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Chapter 5: The First Anal Lesson

Author: Ceenem
last update publish date: 2026-04-14 17:32:08

The next morning brought a heavy, humid heat to the North Georgia lake house that made the air feel thick and lazy. Maya woke tangled in the sheets, her body deliciously sore in all the right places from the intense encounters of the previous day. Tyler had already left again for another early fishing trip with his friends, promising to bring back enough bass for a big dinner that evening. The house felt quieter than ever, the silence heavy with anticipation and the weight of everything that had already happened between her and Richard.

She found him in the guest room, the one farthest from the main living areas and the master bedroom where Tyler slept at night. He had cleared the bed of extra pillows and laid out a few carefully chosen items on the nightstand: a large bottle of thick, clear lube, a small black butt plug with a flared base, and a soft towel folded neatly beneath them. The sight sent a flutter of nervous excitement through her stomach.

Richard stood by the window, wearing only a pair of loose black shorts that hung low on his hips. Sunlight streamed in and highlighted the hard, defined lines of his pale, muscular chest and the faint scars from years of physical labor in construction. When he turned to look at her, those piercing ice-blue eyes locked onto hers with calm, commanding authority that made her knees feel weak.

"Close the door," he said quietly, his voice low and steady.

Maya obeyed without hesitation. The soft click of the latch sounded final in the silent house, sealing them away from the outside world.

"Today we are going to take the last part of you that Tyler has never had," Richard continued as he stepped closer. "Your tight little ass belongs to Daddy now. We are going to train it properly, slow and thorough, until you are begging for my cock there whenever I want it."

A shiver ran down her spine. She had never done anal before, not even with Tyler. The idea both terrified and aroused her beyond words, stirring a deep, dark curiosity that made her pussy tingle with fresh wetness.

"Strip for me," he ordered.

She pulled off the thin tank top and shorts she had thrown on after waking, standing completely naked before him. Her heavy DD breasts rose and fell with quick, shallow breaths, her dark nipples already tight and sensitive. Richard’s gaze traveled slowly and deliberately over her smooth mahogany skin, lingering on the dramatic curve of her tiny waist, the wide flare of her hips, and especially the round, juicy ass he planned to claim completely today.

"On the bed," he instructed. "On all fours, face down, ass up high."

Maya climbed onto the mattress, her heart pounding loudly in her ears. She positioned herself exactly as he wanted: knees spread apart, chest pressed down to the cool sheets, back deeply arched so that her thick ass was presented high and completely vulnerable. The position made her feel exposed, submissive, and incredibly turned on. She could already feel her pussy dripping with arousal, a thin trail of wetness beginning to slide down her inner thigh.

Richard moved behind her with deliberate calm. His big, strong hands caressed the full cheeks of her ass, spreading them gently apart to reveal the tight, dark rosebud nestled between them.

"So pretty and completely untouched," he murmured, his voice thick with appreciation. "Perfect for Daddy to train."

He picked up the bottle of lube and warmed a generous amount between his palms until it was body temperature. The cool gel touched her first, a thick drizzle applied directly over her asshole. Maya gasped at the slick sensation. Richard’s finger followed immediately, circling the tight ring of muscle in slow, soothing strokes that made her relax despite her nerves.

"Relax for me, baby girl. Breathe deep and slow," he coached gently but firmly.

She tried to follow his instructions, inhaling deeply and letting it out in a long exhale. His finger pressed lightly against her entrance, not pushing inside yet, just teasing and massaging the sensitive muscle until it began to soften under his touch. When he finally slipped the very tip of his finger inside, Maya let out a shaky moan. The feeling was strange, intensely intimate and slightly invasive, but the generous lube made it surprisingly smooth and not painful at all.

"Good girl," Richard praised, his deep voice a constant, reassuring anchor. "Just the tip for now. Let your body get used to the feeling. You are doing so well already."

He worked the single finger in and out with exquisite patience, twisting it gently, adding more lube whenever he felt the slightest resistance. Maya’s breathing grew heavier with every careful stroke. The initial discomfort quickly faded, replaced by a deep, building fullness that radiated outward and made her pussy clench and drip even more onto the towel beneath her.

After several long minutes of gentle preparation, he slowly added a second finger. The stretch increased noticeably. Maya whimpered softly, her hands gripping the sheets tightly as her body adjusted to the new sensation.

"Too much?" he asked immediately, pausing his movements to check on her.

"No," she whispered, her voice already breathy with need. "Keep going, Daddy. I want it. I want everything you give me."

He rewarded her honesty with a soft, lingering kiss on the small of her back. His fingers continued their work, scissoring carefully to loosen her further, always generous with the lube. The wet, slick sounds filled the quiet room, obscene and intimate at the same time. Richard talked her through every step, his calm, gravelly voice guiding her and keeping her grounded.

"You are opening up so beautifully for me," he said softly. "This tight ass is going to take my cock so perfectly one day soon. But today is about training. Today is about making sure you learn to crave having me back here, stretching you, filling you, owning you completely."

When three thick fingers finally slid inside her, Maya was panting hard, instinctively pushing back against his hand to take more. The fullness was intense now, bordering on overwhelming, yet the pleasure that radiated from her ass straight to her swollen clit was undeniable and growing stronger with every careful thrust. Richard curled his fingers gently, massaging her inner walls while his other hand reached underneath her to find her clit and rub it in firm, slow circles.

The dual stimulation pushed her higher and higher. "Daddy… oh fuck… it feels so good," she moaned, her voice breaking with pleasure.

He kept her right on the edge for nearly twenty minutes, stretching her carefully, teasing her relentlessly, bringing her close to orgasm again and again but never letting her tip over completely. By the time he finally withdrew his fingers, Maya was trembling uncontrollably. Her asshole stayed slightly open for a moment, glistening with lube, before slowly tightening again. Her pussy had left a noticeable wet spot on the towel.

Richard picked up the small black plug from the nightstand. It was tapered, smooth silicone with a flared base designed for safety and comfort, perfect for a beginner.

"This goes in next," he explained calmly, coating it generously with more lube until it shone. "You are going to wear it for a while. I want you to get used to the constant feeling of being filled back here while we move around the house together. Every step, every bend, every time you sit down, you will remember who owns this ass now."

He pressed the tip of the plug against her loosened hole and pushed it in slowly and steadily. Maya breathed through the stretch, the burn pleasant and manageable thanks to all the preparation. The widest part popped past her tight ring with a soft sensation, and the plug settled fully inside her, the base resting flush against her cheeks.

"How does it feel?" Richard asked, giving the base a gentle, experimental tug that made her gasp.

"Full," she admitted, her voice shaky but honest. "Strange… but really good, Daddy."

He helped her stand up carefully. The plug shifted inside her with the movement, sending sparks of new sensation through her body. Walking felt completely different now. Every step pressed the plug deeper, rubbing against sensitive nerves she had never felt before. She could not hide the way her hips swayed or the soft whimpers that escaped her lips as she moved around the room.

Richard made her wear the plug for the next two full hours. They moved through the house together as if it were any normal day. He made fresh coffee in the kitchen while she tried to act casual, helping him load the dishwasher. The plug pressed deeper every time she bent over or sat down on the tall bar stool at the counter. Richard watched her the entire time, his ice-blue eyes dark with satisfaction as she squirmed, blushed, and occasionally bit her lip to hold back a moan.

When the timer he had quietly set finally went off, he led her back to the guest room without a word.

"Back on the bed," he said. "Same position. Face down, ass up."

Maya assumed the pose eagerly this time, her body already conditioned to crave what came next. The plug was still nestled deep inside her. Richard removed it slowly and carefully, her asshole staying slightly open for several seconds afterward, glistening and ready.

"Now for my cock," he said, his voice thick with raw lust as he coated his thick white shaft generously with lube. The head looked even bigger and more intimidating when he pressed it against her prepared entrance.

"Push back against me when you are ready," he instructed. "You control the pace at first. Take as much as you can, then I will help you with the rest."

Maya nodded, breathing deeply and steadily. She pushed back slowly. The fat head of his cock breached her tight ring with a distinct pop that made her cry out softly. The stretch was significantly more intense than the plug, a deep burning sensation that bordered on too much at first. She paused, panting hard, adjusting to the size of him.

"Easy, baby girl. You are doing so perfectly," Richard encouraged, his hands stroking her hips and lower back soothingly. "Keep going when you feel ready. I am right here with you."

Inch by slow, careful inch, she worked herself onto his thick cock. Richard remained perfectly still, letting her take control and set the rhythm. When she had managed to take about half his considerable length, the fullness became almost overwhelming. Tears of intense sensation pricked at the corners of her eyes, but beneath the burn was a deep, dark pleasure unlike anything she had ever experienced.

"More," she whispered desperately. "I want all of it, Daddy. Please give me all of it."

Richard took over then, gripping her wide hips firmly and feeding the remaining length of his cock into her ass with slow, steady pressure. When his hips finally pressed flush against her round cheeks, they both let out deep, satisfied groans. He was buried completely inside her, every thick inch stretching her virgin ass to its limit.

"Fuck… you feel incredible," he growled, his voice strained with the effort of holding still. "Your ass is gripping me so tightly, like it never wants to let me go."

He stayed buried deep inside her for a long minute, letting her body adjust fully to the invasion. Then he began to move, starting with slow, shallow thrusts that gradually grew longer and deeper as she relaxed around him. The sensation was completely different from vaginal sex, tighter, more intense, every single nerve ending lighting up in ways she had never imagined possible.

Maya’s moans grew louder and more desperate with every thrust. The initial discomfort had completely melted away, replaced by pure, mind-melting pleasure that built rapidly. Richard reached underneath her and rubbed her swollen clit in firm, steady circles while he fucked her ass with increasing confidence and depth.

"Look at you taking every inch of your father-in-law’s cock in your virgin ass like such a good little slut," he rasped, his breathing growing ragged. "Tyler could never give you this feeling, could he? He could never stretch you and fill you the way Daddy does."

"No, Daddy… never," she gasped, pushing back to meet every powerful thrust now. "Only you… only you can make me feel like this."

He fucked her harder, the wet, slick sounds of lube and skin filling the quiet guest room. Maya pushed back eagerly to meet him, completely lost in the overwhelming sensation. When he angled his hips just right and hit a sensitive spot deep inside her ass that sent stars exploding behind her eyes, her orgasm crashed over her harder than any she had experienced before. Her pussy gushed onto the towel beneath her in powerful spurts while her asshole clenched rhythmically and tightly around his thick shaft, milking him.

Richard followed right behind her, burying himself to the absolute hilt with a deep, guttural groan. Hot, thick ropes of cum flooded deep into her ass, pulse after heavy pulse filling her until the excess leaked out around his cock despite how tightly her body gripped him.

They collapsed together onto the bed, Richard still buried deep inside her, both of them breathing hard and covered in a light sheen of sweat. He kissed the back of her neck tenderly, his arms wrapping around her possessively.

"That was only the first lesson, baby girl," he whispered against her skin. "We are going to train this beautiful ass every single day until you can take me whenever, however, and as deep as I want. You belong to me completely now."

Maya smiled weakly, her body still buzzing with powerful aftershocks and the deep, satisfying knowledge that she had given him something so intimate and forbidden. Outside the window, the lake sparkled innocently under the bright afternoon sun, completely unaware of the intense surrender happening inside the quiet guest room.

Inside, Maya’s complete surrender to her commanding father-in-law was becoming more total and addictive with every passing hour.

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