The Making of a Sissy Boy Slut

It was speech day, at the end of term, and we were all supporting the headmaster in our prefect role, welcoming parents and guests and applauding during the speeches at the right moments as we had been instructed.

Watching from the back of the large hall, I thought that the headmaster sounded a little slurred and was concerned whether he would still be able to give me a lift back home once the ceremony had finished, particularly as my father was away working and the night buses were infrequent at best.

However, my worries were unfounded as, once all the guests had departed, the headmaster came and found me to tell me that it was time to leave. During the journey, which took about 30 minutes, the headmaster was in very high spirits, telling me how successful the evening had been and how well I had been doing at school and, from his animated conversation, it became apparent that he had indeed had a few sherries earlier, as he began giving me his opinion of quite a few of the other teachers, information that I felt sure he should not be divulging to a 16 year old pupil. Soon the conversation reverted to my performance and how he had helped me during a particularly difficult patch I had had with the police when I had run away from home. The headmaster told me that, if it hadn’t been for his intervention, then the police would certainly have taken it further. However, he reassured me that the case had now been closed. I thanked the headmaster profusely, feeling both embarrassed that I had put the school in a difficult position but also very proud that I had such a powerful ally as the school head! The headmaster said that he was sure that there would be a chance in the near future for me to thank him properly and I assured him that I would do anything I could to repay his trust and kindness.

Indeed, when we arrived at my home, I thought this would be an ideal opportunity to start to show my gratitude by asking him in for a drink, something that I would never normally have considered but I had also been drinking from a small hipflask that I had secreted away and been sipping in the boys toilets most of the day! I was quite merry by the time the headmaster thanked me for my hospitality and I showed him into the house and asked him to make himself comfortable in the lounge whilst I prepared some drinks.

Having the headmaster sitting in my lounge, whilst I made a couple of gin and tonics in the kitchen, was becoming quite a thrill for me. I couldn’t wait to tell my friends at school that I had shared an alcoholic drink with the head in my house. Indeed, I planned to get him very drunk so as I could maybe find out some other interesting fActs about the other teachers and maybe even some of the pupils: information that I could use to my advantage later I was sure.

As I walked into the lounge, I found the headmaster seated on the sofa with our cat lying across his lap. He was stroking it affectionately and the cat was purring contentedly. Moving the remnants of my unfinished breakfast to one side, I placed the headmaster’s drink on the coffee table and sat down at the other end of the sofa. We then started chatting about the school in general, until the gin started to take effect and the head again started to talk about things that he should not really share, particularly things that some of the older boys had been up to in the toilets. He even mentioned some names and told me about the punishments that he had had to give them, including even the cane. It turned out that he had even been assisted by a couple of the women teachers on occasion and he confided in me that they really seemed to enjoy thrashing a young man’s bottom! I asked the head if that was across the trousers and he told me that, in extreme cases, he even had to order them to lower their trousers and pants and cane them on their bare behinds! I must admit to feeling a little excited about the vision of these naughty boys bent over the headmaster’s desk, their trousers and pants around their ankles whilst the head, with two mistresses watching, caned them severely across their backsides. As the gin had an effect on me also, I even had the courage to ask if he could see any of their private bits during the caning and the head told me that their hairy little ball sacs were usually visible and that sometimes the boys even got a little excited and their stiffening little penises would start protruding below their balls before standing to attention. The headmaster told me that, one time, he had to give a boy an extra ten strokes of the cane as his little peewee had dribbled some fluid onto the head’s desk and smudged some papers that he had been marking.

At this point, the cat decided to move off the headmaster’s lap and come and sit on mine, which was just as well as it helped mask a little bit of stiffness that I was getting in my pants!

“What a friendly little pussy you have” the headmaster said as he moved along the sofa to sit beside me and started to stroke the cat as it purred contentedly on my lap.

Gradually, the headmaster’s hands started to brush against my thigh as his hand took a wider path during each successive stroke.

“Nice pussy, lovely pussy” the headmaster crooned as his hand almost gave up stroking the cat completely as he rubbed up and down my left thigh.

At this point, and despite the alcohol I had consumed, I was beginning to feel that the situation had got a bit out of hand, however I was dumbstruck and frozen to the sofa, both feeling excited at what was happening whilst also feeling overawed by this powerful man taking an interest in me that I could only guess was of a sexual nature. I even felt myself responding, judging by the swelling that was occurring in my Y fronts, despite never having been touched by a man (or a woman for that matter) before.

I considered jumping up and making some excuse, however stayed riveted to the seat, both from fear and excitement, as the headmaster’s hand now blatantly rubbed up and down the length of my crotch. So instead, I decided to take the easy way out, closed my eyes and pretended that I had fallen asleep, in the hope that the situation would somehow remedy itself or I would wake up in the morning and everything would be back to normal!

But no, the headmaster didn’t stop and, indeed, became more and more ardent with his rubbing, still crooning about the beautiful little pussy even though the cat had long since left the room in disgust as it was no longer getting any attention!

Gradually, to my horror, I felt my flies being slowly lowered, but continued to fane sleep as the headmaster gently inserted his hand into my trousers. The head pulled aside the fly in my Y fronts and gently pulled my small erect member from within the confines of my clothes. My little cock was, by now, standing to full attention and, to my dismay, I could even feel a few small drops of that sticky fluid oozing from the little eye in the bulb. The headmaster obviously noticed this as well as he whispered:
“Oh you naughty little boy, you are getting very excited aren’t you. I can see a little bit of naughty wee coming out of your little prick, you naughty boy! Let me rub that into you before it stains your trousers.”

With that, the headmaster grasped my little cock head between his thumb and forefinger and squeezed, quite hard, causing me to open my eyes and gasp as I was confronted with the view of my little cock sticking up from my pants whilst my headmaster grasped it and slowly milked out small drops of my love juice which seeped down the purple knob before running onto the back of his hand.

“Ah, so you’re not asleep after all, you little minx” the headmaster said.
“ Here, clean this mess off my hand like a good boy or I will be very angry with you for getting all so excited, you little slut boy” he said as he put his hand with the sticky liquid to my mouth. Submissively, I licked gingerly at the salty liquid until it was all cleaned up, just as a good boy should.

His hands then dropped to my chest and I could only look on as a frozen spectator as Sir loosened my regulation tie and slowly unbuttoned my white school shirt, pulling it to one side to expose my little boyish nipples which, by now, were standing to attention like two frozen cherries. Delicately, the headmaster took both bubbies between his thumbs and forefingers and squeezed firmly.

“Please don’t hurt me” I said with a pleading tone, dipping my eyes submissively.

“Now why would I want to hurt such a beautiful boy” said the headmaster, smirking. “Just be a good little chap and consider how you can repay me. You can start by addressing me correctly” he said, whilst squeezing my nipples even harder, causing me to gasp both in shock and fearful excitement.

“Please don’t hurt me, Sir” I stammered submissively. “ Just tell me how I can be good for you Sir” I blurted out, “I just want to be good boy”.

“Well you can start by standing up for me” the headmaster said, drawing me to my feet between his knees by tugging again on my nipples. In one movement, the head pulled my trousers and pants down so as I was standing between his legs with my underwear around my ankles and my shirt open, with nothing to hide my nakedness other than my tie hanging between my chest.

“Now let’s take a proper look at you” the head said, grasping my boyish cock firmly at the base as he delicately cupped my furry little balls within his other palm and squeezed them gently. To my horror, this caused yet more juice to escape my cock which by now was emitting a continuous flow of sticky liquid to run down the shaft and collect in a pool on the carpet.

“You really are a messy little slut boy” said the head, “now turn around and lets see what else you have to offer”.

“Please teach me how a little slut boy should behave Sir! Please show me how a naughty boy can be good!” I blurted as he spun me around to face the coffee table so quickly that I tripped on my trousers around my ankles and fell to my knees with my body across the table. I was now completely under his spell, burning with lust and just wanting to do anything to please this powerful man who had me totally in his control.

“Good” said the headmaster, “you are clearly learning how to address your master. Now stretch your arms and take hold of the other side of the table whilst I examine you”. Breathlessly, I grasped the far edge of the table and waited motionless for what was to follow. I could hardly contain my excitement as the head slowly stroked both of my buttocks before gently prising apart my tight bum cheeks and blowing gently on my hairless bum hole.

“What a charming little boy cunt we have here” said the head huskily. “I think we need to give this naughty boy some friction training”.

“Oh yes please give me some friction training Sir!” I exclaimed, not having a clue what was to follow.

Reaching between my knelt legs, the head then scooped up some of the pre-cum that had puddled on the floor with his fingers and began smearing it between my crack, gradually grazing my puckered anus with his nails and massaging the fluid into the hole until it started to respond, the sphincter muscles relaxing until he could just insert the end of his forefinger inside. The sensation was incredible, causing me to moan and say “Yes please Sir, make me a bad boy Sir and put your fingers inside my naughty little boy cunt!”

At this the headmaster stopped abruptly and slapped me several times across the buttocks.

“That is NOT the correct way for a good little slut to behave!” said the head. “Your body is for me to enjoy any way I wish. You do not determine what is to happen. Now just be a good slut and do as you are told” he said.

“I’m sorry Sir, I promise to be a good little slut boy for you from now on!” I stammered, as the headmaster resumed gently massaging my winking hole.

The head then slowly inserted a finger deeper into my anus until it felt like it was all the way in. Then he gradually turned it left and right before finding what he was looking for. My god I was in heaven as his finger found my little love button and gently probed and massaged it until I was beside myself with lust.

“That’s your naughtyy little button” said the head,”and it can give you lots and lots of pleasure. See how your clitty is pumping out your naughty goo?” The headmaster was quite correct as I could feel my little peewee pumping out its cream with renewed vigour.

The head then reached into his pocket and withdrew a wide elastic band which he doubled up before taking hold of my little balls with one hand and, twisting and pulling down on them, secured the band around the base of my scrotum. The feeling was initially quite scary but, once the band was in place, the tight feeling that it gave to my ball bag was incredible. Gently, the head patted my tight balls dangling invitingly between my legs, as he continued to probe deeply within my bottom.

After what seemed like an eternity of heavenly feelings emanating from within my bowels, the headmaster withdrew his finger from my anus and offered it up to my mouth.
“Now be a good little slut boy and clean up your mess, the head said as I took his finger into my mouth and sucked it until he was satisfied that all the stickiness had been licked off.

“Good boy” he said, “now let us see if your sissy hole knows how to accept a master’s cock”.

I suddenly felt something much bigger than the headmaster’s fingers pushing ardently against the opening of what I now thought of as my boy cunt and I could here him utter a low groan as he tried, unsuccessfully, to penetrate my bowels. I strained to accommodate this new much larger object forcing its way in but, despite being told to relax and push back, I simply could not take in this man sized weapon. The headmaster withdrew and then, scooping up some butter from the plate that I had left on the table from breakfast, lubricated up his enormous purple knob with it before wiping his fingers clean across and around my rectum. This time, the head just managed to squeeze the bulbous end of his tool into my buttered up bum hole but that was as far as he could get. However, by pushing ardently back and forth I was able to allow him to gain entrance of about one of two inches before the tightness of my sphincter resulted in the head’s cock spewing forth its salty spunky load deep into my bowels.

“My God you are a tight little slut, aren’t you!” the head exclaimed as he ensured that every last drop of his jism ended up in my cunt. It was with great relief that I felt the head finally withdraw his cock from within me as I felt like he was going to split me in two, however my ordeal was not quite over as I was now presented with my master’s spent cock directly in front of my face.

“Now big a good little sissy boy and clean me up” said the head as he took hold of my cheeks and pushed his still stiff cock to my lips. Fearfully, I opened my mouth to accept his member as the head thrust forward in an attempt to fuck my throat. The sensation caused me to gag and immediately pull back. I was rewarded with a sharp slap around the face.

“Do not disappoint me again” said the headmaster. “This really will not do. Not only can you not satisfy me with your boy cunt, your throat is no use to me either! Well, we will have to fix this as soon as possible”.

With tears in my eyes, partly from the throat fucking and partly from the shame of letting the headmaster down, I exclaimed “I am so sorry Sir, please teach me how to satisfy a real man Sir, I promise to be good in future!”

“Well ok then” said the head, “there may be something we can do. When is your father back?”

“He is away for another week, Sir” I mumbled.

“Right, that will give us plenty of time to turn you into a useful little sissy boy, IF you follow instructions. Do you want to become a good little sissy boy?”

“Oh yes please Sir, please make me a good little sissy boy for you!” I exclaimed, not knowing what a sissy boy was but wanting to use the headmaster’s language.

“Your training starts tomorrow. Miss Bolton will conduct your training and will call on you at 10am sharp. Be sure to do EXACTLY as she tells you, or I will hear of it and you will be punished. When Miss Bolton believes you are prepared then I will come and try you out again”.

“Thank you, thank you Sir, I promise to be good and train well” I spluttered.

“Very well then” said the headmaster. “Your first instruction is to leave the band around your little balls until Miss Bolton arrives. After I have gone, you may relieve yourself but be sure to collect your sticky mess and leave it in the fridge to await Miss Bolton’s arrival”.

At that, the headmaster departed. It did not take long before I was wanking furiously into a ramekin, before storing it as instructed and wondering what sort of training Miss Bolton, my form teacher, had in store for me tomorrow.

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 her. 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 have 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 the 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 phallus 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, my 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 passage. 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”.

With 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 my 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 you 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.

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.

 

I spent the next hour on my own, cleaning myself up and tidying away the training equipment in the kitchen, until my attention was drawn to preparing my cum meal for the following evening. Miss Marsh had left me with a small Tupperware container, complete with lid so as it could be transported easily during my journey the following night, though I had no idea where I was to be taken. Miss Marsh had left specific instructions that the container should be filled to the brim with my ball cream but, having already come twice that day, I had doubts as to whether I would be able to manage one more spurt, let along fill it.

Seeking inspiration, I put on my sissy panties and, with my little cock and balls hanging through the slit, swinging gently by virtue of the weight around my scrotum, I picked up the holdall and settled onto the sofa in the lounge, placing the Tupperware container on the coffee table. As I rummaged through the holdall looking for something to get my juices running again, I pulled out the nipple clamps and chain and tentatively refastened them to my budding nipples. By tugging gently on the chain, I could feel the sap rising in my loins and a faint stirring happening between my legs. Encouraged, I took out the black butt tamer that Miss Bolton had used the previous day to open up by boy cunt to such good effect and placed it on the coffee table. Squeezing a large dollop of lubricant onto the helmet shaped shaft, I crouched with a foot either side of the corner of the coffee table and, pulling aside my panties, gently lowered myself onto the phallus.

This time my sissy hole opened willingly to accept the first bulb and I commenced gently bouncing up and down, allowing it to penetrate me ever deeper with each downward thrust, until I could feel the second knob pushing urgently against by botty.

With a determined grunt I sank further onto the shaft, feeling my sphincter being stretched to accommodate the second huge cock head as it finally popped inside and, in so doing, drew yet more of the shaft further into my bowels. Feeling nicely filled, I gripped my rapidly swelling boy clit with one hand and pulled down on the ball weight with the other, pumping my naughty cock until it was fully erect. I was starting to produce more of my goo but, after 10 minutes and despite being fully engorged, I could not tempt any more sissy juice out.

When I was almost ready to give up and was wondering how on earth I was going to provide sufficient cum for the following evening, I looked up and saw the man who had accosted me in the shop watching me from the doorway.

“Wha..what are you doing here!” I stammered, frantically trying to conceal my predicament as I covered my private parts with my hands whilst still impaled on the butt trainer.

“I saw you through the window” smiled the man, “and thought that you could do with some help. The door was open so I came in to offer my assistance”.

“I..I’m fine” I stammered, the colour rising in my cheeks. “I think it best if you go sir” I blurted whilst trying to raise myself off the dildo in my arse which refused to budge as my sphincter muscle had contracted, holding it firmly in place. Ignoring my pleas, the man approached me and placed his hands on my shoulders, pushing me gently back down and, thus, forcing the final, and largest, bulb up into my rectum so as it was now fully inserted and my bum cheeks were flat against the coffee table.

“Now that’s no way to talk to me after I helped you in the store this morning” replied the man. ”The shop owner was quite suspicious but I have told him that you had a tummy problem and that there is nothing to worry about, though I could change my story if you are not suitably grateful. Now tell me the problem and what those ladies were doing here earlier on”.

“Feeling that I had no other choice, I quickly recounted to him what had happened over the past couple of days. The man listened intently, all the while standing between my thighs with his hands resting on my shoulders. As I related my story, I could tell that he was becoming excited as a huge bulge became evident in his trousers just in front of my face, though that was the only outward sign that he was becoming aroused.

When I had finished my story, the man said:

“Well I can certainly see your predicament. I take it that, if you do not provide sufficient cock cream for your Mistress then you will be punished severely, so I think it best if you let me help you”. With that, the man removed his right hand from my shoulder and pulled down his flies, releasing his cock which sprang up to attention immediately in front of my face. It was uncut and must have been at least eight inches long, in fact it was the largest cock I had ever seen and completely hairless. I just sat there hypnotised by his manhood as it gently bobbed up and down until he took hold of my jaw, pointed his weapon at my mouth and eased forward.

“Now be a good little sissy boy and show me that you have learnt how to please a man” he said as his shiny knob parted my lips and entered my mouth. “Lick and suck the head” he commanded as I started to run my tongue around and around the bulb, saliva running down my chin as I did so. Gradually, the man eased his huge weapon further and further in until it was touching the back of my throat and I was only able to run my tongue up and down the underside of the shaft. Feeling a gag reflex building, I remembered Miss Bolton’s instructions and, holding back the panic growing inside me, started breathing deeply through my nose. Gradually, I was able to accommodate this new master’s cock as he began rhythmically fucking my tonsils.

“Now fondle my balls” said the man. Obediently, I reached up and cupped both his hairless balls in my hand and started stroking them, letting them roll gently in my palm. “Squeeze them gently and suck on my cock harder” said the man as his thrusting became more ardent and my saliva dripped onto my thighs, mingling with my wee juice that had again started to flow. Taking my other hand, the man guided it around his buttocks and pushed my fingers into his crack. He then took one of my fingers and urgently started probing around until the tip was touching his anus. “Now finger my butt hole you little minx” he said throatily.

Remembering the first lesson with my mistress, I removed my fingers from his crack and, scooping up some saliva and goo and nervously pushed my index finger a little into his tight hole. As I pushed, I could feel the muscle relaxing a little, allowing me to gain further entrance until my finger was buried deep inside. Continuing to massage his ball sac, I began rotating and wiggling my finger until I could feel his swollen knob throbbing uncontrollably in my throat.

Just as I was beginning to enjoy the experience, I felt him pull back slightly and then he gripped my head with both hands. Without warning he let go his load, spewing a mass of sticky love cream into my mouth.

“Yes, that’s it, take my sticky load you little slut!” he exclaimed as jet upon jet of his cum streamed into my mouth. ”Do not swallow” he commanded as, withdrawing his still throbbing member, the man picked up the Tupperware container from the coffee table and offered it to my lips. “There, now let the cum dribble into the dish” he said, as I let the porridge dribble from my mouth into the plastic pot.

“There we go, hopefully that will get you started” said the man, zipping up his flies and pinching me on the cheek. “Now I suggest you scoop up what you can from your thighs and put that in the dish as well. Here is my card, I will be expecting you tomorrow at 10am sharp and we will see how much more we can fill this dish before your appointment tomorrow night”.

The man then left as abruptly as he had arrived, leaving me horny but far from sated with the huge plug still in my arse, the weights pulling heavily down on my sac and my nipples still being pinched by the clamps.

Removing the nipple clamps with a sharp cry as the blood rushed back into my nubs, I eased myself gently off the dildo impaled in my botty and tidied myself up in the bathroom, letting the lubricant ooze out of my butt hole to sooth my stretched little ring. Examining the man’s card, I realised that he only lived about half a mile away but was unsure if I could pluck up the courage to go round there.

The next morning, feeling deeply rested but permanently horny, I pulled my sissy panties up over my bottom, put on my shorts, t-shirt and sandals and went downstairs.

Whilst eating breakfast, I spied the man’s card again on the kitchen table. Looking in the fridge, I despaired at how I was ever going to fill the container with my cream as I had been instructed and thought maybe I should enlist his help again. I admitted to myself that I had found the whole experience very erotic and could even now feel my juices rising and my little boy clit starting to firm up. And so, before I could think myself out of it, I popped the cum pot in my pocket and headed off to his house, both nervous and excited about what the day had in store for me.

Arriving at his door punctually at 10am, the man greeted me with a welcoming smile and bid me enter. Sitting me down in the lounge, he assured me that he was trying to help me but that I must put myself in his hands and he would endeavour to extract sufficient cum cream from me so as to ensure that my mistress would be very pleased. Handing him the Tupperware container that he had added to the previous day, he ordered me to remove my clothing. As I took off my t-shirt, my cherry nipples were stiff and perky and the man could not help himself as he stood in front of me, squeezing and twisting and tugging on my little bubs as I both winced and groaned at the multiple sensations of pain and pleasure coursing from my chest down to my groin.

Realising that he was preventing me from removing any further clothing, the man sat back down on the sofa in front of me and instructed me to continue undressing. As I lowered my shorts, my pink sissy panties were exposed, which drew a little gasp from the man. Beside himself, he took hold of the panties on each side and slowly drew them down over my buttocks and thighs until they were lying at my feet. He drew another sharp breath as my little cock with the steel weights around my ball sac came into view, dangling invitingly right in front of his face. The flow of my naughty wee had already started and my prick was at half mast, dribbling a little of the clear fluid in a line of about six inches, swinging to and fro as the man cupped my little balls and squeezed gently. This caused my little boy clit to bob straight up and point directly at his face.

Removing his hand from my balls, the man then took a ruler from under the sofa and started to flick the underside of my balls with it, pulling the end back with one finger and letting it spring back up to gently slap my taut sac that was weighted down by the steel ring. At first the sensation was ok but a little scary, but then the man started increasing the amount he was pulling the ruler back, causing my poor little balls to be slapped harder and harder until I was feeling real pain between my legs and begged him to stop.

“Please sir, don’t punish my poor little balls any more, sir. I can’t take anymore, it’s hurting me!” I cried as tears began flowing from the corners of my eyes. Indeed, my clitty had lost its initial hardness and the flow of goo had stopped several minutes ago.

“Excellent” said the man, “we seem to have stopped wasting any of that valuable cum. Now follow me into the next room and we will start the collection process.”

Removing my sandals and following him into the next room, I saw what looked like a steel box frame made of scaffolding pipe in the centre of the floor. At one end was a padded bench and the sides and top of the frame had leather straps and buckles attached.

“Now kneel on the bench and lean across the horizontal bar in front of you” said the man.” That’s right, now stretch your arms across to the far side and hold onto the bar”.

Following the man’s instructions, I knelt down over the bar and stretched out my arms. Before I really knew what was happening, the man had fastened my thighs to the vertical bars either side of me with the attached straps, pulling my legs wide apart as he did so. Drawing a strap across my back, he then attached this to each side also, ensuring that I could not raise myself up. Finally, he secured my wrists to the far pipe with the attached cuffs.

“There, that should hold you in the perfect position for extracting your love cream” said the man as I considered my predicament, stretched over this steel frame with my thighs drawn wide apart and my balls and young manhood dangling down at the mercy of anyone who should wish to use or abuse them.

From my prone position, I could not see what the man was doing behind me but could hear him rummaging through a cabinet until he obviously found what he was looking for and came and knelt behind me. Taking my soft little prick in his hand, he drew it back through my legs and then, to my horror, I felt something tube-like being inserted into the little eye in the knob.

“Wha-what are you doing!” I exclaimed, as I felt a thick fluid being forced down my little wee hole.

“Just relax and you will be fine” soothed the man. “I am not going to hurt you, I am here to help you”. With that, the pressure in my boy clit subsided as the syringe was removed. I could feel some sticky goo dribbling out as the man again grasped my little pecker just under the bulb and I felt another foreign object urgently pressing against the eye and, gradually, entering my pee tube! I was feeling quite a stinging sensation in my willy and cried out in pain, but it soon subsided as I felt the object, which was a smooth hollow metal tube inserted about two inches inside. Just as I thought the man had pushed it in as far as it would go, I could feel the tube getting larger and stretching my little eye further and then the stretching sensation eased as the flared bulb fully entered me and was sucked in a little more until the end was gripped tightly.

Relaxing slightly as the pressure abated, I began to become accustomed and even a little excited by this new sensation of a heavy metal object inserted in my wee hole and weighing the end of my boy cock down, causing it to point at 45 degrees to the floor. Looking down between my thighs, I could see the man attaching a plastic tube to the metal pipe that was about 12 inches long and had a little container at the end.

“Now this will ensure that all of your sissy cum will be collected and not a drop will be wasted” said the man as he then went back to the cabinet and returned with a small metal box with wires attached. The man placed the box on its end so as I could see a number of dials on it and then attached one wire to the metal tube sticking out of my poor willy and the other, with the help of a sticky pad, to the clamp weighing down my balls.
**
Moving halfway down my body, he then focussed on my little cherry nubs. Squeezing and tugging on my delicate little nipples, he gradually made them point down to attention and increase in size before attaching a clamp to each nipple linked by a silver chain, something that I was now very familiar with. Adjusting each clamp, the man increased the pressure on my little bubbies until it was difficult for me to determine whether I was actually experiencing pain or pleasure, though when he pulled down on the chain I did let out a little cry as my nubbies felt like they were going to be ripped off! He then took what looked like a large fishing weight from his pocket and attached it to the middle of the chain so as my poor nips were tugged down as the weight swayed to and fro with the slightest movement.

Moving back to the box with the wires attached, the man began adjusting the knobs until I saw a small screen illuminate and then he began to explain what was to happen to me. “This box is called an Estim device” he said, making further adjustments. “The device will pass a small current through your genitals which will stimulate the flow of your seminal fluids and ensure that you have a bountiful supply to take to your party tonight” he assured me as, gradually, I felt the strangest sensations building in my groin.

At first, I felt a tingling right at the end of my willy, then the sensation moved right the way down my tube like a kind of wave passing to and fro between my balls and my rapidly swelling purple bulb at the end. Then, as the man again adjusted the knob, it felt like my little balls had been gripped in a vice that was alternately released and re-applied, pumping them until I could feel my juices starting to flow along the length of my now fully erect clitty. The feeling was incredible as the man moved the dials to give me both gradually increasing tingling sensations and then a pulsing heat that ensured that my goo was by now flowing out of the metal pipe sticking out of my purple bulb and down the clear plastic tube until, with amazement, I could see little droplets puddling into the bottom of the container at the end. I was in heaven as the man turned the machine up another notch and got to his feet.

“Right, you seem to be nicely settled in” said the man. “I am now going to leave you for half an hour and see how much of your cum we can collect. The machine is in ramp mode so you will feel the pressure gradually mounting. Just go with it and you should find the whole experience intensely pleasurable”. With that, the man turned and left, closing the door behind him.

I was in ecstasy, bound to this scaffolding in the most lewd position with tubes connected to my clitty to collect all the fluids being forcefully pumped out of me in the strangest of fashions. Every now and then, just as I was getting used to the sensations, the machine would automatically increase the pressure, causing me to gasp as I forced myself to relax and accommodate the heightened current passing through my genitals.

After maybe 10 minutes or so, an urgency was building throughout my whole body and, incredibly, I felt myself close to coming as the machine again raised the current a notch until, unable to control myself, my balls let loose their sticky porridge and I almost fainted with the overdose of sensations as my cum flowed up my prick and through the metal pipe, running smoothly down the tube and collecting in the pot at the end.

But of course, as my horniness subsided, the machine continued to ramp up the sensations which by now were becoming quite uncomfortable to say the least. I tried crying out to the man that I had come and would like to be released, but either he did not hear me or refused to come to my assistance as the electric pulsations continued.

On the verge of panic as the heat continued to build in my, now, deflated boy clit, I tried hard to focus on something else and began thinking back to what Miss Bolton and Miss Marsh had been doing to me the days before. Amazingly, I felt the blood returning to my little prick and the horniness through my body starting up again. As my clitty grew in size, the sensations again became quite pleasurable as I watched in fascination as some of my sticky cum, which must have been stuck before, began again flowing down the tube. After another few minutes, I was at full mast and a new continuous flow of goo was dribbling into the pot. As I began to believe that I could have another orgasm without even touching my private parts, the door opened and, stretching my neck around, I could see the man returning to check up on me.

“So how have we been doing then, my young man” he said, as he examined the transparent container beneath me. “Ah I see you have had a proper come this morning, and plenty of sticky goo collected as well” he smirked. “Lets see if we can improve on what we have already managed” he said as, returning once more from the cabinet, I felt him start flicking my weighted balls with his fingers whilst squeezing out some kind of lubricant between my crack. With one hand again adjusting the knobs of the box so as the sensations moved to a more intense throbbing, pulsing feeling in my balls and the tip of my prick, I felt the man’s fingers between my buttocks as they gently stroked across my little puckered anus, finally resting against the brown hole and then urgently penetrating me as I gasped with lust.

With two fingers inside me, the man began massaging the walls of my bottom, in and out and around and around, kneeding my naughty button buried deep inside me and causing floods of my love juice to dribble down the tube.

Just as I thought I was about to lose control of myself again, the man stopped finger-fucking my bottom and stood up. As the urgency in me subsided and I was about to beg him to continue, I heard the sound of a zip being lowered behind me and then a bulbous knob pressing against my bum hole. Before I could make any protest, with a single forward thrust the man buried his massive cock head deep inside me. He then began rhythmically fucking my poor hole, in and out, in and out, almost pulling out completely before ramming his meat back up into my shoot. With the machine pulsating and alternately gripping and milking my balls, and my purple knob throbbing uncontrollably, the cock in my anus was pounding against my love button and driving me wild. What’s more the thrusting I was receiving was causing the weight and chain attached to my nipples to swing back and forth, tugging incessantly at my swollen bubs. With a loud wail, I completely lost control of myself and my cum spewed forth for what seemed like minutes. Jet upon jet of sissy cream was extracted from my balls and flowed easily into the container until it was full to the brim. With one final almighty thrust, the man grunted loudly and let rip his seed deep into my rectum.

“Take my dirty love juice you little sissy slut! Feel my cock pumping you full of my semen you cock whore!” he exclaimed as I felt his weapon throbbing uncontrollably inside me and filling me to the brim with his semen.

After a few minutes, the man withdrew his spent cock and turned off the machine.

Moving to the front of the apparatus, the man presented his sticky cock to my face. “Now clean me up like a good boy should” said the man, offering his slimy shaft up to my mouth whilst pushing down on the back of my head. Like the good little sissy that I had become, I opened my mouth wide to accommodate his angry purple head and sucked deeply, alternately circling my tongue around his swollen knob and bobbing my mouth up and down to ensure that all the sticky goo was cleaned from his phallus.

Withdrawing from my dribbling mouth, the man disconnected the now full container from the end of my flaccid prick and withdrew the tube from my pee hole. Once he had removed the restraints that had pinned me to the frame, I was ordered to crouch down whilst he filled my Tupperware pot with the mixture of love juice and cum from the container. Finally, he held the pot beneath my bottom hole.

“Right young man, now I want you to squeeze out all my lovely cream from your hot botty” he said. Pushing down, and with several embarrassing fart noises, his cum bubbled and eventually dribbled out of my bowels into the container.

Holding the pot up to my face, I was pleased to see that it was absolutely filled to the brim with sticky porridge. My mistresses will be very pleased with my performance today, I thought happily as the man replaced the lid and ordered me to get dressed, removing my nipple clamps as he did so. My sore little bubbies were quite extended after the punishment they had taken and I rubbed them vigorously to get the blood flowing back into them. Red faced, both from shame and at what I had let happen to me, I quickly dressed end excused myself before making a hasty exit with my full pot of cream.

The next morning, having gone through my normal ritual of showering and using the douche on my boy cunt as I had been instructed by my mistress, I pulled on my silk crotchless panties and admired my ball weight hanging freely between my legs. Ravenous from the previous day’s adventures, I went downstairs to get some breakfast. However, the only “milk” I could find in the fridge was my boy cream which was being kept nice and fresh in the Tupperware container. So having quickly donned my shorts, sandals and a t-shirt, I set off to the local corner shop.

As I approached the shop, I was surprised to see Mrs Patel, the ample bodied wife of the owner, standing by the door with a plaster on her forehead. Bidding her a good morning, I eased past her and went directly to the cold cabinet where I selected a milk carton and walked towards the counter. A teenage asian girl that I had not seen before was standing beside him. She was a pretty, petite girl with long jet black hair falling to her waist. She had an attractive face and smiled strangely at me as she gave me a wink, which I thought most peculiar.

“Hello” I said, introducing myself. “My name’s Michael. I haven’t seen you here before.”

“My name is Sikta” said the girl. “My parents have gone back to India for a while and Mr and Mrs Patel agreed to look after me for a bit. “

“Do you like it here” I asked, admiring her budding tits that I could just make out beneath her silk blouse.

“Oh yes, they look after me very well. They are very close friends of the family, almost like an auntie and uncle really. They have made me feel very welcome”

“Maybe we can spend some time together if you are going to be here for a while” I suggested hopefully.

“Oh, I’m not sure that will be possible” said the girl, frowning. “Mummy and Daddy left specific instructions that I was not to mix with boys. Anyway, I think you are in a lot of trouble”.

Before I could find out what she meant by this, Mr Patel had taken the milk from me and fixed me with a cold stare as he leant over the counter.

“So, if it isn’t our neighbourhood pervert teenager daring to show his face in here again!” said Mr Patel angrily as his wife sneaked up behind me and grabbed hold of my arms. Looking around with alarm, I noticed that Sikta had quickly moved from behind the counter, closed the shop door and pulled the shutter down. Dropping the latch on the door, she fixed me with a wicked grin as she leant against it with her arms folded.

“I don’t know what you mean, Sir, there must be some mistake!” I stammered, trying to wriggle out of Mrs Patel’s grasp.

“You see my wife has injured her head?” Mr Patel asked, “Well that is because she slipped on that filthy slime that you left on the floor the other day! I thought you were behaving strangely but the man that was behind you explained that he saw you masturbating in the queue! You dirty little boy! What do you think you were doing? This is a respectable establishment! “

“Oh my god, I am so sorry sir!” I blurted out. “I don’t know what came over me. Please let me make amends”

“Well, we shall see about that” said Mr Patel. “Get into the back room and we will decide exactly what is to become of you!”

At that, Mrs Patel took hold of my arm and led me into the back room, closely followed by Sikta, whilst Mr Patel made to re-open the shop.

The back room must have been their living room as it was elegantly furnished with expensive looking soft chairs, cushions and a beautifully decorated rug covering the floor. However, I had little time to take in my surroundings before Mrs Patel addressed me from one of the chairs as Sikta closed the door behind her.

“Ok young man” said Mrs Patel, “clearly you have been a very naughty boy and should be punished. I have a very nasty cut on my head where I slipped on that filthy mess you left on the floor, so it is only right and proper that I should administer the punishment.”

Seeing no way out, as the door was guarded and Mr Patel was out front, I could only agree with what Mrs Patel was proposing, so I simply stood there with my head bowed and said “Yes, Mrs Patel, I have been a very naughty boy and should be punished”.

“Good” said Mrs Patel, “I am pleased that you have at least seen the error of your ways and are willing to comply. However, to ensure that you do not have a sudden change of heart, your hands will be secured. Sikta, attach the cuffs.”

Before I knew what was happening, the girl had dutifully pulled my hands behind my back and locked them tight.

“Excellent work, sweetheart, now kindly remove Michael’s shorts and pants ready for his punishment.”

Immediately, I started remonstrating, however this just led to my receiving several hard slaps across the face from Mrs Patel.

“How dare you complain!” said Mrs Patel, “I could sue you for the injury you caused and you could go to jail, you filthy little boy! Now take your punishment and stop making such a fuss!”

Compliantly I lowered my stinging face whilst Sikta moved in front of me and, taking hold of my shorts by the waist, pulled them down to my feet. This action was met by a gasp from both of them as, not only could they now see that I was wearing my regulation girlie split crotch panties, but that the weight tugging down on my balls was hanging through the slit in full view of my captors.

“My goodness, what do we have here!” said Mrs Patel, “Well if it isn’t a little sissy boy standing before us! And it looks like he has been getting some attention too! Sikta, remove the sissy’s panties and bring her to me”

With that, the girl drew down my panties completely and removed them, together with my shorts, and threw them into the corner of the room.

“Ok, over my knee you little slut” said Mrs Patel as she drew her long dress up to her waist and I was bent over her bare copious legs. Slightly parting her knees, the Indian matriarch reached underneath and, catching hold of the ball weight, pulled it down hard whilst closing her vice-like thighs at the same time and thus trapping my balls and little cock between her ample flesh.

“Ow!” I exclaimed, as she secured my prick and balls between her legs.

“That’s to ensure that you don’t wriggle around to much” said Mrs Patel as she commenced raining hard slaps down on my quickly reddening bottom cheeks.

After several dozen smacks, my bottom was blushing up nicely, however Sikta was clearly not satisfied with the severity of the punishment.

“He isn’t making much noise, is he auntie?” said Sikta, who had been closely watching proceedings positioned, as she was, on all fours with her head under the woman’s thighs so as she could get a good view of my little prick and tight balls secured in their steel ring being squeezed between her Mrs Patel’s legs. I must admit that, with each smack of her hands, my boy clit was made to rub against her thighs and I could feel it swelling down there as my arousal mounted.

“Maybe the naughty boy should get the same treatment as I do when I’m naughty” said Sikta as she delicately flicked the end of my stiffening peewee with her finger and thumb, causing it to sway to and fro like a pendulum.

“Quite right too” said Mrs Patel, pushing me off her lap onto the floor. “Now sissy boy I want you to remain on all fours whilst I get what I need. Keep an eye on her Sikta and make sure she doesn’t move”.

With that, Mrs Patel left the room but no sooner had she closed the door than the girl sat down on the floor and looked at me with an evil look in her eyes.

“I’ve never played with a naughty boy before, especially one who looks like a girl” said Sikta. “Does that metal ring around your little balls hurt very much?” she asked, as she gave it a gentle tug.

“Ouch!” I exclaimed, “it does when you pull it so hard!” I cried.

“Well you still have sticky stuff coming out of your little wee hole” said Sikta, “so it can’t be all that bad. Let me rub it better for you”. With that, the naughty girl grabbed hold of my stiff little prick and started tugging it up and down, moving the hood over the purple knob and collecting my juices in her hand before tugging the skin right back to the base. I must say, this new treatment was much more pleasant than the spanking I had been receiving and I started moaning softly whilst rhythmically moving my hips.

“This is fun!” said Sikta, “I like having a sissy boy slave to play with”.

“Thank you for being nice to me” I gasped as the girl held my foreskin back firmly with one hand whilst massaging my juices into the knob. Round and around her little palm went on the head, polishing it until it was glistening with my pre-cum.

After a few minutes of this treatment, the girl tired of rubbing my engorged bulb and turned her attention to my little balls, alternately pinching, squeezing and slapping them until I didn’t know whether to cry or moan. Taking a ball between the thumb and forefinger of each hand, she delicately rolled my plums in the skin of my sac before applying ever increasing pressure on them as she pinched each nut until I had to beg her to stop.

“Ow! Please don’t do that anymore!” I begged, as the punishment she was inflicting on my bruised and swollen plums became unbearable.

“Well ok then” said Sikta, “but you really are a sissy spoilsport. Your little lollipop has got all shrivelled up now. Why won’t it play? I want it to cry some more”. With that, the girl took hold of the purple end again and, with a finger and thumb either side of the eye, opened up my wee hole so as she could see if there was any more juice to come out.

“I can’t see any in there” said Sikta. “How do you make it? Make me some more now!”

“I don’t know how I make it” I said, “but it is usually when it is hard and I am excited”.

“How about if I show you mine” said Sikta, “Would that make it go hard again?”

“We could try” I said, trying not to sound too excited.

With that, Sikta stood up beside me and, lifting her dress, pulled down her white cotton panties, throwing them into the corner of the room. Resuming her position in front of me, she then raised her skirt, thrusting her hips towards me until her private parts were right next to my face. I gasped longingly at the sight of her moist little crack, the inner pink lips glistening with her own juices.

“Why is your little cunny all bald?” I asked, unable to take my eyes off this beautiful girl’s treasures.

“Oh that’s because I have always been told to shave the hair off so as to keep it nice and clean. They check every Sunday afternoon to make sure I have done a good job. Sometimes they even help me to make sure I get in all the little creases.”

“Where does your wee come out?” I asked, intrigued.

“Oh that’s easy” said Sikta. “I have a little wee hole just like you but mine is just inside. Look, can you see?” she asked me as she parted the folds of her juicy lips, exposing the pinkness of her body to me and, with one small finger, pointed out the little hole hiding just inside.

“Oh yes, I see. Thank you, little Mistress, you really are being nice to me” I said, my eyes riveted to her hot little hole.

“That’s ok, and it certainly seems to have done the trick!” Sikta exclaimed, pointing between my legs at my stiffening boyhood. Kneeling down, she took hold of my swollen little cock again, gripping it just under the mushroom head. Again she opened up my wee hole as far as it would go, causing some more transparent juice to drip out and run over her fingers. Taking her little finger, Sikta scooped up some of it and, whilst holding my wee hole open, put the tip at the entrance to my little eye and pushed gently, trying to get her finger inside. She alternately poked and twisted her little finger at the entrance to the smallest of my holes until I could just feel the tip inside, her nail grazing me slightly but not unpleasantly. I was just thinking if the punishment I had endured yesterday had opened it up when I became aware that “aunty” had returned to the room and was standing above us with her hands on her hips and a stern expression on her face.

“And what do you think is going on here?” demanded Mrs Patel as Sikta quickly stopped what she was doing and regarded her with a sheepish look.

“I’m sorry Aunty but I couldn’t resist playing with the slave” said Sikta. “Please don’t punish me!”

“That’s ok, my little angel” said Mrs Patel. “I suppose it is about time you had some contact with boys your own age. You can continue your explorations in a minute but let’s sort out the little slut’s punishment first. Move around the back and hold her botty cheeks open whilst I administer the treatment”

Kneeling behind me, Sikta obediently placed her fingers both sides of my boy cunt and prised open my cheeks, causing my little bum hole to wink nervously.

“Now then slut” said Mrs Patel, “You are about to receive what is called a figging and it is for naughty little girls like you who do dirty little things”.

With that, Mrs Patel positioned the peeled ginger at my pouting opening and slowly inserted it until I felt my boy cunt muscles suck it in greedily.

At first, I did not notice anything other than the feeling of something being forced inside me. However, after some moments, I became aware of a heat gradually spreading deep in my bowels. A few moments later and the sensation was far from pleasant as the burning increased and I started whining to Mrs Patel that my bottom was on fire.

“Can I move it about like Uncle does? Please Aunty?” begged Sikta excitedly, ignoring my remonstrations.

“Yes of course, dear” said Mrs Patel, smiling sweetly at the girl. “But don’t be too gentle because sissy boys are stronger than girls”.

With that, Mrs Patel sat back down on the chair and dragged me across her lap. Through the ever increasing heat rising in my botty hole, I suddenly felt small hands prising my cheeks apart again, closely followed by first one, then two thin fingers being inserted into my burning bum! Having managed to easily get her two fingers in, Sikta slid in a third and then, grabbing hold of the end of the ginger plug, began wriggling it about inside me. The rotation of her fingers caused the ginger to continually rub against my naughty little button which, to my horror, began to send pleasant sensations to my prick which was starting to swell at an alarming rate, pushing itself through Mrs Patel’s thighs until the little purple head was poking out underneath.

“Well I do think our little sissy boy is beginning to enjoy this” said Mrs Patel. “Try inserting more fingers and do be harder, this is meant to be a punishment!”

With that, Sikta got onto her knees between my parted butt cheeks and, whilst Aunty held my cheeks wide apart, she inserted her last finger and then her thumb as well! By this time, my poor little bottom was being stretched to its limit and I started complaining ever louder as I wriggled on Mrs Patel’s lap. However with a sharp smack from a hairbrush on my already reddened cheeks, I quickly remained still again.

“Stop moving about so much” said Mrs Patel “or you will get far worse. Now Sikta, let’s see how much you can get in there”.

“Oh aunty, I think I can get it all in!” Sikta cried excitedly as, with a final thrust, my rectum was forced wide open to accommodate the little girl’s entire hand as it slipped right up my back passage. Once her fist had forced its way completely inside my poor abused hole, the sphincter muscle clenched down hard around her wrist and some of the pressure was released.

“It’s all in, Aunty!” Sikta exclaimed. “I have my whole hand up the naughty girl’s bottom!”

“Good girl, Sikta” replied Mrs Patel. “Now move it about a bit and let’s see how much this sissy boy can take”.

With that, she began moving her arm backwards and forwards, twisting her hand around as my boy cunt was well and truly fisted by this excited girl. After a short while, Mrs Patel resumed spanking my cherry red cheeks with the hairbrush until I was alternately moaning and crying with the thrashing and fisting I was receiving.

However, as the friction on my love button increased and the heat of the ginger abated, I could feel the pressure building up in my little balls as more and more goo dribbled out of my cock until it was running between Mrs Patel’s thighs and onto the floor.

“Oh look Aunty, the naughty girl is sliming all over the floor!” exclaimed Sikta. “Can I touch it again, please please?”

“Yes of course dear” said Mrs Patel, but don’t stop moving your hand around in her cunt; we don’t want her to enjoy it too much”

Needing no more encouragement, Sikta grabbed hold of my engorged prick and started milking it like I was a cow, fisting my poor botty hole with increased vigour as she extracted more and more of my love juice until it was puddling beneath me.

The urgency continued to build in my plum sac, despite the severe stretching of my sphincter. I felt my sap rising as the little girl’s hand continuously rubbed against my button. I began moaning and thrusting my hips in time with the pumping action that Sikta was applying to my prick until, just as I was approaching the point of no return, Mrs Patel ordered her to stop. .

“That’s enough now darling” she said. “I think the slut is enjoying her punishment far too much. Now stop your play and take your hand out the sissy’s cunt”.

With a loud plop, Sikta withdrew her hand from my burning bum and, with a sigh, left my twitching prick alone. Pushing me onto the floor, Mrs Patel took hold of it and applied several hard slaps to my swollen purple knob until I was almost crying and my boyhood was shrinking away from the pain.

“That should stop the little slut making any more mess” said Mrs Patel, aiming a final hard slap right across my little ball sac. “Now we need to decide what to do with the sissy next”

“Oh please Aunty, can I play with her peewee and balls again? You did promise Aunty please!” said Sikta, hopping from one foot to the other.

“Well ok then” said Mrs Patel. “I see no reason why we should not continue your education whilst we have the slut at our disposal. Come here slave and sit on my lap, legs nicely spread apart so as Sikta can get a good look at you”.

Thankful that the slapping had stopped. I obediently took my position on Mrs Patel’s lap, my back to her and my legs dangling over hers so as to completely open my private parts to the girl’s examination.

“Now kneel between her legs and take a good look at her private parts” said Mrs Patel as she stretched her arms around me, took hold of a nipple in each hand and squeezed firmly. This had the immediate result of causing my little prick to twitch up, as the girl squealed excitedly.

“Oh look Aunty, her little peewee is growing again!” she exclaimed.

“Grip it firmly and pump it slowly up and down. That’s it, now cup those little nuts and give them a squeeze. That should make her little prick nice and hard for us” instructed Mrs Patel, as Sikta gripped my rising member. Moving her little fist up and down, she greased the swelling bulb with my juices as she softly squeezed and rolled my little plums in the palm of her other hand.

“It’s getting nice and big now, though it’s not as big as Uncle’s” said Sikta. “Can I give it a little licky? Please Aunty?”

“Of course dear” said Mrs Patel, “you can suck it a little bit if you like as well”.

My heart missed a beat as I heard her say this, particularly when she increased the pressure on my nipples at the same time. No one had ever licked my clitty before!

Shifting forward slightly on her knees, my little mistress took a firm grip of my balls, and pulled down hard at the base of my prick, exposing the engorged purple knob. Reaching her head forward, I watched frozen as her little pink tongue poked out of her mouth and flicked delicately at my glistening head. I could not help but groan as her hot wet tongue gently grazed up and down the underside of my prick, collecting sticky pre-cum with each upward movement before running it back around the knob. Indeed I was in heaven as, shuffling forward a little more, I watched in awe as her head moved down over it, her mouth opened and, before I knew what was happening, she had engulfed my knob inside her mouth. The heat from her tongue and cheeks was incredible as she continued to lap around the head of my shaft, alternately sucking firmly and then bobbing up and down.

“Yummy this tastes good!” said Sikta. “It’s getting all salty and wet.”

After a few delirious minutes of heaven, she grazed her tongue right down my shaft and gripped my weighted-down balls even harder as she flicked her tongue over my little plums. Just as I thought I could take no more of this wonderful torture, Sikta sat back on her knees and exclaimed:

“Oh Aunty, I can see your panties are getting all wet! There’s a little damp patch on them!”

“Yes darling” said Mrs Patel, “I confess to finding this rather exciting and may need you to give me a one of your lovely relaxing massages. Can you reach underneath the sissy and help me?”

“Of course Aunty” said Sikta enthusiastically. “It’s my duty as a good house guest. That’s what you tell me, isn’t it?”

“That’s right sweetheart” said Mrs Patel. “Now pull aside my wet panties and make Aunty feel better.”

Needing no further encouragement, Sikta slid her hand beneath my buttocks until she must have hit the target as I could hear Mrs Patel groaning behind me.

“Oh yes, that’s good darling. Keep rubbing on that little button just like I showed you” panted Mrs Patel as I felt her grinding her hips forward to meet the girl’s probing fingers. “Yes, yes, squeeze that naughty little nub. Now see how many fingers you can get inside. Oh yes, that’s it, push them all inside me just like that. Don’t stop, don’t stop, oh yes baby yes!”

Whilst satisfying Aunty’s needs, Sikta eased back a bit and then, to my pleasant surprise, continued bobbing her head up and down on my little prick. Before long, my moans were mixing with Mrs Patel’s groaning such that we were completely oblivious to Mr Patel walking into the room.

“What’s going on!” I heard a male voice say as Mr Patel was confronted with the sight of this luscious girl fist fucking his wife whilst sucking up and down on my greasy knob.

Two loud plops ensued as Sikta simultaneously removed her fist from the woman’s cunny and her mouth from my prick.

“Oh hello Mr Patel” said Sikta “I was just improving my education of boy’s private parts. Aunty said it would be ok. But she got a bit excited so I had to give her one of those special massages she taught me”

“That’s ok” said Mr Patel, “but I do believe you will need some further education from us this evening. However, now it is my turn to have some fun”.

At that, Mr Patel stood above her, loosened his belt and dropped his trousers and pants around his ankles.

“Now be a good girl and give me one of your special lollipop massages” said Mr Patel, as he took hold of the girl’s head and steered her mouth towards his hardening cock. Sikta obediently opened her little mouth, thus allowing his thick manhood to work it’s way down her throat. Backwards and forwards Mr Patel guided Sikta’s head, thrusting in and out whilst the girl made little gurgling and gagging noises as sweet little tears rolled down her cheeks.

“There’s a sweet child” he said, whilst pulling his throbbing member almost completely out of her mouth before ramming it all the way back in. “Suck nice and firmly and don’t forget to massage my nuts like I’ve taught you” as Sikta obediently fondled his hairy ball sac. I watched this wonderful show for several minutes before Mr Patel pulled his huge tool out of the girl’s throat and then started slapping his swollen knob on her forehead.

“Now suck those fat plums, sugar” he commanded as the dutiful girl took first one, then the other hairy ball into her mouth and sucked for all she was worth whilst Mr Patel’s cock dribbled pre-cum onto her nose and cheeks.

“Now wife” said Mr Patel. “Make yourself useful and prepare that sissy slut for me”.

“Yes husband” said Mrs Patel, as she shoved me from her lap onto the floor. “Now get on all fours like a good slut should” instructed Mrs Patel as I hastily complied, allowing myself to be positioned with my arse pointing up towards the ceiling.

“Hold the sissy’s cunt cheeks open for me!” ordered her husband as, stepping over Sikta, Mr Patel took hold of his huge cock and knelt between my outstretched thighs.

Grabbing hold of my hips, I felt him position his throbbing brown member at the entrance to my boy cunt and then gently ease the swollen mushroom past my sphincter as I gasped from the size of it. Slowly at first, but with ever increasing ardour, Mr Patel forced his oily pole deeper and deeper into my hungry pink hole until I could feel his heavy semen-filled bollocks slapping against my bum cheeks. Just as I thought I could not take any more, I felt his huge weapon expand to stretch my bum hole to its limits. With a loud grunt, Mr Patel gripped my hips firmly, pulling me forward until his cock was buried deep in my bowels.

“Argh!” I cried, as the shopkeeper let forth his seed, emptying his aching balls and filling me utterly as, with an almighty cry, he deposited his spunk deep inside.

“Take that you dirty sissy whore!” he screamed as I felt his semen drenching the walls of my bum. Load after load of his sticky hot cream hosed into me as I was held tightly against him, his fat cock twitching and throbbing all the while.

Several minutes passed before I finally felt his shaft deflating and he withdrew his dripping member, closely followed by copious amounts of his semen oozing down my crack and over my balls. With a final slap across my arse cheeks, I was unceremoniously shoved forward and fell spread-eagled on the floor.

“Now get out of my house and don’t come back here!” Mr Patel yelled at me as I hurriedly dressed and ran out the shop, dripping semen from my poor inflamed cunt down my legs but not daring to look back until I was back safely behind my front door. It was only lunchtime and I still had my Mistresses’ party to attend this evening. It was going to be a long day..

#Making #Sissy #Boy #Slut

The Making of a Sissy Boy Slut

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