Evan's Rules: The Missing Piece

It wasn't under the table. It wasn't under the couch.

Evan searched frantically through the junk drawer, unsure if the missing piece he was so desperately seeking had somehow magically materialized in the last stop of all odds and ends, but he had no luck there.

He honestly didn't need this missing piece in order for the device to work. The ones he already had waiting on the table were perfectly good, all correct and able to adequately restrict him in all the ways she wanted. It was honestly excessive, the sheer amount of parts this chastity device came with.

As he shuffled towards the living room to look through the couch again, he caught a glimpse of the time out of the corner of his eye. She would be here any minute! He began to panic strip, almost falling in the hallway of his apartment as he stepped out of his pants. Rule 6, "you will be naked and waiting for me at the door when I arrive."

The young man could only cross his fingers as he heard the familiar click of her heeled boots walking up the 2 flights of stairs to his apartment. Hurriedly shoving his recently disrobed clothes into the hall closet, he assumed his submissive pose (arms behind his back, head down) at the door in the nick of time.

She opened the door with her key (Rule 17, a later addition: "your home is mine to enter as I please") and strode in with her typical confidence. The cold outside air brought a shiver over Evan's naked form, and as usual, she left the door open exposing him to the hallway just a tad longer than she needed to.

"Good evening, Mistress Becca, thank you for gracing me with a visit tonight." Evan intoned, another ritual checked off the list. He took her coat as she sighed in relief, enjoying the warmth of prewar steam heat.

"Good evening to you, Evan. Cold out there today." That was the extent of the small talk she felt obligated to engage in. "Did the toy I ordered arrive?"

"It did, Mistress, I.. have it out in the living room like you said." he responded, barely able to keep the trepidation from overtaking his voice. He swallowed hard and convinced himself he'd pulled it off.

He had not, though. She had been with him long enough to pick up on that sort of thing, and raised an eyebrow wondering what sort of mistake he'd managed to make this time. She hung her own scarf, and in her head the plan from tonight was already shifting and changing. But theirs was a dynamic built on structure and routine, so first things first.

They walked into the living room, a naked Evan following behind. There was a tall backed and armless chair in the center of the room, and a coffee table over which the myriad parts to a chastity device were displayed. One singular cone for his cock, but many sizes of ring, spacer, locking device, and so forth. A surprisingly complicated process for such a simple goal. Why, there were so many- ah. She noticed what had her errant submissive so squirrely, and justifiably so. But she kept that knowledge to herself, sitting in the chair so they could follow through to the next item on their usual agenda.

A rueful Evan stood attentively in front of her, presenting freshly groomed nether regions to the woman who owned them. (Rule 7, "You will maintain my property clean shaven at all times.") She took the rapidly hardening cock in her hands, pulling it up and to each side, searching for any sign of a lazy shave job. There were none.

"Very good, Evan. I see last week's punishment made you a much more conspicuous groomer this time." The member throbbed in her hand as she brought up last week, and he agreed shamefully.

"Yes Mistress, thank you Mistress." She motioned for him to turn around. He did so slowly, still somehow ashamed to have her inspect her property like this. He put his hands on his knees in front of her, and she pulled apart the cheeks of his rear end to make sure his asshole was equally hairless and clean.

"Ok, all right back here too. Boys are so messy, it's better when someone like me makes sure they take care of things, isn't it?"

"Yes Mistress, thank you for your discipline." he replied, practically automatic. She patted his rear twice.

"Rule 4 time. Over my knee." Evan scowled at her declaration. Rule 4, his least favorite: "You will submit to a weekly maintenance spanking to further improve your behavior." He eased his way down to her favored position, prostrating himself over her slender lap. She hiked up her dress as habit maneuvered his cock between her legs, a small measure of satisfaction always passing over her as he settled in like this for her. He dangled there, gazing at the back of her firm legs in intimidating heeled boots, as he awaited what was to come.

"Oh, don't huff so much Evan. Youve been good with your weekly anal practice videos, so this will just be a very standard spanking. No slipper or ruler needed." He gritted his teeth remembering past failures that had warranted such things. Rule 9, "you will send me a video once a week of you playing with a dildo in your ass for my benefit."

She rubbed her right hand across his bare cheeks for a moment, familiarizing him with the feel. Reminding him what flesh on flesh felt like. Evan watched with dread as she reached for the classic hourglass on the table to their left, right in front of his face. It was a 5 minute timer. She flipped it... and then she struck, the sharp crack of her firm hand against his quivering rear end. He always jumped on the first blow, but this spanking had quite a lot left to go, so he would have to calm his bucking and endure.

Again and again she landed strikes on his rapidly reddening ass, a rhythm that made her feel so alive and in control. The regularity, the ritual, the way he danced under her hand as she continued. All of these made the heat between her legs build, though not nearly as fast as she was igniting on his bottom. The sand in the hourglass fell slowly as she continued the maintenance apace.

Small spots remained visible through the crimson coloration, remnants of bruises from his punishment the week before. Becca didn't hesitate to overwrite them, each time making him breathe in harder. Her mind drifted slightly without letting up on the spanking in the slightest. She knew what he'd done wrong, and it was her role to correct him. How would she best do that? On her lap, the boy squirmed more and more. The sand ran out. She had her idea.

"Alright then, that's all done sweetie. You can stand up." she said in a soothing voice, and stand up he did. An awkward but clear erection was present, in addition to a shining spot on her bare thighs where his cock had been positioned.

"That was an exciting one, was it?" She asked, running her finger along the part of her leg his precum had lingered on. She gathered what she could up.

"Yes, Mistress." he answered honestly, following that left hand and guessing where it would go.

Becca stood up, and put the cum-laden finger in front of his face expectantly. This was Rule 15 after all: "You will clean up your precum with your mouth." Her boy did as he was supposed to and put it in his mouth, sucking at it greedily. The leaky offender responded in kind, bobbing in front her with excitement.

"Why don't you sit down in that chair, Evan. You've done so well, and I have some things I want to discuss with you." she said, maneuvering him down without removing her finger from his mouth. He winced as his sore behind made contact with the hard chair, but she did not let him stop sucking her finger enough to complain.

In fact, to his sincere surprise, she got down on her knees in front him.

"You did so well taking your spanking, and following your rules all week." Becca's voice was sultry and deep. She spat in her right hand, and took hold of Evan's intensely hardening dick.

"After how hard a punishment you had last week, I had high expectations. You've followed through with them, haven't you?" She led him on, jerking his cock up and down slowly and deliberately. She put a second finger from her other hand in his mouth, forcing the boy to nod stupidly around them as he continued to suck. His eyes said just how close he was, and she intensified. Just as he started to make noises of protest, her right hand let go.

"Good boyyy, remember Rule 3. You only cum with Mistress' permission." she reminded him, only to immediately resume edging. He moaned again as she started over, working his shaft up and down, starting to give over to the feelings washing over him. She stopped once more, prompting begging looks and a haggard demeanor. But with a steely smile, she moved her hands again, this time with a particular intent. The boy merely closed his eyes and once more let his guard down, getting close even faster than before.

"You even laid out all the pieces of the device for me, baby. How sweet. But I noticed something... There's a piece missing." She loved watching his face change. The eyes went wide, and his cock softened in her hands. Evan scrambled for excuses, but the rest of her left hand held his jaw shut tight.

"I know you're about to lay out excuses, Evan, but I don't want to hear them. I'm aware it's a piece for the extra large size, and you...ha, you won't be needing even a medium for your meager little cock. But it's the principle of the thing." she went on, and his dick betrayed his feelings, swelling once again.

"I wanted the toy here, and you carelessly lost a part. I don't care how or why. Let me explain what's going to happen for the rest of the night." her tone hardened, hands not changing their speed or letting him speak. She got off her knees, bending over him menacingly as she continued.

"When I let go of this cock, you will go to the bedroom and get the hairbrush. You're going to bring it back to me, and ask me to punish you for your carelessness. I will certainly oblige." she continued. Evan whimpered fruitlessly at her words.

"The hairbrush will almost certainly dispose of this pathetic excuse for an erection, so we'll fit the chastity cage on and lock it up good and tight after. Only then, when you're a sniffling, disciplined, locked up little slut, will you be allowed to service me and bring our evening to a close. You can forget about any orgasms this week, that key is coming with me. You will do all of this perfectly and without question. After all, Evan, what's Rule #1???" Becca asked, removing her hands and stepping back from the gasping, drool-covered boy.

With a ruined orgasm pooling at his feet, he answered.

"I will obey my Mistress always, and enjoy it."

He did.