Sissy Call Girl

The ceiling paint was flaking like dead skin, shedding in tiny curls that landed on the cluttered floor. Jesse lay on his mattress—cold and hard—staring up at the moldy crater above his bed like it might someday collapse and end things for him. That’d be a mercy. No calls back from the job interviews, fridge humming empty, and rent was due in two days. Landlord had stopped being polite two months ago.

His phone vibrated. Not a job offer. Not even a friend. Just another "final notice" from the power company.

He sat up, scratched the stubble on his chin, and stared at the cracked mirror leaning against the wall. His real clothes—the ones that made him feel something, anything—were tucked in a suitcase beneath the bed. His secret. Silk and lace. Nylon and fishnet. The kind of fabrics that never judged him.

He hadn’t worn them in a while. Not since things got this bad. It felt wrong to indulge when everything was crumbling. But now? Desperation was louder than shame.

He slid the suitcase out and popped it open.

The scent of talcum powder and synthetic perfume wafted out—a ghost of better nights. Jesse’s hands trembled as he ran his fingers over a black satin bra, the cups slightly wrinkled from being folded too long. He wasn’t good at this. The padding was uneven, and his chest was flat. His makeup attempts were smudged and amateurish at best. But when he wore these things, he could pretend. Pretend he was someone else—someone with control. Someone desirable.

He peeled off his hoodie and boxers, then tugged on a pair of high-waisted black lace panties, the kind with scalloped edges and a sheer mesh panel in the front. They hugged his hips tight, cutting into the soft flesh there. Next came the bra—he adjusted the straps, stuffed it with tissues. He’d seen tutorials online, but his hands were clumsy. Still, under the dim light, he could start to see her. Her. The version of himself he never named.

He grabbed a pair of sheer thigh-high stockings and worked them up his legs, fumbling with the elastic bands. They rolled at the top—he needed garters. He made a mental note. Always things to fix. Always things missing.

The makeup came last. Foundation too pale, eyeliner wobbly, lipstick bleeding at the corners. But when he stepped back, the reflection didn’t mock him. It invited him.

A whisper of a thought slithered into his head. A message from a forum he’d browsed in the past. A man had posted there once, blunt and cruel: “You want money? Men pay for it. Play the fantasy. That’s what they want.”

Jesse stared at himself, at the trembling imitation of femininity he barely knew how to construct. He hated how right it felt. He hated that he was even considering it.

But rent was due. And no one was coming to save him.

---

The street outside was wet with last night’s rain, and the city smelled like hot garbage and cheap cologne. Jesse sat hunched over his laptop, stealing Wi-Fi from the diner across the alley. His fingers hovered over the keyboard as he stared at a search bar that read simply:
"How to start escorting."

He’d been here for an hour. Clicking links, closing tabs. Reopening them. Some sites looked clinical—escort agencies, full of strict rules and polished photos. Others were darker, seedier. Direct ads, short bios, grainy selfies. Discretion guaranteed.

Jesse's heart thumped as he clicked through a site that let users post their own ads. Categories like companionship, fetish-friendly, passable only. He didn’t like how often that word came up: passable. He knew he wasn’t. Not yet. But maybe... convincing enough?

He read ad after ad—some written like Craigslist personals, others like seduction scripts. They used words he didn’t think applied to him. Shemale. Trap. Slutty crossdresser. Ugly words. Dehumanizing, but useful. He took notes. Copied phrasing. Studied their profiles the way a thief studies alarm systems.

He didn’t have professional photos. Just a few half-decent selfies in soft lighting, where makeup and angles did most of the work. He wore a mesh bodysuit in one, barely covering the makeshift padding of his chest, paired with fishnet tights that were starting to ladder along the thigh. He posed on his bed, legs crossed, face half hidden behind tousled synthetic bangs.

He hesitated, then uploaded the image.

Username: Lacey_J
Category: Crossdresser / Discreet
Age: 22
Services: Massage, Oral, Light Domination
Rate: $150/hr
Location: Downtown / Discreet Apt
Description:

"Young CD, new but eager to please. Slim, smooth, soft-spoken. Looking for generous men who appreciate femininity in all its forms. Light fetish-friendly. 100% discreet. No drama. Message me with your desires."

He read it over three times. It didn’t sound like him. But it didn’t have to. It sounded like her. The woman he was trying to become.

He hit Post.

His stomach knotted immediately. He was half-hard and half-ashamed. There was no coming back from this. He shut the laptop and slid it under the bed. Then he stood, peeled off his sweats, and walked to the mirror.

He started the transformation again, but this time with more intention.

A black lace bodysuit clung tight to his slim frame, the fabric sheer across the stomach, with a plunging neckline that barely held the stuffed bra in place. His stockings were laddered again—he made another mental note: buy new ones. He clipped on a makeshift garter belt, cheap elastic from Amazon. His heels were the only decent thing he owned—a pair of patent leather stilettos, black with red soles, scuffed but still deadly.

His makeup was improving. He spent an hour fixing it this time. He watched YouTube tutorials and followed every step. Contour, highlight, overline. Lipstick like blood on his mouth. Smoky eyes. Long lashes.

The person in the mirror was still Jesse. Still awkward. But under the dim yellow light, with the right angle, she looked like someone a man might pay to touch.

His phone buzzed.

A message.

“U host? 9pm tonight. 1 hr. Want you dressed. Heels and something slutty. $200 cash.”

He stared at the screen, frozen. His mouth went dry. Then he typed:

“Yes. I host. I’ll be ready.”

It was 6:40 PM.

---

By 8:30, the room reeked of dollar-store vanilla spray, trying and failing to mask the mildew creeping from the corners. Jesse had cleaned like a man possessed—scrubbed the bathroom sink with a sock, wiped the mirror with an old T-shirt. The bed was made, sort of. Sheets pulled tight over a dented mattress, throw blanket arranged like a showroom display.

His heart wouldn’t calm down. It ticked like a bomb behind his ribs.

He was fully dressed—or rather, fully undressed in the right ways. The red lace lingerie set was his boldest piece: a balconette bra, low-cut and straining around its tissue-and-sock filling; matching panties, high-cut to expose his narrow hips; and a garter belt that barely held up the new black stockings he’d stolen that morning from a boutique dressing room. They fit like sin. His heels made his legs look longer, thinner—almost elegant.

He wore a choker: faux leather with a tiny heart-shaped pendant. It made his throat feel smaller, tighter, more feminine.

He stared into the mirror for the hundredth time. His eyeliner had smudged slightly—he fixed it with a Q-tip dipped in spit. Foundation was caked in places, but under dim lighting, it passed. The cheap wig—brown with auburn streaks—sat slightly askew. He adjusted it. Again. Again.

Every time he looked away, it shifted back.

8:55.

The knock was soft. Just two taps.

His stomach flipped. He felt cold and flushed at the same time. He hesitated, staring at the door like it might explode. Then, mechanically, he walked over and opened it.

The man was older—mid-40s, maybe 50. Balding, tanned, with a gut pressing against a tight gray Henley. He looked Jesse up and down, then smiled, slow and casual.

“You’re Lacey?”

Jesse nodded. “Y-yeah. I host. I mean… yeah.”

The man stepped inside. Didn’t ask, didn’t wait. He looked around once, then tossed a wad of folded bills onto the nightstand.

“Cute voice,” he said, unzipping his jacket.

Jesse swallowed hard. “Thanks.”

The man sat on the edge of the bed and patted his thigh. “Come here.”

It was surreal, like watching someone else step forward. Jesse’s heels clicked softly on the floor as he crossed the room, every step a strange ballet of balance and shame. He sat beside the man, knees close together like he’d seen in videos. His garter strap tugged slightly at the lace hem of his panties.

The man reached out, fingers tracing Jesse’s thigh.

“First time?”

“…Yeah,” Jesse whispered.

The man grinned. “Don’t worry. I like ‘em fresh.”

Jesse forced a smile. His heart was a jackhammer. Every instinct screamed get out—but he didn’t move. Couldn’t. He just nodded, tucked a strand of fake hair behind his ear, and tried to disappear behind the makeup.

-

They didn’t kiss. Jesse was grateful for that.

He played his role—silent, pliant, breathing through the panic. The man grunted, praised his legs, called him “bitch” once, but not harshly. Jesse shut his eyes. Focused on the texture of the sheets. The heat of the man’s breath. The distant hum of the mini fridge.

When it was over, the man stood, pulled his pants up, and grabbed his jacket.

“Nice,” he said, like tipping a waitress. “Might hit you up again.”

Jesse didn’t answer. Just nodded.

The door closed.

Silence returned.

-

He stood on shaking legs and peeled the lace panties from his skin. There was a small tear along the seam now. His inner thighs were sticky. He didn’t cry—but he wanted to. Instead, he walked to the mirror.

The wig was slipping. Lipstick smeared. But under all the mess, he looked at the painted stranger staring back.

This is who I am now, he thought.

And maybe… just maybe… this girl might survive.

---

The door clicked shut behind the man, and Jesse stood frozen—heels still on, the scent of cologne and sweat clinging to every inch of his body. The room felt hollow now. Silent, but not peaceful. More like a crime scene after the sirens have faded.

He didn’t move until the tick of the clock on the microwave brought him back. 9:58 PM.

He peeled the lace panties down slowly. They stuck to his thighs. A smear of something white had leaked onto the gusset. The sight made his stomach turn.

In a trance, Jesse shuffled into the bathroom. The overhead light buzzed and flickered. The mirror above the sink caught his face—half-makeup, half-naked, a smear of red across his cheek like a wound. Lipstick. Or maybe his own shame. He didn’t know anymore.

He turned on the water. Hot. Too hot. Steam fogged the mirror. He stepped under it fully dressed in lingerie, letting the water hit his face, his chest, until it soaked through the padded bra and clung to him like a second skin. He slid down to his knees in the tub, still wearing the heels, and finally let the first sob out.

It came from somewhere deep—old pain, new guilt. The kind of crying that made his throat hurt. He scrubbed himself with a washcloth that smelled faintly of bleach, not caring how hard he rubbed. He dug it between his legs, up his thighs, into the soft, sore spots where the man’s hands had been.

Get it off. Get it off.

He was still crying as he stripped the rest of the lingerie off and dropped it in a heap beside the tub. The red lace bra looked so innocent in the pale bathroom light. Like it didn’t know what it had been part of.

Jesse wrapped his arms around himself and let the water run.

-

What did I just do?

The question wouldn’t leave him.

He’d sold his body to a stranger. Let a man touch him, fuck him—not violently, but purposefully. Jesse remembered the weight of the man’s hand on his thigh, the way his breath had caught when Jesse moaned. And he had moaned. Not just to please, but because part of it—God help him—felt good.

His own dick had strained against the panties. Hard. That was the worst part.

He clenched his jaw.

It hadn’t all been horror. It hadn’t all been survival. Somewhere in the performance, his body had responded. Heat. Tension. Pleasure. It crept up on him like a betrayal. When the man pressed against him, when his hands ran over Jesse’s stockinged legs, when he called him “good girl” in a voice so low it made his stomach twist—

Jesse wanted it.

Or at least, part of him had.

And that part scared the hell out of him.

Was it the power? The attention? Or… something deeper?

He tried to dissect the feelings like roadkill on a table. The man’s weight on him. The press of lips against his neck. The arousal in his own body—real, undeniable.

He had never kissed a man. Never been with one. Not like this. His porn history was erratic — girls in stockings, soft curves, and sometimes rougher stuff he didn’t talk about. But this? This was real.

Was he gay?

He didn’t think so.

Bi?

Maybe.

But no label could explain the war inside him—the push and pull between disgust and desire. He wasn’t supposed to want it. It was supposed to be a means to an end. Rent. Survival. Not... pleasure.

His crying slowed, but didn’t stop. He curled tighter under the spray, trembling. The water wasn’t hot anymore. Just lukewarm and loud.

He thought of the way the man looked at him. Like Jesse was something else. Not a man. Not exactly a woman. Just... useful. And for a brief, terrifying moment, Jesse had liked being that.

He’d felt beautiful. Filthy, yes. But powerful in a way he never had as just himself. Jesse was invisible. But Lacey—she made people stop and stare. She made them want.

And what did that say about him?

Who was he becoming?

-

He stayed in the shower until his fingers wrinkled, the floor puddled, and the hot water gave out completely.

When he stepped out, dripping, he avoided the mirror. He dried off slowly, wrapped the towel around his waist, and sat on the floor next to the discarded bra.

He didn’t know if he hated himself.

He didn’t know if he should.

---

Jesse didn’t sleep that night.

He lay on top of the covers in an old T-shirt and boxers—his boy clothes—staring at the ceiling like it might answer the questions twisting in his chest. The apartment was quiet except for the occasional drip from the bathroom faucet and the creak of old pipes. He felt like a ghost in his own space.

Every detail of the night replayed in his head like a fever dream: the man’s voice, the heat of his touch, the moment Jesse realized his own hips were moving—just slightly—in rhythm. And after, the way he’d collapsed in the shower, filthy and full of questions.

But now… now it was just stillness.

The money sat on the nightstand in a folded roll. Two hundred, crisp. More than he’d made in months.

He stared at it like it was something radioactive. Like it might burn through the wood and carve a hole into the floor.

-

Morning came like a blade through fog. Jesse pulled the curtains shut. Sunlight felt too honest.

By noon, he was back at the mirror—fresh-faced, shirtless, knees crossed beneath him. His laptop sat open beside him, muted video tutorials looping endlessly.

He tried again.

Foundation, blended with careful strokes. A bit of peach corrector under the eyes. Soft brown contour across the cheeks, jawline, and the slope of his nose. Mascara. Gloss. A nude lip this time, not the garish red from the night before. Less performative. Less whore, more real girl next door.

The wig was brushed out, pinned more securely. He wore a camisole this time—white satin with lace trim—and a pair of soft, pink cotton panties that hugged his hips with a delicate bow at the front. No garters. No heels. Just comfort. Just her.

He wasn’t dressing for a client.

He was dressing for himself.

And that scared him more than the sex.

-

He stood, paced, then opened the closet—really, just a bar hanging inside a half-broken wardrobe. Half his guy clothes. Half hers. The femme side was growing: a pair of black patent pumps, a navy pleated skirt, an off-shoulder knit dress he hadn’t dared wear yet.

He ran his hand over the fabric, fingers pausing on a pale pink silk blouse he’d found at a Goodwill six months ago. He took it off the hanger and slipped it on.

The way it draped over his frame—light, smooth, almost fluid—sent a shiver down his spine.

He looked in the mirror.

Lacey was getting clearer. Still blurry, still incomplete. But she was there.

A flicker of something passed through him. Not confidence. Not quite. More like… ownership. This body, this presentation—it was his. Not a performance. Not entirely.

That realization settled like a stone in his gut.

He remembered the man’s hands. The way he’d said “good girl” like it was a command, not a compliment. Jesse had played along. At first because he had to. Then because… something in him had wanted to.

Was that her?

Was that Lacey?

Did she like being wanted? Touched? Was he hiding behind her, or was she the one breaking free?

He sank onto the edge of the bed.

His hand slipped down between his legs.

He touched himself, slowly, tentatively—not with the urgency of shame like in the past, but with curiosity. Deliberately. The silk blouse brushed against his forearm as he moved, and the sensation of soft fabric and soft skin and soft moans twisted into something else entirely.

He pictured the man again. His voice. His breath. Not his face, but the way he’d taken Jesse.

And Jesse came—quiet, breathless, thighs trembling.

He didn’t cry this time.

But when it was over, he lay back and stared at the ceiling.

“I don’t know what the fuck I am anymore,” he whispered.

And there was no answer.

-

Later that night, he sat at his laptop. The escort site was still open. His ad had gotten four new messages. All of them crude. One offered more money.

He didn’t reply.

Not yet.

But he didn’t close the tab, either.

---

Jesse told himself he wouldn’t respond. Not yet.

But by nightfall, curiosity outweighed hesitation.

He clicked through the messages like someone flipping through a box of old matches—small things that could start fires if handled wrong.

One caught his eye:

“You were recommended. Discreet. Respectful. I like new girls. $250 for an hour. I want you soft. Pretty. No games.”

There was something about the wording. Direct, but not cruel. No dick pic. No weird demands. Just clear.

Jesse read it again. Then again.

And replied.

“I can do soft. What day?”

They set it for Thursday. Two days away.

-

He stood in front of the mirror in the dim yellow glow of his single bathroom bulb. The lace panties were navy blue tonight, high-waisted with a mesh back that clung between his cheeks in a way that made him feel… exposed. Honest. The matching bra was a padded demi-cup that gave him just enough shape to trick the eye in dim light. He layered a mesh chemise over it, a soft gray that hit mid-thigh, with tiny embroidered stars along the hem.

He’d read somewhere that softer presentation sold better if the client wanted “girlfriend vibes.” But this wasn’t about what they wanted anymore. Not entirely. It was about what felt right.

And this felt dangerously right.

He shaved again—everywhere. His chest, his legs, even the tops of his arms. The ritual took over an hour now. Skin smooth as silk. Hairless. Vulnerable.

-

He ventured out the next afternoon. Hood up, sunglasses on. He hit a cheap beauty store two blocks over and lingered in the lingerie aisle longer than he should have. No one said anything, but he felt the stares. Felt the heat crawling up his neck.

He bought a set: soft pink with tiny bows and delicate floral lace, clearly meant for someone smaller than him. But it called to him like a dare. Like it needed to be worn.

He also bought a peach lip gloss, a compact powder, and a bottle of light perfume—jasmine, vanilla, and something muskier underneath.

He didn’t recognize himself anymore.

That was both a relief and a curse.

-

The next night, Jesse stood fully dressed at the window. He didn’t turn on the lights.

He just watched the city buzz beneath him—cars groaning down cracked roads, people on corners making quick exchanges, women in miniskirts laughing too loudly with men who didn’t care about their names.

He pressed a hand to the cool glass.

Was that him now?

One of them?

He didn’t feel like a boy anymore. But he didn’t know how to be a woman either. Lacey was becoming more than a mask. She was creeping into his days. Into how he sat, how he moved, how he spoke to strangers.

He tried to remember when the lines between Jesse and Lacey were clear.

They weren’t anymore.

And maybe they never had been.

-

He dressed up again. Not for a client. Just for himself.

A white satin slip dress, barely holding to his slim shoulders. No bra. Just soft forms beneath. The new perfume dabbed at his neck and wrists.

He walked the length of his small apartment in low heels—three inches, manageable. Each step a performance. His hips swayed more easily now. He didn’t think about the movements anymore. They just happened.

In the mirror, he saw her again.

Not Jesse in drag.

Not a boy pretending.

But Lacey.

He whispered her name. Just once.

It didn’t feel fake.

It felt true.

And terrifying.

-

He sat down on the edge of the bed and checked his messages.

The man from Thursday had confirmed. “Bring that soft voice. I want to feel like I’m with a real girl.”

Jesse bit his lip. Heart fluttering.

He whispered to himself again, voice breathy and uncertain:
“I didn’t know I could feel like this.”

And meant it.

---

Thursday night arrived with a metallic taste in Jesse’s mouth.

He told himself he wasn’t nervous. Told himself this wasn’t like the first time. He knew the shape of it now—what to expect, how to act, how to survive. But his reflection said otherwise.

The mirror framed her perfectly.

Lacey.

The new lingerie set clung to her skin like it belonged there. Pale pink lace that dipped between her thighs, a bow teasing over the waistband. The underwire of the matching bra lifted her chest into a soft, convincing curve beneath the low neckline of a ribbed mauve bodycon dress. The dress was tight—obscenely so. It cinched in at the waist and rode high on the thighs. It said: Take me, but treat me gently.

She’d paired it with nude stockings and a soft cardigan that hung just off her shoulders. Pretty, subtle, safe.

The wig was secured tighter now. The loose waves framed her face in the soft light of the table lamp. A little blush. Peach gloss. Mascara, applied more confidently this time.

And the perfume.

Always the perfume.

She breathed in, and Jesse felt his stomach twist.

You’re not faking it anymore, he thought.

-

The knock came at 9:12 PM.

Three soft taps. Not like the last guy, who pounded the door like he owned it.

Lacey opened it slowly.

The man standing there was tall—clean-shaven, late 30s, blue suit jacket and loafers. Looked more like a banker than someone who’d pay for company. But his eyes said everything.

Hungry.

Curious.

Cautious.

“Hi,” Lacey said, voice soft. Breathier than Jesse’s, pitched just above his natural range.

The man smiled. “Lacey?”

She nodded.

“You’re beautiful.”

She lowered her gaze and stepped aside. “Come in.”

-

He was gentler. He didn’t rush. Didn’t paw at her. They talked first.

He asked her questions like she was a person.

Where are you from?
What music do you like?
You always dress this pretty?

She answered in vague truths. Let him build the fantasy. Let him believe.

And something strange happened.

She started believing it too.

-

When he touched her, it wasn’t frantic or animal. It was… delicate. Thoughtful. He ran his hands over her stockings like he was touching something sacred. His mouth brushed her neck. His breath sent goosebumps across her collarbones.

“You’re soft,” he whispered. “You smell amazing.”

Lacey’s heart beat faster.

She let him lay her back on the bed. She closed her eyes.

This time, when it started, she didn’t feel like she was watching herself from outside.

She was there.

Present.

He whispered things in her ear—sweet things, dirty things—and she responded. Her body arched for him. Her lips parted. She gave in, not because she had to…

But because she wanted to.

She came quietly this time. Not from his touch. From her own. But it happened while he was still inside her, and something about that—about being open and taken and real—shook her to her core.

After, she lay next to him in silence.

He didn’t leave right away.

He stroked her hair.

Told her she was beautiful again.

Left a tip in cash folded neatly under her perfume bottle.

And kissed her cheek before he walked out the door.

-

The moment it clicked shut, she was alone again.

Lacey slid down the wall and sat on the cold floor in her dress, heels still on, thighs slick, her heart echoing in her ears.

And for the first time, Jesse didn’t cry.

He felt…

Confused.

Shaken.

Alive.

And deeply, achingly lonely.

-

Later that night, wrapped in a bathrobe and clutching a mug of lukewarm tea, Jesse scrolled through his messages.

Another client had messaged.

Someone new.

But this time, Jesse didn’t respond right away.

He looked at his reflection in the dark window. Not the mirror. Just the black glass and his faint outline staring back.

Was he falling into this?

Or was he finally finding himself?

He didn’t know.

And that uncertainty terrified him more than any man ever could.

---

Jesse glanced sideways at Marissa as they walked down the cracked sidewalk, the summer heat pressing in like a heavy blanket. She was the one constant in his fractured world—his friend since high school, a spark of light in an otherwise dim city. Marissa was everything Jesse wasn’t: loud, confident, impossibly sure of herself, with wild curly hair that framed her freckled face and sharp hazel eyes that seemed to see right through him. She worked as a barista by day and an aspiring musician by night, always chasing dreams Jesse wasn’t sure he had anymore.

They’d been inseparable once. Now, every time he tried to confide in her, he felt the distance growing.

“Marissa,” Jesse said, voice low, uncertain. “I need to tell you something. Something I’ve never told anyone.”

She slowed, turning to face him, eyebrows knitting together. “Okay... shoot.”

He swallowed, feeling the words scrape raw inside. “I’ve been crossdressing for years. Not just for fun, not just sometimes… I live parts of my life as a girl. I dress up. I try to look pretty. But I keep it secret. Because I’m scared. Scared what people will think.”

Marissa’s eyes widened, surprise flickering across her face. “Wow. I... didn’t know.”

Jesse’s voice shook, a rush spilling out. “And it’s more than that. I’ve started escorting. I meet men. They pay me. I dress up—heels, stockings, lingerie, makeup that I’m still learning how to do right. It’s scary. It’s... complicated.”

He paused, heart hammering. “The first time... I was terrified. I didn’t know if I could do it. But when I was with them, in that moment, I felt... wanted. Like someone saw me for who I wanted to be, not the mess I am.”

His voice cracked. “But afterwards, I feel dirty. Used. I cry when I wash off their scent and the things they leave on me.”

He looked up, eyes searching hers. “I don’t know what to do with it. Or what it means about me.”

Marissa shifted uncomfortably, running a hand through her hair. “Jesse, that’s... a lot. I get wanting to explore yourself, but escorting? That’s dangerous. And... it sounds like you’re hurting yourself.”

Her words weren’t cruel, but her tone was heavy with worry and disbelief.

Jesse’s throat tightened. “I know. The money helps with rent. I’m drowning. But I guess part of me feels alive when I’m Lacey. Like I’m not just failing.”

Marissa shook her head slowly, voice softer now but firm. “You don’t have to do this alone. There’s other ways.”

Jesse swallowed hard, biting his lip. “Maybe. But I don’t see them.”

-

That night, Jesse sat on the edge of his bed, the glow of a new email harsh in the dark—a job offer, a real one. A receptionist position at a nonprofit, stable pay, benefits, a way out of this endless struggle.

But the thought of taking it felt like a betrayal. Taking it felt like giving up Lacey.

He stared at the phone, heart heavy with confusion.

-

Later, The Rusty Nail dive bar swallowed him whole. Sticky floors, buzzing neon signs flickering in and out, the stench of stale beer and sweat thick in the air. The music—a rough, grating mix of punk and blues—pounded against his ribs.

Jesse sat alone, glass in hand, the whiskey burning but somehow not enough. Each shot pulled the ache deeper inside him, mixing with the raw shame and longing that refused to quiet.

Then he saw him.

A young man, maybe early twenties, standing across the bar. Androgynous, with delicate features—a sharp jawline, high cheekbones, dark hair falling in soft waves. His loose white shirt hung off narrow shoulders; tight black jeans clung to long legs. He looked out of place in the grimy dive, but his eyes flicked to Jesse’s, curious and unafraid.

Jesse swallowed the lump in his throat and slid closer.

“Hey,” he slurred, voice thick with drink. “Want to dance? Or just... talk?”

The man hesitated, then nodded, a small smile touching his lips.

They moved toward the tiny dance floor, bodies awkward in the dim light. Jesse’s heart raced—not just from the booze, but from something deeper, a desperate hope.

His hands trembled as he reached out, brushing the man’s arm lightly.

The man’s skin was warm, soft.

Jesse leaned in, lips seeking connection.

The kiss was short, awkward—a misstep.

The man pulled back, eyes apologetic but firm.

“I’m sorry. Not interested.”

Jesse’s cheeks burned; humiliation tightened his throat. “Okay... I—”

But he pressed on, voice cracking. “Please. Just a chance.”

“No,” the man said again, stepping away.

Jesse stumbled back to the bar, head spinning. Shame and loneliness wrapped around him like a noose.

He stared at his reflection in the cracked mirror—lost, broken, invisible.

-

Outside, the humid night wrapped around Jesse like a suffocating shroud. He lit a cigarette with shaking hands, inhaling the acrid smoke deep.

“Who am I?” he whispered to the dark.

The night swallowed his words.

---

The next morning, Jesse woke with a headache like broken glass behind his eyes. The light filtering through his blinds felt like judgment. His phone buzzed—a message from Marissa.

“Can we talk? I didn’t sleep.”

He hesitated, thumb hovering over the screen. He hadn’t expected her to reach out again—not after everything he said. Not after the way she looked at him, torn between concern and confusion.

He typed back:

“Yeah. Come over.”

-

Marissa showed up just after noon, wearing a loose vintage tee, her curly hair bundled into a lazy bun. She looked tired but determined.

They sat on the couch, the silence long and strained. Jesse stared at his chipped coffee table. Marissa stared at him.

Finally, she spoke. “I’ve been thinking about what you told me.”

Jesse nodded but said nothing.

She leaned forward. “I know I was weird about it. It just… caught me off guard. But I don’t want to be that kind of friend. I want to understand.”

Jesse blinked. “Understand what?”

“All of it,” she said. “Not just the escorting. The dressing. The feelings. Who you are when you’re like that. I feel like I only know half of you.”

Something in her tone—honest, maybe even eager—made his chest tighten. “I don’t know if I know who I am when I’m like that,” he said softly.

Marissa sat back. “Then maybe we figure it out together.”

He stood slowly and walked toward the bedroom. Paused.

“Come with me,” he said.

-

Jesse opened the closet door and pushed aside the thrift-store hoodies and faded band tees. Behind them, hidden under an old sheet, was a black suitcase. He hesitated before opening it.

Marissa watched in silence.

Inside: delicate things. Pieces of himself he only allowed to exist in stolen hours and quiet rooms. Sheer thigh-highs folded neatly next to padded lace bras. A red satin corset, still creased from lack of use. High heels with scuffed soles. A soft pink wig curled in tissue paper. Lipstick tubes. A pair of long gloves. A black mesh bodysuit. A garter belt with gold clasps.

Marissa’s breath caught. “Wow.”

Jesse’s eyes didn’t meet hers. “I know. It’s a lot.”

“No,” she said quickly. “It’s... beautiful. Like a different person lives in this suitcase.”

He gave a dry laugh. “Sometimes it feels that way.”

Marissa knelt beside him, carefully lifting a pair of sheer panties with lace trim. “Do you actually wear all this? Like... full-on?”

“For the job.” His voice was low. “But not always. I’m still figuring out what works. Half the time I feel like a guy in drag. The other half... I feel like her. Like someone softer. Lacey.”

“Lacey,” Marissa repeated, running her fingers along the edge of a padded bra. “That’s the name?”

He nodded. “Yeah.”

She glanced at him sideways. “Do you enjoy it? I mean… being with men?”

He hesitated, the air suddenly too heavy. “The first time was terrifying. But… there’s this moment when I’m with someone, when I’m dressed, when he touches me, and it’s like… I disappear. Jesse disappears. And it feels good. Not just physically. It’s like I get to be wanted. Not for who I am, but for who I’ve created.”

Marissa was quiet for a long time. Then, carefully, she asked, “Do you like men?”

Jesse swallowed. “I don’t know. I don’t think I’d ever want a boyfriend. But when I’m Lacey... it’s different. The rules change.”

She nodded slowly, lips pursed, as she lifted a black mesh teddy. “Do you pick all this out yourself?”

“Yeah,” he said. “Mostly from second-hand shops. Online sometimes. I research stuff—watch tutorials. I’ve gotten better. It takes forever to get the makeup right. The first time I looked like a raccoon.”

Marissa laughed—sincerely. “I would’ve paid to see that.”

The tension eased a little.

She turned serious again, holding up the corset. “This is gorgeous. Do you wear this when you go out?”

“Sometimes. Depends on the client. Some like classy. Some like trashy. Some don’t care what I wear, as long as I act the part.”

She placed the corset down delicately, like it was something sacred. “And do you always act? Or is Lacey real?”

Jesse sat back on his heels. “I don’t know. She started as an escape. But lately... it’s harder to take her off.”

Marissa looked at him, softer now. “I didn’t expect to feel like this. I thought I’d be freaked out. But I’m... fascinated. Like I’m seeing you for the first time.”

He exhaled. “I was scared you’d hate me.”

“I don’t,” she said. “But I don’t fully understand either.”

“That’s okay,” he said. “I don’t expect you to.”

They sat in silence, the suitcase open like a confession between them.

-

That night, after Marissa left, Jesse stared at himself in the mirror—barefaced, unpainted. Just Jesse.

But her questions lingered. Her curiosity. The way her fingers had touched the lace like it meant something. She hadn’t run.

And that mattered more than he could admit.

---

The messages started just after dusk.

6:12 p.m.
“You’re available tonight, yeah? I want a real sissy. You fit that bill?”

Jesse stared at the screen, the glow lighting his gaunt features. He hadn’t eaten all day, again. His cheekbones were more prominent lately, and there was a hollowness beneath his eyes that no sleep could fix. He hadn’t shaved in two days, and he rubbed at the gritty stubble on his jaw, as if trying to scrub Jesse off his own face.

6:14 p.m.
“Send me a pic. Full outfit. I want to see you dolled up like a good little fucktoy.”

6:17 p.m.
“Wear something trashy. Leather, mesh, heels, no bra. Paint your mouth red. You’re not you tonight—you’re nothing but a wet hole.”

That last line clanged in his brain. Just a hole.

He could say no. Could turn off the phone, take the job offer, forget all of this.

But instead, he got up, moved to the case under his bed, and unzipped the suitcase that contained someone else entirely.

He dressed methodically. Black mesh bodysuit, tight enough to show everything. The leather miniskirt—high-waisted, worn low enough to flash the garters clipped to fishnet thigh-highs. He tucked, adjusted, cinched. Laced himself into a shape that wasn’t his own.

The wig tonight was sleek, raven-black, with a straight fringe and blunt ends at the jawline. It suited the mouth he painted blood-red—overdrawn, wet-looking, lewd.

Contouring hollowed out his cheeks. Lashes turned his eyes into something doe-like and filthy at once. He gave a practiced look in the mirror, half-lidded, pouty.

Lacey looked back. Jesse was gone.

-

The knock came at 8:47 p.m.

Lacey answered, standing tall in her heels—six inches of glossy black patent. The apartment smelled like perfume, latex, and nerves. She opened the door with the practiced grace of a girl who knew her place.

The man filled the doorway. Tall. Mid-forties. Worn boots. Stubble just beginning to gray. He had the look of someone who didn’t ask for things. He took them.

His eyes swept down her body slowly—stockings, skirt, mesh, lips. He let out a low whistle.

“Fuck,” he said. “You’re perfect.”

Lacey stepped aside. Her heels clicked on the floor, her posture demure but deliberate. She didn’t speak.

He walked in, unzipping his jacket and tossing it onto a chair without asking. He smelled like cigarettes, old leather, and something colder underneath.

“Turn around,” he said.

She did.

He chuckled darkly. “Nice ass. Bet it’s tight too.”

Lacey said nothing. That wasn’t what she was here for.

“Did you shave for me?”

She nodded.

“Good little slut. No talking unless I tell you.”

-

He didn’t waste time.

His hands grabbed her roughly, sliding under the mesh to grope at her chest, pinching through fabric. The bodysuit dug into her skin as he pulled her closer, tugging on the collar she’d buckled tight around her throat.

“You’re not a real girl,” he growled, lips brushing her ear. “But you fuck like one, don’t you?”

She swallowed. Her breath came shallow.

“You’re just a made-up little cumrag. No name. No past. Just a painted-up hole for real men to use.”

His hand slapped her ass, hard enough to sting. She flinched, but her body responded—heat coiling in her stomach, breath quickening. Shame clung to her like sweat.

“God, you’re already hard,” he laughed. “You fucking love this, don’t you?”

Lacey nodded.

“That’s what I thought. Dirty little thing.”

He bent her over the bed. The skirt flipped up, baring her ass. She heard the unbuckling of a belt. The tearing of a foil wrapper. She bit her lip so hard she tasted blood.

-

The room filled with filthy words. He called her every name he could think of—slut, freak, tranny, whore, hole. Some part of her flinched with each one.

And yet...

The deeper it went, the more her body betrayed her.

Her back arched. Her breath hitched. She moaned into the mattress. Each slap, each degrading whisper, made her feel less like Jesse and more like something else entirely.

It was the most humiliating thing she’d ever done.
And she wanted more.

When he finally finished, he pulled out, slapped her ass once more, and stood up without a word. She stayed face down on the bed, legs shaking, lips swollen, makeup a ruined mess across her cheeks.

-

He lit a cigarette at the door.

“You’re a filthy bitch,” he said. “You enjoyed that.”

She said nothing.

He fished into his wallet, pulled out several folded bills, and tossed them onto the table.

“Buy something pretty,” he said, smirking.

She looked up, mascara streaking down her cheeks.

He added, almost as an afterthought, “But I want pics. Lacey better send me something nice.”

Then he was gone.

-

The silence hit like a gunshot. She sat up, her body aching, thighs sticky with lube and spit and something darker. Her own cum.

The collar felt tighter now.

Lacey peeled off her wig and tossed it to the floor. One lash came off with it, fluttering to the floor like a black insect.

Jesse crawled to the bathroom. The heels were too much. His knees scraped the tile.

He turned on the tap and started to scrub. His hands shook. Water turned gray with foundation, lipstick, and sweat.

Then came the smell—his body, the man’s cologne, the inside of his mouth, all clinging to his skin. He gagged.

He cried quietly, crouched under the sink. His ribs shook with every breath.

Buy something pretty.
I want pics.

He pressed his forehead to the tile.

He hated what he had become.
And hated that part of him—deep, raw, trembling—wanted to do it again.