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.
