Aunt and Nieces Teach Me to Fuck

Silas had always known the unspoken rules in his step-aunt’s house, even when they left his cock straining against whatever pair of silky panties they picked for him. At twenty-two he had spent years being lovingly feminized by his thirty-eight-year-old step-aunt Josephine and her two twenty-four-year-old step-daughters, Francesca and Bianca. They dressed him in their lingerie—lace bras cupping nothing but skin, panties so snug they traced every ridge of his dick and the heavy hang of his balls—then eased him into clinging dresses, buckled him into heels that arched his feet and swayed his hips, settled long wigs over his shoulders, and painted his face until the mirror showed a sexy girl. They taught him how to move, the slow roll of his pelvis, how to speak in a softer, breathier voice, how to sit and glance and behave like someone who wanted to be looked at and touched. The constant cross-dressing created a deep sexual tension none of them had acted on, a thick heat that rose whenever Josephine’s fingers brushed the inside of his thigh while she straightened a stocking or when the sisters laughed and tugged his panties lower to admire the bulge they refused to hide. That tension had simmered, unspoken and aching, ever since he turned twenty; all of them pretended it was only dress-up until the night he walked in on Francesca and Bianca eagerly fucking each other with strap-ons.

He was still in the red lace and black wig they had put on him after dinner, heels clicking on the hall floor, when he pushed the bedroom door open. Francesca knelt behind Bianca on the wide bed, a thick flesh-toned strap-on buckled tight at her hips, driving it into her sister’s soaked pussy with hungry, wet strokes. Bianca’s face was buried in the sheets, ass raised, moans open and shameless, her own harness tossed aside. Sweat shone on their skin, breasts swaying, nipples tight. They did not stop when they saw him. Francesca only slowed, letting the glistening cock slide almost free before sinking it deep again, and grinned over her shoulder.

Francesca’s voice was husky with pleasure. “Come here, pretty girl. You’re finally old enough to be taught more. Get on this bed and taste what you’ve been dressing up for all these years.”

Silas crossed the room without hesitation, cock already rigid inside the lace. They pulled him between them, kissed the makeup from his mouth, then guided his face down. He ate Bianca first, tongue tracing the slick length of the withdrawing strap-on before plunging into her pussy, lapping the flood of her juices while Francesca kept a steady rhythm that pushed more flavor onto his tongue. Bianca came with a sharp cry, thighs clamping around his head. They switched at once. Francesca straddled his face, grinding her wet cunt over his lips, the bobbing strap-on brushing his wig as he sucked her clit and licked until she shuddered and soaked his chin. Only then did they free his cock. It sprang up, flushed and leaking. Francesca sank onto it, hot and tight, riding with rolling hips while Bianca kissed him and pinched his nipples through the bra, calling him their good girl. They took turns, Bianca’s ride slower and deeper, clenching around him until he felt every ripple. He came hard the second time she took him, pulsing thick inside her, and they kept moving until he was spent, trembling, lipstick smeared, wig tangled, happier than he had ever been.

Josephine’s voice cut through the afterglow from the doorway. She stood there at thirty-eight, work blouse still buttoned, eyes dark with something hotter than surprise. “Girls. Out. Now.” Francesca and Bianca slipped off him, grabbing robes, but they smiled at Silas as they left. Josephine locked the door. She looked down at her step-nephew sprawled in ruined lingerie, cum drying on his stomach, face shiny with her daughters’ pussy. “So this is what you’ve all been building toward. Come here, sweetheart. Your aunt is going to finish what they started.”

For the next month she kept him entirely to herself. Every night she dressed him—stockings, corset, the wig she liked best—and fucked him with slow, intense hunger. She rode his cock while he sucked her tits, made him eat her until his jaw ached, taught him how to arch and moan like a girl when her fingers pressed into him, how to beg in that softened voice for more. She never let the step-nieces join during those weeks, deepening every lesson until Silas moved, spoke, and came exactly like the hot girl they had always seen in him. At the end of the month she called Francesca and Bianca into the bedroom where he knelt in full makeup and a tiny dress. “He’s ready,” Josephine said. “It’s time we teach him how to fuck like a hot slut.”

Francesca and Bianca invited two of his friends the following evening. Cedric, twenty-three, and Liam, twenty-four, had dropped by more than once while Silas was dolled up and had repeatedly said how hot she looked, how they wouldn’t mind if the pretty thing ever wanted to play. They arrived already hard, cocks outlined in their jeans. The women had Silas ready in a sheer babydoll, lace panties, heels, and flawless makeup, wig falling straight down his back.

“On your knees, baby girl,” Bianca said, guiding him onto the rug while the men watched and freed themselves. “We’re going to teach you how to suck cock the way a hot slut should.” Cedric stepped forward first, thick and curved. Francesca wrapped Silas’s fingers around the base, showed him the angle, then pressed the head to his glossy lips. “Open. Tongue first.” Silas opened eagerly, licking the salty slit, then taking the head in, cheeks hollowing as Bianca coached every motion. “Deeper. Relax your throat. Good girl.” He bobbed, spit slicking the shaft, until Cedric groaned and pulled free so Liam could take a turn. Liam was longer, smoother. Silas alternated between the two hard dicks, sucking one while his hand stroked the other, the nieces’ fingers in his hair or under his chin, correcting him, praising every wet slurp and soft gag. They made him deepthroat both, holding him down until his nose met skin and mascara smudged, then letting him gasp before pushing him back onto the next cock. When Cedric warned he was close, Francesca kept Silas sealed around him. The first thick load flooded his tongue; he swallowed, throat working, a little leaking from the corner of his painted mouth until Bianca wiped it and fed it back between his lips. Liam lasted only minutes longer. Silas sucked him sloppy and deep until another hot pulse filled his mouth and he drank that down too, licking the slit clean while both men shuddered.

They bent him over the couch at once. Josephine flipped the babydoll up; Francesca tugged the panties aside. They lubed his ass in generous, glistening strokes, fingers working him open while he moaned. “This hungry little pussy needs cock,” Bianca murmured, scissoring two fingers inside him. Liam moved behind, hard again, and pushed in slow. The stretch burned then melted into fullness as his dick sank all the way into Silas’s lubed ass—his pussy—until hips pressed flush to ass. Cedric knelt on the cushions in front and fed his renewed erection back into Silas’s mouth. They spit-roasted him hard. Liam fucked his ass with deep, driving strokes that jolted him forward onto Cedric’s cock; Cedric thrust into his throat, using his mouth like the second hole it had become. Spit ran down Silas’s chin. His hole clenched and fluttered around the thick invasion, pleasure sharp and endless.

Josephine, Francesca, and Bianca settled on the facing sofa, dresses hiked high, and masturbated without shame. Josephine rubbed tight circles over her clit, breath hitching. Francesca buried two fingers in her own cunt and fucked herself in time with Liam’s thrusts. Bianca pressed a small vibrator to her clit, free hand squeezing her breast, eyes locked on the sight of their step-nephew getting railed at both ends. They came in waves while the men kept pounding—Josephine first, hips bucking, a low cry torn from her throat; then Francesca, gushing around her fingers; Bianca shaking through two sharp peaks, vibrator buzzing louder. Silas took every stroke, drooling around Cedric, ass gripping Liam, the obscene wet sounds filling the room. Liam gripped his hips and buried deep, flooding his ass with cum. Cedric pulled out at the last second and painted the final spurts across Silas’s tongue and lips so he could swallow what he caught, then pushed back in to let him suck the rest clean. They kept the rhythm until everyone was spent, Silas’s hole leaking, mouth shiny with spit and cum, body trembling in the heels and wig, blissed-out and glowing under their stares.

After the men zipped up, thanked them, and left, the house fell quiet. Josephine, Francesca, and Bianca surrounded the cum-covered Silas where he still knelt, kissing him tenderly, tasting salt on his lips, wiping smeared mascara with gentle thumbs. They praised him in soft voices for what a perfect hot girl he had become, promising many more nights of the same taboo lessons. They helped him to the wide bed, stripped away the sticky lingerie, and drew him into the center of a slow, sensual group cuddle, warm bodies pressed close, hands stroking his spent cock and tender hole with nothing but affection.

Josephine’s mouth brushed his ear, the last words before sleep. “Tell us, pretty girl—do you want your step-aunt and step-nieces to teach you how to take two cocks in that pussy next time?”