Lessons

(I want to thank everyone again for their support and feedback! Holy cow, over 15,000 reads between the two stories! I have no idea how that stacks in comparison to other stories here, or if that's some sort of average, but it's awesome. The story's taking a nice sexy turn, and without spoiling too much below, there's going to be a bit of play with it, but this is not going to become a fully infantilism-themed story, though it will contain some "mama" calling and gratuitous amounts of breast sucking. And, as requested, we finally get to the sexy! Hope you enjoy!)

His clothes stared up at him from the box almost accusingly. He shifted anxiously, looking at the small padlock in his hand and back to the metal box laying on the floor that held his freshly discarded clothes. The note had said that he could get them back whenever he wanted if he felt uncomfortable, but since it would be locked, he'd have to ask. That was enough in itself to make him hesitate.

"Come on, Ryan." He said to himself quietly, kneeling down and closing the box. His hands shook, pausing for only a moment before clicking the lock closed over the box, a mix of anxiety and relief washing over him as he sealed his fate for the evening.

He walked back to the counter where he'd set the latex undergarments and the powder to help them slide on, wondering how he was going to do this with the almost painful erection he had. Gently dabbing the inside of the latex with the talcum powder, he stepped first one leg in, then the other, slowly sliding them up. They were already hugging him tightly, and weren't going to leave an inch of his body to the imagination. His cheeks flushed a bright red as he slid them up, his cock pinned up against his crotch as he felt them hit his waist, leaving a clear outline of the hard bulge straight up along the front.

Still squirming a bit in the awkward confines of his new garment, he made his way to the refrigerator, where there was indeed a cold bottle of wine waiting. He took it out and then took a crystal glass that was resting conveniently on the counter. Of course he knew she'd placed it there, but it didn't matter. He stopped at the threshold of the kitchen, biting his lip nervously. He had never felt more self conscious than he was now, even during his first days using the public lockers in high school.

"Ryan? Where's my wine?" The call from the living room shook him out of his daze, and her slight tone of expectation was enough to urge him on, his submissive fires already raging from how much he had done before now.

"C-Coming, Mistress!" He called back out to her, and with one slow breath, stepped out, the bulge in the front of the latex getting impossibly harder as he made his way out, pale flesh all exposed to her. She smiled warmly as he moved out, which helped relax him a bit, until he looked down from her smile. Her robe was fully open now, the bountiful curves of her breasts exposed, the open robe just barely covering her aureola. Her thighs crossed, and a slight slip of pink material rested around her thighs, thought it wasn't likely concealing much. He nearly dropped the wine at the sight of her so exposed.

"You're beautiful..." He said almost without realizing it, forgetting his anxiety and nervousness, and his nearly nude state, as he just took the sight of her in. She was stunning, red curls cascading over her shoulders, bright green eyes staring right at him, each curve of her soft body making him more aroused and intoxicated by her than he ever thought that a woman could make him. She giggled lightly, bringing a slender hand up to her lips and beckoning him over.

He stepped forward, needing no more guidance than that, smelling the light scent of perfume that she must have put on. He licked his lips gently. She reached out with her hand, each of her nails painted a perfect ruby red and took the crystal glass from him, gently holding it in her hand and up towards him. Snapped out of his trance, he glanced down at the bottle, which had been mercifully left open, forgoing the need for a corkscrew. He lifted the cork out and tilted the bottle forward, the smooth red liquid pouring into the glass. When it was full enough he tilted it back, setting the cork back in, but not so tightly he couldn't remove it if asked.

"I'm a bit surprised, really. I wasn't sure if you'd go for it, little Ryan. I'm impressed..." Her free hand slid down, gently tracing a finger down the line of the bulge. "...in more ways than one." She gave that soft giggle once more before sipping her wine, nodding to the floor beside her once more. Ryan slid down onto his knees, still blushing, squirming as he fought his natural instinct to take care of his arousal in the way he'd done for so many years.

"Would you like some wine?" She asked after a few minutes. He glanced up and nodded.

"Y-Yes, Mistress. Please." He said, licking his lips as every inch of her flesh seemed even more imposing from the angle he was at. She nodded and picked up the glass, setting it on the ground just at her feet.

"Fill it." He obliged her order, and he knew now that she didn't give requests, but orders, taking the bottle of wine and filling the glass once more. She slid one of her feet down, gently holding the neck of the glass between her toes, her other foot lifting up and dipping into the glass, toes dipping below the surface of the ruby red liquid. "Go, little Ryan. Enjoy." She said, her voice growing slightly heated, the air of control she usually held even more intense. Ryan looked up to her and down to the glass, licking his lips. "Your tongue." She said, her voice a bit more stern.

Ryan looked down at the ruby nails of her toes resting in the ruby liquid of the wine, gently sliding forward, having to get onto his hands and knees, rear in the air as he leaned down. His lips rested just on the surface of her foot as he slid his tongue out, starting to nervously taste the liquid. He wasn't able to lick the liquid up at all without his tongue dragging over the flesh of her toes and foot, feeling the smooth flesh under his tongue. He licked and panted softly, going at first from lapping up the wine to soon licking obediently at her foot.

At some point she moved her foot out of the long empty glass, and his lips went with it, his tongue now sliding between her toes, licking at the ones that hadn't been submerged in the wine, lips dragging over the top of her foot and around the heel, licking at the arch underneath. His cheeks flared red as he panted with each lick, enthralled in the sensation of his submission. She lifted her foot that had been holding the glass and tipped it gently under his chin, guiding his lips upward. His tongue drug over her ankle and up the tender flesh of her calf, lapping hungrily at her leg.

"That's it, boy. Lick higher, but slowly. Savor it. Use your hands, it's okay." Her voice was thick with need as he slid up, taking her saliva slick foot in his hand, gently touching her as his mouth slid up, breathing in the intoxicating scent of her flesh, slowly, ever so slowly, creeping his face up towards the warmth between her round thighs. His own arousal throbbed painfully, and the foot no longer occupied by tipping his chin slid down, big toe gently dragging up and down the thick bulge.

"Such a good slave. You're going to do fine, little boy. You're mine." She whispered out gently. His face continued to face her body as he licked and kissed over her knee, but he felt her shift slightly, her fuzzy robe now sliding down over her shoulders and off. "Don't look." She ordered him harshly, stroking a hand through his hair gently. "God I can't wait anymore, it's been so long."

Her hand suddenly wrenched his hair tightly in its grasp and pulled his head upward, making him grunt a bit in discomfort. His line of sight was soon consumed with the flesh of her body as she pressed his head between her thighs, gasping as she wrapped her legs around his head gently.

Before anything else, the scent of her sex was overwhelming. It made his cock throb painfully, the tight material only making him more aware of his arousal. The soft feel of her sex against his mouth and the warm taste of her juices took over his senses. He'd never gone down on a woman before, but he began to move out of instinct, hungrily licking and sucking at the soft lips, tongue sliding out as he tasted her juices, dragging along a thin material that kept him from pressing the muscle into her.

Her hands grabbed his hair and pressed his head farther into her sex, the slick lips sliding over his face, as for a moment she simply humped herself against him needfully. He wanted nothing more than to fill the need that she was showing him, his lips and tongue working hard on her to bring her to the pleasure that she so desired, and he would be so denied. Her foot continued to shakily stroke up and down his bulge, the slick feel of his precum smearing the inside of the latex.

She pulled his head back for a moment, pressing him back onto his back as she stood over him. Her heavy breasts, each with just a bit of sag from time, and their considerable size, were now bare before him, bright pink nipples hard on the tips. She hooked her thumbs into the waistband of her pink thong, sliding it down and letting it fall off her legs. She leaned forward, starting to slide down, keeping him pinned on his back on the ground. She gently lowered herself down, letting her slick mound press down against his face as she smothered him with her sex. He resumed his oral pleasure of her as she rested her weight on his head, long, intense moans passing through her lips with each lick.

His tongue sought and found the slick inner walls of her passage, slipping forward into her. The taste of her flesh and juices filled him, flicking and vibrating his tongue inside of her. Her moans were a clear show of her enjoyment, so he continued, licking and flicking his tongue inside of her, only stopping when he had to breath. She took one of his hands, which had simply been laying at his side and brought it up, pressing his fingers into the soft flesh of her breast. His hand eagerly began to grope and squeeze as she ground her hips against his mouth, lifting for only a moment when she felt he needed a deep breath.

His fingers found and began to rub and squeeze at her pink nipple, teasing the hard nub as he continued to eat her out. She panted hotly as she pressed down against his face, cutting off his air for a moment as his mouth soon filled with a rush of her juices. She pressed hard against him, grinding hotly as she screamed in pleasure, orgasmic bliss overtaking her. His own cock began to twitch, the pleasure of knowing he had brought his mistress – and that was how he thought of her now, as his mistress – enough to put him right on the edge. It wouldn't take much to bring him off to pleasure.

"Mmmm, damn." She slowly lifted herself off, his face almost entirely soaked with her juices as she rose, panting softly as she looked down at him. She took one of her feet, gently sliding it along the length of his cock. His back arched as he moaned, and he felt like he was going to lose it, just as her foot reached the head of his cock... and was lifted off. "No, no. Not for you tonight, little boy. This night is about Mistress." She smiled and moved back to the couch, still panting, her already beautiful body now glistening with the light sweat of her sexual exertion. "Come up here, little Ryan." She patted her lap.

It took Ryan a moment to get himself up, his entire form still shaking from his near-orgasm, as well as the sensual assault she'd made on his body for her pleasure. He crawled to her, sliding onto the couch and sitting on her lap. Almost immediately she took the back of his head in one of her hands, pressing his still slick lips against one of her breasts, resting his head on the ample valley of her soft cleavage. He breathed deeply, the scent of her flesh, lightly perfumed, putting him in yet another daze. It seemed so easy for her to take away his conscious thought and reduce him to putty. And he loved it.

"You know, it's been so long since I've had someone do so well, little Ryan." She stroked his head as he nuzzled into her breasts, the soft flesh gently pressing under his face. "I'm so glad I chose you. You'll make a wonderful slave." She gently slid his head from the cleavage between her breasts to the tip of one, letting his lips gently wrap around one of her stiff pink nipples. Instinctively he began to suck on it, licking lightly at the nub between her lips. That licking earned him a sharp swat from her hand on his rear. "No, little boy. You just suck." She said softly, almost sickeningly sweetly. He obeyed, sucking warmly on the nub between his lips.

He didn't notice until his cock felt it that one of her hands had slid between them, and as he sucked on her nipple like a child, her hand stroke up and down the bulge of his cock in the front of the latex. He tried to pull his head back to moan, but she had a firm grip on the back of his head and kept his lips pressed forward.

"Suck." She commanded of him, and he obeyed, even as he moaned from the pleasure of her fingers on him. He ground his hips up against her, panting and sucking as he felt the climax welling up inside of him. She looked down to him, and though he couldn't see it, her grin was wicked. "If you cum, little boy, you'll have to leave it in there all night. So go ahead if you want. But don't think you get a fresh pair once you're spent." He almost bit his lip at that, catching himself just in time of biting on her nipple as he sucked in deeper.

His entire body clenched up with each stroke over his hard cock, each time her slender fingers stroked over the swollen head through the latex he felt his balls fill with the cum he'd soon release. He fought it, entire body shaking, as she continued to hold his head to her breast, and continued to tease his throbbing cock, pushing him closer and closer to the brink.

"Go ahead if you want to, little boy." She whispered, her voice dropping slightly as she whispered even quieter. "Cum for mama."

That set him off. Try as he might, those three words, that soft, sultry, throaty whisper was too much for him to take. He moaned loudly, muffled by the flesh of her breast as his cock swelled up, shooting a thick load of cum into the latex underwear he wore. He continued to shoot thick, hot ropes of cum inside of it, feeling it sliding around the length of his cock, soaking the front and sliding down between his legs, panting as he felt himself continue. It was a more intense orgasm than he'd ever felt in his life, even after his physical cumming had stopped his thighs still felt numb with the pleasure.

She pulled his head back slowly after a moment, smiling warmly as she squeezed the cum covered crotch just below the latex, rubbing it gently into him as she lay him back. She let him lay back on the couch, and straddled his middle, slowly making her way up his still heaving chest to his face, her slick mound once more drooling with arousal.

"My turn again, my little boy." She panted out as she lifted her hips up over his face once more.