Peg Task - Anon Domme

I was alone sitting in the courtyard, waiting for something to happen or for a familiar face to arrive. Then out of the shadows of the tree a familiar voice “Hello Miss, long time no see” A big smile across his face and a cheeky glint in his eye. This boy I knew well, he and I were frequent play mates a while back.

I beckoned him to join me at my feet and asked him if he was free to indulge me, he nodded and said he was without a Mistress currently and he would be honoured to indulge any of my desires”

It pleased me that this was the case, while I did not want for a boy of my own at the moment I did want to play. “Ok boy you will need 5 clothespins, a timer”… “oh and a gag to hide the screams” I laughed.

“Yes I have pegs right here with me Miss”

I smiled, “Ok Boy then let us begin” knowing this boy well, I knew that he was able to apply the first peg upon the tip, it was held in place attached to his foreskin, which at this point was loose as he was not fully erect.

“It is secure Miss, should I start the timer?”
“Yes boy of course – 20 minutes on the timer, place all four pegs upon your scrotum, just the skin we don’t want permanent damage now do we”

He winced as he applied the pegs neatly and nodded in agreement.
I instructed him to take a hold of himself and to stroke slowly for exactly one minute. I then continued to talk of his reward if he made it through the task. He groaned occasionally a delightful sound for me, one that I had missed greatly.

“One minute Miss” he blurted out.
“Ok Boy stop stroking and flick each of the pegs in turn starting with the tip” I could hear him flicking the pegs but he made no sound, “BOY! You are not doing it hard enough I said sternly do it again, if you are not in pain then you are not doing it correctly”
“yes Miss, thank you Miss”
Once he was complete I instructed him to begin stroking again, I could hear in his moans that it was getting to him, the tight peg on his tip and the clamped pegs in his sack, oh how I had missed the grimacing sounds that now escaped the boys lips.

“One minute Miss” he yelped
“Already!” I sighed, “ok flick the pegs this time twice each peg.”
He looked so angelic on his knees, and his face getting more crimson as the time passed, we continued this alternating of stroking and flicking for 10 minutes, then as the next rotation was about to begin the boy made a mistake, he forgot to address me as Miss. Well this of course can not be tolerated.
“on your feet boy, and turn around and present your buttocks to me,” he stood gingerly and bent over slightly exposing his fleshy behind, I stood and reminded him again that at all times I was to be addressed as Miss, and he was not to forget this, I swung my arm back and firmly and with a loud crack brought it forward and made contact with his arse, once, twice, three times a charm, then to the other cheek, Once, twice, three times a charm, “and what do you say now boy?”
“Thank you Miss, this boy does not deserve your mercy”

I cackled and told him to get on his knees, he continued with stoking and flicking for a further 10 minutes, I could tell by his voice and the breaths he was very close to the edge, I was surprised that the peg placed upon his tip had not been forced off by his erectness, I ordered him to remove it, the sounds I heard were a delight, as the blood rushed back to his skin, he was rock solid and the peg was slick with precum on the edges, I told him to clean the peg before discarding it, he took it into his mouth and sucked it clean, “Good Boy” I smiled back.
“You will slowly remove the pegs from your sack, and keep stroking, when the last peg is removed you will have less than a minute to cum, if you do not cum then you will be denied. Do you understand?”
Panting heavily obviously excited at the prospect of cuming he nodded and said Yes Miss, Yes I understand”
I sat back and watched him, pumping his stiffness as he pulled the pegs off one by one, the moans getting louder, his face turning all shades of red as the last peg was removed, he looked up at me, his grip tightening even more, I smiled, and within the minute he had been gained released, he was a sweaty heap on the floor, his head hanging low he whispered “thank you Miss”
I stood up and with a click of my heels I was gone. I assume he was in a better state by the time the next person who arrived in the courtyard. Good boys are hard to find, even harder to keep.