Whitzz/544K-RP-Datasets huggingface dataset:
Thread: Sissy Princess Among Thieves [dani_honey & Reydan]

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. Ohhh hh 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.
Thread: Sissy Princess Among Thieves [dani_honey & Reydan]

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.'
Thread: Sissy Princess Among Thieves [dani_honey & Reydan]

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.
Thread: Sissy Princess Among Thieves [dani_honey & Reydan]

'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.
Thread: Sissy Princess Among Thieves [dani_honey & Reydan]

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?'
Thread: Sissy Princess Among Thieves [dani_honey & Reydan]

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.
Thread: Sissy Princess Among Thieves [dani_honey & Reydan]

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.
Thread: Sissy Princess Among Thieves [dani_honey & Reydan]

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.
Thread: Sissy Princess Among Thieves [dani_honey & Reydan]

H-aaa h ! 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.
Thread: Sissy Princess Among Thieves [dani_honey & Reydan]

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?'
Thread: Sissy Princess Among Thieves [dani_honey & Reydan]

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.
Thread: Sissy Princess Among Thieves [dani_honey & Reydan]

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?'
Thread: Sissy Princess Among Thieves [dani_honey & Reydan]

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.