The bills were still on the table, right where he left them.
Jesse stood in the kitchen with a mug of cold coffee in his hands, staring at the money like it might bite his fingers off. He hadn’t touched it. Not since last night. It was too clean, too neatly folded: offensive in its crispness.
In reality it was anything but clean money.
Dirty money.
He kept hearing the man’s voice in his head.
“Buy something pretty.”
It made his skin crawl.
But… the rent was overdue. He had two unopened envelopes on the counter stamped with red lettering. A job offer—some low-level inventory role at a warehouse—was still in his inbox, waiting. It wouldn’t pay well. But it would be real. Respectable.
And yet…
He picked up the cash. Counted it again. Three hundred and fifty. More than he’d made in weeks.
He swallowed hard. Then whispered aloud, bitterly:
“Fuck it.”
—
Marissa was already waiting at the diner, curled into the booth with too much to say and no idea where to start. Her hair was tied up in a messy topknot, her eyeliner slightly smudged, and her expression somewhere between excitement and suspicion.
“You look like hell,” she said, grinning as Jesse slid in across from her.
“Didn’t sleep,” he muttered.
“Why not?”
Jesse looked around, just to be sure no one was close enough to overhear. Then he exhaled and leaned in.
“I hosted again. A new client.”
Marissa’s eyes widened immediately. “Last night?”
He nodded slowly.
“You did it again?”
He nodded again, more reluctant.
She blinked, then leaned forward, voice dropping into a hush. “Was it… I mean, how was it?”
There was something electric in her voice—not judgment, not even concern. Just fascination. Curious, raw fascination.
Jesse hesitated. “He was rough.”
Marissa bit her lip. Her nails pattered the tabletop in anticipation.
“He called me a sissy. A whore. Spat on me. Slapped me. Treated me like…” Jesse trailed off, ashamed of the heat rising in his cheeks. “Like I wasn’t human.”
She waited. Patient, eager.
“And?” she asked.
He shook his head. “I don’t know why, but… I liked it. I really, really liked it.”
Marissa’s pupils dilated. Her breath hitched just slightly.
“Holy shit,” she whispered. “That’s… I mean, that’s intense.”
Jesse sat back, his voice trembling now. “I don’t even know what’s happening to me. I felt disgusting afterwards. Like I wanted to crawl out of my skin. But also…”
“Also?”
“I felt wanted. Not as Jesse. As… as Lacey.”
Marissa looked at him, and for once, there wasn’t discomfort in her face. There was hunger. Thoughtfulness.
“I’ve been reading about this,” she said suddenly. “I went down this whole rabbit hole after you told me. About crossdressing, sissification, feminization kink. Gender performance. All of it.”
He blinked. “You what?”
“Yeah,” she said, her cheeks going red. “I spent like four hours on Reddit and some really ‘out there’ Tumblr blogs. I couldn’t stop.”
“Jesus.”
“It’s fascinating, Jesse. I mean… Lacey,” she whispered, eyes mischievously darting around the diner. “This whole other you. The way you talk about it. The way you dress, the way you… change. It’s like… magic. Transforming into someone else.”
He looked down at his coffee. “It doesn’t feel magical.”
“Oh it is, Jess… and I kind of want to see more.”
He glanced up.
“I want to go shopping with you,” she said. “Lingerie. Panties. Stockings. Everything. Anything.”
His mouth fell open slightly. “You’re kidding.”
“No. Come on. You’ve just got some money, right? Might as well spend it like the dirty little slut you are,” she teased, her voice dropping to a sultry mock-whisper.
Jesse blushed. But he laughed, too.
“I can’t believe you’re into this.”
“I didn’t say into it,” she said, sipping her soda. “I said I’m curious.”
He raised an eyebrow.
“Okay,” she added. “Maybe a little into it.”
—
The boutique was a strange kind of heaven.
It sat on a narrow, gentrified corner near the edge of the district, nestled between a vegan café and a plant store. The sign above the door read “Chasing Risque”—a Boutique for the Bold.” Jesse immediately panicked by how feminine it looked, how exposed the window display was—mannequins in feather-trimmed robes and pearl chokers, high heels posed like weapons.
He hovered at the threshold, adjusting his hoodie like a disguise. Marissa nudged him.
“Don’t be a baby,” she said, and pushed the door open.
Warm air flooded over them—floral-scented, tinged with vanilla and something expensive. The inside was a delicate maze of curved clothing racks and plush velvet benches. Pastel silk robes whispered from hangers. Thigh-high stockings curled in clear plastic tubes like candy. Mannequins wore chokers and crotchless lace panties with no shame whatsoever.
And behind the counter stood a man who looked like he had never worn anything drab in his life.
He was tall, lean, with copper-colored hair shaved short on the sides and long on top, swept up into a soft curl. His shirt was sheer black, showing a taut chest and a gold nipple ring. He wore eyeliner sharper than Jesse’s razors, and strewn across his face was the kind of smirk that could cut glass.
“Welcome to Chasing Risque,” he said, eyes lingering just long enough on Jesse’s mouth. “Looking for something nice or… naughty?”
Jesse froze, but Marissa didn’t miss a beat.
“Definitely naughty,” she said, grinning. “He’s got a date.”
The clerk raised a brow, amused. “Lucky boy.”
Jesse blushed deep red.
“Don’t be shy,” the clerk purred, gliding out from behind the counter. “You’ve got the frame for it. Sharp cheekbones. Innocent eyes. A deadly combination. What’s your name, sweetheart?”
Marissa jumped in. “Lacey.”
Jesse shot her a look.
The clerk’s smile widened. “Ooh, Lacey. Cute. Fitting.”
Jesse swallowed. “It’s… for fun. Mostly.”
“Well,” the clerk said, stepping closer, “fun is kind of our specialty.”
Marissa leaned toward Jesse’s ear and whispered, “Flirt back, come on. He’s gorgeous.”
“I don’t know how,” Jesse hissed under his breath.
“Pretend you’re Lacey. She knows how.”
Jesse turned toward the clerk, feeling his cheeks flame. “What would you… recommend?” he asked awkwardly, voice dropping an octave without meaning to.
The clerk didn’t even blink. “Something to make you feel like the filthy little minx you are.”
Marissa cackled.
He gestured toward a nearby rack. “This mesh set? Sheer bra, matching thong, garters, the whole fantasy. In blush pink or blood red.”
“I… I like red,” Jesse said.
The clerk gave a knowing smile. “Of course you do.”
He slipped away to grab the size.
“Holy shit,” Jesse whispered to Marissa. “He’s into this.”
“No kidding. You should ask for his number.”
“I think he wants to sell me lingerie, not date me.”
“Same thing in his world.”
—
They spent almost an hour exploring.
Marissa flitted between racks like a kid in a candy store, holding up panties and slips, yelling “This is so you” every few seconds. Jesse’s basket filled with silk, mesh, lace in every wicked cut imaginable—g-strings with velvet bows, a see-through teddy with heart-shaped nipple covers, a garter belt so delicate he was afraid to touch it.
They giggled like teenagers dodging parents, whispering jokes about “how sometimes the least amount of fabric costs the most” and the absurdity of pearl thongs. Every now and then, the clerk—whose name tag read Theo—would slide up beside Jesse with a suggestion:
“Try this one. Pairs well with red lipstick and ambiguous morals.”
Marissa loved every second of it. She egged Jesse on, encouraged the banter, teased and whispered things like “You’re blushing,” and “I swear you’re getting hard.”
She wasn’t wrong.
The shame came in waves, but so did the thrill. Being seen. Being wanted. Being Lacey—in secret, in public, in transition.
Holding pieces up to check the fit: the lingerie masked Jesse like camouflage. Meanwhile it drew a big line ending with five exclamation marks under Lacey’s name.
Lacey.
—
They left with three full bags.
As they stepped out into the chill evening air, Jesse exhaled like he’d been holding his breath inside the whole time.
“You were amazing in there,” Marissa said. “Lacey’s got game.”
“I wanted to die,” Jesse muttered, but he was smiling.
Marissa bumped her hip into his. “You loved it.”
He didn’t answer. But he didn’t deny it either.
—
Later that night, the apartment was silent.
Jesse stood in the middle of the room, holding the red silk bag from Chasing Risque like it was some kind of top-secret dossier. The light outside had faded into that dusky violet that made everything look slightly unreal—too soft, too quiet, like the world was pausing to let him catch up.
He placed the bag on the bed.
For a moment, he just stared at it, his stomach tight with anticipation and guilt. The weight of the money—dirty money—still lingered on his conscience, but he’d spent it anyway. He told himself it was for Lacey.
Did that make it okay?
He peeled off his hoodie and jeans, layer by layer, until he stood in nothing but his boxers. The air felt different against his skin now, more aware, more sensitive. He opened the bag carefully, almost reverently, and pulled out the lingerie set.
Blood red.
The garter belt shimmered faintly in the dim light, delicate floral lace with tiny gold accents. The matching bra was lightly padded, structured enough to shape his chest into something more rounded, more… her. Stockings came next—sheer black, glossy like wet ink.
He slipped into the bra first, adjusting the straps slowly, fingers trembling.
Then the garter belt. The hooks were fiddly—everything was new, tight, and unfamiliar. He clipped the stockings into place, adjusting them with quiet precision. His reflection stared back at him from the closet mirror, silent and unreadable.
Then he stepped into the matching panties.
They hugged his hips perfectly. There was something profoundly intimate in the way the fabric moved against him—softer and more gentle than any touch he could remember.
He stood in front of the mirror for a long time.
There she was.
Not perfect. Not polished. But real.
Lacey.
Her lips weren’t painted, and her wig wasn’t on. But it was her—emerging through the haze of shame and desire and confusion. The lines of her body weren’t feminine in the way magazines would want, but there was grace in the angles, a kind of meaningful beauty in the way she carried herself.
And Jesse—well, he was still in there too. Watching.
A war played out in silence.
Who was this for?
The men? The clients who texted with demands and slurs and promises of money?
Marissa? Who now looked at him like a living puzzle she was eager to solve?
Or was it just… for himself?
Was that what scared him the most?
He ran a hand slowly down his thigh, feeling the stocking shift, the whisper of silk and lace over skin. The sensation made his breath hitch. Not because it was erotic—but because it was him. This body. This skin. This… truth he’d buried for so long.
Lacey looked back at him with mournful eyes.
He whispered her name.
“Lacey.”
And for a moment, he didn’t feel ashamed.
—
There was a knock on the door.
Jesse, still in full lingerie under a gray bathrobe, froze. He didn’t need to check the peephole—he already knew it was her.
He hesitated for a moment, then opened the door.
Marissa’s eyes widened immediately.
Her lips parted, but she didn’t say anything. She just stood there, looking him—her—up and down.
The robe slipped open slightly at Jesse’s chest. Red lace peeked through.
“Oh my God,” Marissa finally said, stepping inside. “You really went all in.”
She circled him like he was a museum piece. Her voice was breathless with intrigue, almost reverent. “I wasn’t sure you’d do it alone. But damn… Lacey’s hot.”
Jesse felt a blush rise to his cheeks. “Stop.”
“I’m serious,” she said, stepping closer. “This is… something.”
Marissa’s eyes weren’t mocking. They weren’t even confused anymore. They were lit up with something else—something Jesse couldn’t quite place at first.
Curiosity, yes. But more than that.
She walked toward the full-length mirror, motioning him to follow. “Let me see you.”
Jesse reluctantly untied the robe and let it fall open.
Marissa let out a low whistle. “Shit. The stockings, the garter—this is hotter than I expected.”
“Don’t,” Jesse warned quietly. “Don’t look at me like that.”
She tilted her head. “Like what?”
“Like I’m your newfound kink.”
Marissa bit her lip. “I mean, maybe a little? But it’s not just that.”
He turned away. “This isn’t just dress-up.”
“I know,” she said quickly. “Like I said, I’ve been reading, a lot, okay? Watching stuff. Talking to people online. I went down this whole rabbit hole about femininity, gender performance—crossdressers, sissies, the works. It’s like… something unlocked in my head when you told me.”
“That’s not comforting.”
“I’m not trying to fetishize you, Jesse—Lacey. I’m just… fascinated. You’re beautiful.”
She stepped behind him, her hands light on his shoulders. “You don’t even see it, do you?”
He didn’t move. “Why are you doing this?”
Her hands trailed down his arms. “Because I’m curious. And maybe turned on. Is that so bad?”
She leaned in close, lips brushing his neck.
Jesse flinched and stepped forward, shrugging her off.
“Don’t.”
“Why not?” she asked, confused.
“Because it feels weird, Marissa. You’re my friend.”
She opened her mouth, then shut it again. Her gaze dropped to the floor.
“Okay,” she said after a pause. “I get it.”
The silence that followed wasn’t angry—but it was heavy. Awkward. Tense.
Jesse reached for his phone on the table.
“I need to send something,” he mumbled.
Marissa raised an eyebrow but didn’t push.
He pulled up the client’s chat.
SissyAdmirerX38:
Red. Garter belt. No panties. I want to see ‘little Lacey’ too.
SissyAdmirerX38:
And one from behind. Spread those cheeks. Over the shoulder look.
SissyAdmirerX38:
Something really femme. Limp wrists. Mean it.
SissyAdmirerX38:
Do these, and there’s more where this came from.
(attached: a $250 transfer)
Jesse looked at Marissa, then stepped into the bedroom.
He set up his phone on the sink, checked the lighting, adjusted the robe off his shoulders, letting the red lace do the talking.
He posed carefully—just enough to be erotic, never enough to be completely exposed. He lifted one leg onto the bed, letting the garters stretch across his thigh. A quick burst of shots. Different angles. Deliberate and numb.
He looked at them afterward. They didn’t feel like pictures of him. They felt like Lacey’s body. Her weapon. Her mask.
He sent the best three.
Lacey:
Hope this is what you wanted.
The reply came instantly.
SissyAdmirerX38:
Perfect. You’re getting better at this, slut.
More soon. I have plans for you.
Another payment appeared.
$300 this time.
Marissa walked in, quiet now.
She looked at the phone, then at him.
“You okay?”
“No,” Jesse said. “But I think I’m getting used to it.”
She nodded, hesitantly.
“Lacey,” she said, softly, “what are you becoming?”
He didn’t answer.
Because he didn’t know.
—
The money kept coming.
And so did the clients.
The newest one, who messaged through the same encrypted app, was older. Polite at first. Well-spoken. He called Lacey “princess” and “my perfect little doll.” But his requests became more specific—clinical in detail, almost like he’d done this a hundred times before. Maybe he had.
Daddy902:
Black lace. Fishnets. Heels if you have them.
Collar optional. But I’d prefer it.
Jesse stared at the message for a long time before responding.
Lacey:
I have what you want.
Daddy902:
Excellent, princess.
He hated how those words made his stomach flutter.
—
That afternoon, Marissa showed up again, unannounced, like she’d made a habit of doing. She knocked and pushed the door open before he answered.
“You dressed up yet?” she asked with a smirk, stepping inside. “Or do I get to watch the magic happen this time?”
Jesse sat on the edge of the bed, holding the black lace bodysuit in his lap. He didn’t look up. “You shouldn’t be here.”
“You let me in last time.”
“That doesn’t mean this is normal.”
Marissa crossed her arms, leaning against the doorway. “Who’s it for this time?”
“A new one,” he muttered. “Wants me in full lingerie. Fishnets. Collar.”
Marissa’s eyes lit up again, that same strange hunger flashing across her face. “You’re really doing it, huh?”
He finally looked at her. “You like this too much.”
“So do you,” she shot back, softer than before.
Jesse said nothing.
Marissa walked over and sat beside him. Her leg pressed against his.
“I’ve been dreaming about it,” she whispered. “You. Her. I don’t even know what to call you anymore.”
“Just… don’t call me anything right now.”
She smiled faintly. “I was thinking maybe we could try something. Together. Just us.”
He turned sharply to her.
“I’m not a toy, Marissa.”
“I didn’t say you were.”
“You want to experiment. I’m not your fucking experiment.”
Her face reddened. She looked away. “I didn’t mean it like that.”
Jesse stood, grabbing the lace bodysuit and heading toward the bathroom. “I have work.”
Tears began to fill Marissa’s eyes as she left. The door slammed in frustration.
—
Lacey opened the door at 9:00 PM sharp.
The client was tall, with silver hair and expensive cologne. His eyes lingered on her chest, then drifted down her legs to the heels.
“Turn around,” he said.
She did.
“Good girl.”
The words hit harder this time.
He stepped inside without another word, brushing past her, the scent of tobacco and musk filling the room. He dropped a small black bag on the couch.
“Put that on.”
She opened it—inside was a slim leather collar with a tiny gold lettering.
It read: “sissy.” All lowercase. A love heart over the ‘i’.
Lacey hesitated.
“Problem?” he asked, already removing his coat.
“No,” she said. Her voice was soft. Lacey’s voice.
She clasped it around her neck.
The client nodded. “Kneel.”
What followed blurred the line between domination and performance. He wasn’t cruel—but he was rough. His words were filthy, his grip firm. He called her degrading names that made Jesse want to disappear—but Lacey? Lacey responded. With moans. With obedience. With something dangerously close to enjoyment.
Her dick had never been so hard
At one point he whispered, “Look at you. Fucking made for this.”
And she believed him. He stroked her to climax through the delicate panties. Wave after wave of pleasure bursting through the lace and running across the man’s bulbous knuckles.
She had screamed out in ecstasy.
He had gently whispered in her ear as she edged closer to oblivion.
“You want this baby girl?”
“… Yes.”
“Say it. Call me ‘Daddy’.”
“… Daddy.”
“Say you want it…”
“I want this… Daddy.”
And that’s when she came. Torrents of cum. A Tsunami of cum. A river of absolute bliss.
Mouthing the words ‘Daddy’ as a stranger – a strange man – stroked her cock.
—
After, as he dressed, he lit a cigarette and exhaled with a satisfied smirk.
“You love this don’t you, princess?”
Lacey said nothing.
He pulled out his wallet and dropped several crisp hundreds on the nightstand. “Best I’ve ever had. There’s a little extra. Buy something pretty.”
He was gone seconds later.
The room smelled like sex and smoke and shame.
Jesse peeled the fishnets off slowly, trembling with adrenaline and disgust. Yet beneath the disgust, buried deep—was satisfaction. And that was what scared him most.
—
The next morning, he sat across from Marissa at a cheap diner, both of them nursing bitter coffee in silence.
“Did he pay well?” she finally asked.
Jesse nodded.
“Do you… want to talk about it?”
“No,” he said. “But I think I need to.”
And somewhere inside, he wasn’t sure if it was Jesse talking anymore… or if Lacey had started to take root.
—
Gent777:
No rush. No script. Just you, how you feel most beautiful.
I’ll bring wine.
Lacey almost didn’t respond.
Most clients were blunt, bordering on cruel. This one sounded… soft. Dangerous in a different way. Not in the way that left bruises, but in the way that lingered in the chest afterward.
Lacey:
I’ll be ready.
He arrived at 8:15. Well-dressed. Clean-shaven. Late thirties maybe. Quiet confidence. And when she opened the door, he just smiled.
“Lacey.”
The way he said it—it wasn’t lustful. It was admiring. Honest.
Jesse had gone further this time. A platinum-blonde wig, layered waves that framed his cheeks. A velvet wine-colored dress with sheer sleeves, paired with lace-topped thigh-highs and black kitten heels. He had even taken time with his makeup—smoky eyes, soft contour, a subtle shimmer on the lips. He looked… not perfect, not polished. But intentional. Feminine.
“You’re stunning,” the man said.
He handed her the wine—rosé, chilled—and a bouquet of flowers. Flowers. Like it was a date.
They sat together on the couch, sipping from mismatched glasses, the tension curiously absent.
“You don’t want to…?” Lacey gestured vaguely toward the bedroom.
“Not yet,” he said with a small smile. “I want to talk to you first. Get to know the woman I’m paying for.”
Lacey blinked.
No one had ever called her that.
He asked about her day. Her interests. Her favorite color of lingerie. It was surreal. Disarming.
At one point, he reached forward and tucked a loose strand of wig hair behind her ear.
“You don’t have to keep pretending,” he said. “I know it’s not just an act for you.”
The words hit like a slap, but he wasn’t wrong.
Later—much later—they did go to the bedroom. But it wasn’t rough. It wasn’t degrading. It was slow. Curious. There were kisses. There were whispered compliments. The way he touched Lacey felt like he was touching someone he cared about. Someone real.
And that—that—was what terrified Jesse.
—
After the man left with a goodbye kiss and another generous envelope of cash tucked neatly into his wallet, Jesse stripped everything off in silence.
The apartment felt empty. Echoey. Too still.
He stared at himself in the mirror—at the red marks on his chest from the bra straps, the smudged lipstick, the carefully shaped brows, the feminine curls of the wig resting on the dresser.
He had money now.
Real money.
For the first time in his life, he could pay rent early. He could afford groceries without calculating. He could walk into a boutique and buy whatever he wanted.
He told himself it was business.
But each time he zipped up that suitcase or closed the wardrobe, he felt something twist in his gut.
Because the truth was, Lacey wasn’t just for clients anymore.
He wore the wigs alone, sometimes. He took selfies in lingerie and deleted them seconds later. He practiced his voice. His walk. He wore perfume to bed.
It was more than money now.
And he didn’t know if he could stop.
—
Later that week, Marissa called him.
“How’re you holding up, Lace?”
“Don’t call me that right now.”
“You okay?”
“I don’t know what I am.”
A pause on the line. Then: “Come over. Bring the blonde wig.”