Making a Woman of Him Ch. 04

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Chester’s journey to womanhood begins
1.9k words
4.37
26.8k
7

Part 4 of the 17 part series

Updated 11/02/2022
Created 02/19/2014
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ElRoylk
ElRoylk
335 Followers

Back in his room he shivered uncontrollably. Lying on his bed, he watched the last four years clear away like a fog in the afternoon. Yvette! His teeth chattered as his body relived the horrible humiliations she had made him go through.

He was supposed to go to college – he'd had enough credits between his private tutors and the private school his mother had sent him to. He had just turned 18, his mother had given him a car...tears started to flow even though he wouldn't let himself cry. The accident, the whirlwind of lawyers and servants and...then, his father...coming back to the house to "help take care of the poor boy..."

He'd hated his father – abandoned at 10, his mother always told him he was better off without the "abusive bastard" as she referred to him. And then he shows up. Elbowed his way back into the house and his life, carting a new wife and her daughter with him. Yvette. A wet spot crept across his pillow as his tears dripped.

His mother had been very protective of him – no girls, no distractions – so when Yvette showed up, he was confused by his feelings. Even now, after four years, her cruel smile was all he could see. That, and her body – how it filled out her clothes – her beautifully shaped breasts filling those custom bras; he licked his lips and tasted the salt from his tears. Her underwear, filmy lace that showed off her bush, framed by her garters and stockings.

He hated himself for getting hard at the memories. He looked down and saw the tip of his penis beginning to lift.Damn her!

"So, what do we have here?"

He stared at the young woman who put her purse down on the foyer secretarial without a thought for scratching the surface.What would his mother say!?But she was gone, he remembered too late, his eyes turning away.

"Yvette – this is my son, Chester. Chester, say hello to your sister, Marylyn's daughter, Yvette."

He murmured something politely and waited, watching as she breezed through the house.

He tried to ignore her, successful only for a day or two, and then she showed up in his room.

"It's polite to knock," he reproached her.

"Your door was open – I thought it would be okay." She sat down on the bed and looked around. "I'm bored. What do you do for fun around here?"

He tried to be polite, but something about her pushed his buttons. She was rude, and a boor, and...and beautiful. He couldn't keep his eyes off of her. She knew it too. He had enough sense to know she knew what effect she had on boys.

"Do you like what you see?" She was smiling at him, watching him staring at the "v" from her collar bone down into her blouse. "That might be fun," she said mysteriously.

He had no idea what she was thinking.

"I have an idea," she said importantly, standing up. He followed her with his eyes, confused by the sudden change in her voice. "Let's tell each other something so secret, no one else in the world knows it."

He didn't know what to make of her, her face a puzzle, entrancingly beautiful but mischievous.

"...fuck my mom."

"What??!" He had no idea what she had said, distracted by her face. As he scanned the echo, she kept talking, thinking he might have been scandalized. "I watched your dad fuck my mom" was what she had said.

"I told you it was something so secret no one else in the world knows it. I'd die of shame if you ever told anyone." Was what she was saying.

He gulped, not knowing where to go with the conversation.

"Your turn, silly!" She punched him lightly on the shoulder.

He had no idea what he would say. A secret he hadn't shared with anyone?

"C'mon. Surely you've done something you wouldn't want anyone to know about?"

He just stared at her, falling under a spell. No girl had ever paid this much attention to him.

"It's only fair, Chester! I told you!" She looked as if she would cry.

He didn't know what came over him but he heard himself say it and was mortified even as the words hit his ears. "I masturbate rubbing my mother's panties."

The effect on her was immediate. She put her hands to her mouth and tried to cover her reaction, but her eyes gave her away. Cruel and laughing at him. He turned away from her and covered his face, humiliated and horrified by what he'd just revealed.

"No. Way." She barely whispered. "That's...too...much."

He looked back at her to see if she was still laughing at him, but she had turned to the door.

"I hope I never see you doing such a nasty thing," she said as she left the room.

Things only got worse from there. The next day he came home from school to see three of his mother's underwear on his bed. He paled, setting his books down. Before he could leave to find Yvette, she was at his door.

"I thought I'd make it a little easier for you – no sense in going into Daddy's room, right?" Her eyes were cold, even though she was smiling.

"What are you doing?" He was nearly in tears.

"I'll tell you what, little brother. I promise not to tell your secret to anyone if you do me the smallest favor."

He wasn't an idiot, but as much as he knew she was blackmailing him, he felt a strange pulse in his groin. "What?"

"I'd like to see you try them on." She said it flatly, as if she was asking for a piece of paper from his binder or a slice of cake.

He looked at her like she was crazy, but the effect on him had been powerful. His emotions were all mixed up.

"You wouldn't..." he whispered. "You promised..."

"Promised? I didn't promise anything. I just was bored and said we should share secrets. That didn't mean I was going tokeepthem a secret." Her smile was anything but comforting. "Oh now, c'mon. You're not going to cry, are you?"

He was on the verge of tears. It was the most humiliating thing he could imagine. Who would she tell? It didn't matter who, he concluded. It was too horrible.

"So? Yeah?" She stood watching him, her eyes as cold as a snake's.

"Now?" He croaked.

"There's no time like the present. That sounds great!" Her face lit up a little.

He remembered he didn't quite know what to do then. His hands seemed no longer to be attached to his arms – they fluttered around, first to his belt and then to his shirt, out to the panties. He wasn't sure what to do, freaking out.

"Hey. Chester. Take a breather. It's not that big a deal, right? You're just going to get undressed for me – no one is upstairs right now – and you'll put them on. I think they're about your size, by the way – your mom wasn't too big a woman, and you're pretty slight."

Just get undressed for her?She said it like it was the most normal thing in the world. He looked at her, his eyes brimming with tears. He couldn't. It was awful. She was awful. But the face that stared back at him was unmoved and he knew he would do it. If not right then, eventually. He looked down at his belt, tears falling onto the carpet and he saw his fingers undoing the buckle.

"So," she said conversationally, "how was school?" She continued to stand, leaning against the door frame.

He mumbled something, pulling open his trousers and slipping off his shoes. It had been an okay day at school, actually, but what did that have to do with what was going on here, now?

"Can you strip down completely naked for me, Chester? I hate to see guys with their socks on. It's pathetic."

He slipped his socks off and felt the cool air all along his legs, the hairs rising up from goosebumps. Looking at the bulged in his brief, he couldn't believe he would be exposing himself to his step-sister. He squeezed his eyes shut and more tears fell.

"Seriously, Chester. Get a grip. You don't think I've seen guys before? It's no biggee. Just take off your clothes and get on with it."

He unbuttoned his shirt and slipped it off, pulling his t-shirt over his head. He could feel his penis getting harder and he couldn't stop from blushing. When he looked back at her face, she was staring at him.

"Do you always blush like that? It's amazing." But the way she said it didn't make him feel she was amazed. He felt like a specimen, like some trophy she was pinning to a board to show at the science fair.

He slipped his thumbs into the waistband of his briefs and before he could think about it, shoved them to the floor, quickly bending over to hide his rising organ. But, he knew staying bent over too long was just silly, so he slowly stood up, his peter beginning to point at her.

"Is that thing loaded, Chester?" She chided him, making him feel even more naked by her stares. "Did anyone tell you how well hung you are?" He thought she was going to come over and touch him and stepped back a little, frightened. She just smiled a little and gestured slightly to the panties. "The mauve ones, I think. Don't you? They look like they're your color."

He turned slightly to reach them, his peter now inexplicably rising further. He was in shock from embarrassment. This wasn't something they'd laugh about over Thanksgiving dinner years in the future. This was...forever. This was totally screwed up and he couldn't stop it. As if he wasn't in his own body, he watched the scene, the naked boy with a huge erection, picking up his mother's underwear while his step-sister looked on. Some awful, sick painting he was posing for. Everything moved in slow motion and all at once, at the same time. He felt the smooth silk slide up his legs, the waistband pulling across his sac...

"Look at me, Chester. I want to see your face as you pull them on. It obviously excites you."

He looked up at her, tears obscuring his vision, the waistband scratching the tender skin under his shaft and then they were on, as high as he could pull them. The material at the crotch hugged his balls, the part in back pulled into his crack. As high as they were, his erection was taller, he knew the head was ballooning out of the waistband but couldn't pull his eyes away from hers.

She was staring at him, taking him in like a camera, memorizing the moment. He was so totally screwed. He started crying, he remembered. Sobbing and begging her to stop. The little boy with the erection in his mother's underwear. So humiliated. So screwed.

Her hands on his shoulders shocked him into silence, even though the touch was tender.

"Shhh...Chester...shhh...you've done it perfectly. Just like I asked. Shhh...don't cry. There's no reason to cry." She drew her hand across his cheek, stroking him, her face right up to his. "This will be our little secret. I promise I won't tell anyone. Shh...I just...well...I just need you to do something else for me..."

ElRoylk
ElRoylk
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AnonymousAnonymousabout 10 years ago
I hope that the one other thing

Was either to shoot himself or foregoing that, shoot her. You couldn't have made this any worse if you had TRIED to make it bad. Illogical, implausible actions abound. Even for fiction this was unbelievable tripe.

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