The Making of a Sissy Boy Slut Part 3

The Making of a Sissy Boy Slut Part 3

The initiation and degradation of Michael, a sixteen year old schoolboy, continues. Michael had previously been seduced by his headmaster but had been unable to fully satisfy him, which lead to a course of training by his form teacher, Miss Bolton. This episode describes the second training session plus an embarrassing encounter in his local corner shop with a dark stranger.

Waking early in the morning, I carried out my ritual of ablutions and showered, paying particular attention to the cleansing of my sore bottom and balls, which were still weighed down by the steel ring that circled my scrotum. Going to the kitchen, where I still could not believe the intensely arousing things that had happened there the day before, I remembered Miss Bolton’s (my form teacher’s) instructions and took the ramekin from the fridge. Surveying the contents, I could see that my pre-sleep masturbation had only managed to half fill the dish with my seed. Looking at the wall clock, I saw that there were still two hours left before my mistress’ arrival, leaving me plenty of time to complete my orders.

Dropping my shorts, I found the sight of the shiny steel sitting atop my little balls strangely erotic and so it was not long before my little peewee was standing at full attention and dribbling it customary amount of copious pre-cum. Grabbing my boy clit with one hand, I reached around my bottom cheeks with the other and managed to insert first one, and then two, fingers into my cunt and frig myself whilst pumping my clitty with my fist. Directing my little wee hole at the ramekin, it was not long before I managed to deposit a second helping of breakfast juice into the bowl which was now almost full. Replacing the ramekin in the fridge, I returned to the bathroom where I cleaned myself up before returning downstairs to await, with some trepidation, the arrival of my form teacher.

A knock on the door at exactly 10am and Miss Bolton marches through to the kitchen without any invitation.

“I like the shorts and t-shirt, nice touch, very sweet” said Miss Bolton. “Right, we have much to do again today so no time for messing about. Fetch your breakfast”

Dutifully, I presented the full ramekin and a spoon to Miss Bolton.

“Excellent, filled to the brim as I instructed” she said,” now come and sit on my lap for your morning treat”.

Without hesitation, I positioned myself on Miss Bolton’s knees as she placed one arm around my waist and collected a large dollop of cum in the spoon with the other.

“Open wide and eat your cum” ordered my mistress. I opened my mouth wide and took my medicine like a good little boy. Half way through my special meal, I started having problems swallowing all my goo, at which point Miss Bolton slid her spare hand inside a leg of my shorts and pulled down hard on the steel ring around my balls.

“Ouch!” I exclaimed, as I frantically opened my mouth wider and struggled to swallow the gooey mess. “Head back!” ordered Miss Bolton, as she picked up the whole ramekin and poured the viscous peppery white slime down my throat, slowly trickling the goo so as it thickly coated the surface of my tongue and tonsils before oozing down into my stomach.

“That’s better” said my mistress as she moved her hand from the ball ring to my stiff little penis and slowly massaged the head around and around, rubbing the juices into my little purple knob. This completely took my mind off the taste of my own cum and I hardly noticed when I had finished all of my breakfast.

My tummy now full of ball porridge, Miss Bolton pushed me off her lap, undid my shorts and removed them together with my girlie panties that I had remembered to put on first thing, giving the head of my clit a little flick as she did so.

“I want you on the kitchen table with your arse in the air and your head down”. “That’s right, now open your legs a little” she instructed as I positioned myself in this lewd position on the table. Removing the tube of lubricant from the holdall that now seemed to have a permanent position on the floor in the kitchen, Miss Bolton began greasing up my sissy cunt with her two fingers before pulling another new strange implement from her bag. This weapon for training naughty boys was, by now, a familiar butt plug shape, about two inches across, but was different than the others in that it had a tube with a bulb attached to the base together with another cord attached to a small plastic box. Not knowing what was to come, I remained motionless in my kneeling position with my balls pulled down towards the table top by the weights and my boy clit starting to again, embarrassingly, ooze a sticky puddle onto the table.

Without further ado, the plug was inserted into my back passage, quite easily I thought, though I let out a gasp as my little bottom was again violated, and then rotated back and forth until my mistress was satisfied that it was a good fit. Taking a metal chain with clips at each end from the holdall, Miss Bolton attached a clamp to each of my nipples and then adjusted them somehow until she could see I was starting to wince from the pinching of my sensitive nubs.

“Now we are going to stretch this little sissy cunt of yours until there is no doubt that you will be able to accept the headmaster’s cock in there” she said as, alarmingly, I suddenly felt the plug expanding in my rectum. Miss Bolton continued to pump the bulb until it felt like the inside of my botty hole was going to pop! By the time Miss Bolton was satisfied that I had been stretched sufficiently, the plug must have expanded to at least double its size as I was letting out little groans of both discomfort and pleasure as the plug was pushing and rubbing against my love button, causing my goo to flow in a constant trickle onto the table surface.

Running her fingers through the pre-cum that was puddling beneath my stiff little dick, Miss Bolton collected a large pool of it in her hand before rubbing it all over my face and inside my mouth with her fingers. She then grabbed hold of the chain attached to my nipples and pulled down, causing my little nips to elongate and create painful yet pleasurable sensations that shot straight down to my crotch. At the same time, my mistress turned a dial on the box attached to the plug and it was like an electric shock had just exploded inside my bowels as the inflated plug started vibrating crazily, creating wild exhilarating feelings inside of me. I could not contain myself any longer and my love porridge jetted out of my clit and all over the table as I screamed in ecstasy.

Suddenly, there was a knock at the door. I started and went to move from my embarrassing and exposed position on the table but my mistress placed a hand on my bottom and told me not to move. “Stay right there, naughty boy, I haven’t finished with you yet!” said Miss Bolton as she went to greet the guest.

I could hear another woman’s voice that I thought I recognised coming from the hall where they were having a hushed conversation that I could not quite make out, though I did hear my name and the headmaster’s mentioned. With rising embarrassment and trepidation, I remained motionless with my butt and private parts exposed and the inflatable butt plug gyrating inside my bowels. Despite my anxiety, I could still feel my clear wee spewing out of my clitty.

“I think you know Miss Marsh” said Miss Bolton as she walked back into the kitchen with another woman. I did indeed recognise her as she was a gym teacher at my school and very fit as well, being about 22 years old, brunette and with a very shapely figure. I could feel my blush rising in my cheeks as I imagined the view that Miss Marsh was getting of my secret places as she was standing directly behind me.

“Hello Michael” Miss Marsh said, with a lustful voice, “I can see you are enjoying your sissy training very much, judging by the puddling on the table!” she crooned whilst dipping a finger into the goo and popping it into her mouth. “Oh yummy, I just love young peewee juice, how inviting your bottom looks!” she exclaimed.

“Well we don’t have time for any more training as I have to leave shortly” Miss Bolton said hurriedly to me. “However, I need some cigarettes and would like you to go to the corner shop and get them for me. Now jump down from the table and put your shorts back on”.

“But what about my bottom!” I exclaimed, “it is all filled up!” Miss Bolton turned down the vibrations until there was just a slight ripple running through my insides and reduced the inflation of the plug to about half its size so as it was comfortable but I could still feel the pressure on my love button.

“There we go, said Miss Bolton as she pulled my shorts up to hide my shame, drawing the tube and cord from the butt plug up between my crack and over the top of my shorts, finally popping the bulb and control box into the right pocket of my shorts. “Now pop your t-shirt back on and no-one will notice” she smiled mockingly as I put my sandals on ready to go to the shops with an inflatable butt plug up my botty!

Handing me some money and telling me the brand of cigarettes that she wanted, Miss Bolton steered me out of the front door, “Now be quick and don’t talk to any strangers!” she shouted after me, as I struggled to walk “normally” for the first time with my bottom filled with a gently rumbling butt plug.

With flushed cheeks from the embarrassment of it all, I walked as quickly as my stretched bottom would allow, hoping to get to the shop and back without seeing anyone, though I was sure that my predicament was well concealed beneath my shorts and t-shirt. Thankfully, I arrived at the mini-mart on the corner without having seen anyone. Good, I thought, just the shop assistant to deal with and then I can scurry home again.

And so it was with dismay that, stepping into the shop, I could see at least 4 other people in there! Keep cool, I thought as I walked through the aisles to get to the till, just act normally. Everything was going fine until I was acutely aware of a man in his thirties staring at me from the end of the aisle as I walked towards him. He seemed to be staring at my chest and it was with a sudden horror that I realised that Miss Bolton had failed to remove the nipple clamps from my bubbies and that they must be visible through my thin t-shirt. In my flustered state, I managed to bump into a display of breakfast cereal and fell to my knees both to tidy up the mess I had made and to pick up the fallen boxes. Rising to my feet again, I raised my head up high and brushed past the staring man, blissfully unaware that my t-shirt had ridden up above the waistband of my shorts, thus exposing both the tube and power cord attached to the plugging device buzzing away deep inside my bottom.

As I joined the end of the queue of people at the cashiers desk, I took a few deep breaths and told myself that no one knew of my secret, even as I thought I could hear a faint humming from my shorts. Indeed, the swollen bulb filling my boy cunt and the vibrating action against my little button had caused quite a swelling in my pants and I could feel the material of my shorts dampening due to the emissions from my wee hole. Just as I was considering how to conceal the damp patch in my crotch, I felt a hand on my shoulder and, looking quickly around, recognised the staring man standing behind me, now last in the queue.

“Turn and face the front, don’t move, and your secret is safe with me” said the man in a low but commanding voice. Fearful that my secret be exposed in such a public place, I humbly agreed and faced the front of the queue. Then, to my horror, I felt the man’s hand venturing into the pocket of my shorts that held the controls. Looking down, I realised that the tubes had become exposed and, before I could adjust my t-shirt, the man lightly grasped the bulb and gave it several slow, firm pumps. The sensations inside my boy cunt were instantaneous and thrilling as the plug expanded to twice its normal size, pushing hard into my love button and immediately intensifying the vibrating action. I almost fell to my knees as the man then turned his attention to the control box, turning it fully to it’s highest setting, creating deep exhilarating waves of vibration rippling all the way from around the entrance to my botty hole right up into my bowels. The sensations hitting my little love button were too much for me to take and, as I began to sway and fall backward, the man placed both hands on my shoulders to steady me as I came forcefully into my shorts, standing in line in a queue in my local mini mart!

Biting my lip so as to avoid screaming out, jet after jet of creamy cum juice spewed from my boy clit, soaking the insides of my shorts and dribbling down the inside of my leg. A few seconds later, I felt the sensations subside as the man again ventured into my pocket and turned off the vibrations, letting go of my shoulders as he did so.

“Can I help you?” said the cashier, as I realised that I was now first in the queue but standing 6 feet from the counter. I mumbled brand of the cigarettes Miss Bolton required, quickly paid for them and stumbled out into the street, almost running the 100 yards or so back home, not once looking back for fear that the man was following.

“Ah Michael, about time” said Miss Bolton, greeting me in the hallway. “Miss Marsh has informed me that the headmaster has to go away urgently on business, therefore he will not be able to attend to you for a couple of weeks. However, he has asked me to ensure that your training continues. Indeed, with two whole weeks of training, he expects you to be an absolute expert in all the ways of pleasing a man”.

Hiding my disappointment, but also my excitement at the thought of being Miss Bolton’s sexual plaything for another two weeks, I hurried past the two women and sat at the table, albeit slightly uncomfortably with the plug still in my botty, concealing the state of my shorts and my cum stained leg. My mistress and Miss Marsh then had a brief discussion about where my continued training should take place, particularly as my father would be returning shortly, and agreed that their house was the best location. Then, without saying goodbye to me, Miss Bolton hurried out of the door, leaving me with her work colleague and, as it had now transpired, her housemate.

“Now then Michael, we will be getting to know each other a lot better over the next few weeks” said Miss Marsh, taking a seat at the table. “Come and stand between my legs so as I can take a better look at you”. Folding my hands in front of my crotch in an attempt to conceal the stain in my shorts, I stood between the open thighs of my seated gym teacher. However, as she moved my hands aside to gain access to the button of my shorts, my secret was exposed.

“My goodness, what has been going on since you left the house!” she exclaimed “It looks like this naughty boy has got all excited and been rubbing himself in public. Now get those shorts off this instant, you bad boy, and take what’s coming to you!”

I nervously lowered my shorts to my knees, strands of cum sticking to the end of my boy clit as I did so, and the controls of the plug now hanging feely between my legs.

Grabbing hold of them, Miss Marsh began pumping the bulb, expanding the dildo in my bowels more and more until my bum cheeks were clenching and I was begging her to stop.

“Oh please no more Miss Marsh, my bottoms going to explode!” I cried as I tried to accommodate the huge phallus in my boy cunt.

“Let this be a lesson to you!” she said throatily as she turned up the vibrations until my legs were shaking uncontrollably. Just as I thought I would faint, Miss Marsh let go of the controls and, grabbing my ball weight in one hand, started slapping my balls with the other, gently at first but then harder and harder, spanking my little balls with an upward motion until the tears started running down my cheeks.

“I’m sorry for being such a naughty boy Miss, please stop hurting me, I will do anything but please stop!” I blurted as my tears fell.

“You must learn obedience, you filthy little slut. Now lie down on the floor and remain still whilst I prepare myself” she said. Gratefully, I got down on my back and waited for what was to follow, the bulb still pulsing uncontrollably in my bowels, but I was too fearful to complain.

Standing up, Miss Marsh pulled up her short skirt and removed her panties, providing me with a terrific view of her private girlie parts as she straddled my face and then, before I knew what was happening, she positioned herself with her back facing me. Gradually, Miss Marsh crouched over my mouth until her musky bum hole was an inch from my lips.

“Now you said you would do anything to stop me hurting you so you can start by licking my butt hole, and make sure you do a good job!” she commanded me, grabbing my liitle balls and cock to steady herself. Tentatively, I opened my mouth and delicately poked at my form teacher’s brown hole with my tongue

“Harder and deeper, or I will whip your little balls until they are blue!” Miss Marsh exclaimed as I feverously licked harder and harder at her dirty hole, even pushing the tip of my tongue into the tight ring.

“That’s it, now deeper you sissy slut. Eat my arse you sissy whore!” she screamed at me as I tried desperately to satisfy her dirty fantasies. With a concerted effort, and assisted by Miss Marsh relaxing her sphincter, I managed to get my tongue about 2 inches into her bottom, which tasted kind of musky but not too bad, particularly as I could smell her wet pussy just an inch from my mouth. The moans from Miss Marsh became louder and louder as I explored her rectum with my tongue, even letting out little farts which blew into my mouth and up my nose, tickling my tongue as her sphincter vibrated as the air escaped.

After a few minutes, I became aware of Miss Marsh’s hand rubbing furiously at her private parts and, as her moans became louder and louder, she moved back a little until it was not her bum but her bald pussy that was stuffed in my mouth. I had great difficulty breathing as she ground down on my face, her pussy juices streaming down my throat as she gyrated her arse around and around until finally, and thankfully, Miss Marsh let out a loud cry and her whole body shuddered and she slumped off me.

Before I had even got my breath back, my form teacher had risen to her feet and, pulling me up very painfully by the chain attached to my nipple clamps, sat herself down on the chair.

With a swift motion, Miss Marsh grabbed me around the waist and swung me over her lap so as my bottom was pointing up at her face. Holding me down with one hand in the small of my back, she began smacking my vibrating bottom, slowly at first but then more and more forcefully until the tears were welling up in my eyes and my bottom cheeks were on fire.

“You will NOT pleasure yourself unless you have been specifically permitted to do so. Do you understand? You naughty, naughty boy” Miss Marsh admonished me, slapping my arse cheeks after each word.

Despite the smarting of my cheeks, the slapping of my bottom was having an affect and I started to harden. Feeling this in her lap, Miss Marsh immediately ordered me to stand up. Taking hold of the ball weight in one hand, she then commenced slapping my stiff clitty with the palm of her hand until I was begging her to stop. My swollen little prick was slapped from left to right, throwing little drops of naughty goo everywhere until my knees started buckling from the pain. Just as I thought I could take no more, Miss Marsh leaned forward and, squeezing my little knob firmly between her thumb and forefinger, gave my it a little kiss on the tip before pushing me away.

“Right, young man, let that be a lesson to you” she said, standing to leave. “Miss Bolton has asked me to remind you not to forget your breakfast tomorrow morning. I will be here to collect you at 6pm sharp tomorrow evening. Make sure that you are prepared”. And at that, Miss Marsh left me on my own to reflect on the day’s extraordinary events, slamming the door behind her.

To be continued…

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