“Lousy sky pirates!” Kit whispered to himself. “Don’t worry Molly… I’ll save your mom. And don’t you worry Ms.Rebecca. Clouds aren’t the only thing I’ll kick to save you if it comes down to it.”

Ms.Cunningham was someone precious to the little bear cub. After leaving Don Karnage and pirate life behind, he found a new place to call home. People he could call family. People that welcomed him with laughs, open arms and making the little cub happy. He was thankful he got as bored as he did with them before meeting Becky and Baloo.

Neither hide nor hair would stop him from saving them if they needed him.

And right now, it was up to the young bear. Baloo was out on his own personal adventure and the only one who knew that Rebecca was nabbed by the pirates. They hadn’t left a ransom or anything so Kit was trying to figure out what their game plan was as he stepped through their hideout. If she was being hurt...

	‘Easy… Don’t get mad. Getting mad will end up with mistakes. Just gotta find her.’ 

Kit made sure to sneak around undetected. He remembered the general layout from his old days hanging around the place. Besides a few boxes and some slight rearranging of old junk, it was mostly the same. All that was really missing was some of his old stuff from the little hobile he called his room.

	“Where is she? Rebecca…” 

	“Man, I can’t tell you how bad I needed that!” Kit heard a voice coming from around the corner he was walking towards, along with a menacing shadow. The bear saw an opening in the wall and ducked into it, pulling a piece of cloth back over it to hide himself. Heavy footsteps landed right beside him “Hope the cute bear likes the big presents we left her!” The heavy voice laughed. “Maybe I should have been more rough…!” 

With every word and laugh coming from the unseen pirate, Kit had to resist the urge to jump out and deck him in the face. But he restrained himself, holding his shaking fist until the heavy stomps of the man’s steps faded to nothing. Kit wanted to kick himself. He still remembers his time staying with the unruly pirates. He had a place to stay but being around them just made him sick the longer he did. If it wasn’t for Baloo…

It he’d probably be the one hurting her along with every other pirate scum at the hideout. 

	‘No…! I’m not like them! I’m not like them!!’ He repeated the phrase over and over. He wouldn’t ever do harm to someone he cared about so much. Especially someone as kind, loving and hardworking as Rebecca. Kit took a few deep silent breaths to steady himself. He peaked out from behind the cloth to make sure it was safe to move. He ducked out and walked down the path the heavy footed pirate came from.

‘Tap’
‘Tap’
‘Tap’

His light footsteps felt like they echoed in the empty hallways but he finally comes upon a familiar door.

	“Lockdown.” It was a rarely used room that Don Karnage would only use in either extreme situations. Or as punishment. The cub himself never went there… But the screams he’d hear back there was enough to keep him from crossing anyone while still a pirate. A knot formed in the bottom of his stomach as hundreds of possibilities ran through his head.

Kit cracked his knuckles to loosen them up before grabbing the knob. His sharp ears didn’t pick up any noticeable movement inside. He steeled himself, took a deep breath and cracked the door open. It was lit but barely. The light bulb flickered, trying to keep itself on but was obviously ready to go off at any second. 

A figure laid on the floor. Getting closer, Kit could see the figure had long flowing brown hair and wore an all too familiar pink sweater. 

	“Rebecca!” He closed and locked the door behind him. “Its okay I’ve come to-” As he approached and grabbed her, he felt something lukewarm and wet instead of her firm shoulder. 

	“W-who’s there…?” Kit froze in place.

Rebecca Cunningham. Respected and hard headed owner of their business. Single mother and go getter. Her makeup was a complete mess with smears that stuck to her fur. Her clothes were torn and ripped from the front. The sparkle and excitement in her eyes had dulled so much that the light of the room seemed like it didn’t affect them. But the most glaring and intense part that left the cub frozen was the ludicrous amount of jizz that had coated her body.

Cum. Spunk. Spluge. Days worth of seed had sunk itself into her golden brown fur and clothes. Traces of it was all over. Her mouth, her now exposed breasts and privates were soaked in god knows how many pirates viile juices.

And here he was. A little kid, touching her defiled body. One of the few people who had become so important to him. By the same people he once hung around barely a year ago. He… Could have been one of the many who could have...

Something in his young mind couldn’t take it. Pulling his hand off her body, Kit’s expression darkened. Hopefulness. Anxiousness. Worry. All of it had replaced itself with two bitter emotions:

Fear and arousal.

	“H-hello?” Her voice was shaking. She couldn’t get a decent look at who it was touching her. Rebecca tried to move and push them away but all she ended up doing was flailing about before falling on her back. She was completely exposed to her young friend. Legs spread and cum seeping out of her used pussy and ass. Even in the dim light, Kit could see everything. 

Rebecca herself felt so tired. The last few days of constant physical abuse had worn her down. Her only food having been the pirates personal sploge being stuffed down her gullet. 

	“Please… Be gentle…”

She… Didn’t see him as her friend. As the little rascal that she’d come to love as a sort of son. She saw his as a pirate. A filthy pirate who only wanted one thing from her. 

Kit looked down at his own crotch and could see the thick tip of his cock starting to bud out of his sheth. Going bottomless as always, there was nothing to hide the burning excitement his body was building at the site in front of him. It was the same sensation he’d feel whenever he was alone late at night and thought about her. Clothes torn, stained. Defenseless and open to any kind of contact. All of this done by pirates. Even if he wasn’t one anymore, he was a pirate before. 

A filthy pirate.

A pirate who did this to her.

Without saying a word, Kit went down on the restrained parent, licking her crotch and lapping up the wasted seed that had collected around her. The first contact brought out a gasp of surprise, followed by whimpers as the cubs tongue went to work on her. She tried to hold in her moans but the first gentle touch she’s felt since being captured was such a welcome change. Her pink flesh was beyond sensitive from the rough days and nights. The gentle contact was enough to leave her trembling with every swipe of his large tongue. Her silent lover wasn’t done however. When he licked up the last trace of cum from her slit, he moved to her thighs and stomach. Kit made sure to lick off every bit of filth that he could gather on his tongue. 

When he was finally done, he checked to see if anything was left. Wet from his tongue but nothing stained her beautiful body.

Yet… 

Suddenly, Rebecca felt and heard a loud slapping that made her jump. The flickering light gave her enough illumination to see the hefty and hard cock that was laying across her sensitive labia. It was bigger and thicker than most of the other sky pirates. Going along the owners waist, she saw a familiar brown coat of fur. The further her eyes scanned the body in detail, she counted and noticed too many familiar details. Dark sweater. Baseball cap worn in reverse.

	“No…” She muttered in the cold room. Her mind tried to come up with plenty of explanations. Her fear only grew as her assailant pressed himself into her, giving her little time to prepare before he finally entered in. “Ahh!” She threw her head back and felt her leg being grabbed as the man inside her pushed into her.

He wasn’t smooth. He wasn’t trying to please her. He stumbled and moved awkwardly as he humped her. The thick cock spread poor Rebecca enough to give her some sense of pleasure. She could barely fight back as he pushed himself down, giving him complete access to her soaking walls. 

	“R-re…” He muttered. He could never get the words out but the more he tried, the harder he’d pound her. The pit in the bottom of her stomach only seemed to make the pleasure all the more sickening. It was as if he used that feeling to bounce it around in her guts, leaving her a trembling mess of sin and pleasure. 

	“Ahhh! P-plea-se go sl-slower…” Rebecca begged.

Her pleads went on deaf ears as her assaulter only sped up. The thick cock inside her pressed the right buttons over and over, giving the poor older bear little else to do but let her own excitement out. She clenched violently around him in a series of spasms. There wasn’t much else to do but simply give him her own pleasure and take whatever he was gonna give back. 

She didn’t have much to wait.

Kit was in a trance. As a male he was simply doing what was natural. He was fucking her. He was trying to claim her. To save her from being owned by worse men. But as her co-worker and more importantly, her friend, he was in a deluded state. He acted on feelings and emotions instead of rationally. 

His hips moved slower.

He just wanted to help her. Kit wanted to save her.

Every stroke became deeper and harder.

He wanted to show her that he wasn’t like those sky pirates. He wasn’t filthy like her. She wasn’t some toy to be played with. Kit saw her as a friend and a woman. 

The young bear hilted himself in her, feeling his heavy fur balls tighten up as he looked down into her scared face.

The flickering stopped. Staring face to face was Kit Cloudkicker and Rebecca Cunniningham. Boss and worker. Son to mother figure. Friends. They watched as the other climaxed, seeing every twisted emotion in the others eyes. Rebecca could feel herself fade away into the dark as she felt the thick syrupy strands of fresh cum soaked her pussy down to the core. Her little womb, forced to drink all of the cubs jizz til whatever couldn't fit in her spilled out. Rebecca’s final vision was of Kit’s innocent face twisted in pleasure, baring his fangs as she grunted. Forcing out his fierce swimmers into her.

Kit could barely keep himself standing as his orgasm finally calmed down. The room was silent save for their heavy breathing. The cold air was replaced with the sweat of sex. The scent of cum hung in the air. The little bear cub found himself fall back against the door, slubbing towards the floor. He saw his now limp cock slack on the ground, shining in the once again flickering light. 

His lifted his head to see only Rebecca. Legs spread with the residue of their activity seeping out of her. It was white and stained her surrounding fur. Just like before… Just like with the pirates…

Light had overtaken the night once again. Rebecca found herself at home, lying in her bed. She remembered everything that had happened. She didn’t know what happened after the last man had come in but she found herself home as if it was a dream. 

She knew it wasn’t. Not from the lack of evidence that should have filled her up. But it was in the way the little bear cub she’s come to know. The way he’d always look at her in a certain way. It never left her feeling sick of anything of the sort. But those eyes sent something shivering inside her:

Excitement.