Crossdress Sissy Forced Pegging

Xavier had always kept his secret carefully, the delicate lace and silk folded into the back of his underwear drawer like forbidden treasure. At twenty-eight he was slender, almost delicate in build, with narrow hips and smooth skin that took to feminine fabrics as if they had been waiting for him all along. He lived with Vanessa, his thirty-two-year-old girlfriend, in their shared apartment, and though he had never quite confessed the full depth of his need, she had found the panties months ago and simply smiled that slow, knowing smile of hers. Tonight she had left the bedroom door open on purpose.

Aisha arrived just after eight, confident in a tight black dress that hugged her full curves, her dark skin glowing under the warm lamps. At twenty-nine she carried herself like someone who took exactly what she wanted. Vanessa poured wine; Xavier, still in ordinary shorts and a soft T-shirt, brought glasses from the kitchen. He felt the faint scrape of his hidden panties—pale pink lace, the ones with the tiny satin bow at the front—against his cock every time he moved. He had put them on that morning for the private thrill, never expecting company.

Aisha’s gaze dropped the moment he turned. The hem of his shorts had ridden up just enough. A scrap of lace peeked out, unmistakable. She laughed low and rich.

“Well, well. Vanessa, darling, your boy is wearing something pretty underneath.”

Xavier’s face flooded hot. He tugged at the fabric too late. Vanessa’s eyes sparkled with wicked delight. She set her glass down and stepped close, sliding two fingers under the waistband of his shorts to tug the lace higher so Aisha could see the full delicate pattern cupping him.

“I told you he was a little sissy at heart,” Vanessa murmured. “He thinks I don’t notice how hard he gets when I leave my lingerie drawer open. Look at him blushing already.”

Aisha circled him slowly, her perfume warm and spiced. She trailed a manicured nail along the visible lace edge. “Mm. Soft little thing. Does he like being looked at like this? Like a girl who forgot to hide her panties?”

Xavier’s cock twitched inside the lace. He could not meet their eyes, yet the shame and heat mixed so perfectly that his breath came shallow. Vanessa’s hand stayed proprietary on his hip.

“He loves it,” she said. “He’s just never had two of us noticing at once. Go on, Xavier. Tell Aisha what you secretly want.”

He swallowed. “I… I like feeling pretty.”

Aisha’s smile widened. She cupped his chin, forcing his flushed face up. “Pretty is a start. We can make you so much prettier. Vanessa and I have talked about turning you into our little plaything. Stockings, heels, makeup, a short skirt that barely covers that tight sissy ass. Would you like that, baby? Being dressed up and used?”

The word used sent a fresh rush of blood into his lace-covered cock. Vanessa’s fingers slipped inside the shorts properly now, stroking the outline of him through the thin fabric, feeling how wet the tip already was.

“See how eager he is,” Vanessa whispered against his ear. “He’s dripping for it. Let’s take him to the bedroom and make him complete.”

They guided him down the hall, one woman on each side, hands roaming. In the bedroom Vanessa flicked on the softer lamps while Aisha opened the bottom drawer Vanessa had prepared weeks ago for exactly this night. Out came sheer black stockings, a garter belt, glossy black heels with delicate straps, a tiny pleated skirt in deep red, a matching bra with soft cups, and a makeup kit.

Xavier stood trembling as they undressed him. Vanessa peeled the shorts down, leaving him in only the pink lace panties that strained around his hard cock. Aisha made an appreciative sound and cupped him through the fabric, squeezing gently.

“So polite and hard already. We’re going to make you beg properly.”

They worked together with unhurried precision. Vanessa rolled the stockings up his legs, smoothing the sheer nylon over his calves and thighs, clipping them to the garter belt that sat snug around his narrow waist. Aisha fastened the bra, then helped him step into the little red skirt; it barely reached mid-thigh and flared when he moved. The heels came next—Vanessa buckling the straps while Aisha steadied him. He wobbled, then found his balance, standing taller and more exposed than he had ever felt.

Makeup followed. Aisha sat him on the edge of the bed and painted his lips a glossy deep pink, lined his eyes until they looked wide and soft, dusted blush across his cheeks. Vanessa brushed his hair into a slightly messy feminine style and slid simple pearl earrings into place. When they finished, they turned him to the full-length mirror.

Xavier stared. The slender body in the reflection belonged to a pretty sissy slut—stockinged legs, arched feet in heels, tiny skirt, lace still hidden underneath, painted face flushed with arousal and nerves. His cock tented the front of the skirt obscenely.

Vanessa pressed against his back, arms around his waist, lips at his neck. “Look at our beautiful boy. Our pretty little slut.”

Aisha stepped in front of him, hands sliding under the skirt to cup his lace-covered ass, squeezing the firm cheeks. “Such a tight little hole waiting under all this. We’re going to stretch you open tonight, Xavier. Both of us. Thick cocks strapped on, taking turns fucking this pretty sissy ass until you can’t think of anything but how good it feels to be used.”

He whimpered. The dirty words, the hands, the mirror image—everything crashed together. Vanessa’s fingers slipped inside the panties now, stroking his leaking cock with slow, deliberate pulls while Aisha’s nails traced the cleft of his ass through the lace.

“Tell us what you want,” Vanessa coaxed, voice honey-sweet and filthy. “We need to hear it.”

Xavier’s hips jerked. “Please… dress me up like this and… and use me. I want to be your slut. I want you both to fuck me.”

Aisha laughed softly, delighted. “That’s it. Begging already. Good boy.” She kissed the corner of his painted mouth, careful not to smear, then turned to the dresser where two harnesses and two thick, realistic dildos waited—one a deep purple, one a warm flesh tone, both substantial and veined.

Vanessa kept stroking him while Aisha stepped into her harness, buckling it snug around her hips so the heavy cock jutted out proud and ready. Vanessa released Xavier only long enough to do the same, the purple shaft bobbing as she settled the straps. They stood before him in their dresses, skirts lifted, strapped cocks gleaming under the light, while he remained their finished product—heels, stockings, tiny skirt, makeup, lace panties soaked through.

Aisha stepped close again, letting the thick head of her dildo nudge the front of his skirt, rubbing against his own trapped cock. “Feel that? That’s going inside you. Vanessa’s too. We’re going to bend you over and take turns opening this tight sissy hole until you’re dripping and begging for more.”

Vanessa’s hands returned, sliding up under the skirt from behind, pulling the lace panties down just enough to expose his ass while leaving them stretched around his thighs. She parted his cheeks with her thumbs, circling a dry fingertip over his clenched hole, promising without entering yet.

“You’re shaking,” she murmured. “So ready. Keep begging, baby. Tell us exactly how you want to be fucked.”

Xavier’s voice cracked with need. He stared at their strapped cocks in the mirror, at his own transformed body, at the two dominant women who had dressed him and now owned the moment completely. The tension coiled tighter, electric and unfinished, his hole twitching under Vanessa’s fingertip, his cock leaking steadily onto the lace still framing him.

“Please,” he whispered, louder now, hips pushing back into Vanessa’s touch and forward against Aisha’s dildo. “Please put them in me. Use my ass. Make me your pretty pegging slut. I need it—I need both of you fucking me tonight.”

Aisha and Vanessa shared a dark, satisfied look over his shoulder, their hands never still, teasing and promising, the thick strapped cocks resting heavy against his body as the night stretched open ahead of them, every filthy intention still waiting to be fulfilled.

They wasted no more time on teasing. Vanessa slicked two fingers with lube from the bottle Aisha had tossed onto the bed and pressed them firmly against Xavier’s twitching hole. He gasped as she worked them inside, stretching him open with slow, insistent twists while Aisha kept the thick head of her strap-on rubbing against his painted lips. “Open that pretty mouth, sissy,” Aisha ordered. He did, tongue out, and she slid the warm flesh-toned cock across it, coating it in spit and gloss. Xavier moaned around the intrusion, hips rocking back onto Vanessa’s fingers.

“Couch,” Vanessa decided, voice thick with hunger. She pulled her fingers free, wiped them on his skirt, and marched him out of the bedroom on unsteady heels, Aisha following with a firm grip on his elbow. In the living room the soft lamps still glowed. Vanessa bent him over the arm of the wide couch so his stockinged legs straddled nothing and his little red skirt flipped up onto his back. The pink lace panties stayed stretched around his thighs, framing his bare ass and leaking cock. She kicked his feet wider, heels clicking on the hardwood.

Aisha circled to the front, knelt on the cushions, and fed her strap-on between his glossy lips again. “Suck it while she splits you open. Good little cum-slut.” Xavier’s mouth stretched wide around the shaft; he hollowed his cheeks and whimpered as Vanessa notched the purple head against his slick hole. She pushed. The thick crown forced past the tight ring in one steady thrust. Xavier cried out around Aisha’s cock, the sound wet and broken. Vanessa kept going until her hips met his cheeks, the full length buried in his guts.

She fucked him hard from the start—deep, slamming strokes that rocked his whole body forward onto Aisha’s dildo. The couch creaked. Xavier’s painted nails dug into the cushions. Every forward shove shoved the flesh cock deeper down his throat; every pull-back let him gasp before Aisha thrust again. “Look at him take it,” Vanessa growled, hands bruising his hips. “Tight sissy ass swallowing every inch. You love being our little fucktoy, don’t you?”

He could only moan yes around the cock stuffing his mouth. Spit ran down his chin, smearing the pink lipstick. His own cock slapped against the couch arm with every thrust, untouched and dripping steadily onto the floor. Aisha held his head by the hair she had styled earlier and used his throat like a second hole, matching Vanessa’s brutal rhythm. The dual filling left Xavier shaking, eyes wet with overwhelmed pleasure, stockings slipping slightly on his trembling thighs.

Vanessa changed the angle, aiming upward, and the head of her strap-on dragged hard over his prostate. Xavier screeched around Aisha’s cock. His balls drew up tight. She hammered that spot relentlessly until his legs nearly gave out, then pulled free with a wet pop. “Floor. Now.”

They dragged him down onto the thick rug. Aisha lay on her back and pulled him over her so he straddled her waist facing away—reverse cowgirl—his lace-framed cock bouncing above her stomach. She reached up, lined his slippery cock with her entrance under the black dress she had hiked high, and sank him inside her wet heat in one drop. Xavier sobbed at the sudden tight grip around his shaft. Before he could adjust, Vanessa knelt behind him, re-slicked her purple cock, and drove back into his stretched hole.

The double penetration tore a raw cry from his throat. Aisha rolled her hips upward, fucking herself on his cock while Vanessa slammed into his ass, driving him deeper into Aisha with every powerful thrust. The reverse angle let Vanessa grind straight against his prostate without mercy. Xavier’s hands braced on Aisha’s thighs; his head fell back, pearl earrings swinging. “Fuck—fuck—please—” he babbled, voice cracked and high.

“That’s it, sissy,” Vanessa panted, pounding harder. “Take both of us. You’re going to come with nothing touching that pretty cock except Aisha’s cunt.” She reached around and pinched his nipples through the soft bra cups. Aisha’s nails raked down his stockinged thighs. The dual friction built fast—tight wet heat around his cock, relentless pressure on his prostate. Xavier’s whole body locked. With a broken wail he came hard, spurting thick ropes across Aisha’s dark stomach without a single hand on himself, hole clenching rhythmically around Vanessa’s thrusting cock. His cock kept pulsing inside Aisha as she milked him through it, laughing low and delighted.

They didn’t give him time to recover. Vanessa pulled out, rolled him onto his back on the rug, and shoved his stockinged legs wide and high until his heels pointed at the ceiling. The little skirt bunched around his waist. His used hole gaped pink and shiny. Aisha wiped his spend off her belly with two fingers, fed it into his open mouth, then swapped places with Vanessa. She slammed her flesh-toned cock into him to the hilt while Vanessa straddled his chest and offered her purple shaft to his lips again.

They took turns without pause. Aisha fucked him deep and fast for a dozen strokes, then pulled out so Vanessa could sink in and pound just as hard, then back again. Their voices overlapped, filthy and loving.

“Such an eager little sissy cum-slut.”

“Look how he opens for us. Perfect pegging whore.”

“Gonna keep this hole busy all night, baby. Ours.”

Xavier’s cock twitched back toward full hardness against his belly, smearing fresh precum over the lace still tangled at his thighs. Every alternate thrust drove him closer to a second edge he wasn’t sure he could survive. Tears of pure overload streaked his makeup. He clutched at their thighs, at the straps of their harnesses, moaning broken thank-yous and more-pleases between the cocks that kept filling his mouth and his ass in relentless rotation.

Aisha leaned down, still buried inside him, and kissed the corner of his ruined lipstick. “We’re nowhere near done with you.” Vanessa pulled free of his throat just long enough to add, “Next we’re taking you back to the bed. Harnesses stay on. You’re going to ride one of us while the other wrecks your throat again. And after that… well.” She smiled darkly down at their trembling, dressed-up slut. “We have all night to turn you into the perfect, dripping, well-fucked sissy.”

Xavier’s hole clenched around the thick cock currently stuffing him. His cock jerked hard against his stomach. The night was still young, his body already wrecked and aching for more, and both women looked ready to deliver every filthy promise they had made.

They hauled him upright on wobbling heels, lace panties still snagged mid-thigh, tiny red skirt flipped uselessly around his waist. Vanessa kept two slick fingers buried in his stretched hole as they marched him back down the hall, Aisha’s hand fisted in his styled hair, guiding every shaky step. His cock bobbed wet and stiff again, smearing precum across his own stomach with each click of those glossy heels. In the bedroom the lamps still glowed soft; the sheets already looked ruined from earlier preparations. They shoved him onto the mattress face-first, then flipped him like a ragdoll until he sat astride Vanessa’s hips.

She had already slicked the purple cock thick with fresh lube. Aisha shoved more of the cool gel between Xavier’s cheeks, two fingers plunging deep, scissoring, coating every rim and ridge until it dripped down his balls and soaked the pink lace still framing him. “Ride it, pretty sissy. Sink that hungry hole all the way down.” Xavier’s painted nails dug into Vanessa’s shoulders as he lined himself up. The thick head pressed, popped past the ring, and he sank in one long, trembling drop until his ass met the harness. The stretch burned perfect and full; his prostate lit up instantly. Vanessa rolled her hips upward, grinding the veined shaft hard against that sweet spot while Aisha climbed onto the bed behind his head, knelt wide, and fed the flesh-toned cock straight between his glossy, ruined lips.

“Throat first,” Aisha ordered, voice low and thick. “Open wide and take every inch while you bounce on her cock like the good little pegging slut you are.” Xavier hollowed his cheeks and swallowed as she thrust forward, the heavy shaft sliding over his tongue and into his throat until her harness pressed his nose. Spit and lipstick mixed immediately; tears pricked his eyes and streaked fresh black lines down the blush on his cheeks. He rose and dropped on Vanessa’s purple cock in the same rhythm, the dual stuffing turning his body into a single wet, obedient channel. Every downward slam drove the head against his prostate; every upward lift let Aisha shove deeper into his mouth. His own cock slapped wetly against Vanessa’s stomach, untouched, leaking steadily onto her dress.

Vanessa reached up and pinched both nipples through the soft bra cups, twisting just hard enough to make him moan around Aisha’s shaft. “Look at you—stockinged legs spread, heels digging into the sheets, hole stretched around my cock like it was made for it. You’re dripping lube and precum all over me, baby. Such a perfect little fucktoy.” Xavier’s mind floated, half shame and half pure electric bliss; every filthy word sank straight into his cock. He wanted to stay exactly here, used and dressed and owned, forever.

They switched without warning. Aisha pulled free of his throat with a wet pop, shoved him forward so he braced on hands and knees over Vanessa, then drove her own thick cock into his already-open hole in one brutal thrust. Lube squelched loudly. Xavier cried out as the new angle hammered deeper, the flesh-toned ridges dragging hard over his prostate while Vanessa reached up, grabbed his hips, and pulled him down so his cock slid between her full breasts, trapped and sliding through the slick valley she made with her hands. Aisha fucked him like she meant to break him—long, punishing strokes that rocked the entire bed, each one forcing his cock to fuck Vanessa’s soft tits. Makeup ran in dark rivulets now; the pearl earrings swung wildly. His hole fluttered and clenched, greedy for more, already so used it stayed slightly open between thrusts, shiny with lube and need.

“Switch,” Vanessa growled after a dozen hard pumps. They rolled him onto his back again, stockinged legs shoved high and wide until the heels nearly touched the headboard. Aisha straddled his chest facing his feet, lowered her soaked cunt onto his mouth, and ordered him to tongue her while Vanessa knelt between his spread thighs and slammed the purple cock home once more. Xavier licked desperately, tasting Aisha’s wet heat, moaning into her folds every time Vanessa’s cock punched his prostate. His own cock jerked against empty air, red and leaking, balls tight. Aisha ground down harder, smearing her juices over his ruined lipstick and chin. “That’s it, sissy—eat me while she wrecks that pretty hole. You’re going to come again just from being fucked and used.”

Vanessa poured more lube straight onto the place where her shaft stretched him, letting it run in thick white rivulets down his cleft and onto the sheets. She fucked him faster, the wet slap of harness against ass filling the room. Xavier’s tongue worked frantically; his hole clenched in rhythmic pulses. The dual sensation—Aisha’s cunt smothering his face, Vanessa’s cock owning his guts—shoved him over the edge without a single touch to his cock. He came hard, thick ropes arcing up his own belly and chest, hole spasming around the invading shaft, thighs shaking in the sheer stockings. Aisha laughed, delighted, and kept grinding on his mouth through it, forcing him to taste her while he pulsed and spilled.

They still weren’t finished. Vanessa pulled out, flipped him onto his side, spooned tight behind him, and pushed back in while Aisha lay facing him, lifting one of his stockinged legs over her hip and sliding her own cock into his mouth again. They fucked him in slow, deep tandem—ass and throat, thrust for thrust—until his second orgasm faded into oversensitive twitching and a third, weaker pulse of clear fluid dribbled from his cock onto the sheets. Lube everywhere: glistening on his thighs, soaking the lace panties tangled at his knees, dripping from his open, thoroughly used hole every time a cock withdrew. His makeup was a wreck—smeared pink lips, raccoon eyes, tear tracks—and the little red skirt was twisted uselessly around his waist. He trembled continuously, hole fluttering empty between fillings, body glowing with the raw, submissive overload of being their shared toy.

Finally the women slowed. Aisha eased her cock from his throat; Vanessa slipped free of his ass with a soft, wet sound. They unbuckled the harnesses together, setting the heavy dildos and straps aside on the nightstand still shining with lube and spit. Xavier collapsed onto his back between them, legs limp, heels still strapped on, stockings half-slipped, cock soft and spent against his sticky belly. Vanessa pulled him onto his side so his back pressed to her front; Aisha curled in front of him, one thigh draped over his hip. Their bare hands—no longer wearing the cocks—stroked his ruined face, his soft cock, the loose wet rim of his hole. They cradled their trembling sissy between warm curves and soft skin, voices dropping to low, filthy praise.

“You took both of us so perfectly,” Vanessa murmured against his ear, fingers lazily circling his stretched, lubed entrance. “Such a good little pegging slut. That tight sissy hole opened up like it was starving for cock. Look how pretty you still look even with makeup all over your face and cum drying on your stomach.”

Aisha kissed the corner of his swollen mouth, smearing the last of the gloss. “Our perfect toy. Dressed up, bent over, ridden, throat-fucked, and filled until you couldn’t stop coming. You glowed every time we buried those cocks in you. Best willing pegging whore we’ve ever made.”

Xavier shivered between them, body loose and aching in the sweetest way, mind floating in submissive bliss. The praise wrapped around the raw stretch in his ass and the taste still on his tongue; he felt owned, finished, complete. Their hands kept roaming—petting his soft cock, stroking the garter straps, tracing the puffy rim of his well-used hole—keeping him right there in the afterglow of being thoroughly fucked.

Vanessa’s fingers pushed two slick digits back inside him just to feel how loose and wet he still was. Aisha squeezed his spent cock once, hard enough to make him twitch. He lay spent and trembling in the ruined makeup and lingerie, glowing under their praise, hole dripping the last of the lube they had pumped into him all night.

Vanessa smiled against his neck and whispered the last filthy truth into his ear while she slowly fucked those two fingers in and out of his open, ruined sissy cunt: “Tomorrow night we’re strapping on even thicker ones and turning this greedy little hole into a permanent dripping cumdump.”