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**Roseyreaping12** · February 7th, 2024, 02:50 PM

Chase lifted his hips a bit to better help lower his pants. He didnt love this but Chase always crummbled and behaved around any type of authority figure. He lay over his knees and just thought as he clung to his lower part of his leg for comfort.

**Sinclair** · February 7th, 2024, 02:54 PM

Theodore was proud at the boys cooperation as he got his pants down to the floor, giving the boys back a soft rub when he felt Chase clutch his leg, knowing this wasn’t easy for him either. “Just try and stay calm, Chase.” He spoke softly as he wanted him to feel he was at least okay, before the man’s hand would raise, and come slapping down firmly across the center of the young man’s backside to get things started

**Roseyreaping12** · February 7th, 2024, 03:04 PM

Chase nodded and said "yes sir" he was trying to stay calm but alot of emotions welled up in the younger man as he yelped and jumped for a second for just a hand and over his issued underwear the man had quiet a sting.

**Sinclair** · February 11th, 2024, 04:11 PM

Theodore nodded in approval of how his smack affected Chase before he got right back to it and continued to smack away firmly across the poor man’s backside, keeping him held securely over his knee as he punished him for everything that’s happened thus far. The man had a solid palm, something Chase was learning now

**Roseyreaping12** · February 11th, 2024, 04:23 PM

He was fighting tears but gave up after the 10th smack or so as he emotionally just collapsed and started to cry, the spanking hurt but wasnt cry worthy yet. He didnt beg or get upset, just cried.

**Sinclair** · February 11th, 2024, 04:26 PM

Theodore noticed and sighed a bit as his hand continued to land, steadily and slowly as he did. He was glad that the young man seemed to be learning the needed lessons, but it didn’t always make things easy for the Warden. He remained firm though and made sure to thoroughly punish the inmate

**Roseyreaping12** · February 11th, 2024, 04:32 PM

"Ah im sorry, im sorry" Chase cried as he just kept apologizing as he looked at the ground tears falling from his greenish eyes. His bottom was already quite and that was with the portection of underwear. He was definitely feeling terrible for his earlier behavior.

**Sinclair** · February 11th, 2024, 04:35 PM

“I’m glad to see you’re apologetic for what had happened, now I’m going to ensure we don’t see a repeat of that again. I hope you behave yourself so that’s the case.” He softly scolded the boy, starting to lower the underwear seeing as he was getting to the breaking point sooner than most

**Roseyreaping12** · February 11th, 2024, 04:38 PM

He whimphered as he was bared, his hand had hurt over his underwear he didnt want to feel on his bare ass. He didnt fuss though just the soft whimpher "yes sir" came his timid reply, he was very respondant to authority figures. His father had kept him in check but once he passed he had noone a uncle who wasnt much in his life and he got in trouble.

**Sinclair** · February 11th, 2024, 04:44 PM

The man respected the young ones behavior when directed by authorities and had a strong feeling he’d be fine with a bit of guidance. With little time to spare, the spanking continued once more, this time across the bared backside of the young man up over the wardens lap