How it all began

Sir’s training progresses with one last orgasm for the sissy

  • Score 8.8 (3 votes)
  • 168 Readers
  • 1005 Words
  • 4 Min Read

The next couple of weeks come and go with me visiting Sir for at least a couple hours each day. The format is the same; whole body inspection, housework, some corrections for poor cleaning or other infringement before being allowed to wank Sir off. Im then sent on my way with his creamy goodness in my belly as a reward. I desperately want more but daren’t ask or hint at more for fear of correction.

One day I arrive once again at 9am on the dot, strip and stand for inspection. This time Sir grabs my bum, squeezing and groping both cheeks whilst telling me “I want this grown. You’ll follow this workout plan daily to grow it and I expect results”. He demonstrates the workout plan I’m to follow daily before issuing me my daily chores.

After hours of work I am sat next to Sir with numerous shoes, boots and other leather wear that I’ve been tasked to polish to a high gloss shine. “So boy how much do you wank when you’re not with me?”. I’m a bit taken back by the question but answer honestly stating about 3 times a day. “What do you think about?”. This is easy I answer. I dream about serving him! “Mmm good answer but you wank too much”. Sir sits back and continues to read his paper, “yes far too much” you repeat. At the end of our time again I am allowed to wank Sir and take more of his cum in my mouth.

I arrive eagerly again the next day. Strip and inspection as normal. This time once inspection is finished Sir walks off and comes back with a suit bag. “You’ve been such a good boy I think it’s time for more of a reward for you. Remember the first day we met and you described the girl you fancied at school and how you liked what she wore. Well I went and bought your old schools uniform for you. Of course I told them it was for my granddaughter but how will they know! I Also bought some of the diamond style tights, hot pink socks and pink thong that you detailed for me so that you can copy your idol exactly! Do you like it?”. I thank you profusely but you stop me with just a hand held high.

“Girls don’t have little dicklets like you though. If you dress up in this you have to wear chastity for a month. Sounds fair? Stop you wanking quite so much too!”. There’s so many questions in my head but the first one is what is chastity. To this Sir shows me this little steel cage which will cover my cock. It looks so small but I know it’s the right size for me. He tells me that my little dicklet is to be put in the cage and padlocked away. He’ll keep the key and allow me out only for cleaning.

I clearly look unsure. “I’m being very fair here. There’s a price for everything and this is the price of my generosity”.  I nod and state in a defeated manner “yes Sir”.

“Good boy. I’m feeling in such a generous mood that I’ll let you have one last orgasm before locking you away. But wait until I’m ready”. Sir walks out the room and comes back with a camcorder. “Kneel boy and look into the camera as you wank. As you wank I want you to tell me in great detail what you think of doing with me”. I’m just staring at the camera, clearly nervous. “ this is just for us to watch back later, maybe I’ll show some friends though. Now boy, start wanking”.

I take my cock in my hand and start stroking. I’m already hard and a little bit wet. Sir takes a small bottle of lube and drips a generous amount in my hand and on my cock. I soon forget about the camera as I begin to talk in detail about how I dream about licking up and down your cock before taking it in my mouth. I close my eyes, “open them boy, look into the camera and tell them what’s next”. I’m so close to cumming. “Don’t you dare cum boy, not yet”. I start to slow down and stop to prevent myself from cumming “don’t slow down or I won’t let you cum”. I speed back up as I start telling the camera how I dream of bending over in doggystyle as Sir’s cock head probes my hole.

“Please Sir, I can’t stop myself cumming”. You tut and hold you hand in front of my cock. “Truly pathetic, you definitely need locking away”. With that I burst, shooting streams of cum into Sir’s hand. He holds his hand to my face, “clean it”. I lick all my cum off your hand before you rub your hand over my hair, “good boy”.

Sir takes a wet wipe and cleans me. I’m still hard and won’t go down. “I know what will work”. Sir leaves and comes back with a mixing  bowl filled with ice cubes and water. “Get over the water and dunk your dicklet until it’s soft. Don’t you dare come back up until it’s totally soft”. I do as I’m told, flinching as it touches the freezing water. I have to hold it under for 5 agonising minutes until I’m sure it’s totally soft. Sir dries me off, puts the ring behind my balls and slides the steel cage into place enclosing my cock. Sir passes me an open padlock, “you May do the honours”. I lock the padlock in place, “thank you Sir”,

“Good girl, you can go and write release date on the calendar a month from now”. I do as I told walking awkwardly as this piece of steel swings between my legs for the first time. “You can wear your outfit once you’re done with your chores. You don’t want to ruin them now so you?!”.

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