Making a Woman of Him Ch. 06

Lying in her bed, Corrine's hand lightly stroking his cheek, he was pulled back to the memory from earlier that day...Yvette stroking his cheek, trying to quiet him from his shame in putting on his mother's underwear. He moaned softly..."This will be our little secret." He remembered her whispering to him, her face right up against his. "I promise I won't tell anyone. Shh...I just...well...I just need you to do something else for me..."

He opened his mouth to protest, but nothing came out. He stood there, his hands by his sides while she gently stroked his face and his shoulders. "What...what...else do...you...want?" He could barely get the words out between sniffles and sobs.

She leaned forward and kissed him, pressing the back of his head with her hand, her lips sealing his mouth, her tongue penetrating him. He couldn't move, he didn't want to move, his hands came up to her back, holding her, not wanting her to leave. He didn't know what was going on, but her kiss flooded him with comfort and release. He took her tongue, as disgusting as it was it seemed to fit: he was disgusting for doing the things he did. She knew it and she was only telling it like it was. Her tongue drifted across his teeth, across his tongue. She took his breath away and then it was over and she was back in front of him, breaking the embrace.

"Not bad for a beginner, Chester. Not bad. But you can do better and I'm going to help you. But about that little favor," she paused looking down at his penis pushing against the waistband.

He was in a little pain – he'd never restricted his peter before, and he'd never been this excited or stiff. He watched her eyeing him and he shifted hoping she'd get it over with, whatever it was.

"You look like you could use a little help there, little brother. You think?"

He didn't know where she was going. "Yes?" he offered.

"It's just a small thing..."she giggled. "Actually,that'snot such a small thing at all, is it."

He blushed more deeply. "What...?" He could barely get the question out, his throat was dry.

"I want to see you do it. In your mom's underwear." She could see he was completely clueless. "Stroke yourself. Masturbate by rubbing your mom's panties. Isn't that how you do it?" She sat down on the bed and waited.

"No..." he whispered. No. No. NOoooo...she couldn't be serious. OHMYGOD. He was screaming inside, his hands flying up to his shoulders and down to his stomach. "You can't be serious..." He stared at her, begging her with his eyes.

"Wouldn't you be more comfortable lying down on the bed?" She ignored him, making room and patting the coverlet near his pillow. Seeing his hesitation, she reached up to take his hand.

As if in a dream, he allowed her to lead him onto the bed, rolling onto his back. She stood up, spreading his legs a little, he didn't know why but he was too far gone to protest and waited. It was inevitable. She wasn't going to go away and he was already too screwed to matter. He felt his fingers brushing against the underside of his erection, the silk smooth and slick on his fingertips.

"Look at me." She said it kindly, as if she was in love with him, but he knew she didn't love him. As much as he wanted to believe she was being kind, he could see the coldness in her eyes. She darted those eyes between his face and his crotch, watching as his motions got more intense, pressing harder against himself, faster until he closed his eyes and his crème jetted out onto his stomach, a large drip landing on his chin.

He could hear her giggling and clapping and it almost sounded sincere, but he didn't dare look at her, his humiliation at what he'd just done flooding in with the guilt. This wasn't the usual routine. This wasn't just clearing out his ductwork. This was something so terribly different and awful, and he knew it wasn't the last time she would be here, watching him.

"That was beautiful, Chester. Beautiful." Her voice wasn't soothing, the compliments more a judgment than a cheer. "You should probably clean up, and I think, if you're really really careful, you won't get any jism on those silk briefs. There aren't that many left, so I'd be careful with them." And she left him to his grief and disgust, alone in the room.

He avoided her as long as he could, getting up early and out of the house before she awoke, staying away for as long as possible, missing dinner three times that week. No one other than Margaret the housekeeper noticed, and it likely didn't matter – Yvette would have found him whenever she wanted, if she wanted.

Sitting at his desk on Thursday night, he heard her, his heartbeat quickening.What now?He was terrified at the power she had over him.

"Hey little brother," her voice soft. "It's been a while..."

He turned to look at her and froze. She was twirling a pair of light blue panties on her finger, her face expectant. She twitched her eyes to the bed and waited. When he didn't react she smiled, wickedly. "There's no one home tonight – servant's night off, Daddy's away. Time to do the deed, little man."

He choked. "Why? Why are you doing this?" He didn't budge from his chair.

"Because. Because I'm bored, because you are a pathetic little thing, and because I like to see you spray your cum on your stomach wearing your mommy's underwear. Now be a dear and get undressed for your sister."

He didn't move, shaking his head and looking down at her feet.

"I really don't want to have to beg you, Chester darling. It wouldn't be fitting for a woman of my station, do you think? Not very polite ofyouto deny me this little favor. Besides...it's got to be a lot of fun for you too, no?"

He looked up at her, pleading with his eyes.

"Hmmm...not that you're in any position to negotiate, after all. I mean, what would the kids at school say when they find out..." She left the threat hanging and turned as if to go.

"No! No...wait...Okay. Sure. Yeah...bring 'em back." He had stood up and was taking his shirt off over his head. By the time she re-entered the room, he was down to his briefs, and as she handed him the underwear, he was naked.

"Wait." She stopped him as he bent to put them on. "I want to look at that schlong of yours. It's fucking amazing." She stood in front of him, her hands on her waist and just stared at the sausage hanging between his legs. "Amazing." She waved at him to continue as she sat on the bed.

He pulled them up, his peter stuffed into place and stood there awkwardly.

"What do you think about when you stroke yourself, Chester?" She stared at him, from his face down to his crotch.

"Nothing in particular. I just like the feeling of them." He looked at the wall above her head and let his fingers start to play across the front of the panties. He could feel his erection starting to build, the smooth silk jolting his arousal. He felt ashamed and embarrassed at performing this in front of anyone, especiallyher, but in spite of it, he was getting hard.

She watched intently as his cock head began to press against the thin material. "You really get off on this, don't you?" She was just being curious, but her tone was like a dagger into him. He blushed, realizing how awful a scene it must look like.

His peter was doubled over, the wrong way, the head pointing down and the shaft bent and uncomfortable. He slipped his hand inside to rearrange it, so it could be free to point up. He knew she could see its head and he closed his eyes to hide from his own shame.

"Unnh, unh, Chester. Eyes open. Look at me. You know you want to look at me looking at you doing it."

He struggled to stare at her face. It was beautiful and terrifying at the same time. If her eyes weren't so cold, he thought, he would be truly be in love. Watching her, feeling his peter getting harder, he felt something snap inside – he didn't know how to describe it, but he no longer felt like protesting. He stroked a little harder.

"Nice, Chester. Really nice." She sounded more bored than encouraging.

He looked at her, his eyes staring at her face, his expression a mixture of agony and arousal as he felt his climax building. He'd never done it standing up – it would make such a mess – and he wasn't sure if he would peak this way.

"Are you close?" She might as well have looked at her watch, the way she asked.

"Ummm hmmmm," he moaned, wishing he could close his eyes and get it over with. Half of his peter was out of the panties, the elastic on this pair was no match for how hard he was. His fingers brushed across warm skin and smooth silk; he wasn't sure which felt better. And then he felt himself going over the edge, his crème spurting out all over his hand, the panties and the carpet.

Yvette gasped and clapped. "Beautiful, Chester! That's just beautiful, but you'll need to get that cleaned up. The underwear might be ruined...too bad..." And she left him, the shame and guilt pouring down into his brain.

He couldn't stop the tears of frustration and shame as he cleaned up the mess. He just wanted her to leave him alone!

Each night, she would come to his bedroom door and look in on him, his heart pounding at the thought of what she might make him do. Some nights, she just stared at him, not answering his questions until he would turn back to his homework. Others, she would make him strip and put on another pair of underwear, repeating the horrible scene.

"At least let me use a tissue, Yvette!" He pleaded quietly, as he got hard.

She dismissed his concerns, waiting until he had cum before walking away.

By the middle of the third week, his emotions began to shift, confusingly. He spent most of the day wondering if she would come to his room, hoping she wouldn't, and then, hoping she would. The nights she didn't come he was relieved and inexplicably anxious, until one night after waiting for her and realizing she wasn't coming, he went to his mother's drawer and removed one of the last clean pairs of underwear. His father wasn't home and he listened carefully for any movement in the house. It was quiet.

Feeling an urge growing in his belly, he quickly removed his clothes in the master bedroom and slipped the panties on, the excitement growing from the smoothness of the silk as it flowed across his skin. Lying down on the bed, blood pounding in his head from the possibility of being caught combined with the arousal in his peter, he ran his fingers lightly over material, feeling his erection.

He grabbed a tissue from the bedstand before he hit the point of no return and within moments felt the rush of semen in his shaft, the pulsing under his fingers and the hot glop of sperm onto the tissue. His sigh was as much from relief as it was from the inrush of guilt and shame. He jerked up at a sound from the hallway outside the door.

"Nice work, little brother. Very nice." She was clapping softly.

He groaned in embarrassment. He felt a small spark of joy at her being there.

"You're a very naughty little boy, Chester. Very naughty. Do you do this every night I'm not here?" She advanced into the room.

He sat up, cleaning himself up with the tissue. He noted with relief the underwear were not stained. "No," he protested. "This was the first time."

"Ummm hmm. Come here, little brother. We need to have a chat."

He rolled off the bed, his penis still caught in the waistband, a drop of semen oozing out. He dabbed at it before throwing the soggy tissue into the trashcan.

"Tsk, tsk, Chester. You don't want Margaret finding that there. Go get it and come over here." He blushed at the disapproval and command in her voice.

Retrieving the mess from the trash, he returned to stand in front of her, his penis still peeking out, his humiliation at his situation blazing in his face.

"I think you enjoy jacking off for me, don't you Chester? I think you secretly wished to be caught. But you're taking quite a risk, don't you think? What if Daddy came home, or Margaret or any of the others came upstairs?" Her hand lightly stroked his shoulder. It was the first time she'd touched him since that first night and the effect sent a jolt through him. "Well?" Her question, as awful as it was hung in the space between them, demanding an answer.

"I...no...I don't think so...I don't know..." He could feel the tears coming on, the frustration of being shamed by her, the need to rush out of the room and bury himself in his covers, curled up in a ball.

"Here's the thing, Chester. I can't be here every night to help you relieve yourself or play your sick little games. If you want to get off with me watching you in your mother's underthings, I suggest you'll have to wait until it's convenient for me. Do you understand?"

How could she twist things around so much!? That's not the way it was! She madehimdo these terrible things! She was being unfair! "That's not fair, Yvette! I don't want to do these things! You are the one making me do it!"

She raised an eyebrow, nodding slightly toward the bed. "I made you dress up and jack off just now?"

He blushed deeper, tears brimming over. "No...but..."

"You'll not do this again without me, Chester. Do you understand? If you feel like jacking off in your mother's underwear, you'll wait until I am there and you'll do it for me, like you want to. Do you understand?" She had both hands on his shoulders, lightly massaging him. The movement sent a glow through his back.

"No..." He looked down, confused.

"'No,' you don't understand? Or 'No,' you don't agree?" Her fingers dug deeper into his muscles, sending the pleasure of pain down his spine.

"I don't understand. Why?" He closed his eyes, the feelings of her fingers relaxing him.

"Because I say so, Chester, and you're not in a position to argue. In fact, I'm not happy with the position you're in right now at all. In the future, when you want to cum in your mother's panties, you'll ask me, in the most polite way you can, naked as the day you were born, on your knees."

His head shot up to look at her. "You...you can't be serious!" He hissed, not wanting to anger her.

"In fact, let's practice that right now, so you can learn how serious I am." She let go of his shoulders and stood back, waiting.

He shook his head, afraid the humiliation rising in him would make him faint. He closed his eyes and slipped the panties off, relieved to let his penis hang free. Kneeling down, he looked up at her, tears falling from the corners of his eyes, his vision blurred. He could barely see her face but knew she was waiting.

"Please, Yvette..." he began, intending to beg her to not make him do this.

"Yes, cute buns?"

He felt his resistance snap again and some sick need for her approval surged up his spine. "Please Yvette...I would like to cum..." he balked, not certain what to say.

She interrupted him, impatient. "Oh my god, Chester. Here. This is the script, since you can't seem to figure it out yourself. For such a smart boy, you sure act stupid sometimes."

He closed his eyes at the insult and waited, just wanting it to be over so he could go to bed and cry, alone.

"My dearest Yvette," she began, her voice pleading, "I am kneeling here before you to seek your permission to stroke myself in my mother's underwear, so that you can watch me cum for your pleasure. Can you say that?"

His mouth was dry as he attempted to repeat what she said.

"Good enough. Now get out of here before someone catches you." She turned and walked out of the room.

After school every day, he would retreat to his room. She would appear randomly at his door, each time waiting for him to decide what to do. At times he screwed up the courage to ignore her, focusing instead on his homework, his heart pounding at the fear of her response. The first time he was shocked when she didn't push. At other times, he would get out of his chair, strip off his clothes and kneel in front of her, reciting the script.

After a month, he had stopped thinking about it, hoping she would be there, looking forward to it all day, his penis hardening at the thought of kneeling in front of her begging to stroke himself. He began to think he might be falling in love. He didn't know what that was, but he knew he couldn't get her out of his mind, the need to be with her, to do what she asked.

He looked up to see her standing there as usual and nearly jumped out of his chair, removing his clothes and kneeling in front of her. He hadn't yet gotten used to being exposed to the hall – anyone coming up the stairs might see him, his penis hanging, his hand holding hers to his lips. He recited his script as loudly as he dared, scared someone would hear him.

"You are so sweet, little brother. Not tonight I'm afraid. I'm so tired."

She'd never acted this way before. He looked crushed.

"I've instructed Margaret to move all of your mother's clothes into your closet. As of tomorrow there'll be no need to scurry about in Daddy's room. You can play dress up right here. Won't that be perfect?" She yawned, not waiting for his response and walked away.

He lay awake that night wondering what Yvette's plan was, his nerves on edge.

When he came home the next day, he dropped his bag off in his room and stopped. His closet was open, revealing all of his mother's gowns, blouses, and slacks. Her shoes were arranged in their hanging shelves and her sweaters, shawls and over-things were neatly stacked. Alarmed, he opened his drawers to see her bras, underwear, and other lingerie. Except for the clothes on his back everything else of his had been removed.

He kept to his room as long as he could, working hard to concentrate on his homework. He heard a light knocking and looked up to see her standing there. He didn't move.

"I see Margaret has made the move. What do you think?"

"I...you...what am I supposed to wear, Yvette? To school? Out? You don't expect me to dress up like this...outside...do you?"

She laughed, the sound like icicles cracking. "Outside? Now why didn't I think of that?" She looked at him wickedly. "Of course not! That would be a scandal, now wouldn't it? Sweet, dear Chester. Not outside the house. No. But if you could do me the smallest favor..."

He felt his heart pounding in his chest, waiting to hear what would be the latest 'small favor' she had in store for him.

"From now on, since you seem to get such a rise out wearing them, I would just love it if you would dress up around the house – breakfast, dinner – whenever you leave your room. You can do that for me, can't you?"

He shook his head, the heat rising along with his peter. The thought! What would the servants say? What would his father say? "Yvette! You can't be serious! How could I possibly live here – it's...shameful!" He whispered the last word, not daring to even think how awful it would be.

"You are such a dear, cute buns. Do you like me?"

The question came out of nowhere, confusing him. "Yes...but what...?"

"Of course you do. You would do anything for me, wouldn't you, sweet buns?"

He licked his lips, nodding.

"How long has it been since you last masturbated for me, little brother?"

Again he was caught off guard by her question. He paused trying to remember. "Maybe it was four nights ago?"

"You must be pretty worked up, hmmm?" She entered the room and sat on the bed.

He didn't know what to say.

"Well, did you have a chance to look at any of the stuff? When you ran your hands over her underwear, did it give you a hard-on?" She asked it innocently enough, but he could tell there was something behind her words.

"No...not really. I just saw all my stuff gone and kinda freaked...a little." He hesitated, turning to stare at the drawer of underwear.

"Let's try something a little different tonight, Chester. Let's see how those stockings and garters work on you. You can use the undies to stroke yourself. Right here – in front of me. What do you say? Something a little different."