Joke Backfired with Female Swim Teacher
Posted: Thu Mar 20, 2025 1:25 am
"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.
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.