The Making of a Sissy Boy Slut Part 5
- 1 year ago
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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. -->
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