tagBDSMMaking a Woman of Him Ch. 11

Making a Woman of Him Ch. 11

byElRoylk©

He noticed Catherine was absent from dinner. He was grateful, but it made him wonder if she was avoiding him. He wouldn't blame her -- the thought of having to spank her in front of the other women at the table caused him to blush. He looked around and seeing as there were several empty seats, he decided it could be explained any number of ways. Apparently, except for Sunday night, dinners were optional.

Still, he wondered what was to happen. What if she passed him in the hall? Would he be forced to spank her no matter what? What if she walked into the bathroom, with the other women present? The image of her baring herself to him and demanding to be spanked threatened to eclipse everything else going on, including the conversation.

"...blushing again! My word, Chester, what could you possibly be thinking?"

He looked up and blushed even a deeper red, if that were possible, smiling gamely.

"I dunno, Corrine, but whatever it was it doesn't seem to stop! Look at the poor boy!"

He cast his eyes down, smiling as best he could at the ribbing and concentrated on his mashed potatoes. The conversation moved on, but he had trouble participating. All he could focus on were images of Catherine's backside, presented to him to spank, and, he shook himself, penetrate.

"I swear, Chester, if you don't stop day dreaming, we're all going to starve! Please pass the butter, man!"

He jumped at the voice and reached for the butter plate, passing it to Genielle, the memories dissolving. He shook his head, finished his dinner and excused himself as quickly as he could, explaining he had a lot of work to do.

In the safety of his room, his door shut, he focused on the remaining homework for the week. He had caught up, but given his new circumstances, he was betting he'd be getting more distractions than fewer in the days to come so he tried to get ahead in his reading assignments.

By the time he looked up, it was 10:00 and surprisingly Roxie hadn't appeared. The images from dinner crept back, his peter starting to swell. As he considered whether to make it an early night and start getting ready for bed, there was a soft knock at the door.

"Chester?" Roxie pushed open the door. "I saw your light on and figured you were still up."

He turned to watch her, framed in the door, her arms clutching a stack of books and her laptop. Thankfully she wasn't in her pjs as he had fantasized, but she might as well have been: she had the shortest cut-offs he'd ever seen, and her blouse was tied around her midriff, her breasts clearly visible without a bra.

"Hi Roxie," he sighed with a little more exasperation than he had intended.

"If it's not a good time, Chester." She seemed to notice.

"Well...no...I'm a little tired, is all." He looked up to see her shrink a little. "Shit. I'm sorry. Come in. It's not that hard." He had been referring to Morten's assignment -- something he had dashed off in less than 20 minutes. She looked down at his groin and smiled.

"We could fix that," she said accommodatingly, setting her books down on his bed.

It took him several minutes to figure out what she had said, long after he had started helping her through the homework. While she was busy thinking about her next outline point, he shook his head, wondering what he'd gotten himself into.

"Hey, Chester. Can I ask you a personal question?" She was apparently satisfied with the progress she had made on the paper and was packing up.

He glanced at the clock -- 10:30 -- and nodded. "Sure." He started cleaning up his own work.

"The other night, at dinner, Beatrice asked you about why you like to dress like a woman. Your answer seemed to satisfy everyone, but I'm still curious. Why do you dress this way?" She sat with her palms on her thighs, her face open and sincere.

He remembered his answer, the one he usually tossed off. But at that point he hadn't regained his memory of Yvette's treatment of him, how he had truly come to be this way. Now, now he couldn't hide the truth...but he wasn't sure how he would explain it.

"I...uhhh...well..." A dozen ways to begin flashed through his brain. "I had...uhm...have a step-sister...Yvette..." His hands started to flutter as they always did when he got nervous. "Shit...She..." He stopped, looking at Roxie, flummoxed. "It's complicated."

Roxie looked at him, concern mixed with curiosity. "Okay...it sounds like you're not ready to really share...that's okay." She started to turn to collect her things.

"No!" He put his hands to his mouth in surprise at the force of his answer. He started to giggle in embarrassment, thankful she was smiling with him. "Sorry. No. I would like to tell someone," he said, relief washing through him. He had always considered it a secret, he realized. A secret he couldn't share.

He remembered the first day she made him dress up in public. It was the three of them, Yvette, Lyssa and himself. Yvette had bought tickets to a Sunday concert in the park specifically as a celebration of Lyssa's first line. She had closed a deal the week before with a small retail company -- her lingerie would be in several boutique stores in the Fall.

As usual, he was stripped naked when Lyssa arrived, his peter hanging loose, his body clean-shaven. As far as he knew it was a typical Sunday -- his father and step-mother had some social affair, the help were off, Yvette and he were taking a quiet coffee in the garden. Lyssa walked around the side and through the gate, a box under her arm.

After each of them kissed on the cheeks in greeting, Yvette cleared a spot on the table for the box. "Are these it?" She was practically clapping from excitement.

Lyssa nodded, opening the box and pulling back the tissue. She pulled up a coral tinged lacy bra with a subtle underwire laying on the inside of the box top, followed by the briefest bikini panties, the front panel clearly designed to fit Chester.

"Ooohh, Lyssa. They're beautiful! I'm soooo jealous."

Chester looked at the ensemble and swallowed, the effect on his peter already noticeable.

"Try them on, Chester! Try them on!" Yvette looked like a school girl.

He got up, humiliated his peter had betrayed him and was now sticking out, swaying as he reached for the underwear. He pulled them on, shivering at the feel of the silk against his legs, until he had them up to his waist. His penis was pulled up, but even with the front panel, it was bulging out, pulling on the waistband.

Yvette tsked slightly at how he had ruined the effect, but urged him to put on the bra.

Standing in front of them, in the open air of the garden he thought he might faint. The feel of the silk against his skin, the two of them inspecting him and some hidden plan on their part only hinted at raised his arousal further. His erection was pushing the underwear out further; he knew he was disappointing Yvette and she would punish him for it.

"Lyssa! They're beautiful. Really. Of course, we'll have to do something about Chester's misbehavior, but I've got an idea for that. And the bra -- it's gorgeous, but it would be far better filled out a little..."

"...no problem," Lyssa said, reaching into her bag. "I thought the same thing." She pulled out two pads of latex.

Chester had no idea what they were, but he watched silently as Lyssa came over, unsnapped the bra and slipped them into the cups. "Hold still a sec," she said, resnapping it into place. "Right?" She turned to Yvette for confirmation.

"Exactly!" Yvette clapped and then frowned. "Except for the mess he's making down there. Let's see." She stepped forward and pulled the panties down, his cock snapping out. "Shit, Chester, you'd think you'd get over it already. It's been months." She took his penis and slowly pushed it down, until it was bent over at the juncture with the top of his balls, shoving it between his legs. "Hold still!"

He winced from the pain, trying to bend at the waist. He felt like his peter was going to break!

With one hand still holding his cock down, she used the other to pull up the panties, locking it in place upside down. "Now stand up straight, Chester! That's no way for a lady to stand!"

He knew she would get more angry if he didn't comply. If he hadn't learned anything else since she'd come into his life months ago, it was that: she would make life worse for him. He eased himself up to a full standing position, the bulge from his bent over peter noticeable but not enough to pull the waistband out.

"Let's see what you look like. A little modeling, please."

He knew what they wanted to see. They had trained him a little over the past several weeks. He walked away, swaying his hips just a little, trying desperately not to wince at the discomfort in his penis. When he got to the gate, he turned and walked back, remembering to hold his hands and arms in just the right position. He blushed at how they stared at him, but the walking helped a little, his erection was softening some.

"Beautiful Lys. Absolutely beautiful. I think I have just the thing to go over the top. Chester? You'll be the talk of the town!"

He stopped, panicked at the implications. "No. No, Yvette. You promised!" He said it softly, tears starting to fill his eyes.

"Promised? I don't recall promising anything. What are you going on about Chester? Get control of yourself." She turned to go inside. "I'll be back with the sheath."

Lyssa stood admiring him, gently arranging a strap, evening the waistline of the panties. She smoothed out the wrinkles in the panties, her hand stroking his buns and the top side of his penis. She felt it pulse in response. "You know," she said softly, her hand lingering on his erection feeling it reacting. "I've never been able to ask you what you think. Do you like my work?" She said it with sincerity.

She'd never touched him before and the feeling of her hand on him sent jolts up his spine. He didn't know how to react, humiliated that his peter jumped against her hand with a mind of its own. "I...uhhh...I love the feeling against my skin." It was true, but it didn't directly answer her question.

"You have a beautiful body, Chester, and even though your proportions have made it a challenge..." She left the thought unfinished, stepping back to admire him. "Let's get that picture taken."

It wasn't the first time she'd photographed him, but he still jumped in response to the request. Yvette had made it clear she wouldn't publish them, but the threat was always hanging there, unspoken. Lyssa had made him sign a release saying she could use the photographs in her portfolio. She claimed it was one of the reasons she'd gotten the recent deal.

He stood as they had taught him, his hands on his hips, turned in 3/4 profile. After a couple of shots, he moved his hands behind his head, turning to face her. The last position, him bending forward reaching for some unseen object, always confused him -- what would anyone be doing in this position wearing underwear?

"Here we go," Yvette came swooshing in, a swatch of fabric over her arm. "It just came back from Lourdes'." She held it out for both of them to look at.

Yvette had taken him to the seamstress a couple of weeks before for a fitting. Of all of the things Yvette had made him do, stripping down to his underwear so Lourdes could measure him was perhaps the most humiliating. He blushed at the memory.

He slipped the fabric over his head, the long tube fitted beautifully to his dimensions. It hung off his shoulders, tapering to his waist in a subtle way, the hem just below his knees. The two women arranged it, pulling here, adjusting there until they were satisfied and stood back to look at him. He could see his reflection in the French doors. A strange feeling came over him -- a shift from embarrassment and humiliation to one of...admiration and...attraction. He looked beautiful in that dress.

"Exactly." Yvette turned to Lyssa. "Exactly right.

"Okay, well the two of us need to get ready. Take those things off, Chester and straighten up. You'll probably want to shower and get yourself all primped. We're leaving in an hour."

"Leaving?" He knew it was the deal, but she hadn't been explicit until now.

"Yes, you stupid boy. We're going to the Garden Philharmonic. It's a charity and we've purchased orchestra seats. Now get going."

"Chester?" The memory collapsed at the sound of Roxie's voice. "Where'd you go?"

He shook his head, clearing the images of that day...the fear and panic of being paraded in public, the transformation into liking people staring at him, the constant stimulation against his penis of the silk. It was the last day he had ever worn boy's clothes, finishing up his high school year dressed as a woman.

He started to tell his story to Roxie, the words starting slowly and then tumbling out like children's wooden blocks from a tipped box. With each revelation, Roxie's eyes grew larger, her breathing quickened, her hands going to her mouth and back again. He could see the range of emotion his story was raising in her: sympathy, embarrassment...arousal.

"Chester!" She stopped him, overcome by a particularly cruel treatment Yvette had inflicted on him. "Why...I mean...didn't you tell your dad? I mean...wasn't he in the least...concerned...?" She couldn't understand how Chester could have been abused this way and no one seemed to intervene.

"She had fixed that," he said, relief at finally being able to tell his story flowing through him. He started to cry. "She had made me tell everyone in the house I had chosen to do this, that it was my decision and that I would appreciate everyone supporting me in it. My father was actually proud of me! Yvette had said he was a secret cross-dresser and I figured it was true." He wiped his eyes, his face wet.

Roxie stood and hugged him, pulling his face into her belly to comfort him. She felt the wetness against her, stroking the back of his head to help him. "You are so wonderful, Chester." She wanted to cry she felt such a surge of emotion. She knelt down, her blouse rubbing up against his face until their eyes met. She wiped his tears, stroking back his hair and leaned in to kiss him softly.

Her lips were so soft, her embrace was so kind. It was like a salve on a burning wound. He felt the tension of the past days fall away from him, the secret of the past four years revealed, and in its exposure, the evaporation of guilt and shame and humiliation. He pushed his lips against her, returning the kiss, her mouth opening in response, her tongue reaching out.

She pushed against him, gently moving back into his chair, her tongue pushing into his mouth. She broke the kiss, pulling back. "Oh, god, Chester! I'm sorry! I'm...you..." She looked at him to see if she'd taken advantage.

He brought his hands up to her face, stroking her, looking into her eyes, his relief overpowering the small amount of confusion at her reaction. "What...please...that felt so great." He pulled her face into his, wanting to feel her lips against him, to explore her mouth with his tongue.

They leaned back into his chair, the shift in weight threatening it to roll out from under them. She pulled back again, dragging him with her.

"C'mon," she stood up, lifting his chin up with her hands. Not waiting for him to stand up, she quickly pulled up her top, her breasts now properly free, and faced him, watching as he stared at her unbuttoning her shorts. "Would you...would it be okay to...be with me?" She kept looking at him as she pulled them off, taking her panties with her.

He had stood up by then, his erection pushing painfully against his slacks. "I've never done it before," he said quietly, his hands reaching to her ribs, letting his fingers play across her skin. He couldn't keep from staring at her bush -- the bright red hair framing the thick lips below. His eyes kept jumping from her head to between her legs. "You look so beautiful naked," he complimented her, momentarily paralyzed by what he was seeing.

She blushed, adding further red to a pale pink palette of skin and freckles. She knew what attracted men to her and she had used it over the years to get what she wanted. The memory of Millard, kneeling subserviently to her, pledging to be her slave, drifted behind her eyes. But this felt different. She wasn't seeking advantage, she was truly stricken by Chester's story, the pain and vulnerability, his openness in sharing, raised a new feeling for her, a feeling of nurturing, of healing. She looked down to see her deep pink nipples erect, the tiny pale shadow of the areolas, so small they were almost nonexistent.

"Kiss me, Chester. Kiss my breasts." She said it as a request, not a demand, reaching forward to offer herself to him.

Her breasts. He stared at them as if he had seen them for the first time. It wasn't the first time, of course, he thought back and realized this was the third time -- the first in the bathroom his first night, the second just yesterday morning when she came to visit him in his room, but it was like he'd never seen them quite this way. As he stared at her nipples, so small and pink, he realized he'd seen more breasts in the past few days than he'd seen in his entire life before. The differences were truly remarkable: Genielle's - large black and pendulous, her nipples a deep pink, the surrounding targets large and carmel colored; June's were much smaller but her nipples were big and her areola even bigger, and Corrine's larger than he could get his hands around, a completely different shape.

Until this week, for him, breasts were what bras were for, something he'd never be properly equipped with. But after being exposed to so many, he began to understand why bras were so complicated and why there were so many.

"Chester? Don't you like them?" Roxie looked at him with a mixed expression, pouting and smiling.

He leaned forward and kissed her left nipple lightly. Opening his lips he just barely touched it with his tongue, running it down onto the skin of her breast, feeling it crinkle. Opening his lips wider, he tried to bring as much into his mouth as he could, letting his tongue lie flat on the nipple. He backed up a little. "Your breasts are so different from Genielle's and the other girls."

"Chester!" She slapped him lightly.

"What? Aren't I doing it right?" He turned back to pay attention to the other breast, thinking he had spent too much on the left.

"No, Chester! You're doing it fine. It's just that it's not polite to talk about other women when you're making love. Don't you know that?" She pushed him away for a second to look at his face. "You really don't have much experience do you?"

He shrugged, trying to focus on her right breast, his tongue reaching out to lick the nipple. They were so small and tight, he just wanted to play with them all night.

"You're a virgin, Chester?" The comment just hit her consciousness.

He nodded, thinking about what he'd been forced to do with Catherine last night. "If you don't count butt-fucking," he said quietly.

She giggled, slapping him again, the innocence continuing to fan this new feeling in her. She took his head into her hands and guided his mouth to her right breast, holding it there. "Mmmm, that's nice, Chester. A little lighter...yes, uhhhhhuhh, yessss." She breathed in and out, letting his tongue send sparks into her chest. She could feel his pants pushing against her, the bulge of his erection pressing into her pubic hair.

She walked backwards, forcing him to bend a little more and take a step, until she felt the bed against the back of her knees. Sitting down, she moaned when he had to pull his mouth away. "Chester," she said as she brought her hands up to his belt. "I'm going to take your penis out, like I did yesterday, and then I want you to lay me backwards, spread my legs and push it inside me. Okay?" She looked up at his face, his eyes glazed a little. He nodded, watching as his peter sprang out, relieved.

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