Kinky Clown MILFS! Pt. 02 - This Again

"But... but..." he let out a defeated sigh.

"Ready to settle down now?"

"Yeah... you... you won't... you'll be nice right?"

Blossom smirked and brought him right up to her puckered lips which engulfed his face. "MMMMMMMMMMMWAH! I'll be as nice as you are small and adorable cutie. Now it's time to go." She lowered him into her cleavage until only his head poked out. "Give it some time hon. I bet you might even like being that small after I show you all the great spots to explore on Mount Blossom." With a final poke of her finger, she pushed his head down into the endless abyss of her cleavage. Picking up the car she started to strut out of the room, making sure to put a little extra bounce in her step for her special passenger. "He feels pretty good in there. Maybe I'll take a page out of Tiny's book and put him 'basement' next time."

As she walked Mikey was squeezed and tossed around in her warm, soft bouncy cleavage. He had no idea what the future held for him, but he had to admit, it could be worse.

Burt moaned as he came to. His eyes widened when he saw he had not been dreaming. Miss Meriweather was sitting Indian style in front of him on a large bed, dressed like a clown. Merry Weather. That's what she called herself. His confused mind began to clear.

"Where are my pants?"

He tried to move.

"Why am I cuffed?"

"I want to talk to you about something."

"What?"

"Clown porn."

His face turned a cute shade of beat red and he sputtered out whatever words he had prepared to say.

"Excuse me?!"

"When did you realize you were into it?"

"Miss..."

She gave him a knowing look.

Merry. There's been some kind of mistake."

"I've seen the art..."

"You've seen my art?!"

"You're art? You make your own?! Wonderful!"

She grabbed his phone out of his pants pocket. Using his face to unlock it she cuddled up next to him and pulled up what looked like the right app. He went to his gallery.

"Please don't."

The early works were all various Harley Quinn fanart.

"That makes sense," she commented.

Fanart of the mime from An Extremely Goofy Movie followed.

"Mimes aren't clowns."

It then evolved into gender swapped Ronald McDonalds and Pennywises. The newest works were generic clowns his own age before aging and morphing into...

"The girls?"

She gave him a shit-eating grin.

"You saw their profiles online. You knew all about this place didn't you. I bet you dropped hints to get the others to come here but not think its your idea. Such a smart little pervert."

"Please. I just want to go home."

"No, you don't. You're scared and feel like you need to run. You want to let this go all the way. You need it to. I know. I'm the same way."

She straddled him, causing her skirt to ride up and reveal her red and white dotted panties. He grew hard under her.

"Have you ever had clown sex before?"

He shook his head.

"You have no idea what you're missing."

The panties were proven to match the bra as it came into view. Merry sent her glasses and hat flying in the process.

She ground herself against him harder.

"Here, let me show you."

Sam stared up at the 9-foot tall behemoth of a clown woman, still smiling down at him. Her eyes obscured through her hair, her hands still pulling on the coils of rope. Naturally, Sam was quite intimidated, only able to lightly shake, as she giggled getting closer and closer.

"Uh um, T-Tiny?"

"Yes?"

"I don't know if I want to play your game... sorry."

Tiny stopped in her tracks. "Y-you don't?"

"Well... it just looks... no, no I don't... huh?" He looked up at Tiny as she started to sniffle and tears started to come down her face.

"WAAAAAAAAHHHAHAHAH," she wailed. "Everyone I want to hug never wants to hug me back, or run's away! I must be a freak!" She stumbled over every word.

Sam was completely taken aback. He went from being scared of her to feeling incredibly guilty in a millisecond. "Oh man," he thought, "I was too quick to judge. She probably didn't mean any harm. Man if I wasn't such a wimp she wouldn't be crying right now. Time to man up and make this right."

Sam walked up to Tiny, who was now on her knees with her hands covering her face. "Uh... hey I'm sorry. I didn't mean to hurt your feelings. I don't mind playing your game."

"You... you don't," she said, picking her head up.

"Not at all. Before we do that... mind if I... hug you?"

Tiny's smile grew so wide he could just barely see the bottom of her eyes through her hair, before she quickly pulled him into the tightest hug of his life, instantly standing up and smothering the top half of his body in her huge breasts, as she cheered, jumped, and laughed joyfully.

"Yay yay yay yay YAY! No one's ever asked me for a hug before! Thank you sooooo much, Sam! Does this mean we're friends?"

Sam did his best to respond though he was surrounded by soft jiggling boob flesh. "Mmm-hmm."

"WOO HOO! Oh, I almost forgot," she said, letting Sam free from her grip, and grabbing her bundle of rope, "Let's play my game first then we can cuddle some more!"

Sam caught his breath and was blushing quite a bit before he looked back up at her. "Okay sure. So uh... what is this game anyway?"

"My friends taught it to me. First I tie you up, then I put some tape over your mouth, and then I do whatever I want with you," she said cheerfully. "They called it kidnapping!"

Sam's smile quickly faded. "That's what I get for not going with my gut," he thought before quickly making a break for it. "Aaaaaaahhh!"

"Oh great, you already know the first part of the game," Tiny said, giving chase.

"Uh, isn't there any other game we could play?!"

"Why? This one sounds so fun! Plus I get to keep you afterwards!"

Tiny was right on his heels. It was clear she was intent on dragging the chase out for the sake of fun. Soon they were off the bridge and close to the sealed door to the previous room. Sam cursed himself for not jumping off the bridge into the safety of the pit. His instincts had told him to avoid that at all costs due to his minor fear of heights and the uncertainty of the pit, though it was probably safe considering all he had seen. Now he had nowhere to go, except to the right side of the room, where he again would reach a dead end, except for the pit on his side. Not intent on repeating his mistake from before, he gulped and jumped over the side.

His descent was quickly halted as his collar was grabbed by Tiny, who wore a delighted smile on her face.

"Ha! I gotcha!"

"Oh crap..."

She hoisted him up until she was face to face with him. Her smile, though, quickly faded into more of a slightly disappointed frown. "Hmmm... that was a bit of a short chase. Maybe we should've played this game outside. It's not really fun if I catch you this quickly," she pouted.

Sam saw this as an opportunity. "W-well, maybe we should play something other than the kidnap game? Like charades, or tic tac toe?"

"Mmmm," she grumbled, "but those are so hard... I never win tic tac toe, and Bongo always makes fun of me for it."

If she wasn't holding him in her grip like he was a stuffed animal, he'd find her pretty cute right now. Instead he put his plan into action. "Oh I know, how about red light green light?"

Tiny smiled at this, but not for the reason Sam had hoped for. "Not falling for that one again. A few short guys like you use that game to get away from me, and Blossom always told me never to fall for tricks more than once, and that if I fall for it for a fourth time she'll get mad." Tiny thought for a moment, and then her face lit up into another big smile. "Hey that's right you never answered my question from before. Remember? At the front door?"

"No no no no no no no," Sam screamed in his head.

"Have you ever been sat on before?"

"Uh... w-well I... you see-" she cut him off.

"Cause I love sitting on cute short guys like you a whoooooole lot, and I've got a pretty big butt."

"Yes, I know-"

"You wanna see it?" Without waiting for an answer she turned around and dangled him right in front of her ass. Sam shivered at the sight, not because it was ugly or misshapen, quite the contrary, it was perfectly round, wide, tall, smooth, and bouncy, but it was huge to the point where it could swallow up his whole puny body without much effort, between her massive butt cheeks. Plus he had seen what had happened to that guy she had butt dropped last time, and he was way taller than Sam. "You can touch it if you want."

"Uh no I'm- mmmmmmph!" Tiny shoved him up against her plump booty and started to rub him up and down the length of her butt crack, though she still had her pants on, it didn't make much of a difference for Sam. "Mmmmph, tmmmph lmm gmmm ommf mmm!" Shouting was completely muffled by her warm butt which seemed very eager to swallow him up in it's soft crevice.

"Ooooooo~~~~~ I like the way you feel back there Sam," it was clear by her tone that her more lustful side was coming out.

"Mmmrrrrmmmph hmmm!"

"Hehe... you seem like the perfect size for a woman like me. I could stuff you into a bunch of different places. It'd be nice to have my boyfriend on me everywhere I go. Sure we've got a bit of an age difference, but Blossom always says that when it comes to love nothing else matters." Tiny's giggling intensified. "Come on Sam give my booty a big hug, for me? Pleeeeeease?"

"Mmm-mmm," Sam shook his head, accidentally digging his head further into her ass.

"Come ooooooon," she giggled as she wagged her ass back and forth, "it's nice and squishy~~~~! You know once we start living together you can sleep on it. It's nice and warm."

"Wmmm wmmmmph?" She pulled him free from her huge caboose. "Wait, I thought we weren't playing that game anymore?!"

"Well, not the normal way, but I'm still taking you. All of my friends picked a cute guy to take for themselves, and I picked you. We're gonna be sooooo happy together!"

"L-l-l-l-l-look Tiny... you're very sweet, and i like you, but-"

"HUH?!" She pulled him back around to her front in another tight boob hug. "YOU DO?! GREAT THEN LET'S KISS!"

"Wait, hold on, we need to have a serious talk first!"

Tiny was through listening as her plump puckered lips headed straight for him. "MMMMMMMMMMMMMMM-"

"Ma'am I've never kissed anyone before I need a moment to- Mmmmmph!"

"MMMMMMMWAH MMMWAH SMOOCH MMMWAH MMWAH MMMWWAH MMMWAH SMOOCH SMOOCH SMOOCH MMWAH MMWAH MMMMMMMMWAH! Wow you look really cute with kiss marks all over you! MMMMWAH MMWAH MMWAH MMMWAH MMWAH MMMMWAH! Do you like getting kissed?"

Sam just went limp in her arms and muttered a neutral response, far too overwhelmed by his intense first kiss. Tiny, however, was more than willing to take that as a yes. "Tee hee! Oh Sam, too cute! I can't wait to cuddle you when we get settled in our next town."

"N-next town? You mean... down the road right?"

"Nope," she said, not picking up on his worry, "me and my friends are packing everything up and heading out tonight. We're going far away to set up shop somewhere else. We're a traveling act after all, and you're coming with us, along with a few other cute guys we caught. That's why I have to tie you up. Honka says 'the only way to keep a man in line is discipline, rope, and duct tape,' she said with a silly impression of her friend, "plus they said that if i don't tie you up you might get out of my butt and run away."

"O-o-out of your butt?"

"Oh that reminds me! There's just one more thing I'd like to try out."

Without warning, Tiny, once again, held Sam to her butt thrusted her massive backside at the wall and pinned him there. It was becoming clear to him that despite her naivety Tiny had quite the mischievous and dominant side to her, as she lightly twerked her ass on him. She leaned over enough until his eyes were free. She wanted him to see this trick of hers.

"Check this out Sam!" She pulled off her big red clown nose and blew into it. Sam's eyes widened as he watched it expand to ridiculous proportions until it was the size of an extra large industrial strength yoga ball. "Ta da! My big red nose doubles as a portable seat!" Sam gulped. "But what's a seat... without a cushion?" Double gulp.

...A few minutes later...

"Wait Tiny hold on I think we should talk abou- tmmmsh mm gmmm mmmph!"

"MMMMMMWAH! There we go," Tiny said as she smoothed a piece of tape over his mouth, "now it's perfect." She looked down at Sam with a big warm grin. She had taped him down, spread eagle to the ball. Sure he struggled all the way, but it did absolutely nothing to stop her. He was starting to realize that not only did she see him as a cuddly stuffed animal, he was about as strong as one compared to her. "I've been waiting to do this ever since I saw you Sam," she spun around, casting the shadow of her massive ass over him, causing him to shiver in fear. "It's bouncy time!"

SQUASH!

Sam's body was instantly compressed under Tiny's soft doughy ass as it dropped down on him. Her immense weight nearly pressed the ball to half its original height. Sam was honestly surprised that the ball didn't pop from all of this. This was an unreal feeling. If you were to somehow look at this scene from below you would see Tiny's huge backside eclipsing Sam's small body almost a dozen times over. In height and width he was nothing compared to the happy clown MILF's ass.

Tiny wasn't close to satisfied though as she bounced up and down on the incredibly resilient ball, laughing all the time and even letting out some pleasured moans. The constant push and pull of her bouncing caused him to, over time, get pulled deeper and deeper into the crack of her ass. Sam had to admit despite her hobo clown look she smelled very nice, even when shoved up against her ass crack, though it did have a bit more of a humid tinge to it.

After an hour of this, she finally got off of her ball and looked at her booty in a nearby mirror. All that could be seen of Sam was his leg jutting out from between her cheeks. With a satisfied giggle she pulled him out of her ass with a quick tug, and sat back down on her ball, placing him in her lap. She stroked his hair for a minute or two as she gazed at his exhausted face. She leaned in and placed one last peck on his forehead. "SMOOCH! I loved every second of that Sam. I know we're a bit of an odd pair, but those are my favorites. This time though I'm not gonna let myself be outsmarted. This time I've gotta make sure there's no escape for you," she said as she pulled out the roll of duct tape she had used earlier.

The strip she had put over his mouth was still there, but she decided to wrap a bunch of tape around his mouth and head several times just to be sure. Then she wrapped some around his torso, pinning his arms to his side, and some around his thighs. Then she pulled out the rope she also had earlier, and tied some more of it around his torso, but also bound his arms and ankles. Sam was far too defeated by this point to even complain. He only looked up at her with curious and somewhat fearful eyes, but even he could help but have his heart warmed a bit by her lovely beaming smile.

Tiny stood up. "It's time for us to go now Sam."

"... Mmmmm... mmm..." He weakly moaned.

"It's gonna be a long trip... buuuuuuut... I think I know a nice place for you to stay where you'll be safe, cozy, and warm." she held him under her arm and started to pull down her pants, including her clown themed underwear, revealing her massive bare booty. All Sam could do was nervously stare, before she mercilessly shoved him against her ass crack. She kept shoving, over and over letting her ass cheeks swallow him up, each shove sending him deeper and deeper into the tight fleshy abyss.

The sensation he was feeling was like nothing else, as he was slowly being sealed between her butt cheeks, with less and less of him free from the grip of her booty with each passing second. Tiny's warm squishy mountains wrapped around him, and hugged his body with a strength he had never felt before. Sam was always bullied for his ridiculously short height before, but he had always stood up for himself as best he could. This wasn't a fight though. This was a clear cut case of a toy being played with. That's all he was at this point. A toy for this woman's massive body to play with. He couldn't fight her, and she wouldn't fight him. From the moment he was within her reach, he was hers, and as the last of his body disappeared between her cheeks. He got acquainted with the surroundings he'd be spending a whole lot of time in for the foreseeable future. Sealed away in this big clown lady's booty prison.

Tiny pulled up her pants. Her butt wobbled around, and her cheeks swayed back and forth as she hiked them up as far as they would go. Sure she was giving herself a wedgie, but she was kinda into that so no big deal. "Hehe, I hope you're comfortable in there Sam. You'll get used to it after a while. And don't worry. Once we get to where we're going, me and you are gonna cuddle and smooch for a whole day! Then you can sleep in my butt cheeks all night and the morning after! Oh after that we should try sex, yeah that'll be fun! Don't worry I have a very comfy mattress so you'll be fine."

Tiny shrunk down her big red nose and put it back on, and gave it little honk to amuse herself. With that done she started to strut out towards the door, making sure her butt bounced around for her new boy toy. "Let's go meet up with my friends Sammy, I can't wait to see their new toys too!"

Merry slipped her panties off and placed them around Burt's neck.

"Looks like a collar. Says I own you."

He blushed at her words. She felt him get harder. She pulled off her boxers to see for herself. She gave a low whistle.

"Looks like I've got plenty to work with."

His face felt like it was on fire from all the blushing. She slid him deep into her both moaning all the way. Without warning she began riding him like he was a bucking bronco.

"Don't just lay there. Join in."

Burt's sexed up mind didn't need to be told twice. He began to thrust in a futile effort to keep up with her. She unleashed him from the cuffs. This only lasted long enough for her to remove his shirt. Soon his hands were restrained behind his back. She pulled him up closer kissing and nibbling on his neck and ear. He moaned and thrusted. He tried to reach out and grab her, too lost in his lust to remember the cuffs.

She laughed at his little efforts and shoved his face into her tits. He immediately began kissing and nibbling of his own.

"Such a naughty little boy, you are."

She tightened her legs around his hips to keep him in place. Merry reached up above her and grabbed a hold of the metal bars in the well-built canopy bed. She lifted them up into the air a few inches above the mattress. She swung them back and forth adding a little extra oomph to their wild thrusts.

"Oh god yes!" Burt shouted.

She let him slip out before throwing him onto the bed. She flung herself onto him, wrapping around him and rolling off the bed with him. Laughing like a madwoman she began tittie fucking him while dragging him under the bed for every wicked trick she knew.

"I can't breathe," Trevor gasped.

"Is that so?" Honka teased.

"Please..."

"Please what?"

"Please let me go."

"No."

"Why not?"

"I was going to kidnap that boy. You took him from me."

"WHAT?!"

"I think a punishment is warranted, don't you?"

Trevor smacked Honka's leg.

"Tapping out are we?" she teased.

"Yes! Whatever! Just let me go!"

She opened her legs and let him fall to the floor. Trevor moaned in pain. She grabbed him by the back of his pants and picked him up like light luggage.

"Hey!"

She walked over to the librarian's desk and tossed him on, face first.

"Watch it!"

She yanked down his pants and underwear in one fell swoop.