Pleasure Slave Cruise Ship [Eaenidu]

[Kuragari]

(Will Roll-9)

"I~I didn't get n~no contract! T~They just grabbed me and brought me here..." Casey protested. However, the mention of such made him squeak in fright, and reluctantly, he went ahead and stripped, squirming as he was soon naked before the boy, his own member twitching and half hard.

[eaenidu]

She, He hummed "Verbal contract or whatever, good you can at least follow orders, now bend over and grab the wall, I'm gonna fuck you until my balls are empty, then we'll finish cleaning up, and before you ask yes you have to do this, as of right now anyone on the ship can give you orders and you have to obey them, but as I'm training you my orders are above anyone besides a Guest or Mistress." He said casually stripping and stroking his cock as he looked at you with a grin.

[Kuragari]

(14)

Hearing such made him squeak in fright, and rather than bend over, Casey instead backpedaled towards the wall as he moved to cover his front and back. "N~No way, n~no way you can just do that... I~I'm not letting you f~fuck me!"

[eaenidu]

Hearing your words he hummed "Oh but I can hun, in fact, I have direct orders to test out both your mouth and your ass. So turn around, bend over, or I stop being nice~" He purred out his threat, reaching to the side and picking up a riding crop with a grin "Trust me~ I'd love for you to fight it~"

[Kuragari]

(13)

Casey shook his head, looking about for a sign of anything he could use to try and defend himself. He wasn't going to let this happen even if he was stuck or trapped here... least not without a fight! He was at least that much of a man!

[eaenidu]

The boy looked at you, then raised an eyebrow "You do know...It's going to be bad enough since you disobeyed me, you look like you wanna hurt me now, if you manage that, how worse do you think the punishment will get, you sold yourself out hun, you don't have the option to back out now, not with your debt." He Said, before slapping you with his Riding Crop, Hard. "Now Slut, Last Warning for a Light Punishment, Bend over, hands behind your back, face on the wall." He spoke with a harsh glare.

[Kuragari]

(Spank+Threat effect on will- 10, Will roll 12-10=2)

The spank and the threat of worse punishment suddenly made Casey realize how serious things were... reminded as well that he was stuck on this cruise ship and had nowhere else to go. With a pathetic whimper, he stopped hiding himself as he turned and braced his hands on the wall, bending over as he turned his head forward in shame.

[eaenidu]

You got another slap on the ass by the boy's Riding crop with a growl from said boy "That's not what I said to do dumb slut, if you can't listen to basic orders I'll give you to a futa that makes the last punishment one look like a saint, You had the chance to brace yourself, Hand behind your back, now." he ordered "You were just getting fucked before but now you're getting punished and if you can't learn to listen I'll punish you some more."

Spoiler (click to show/hide):

9/100 Sissiness

[Kuragari]

(Nat 1-10=-9)

Casey yelped, throwing his hands behind his back and whimpering as he tried to practically smash his face into the wall. "M~Mercy, sorry, s~scared, d~do anything! Anything at all!" He said, terror and anxiety clear in his voice as he whimpered and whined, now worried he'd messed up too much and was going to be hurt so much.

[eaenidu]

The boy snorted, but soon enough you found your arms bound behind your back, tied tight from fingertips to elbows, then you felt something latch onto both your feet, a spreader bar, one was added at your knees too, then rather roughly your cock was shoved into a chastity cage, the problem was that the cage had a set of spikey balls in it, a strong of them that went into your cock tip, they weren't sharp, but they weren't comfortable in the slightest, and the tip of the cage had bristles on it, to constantly tease the tip of your cock, and more on the sides to tease your glans. And only once that was secured did the boy grab your hands and a handful of your hair before he roughly started to fuck you into the wall, calling you names like a "Filthy Slut" and "Fucking Greasy Whore" that made your body fill with shame.

Spoiler (click to show/hide):

31/100 Sissiness

[Kuragari]

Casey didn't resist in the slightest, simply whimpering. A small part of him found a prickle of excitement rising up at some of this, a secret shame of his being that he'd looked up some of these things before... even chasity cages, though he'd always imagined it'd be a girl putting such things on him. He gasped and squirmed here and there, panting hard once he was caged, the thing making it hard to focus.

Then the fucking began, Casey yelping and whining, even as the boy's cock struck against a spot every so often that made his body shiver and jolt, cock straining against the confines and making him whimper and whine more. Several times he wanted to turn his face and beg for the boy go a bit easier... but he kept his face pinned to the wall, biting his lip sometimes as the jolts of pleasure overcame some of the discomfort or strain he was feeling, the teasing names only making him blush more as pre-cum drooled out of the cage.

The only time he did say something was when he felt something starting to build... "S~Something... a~aaah... b~body growing... t~tingly... a~all over..." He managed to gasp out, not sure if should have said that or not.

[eaenidu]

The boy growled in your ear "You better not cum before I do slut~ Shake that ass~ make me flood your lewd little fuck hole and then you can cum~ I'll punish you more if you cum first~ Even after I cum you're not allowed to without permission~" he told you, giving you a light spank with the riding crop "So beg~ Beg me to cum inside you like the filthy little whore you are, beg me to try and breed your worthless boi-pussy~ Beg and if you impress me~ I might just let you cum~" He purred slapping your ass, with the crop with every "Beg".

Spoiler (click to show/hide):

34/100

[Kuragari]

(Will Roll-8, resist climax 16)

Submitting once again, Casey whimpered and whined, taking a moment to first start shaking his ass and thrusting back into the boy's thrusts as the tingly feeling grew stronger and his ass started to cling to the boys pillar more. Hearing the threat, Casey resolved to keep from cumming into he was told to, and with a shiver, he allowed his will to chip away more as he said,

"S~Stuff m~my u~useless b~boi pussy, f~fill it with so much cream i~i'm leaking it for days... u~use this cheap greasy c~cocksleeve t~til you're drained, flood me w~with so much that c~calling me a cum s~sock fits me better!"

[eaenidu]

The Boy seemed to love that as he got even rougher his cock slamming into that spot inside you again and again, you wanted to dislike it, but his thrusts were making it hard and hard to resist cumming, before he finally after minutes of leaving you stuck on the edge started flooding your ass with more cum than you'd ever shot at one time before, flooding your ass just like you begged.

Spoiler (click to show/hide):

36/100 Sissiness

[Kuragari]

Panting, quaking, shivering and shuddering, his yelps and whines of discomfort and pain had started to shift more towards gasps and moans that sounded a tad more feminine than he'd ever have imagined coming from his throat. He even found that he wasn't having to purposely shake and roll his hips as much, his body seeming to do so now on instinct. As he felt the boy begin to cum, Casey managed to keep from cumming, even as he desperately wanted to.

"P~Pleaseh, c~can... c~can c~cum s~sock... c~cum?" Casey asked, figuring perhaps if he used that term it'd be in his favor, seeing as it had seemed to excite the boy.

[eaenidu]

The Boy hummed and thought about it before grinning "No~ Not yet~" pulling you from the wall and pulling you over, he promptly forced you to kneel down and shove a dildo that was twice his size up your ass "Clean my cock, then you can bounce and cum as much as you like~" he ordered smacking his cum coated cock on your face.

Spoiler (click to show/hide):

36/100 Sissiness

[Kuragari]

(Resist cumming-11, will roll- 4, Sissy gain-2)

Whining and whimpering, Casey then squealed as his ass was stuffed so by something much thicker. He gasped and gurgled a bit, but kept himself in place as he blushed and found himself face to face with the cum coated cock than had been up his own rear.

Too afraid of what would happen if he didn't obey exactly as told, Casey started licking the boy's cock clean, feeling more ashamed and embarrassed as he did his best to not let his hips move, lest he wind up bouncing on the dildo.

[eaenidu]

He giggled and pet your head, "Good~ Bitch~ Good little cock hungry whore~" and continued on with the insulting and degrading names...but at least he was praising you now, even if that was causing all kinds of trouble with your head. Doubly so now that his thrusts were soft, gentle even "If you'd a good like cum toy the rest of the day you can even earn a reward you'd like that right~?" He purred "Good sluts are rewarded bad ones are punished~ Hey~ my cocks all clean~ So you can cum now~ But if you can hold off while bouncing on that dildo and make me cum again first, I'll give you a reward~" he promised rubbing his drool covered cock on your face.

Spoiler (click to show/hide):

38/100 Sissiness

[Kuragari]

(Try to hold out til Boy cums- 11, Sissy roll-8)

The praise, as degrading as the terms were at times, made Casey's head feel weird. He didn't know how to feel about it, or how the soft, gentle thrusts against his face and lips were such a contrast. As he heard that if he was good and could make him cum again he'd get a reward, he found himself unable to keep himself from trying for such. The terror from before lingering and serving as motivation as he kissed and licked all along the boys tip as he began to move his hips, now that he had permission.

He even, after a minute, parted his lips and took in the boy's cock, though he was only really able to suck and bob along the first 3 inches or so, his throat protesting trying any further.

[eaenidu]

The boy grabbed your head and gently began pushing his cock in deeper and deeper, he wasn't massive, he wasn't even bigger than you, but somehow, getting dominated by someone with a cock smaller than your own made this even more degrading and filled you up with an even deeper feeling of shame and sluttiness, like, you had to be a slut, a whore, like he said you were letting him fuck your face practically to try and win a reward, even though he hadn't cum, you found your throat slowly opening for him.

Spoiler (click to show/hide):

46/100 Sissniness