Chapter 451 - : 451 : Valerina’s First Anal & Pearly Gate!
Aiden looked down at Valerina, who was leaned on his chest after their intense Face Off 69. She was breathless, her massive breasts rising and falling, her face flushed and lips swollen from taking him deep. He leaned in close and spoke softly.
"Your ass is left, Valerina."
She looked up at him from where she lay against his chest, golden eyes wide and shy. Her voice came out small and hesitant.
"But... I have never... No one ever..."
Aiden grinned, his hand gently stroking her hair.
"That’s even better. Your asshole is mine, always. From beginning to end."
Valerina whimpered softly, her cheeks burning.
"But... it’s dirty down there."
Aiden leaned down and kissed her cheek tenderly.
"It’s alright. Nothing about you is dirty."
She bit her lip, still nervous but trusting him completely.
"Please be gentle with me."
He smiled and reached over to the bedside table, picking up a glass of water. He brought it to her lips.
"Drink up. You’ll need it."
Valerina nodded shyly and let him tilt the glass, drinking slowly as he fed her. When she was done, he placed the glass back on the table.
Then he looked at her again, his voice calm but firm.
"I will fuck your ass in a pose I haven’t done with the others."
Valerina gasped in surprise, her eyes widening.
"Sir, wouldn’t it be better if you do it normally for my first time?"
Aiden shook his head gently.
"It’ll be better. I will hold you all the time."
She looked at him for a long moment, then nodded shyly, her voice barely above a whisper.
"...Okay."
Aiden helped her move into the Pearly Gates position on the massive bed. He lay on his back first, knees bent and feet planted for leverage, then gently guided Valerina to settle on top of him on her back. Her body aligned perfectly with his, head resting beside his own and slightly above, both of them facing upward. She spread her legs and bent them, planting her feet on the bed to stay balanced while her full weight rested against his chest and torso. This intimate stacked position let him wrap his strong arms completely around her from below — one hand splayed across her waist, the other free to roam her body — holding her tightly the entire time. It was perfect for deep, slow anal penetration; her body weight helped her settle gently onto him while he remained in complete control, kissing her neck and whispering directly into her ear.
Valerina’s brown pleated skirt was still bunched up around her waist, and her open cream blouse hung loosely off her shoulders. Her massive breasts rose and fell freely with every breath, fully exposed. He slicked his massive cock with the mixture of their earlier fluids and her own abundant wetness, making sure it was well-lubricated.
He angled his hips and guided the thick, veiny head of his twelve-inch cock between her cheeks, pressing it firmly against her tight, untouched asshole. Even the pressure of just the head made Valerina tense up.
Aiden kissed the side of her neck, then spoke softly against her ear.
"Relax for me, Valerina. I’ve got you. I’m right here."
He began to push upward, very slowly and firmly.
The fat head of his wrist-thick cock pressed against her virgin asshole, stretching the tight ring. Valerina gasped sharply, her body going rigid as the first real stretch hit her.
"Ahh... Sir... it’s... it’s stretching..."
She could feel every inch of the thick, veiny head forcing its way inside. There was a burning stretch, a deep pressure she had never felt before. Her extremely sensitive body reacted intensely — her pussy clenched around nothing while her asshole tried to adjust to the massive intrusion. A thin layer of natural anal mucus helped ease the way slightly, but the sheer girth still made her whimper. In this position, with her lying fully on top of him, the pressure felt even more overwhelming, like her own body weight was helping to impale her slowly onto his cock.
*It’s so big... bigger than I imagined... and lying on him like this makes it feel even deeper... it’s stretching me so much already... it burns a little but... Sir is being so gentle... I can feel every vein on his cock as it goes in...*
Aiden kept pushing slowly, giving her time to breathe. Inch by thick inch sank into her. The head finally popped past the tight ring, and the rest of his massive cock began to follow. Valerina’s breathing turned into short, shaky gasps. She clutched at his forearms where they wrapped around her, her nails digging in lightly.
"Sir... it’s so thick... I can feel it opening me up... ahh... it’s going deeper..."
Aiden kissed her neck again, slow and reassuring, while continuing to push upward at a careful pace. One hand stroked her stomach gently as he held her close in the Pearly Gates position.
"You’re doing so well, Valerina. Your asshole is taking me so perfectly. Just breathe... I’m right here with you."
More of his twelve-inch length disappeared into her. The stretch was intense — her tight virgin hole had to accommodate his full wrist-like girth. Every vein and ridge dragged along her inner walls, creating a deep, full sensation that made her moan despite the initial discomfort. Natural lubrication from her body helped, but the pressure was overwhelming in the best and most intense way. Because she was lying on top of him, every inch felt even more complete, her body settling heavily onto his cock.
*It’s reaching so deep already... I can feel him in places I’ve never felt anything before... it’s stretching my ass so wide... it hurts a little but Sir’s kisses on my neck make it better... I trust him... I love him so much...*
Aiden paused when he was about halfway in, letting her adjust. He kissed the curve of her shoulder and whispered more praise.
"You feel incredible. So tight and warm around me. Your body was made for this. I’m going to take care of you."
Valerina nodded against the side of his face, her voice trembling.
"It feels... so full, Sir... like you’re filling every part of me... please... keep going... but slowly..."
He resumed pushing upward, slower this time. The remaining inches of his thick, veiny cock sank deeper into her intestine. The stretch reached new depths as he finally bottomed out, his entire twelve inches buried inside her ass, the head pressing far into her guts. Her lower belly showed a faint bulge from how deep he was.
Valerina let out a long, shaky moan, her body trembling in his arms.
"Sir... you’re all the way in... I can feel you so deep in my intestine... it’s so much... but you’re holding me... it feels good when you hold me like this..."
Aiden stayed completely still for a long moment, letting her get used to the feeling of being so completely filled. He kissed her neck, her shoulder, the side of her jaw — constant gentle affection while his massive cock remained buried deep inside her ass. His hands roamed up to cup her massive breasts from below, thumbs brushing her nipples.
"You’re amazing, Valerina. Taking all of me on your first time. I’m so proud of you."
He began to move, but only in tiny, slow upward thrusts at first. Just rocking his hips gently so she could feel every inch without being overwhelmed. The Pearly Gates position kept their bodies pressed together completely, allowing him to kiss her neck and whisper praise with every small movement while his arms stayed wrapped tightly around her.
As her body slowly relaxed around him, he gradually increased the depth and pace, still staying gentle. Every upward thrust pushed his thick cock deep into her intestine, the veiny shaft dragging along her sensitive inner walls. Valerina moaned softly with each movement, her hands clutching at his arms.
"Sir... it’s starting to feel better... the stretch... it’s turning into something warm... ahh... you’re so deep inside me..."
Aiden kept his promise — he held her the entire time. One arm stayed wrapped around her waist and chest while the other stroked her breasts or slid down to gently rub her clit in slow circles. He kissed her neck constantly, slow and loving, even as his thrusts became a little deeper and more rhythmic. Occasionally she turned her head and he met her lips for a deep, tender kiss.
"You’re so beautiful like this," he whispered between kisses. "My shy Valerina taking my cock in her ass for the first time. You’re perfect. I love how tight you feel around me."
Valerina’s moans grew a little louder as the initial discomfort faded and pleasure began to build. The deep, full feeling of his massive cock moving inside her intestine was unlike anything she had ever experienced. Because she was lying fully on top of him in the Pearly Gates position, every thrust pressed their bodies together even more intimately, her massive breasts jiggling in his hands.
"Sir... it feels good now... really good... I can feel you moving so deep... please... keep going..."
Aiden gradually built up the pace while still remaining gentle and controlled. He never stopped kissing her neck or praising her. His hand slid down to squeeze her wide hip as he thrust deeper into her ass.
"You’re taking me so well. Your asshole is gripping me perfectly. I’m going to fill your intestine with my cum, Valerina. All of it belongs to me."
She nodded against the side of his face, her voice soft but full of trust.
"Yes, Sir... it’s yours... everything is yours..."
He kept fucking her ass in the intimate Pearly Gates position for a long time — slow, deep, and steady upward thrusts. Every thrust reached far into her intestine, the thick head pressing deep inside her. Valerina came twice from the overwhelming fullness and the constant gentle stimulation, her body shaking in his arms as she moaned his name, her pussy fluttering and dripping onto his lower stomach.
When Aiden finally approached his own release, he held her even tighter. He kissed her neck deeply and thrust all the way up, burying his entire length in her guts.
"I’m cumming, Valerina..."
He came hard, thick ropes of cum flooding deep into her intestine. Because he was buried so far inside, every pulse pumped directly into her guts, filling her completely. Valerina moaned softly at the warm, full sensation, clinging to his arms as he emptied himself inside her.
They stayed locked in the Pearly Gates position for a long while afterward, Aiden still buried deep in her ass while he kissed her neck and shoulder gently and stroked her hair and breasts.
"You did so well," he whispered. "I’m so proud of you."
Valerina nuzzled back against his chest, completely spent but glowing with love and trust.
"Thank you, Sir... for being gentle... I love you..."
He kept fucking her ass in the intimate Pearly Gates position for a long time — slow, deep, and steady upward thrusts. Every thick inch of his twelve-inch cock dragged along her sensitive inner walls, the fat head pressing far into her intestine with each deliberate push. Valerina’s body trembled continuously against him, her back pressed flush to his chest, her massive breasts rising and falling heavily with every shaky breath. Aiden’s strong arms stayed wrapped tightly around her from below, one hand cupping and squeezing her left breast while the other slid down between her spread thighs. His fingers found her swollen clit and began rubbing it in slow, firm circles that matched the rhythm of his hips.
"That’s it, my sweet girl," he murmured against the side of her neck, his voice low and rough with restrained desire. "Just feel me. Feel how deep I am inside your tight little ass." He squeezed her breast harder, thumb and forefinger pinching her stiff nipple until she gasped. "Your body was made for this. Made to take every inch of my cock."
Valerina moaned softly, turning her head just enough for him to capture her lips in a slow, deep kiss. Their tongues brushed as he continued the lazy upward thrusts, never pulling out more than a few inches before sinking back in to the hilt. The position kept them locked together so completely that every movement made her feel owned, filled, cherished.
"Ahh... Sir..." she whispered when he broke the kiss to suck gently at the tender skin just below her ear. "It feels... so full. Every time you push in I can feel you in my belly..."
He smiled against her skin and sucked harder, drawing the flesh between his lips until a dark hickey bloomed. "Good. I want you to feel me everywhere." His fingers on her clit pressed a little firmer, rubbing faster now. "Look at how wet your pretty pussy is getting. Dripping all over me while I fuck your ass. Such a good girl."
She whimpered, hips twitching involuntarily. The dual stimulation — the deep, relentless fullness in her ass and the steady pressure on her clit — was already pushing her toward the edge again. Aiden felt it in the way her asshole fluttered and tightened around his cock. He squeezed her breast again, rolling the nipple, while his cock continued its slow, deep invasion of her guts.
"Sir... I’m close again..." Valerina’s voice was breathless, almost pleading. "Please... don’t stop..."
"I’m not stopping, baby," he promised, voice thick. He thrust upward a little harder, grinding the head of his cock against the deepest part of her intestine. At the same time his fingers rubbed her clit in tight, fast circles. "Cum for me. Cum with my cock buried in your ass."
Her orgasm hit hard. Valerina’s entire body seized, back arching against his chest as a broken cry tore from her throat. Her pussy clenched and fluttered visibly, a fresh gush of wetness soaking his lower stomach and the base of his cock. Her asshole spasmed wildly around him, the tight ring gripping and milking his thick shaft in rhythmic pulses. Tears of overwhelming pleasure pricked at the corners of her eyes.
"That’s my girl," Aiden groaned, holding her through it, still thrusting slowly, drawing the orgasm out, his fingers gentled on her clit but didn’t stop. "So beautiful when you cum for me. Squeeze me just like that... fuck, you’re so tight."
Valerina sobbed softly through the aftershocks, body twitching. "Sir... it’s too much... but it feels so good..."
He chuckled darkly against her skin, giving her breast one last firm squeeze before sliding his hand back to her ass. He gripped one cheek, spreading her slightly. "We’re just getting started, Valerina. Your ass feels too good. I’m going to make you cum again and again until you can’t think straight."
He began to fuck her a little harder — still controlled, but the thrusts deeper, the pace gradually increasing. Each time he bottomed out, the faint bulge in her lower belly became more pronounced. His hand returned to her clit, rubbing steadily while the other hand roamed between her breasts and her ass, squeezing and kneading the soft flesh. He left another hickey on the side of her neck, sucking until she moaned loudly.
"Tell me how it feels," he demanded between kisses to her shoulder. "Tell Sir how his cock feels stretching your virgin ass."
"It feels... huge," she gasped, voice hitching with every thrust. "Like you’re splitting me open... but in the best way. I can feel every vein... every time you push deeper it’s like you’re touching my stomach... ahh! Sir, right there—"
He angled his hips and gave a particularly deep grind, pressing the head firmly against that sensitive spot inside her. At the same time he pinched her clit lightly between two fingers and rolled it. Valerina’s second anal orgasm crashed over her almost immediately. She cried out louder this time, thighs shaking, toes curling hard against the bed. Fresh tears slipped down her cheeks as her pussy squirted a small, hot rush. Her asshole clamped down so tightly around his cock that Aiden groaned loudly, his control wavering for the first time.
"Fuck... Valerina..." His voice was strained. He squeezed both of her breasts hard, thumbs flicking her nipples while he kept thrusting through her orgasm. "You’re going to make me lose it if you keep squeezing me like that. Your ass is so fucking tight... so perfect..."
He started fucking her harder still — long, powerful upward strokes that made her body jolt against him. The wet sounds of his cock moving in her ass filled the space between them, mixed with her soft cries and his heavier breathing. His fingers never left her clit, rubbing faster now, two fingers sliding through her soaked folds before returning to the swollen nub.
"Sir... I’m going to cum again..." she whimpered, voice breaking. "Please... please don’t stop... it feels too good..."
"Cum then," he growled against her ear, nipping the lobe. "Cum on my cock while I fuck your ass. I want to feel you fall apart again."
Her third orgasm hit even harder. Valerina wailed, body convulsing so violently that Aiden had to hold her down with both arms wrapped tightly around her middle. Her pussy gushed again, soaking them both. Tears streamed freely down her face now — tears of pure, overwhelming pleasure. She sobbed his name, "Sir... Sir... I love you... I love you so much..." while her asshole milked him in desperate, fluttering spasms.
Aiden was breathing hard now, sweat beading on his skin where it pressed against hers. The extreme tightness of her virgin ass — the way it gripped him like a hot, velvet fist every time he thrust in — was finally cracking his legendary control. He tried to stay slow, tried to keep the pace measured, but every squeeze of her walls around his cock sent sparks of raw need shooting up his spine.
"Valerina..." he rasped, voice rough. "Baby... you’re too tight. I can’t... I can’t hold back anymore..."
His hands slid down to her ass. He gripped both cheeks hard, fingers digging into the soft flesh, spreading her wide. Then, with a low, animalistic groan, he started using his grip to slam her up and down on his cock.
The change was sudden and intense. Instead of just thrusting up into her, he lifted her hips with his strong hands and dropped her back down onto his upward-driving cock at the same time. The force drove him even deeper, the head of his cock punching far into her intestine with every brutal downward slam. Valerina cried out — a high, broken sound of shocked pleasure.
"Sir! Ahh—! Oh god—!"
"That’s it," he snarled, lost in the feeling. "Take it. Take every fucking inch." He slammed her down again and again, using his planted feet for leverage to thrust up powerfully while his hands controlled her body like a toy. Her massive breasts bounced with every impact. "Your ass is mine. This tight little hole belongs to me now."
Valerina could only sob and moan, tears flowing freely down her cheeks. The pleasure was so intense it bordered on too much. Every hard slam sent a shockwave through her, the deep anal penetration on every downward drop pushing her straight into another orgasm.
"I’m cumming—! Sir, I’m cumming again—!" she wailed, voice cracking.
Her fourth orgasm ripped through her. She screamed, body shaking violently in his iron grip. Her pussy squirted hard this time, a hot rush soaking his lower stomach and balls. Her asshole clamped down so tightly it almost hurt, but the pressure only drove Aiden wilder. He growled and fucked her through it, never slowing, slamming her up and down on his cock like he couldn’t get deep enough.
"Again," he demanded, voice hoarse. "Cum again for me. I’m not stopping until you can’t cum anymore."
He released one ass cheek just long enough to reach around and rub her clit with rough, fast strokes while he continued slamming her down. The dual assault — deep, punishing anal thrusts and relentless clit stimulation — sent Valerina spiraling into a fifth orgasm almost immediately. She cried openly now, tears streaming, voice hoarse from screaming his name and broken pleas.
"Sir—! Please—! I can’t—! It’s too much—! Ahh—!"
But her body betrayed her words. She came again, harder than before, a full-body convulsion that left her limp and trembling in his arms. Her pussy gushed once more, and her asshole fluttered wildly around his pistoning cock. Aiden was panting now, sweat dripping down his temples. The feeling of her virgin ass gripping him so impossibly tight while he used her body like this was destroying what little control he had left.
"Fuck... fuck, Valerina... I’m going to cum," he groaned, voice breaking. "I’m going to fill your guts... fill your stomach with my cum. You’re going to take every drop."
He slammed her down one final time and held her there, buried to the absolute hilt. His cock swelled and pulsed violently inside her. With a deep, guttural roar he started cumming — thick, heavy ropes of cum pumping directly into her intestine, flooding her guts so deeply and forcefully that her lower belly visibly swelled outward with the sheer volume. The warmth spread rapidly, filling her so completely it felt like it was reaching her stomach. Pulse after pulse, he emptied himself inside her, hips jerking upward in short, involuntary thrusts as he drained every last drop into her overstimulated body.
Valerina came one last time from the overwhelming heat and pressure of being filled so deeply. She let out a broken, sobbing moan, body twitching weakly as her sixth orgasm rolled through her in exhausted waves. Tears continued to slip down her cheeks, but they were tears of complete, blissful surrender.
Aiden stayed buried inside her for long minutes afterward, chest heaving, arms wrapped possessively around her trembling form. He kissed her neck softly now, gentle presses of his lips over the hickeys he’d left. His hands stroked her breasts tenderly, then slid down to rub slow, soothing circles over her swollen clit and the stretched rim of her asshole where they were still joined.
"You did so well," he whispered, voice hoarse but full of love. "My perfect girl. Took everything I gave you. I’m so proud of you, Valerina."
She could only nuzzle weakly back against his chest, completely spent. Her body felt heavy, boneless, every muscle trembling from the intensity of her multiple orgasms. The deep, warm fullness in her guts made her feel claimed, marked from the inside out. She turned her head just enough to brush her lips against his jaw.
"Thank you, Sir..." she mumbled, voice thick with exhaustion. "For... for being gentle at first... and then... for letting go. I love you... so much..."
Aiden kissed her temple, then the corner of her eye where tears still lingered. He didn’t pull out. Instead he stayed buried deep inside her ass, his cock still plugging her full of his cum. One hand continued to stroke her hair while the other rested possessively over her slightly distended lower belly, feeling the warmth he’d put there.
"Rest now, baby," he murmured. "You earned it. Sleep. I’ve got you."
Valerina’s eyes fluttered closed. The combination of emotional intensity, physical exhaustion, and the deep, satisfying fullness inside her pulled her under almost immediately. She fell asleep right there in his arms, still impaled on his cock, still wrapped safely in his embrace, a small, content smile on her lips and fresh hickeys blooming across her neck and breasts.
Aiden held her like that for a long time, watching her sleep, occasionally pressing soft kisses to her hair and shoulder. His hand never stopped its gentle stroking — over her breasts, her stomach, the curve of her ass.
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END OF Chapter : 451 : VALERINA’S FIRST ANAL & PEARLY GATE!
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