The degradation and training of Michael, a naive sissy boy, continues. The strange man from the previous episode surprises Michael at home and introduces him to the delights of man pleasuring.
It is recommended that you read the previous episodes as this story is halfway through Michael's training. I hope you enjoy, but if older men dominating teen males does not do it for you, then you may prefer the previous femdom episodes. All constructive feedback gratefully received. x.
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.