Target

The Target parking lot baked under late-morning sun, rows of minivans and SUVs glinting like armor. Elena locked the car, slinging a small purse over her shoulder. Jordan’s heart hammered—crop top riding high, shorts loose but riding higher when he walked, white crew socks and sneakers scuffed. The cherry gloss still tasted on his lips; Alex’s number burned in his phone. Just a dress, he told himself. In and out. The asphalt radiated heat through his sneakers, the air thick with exhaust and distant barbecue.

Elena’s hand found his lower back, guiding him through the automatic doors. Cool air hit like a slap, carrying the scent of popcorn and plastic. Red-shirted employees bustled; families pushed carts loaded with back-to-school supplies. He tugged the hem of his crop top lower—pointless, the faded logo still sitting an inch above his navel—and followed her into Target’s Saturday-morning chaos. Kids screamed near the toy aisle, carts clattering, some pop song leaked from hidden speakers. His pulse was already sprinting.

Elena’s hand settled at the small of his back, thumb brushing bare skin. “Breathe, Joanne,” she murmured, lips close to his ear. “You look adorable. No one’s staring.”

They were—at a shy, cute coed, not a man dressed in girl's clothing. A teenage boy pushing a flatbed of boxed furniture did a double-take, eyes flicking from Jordan’s legs to his face, then away—liking what he saw. Heat flooded Jordan's cheeks. The shorts snug, the frayed hem tickling his thighs with every step.

She steered him past the grocery endcap, straight to women’s clothing. Racks of sundresses and cropped tees blurred together. Elena plucked a simple navy wrap dress from a hanger—knee-length, modest neckline, exactly what they came for. “Let's start here,” she said, pressing it into his arms. “But we’re not stopping at one dress.”

Jordan’s stomach turned. “What do you mea—”

She stopped him with a look, then softened it into a smile. “Sarah already thinks you’re Jordan’s younger sister, visiting us for few days. We keep the story airtight for the whole week. You in?”

He swallowed. The lie from last night still tasted metallic on his tongue. “A week?”

“Seven days.” Elena’s fingers tightened on his hip. “You’ll thank me.” Not waiting for an answer, she loaded the basket: a soft pink pajama set with tiny white hearts, padded bras, matching hipster panties with discreet lace trim, low-heeled black flats. A denim skirt. A cropped hoodie. Then, from the hangers, a bright orange sundress—square neck, knee-length. “For picnics, and dates,” she said, winking.

The fitting rooms sat at the back, past housewares. A mom corralled two toddlers ahead of them; the attendant handed Elena a plastic “5” and waved them through. The hallway smelled like new plastic and lemon cleaner. Elena chose the largest stall, locked the door, and hung the navy dress on the hook.

“Strip,” she said, voice low.

Jordan peeled off the crop top, and took off the borrowed bra. The air-conditioning kissed his nipples; they tightened instantly. His reflection in the mirror showed a stranger—narrow shoulders, smooth chest, the faint outline of ribs. Elena’s eyes tracked every inch. She stepped behind him, palms sliding down his sides, thumbs hooking into the waistband of the denim shorts.

The denim slid down. He stepped out, socks bunching at his ankles. He stood in nothing but Elena’s panties—already damp at the front. His cock strained against the fabric. Shame burned hot and sweet.

Elena’s fingers traced the waistband. “Look at you,” she said. “Hard already. Good girl.”

He whimpered. The word girl landed like a slap and a kiss at once.

She handed him the padded bra. He fumbled with the clasp; she helped, adjusting the cups until soft foam pressed against his flat chest, giving the illusion of gentle curves. The mirror showed a nervous girl in her first push-up bra. His throat closed.

Next, the matching panties. He slid Elena’s down his thighs; his cock sprang free, flushed and leaking. The new pair was snugger, lace scratching lightly against sensitive skin. The padding in back rounded his ass. Elena cupped it, squeezed.

“Perfect,” she breathed.

The navy wrap dress whispered over his head, fabric cool against overheated skin. It tied at the waist, skimmed his hips, ended just above the knee. Simple. Elegant. His reflection looked normal. Pretty, even.

Elena’s smile turned wicked. “Now the fun stuff.”

She made him try everything.

The pajama set first—shorts so tiny the curve of his ass peeked beneath, camisole clinging to the fake breasts. He caught his own wide eyes in the mirror and felt dizzy. Elena knelt, mouth brushing the inside of his thigh through the thin cotton. “Imagine sleeping in these all week,” she said. “Waking up hard, knowing I dressed you.”

He moaned before he could stop himself. The sound bounced off the stall walls.

Denim skirt next—mid-thigh, frayed like the shorts but tighter. It rode when he bent. Elena spun him, palms skating up bare legs, stopping just shy of where the lace ended. “Bend over,” she ordered. He did. The skirt lifted; cool air hit his ass. Her finger traced the cleft through the panties. “Anyone in the hallway could hear you right now,” she said. “If you make noise.”

He bit his lip until it stung.

The cropped hoodie was soft, oversized, but cropped high. The flats pinched his toes, but they lifted his posture just enough, made his legs look longer. Elena watched him walk the narrow stall, hips swaying without permission. Every step rubbed lace against his cock.

She saved the casual outfit for last: high-waisted jeans that hugged his padded hips, a ribbed white tank that clung to his fake curves, and a lightweight cardigan in pale lavender. He looked like he belonged on a campus quad, not in a married man’s life. The jeans pressed the padding tight; every movement reminded him what was underneath.

Elena crowded him against the mirror, hands sliding under the tank. “We’re buying it all. And you’re wearing the jeans outfit out. The blue dress for tonight. Joanne is here to stay until next Sunday.”

His knees buckled. “Elena, please—”

“Say yes.”

He swallowed. “Yes.”

She kissed him hard, tongue claiming, teeth nipping his lower lip. When she pulled back, his lipstick—hers, applied in the car—was smeared. She wiped it with her thumb, then licked it clean.

Outside the stall, the attendant chatted with another shopper. Laughter. His heart hammered so loud he was sure they heard it.

Elena gathered the tags, ripped them free with small scissors from her purse. “I’ll pay.”

He stepped into the hallway in the new jeans, new top, new skin. The cardigan sleeves swallowed his hands. He caught his reflection in the security mirror—wide-eyed, flushed, unmistakably feminine. A middle-aged woman near the socks glanced over, smiled politely like he was just another Target girl. His stomach flipped.

At the register, Elena chatted with the cashier about the weather while Jordan stood silent, arms crossed over the soft swell of padded breasts. The total climbed—$312.63. Elena swiped her card without blinking. The cashier bagged everything in pink plastic, handed it over.

“Have a nice day,” she told Jordan with a wink.

He managed a squeaky “Thanks.”

Back in the parking lot, the noon sun was brutal. Asphalt radiated heat up his bare ankles. Elena opened the passenger door, guided him in. The seatbelt crossed between the bralette cups. She leaned over, buckled him, kissed his temple.

“Sarah’s at six,” she said. “Then home. Then I unwrap my sister-in-law properly.”

His cock throbbed against padded lace. He stared at his painted toenails—Elena’s idea, done in the car—peeking from the flats.

She started the engine. “Choice time, Joanne.” He blinked. “Choice?”

She grinned. “We have six hours before dinner. Option one: we go for lunch, we stop at the park, take a walk in daylight, let the world see Joanne. Option two: we go home, I edge you until you beg. Option three: you message Alex, and invite him for a lunch date.”