Cheap Straight Man Tries a Crossdresser

The sodium lamps along the industrial strip threw a sick orange light over cracked asphalt and chain-link, and Magnus drove slow in the old pickup, elbow out the window, radio barely a murmur. Forty-two, forearms still gray with drywall dust from a day of framing houses he would never own, he carried his cheapness the way other men carried a wallet. He did not want a motel. He did not want a woman who knew what she was worth. He wanted the lowest end of the street, the ones who looked at his rusted truck and did not laugh him off, and he wanted them for less than a tank of gas.

He rolled past the first corner and saw Paulina under the awning of a closed welding shop. Thirty, she looked, though the night and the cheap mascara dragged lines around her mouth. A denim skirt washed thin, heels that wobbled on the curb. When he stopped she came over with the tired smile of a woman already turned down twice.

"You looking, baby?" Smoke and gravel in the voice.

"Depends what you're asking." He kept both hands on the wheel. Straight as a nail, he liked to tell himself, and he liked women just fine when the price was right. "Quick one in the truck. What's the rate?"

Paulina leaned on the door. Cigarette smoke and drugstore perfume. "Forty for the mouth. Sixty if you want more. I'm not doing bare for less than eighty, and even then I think about it."

He snorted. "Forty for head? I've seen better deals behind the lumber yard. Twenty."

"Twenty won't buy you a handshake." Some of the smile left. "I'm desperate, honey, not free. Thirty-five and I'll make it good. I've got rent."

"Thirty-five is still too much." He looked her over, the worn knees, the chipped polish, the way she kept glancing down the dark like a cop might step out of it. Lowest end, sure. Not low enough. "Maybe next time."

"Cheap bastard," Paulina muttered, stepping back. She did not chase the truck. Women like her had learned not to run after men who haggled like they were buying scrap.

He drove two blocks, past a lot of stripped cars, and found Giselle near a flickering light by the railroad spur. Twenty-eight, she said when he asked, like the number might sweeten anything. Thinner than Paulina, red tank top, skirt so short the night air raised goosebumps on her thighs. Sharp tired eyes. She was at the window before he fully stopped.

"You cruising or you lost?"

"Cruising. What do you charge?"

"Mouth's thirty. Full service fifty. I'm not proud tonight." Flat, no performance. "Cash up front. I'm not getting stiffed by another construction guy who thinks his dick is a coupon."

Magnus almost laughed. "Thirty for a blowjob in a truck that smells like sawdust. That's rock bottom to you?"

"That's eating tomorrow." She tapped the door with a bitten nail. "You want cheaper, go find a ghost. I'm already the bargain."

The offer sat in his gut like a temptation he refused on principle. Thirty was less than Paulina. Still too much. Forty dollars in the wallet, and he hated spending more than half of it on anything that did not keep the truck running. "Twenty. I'll throw in a cigarette."

Giselle's mouth tightened. "Get lost, then. I'm worn out, not stupid." She pushed off the door and walked back toward the light, hips swinging out of habit more than hope.

Magnus put the truck in gear. The tightness in his jeans had not gone anywhere. He wanted a mouth. He wanted it cheap enough that he could tell himself he had won. He rolled on, deeper into the stretch where the warehouses ended and the streetlights started to die, looking for something even lower than the women the street had already used up.

The last working lamp on the block buzzed and stuttered over a patch of oil-stained concrete, and under it stood somebody Magnus almost drove past. Then the figure lifted a hand, lazy, and the cheap blonde wig caught the flicker. Tight black mini-dress, hem high on long legs, heels scuffed at the toes. Heavy makeup, lipstick a little smeared at one corner, lashes thick enough to cast shadow. Twenty-five, if Magnus had to guess, and desperate in a way that showed in the posture more than the clothes: shoulders a touch hunched against the cold, weight shifted like standing still cost money.

Magnus slowed. Up close the jaw was a man's jaw under the powder, the throat a little too thick for the choker, the hands large where they rested on the thigh. A crossdresser working the same curb the women had given up on. Magnus's first instinct was to keep rolling. He liked women. He had always liked women. Then the mouth opened, painted and filthy, and the voice that came out was low and rough and completely unashamed.

"You lost, daddy, or you just cheap?" Sergio said, stepping to the window. The wig slipped a fraction. He did not fix it. "Name's Sergio. Twenty-five, if you're the type who asks before you spend. Everybody else drove past me tonight. You stopped. That means you're hunting a deal."

"I don't do guys," Magnus said. His eyes stayed on the mouth anyway. Full lower lip, gloss catching the orange light, the kind of mouth that looked like it knew work.

Sergio laughed, short and dirty. "You don't have to do a guy. You have to do a mouth. Mine works the same as any woman's. Better, if she's tired and I'm hungry. I suck cock like I get paid to live, because I do. No teeth unless you beg. Throat all the way if you don't yank. You can call me whatever gets you hard. I don't care what you tell yourself in the morning."

Magnus's cock gave a thick, traitorous pulse against his zipper. The idea landed mean and simple: head, almost nothing, a mouth that promised to work. He had turned down two women for less humiliation than this, and the humiliation was doing something to him he did not want to name. "How much?"

"Fifteen," Sergio said, immediately, like he had been waiting to undercut the whole street. "Mouth, in the truck, you finish wherever you want as long as it's not in my wig. Twenty if you want my ass, and I'll bend over right here if you're too proud to park. Bare if you're clean enough not to lie about it. I'm not playing nurse. I'm playing cheap."

Fifteen. Less than a pack and a coffee. Magnus's hands tightened on the wheel. He could already picture that painted mouth stretched around him, the wet sounds, the way a bargain felt better than the thing itself. His pulse knocked in his throat. Straight, he told himself. Just a mouth. Just a hole that talked filthy and cost nothing.

"Get in," he said. The words came out rougher than he meant. "Don't touch the radio."

Sergio's smirk went bright and mean. He came around the hood, heels clicking, and climbed into the passenger seat with the mini-dress riding so high Magnus saw the dark line of cheap panties and the soft shape of a cock tucked under them. The cab filled with hairspray, sweat, and the sweet chemical smell of lipstick. Sergio shut the door and looked at him sideways, lashes low.

"Drive somewhere dark," he said. "And keep your money where I can see you didn't forget it. I'm desperate, not new."

Magnus pulled away from the dying light, cock already thick against his thigh, the cheapest decision of the night sitting right beside him and smelling like a woman he could almost pretend was one.

He took the alley behind the old mattress warehouse, where the dumpsters blocked the view from the street and the only light was a security lamp with a cracked cover, throwing everything into hard bars of white and black. He killed the engine. The tick of cooling metal was loud. Sergio did not wait to be told. He slid across the bench seat, one hand already on Magnus's belt, the other braced on a dusty thigh.

"Fifteen gets you this," Sergio said, voice gone husky. "You want more, you say so before you blow. I don't do refunds and I don't do shy."

"Just shut up and use that mouth," Magnus said, but his hips had already lifted so the belt could come loose. Consent sat plain between them, ugly and mutual: Sergio wanted the cash and the cock, Magnus wanted the release without spending like a man who had any pride left. Neither of them was drunk. Neither of them was guessing.

Sergio got the jeans open with practiced fingers and dragged them down with the boxers. Magnus's cock sprang up thick and flushed, the head already wet, veins standing along the shaft from all that denied haggling. Forty-two years of swinging a hammer had not made him pretty, but it had made him heavy, and Sergio made a low hungry sound at the sight of it.

"Fuck, that's a working man's dick," he murmured, and then he dropped. Not onto the seat. Out of the truck, knees on the alley grit, dress hiked, wig tilted, face tipped up between Magnus's spread thighs where the door hung open. The night air hit Magnus's bare skin. Sergio's mouth hit hotter.

The first lick was slow and showy, tongue flat up the underside, gathering the salt at the slit and smearing lipstick along the ridge. Then Sergio sealed his lips around the head and sank, wet and sudden, taking half the length in one greedy slide. Heat. Suction. A slick tongue working the frenulum like he had mapped it on a dozen cheaper men before this one. Magnus's hand found the cheap wig and fisted it without thinking. The hairpiece shifted. He did not care. Sergio moaned around him, the vibration running straight into his balls, and bobbed, sloppy on purpose, spit already shining on his chin and dripping onto the dusty floor mat.

"Jesus," Magnus gritted. The mouth was as good as promised. Better than Paulina would have been at twice the price, better than Giselle's tired offer, a warm wet glove that knew when to hollow the cheeks and when to gag itself deeper just to hear him curse. Sergio took him to the back of the throat and held, eyes watering, mascara starting to run, throat fluttering around the head. He pulled off with a filthy string of spit, stroked the wet shaft with a big hand, and went down again, faster, noisier, the sounds obscene in the quiet alley. Slurp. Gag. A wet pop when he came up for air and immediately chased the cock back in like he was starving for it.

Magnus watched the painted lips stretch, the heavy makeup smearing, the man's throat working, and something in him snapped past the lie he had been telling. Turned on. Fully, meanly turned on. Not despite the wig and the dress. Because of the performance of them, the cheap costume wrapped around a mouth that worked, and the body kneeling in the dirt like it had been built to be used for fifteen dollars and a little cruelty. His balls drew tight. He was not going to waste this in a throat when there was more on offer for almost nothing.

"Up," he said, voice wrecked. "Ass. Now. On the hood."

Sergio pulled off, lips swollen, chin shining. He grinned with cum-slick spit on his teeth. "Twenty total, then. Bare. I want it. Don't go gentle and don't pretend you didn't ask."

"I asked." Magnus hauled his jeans up just enough to walk, cock jutting, and came around the front of the truck. The hood was warm from the drive, gritty under his palms. "Bend over. Dress up. Panties down. You push back or I stop. That's the deal."

"Deal," Sergio said, already moving. He planted his hands on the hood, arched, and let Magnus yank the mini-dress to his waist. The cheap panties were damp at the front where Sergio's own cock had leaked against the fabric. Magnus dragged them down to mid-thigh. Sergio's ass was bare to the alley, smooth enough that he must have shaved, hole pink and tight between firm cheeks, his cock hanging half-hard beneath, painted nails scratching at the paint of the truck. Twenty-five, willing, looking back over one shoulder with ruined mascara and a challenge in his eyes.

"Spit," Sergio said. "Or use mine. I'm not carrying lube on a night this broke. Just get in me. I can take a raw fuck. I want to feel every inch of that cheap bastard cock."

Magnus spat into his palm, slicked himself, spat again against the hole and worked two rough fingers in because he was not interested in tearing anything he had not paid to ruin. Sergio hissed and pushed back onto the fingers, greedy, opening, the muscle fluttering and then giving. "Enough. Fuck me. Put it in."

He lined up and drove in.

The first thrust sank halfway, tight heat clamping around him so hard his vision sparked. Bare. Nothing between his cock and that clutching ass but spit and want. Sergio cried out, a high broken sound that did not match the low voice, and shoved backward, taking the rest in one desperate roll of his hips until Magnus's balls slapped skin. Buried. Raw. The crossdresser's hole gripped him like a fist in a velvet glove, hotter than the mouth, deeper, fluttering every time Magnus held still for half a second.

"Move," Sergio gasped. "Don't you dare just sit there. Fuck me like you paid for the whole night and you're mad about the price."

Magnus grabbed the narrow waist, dress bunched in his fists, and started to pound. Hard. Dominant. The truck rocked on its shocks. Each stroke dragged almost out and slammed home, the wet smack of hips on ass echoing off the warehouse wall, spit and slick making the friction filthy and perfect. Sergio's hole stretched around the thick shaft, clinging on the out-stroke, swallowing him on the in. Magnus watched himself disappear into that painted, willing body and felt the last of his hesitation burn off. Straight man, cheapest hole on the street, and he was fucking it like he had been starving.

"That's it," he growled, one hand leaving the waist to shove Sergio's chest flatter against the hood. "Take it. Push back. You wanted a working man's dick, you earn it."

Sergio earned it. He braced his heels, arched harder, and met every thrust, ass slapping back into Magnus's groin, moans spilling out of him without shame. "Fuck, yes, deeper, right there, ruin me, I can feel you in my stomach, don't stop, don't you fucking stop." His own cock swung and slapped his belly, fully hard now, dripping onto the bumper. The wig had fallen sideways. Makeup ran in black tracks. He looked wrecked and he sounded grateful, shoving himself onto the bare cock like the pounding was the only warm thing that had happened to him all week.

Magnus fucked him harder. The alley filled with the rhythmic knock of the truck, Sergio's broken moans, the wet filthy sound of a raw ass being used. Sweat slicked Magnus's chest under the work shirt. His balls swung heavy, smacking Sergio's taint, each impact sending a jolt up his spine. He reached under and found Sergio's cock, not gentle, just a rough stroke to feel how hard the man was from being bent over and bred open. Sergio sobbed a laugh and pushed back harder.

"You like that," Magnus said, not a question. "Cheap little crossdressing whore, taking it bare on a hood for twenty bucks. Your hole's sucking me in. You were made for this."

"I was made for getting paid," Sergio panted, but his voice cracked on the next thrust, and he ground back in a circle that made Magnus's knees threaten to buckle. "And I like it. I like your cock. I like you using me. Cum in me or on me, I don't care, just don't pull the money. Fuck, harder, Magnus, harder."

He had not given his name. Sergio must have heard it somewhere, or guessed from the way men like him introduced themselves when they thought they were in charge. It did not matter. Magnus set his feet and gave him harder. Long brutal strokes that punched the air out of Sergio's lungs, then short grinding ones that kept the head rubbing deep, then long again until the slap of skin was constant. Sergio's arms shook. His hole spasmed, clenching in rhythmic pulses that milked Magnus from base to tip. Precum and spit slicked Magnus's balls. The smell of sex and alley dust and cheap perfume rose thick between them.

Magnus felt the orgasm gathering low, a hot wire pulling tight. Too soon if he wanted to pretend he had control, perfect if he wanted to finish like the cheap man he was. He fucked through it for another dozen strokes, chasing the edge, watching Sergio's back bow, the dress wrinkled beyond saving, the panties tangled at his knees, the willing body taking every inch raw and asking for more with the roll of his hips.

"I'm close," he snarled. "On your knees. Face up. I want it on you."

He pulled out in one slick drag. Sergio whimpered at the sudden empty ache, hole fluttering open and wet, then scrambled off the hood because he had agreed and because he wanted to see it. Magnus spun him by the shoulder. Sergio dropped to the concrete, knees hitting hard, wig finally giving up and hanging from one pin, face tilted up, mouth open, tongue out, mascara ruined, lipstick a red smear. His cock jutted, flushed and leaking, and he did not touch it. He just waited, chest heaving, eyes bright and wrecked and eager.

Magnus stroked himself twice, three times, the shaft gleaming with spit and the tight clutch of Sergio's ass, and came.

The first rope hit Sergio across the mouth and cheek, thick and hot, striping the tongue he had offered. The second landed over one eye, clotting in the lashes. Magnus groaned, deep and helpless, and kept stroking, painting the upturned face in heavy white streaks: nose, lips, chin, a fat pearl dripping from the jaw onto the choker. Sergio held still for it, moaning, letting the cum coat him, then licked what reached his mouth and smiled like a man who had won a bet with the night. Magnus's knees shook. He milked the last of it onto Sergio's forehead and stood there, cock twitching, staring at the mess he had made of the cheapest thing on the street.

"Fuck," he said, wrecked. "Look at you."

Sergio blinked through cum and mascara, still catching his breath, still on his knees in the alley grit. "I'm looking at you," he said, voice hoarse and pleased. "And you look like a man who just found a new low."

Magnus tucked himself away with hands that were not quite steady and zipped up. The night air cooled the sweat on his neck. He dug in his pocket, came out with a crumpled ten and a five and a few singles that might have been laundry money, and tossed the wad onto the concrete between Sergio's knees. It landed half on a smear of dust, half against a bare thigh. Twenty, more or less. He did not count it twice.

"Stay down there till I'm gone," he said, already walking to the driver's side. His voice had its cheapness back, the bark of a man who had gotten more than he paid for and intended to pretend it was nothing. "I'm not your ride home."

Sergio laughed, breathless, and dragged the back of one wrist across his cheek, smearing cum into a shiny streak he did not bother to hide. The smirk stayed. Satisfied. Used and paid and already calculating the next curb. Magnus climbed in, started the truck, and backed out of the alley with the radio still off. The headlights swept over Sergio once: knees apart, dress rucked up, face glazed, eyes following the taillights like they might turn around. They did not. Magnus pointed the pickup toward the darker end of the industrial strip, cock still sensitive against his zipper, mind already turning over the next block, the next desperate price, the next mouth that might work for even less. He could still smell lipstick on his fingers. He did not wipe them.

In the side mirror, small and then smaller, Sergio stayed where he had been left, wiping his face with that same filthy smirk, counting the crumpled bills with his other hand. The alley took him. The street opened up. Magnus rolled the window down and let the night hit his face, already hungry again, already cheap, already sure he would be back on these curbs before the week was out.

A voice carried after the truck, rough and bright and utterly unashamed, the last thing the alley gave him.

"Same price tomorrow if you bring that cock back, or are you gonna get even cheaper on me?"