This is part 2 of the story of the sexual manipulation of teen boy Michael by his headmaster, teachers and other figures of authority who are fortunate enough to have the opportunity to exploit his increasing desire to be dominated and humiliated.
If you have not already done so, it may be best to read part 1 first.
Your comments and ratings are always welcome. I hope you enjoy the series. M ------------------------------------------------------------------------------------------------------ The next morning, as I gradually awoke from a restful sleep, I became aware of atightness in my groin.
With a start, the previous evening's events flooded back to me as I reached down to find the thick elastic band still stretched around my testicles. My little penis shot up as I recounted what the headmaster had done to me the night before and suddenly remembered that I was to be receiving a visitor within the hour.
In somewhat of a panic, I jumped out of bed and went to the bathroom where I emptied my bowels and showered, paying particular attention to the washing of my private parts, just in case I was required to present them to my form teacher during her visit.
At ten o clock sharp I was waiting nervously at the kitchen table when the doorbell rang. Walking timidly to the door, I opened it and was greeted by Miss Bolton standing there in a knee length leather trench coat and carrying a holdall. "Good morning Michael, I believe you are expecting me. Are you alone?" "Yes Miss Bolton" I stammered. "Good, well take my bag and let's be getting on then. We have a lot to do and so we should start immediately" Miss Bolton said as she walked past me and indicated for me to follow teen nude beach sex can you trust your girlcrony leaving her alone with your father. Closing the door, I followed meekly into the kitchen where she placed the holdall on the kitchen table and proceeded to remove her coat.
As I stood in the doorway watching the coat peel away from her body, I was transfixed by the vision that confronted me. Beneath the coat, Miss Bolton was wearing a black shiny corset that cut just beneath her copious breasts, leaving the gelatinous orbs fully exposed and hanging heavily halfway to her waist. Beneath the corset and covering her crotch was a pair of panties made from the same shiny black material and cut tightly between her legs, clearly showing the plumpness of her labia.
The outfit was fully complemented by the thigh length black leather boots laced up the front and polished to a high gloss. It was with difficulty that I managed to drag my eyes away from the deliriously beautiful sight of my teacher's huge tits as she walked to the table and unzipped the bag.
Miss Bolton motioned for me to take a seat and then sat opposite to address me. "Right then Michael" said Miss Bolton commandingly, "the headmaster has informed me of every unfortunate detail that occurred last night and how you have deeply disappointed him. The head has also told me that you deeply regret being unable to pleasure him satisfactorily and that you have agreed to work to your utmost ability, under my direction, to rectify your failings in the shortest possible time so as you can repay his kindness.
Do you agree that this is the situation?" "Oh yes Miss Bolton, I want to learn how to be a good boy for the headmaster and repay his kindness" I stammered, trying desperately not to stare at my teacher's breasts. "Good, I am pleased that we are in agreement as that will make the proceedings so much easier" said Miss Bolton. "But first, I want you to understand that the reason I am wearing such an alluring attire is not for you to think that I am available to you.
The reason is that I want you to be in a constant state of arousal whilst I am in your presence as this will make your training more bearable for you. You are not permitted to touch me without my explicit permission and you must do exactly what I instruct at all times. Do you understand, boy?" "Yes Miss Bolton". "Excellent. In future you will address me as Mistress. So, you may now commence by showing me what a good boy you are and present yourself to me naked." Nervously, I took to my feet and started undressing.
First I removed my upper clothes and then slowly lowered my trousers and underpants. I was not wearing any socks. Standing naked before my form teacher, I could feel the redness filling my cheeks and also, to my embarrassment, a stiffening stirring in my loins. My Mistress then searched within the holdall and pulled out what looked like a pair of ladies sexy panties but with the crotch removed. "These are your new sissy panties that you will wear from now on in my presence" my Mistress said as she motioned me to raise one foot and then the other as she pulled them up my legs whilst seated before me.
As I felt the silk panties rubbing against my thighs as they were slowly raised, my little peewee shot up to attention and, shockingly, brushed against Miss Bolton's face, leaving a thin trace of sticky goo across her cheek. "Now this will not do at all, you slutty boy" said Miss Bolton, wiping the goo from her face.
"The head warned me that you leaked like a sissy slut. I will have to resolve this at once". Pulling a pink silk ribbon from the holdall, Miss Bolton then prised my, by now, fully erect member through the slit in the pink silk panties and tied the ribbon firmly around the base of my penis. "There, that's much better" she said, as the ribbon constricted the blood in my little cock which by now was growing increasingly larger, particularly the bulbous end which was starting to turn quite purple.
"That should stem the flow until we ready to use your sissy cunt lubricant" she said, tucking my cock back inside my panties. "Now tell me" she asked, "did you have to relieve yourself last night and did you do as your Master instructed?" "Oh yes Mistress" I stammered, embarrassed. "I had to because I was so excited.
But I did as my Master told me and put it in the fridge." "Excellent" said Miss Bolton. "Now go and get it like a good little boy and bring me a spoon".
Opening the kitchen draw, I took out a teaspoon and then retrieved the ramekin that contained my load from the night before. Passing it to my Mistress, she remarked that I must have indeed been very excited as the ramekin was almost half full. "Now come and kneel between my legs like a good boy and cum on ass of hot brazilian wench your breakfast" Miss Bolton ordered as she parted her thighs sexily and I took my place on the floor between them.
Taking the ramekin in one hand, Miss Bolton used the spoon to scoop up a thick dollop of the cum and offered it to my mouth. "Now open up, little boy, and eat your breakfast" she ordered as I gingerly opened my mouth and she inserted the spoon, tipping it slowly so as the goo dribbled sloppily onto my tongue.
"Now close your mouth and swallow!" Miss Bolton commanded. Swallowing, I felt the sticky cum slide down my throat and was pleased to note that it did not taste too bad after all, a little salty and metallic, but not as bad as I had expected. Spoon by spoon, my sticky semen was fed to me until the ramekin was almost empty, at which point I was ordered to lick it clean. "Excellent" said Miss Bolton as she placed petite mexican teen slut loves big dicks mexicana amateur ramekin and spoon on the table, "now that wasn't so bad was it".
"No Mistress, thank you for my breakfast Mistress" I said. "In future, when you relieve yourself, it must always be in this way and you must keep it nice and fresh in the fridge.
Now to the specifics of your training: I understand from the headmaster that your little boy cunt is far too small to accept his generous cock and that you were even unable to satisfy him with your sissy mouth. Both these problems we will work together to rectify. You should be very grateful to the headmaster for giving you the opportunity to redeem yourself." "Yes I am very thankful and will show my gratitude next time I am allowed the chance to pleasure him" I agreed.
"Ok now let's get started" she said. Miss Bolton then took some sort of harness from the holdall and attached it by means of two straps and buckles around her waist and between her thighs. She next took a red cock shaped object from the bag and attached it to the front of the harness.
My form teacher suddenly looked as if she had grown a full sized erect penis from between her thighs! "This is your Mistress' cock with which you will become very familiar" she said. Miss Bolton then took out a large metal object shaped like a cone which was about 6 inches tall and 4 inches in diameter and placed it on the floor in front of the chair.
She then removed a tube of lubricant from the bag and placed a large gooey blob on the top of the cone. "This is a butt plug trainer with which you will also become very familiar with!" she smirked. Removing another circular type metal object from the bag, and sitting back down on the chair, Miss Bolton commanded me to stand facing her. She then drew down my panties and, taking a firm grasp of my balls and sac, removed the elastic band and then proceeded to secure the metal ring around my balls.
"Your Master has provided you with this gift which you must wear at all times" she instructed, attaching a small pad lock as she did so. Having finished attaching the ball weight, she removed her hand and let it pull down on my little balls and scrotum.
The feeling was incredible as the heavy tugging sensation caused my little prick to grow as even more blood rushed into my ribbon-tied prick and I flushed red to be standing in front of my form teacher, naked save for my girlie panties around my ankles and with a fully erect boy clit! I was then turned around whilst Miss Bolton attached leather cuffs to my wrists which she secured together behind my back with a metal clamp. "Now" said Miss Bolton "I want you to kneel astride the butt plug between my thighs and lower your little cunt until the tip of the plug is just touching your dirty little hole".
I did as instructed then my Mistress stood up and positioned her legs either side of my knees and, gripping my head between her thighs so as her cock rested on my forehead, gradually eased her weight down upon me until I could feel the tip of the plug slowly start to invade my most intimate hole. Initially, the sensation was quite pleasant; particularly as I could fell Miss Bolton's bare thighs pressing against the sides of my head and smell her musky scent however, as she continued to push down, the plug began stretching my boy cunt wider and wider until I thought it would rip apart!
I opened my mouth to cry out but, just at that moment, Miss Bolton moved backwards and, gripping her big red cock in one hand, grasped the back of my head with the other and forced her rod deep into the back of my throat.
My eyes immediately began watering and I was choking on her cock and trying to gag, though this was impossible due to the thick shaft being lodged in my throat.
What made it even worse was that the more I wriggled, the more the plug in my bottom ventured ever further up my ass. Just as I was on the verge of panic, my Mistress gripped my head now with both hands, securing the knob of her shaft deep in my throat, and gently said: "Relax and breathe deeply through your nose.
Try it". Flaring my nostrils, I concentrated hard and began drawing breath through my nose, which gradually calmed me as I found that I could indeed breathe whilst this monstrous weapon was violating my windpipe!
"There's a good boy" Miss Bolton crooned, "You can take a cock down your throat after all.
You can thank me later but for now we need to get you accustomed to a moving object in there". At that, Miss Bolton commenced slowly fucking my face and throat, almost drawing the huge asian milf teasing watch more of her at ulacamcom to my lips before steadily pushing it to the back of my throat and beyond until it had all but disappeared inside me.
In and out that monstrous cock went whilst I became more and more used to the sensations and could finally breathe relatively comfortably. I started making little moaning noises as the saliva ran from either side of my mouth onto my waiting erect peewee head that by now was a throbbing purple bulb as I became even more excited and the blood continued to flow into my constricted shaft. This my Mistress took as full cooperation and so increased the thrusting into my face until she herself became excited and began shouting out: "That's it little sissy boy, take my hard cock down your throat you little fuck toy!" she exclaimed loudly.
"Act like the little boy slut you are and suck that cock!" After about 10 minutes of continuous throat fucking, by which time my stomach, thighs and groin were covered in my saliva, Miss Bolton finally withdrew here rubber phallus, stepped back and surveyed me.
My face was wet with tears and my lips were swollen from the face fucking. My little cock was now not so small as it was engorged with blood and the purple knob was throbbing fiercely. My hips continued to circle around involuntarily, massaging the huge plug ever deeper into my boy cunt as a knelt in a pool of my own saliva.
Though despite my excitement, no fluid had escaped my prick as the pink ribbon secured tightly around the base of the shaft prevented any of my naughty goo from oozing out. "You have performed very well, lesbian drinking spit wet kissing little sissy boy.
The headmaster will be very proud of you when I report back to him" Miss Bolton said. Now we need to concentrate on that little fuck hole of yours and see if it is any more accommodating".
At that, Miss Bolton unlocked my wrist cuffs and instructed me to lie on my back on the kitchen floor. Grabbing hold of both of my ankles, she then drew them over my head and re-secured my wrists behind my knees so as I was folded in two with my cock and balls hanging down directly above my face.
My balls swung invitingly to and fro as the weight pulled down heavily on them. Miss Bolton gave them a few little smacks, causing me to squeal, before removing a large funnel from her holdall and inserting the end into my mouth. "Now hold the funnel in place so as the wide end is directly below your little cock or I will be smacking your little ball sac a lot harder!" she said.
Next, my Mistress undid the pink ribbon around the shaft of my penis.
Immediately, a thick flow of sticky goo began flowing from the little eye in my purple knob and ran into the funnel that I was holding for dear life with my teeth. Soon, I could feel the thick salty liquid running onto my tongue and then down my throat in a steady flow as the goo just kept flowing and flowing for at least a couple of minutes before steadying to a slow dribble.
Standing directly facing me behind my upraised arse, Miss Bolton could look directly down on my puckering boy pussy, which I could feel was winking uncontrollably up at her after the effects of the butt plug treatment.
Miss Bolton let a large glob of saliva run from her lips and guided it directly onto my hole, pulling my bottom cheeks apart to open me up so as the spit flowed directly into my bum. Pushing first one, then two fingers into my cunt, one from each hand, I then received a thorough massage of my back horny blonde slapping and make wet body with oil wecamnet. Miss Bolton allowed her fingers to alternately penetrate me deeper, before pulling them apart repeatedly so as she could see deep into the depths of my bowels.
The unrelenting dilation and friction training that my hungry little bottom was receiving caused the flow of pre-cum emanating from my wee hole to resume with renewed vigour. Miss Bolton removed the funnel from my mouth but commanded me to remain with my mouth open, resulting in half the flow of my goo to stream down my throat whilst the rest painted itself stickily all over my face and hair.
"That bottom trainer has certainly worked it's magic" said my Mistress, "you have really loosened up back here. Let's see what else we can stuff up your little bum hole".
Suck three large schlongs makes her happy that, Miss Bolton took yet another large black phallic ridged implement from her bag and showed it to me: To my innocent eyes, it looked like three man-sized cock heads stacked on top of each other, each head wider and more scary looking than the previous one.
"This is called the Intimidator" said Miss Bolton. It will certainly stretch this little butt hole of yours, have no doubt!" she smirked sadistically. Pausing the fingering of my bum for a few moments, Miss Bolton applied a generous dollop of lubricant to the end of the Intimidator before resting the first cock head at the entrance to my violated bottom before shoving it down hard into my bowels about 2 inches.
I gasped as I felt my sphincter muscle again stretched to what I thought was it's limits. "There goes the first cock head" exclaimed Miss Bolton triumphantly as she eased the Intimidator in and out of my stretched arsehole. Gradually, I became accustomed to the increased girth of this latest object to rape my swollen boy cunt and little moans again escaped my lips as the flow of pre-cum resumed with gusto, smothering my face and lubricating my tonsils as the dildo was pumped in and out, up and down.
Then suddenly my euphoria was again shattered as the plug was thrust suddenly hard down and the girth increased several inches, again stretching me to new limits.
But my lust was by now at such a level that it only took a few moments before I was once again able to accommodate its size and my moaning resumed. After what seemed like hours of increasing pleasure, but was probably only 5 minutes, a final hard thrust by Miss Bolton and the last and largest of the cockheads was rammed into my poor butt, burying the entire apparatus deep in my bowels save for the final couple of inches that my Mistress used to pump the dildo into my bum. As Miss Bolton sensed my ever increasing lust and horniness and anticipated my rising juices, she replaced the funnel in my mouth which just amplified my moaning even more.
All of a sudden, my Mistress began rotating the device, creating friction against my love bud deep inside my naughty pussy.
Simultaneously, she tugged down on the ball weight secured around my scrotum towards my head. It was more than I could stand and, with a final deep moan, jet upon jet of white creamy love juice exploded from my wee hole, falling and shooting into the funnel between my lips, filling schoolgirl couldnt await to be screwed japanese and hardcore greedy mouth before running thickly down my throat into my stomach.
I swallowed and swallowed, taking all of my naughty seed, until my swollen cock finally stopped pulsating and the flow of semen subsided. But the violation of my love hole was not complete, despite the fact that I was well and truly spent. Removing the phallic weapon from my anus with a flourish, causing copious amounts of lubricant to drip down my back and across my balls, Miss Bolton released my wrist cuffs and commanded me to present my rear end on all fours.
Positioning her knees either side of my buttocks, she placed the tip of her phallic member at the entrance of my love hole, grasped tightly on either buttock with her hands and rammed her giant red cock into the depths of my cunt.
On and on Miss Bolton fucked her dildo into my love channel until my very being was centred on that most intimate part of me. The pounding that my love button was taking eventually produced results as my limp prick commenced growing with renewed vigour until the purple knob rubbed against the tiled kitchen floor with each forward thrust. Just as I felt that I might soil the kitchen floor with my love juice, the thrusting ceased and Miss Bolton withdrew her tool from my bowels.
"You have performed excellently today my little boy slave. Your sissy cunt is well stretched and lubricated and you have the makings of a fine cock sucker. I trust that jerk off to feet hd punish my nineteen yearold culo and mouth will not think it bad manners on my part to leave you in a state of sexual arousal, however it is important that you have some of your dirty seed for breakfast tomorrow, so do not disappoint me.
I expect that ramekin to be overflowing with your semen when I return at 10am sharp. Now make sure you get a good night's sleep as we have more work to do tomorrow" At that, Miss Bolton slipped on her leather coat, threw her training tools into the holdall and departed, leaving me in a sticky puddle on the kitchen floor, aroused but by no means sated.