A New Type of Pain ((Private for me and LivingbyLies))
 

Alex was one of those typical problem children that you hear about in quick-fix ads between children and parenting. Except he wasn't a quick fix. During his high school years he had spent numerous days in jail, prison, and even went to a military school for a while. Nothing worked. His parents on the verge of a mental collapse enrolled him at the last minute (1 day before he turned 18) into a private school. They shipped him off without saying a word to him about the school, all he knew was that once again they were TRYING to reform him. Good luck with that!

So as the bus stopped at the school and Alex got out he did a double-take. This place was huge! It was a castle so big it almost would have made Hogwarts small! Alex smiled and looked about as he got oriented.

The first thing that came out of his mouth as he grabbed his bag and walked up to the gate was "Bring it on bitches!"

((Hope that's an okay start, and hope you are okay with the mid-evil atmosphere I thought it might set a goth sort of tone for the setting.))

(Dungeons galore! I like.)
"That is not acceptable speech, young man," Mrs. Ruth Lesseck said, stepping out from behind the gate. She appeared to be fairly young, late twenties perhaps, and wore a very professional teachers uniform, almost vintage in the style. "You will come with me to your room now. I've been told that you are a... special case, and so of course you will be dealt with as such."
She led him through the gate, and onto 'foreign soil.' Due to a geographical loophole, across that line he was no longer in the United States, and was instead on the property of... The Lesseck Family Estate. "I will give you one warning. Behave yourself, or suffer the consequences, " she added, before turning to walk him to his room.

"I'm not young I'm almost 18 bitch!" Exclaimed Alex as he gave lip to Mrs. Lesseck.

"Or what bitch? You going to spank me? You going to make me cry for my mommy?" He said mockingly as she led him to his 'room'.

"You know if you abuse me in any way since I'm an American citizen I can have you prosecuted for First Amendment Rights." That's what Alex thought anyway. He had used that excuse many times before and it usually worked.

"YOU are the least of my worries woman." He totally disregarded Mrs. Lesseck.

"Well then," Ruth Lessieck said, leading him into his room. "You've used your one warning, little boy. Now, what was that you said? Spank you until you cry for mommy?"
Like a lightning bolt, her hand was suddenly on his wrist, twisted behind his back and forcing him forward. He didn't even have time to call out before he was bent over a desk, one arm pinning him in place with apparent ease.
"Lesson one, little boy. The first amendment protects religious freedom and the freedom of expression," she said, before bringing her hand down like a sledgehammer on his butt. "Lesson two: We're not in America anymore."

"I didn't think you would take me so seriously!" Laughed Alex as he literally prepared for a spanking.

He wasn't worried about a spanking really. He had had plenty of experiences with those (especially at military school actually) and knew how to handle it.

He squeezed his glutes together really hard when her hand hit and he grinned slightly while wincing. "Ow, your hand is a little rough could you put on some lotion or something please?" He said with a snarky attitude.

Yeah the spanking hurt a little but he had had much, much worse and he was one stubborn little boy.

Ruth sighed, stopping the Spanking momentarily and taking a minute to raise the stubborn boy's arms to the corners of the desk, where two wrist cuffs were waiting to keep his hands pinned there. Making sure he was secure, from a pocket she pulled a small tube of white cream and a pair of rubber gloves. Snapping on the gloves, she squirted a bit of the cream in one hand, pulled down his pants, and began rubbing it on the exposed skin.
"We'll let that set in," she said, his skin already beginning to tingle in irritation.

Ruth knew her stuff for sure. That cream stung like nothing else!

"Unh! Okay at first I thought you were an asshole, now I KNOW you are an asshole." He said as he pinched his finger with his fingernail to distract him from some of the pain. It was slightly irritating and annoying.

"Can't we all just get along?" He asked biting into his lip too, to help with the bothersome feeling.

Ms. Lesseck smirked, but didn't respond as she was preparing another tool for his humiliation as the cream worked its magic. "Every word out of your mouth just gets you further in trouble, little boy," she warned, as she got something together out of his line of vision. A moment later, he could feel something being inserted deep into his ass, a small capsule.
"Now, how are you feeling?" She taunted, massaging the stinging cream into his skin. "Is da wotion making your botty feel better?"

Alex was in pain but he wasn't going to let his captor get the benefit of seeing that.

"Oh yah massage my left cheek more will you? The little circles fit you well I think."

When he felt that thing being inserted into his ass he bit his tongue so he wouldn't cry out from alarm.

"Oh further woman! Further! I bet you like going in deep don't you?!"

((Hope you don't mind my active resistance. I think it makes the roleplay quite fun!))

(Indeed. You being an ass just makes me more motivated to get you into deeper trouble. Please, continue!)
Lesseck sighed. "If you insist," she said, sliding in two more of the glycerin suppositories. The poor boy wouldn't last half an hour before he couldn't hold it any longer, and that's if he was lucky.
"Now, where were you? Oh yes. Spank you until you cry for mommy." Pulling back her hand, she brought it down even harder than before on the burning, sensitive skin.