Sissy's First Anal with Daddy

The apartment held its breath with them. Heat clicked through the vents, and Simone’s heels made a small, nervous sound on the hardwood as she came out of the bedroom and stopped where the lamplight could find her. Twenty-four, and she had dressed for this confession like armor she hoped would become an invitation: pink satin bra lifting the soft shape of her chest, matching panties edged in lace, a garter belt, blush stockings, and black heels that made her calves ache in a way she liked. Her makeup was precise. Her hands were not. They kept drifting to the hem of the panties and worrying the lace until the elastic bit her hip.

Darius sat on the edge of the couch in a black T-shirt and gray sweatpants, forty-two, broad through the shoulders, watching her the way he always did when she came out like this—trying not to rush her and already failing. His eyes traveled the stockings, the lace, the careful line of her mouth, and stopped. Something in his lap had changed. The sweatpants did nothing to hide it.

“You look unreal,” he said.

She stayed a few feet away because if she got closer she might hide the sentence in a kiss and never get it out. “I need to tell you something before we do anything. And I need you to be honest if you don’t want it.”

He leaned forward, forearms on his knees. The bulge shifted with him. “I’m listening.”

Her voice came thinner than she wanted. “I want you to be my Daddy tonight. Not as a joke. I want to call you that, and I want you to take me there. Nobody has ever been inside me like that. I’ve used fingers. I’ve wanted it. I’ve never let anyone have my ass. I want it to be you. I want your cock to be the first thing that opens me, and I want you to make me feel like a complete woman with it.”

The quiet after the words was hot. She watched his face because consent was an answer, not a mood, and she would rather hear no than invent a yes.

Darius exhaled like she had struck him. His palm pressed once, briefly, over the front of his sweatpants—not a performance, just his body answering before his mouth did. When he looked up, his eyes were dark and steady. “You want me to be your Daddy.”

“Yes.”

“And you want me to take your anal virginity. Tonight. Slowly. Only while you still want it.”

“Yes. I’m nervous. I still want it. I’ve wanted it for months and I kept not saying it, and I’m saying it now.”

He stood. The difference in their height made her tip her chin. He didn’t touch her yet, and that restraint made her thighs press together. “Then yes. I want that. I want to be your Daddy, and I want to be the one who opens you. You’ll tell me if it’s too much and I’ll stop. But if you want me to make you feel like a woman with my cock, Simone, I am already hard just looking at you, and I am not going to pretend I don’t want every inch of this.”

The promise went through her like a current. Her nipples tightened against the satin. Between her legs, her clit stirred and began to swell, a small insistent pulse she couldn’t ignore. She nodded, and the nod felt like stepping off a ledge she had chosen on purpose.

“Say it,” he said, softer. “So I know you mean the word.”

“Daddy.” It feminized something in her just to give it to him. Her shoulders dropped. Her hips tipped. “Please be my Daddy tonight.”

“Good girl.” His thumb brushed her cheek, warm and careful. “My pretty girl. Come here.”

She went. The heels made her sway, and when she reached him he set both hands at her waist, not grabbing, just holding her there so she could feel how hard he already was through the cotton. The heat of it against her belly made her breath hitch. He smelled like soap and the cedar of his cologne, ordinary and devastating. She rose onto her toes and kissed him, and he kissed her back slow, mouth open, letting her set the pace until her nervousness melted into hunger and she made a small sound against his tongue.

“Kneel for me,” he said when they broke apart. “If you want to.”

She wanted to. The rug was soft under her knees. The heels stayed on, awkward and pretty, her stockinged calves folded beneath her. She looked up at him from that height and felt the pink lingerie become exactly what she had hoped: a frame for the woman she was asking him to take. Her hands found the waistband of his sweatpants. She paused, eyes on his, and he nodded.

“Go on, baby. Show Daddy how sweet that mouth is.”

She drew the sweatpants and his briefs down together. His cock sprang free, thick, heavy, already flushed dark at the head, a clear bead gathering at the slit. The sight of it made her mouth water and her hole clench on nothing. She had taken him in her mouth before. Tonight it felt different, ceremonial, like she was warming the thing that was going to change her. She wrapped her fingers around the base and felt the heat, the pulse, the weight that made her wrist look delicate. A shiver ran up her arm.

“God,” she whispered, and licked the bead away. Salt. Skin. Him.

Darius’s hand settled in her hair, not forcing, stroking, guiding her closer. “That’s it. Pretty sissy. Look at you on your knees in all that pink, worshiping Daddy’s cock like you were made for it.”

The word sissy landed in her chest and spread. It should have stung. Instead it lit her up. She took the head between her lips and sank, slow, letting her tongue flatten along the underside, feeling every vein, the flare of the crown, the way he thickened when she hollowed her cheeks. Her lipstick smeared. She didn’t care. She bobbed, wet and careful, one hand stroking what her mouth couldn’t reach, the other braced on his thigh. Spit shone on him. Each time she pulled back she watched herself—pink bra, flushed cheeks, his cock glistening between her lips—and the picture made her clit leak a thin strand against the lace.

“Such a good girl,” he murmured, thumb rubbing her temple. “Daddy’s pretty sissy. You feel how hard you make me? That’s all for you. All for that untouched little hole you’ve been saving.”

She moaned around him and the vibration made his hips twitch. She took him deeper, eyes watering, throat fluttering, then pulled off with a wet sound and pressed kisses down the shaft, along the heavy sac, back up to the leaking tip. Her own arousal was a throb now, panties damp, ass clenching in helpless little pulses every time he called her pretty. The dirty talk didn’t degrade her so much as dress her. Every praise put another ribbon on the woman kneeling at his feet.

“Daddy,” she said, voice wrecked, forehead against his hip. “I can’t just use my mouth. I need you. I’m shaking. Please.”

“Tell me where.”

“In my ass.” The confession came out raw. “Please claim it. I’ve never had anyone there and I want it to be your cock. I want to feel you make me yours. I want to feel like your girl all the way through.”

He cupped her jaw and made her look at him. “You sure? Say it clear.”

“I’m sure. I want it. I consent. Please, Daddy, take my virgin ass.”

Something in his face went tender and hungry at once. “Then get on the bed. All fours first, so I can see what I’m being given. Then we’ll do this the way you need.”

She stood on unsteady heels and walked ahead of him into the bedroom, feeling his eyes on the sway of her lace-covered ass. The bed was already turned down, a towel spread, a bottle of lube on the nightstand where she had put it an hour ago with shaking hands. She climbed up, heels still on, and lowered herself to her elbows, back arched, panties clinging to the curve of her ass. The pose made her feel exposed and desperately feminine. Her whole body trembled with the kind of need that had nowhere left to hide.

Darius came up behind her and ran both palms over the stockings, up to the garters, then hooked his fingers in the panties and drew them aside, not off, baring her. Cool air touched her hole. She whimpered.

“Beautiful,” he said. “Pink, tight, nervous. Daddy’s going to take such good care of you.” He kissed the small of her back, then the swell of one cheek, and she heard the cap of the lube. A moment later a slick finger circled her rim, warm from his hand, patient. “Breathe, baby. Push out a little. Let me in.”

She did. The finger breached her slowly, a smooth intrusion that made her gasp and grip the sheet. It burned in a thin bright line and then settled into a stretch she could hold. He worked it in and out, added more lube, added a second finger when she nodded and said yes, please, more. The burn deepened. Her rim fluttered around him. When he curled his fingers and found the firm swell inside her, pleasure detonated low in her belly and her clit jumped, leaking freely onto the towel.

“Oh—Daddy—”

“There she is.” His voice had gone rough. “That little spot. Feel how your body wants to open for me? You’re dripping, sweetheart. Your clit is a mess and I haven’t even given you my cock yet.”

“I need it,” she panted. “Please. I’m ready. I want to see your face when you take it.”

He withdrew his fingers carefully, and the emptiness made her whine. “On your back, then. Missionary first. I want to watch you while I open you. I want you to watch me.”

She rolled over, heels scraping the sheet, and he helped her out of the panties at last, leaving the bra, the garters, the stockings, the heels. The lingerie without the panties felt filthier, more complete, a woman dressed for being taken. He knelt between her thighs and hooked her legs up, ankles near his shoulders, the heels framing his face. Lube shone on his cock. He stroked himself once, twice, slicking the whole thick length, and the sight of that heavy cock poised at her virgin hole made her heart hammer.

“Eyes on me,” he said. “You tell me every second. Green, yellow, red. You know what those mean.”

“Green,” she said, already breathless. “Please. Green.”

He pressed the head against her rim. The pressure was blunt, enormous, nothing like fingers. Her body resisted on instinct, a tight ring of muscle refusing the impossible width, and then she bore down the way he had taught her with his fingers and the head began to sink. The stretch burned. It burned in a bright, spreading ring that made her eyes water and her mouth fall open and her hands fly to his forearms. She felt herself being opened millimeter by millimeter, the flare of his crown forcing her rim wider than it had ever gone, a hot ache that bordered on too much and stayed, by her own choice, on the side of want.

“Daddy—oh God—you’re so thick—”

“I know, baby. Breathe. You’re taking me. Look at that. Your pretty hole is swallowing the head. Such a good sissy. Such a perfect girl.”

The head popped past the tightest ring and she cried out, not in refusal, in shock at the sudden fullness. He stopped at once, buried just inside, one hand stroking her thigh, the other braced beside her head. “Color.”

“Green,” she gasped. “Don’t pull out. Just—stay. Let me feel it.”

She felt everything. The burning eased into a deep, throbbing stretch. Her rim gripped the groove behind his crown like it didn’t want to let go. Inside, the thick shaft pressed against places she hadn’t known could feel this claimed. Every breath moved him a fraction and sent sparks up her spine. Her clit, untouched, stood flushed and wet against her belly, leaking in a steady thread. The feminizing of it hit her harder than the stretch: this was what his cock did. It didn’t just fill a hole. It rearranged her. It made her hips tilt like a woman’s, made her chest arch in the pink bra, made her voice go high and needy, made the word Daddy fall out of her like a prayer. She was being opened and owned, and the ownership felt like femininity poured into her from the inside.

“More,” she whispered. “Please, Daddy. Give me more of you.”

He sank another inch. Then another. The fullness became overwhelming, a heavy occupation that pressed her prostate in a slow relentless drag. Pleasure bloomed behind the burn, deep and molten, and her clit jerked, spilling another clear pulse onto her stomach. She could feel the shape of him, the veins, the impossible thickness splitting her open, the way her body clutched and fluttered and tried to pull him deeper even while it trembled.

“Jesus, Simone.” His jaw was tight. “You’re gripping me like you never want me to leave. So tight. So perfect. Daddy’s cock is all the way—almost—there.”

He bottomed out with a low groan, hips flush to her ass, and she sobbed at the completeness of it. Full. Stuffed. Feminized down to the root. She could feel his heartbeat inside her. Her heels dug into his back. Her rim burned sweetly around the base, stretched to its limit around Daddy’s thick cock, and the pressure on that deep spot made her clit leak without a single touch.

“Move,” she begged. “Please move. I can take it. I want to feel you fuck me.”

He drew back slowly, the drag exquisite and obscene, her rim clinging, and then pushed in again, a long smooth stroke that punched a moan out of her. He found a rhythm, not rough, deep and steady, each thrust a lesson in how thoroughly he owned the place no one else had touched. She felt the burn flare and fade and flare again. She felt the overwhelming fullness every time he seated himself. She felt the prostate pleasure build in waves that made her toes curl in the heels and her clit drip onto the towel. And threaded through all of it was the intensely feminizing sensation of being opened by him—of Daddy’s cock turning her into something soft and taken and glowing, a woman spread in pink lingerie while a man who had promised to complete her did exactly that.

“Your sissy pussy is gripping me so perfectly,” he praised, voice wrecked, eyes locked on hers. “Listen to how wet you are. Feel how you take Daddy. This hole was made for my cock. You’re my beautiful girl. My perfect sissy. Taking every inch like you were born to be filled.”

“Yes—Daddy—yes—” She could hear herself, high and wrecked, and the sound feminized her further. Each thrust shoved a broken plea out of her. Her hands slid from his arms to his shoulders, pulling him down so she could kiss him sloppy and desperate between moans. The missionary closeness made it intimate and filthy at once: his weight, his breath, his cock carving a home inside her, her stockinged legs hooked around him, her clit smearing slick between their stomachs.

When the stretch had melted into a hungry ache and she was pushing back to meet him, he kissed her forehead and said, “I want you on your knees again. Doggy. I want to watch this pretty ass take me. You want that?”

“Yes. God, yes. Don’t stop wanting me.”

He pulled out carefully. The sudden emptiness made her gasp and clench on nothing, rim fluttering, a lewd wet sound in the quiet room. She rolled over on shaking arms and got onto all fours, back arched, heels planted, ass presented. She felt obscene and radiant. Darius knelt behind her, one hand spreading her cheek, the other guiding himself back to the loosened, shining hole.

“Color.”

“Green. Please, Daddy. Put it back in. I feel empty.”

He pushed in easier this time and still the stretch burned, a fresh bright ring as her body remembered how thick he was. The angle was different. Deeper. Meaner in the sweetest way. The head dragged hard over her prostate on the first full stroke and she cried out, arms buckling, face in the pillow, clit jerking and leaking a hot spurt onto the towel beneath her.

“There,” he groaned. “Right there. Listen to you. Daddy’s going to fuck that spot until you cum for me without even touching yourself. Can you do that, pretty sissy? Can you cum on Daddy’s cock like a good girl?”

“I’ll try—oh—I’ll try—”

He set a rhythm, hips snapping in measured thrusts, the sound of lube and skin filling the room. She felt every inch. The burning stretch at her rim each time he withdrew to the crown and drove back in. The overwhelming fullness when he buried himself and ground, stirring her insides. The deep prostate pleasure that rolled through her in electric pulses, making her clit leak and throb and leak again, a helpless little fountain she couldn’t control. And over all of it, the feminizing thunder of being taken this way: face down, ass up, pink bra straps sliding off her shoulders, stockings taut, heels kicking, Daddy’s thick cock opening her and owning her and praising the way her sissy pussy gripped him like it had been waiting its whole life.

“So perfect,” he said, one hand on her hip, the other sliding up her spine to hold the back of her neck, gentle, possessive. “Look at this ass taking me. You’re milking me, baby. Every thrust. My beautiful sissy. Daddy is so proud of you. You feel like a woman? You feel how my cock makes you one?”

“Yes,” she sobbed into the pillow. “I feel it. I feel like your woman. I feel you everywhere. Don’t stop. Please don’t stop. I’m—Daddy, I’m close, I’m so close and you’re not even touching my clit—”

“I don’t have to.” His thrusts stayed deep, rhythmic, relentless in their care. “Your body knows. Let it happen. Cum for Daddy. Soak that towel. Show me what my cock does to you.”

The orgasm built from the inside out, not a sharp peak but a swelling that took her whole pelvis. Her rim clenched rhythmically around his shaft. Her prostate sang under every stroke. Her clit pulsed and spilled, untouched, painting the towel, and then the wave broke and she came hands-free with a shattered cry, thighs shaking, hole fluttering wildly around him, vision whitening at the edges. Pleasure poured through her in long convulsing rolls. She felt feminine and wrecked and holy. She felt owned. She pushed back onto him through it, greedy for every last inch while her body clenched and leaked and sang.

“That’s it—that’s my girl—fuck, Simone, you’re cumming all over me—”

Her orgasm dragged him over. He groaned her name, then “Daddy’s gonna fill you, baby, you want it, tell me you want it—”

“Yes—fill me—please, Daddy, I want your load, I want to feel it—”

He buried himself to the hilt and came, cock throbbing in thick pulses she could feel one by one, heat flooding her virgin hole, a startling liquid fullness added to the stretch. She moaned at the sensation of being bred open, of his cum painting her insides, of the way her fluttering rim milked him for every drop. He stayed deep, hips twitching, emptying himself while she trembled under him, aftershocks still rolling through her clit and her stuffed, burning, blissfully used hole.

They didn’t separate. He eased them both onto their sides, still inside her, his chest to her back, one arm under her head, the other hand stroking slowly from her bra to her belly to the trembling top of her thigh. His cock softened only a little, plugging his load inside her, and the gentle stretch of it made her feel kept. He kissed the damp hair at her temple. His breath was warm on her ear.

“I’m so proud of you,” he whispered. “My beautiful sissy. You took all of me. You came so perfectly. You felt like a complete woman on Daddy’s cock, didn’t you? God, you’re glowing. My pretty girl. My good girl. I love how you grip me even now.”

She was glowing. Her body hummed, rim sore and satisfied, belly warm with him, clit sensitive and slick, stockings twisted, heels half off. For a long minute she floated in it, held close, praised, filled, the feminizing echo of his cock still singing through her. She had asked for this. She had gotten exactly this. The want had been real, the yes had been real, the pleasure had been so real she could still feel it pulsing.

Then his hand stroked her hip again, tender, and he murmured, almost sleepy, “Daddy’s perfect little sissy. That’s all you needed. That’s who you are.”

Something in the sentence snagged.

She stared at the far wall, at the ordinary lamp, at the towel bunched under her hip, and the glow didn’t vanish so much as thin. The stretch inside her was still sweet. His arm was still safe. She had begged for every thrust and she did not take that back. But the word he kept wrapping her in—sissy, sissy, sissy—sat differently now that the hunger had ebbed. She had asked him to make her feel like a complete woman. Lying there, plugged full of him, listening to him name her as if the woman had been a costume and the sissy was the truth, she felt a small cold doubt open under the satisfaction.

She didn’t pull away. She didn’t know yet if she should. Her rim fluttered weakly around him, sore and full, and her voice, when it came, was quiet enough that he might have mistaken it for afterglow.

“Darius,” she said, not Daddy. Her throat tightened. “I loved it. I did. I just… I don’t know if that’s who I am.”

His hand paused on her waist. The apartment was quiet again. Inside her, his cock shifted with a soft, wet ache, and the doubt stayed, warm-bodied and unwelcome, glowing right alongside the pride he had promised her.