Sissy Princess Among Thieves [dani_honey & Reydan]

Dusk had already begun to settle outside, but the castle was far from asleep; distant sounds of battle echoed faintly in its empty hallways. The city of Sungate was under siege! The mighty and ruthless Rhion Empire had attacked the capital of the Sunn Kingdom, and within only a few days, they had wrested control of the city. Now, the only place still holding out was the castle, which housed the royal Sunn family, who had long been the rulers of Sungate. However, judging from the sounds of chaos that were spreading like wildfire throughout its halls, the castle would be flying the Rhion standard before nightfall. With the knowledge of this impending doom weighing down on her, a young woman – one of the castle's maids – hurried along a corridor, her long chestnut hair flowing behind her.

She practically burst through the door as she entered a luxurious-looking bedroom that was dominated by a plush queen size bed at its center. The lavish décor of the room and its gaudy purple color scheme made it fit for a princess. Sitting on the side of the big, soft bed was a slender boy who looked like he had just woken up from a nap; his golden blond, shoulder-length hair still seemed a touch disheveled from sleep. The boy – who couldn't have been taller than 5'3'' – was dressed only in a shirt and a pair of panties. His pretty face looked strikingly feminine; it was difficult to see him as anything other than a flat-chested girl. Even his hips seemed unusually wide for a boy, and there wasn't a hint of masculinity to his smooth, sexy legs. Fitted snugly around his neck was a black velvet choker with a one-of-a-kind jewel attached to it that glowed with a brilliant amber hue – the Sun Star. It marked him as the offspring of King Edward Sunn – the effeminate boy was none other than Prince Samuel Sunn, the 16-year-old heir to the throne.

"Oh. Hello Miesha," the young prince greeted the maid, letting out a cute, drawn-out yawn.

Getting up off the bed, he adjusted his panties. The striped, baby blue & white panties were every bit as cute as their owner, but they almost looked like they were a size too small, as the material appeared stretched to its limit in its poor attempt to cover the boy's plump, tempting rear. Despite the tightness of the underwear, there was nary a bulge in sight up front... the prince must not have been very "gifted" in that department. The comfy, cream-colored shirt he was wearing had puffy sleeves and seemed to conform to his delicate build, highlighting his tiny waist and narrow shoulders.

"Sam! Thank goodness you're okay, m'lord," the maid, Miesha, rushed to hug the boy, making him blush. She continued, beseeching him, "But we have to go, now!"
"W-what? Surely, the castle can't have fallen...! Daddy said—" the prince seemed to be in disbelief. His soft, girly voice matched his appearance to a T.
She shook her head, interrupting him, "The castle is no longer safe, Sam. The Rhion could have already made it inside the throne room."
"But, but... shouldn't I go help Daddy then?" the boy took an uncertain look at the wall, where a garish-looking two-bladed sword – his weapon of choice – was mounted.

The prince was a paladin-in-training after all, so he did have some practice. Swordplay wasn't his strongest suit, however; he was better at healing others and supporting them with his magic. The male instructors at the Order of the Pure Dawn were especially fond of making the novice paladin lay his hands on them in an effort to heal them. Totally for the purposes of training, of course...!

Miesha gave him an exasperated look, "Don't be silly, m'lord! It's too dangerous!"

"You have to escape, via one of the secret passages," the maid explained, clearly having gotten her instructions from someone higher up. "Don't worry about getting dressed. One of the knights, Sir Justan, will be waiting for you in the passage. He'll arrange for everything once you're safe, including clothes. Follow me, Sam!"

The maid led the way – crown prince in tow –, passing through several rooms until the pair arrived at the end of a hallway. After a quick pull of a conspicuous candlestick, a secret door revealed itself in the tapestried wall. The two parted ways, and the boy descended a winding stairway which led further down into the dimly lit secret passages beneath the castle. Sam grabbed a torch from one of the sconces flanking the passage on either side. The boy's pale green eyes shone beautifully in the torchlight. He had never been to these tunnels before, but he had heard that they interconnected with the family crypt. Just when he thought he had gotten lost in the maze of tunnels, the boy spied a shape lying on the ground, motionless.

"Eep...!" a startled gasp escaped the boy's pink, pillowy lips.

It was the body of Sir Justan, the knight whom he was supposed to rendezvous with! The man, clad in plate armor, had collapsed to the stony floor. It looked like foul play... Oh no! Did one of the Rhion soldiers get to him? the young prince thought, alarmed. However, he wasn't about to turn back. Steeling his resolve, Sam forged ahead into the darkness.

Soon, he heard low voices coming from up ahead. They didn't sound like Rhion soldiers. And they were heading the same way he was: away from the castle and out into the city's streets. They weren't moving very fast, so he had managed to catch up to them, skipping quietly barefooted. As he got closer to the shadowy figures, he realized why: they were burdened with loot – sacks of stolen treasure from the castle! They were a bunch of thieves...! They had no doubt raided the family crypt, taking advantage of the turmoil the castle was in.

"Hey! HOLD IT!" the young prince's girly voice rang out, stopping the group dead in their tracks. "That belongs to my family! Give it back, you... you lowlifes!"

The petite boy held his torch aloft and placed his other hand on his hip, expecting the scoundrels to yield to his (very) imposing presence. That's when he remembered that he hadn't taken his weapon along. That, and... he was in his panties.

"Uuuhm..." a troubled expression arose on the sheltered teen's pretty face as he found himself face-to-face with some of the city's less than upstanding citizens.

As the Prince stood there, his feminine form silhouetted against the flickering torchlight, the shadowy figures stopped. A whispered conversation took place, in hurried pace, among the group and then one of them was striding down the tunnel towards the Prince. Before Sam could even react a gloved fist clutching a leather blackjack came swinging out of the darkness and clobbered him over the head. He was senseless before he even hit the floor.

It took two days for Sam to awake, the shock and trauma of the siege and his kidnapping clearly taking its toll on the boy. Around him the siege ended, his parents' heads spiked on the city walls and the citizens of Sungate subjugated under the heel of the Rhian army, and the ordinary people of the city were forced to try and rebuild the pieces of their shattered lives.

Finally, waking, Samuel was confronted by a group of men and women arguing over his bed. The sheets and blankets were coarse and cheap, the pillow lumpy and slightly smelly, and the room around him was pokey and dark.

Apart from a large, hulking, man leaning against the far wall by the door with a bored expression, all the other people in the room with the young prince were arguing heatedly.

'You must have had a reason for bringing him with you Heddon, for fuck's sake' swore a darkhaired woman, her pale skin shining in the soft candle light of the small room. 'I mean, otherwise you've just put us all at risk for a whim'.

'As I've said - he's valuable. You know who he is. You all know what he's worth' protested a thin, weasely looking man, eyes darting around the group.

'I was asking Heddon, Wrest' spat the first woman, directing her venom at a dark, handsome, man with a heavy scowl and annoyed demeanor. He didn't answer, just glaring at the woman, until she threw up her hands in annoyance.

'You know....he's not bad looking' chuckled an older, more sensual, woman who's dark skin tells you that she comes from far-off Halura. 'I could make use of him in the brothel down by the harbour. I'm sure more than a few well-paid Rhian nobles and...'

'Enough' said the final figure, a tall woman with a white eyepatch covering her left eye. 'The boy is awake. I suggest we hold our chatter for the moment'.

She looked down at the Prince's soft, pampered, face with a neutral expression. 'Do you know who you are young man? Do you know what happened to you?'

The effeminate boy's slender body stirred beneath the tatty blankets. Used to the soft beds and silky pillows of the castle, it must have been quite a shock for the young highborn to rest in such squalor. Sam turned in his sleep slightly, which caused the blanket to seductively drape over his lower body, giving a nice view of his round, pantied booty. The dark-skinned Haluran was right: this little sleeping beauty – who looked more princess than prince – would have no shortage of customers at the docks. Unlike the woman's, Sam's skin was fair, and his pampered lifestyle had left it remarkably soft and smooth, almost like a doll's. The teen's alluring green eyes opened slowly, concentrating on the face of the tall woman addressing him.

Ohhh... What happened? Sam thought hazily, sitting up on the bed. There was a faint throbbing in his head, which made him paw at it cutely.

He answered the woman's question, his youthful voice brimming with confidence and self-importance, "I am Samuel Sunn, Prince of Sungate."

While delivering the prideful declaration, the boy idly played with the jewel on his neck, brushing against it with his dainty fingers. The Sun Star marked its wearer as a member of the royal family. Although anyone could don it, it was enchanted so that it would only glow when worn by a Sunn. Its bewitching amber gleam no doubt drew the attention of every rogue in the cramped room... well, of those who weren't admiring the boy's bare legs.

"The castle – it was attacked! I was making my escape, when... when..." Sam trailed off, sounding a bit flustered. His gaze wandered to some of the people behind the tall woman, who looked familiar somehow. "Y-you... ack! It was you! You were the ones who stole from the crypt!"
The boy's tiny body shook with indignation, "You better let me go, or... Or Daddy will be here with an army!"

They all looked down at him, their gazes much more lingering, and the silence much longer, than was comfortable. Eventually, the woman wearing the white eyepatch cleared her throat. She was striking, rather than beautiful, her face cut across by a silvery scar that slashed diagonally across the eye-socket covered by the patch. Her greying hair, dark brown shot through with white, was pulled into a tight bun at the back of her head giving her angular face a severe expression.

'That is the last time you will declare your real identity openly' she said, in a tone that demanded obedience. Her eyes softened a little as she saw the little young man shaking with indignation and fear. 'There is no army...and, I'm sorry to say, you have no father any more. King Edward was killed in the fighting...along with your mother the Queen. Rhian forces are looking for you.' She sighed, pressing her fingers into her brows. 'Whilst it was never my intent to have you brought here, you should thank Heddon and his team. If they had left you in the castle, you would be dead now.'

She leaned in, trying to impress the seriousness of the situation on the girlish young man. As she did, though, her eyes lingered on his soft feminine features and she felt her trousers tighten a little. The cock that Amalda had been born with twitched a little in the Master Thief's trousers. There was something appealing about this young man - the brothel mistress was right. What to do with him?

'I cannot let you leave, Samuel, but I will not simply throw you in prison either. You will have to...start a new life with us. Amongst the thieves and the outcasts of the city. It will be dangerous, and revealing your identity will only lead to your death, but then again it will be the only place you will be safe. The only place where you could live some semblance of a life.'

She patted his shoulder awkwardly, feeling his soft flesh, and sighed. 'I suggest you go across the corridor to the bathhouse and freshen yourself up. Then you can come and see me about your new life. Take your time. You have been through a lot - take your time to think'. The others began to troop out of the room, after Samuel was shown where the bathhouse was, but Heddon lingered in the shadows out of sight. The grizzled thief had been admiring the young Prince's feminine form as well...and intended to see him alone in the bathroom.

"It can't be..." the crestfallen boy let out a sniffle. Hearing about the fate of his parents was a heavy blow for Sam.

Even as he had been making his escape though, he had suspected that something terrible might have befallen them; it was partly the reason why he had kept running, even after stumbling across Sir Justan's corpse in the tunnels. Still, it all seemed like a bad dream. At the royal court, Sam had just been a pretty face; the prince, young and innocent, had been oblivious to the political machinations that led to the fall of the kingdom. All of this had come as a complete shock to him. Now, all alone and hounded by the Rhion, he didn't know what to do. At this point, it was almost a relief to be told what to do, which is why the boy obediently listened to Amalda's words, nodding every now and then as she spoke. Of course, the tall shemale's height and domineering presence also played a part in making the feminine teen compliant.

"O-okay, I'll think about what you said," Sam agreed to go along with her suggestion for now. Besides, he could really use a bath.

Entering the small bathhouse, he could feel the rise in humidity on his skin. Further in, there was a simple, wooden bathtub that was filled with warm water. Next to it, on a squat oaken stool, a pink bar of soap and a small phial of oil with a sweet, girly fragrance had been prepared. It was a far cry from the bubble baths of the castle, but he was still looking forward to it.

Not realizing that he had been followed, the boy proceeded to strip. He pulled off his fancy, puffy-sleeved shirt, revealing his slender, soft body. The teen had no muscles to speak of, but his flat tummy and tiny waist more than made up for it – in the eyes of men, at least. Next came the panties: the boy slid them down, slowly, exposing his perfectly round ass. Stepping out of his cute underwear, he let it fall into a heap along with his shirt. Fully naked – save for the black velvet choker around his neck –, the boy sauntered towards the tub, his shapely hips swaying. Standing on tiptoe, he leaned over to run his hand through the water, feeling its pleasant warmth. Sam let out a happy sigh, apparently not minding the fact that he was presenting his lovely booty to a man.

Heddon watched from the shadows, enjoying the feminine form of the young man stripping off before him. The slender waist but shapely, almost fertile-looking, hips and ass aroused some dangerous passions in the scarred thief as he watched the young Prince. The years of pampering the young paladin's royal life had afforded him soft skin and luxurious hair. Fingers that had never seen a real day of work in their life.

The thief, his cock straining in his pants, began to step out from the shadows before a hand landed on his shoulder. 'Leave' the Guild Mistress said, her low voice full of command. Heddon paused, considering, but his will to obey outdid his desire to approach the young man.

Hearing the lock click behind her as she locked Heddon out, Amalda stepped out of the shadows. 'I thought I would come and see you down here' she said, untying her ponytail. The face that had been so severe before softened as her dark hair came free. Her eyes lingered on his pert bottom, her own cock stiffening in her pants to an almost unbelievable hardness.

'You know, I have been thinking about your situation' she said, and, as he watched her, she slipped out of her top, revealing mature but well-formed breasts, 'You may not like the suggestion' she said, moving closer to him and cupping his cheek, 'but you could pass for a young woman. A disguise that might save your life. But we would have to do something about this...' she reached down and gently tapped his little cock with a finger.

'I have some ideas' she said, stepping back and undoing her belt. 'Because you see' she added, letting her trousers drop with a predatory smile, her thick cock dwarfing the young man's, 'I have a similar problem - born a woman but with a shaft I need to hide'.

She waited, letting the sight of her swollen cock sink in, eating up the boy with her eyes.

Sam wasn't taken aback by Mistress Amalda joining him in the bathhouse, since he was used to being attended upon during bath time; the young prince was accustomed to a retinue of servants washing his hair and lathering his body in soap and lotions.

"Oh, hello!" the girly teen chirped out a greeting. He was busy rubbing the sweet-smelling oil that had been prepared for him all over his body. Soon, his naked form was glistening with an alluring wet sheen. Judging by its girly scent, it was clearly something meant to be used by women, which seemed appropriate given what sort of disguise Amalda had in mind for the boy...

"A w-woman?!" Sam repeated her scandalous suggestion, blushing like a maiden. The boy's embarrassment only deepened when his cute little cock was poked at. The puny thing measured just barely over three inches – how adorable! He tried to protest, feebly, "B-but... I'm a paladin! Paladins are supposed to be brave and manly, and—"

He wanted to say more, but his thoughts came to a grinding halt when the tall, busty shemale decided to show what she was packing. The boy's pretty green eyes widened in awe at the sight of her huge, erect cock. When she had bared her breasts, he had taken a curious, passing glance at them, but now the boy was clearly staring.

"It's... so big..." he uttered in disbelief and what seemed like admiration. "I mean, err, I can see how it would be tough to hide...!"

Realizing that he was getting visibly "excited", Sam quickly turned around. He timidly peered over his shoulder, giving the hung lady a sheepish smile, "Umm, would you like to join me? I'm not used to bathing by myself..."

The tub wasn't very spacious, but they would probably fit, provided that Sam didn't mind sitting on the woman's lap.

Amalda noted with interest that the young man paid no more than passing attention to her ample breasts but was transfixed by her cock. She hadn't suspected that the young man would be as suggestible as all that, or as accepting. Most men and women considered her kind freaks to be looked down upon - it was one of the reasons she had dedicated her life to living and working in the shadows. The knowledge that the young man before her with the soft, feminine lips and pert ass did not instantly hate her for being different. If anything, it made the Guild Mistress harder, the swollen head of her cock leaking a little pre-cum.

She stepped up behind the young man, placing a possessive hand on his hips as she agreed to his request. 'How could I refuse such a polite request' she smiled 'I can tell you were very well-bred indeed'. And Gods I would love to breed you she added silently.

She moved around him into the warm water, sinking back against the wooden edge of the tub, and half helping half lifting the young man down onto her lap. Her soft breasts cushioned his back as he settled against her chest and she felt his soft, girlish, hips wiggle delightfully against her lap.

Her monstrous cock stuck out of the steaming water, dwarfing his own, and she shifted slightly so that the two mismatched shafts pressed together. 'You know' she said 'the trick to passing yourself off as a woman is to suppress your masculine desires...and the evidence of them'. She purposefully ignores his protest earlier about Paladins being manly. 'The easiest way is to masturbate in the morning when you awake, to ensure your cock is less excited and visible through your clothes.' She gently rubbed the two cocks together by moving her hips. 'Do you know what I mean Sam?'

The girly teen happily settled onto the woman's lap, resting his pretty bum against her thighs. He could feel the tension leaving his body as he sunk into the pleasant warmth of the water. Sighing contentedly, Sam reclined his head, resting it against Amalda's chin. The boy closed his eyes and enjoyed the sensual bath, losing track of time.

Alas, the innocence of the moment was not to last: he could feel the shemale's hardness poking him, pushing against him insistently. Apparently, the Guild Mistress' advice of suppressing one's masculine desires only applied to little sissies like Sam. A flush crept across the boy's cheeks, and his embarrassment only grew worse when the topic turned to masturbation. Sam was a chaste, proper young prince, after all. He wasn't really sure what Amalda meant, but he didn't want to appear clueless either.

"I-I think so...!" the boy's soft, girly voice trembled slightly as he felt the woman's overpowering erection against his tiny little thing; she was so much bigger and harder than him that her dick just bullied his around. He could feel his earlier arousal flare anew, but he tried to ignore her teasing. After all, it's not like he liked dick or anything! He was a pure, virtuous paladin, only interested in wholesome things.

"Mmm~..." a cute little sound escaped Sam's soft, full lips. He could feel Amalda's fat dong pressing against his smooth ballsack. He had never felt so turned on before in his young life. Soon, the boy's legs parted slightly, giving Amalda's thick cock even more free reign. The prince squirmed in her lap, grinding his haunches pleadingly against her, but it was no use.

"Ohhhhh—" the boy let out a barely suppressed, girly moan. He spurted several times beneath the surface, his tiny penis twitching helplessly in the presence of the shemale mistress' superior manhood. Just like that, the petite boy had been drained of his masculine desires. Blushing fiercely, the young paladin stammered, "E-excuse me, I don't know w-what came over me...!"

Feeling rather dirty all of a sudden, Sam reached out for the pink bar of soap. As he leaned over the tub's edge, his bubble butt was mere inches from Amalda's face – countless water droplets created a wet luster to the teen's delicious rear.

It was clear to the older woman that the girlish little Prince had no real idea what she was talking about. His cheeks were flushed and his voice had a delightfully high pitch to it as he squeaked his answer to her teasing questions. The two cocks rubbing together, one pathetically small and one large and angry, were clearly pushing him over the edge and her hands instinctively found his hips as his little shaft shuddered and orgasmed. It was almost amusing and she had to suppress a chuckle as the young man stammered his apology, his face now beetroot red.

As he leaned forward, for the soap, he presented her with a perfect view of his tight little ass. She could see his rosebud, so tight and enticing, winking out between the plump little cheeks. She was half tempted to rise up, cascading water, and force her huge shaft straight up his little ass. But a life on the street, making crumbs count, had made Amalda learn to cherish every little thing that came her way. When you hadn't eaten for three days straight as a street urchin you made sure to savor the loaf of bread you stole and not eat it all in one go.

Instead she stood and leaned into his back, her large cock nestling between his moist ass cheeks. It throbbed with need. Her breast pushed against his back and her breath was hot on his ear. 'See, now you could pass for a girl much more easily' she said, nudging his spent cock with a finger, 'but I still need your help. You need to learn how to ease your cock to pass yourself off as a woman'. Holding his hips, she guided him back to their sitting position, her erect shaft rising again between his spread legs. She took his hands and, guiding his quaking body, wrapped them around her shaft.

'You need to rub the cock' she said, breathing hot onto his ear 'rub it to relieve the arousal that might give you away.'

"Hwaah~!" Sam gave a silly, startled yelp when Amalda came up behind him, almost dropping the soap he had picked up. Instinctively, the teen's legs parted ever so slightly when he felt her powerful erection between his butt cheeks. Her hot breath tickled his ear, melting away any thoughts of resisting the perverted shemale; the dove-eyed, suggestible boy was putty in her hands. Back on her lap, Sam handed the soap over to the woman, allowing her to scrub him down while he had something else to play with. Something more to his tastes.

"Doing this..." Sam eyed her throbbing member with uncertainty. "Will it really help me with my disguise?"

The petite boy needed both of his hands to fully wrap around Amalda's impressive girth. Her size made him gulp, but it also seemed to fascinate the girly prince; he got to play with a real cock for a change. Tentatively, Sam slid his dainty hands – made slick from handling soap – down her length, all the way to the base. He could feel the lust coursing through the massive penis, which seemed to like the sissy's touch very much. One of his hands snuck lower, gently caressing her nutsack, while the other slowly stroked her entire length. When he reached her glans, he decided to cup it, delicately teasing her sensitive ridge with his pretty nails; his hand came away coated with a clear fluid, but he didn't seem fazed by it.

"A-am I rubbing it right?" the boy sought the mistress' approval, like a cute puppy looking for a pat on its head.

Soap bubbles had begun to form in the water as Amalda cleaned the boy, massaging his slender shoulders and back. As he felt her hands going lower, Sam raised his leg to accommodate her touch, his perfectly manicured toes peeking out from the soapsuds. In response to her caresses, the prince tightened his grip on her shaft, pumping it faster, coaxing the shemale's heavy, cum-filled balls to give up their load.

'Mmm yesssss' groaned Amalda, the mature woman leaning back against the tub to fully enjoy the soapy handjob she was being given. Each touch of the little Prince's hands on her shaft felt heavenly, especially the tender attention he gave to her glans, his nails coaxing a little precum from her swollen balls.

'This will help you blend in as a woman' she moaned, rubbing his feminine little shoulders as he worked her cock. It wasn't a complete lie, she told herself, as the boy would find himself in situations where he'd need to rub one out. Or maybe rub someone else off....

Thinking such lewd thoughts, combined with the soapy pleasure Sam was visiting on her cock, pushed the Guild Mistress over the edge. She came in a rush, harder than she had done in years, and the pent up sexual frustation of months was visited all over poor old Sam. Rope after rope of hot, sticky, cum shot from the swollen head of her cock. It spatted his face, his neck, his slender chest, and, as she screamed in pleasure, the final ebb dribbled down over his small hands.

'Gods' she moaned, fighting the urge to just bend him over and fuck him, and gently turned him in her lap to enjoy the sight of him drenched in her seed. 'You need to wash yourself off' she smiled, slipping out from under him and climbing out of the tub. She patted the pile of clothes she had brought in with her - a simple serving girl's brown dress with sleeves to the wrist and a skirt that reached to the knee.

'Come to my office, at the top of the building, when you're cleaned up' she smiled and, impulsively, leaned in and kissed his little forehead before smiling down at him.

The sudden blast of jizz caught the unsuspecting boy by surprise, making him flinch. His pretty face took the brunt of her ejaculation, as Amalda's thick cock had been pointing right at it. It was a fitting reward for the little sissy for his efforts: a warm, creamy coating of goo. Eww, it got all over me... the prince thought, pouting cutely, although he didn't look too upset about receiving his first-ever facial.

"There's so much of it...!" he remarked as Amalda turned him around. It looked like at least three men had emptied their balls on the teen's face. One dollop of cum had even landed on his left eye, forcing it shut. Maybe he could get a matching eyepatch to hers... or not. Sam wiped it off, blinking his beautiful, pale green eyes a few times. His vision cleared, the boy followed Amalda with his gaze as she got out of the tub, admiring her fit, mature body.

When she placed a kiss on his brow, Sam couldn't help but return her smile. Looking up at the tall, striking shemale, he quickly nodded, "O-okay, I'll meet you there."

Following her advice, he set out to clean himself. However, when the mistress was out of sight, curiosity took hold of him... Sam scooped up some of her sperm with his fingers and peered at the white stuff inquisitively. He took a tentative lick, ready to spit it out at a moment's notice, but... Hmm~, the boy seemed to approve of the taste! Thoughts of lapping up the rest of the shemale's tart ball juice pervaded his mind, but the cute paladin valiantly resisted the embarrassing temptation. Sam hurriedly washed himself, desperate to cleanse both body and soul.

The boy emerged from the tub, his smooth, flawless skin glistening with beads of moisture. A sweet, fresh smell wafted from his lush, honey blond hair, which clung to him wetly. Toweling off, Sam changed into the clothes laid out for him. The brown dress was a perfect fit for him; it was meant for a small, slender girl, after all. Smoothing the skirt down over his broad hips, Sam was a bit troubled by the distinct lack of panties to go along with the outfit...! Aside from the fancy jewel on his neck, the boy looked every bit the part of a cute serving girl.

It didn't take him long to find the stairway leading to the upper floors. While ascending the stairs, the boy heard muffled, indistinct voices from the other side of the wall. It sounded like there was a shop or a tavern next door. Whatever it was, it probably acted as a front while most of the business took place in these shady backrooms. Reaching the top, he noticed that two guards – both of them a foot taller than him – were posted outside the door leading to the Guild Mistress' office. Used to ignoring the presence of guards, the girly prince tried to just waltz right past them.

"Not so fast, missy," one of the guards stopped him, his brawny hand holding the boy back. "I have to search you."
"Oh, r-right..." with a resigned sigh, Sam submitted to the pat-down.

They had been told to expect him, of course, but they decided to have a little fun at the boy's expense. Sam could feel the man's big, rough hands sliding down his narrow waist. They moved further down, tracing his feminine curves. The boy gasped softly when the man's hands slipped under the hem of his skirt and squeezed his thighs. With a final pat on the bottom, the prince was let go, allowing him to meet with the mistress.

By the time that Sam has dressed and made his way up to the office, Amalda had regained her composure and was back to the slightly severe guildmistress she had been when the young Prince had first awoken from his stupor. Still, her eyes couldn't help but slink over his form as he maneuvered past the gropey guards that kept her office safe.

'Come in little one' she purred, nodding to a space before her desk.

A dark man, old and slightly gnarled, was reclining on a couch by the wall. Wrapped up in a thick black coat he looked like an old crow, bony and sharp-eyed. His eyes, unlike Amalda's, were purely evaluative. They focused particularly on Sam's hands.

'This is Hugo' Amalda said to the young man, her eyes too narrowing to a more serious focus. 'For decades he has been our trainer of thieves. We have...decided how best to put you to work for our syndicate. But before that we need to test your capabilities. Hugo here feels you have the makings of a thief, but needs to see you perform'.

She nods to the older man, clearly not anticipating or inviting any comment or objection from the former Prince.

Hugo, folding his gnarled hands in his lap, turns to address Sam.

'I have hidden three rings on sailors in the dock area' he said, his voice a rasping hiss. 'One gold, one silver, and one bronze. You must retrieve them. You will know the sailors when you see them as all are Orcs from the Rugged Coast. They stand out easily.'

'Try not to get caught' Amalda added, steepling her fingers before her angular face. 'And try not to linger in the docks. Since the Rhion invasion there have been no whores or brothels allowed throughout the city and many men are...restless. Particularly visiting sailors. I trust even someone of your rarefied background knows what I speak of?'

Even though he was a bit unnerved by him, the girly prince waved hello to Hugo upon being introduced to the man. The boy followed his sharp gaze and looked down at his hands. They were significantly smaller than most men's, and quite dexterous as well; with a little training, Sam would make a great pickpocket. Of course, the young paladin seemed none too pleased about having the "makings of a thief", but knowing that he'd only be retrieving the rings instead of stealing them quelled some of his misgivings.

Listening attentively to the wizened old rogue, the boy arched his eyebrows at the mention of orcs. He had never seen one in the flesh, but he had heard stories about them: big and brutish, with a propensity for violence and breeding... interracial breeding, in particular. As cosmopolitan as Sungate was, it was still a rare sight to spot bestial humanoids within the city; they were mostly confined to the slums. Although their savage nature concerned him, the boy was admittedly a little curious about seeing an orc for the first time.

"...I understand. I'll be careful," Sam assured the mistress. He got the gist of her warning, but... surely, no one would confuse a distinguished personage such as him for a working girl, disguise or no.
"Don't worry, I won't fail!" the petite boy said, puffing out his chest confidently. "I'll be back with those rings before you know it!"

Sam turned around, sending his skirt fluttering about his smooth legs, and made his way downstairs. His outfit had come with a pair of beige wedge sandals, which subtly enhanced his feminine posture, making him stick his butt out. Thankfully, they only had 3-inch heels, which made it easier to adjust to the ladylike manner of walking for a beginner like Sam.

The hustle and bustle of the city greeted the girly teen as soon as he got out onto the streets. The run-down state of some of the surrounding buildings made him quickly realize that he was in the city's Dusk side – the poorer part of town. Sungate was roughly divided into two halves, separated by a river: Dawn and Dusk, both of which were comprised of several smaller districts. The royal castle, the nobles' residences and many of the temples could all be found in the Dawn side, while the Dusk was home to the docks and the slums, among other things. Sam didn't really know his way around these parts, but finding the waterfront wasn't that difficult: all he had to do was follow the piercing cries of the seagulls.

Narrowly avoiding a Rhion patrol, the boy arrived at the harbor, where several large galleons and smaller sloops were moored. He could see dozens of men scattered throughout the various piers, loading large, heavy-looking crates and barrels to and from the docked ships. Scanning the crowd of sailors, the boy tried to find his "marks", the orcs Hugo spoke of. Curiously enough, there were no women to be seen – apart from Sam, that is. Watching the men, he noticed that many of them were shirtless, with tanned or swarthy skin. His eyes were drawn to their muscular chests and backs, glistening with sweat under the midday sun. With a dreamy sigh, the boy resumed his search for the orcs, trying to maintain a low profile.

Dusk was never the nicest part of Sungate before the Rhion invasion and, after the bloodshed and turmoil, it was even more seedy and dangerous than before.

Sam found himself, as he worked his way through the streets of hulking, half-clad, sailors and dock-workers, on a single run-down waterside road. There were piers jutting off from the left hand side into the ink-black sea, some with boats bobbing at anchor at the end of them, whilst a small cluster of buildings sat on the right in a bedraggled row. There was a seedy looking bar, called the Winking Mermaid, closest to him. Sounds of raucous laughter and chatter spilled out through the cracked door. It looked rough. Further up the street was a boarded up building with tinted windows. It was called the Wildcat but otherwise gave no clue as to what it had been before being shut down. Finally, there was a rope and sail shop, closed for the night, with a drunken tramp slumped in the doorway.

There were a few sailors and dockers on this street, and most of them seemed quite interested in Sam, casting him sideways glances as they went about their business. There was, however, only one Orc. Leaning on a rail overlooking the inky water this particular Orc was muscular, his dark green skin a mass of tattoos and whitened scars. His hair was greying a little, and his face as ugly as any of his kind, but on his right hand glinted a silver ring.

Oh! There's one, the prince figured he was off to a promising start upon coming across his first orc. He would likely find the rest of them in the nearby bar; the Winking Mermaid seemed like the sort of place that would appeal to the gruff denizens of the Rugged Coast. Ignoring the hungry looks he was getting from some of the sex-starved longshoremen, the girly teen drew closer to the orcish sailor, intrigued by his green, inked skin. However, the boy's earlier optimism turned sour once he saw the glint of silver on the orc's big, blocky hand. Drat! Sam silently cursed his bad luck; the orc was actually wearing the thing! The boy had been prepared to pilfer it from his pocket, but how was he supposed to get his ring now?

Determined to complete his task, Sam sidled up to the big orc, joining him at the railing. The air here smelt of brine, and the gentle sea breeze sent the boy's blond hair blowing about his pretty, effeminate face.

"H-hello there, sailor," he gave the orc a tepid greeting. The crossdressing boy didn't have to try too hard to alter his voice to match his disguise – there was no mistaking him for a man.
"Fresh off the sea, huh?" while talking, Sam glanced at the sailor's shiny ring, acting surprised. "Ooh, I see you've found some booty – that's a pretty ring!"
"Umm, could I have it? Pretty please~...?" the petite boy pleaded with puppy-dog eyes, his tiny hand softly caressing the orc's right. Sam ran his nails teasingly against the ring's silvery surface, playfully trying to pry it off.

The older orc turned to him, watching his little hand play over the silver ring, and his face was nowhere near as terrifying as Sam might have expected. Criss-crossed with scars his older visage was almost pitying as it ran up and down Sam's body, taking in his perfect little form.

'If I was a younger Orc' he said, his voice an amused growl, 'I'd suggest trading my booty for your own haul'. His hand, one meaty hand, had slid up Sam's thigh and under the young man's skirt before he could react. A heavy thumb, thick as a spear handle, pressed lightly against the rosebud of the boy's ass. If the orc was surprised by the lack of underwear, he didn't show it.

'But I'm too old for that crap now' he muttered, looking back out to see and dropping his hand away as quickly as it had appeared. 'I need a favour instead'. He jerked his head towards the boarded up building with the Wildcat sign. 'See that place? It used to be a whorehouse missy. And if we'd met twenty years ago, I'd be stretching your little pussy out right now in there. But as I say...to old' He sighed. 'No...I put away a little coin in there now and then. But since the Rhion closed it down, I've been unable to reach that stash.'

He eyed Sam warily. 'You want this ring? You go in there and get it. I'm too big - the guards would see me breaking open the boards, but someone as slender as you could slip between the gaps and inside. I hid the coin behind a picture of a black girl with her knockers out - you'll know it when you see it'. At this he gave a leering smile before continuing. 'Don't think about stealing any - its bronze trade tokens. Worthless unless you have a buyer like I do. So bring them back, and you can have this ring'.

It seemed like a reasonable offer, although there was little way of telling what or who might have made the former bordello their homes.

"H-aaah~!" the boy gasped cutely when he felt the orc's large hand on his bare ass. With no panties to protect him, Sam was quite vulnerable to a man's touch – and very sensitive; the thick thumb pressing against his rear entrance made the girly teen's legs tremble. The boy fidgeted with his skirt in embarrassment after the gropey old orc withdrew his hand; not used to getting this sort of male attention, the prince didn't know how to react. But he knew enough to blush even harder when the sailor commented about stretching his pussy – he was being talked to like a whore! Sam glowered at the crude orc, but he managed to look more adorable than menacing.

Although he was a bit skeptical of the orc, Sam was intrigued by his offer; a fair trade seemed preferable to the young paladin over underhanded tricks.
"A secret stash..." the boy contemplated out loud. He peered curiously in the direction of the brothel and nodded his head, before turning back to the sailor.
"Okay... I'll do it. But," Sam paused, and poked his finger in the orc's muscular, tattooed chest. "I'll hold you to that ring."

Spurred on by his new task, the boy approached the boarded-up Wildcat, looking for a way in. Going around to the side of the building, he noticed that one of its tinted windows was ajar, and the boards barring it had come loose. Even so, it only amounted to an opening for children and petite girls. Glancing around to make sure the coast was clear, Sam wriggled through the window – his womanly hips and bottom making for a tight squeeze.

It was dark inside, but the rays of daylight filtering in through the boarded windows allowed him to see. Sensual red tones dominated what appeared to be a dressing room. There was a row of armoires against the wall on one side, while the other had several vanities, where the whores used to do their make-up at. It looked the Rhion had turned the place inside out during their raid, confiscating most of the indecent outfits and sex toys. However, several skimpy costumes still remained – some of which looked like they'd fit Sam quite nicely.

"Oh, what's this?" the boy looked down quizzically at the floor. He had almost tripped over a pink handbag – it had probably been dropped in a hurry by one of the girls who used to work here. Besides being an essential accessory to any young lady, it looked cute. On a whim, Sam picked it up and slung it over his shoulder. I might need this to carry those tokens, the boy figured.

Adjoining the dressing room was the lounge, which was beyond a velvet-curtained doorway. The boy made his way in, his pretty eyes adjusting to the dim light.

The air in the building was musty but still held a hint of perfume and erotic musk. Everything in the place, even though it had as Sam observed been overturned by the Rhion during their break-up of the prostitution in the city, seemed to exude everything sensuous and sexual. There were a number of articles of clothing that he could pick up, if he had the mind to, including a rather kinky bunny girl outfit and one dress that seemed to be little more than holes and the odd strategically placed string of material.

There were probably more items scattered throughout the building, but only a determined search would have turned them up, and would have more than likely attracted the unwanted attention of patrols or other passersby.

As it was, Sam's rummaging around with the handbag had attracted the attention of something in the ruined Wildcat. As he pushed through into the lounge, he was confronted by the sight of a slender, perfectly proportioned, woman. Or almost a woman. Her skin was pale, her irises electric green, and her hair long and blood-red. All she wore was a bodice and panties, her long legs stretching out before her as she sat cross-legged on the edge of a seat. But what was perhaps most shocking was her small, delicate, bat-like wings and her long, sinuous, tail.

'Hello little one' she smiled, revealing sharp teeth between plump luscious lips. 'What brings you here?'

Not expecting to find anyone in the closed down brothel, Sam was surprised by the mysterious, red-haired beauty. With the way she was dressed though, she didn't look out of place. Her strange features – wings and tail...! – reminded Sam of the time the instructors at his paladin order talked about succubi and their evil ways. But, he was probably overthinking it... probably. Besides, for a sissy like Sam, an incubus would be the more threatening creature to come across.

"N-nice tail you've got there, ah-haha..." Sam's compliment was accompanied by nervous laughter.

The woman was resting her rump on a luxurious, tufted velvet chair, and her long tail hung off its side, resting partially on top of a cushion. There were many cushions of various sizes strewn about the room, some of them adorned with elaborate brocade, all of them soft and velvety. Chaises and fancy loveseats were placed in the lounge, allowing the clientele to wait while the girls lined up for them. With the way her eerily green eyes appraised him while awaiting his answer, Sam imagined that this is how those girls must have felt like while presenting their bodies to the customers.

"I'm on a quest," the boy declared with some aplomb, before clarifying, "Well, um, an errand, really..."
"I'm looking for a girl. Err, a painting of a girl. Black. Big boobs," he explained, making himself blush partway through.

Looking around, he noticed several paintings hanging on the walls – their sexual nature coinciding perfectly with the ambience of the room –, but none of them matched his description. One of them featured a collared Asian girl on her knees, her leash being held by a man blending into the picture's shadowy background. For some reason, it was easier for Sam to imagine himself in the girl's place – on his knees, naked, subservient to men. Another one was of a blonde girl wearing a jewel on her neck that looked very much like the Sun Star; she had more than a passing resemblance to the prince. Hey, what the hell?! the actual prince thought, annoyed by the slutty copycat. Cheap knockoffs of the Sun Star were not uncommon, and were quite popular among young women, which is largely why it wasn't as big of a risk as one might think for him to be walking around with the jewel in plain sight. The pictured blonde must have been very popular with the noblemen who had a desire to bed the young prince; unable to live out their fantasies with the little highborn sissy, they settled for the next best thing. If there were any other paintings, they must have been upstairs, where the bedrooms were.

"Wait, do you work here? I thought the Rhion shut this place down," the boy kept his voice low, not wanting to attract undue attention.

The woman with the sinuous tail was also looking at the pictures on the walls. And at the Sun Star on the choker around Sam's neck. She smiled. Like a wolf eyeing a lost little lamb.

She pushed off the seat, the movement designed to parade her body before the young man, and began to circle him. Her tail trailed around, snaking over his girlish little legs, and the heat of her gaze prickled his skin. 'You could say I'm more of a...long-standing guest' she purred, her voice like molten gold, and her tail encircled one thigh for a second before releasing. Behind him, she stepped close and drapped her arms over his shoulders. One hand toyed with the choker around his neck whilst the other stroked his chest through the front of his dress. 'I'm not surprised there are so many pictures that look like you here darling' she whispered, her breath hot on his ear, 'you're a little cutie. I bet the men just love fucking your tight little...' Her probing fingers, working their way lower to his crotch, brushed up against his little prick. She giggled. 'My mistake...your cute little asshole' she said with a laugh.

'I know where the painting you're talking about is' she said, releasing him and slinking around to face him. 'Why don't you follow me?' Not waiting for him to answer, she snaked her way up the stairs, letting her own perfect ass shake before him as she walked.

'Tell me...' her voice floated down to him as they climbed the dusty stairs '...what are you here for darling? What's the significance of the painting?'

"Ohh~, that tickles!" Sam protested playfully when her supple tail coiled around his silky smooth thigh; it had an almost leathery texture to it, which felt wonderful against his bare skin. Trapped in her seductive embrace, the boy blushed as she misidentified his sexuality. With Sam though, it was a very easy "mistake" to make. Even when he wasn't crossdressing, the little sissy definitely looked like someone who was exclusively interested in a thick, hard cock.

"N-no, that's n-not how it is...!" he tried to deny her dirty whispers, his girly voice getting breathy. The boy wanted to say more, but the feeling of her fingers playing with and massaging his choker made him reflexively swallow. He ended up weakly mumbling something unintelligible – and unconvincing –, before meekly following after the woman.

"I was told there's a hidden stash of trade tokens behind the picture," the boy said in a hushed, conspiratorial tone as he caught up with her on the landing. Still getting used to walking in heels, the prince had taken cute, mincing steps on his way up. "An orcish sailor wanted me to bring them to him."

'So you like a pleasing Orcs do you little girly girl?' the Succubus's voice floated back over her shoulder, the suggestive tone making the question sound smutty and perverse. As the demonic beauty turned, she cocked her head slightly as she enjoyed the sight of Sam tottering up the dusty stairs in his small heels. The boy was clearly not used to walking around in such feminine footwear but, by the dark gods, his body was built for it she thought. His hips swayed deliciously and the cute little expression of concentration on his young face convinced the demon that her decision was the right one.

The decision, of course, to work her demonic influence on the boy and corrupt him into a sissy-boy who craved carnal pleasure above all.

She smiled as he reached the top, and led him into a bedroom. Despite the must of abandoned space, the room was plush and luxurious, with a big four poster bed with deep red hangings surrounding it. A picture of a winking black girl, whose upper arms were pushing her breasts towards the viewer, hung on the nearby wall. Reaching behind it, the Succubus deftly unhooked a small pouch that jingled as she tossed it over to the young boy.

'Fancy seeing something interesting?' she purred seductively, and not waiting for a reply took him by the hand and led him over to a large mirror that hung on the far wall. It had a dark, curling, frame that had been carved to resemble some sort of creeping plant. Its surface was tarnished, streaked with dust and dirt, but there was something faintly special about the antique. The Succubus ran a finger down it and, suddenly, the surface rippled like dark water.

'Have you ever wondered what it would be like to be a girl?' she whispered, looking at him intently. 'Maybe what it would be like to be those girls from the pictures downstairs that looked like you?' As she spoke a mirror image of the room swam into focus. Except it wasn't an exact copy. The room in the mirror was cleaner, more lived-in, and there was a tall middle-aged woman standing talking to thin air. Or, rather, she seemed frozen in the act of talking as if to someone who wasn't there about Sam's height.

'This mirror will let you know what that would be like' she said, her tail snaking up his back again suggestively. 'You just have to step on through...'

The succubus' teasing gibe about pleasing orcs made the effeminate teen recall his encounter with the orcish sailor. Specifically, the feeling of his big, thick thumb nestling between his ass cheeks and pushing against his little pucker. The memory was so vivid and distracting that it made the tottering boy almost stumble in his cute wedges. Aah, w-what am I thinking?! I'm still the prince! the girly highborn's pride resurfaced, clearing his jumbled thoughts. T-that's right, I'd never stoop to doing anything with a smelly orc! Obviously, such a thing was unthinkable: a member of the royal family, having an orcish liaison? Pleasuring orcs barely befitted cheap whores, let alone the Sunn heir.

Sam followed the woman into the bedroom, his pretty eyes lighting up at the sight of the painting.
"She's pretty!" the boy said with an innocent smile, admiring the big-titted black beauty. For some reason, seeing her voluptuous form made the boy wonder what it would be like to have breasts. Sam blushed as he pictured himself with a pair of round, firm boobs, but that wasn't all: he imagined a pair of hands – a man's hands, large and rough – cupping them from behind. Lost in the fantasy, the teen's pink nipples stiffened under his dress.

The sound of the jingling coin pouch flitting towards him brought the boy out of his reverie, but he was too slow to catch it in time; with a faint thud, it bounced off his shoulder and slumped to the floor. Giving the woman an apologetic look, he bent down to pick it up. Fortunately for her, the clueless boy – who had his back to her – had decided to bend at the waist instead of the knees, providing the succubus with a lovely view of his plump rear. The petite prince's skirt was just barely long enough to hide his assets from her penetrating gaze. If the evil demoness had her way, the young boy would no doubt be spending a lot more time in such poses – face down, ass up.

Seeking to store his latest acquisition, Sam opened his cute, pink handbag, but, contrary to his expectations, it wasn't empty. The purse contained a full make-up kit – compact, liquid mascara, eyeshadow, eyeliner –, which could be used to achieve any number of steamy, slutty looks. Among the cosmetics was a tube of frosty pink lipstick, which looked like it was made for the prince's pouty, pillowy lips; the inviting color would be a perfect way to let men know what his mouth was for. For his pretty nails, there was a glossy, blush pink nail polish – its lovely shade striking a balance between innocence and feminine beauty. There were other items of note as well, but the boy didn't know what they were for. A purple ball, tied to a black, leather and chain-link strap, peeked out from the purse. Not realizing that its purpose was to silence disobedient sluts, Sam mistook the ball gag for some innocuous toy. He also struggled to understand what the clear, glasslike butt plug he spotted was used for; its thick, tapering shape gave him no indication that it was supposed to be inserted into sissies like him, keeping them plugged when they weren't being used by men. The see-through plug would allow anyone to peer inside of him while his tight little asshole was being stretched open. The handbag's previous owner was clearly a whore, but the more things change, the more they stay the same... Stowing the pouch inside, the boy quickly closed the purse, but not before the succubus, who had come up behind him, managed to get a glimpse of its contents.

"Mm?" the boy tilted his head inquisitively when the woman led him to the strange mirror. It seemed out of place, somehow, but before he could figure out what was bothering him about it, she asked him an unexpected question.
"I—" he hesitated. "I've thought about it, s-sometimes..."
It was hardly surprising that a boy as feminine as Sam would have some confusion regarding his gender. Being forced to dress like a girl wasn't helping; it was easy for the line between disguise and who he really was to get blurred. Still a teen, the prince's identity and sexuality were quite malleable; with a bit of "guidance", the succubus could awaken his inner sissy.

The boy watched as the mirror's murky surface became clearer, forming an image. It felt like he was watching a picturesque scene in some giant snow globe. The more he looked at it, the more the world beyond the mirror beckoned him. Sam took a tentative step, and then another, all the while the succubus massaged him with her tail as if to say 'good girl'. The boy extended his leg, touching the mirror with the tip of his cute shoe – it sunk in without resistance, sending ripples along the watery surface. He felt the demoness' hand on his lower back, half patting, half pushing him, until his whole body was swallowed up.

It was a disorientating experience, and the boy felt disconnected from his senses. After a while, however, he could hear a woman's voice. Blinking his eyes, he found himself looking up at a tall woman. She looked the part of a madam, and the commanding presence she exuded made it clear that she viewed her girls as little more than property. Her voice slowly came into focus...