Cheeky Milf Job Tiny guy BIG jobs chapter 16 by Ello

After a few days of recovery, and nightmares... You eventually receive a new email. You see it's from Cindy directly instead of the agency.

"Hi Aaron! I hope you're doing well, sorry again for... Well all of that the other day. Anyways I got a link for you here for a product to test! It's more, let's say delicate so not exactly the kind of stuff that would get posted with the listing site. It might look sketchy but it's totally legit I've tested stuff from them before so no worries. Due to the sensitive nature of the work the contract will only open once so make sure you're ok with it and read everything through! Don't forget to ask for more too it's near the bottom. Go high they will almost always accept the bonus you want."

Hope to see you soon!"

You open the link and lenthy job contract pops up. The description is only a couple lines but it's followed by tons of clauses covering the companies ass. You try to click to zoom in on the description but accidentally click accept and it auto signs digitally and closes.... "What the!?" You say as you try to open the link again but it refuses to open. Instead you get a call from Cindy.

"Hello?"

"Good morning Aaron!! Oh my gosh I just got the message you accepted how fun! A drone is already on the way it'll bring you over we're gonna work together on this one! Oh wait haha looks like we live in the same building!? I didn't even know we had a tiny housing section. Come to the 10th floor unit 1069." She hangs up.

"What the hell did I get myself into?" You ask dejectedly as you go to the tiny elevator and take it to the 10th floor. You've never had to go up there as it's normal sized apartments. The elevator comes up to a tiny only hallway that ends in a normal sized one with no more amenities for tiny guys. You carefully keep to the walls and look for 1069. You finally find it and call Cindy on the phone.

"Be right there!!" She answers and immediately hangs up. You feel heavy footsteps approach the door alarmingly fast. The door opens and your eyes buldge as you stare up at the nearly naked Milf clad only in a bra and underwear as she smiles down at you.

"I uh Cindy you're practically naked!"

Cindy shrugs her shoulders and picks you up bringing you inside and closing the door.

"Haha yeah. I figured it's not a big deal for this job at least." She says as she drops you onto her massive breasts. Your feet instantly getting wedged in her cleavage.

"Wait what!?" You ask.

Cindy laughs "oh stop messing with me hahaha." Her tits jiggle as she walks, her cleavage opening up for a moment and swallowing more of you! Your crotch getting sandwiched tightly as her giant tits slap back together and squish your legs and cock. A mix of pain and pleasure as her soft jiggly flesh clamps onto your sensitive area.

"Actually you're supposed to be naked for this! Though I guess you didn't want to go through the building like that hahaha!" Her tits jiggle again swallowing you so only your tiny head is sticking out. Her flesh jiggles and crashes against you pressing you together, your boner twitching happily.

"Wait" gasp "what are we..." Gasp "tes-" -CLAP- her tits separate and swallow you in her cleavage completely squishing you silent.

Finally Cindy arrives at her room and pulls out a box. "Oh please I know you read the contract." She looks down to see you gone. "Oh! Aaron?" She digs her fingers between her chest and plucks you out. "Oops hope you were able to breath in there haha" she roughly takes off your clothes giggling as your boner pops out pointing at her. "Naughty boy" she says gently brining the tip of her finger onto your dick and making it vibrate as she gives it a soft twitch.

You moan softly which makes her laugh as she places you on the bed and faces away. You are about to ask again but her giant pantie glad ass is in front of you. She wiggles her hips and starts to take off her panties!

"What is going on!" You think to yourself as your boner rages as the Titanic milf pulls down her underwear revealing her giant bare ass do you, a glimpse of her butt hole as her cheeks part dor a moment before slapping back together.

She then turns around holding a thong but it is disconnected missing the part that would go between her ass cheeks. Instead there are tiny handcuffs on each end. Your eyes widen.

"See what I mean about these jobs? It can get a little kinky hahaha! Ready to get strapped in?"

"Woah strapped on? Cindy I think there-"

"I'm surprised you accepted the job so fast! I mean for me it was a no brainer and the pay is 10 grand!"

Your eyes widen and turn into dollar signs for a minute! With that kind of money you can really start stacking up some wealth! But at what cost? Your thoughts are cut off as Cindy grabs you and cuffs your wrists to the top part and your ankles to the bottom, your body completing the ass floss portion of the thong.

"I mean... That is a lot of money Cindy but..."

She's already lowered you to the floor, her bare feet stepping into the loops.

"I know right! 10 grand for just a day is nuts that's why it's so easy for me to say yes! Even so I asked for double and they accepted! Crazy right?"

You are sweating as she starts to pull you up like an elevator of doom as you slide up her legs towards her ominous ass... A living thong for a day?!? This is crazy!!! And to survive this giant ass!!! Even for 10 grand... Though it is a lot of money... Did she say she's getting double!?

"But anyways your portion is only like $1,000 which is why I'm surprised you accepted so fast you should have made them match the 10k at least! It's fucked up that they try to pay tinies so much less."

"One thou-umphh" you were outraged and about to complain but by now she's pulled the straps and your face is starting to dig into her ass crack muffling you. Your boner pokes against her soft skin pulsing wildly while fear takes over your mind.

"I guess your expenses are pretty low though huh so I guess it's still a fair rate? You know better than I would haha. Ugh they sent a size too small..." She says as she wiggles her hips and pulls painfully stretching your arms and legs as your face and torso starts getting eaten between her ass cheeks, your screams muffled as her butt wiggles and claps you flat as her cheeks collide.

"Sorry Aaron this might hurt for second..." She pulls again, it feels like your arms and legs are gonna rip off as they stretch to their limit but suddenly your body gets slingshotted between her asscheeks and pulled taught against her anus. Your dick jammed straight in instantly getting clenched, orgasming like a tube of toothpaste getting squeezed to hard as you cum in her ass hole.

She gasps for a second and moans then wiggles her hips. You scream against her butt hole but it sucks more of you in and clenches folding you in half and crushing you flat in it's tight folds. Only your face barely pokes out, your stretched limbs taught and burning.

"Tight.... But pretty comfy! How are you holding up?" She asks and listens but gets no answer. "No need is good news right? Let's see" she bends over to touch her toes and test the thong. Your limbs feel like they're gonna snap barely able to hold such a Titanic ass and hips, your face now swallowed and crushed in her anus.

"Yeah that'll work!" She says as she stands back up and clenches her anus a few times. "Wow you're really in there huh?" She says as she feels your body squish in her sensitive anal folds. "So weird but also feels good! This will be fun!"

You are mentally screaming as her anus smashes you like a trash compactor! You can't spend the day as a thong and butt plug for Cindy's giant ass!! -SQUELTCH- her anal folds smash you wallpaper against the walls of her ring.

"Oooh that's nice more of that!" She clenches repeatedly mashing you like gum and squeezing every drop of semen out of your pulverized flat dick....