Tiny Tinder Academy – The Resort: The Swim Instructor and his Cock-Ring

Later that afternoon, after a stunningly good lunch of kale and fruit, Caley found herself looking. Hunting, more like. Her biking partner that morning had been very well endowed, and though he was gay, Caley found herself craving something in addition to Zac who was currently being held tight right against her opening. She’d found it was incredibly comfortable to hold him there, but knew if she shoved him within, then she’d spend the day masturbating with his tiny form instead of exploring the resort.

She quickly discovered the pool that her room overlooked was far from the only one, and while she skipped the salt-water pool, the third pool drew the most interest. It was a simple square pool with crystal clear water, but it’s other contents drew her eyes. Before she knew what she was doing, she’d stripped down to her pink thong and red sports bra.

“You made it just in time!”, said the model with a chiseled jaw and short black hair as she entered the pool. The water was up to his waist, just below her breasts, and the size difference made her wet in a way that had nothing to do with the water.

Zac struggled against the pink material that held him, but knew it was useless. When she walked, he’d held still so as not to get his sister excited that her wetness covered him, but through the thin material he’d been able to see where they were when she peeled her shorts off, and he’d seen the water fast approaching as she walked down the ramp. Suddenly desperate to avoid drowning, he tried to pry an arm around the material of Caley’s panties, but the elastic easily overpowered him.

Changing pace, he tried to push his way up into her. Yes, he hated the idea, but his brain refused to understand that he was functionally immortal and that he literally couldn’t drown. For Caley, all his efforts amounted to a feeling similar to being fingered by an enthusiastic, but inexperienced teenager.

Zac screamed as Caley waded into the exercise pool and joined the water aerobics class just as it began.

Cool water surrounded him from below and steaming heat from above. Low bass rumbles reached his ears as Caley started to move, at times almost giving him enough room to free himself, and at others pushing him harder against her sex. After a time, he forced himself to calm down from his survival reactions and found himself with his eyes closed and desperately hugging the material of her thong as it threatened to send him inside her once again.

His body screamed with the urge to breathe again, but he’d already filled his lungs with water. All he could do was hang on as his world churned. Once, during a rare break in the chaos, he pushed his face hard against the material and saw other pairs of legs in the distance, some clothed, some not.

Where am I?!, he wondered desperately as Caley started lifting her knees high in rhythm with the music he could faintly hear through the water. His question remained unanswered as Caley followed the instructor’s commands eagerly.

“That was a great class!”, Caley said to the instructor after the rest of the participants had wandered away. Water aerobics were especially difficult and few of them had any energy left over. Luckily, Caley had frequently taken these classes to augment her stamina while dancing and still felt relatively fresh, though her legs were a little weak after the bike class that morning.

“Well thanks”, he replied in a deep voice, meeting her eyes with a smile. A smile that felt vaguely predatory. He looked around the pool and surrounding area to double check he wasn’t leaving a guest in the water alone, then followed her up the ramp. She knew his eyes were on her ass, and she loved it.

After an eternity the water receded and Zac gulped in a breath of air; it was saturated with Caley’s scent, but his lungs demanded it. Above him, she was smooth and slippery and he hoped after whatever had just happened, she’d want to take a nap. Or do anything that left him alone.

“Oh, whoops!”, he heard her say from above, “Someone dropped a penny!”

His heart fell as her legs moved sideways and the floor rushed upward suddenly. There was a moment of confusion, then he pushed his face against the fabric of her thong and realized what had happened: she’d gotten on all fours.

“Oh darn!”, he heard a man’s voice say with barely hidden laughter. A massive shadow seemed to be kneeling behind her. “The waistband on my shorts is too loose!”

Zac screamed when he saw the man’s cock fall free from his shorts, a beast far larger than Zac was. Neither giant heard him, and he knew neither would card. Caley moaned and easily overrode his scream when the man rested the tip of his cock on one of her cheeks and pulled her thong to the side.

Zac’s scream turned into a breath of relief when he realized he wasn’t going to be pounded into her by that monster, but that quickly turned into fear again when the massive cock pistoned straight into her opening right next to him. The material of her thong was keeping it from touching him; pulling it aside had only tightened it on him as a prison. But at least he wasn’t being used for her pleasure.

After what seemed like a mile of cock slid into his sister, part of the cock remained outside, and Zac realized the man must have bottomed out. But he wasn’t ready for what happened next.

“Hi!”, said a bizarrely cheery voice from right next to him.

“Whoa!”, Zac said as he realized who spoke.

Wrapped tightly around the base of the giant’s cock was what at first appeared to be a dark cock ring. On closer inspection, Zac realized it was actually a tightly stretched tiny whose face was now only inches away.

“I know, right?”, the woman said as the giants above them spoke briefly. “Aren’t I the luckiest woman eeee-ver!?”

Her question faded into the distance as Zac watched the massive cock pull back, then slam forward again. The woman-turned-cock-ring let out a delighted squeal with each thrust and it was clear that she was having the time of her life.

Please let this end, please let this end, Zac prayed silently as the two giants violently rutted above him. The new addition threatened how much his mind could take.

“This!”, the cock-ring woman screamed with one thrust, “Is!”, she screamed on the next, “Awesome!”

Zac tuned her out as best he could, but before long, he knew the situation was about to change. The thrusts were more erratic, the sounds changing from short words to animalistic grunts. And after all this time inside of her, Zac knew Caley was about to orgasm.

Caley held off as long as she could while the trainer, whose name she hadn’t bothered to learn, shoved as much of himself inside her as would fit. But when it was clear his moment was at hand, she let herself go. The blonde pushed a towel into her mouth as she screamed and when her pussy spasmed around the massive rod, she felt a rush of heat within, triggering another orgasm as he finally pushed hard enough to get his hips against her ass. She was so full of cock that Caley was sure if she looked down, her stomach would have the outline of the head of his cock against her abdomen.

And then, when the cock stopped twitching, and long before Caley was ready, he pulled himself free.

“Oh!”, she moaned as she felt her pussy twitch in response, feeling momentarily empty, she wished he would stick it back in. But she knew, like he’d told her, he only had a few minutes.

“Wish I had more time to give you”, she said with an apologetic tone as he stood, and she slipped her thong back over her opening just as his seed started to leak out.

Caley looked back at him to see just how much cock she’d been filled with and caught sight of him tucking it away.

“Uh, what was that?”, she asked as she saw his cock ring; she’d heard of them before, but never used one. It looked significantly less metallic than she’d expected.

“Oh, don’t worry about her”, he said, pulling his rapidly shrinking and softening cock free again to show her. One hand spun the ring around until Caley could see the tiny black woman smiling hugely up at her. Caley gasped when she realized it wasn’t a metal ring, but a tiny guest who had been stretching around the largest member she’d ever seen.

“She didn’t pay her bill, so we’re keeping her as a tertiary toy until she’s earned enough.”

Caley felt heat in her belly as the cock vanished and the trainer helped her to her feet. The idea of being stuck here and being used for months on end was surprisingly appealing.

“Don’t!”, he said with a laugh, knowing what she was thinking. “Some days, she gets a fun job; most days, we use her to clean out pipes and grease traps.”

Zac recoiled in disgust as the giants talked. His temporary reprieve had been instead replaced with something far worse than what he’d already hated: desperate to avoid it, he held his breath. But instinct won out once again and his mouth filled with the salty seed of the man who’d just cum inside his sister. Every step covered him more in his spunk and Zac knew it would take years of therapy to avoid screaming every time he saw his own jizz after this experience.

Briefly, he wondered if the trainer was the reason Caley had asked about an extended stay. Perhaps she wanted to shrink him down and use him as she had himself. Zac was surprised to feel a twinge of jealousy at such thoughts.

***