Jake was nineteen and had spent his whole life in Sydney's western suburbs pretending to like footy and trying not to stare at his mates' dads for too long at weekend barbecues. He was slight, narrow-hipped, with skin that burned pink in the Bondi sun and a mouth that was always slightly open, like he was waiting for something to be put in it.
He found Marcus on a Tuesday night at 11:47 pm, swiping through Grindr in his childhood bedroom in Penrith while his parents snored down the hall.
Marcus was forty-six. His profile photo was just a suited torso and a Rolex, but his bio read: *Looking for a smooth young thing to spoil and ruin. Prefer shaved. Prefer obedient. Prefer calling me Sir.*
Jake's stomach flipped. He typed: *I'm smooth. I'm obedient. I can call you anything.*
Three dots. Then: *Darling Point. Tomorrow. 8pm. Bring nothing but your ID and a pair of your girlfriend's knickers.*
Jake didn't have a girlfriend. He stole a pair of his mother's—white, high-waisted, a bit big on him—and spent the next twenty hours shaving. Everywhere. Legs, arse, chest, arms, the soft patch above his cock. He nicked his balls twice and didn't care. In the Uber over the Harbour Bridge, he could feel the lace against his freshly shaved skin and it made him so hard he had to hold his phone over his lap to hide it.
Marcus's apartment occupied the top floor of a converted Victorian mansion on New South Head Road, overlooking the black water of the harbour. The doorman didn't blink. The elevator was brass. When the door opened, Marcus was standing there in a charcoal suit, no tie, holding a scotch.
"Jake," he said. Not a question. A diagnosis.
"Sir," Jake breathed.
Marcus looked him up and down, reached out, and hooked one finger under the waistband of the stolen knickers, visible above Jake's jeans. "Mother's?"
Jake went red. "I… couldn't get…"
"Shh." Marcus pulled him inside by the elastic. "We'll get you proper ones."
—
The first night, Marcus didn't fuck him. He *prepared* him.
He ran a bath in a marble tub big enough for three. He made Jake strip while he watched, sipping his scotch, and when Jake stood there pink and naked and trembling, Marcus walked around him slowly and touched every inch of shaved skin with appraising fingers.
"Turn."
Jake turned.
"Bend."
Jake bent, hands on his knees, arse presented. Marcus knelt behind him—actually *knelt*, the suit creasing—and spread Jake's cheeks with both hands and blew a stream of cool air against his hole.
"Jesus," Jake whimpered.
"You're going to be perfect," Marcus said, and then he licked him. One long, flat, possessive stroke from taint to tailbone that made Jake's knees buckle and his cock leak onto the Turkish rug.
After the bath—Marcus washing him like a child, fingers lingering in every crease—he led Jake to a bedroom that smelled like cedar and money. There was a drawer open. Inside: silk. Rows of it. Panties in every colour, holding bras with falsies, a schoolgirl skirt, a maid's outfit, stockings with seams up the back.
"Pick a colour," Marcus said.
Jake's hands shook. He chose pink. A tiny, slippery, high-cut thong that felt like water against his skin. Marcus made him put it on, adjust it, turn around. The fabric cut into his arse and cupped his cock in a way that made it look small and harmless.
"There's my girl," Marcus said, and something in Jake's chest cracked open and spilled warm honey into his veins.
He let Marcus push him onto the bed, let him tie his wrists to the headboard with silk ties, let him edge him for two hours—bringing him to the brink with a lubed fist, then stopping, over and over, until Jake was crying real tears and begging in a high, broken voice he didn't recognise.
"Please, Sir, please, I need it, please—"
"What do you need?"
"To cum, Sir, please let me cum—"
"No." Marcus let go entirely and stood up. "Not tonight. Tonight you learn that your orgasm belongs to me. Your cock is a clit. Your arse is a cunt. And you don't cum unless I say."
He untied Jake, kissed his forehead, and sent him home in an Uber Black with a bag of new lingerie and a plug in his arse that he wasn't allowed to remove until morning.
Jake sat in the back seat with the plug pressing against his prostate and the lace riding up his crack and realised, with a clarity that felt like falling in love, that he had never been happier.
—
The training took three months. Marcus taught him everything: how to walk in heels (start with three inches, work up to six), how to do his makeup (foundation to hide the beard shadow, contour to give him cheekbones, eyeliner that made his eyes look wet and desperate), how to take a cock—first fingers, then a small plug, then a big one, then Marcus's thick, uncut, heavy dick that filled him so completely he saw stars.
"Push back," Marcus would growl, hand on Jake's throat, pinning him face-down into the thousand-thread-count sheets. "Push back and take it, you little slut. This is what you were made for."
And Jake would push back, and take it, and moan like a porn star, because it was true. This was what he was made for. University—he was doing Communications at UTS—felt like a dream. His mates, the pub, the footy, all of it felt like a costume he'd been wearing for someone else. This—the lingerie, the submission, the way Marcus called him *good girl* when he took the whole length without crying—this was real.
Marcus gave him a key to the Darling Point place. Gave him a credit card for "wardrobe expenses." Jake started wearing panties under his jeans to lectures. Started sitting in the back row, squeezed into a tight jockstrap Marcus had bought him, grinding subtly against the chair, thinking about the night before when Marcus had fisted him slowly until he'd had a prostate orgasm so intense he'd blacked out for ten seconds.
He was a sissy. He was Marcus's sissy. And he loved every fucking second.
—
He met Sarah at a gallery opening in Paddington, two years in. She was curvy, loud, laughed with her whole body, worked in marketing, and thought Jake was "sensitive" and "in touch with his feminine side" because he liked to cook and didn't mind carrying her purse.
He didn't love her. Not the way he loved Marcus. But he liked her, and his mother was asking questions about girlfriends, and Marcus had started saying things like, *"You should get a wife. A cover. Someone to bring to Christmas. It makes the secret sweeter."*
So he proposed on a beach in Byron Bay, knee in the sand, and Sarah cried and said yes, and Marcus paid for the honeymoon in Fiji and fucked Jake in the airport hotel bathroom while Sarah was downstairs getting a SIM card.
The wedding was at a winery in the Hunter Valley. Jake wore a suit that cost more than his car and a pink lace thong underneath that Marcus had picked out. During the vows, he could feel the lace cutting into him and he thought about the night before, when Marcus had made him kneel in the bridal suite and suck him off while the wedding planner set up chairs outside.
"You belong to me," Marcus had said, coming on Jake's face, his wedding tux hanging open. "Even when you say 'I do.' Even when you kiss her. Your cunt is mine."
"Yes, Sir," Jake had whispered, licking his lips.
—
They bought a terrace in Newtown. Sarah decorated it with Pinterest boards and throw pillows. Jake kept a locked drawer in his home office where he kept his lingerie, his makeup, and the chastity cage Marcus had bought him—a pink plastic thing that locked with a tiny key Marcus kept on his Rolex chain.
The arrangement was simple. Three times a week, Jake told Sarah he was going to the gym—Fitness First on King Street, back in an hour. Instead, he took an Uber to Darling Point. He'd arrive shaved, wearing whatever Marcus had texted him to wear—sometimes just a coat over lingerie, sometimes a full schoolgirl outfit under his tracksuit.
Marcus would be waiting. Sometimes with a drink. Sometimes with a paddle. Sometimes with another man—an NRL player once, a politician twice, a property developer who liked to watch—and Jake would perform for them, would let them use his mouth while Marcus used his arse, would thank them when they came on his face.
He learned to take it rough. Learned to love the pain. Marcus would fuck him until he was raw, then make him sit on a plug while they had dinner—Marcus eating steak, Jake in a maid's outfit eating nothing, watching, his cage straining—before sending him home with cum leaking out of him, soaked into the lace, the smell of sex all over him.
And then he would kiss Sarah hello, make her tea, ask about her day, and go to bed smelling like another man's cum, and the thrill of it—the sheer, filthy, electrifying *wrongness* of it—made him harder than anything ever had.
—
The near-misses were the best.
Once, Sarah came home early from a conference call and Jake was still in the kitchen, wearing just a pink apron and stockings, cooking Marcus's dinner. He heard the key in the lock and had three seconds to rip everything off and stuff it under the sink. He stood there naked, heart hammering, when she walked in.
"Why are you naked?" she laughed.
"Just got out of the shower, babe. Didn't have time to dress."
She didn't notice the lipstick smudge on his collarbone. Didn't notice the faint smell of poppers in the air. She kissed him and went upstairs, and Jake leaned against the counter and shook with adrenaline and came a little in his cage just from the rush.
Another time, Marcus called him while Jake was fucking Sarah—rare, missionary, eyes closed, thinking of Marcus—and Jake actually answered, holding the phone to his ear while he thrust.
"Are you in her?" Marcus asked, voice low.
"Yes, Sir," Jake whispered.
"Stop. Pull out. Go to the bathroom and put your plug in. Then finish in her while you're full of me."
Jake did it. Pulled out of his wife, went to the bathroom, shoved the plug in dry, gasping, went back, slid into her, and came in thirty seconds with Marcus's voice in his ear saying, *"Good girl, good little slut, mine, you're mine."*
Sarah thought it was the most passionate sex they'd ever had.
—
It went on for years. Jake got promoted at work—Marcus's connections. Sarah got pregnant—artificial insemination, Marcus paid for that too, wanted Jake to have a "proper family." Jake wore his cage to the ultrasound. Wore it to the birth. Wore it to parent-teacher nights, underneath his sensible dad clothes, while Marcus texted him photos of the key.
*Tonight,* the texts would say. *Red knickers. The ones that cut. Shaved smooth. I want to see marks tomorrow.*
And Jake would comply. Would slip out after the baby was asleep, would take the Uber, would spend hours being used like a toy—spanked until he couldn't sit, fucked until he couldn't walk, made to beg and cry and worship—and then come home and kiss his daughter goodnight and sleep next to his wife with Marcus's cum still inside him.
He was thirty now. Still smooth. Still obedient. Still Marcus's sissy slut, more in love with his secret life than ever.
Sometimes, lying in bed at 3 am with Sarah snoring softly beside him and his phone glowing with a new message from Darling Point, Jake would touch his cage and smile into the dark.
He had everything. The wife. The kid. The job. The respectability.
And he had Sir. He had the lingerie. He had the shame and the thrill and the filthy, perfect knowledge that he was owned.
He was a sissy. He was a slut. And he would never, ever stop.
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