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A Kinky Halloween Sleepover

Halloween of course, is known to be one of the most fun evenings of every cub's cubhood; a day in which cubs can fully live out their fantasy of being whatever superhero, princess, or scary creature they want to be. Costumes of all kinds can be seen on the night of October 31st, cubs bouncing from door to door fulling up bags, buckets, and backpacks full of delicious sugar-filled candy.

No exception to this were little lion cub Milo and his best friend Jessica, a cute little mouse girl. Both cubs were seven years old and in the same second-grade class in school, having known each other since their first day of Kindergarten. She and Milo had become fast friends on that first day of school and were now nearly inseparable, so it made sense the two would spend the most fun evening in October together. The two cubs even decided to go in costumes that complemented each other based on their favorite game: Cops and Robbers. Milo, of course, went as the caught robber dressed in the standard black-and-white striped prisoner costume while Jessica went as the police officer, dressed in a girl's police officer skirt costume complete with badge and handcuffs. Except these were not the standard plastic toy handcuffs you would find at the dollar store; no these were the real deal. Stainless steel with no safety switch release, whoever ended up in these cuffs would be trapped in them until little Jessica decided to break out the keys and grant release. Jessica quite knew who she'd be using them on later tonight, she was very much looking forward to it.

It was at about 5 pm on Halloween evening that Jessica arrived at Milo's house, already fully dressed in her costume for the evening. Greeted at the door by Milo's mom Rebecca, Jessica quickly bounded up the stairs to her best friend's bedroom, having been there so many times that she could get there blindfolded. Knocking on the door and announcing her presence to her best friend, she quickly entered upon hearing him telling her to come in. There she found the lion cub lying on his bed engrossed in a comic book. Like her, Milo was also already in his costume, the black and white stripes making him look more like a white tiger than a lion cub. Noticing that Milo was so engrossed in his comic, she prepared to surprise him with her presence. Ducking down slightly, Jessica set up to pounce. Seeing that Milo was still extremely distracted, Jessica made her leap, landing on the lion cub and finally pulling his attention away from the comic book in his paws.

"Nice to see you noticed me, doofus," Jessica remarked dryly as she finally had the little lion's focus.

"Jessi, how long have you been there?" Milo asked, astonished that she caught him so off-guard.

"Long enough to see that a comic book is more important than me..." Jessica replied in an obviously over-dramatic tone. "How could you, I thought I was your best friend..." she continued with a clearly fake pout.

"I'm so sorry, Jessi," Milo apologized, feeling really bad that he had gotten too engrossed in his comic. "I just got so into this new comic and I just didn't see you--"

"Relax, I was just joking!" Jessica laughed. "You shoulda seen your face when I landed on you, it's like all the air came outta you!" she continued through bits of laughter.

"Jeez, I thought I was gonna choke for a second," Milo remarked, "Okay okay, you got me. Nice costume, you look real pretty!" he exclaimed, finally taking a look at her police officer costume.

Jessica blushed at her best friend's comment, but managed to be able to reply to him. "Thanks, you look so cute in yours too! Are you wearing a cup under there? I felt something when I pounced on you..."

Now it was Milo's turn to blush. His eyes looked downward in slight nervousness before he made eye contact with his best friend again.

"Milo, are you okay?" Jessica asked, concerned about the lion's behavior.

"Yeah, I'm fine..." the little cub trailed off, not exactly convincing his friend. Before she had a chance to question him, he continued; "Jessi, can I show you something? Promise me you won't think I'm weird?"

"Milo, we've seen each other naked a bunch of times, what are you so nervous about?"

Jessica was right, the two cubs often played naked together whenever they had sleepovers like the one they were to have tonight. "Okay, I'm just gonna show you, alright?" Milo asked, receiving a nod from the mouse. Taking a slight breath, Milo placed his paws onto the waistband of his costume pants and pulled them down along with his underwear, revealing just exactly what Jessica had felt when she tackled her best friend: A steel chastity cage locked securely on her best friend's most private of places.

"Whoa, you're locked up!" the mouse exclaimed, knowing exactly what it was her friend was wearing. She, like all other cubs, have seen them sold in various stores, but she never expected to see Milo wearing one.

"Yeah, I am!" Milo giggled, starting to enjoy showing off. "You don't think it's weird, do you?"

"No way, it's freaking cool!" she giggled, "It looks so cute all locked up in there!" she said as she took a closer look at the cage on her friend's penis. "How long have you worn it?"

"About a month now, off-and-on," he replied.

"You've been playing with this thing for a month and you never told me? I'm hurt!" she exclaimed again in the same playfully over-dramatic tone from before. "I thought I was your best friend!"

"Well..I was afraid you'd think I was weird and not wanna be my friend anymore..." Milo trailed off, not meeting his friend's eyes. Suddenly Jessica felt a little bad.

"What? No way! I think it's cool, and even if I didn't I'd still wanna be your best friend!" she told him directly before glomping him again in a hug. Milo sighed in relief, returning his best friend's hug, glad he didn't have to worry about losing her. Jessica started giggling again, causing a look of confusion to appear on Milo' face.

"What's so funny now?" he asked.

"I just noticed," she said through her giggles, "You're a prisoner for Halloween...and your peepee is a prisoner too!"

Milo too giggled when she said this, "Yeah I guess you're right! I guess I have a bad peepee then, huh?"

"So bad it has to be in it's own jail!" Jessica giggled before asking to take things a step further. "Can I touch it? I wanna feel how it feels."

"Sure!" Milo said, excited at everything happening so far. Milo jumped back onto his bed and spread his legs apart, giving his best friend full access to his nether regions. Jessica tentatively reached her hand out to feel the steel cage securely locked around her best friend's genitals. Jessica moved the cage around, lightly fondling Milo's penis and balls. She noticed Milo's breaths becoming a little shorter as she did this, as well as the cage looking like it was pushing away from his body. "Oooh!" Milo gasped as she kept up her movements. Jessica giggled as she realized that her friend was trying to get an erection, the cage preventing that from fully happening.

"Are you trying to get a stiffie right now?" she asked, again unable to contain her giggles.

"Yeah, I can't help it with you touching it right now," Milo grinned, not minding any of this one bit. He loved it when he tried to get hard in his cage.

"How does it feel? Does it hurt trying to get hard?" Jessica asked, concerned she might be causing him pain.

"Nah, not really...I can feel it pushing on the cage, but it doesn't hurt. Feels really neat, I usually try to play with myself when I wear it!" the lion cub exclaimed. "It feels better when you do it, though."

"Oh you like this, huh? You're silly!" Jessica said as she fondled his locked up bits. "So...who has the key?" she asked, trying but failing to be subtle about it.

"Well...most of the time my mom has it, but it's with me right now," Milo responded, carefully weighing if he should continue with what he wanted to say. "Umm...would you like to have the key?" he asked nervously, hoping she wouldn't be too weirded out by the question.

"You'd trust me with it?" Jessica asked, astonished he asked that of her. It was what she wanted, of course, but she wasn't expecting to get it.

"Of course, Jess!" Milo declared. "You're my best friend, I wouldn't just trust anyone with it!"

Jessica blushed again, flattered that her best friend trusted her so greatly. "Well...yeah I'd like the key!" she said excitedly. Milo responded simply by walking over to his dresser and fishing out a silver key from his top drawer. Walking back over to his best friend, Milo took her right hand with his left paw and with his right paw, placed the key into his best friend's hand.

"It's all your's now!" Milo said as he handed the key over to her. Jessica quickly pocketed the key before breaking out into a sing-song voice.

"I've got your key, I've got your key!" Jessica playfully taunted her best friend, noticing him again trying to get an erection in his cage. "Stop trying to get a stiffy, you know that's bad!"

"I told you, I can't help it! Showing it off makes me excited!" the lion laughed, enjoying his bit of exhibitionism with his closest friend.

"Alright cubs, you ready to go trick-or-treating?" Rebecca's voice came from outside the room.

"Yes, mom!" Milo replied thorough the door.

"Yes, Ms. Grant!" Jessica replied at the same time before turning her attention back to Milo. "You're in for it later!" she declared with an evil grin.

"I can't wait!" Milo replied, an excited smile on his face as he imagined what was in store for him when they got back later that night.

In the true spirit of Halloween, both the lion and mouse cubs rocketed from door to door throughout their neighborhood in the quest to acquire as much candy as possible. Finally, when their bags were as full as they could get, the two cubs and Rebecca returned to the Grant house, the two cubs immediately making a beeline back for Milo's room. As soon as they got inside, the little cubs dumped their Halloween candy out into two separate piles, one from each of the cub's bags. Just afterwards, Milo and Jessica followed what was now an established routine for their sleepovers and decided to go bottomless for the rest of the night. Milo quickly removed his pants and underwear, leaving him only in his striped prisoner shirt, while Jessica took off her skirt and panties, leaving her only in her police officer shirt. Both cubs giggled as their genitals were now in full view of the other, Milo's covered only by the cage still securely on his penis, while Jessica's small vagina was clearly exposed. Feeling like the little criminal he was dressed up as, Milo made sure Jessica was looking as he stole a pawful of candy from her candy pile.

"Hey, that's my pile, you thief!" Jessica yelled out with a smile on her face. She knew exactly what Milo was doing.

"Finders Keepers, what are you gonna do about it?" The lion cub taunted in a reply, egging his best friend on.

"How about this?" the mouse girl answered as she again pounced on her lion friend and pushed him face-down into his bed before pulling his arms behind his back and holding him down. "You're under arrest for theft, you naughty boy!" Jessica cried out through the giggles from both cubs. Milo offered practically no resistance as she tackled him, he enjoyed every bit of what she was doing and it showed obviously as his penis again attempted erection inside of its steel prison. This, of course, did not go unnoticed by Jessica.

"To your cell with you, prisoner!" Jessica ordered, pointing to the top of the lion cub's bed. Giggling, Milo quickly placed himself on his bed, excitedly awaiting what was to happen next. "On your bed, face up!" the mouse girl ordered, making it clear there was no room for argument. With a smile, Milo happily complied as he submitted himself for his 'punishment.' Jessica, meanwhile, reached underneath the lion's bed to retrieve what she would need to punish him. Pulling out a box, Jessica opened it up to find, among other things, exactly what she needed: Four sets of handcuffs, two cub-sized and two adult-sized; and a small black butt-plug. Milo too saw exactly what his best friend pulled out and smiled widely, excited for what was in store. Milo immediately assumed the proper position that he knew the mouse would want him in: Arms above his head and legs spread apart widely.

"Good boy," the girl praised, "Stay still while I get you all cuffed up." Jessica first took one pair of the cub-sized handcuffs and secured one cuff to her friend's right wrist and attached the other end to the cub's bed. She quickly did the same with his left wrist, rendering the cub's arms immobile. Taking the adult-sized cuffs, the mouse took hold of Milo's right ankle and moved it into position above his head, cuffing the ankle to the headboard as well. She did the same with his left ankle, leaving the little lion locked to his bed with his caged dickie and little butthole exposed to her. Milo blushed, he loved being locked up in this position and it showed with his little prick desperately pressing up against the steel confines of his cock cage.

"This is what happens when naughty lions steal from a police officer!" Jessica declared with a grin and she stood over Milo's cuffed up form. "Time to punish your butt for your crimes!" the mouse said as she lubed up the butt plug and slowly and carefully inserted it into the lion cub's rear hole. Milo gasped as the plug entered him, his little cock pressing even harder into the confines of his little cage. "Aww, do you like that, Milo? I bet your peepee wants to get so stiff right now, huh? Well, too bad! Prisoners like you have to have their peepees locked up in jail!"

"I'm sorry, Officer!" Milo said, playing along with his best friend. "Yes, my peepee and butt deserve to be punished! Keep my peepee locked up in jail for as long as you want!"

"Good boy. Now...be quiet and make me feel good! If you do a good job, I might let you out early!" Jessica said as she lowered her little pussy onto Milo's mouth. Milo eagerly stuck his tongue out to taste the sweet taste of his best friend's cunny. This was something Milo could easily do all day, whether or not he was tied up. His little cock pressed very hard against the confines of his cage as he maneuvered his tongue over, under, and into his best friend's most intimate place, tasting the honey-sweet nectar dripping from within. Jessica's words had since ceased by now, fetching moans and pleasure taking over as she was overtaken by the wonderful sensation on her nether regions. Jessica screamed out extra loud as Milo ran his tongue over her swollen clitty button, the juices flowing onto his face even faster now. Up, down, left, right, in, and out went the lion cub's tongue as he steadily ate his best friend out closer and closer to her inevitable climax. Finally, the mouse girl shook and her juices squirted out, drowning the lion cub in her tasty and sweet-smelling nectar. Spent from her orgasm, Jessica moved her pussy away from Milo's mouth and removed the cuffs from him, freeing him from his 'cell.'

"That was the best Halloween ever," Milo declared, basking in the afterglow of what had just happened.

"Yeah, it was awesome, all of it," Jessica agreed, both cubs now snuggling together on Milo's bed, sleep not too far off from both of them. "Do you want to take off your cage?"

"No way! I told you that you can keep it locked up as long as you want, I meant it!" Milo hastily declined, enjoying what had happened so far and not wanting it to end.

"Seriously you mean that?" Jessica asked. "In that case...I'll unlock you in one week!" she said, an evil grin again spreading onto her face.

"A week? Wow...I've never gone that long before...cool!" Milo giggled, excited at the prospect of not a whole week straight in peepee-jail. His penis again tried to harden hearing the news. Jessica giggled, seeing it again straining.

"You're excited," she said through a yawn. "We'll see how much you like this once your week is up! If you still like it as much as today, then you're weirder than I thought!"

"But you like it!" Milo replied knowingly.

"Yes, yes I do," Jessica sleepily replied, tiredness quickly overcoming both her and the lion she had since snuggled up with. Pretty soon, both cubs had drifted off to sleep, dreams of what happened that evening running through their subconscious minds.