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Out of the frying pan... (Deerpoob X Lyra)

"K-Knickers...." he said as much to himself as to her, looking down he sighed and nodded without another word.

Going to the trunk he dug through it....she wanted him to be dressed up? he would dress up...taking out a dark green dress similar to the one he had on before, a pair of underpants just like she had said would be in there, the small locket and even a pair of shoes, high heels but thankfully not too tall. He quietly began to dress, sitting on the bed and looking at the floor, what was he doing? he was just surviving, just like he had always done, just survive, that was all that mattered, still this was the most humiliating thing he had ever, but it could be worse right, none of the crew had seen him, or attempted anything, if we was lucky he might even get something out of the attractive captain.
 
By the time Katey got back, she was smiling brightly. "Ohh, don' ye look lovely?" she cooed, standing before him. "But yer face is so serious. Don' ye like ter look pretty fer me, Princess?" she asked, placing a finger under his chin and tilting his head back to get a better look at his face. "Here, stand up so I can have a proper look at ye, and do give us a smile, love," she commanded, but there was no particular harshness to it. So saying, she pulled out the dining chair from the table to watch the show.
 
His cheeks burned under her stare but he forced a smile onto his face, it was surprisingly pleasant in a sort of androgynous way, it would make men more trusting of him, he seemed harmless, and to women it would probably make them smile right back, it disappeared after a moment, and he looked away "did you bring some food?" he asked, standing up as straight as he could comfortable, the dress was designed to show off a woman's figure and although he lacked the breasts he filled it out surprisingly well, no doubt pleasing her. He forced himself to smile again, what else could he do? as she got the chair she would notice a small collection of other things he had gotten out and considered but ultimately left off, bracelets and headbands, even a choker and gloves.
 
"Knew I fergot someat," she chirped, springing to her feet. "I'll be right back, so don' ya be goin' nowhere," she told him with a wink, knowing very well he wouldn't. It wasn't a few minutes later she returned with a bowl of stew and some hard tack and a cup of grog. She set the food down on the table before turning back to him. Caressing his cheek affectionately, she whispered to him, "You do look lovely in tha'," before kissing his forehead. "Oh, an' one more thing. I want ter see yer knickers. Turn aroun', bend over, and lift up yer dress. Make sure ye keep yer legs together. Don' want ya thinkin ye can get away with anythin'."
 
He looked at her, cheeks seeming to be permanently dyed red and he sighed, closing his eyes and turning away, he hiked the dress up, revealing his pale legs before bending over, keeping his legs tight together, it was near impossible to tell him from a woman from this angle, the bulge from his member was in the front, blocked by his legs, he frowned, realizing she had probably intended it to be that way....if she wanted a woman so bad why didn't she just bring one on board? she had the money....why waste her time with him?
 
"Very Nice," she commented, leaning forward to give the boy's ass a bit of a grope. "Now tha's more like my Princess," she complimented with a peck on his cheek before kicking off her boots and flopping down on the bed. "Enjoy yer meal, love," she told him with a wink, which is when it became apparent... she only brought rations for one person. "Oh, and remember ter keep yer back straight and legs togetter when ye sit." Then, apparently in anticipation of the wait, she leans back against the headboard with her hands tucked behind her head and her legs crossed one over the other, and she ck=loses her eyes.
 
He sighed and quickly dropped the dress back down, sitting as she insturcted and ate eagerly, thought still carefully as he assumed she would comment on that being more like a thief then a princess, he did wonder about the food only being for him, maybe she ate with the crew? he couldn't know for sure. Soon he was finished and turned to see her, seemingly dozing off. He stood up and put his dishes by the door quietly, then looked around, attempting to peek out the windows, they were sealing up tight, why was that?
 
One eye peeked open at boy's footsteps, following him around the room. "There ain't nothin ter see out ther asides the sea anyway, love," she told the man, eye closing again. "The sea can be a very borin' place without someat to liven it up," she continued, possibly referring to his situation. Still, she didn't move from her position and she hadn't given him anymore commands.
 
He jumped a little and turned to look at her "Ya I guess your right....I was just curious why there boarded up more then what was out there..." he said, walking back and sitting carefully on the chair at the table, looking at her "Is there something I can do?" he asked, rubbing his arm, he didn't want to sound like he was complaining, but he was getting bored, he sighed and looked at her, looking perhaps just a little too long before letting his eyes quickly wander around the room, a light blush forming on his cheeks.
 
"There's plenty o' things ye could do. Question is, do ya want ter do 'em," she teased. "Alrigh' alrigh', what is it ye want ter do? I'll tell ye if'n ya can do it or not," she offered seriously, finally opening her eyes. "After all, entertainment isn't my job," she told him, flashing him a cheeky smile. "I'll tell you what ya can do though, love. Give us a foot rub."
 
"a foot rub...." he said softly and nodded "alright....I guess I can do that." he figured it might keep her in a good mood, he didn't say what he wanted to do, not wanting to annoy her by merely suggesting it, He quietly went to the side of the bed and sat on the edge, looking over at her and waiting for her to offer her feet to him, he looked down, eyes traveling across her body, years at sea must have kept her in pretty great shape.
 
"Well, what are ye waitin for?" she asked wiggling her toes on the bed. "Ye ain't got ter be shy wit' me Princess. It's just us girls here after all," she tells him with a playful wink. "I'm gonna have ter break you o' tha' sooner or later. It's startin ter ware on me nerves," she mused. "And ye ain't got ter be such a sourpuss, neither. Yer allowed to talk ya know," she told him. "Actually, nows I think about it, I don' think ye ever e'en told me yer name Princess."
 
"im just...not very talkative thats all" he explained and gently took her left foot in his hands, rubbing at the soles and inbetween the toes, glancing up at her, really wishing she would stop with calling him a girl, but he knew she wouldn't

When she asked his name he sighed, knowing she would easily turn it into a girls name "Daniel...." he said softly, looking down and rubbing at her foot a little harder. He had alot of questions, and he hoped she might answer some now that she was encouraging him to talk "so...how did you get so strong? I've known men twice as big as you that couldn't do what you did..." he touched his neck and looked at her curiously.
 
"Must be all this clean livin'," she told him jokingly. "Nah, tha's a long story and I'm no' sure it's one yer ready ter hear," she explained, not sure if he would ever be ready to hear it. "Le's jus' say I'm no' your average girl and leave it at that fer now."

"So, any other questions, Princess?" she asked, purposefully avoiding the obvious attack on his name. In her mind, his name was his and she wasn't going to take it from him. She'd just stick with her little pet name. "And the answer to yer question 'bout the windows has already been give afore ye ask it again. I no like the sun in me eyes while I'm tryin ter sleep," she said, pre-empting any more questions about that particular subject.
 
He nodded and sighed "alright....." he bit his lip, wondering if he should ask his next question "why....do you insist on treating my like this? do you like women?" he looked away, worried he might have touched a nerve, he quickly switched to her other foot, massaging the sole and working it till she was comfortable, hoping she wasn't going to be mad at him for such a blunt question, but his curiosity was acting up again.
 
She merely shrugged as she allowed her other foot to be picked up. "Sure, I like women. I like men too. It's all good fun. Somethin' ter keep the boredom away. As fer why yer dressed that way. It's a punishment pure and simple. I actually had a bit of pity on ye. The normal punishment for thievin' is ter be marooned on an island with jus' a pistol. Instead, I'm jus' brandin' ya as one in me own special way, and this way it's not e'en permanent. Once ye decide ter leave, ye can jus' go back ter wearin men's clothes. Though ye'd be a fool ter not sign back up," she said, matter of factly. "Anyway, once yer done wi' tha' come up here," she said, holding out her arms as if awaiting a hug.
 
He nodded "fair enough..." he said simply rubbing still "i guess i shoukd be thankful then...but i swear to you i wasn't intending on stealing from the woman i was saved by...merely curious is all" he blushed "a fool not to come back here? Not that your the worst woman ive ever met why would i want to deal with being dressed like this any longer then i had to?" he spoke honestly.

He gave her an odd look as she held out her arms "um..." he felt a little nervous but shuffled up the bed to her, and began to lean in to hug her, all in all things werent so bad, embaressing yes but again better then dead.
 
Katey pulled him down to her, cradling his head on her chest and began stroking his hair. "Why fer the money o' course," she said as if it were the most obvious thing in the world. "Yer pretty much me own personal cabin boy and that means ye get half a share of anythin' we take while yer part of the crew. And with what this crew takes tha's no small amount," she explains. "An' ye have ter admit, yer job so far hasn't been especially strainin. So far, all ye've been asked ter do was look pretty and give me a footrub. A few years o' that and ye'll be ready to retire and comfortably. Jus' think about it, Ye'll be able ter afford all the pretty dresses ye could ever want."
 
He couldnt help but chuckle, she was a strange woman to be sure "A share huh...as a kid i always wanted to be a pirate, i realized over time it wasnt exactly all fighting and sailing..." he looked around "but this isnt so bad, better then any of your crew im sure..." feeling brave he spoke his next words quieter "id bet they'd kill to be in my position, dress and all..." he forced himself to look up at her, like he had a chance with this woman she probebly enjoyed the large burly type, not this scrawny little man wearing a dress, and yet he still felt the need to say what he did. "your right...maybe I will want to stay, thought ill be sure to bring more clothes....and no dresses" he smiled a little, combined with his deep green eyes his smile had a very soothing attractive quality, it was a wonder more women didnt fall for him, maybe he just didnt smile much.
 
"Oh no, as long as yer a part o' my crew ye'll be in a dress, and ye can lay to that. I like my Princess too much ter have it any other way," she said, her voice jovial, but somehow it was clear she wasn't joking. Still, her expression was almost... affectionate. "And besides, after this evenin', ye can no' tell me ye don' enjoy it too. What with the way ye were buckin yer hips and moanin like a girl," she challenged, her voice a husky whisper as her hand began to creep under his dress again while she continued to stroke his hair.
 
He sighed embaressedly, so much for that... He looked at her with a sort of fake angry look, but it quickly changed to a blush as her hand tugged at his dress and he looked away, embaressed at how just this could arouse him, just the thought of her touching him.
 
Her hand came to rest on his inner thigh as she gave him a peck on the forehead. "There ye go again. Jus' relax and enjoy it. There's no reason ter be embarrassed," she cooed as her thumb began moving slowly back and forth to gently caress the flesh of his leg. Meanwhile, the other hand casually brushed his hair away from his neck, allowing her fingers to gently glide along the artery there. "If ya'd jus' let go and stop thinkin' about it so much, you'll learn how nice it can feel ter be pampered a bit."
 
He closed his eyes and let out a small groan "pampered...." he didnt mind the sound of that, here he had food, a bed, comfort, and he would make money just being here...he felt he really could stay here, it would work, he found himself smiling "i like the sound of that..." he whispered, legs tensing up a little as she trailed her fingers across his thigh.
 
The woman simply smiled before tilting his head back and kissing him. It wasn't a hungry kiss but it was deep, and as it continued her hand began to gently guide the boy's legs apart before moving upward. Her fingertips came to rest over that smooth area between his legs, cupping his balls in her palm through the panties there. Ever so softly, her fingers glided in circles over that spot with a feather's touch.
 
He made a small noise as she kissed him but he kissed her back, leaning into her body, legs shaling
Lightly as he felt her hand sliding up his leg, her hand was so nice, delicate touches on his privates, it didn't take long for his member to begin hardening, growing stiff under her gentle fingers. He kissed her back a bit harder, tasting her lips and finding himself wanting more, needing more.
 
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