Tiny Tinder Academy – The Resort: Zac Starts to Cum 'Round

Several days later Zac found himself in an odd position that he hadn’t been in for far too long. The days had passed in a blur of first defiance and anger, than unrestrained pleasure. He’d spent so much time inside his sister that he often didn’t know if it was day or night, and he didn’t care.

He was living his greatest fantasy, and it was as great as he could have hoped for.

So he was unaccustomed on a dinner tray while Caley finished her dinner. He’d spent so much time on and in her body he felt cold, though he knew that was just an illusion of his mind.

Idly he strode about the shiny silver tray, letting his eyes adjust to seeing things in the distance once again. He was only a few inches tall, but the handle of her butterknife still came up to his ankles, her plate up to his waist. While he knew it would be incredible to run around her room at his current height, for some reason, he couldn’t quite find the willpower to seek independence.

Zac felt primally connected to Caley in a way he couldn’t explain. The sexual satisfaction he’d gotten in the past several days was incredible and addictive.

“So”, she said as she put down he napkin, “I think we’re both enjoying your change of mind lately, don’t you agree?”

Caley leaned forward and rested her elbows on the table. Zac pulled his eyes from her breasts, small but massive compared to him, and looked her in the eyes. He didn’t bother to respond; even at his size he was sure she could see his growing erection. She had set her phone to his side and had secretly started recording via the camera app. Zac’s attention was completely focused on her.

“Did you realize today is our last day at the resort? I was wondering if perhaps you would like to extend your stay a day?”, she asked, continuing as she pushed her butterknife in a small circle. Zac had to leap over it to avoid getting struck by the handle. “What do you think?”

Zac paused as he looked up at her. She stopped the spinning knife just before it could knock him over.

“Uh, what are you talking about?”, he called up to her. “We have the option to extend our packages?” He vaguely remembered the conversation Caley had with the receptionist long ago, but had almost completely forgotten about it.

“Yes, they’ll allow us to extend out a day or more. I was thinking one more day together would be fun.”

“Hmmm. Yes, that does sound fun. And, you know, I had planned an extra day off anyway to kind of resettle before finishing out my summer job. There’s just one problem sis…”, he said, letting the sentence trail off.

“Yeah, and what is that?”

“I pretty much used up all my savings for this package. I’m pretty sure I couldn’t afford the extra day”, he said, feeling somewhat saddened as he spoke his truth.

“Not a problem, bro. I could pay for both our extensions”, she said, smiling.

On the tray, he began jumping up and down excitedly. “Really? You’d do that? That’s so awesome, sis!”

“So, you’re up for it?”, she asked, wanting to confirm his approval.

He smiled and gave her a thumbs up.

“Awesome. I’ll go talk to the receptionist tonight and let her know of our plans.”, she said, sneakily tapping her camera app recording to off.

“Now that we’ve settled that, I have a reward for you”, she gave him a broad grin, her teeth gleaming as they rose to her gum-lines.

“A..reward?”, he asked, a little unsure of her intentions.

“All that time in my body”, she said, giving him a pointed look and gesturing up and down her naked torso, “and you were always content and happy as my toy, however I wanted you.”

Zac didn’t miss the emphasis in that statement.

Caley looked down at him innocently and blinked her blue eyes.

"There’s gotta be something you wanted, right? How about you pick what we do tonight and tomorrow?”, she offered.

Zac paused and looked around the room. He thought about everything he’d been through, both willingly and not. The very idea that he was getting the option to choose something was so out of left field he hadn’t even put any thought into it.

But he’d learned a lot about what Taylor liked, and realized he’d spent very little time in one of his favorite fantasies.

“How about some butt plug time today…and some pussy time tomorrow?”, he asked loudly, and instantly a wave of awkwardness rushed over him. Despite everything, it still felt weird asking his sister to slide him into her ass or pussy; but the smile that came across her face put him at ease.

Minutes later, a stewardess arrived with the brightest pink toy Zac had ever seen. Caley thanked the woman and took it gently, sitting it sideways on the tray next to Zac. Seeing it in front of him, longer than he was tall, something didn’t seem quite right to Zac. It’s widest point seemed far too large to fit into a woman of Caley’s size and stature, it’s base seemed a little too wide as well. At it’s tip, Zac saw no opening for him to crawl into, only one at the base.

He walked around it again as Caley stepped away briefly before returning with a bottle of lubricant.

“Uh…”, he said as he held up a hand, “This isn’t quite what I – gah!”

Before he could finish speaking, Caley had picked him and the toy back up, holding it upside down from what Zac had hoped for. Instead of being pushed into it headfirst, so only his feet were exposed as she wore him, his feet were being inserted. A light bulb went off in Zac’s head just as he slid in past his shoulders. Just as he started to try and talk to Caley again, she gave him a stern look and he felt the toy squeeze him on all sides as he grew slightly.

She made a satisfied noise and flipped the toy upside down. Zac couldn’t find the air to speak, but he heard the cap of the lubricant bottle pop open and the toy shook as she applied it liberally. A small amount of the slippery liquid dripped all the way from the tip of the toy to settle on the back of his head.

The, from his upside down and awkward vantage point, Zac saw Caley put her foot on the bed and lean forward.

“Good choice bro!”, she said happily

The plug moved forward suddenly and hit soft resistance. Zac heard her groan and the soft plastic around his ankles squeezed slightly harder. Then the tightness of her sphincter loosened, allowing more and more of the toy to slide inside her back door. Soon Zac’s vision was occluded by the growing mounds of her toned backside, held apart by one hand.

Then, without warning, her sphincter stretched past the widest part of the toy and forcefully closed around the more narrow neck of the plug. Zac squawked in surprise as the toy settled deep in her bowels.

He felt Caley shake and moan as she got used to the toy. Testing, he pushed against the tight material holding him and he felt it move slightly, but not nearly enough to allow him to get an arm free. Caley gasped when she felt it though, and Zac knew it was enough for him. Then she released her cheek and put both feet on the ground.

Zac felt odd being upside down once again, and the swaying of her hips as Caley walked felt even stranger. Then Caley did something that made him laugh hysterically despite the ‘wrong’ part of him sticking out of her.

Caley bent forward in front of the long mirror in the bathroom and pulled her cheeks apart once again. The large toy felt wonderful and every step was incredibly stimulating. But she had to see.

And just as she had planned, instead of seeing her tiny puckered brown hole, in it’s place she could see Zac’s smiling face surrounded by the pink base of the toy. Satisfied with how her toy was situated, Caley stood straight again and began planning what she would do the following day.

“Hang gliding could be fun”, she said to herself, momentarily forgetting Zac.

--

Zac couldn’t believe how long Caley left him in for. Not that he was entirely sure, of course, but he never could have guessed his sister would enjoy an anal toy for so long. Time had lost it’s meaning. He was only removed for her to do her business, then he was quickly replaced.

She went about her day with him safely stored in her backside, happily pretending everything was completely normal. And for this resort, it was.

More than once, Zac found himself face to face with a giant or giantess who, in the midst of going down on his sister next to the pool, saw his plight and spared him only a giggle and a lick before returning to their main goal. Less comfortable was the feeling of a giant’s balls resting against his face while someone plowed into his sister, but even as their mixed fluids leaked out of her used pussy and onto his face, Zac felt oddly satisfied beyond anything he could have imagined.

The only thing that could have made the situation better was if he’d been able to move enough to pleasure himself. The inability to reach his manhood was driving him crazy.

Finally, after a day of having Caley’s thong bikini pressed against his face, blocking the sun while she went down on several guys on the beach, Zac felt himself slide out of her ass for the last time. She flipped the toy upside down, gave him an oddly sad look, then sat him on the same tray that had held her delivered breakfast. He felt himself being sized again. He estimated he was between two and three inches tall.

“Hey, uh”, he called as she walked away, sensing the change of energy, “what’s going on?”

There was no response beyond the start of the water from the showerhead. Suddenly, there was a jerk and his stomach flipped as a waiter removed the tray from Caley’s room. Zac panicked as he was taken away.

“No! Wait!”, he yelled, but the waiter ignored him. Zac couldn’t even be sure if he’d been heard, the pink toy he was encased in was rolling around slightly as the waiter put it on a cart which slowly was filled with more and more trays as the staff finished cleaning other rooms.

In his panic and distress, he didn’t realize something extremely important. He hadn’t been abandoned and forgotten. He was being taken away by the cleaning staff.

“My time can’t be up already!”, he yelled at the disembodied voice above him.

***