Virgin Femboy Prepares His Ass for Fucking

Yvonne stood in front of the full-length mirror in her bedroom, heart hammering against her ribs as she smoothed the delicate pink lace of her panties over her hips. At twenty-two, she had spent years dreaming about this night, about finally offering up her untouched ass to the woman she loved. Her body was soft and feminine—smooth legs shaved bare, a slight curve to her waist from the estrogen she had started taking two years ago, and a pretty little cock that twitched half-hard against the lace whenever she thought of Selena. She turned sideways, glancing over her shoulder at the pale, unmarked cheeks of her ass, the tight pucker still virgin and pink between them. Tonight that would change.

The doorbell rang, and Yvonne’s breath caught. She padded barefoot to the door in nothing but the lingerie set—a matching bra that cupped nothing but still made her feel pretty, and those tiny panties that barely covered anything. When she opened it, Selena stood there in a tight black dress that hugged her curves, her own cock already tenting the fabric slightly from the walk up the stairs. At twenty-eight, Selena was all confidence and heat, dark hair falling past her shoulders, eyes locking onto Yvonne with hungry approval.

“Fuck, look at you,” Selena murmured as she stepped inside and shut the door. “My pretty virgin femboy, all dressed up like a present. You ready for me to ruin that tight little ass?”

Yvonne’s face flushed hot. “Yes. I’ve been thinking about it all day. My hole feels so empty just knowing you’re here.” She led Selena straight to the bedroom, where she had laid out lube, a small plug, and a slim curved dildo on the nightstand. The air smelled faintly of the cherry body wash she had used in the shower earlier, scrubbing every inch of herself clean, especially between her cheeks. She had even spent twenty careful minutes with the showerhead and a soft cloth, making sure she was spotless inside and out.

Selena sat on the edge of the bed, legs spread, and crooked a finger. “Show me. Bend over and let me watch you prepare that smooth virgin ass. I want to see every little twitch.”

Yvonne’s stomach fluttered with nervous excitement. She climbed onto the mattress on all fours, ass toward Selena, and reached back with both hands to spread her cheeks. The cool air kissed her hole. It clenched instinctively, still so tight it barely looked like it could take a fingertip. “It’s never had anything in it,” she whispered, voice shaky with want. “Not even my own fingers all the way. I saved it for you.”

Selena’s breath went rough. “Goddamn, baby. Look at that pretty pink femboy hole winking at me. So soft and unused. Start with the lube. Slick it up nice and slow while I watch.”

Yvonne grabbed the bottle, flipped the cap, and poured a thick stream of clear gel right into her crack. It was cold at first, making her gasp, then warmed as she rubbed it in slow circles over her pucker. Her fingers trembled. She pressed one fingertip against the tight ring, not pushing in yet, just massaging the slickness around and around until her hole glistened and softened a little under the pressure. Behind her she heard the rustle of fabric—Selena hiking up her dress and freeing her cock, stroking it lazily while she watched.

“That’s it,” Selena praised, voice low and filthy. “Get that virgin ass nice and shiny for me. Push back against your finger. Show me how eager it is.”

Yvonne whimpered and pressed harder. The tip of her finger slipped inside to the first knuckle, and the stretch burned sweetly. Her cock jumped against the lace of her panties, already leaking a wet spot. “It feels so tight. Like it doesn’t want to let go.” She worked the finger deeper in tiny thrusts, coating her insides with lube, the wet squelch filling the quiet room. Her free hand kept her cheek spread so Selena had a perfect view of the shiny finger disappearing into her.

Selena leaned forward, the heat of her breath ghosting over Yvonne’s lower back. Then her lips brushed the nape of Yvonne’s neck, soft at first, then open-mouthed and hungry. She kissed along the side of Yvonne’s throat, teeth grazing lightly, while one hand slid up under the lace bra to pinch a nipple. “Look at how eager your pretty femboy hole looks,” she whispered against Yvonne’s skin, the words vibrating through her. “All wet and fluttering around your finger like it’s begging already. Fuck, Yvonne, you’re going to feel so good stretched around my cock. That virgin ass was made to take me.”

Yvonne moaned, pushing her finger in and out faster, the burn easing into a hot ache. “Selena… please. I need more. Help me stretch it. Train my ass so I can take you. I want your fingers in me—your toys—everything. Make me ready.” Her voice cracked into a desperate little beg. “I’ve waited so long. Don’t make me do it alone.”

Selena’s cock throbbed visibly as she climbed fully onto the bed behind Yvonne, still kissing her neck and shoulder, leaving wet trails. “Say it again. Beg me properly, baby.”

“Please stretch my virgin hole,” Yvonne gasped, pulling her own finger free with a soft pop. Her ass clenched on nothing, feeling emptier than ever. “Use your fingers first. Then the plug. Fuck me open with the toys until I’m loose enough for your cock. I want to feel every inch training me. Tell me how slutty my ass looks while you do it.”

Selena groaned and squeezed a fresh dollop of lube onto two of her own fingers. She pressed the pads against Yvonne’s shiny pucker, rubbing slow circles that made Yvonne rock back instinctively. “Such a good girl, asking so nicely. This tight little femboy ass is mine tonight. Gonna open it up slow, get it dripping and ready.” She pushed both fingertips in at once. Yvonne’s hole resisted for a second, then yielded with a wet stretch that drew a broken moan from her throat. Selena sank in to the knuckles, curling and scissoring gently, feeling the virgin walls flutter and grip.

“Oh fuck—yes—” Yvonne’s arms shook. She dropped to her elbows, face pressed into the sheets, ass still high. The dual stretch burned deeper than her own finger ever had, a perfect full ache that made her cock throb untouched. Selena’s free hand stroked down her spine, then slapped lightly against one cheek, watching it jiggle.

“Look at you taking my fingers like you were born for it,” Selena murmured against her ear, still kissing and nipping the side of her neck. “Pretty pink hole stretched around me, so greedy. You feel how hot and soft it is inside? That’s all for me. Gonna add a third soon, then slide that plug in deep so you stay open while I play with you.”

Yvonne pushed back hard, fucking herself on the two fingers, the slick sounds getting louder. “More. Please, Selena, stretch me wider. I need it. My ass feels so empty without you filling it. Talk dirty to me—tell me how you’re going to ruin your virgin femboy.”

Selena worked a third finger in beside the others, slow but relentless, twisting until Yvonne’s rim was taut and shiny around the thick intrusion. The burn spiked, then melted into throbbing pleasure that shot straight to Yvonne’s dripping cock. “That’s it, take it. This ass is going to look so wrecked when I’m done training it. Plugged and finger-fucked until it gapes a little, all pink and used, ready for my cock to slam home. You’re going to come with my fingers buried in you, aren’t you? My sweet slutty virgin, begging to get her hole ruined.”

Tears of overwhelmed need pricked Yvonne’s eyes, but she only moaned louder, rocking harder. “Yes—don’t stop. Keep stretching me. Put the toy in next. I want to feel it deep while you keep kissing me and telling me how good my ass looks stretched for fucking.”

Selena eased her fingers free, leaving Yvonne’s hole twitching open for a second before it clenched shut again. She grabbed the small black plug, coated it thickly, and pressed the tapered tip right against the fluttering entrance. “Ask for it one more time.”

“Please,” Yvonne sobbed out, voice raw with lust. “Stretch my virgin femboy ass with the plug. Train me. Make me ready for your cock. I need it so bad I can barely think.”

Selena pushed. The plug sank in steadily, thicker than her fingers at the widest point, forcing Yvonne’s rim to stretch white-hot around the girth until the base finally seated flush against her cheeks. Yvonne cried out, body shaking, the full heavy presence inside her lighting up every nerve. Selena’s mouth found her neck again, sucking a mark just below her ear while she twisted the plug gently, working it deeper, her other hand sliding under to cup Yvonne’s lace-covered cock and give it a slow stroke.

“Perfect,” Selena growled against her skin. “Look at that pretty hole swallowing the toy like a hungry little mouth. You’re doing so fucking well, baby. This is only the start. I’m going to keep you stuffed and open, fingers and toys trading places, until you’re dripping and begging for the real thing. Your virgin ass is mine to stretch and fuck, and I am nowhere near done with it yet.”

Yvonne’s whole body pulsed with the dual sensations—the thick plug filling her, Selena’s hand teasing her cock, those filthy whispers vibrating against her throat. She pushed back onto the toy, already aching for the next stretch, for more fingers, for the longer dildo waiting on the nightstand, for the moment Selena would finally replace everything with her own hard cock. The tension coiled tighter between them, sweat slicking their skin, mutual need crackling like static, both of them right on the edge of something deeper and filthier still to come.

Selena gave the base of the plug one last slow twist, then eased it free with a wet pop that left Yvonne’s hole fluttering open, shiny and soft. She reached for the harness waiting in her bag, the thick silicone cock already locked into place, and stepped into it with practiced ease, buckling the straps snug around her hips so the base pressed firm against her own throbbing length. Lube slicked the shaft until it gleamed. “All fours, baby. Present that stretched femboy ass. I’m putting every inch in you right now.”

Yvonne scrambled into position, knees spread wide on the mattress, back arched, lace panties yanked down just enough to bare her cheeks. Her small cock hung heavy and dripping between her thighs. She looked back over her shoulder, eyes glassy with need. “Fuck me, Selena. Fill my virgin hole. Please—make it yours.”

Selena knelt behind her, guided the blunt head to the glistening pucker, and pushed. The rim stretched wide around the thick tip, a burning slide that forced a broken cry from Yvonne’s throat. Inch after inch sank deeper, the toy spreading her virgin walls until Selena’s hips met her ass and the full length was buried. Yvonne’s fingers clawed the sheets. “So deep—oh god, it feels so fucking full—”

“That’s it, take it,” Selena growled, gripping her hips hard. She pulled almost all the way out, then slammed home again, setting a steady, deep rhythm that made Yvonne’s whole body rock forward. The wet slap of skin on skin filled the room. Every thrust dragged over her prostate, sending sparks up her spine. Selena pounded her harder, the strap-on pistoning in and out of the slick, stretched hole, watching it cling and stretch around the thick shaft. “Look at this pretty ass swallowing my cock. You’re taking me so deep, virgin hole stretched open just for me. Such a good girl.”

Yvonne moaned helplessly, pushing back to meet every thrust. Her small cock bounced and leaked with each impact. “Harder—please, ruin me. I can feel it all the way in my stomach. Don’t stop fucking your femboy.”

Selena answered by driving deeper, one hand sliding up to fist Yvonne’s hair and arch her back further so the angle turned filthy and perfect. The toy slammed home again and again, the stretch now pure molten pleasure. Yvonne’s rim was glossy and puffy around the plunging shaft, taking every brutal stroke like it was made for it. Sweat slicked their skin. Selena’s own cock throbbed unused against the harness base, leaking as she watched her girl get wrecked.

After long minutes of that relentless rear pounding, Selena pulled free with a wet sound. She flipped Yvonne onto her back in one smooth motion, hooked those smooth legs over her shoulders, and folded her nearly in half. The position opened her completely. Selena locked eyes with her as she lined up again and thrust back in to the hilt. The sudden depth punched a raw scream of pleasure from Yvonne.

“Look at me while I breed this tight ass,” Selena ordered, voice rough. She started fucking hard and deep, the strap-on dragging over the swollen prostate with every stroke. Their faces were inches apart. Yvonne’s eyes stayed locked on hers, wide and wrecked, mouth open on continuous moans. “Stroke that pretty little cock for me. I want to watch you come while I fuck you open.”

Yvonne’s hand flew between them, wrapping around her small, leaking shaft. She stroked fast and messy in time with the deep thrusts, the dual sensation driving her higher. Prostate sparks built under each slam of the toy, her hole clenching greedily around the thick intrusion. “Selena—I’m so close—your cock is hitting it perfect—don’t stop—”

Selena kept the eye contact intense, hips snapping harder, burying herself to the base over and over. “Come for me. Hands-free if you can. Milk this cock with that sweet virgin ass. Show me how good it feels to get fucked open for the first time.”

Yvonne’s strokes faltered as the pleasure spiked too high. Her hand fell away. The pure prostate pressure from the relentless thrusting tipped her over. Her small cock jerked hard against her belly and she came in long, shuddering pulses, thick ropes painting her soft stomach and the lace of her bra without a single touch. Her hole clamped and fluttered wildly around the strap-on as the orgasm ripped through her, body shaking, thighs trembling against Selena’s shoulders, a broken sob of “yes—coming—fuck—” tearing from her throat.

Selena never slowed. She fucked her straight through the climax, each deep thrust milking more tremors out of her, watching every twitch of pleasure cross Yvonne’s face. Only when the last spurt had landed and Yvonne was whimpering from oversensitivity did she finally ease the thick shaft free. The empty hole winked open, slick and used. Selena unbuckled the harness quickly, set the strap-on aside, and stretched out beside her.

She pulled Yvonne into her arms, one leg thrown over her spent body, and gentled her hands over the sweat-damp skin—stroking down her side, cupping a soft hip, fingertips tracing the mess on her belly. Soft kisses landed on Yvonne’s temple and the mark already blooming on her neck. “My perfect good girl,” Selena whispered, voice warm and proud. “You took every single inch so beautifully. That virgin ass stretched open just for me and you came so hard from it. I’m so fucking proud of you.”

Yvonne melted against her, still trembling, small cock soft and spent between them. She nuzzled into Selena’s chest, breathing her in, the ache in her well-fucked hole a sweet, constant reminder. Selena kept caressing her—slow circles over her back, a tender squeeze of one ass cheek, lips brushing her hair—while the aftershocks faded into floating bliss.

Selena tilted Yvonne’s chin up so their eyes met again, thumb stroking her lower lip. “Next time I want you to ride me until you can’t walk straight. Think you can be my good girl again tomorrow night?”