Joke Backfired with Female Swim Teacher

[jllash]

"Alright, Jim," the swimming teacher called out, "time for laps!"

The last day of swimming lessons and he had the whole pool to himself. The other students in his class had all disappeared for summer vacations, leaving him and the young, fit instructor, Rachel. She was young but still some years older than him, and had a way of making him feel both safe and awkward with her authoritative yet kind demeanor. Her red swimsuit clung to her in all the right places, and he couldn't help but admire the way she moved with such grace and confidence.

As he began his laps, the prank he'd been mulling over grew in his mind. The pool was eerily quiet, the only sound the rhythmic slap of water against the tiles. Rachel watched him with a casual gaze from the edge of the pool. He had always been a shy boy but he felt like he would never get a better opportunity than this. His plan was to remove his swim trunks in the pool and toss them to Rachel. Sure, it's a bit juvenile but he thought Rachel would find it hilarious, toss them right back, and they'd both get a good laugh out of it. He felt a thrill of mischief and decided to make his move.

Reaching the end of the pool, he paused at the wall, his hand grasping the edge to keep himself afloat. With some awkward tugging, he struggled out of his swim trunks, a cheeky grin spreading across his face. He tossed them out of the pool towards Rachel, landing on the pool deck with a light splat. Rachel's eyes widened in surprise, and he expected her to laugh and toss them back. But she remained silent, staring down at the soggy trunks as they lay by her feet.

"Hey, Rachel, toss 'em back?" he called out, his voice echoing through the cavernous room.

Her eyes remained on the swim trunks, and she feigned ignorance. "What are you talking about, Jim?" she replied, a smirk playing at the corners of her lips. She saw an opportunity to tease him a little and she took it. For him to perform such a brazen stunt, she just had to teach him a lesson.

Panic began to set in. He hadn't anticipated this turn of events. "My, uh, trunks," he stuttered, feeling the cool water of the pool against his bare skin. "Could you, maybe, toss them back to me?"

Rachel's smirk grew into a full-blown smile as she glanced up at him. She had the upper hand now, and she was going to enjoy it. "Oh these trunks?" she teased, picking them up with the tips of her fingers as if they were contaminated. "I just found these and I was thinking of taking them to the lost and found."

Jim felt his cheeks burn with embarrassment. He was naked in the pool and she was toying with him. "Come on, Rachel," he pleaded, "It was just a joke, I'm naked!."

Rachel looked at him with a mischievous glint in her eye. "I know you're joking, Jim, but you know the rule: you don't get out of the pool until your lesson is done. And this looks like it needs some drying off," she said, draping the trunks over the back of a nearby chair. She sat down, crossing her legs, and leaned back, watching him with amusement. "Looks like you're going to have to swim a few more laps without them."

Jim's mind raced. He didn't know what to do. The water was cold and he felt exposed, but Rachel had made it clear that she wasn't going to let him off the hook easily. He took a deep breath and pushed off the wall, trying to ignore his nakedness as he swam. Rachel's eyes followed him, her gaze catching an occasional glimpse of his bare buttocks as continued swimming. Each stroke brought a fresh wave of embarrassment, but he couldn't help feeling a strange thrill at the same time.

He reached the other end of the pool and then came back, his cheeks flaming, and hoped she would take pity on him. "Rachel, seriously, please toss them back," he begged, his voice cracking.

Rachel's smile grew more playful as she watched him struggle with his embarrassment. "But you're doing so well, Jim. Just a few more laps and we're done," her eyes glinting with the delight of watching him squirm.

He couldn't believe this was happening. Rachel had always been so professional, so kind to him, but now she was enjoying his discomfort. He took a deep breath and started back on his next lap, trying to keep his body under the water to hide his exposed parts. He felt a mix of mortification and the weird thrill of being watched by Rachel.

The water felt colder and more revealing with each stroke. His face was hot, but he forced himself to keep swimming. Rachel remained seated, her eyes following his progress. She was trying not to laugh, the smirk on her face growing wider. She leaned forward in the chair, her elbows on her knees, the fabric of her swimsuit tightening around her as she watched him intently.

As he completed his final lap, he hoped beyond hope that Rachel would finally throw him a bone, toss him the trunks, and put an end to his humiliation. But she didn't. She just sat there, her gaze unwavering, a glint of mischief in her eyes. "Looks like you're all done," she said sweetly, "you can come out of the pool now, and you better hurry, the next class will be here any minute."

Jim's face fell. He had to get out of the water and walk over to her to get his trunks. The thought of his nakedness being on full display made his heart race, but he had no choice. He climbed out of the pool, trying his best to cover himself with his hands as he approached Rachel. The cool air hit his skin, making him shiver, and he couldn't help but feel vulnerable as droplets of water slid down his body.

Rachel's smile never faltered as she watched him, enjoying the sight of his embarrassment. "You really should keep track of your things, Jim," she said, her tone light and teasing. "You don't want to lose something important like that again."

With as much dignity as he could muster, he snatched the trunks from the chair and turned away from Rachel, his bare butt exposed to her. He was sure his face was as red as a lobster in a pot. The trunks were cold and wet, clinging to his hand like a soggy rag. He tried to pull them up, but they kept sticking to his skin, making it difficult to step into.

Rachel watched his clumsy attempts with a wicked smile. She had never seen him naked before, and she had to admit, it was entertaining.

She tries to think of something that she could do to prolong his exposure and she gets an idea. "Time to end the lesson with some stretches," she instructed.

Jim's heart sank as he looked over his shoulder at her, his eyes wide with horror. "Stretches? Now?"

Rachel nodded, standing up from her chair. "Yep, it's all part of the cool down process. We wouldn't want you getting cramps, would we? Now come over here and face me."

Jim reluctantly turned around, he still held his trunks and he used his hands to shield his privates from her gaze. Rachel stepped closer, her eyes sweeping over him. He could feel her eyes linger on his hands covering his bare crotch.

"Come on, Jim," Rachel said with a hint of challenge in her voice. "You're not going anywhere until you've done your stretches."

Jim's cheeks burned. He knew he was blushing, and it made him feel even more exposed. He wanted to protest, to argue, but the words got stuck in his throat as he faced her, his hands clutching his swim trunks tightly.

The truth was, Rachel had a certain authority over him. She wasn't just his swimming instructor; she was someone he had always looked up to. The idea that she might tell his parents about his prank was terrifying. He didn't want them to know, and he definitely didn't want to be seen as a troublemaker.

But as much as he wished the ground would swallow him up, there was also a weird part of him that felt... thrilled? Exposed, yes, but also kind of excited. It was like he was in a secret club of embarrassment that only the two of them knew about. He knew Rachel was enjoying the power she had over him, and a small part of him was actually enjoying it.

"Alright, Jim, let's start with this one," Rachel instructed, her voice calm and steady.

She began with raising one arm above her head, and then bending to touch the opposite toe, her breasts bouncing gently in her tight red swimsuit. She repeated the maneuver with her other arm.

With trembling hands, Jim mimicked Rachel's stretch, his arm rising above his head then bending to touch his opposite, while his other hand kept a firm grip to shield his privates, then repeated with the opposite arm, always being careful to keep himself covered. Rachel watched him with a knowing smile, enjoying his squirming.

"Now, let's move on to ankle circles," Rachel said, placing her hands on her hips.

Jim watched as Rachel began to rotate one ankle in a slow circle. She switched to the other ankle, her abs tensing with each movement.

"Come on, Jim," she coaxed, "exactly as I did it."

With his face burning hotter than the sun, he copied Rachel's ankle circles, his own foot moving tentatively. He started to lose balance as he raised his foot and his hands went to the sides instinctively without him even realizing it, the coldness of the air hitting his most sensitive parts as he rotated his ankle. Rachel's gaze immediately dropped to his now exposed genitals.

The sight of his small penis made Rachel stifle her laugh. It was so tiny, it was almost comical, and she couldn't believe she had him standing here so utterly naked and at her mercy. There was something uniquely entertaining about this, standing before her following her stretches completely bare, ultimately because he had tried to play a little joke on her by tossing his swim trunks. But Rachel wasn't going to let him off so easily.

She decided to up the ante. "Now, let's do some lunges," she said, her voice still playfully calm, as if this was all perfectly normal.

Jim's eyes widened as he watched Rachel take a long, slow step forward, her back leg straight and her front knee bent and her arms stretched to the side. He knew he had to follow suit, but the thought of exposing himself even further was humiliating.

With trembling legs, he stepped forward and bent into a lunge, his arms stretched out to the side to mimic Rachel's pose. Feeling a thrill at his humiliation, she watched him, his nakedness even more on display.

"Great, now hold it," Rachel instructed, her eyes dancing with amusement.

Jim froze in his lunge, his penis and balls dangling in the cool air. Rachel took a slow, deliberate step around him, her eyes sweeping over his bare body as if she were committing every detail to memory. He could feel her gaze on his exposed butt, and his face burnt even hotter, his whole body a canvas of embarrassment.

"Hmm, not quite right," Rachel said, her voice filled with mock concern. "Let's work on your form."

She moved so close that he could feel the heat of her body, her breath tickling the hairs on his back and neck. His face burned as he realized she was savoring his humiliation.

Her gaze lingered on his penis, which was now shrunk to almost nothing due to the cold water and his embarrassment. Rachel felt a strange thrill seeing him so vulnerable. She reached out and swiftly pushed her finger against his butt cheek, sending him off balance.

Jim yelped and stumbled forward, his arms flailing as he tried to keep himself from falling flat on his face. The cold floor slapped against his palms as he barely managed to stay upright, his cheeks burning with a mix of humiliation and a weird, unexpected pleasure. Rachel's touch had been quick and light, but it was electric, sending a jolt of sensation through his body.

"Now we're even," Rachel stated, giggling to herself as she took a step back. Her voice filled with teasing mischief. "The audacity of you tossing your swimsuit at me like that. You're such a little rascal, consider that your punishment."

Jim's face was beet red and his eyes were glued to the floor. He felt utterly humiliated but couldn't argue with her logic. "Fair enough," he murmured, his voice barely audible. "Can I get my swimsuit on now?"

Rachel chuckled, the sound echoing through the empty pool area. "Alright, lesson is over," she said, her eyes twinkling with amusement. She took a step back, enjoying the final moments of his exposed naked body.

With a sigh of relief, Jim reached for his swim trunks, his hands shaking as he struggled to pull them up his legs. They clung to his skin, and after a few tries finally he was able to step into them, the feeling of modesty restored was worth it. Rachel watched him dress with a smug expression, savoring the moment.

"You know, Jim," Rachel began, her voice still carrying that mischievous lilt, "this was fun, we should do it again some day."

The words hung in the air like a taunt, and Jim felt his cheeks burn even more. "I don't know, I think I bit off more than I can chew," he mumbled, trying to escape the situation while still maintaining some semblance of dignity.

Rachel's laugh was light and airy, and she gave him a playful wink as she walked into the women's locker room, leaving him standing on the pool deck.

[Lola]

Nice! I like that he has a small penis! Double the embarrassment

[Awewe]

Really a good story. Could you make a sequela?

[Awewe]

I really liked this story, cant wait for another

[jllash]

New story, similar idea, Jim has been taking swimming lessons at a distance neighbor's backyard pool, only this time he forgot to bring his swimsuit!

"You're late," Mrs. Castellanos called out as she opened the door to the sight of Jim, flustered and out of breath, his cheeks a rosy hue.

Jim looked at his watch, his heart sinking. "I'm sorry, I... I was running behind and I ran as quick as I could."

Mrs. Castellanos's smile grew wider. "Well, no harm done," she said, "But we've got to make the most of the time we have left." She gestured towards the backyard, where the pool water glistened in the late afternoon sun. "You know the drill. Get changed in the bathroom and I'll be waiting by the pool."

Jim's stomach clenched as he nodded and followed her into the house, his mind racing. He had always been shy about changing in front of others and had gotten in the habit of wearing his swimsuit under his clothes. But as he patted his hips and felt the absence of the familiar fabric, his heart sank. He had forgotten it. The idea of going back home was unthinkable; he'd never make it back in time for the lesson.

"Mrs. Castellanos," he stammered, his voice barely above a whisper. "I... I forgot my swimsuit."

Mrs. Castellanos's eyes widened, but she quickly regained her composure. "Well, that's a first," she said, her tone a blend of amusement and understanding. "Can you run home and grab it?"

Jim's face fell as he did the math in his head. "It'll take me 30 minutes to walk back, and another 30 to get back here. That's the entire lesson," he said, his voice tight with anxiety. "Maybe we could reschedule it for tomorrow? Or refund this one?"

"I'm afraid I'm all booked up," she said, "And my policy is quite clear. No refunds within 24 hours, I can't make exceptions."

Mrs. Castellanos's smile grew mischievous. "Now, here's a thought," she said, "Why don't you go without a suit?"

Jim's panic grew. He knew he couldn't afford to miss a single lesson, not if he wanted to join the school's swim team.

"But..." he stuttered, his cheeks burning "then I'll be naked!"

Mrs. Castellanos raised an eyebrow. "Well, yes," she said, her tone unbothered, "But it's just us here. And I promise you, it's nothing I haven't seen before."

Jim felt his face flush even deeper. "I... I don't know," he mumbled, his voice trailing off.

Mrs. Castellanos's grin never wavered. She leaned in closer, her eyes sparkling with an unspoken challenge. "Look, I'm not here to make you uncomfortable," she said, "But you're here to learn to swim, and I'm here to teach you. If you're really serious about the team, you can't let a little thing like this hold you back."

Her words hit home. Jim knew she was right. He had been dreaming of the swim team for months. He took a deep breath and nodded, his voice shaking slightly. "Okay, I'll... I'll do it."

Mrs. Castellanos clapped her hands together. "Great! You can change in the bathroom, I'll wait for you out in the pool."

Jim's knees felt like jelly as he made his way down the hallway, his mind racing with what-ifs. He closed the bathroom door behind him and took a deep breath. The cool tiles against his bare feet brought him back to reality. He slowly unzipped his pants, his eyes darting around the room, as if searching for an escape route. But he had made his choice. He stepped out of his jeans and pulled his shirt over his head, his heart pounding like a drum in his chest.

Stripped down to his boxers, he took another deep breath and pushed them down, feeling a mix of embarrassment and liberation as the fabric fell away from his skin. He folded them neatly and placed them on the counter, then paused, his hand hovering over his towel. He took one last look at his reflection in the mirror, the fear and apprehension in his eyes. With a final nod to himself, he wrapped the towel around his waist and stepped out into the hallway.

The sound of the water in the pool grew louder with each step he took towards the backyard. Mrs. Castellanos was already in the water, her blonde hair tied back in a tight bun, her head immediately turning to him as he stepped out into the backyard.

"Looks like you're ready," she said, her voice carrying a hint of teasing.

Jim nodded, clutching the towel tightly around his waist, his eyes on the ground. The heat from the sun washed over him, and the coolness of the water beckoned. He took a few tentative steps closer to the pool, his mind racing. The chlorine scent filled his nostrils, bringing with it a strange comfort as it reminded him of his purpose here.

"Remember," Mrs. Castellanos called out, "You're here to swim, not to be shy. Drop the towel and let's get started."

Jim's heart skipped a beat as he looked at her. She was right; he was here to learn, not to hide. He took a deep breath and let the towel fall, feeling the cool breeze kiss his skin. He stepped closer to the pool, his feet sinking into the soft grass beneath him.

Mrs. Castellanos's eyes dropped to his naked body for a brief moment before returning to his face. Her professionalism was reassuring, but the smirk playing at the corner of her lips hinted at the amusement she was holding back.

"Good," she said, nodding her approval. "Now, let's get in the pool. I've got some new drills for you today."

Jim took a tentative step forward, his bare feet feeling the coolness of the concrete poolside. The water rippled invitingly as he took a deep breath and jumped in, the sudden coldness enveloping him in a way that was both shocking and calming. He had done it. He had faced his fear.

Mrs. Castellanos didn't miss a beat, launching into the new drills with a renewed enthusiasm. Jim's mind focused on the task at hand, pushing his nerves aside. He felt more weightless than ever in the water, the gentle caress of the liquid against his skin a stark contrast to the towel he had dropped just moments before. Time flowed like the water around him, and soon, the lesson was up.

Mrs. Castellanos called out, "Alright, last lap, give it your all!" As he approached the edge, his muscles burned with effort, but a strange sense of pride filled him. He had done it. He had swum naked, and the world hadn't ended. As he finished his last lap, the sound of the gate opening echoed through the backyard. He stopped swimming and his head snapped up in horror to find Brittany, a fellow student from school, standing there with her own bag of swim gear.

He realized he'd gone over his allotted time. His heart raced as he sank lower into the water, trying to hide his nakedness. Brittany calls out "Hi Mrs. Castellanos!", then her eyes landed on him with a startled expression. "Jim?" she said, her voice laced with confusion and surprise. "What are you doing here?"

Jim's cheeks burned with embarrassment as he clutched the edge of the pool, trying to keep his body as covered as possible. "Uh... I'm just... I take swimming lessons here, trying to get on the swim team," he managed to stammer out, hoping that his voice didn't betray his mortification.

Mrs. Castellanos looked over at Brittany, her smile unchanged. "Brittany! Right on time as usual. Jim here is just finishing up."

Brittany nodded, looking from Mrs. Castellanos to Jim. "Oh, okay," she said, still oblivious to his state of undress.

Mrs. Castellanos's eyes gleamed as she took in Jim's flustered expression. "Brittany, why don't you go ahead and change in the bathroom?" she suggested, her tone light. "Oh and can you be a dear and toss that towel in the wash."

Jim's eyes widened in panic as he realized she meant the towel he had dropped on the pool deck, the only thing that can provide him modesty.

Brittany picked it up with a cheerful smile, "Sure thing, Mrs. Castellanos!" she called over her shoulder before disappearing into the house.

Jim's mind raced as he sank lower into the water, his body feeling like it was on fire with embarrassment. He knew he couldn't stay in the pool forever, but the thought of getting out and facing Brittany was almost too much to bear. Mrs. Castellanos's eyes sparkled with a mischievous glint as she watched him squirm.

"Alright, champ," she said, her voice carrying the same casual tone she'd used all lesson, "It's time to get out. You've done great today."

"But I'm still naked," he said, his voice muffled by the water as he clutched the pool's edge. "And there's no towels! And my clothes are in the bathroom where Brittany is getting changed..."

Mrs. Castellanos chuckled lightly. "I'm afraid you'll have to make do," she said, her eyes dancing with amusement.

Jim's mind raced as he contemplated his options. He couldn't just race to get his clothes back with Brittany in the house, but she would inevitably come back and get in the water and see him naked, regardless. He was trapped.

Mrs. Castellanos noticed his distress and waded closer to him. "Don't worry," she said, her voice soothing, "Brittany is a good sport. She won't mind."

Jim's eyes widened further. "But..."

"But nothing," Mrs. Castellanos interrupted with a firm, yet kind tone. "You're already in the water, and you can't swim home. Just go out there and get dressed. She's your age; she's not going to think anything of it."

With a deep sigh, Jim nodded, realizing he had no choice. He climbed out of the pool, the water dripping off his body, making his skin feel even more exposed. He took quick, awkward strides across the pool deck, trying to keep his hands covering himself.

Just as he approached the bathroom, the bathroom door opened, and Brittany stepped out, her eyes widening at the sight of him. She was dressed in a sleek, blue swimsuit that hugged her body, her hair tied back in a ponytail. For a moment, the world seemed to stand still as their eyes met.

"Oh my gosh, Jim," she giggled, barely containing her amusement, "You were actually swimming naked?"

Jim's face was a deep shade of red as he nodded, trying to keep his eyes glued to the floor. "I... I just forgot my swimsuit this one time," he mumbled, his voice thick with embarrassment.

Brittany's giggle grew into a full-blown laugh. "You're so weird, Jim," she said, shaking her head. But there was a glint in her eyes that told a different story. It was the same glint that had often accompanied her cruel teasing at school.

"Brittany, please," he begged, his voice trembling, "Could you just grab my clothes for me?"

"What's the matter, Jim?" she taunted, "Afraid I might see something?" She took a step closer to him, her eyes traveling down his body with an unabashed curiosity.

Jim shrank back, his arms tightening around himself. "B-b-brittany," he stuttered, "Could you just get my clothes?"

Brittany's smile grew wider as she took another step towards him, her eyes sparkling with malicious delight. "Why should I?" she said, "It's not like I haven't seen it all before." She leaned in closer, her voice dropping to a whisper. "But maybe I'd like to see it again."

Jim felt a cold sweat break out over his body. He knew Brittany's cruel streak from school all too well.

"Come on, Jim," she said, her voice a mix of amusement and challenge. "You're already naked, just put your hands at your sides. What's the big deal?"

"No way," he replied, his voice firm despite his embarrassment. "Move out of the way so I can grab my stuff."

Brittany's smile grew, and she stepped closer, blocking his path. "Wouldn't it be a shame if word got around at school that you took naked swimming lessons?" she threatened, her eyes gleaming with mischief. "I'm making it easy for you, put your hands at your sides and nobody will know."

Jim's mind raced. He knew Brittany's reputation for spreading rumors, and the thought of the whole school finding out about his predicament was too much to handle.

"Fine," he murmured, his voice barely audible. He slowly lowered his arms to his sides, feeling a mix of vulnerability and anger wash over him.

Brittany's eyes scanned him up and down, and she couldn't help but let out a snicker. "Looks like you're not all that you're cracked up to be," she said, her voice dripping with sarcasm as she took in his small penis and patchy pubic hair.

Jim made a move to push past her into the bathroom and she moved aside, his cheeks burning with a mix of anger and embarrassment. Panic set in as he realized his clothes are nowhere to be found. He spun around, his eyes frantically searching for them. "Where are my clothes?!"

Brittany's laughter filled the air as she leaned against the bathroom doorframe, her hand over her mouth, trying to stifle her giggles. "Oh, I put them in the wash with the towel," she said, her eyes glinting with mischief. "They were on the floor so I thought they were dirty."

Jim's heart sank as he realized he had been played. "You can't do this to me," he said, desperation creeping into his voice.

"Oh, but I already have," Brittany said, her smile widening.

[Jeepman89]

I hope it was shrinkage from the swimming. I'm sure he has a regualr sized dick. Hopefully.