Playing For Keeps
By Paul Calhoun
A medieval scallywag gets locked up in a courtesans' boudoir that had been renovated as a temporary jail. The only way out is in the wardrobe!

Ronal staggered into the room, hearing the door slam shut behind him. He looked around and mentally congratulated Sir Jins on his good work. For a converted bedchamber, his cell was an effective prison. Ronal was the son of the Duke of Geryman and so when Sir Jins caught him poaching on his land, there was no politic way he could have thrown the young scallywag into the dungeon. Not that Ronal was likely to stay there; he was renowned across four nations for his ability to escape almost any jail cell. His father turned a blind eye because Ronal often returned with useful information for him, often gleaned from the murmurings of lovers he took, daughters of noble houses who often contributed to his legend rather than admit that they had gone with him willingly.

Sir Jins had a special axe to grind against Ronal since he was well known amongst his peers for his carnal appetites. Ronal was a danger to his harem. In fact … Ronal opened the wardrobe and confirmed his suspicions. The purple bedspread and brightly colored carpets had been the first clue, but the closet full of gowns and feminine smallclothes made him sure that he had been installed in the hastily repurposed chamber of one of Sir Jins’ many fair maids. Sir Jins had probably expected that this would make it impossible for Ronal to put together a disguise and that the bars on the windows would keep him from escaping. How little Sir Jins knew of Ronal, heir to the Duke of Geryman.

Ronal was being treated reasonably well and his guards were almost as comely as those Sir Jins took to bed, so he took his time in planning his escape. Every other day he would somehow lose a water skin and he spent his free time picking at the carpets until they were almost totally unraveled. On rare occasions, a changing of the guard had one of his jailers arrive late which gave him a few minutes to practice the voice he’d have to use. There were precious little cosmetics left behind, so he supplemented his supply with charcoal from the fireplace. It would be a touchy thing, but he had nothing better to do.

He’d been keeping track of the guards and knew that there was one who was constantly late and took him less seriously than the others. On a day he knew she was going to be on duty, he started on his plan. He’d ransacked the wardrobe for what he needed and had it all laid out in advance. He started with a silk shift — a luxury that Sir Jins lavished on all of his girls despite the enormous cost — to protect his skin from the second item, a boned corset which he tightened until he felt like his ribs were going to crack. He’d seen Sir Jins’ girls; they were very shapely. He filled the cups with full waterskins and a couple of test bounces were enough to give him further confidence. They also brought his attention to the next part of his disguise.

He’d looked at the thick petticoats that were the latest fashion and thought about whether he’d need to bind himself to hide the bulge which would give him away in an instant. He’d come to the conclusion that he didn’t dare risk it, so he tied the female loincloth as tightly as possible after tucking his manhood between his legs, ignoring how his eyes watered. He squeezed a couple more waterskins into them and dropped the underdress over his head and then the multilayered petticoat. He finished by stepping into the blue velvet gown which covered the lower layers and gave the appearance of a single unit garment. He took a small amount of pride in how far he was able to tighten the laces on it. He fluffed out the skirts and tugged on the sleeves to make sure everything was in place.

There was no mirror, so he was forced to apply the makeup he’d found or simulated by feel. As he applied the powder, kohl, rouge and reddened his lips, he could only hope that he was doing a good job. He was extremely proud of the makeshift wigs he’d created using the woven pad underneath the carpet as a base and the threads from it as hair. Teasing it out, he’d produced a passable red, a very good black and an almost supernaturally luminous, fluffy blonde using the gold thread from the tassels on the rugs and curtains. It was the last that he settled on his closely cropped scalp, turning it and pulling it to and fro to get it into a position that would look good. When he took a step, it almost fell off and he could tell a casual head toss would result in it flying away. He found some of the previous day’s dinner that had yet to be cleared away and smeared some of the sticky pudding on his head before trying again. It felt disgusting, but it did successfully hold the wig on, so he couldn’t complain. He quickly washed his hands, shoved the extra wigs into his bodice and tried to ready himself mentally for what would happen.

He had to work to pull his shoulders back like the girls had been taught to and hoped no one would notice he wasn’t wearing their soft slippers, opting to retain his boots in case he needed to make a quick getaway. Taking a deep breath — and inflating his velvet and linen covered false bosom — he affected a panicked expression and gave full voice to the female tone he’d been practicing. “Help! Help!” He called, trying to pitch his voice up while adding a breathiness that made him sound less like a castrati.

“What’s going on in there?” The lax guard opened a peep hole in the door.

“Help me!” Ronal sobbed. “The Duke’s son escaped and locked me in!”

“How did this happen?” The guard said, opening the door.

“I was giving him his dinner when he overpowered me.” Ronal looked down in mock shame. “I guess I wasn’t paying attention.”

“You’re damn right about that.” The guard realized who would be blamed if she made a fuss about it and her expression softened. “Go on.” She said. “I’ll see that he’s caught again.” As Ronal hurried away he heard her mutter, “I’d better find him or his lordship will have me staked out over an anthill.”

Ronal didn’t like the sound of that but he couldn’t be worrying about every guard who worked for one of his enemies. He thought about making a break for it, but the encumbering dress made that impossible, even if he’d been able to draw enough breath past the corset to sustain quick movement for more than a few seconds. He wasn’t even sure how women managed to get their fluffy, voluminous skirts through doors without getting caught on something, much less took anything more than a tiny step without treading on them. Instead, he swept along at a mince, hoping he looked like one of the girls on an errand for Sir Jins. He was very aware of how the thick skirts swayed from side to side as he did his best to imitate the hip swinging gait of one of the courtesans and how his chest bounced slightly out of sync from his head of literally golden blonde hair.

Ronal was on his way to the main hall and freedom, but didn’t know that between his cell and the way out was Sir Jins’ own suite. As he flounced past, Sir Jins opened the door and saw him. “You there! Who are you?”

Ronal stopped, cursing inside. He had to work hard to put a pleasant smile on his face before turning to look at Sir Jins. “Me, sir?”

“Yes, you. What are you doing here?”

“I’m — I’m tribute, milord. Recently arrived from the town of …” Ronal racked his mind. “Kadorall. The mayor sends his regards. I’ve been getting settled in before being presented to you.”

Jins leered at Ronal, taking in the ample bosom, narrow waist and the soft rounded rear that couldn’t be completely hidden under layers of soft petticoat. “You look quite presentable to me, my darling.” He licked his lips. “Yes, very good.” He stood aside. “Why don’t you make yourself comfortable in my chambers and let me get to know you?”

Ronal was appalled, but managed a weak titter. “Milord is too generous,” he said as he swept past Sir Jins.

“On the contrary,” Sir Jins said, cupping Ronal’s bottom as he passed and closing the door. He moved his grip up, putting his arm around Ronal’s shoulders and guiding him towards a sumptuous couch. He sat and settled Ronal on his knee. “What is your name, my dear?” He said, kissing Ronal’s bare forearm.

“R — Reeanah.” Ronal stammered, fighting to keep his voice pleasantly feminine.

“What a nice name.” Sir Jins wrapped his arms around Ronal’s middle. “What a nice slim girl you are.” He bounced Ronal on his knee and his hands wandered upwards. “And so well endowed. I must remember to reward the mayor of Kadorall.”

“Milord flatters me.” Ronal gulped.

“Not at all.” Sir Jins stroked the golden wig. “You have such lovely hair.” He murmured. Then he set Ronal down next to him and stood up. “And so reserved, so proper. I love a nice shy girl. They always color so prettily when I ask them to honor themselves by doing me a favor.” His trousers fell to the floor. “Let’s see if your tongue is as clever when dealing with my manhood as it is when speaking to my ears.”

Ronal steeled himself and discharged his office until Sir Ronald discharged the staff thereof. It was a constant battle against the need to gag, the desire to run away and the urge to close his eyes. Somehow he succeeded in casting the occasional loving glance up at Sir Jins, who was looking at him with a mixture of affection and lust. When Sir Jins had been satisfied, he took Ronal’s hand and helped him up. “That will be all, my dear. You will be a prized addition to my household. Go and see the mistress of the courtesans now for your assignments.” He pulled Ronal into a turgid kiss, apparently not minding the seed which still clung to the tongue of the feminized Ducal heir. The movement also crushed the skirts into him, making Ronal glad that he’d securely fastened himself rather than trusting their camouflage. After an interminable period of letting Sir Jins paw at him and being forced to reciprocate his advances, Ronal was dismissed with a push on the behind that sent him scurrying out of the suite.

He learned a moment later where Sir Jins had been going when he’d waylaid Ronal because he was less than two steps from the suite when an imperious female voice called, “You there! Hold up!”

“Ah, Mistress Trebula.” Sir Jins said. “So good of you to come find me. I was unfortunately distracted by the new girl.”

“New girl?” The mistress of the courtesans looked at Ronal, who didn’t have to work at shrinking in on himself and looking like a frightened rabbit. “Never seen her before in me life.”

“No? She arrived recently; must have been looking for you when I found her.” Sir Jins said airily. “See to it that she’s taken care of. I think I’m going to enjoy having her. Oh, the reason I wanted to see you is because dear Misha is getting a little too practiced. Give her the usual retirement package.”

Sir Jins closed the door and Mistress Trebula looked at Ronal with friendly impatience. “Come along then,” she said brusquely. “We need to get you cleaned up and settled in. What’s your name, girl?”

“Reeanah.” Ronal said as he tried to follow Trebula’s quick pace while retaining his decorous appearance and a little bit of breath to speak with.

“That’s the best you could come up with, huh?” Trebula asked.

“My lady?”

“Oh nothing.” Trebula continued as if satisfied with Ronal’s response. She showed him into a large parlour filled with young females in various states of undress. “That will be your cell,” she said, pointing to a tiny room with a clean cot. “If you please his lordship well enough, you’ll get something you can entertain in. For now you’ll need to get washed up and ready to present yourself officially to his lordship at supper. When you’re not entertaining, you’ll be carrying messages and doing other odd jobs around the place. There’s always enough to keep busy.” She bustled out, leaving Ronal surrounded by nubile young women and no way to appreciate them as he’d like to.

“Hi,” a honey blonde said, brushing her hair. “Where are you from?”

Ronal had difficulty not staring. The blonde was only wearing smallclothes and a shift, baring her long legs and large breasts. “I’m from Kadorall.” He squeaked.

“Oh really!” The young lady was on her feet and pushing her cleavage into him in a moment. “I have an uncle in Kadorall. Do you know Goodman Gimt?”

“Uh, sure.” Ronal said. The other girls were all smiling — some were even laughing - and he relaxed. “Very nice man. I’m Reeanah by the way.”

“Jinny!” The blonde hugged Ronal, who was now even more glad that he’d bound himself rather than trusting his thick petticoat, since this was a situation to give rise to his ardor. “I’m sure we’ll be very good friends.”

“I’d like that,” Ronal said truthfully.

“Oh, but you need a bit of a touch up,” a redhead said, taking Ronal’s hand and pulling him over to a vanity. “Let us help.”

Over the course of having a makeover and talking to the girls, Ronal loosened up and started to forget that he wasn’t another young courtesan brought in to satisfy Sir Jins’ needs. “Does he usually — ehem — test us out before we get settled in?”

“When he can,” a pale black haired beauty — Yindra — said. “You get used to him occasionally taking you off of something you’re doing and then taking everything off of you.” She giggled. “He’s not a hard person to work with. Well, he’s not hard for very long.”

When the girls had finished, Ronal looked at his reflection and wished he could stay like this a little longer. He’d never gotten to know many women he’d met in the way he knew these courtesans and it was nice to — metaphorically — let his hair down and talk to them on equal footing. No sexual tension, no worries, just a laughter and fun. Plus with their help he made a really pretty girl.

“It’s close to supper now,” Jinny said. “We’d better go down and join Sir Jin.”

That led to a long discussion amongst the assembled ladies as to what they ought to wear. Ronal had to endure watching them take out a multitude of garments to try on, which meant watching them change out of a multitude of garments. His thoughts of sorority were temporarily banished as he did his best to give a genuine opinion whenever asked and not staring at the expanses of skin and flesh. He was shifting uncomfortably in his seat when to his horror they began talking about his wardrobe.

“I know you haven’t been given anything yet, but really we can’t let you go in something he’s seen you in.”

“It’s a very nice gown, but a little old fashioned, don’t you think?”

Ronal was throwing up his hands and protesting, but the ladies wouldn’t take no for an answer. Mercifully, they only stripped him of his over gown, changing it for one with a red velvet skirt and a red and gold brocade bodice.

“See? It matches your hair so much better.” Jinny said. “Here let me adjust this.” She tugged and pulled, getting the gown to settle on Ronal’s false curves more naturally. Had Ronal truly possessed some of the assets the young ladies did, he would have felt scandalized.

“Good!” Jinny took his hand. “Now that we’re all ready, let’s go.”

Ronal enjoyed a very tasty meal and didn’t have to work to blush prettily when Sir Jins raised a glass to him and praised his comeliness and his charm. The young ladies he’d been placed with made good dining companions and he sighed with relief when he found out that it was Yindra who was being called in to share the lord’s bed that night. “I’m not sure I’m up to serving him like that yet.” He confided to her.

“Don’t worry,” she said brightly, smiling at him and patting his hand — now with painted nails courtesy of their hospitality. “Sir Jins won’t ask you to spend the night for a little while yet, though you may be called for other duties as early as tomorrow.” She left in a swirl of newly washed skirts and perfume. Ronal began to wonder if Sir Jins wasn’t on to something.

Ronal really wanted to stay, but he knew what would happen if he did. They’d bedded down with a minimum of fuss, though when Jinny had offered to let him share her bed if he got cold, he worried that his improvised binding would burst. Even if he’d wanted to, he knew he wasn’t going to sleep with so many lovely females that close. So with regret, he waited for the girls to fall asleep and stole out, borrowing a bag to pack the dress he’d stolen along with the one he’d been given and the wigs. Through some ingenuity he’d succeeded in getting some new smallclothes and changing into a nightgown without the courtesans seeing that he was still wearing a tight corset stuffed with water skins. He was beginning to worry that his innards would never be the same after this adventure.

His fortune was still running low, evidenced by the fact that he met the captain of the guard — a large, black haired woman armored even in Sir Jins’ own keep and carrying a sword - halfway down the hall. He cursed himself for not realized that such a high ranking person would naturally be guarding Sir Jins’ most prized possessions, the flowers of his court. A plan formed as the armored woman bore down on him. “What’s your business?” She asked gruffly.

Ronal tried to memorize how she talked. “I was looking … I was … I …”

The guard stepped forward. “Out with it, girl! What are you doing out of your harem?”

Had the captain been at all wary of this slim blonde beauty, she would never have been taken the way Ronal did. He struck her in the solar plexus as hard as he could and followed up with some blows he’d learned from his arms master. It was still a struggle; the woman was a professional and Ronal’s surprise was effectively negated by the unusual center of gravity that his watery padding gave him as well as the breath restriction from his corset. When she was finally laid out, however, Ronal dragged her into a secluded corner and stripped her. His golden wig was traded for the black one, a little longer than the guard captain’s but not so much as to draw attention. He breathed a very long sigh of relief at being able to put the corset away. The guard captain was still built like a lady, but not quite as drastically as the courtesans and her armor would suffice to mold him. Though he had to retain the padding, he felt much better strapping himself into her armor — though not too good because it pinched - and putting on her sword. Her boots had to be discarded as too big but his would look good enough. He felt almost sad wiping off the cosmetics, but consoled himself with the thought that he’d packed some away during his escape. If he wanted to … experiment … he was sure he could find a willing partner in his own land.

Taking on a more authoritative stride, Ronal slung his bag over his shoulder and made for the drawbridge. He threw a few salutes, but was not challenged until he reached the gate. “What is your business?” A guard asked.

“Orders from his lordship,” Ronal felt his throat tearing at the combination of higher pitch and gruffness he had to maintain to sound like the captain. “Let me pass.”

“Yes, ma’am.” They traded salutes and Ronal departed, staying on the road until he was sure he was out of sight and then cutting into the forest. He was sure he’d lose them. It would be at least morning before anyone asked after Reeanah and even longer before the guards admitted they’d lost him.

In the harem, Jinny rolled over. “Has he gone?”

“Yeah.” Came a murmured response.

“Good. He was sweet, but I don’t think he could have stood spending the whole night wrapped up in that stuff with us sleeping next to him.”

“Funny, though. Especially when you made up that bit about your uncle.”

“It was fun seeing him panic like that. I can see why Sir Jins made the mistake; he looked adorable trying to think of a way out. Good night.”

“Night, Jinny.”

Three days later, Ronal was wandering the wilderness and starving. He hadn’t had time to pilfer any food and there was precious little that could be caught with a sword and the makings for a female disguise. He’d thrown the armor in a ditch; there was no situation in which it would have helped. He stopped by a stream thinking that at least he wouldn’t die of thirst and considered his options. Over the sound of the water he heard the industry of a small town. He’d passed three or four, straddling the road while he passed around them in the forest. He really didn’t want to ask for help since he had yet to pass the border and they were Sir Jins’ subjects. That meant that they likely knew who he was and that Sir Jins wanted him. There was probably even a reward. He couldn’t risk in.

On the other hand… His gaze strayed to the sack, bulging with its cargo of femininity. They’d be on the lookout for a young man of his description and maybe even a beautiful girl with golden blonde hair, but a young woman who didn’t match the descriptions might win their pity if not their love. Maidens in distress were still a common enough sight in smaller communities, runaways from worse lives looking for a better group of people to settle down with. There was often a lack of females of a proper age, so the towns were careful to treat them with kindness in the hopes that they’d stay and marry a local son who was otherwise doomed to go far afield for a mate.

Ronal had little choice, so he began as soon as he’d finished formulating his scheme. As much as he dreaded it, he put on the soft shift and laced himself back into the corset, going as far as to hook the ends over a tree branch and pull with all his might. He needed to be absolutely sure he would be mistaken for what he wanted to be. His filled waterskins were installed in the appropriate locations and tested by a few jumps to make sure they were still adequate. Already seeing stars, but resolute, he made a snap decision to go with the red brocade gown once he was in the petticoats and other underlayers. Sir Jins was more likely to remember his whore as she was working than at dinner. He was disappointed that he couldn’t use the golden wig, but that was too distinctive and the black was right out as well, so that left the red. Everything was the worse for wear and he had to use a little mud to stick the wig on, but that was fine. It all added to the illusion of a runaway who had nothing but the fancy clothes on her back.

He had the river for a mirror, so he was very careful with the cosmetics. He’d learned a little from the harem and was meticulous with location and amount. The look had to say ‘I ran away and now I want to make the best impression I can given that I’ve been wandering the woods.’ Having good makeup but dirty clothes would send that message clearly or so he hoped.

Looking at the rebuilt and redheaded Reeanah’s reflection, Ronal was very happy to see a frightened but pretty girl looking back. Her red hair was dull — he couldn’t help what he’d had to work with — and her clothes were the worse for wear, but she looked like she’d made an effort. Rubbing her curves, she was also aware that though her rump was shapely and symmetrical, she had one boob larger than the other. She reached into her bodice and drew out the end of a waterskin. Wrapping her red lips around it, she suckled on her teat until the breast was the same size as its neighbor. A queer expression of longing crossed her face as she put it back and she clutched at her petticoat, rubbing her thighs together. With no one looking, Ronal was freer to react to the reflection of himself as a female doing these things and though it meant soiling the smallclothes he’d bound himself with, he had to get some relief before he went into town.

Goodman Ferd was the first person to see the willowy young lady staggering towards their hamlet. She had a light bag and had obviously gone to great pains with cosmetics, but was travel worn and appeared ill. He called for others and those that were in town that day turned out to help, catching her as she fell into their arms. The girl — Reeanah as she told them her name was later — was taken to the home of Goodman Tarsk, who had recently lost his wife and had the room for her. After being given water and a little food, she explained herself.

“I was,” she blushed, “I was one of Sir Jins’ girls. He said I was too reserved and sent me away with no pension.”

Ronal had gambled on the peasants not knowing too much of Sir Jins beyond his reputation and was rewarded by scowls at Sir Jins and kindly words for her. He brushed his hair back out of his face and smiled bravely. “I can work for my food if I have to, but I’m so hungry.”

“Don’t you worry about that, my dear,” Tarsk said. “We’ll get you back on your feet and then we’ll worry about what to do about you. My son will be back from the fields at sundown and then we can eat a proper meal. For now, you can have this,” he gave her a loaf of brown bread and some ale. “Now you just get your strength back.”

Ronal gladly took the food and thanked the man profusely. The mention of his son was exactly what Ronal was hoping for and he ate with a relish born of having not had much in the last couple of days. The farmer asked him questions and he answered as best he could, trying to keep things simple so he could remember this wayward young lady’s backstory in case he needed to repeat any of it. When he was done, he brushed the crumbs from his skirt and closed his eyes. “I’m so tired,” he said. True, but the pitiable little whimper he added was manufactured.

“Lie down, dear, and we’ll wait for Goerg.” Tarsk said. “He’ll be home soon.”

Ronal was given the peasant’s own bed to sleep in and nodded off despite the corset and binding round his nethers. He awoke when the door slammed and did his best to tidy up his wig and gown before going to meet the strapping young man who was waiting for him.

The part he was playing was well known to him, though he’d only played on the opposite side before. ‘Reeanah’ ate and flirted lightly with Goerg, who had evidently never played the game, since he seemed gobsmacked by Ronal’s attentions. The thin-waisted redhead who laughed at all his jokes and never took her large green eyes off of him was a dream come true in this tiny community. In those rich clothes, she seemed like a princess of old and even held herself like someone of that class. The fact she was paying such close attention to him left him tongue tied at times. This only made Ronal smile more prettily and press harder with handtouching and giggles at everything Goerg said. The food was plentiful as befitted farmers and it was no trick for Ronal to hide two livers and a knife under his gown. Seeing Goerg’s expression, he was sure he’d need it.

When the meal came to a close, Ronal excused himself and departed with a swish of skirts and an only slightly exaggerated hip swing. Looking over his shoulder to see Goerg still looking at him, he smiled and — after looking obviously at Tarsk to make sure he wasn’t looking — blew the young peasant a kiss.

The moment he had a bit of privacy, Ronal went to work. He undressed for bed — leaving on the corset and underdress for ‘modesty’ — and started in on the next part of his plan. He sliced one liver in half and pressed the halves over his ‘breasts’ until they stuck. The texture wouldn’t be perfect, but it would mimic skin well enough when dried and better than the leather of the waterskins. He wished he could have found some beaten lamb skin but that was for later if a later came. He then very, very, very carefully carved the other liver, scooping out some of the inside through the complicated slit he’d made in it. He knew what the real thing looked and felt like, but Goerg wouldn’t know as well and could be fooled — he hoped — by a pleasant feeling imitation. On the other side of the liver from the slit, he carved a phallic indentation and then threaded one of his feminine loincloths through the middle. He took off his binding cloth and substituted this, tying it tightly at the sides and testing it by thinking of how he looked to see if it would hold him in. It did and he put another pair of smallclothes on over the simulated loin.

He lay in the darkness, waiting for the creak which came after a short period of time. “Who’s there,” he whispered.

“Goerg.” The young man replied. “May I …”

“Come in,” Ronal smiled, unsure if the man could see him. “I was hoping you would come.”

Goerg required only a little motivating to climb into bed with Ronal. When the touching came, Ronal thought he did a very nice job of pretending the right sounds and gestures. When the young man mounted him, there seemed to be no fault found and soon he was snoring quietly next to Ronal. For his part Ronal didn’t know what to do next. He’d have to marry Goerg if he stayed, which would be great cover. He’d just have to see what the morning brought. He wasn’t totally dissatisfied. The buck had been energetic enough to stimulate him and it was kind of fun playing the damsel for once. He dropped off, thinking about what he’d do if he ever saw someone who looked like he did now asking for help.