk, and perched on the offered chair.
“We’ll have to remove this I’m afraid, don’t worry, you’ll get a cock back in there later I’m sure.” said Madame, as she gently unbuckled the gag and slid the dildo out of Jenny’s mouth.
She found her make up bag, and got to work. Nails, lips and eyes were all made up to the best of Madame’s ability, and Jenny practically glowed with excitement at her new look.
Lips glossy and plump, eyes dark and sultry, nails red and slutty, Jenny looked every inch the naughty schoolgirl. Out on the town and looking for some action, that was the look she now had. Madame was feeling rather naughty too now; Jeremy had suddenly become quite the minx as Jenny.
“One last thing to complete you,” Madame said, gently inserting Jenny’s pink stockinged toes into a pair of red heels.
Not as high as Madame’s, that would require practice, but a pair of pretty, red patent leather shoes with a 2″ heel.
“Now that I’ve done so much for you it’s about time you do something for me. Kneel.”
Jenny quickly obeyed and looked up expectantly into Madame’s eyes. She slowly pushed her feet apart, spreading her legs, while lifting the heavy material of her skirt. Jenny felt her nipples tingle again at the gradually building expectation as Madame’s stocking tops, and then panties came into view.
Inch after inch of lace frills, then a hem of deep red, blending into a lighter and very sexy bright red. Bows of pink satin appeared, dotted around the top of the frilled top hem completed the wondrous sight. Jenny made a very slight whimpering noise at the beauty and was guided, face down into the frills. Madame Jenoix had obviously been very aroused for some time, and this had made her panties quite patently wet, a large moist patch glistening under the lucky sissy’s face.
Madame was keen to prolong both their excitement, and held her quivering girl there for some time, able to do nothing but breathe in the musky aroma of her Madame’s passion. Jenny poked out her tongue slightly, and lapped gently at the dark pink patch, revelling in her first glorious taste. She tasted again and again, ever more eager to enjoy all of her Madame’s lust for this pretty young girl. Knowing that she been the cause of the ever widening moistness in Madame’s underwear made it all the more exciting, Jenny’s eyes widening as she saw her teachers fingers reaching down to her crotch again.
Placing one finger under Jenny’s tongue and gently lifting, tongue still pleasantly active, Madame used her other hand to pull the crotch of her panties across to the side. Sissy Jenny finally got to see her first real pussy, in the most fantastic and incredible of ways.
Madame continued to hold the girl away, burning for her tongue but wanting to tease her, taunt her, and control her. She kept her panties pulled across with one finger, used another two to gently separate her lips, and the fourth to slide, glacially slow, inside her well lubricated and almost steaming hot pussy.
She slid her finger inside, watching Jenny’s delighted face, then moved her finger deeper.
“Have you ever seen a girl like this before?” she asked.
Jenny shook her head, never having been intimate with anyone.
“I haven’t even kissed a girl before.”
Madame felt sorry for the sissy, it was obvious she was completely inexperienced. That would soon change. Noting that Jenny was completed mesmerised by Madame’s probing digit, gliding wetly in and out of her dripping pussy, she decided some interrogation might be possible.
“Have you been spying on pretty girls long?” – Jenny’s head shook gently, pretty hair flowing around her face.
“Have you known you were a sissy and been dressing up for long?” – the tiniest of nods this time, rewarded by Madame removing her pussy covered finger and pushing it into sissy’s mouth instead.
“Do you enjoy being a girl?” – a more obvious nod this time, Jenny’s mouth sucking on her teacher’s finger while licking at it with her tongue.
“You make a very pretty girl; you look so sexy. I like it when sexy girls kiss me. Would you like to kiss me?” – a vigorous nod this time, eyes finally breaking away from Madame’s most intimate place and looking into her eyes, almost begging.
“That’s wonderful, I can’t wait to kiss those ruby red lips. Forcing my tongue into your mouth, being your first experience, all so perfect. I’ve been pleasured by many young girls here, so many over the years. Some wanted me for my body, some feel desperately in love, some I forced into performing for me, some were looking for a way to fix their grades. But, of all these girls, you are my first virgin. I shall treasure and enjoy you. Now another question, you might not have kissed a girl, but have you ever played with another boy? Maybe just for fun, licking his cock or running your soft hands up and down his stiff penis until he came for you, his hot white cum shooting up and splashing your eager face. Then running down, dripping on to your fingers, where you take a sneaky lick from when he’s not looking, enjoying the taste of his manhood. Have you done that?”
Jenny, still looking adoringly at Madame, had begun to blush again while she spoke. By the time Madame asked her question, Jenny had taken the finger deeper into her mouth, and was trying to hide her flushed, red face in Madame’s frillies panties.
“Oh it’s okay sissy, I don’t mind if you’ve played with other boys before. So long as I’m the first to have your tongue in my pussy, and the first to watch a man force his big hard cock up your tight, creamy virgin ass.”
Jenny whimpered again, finally breaking his line of sight with Madame and buried his face in her lap.
“There there,” Madame cooed, stroking her long soft hair, “Its okay, I’ll be there with you, holding your hand, your face in my pussy just like now; lapping away. I’ll hold you tightly, your pretty little body quivering against me in whatever pretty dress I pick out for you. Then your first man will push you to your knees, slowly lift up your dress and then slide your panties aside, exposing your precious little sissy pussy. I will have made sure your pussy was nice and wet for him beforehand, inserting my latex gloved fingers, covered in slippery lube, up inside you while you tell me how much you love me. Then he’ll take his rigid, throbbing cock which you would have just kissed and licked to perfection like a good girl, and gently but firmly enter you for the first time. You’ll probably squeal, and it will hurt, but we will hold you down, and I’ll watch as he fucks you, faster and faster, harder and harder, making you scream with pain and pleasure, raping your too small hole before finally giving you his gift. A wonderful big load of his juicy, gooey man cum shooting deep up inside you like an enema. Then, after he’s done he’ll pull out and you will clean his cock for him, licking up all the cum like any pretty little pink princess would.”
Jenny was still buried in Madame’s lap, hiding amongst the frills and between her stocking tops. Madame Jenoix could see her quivering, whether in fear or excitement didn’t really matter. Jenny was going to do all those things whether she wanted to or not.
“But that’s for another time, nothing to bother your pretty little head about. Talking of head, it’s about time you gave me some. Let me show you how. Head up, just there, perfect, now tongue out and place it just *ah* there. Now just gently lap there like a kitten with a bowl of milk. And don’t stop until I tell you to move.”
Jenny eagerly licked at her soft, warm and wet pussy, having been shown where Madame’s clitoris was. Her first taste of a girl, and what a girl! His beautiful ballet teacher had become her beautiful and kinky sex teacher. She did her best not to think of the promises of anal rape, and instead concentrated on the little bud of Madame’s joy. Her tongue was being well exercised, Madame making soft, moaning noises as her new pet pleasured her.
After a while, she guided Jenny’s mouth down a little, nose nestling gently against the outside lips of her clit and tongue pushed smoothly downwards to Madame’s pussy. Teacher and pupil settled down, Madame watching Jenny’s pretty hair as she bobbed up and down licking lovingly at her pussy.
This lasted for some time, until Madame reached her third orgasm at the young boygirls touch.
“That’s enough my little flower,” Madame told Jenny, “now it’s time for me to return the favour.”
Jenny lifted her head, looking a little disappointed at being stopped. She thought this had been her reward all along! Wondering what could be in store for her, she sat back on her knees facing Madame.
“What pleasure should I inflict on my beautiful, pretty, slutty and very well behaved girlfriend? What delicious treat is in store for you? Well unfortunately for you it won’t be involving this.”
Madame pulled back her leg, then slid it forwards and up in between the sissy’s legs. She poked her leather, stilettoed shoes up inside Jenny’s skirt and ran the toe along her panties, then pushed the sole of her shoe back along her sissy clit, back and forth causing Jenny to squirm and squeal in delight.
“No I’m afraid this won’t be getting to squirt your sissy juice with me tonight. Maybe one day I’ll let you rub it against my shoe until you make your special cream all over them, before you lick it all up like a good girl. But no, not that tonight. You are going to be my little sissy princess in uniform all evening for me, and princesses don’t make cream out of their clitties. No I have a much better idea. Pop yourself up and sit on the desk for me.”
Jenny promptly followed instructions and let Madame fuss about her again, straightening her stockings, puffing out her skirt, tidying her blouse before finally fixing her make up.
While touching up Jenny’s lip gloss, she said “There, can’t have you looking like a cheap whore who has just been fucked in a run down motel can we? You aren’t some slutty hooker, drinking cum for five bucks a shot. No, you are my perfect little prim princess, when you take some mans hot jism in your ass, face and mouth you are going to look impeccable. And you’ll make a lot more than five dollars a go.”
Smoothing out Jenny’s eye shadow before reapplying some fresh make up, she said “but I do keep getting carried away with your bright future. Let’s concentrate on here and now. Your attentive tongue deserves a reward, so I’ll let you worship me with it. I know you’ll enjoy that, I’ve been teasing you with my shoes for a few years now, I can always spot the boys with shoe and stocking fetishes. I love the way the tiniest little dance of dangling my heels from my toe, or running my long, bright red painted nails down my stockings can make your panties grow. Such fun sport. So down you get, I want my shoes so clean you could eat your dinner from them. Hmm, that could be fun… Oh, wait, stay there, I have a better idea. You’ll just have to wait to worship my shoes. I do have a little present for you, it’s a surprise though so you’ll have to wear this.”
Madame took a pair of black panties and put them over Jenny’s head and eyes, before taking some more spare stockings and tying them around to make a blindfold.
“And to make sure you don’t interfere,” Madame walked behind her schoolgirl and took her hands before tying them firmly to the desk. Returning to the front, she spread Jenny’s legs apart, lifting her shiny red heels and tying these tightly in place to opposite desk legs.
Forcing the large penis gag back in to Jenny’s mouth, she said “I think you’d look good in petticoats, pretty one. I’ll have to find some for you. Big, frilly, lacey petticoats with lots and lots of layers to push out your skirt. It makes it easier for everyone to see your stocking tops, and when you bend over everyone will be able to your beautiful frilly panties. Definitely you should be in petticoats. Oh what fun for you! It will be your first petticoating! Perhaps a corsetting too, give you more of a girly figure than you already have.”
All the while she was talking, Madame had been stroking Jenny’s legs and caressing her fingers gently over the bulge in her frilly French knickers.
Reaching inside, Madame pulled out Jenny’s sissy clitty, which had been straining against the tight French lace. Running a fingernail down the base caused Jenny to jump sharply on the desk, squealing and mewing at the suddenness of the pleasure.
Madame smiled, enjoying the affect she had on the boy, as she always enjoyed the affect she had on boys. Sissifying and controlling them like Jenny made it so much more fun though.
“Are you ready for my present? Legs spread and exposed like the whore that you are? Good.”
Madame said as Jenny nodded vigorously, obviously hoping Madame had forgotten her earlier statement about not playing with her clitty.
Removing a keyring from her pocket, she unlocked and opened the bottom drawer in her desk. Pushing her various dildos, vibrators, butt plugs and other sex toys out of the way, she found what she wanted at the back of the drawer.
Retrieving it, Madame made a few adjustments before taking hold once more of Jenny’s throbbing clit.
“Now hold still.” she said, sliding the cage over his cock and balls.
She adjusted it some more to fit perfectly around him, then slid the metal bars into place and clicked the lock shut.
“There you go sissy, my little present to you. Do you know what it is?”
Jenny shook her head, obviously confused and frustrated at the lack of any attention to her now fully encaged penis.
“Well let me show you.” she said, untying the stockings from around her head and then pulling off the panties obscuring her view.
“Look! Aren’t you lucky! I’ve given you my very own clitty cage. It keeps your private bits nice and safe, and will be a constant reminder that you are my property now. It is even engraved, look it says here along the top, ‘This Sissy is property of Madame J’. You are a very lucky girl being my property. But that has some responsibilities attached. Like you have to keep pure and not play with yourself. You belong to me now, and only I am allowed to milk your sissy cream from you. You’ll still be able to go tinkle and shower of course; I’m not a cruel mistress. Now back on with your blindfold and let’s get you into position for the next game.”
Madame untied one ankle and one wrist, flipped the Sissy around and tied her up again, this time bent over the desk face down, with her cute little panties up in the air after Madame gently lifted the hem of Jenny’s dress up. Madame leaned over her, wrapping her arms around the quivering girl and stroking her gently, slowly reaching one hand to play with a nipple, while the other hand moved up to stroke Jenny’s neck.
She kissed her softly and whispered into the Sissy’s ear. “Just stay there, sexy. I’ve got a special treat for my perfect little princess, just the thing.”
With one final squeal caused by a vicious pinch of a nipple, Madame Jenoix stood back up and reached back into her drawer, retrieving one of her favourite toys, a strap-on dildo. It wasn’t quite the biggest in her collection, but it was still nice and thick and long, certainly big enough to take this little slut she thought.
She stepped in to the harness and lifted it up, pulling the straps tight around her perfectly formed backside before adjusting the dildo so it sat nicely, hard up against her happily purring pussy.
She bent down again to Jenny’s ear. “Now just take a deep breath and relax. This is my special present for you, I’m going to treat you the same way I do all my girls so I hope you enjoy this as much as I will. Remember, make sure you relax.”
As Madame was talking she slowly pulled down the tight little panties hiding Jenny’s pussy, pulling them down as far as her outstretched legs would let them go. She then got a large metal pump, and pushed the nozzle deep inside Jenny’s now wriggling anus, at least three inches in, before pushing on the handle and depositing a large load of slippery lube up inside her.
Jenny squealed again around her gag, shaking her rump as Madame slowly pulled it back out again, still pushing the handle in to fill Jenny with even more of the lube all along her tight pussy hole. Another generous dollop on the dildo, a good stroke to cover it, and she was ready to take this scared, quivering little girl’s virginity.
Maybe not in the way Jenny would like, but definitely in a way that Madame would enjoy the most. She pressed the end of her plastic cock up against Jenny’s puckered hole and began to push her slippery, gooey member slowly forward, entering inch by thickening inch, stretching her ass-pussy to the accompaniment of an equally gradually increasing squeal from Jenny.
She could do nothing though to stop the thick cock entering her, which even with the lubrication was still hard and painful, and squealed louder and louder, causing Madame to smile, loving the feeling of violating this little slut.
The base of the dildo pushed hard against her pussy and clit, which she enjoyed as she pushed another inch or so, before pulling out and ramming it back in again, causing more squeals from Jenny. She thrust her cock harder and deeper each time, the rougher the better, getting lost in the feelings in her pussy as Jenny writhed around, squealing as loud as she could around the huge gag in her mouth.
Eventually Madame Jenoix’s cock was fully buried in the Sissy’s ass-pussy, at which she stopped, much to the relief of Jenny. Reaching up once more, Madame held Jenny tightly to her, gently wiggling her hips to keep up the feeling in her pussy as she played with Jenny’s nipples again, causing her to moan in pleasure and arousal with the cock still buried deep in her ass. Jenny’s squeals soon turned pleasurable again, and Madame took this as her cue to start fucking her in earnest. She pulled out the whole way before ramming her giant penis hard back in, taking the little sissy all the way before fucking her over and over again, Jenny’s sissy pussy stretched to accept her anal invader as she squealed in delight at the hard fucking.
“Take it you little slut, take my big, hard cock in your pussy. Squeal for me, I love listening to my little faggot whores as they hurt for me. I’m going to fuck you hard now so I can get some pleasure out of this too, nobody likes a selfish bitch.”
Madame fucked Jenny roughly for some time, enjoying the feeling as the dildo bumped up against her pussy every time she took the sissy to the hilt of her cock. Finally satisfied and feeling happy, she slowed down and then pulled out the dildo.
“Well, I’m done with you now. I’ve had my fun for the day, it’s time to go home and fuck myself silly with my vibrators and dildos while I think of my pretty little girl straining against her cage all night thinking of me. Oh, I’m feeling quite flushed already, maybe I’ll pop some love eggs in for the drive home. Your clothes I assume are back in your grubby little cupboard and your disgraceful uniform is in the shower room. I suggest you take it, your new uniform and yourself home. You might want to deal with your make-up too, I’m sure your friends and family wouldn’t be too happy about you turning up like a painted Jezebel. You will be in your cupboard again after my next evening lesson, waiting for me in your new uniform. I will leave your gag, a wooden chair, and hand and ankle cuffs for you to restrain yourself with. I’ll expect you to be tied fast to the chair and gagged waiting. If not, you will be restrained and left in your schoolgirl’s uniform in the middle of the hall over night for the cheerleaders to find you.”
Jenny, once released, was left to tidy herself up. Collecting up all her clothes, she hid them in her cupboard before returning to the shower room and washing all the make-up off. Clean and dry, Jenny became Jeremy once more. He found his regular clothes and then headed back home.
As Madame Jenoix had taken his camera he didn’t have any new video to watch, but instead had his memories of the evening. Having been left frustrated by Madame had been agony, and he wasn’t sure his erection would ever disappear again. Jeremy even spent a while trying to masturbate through the cage but with a complete lack of success. Eventually he dropped off to sleep, backside still throbbing, ready for school the next day.
It didn’t get much better then. He was woken by his erection straining against the cage causing quite a bit of pain and ended up taking a cold shower. This helped for a bit, but the combination of feeling the cage round his cock and the beautiful girls at his school, many of which he’d seen naked, conspired to give him a hard time all morning.
He found a note in his pigeon hole at break reminding him to be in place as ordered, although how he could ever forget the things Madame had done and said to him he didn’t know.
He was even thinking about what she had told him about sucking cock. It had always just been a vague fantasy, much less real than his thoughts about girls, but now it looked like his first time might be forcibly taken from him. His incredibly sexy teacher had made it quite clear she was going to watch him sucking cock for her, and probably even be fucked by men. Jeremy didn’t really want his virginity to go to some strange man while Madame looked on and laughed, but it didn’t seem he had much choice. His guilty, dirty, sordid secret was now no longer a secret and he was being sexually blackmailed.
“What on earth will happen this afternoon? She will have time to prepare today, she might have anything in mind.” he thought on his way to lunch.
Later on Jeremy made his way to the gym hall again, disappearing off quietly when given the opportunity. Sneaking to the cupboard, he could hear the girls getting ready as he stripped, dress in his new uniform, and then took a look at the items Madame had left for Jenny.
As stated, she found the chair, metal with a very sturdy frame, and the other toys. Jenny first inserted the gag, taking a little more care than Madame had. She was grateful for the velvety lining, smoothing off the hard leather, and then had an unexpected tingle go through his body as she took the big, hard black cock in her mouth. Trying not to think about it, she inspected the restraints. They were basically handcuffs, except with a fuzzy pink lining for comfort and the ankle cuffs were a little larger.
Jenny was just wrapping the cuffs around her ankle when she noticed another little package on the floor where the restraints had been. Sure that it wasn’t there the day before; she put he cuffs back down and opened the box. Inside was a large, pink realistic dildo with a flat, flared base. There was also a little note.
“Hello sissy. Hopefully by now you are already dressed and ready. Here is a little something extra to remind you of me while you are watching. He’s a big boy, and very eager to meet you, but you might want to use the lube I’ve left so he can enter you more easily. Have fun, Madame.”
Sure enough, under the note was a small sachet of lubricant called Hard Anal Pleasure for Girls.
“Well that explains where it goes, anyway.” Jenny considered.
Carefully opening the sachet, the sissy poured the contents over the butt plug and massaged it all over with her fingers. She was happily pleasuring the dildo for a while before realising what she was doing and quickly put it down. Pulling her panties down with her clean hand, she remembered how Madame had slid her finger into Jenny’s ass to help lubricate, and so Jenny did the same.
She slowly inserted her finger, dripping with lubricant still, up into her own ass and moved it around to get her sissy pussy wet for the big cock. Feeling ready, Jenny put the cock on the seat and gently lowered herself on to it. It was really quite big, but not as big as the one that Madame her fucked her with and was slow to enter.
Jenny could hear the girls in the gym outside, and caught the occasional glimpse of pink leotards and tight, firm bodies prancing around. Her sissy clit grew a little in the cage, and feeling more horny she was able the take the big anal intruder all the way inside.
The feeling as the main part of the plug entered her was incredible, followed by a last quick push as the end tapered quickly back in causing her ass to hold it tightly inside. Taking a few seconds to catch her breath and get used to the feeling of having a large cock in her pussy, Jenny relaxed again. She wiped her hands before readjusting her underwear and uniform over the buttplug before moving her attention back to the cuffs.
Firstly she put the ankle cuffs on, the other end of each cuff around the chair leg, and then the wrist cuffs. It was a little fiddly, but Jenny managed to get the cuffs fastened to the chair and settled back to watch today’s show.
Jenny looked quite a sight, schoolgirls uniform on, gag in her mouth, cuffed to a chair and wiggling occasionally on the buttplug inside her. But she soon started enjoying the view of the girls in the gym hall doing their exercises. Madame was at the front like normal, and was instructing the girls in their warm up.
Today, and Jenny wasn’t sure if this was for his benefit, this seemed to consist of all the girls bending over away from him, giving him an amazing view of these girls backsides with their tight pink leotards stretched along their beautiful behinds. Quite a number of the girls were a little bit more well endowed in this area, and their leotards had been pulled into the crack giving him an almost unhindered view.
They were then instructed to turn around and repeat, this time giving him a lovely view of perfect teenage breasts jiggling about braless in their leotards. The sight of all these gorgeous creatures prancing and bouncing around in their frilly pink leotards was having a major effect on Jenny, not that she could do anything about it. Even if she wasn’t handcuffed, the clit cage was very effective although it seemed to almost make her even hornier than if she wasn’t wearing anything.
Madame put the girls through their paces, then after about ten minutes she stopped briefly while the girls practiced how high they could stretch their legs up, giving Jenny varying views of tight pink leotards stretched up into pretty pussies.
Madame reached into her bag and pulled something out. Looking straight at Jenny’s cupboard she smiled wickedly before pressing the thing in her hand. Suddenly the cock in Jenny’s pussy thrust up inside her!
She squealed slightly, but luckily the ballet girls were making too much noise for her whimpering to be heard as she felt the dildo fucking her ass remorselessly. Unable to get up or adjust anything, Jenny was now being fucked hard in the ass and loving it.
This continued for the whole lesson, with Madame occasionally adjusting the speed and force of Jenny’s anal plug up and down.
Eventually the lesson finished, with Jenny now feeling quite exhausted by the ferocious fucking she had endured. Quite a bit of pre-cum had come out of her clitty and made a little wet patch in her uniform making her anal excitement quite obvious.
More desperate than ever to orgasm now, Jenny watched the girls retire to the showers and changing room. On the way out, Madame twisted the control up to maximum and then went to watch attentively as the girls showered. Jenny was now almost bouncing on the chair with the force of the cock in her ass, pounding her unceasingly. She could feel her nipples rubbing against the inside of her blouse; the silky feel was driving her mad at the sheer amount of pleasure.
Eventually Madame Jenoix returned and opened the cupboard. Smiling at the incredibly frustrated sissy, she turned the speed of the butt plug down a little and then began to talk.
“Hello there sweetypie. How do you like your new friend? You’ll be seeing a lot more of him I can assure you; he just loves your tight little ass. Now let’s get you to my office where we can play.”
With that she reached down and unlocked Jenny’s ankle cuffs, allowing her to move around a bit, although not easily still in her heels and hands tied behind her back. The teacher then released Jenny’s hands, before cuffing them to each other. Madame then lifted the sissy up and, reaching beneath Jenny’s skirt, took hold of her caged clitty and attached a long metal chain to the end. Tugging on it as she went, Madame walked quickly to her office with Jenny tottering along behind, desperately trying to keep up on her heels.
After arriving, Jenny was once more restrained to the desk, although this time led flat on her back.
“Now then, the moment I’ve been looking forward to. Tongue time!” Madame Jenoix said, smiling down at Jenny.
She climbed up on to the desk, straddling the sissy. Still wearing her pink leotard, Madame Jenoix pulled the lowest part away to show her crotchless pink tights underneath. She slid one finger in, swirling it around her wet hole, before taking it out and rubbing it all over Jenny’s swollen, caged clitty head. The sissy girl writhed around on the desk as Madame teased her, before letting her clitty go. She then removed Jenny’s gag and lowered herself on to her playthings mouth.
Madame spent some time riding the sissy girl’s tongue, enjoying making the pretty thing perform for her. If Jenny went to slow for Madame, she would kick her sissy clitty with her high heels, prompting the sex slave to get busy again.
“Oh such a good girl, I’m sure your tongue will make everyone who gets to use it happy, although it will take some training to make you a perfect sissy slut. You’ll need lots more anal training too, although it is fun watching you wriggle around when taking really big cock. I hope that never stops.”
This routine became Jenny’s life for a while, her afternoons spent being mercilessly teased and used by her mistress. Jenny became very used to Madame’s ever-growing strap-ons too, and soon learned to closely associate being used like a slut with pleasure. Never allowed out of her cage, she became insatiable for Madame’s cock, as when it was inside her was the only time she got played with. This continued for several weeks, until eventually…
“Could Jeremy pleased be excused? He has been requested by the Headmistress.”
Jeremy couldn’t believe his ears; he’d never been called in front of the Headmistress before. She was a tall imposing woman, and was known to still use the cane. Secretly, Jeremy harboured a crush on the harsh looking, powerful lady, as he tended too with any Mistress-like lady. With the entire class staring, Jeremy stood and left the classroom, walking slowly along the corridor to the Headmistress’s office.
What could she want? He thought. I hope she hasn’t found out about Jenny, or what I’ve been doing with Madame… Jeremy was desperate to keep it quiet; he definitely didn’t want his parents to find out, or to affect his university chances.
Jeremy knocked on the office door, and was led in to the reception area by the Headmistress’s PA. She was a completely different type of girl; slim, young commercially beautiful and with long, blonde hair flowing down her shoulders.
Jeremy started becoming aroused again, and thought about what it would be like to spend the afternoon eating her pussy, or licking her delightfully long, black platform heels.
“Come in and sit down there. And keep your hands to yourself, I’ve heard what you’ve been up to.” she told him, pointing to a seat.
Jeremy sat down, now absolutely petrified. They knew! He couldn’t even appreciate the girl in front of him, in her lovely trouser suit. It looked great on her, accentuating her lovely figure and full breasts. She seemed to be making a point of walking around the office, bending down, adjusting her stockings, playing with her shoes. Jeremy loved watching her, but was too scared and nervous to get aroused. Eventually his time came, and he was called in to the office by the Headmistress.
“Now the question is what are we to do. First of all is punishment I think, and then based on how well you take it I’ll decide what I will do to you next. First of all though let’s get you more comfortable. Strip naked so I can examine you, and then you’ll put on this outfit for me. I know how much you like dressing as a girl, so you’ll enjoy this. And not a peep out of you!”
Jeremy had been well conditioned to taking orders by now, and quickly dropped his clothes. He then stood to attention in front of the Headmistress, who smirked as she took a good look at his slight frame, and especially his sissy clitty cage. Now he was stood closely to her, he could get a good look at what she was wearing. A long, tight black skirt wrapped her tightly, her legs sliding against each other in their expensive silken stockings. A white blouse topped it nicely, with a sharp, well-tailored blazer.
“Well it looks like you’ve been well looked after, no hair at all on your girly body. Wonderful. Now why don’t you pop these on for me.”
The Headmistress handed Jeremy a small pair of pink panties, heavily ruffled. He took the frilly pile of lace and slipped them up over his smooth, hairless legs. They were elasticated at the back and pulled up into him, giving him the cutest looking backside, which delighted the Headmistress.
“Ooh aren’t they pretty! I bought them especially for you. I just knew your little backside would look gorgeous in them, I can’t wait to share your tight little backside with my friends.”
She then squeezed his buttocks, groping him firmly, before handing Jenny a pink suspender belt. She held it around her waist, before turning around to allow Mistress to fasten it at the back. Next was her stockings, seamed, pink and silk.
“You really are such a good girl aren’t you? Not a single complaint from you as I sissify your girly body to my whim. Perfect, now lift your left leg up and I’ll roll these pretty pink frilly stockings up your leg like a good slut.”
Mistress took the stockings carefully over her fingers before stroking them slowly up Jenny’s leg. The silk felt wonderful against her freshly waxed legs (one of Madame Jenoix’s little pleasures). Jenny’s clitty twitched about in her tight frilled rumba panties, and she stroked the lacy stocking tops as they reached the top of her thighs. They had little pink bows around the top, and Jenny fastened her suspenders as Mistress began on the next leg. Once both stockings were rolled up, Mistress spent some time fiddling with them and straightening the seams so they were perfect as well as enjoying the silky feeling. Once done, she stroked her own stockinged legs up between Jenny’s, both girls enjoying the intense feeling of the beautiful material. Jenny then took a lovely, ornately embroidered basque from Mistress, pink with delicate red roses sewn along the seams. Tiny pink bows decorated the frilly edges and tickled Jenny as Mistress helped her slip into the fancy garment.
The Headmistress was getting more excited now, and quickly presented Jenny with her dress. It looked like something a small girl would want, a pretty pink princess outfit, dripping with bows, hearts, frilly lace and lots of ruffles all over. Jenny just stared, it was like something out of a dream, she had never imagined being allowed to wear anything so incredibly sissy, especially not in front of a woman.
Jenny immediately put her hands up, ready for Mistress to slide the dress over her head and tighten the waist cincher. She quickly did so, getting very excited at playing dress up with her very own sissy doll.
“Oh you are just darling Jenny, just so delightful. Pop yourself in front of the mirror here and we’ll just do your make up. There are a pair of shoes waiting for you, you can slip those on and do up the buckles while I get prepared.”
Jenny rushed over to the stool in front of the mirror and pushed her stockinged feet into the girly heels waiting for her. They were once again pink, with even higher heels than she was used to. Patent, shiny leather, they gleamed and encased her feet completely. They were like a stiletto heeled pair of ankle boots, and took her a little while to get them on as they were quite tight, and the heels made it even more difficult. Jenny had become so engrossed in her new shoes she didn’t even realise that the Headmistress had called her by her sissy name!
Once Jenny was settled, Mistress started fussing over her make up. Lots of red lipstick, shiny lip gloss, dark mascara and all the lovely things to make Jenny even prettier. She also fastened the collar of the dress around Jenny’s neck, a stiff metal collar, which she locked in place with a small padlock to prevent anyone from removing the dress.
Jenny felt so privileged to have so much attention that when the Headmistress sat down on her seat and beckoned Jenny, she bounded straight over. Sitting sideways in her lap, Jenny beamed in her beautiful new outfit, and felt every part the girl she looked.
Headmistress spoke. “Now that’s much better isn’t it? I think we shall have to keep you in this kind of outfit as much as possible, you are much more amenable like this. But I need to talk to you about what you’ve been doing. Filming the girls in their pretty outfits just isn’t on now, is it? As a school it is very important to maintain our image. And that costs money.”
At this point the Headmistress slid her hand under Jenny’s skirt and started playing with her through the silky soft material of her panties, running her fingernails under the cage.
“Luckily, we are very blessed with a group of people who are happy to give money to our school and help us to run it in the way we like. In return, we perform certain services for them. For example, we record all our sports teams in action, and send copies to our friends. Well, you might say, that’s normal. Except our cameras focus on the cheerleaders exclusively and are positioned to give the best upskirt shots we can manage. You’ve given us some great ideas for extra videos we could be making, and I think a new ballet range could be on the cards. And for our biggest donors, a shower range. That should get the money rolling in, lots of naked, wet teens rubbing themselves before getting dressed in their school uniforms. Yes I’m sure that will be popular. Maybe if you are well-behaved and do everything your Mistresses tell you, I might even let you help with the editing. So, you’ll see why I can’t let a competing force enter our market.”
“That is one business we have. There is another one, that is more pertinent at this moment. Sometimes we have girls that have been so naughty that they are going to be expelled, just like you. Now, this is a very prestigious school, and being expelled from here is likely to ruin your prospects. These girls are sometimes very pretty, just like you. We give them an alternative, something that will let them stay here and continue to get good grades. Our donors don’t just like to look at the girls, they also like to fuck them, and they pay very well for this service. The prettier the girl, the more they pay, and the more people want to fuck her. The very pretty girls get fucked a lot, in all kinds of nasty ways. They could complain, but we always have lots of evidence of their misbehaviour. Of course, sometimes the really pretty girls are very well-behaved, good girls, and we aren’t able to catch them giving blowjobs or fingering themselves in the bathroom. This is a problem for us, so we take steps to put them in a position to get caught. We have some very handsome and charming friends, who are more than happy to come in and turn our good girls into dirty whores. All captured on camera of course, girls dressed in stockings and suspenders and uniforms playing with themselves while sucking cock before getting fucked by three or four guys. What would their parents say? So, once they’ve watched the video, they become very compliant.”
“Which is where you come in. Some of our friends like to fuck little girls like you in the ass, which can prove problematic. Even girls who are being blackmailed often balk at anal. Luckily,” Mistress pushed her hands up inside Jenny’s dress, found her nipples and started tweaking them with her long nails. “You are a filthy, dirty whore who loves being fucked in the ass, which makes you perfect. So you are going to be used in the way that all sluts like you should.”
Mistress pinched Jenny’s nipples, causing Jenny to squeal like a girl in pleasure.
“As I’ve already said though, first of all you are to be punished and tested. You are going to get up, lift up your dress and pull down your panties. You’ll need to get used to that anyway, exposing your ass for use is going to be a common theme for you. Do it now.”
Jenny reluctantly stood up as Mistress removed her hands from Jenny’s dress, then even more reluctantly lifted her dress at the back and pulled down her pretty knickers. Even this felt good; the soft, frilled silky panties stroked her private place and then ran down her stockings, a terribly thrilling sensation.
She pulled them down to her knees, then followed Mistress’s prompts and bent over her lap, with her little backside lifted high up into the air completely exposed.
Headmistress ran her hands over her peachy white ass, loving the quivering little girl over her knee completely submissive to her.
“Your lovely little backside is just delightful, but it can be improved with a nice rosy red glow I think. Squeal and whimper as much as you like, my secretary loves listening to sluts being punished.”
Without warning, the Headmistress lifted her hand and brought it down again hard against the sissy girl’s cheeks. Not stopping to pause, she spanked her again and again, raining blows down on the soft flesh of the sissy. Jenny, at first too shocked, didn’t make a noise for the first few seconds until the fifth or sixth slap on her ass before she started squealing and wriggling in the Headmistress lap. Each time she wriggled her little caged clitty felt some of the Headmistress skirt rub against it causing delight as she had her sissy pussy punished.
“That’s a good girl, make lots of squeals for mistress.” the Headmistress said, spanking her again and again. “And now you can just whimper for me. Stand up and present your clitty to me.”
Jenny quickly stood, not wanting another spanking. Lifting her dress up, Jenny presented herself to Mistress, leaving her pink panties round her ankles.
“Good girl. I do like well-behaved little sluts who do what they are told. Now then we come to our next little test. For this you’ll need a blindfold at first, we wouldn’t want to scare you would we. So let me just put this on you.”
The Headmistress turned Jenny’s head to fasten the blindfold over her eyes, preventing her from seeing anything except the inside of the pink satin material over her eyes. The Headmistress then clicked the intercom and said “Miss Jones, now please.”
There was a short pause and then Jenny heard the secretary come in, her beautiful long heels clicking along the floor. Jenny was immediately embarrassed to be seen by another young pretty woman who had already made her disgust known.
“You were right about this little faggot then, guess she’ll provide some entertainment at least. Okay, you can come in now.”
Jenny wasn’t sure who Miss Jones was talking to, but she heard another set of footsteps enter the room. They walked over to Jenny and stopped in front of her.
“Now is that any way to greet our guest Jenny? Do you want another spanking or are you going to say hello properly? Now, down on your knees, open your mouth and unzip his trousers.”
Jenny’s mouth dropped open at this point regardless, not quite believing what she had said. Did Headmistress want him to suck a real cock? Her answer came very quickly.
“Open your mouth and start gobbling that cock before I get angry!”
Jenny quickly knelt down in front of the unknown man and, with trembling fingers, slowly undid the buttons on his trousers. She could feel his cock hardening under her fingers, and reached her red painted fingernails inside, fishing around before grasping his hard, throbbing penis and pulling it out. Jenny could sense the warm flesh in front of her face, and gradually moved her mouth forwards, red lips sliding apart, tongue slipping out to lick her lips as she approached the head.
She took the head of the cock smoothly in to her mouth, tongue sliding underneath it and running along the soft skin. He took control at that point, taking hold of the back of Jenny’s head and pushed his cock into her. Jenny resisted a little, but he allowed no resistance as he forced his large manhood into her face.
At this point Jenny heard the Headmistress at her ear, “Mmm good sissy, suck that cock for me. Enjoy as he fucks your mouth, taste his cum as you pleasure him. This is going to be your life from now on, dressed as a slut, sucking cock and drinking lots and lots of hot sticky cum. If you are good I’ll reward you with my strap-on later, I know how much you love taking big hard cock in your ass. Madame Jenoix told me all about you and the things she did with your delightful young body. Fancy getting caught in stolen girls clothes and masturbating in a cupboard, you belong to me now. I hope you are enjoying that rock hard penis; I can see your first client is enjoying you. You are going to get your first taste very soon.”
Jenny felt the man grasp her head more firmly and speed up, fucking her mouth harder and forcing his cock deep in to her mouth, almost causing her to gag. Headmistress slid her hand up Jenny’s skirt, and expertly removed the clit cage that the sissy had been wearing for so long now. Her little clitty suddenly jumped after being released, and Jenny moaned as she felt Headmistress take hold of her and started stroking. Headmistress could see how excited Jenny was and, noting how close the man fucking her face was to cumming in her mouth, she grasped Jenny’s clitty and started tugging her quickly.
Her other hand pushed down inside Jenny’s pretty dress and started flicking her nipples, causing Jenny to start making cute little squeaking noises as she was pleasured.
“That’s it my sweet, enjoy the cock, feel how good it feels when you please me. I love watching you taking nice big cocks in your mouth, and when you make me happy I’ll play with you. After you drink his hot cum down, I’ll let you shoot your cum on my shoes and then you can lick my heels clean as Madame Jenoix fucks your ass with her strap-on. Yes that’s it, suck him hard, lick his balls, and enjoy the soft, silky feel of your pretty pink dress against your skin. Oh you are so cute and pretty, you look so sweet with your slutty make up and princess dress. You are going to be made to take cock in every possible way. Here it comes!”
Jenny felt a change in the rhythm of the man fucking her face just before he stopped and shot all his cum into her mouth. Hot, juicy ribbons of salty jism spasmed into Jenny’s mouth, filling it quickly as she used her tongue to entice all she could out.
Jenny couldn’t believe how good it felt to be used like this, especially with Mistress playing with her nipples and clit at the same time. She sucked and sucked at the still hard cock in her mouth, listening to the owner groaning as Jenny greedily took it all in to her mouth. The cock was pulled from her mouth, swinging as it came out before slapping back against Jenny’s face.
Mistress giggled at this, then said “Oh Jenny you are such a little whore. Now open wide for us, we want to see all the cum in your mouth.”
Jenny heard a few quiet clicks, which sounded awfully like a camera…
“Good girl, now swirl it around your mouth and tell us how much you love all that cum before swallowing it all down. Then you’ll get to cum yourself.”
Jenny ran her tongue around her mouth, pushing the mass of jism around and around, flicking it up and letting it run down her tongue to the back of her throat. As it dribbled back, she gulped the first lot down, and felt Mistress flick her nipple, causing a rush of pleasure as the cum went down her throat. Again and again she gulped more of the cum down, each time Mistress flicking and playing with her nipples and clit to pleasure her and help her associate drinking cum with physical enjoyment.
Eventually it was all gone, and Headmistress gave one final pinch to each nipple causing Jenny to squeal again.
“Filthy whore, covered in cum and dressed like a slut. Lift up your dress and jerk your little clit for us, I want your sissy cream all over My beautiful shoes.”
Jenny pulled up the front of her dress and started playing with herself furiously, finally released from the bondage that had stopped her for so long. She felt the tip of Mistress’s shoe tap the end of her clitty, and just as she was about to cum her blindfold was ripped off. Still tugging away, she squeaked loudly as she came, and in that fabulous moment of orgasming all over her Headmistress’s shoe she saw her audience at last.
Not only was she being watched by Headmistress and Miss Jones the secretary, but the wonderful cock she been sucking belonged to her English teacher! Madame Jenoix had also entered the room, and was standing next to Miss Jones having her breasts fondled as she filmed Jenny’s humiliation. She smiled at Jenny as she zoomed in on her cum-stained face. Headmistress lifted her shoe up to Jenny’s mouth and pushed the cum covered leather hard into the sissy’s mouth.
“Lick it up whore. Not so nice being on the other side of the camera is it? I hope you enjoy eating your cum from my shoe, you’ll be getting a lot more very soon.”