“I don’t know, Boss, I don’t think it can fit.” His eyes had widened when she pulled the plastic package out of the plain red shopping bag. The company that made the toy was know for its reliable quality and ethical manufacturing- but like everything of that nature bore the warning that it was “for novelty purposes only”, at least if you bought it in those states that gave you a criminal record for doing the naughty with an object explicitly designed for that reason.
This was Canada, so she’d bought the big black butt plug with complete impunity, and talked with the clerk for a good fifteen minutes about anal sex first. Broaching the edge of the plastic bubble pack with a pair of scissors, she sawed and crunched.
“I would work better if you used the can opener, Boss.”
“Shut up, Sweetpea,” she said affectionately, prying the plastic apart like a stubborn clamshell. The hard edges bit at her fingers, but she persisted until she wriggled out the entire, solid and heavy black silicone plug and thumped it dramatically, flared bad down, on the table.
He looked at the heft of it, and tried to imagine it inside him. “I still think it’s a bad idea, Boss.”
“It was on sale!”
“Yeah, for how much?” It’s not that she couldn’t afford it, but she was always trying to downplay the effort when she got him a gift. He thought it was cute.
“Fifty bucks. Down from sixty,” she looked pleased and a bit defensive. “I consider it a goal for you. Besides, it’s only a smidgen bigger than my fist.”
He made a hand waving gesture over his shoulders, “You’re the Boss…”
“Don’t you forget it, Sweetpea.”
She did try the toy, over the weekend, but found that he got hung up on the widest point. Not one to be perturbed by a challenge, she gave him a break, until presently he forgot about it, the toy living in its own ziplock bag. They played with other things, over the weeks, fucking and fisting and strapon sex, and other normal couple things until one Saturday night, cozied up together, she decided it was time…
The swishy, latex dipped, double bamboo cane was another acquisition from the same sex shop, bought several months ago at a post Valentine’s clearance event. She loved how easy it was, and he loved to hate it- it hurt like a bitch, and was just on the cusp of too much in one go, but of course a part of him craved the excessiveness. This feeling of horrible-wonderful was of course only helped along by the fact that his nuts were now connected, via well wrapped rope, to a little metal hook in one of the big heavy ceiling beams, something she had attached, through the loop, to his big toe, so he was standing like a particularly uncomfortable flamingo. On a piece of plastic waffle mesh that was ever so slowly imprinting his other foot with grooves.
To make things more interesting, from time to time the cane would zip down against calf, or thigh, or worse, his upturned sole. She was looking for the misery point, herding him there.
“I can’t Boss, I c-can’t…”
“Would you like to sit down?”
“Yes,” he said, small voiced.
“Okay, you need to wait for another minute.” She loved that quiet admission that she had broken him, but she wanted done with him. “I’ll count it off for you.”
He whimpered and nodded, and she made sure he could hear her run from sixty, letting him see she wouldn’t cheat. When she unhitched him, he sagged like a puppet with cut strings, limping on his tenderized feet.
“Com’ere Sweetpea, time to sit down and get the weight off.”
And then he saw the chair set up, with the plug sat in the middle of it.
“Oh, fuck no, Boss…” he said, weakly.
She had the pharmacy brand KY in her hand now, “How much of this I let you use is entirely determined by how much shit you give me, Sweetpea.”
“Yes, Boss.” He caught the lube clumsily, made sure to use as much of it as he thought he could get away with. Usually he was lucky if she let him have a pea sized dollop, which meant she was serious. Still a little pain drunk, he sat down.
The blunt tipped wedge of the plug opened him, like a foot in the door or her fingers on the plastic package, pushing and hurting, but also have a certain pleasurable intensity. Gravity and his own efforts forced it in further, and despite the lube slickness, pulled wet tears up in the corners of his eyes.
It was easier, at least, than before, but he still stuck at the widest point. He whimpered.
“Now Sweetpea, I want to see your butt touch the chair,” Her voice was all fake stern, her face lit with a sadist’s empathy.
“I know you can do it. I’ve seen you take more, you greedy little slut!”
“Bosssss…” He was crying properly now as the widest point slipped in, giving him incredible fullness. She took a step back, watching him.
“Hurts, doesn’t it? It’s nice.”
This particular piece is stitched together from my own and other people’s experience. Let’s just say I have cool friends.