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Chapter One Getting Kitted Out
Walking into Spencers Gentlemen's Outfitters was like going back in time, even for a town where several recent decades appeared not to have happened and this was several years ago when I was just a kid of just turned fourteen. Which makes it a really strange place for me to be, seeing that this was the first week of yet another break from school where I was living alone in my Aunt's cottage. But more about that later. Right then I was on a mission.
With my mission in mind, I ignored all the stands with their neatly arranged displays of clothing from another time, heading instead straight to the back where a somewhat stuffy looking man was waiting behind the bare wooden counter, all the while holding the note in my hand, as if it would explode into flames at any second.
"Can I help you, Son?" Mr. Spencer asked, his eye brows raised, perhaps permanently from having someone under the age of fifty in his shop.
"I've got a note for you from my Aunt," I told him, pushing the neatly typed envelope over the counter, so he could see that it was addressed to him personally.
"I see." he said, not that he could see anything yet but he would very shortly once he started to read.
Without saying a word, he picked up a small knife with which he used to open the letter that I'd so carefully sealed, withdrew the folded paper from inside, and looked it over. His eyebrows not showing the slightest sign of surprise of the words he read.
"You are the Kyle Smithson mentioned in this note. The nephew of Miss Blackwood-Smythe?" was his first question, and an odd one at that given the note said I was, and I'd just given him the note. But then notes like the one he was holding often have that effect on people. Something which I was going to being putting to good use that summer.
Anyway, I told him I was, so he asked the next question. This one I was at least expecting.
"Your Aunt has requested we furnish you with a school uniform, as you are in need of some discipline," he looked me up and down, sneering slightly at the jeans and shirt I had on, even though neither were particularly scruffy. "The style of uniform your Aunt has requested is no longer sold, as schools generally do not require their pupils to wear shorts all year round."
"That's a great shame," I said, taking my cue, "Aunt Aggie really wanted me to have a nice pair of shorts just like she remembered boys my age wearing when she was young. She'll be very disappointed if that isn't going to happen."
I let that last bit hang in the air, so that it would sound exactly like the threat it was meant to be. Of course, normally store owners won't take a threat from a skinny little kid barely into his teens, but in Blackwood, my Aunt's name carried a lot of wait. The town was named after her family, after all, and she still owned a fair part of it.
"Well," the proprietor said after he'd had time to think about all the business he could be about to loose, "We might have some old stock down in the basement, if you would care to come back in a couple of days we may be able to find something to suit you."
"I'm afraid, as my Aunt made clear in her note, that as I only have the clothes I'm standing up in, that I will be needing them before then. Is there no way we could go and look for them now. Perhaps as my Aunt suggested, the Saturday boy could help me?"
Written down that sounds like I was being at best cheeky, or at worst, plain old bratty, but I came from a good family – albeit a very minor branch of it – and was rather used to getting my way, even if I sometimes had to resort of subterfuge to get it. Plus I wasn't beyond, fluttering my eye lids, and giving a coy smile, which given my overall boyish appearance more often than got me what I wanted. Just like it did on this occasion.
"Yes, yes, that is a good idea. I will get Master Spencer to help you. If you would care to wait there a moment."
Given how long it had taken to set all this up I was only to happy to wait for the few minutes it took the owner to dash into the back room to fetch his assistant, especially as it gave me the perfect chance to retrieve the note, and tuck it back into my pocket, out of the way just as the voices returned.
"The lad requires a traditional school uniform. You will find them down in the basement. He is to be fitted out completely and the price added to Miss B-S's bill. Understand?"
Walking onto the shop floor behind the owner was a teenager who I knew helped out in the store when he wasn't at school. However, although I'd called him such, he wasn't the Saturday boy – it was a Tuesday – but the owner's son, something that was fairly clear when you saw them together, as they shared the exact same colouring, and demeanor. Mark Spencer was sixteen, and about to go away to collage to study, clothing design, something which seemed rather pointless given the nature of his dad's shop, but then they did need to do something to get more customers as the place was deader, than the graveyard at the other end of town.
Having been given his instructions Mark turned to me, looking every bit as handsome as I remembered him from my last time in the store. Not that he seemed to remember me, which was handy. Instead, he just asked me to follow him down into the store room, which I did, moving past row upon row of unopened stock, that looked like it had been there longer than I'd been alive.
"This is where we keep the prep school stock, although as you see, we haven't had much call for it recently since most of the schools around here changed into wearing longs. However you should be able to find some shorts here, as well as caps, blazers and everything else you need. If not, as my father no doubt told you, we could probably get it made for you, but that will take extra time."
I was barely able to speak. Not for one moment had I imagined they had quite as much as this down here and certainly that they would be able to make some of the other items I had in mind to wear. That though would be for later. First I had to get a uniform sorted out, before I set about getting myself a tutor. "I'll take them all." I told Mark, a little too enthusiastically.
Mark said nothing, just gave a little nod, and started going through the boxes, taking out various items that he may think were suitable, while putting others to one side, to repack later. It not being long before he had a good collection. Only then did he ask the question I'd been waiting for.
"Would you like to try them on, prior to purchase?"
"Yes, I think I should." I smiled at him, at which point Mark informed me there was a customer changing room up in the main shop, but by then I already had my jeans around my ankles and was stepping out of them.
"Ah I see you are wearing boxer shorts."
"It's what all boys my age wear." I lied, which while perfectly true for most fourteen, wasn't actually always the case for myself, as I had an entire range of underwear that was really not typical hidden away at home, a long with a lot of other clothing I'd collected in the last couple of years. Still, on occasions like this, where people were likely to see my underwear, I did tend to go with the more excepted versions, just to be on the safe side.
"I'm afraid they will not do with your uniform, as they could bunch up and become uncomfortable as well as spoiling the cut of the cloth." exclaimed Mark sounding much more like his father than he probably realised.
"Oh right, we wouldn't want that, would we." Sometimes sarcasm gets the better of me. I covered up quickly though, "My aunt wouldn't like that. Have you got any briefs?"
"Of course. I'll just go upstairs and get them. One moment."
He was only gone for a few moments, but by the time he was back I was totally naked, and standing in a way that made sure he couldn't miss the redness of my bare bum. Disappointingly Mark didn't say anything about it, which was a shame as I'd put a lot of work into doing that.
Did you know that spanking yourself just isn't as easy as it sounds? It's actually quite difficult, to get the angle right, and get even coverage, especially if you are using your hand as my left hand just isn't as strong as my right, leaving that side, a different colour.
Still, using one of Aunt Aggie's old style hairbrushes with the big flat back on the head, does a really good job, especially when I set the time for how long I have to spank myself for, and stick to it, no matter how much it stings, and even if I start to cry, which I had done just a before I'd left The Cottage to come to the clothing store. My bum, I knew, would have lost none of the bright scarlet sheen, that had made sitting still on the bus into town almost impossible, even though jeans and boxer shorts.
"Here are the briefs that should fit you." Mark handed over the package, in such a way that I didn't need to turn around, just like the professional he no doubt was. Artfully turning his own back to fiddle with something that didn't need fiddling with, while I pulled them up my legs, and tucked my tackle down inside them.
"Try these shorts first. I think these will be the ones your Aunt was be looking for."
Taking the shorts from Mark, I stepped into them, feeling the smooth white lining, slipped up easily over my thighs, although I did get something of a shock when I went to fasten the zip. There wasn't one.
"They have a button fly." explained Mark,although I'd already discovered that. "It's how they were back in the old days. They even have a button on the inside for braces rather than belt loops."
I hadn't thought of braces, but it was too late to change the note now, without giving the game away, so instead I just fastened the waist button first, and then worked out how to do up the somewhat unfamiliar fly.
"It's easier to start from the bottom and work up. Those, like the briefs, are for an eleven year old in his final year, but I think they should fit you just fine."
There was no mocking in Mark's tone, as there was occasionally from my mates at school about how I was shorter and smaller than nearly all of my peers. Not that I minded as I could take a joke, in fact I rather liked being the subject of a good joke and as you'll discover it takes a lot more than words to humiliate me. Plus I really liked being as boyish as I was, as it meant I could get away with so much more than they ever could, looking even the slightest bit like an adult.
"If you are going to have a full uniform in the old style then you will also need, some short sleeved shirts, some long socks, a couple of armless v-necked jumpers, a blazer and a cap, which I think we have somewhere."
"What about shoes?" I asked, finally managing the last of the buttons holding back the semi stiffy I was getting. "What sort of shoes should I have?"
"Sandals, usually for school. Not sure we've any that will fit you but I'll have a look."
Seeing that it was all going so well, I decided to push my luck and ask for some casual clothes, of a style to go with the school ones.
"We have both corduroy and khaki shorts, which should do you, and plenty of shirts and socks." Mark informed me, adding them to the already growing pile, "What about a PE kit? Did your Aunt want you to have one of those too, as that would be everything on the school's list."
"If it was on the school's list then I'd better have it." I nodded, picking up one of the shirts Marc had laid out and slipping it on finding it to be a surprisingly good fit over my slender torso.
"All this is going on your Aunt's bill, is that correct?"
"Yes, Aunt Aggie said I could spend anything I want," I told him, probably telling him the first true thing since I'd arrived in the store which oddly made me blush. So I bent down to pull on the lock socks so Mark wouldn't be able to see my face.
"The socks should be rolled up over your knee and then folded down to show the school colours."
It was a needless instruction as I already knew that, but I did as he told me before putting my trainers back on again. They didn't really go with the image I was after but they were all I had.
"Oh wait. I think I know where there's some sandals."
Mark was only gone for a second, before he came back with a pair of traditional Mary Jane style shoes, that were every bit the perfect thing I wanted. All open panels with a large buckle going around the top of the foot to hold them on. They were also a perfect fit.
"Good, and I see you can tie your own tie. Aren't many boys your age who can do that. Try this jumper."
"I've had practise." It was the truth I did have having being doing proper Windsor knots from some time now, rather than the either massive, or tiny ones that most of my peers favoured on the rare occasions that they actual wore a tie that wasn't strung on elastic.
"Now the blazer. It doesn't have a school crest, but they just iron on so I can put on in if you want one."
I said I did, slipping my arms into the school jacket while Mark held it open for me. A quick shrug pulling it up onto my shoulders where it sat, so naturally it was like I'd worn one all my life. Which was about as far from the truth as it could me.
There was only the cap to go but Mark wouldn't let me put that on, as they were only to be worn outside. "Wearing one inside, was a punishable offence and you wouldn't want that would you," he said, with a smile, that said far more than his words had.
"There, you look like a little boy from a prep school, just like your Aunt wanted." Mark stood back to admire the clothes I was wearing, which is something I really wished I could do but there were no mirrors in the stock room.
"Now if you'd like to get changed back into your own clothes I will have everything packed up ready for delivery."
"Can I wear them home." I asked, again with too much enthusiasm, that lead to a smile on Mark's slightly spotty face, and a quick backtrack from me. "I think my Aunt would like that."
"Yes, she probably would but you are aware that people will be able to see your various colours of your legs."
Peering around behind me, I smiled as I saw what Mark meant. Most of my legs were brown from the sun, but for the tops of my thighs which were a bit were a bit on the pale side, except around the back where I'd smacked some redness into them.
"That's okay." I said, and it was too. I wanted people to see my legs, and probably a fair bit of the rest of me too. That's why I'd arranged to stay at Aunt Aggie's cottage on my own, for the entire summer. So I could get up to any and every game in a long list of things I wanted to do. The least of which was for people to think I was a naughty little boy, in shorts who got spanked. That was just the start of it and it was the notes that were going to make it all possible.
"Well, if there is anything else you or your Aunt will be requiring, then please don't hesitate to let us here at Spencer's now."
"There is one thing?" I said, looking at one item in particular on the pile Mark had made.
"What is that young man?"
That Mark had called me that, despite his only being a couple of years older than me, gave me a slightly thrill, adding to the excitement behind my voice as I asked if the PE plimsoll could also be used to give a naughty boy a spanking.
For the first time since I'd met him Mark Spencer, was put on the back foot by my question although to give him his due he recovered quickly enough. Picking one of them up by the heel he flexed the toe part with his other hand, proving just how flexible they were. "Yes, I believe they could be."
"Would it be possible to have a demonstration, do you think?"
"A what?"
"A demonstration. IT's how naughty little boys in shorts would get punished back in the old days, isn't it?"
"Yes, but
"
"And isn't it your store's policy that all items you sell can be tried out before they are purchased?"
"Yes, but
"
Mark's protests stopped when I turned my back to him, bent over, flipped up the back of my blazer, and put my hands on my knees. My short covered bum pointing directly towards him. "Can you try them out for me, please?" I asked, in my best little kid voice.
"I don't know." Mark was more than a bit flustered, but if there's one thing that a teenager can't resist it's the chance to smack the bum, of a younger boy, even if they don't realise it until the opportunity is presented to them, like I was doing to Mark and which he gave into with a hearty "Oh what the hell"
Moving quickly around to my side, Mark grab hold of my waist, with his left hand, while his right hand went to work with the plimsoll on the seat of my new shorts, if only six times.
"That appears to work." Mark said when he was done.
"Matter of opinion." I murmured, standing up.
"Yes well, that's as may be but it's not as if you have actually done anything
" Mark didn't finish his sentence as by then I had the school cap on my head, in what was a clear breach of scholastic rules.
Now Mark didn't need any more manipulation on the subject. With a "Oh right. In that case." he sat himself on the side of the nearest table, grabbed me about the waist, and plopped me right down over his lap, where he went to real work with the living room.
WHACK! WHACK! WHACK! WHACK!
There was a good bit of weight behind the blows that crashed down on my bottom, giving them a lot more effect than the hairbrush had earlier, even though the double thickness of the shorts and the briefs.
WHACK! WHACK! WHACK! WHACK!
My bum was soon getting past the point of stinging, as Mark made sure to visit the rubber sole of the living room on every part of my backside, with a precession that I could never manage on my own.
WHACK! WHACK! WHACK! WHACK!
Tears stung into my eyes, but I managed to hold it together, just about, as this after all was a long way from being my first ever spanking, even if the bus ride home was going to be a strictly standing room only affair.
"There's how is that." I was asked when a slightly out of breath Mark, allowed me to stand up once more, having given the living room a very good practise run.
"Good." I answered honestly, unable now to resist reach back behind me to give my burning bum a bit of a rub, just like prep school boys would have done through the years.
"Well, Like I said, if there's anything else you want, you know where to come."
And indeed I did. I even asked him if he knew of any good tutors, and if there was a scout pack I could join before I left the shop with a sore bottom and an erection that needed some serious attention, assuming I would ever be able to unfasten those stupid buttons.
Chapter Two How the Dressing Up Started
"Are you going to wear that?"
Those were the words Luke Taylor said to me two years earlier that pretty much started my secret life of getting dressed up in what should have been humiliating clothing, and it happened in Blackwood.
Summers with my Aunt Aggie were the highlight of my life even at twelve, as Aggie let me do just about anything I wanted to, and with her standing in the town I could have got away with anything. Only I didn't realise that then. Instead I was just happy enough doing normal boy things, like watching TV and eating. That is until Luke Taylor let me see what was hanging in his closet.
The Taylor's were renting a cottage in Blackwood from my Aunt, who still owned a fair number of properties in the small town, and given Luke was only a year younger than me, I started to hang out with him more and more, getting up to this and that, but no matter what we played, there was always something I wanted to do more than anything else, and that was to try on the clothes in Luke's closet
Now, I know that sounds weird, especially as the clothes weren't even Luke's but had been there for years from when the cottage was rented out for couples getting married as it was right next to the parish church. And yet, while he and I were both content to go around in the same jeans and T-shirts I had always wondered what it would be like to wear other clothes, especially something that no one my age would be seen dead in, like a sailor suit. It wasn't even anything special, just a pair of navy blue shorts, with a white shirt, that had some brass buttons on, and a flap at the back. Yet, I wanted to wear it. But how?
Then two days before I was going to return home, I found out that the Taylor's were going out for the entire day, which it seemed would be my only chance to play dress up, just as I had done as a little kid. All I had to do was plan a way to get into their cottage which was easy enough as Aunt Aggie had keys to all her property hanging on a big board in her office.
The next morning I got up in time to see the Taylor's car pull away from the house, and I was on my way. Telling Aunt Aggie I was going out to play – not a lie, although she wouldn't have cared either way – I headed straight to the Taylor cottage, nipped around the back and let myself in through the kitchen door.
Despite being alone I crept as quietly as I could up the back stairs, and into Luke's room, which was the right at the back at the top of the stairs meaning that within a minute of entering the building I was standing there standing looking into his closet at everything I'd been dreaming about.
Luke Taylor was a typical boy in that clearly he never hung anything up, but then why should he as it wasn't his room, and he was only there for a few weeks, so he was pretty much living out of his suitcase, which was opened in the corner. His clothes scattered around it like they'd been murdered. Not that I cared about any of that, as I stepped over it all to get to the closet.
My heart was thumbing in my chest, while something else was throbbing in my jeans, as I reached out for the knob and slowly pulled it towards me. There hanging, right at the front, just as I remembered it was the sailer suit, in it's protective covering.
Reaching in, I pulled it down from its hanger, holding it in front of me as I walked over to the mirror to see if I could see how it would look on me. NOt that it really mattered as I'd already made up my mind to wear it, only I never got the chance as it was at that moment that Luke said those words that were to change my life:
"Are you going to wear that?"
I turned to see my friend standing in the doorway with a lop-sided grin on his face. At the same time, I attempted to hide the sailor suit behind me, as if I hadn't already been seen with it.
"Oh hi Luke, what are you doing here?"
Without moving, or loosing the smile, Luke replied that he'd ducked out of the family trip at the last moment, and was meant to be catching up with his school work, which he'd been doing, downstairs, until he'd heard come to see who was going through his closet.
"I wasn't." I blurted out although we both knew I was given the evidence was still in my hands as Luke was quick to point out.
"So what's that behind your back then?"
"Nothing." I tried, not yet having taken up my later policy of fronting things out.
"Looks like the sailor suit from the closet to me. But what are you doing with it?"
"It fell off, and I was just putting it back." I really wasn't that good at lying back then.
"You know," Luke took the sailor suit from me, "The note on this says it is for a ten year old, but I bet you could wear this if you wanted to."
The words made me freeze to the spot. Had I heard him right. Did Luke think I should wear it? Was he encouraging me to wear it? Why would he do that? These were the questions that were going around my head back then, in the days before I realised just how much fun people get from seeing boys all dressed up in weird stuff, and how much fun it can be to be dressed up.
Of course I was also aware that it could be some sort of trap Luke was laying for me, but up until that moment we'd always got on really well, and well, Luke just didn't seem the sort of kid that would bully enough one, just for the sake of it. He could even see what was going on in my head, judging by his next comment.
"Don't worry I won't tell anyone, if you want to dress up. It'll be our secret."
I was twelve then, and he was eleven so we were still young enough to be excited by the idea of having secrets in a way that could tie the two of us together. So a cold chill of excitement ran down my spine as I thought about it but I didn't say anything, leaving it to Luke to decide where to take things which he did in the same way he had for every game we'd played. By making rules.
"Of course, we'd have to have rules." he said, "First we don't tell anyone."
That I agreed to, which is odd given that everything else I did that was a follow up to this moment, I very much didn't do in private.
"Second, we have to behave in the way you're dressed, and that you stay dressed until it's time for you to go home, or my parents come back, whichever is first."
Again that one made perfect sense, and I agreed to it without thinking about it, despite what he said next.
"Now do you want to see what you're going to be wearing!"
"But I thought," I held up the sailor suit.
"Oh no, there's something so much better than that in the other bedroom. Come on."
He led me into the room next to his which oddly enough I'd never been in before. It was exactly the same as his, but clearly laid out for a girl. The comparison going right down to not just the closet but what was inside the closet where there was another sailor suit, only this one was for a girl.
The dress was make of a much silkier material than the boys version, with added lace and even a few bows attached all over it. A lacy collar around the neck, the shoulders puffed up before coming down to the elbows, where they were bought back together again. Instead of shorts there was a skirt, or actually two skirts as I found out later. The lower one being of the same navy blue as the shorts had been, but over that was a second layer made of white mesh onto which little white bows and even more lace had been fastened. A large wide ribbon went around the waist, and could be tied at the back. There was even a petticoat to make the skirt stand out more.
"This is PROPER dressing up," Luke said, putting the dress on the unmade bed while he went over to the chest of drawers and pulled out some more things. "You'll need underwear, and socks. Oh and shoes."
The shoes were in the bottom of the closet which apparently Luke knew about although just how he knew where everything was I never thought to ask until much later when it was already too late, which is a shame, as I think we could have had great fun both dressing up, but alas that never happened.
"Right that's everything. I'll leave you to put it on, but if you need help, just ask."
Again, I should have asked how an only son, with no sisters, knows so much about girl's clothes but I never did, just let Luke slip out of the room and leave me too it.
Now I was in a quandary. One the one hand I wanted to dress up in all this stuff for reasons that I didn't quite understand at twelve. Yet on the other hand, I know I shouldn't want to, and should probably keep things like that to myself. However, Luke promised to keep it quiet and, after all he had dared me – sort of – to do it, and to a boy there can be nothing worse than refusing a dare from a friend.
While I was thinking all this I found myself casually fingering the strange underwear which were white and silky with ruffles attached to the outside all around that I couldn't help but wonder what they would feel like on. Clearly there was only one way I was going to find that out. And didn't think there would be another chance for me to find out. Mind you I was wrong about that last bit, but I didn't know that then.
Having removed my clothes, I felt a chill of excitement before I even stepped into the knickers, but my the time I had them pulled up where they should go, the silkiness was so unlike anything that I'd felt before, that I was causing a tent in the front, that was going to be pushing me forward to try so many new things over the next few years.
I was surprised that the socks felt like the underwear. All soft and silky as I'd just assumed that socks were socks. These though were so much better, even with the three rows of lace trim near the top. They came all the way up to my knees, feeling so soft and warm on me.
Now it was time for the for something I hadn't put on before. A petticoat. This one was made out of a smooth, nylon material, with white flower lace attached to the edges. It came in three layers of soft lacy ruffles that caused it to flare out slightly on it's own, which gave me some trouble in trying to find the part where I was to put my head through and was blinded for most of the time I was pulling it down to my waist. Yet once it was in place, I rather enjoyed the touch of the ruffles rustling around my legs.
Removing the dress from the hanger I felt the cool and silk in my hands,as I raised it up over my head, and pulled it down, sliding my arms into the sleeves as I did so. It was just like putting on a big jumper, just as Luke had said, although with this you had to spread it out across the petticoat rather than just letting it hand as you would do with a pullover. What's more, was that the petticoat didn't stay down, even when I pressed it, but would spring right back on it's own, which was the weirdest feeling in a day or rather weird feelings.
There was only the shoes left, which I put on in the very boyish way of just jamming me feet into them, until the heels clipped down.
"You done yet?" Shouted Luke from the hallway, where he'd obviously been waiting and quite probably staring through the keyhole, waiting to ask that question and be invited in.
"I can't get the dress zipped up," I shouted back,
Luke volunteered to do it, coming into the room even before he'd finished saying just that, only to stop and stare at me. "Wow, you look great." He stared me up and down, "Wait something's not quite right."
Going behind me, he made short work of raising the dresses' zip all the way to the top, and clipping it in place so it wouldn't lower again. He then pulled the sides of the ribbon around my waist together and fastened them in a large bow.
"That's better. Oh wait. You're shoes."
Kneeing in front of me, Luke almost had to put his head under my petticoat in order to first unbuckle the shoes and then, once he'd got my feet in right, rebuckle them good and tight.
"Come and look in the mirror."
Oddly I hadn't thought of that having totally missed that unlike Luke's room, and probably the only difference between the two rooms, was that this closet had a mirror on the front. Just a shame no one had shut it so that I could see it until the moment Luke did as otherwise the way I looked wouldn't have been so much of a shock.
I could hardly believe what I was seeing never having encountered just how much a different choice of clothes could so radically change how someone looks. Sure I knew the person I was looking at was me as it had my face, and perhaps most oddly my hair cut, but from the neck down, I looked every bit like a small girl. You couldn't tell I was a boy at all, even if my own boy parts, were seemingly desperate to escape from the knickers they now found themselves trapped in.
"Come on, let's go downstairs," suggested Luke, even taking my hand which is something he'd never had done if I was dressed like the boy I really was.
It was tricky to follow Luke Taylor down stairs to the front room of the cottage his family was renting but not from any reluctance on my part, as I wasn't even thinking about that. Instead, it was the tight shoes and the sensation of the petticoat rustling against my legs, that caused the skirt to sway back and forth as I moved that made it a struggle to walk, as I just wasn't used to walking like a girl. Luke though knew what I was doing wrong, and again, I never thought to ask just how he knew.
For couple of hours, Luke taught me everything I needed to know in order to act like the little girl I was dressed up as. He showed me how to walk, and especially how to sit down so I didn't get swallowed up in a mountain of lace and petticoats.
"You know, if it wasn't for that haircut, you could probably pass for a real little girl." Luke announced when we were apparently done with my training. "Perhaps we should get you a hat and go outside to see if anyone spots you're a twelve year old boy not an eight year old girl."
"Won't people laugh at me?" I said, not as horrified by the idea as I probably should have been.
"No, not if you do it right and anyway, if anyone does then you can just tell them you are being punished for something, and they won't say anything about it."
"Really?"
"Yeah really!" Luke said with some conviction but once more I missed a chance to ask him just how he knew that. "You can get away with loads when people think you are being punished, or when you have a note explaining stuff."
"A note?"
"Yeah, like at school, when your parents say you can't do PE or something. Adult will let you do anything as long as you have a note saying that you can."
That was the first time I'd heard about the power of the note, and in the years that followed I turned note writing into an art form, especially once I discovered my Aunt's headed paper and the old typewriter that could turn my childish scrawl into an official looking massif with just a bit – well a lot – of practise.
Anyway, that's pretty much were my first day of dressing up ended, as it wasn't long after that when we heard Mr. and Mrs. Taylor coming home, leading the pair of us into a mad rush to get back upstairs, the dress back in the closet and me into my boy clothes, before they could wonder what we were up to. If only we'd had the foresight to write a note, there and there things may have turned out differently, but as it was, Luke and his family left a day later, and that was that.
At least it was until I started to put my own plans into action, following a few other experiments, when the power of the note, got me an entire summer at Aunt Aggie's cottage, while she had a holiday elsewhere. Not that my parents realised that last part of course. But then, that's what notes can do.
Chapter Three Learning A Lesson
At the sound of the door knocker being, well, knocked, I slowly got up from where I'd been sitting waiting for my first experience of the summer to arrive. Carefully I checked everything was ready. The small old fashioned wooden desk, with the flip top lid, was positioned just to one side of the Aunt Aggie's front living room where I'd set up a small study area, close to the sofa and comfy chairs.
The door knocked again, making me smile, yet still I didn't hurry, taking my time to ensure my knew short sleeved school shirt was tucked into my shorts, in the smartest way possible, whilst at the same time, loosening my tie slightly, and making it crooked, as if I didn't want to wear it. Only then did I head off to answer the door.
"Hello," said the youngster standing there his hands clasped behind the his back slightly bunching up his otherwise immaculate jacket, pulling it back from covering the button down shirt, and heavily pressed chino, "Is Miss Blackwood-Smythe at home?"
I told him my Aunt wasn't, which was true, although I may have made it sound like she'd only just left rather than hadn't been there for weeks, and wouldn't be for several more. This seemed to confuse him, as well it might.
"Oh, but I got a note from your Aunt, to come around to be interviewed about some tutoring. My name's Andrew James."
All that I already knew of course, just as I knew that Andrew was just going into his final year at the local prep school where he would continue to be a prefect, with a good chance of becoming head boy. This not only meant he had experience in tutoring other boys, but that he knew just how to discipline them as all. And that's just what I wanted. I mean, that's what my Aunt wanted for me. According to the note he'd got anyway and which was about to be confirmed in another one.
"I'm Kyle," I told him, very nearly offering him my hand to shake, before deciding that would have been much too formal and not all in the character I was attempting to portray. "My Aunt left you a note."
Taking the envelope I offered him from the hall shelf, with his name neatly typed on the front Andrew, ripped it open and little rashly, making himself blush, before read through it quickly, taking in a repeat of the information I'd already told him but which would appear more official from Aunt Aggie's headed paper.
"Okay then," he said when he was done, taking control just as I hoped he would, "I guess, we'll be spending some time together over the next few weeks."
"Looks like it." I tried not to smile.
"It says here," Andrew flicked the note in his hand, "That you are to be dressed smartly at all times, and I see you've made a start on that."
"Thanks," I blushed a little, my fingers picking at the hem of my shorts, as I caught him looking me over in the uniform from Spacers' store that I was wearing.
"Your tie is crooked though. Here let me fix that."
He did it so fast that I barely had time to take in his words, before my tie was not just straightened, but also tightened and raised, into the proper position, at my throat.
"There that's better." he stepped back again, "YOu do know that's a junior boy's unform don't you? Makes you look like a little kid, but I guess, from the way you've been behaving, that's rather in keeping isn't it?"
I smiled but said nothing, as clearly Andrew, had taken on board the back story the notes he'd been sent had given him about how I was a naughty little scamp, who needed taking back under control, with a firm hand. Something that he was expected to have. All for my own good of course.
"How old are you anyway?"
It was a standard question for boys to ask each other the first time they met, and I'd been expecting it, given that I'd deliberately left it off both the notes, so that I'd have some option about which way to go when the time came. That time was now, and I quickly ran through the choices open to me. First would be to openly lie, and say I was the ten or even younger that the uniform marked me out as. However there were some issues with that, not least of which was my size which may have been slightly on the short side for fourteen, would have still been somewhat lanky for ten year old. Then there's the matter of when Andrew got to see me naked, which if everything went to plan he would. Often.
The second choice would be to make myself the same age as Andrew. This would make sense physically, but would perhaps not work out so well if he thought he was just bossing around one of his peers. The sense of kinship boys of the same age, might be an issue. So instead I went with my true age. Sort off.
"I'm fourteen." I said and waited for the expected response, which wasn't long coming.
"Really. Fourteen. But you're my size, and what's with the shorts?"
Dropping my head, as if I was embarrassed I told him, "I'm being punished. Aunt Aggie says I behave like a little kid so I'm going to be treated like one."
"Ah right," Andrew sighed, "So that's what the notes meant. I get it now!"
Not wanting any more conversation on the matter, as I hadn't really worked out too much of a back story for myself, I suggested with move through to the living room, away from the front door, trying as I did to imply that I didn't want anyone seeing me in my 'punishment' juvenile clothes. That made Andrew smile but soon he was gaping in awe at Aunt Aggie's cottage just like everyone did when they first got inside.
The Cottage wasn't actually a cottage at all, that was just what Aunt Aggie liked to call it that. It was actually manor house, if not technically a stately home. Not in the same league as Downtown Abbey of course, but a long way up from the houses the rest of the village lived in, even someone from a clearly well off family like the James'. It was also ancient, in places, such as the bits I lead Andrew through, with exposed woodwork here and there, along with the occasional bits of armour, and other historic artifacts that belonged to the Blackwood family.
However, despite the age of the centre of the Cottage, it had been greatly expanded over the centuries, with a lot of it being pretty modern, such as the living room we eventually ended up in, sitting down on the sofa, to begin Andrew's interview for his role as my tutor.
I started in gentle, beginning with questions about Andrew's school and his role there, what it was like, and general things like that, slowly putting him at easy before I got around to the things I really wanted to know and which were the reason he was there.
"So are you allowed to punish the boys you look after?" I asked, with my best cheeky grin.
"I am." Andrew nodded.
"How?" I pushed,
"Anyway I want to."
"Really," I whistled through my teeth as if I was dismissing the idea, even though I knew that's what Andrew had been told. "So if I don't do what you tell me to do, what are you going to do?"
A grin flickered onto Andrew's face for a moment, making the tiny, faint hairs on the top of his lip, stand up, before he gave me the answer he clearly thought would shock me, "I'd spank you. Hard. With a hairbrush."
"Oh right." It was my turn not to smile as I challenged him. "Go on then. I dare you."
Not giving him the chance to answer, I got up from the sofa, and went to fetch my favourite hair brush which was nice and heavy with a seven inch long handle, and a head that was about four inches square. It was perfect for spanking myself. Now I was going to find out if it worked as well when someone else was using it on me.
"Are you sure about this?" Andrew took the brush from me, turning it over his hands. "You haven't actually done anything wrong, yet."
"Sure I have. Why do you think I'm dressed like this in the middle of summer?"
"Yeah, there is that," he mumbled once more looking at my uniform with its grey short sleeved shirt, tight little shorts and knee socks which I'm slightly ashamed to say, had by this time slid down to my ankles.
"And my tie was crooked," I added, just as I'd planned too, before going in with the killer, "Anyway, how else are you gong to prove to my Aunt that you are the right kid to tutor me, if you can't even give me a spanking?"
"I guess!" he shrugged, obviously not wanting to loose the job for which he was getting nicely rewarded, not from my Aunt, but from my own savings, albeit savings that Aggie was the main contributory too, and had told me to spend on what ever I wanted, although hiring another boy to spank me probably wasn't what she had in mind.
"So," I continued, "if you're going to do it then you'd best do it properly."
"Properly?"
"Yes, make sure it's a proper spanking, and that you are in charge the entire time."
"Oh right. Yes. I see." Andrew mumbled looking down at the hairbrush still in his hands.
"So," I prompted, "What do you want me to do?"
Andrew thought for a moment, making me wonder if he had, in fact, every actually spanked someone before or not. Or if I'd just caught him on the hop with my demand. Turns out it was the latter.
"Right then. First you pull your socks up." He said, moving to sit on the centre sofa cushion, "Then lay down over my lap, with your hands on the floor and your head down as far as possible."
Perfect. That was the exact way I had in mind, and no, this wasn't my first spanking by a long shot. Still I couldn't help shivering slightly as I did as I was told. Positioning myself not exactly as Andrew had said, but making a couple of minor adjustments that would put the tightly stretched seat of my shorts, raised nice and high on his lap, making it the best possible target it could be. One that Andrew certainly wouldn't be able to resist. And he didn't
WHACK!
There was no stopping him once he started. Little more than a second or two between each of the blows, Andrew bought the hairbrush down again and again, spanking each of my buttocks in turn, with good sharp blows.
WHACK! WHACK! WHACK! WHACK!
Tears quickly sprang to the corners of my eyes. Much quicker than they every had done, when I spanked myself, but then this was different in so many ways. The position for one was far more traditional and seemingly suited to a boy being spanked, than the standing way I had to do it to myself.
WHACK! WHACK! WHACK! WHACK!
More blows followed and then Andrew stopped, as he realised something was wrong.
There was a brief pause while he considered what that was, then he shifted by body a little bit further forward, and then took an even firm grip on the hairbrush handle and got right back to work.
WHACK! WHACK! WHACK! WHACK!
Four blows landed in quick succession, all on the same spot, before another four turned up somewhere else. An approach that had an instant reaction from me.
"OW! Ouch!" I yelped, as wetness appeared on my face.
It was obvious now that Andrew knew exactly what he was doing, and that my hunch that he'd be perfect for the role as my tutor and disciplinarian was spot on. Clearly was intent on spanking me very soundly in deed, with no part of my bum to remain untouched as that hairbrush cracked up and down, all over the seat of my shirts, in a rhythm and pattered that left me openly crying right up to the point he stopped.
"Stand up Kyle." he told me, waiting, leaning back on the sofa while I slowly and somewhat painfully levered myself off his lap, up onto my feet.
For a moment I stood there, sniffing slightly, until I could trust my voice to issue my challenge, "Is that it?"
"Why do you want more?"
"Well if you call that a spanking?"
"I do, but," Andrew looked up at me, "What do you call a spanking?"
"One on the bare."
"Is that right?"
"Yes it is."
"Well, in that case you can have another twenty, just as soon as you take down your shorts and underwear."
It wasn't appropriate to smile given the burning in my bottom already, so it was lucky that the buttons on my shorts, caused me to have to look down as I still wasn't used to them, thus hiding my face from Andrew, until I had unfastened my shorts, and push them down to my knees.
"Briefs?" my young tutor questioned, "Guess that's part of your punishment too. Go on get them down."
The the tight white nylon in which my lower regions were encased had to be more peeled down that pushed down, as they were a very figure hugging style. Plus I had to turn my back to Andrew, who was still sitting on the sofa, so he wouldn't see just how much I was enjoying this.
Keeping my back to him, I moved across to one of Auntie's big chairs onto which I placed the palms of my hands, with my head lowered down between them. This made my bottom into an entirely new target, one which I was sure, by now, he wouldn't be able to resist.
I was right.
Almost leaking up from his seat, Andrew raised the tail of my shirt from my back, had himself a little appraisal of his work so far, and then took up a position behind me, adjusted his grip on the hairbrush to suit, raised it high above his head, and then bought it down hard.
WHACK!
A surprisingly high pitch gasp came from my mouth as that first blow landed of that second batch landed but Andrew ignored it as he commenced to beat me slowly and methodically. Two whacks on one cheek, followed by two on the other. Each was very hard, and in almost the same place as the one that had been before it, until I was howling as the wood stuck my bottom. Needless to say, despite the pain I stayed in place right where I'd put myself up until the final blow had landed. Only then did I allow myself to give in to the intense pain I was feeling and to fall down into a crumpled heap, almost curling up on the large arm chair, where I would remain for several minutes.
"Are you okay Kyle?" Asked Andrew eventually, probably wondering if he'd gone too far.
"I'm. Okay. My bum stings."
"I bet it does. It's really red too."
Actually it was a bit more than red, which would lead to me having to spend most of the next day standing up, and sleeping on my front. It also meant I had to put a couple of other things off, until the marks were somewhat less obvious. Still it was well worth it, as now I was sure I had the right kid to be my tutor.
Sure enough in the next couple of days, Andrew James received another note on my Aunt's headed paper saying that she was very impressed with the way he looked after me and offering him the job of being my tutor and for all intents and purposes my prefect, on the days when she would be unable to do the job herself. These dates I made sure were nicely spread out so that my bum would have a lot of time to recover between them, as there was no way I was not going to be spanked again. I just knew it.
Chapter Four Padding Things Out
"Are you the boy with the nappies?" Shaun Hunter asked me bluntly. Clearly the idea of a fourteen year old wearing nappies clearly not bothering him one bit, just as I hoped it wouldn't when I – or rather one of my Aunt's notes – offered him the job as my babysitter.
Naturally I told him I was.
"Good," Shaun nodded, nudging the boy next to him who clearly been examining the way my trousers were hanging on my body for any tell tail signs. "This is Aha, he helps me out."
I hadn't actually expected a second boy to be there. The job of babysitter was odd enough for one thirteen year old boy to do, let alone a twelve year old as well.
"You can talk can't you?"
"Yes."
"Good. One other things. Sometimes we'll have Sasha's brother with us, as he's only nine, so can't stay home on his home. Your Aunt said that would be okay."
She'd said no such thing, but that made no difference. Shaun wasn't exactly pausing in his check list.
"You have you're own nappies, right?"
I nodded. "Up in the nursery."
"You have a nursery." Aha blurted out, much to Shaun's annoyance.
My Aunt's cottage had a lot of rooms, which could and had been used for a lot of things over the years. On my previous trips, when Aggie had been there I hadn't really been all that interested in them, as most of the adventures I had then, took place outside but now I had the place to myself I had the run of the house and made several discoveries that gave me even more ideas than I'd arrived with. Well no so much new ideas, but additions to things that I'd already been planning. Which is why I spent the days after my first spanking from Andrew James, cleaning out the nursery.
You see being spanked in school shorts wasn't the only plan I had for my summer. I also wanted to dress and be treated like a baby. Well, no so much a baby as after all they don't actually do anything but more like a toddler. One how can walk, and maybe talk, but who still needs most things doing for them. Of course I don't mean that I actually wanted to be a three or four year old. Just be treated like one up to and including wearing nappies.
Now I know that's an odd things for fourteen year old to want to do, but it wasn't the first time. I'd actually worn them the year before, more or less by accident, and I'll tell you about that shortly, but this time it was going to be slightly more permanent. Or at least when I wasn't in shorts getting spanked, anyway.
Thankfully the nursery was in a different part of the house to those Andrew James would be seeing, during his time at my tutor, which is just as well as it would be difficult to explain the smell of baby powder, that was in the air, not to mention the large white crib, with the bunnies stencilled on it. Then there was the changing table that was stocked with large disposable nappies, and some cloth, with plastic pants, and nappy pins. Everything in fact that a baby would want, just in a size that was big enough for me.
A big chart on the wall, surrounded by cartoon characters, would let me know which days I would be sleeping here, which days in my 'normal' bedroom, and which days I'd be elsewhere. Everything was encoded of course, and if asked I could just explain that these were the days my Aunt was leaving me in someone else's care although for that to be true, first I had to get myself a baby sitter. Which is where Shaun and Aha came in.
"Are you wearing a nappy now?" Shaun asked and I nodded having put it on myself. That morning.
Taking one of the nappies out of the neat stack I'd made under the changing table, I Open up the nappy on the top of the changing table, I set about climbing up there, using the foot holes built into the sides which I didn't really need, but which added to the experience of being a baby given that no one was going to be able to pick me up, like you would a real baby.
Sitting on the nappy bought back so many memories of the year before, as did the smell of the sprinkled baby powder that floated down between my waist and thighs, making a nice little snowman of my erection.
Reaching down between my legs, I ignored everything that was going on down there, to grab the front flap of the nappy, which I pulled back up, covering up my excitement. Spreading out the flaps across my hips I lay down, twisting myself slightly to bring up the side flaps to meet them. Pulling everything all good an snug, before I used the four provided tapes to secure the nappy in place. A quick test around the waist and leg openings, showed that I was every bit as good as putting a nappy on myself, as I thought I was.
That was it. I was wearing a nappy and ready to start my first day under the second of the regimes I'd worked out. From now on, the days that designated it, I would wear a nappy all the time. Under my clothes if I went out, but, if I was in The Cottage, than that would be all I would wear, just like a toddler would. Changes would be done on a strict time table, rather than when I needed them, and the rest of the time I would do the things that a toddler would. Play in a playpen, eat my food from a high car, and sleep in the crib.
"Right then," Shaun finished his list, "Show me where the nursery is, and I think that's everything."
A few minutes later we were there, and both boys were suitably impressed. More impressed than twelve and thirteen year old boys, probably should be with an oversized nursery.
"Right then, let's see how all this works shall we. Can you get up there yourself?"
The 'there' in question was the changing table, and of course I could and did, trying to make it look like it was something that I'd done hundreds of times before, rather than just a hand full.
"Can't we wait until Sawyer's here?" asked Sasha as I made myself comfortable, waiting for a younger boy to take my sweat pants down.
"We can't leave him wet. How's that going to look, on our first day?"
"Yeah but," Aha started to complain then changed his mind when my sweat pants came down and he could see just how much liquid the nappy I was wearing was actually holding. "Okay fair enough!"
Yes, I wet myself. Purposely, and that's not easy to do when you're not used to it. In fact I'd been wearing the nappy for several hours before the boys arrived and had been drinking water nearly all that time, just to make sure they were under no disillusion that I actually needed to wear nappies. Thankfully as this wasn't my first time in nappies as an older kid, I knew that when I did wet that I had to let it go slowly, rather than all at once like you would normally. There was no firing a hose into the toilet when you were in a nappy, as such a sudden downpour could flood the nappy faster than it could cope with, and that had terrible consequences for your clothes. Assuming you were wearing any, of course.
Shaun went to quick work. Pushing me down, gently but firmly until I was laying back on the changing mat, he made quick work of releasing the four tapes, and then pulling down the front of the nappy. This naturally gave the pair of them a first class view of my tackle, which also naturally gave rise to the usual sorts of comments.
"It's not very big is it?" mumbled Aha in a whisper that could have probably been heard on the other side of the village.
"About as big as yours." countered Shaun reaching for the open package of baby wipes fixed to the side of the changing table.
"Is not. I'm bigger than that."
"Yeah, but his has been stuck in a puddle of cold wee," pointed out Shaun, which was a very fair point, not that it made that much difference to be honest but still it was nice of him to say so.
"He still looks more like Sawyer, than me."
Shaun giggled, "If you say so,"
By this point in the conversation, I'd been cleaned down, and was ready for the nappy to be removed. This turned out to be a two boy job, and explained why Shaun and bought Aha with him. The younger boy, holding my legs up – with my help – while Shaun snatched the damp padding from under me, and slipped a new dry one back in its place, before I was laid back down again.
"Right then let's see how he reacts to this."
Raising my head to see what Shaun was talking about, I spotted the bottle of baby lotion in his hand along with the mischievous look on his face.
Aha smiled, "Go for it."
Squirting some of the liquid into the palm of his hand, Shaun set to work rubbing it into the my skin in the areas that had been, and which would be, covered by the nappy. This naturally included my tackle, which reacted in the way they were always going to, when something slippery comes into contact with them.
"How are we going to get the nappy on now?" wondered Aha surprisingly without giggling.
"The same way we always do," answer Shaun, with a glint in his eye as his hand closed around my erection and started to rub.
It only took a few seconds – I was a teenager after all – and everything was back to normal size, although a new baby wipe was needed to clean up a bit before baby powder could be sprinkled around, and the nappy finally fastened around me loins once more.
"Good that's done," Shaun didn't specify if he was referring to changing my nappy or the hand job he'd just given me, both of which, it has to be said, he'd done really well. "Now he doesn't get his trousers back for the rest of the day, but we do get to feed him. Or maybe we'll let Sawyer do that when he gets here."
"Yeah, Saw will like that."
"Good, let's get downstairs then and you go and find where he's got to."
IT wasn't long before there were three boys looking after me. Two of whom looked like carbon copies of each other, just with one, being a head shorter than the other. That was Sawyer.
"He's a cute baby," was the first thing the nine year old said when he saw me, apparently totally unphased by the sight of a teenager wearing a nappy and very little else. "Can I change him?"
"Sorry Saw," Shaun ruffled his hair, "We just did that."
"Oh you guys get all the fun." the little lad pouted, before brightening, "Hey can I feed him then?"
The older baby sitters turned to give each other grins, "Sure why not?"
Sawyer looked back at me, "He'll let me, wont' he?"
"Course he will. He'll do everything you say, won't you Kyle?"
That last bit was addressed to me – probably the first thing any of the boys had said to me in some time – and I nodded my assent sensing that there was going to be some fun to be had.
The nursery had an eating area set up on one side that I could have easily walked over to, but at Sawyer's suggestion I crawled over there on my hands and knees just 'like a baby would' while Sawyer walked behind me, making very little secret of the fact he was looking at my big padded bottom.
"Right, this is Sawyer's first time feeding a big baby, so what do you do first?"
"Get the baby into the high chair?" Answer Sawyer, giving a little jump that he knew the right answer, before being faced with the reality of relative sizes. "How?"
"Ask him?" laughed his brother before Shaun corrected him.
"Tell him. YOu're in charge."
Pausing to get the words right, Sawyer eventually told me: "Baby Kyle get into the high chair."
I did as I was asked, putting my feet onto the footrest, raising myself up level with the seat and then spinning around so that my padded bum, came down in the seat. At this point, Sawyer finally had something to do, pulling the belt that was attached to the sides of the highchair, and fastening it, tightly across my nappy.
Satisfied I couldn't fall out, Sawyer then picked up the feeding tray, and carefully slotted it into the groove set into the armrest, pushing it steadily into place, until it locked with a click, with it resting pretty much against my stomach.
Looking to his brother's friend to make sure he'd done it right, Sawyer's face broke into wide smile when Shaun nodded his approval. It's just a shame that the added confidence this apparently gave the young boy, lead him to make a costly mistake.
"Apricots," Sawyer read the label on the jar of toddler food I'd purchased with the sort of face nine year olds often have when confronted by something that's good for them.
Emptying the jar into a plastic bowl, Sawyer placed a matching spoon into the disc and then placed it on the feeding tray in front of me. He then spent a few seconds checking that he had everything, looking for something he'd forgotten which turned out to be a drink.
Turning to the small fridge, he had his back to both me and the other boys, so he didn't see the three of us look at each other and then down at the way the spoon was positioned in the bowl, in a way that any one with experience of real babies would never had done.
Sawyer also didn't notice when Shaun lent down and whispered into my ear: "Go on, he needs to learn what happens when you leave something in a baby's reach." Mind you, he certainly noticed what happened next.
A split second later and the spoon was launched via my hand coming down hard on the handle, sending a surprising amount of the creamy fruit high into the air in a slow motion arc that didn't stop until landed right as Sawyer turned around, only to have his face liberally splattered.
For a second there was silence, as everyone looked at everyone else. Then Aha made a dash for the door, leaving a trail of giggles behind him, while Shaun was content to bit his lip. Sawyer on the other hand was rather less amused.
"Bad baby," he yelped, clearing the mess from his face with his sleeve, making it look even less appetising, something which I didn't think was entirely possible. "Now you're going to get it."
"You have to learn not to leave the kid's you're looking after unattended." I said to him, which really didn't help the situation one bit.
"Yeah, but you have to learn what happens when you throw food." the little lad said, pulling the tray away from in front of me twice. The first time it didn't move as it was still latched into place. Then Shaun flicked something and it came away, suddenly, nearly sending Sawyer falling backwards. The nine year old didn't find this as funny as I did.
"Come here," he took my hand and attempted to pull me towards him, but the seat belt was still fastened around my lap, so I wasn't going anywhere, although the high chair did slip a few inches across the tiled floor.
Still bit his lip, Shaun reached to the back of the chair, pressing something that released the seat belt, and then it was my turn to fall slightly forward, as Sawyer hadn't stopped pulling on my arm, causing me to tumble slightly out of the chair, right across the little lad's lap.
I'm not sure if it was what Sawyer had planned to do, but as I'd been released from the high chair and come flying towards him, he'd taken a step back, stumbling into a normal chair onto which he'd had little option but to sit. Then, as I was still travelling forwards, there was no where for me to go, but across his legs, until my hands – not free from his indecent pulling – could catch myself on the far side.
"Hey!" I complained but that soon changed as there was a sudden loud smack and sharp pain in on one of my buttocks.
Turning my head, I looked back wondering what had happened only to see that Sawyer was holding a wooden spoon which was now heading towards my padded rear for a second blow.
"Hey!" I repeated, slightly stunned at this turn of events, as apparently were the other two boys. Aha now having returned from the living room with some advice for his kid brother.
"He's got a nappy on Saw!"
The spoon raised for a third time, but changed direction on it's decent, heading not for the thick padding that covered my bottom, but instead down to the bare and surprisingly tender flesh at the backs of my thighs.
"Ouch!" I cried, imagining the impression of the spoon's head making itself into a contrast to my skin. NOt that there was a contrast for too long as soon another impression joined the first on my other leg.
"Okay, okay," I hollered. "I'm sorry."
"Are you going to be a good baby?" Demanded Sawyer, the spoon raised in an obviously threatening fashion.
"Yes," I promised.
"Good cos if you're not then next time you get spanked, the nappy comes off."
Having been suitably put into my place, I got up from the little kid's lap and returned to the high chair, which I climbed up into and say down, even though the stinging in my thighs made it a little bit uncomfortable, although not as much as having an erection in a tight nappy.
Once everything was settled back, Sawyer took over feeding me once more, doing the entire "Train into the tunnel" thing with the spoon, until all the mushed up fruit was gone. Thankfully it didn't taste all that bad. At least not as bad as it looked but then that would take some doing. Not that I'm about to make it part of my normal diet or anything, but you get the idea.
Once the meal was over my baby sitters, were pretty much done for their first day and although I couldn't tell them, they'd more than passed the test and I'd be seeing more of them later on during this stay at Aunt Aggie's cottage. They would be getting a note to that effect shortly along with some new information, that was going to make things very interesting indeed.
Chapter Five To the Back and the Side
A year earlier, I stood at the gate of the holiday cottage, clutching a bag of stolen items in one hand, a note in the other, stealing my nerves and going over for the millionth time, just what I was going to say and do in order to get myself spanked without an adult, especially my Aunt, getting involved. It would be the very first time I would do this, but, as you know not the last.
By the time I was thirteen, I had taken to spending quite a lot of time secluded in my room, indulging my new passion for being spanked. It had all been triggered during my twelve summer at Aunt Aggie's during an encounter that I'll tell you about later, and which had nothing to do with Luke Taylor. It did however turn me into a life of crime, albeit a very short one.
Of course living at home, with everyone else, didn't give me much chance to try out the practical side of the activity, but all the same I managed to fit in a few experiments, none of which were all that successful as I wouldn't perfect the technique until the following spring. Mind you I had a pretty good go at it.
So with that in mind, I headed off down to Aggie's for the summer, that would, end up opening my eyes to so many new things, only one of which was spanking. There was one thing I was certain about though. I really wanted to recreated the events from the previous summer, at least as much as I could.
It would be this somewhat obsession that would end up with me both breaking the law, and discovering just how a simple note could get me what I wanted, and all down to a pair of little boy swim trunks I saw hanging on a line on one of the holiday cottages in Backwater.
I guess to move thirteen year old boys, it was just a line of washing, hanging out to dry, no doubt following the family renting the cottage having been to one of the nearby lakes where swimming was permitted. I'd been there plenty of times myself, when I was younger but now, as an official teenager, I was looking for more exciting thing than just playing in the shallow water, building sand castles, and things like that. Mind you it had been fun the previous year, just not for those reasons.
For three days those suits hung on that line, probably not getting any dryer, as there was more than a fair amount of drizzle in the air that summer, but for me it was as if they were teasing me. Wanting me to wear one of both of them, just as I had back when I was twelve. Then I bought the suit myself which had been a thrill all of it's own, but then so was stealing one.
It happened an evening or so later, as I lay in bed thinking about being spanked for about the three hundred and something night in a row, when once more I happened to be walking past the holiday cottage where the family were staying and sure enough there the suit was, just hanging there, in a pale blue, with a cartoon character on the front, and another across the seat.
For some reasons I just couldn't help myself. Even before I realised what I was doing I was walking up to the cottage, opening the little wooden gate, stepping up the path and onto the lawn that were on either side, to where the washing line was hanging, waving slightly in the breeze.
I didn't even look around as I reached up to caress the soft nylon of the swim suit. My hand working its way up to the pegs on either side, releasing them so the suit fell down into my hand, where I clutched it to my wildly breathing chest, before, finally realising what I was doing and get the hell out of there.
Never having done anything like that before, I was wracked with guilt, hiding the suit in the bottom of the closet in my room at Aunt Aggie's the moment I got back, and then spending a heavily anxious evening fretting that someone had seen me and would be marching up to knock on my Aunt's door any second. When that happened happened by the following morning, I finally allowed myself to start to relax.
BY the time the afternoon came around, with twenty four hours having passed since my crime I finally started to relax and allow myself to think that, perhaps I'd got away with it. And if that was the case, then it was time I got to enjoy the spoils of my crime.
Aunt Aggie was out, which was handy, when I went to the closet and took the suit out. Taking off my clothes I put the suit on, pulling it up my still hairless legs, until it was snugly around my waist where it did everything the one the previous year had done. Pulling my bum up and together, shaping it into that perfect spanking target that I wanted, whilst, at the front, doing much the same to my tackle, until there was little there to be seen. Or would have been was it not for the erection that was poking the front out in a rather obscene and yet equally exciting way.
Walking around The Cottage wearing nothing but the skimpy childish swim suit, excited me more than I could possibly describe back then, and I'm not entirely sure that I could put the mixed bag of emotions I felt into words even now.
I'd already decided what I was going to do whilst I was wearing them, and where I was going to do it, down in Aunt Aggie's study which seemed to be perfect place for a naughty little boy to be spanked. Even if he was going to be spanking himself, like I was.
Aunt Aggie has a foot stool that at that time I thought was perfect for self spanking, before I found out it was easier to do it standing up. Back then, I went for the more traditional bent over theory, with myself bent over the stool, the edge of which pressed into my lower belly, which rested on it, with my knees on one side.
Having assembled a small collection of things I could spank myself with from around the house, including wooden spoons from the kitchen, a hairbrush (not the one I would later use but a smaller one), a old shoe, and even a rolled up magazine. All of these I used one by one, on my tightly nylon clad bum, with all my usual carefulness to ensure that I was covered on each check from top to bottom, until I started to feel the by now familiar sensation of my budding orgasm that would end in a way that I wasn't even expecting.
In all my previous solo games, I would spank myself until I was so hard that I couldn't not stop and don something about that but this time I wouldn't need to.
Perhaps it was the way the edge of the stool was pressing into my groin, or it could have been the way my tackle was all bunched up in that too small suit, but more than likely it was both these things together, along with the spanks I was inflicting on myself were sending just the right shocks of pleasure that there was no time or even inclination for me to stop until it was too late.
A flurry of spanking sent my mind spinning as intense waves of pleasure shot out from my bum, bathing my entire body in their glow, before leaving a somewhat stickier deposit in the small suit.
That was the first time, but of course it wasn't the last time I spanked myself to orgasm, nor of course was it the last time I came whilst being spanked, not by a long way. Yet while at the time it was the greatest thing ever, it soon oddly became something of a let down for reasons that are as hard to explain as why I was doing it in the first place.
The slow build up the spanking. The anticipation of it. The getting dressed. Getting the implements from around The Cottage. Getting into position. All of these were great. But there was always something missing. Something that just didn't seem to be quite right and would never be right as long as I was spanking myself.
Sure there were times when I was able to spank myself either long enough or hard enough to make my bum sting enough that sitting down for the rest of the day following it was tricky. I even managed to do it when I could feel the after effects of the spanking the next day. I had even made myself cry. However, none of this was just how I wanted it. How I thought it should be. The way a real spanking was done, where I had no control in what was going on. The problem was just how did I go about doing that. The same question I'd been asking myself since that first time back when I'd been twelve.
The summer drew on, I became involved in other activities which you'll be hearing about later on, but I still returned to the stool from time to time, as although it wasn't perfect that was all I had, yet I never stopped thinking about ways to get myself a real spanking, only to trigger a serious of events that got me a lot more than one spanking. It got me a whole heap of them, and all thanks to a note.
I wrote the note in question but it was based on one sent to my Aunt, carried by the paperboy, who was using it to explain that it wasn't his fault about the deliveries being mixed up and it got me thinking. If a note could get you out of trouble, than surely it could get you into trouble as well.
All of this is why I ended up standing on the porch of the holiday cottage, knowing that there was only one person at home as the rest were with Aunt Aggie up at the house, giving me the perfect change to live out one of my wildest fantasies.
Suddenly the door opened, and I found myself facing an older boy who stood framed in the soft light coming out of the cottage and I found my voice no longer worked.
"Yes," the youth inquired, "What do you want?"
I tried to speak but my mouth wouldn't go any further than just falling open and staying there.
"Are you sick? Lost? Hurt?" he asked, cocking his head to one side, like a dog that doesn't understand something, which really went with his long and somewhat unkempt hair.
"Sorry," I finally managed, which wasn't much but at least it was a start. Of sorts.
"Sorry about what?" he asked, and finally I had my in. Holding out the note for him to read.
Silence fell while the youth read the note, which was short and too the point, stating that what I'd done, and what should be done about it.
"IT says here," the youth waved the note at me, "that I should spank you. Is that right."
"Yes," I replied and really should have left it there, but of course I didn't. Now my mouth was working I didn't seem to be able to shut it up, "I'm sorry for taking your stuff, and I need a real spanking just like it says in the note, so that I know not to do it again. And no one needs to know about it or nothing."
During my speech, which I've shorted a bit, I shoved the bag across so the youth had little option but to take it and look inside. I'm not sure whether it was the way I did that or my constant talking but between the two of them the youth started to add up all the pieces until he had the situation more or less summed up perfectly.
"So you want to be spanked and you want me to spank you?"
That wasn't what the note had said at all, but then that was the first note I'd read. By the following year I'd be much better at that. All the same it was where we were at so rather than argue it and stick to the plan – like I said my first time and everything – I just nodded.
"How old are you?"
I told him I was thirteen which after all I was, only he didn't believe me. "Really, we're the same age?"
"It's true," I said, adding some stuff about being small for my age, and feeling like a little kid. Stuff that I really hadn't told anyone else which seemed to amusing him. Still it did the job. at least on that point.
"So why do you think you need to be spanked?" he asked. "Or do you want to be spanked?"
Again, this shaggy haired kid no older than myself, yet seeming so mature compared to me, had hit the nail so very firmly on the head.
"Want!" I admitted.
"Have you been spanked before?"
It was the logical next question, and one I had prepared an answer for, which would have been to tell a story based upon what happened last year, that would have had some truth mixed into it yet, instead, for some reason, I just blurted out that I had, but not properly.
"So that's why you want to be spanked is it. To find what it's like?"
"Yes."
The answer was much to fast, and yet so honest. I had an extreme interest in spanking, and somehow this boy had worked that out already, just from meeting me a few seconds earlier.
"Okay," he said, having glanced into the bag again, "What's your name?"
I told him, and he told me his, which was Dylan Edwards.
"Well, Kyle," he said, "This is going to be your lucky night, although you may not think so later."
"What do you mean?"
"I mean, once this starts there's no turning back. If you want a real proper spanking then that's what I'm going to give you."
I nodded, unable to do anything else at this point. My mind was rebelling. I was just standing there agreeing to get spanked. Dylan wasn't even finished with his conditions yet, and I was already about as hard as I could get.
"It will not stop until you have learned your lesson no matter how much you want to and even if you cry. Understand?"
I nodded, fearing that if Dylan didn't stop talking then it would be too late and I'd have already reached the point I was most looking forward to at the end of the spanking.
"Very well, in that case, you can start by stop playing with yourself and putting your hands on your head."
I hadn't actually been doing that, as much as I wanted to, but all the same a snatched my hands away from my groin as if I'd been caught mid wank, which made Dylan smile as he moved forward to catch the him of my t-shirt and pull it swiftly up and off my body, before I even realised what he was doing.
"Now, let's get this thing started."
WIthout another word, Dylan reach over and took my wrist from on top of my head and pulled me forward as if I was a little kid, which is exactly what I was feeling like next to him, especially now I was shirtless. He seemed to tower above me, even though he was in reality only a few inches taller than I was. All the same I allowed him to lead me over to a large chair that was positioned at the end of the porch railings, into which he sat pulling me across his lap.
Felling myself falling, face down I should have panicked but I felt like I was being controlled which was what I wanted, so I allowed myself to be positioned with my legs between Dylan's, his own coming across the back of them, holding them in place. A hand around my shoulders held my upper body in place while his right hand had unfettered access to my bottom, as it soon proved.
There was no build up. No anticipation rather what had already gone on both inside my head, and on the porch steps. Dylan just started spanking as soon as I was in position, and he didn't let up at all.
By the time I felt like I wanted to move I really couldn't. The spanks were coming hard and fast, alternating from one of my buttocks to the other, until the sting really started to build up in a way that you just can't do when you're spanking yourself.
On and on the spanking went, while rears started to appear in my eyes, catching me almost entirely by surprise, while wasn't a surprise at all, was the erection that continued to press down into Dylan's leg even as he continued to spank me.
After a few more minutes I had tears trickling down my face, yet I wasn't sobbing or crying out, or doing any of the things you think a boy would do when he was getting spanked, leading Dylan to call what turned out to be a tempery halt to what he was doing.
Release the lock he'd had on my legs, he lifted me from his lap, pushing me up until I was standing before him, the tent in the front of my thing summer shorts all to obvious as it pointed right back at him.
"Looks like you are going to need something more than my hand," he said, looking directly at my groin, "And I think it's time you got spanked on the bare."
There were two things in that sentence that I had to deal with. Both of which I wanted, and both of them I wanted, even thought my bum was already rather sore, and I had tear tracks running down my face, I agreed to both.
Reaching down, Dylan pulled off his own slipper, flexing it in his hand, so that it slapped down into the palm, with a shark crack that made me jump a little, but not so much as when he pulled my shorts down.
A moment later I was back over his lap, my legs clamped between his thighs, while his hand on my back held me in place, as his other hand explored the work he'd already put into my spanking.
"Your bum is a nice shade of pink," he said, brushing his fingers over my rear, "But lets see if we can make it a bright red before we're done, shall we?"
The question was rhetorical of course, which was just as well as I couldn't talk, note once the soft, flat rubber sole of Dylan's slipper had started to gently roam across my bum. Then it was gone. Raising up, ready to come down in a sharp crack.
The slipper proved a much more flexible spanking implant than Dylan's hand had been. It managed to reach every single part of my rear, including, but not limited to, the sides, the middle, my sit spot, and of course the cheeks themselves.
It was after less than a couple of minutes of this that my resolve finally broke. The tears had returned fresh and wet to my eyes, and my bum felt like it was on fire, as I called out that I was sorry about stealing the swim suit, not that it made that much difference as Dylan continued to spank me.
Another ten blows landed, or it could have been twenty or even two hundred for all I knew, as I really wasn't counting any more. All I could think about was the fire that had been lit on my bum, and I even did the one thing that I thought I would never do. I asked, and then begged, for the spanking to stop.
"Naughty little boys don't decided when their spanking is over," Dylan told me in no uncertain terms, as he finished up with a few more whacks of the shoe, just to make his point.
In the end I lay there for several minutes passed the last blow, crying until I realised the spanking had stopped. My bum was on fire, as I was pulled up to my feet once more and told to go and stand in the corner which presented a problem as there weren't actually any corners as such.
In the end, Dylan decided that I could stand facing the wall, of the holiday cottage with my bum facing both towards him and the road beyond the face, as a warning to anyone else thinking they could steel from them. Not that anyone would be likely to come up the road but it was something for me to think about while I was standing there on slightly wobbly legs.
For only thirty minutes – the longest Dylan would risk it before his parents came home – I remained in place, my bum burning, and yet with still most of an erection. I hadn't come whilst being spanked which I would later look back upon as a disappointment, yet my only one about the entire encounter that wasn't yet over for when I was getting dressed again, Dylan had some news for me.
"That swim suit wasn't mine you know," he said, flatly, "So really I shouldn't have been the one to spank you for it. I mean I could hardly wear these could I?"
Looking up I saw him holding the swim suit I'd worn up to himself and clearly he couldn't have worn it, but if it wasn't his then who's was it.
"They belong to my cousin," he said, "He can only come down at weekends, but he'll be here in a few days so you could apologies to him then if you want?"
So it was that walking home, with my bum still burning inside my shorts, thoughts of my first proper spanking didn't really get to run through my head as I was too busy planning how I was going to get spanked again, this time by Dylan's cousin. Now that was something that turned my semi into a full on erection once more.
Chapter Six Dress To Impress
After checking that no one else was watching and that the last of the girls had indeed hurried away for the final words of advice, I ducked through the bushes that had so far concealed me and made my way through the open door, into the hall used by the BSAD society.
It was another of my Aunt's pet projects which is why it was named after her. The Blackwood-Smythe Armature Dramatics Society to give it the full name, but even my Aunt called it the BSAD, or rather B-SAD, as she said it just made her smile. Given that she was paying for it out of her own pocket, they were hardly going to complain, now were there. Plus, being related to the one and only patron gave me the perfect, legitimate reason to be there. Well most of the time anyway.
A few times I'd helped out with the props, finding the things they needed for their current production, but mostly I just ran notes back and forth from my Aunt as she gave advice, on things like costumes, and just how many extras the show needed. She even volunteered her niece Kylie for a role. Not that anyone involved had actually met Kylie and there was a good reason for that. She didn't exactly exist. Kylie was me.
All of that is why I ended up standing in front of the costume rack that was filled with a couple of dozen pretty dresses, searching for the one that ordered in my size.
A frilly pink party dress, with white lace trimming around the bodice, collar and lower hem. The sleeves were even more lacy, and puffed out to make the dress look even more feminine. A wide white ribbon circled around the waist ending in a giant bow at the back. It was, as you've probably noticed, not that dissimilar to the sailor suit dress Luke Taylor had talked me into back when I was eleven. Only this one was made to fit a small fourteen year old.
Not knowing how much time I would have while the rallying speeches were being made in the main part of the building, I pulled the dress out from the rack and turned my attention directly to the one behind it that held a selection of petticoats. I already knew which one I wanted, picking a lacy white one with a good five layers to it that would be sure to make the short skirt flare out in just the way I wanted it to.
Moving onto the next table, I picked up a pair of white tights, and shoes, before at the last section taking a strawberry blonde wig, with lots of curly curls from where it was sitting on a stand labeled, handily "Kylie."
A small changing cubicle had been set up in the corner, which although it was little more than some fabric hanging from lines stung between some posts, would give my some privacy should someone walk in during the one part of the procedure that would be the hardest to explain away as 'helping out'.
With the dress and petticoat hanging up on the provided hooks, I quickly slipped out of my regulation teenage boy jeans and sweatshirt to expose just how well I was prepared for today's adventure.
The white lacy bra, and pink nylon knickers, were something I'd borrowed earlier in the week, once I'd found out that B-SAD didn't provide underwear with it's costumers, the assumption being that the actors would wear their own. Well in my case that was hardly going to work, which is why I'd been routing through lost property until I found something suitable. Just a shame they didn't match, but you can't have everything.
Funny thing was the outfit Kylie would be wearing didn't really require a bra as it was something more suited to a seven or either year old girl, rather than someone in their teens, but having the appearance of breast would make people less likely to suspect I was actually a boy. At least that's what I kept telling myself, as I used a couple of socks to bad the bra out, having worn in flat under my shirt, so as not to give the game away.
The tights were first. After removing them from the packaging, I rolled them down like I'd taught myself, before putting my bare foot into the end, where it easily slipped down to the correct part. I then repeated this with the other foot, before I started to work the tights up my legs, ensuring there were no wrinkles or snags along the way.
Once the tights were at the top of my legs, I pulled them up over the knickers, especially careful not to catch them on the snag point that my erection had become, until finally the tights were as high as they could go, which turned out to be just about passed my belly button.
My legs looked really great in tight, it has to be said. Still a bit boyish, despite the white sheerness of the covering, thanks to the muscle definition I was starting to get, but that really wouldn't matter once I had everything else on.
Slipping the petticoat over my head instantly lead to me being lost in a sea of white crinoline and lace, until I was able to pull it down around my waist by which time the cool sensation was starting to caress every nerve ending on my body, leading to a small shiver of excitement going up and then down my spine. The various petticoats that made up the single garment then flaring out from my loins just like they were meant to, hiding everything that was standing up in a way that the kickers and tights alone would never be able to do.
Putting the dress on was a little more awkward as I had to lift it up over my head, and at the same time thrust my hands into the lacy puffed out sleeves until the entire thing fell down around my body. The final part of the operation being the most difficult as zipping it up the back wasn't meant to be done by the person wearing it. Turns out it was possible to do it. Just tricky. Once done though I was pretty much sealed into the dress, with little hope of getting out of it. Certainly not in a hurry.
My feet slipped into the black patent leather shoes, although I did have to bend down in order to fasten them up once more, before I could stand straight once more and place the wig on my head. THankfully the school boy style short back and sides for my other adventure that summer, meant I didn't need to use a hair net especially as the wig was much longer than I was used to. The blond curls falling across my bare shoulders and around the back of my neck in a way I just wasn't used to.
Dressed now I carefully hid my own clothes, before I stepped out into the main room, heading for the full length mirror on the other side of the room, but first passing a small make up table set in the corner. Playing a little girl as I was I wouldn't be needing any actual make up on my face but I did want to spray myself with a small bottle of perfume that was there just in case the rumours were true that boys smelt different to girls.
Practising walking like a girl, I pretty much sashayed across the room to the mirror, where I was more than pleased with the result of my handiwork. I'd come into the room your standard teenage boy but I would be leaving it, looking every bit the part of a little girl, with the exception of the slight bumps in the front from the bra. Still the lacy petticoat just peeking out from under the skirt, almost made up for that, in knocking those crucial years from my appearance.
I was now ready to meet my public as Kylie for the first time, only I didn't need to as I was still standing in front of the mirror when the door to the changing room opened and a head poked itself in.
"Ah, there you are. You must be Kylie Smithson?"
"I must be." I replied, a little bit shocked that Mrs. Whiteapple had found my but at least the disguise appeared to be holding up.
"Come on, we've got to be going or else the bus will leave without you. Lucy should have rounded you up already."
Lucy was Mrs. Whiteapple's daughter, who was the same age as me, fourteen, but she had the habit of acting as if she was in her sixties, always taking control and bossing the younger kids about, but then when your mum runs the group then I guess you're bound to end up like that. Still I was a little taken aback when she reached out and took my by the hand, starting to pull me out into the hallway.
"Wait," I cried, "I'm not ready yet."
"You're not?" Mrs. Whiteapple looked me up and down. "Oh right I see it. You're meant to be a little girl so where's your
" she looked around for a second before spotting what she wanted. "Ah here it is."
Picking up the small doll from the pile, Lucy, pushed it into my arms, noting as she did that it had a dress that matched almost perfectly the one I was wearing, just as my Aunt had suggested. Which will teach me for being so though I guess.
"Right that's better. Now you look like the perfect little girl, so come on. You don't want to keep Lucy waiting do you?"
This wasn't quite how I'd planned things, as in my head I was just going to creep out of the changing room and merge myself in with the real girls, and hope that no one would realise I some bits between my legs that they didn't. Thankfully I'd already hidden my boy clothes, before Mrs. Whiteapple had burst into the changing room, so they wouldn't be giving me away. Now I could only hope that nothing else would.
It wasn't a long trip mainly due to the building being so small, but it flashed passed in mere seconds before I was once more bathed in sunlight, emerging into a scene that looked like some sort of giant fancy dress party, with girls of various ages dressed like animals, or a total cross section of people, from little kids right up to little old ladies, in fact all of the characters that the play they were to perform required. A play that had been suggested – you guessed it – by my Aunt.
"Lucy. Lucy. Can you come over here."
Hearing her mother's cry – well she could hardly miss it – Lucy Applewhite, emerged from the crowd dressed in an outfit that wasn't too dissimilar to the one I had one, only it was in an oddly more boyish blue.
"Ah you two look so cute, I wish you would dress like this all the time," gushed Mrs. Applewhite like only a mother could, and getting just the reaction that stopped most of them from doing it more often.
"MUM!" Lucy hollered, even louder than her Mother, drawing more attention to her, rather than less, which is probably what she wanted. One thing was clear,. Lucy certainly wasn't as keen on being dressed like this as I was, which made me smile despite everything else, and what came next.
"I've got to get some pictures of you all dressed up like this. Now, where's my camera?"
"Oh great that's all I need," sighed Lucy, but remaining where she was as her mother wondered off, leaving the two of us together. "So you're Kylie Smithson. We've heard a lot about you, but you never turned up for rehearsals."
"Er yeah," was all I had to say before Mrs. Applewhite returned with a camera.
"OKay, you two girls stand together. Oh and remember that little girls actually like their mother's taking their pictures, so no pouting. Oh and Kylie, hold your head up so we can see your pretty face."
The camera flashed several times, blinding everyone on that particular side of the planet followed by a cheer which had nothing to do with the photo opportunity and a lot to do with the battered old bus that choose that moment to pull into the car park.
"About time too," mumbled Lucy, before taking my arm, "Come on Kylie, let's get the good seats."
Suddenly I was travelling forward, partly pulled by the girl holding on to me, and partly pushed from behind, as the rest of the cast, surged towards the bus giving me no time to act on any of the second thoughts that were rushing through my head, until I found myself mounting the steps onto the bus and by then it was already too late.
Chapter Seven Getting Tutored
Noting the time, I moved over to the wardrobe where I kept my totally un-regulation school uniform. Andrew James would be here in about ten minutes ready for my second tutoring session, and it would ruin everything if he saw me dressed in jeans and a sweatshirt.
I'd already decided that wearing the entire thing, whilst indoors would be a bit of overkill and would probably look a touch odd, as old fashioned schoolboys don't tend to wear their cap and blazer at home, so I left those off this time, hoping that I'd get the chance to wear them at a later date. For now I'd just have to make do with the rest of the uniform.
Removing my modern clothes I replaced them with a nice crisp short sleeve white shirt, that I button up to the neck, adding the tie to give it that nice formal look. Meanwhile further down my body, I pulled on a nice pair of wool long socks that came up to just below my knees, where I turned them over. I wasn't going to wear shoes for the same reason I wasn't wearing my jacket, so that just left the grey school shorts, to be tugged up to my waist, and for my shirt to be tucked in before I picked up my improvised schoolbag and head downstairs to wait for my tutor.
Andrew turned up right on time, just like I knew he would as, after all, he'd been told in the note that had employed him for this session that time keeping was very important. Just like all discipline, of course.
As with the first time he'd knocked at the door, Andrew gave my the once over, clearly surprised that I would be dressed so formally during the holidays, despite what I'd earlier told him about it being part of my punishment.
"I've got a lot of work today," I told him, when he asked what we were going to be doing, pointing towards the desk that was still set up at the side of the living room and which was now piled high with the books I'd collected for the occasion.
"Okay then, I guess you had better get on with it, then," Andrew said, before settling himself down on the sofa rather than into the chair set up beside my one, which I'd have preferred. Still I let him have his rest. for a while anyway.
"I don't get this," I explained about fifteen minutes later, throwing down my pencil, and leaning back in my chair.
"WHy's that?" Andrew didn't even look away from the TV when he asked, but that would soon change.
"Well, when I'm at school doing this stuff there's all the other boys around, to help me, and the teachers to test me, now there's no one."
Suddenly Andrew remember why he was there, "I'm here!"
"But you can't help." I slouched back even further, making sure that my legs spread themselves around the front of the chair, so that my thighs were splayed enough to flash the white lining from inside my shorts, as well as virtually all my legs. "NOt like they can."
"Why can't I? I can do anything your teachers do. Your Aunt said so in her note."
That was true, and it was just what I was counting on, of course.
"Well," I said carefully, as if I was thinking about it, "There is one way that will make sure I get to learn everything."
"Which is?"
"BUt you probably won't like it."
"What is it?"
"You have to quiz me,"
Andrew sighed, "Is that it. I can do that?"
"If I get the question wrong," I purposely paused there, giving it a few seconds before I continued, "Then I have to be punished."
"Punished? How?"
"Depends on just how wrong I get the question." I skirted around the question he really wanted to ask, before giving him something to go with, "But that's totally up to you. Aunt Aggie knows you can punish me from last time."
He knew what I meant by that, just as much as I did. Which was the point of course.
"There are some things you can use over there," I pointed towards the sideboard behind the door we'd entered through, meaning that Andrew hadn't noticed what was there then. Now though he really did now that he knew what the long wooden ruler and the short strap were going to be used for.
"I can use these?"
"Yes," I went over the rules for the spanking game I'd made up for him, "For a small mistake you can still use your hand, probably on my legs. For a minor one, the ruler on my shorts and if I really mess up then you get to use the strap on my bum.
"Okay," he picked up the strap and gave is a tenderize slap into the palm of his hand, clearly not prepared for just how much that would sting, given the look on his face.
"And you have to ask all the questions on the sheet. No stopping."
"Okay," Andrew took the sheet I gave him, running his eyes quickly down the questions I'd typed out on one of Aunt Aggie's headed notes. His brows furrowing as he tried to work out the answers to some of the more difficult ones, just as I hoped he would.
While he was reading the questions I got myself into position, getting up off the chair and then on it again. Standing on the seat, with my hands on my head. "I'm ready." I told him. "Read the first question."
Andrew did as I asked him, looking down on the sheet and reading it out slowly. When he was done, I paused, giving myself enough time to appear to be working out the correct answer before I said it.
"That's right." he said, picking up a pencil from my desk to mark the question of as done, which he also had to do for the next two before he came to one where he get to put a cross.
"Wrong, I'm afraid, so I guess that means a hand slap."
The words were probably to confirm that he understood what was going on as much as to inform me as to what was going to happen, which was that I was about to get a stinging slap on my right thigh, just below where the hem of my shorts had raised up the moment I put my hands on my head. That much I was expecting. What I wasn't expecting was for him to do the same to my left leg, and to do it a bit harder.
My socks slipped slipping slightly on the smooth wood of the chair caused me to wobble a bit on the chair leading to a suggestion that I take them off from Andrew which seemed a sensible thing to do.
Back up on the chair I was now a lot more stable which was just as well as I got the next question that little bit more wrong than the one before leading to the same punishment as previously, just a little bit more of it.
Starting at my shins, which had been previously covered by my socks, Andrew slapped his way up the outside of both my legs, taking each one in turn, until he reached up to the shorts once more. Here though he didn't stop as he had done last time, but reaching out from behind me, where he'd been standing, he grabs hold of the waistband and gives it a good hoist upwards, until I am all but getting a wedgy. This though does, as he points out both in words and actions, give him more areas where he can slap me.
A couple more questions went past without anything happening other than my legs continuing to sting. Then it was time for me to make another mistake, and one that was noticeably worse than anything I'd done before, so that Andrew would reach for the ruler.
Holding the long strip of very flexible wood in his hand, Andrew bent it nearly in too, so as to judge just how bendable it was, before he took up a position beside me holding the ruler out level to give me the gentlest of taps on the back of my knees, as a bit of a tester before he got down to business.
The anticipation was almost a killer, with part of me wanting to shout for him to get on with it, but Andrew took his time, flicking the ruler back and forth higher and higher up the back of my thighs, until it came level with my rear. Then there was a pause. A swishing sound. Then the ruler was embed into the material of my shorts.
Time seemed to freeze. Nothing happened. No sounds, no feelings nothing. Then there was a sudden burning pain in my rear, that felt like a red hot stick had been pressed on my flesh.
Instantly my hands flew down from my head to put out the fire which was a complete break of the rules I'd made up for myself. NOt that I'd told Andrew about this one, but he must have worked it out for himself from when I put them up there in the first lace. He probably thought that's what my Aunt insisted on. And if Aunt Aggie did it that way then he had to two.
"Seeing as you can't keep still, the next time you get something wrong, then your shorts are coming down."
It was tricky to think about anything once that threat was made. Sure I knew it was going to happen sooner or later, but I'd planned on it being later. I'd even worked out which question it would happen on and it wasn't any of those coming up shortly. That said, now it was all I could think about which made remembering the answer to the questions I wanted to get right, impossible as I proved on the very next one, which I answered with the answer for the next one. Hopefully Andrew wouldn't notice, especially as he was making himself busy taking my shorts down.
Again I'd expected to do this myself, even if that meant fiddling with the fly buttons that still gave me trouble despite the fact I'd been wearing the shorts for several days now. Andrew though, had no such problems, and I don't think it was just down to him being able to see what he was doing, as my groin was almost directly at his eye level. Perhaps it was one of his duty as a prep school prefect to help the littler kids – who tended to wear shorts like these – dress or undress for gym or other reasons, but whatever it was, he had my fly open in seconds. Yet he can't have been that good as he managed to nudge the bulge in my pants several times whilst he was doing it, which I bet wasn't normal practise.
"Legs together," he commanded, which I did, letting the shorts fall the rest of the way down from my thighs, where Andrew had pulled them.
Thinking about any more slipping problems, I quickly stepped out of them, and nudged them over the sides of the chair with my feet.
Fingers brushed across my bottom, as Andrew lifted my shirt up from where it had fallen over the area he was clearly most interested in.
"If my shirt is in the way, I can remove it." I offered, wondering if he'd go for it.
He did.
There was no help this time. Andrew content to stand back and let me take my own shirt and tie off and to then droop them both over my desk completely covering the work I hadn't been doing earlier.
"That's better," I heard him mumbled and I couldn't disagree as I stood on that chair now wearing only an old fashioned shoulder strap vest, that barely made it down to my waist, and a pair of old stye white briefs, that barely made it up to my waist, and which I knew totally encased my bum, in a good tight little package that was eager for a spanking. There was also the start of a tent in the front, but Andrew choose to ignore that as he once more picked up the ruler and got set to tease me just as he had done with his hand.
Standing directly behind me, as I turned sideways on the chair, Andrew James, slotted the ruler between my slightly opened legs, and began waving it from side to side. Naturally this meant that he was tapping the thin wood on the insides of my ankles, and then started to work his way up.
By the time the ruler was coming onto my thigh, just a few inches below the level of my clothing, I felt my willy start to shift in its tight pouch as it continued to wake up.
By the time the ruler was operating just below my underwear, there was no way I could hide what the spanking was doing to me, but as Andrew was still behind me, there was a chance that he hadn't seen it. Then though he moved to my side, as he got ready to let my briefs feel what my shorts had before.
There was an audible swishing sound, then the WHACK as the ruler made firm contact with both cheeks of my bum at once. This was followed by a lot of stinging sensations, and a bit more of the fire I'd felt before, along with the strong urge to go up on tip-toes as if that could help ease everything I was felling.
"Well taken," Andrew complemented me, as he returned the ruler to pick up the question sheet once more.
Keeping his back to me for a few seconds Andrew appeared to be looking down the sheet perhaps to see where we'd got to but from my elevated position, I could see that whilst he was holding the sheet with one hand, his other was making some adjustment deep in the pocket of his jeans.
Then three questions later, despite my trying to get things back on the schedule I got another question wrong. At least I think I did. I gave the answer I'd memorised, but clearly I must have remembered it wrong, for it wasn't right.
"OH dear," Andrew's voice sounded strangely theatrical, "Think it's time you took some of your punishment on the bare, don't you?"
I did, but the question was rhetorical so I said nothing, just bought my legs together so my underwear could be taken down, knowing full well that this would also give the briefs that little more play so that my almost totally fully stiff erection would be straining at the front.
Oddly Andrew continued to ignore what was now literally directly in front of his face. Instead his hands came up to my waist, and after hooking his thumbs into the waistband he peeled them down to my ankles in one continues motion. Naturally as it gained it's freedom my erection sprung up, and then continued bobbing around in front of me, in time to my pulse, waving in the same air that was now starting to cool my bum.
"Right now I think we will fold your vest up out of harms way." announced Andrew as if there was an audience watching what he was doing, which there wasn't, although there could have been as by standing on the chair I was right about level with The Cottages windows, so in theory someone could have looked in and seen what was happening. Which was an exciting idea if unlikely in reality.
Whilst these thoughts were in my mind, my young tutor, set about moving my short vest further up my torso, by rolling it into a neat little belt that was up under my arm pits by the time he'd finished. Of course my vest was never going to get in the way of what he was going to do so clearly there was some other motive for doing it. Perhaps he just wanted to delay things, or it could be that he wanted to tease me some more. Whichever of these it was, or something else, then there was certainly some teasing of my willy, was got rubbed numerous times, by various parts of Andrew's body, which ensured that there was even less chance of it going down any time soon.
"Spread your legs as far as you can," instructed Andrew picking up the leather strap I'd provided him with.
Doing the best I could I turned so I was standing diagonally on the chair and then spread my feet to the corners which wasn't the most comfortable I'd been especially as it strained my thighs a bit, and of course making my pointing willy even more unmissable now that it had a slight dampness at the tip.
Without another word Andrew went to work with the strap, continuing the processed he'd begun when I'd been in my underwear. Placing the strap between my spread legs, and then slapping it from side to side, raising it slightly up all the time so as to leave a trail of redness from my ankle right the way up to the very top of my legs, right where they met and where my tackle was hanging down, very much exposed.
Despite the blows being slow and shallow I could feel each and every one of them, as they built up, and yet there was surprisingly little pain. That though wouldn't last.
The reddening of my legs was only a built up as once Andrew was satisfied with their colour he turned his attention back to the more traditional part of a boy for punishment, and still using the strap went to work on my bum.
There was a gentle slap across my rear, followed a few seconds later by what turned out to be a real blow, that made me wobble on the chair so much that Andrew had to grasp the only part of me that was within his reach.
A gasp escaped my lips not from the blow to my already stinging bum, but at the hand that was now clamped around me hard willy. It was something that I hadn't expected to happen until quite a way further down my plan, if at all. Not that there was anything I could do about it now. Not as another blow from the strap turned my bum into fire, and caused my hips to push myself into the hand.
The punishment continued. The strap landing on my bum, in various places as Andrew changed the height of the blows, moving the strap up and down, so that all of my bum got to feel the sting of leather. Meanwhile, his other hand kept a firm, yet unmoving grip on my excitement, leaving it down to me to thrust myself through his fingers, whenever the strap landed.
"Oh God," I groaned, making my first comment on the situation, but that too had nothing to do with the spanking and everything to do with the manipulation of my willy.
"Keep still!" barked Andrew even though the only movement I was doing was down to the spanking I was getting and was pretty much involuntary, especially by this stage, when the end game was already in sight.
And so it happened. The strap landed again, right in the centre of my bum. My hips thrust themselves forward, pushing my willy through the tight, yet now slick grasp, and then that feeling that every teenage boy knows only too well, overcame me.
My orgasm made the chairs wobble, and would introduce some new stains to the ancient living room carpet as I shot a load out in an artful arc from the raised position up on the chairs. The angle would have made for a great rainbow, only without all the colour, obviously.
"Wow!" commented Andrew, before he got himself back into his tutor's role. "You are going to have to clean that up after the lesson."
Even though it wasn't easy for me to talk I told him that I would.
"Good. I think that's probably enough learning for one day don't you." he smiled at me, trying but more often than not failing to maintain eye contact with me as his gaze wondered down to my still semi-stiff willy, and the mess on the floor. "Why don't you put your uniform back on and we'll talk about some of the other lessons we can do."
Chapter Eight Baby In Trouble
Shaun, Aha and Sawyer were right on time for their second time as my baby sitters but apparently I was late, a or possibly earlier, depending on how you see it, as my nappy was already wet.
"Did you wet yourself over night?" asked Shaun, giving me a look that said he already knew the answer, even though that wasn't entirely accurate given that I didn't actually sleep in the nappy, but had only just put it on. Truth was, the wetness was actually apple juice, as I'd been totally unable to go in the nappy despite that being a somewhat vital part of my plan. Talk about irony.
"Will have to change him before we take him out?" bounced Sawyer, on the balls of his feet with anticipation.
"Yes I guess we will. Come on let's get up to the nursery. Aha, you bring the stuff."
There was a heavy looking back over the middle boy's shoulder, which I pretended to notice for the first time, whilst asking about something else I already knew the answer to, "Out? We're going out?"
"Yes," Shaun called over his shoulder as he headed through The Cottage to the room I'd set up for my baby-self, "Your Aunt says you need some new things so we're going into town to get them and to check out a couple of other things."
Sawyer giggled, with his hand over his mouth, making him sound like a cartoon dog until his eagerness nearly caused him to walk right into his brother, at which point, under the threat of a clip around the back of the head, he managed to pull himself together.
When we reached the nursery, I'd had a chance to think about what was going to happen to come up with a plan to stop it. Nothing complicated, as it was meant to have been thought up on the spot, which is why it was also a little cliched. "I can't go out. I'm sick."
"Sick. Your Aunt didn't say you were sick." Shaun didn't stop setting up the changing table for me forthcoming change, as he spoke.
"She didn't know." I explained, "It's just come on. It's my stomach."
"We'll be the judge of that but for now lets get you changed. Hope up onto the table."
I did as I was asked, just like it was something I did everyday. Putting my feet into the foot holes on the high table, to raise myself up, and then spinning around to lay down on my back on the plastic covered top, leaving my legs hanging over the end.
"Can I dod it?" Sawyer offered the instant I was in position, but Shaun just pushed him out of the way without a word, as he started to remove the tapes holding the nappy closed, before he asked Aha to help him instead. Together they grabbed hold of my knees on either side and hoisted my legs up, which allowed the wet nappy to be pulled out from underneath me, leaving me now totally naked.
Still trying to get in on the act Sawyer held the tub of baby wipes even though he didn't need to, as Shaun could have easily reached them from where they had been. By doing so though, allowed the nine year old to remained by my side, staring down intently between my legs as the last of the apple juice was cleaned from around my tackle which was a relief as turns out apple juice is a lot more uncomfortable than wee.
"Turn onto your stomach for a moment," I was instructed although I really didn't have to do anything as between them the three boys pretty much did it for me until I was all but bent over the end of the changing table it what would have been the perfect position for a spanking. Only that wasn't what Shaun had in mind.
From under the table he produced two items, which he placed somewhere where I couldn't see them but his friends could, leading to Aha to ask what they were for.
"Well, if he says he's sick then we have to check it out to see if he is, by taking his temperature."
It was at this point that I pretended to cotton on to what he was going to do, and started to say I felt a lot better but of course it was too late by then as Shaun was had already unscrew the cap on the Vaseline and was dabbing the tip of the rectal thermometer in it.
Sawyer spotted that I was trying to get up, leaping over to press me back down again onto the table, not that his slender weight would have really made that much difference, as I could have easily have pushed him off if I wanted too, which of course I didn't.
Following whatever course he'd been on before he became a babysitter Shaun gave the thermometer a good shake and then, while Aha held my buttocks apart pushed the bulb against my bum hole until it started to slide inside.
"This is how baby's get their temperature taken," he explained even though no one had actually asked why he was doing it that way, which perhaps they should have.
For a good five minutes we all remained in the same positions. My laying face down on the changing table with my legs hanging over the end. Sawyer, half resting his upper body on my back. Aha needlessly holding my bottom open, while Shaun's hand rested over my opening, also needlessly holding the thermometer in place.
Eventually, time was up and Shaun removed the thin glass tube from my bottom and read off what was a perfectly normal temperature, despite the totally unordinary situation.
"Okay, baby Kyle isn't sick so we can continue with the plan. Turn him back over."
Rolled onto my back, the three boys discovered what having something stuck up my bum can do to me, but despite some knowing looks and a little giggling from Sawyer, none of them mentioned it as I was once more put into a clean fresh nappy, which was taped snugly into place, before being covered by a pair of pale blue tinted plastic pants.
"Hey I don't wear plastic pants," I protested,
"You do now," I was told in no uncertain terms, Shaun giving the waistband a good snap, "It's one of your Aunt's new ideas, along with this shirt. Get him up boys."
The brothers took hold of my arms, pulling me from the changing table until I was standing on the floor. They remained holding me there while Shaun moved around checking that the nappy was totally covered by the plastic pants, pushing anything that poked out, back through the tight elastic around my legs and waist. When that was done he went over to the bag Aha had bought, and removed from it a pale blue short sleeved shirt that perfectly matched the plastic pants.
"Arms out!"
IN what should have been a surprise move, had I not ordered it that way, the shirt went on from the front, rather than the back. My arms pushed into the sleeve holes, before the body of the shirt was pulled onto my chest, and across my shoulders, where the small buttons were fastened up my back, right where I wouldn't be able to reach them.
"Feet next! Sit him on the table."
Attempting to lift me back into a sitting position on the changing table, the brothers sort of dragged me instead, with me doing most of the work, even giving a little jump so my feet would be clear of the floor, allowing Shaun to take a pair of pale blue ankle socks from the bag and put them on my feet. These were followed by elasticated shoes, that were pushed on top, and which crumpled my toes up a bit. Not that it mattered as I wasn't going to be doing much walking that day.
"Now hold out his hands."
WIthout being asked, I made my fingers into a fist, as I knew this would make what was to follow so much easier as Shaun produced a roll of packing tape, which he proceeded to wind around my clenched hands until they were just two helpless stumps at the end of my arms. Of course, they didn't really fit into the image they were trying to get for me, but a pair of oversized blue woolen mittens did that, as they were pulled over each hand and tied in a neat bow around my wrists.
I'd said nothing for some time. Not when even when my hands had been rendered helpless, but now I did, asking what they thought they were doing and generally making a right old noise, just to give them an excuse to use the last item from the bag.
"Aha, get the punishment dummy will you, so we can keep the baby quiet."
Sawyer reacted faster than his brother could, racing across the room to the bag while the two older boys held onto my arms, coming back waving the item in front of my face in triumph. It was an oversized baby's dummy, with a round pale blue plastic circular mouth cover, and a ring on the front. There were two long blue ribbons hanging from the sides of the face plate that could be used to hold it place.
"One, two, three. Now!" There was no discussion. No asking for me to open my mouth so they could put the dummy in. The three of them just assumed I wouldn't have cooperated no doubt because they themselves wouldn't have done. So instead, they just went into action. Aha holding me still, while Shaun pinched my nose until I had to open my mouth to breath, at which point Sawyer quickly forced the soft bulb of the dummy deep into my mouth, filling it completely. They then wound the securing ribbons around behind my head, and then tied them tightly at the back.
"Now that's going to keep little baby Kyle quiet. Now let's show him what he looks like."
Again taking hold of my arms, the two older boys marched me towards the nearest mirror with a still bouncy Sawyer leading the way. All of them waiting to see what my reaction would be when I saw what I looked like.
What I looked like, was not surprisingly an over grown baby. The backwards shirt was short, showing a little bit of my trim stomach, above the waistband of the plastic pants, my long bare legs, added to the juvenile appearance. The entire outfit colour coordinated perfectly in pastel shades of baby blue, that left no doubt that I was dressed as a baby. And then there was the message carefully stuck to the shirt stretched across my chest, that said just one word. BED WETTER.
"You see, your Aunt thinks that if you are going to carry on behaving like a baby then it is about time you were treated like one, and that everyone saw just what a baby you were." explained Shaun, quoting almost verbatim from the note I'd sent him.
"Can I get the chair now? Can I? Can I?" Sawyer was so excited it was likely that he'd be the first to wet himself so Shaun allowed him to run ahead while he and Aha bought me around to the back yard, where another surprise I knew all about was waiting for me.
Made of steel tubing with a vinyl seat, the pushchair was old fashioned but built very solidly, even before the extra parts had been attached to make the occupant even more secure. I was pleased to see the three baby sitters had done everything they'd been asked to do, although quite where they'd found the pushchair in the first place I never did find out. One thing was certain though, it was perfect for what I had in mind as I soon discovered once Shaun and Aha had taken me over to it and sat me down.
Completely missing the fact that I wasn't resisting in the slightest, the three boys went to work fastening the restraints around me, starting with those the chair had come with.
Two leather straps, like overly long shoe buckles, came over my shoulders, and hung down on my chest. Another two similar straps came around from the back under my arms. These four were then all fastened together, in a rather complicated way, that gave the boys a bit of trouble to get both right, and tight enough to hold my firmly against the back of the chair.
While the older boys were doing that, Sawyer, saw to the somewhat more standard waist strap, which he buckled across my belly, pulling it so tight that I had to suck in my tummy, so he could get the pin in the hole he wanted to use. He then moved down to my feet which he picked up and put on the foot rests, before making sure they would stay they via the dog collars that had been screwed to the framework.
A further set of similar leather dog collars were fixed further up the main frame at the front. These were for my knees. On fastened on either side, ensuring that my legs would not just be unable to move, but would remained splayed open all the time I was in the chair.
There was a bit of pushing and shoving during the fastening of the second of the knee straps as Sawyer was getting in the way of the older boys as they pulled my right arm down the outside of the pushchair where they were each fastened in place by straps at the wrist, elbow and up near my shoulders.
The final strap was one that Shaun did on his own as it went around my neck. This he did carefully, with surprising gentleness – My aunt's note had told them not to humiliate not hurt me – but all the same very firmly, so that once it was done up I would have restricted movement in my head, as well as everywhere else.
By the time the boys were finished I was tightly restrained in the pushchair, totally unable to move, or even shout as the dummy totally filled my mouth, so that I could just about manage some mumbling but that was it. Something which Sawyer in particular appeared to find particularly amusing.
"Here's what's going to happen," Shaun explained when everyone had finished being amused by what had been done to me. "We are going to take you into the Blackwood, so that everyone can see what a baby you are, and perhaps we'll meat some people you know, then we'll bring you home in time for tea."
There was little chance of me being recognise as no one really knew me in the town despite the number of times I'd been there, so I wasn't really worried about that. What I was however was excited. Very excited. My only wish being that I could have got my hands inside my nappy to take care of the rampant erection that would have been making itself very obvious had it not been for the double action of the tightness of the nappy and plastic pants, along with the way I was forced to sit in the pushchair, somewhat hunched up. Not that anyone would be able to miss that I was wearing a nappy – not with the way my legs were forced open – just not any sign of how much I was enjoying what should have been a very humiliating experience.
Sawyer once more went in front, opening doors and gates, as Shaun and Aha took turns pushing what was a heavy pushchair when it was empty, but now was even more so, now that I'd been added too it. Shame they didn't think to oil the wheels when they were adding all the straps that held me, but still they were fit young lads, and even if they hadn't been, before by the end of the day they would be, especially considering all the hills there were in Blackwood.
Aunt Aggie's cottage isn't that far from the part of the town named after her, that the boys were taking me to, but all the same it wasn't long before my situation started to attract attention. NOt that anyone came to my rescue, although some did ask questions as too what was going on to which Shaun would explain that I was being punished for wetting my bed and acting like a baby. As per their instructions they never mentioned my name, or my Aunt's, just that they were doing what they were told, which was enough back then, for them to be left to get on with it.
The best reaction came, not surprisingly from other kids especially those who were in a similar situation to me, due to their age rather than nocturnal accidents. The real toddlers all stared wide eyed at the big boy in nappies, while those a little older often looked worried that their own parents would get ideas, which I really hoped they didn't as it would have been totally cruel to do that to a kid who didn't enjoy it.
A small park sat near the middle of town, which is where I was taken. Pushed to the children's playground at one end, opposite the playing field where boys my own age played a somewhat random game of football, that seemed to involve them regularly changing sides but which was all in good fun. They even invited my babysitter to join in, totally ignoring me, as teenagers tended to do with any little kids, until one of them noticed that I was bigger than most toddlers at which point the entire story came out.
There followed some more laughing and pointing, but also some concerned looks, and even some questions after my general welfare which was nice if unexpected. Mind you, none of them made any attempt, or even suggested, that I be let go. NOt even teenagers back then, would have gone against something an adult had asked for.
IT was while we were sitting in the park that Shaun announced that it was lunch time, sending Sawyer off to the shops to by sweets and drink for them, while I was too be treated to something more fitting to my current status in the form of baby food.
A plastic bowl, with matching spoon was produced from the carrier under the back of the pushchair, and filled with the contents of a few jars of pre-made baby food. While Shaun got this ready, Aha, pulled the ribbon that released the dummy from my mouth, my jaw aching as he pulled it free. Staying in position behind me so he could tie a bib around my chin.
"Open wide Baby Kyle," announced Shaun in a voice loud enough to guarantee an audience as he started to feed me, taking care to smear plenty of the overly sweat, sticky mush around my mouth, as if I wasn't totally cooperating with the operation, just like a proper baby would.
The meal didn't last long, for which I was thankful as baby food tastes horrible, and then it was time for me to have a drink. Sawyer was back by then, so this was handed over to him. THe nine year old taking up the big baby bottle of milk and thrusting the rubber teat into my mouth, threatening to pinch my nose if I didn't drink it all down, even though I still made no resistance to him.
Eventually the bottle feeding was over much to Sawyer's disappointment. He did get to remove my bib and put the dummy back in my mouth which seemed to cheer him up even though he couldn't get the ribbons tied tight enough behind my head and had to ask his brother to do it.
The walk back to The Cottage was seemed quicker and rather dull as by then everyone who was out and about in Blackwood had already seen me and no longer seemed interested which was a disappointment, but all in all it had been a great day, and I hadn't even used my nappy next. Well not for what it was intended for. I had made some wetness in there. The sticky sort at the front, that felt a lot like apple juice, but which was really a lot more fun. Still the day might have been nearly over but the night was only just about to begin.
Chapter Nine Making Myself Available
"Where is he?" asked the first voice, in a surprisingly high tone, as two sets of footsteps came towards the point where I had been waiting for them, since I'd seen them approaching the secluded lane that led down to one of the out buildings that were dotted around Aunt Aggie's cottage.
"The note said he'd be in the shed at the end, so let's go look there," remarked a second more mature voice that belong to Blackwood's premier bully, Joe Danto.
Remaining where I was, for very good reasons, I heard the steps come closer, crunching up the shingle track to the door I was facing, then there was a pause accompanied by a shadow falling over the window, followed by a voice.
"Hey Donny, he's in here, you gotta see this."
The second voice was slightly further away, the younger brother of the duo, always more timid despite also have a fearsome reputation, "What? What is it?"
"Come see for yourself."
"Is it like the note said?"
There was no answer to that question as by then the shed door was opened, allowing sun light to flood in and illuminating me in the process. the sight of which clearly took the voice of both the bullies at once, and why not. It wasn't every day they were told there was someone waiting for them to do whatever they wanted to. I'm still surprised they actually followed it up, and never suspected I was a trap of some sort. BUt then bullies always tend not to be all that bright, do they.
The looks on their faces though were priceless. Both of them standing there, with their mouths hanging open, totally speechless, for what had to be the first time in their lives. Neither of them saying anything, or even moving as they stared at me.
And the reason for this?
Well, I was kneeling on the ground, almost totally naked, with my hands and feet chained to a post hammered into the floor, wearing a mask over my eyes, and with my mouth taped closed. There were some other things too, but they couldn't see those yet. Instead their eyes were staring at my erection which was, after all, staring right back at them.
"There's another note?" Donny eventually broke the silence pointing to the paper that was stuck to my chest with tape.
Joe remained silent, but he did come a few steps further into the shed so he could read the letters I'd helpfully made as large and simple as possible for him.
"What's it say?" prompted Donny.
"Shut up I'm reading." Joe said and so was I. Reading the words he was reading on his lips, as he worked his way through the short message, twice, before repeating it to his brother, even though Donny could have read it in half that time. "It says: 'Remove my Gag and I will tell you everything.'"
"Well, go on then. Take the gag off him."
"I'm doing it, ain't I?"
Actually Joe wasn't when he said that but he did a short while later, ripping the tape from my lips with a little too much force, which left me having to moisten my lips with my tongue for a few seconds before I could give them my prepared speech. Not that Donny was prepared to wait that long.
"What are you doing here?"
"I'm a gift." I said. Okay so it wasn't much of a speech. It got Donny's attention though.
"What does that mean?"
"I am being offered to you do with as you wish, so that you will leave some of the other boys in Blackwood alone."
That was more of a speech, but I'm not sure Donny bought it, or at least thought that he could, without actually admitting that he and his brother were bullies, which is something that bullies don't like to do for some reason. However, Joe wasn't so deep thinking: "What can we do with you?"
"Anything you want!"
"BUt you're tied up. We can't do nothing whilst you're tied up."
I looked towards the back of the door they'd just come through, "There are keys there for my hands and feet, but not for mu neck."
"Your neck?" the sixteen year old repeated, coming closer so he could peer around behind me, finally noticing the leather collar buckled around my throat, which was sealed with a padlock that also connected it to a long length of chain, the other end of which was locked to the floor of the shed. They didn't know this but that chain was also just about long enough for me to be able to reach the keys hanging on the door myself, but that thought never occurred to them. Thankfully.
Donny still didn't look convinced, so I gave him the rest of my sales patter, "I am yours, no questions asked, until the time stated on your note. You may do anything in that time, and some items have been provided to help you."
This time I looked towards a corner of the otherwise empty shed, where a cloth covered some items on the floor in an inciting way. Naturally the bullying brothers couldn't resist going to have a look which was good as it would answer quite a view of their questions.
Once more they were struck dumb as they looked down at the items I'd laid out for them to see. Some of which were fairly ordinary, at least in the terms of what I'd heard about what these two did to their victims. Rolls of duct tape, chains, padlocks, even some handcuffs were at once end, but it was the items at the other, that they were most interested in. Things that I'd made myself, and which could only be for one thing, given the tub of vaseline that was set beside them.
"Can? Can we use those?" Joe asked, although it wasn't all that clear if he was asking me, or his brother. Not that it mattered as neither of us actually answered him for Donny had his own question. One that was rather more pro-active, and straight to the point.
"If I ask, will you suck me off?"
I paused, before answering, just to savour the surprised look on Joe's face. One that was about to get even more surprised, as I said that I would and that they could fuck me too although they'd have to remove the plug in my bum first.
Clearly Joe wanted to ask something about that, but Donny had already got the answer to his question and he wasn't about to wait any long to act upon in, as he was already unbuckling his belt and pushing his jeans down to his ankles, along with is boxer shorts. "Okay," he said to me, "Suck me."
Shuffling forward with his trousers around his ankles, Donny stood directly in front of where I was still kneeling, raising himself up slightly onto the tips of his toes so that his semi hard erection was brushing against my lips.
Casually I glanced up at him and then opened my mouth taking all of his slender length inside in one gulp. Then if that wasn't enough for him, I also sucked on his hairless balls as well, pushing my face all the way down until the few strands of pubic hair he had tickled the end of my nose.
Behind the action, in a place where I couldn't see given my eyes were pull of Donny's pubic bone, Joe clearly decided he wasn't going to be left out of this party, and was totally naked in a few short seconds. Not overly tall for his age, Joe had a good build on him, explaining why people, especially those younger than him, would be scared of him. He clearly worked out, or at least did something that kept him fit, and was a natural blond, given that the hair colour extended down to the bush around his more than ample erection. His body was nicely tanned too, showing that he liked to show it off, although his was deathly white, below the waist, unlike myself with my almost fully body tan.
At thirteen, Donny Danto, was a time bomb waiting to go off, especially when it was offered up to him on a plate like I was doing, meaning that it only took as long as Joe took to remove his clothes before the younger boy was spurting his few spurts of thin juice into my mouth.
"Wow, that was great." he staggered backwards nearly falling over the clothing bunched around his ankles. "You've gotta try that Joe."
"Yeah think I will."
The bigger boy moved in front of me his erection waving already slick before my face. My mouth opening ready to take it in, expecting another quick result as with his brother but instead, Joe surprised me by pulling back just enough so that the only part of him I could reach was the very tip of his erection, even if I strained against the chains that held me down.
"Easy boy!" the youth sniggered, patting me on the head, as he moved his hips slowly forward allowing me to lick and then kiss the end of his prick.
There he paused, getting used to that sensation before moving again, just an inch or so, with his hips so that the entire crown slipped into my mouth. My lips locking around the underside, holding it there as my tongue went to work, moving over everything that was now in my mouth but paying particular attention to the slit in the middle that I knew would drive him crazy.
Surprisingly for a nearly sixteen year old boy Joe had remarkable control, and was used to being in charge, although this could well have been the first time he'd had a willing boy sucking on him. All the same he choose what to do and when to do it, which was great with me as that's just what I wanted him to do.
Slowly he continued moving forward, feeding me more and more of his prick until I had the entire length inside my hot sucking mouth, and yet there was still a bit more trying to get inside me.
This wasn't the first time I'd done this, so I knew what to do when I felt the head of a prick pressing against the back of my mouth. There was a slight cough like I was choking but then, I was able to get my muscles under control, and allow Joe's erection full access not just to my mouth but to my throat as well, into which he slipped until there was no more of him to go and once more I found my nose pressed into Danto pubic hair.
Caught by surprise Joe didn't seem to know what to do once he found his prick totally inside my face, but thankfully, his brother was on hand, to remind him that I had to breath, getting Joe to pull back a short bit so that I could do that.
From that point on, Joe knew what to do on his own and soon he was rhythmically pushing his erection in and out of my helpless mouth, slowly increasing the speed as he did so, as the sensations I was creating in him, got ever harder to control.
All in all, Joe probably lasted nearly ten times as long as his brother had, but then as Donny had blown his load within minutes that's not really saying that much. That said, there was a lot more to Joe's orgasm than their had been to Donny's. Still I managed to swallow it all, back in the days when there was no danger in doing that. Or at least none that any one had told us boys about.
"That. Was. The. Greatest." panted Joe, saying each word like it was it's own sentence.
"Yeah, well you have a rest, cos I want to do something else with him."
Joe didn't need to be told twice, mostly because he could barely stand up, so he moved over to the side where he could lean on the side of the shed while Donny went to work with the keys releasing me from my kneeling position but not releasing my hands from the handcuffs, although he did remove the chains from my ankles.
"What you doing?" Joe managed to say an entire sentence in one breath, albeit a short one.
"I want to see his bum."
The explanation was somewhat unneeded as by then, Donny had got me to lead forward, so my head was on the floor, and as I was still kneeling that raised my bum up in the air, allowing him to look all he liked at what turned out not to actually be my bum itself but rather what was between them.
"He's got something up his bum!"
Obviously I knew this already, but Joe clearly hadn't caught the mention I'd made of it earlier, so he came shuffling around to see what his brother was talking out, which was the small black ring of folded electrical cable that was poking out of my hole.
"What's that for?"
"It's so I'm already ready to fuck." I explained even though (a) the question hadn't been addressed to me and (b) it wasn't actually true. The truth being that I liked having things stuffed up my bum, and had done for some years.
"Can we take it out?"
Again, might have been a rhetorical question but all the same I answered it, saying that they could, as long as they put it back again when they were done, as they had to leave me in the same condition that they found me.
Putting his hand on the small of my back, Donny slid his finger into the small loop and started to gentle pull while I willed my sphincter to expand as the homemade butt plug started to come out of my hole. The thin cord soon widening to roughly the size of a small golf ball, before it started to slim down again until it finally came all the way out.
"Wow, look at the size of that!" Donny held the plug up so his brother could see it, both of them clearly amassed that it had been right up my bum, even though it wasn't the largest I'd had up there by a long way and wasn't even all that much bigger than the erection now pushing out from the Joe's loins. The comparison of which bought to the older boy's mind something else he could do.
"Hey, Donny do you want to..?"
"No, mine won't fit in there. You do it. I'll go round the other end."
Getting up from where he'd been squatting behind me, Donny made the short journey back to my mouth, where he wasted no time in filling with his pricklet, even before I got the chance to tell him that his wasn't too small to go in my bum, which was happy with anything that was put inside it, no matter what the size. Not that Donny was actually all that small in that department anyway at least not for his age. Of course compared to his two year older brother, he probably thought so. Still that wasn't my problem as I was about to have a prick in each end of my body, which just about the perfect ending to the perfect encounter even if Joe did forget to use an lubrication.
Thankfully, due to the plug I'd made for my own bum, my hole not only wasn't all that tight, but was also readily slicked up, allowing the fifteen year old entry without too much fuss. Then I used my anal muscles to clamp down on the invading member, just as I had the entire length of the younger Donta prick in my mouth.
The simultaneous action, drove both brothers to fuck me like their lives depended on it, while I knelt between them, my hands still cuffed behind my back, putting quite a strain on my spine as I was buffeted from behind, by a pounding youth, and performed a near perfect blow job on a boy just a little younger than myself.
It didn't take long. Not just for both of them to shoot their stuff inside me, but also for me to shoot a fair amount myself onto the ground beneath us all. And no, one was touching my prick at all. IT just went right off by itself, just like it often did when someone, or something was working away up my bum.
After that the scene fell apart fairly fast, as there's nothing less active that teenage boys who have shot their load, especially when they've done it twice like the brothers had. I for one would have liked to have continue on for another round, but somewhat surprisingly the brothers, once they recovered their sense, suddenly became concerned that someone would find them there with a chained up naked boy, as if this would somehow ruin their reputation.
Before they left, but only after they'd got dressed again the did complete the terms and conditions of the gift they'd been given, carefully re-inserting the plug in my well fucked bum, taping my mouth, and chaining me back into the kneeling position that they found me in. Only then did they leave me with my prick hard once more and still pointing at them.
As they left I heard Joe asking his brother, if they could come back later as I would still be there, given how well I was chained up. However, even as he spoke, I was already mostly free as naturally I'd built in a release system to my self bondage. The locks to which I'd provided keys, also having quick release buttons on them, just in case I needed to get out of them in a hurry. Not that I took everything off straight away. Not until I'd added to the puddle of boy juice on the floor in front of me. the gag doing a very nice job of preventing me making too much noise, just as they always did.
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