Making a Woman of Him Ch. 16

The rest of the week practically flew by. Pre-finals preparations had put everyone on edge. Everyone that is except Chester...and Yvette. For his part, he simply continued working through his studies, unconcerned about a few tests, final papers, or oral arguments. For her part, she expected him to attend to her as she always had, but it was clear the dynamic had been broken. She wasn't sure what the new dynamic was, but it didn't make her happy.

It was only a couple of days since the "transition" as Chester had come to think about it. They sat across the table at a small café for dinner.

"What do you know about these young men?" She feigned disinterest, sipping her wine, but he knew better.

He paused, feeling more at ease than he'd felt with her since...he couldn't remember when. She was asking him, putting him in a position of importance. He let the feeling wash over him, not willing to leave it alone.

"What?" She looked at him, confused he wasn't responding to her. She smiled grimly. "Oh. I get it. Well, don't gloat too long, little brother. It's not good sportsmanship. And who knows, the table may turn again."

He just shook his head, knowing she'd never change, but feeling free of her influence. Finally. "Millard comes from excellent stock," he began, reciting the background Roxie and the others had given him. "4th generation royalty or something. Great-great is/was an Earl."

She looked unimpressed. "They're as likely to be poor as anything else. Earls don't mean much."

He tipped his head, puzzled. "Whatever. Apparently his family's got some land. Like half the state of Vermont or something. You can get the particulars from Roxie if you need them. He's got a lot to lose, that's for sure, or to give...depending on how you look at it." He smiled, pleased with his small attempt at humor.

She didn't acknowledge it. "And the other one?"

"John Capstold. Noveau Riche, according to what I learned." He was reciting the facts as he'd practiced them. John was going to be a tougher sell, if he wasn't careful. "Folks came into some money through odd circumstances: an inheritance or lottery. Something. Anyway, they're more than flush, but it's clear they've not learned discipline. Typically, John's not up to managing the fortune they've built up. He wasn't born into it, so it's...heck. You know the type, Yvette." All scripted, practiced in front of the mirror, and all true, but the women kept telling him presentation was everything.

She nodded, knowingly, and distracted, preoccupied by the possibilities, her mental calculator going crazy, working through the scenarios.

"Doesn't this feel a little...cheap?" He couldn't resist the need to share his discomfort at enabling Yvette's next steps.

"Cheap? How so?" She looked at him confused and then laughed, a high bird-like trill. He felt his jaw tighten. "Chester, grow up! The stakes are anything but cheap. These boys know what they're getting into – and if they don't, well, it's time to go to school."

He looked down at his plate, wondering if having all this money was really worth it. Maybe he should just let her have it.

She interrupted his thoughts. "And what they had been doing to Catie..."

"Catherine," he corrected her.

She shook her head annoyed at the interruption. "Catherine. You're certain that will be enough...leverage?"

He shrugged again. "It's all news to me. Roxie has plenty on Millard, as far as she's said...I've only seen one instance, and it was pretty horrible. But if she's got stuff like that on both of them, it shouldn't take much convincing."

She sighed, turning her attention to her drink and her meal – it all sounded so...sophomoric. Her options were limited. It was clear Lyssa's endeavor wasn't going to turn the corner any time soon, and she couldn't go back to Daddy for more funds; he'd made that clear last year. Traveling took juice, a lot of it, and damn if she was going to change her lifestyle. She'd been living this life for far too long to let it go. No, she needed cash, and she'd need it before the year was out. If it meant sinking her hooks into a different vein, well, maybe that wasn't such a bad option. Get rid of the sick step-brother.

She looked at him as if for the first time: pathetic, weak and likely under the thumb of that middle-class bitch Roxie. He was lost to her, in any event; Arthur had made that much clear. He was of no further use to her, so he could rot in Roxie's hell for all she cared. But right now, he seemed to be her only avenue to a new source of funding, so she put up with him.

"Fine. I'll try my best. Now let's not talk about it anymore." She looked back at him before returning her attention to her dinner.

* - * - * - *

"How did it go?"

Roxie approached him before he'd had a chance to close the front door. She was in her pajamas – a sheer silk ensemble he recognized from one of the New York houses. The rest of the house was dark, with only a table lamp on in the living room – it was pretty late he realized.

He shrugged out of his coat and looked at her, suddenly shy. "Okay, I think." He lowered his eyes.

"Did she bite?"

He thought she meant literally for a moment and looked up to reassure her when he realized what she was asking. "Yes. I think she'll be calling you for whatever you've got."

She helped him hang up his coat and turned to him, sliding her arms around his ribs, resting her head on his shoulder.

"Chester?" She pulled back to look at him.

He saw something in her look, a glint of mischief and a...tenderness...he'd not seen since...he couldn't remember when...his mother? "What?"

"I'm..." she hesitated, her hands sliding down the sides of his blouse to rest on his waist. "I think I'm falling for you." She stared at him, waiting.

Vulnerable. She looked vulnerable and it triggered an emotion he'd never felt before. Protective, predatory. He mentally shook his head, keeping his face still and looking back into her eyes. At the same time he wanted to bite her, bite her neck, inflict pain and take out all of the years of humiliation he'd been suffering, even as he felt a flood of compassion and warmth. He was afraid if he opened his mouth he wouldn't stop himself. The new feelings raised his heartbeat from anxiety. What is going on?

She moved her fingers, pulling the blouse out of his slacks and quickly unbuttoning it, running her fingers up his smooth chest. "The other day...in my room. I'm sorry if I went over the line." Her hands returned to his waist, undoing the clasp on the slacks. He realized she was stripping him in the front hall of the house where anyone might catch them. He gasped as she peeled his clothes down, his peter springing out into the cool air.

"Roxie," he finally whispered. "We...you...not here!" He waved his hands around at the darkened rooms and the stair, expecting at any moment someone might appear.

She was kneeling now, slipping the pumps off his feet and moving the pile of clothes aside. "You're right, Chester. Come with me." She handed him his clothes and led him by the elbow to the living room, where, if anything, he felt even more exposed. His peter jumped at the thought of being caught. This was public space, not just the council floor – it would be terrible for both of them. He shivered at the possible consequences.

"Shhhh, Chester. Sweetheart. It's okay. Do you know how late it is? Nobody is coming down. I've been waiting up for you." She stroked his back and buns, letting her fingers drift between his thighs. "I couldn't keep my mind off of you...all night. I gave up studying. All I could think of was you, kneeling on my floor, the look of complete desire on your face when I asked you to eat me out." She pushed on the top of his butt, suggesting he should kneel down again. "You liked that, right?"

He understood what she wanted and felt his heart jump at the memory of submitting to her, of how good it felt to push his mouth against her vagina, the taste of her. That other thing, that predatory feeling, it simmered under the surface biding its time.

"I..." She turned to face him, his mouth level with her waistband, "I think I'm falling in love with you, Chester." He looked up to see that expression again, vulnerable mixed with desire. The mischievous glint was there too, but it might have only been a trick of the light. She slipped her briefs down, her red bush pulling his attention back.

He leaned forward, moving his hands to her cheeks to support himself, when she backed up and turned, making him lose his balance, falling onto all fours. Confused, he looked up to see an impish smile as she sat down on the sofa, spreading her legs.

"Could you imagine spending the rest of your life with me?" She asked it quietly, even as she reached forward to take his head in between her legs. "I've so needed your mouth on my pussy, Ches. Ohhhh, two days is far too long to wait...yesss, Chester, shove that beautiful tongue into me."

Like a crocodile, that feeling broke through the surface as he felt her juices on his lips. He took her soft inner folds between his teeth and bit down gently, pulling the leaves out and back.

"OH! Chester! Yes! God! Yes, I love that!" Her hands pulled at his ears, stroking him, urging him on.

Grunting he buried his face into her, rooting like a pig looking for truffles, his nose rubbing against her clit. Sliding up, he took the small button between his lips, pressing them together.

"OHHHHGODDD, Chester!" She moaned quietly and jerked as he shifted her clit in between his teeth.

He'd never done anything like this before, but she had unleashed something. Part of him wanted to hurt someone, but he couldn't believe it was her...Yvette? He didn't stop to think, continuing to work his mouth against her open vagina trying to force another moan from her.

Minutes later, her hands pressing against his head, he felt a rush of pride as she climaxed on his face. The crocodile inside smiled and sank below the surface, satisfied for the moment. He sat back on his heels, listening to her ragged breathing.

"Thank you, Chester. Thank you." She looked down at him, her eyes glistening. "I couldn't have slept tonight, just thinking about the other day..." She reached down to stroke his cheek and eventually stood up, pulling his chin up.

He got up, his peter standing up, stiff and swollen. He blushed at his arousal; he still was embarrassed at his erection, even though he knew it was silly. She reached down, put her hand around it and pulled on it.

"Grab your clothes, Chester. Let's go upstairs."

As she pulled him up the stairs by his penis, the memory of something she'd just said hit him like a soft pillow. The rest of his life?

"Roxie?" He whispered as they got to their floor. "What did you mean about imagining this for the rest of my life?"

They got to his room, moonlight helping them find their way. She turned and hugged him, pressing his erection between them. He couldn't see her face, but he imagined that look and he felt his peter pulse.

"Could you?" She whispered. "I'm having...I really...I'm in love with you, Chester. I'm falling deeply in love with you..."

* - * - * - *

"Lower." She stood behind him, her foot pushing his knees apart. "Get your head on the ground."

Millard's arms were pushed out in front of him on the rug, his knees spread as far as they could go. Putting his head down would mean raising his hips – he wasn't that flexible.

She looked at his ass, spread open, his bare back and buttocks. The hair would definitely have to go. Perhaps tonight...yes, she thought, and she liked the possibilities that drifted into her thoughts.

"Now, you were saying?"

"I umyr svnt."

"Do NOT raise your head! But you'll have to speak up, mumbling won't do at all. Say it so we can hear it. Enunciate!" She pushed the toe of her shoe against his asshole and he jerked.

"I AM YOUR SERVANT." He was sobbing a little, whether from fright, humiliation or pain, she wasn't sure, but in any event she didn't care.

"Yes, you little cunt. You are. For quite a long time. But it's clear you'll need training. You've risen above your station, haven't you, you little cocksucker. Cocksucker...have you ever had the pleasure?"

She had walked around to his head, poking at his ear.

"Well?"

"NO!"

"Hmmm...not very well mannered, are you? So much for you to learn. How tiresome of your former mistress." She sighed. "Manners will be the first lessons apparently. 'No, mistress'. That is what any pony-boy would say to his mistress, hmmm?" She put her shoe on the back of his head. "Say it!"

"NO, Mistress! I've never sucked cock."

She looked up at John, fidgeting. "And you. On the floor. We'll put that thing to good use, or perhaps you'd like to be pony-boy's first?"

His eyes flared in anger, his protests reduced to grunts by the gag. The black latex phallus bobbed in front of his nose.

"Really. Really?" Yvette walked around to him, her head nodding toward the television. "I thought we'd been through this already."

He squinted, his eyes shifting from defiance to fear to anger. He reluctantly bent to the floor, his knees between Millard's spread legs.

"Since you had the little toy, I assume you know how to use it. And given both of your familiarities with anal penetration, let me see how you think it's done." She moved to the desk, inspecting a tube. "Hold on. I'm not interested in that much struggle."

She handed the tube to John, her intentions clear, returning to the bar to sip her drink. It was really too good a scene to leave for her memory alone, she thought, looking around for her phone. By the time she focused the viewfinder on her new pets, John had spread a coil of lube on Millard's asshole.

"Please, John. Don't!" He pleaded quietly, as if there was some way he could change his situation. "We'll figure something out. There's got to be a different way. AhHHHHHHSHITTTTT FUCKKK!"

Whether John thought there might be a different way out or not, he had no intention of defying the bitch. At the same time, he'd never touched another guy's naked skin before, not counting the touch football games; he struggled to position the dildo without having to actually put his hands on Millard. He had brought the dildo right up to his friend's ass and began pushing it in. Surprisingly, it went in easier than he would have expected, and even more surprising, pushing it in gave him a sense of power. Almost as powerful as when he tormented those stupid cunts. He always was a pussy, he thought, the shouts of Millard's agony only spurring him on.

She felt herself getting wet watching the little sadist work his jaws against the gag, pushing further into Millard's ass cheeks. Millard's protests were empty, after all. If he really didn't want this, he knew how to put a stop to it.

John had shifted his knees back to give him more room to maneuver, pushing hard against Millard's open ass. Bottoming out, he started reversing but Millard was clenching hard and the lube wasn't sufficient to overcome his resistance. With the gag in his mouth he couldn't talk Millard through it: he would have to use his hands if he was going to pull out. As he brushed his fingers across Millard's straining thighs, he felt his stomach lurch. He was stuck, breathing as best he could through his nose, the stench of Millard's asshole causing more cramping. A blinding white pain shot up his spine, the result of Yvette slapping his ass with what turned out to be a leather belt.

He spread Millard's thighs with his hands, ignoring the cramping and nausea and began to pull out, the resistance of Millard's rectum against the dildo transmitting directly into his jaws.

"Let's see if you can get him to spew, snail-cunt." She refreshed her drink, feeling the breeze against her skin as she walked. Her reflection in the French doors made her clench a little – her breasts bobbing nicely, her bush neatly trimmed. It had been so, so easy to get them to...cooperate. The ice clinked. She splashed some scotch into the glass and swirled it, rewinding the day.

"Henry Millard, is it?" She read the dossier Chester had fumbled together, her feet up on the table, the sun glancing off the marble counter in her hotel room.

"Just Millard, Ms.?..." His voice sounded nasal over the phone.

"McMillan. Yvette McMillan. I'm Chester's sister. I'm in town for a couple of days, and Roxie suggested I give you a call."

She let the silence dangle between them.

"And?" His voice sounded a little more strained.

"I believe she may have mentioned I would be calling. I believe you and she had an arrangement?"

His intake of breath was all she needed.

"Right then. So, I'm at the Register. Room 407. Shall we say, 15 minutes?" She had no idea where anything was, but she assumed he lived on campus, practically a stone's throw from her window.

"Ms. McMillan...I...er...I've got a prior engagement this evening..."

"Ummhmmm. And your buddy, Capstold. Give him a call. I expect both of you over here in 15 minutes. Do I need to go into details?" She looked out the window at the bright spring clouds. It was really too beautiful a day to spend inside, but the anticipation of breaking the two boys made up for it.

"Uhhh...John? Hold on, Ms. McMillan."

She could hear muffled conversation; she took the moment to inventory the room.

"Could you perhaps be available tomorrow, Ms. McMillan. We both have prior...er...dates this evening...?"

"15 minutes," she said with quiet threat. "The Register. Room 407. And bring all of your toys. You won't be disappointed."

She was a little surprised they showed up as promptly as they did: a light knock on the door 13 minutes later.

"It's open, please come in."

The two young men came in, smartly dressed, Millard with a look of apprehension, John, defiance. He carried a small valise – leather, antique – in a way that led her to believe it was heavy.

"Thank you for indulging me, gentlemen." She got up to meet them, the sheer material of her robe leaving little to their imagination. If it confused them, all the better. "I think we all know why you're here, but if there's any doubt in your mind, let me set matters straight.

"It seems," she directed her remarks to Millard, "that your lady-friend, Roxie, has taken a shine to my brother. As he had previously been under my...guidance, the new situation has become terribly inconvenient." As she spoke, she turned to a small side table and picked up the TV remote. "Please, set the bag down and take a seat." It was more a directive than a request.

Although both were wary, Millard appeared to accept the situation, while John's hesitation suggested he wasn't going to stick around much longer without a good reason. As they settled in, the display lit up, an image of Millard spread-eagled on the bed, his mouth held open, his cock in some kind of contraption.

Millard's gasp of surprise was masked by John's "What the fuck, Millard?"

"She...she didn't...fuck." Millard looked around at the hotel room as if it was closing in, avoiding the screen.

"What. The. Fuck. Millard?" John's attention was welded to the images and the sounds of Millard's gasps and cries as he struggled with something unseen tormenting him.

Millard looked confused. "Really, Ms. McMillan, I'm not sure what...it's...you're not..." He couldn't get a sentence out, his hand waving at the screen, trying to avoid watching himself, remembering that night and knowing what was coming next. His throat was starting to constrict.

She ignored the video – she'd seen it enough over the past day to almost have it memorized – advancing to the next chapter. It was Catherine, tied up and screaming, John fucking her hard in the ass.

"Now that's more like it," John said with snarky ease. "I don't know what the fuck you were doing there Millard, but this I can get into." He looked up at Yvette, challenging her to say whatever she had on her mind.