Olly had never been one for luxury; when he was young it was simply unobtainable, and as he’d grown older he’d fostered a slight contempt for “the finer things in life” on the grounds that they fronted a lifestyle that held its space by breaking the backs of those beneath it.
Despite all that he found himself at Lucaria Bainbridge’s house, feeling small before the spread of micro-salads, lobster, and other such delicacies presented on old–but meticulously maintained–crystal. The covered deck they dined under was bright and sunny and decorated by innumerable exotic plants that thrived both off the sunlight and the close care of the house staff.
Ms. Bainbridge was an esteemed member of the city council and as such held a measure of power Olly was unlikely to ever grasp. She sat across from him at their two person table, blue sundress immaculately flattering her heavier figure, blond rivulets of hair flowing to frame a rounded, comely face. She was taller than he was–not a difficult feat–and even when sitting had an air of polite influence that begged the pardon of anyone who dared to second guess her.
“Do try the wine, dear, it’s a vintage.” *Command* was a strong yet fitting phrase for the light words that danced from her lips. Olly didn’t care for commands, particularly when aimed at him, but leadership at his nonprofit had been so thrilled when Ms. Bainbridge had taken an interest in him after a presentation he’d given the council on the local homeless crisis.
He took a sip of wine; quite frankly he couldn’t tell the difference between it and the bottle of red his roommate had brought home the week before, but he wasn’t going to say as much. For good measure, he took a couple more sips before lowering the glass with a tight smile.
“Thank you again for having me over, Ms. Bainbridge,” he said, as graciously as he could manage. Her laugh was like singing glass.
“Of course, darling. I was so impressed by your presentation, and more than that, *you* are quite the intriguing young man!”
Olly had to blink at that. *Intriguing.* He sipped at the wine once more to forego a response, hoping the socialite in her would be willing to pick up the slack in the conversation. Her smile widened further.
“Straight from France, you know,” she said, nodding at his glass. “I tend to be partial to Italian wines myself, but it was a gift from my cousin. The man spoils me ever so much.”
Olly blinked again, slower this time, nodding along to her story in an attempt to at least seem present. Her voice tinkled like wind chimes. His eyelids were heavy.
“Are you alright, dear?” she asked, and her concern didn’t sound real–but nothing seemed real with the way the world was tilting, and Olly had to press a palm to his forehead. He didn’t register the predatory smile on her face as his vision faded.
*
Cool air nipped at his skin as Olly awoke, and he couldn’t move. He tugged at his restraints, breath quickening and head pounding. His head wouldn’t turn thanks to a tight strap across his forehead, and it was too dark to see most things, but as he regained the rest of his senses he could deduce a little:
He was naked, laying prone with his legs raised and spread as though for a gynecologist’s appointment. Every limb was tied down. His binder had been removed, freeing his breasts and leaving his nipples hardening in the cold, as had his boxers; his pussy was exposed to the room at large, however big it may have been.
A door opened, flooding the room with light, then closed behind the imposing figure of Lucaria Bainbridge, no longer in her sundress. She flicked a switch on the wall and lights above him blared on, forcing him to squint as she strode around the table to his head and leaned over him.
She’d changed into a short-sleeved blouse and slacks, and pinned her hair up. She smiled as though he’d just walked into a party and he was her favorite person in the world.
“I was hoping you’d wake up soon,” she said, almost disappointed in him for not doing so sooner. “You certainly took to that rohypnol a touch too well.”
“What the fuck?” was the only thing he could think to croak. He wasn’t expecting the heavy slap that landed across his cheek.
“That’s not how we speak in my house,” she said sternly. She straightened up, walking back toward his feet, settling between his legs. She took a finger and traced up his slit, coming to rest on his testosterone-engorged clit.
“What are you doing? Stop!” he said, voice rising and cracking. He continued to fail at breaking free from his restraints.
“That’s enough,” she said, pinching his clit between two fingernails. He bellowed in pain. “I *will* gag you. No one will hear you anyway–I just don’t care to listen to my property scream so boorishly.”
He began to object, only for her to bear down on his clit again. The pain wasn’t quite intolerable, but it was close, and he whimpered as she released it. She went out of his line of sight–he could hear her rummaging, and she returned with a silicone circle hanging from a strap. She ignored his attempts at thrashing as she forced his mouth open, securing the circle between his teeth and latching the straps around his head. Drool immediately accumulated in his open mouth, and would have leaked out if he weren’t on his back. She then produced a plug that she inserted into the ring, and suddenly he could only breathe through his nose.
“Better,” she said, voice tinged with disdain. She ran fingers over his naked body, leaving goosebumps in her wake, as she returned to stand between his legs. “Now where was I…*yes.”* With only the slightest amount of natural lubricant available, she plunged two long-nailed fingers into his pussy.
“I’m sure you’ve gathered by now, but when I met you at the council meeting I knew you had to be mine. I didn’t realize you were trans, of course…but that’s no problem. I *was* rather looking forward to milking your cock raw and crushing your balls, but I’m certainly not opposed to learning a new equipment set.”
Knuckle-deep, she twisted and turned her fingers, scratching inside his vagina. His hips bucked, but she didn’t withdraw. She scissored, stretching him as far as she could, then added another finger. She licked the fingers on her other hand and began toying with his clit, stroking up and down, soothing the still stinging fingernail marks. Against Olly’s will his pussy began leaking, clit stiffening at the attention. He whimpered, muffled by the gag, as she ran the smooth top of her nail up the underside of his clit, then added yet another finger into his pussy.
Olly was panting by the time she inserted her entire hand, forming a fist once it was inside. He was fuller than he’d ever been, and his body responded with ardor. She pumped her arm in and out of him, twisting and grabbing as she did, all the while teasing his clit. He could feel himself approaching the edge, the councilwoman’s hand buried in his cunt, but just before he fell over she withdrew both hands, stepping away.
It was the least satisfying orgasm of his life.
Ms. Bainbridge smeared his juices across his torso, wiping her hand and forearm clean. “I’ll have more fun with that hole later,” she said sweetly, tracing the base of his tired clit with one fingernail. Stepping up to lean over his head again, she twirled her fingers in his hair and murmured “I’m going to destroy you, darling. You’ll be so *pretty* all gaped and shaking and covered in fluid. And once I’m through with you, it won’t matter where you go or what you do: your body will be *mine.* I’ll leave you to think on that while we get started on your other hole.”
She left his view once more. Olly’s pussy ached, stretched and trying to readjust to its emptiness, and his entire body hurt from struggling and writhing against the restraints. When she returned she waved two items in his line of vision: an obscenely large neon pink dildo, and a more reasonably sized (yet still somewhat frightening) steel butt plug.
“Can’t have that cunt of yours closing up, now can we?” she asked, and he shivered as she rubbed the length between his lips to pick up the remaining moisture. Tears gathered in his eyes as she lined the head up with his deformed entrance and slid it in–it somehow seemed to stretch him further than he already had been–and allowed it to bottom out before fiddling with the restraint system to secure it, keeping it from sliding out of its own accord. She then bent under the table he was laying on, emerging with the plug now dripping with lube.
“And *this* will get us a nice start on the ass.” She sounded delighted, more like a kindergarten teacher observing her students’ artwork than a deranged, sadistic public servant. The metal was cold on his hole as she pressed, pressed, pressed it inside of him.
Olly thought he might burst open; a low whine escaped him, earning him a light swat to the inner thigh. With all the other sensations happening, it felt like a much stronger hit.
Ms. Bainbridge stepped back to admire her handiwork, producing a phone from her pocket and snapping a few pictures. “I have a dinner party to attend,” she said brusquely, stowing the phone. “And *you’re* going to lay there and imagine everything else I’m going to do to you. Bear in mind, I’m *very* creative.” Leaning in close to his sore clit, she spoke softly, allowing her hot breath to encompass it “I bet this little thing can flatten like a cock. And those tits have *endless* possibilities.”
With that she turned, hitting the light switch as she left the room, leaving Olly cold, aching, and ever so full in the dark.