Making a Woman of Him Ch. 01

"Who's he?" Millard pointed to the slight figured guy passing hors d'oeuvres through the crowded party room.

"Chester," John responded, screwing up his face. "He's kind of queer."

"I'll say. Isn't it a little late to be rushing?"

"Oh, he isn't rushing," John paused to take a swig from his beer. "No...Chester was accepted last fall. He just dresses that way."

"But...since when is this house, like, gay?" Millard looked more amused than alarmed.

"Shit, no. And I was out voted. Not because I give a shit what the guy likes to take up his ass, but I just didn't think his...tastes...fit with the house."

"He looks kinda young to be in college...you sure he's even legal?"

"Fuck you, Millard. Besides, he's older than you."

"No fucking way. Really?"

"Yeah, he's old enough to be in graduate school, but he doesn't have enough credits...whatever. Why the fuck should I care?"

The two stood, silently watching Chester move through the crowd, his French Maid's costume raising eyebrows from every one of the guests when he passed by.

As John swept his eyes back through the crowd they caught Corrine's for just a moment. She raised her eyebrows and nudged her head in Chester's direction. John just shrugged and tipped his glass to break contact.

"So what's up with the new maid?" She startled him, appearing next to his ear faster than he could have imagined.

"Please. I don't want to talk about him." He cleared the beer from his throat.

"When did you guys get so equal opportunity?"

Corrine could be...so difficult. "Look. He rushed, the house voted. He got in. I couldn't believe it, but here he is. I figured he wouldn't last a week. In fact, he took such a hazing that first month I didn't believe he'd even stay in school. But here he is." She made him more nervous than usual.

"Nice outfit."

"Shit. That's nothing. You should see his closet. Some of the guys tossed the whole thing out, and a week later he had it restocked. Evening gowns, full length gloves, skirts. Shit."

"What's his name?" She seemed to have taken an extraordinary interest in the little shit.

"Chester. Chester McMillan."

"Oh. McMillan."

"Like, I should know what that means?" He knew he was treading on thin ice, but leave it to Corrine to keep tabs on all of the People One Should Know.

"No. I wouldn't expect you to know. McMillan - only one of the wealthiest families in the region. Railroad money from way back. He's been raised on kilts. Maybe that explains it." She continued to sip from her drink staring at John. He gave a shrug.

"Whatever. Anyway, we laid down the rules - no fucking around with other guys in the house, keeps a 3.5 or better, and he watches his ps and qs."

She raised an eyebrow, her face smug. "And?"

"Fucker's a genius. 4.0 as far as I can tell, and I never see him do any homework. Housework, yes. Homework, no."

"I noticed the place had a woman's touch." She let her hand drift down John's shirt, her fingers rubbing his nipples through the material.

"Fuck." He shivered a little. "You should see this guy clean. Like a mother-fucker. Every time I come home he's dusting there, vacuuming here. That's one thing I'll say for him, we've never had such a spotless bathroom since I've moved here."

"Hmmm...it gives a woman ideas," she stared at John and turned to look at Chester. "What makes you think he's gay?"

The question stopped both of them. They looked down at her like she was crazy.

"Doh?"

She dropped her hand to her hip and stood back. "Seriously. Just 'cause he cross dresses and likes to keep house? Ever see him with another guy?"

"No fuckin' way. Like I said. If he brought one home, he'd be kicked out."

"On campus? Does he hang at the Queer Lodge?"

"Now how would I know that? I don't go drinking over there?" John wasn't ready for Corrine tonight. He could tell she was building up to something, and he couldn't take whatever it was. It wouldn't end well for him. It usually didn't.

"Cleans house, eh?" He could see a glint in her eye. "Would you guys be willing to lend him to us for a week or so?"

"Mmmmm," He stalled trying to figure out her angle. Corrine always had an angle. "I don't see why not. Overnights?"

"Hey, not a problem, right? If he's gay we're in the clear, and I can see where his fastidiousness could come in handy. Wendy's out this semester on Junior Year Abroad. He can sleep in her room.

"Let me check with the council, but I'm sure they'd be fine. By the way -- how old did you say he was?"

"I didn't. To you." He paused, hoping she'd just go away. "22. I think."

"Wow." She turned her attention to another part of the room, their conversation over.

The two of them breathed a sigh of relief, shaking their heads wondering what she was brewing.

* - * - * - *

She watched as Chester walked up the drive, tugging his rolling suitcase behind him, a large handbag on his shoulder. She noted his outfit: a lightweight periwinkle cotton blouse, a pair of Italian cut slacks and low key blue pumps. He appeared nervous.

She opened the door to his knock, hoping to disarm him with a smile.

"Chester! How great you could come! My name is Corrine and I'm the house lead. Please come in!" She stepped aside to let him into the foyer, his suitcase bumping up over the threshold.

He stood looking around, uncomfortable and quiet.

Corrine continued. "You've picked a perfect time to come over. Almost all of the girls are at classes or out, so this should give us a chance to get to know one another and settle you in. Let's get you into your room."

She turned towards the stairs, looking over her shoulder to make sure he understood to follow her. Assured he had gotten the message, she ascended. "One of our girls is spending the semester abroad, in Florence actually, so her room is available. Usually we'd put a guest in the guest room, but I think Wendy's would be a better spot."

She waited at the top of the stair, watching him drag the suitcase behind him. He never met her gaze directly, always looking down or back. Terminally shy, this one. She continued to prattle. "I think you'll like these girls," she pointed to the doors as she passed them, each decorated with small blackboards, stick-on flowers, posters of rock stars. "And I understand you like to clean, right?"

He looked up at her at that and gave a shy smile and quickly looked away.

"Here we are," she stopped at an open door, the room brightly lit by the south facing windows. Wendy had a great room, overlooking the back yard of the house; a single with a lot of storage. Corrine stepped inside and let him pass through taking a long look at his tight ass, held snugly by the designer slacks.

She took a seat in the rolling desk chair and pointed vaguely to the rest of the room. He set the suitcase in the middle and stopped to look around. The room was mostly peach and coral, stuffed animals on bookshelves, a painted desk in the corner, a throw rug in center. She watched as his eyes fell on the bright pink coverlet and just stopped and stared.

"I know, right? I mean, it's a little over the top, especially in this light, but when it's dark you can't really tell what color it all is." She looked up to see him blushing and tried to imagine what he thought was so embarrassing.

"So, let's see. I think the bureau is practically empty. Why don't you go ahead and unpack your things in that and then I can give you more of a tour."

He hesitated and looked around, as if he needed to escape, darting glances back at her. He hunched his shoulders a little and lifted the suitcase onto the bed, unzipping it.

"We have our Council dinner tonight. You picked a great day to start your stayover; everyone will be there and you'll have a chance to meet them all." Her eyes grew larger as he began to empty the suitcase: neatly folded blouses, skirts, a couple of formal gowns, several high heeled open toed sandals, and then the lingerie. Stacks of it.

Corrine took great pride in knowing her lingerie, but she couldn't place it from where she was sitting. "Wow. That's beautiful stuff. Who's the designer?"

"It's from Paris," he practically whispered so she couldn't hear the last part. It was the first words she'd heard him utter.

"Paris. Who?"

"LolaLuna. Actually, a designer from LolaLuna. She's a friend of the family's." He didn't look up and was blushing the entire time. He finished unpacking and began putting the clothes away. As he hung the dresses in the closet, an idea occurred to her.

"Um, Chester?"

He stopped and looked at her.

"I was wondering," she looked down, as if she too were too shy to look him in the face. "Would you...would you consider modeling a couple of those pieces for me?" She quickly looked up to see his reaction.

His eyebrows shot up and he looked her in the eyes to see if she really meant it. Seeing her staring directly at him, without a hint of amusement, he blushed again, realizing what it might entail. "Uh, maybe..." He looked back down at the floor.

"That would be so cool." She saw he wasn't reacting. "Oh! I thought...maybe, like...right now? We have time now. No one will be back for dinner for a couple of hours so we wouldn't be interrupted." She gave what she hoped was an encouraging smile.

He started to shake his head, looking down and around, but didn't say anything.

"I'd really love to see what those look like on you. I'd offer to try some on as well, but I don't think we're the same size." Again, she tried to make sure he didn't hear any trace of teasing or condescension.

"I...guess." He didn't know what to do with his hands. They flitted around his waist and out again.

She got up and closed the door and sat back down again, rolling slightly away from him to give him space. His fingers slowly went to the top button of his blouse. One by one he released the buttons, all the while looking down at the floor to avoid her eyes. He undid the belt buckle, unbuttoned the waist band and carefully pulled the blouse out of the loosened waistband.

He even undresses like a woman.

He slipped the blouse off and pulled a hanger from the rod. His chest was completely clean shaven, nicely toned muscles from his shoulders to a six pack. Corrine registered a little surprise first at the lack of a bra, but then at seeing his underarms completely clean shaven as well, giving her a little jolt at the thought he shaved everywhere. Well, we'll soon see. The image of his penis being smooth aroused her unexpectedly.

He lifted first one and then another foot behind him to slip of his shoes. She noted he was wearing pantyhose and suppressed the urge to shake her head in disbelief. As his fingers slipped into the waistband he hesitated again, and she thought she could see a definite bulge at the crotch. He's getting excited by this! The thought started her imagination going in six different directions.

She watched as he slipped the slacks down his waist. They were so tight they pulled the panty hose tops with them along with the cotton bikini briefs. As he pulled them down, her earlier guess was confirmed: he was completely shaved from his waist to the crease where his shaft met his abdomen. She watched, fascinated, as the complex of pants, pantyhose and briefs pulled across his penis, slowly revealing it, until it sprang out, released. It was much larger than she expected for a guy of his slight stature. In fact, it might have been the largest cock she'd ever seen. By the time he had peeled his clothes off and stood naked in front of her, he was at half-mast and growing. Her own arousal was growing along with it. She stared, wondering how far he was willing to let her push him.

He was blushing so much he was pink from his forehead to his nipples, but he never looked up at her. Instead he busied himself separating his clothes and neatly folding them on the bureau. The distraction seemed to help him; his (not so) little man bobbed around a little lower than before. Even so she continued to marvel at his size.

He opened a drawer and selected a black lace set of panties, garter belt and camisole. "This is one of my favorites," he said quietly, looking up at her.

"I'd like to see you in it, Chester. But could you just hang for a sec?" Smiling at her choice of words, she was curious to see how big he would get when he was fully erect. Of course, nothing was hanging on him at this point -- his sac was tight and his cock was practically sticking out.

Now he really didn't know what to do with his hands. He put them on his thighs, then they drifted up to his shoulders and back again. His eyes darted around the room, down to his growing erection, back to her feet and up to the wall above her head.

"It's okay, Chester. It's just us girls, right? I've just never seen a girl quite so nicely built before is all." She rolled up close to him. "Here, give me your hands, sweetie." She reached up and took his closest wrist guiding his palm to his tight buns. He brought the other one down on the other side and stood stock still. His penis continued to grow.

"You have a beautiful little man, Chester. Actually, it's not so little, is it?" She looked up at his face. He couldn't meet her eyes. "Would you mind terribly if I touched it? I'm not sure I've ever seen a penis quite this size before." She hoped her face communicated the right sense of innocence. She wasn't lying, but she felt he was so sensitive he might shut down at the first sign of deception.

"I guess..." he whispered, nodding slightly, his eyes closed.

She brought her left hand up to it, letting her fingers graze the underside from the head to his completely shaved balls.

He breathed out a sigh but didn't budge his own hands. She took this as encouragement, grasping her fingers around his shaft and squeezing it gently. It swelled further, pointing nearly backward toward his navel. She could feel the blood pumping in it and couldn't imagine it getting any harder...or bigger. It was truly a magnificent cock.

"When was the last time you gave yourself some relief, Chester?" She opened her hand slightly to make it easier to slide along his shaft. She looked up to see him, eyes closed, straining not to look down at her. She looked down at his balls, smooth, hairless, and then further, his legs shaved smooth. She moved her hand up to the ridge of his penis, squeezing slightly at the top. He moaned.

She was curious, was he shaved everywhere?

"Chester," she inquired softly. "Could you pull your hands apart, just a little?" She moved her free hand on top of his knuckles closest to her, helping him. He pulled his ass cheeks apart exposing his brown ring to her. Damn. Not a hair on him anywhere.

He moaned as her fingers moved back down. She took her free hand to feel his balls. The sac was so smooth and unwrinkled, holding their precious cargo tight up to the base of his cock.

"Chester?" She asked again. "You'll tell me when you are going to release, okay?"

He moaned again, his legs tightening.

She wasn't sure what she was going to do. She continued her gentle pumping motion. On the one hand, she wanted to see how far he would ejaculate. She traced the trajectory of imaginary white globules through the air, the plopping sound as they hit the floor. But then she looked and saw they'd get all stuck in the carpet. On the other hand, she would love to have him come in her mouth. Not only did she crave the taste of semen, she wanted to help him feel a little better, maybe soften the blow (so to speak) of this surprising change of plans she had sprung on him.

He started vibrating at the top of his thighs as if battling an internal war. She felt his balls tighten further, if that was even possible, and knew he was close. She slipped her index finger off his balls to push on the muscle between his hole and his sac and it was more than he could bear.

He gave a soft moan.

She felt the liquid bubbling up through his shaft and decided to let it fly. There would be other opportunities to taste him. Besides, he likes to clean so much, I'm sure he'd be delighted to pick up after himself. And then it burst out of him, the thick white stream shot several feet in an arc with a satisfying plop onto the carpet. She moved her hand, milking him as the next batch moved through him. It popped out in a short volley leaving a thin strand to drape across her fingers. This was the part she loved, when boys got so sensitive just after they came. She moved her fingers up to touch the head, causing him to jerk as she lightly stroked it. Scraping her thumb across the open hole, spreading the remaining semen across his glans, he jerked back, opening his cheeks a little more to the cool air.

She leaned forward to brush her cheek against his smooth thigh, wrapping her arm around his ass and between his legs to hug him closer to him. "That probably felt good, hmm Chester? It seemed like a long time since you last came, yeah? When was that?" She asked her questions gently, softly, hoping he would confide in her.

"I only relieve myself on the first Sunday of each month," he almost sounded as if he was crying.

She quickly sat back and looked up at him, keeping her hand on his softening cock, continuing to ease the remaining liquid from him. There was a tear forming at the corner of his eye, now open and looking down at her. She didn't know what to make of his confession.

"Hey! Let's get cleaned up. I can show you the bathroom and continue the tour." She tried to change the atmosphere, but didn't move, keeping her hand around his shrinking member.

He looked around, confused. "But...my lingerie...?" They both looked at the lace ensemble resting on the drawer.

"Hmmm...you're...still...ummm...dribbling a little bit, yeah? You wouldn't want to get any of your jism on your underwear, right?" She pressed his softening shaft one more time for good measure to reinforce the point. A small blob of semen emerged.

He nodded, embarrassed. "Okay...I'll just throw on a robe...?"

She let go of his penis and stood up. "Don't be silly. No one will be back for ages." She walked to the door to invite him into the hall, watching his thing and licking the remnants of his cum from the back of her fingers. It's so huge, just hanging there!

"Down here is the main bathroom," she was several steps down the hall before he reluctantly followed her, naked, his cock swinging. "Three stalls, three showers and a bathtub. We get boys here all the time so don't worry about being the only one with a y-chromosome in the house. If you need a little more privacy there's a single bathroom on the main floor as well." She entered the bathroom beckoning him to one of the sinks. Warming the water she probed a little further into his sexual experience. Just because he cross-dresses, doesn't mean he's gay. The possibilities, if true, began to blossom in her imagination.

"That wasn't the first time someone did that with you, was it?" She washed her hands under the faucet, looking at his face and letting her gaze stroke the front of his body, coming to rest on his bald cock and balls.

He swallowed and looked away. It wasn't, but his mind was swirling with confusing emotions -- why did she just do that? It wasn't the first Sunday! What would happen if he got out of cycle? It wasn't the first time, but he wasn't going to tell her who he had done it with before! A faint memory bubbled up, more an emotion than an image. He shivered a little, blushing.

She reached for a paper towel to help him clean up. "Well, thank you for letting me be the first. I really enjoyed it. I think you have a beautiful body and I'm very impressed with your penis. You have nothing to be embarrassed about!" She ran a stream of water on the towel and turned to hand it to him. Once again, he was blushing from forehead to nipples.