Sam walked down the staircase into the group house's common area and saw Kelly sitting on a couch. Dressed in a shapeless t-shirt and faded jeans, she didn't look like anything special, but he knew better. At the sound of his footsteps, she looked up from her laptop, one eyebrow slightly raised in inquiry.
"Fancy meeting you here," he opened.
"I do live here," she said, "What brings you by?"
"Just finished talking market stuff with --" he gestured back up the stairs at a cluster of bedrooms. "But now that that's done and you're here, would this be a good time to, ah... redeem the bets from Sunday?" He smiled. "Unless you're in the middle of something, of course."
She paused, closed her eyes and ran her hands from shoulders to hips as if checking on something internal. "Yeah, I'd probably be up for that. And I was just reading clickbait anyway." She closed the laptop decisively.
"Glad to rescue you from that, then."
"Oh, yes. Rescue," she said, putting a double layer of sarcasm into her voice. "You know, I issued a bunch of tokens that game and then they changed hands a bunch more. What did you wind up with?"
"Twenty cane strokes to your breasts."
She gave a happy little shiver. "Definitely up for that." She bounced to her feet. "Shall we?"
"We shall."
They walked together down the next set of stairs. Living in a six bedroom group house had its frustrations, but it also had benefits. Like enough room to comfortably host poker games. And a common basement that could be made into a decently equipped dungeon. The former sometimes involved the latter.
He wasn't sure exactly which of the residents were in relationships with each other at the moment, but all were sexually comfortable enough with each other (and with frequent visitors like him) that mere strip poker had lost its edge. So they'd raised the stakes.
(There'd been a long discussion of game theory and how to define a raise, but they'd thrown it all out and gone honor system. Thus far, this had worked.)
They arrived in the dungeon and she casually peeled off her shirt. She had nothing on beneath. "Where do you want me?"
He took a moment to admire her breasts: a bit more than a handful each, perky, with dark nipples already erect, bouncing slightly from the energy with which the shirt had been removed. Then his verbal loop ran her question past him again and he answered, "St Andrew's Cross good?"
"Sure," she said, leaning back against it and raising her arms.
He gently buckled her wrists into the cuffs, then ran his hands down her arms, through her shoulders and onto her chest. First tracing the skin lightly, then pressing deeper, pushing her soon-to-be-caned breasts to and fro, and massaging the solid muscle beneath. Then he pulled back to rest his fingers gently on her nipples, leaned forward, and kissed her lightly on the mouth. She returned the kiss with equal lightness.
"Like you," he said.
"Like you," she answered.
He stepped to the side briefly to examine the selection of canes hanging on the wall. He selected a long thin rod of clear lucite -- probably the meanest cane on the wrack.
"Eep!" she said, and gave a shudder considerably less happy than the one from earlier.
He gave an evil smile. She returned the smile uncertainly.
He stood to her right and extended the cane, laying it softly across her breasts, halfway from the nipple to the upper crease. He pressed it to her ribs firmly, enjoying her fear.
Then he drew the cane back and brought it forward at full speed with a solid crack.
She let out an incoherent "gaah!" -- half scream and half gasp, mangled further by the panting that followed.
He waited for the panting to subside, then delivered another blow, perhaps half an inch below the first one.
Again an incoherent noise and a sharp inhalation, but quieter this time.
Slowly, he delivered three more blows. Each time the reaction was more muted, and a serene smile had started to appear about two seconds after each strike.
After five stroke he paused, looked at her chest and how the cane lay upon it, and commented, "This isn't really hitting symmetrically, is it?"
"No," she agreed, her voice only slightly dreamy, "left boob is certainly getting it harder. End-of-the-cane swings faster as it were."
"Well we can't have that," he said, and crossed to her left side. Lining up the cane was a bit more difficult from here, but he found a place.