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All characters in this story are over the age of 18, the situations in this story are entirely fictional and creations of the author, and any resemblance of characters to existing persons living or dead is purely coincidental.
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(This is a sequel to the first story “Jimmy Learns a Lesson about Teasing” and takes place the next day)
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Jimmy slept soundly dreaming about the woman who exposed him yesterday. Jimmy had the habit of showing off on the beach strutting in front of women with his slim 5’9″ beach body. Today he was glad he had been outed even if it meant he would be embarrassed to encounter any of the women that witnessed it. Brenda, the fitness instructor he met, had stripped him, spanked him, and given him release, in the most embarrassing way. It happened at a reunion party the night before where she warned him not to tease women on the beach anymore…. or else!
Brenda’s friends had left Fort Walton after the party, and Jimmy strolled the beach this afternoon hoping to find her. There was the matter of recovering his shorts and t-shirt which she had taken. That was an excuse. He found her irresistible from the first moment he saw her athletic body and confident look, and the time they spent together yesterday before the party was endearing.
Brenda had mercifully let Jimmy walk home holding up his baggy swim trunks, less the drawstring which she kept. So today, he was reduced to wearing his old swim meet speedo under his shorts and polo shirt. Normally, he only used the speedo now in the tanning booth so that untanned areas would not show above or below his regular baggy swim trunks.
Jimmy reached the condo building overlooking the beach where Brenda was staying and knocked at her door with no answer. Not to let the walk go to waste, he spied the large beachside swimming pool where the guests were lounging and thought he could wait there for Brenda’s return. Given the proximity to many golf courses, he wasn’t surprised to see pool guests that were older women since their husbands were likely out golfing, and they preferred the gentleness of the condo pool instead of the beach with all the youngsters. He found an empty lounge chair and laid out to enjoy the sun.
Brenda had indeed been out on the beach. To pay for the trip down to Florida for the reunion, she had landed a job at the condo building which had advertised free yoga lessons for the many wives of the golfers attending the local tournament. This morning was the first sunrise session where she led twenty middle-aged women on the beach in beginner yoga exercises. For that she was wearing her one-piece swimsuit and a sweatshirt tied around her middle. Standing 5’10”, her all toned muscle didn’t take away from her curvy hips, B cup breasts, and dazzling smile. The women all loved the session and took a strong liking to Brenda. It was as if they all wanted to adopt her as a daughter. After the sunrise session, Brenda went for her morning beach shore run and then met some of the older women who treated her to lunch at one of the many cafes.
Gladys and Janie watched Jimmy from behind their sunglasses as they lounged at the opposite end of the eighty-foot-long condo pool. They were guests at the condo and had just gotten back from the local day spa having enjoyed an early afternoon mani-pedi together to relax with their poolside drinks. They had also attended the free sunrise yoga lessons. Any observer would have said that Gladys, a taller woman, had a voluptuous curvy middle-aged figure. Her side-kick Janie was a petite sprite rocking youthful blue skorts and pink bikini top. They loved coming to Florida with their husbands every year. But their husbands seemed more interested in hitting a ball on the golf course these days. So mostly they made their own sport of fantasizing about all the shirtless young men on the beach. Gladys and Janie would whisper commentary to each other, bordering on erotic, about the young men they saw wherever they went.
Gladys, who wasn’t known to be shy, motioned in Jimmy’s direction, “Oh Janie. There’s a cute one.”
Janie replied, “I’ll say. I hope he goes in for a swim.”
Gladys giggled, “You just want to see him in his bathing suit.”
Jimmy kept a watchful eye in case Brenda came in from the beach. He looked up at the condo building which had ten floors of units with balconies. He saw just a few people out and some towels drying over the balcony railings. The pool before him was strewn with a few foam floats.
Jimmy noticed the two older women on the opposite end of the pool in lounge chairs and another group at a table to the side having drinks. Maybe they were looking at him behind their sunglasses? That thought always made him smile. The sun was out and hot. It was a good excuse to slink off his shirt to enjoy the “reaction” from any women. Leaning forward in the lounge, he slowly pulled his t-shirt up and over his head revealing his nicely tanned and hairless chest. He glanced over at the women.
Janie was indeed watching Jimmy from behind her silvered sunglasses. Boldly, she gave him a gentle nod of approval as she sipped her drink through a straw. Jimmy didn’t miss the message.
Gladys looked over at her friend and simply said with a smile. “There you go.”
Janie kept her head straight looking right at Jimmy and responded, “Hmmm nice chest. But let’s see if we can get the whole picture.” Without lifting her right hand from the chair, she used her index finger to first point to her own skorts and then a couple of quick strokes in the air downward. Then pointed the index finger at Jimmy.
Gladys saw what Janie did and moved her head to look straight at Jimmy expectantly raising her eyebrows as if to say, “Well fella? It’s your move.”
Jimmy knew what Janie and Gladys wanted when he saw the not-so-subtle signals. They wanted the Khakis off too. What good fortune he was having! He got up and did a little stretch, pulling his abdomen in to allow the khakis room to slip. He couldn’t resist the opportunity to do a little teasing given the possible appreciative audience.
He unsnapped his Khakis and unzipped them slowly enough to be the tease he could not resist being. For suspense he reached over to take a drink from his water bottle with one hand, while he sinched the khakis down on one side with the other hand. Doing the tease always got him aroused and he could feel his maleness start to engorge. His speedo made it obvious and that got him even more excited. He had now forgotten all about the stern warning Brenda gave him in their encounter the night before.
As Jimmy’s shorts dropped, Gladys’ eyes widened and she gasped, “oh my! I thought men only wore those at swim meets!” She said it so quickly, Janie had to smile at her friend’s obvious excitement. Gladys added conclusively “It’s so skimpy! Oh, this boy is a showoff.”
Janie flashed Jimmy a big smile as she looked him over and gave an even more obvious nod of approval. She could see Jimmy’s erection on the verge of indecent exposure poking in his speedo. She giggled to Gladys, “yes indeed he is a showoff and with a nice package too!”
Just then Gladys shouted out, “Brenda!! Brenda darling!” as she waved heartily in the air to Brenda who was strolling by the pool gates on the way to her condo unit.
Brenda noticed the two women and diverted into the pool area. When she was close enough not to shout, and noticed the drinks in hand she said enjoyably, “Hi ladies. I see you’re enjoying your afternoon.”
Gladys motioned for Brenda to sit with them saying, “Come. Come, and join us. We had such a wonderful morning at your yoga class dear. It was so refreshing in the morning air.”
Jimmy saw Brenda before she entered the pool area and snapped back to reality. Fortunately, she had not seen him. He could not have her spot him there, down to his speedo in front of groups of women with an obvious boner! Jimmy thought quickly and quietly slipped into the pool and hid in the corner facing away from Janie, Gladys and Brenda hoping Brenda would leave soon. Then he could get “decent” and go knock on her door.
Gladys and Janie happily conversed with their new young friend. They ordered Brenda a drink and started to have a nice visit. Sometimes their conversation was spiked with laughter. Jimmy could hear the laughter and knew Brenda was still there for what seemed an eternity without having to turn around. Eventually the conversation came around to Janie confiding how she wickedly enjoyed watching all the young men on the beach.
Gladys confirmed Janie’s interest enthusiastically to Brenda saying “What else do us older gals have to do darling? Besides the young men today are all so cute. Some of us were thinking of sneaking out to an all-male review we saw at a place down the road.”
Gladys, Janie, and Brenda shrieked together with laughter at that.
Gladys went on, “but I think we already got a little entertainment this afternoon” as she peered over Brenda’s shoulder to see if Jimmy was still around. She spotted his head just above the water on the opposite end of the pool and his arms folded on the apron facing away from them.
Brenda looked around squinting and realized who it was. A wicked smile crossed her face as the festivities of the prior evening raced through her mind. She turned back to Gladys to inquire, “Oh? Just what have you girls been up to?”
Janie giggled, “Hmmm, just a cute guy rocking a speedo at the end of the pool there. Before you came, he was strutting his stuff for us.”
Gladys added “Oh I don’t know about that, but he did strip down for us so nicely and slowly. Maybe he’s one of the male review performers.”
Janie argued “Oh, come on Gladys. He was showing off a full-on boner facing us in tiny speedos!”
Brenda had heard enough. She had to tell them, “Ladies, that’s Jimmy. He visits Fort Walton a lot. He’s not a stripper but how do I say this, … He’s a serial teaser and goes around doing that to women just like you.” Brenda’s jaw then dropped when she realized something.
Gladys saw the look on Brenda’s face and said, “What?”
Brenda explained her revelation, “OH MY GOSH! I think he’s over there hiding! I outed him last night to a group of my friends and he probably spotted me here with you.” She smirked, “I warned him there would be consequences if I caught him teasing again.”
Gladys and Janie leaned forward in their lounge chairs seriously intrigued.
Glady’s asked, “Just what could you do about it? It’s true that anyone would say he was indecent wearing that tiny speedo in public. Are you going to report him?” Then she laughed, “I hope you don’t get him kicked out. He’s just too cute!”
Brenda responded “Oh heavens no Gladys. We can handle this ourselves. After all, you ladies came here for some fun, didn’t you? What could be more fun than teaching Jimmy over there a lesson he apparently needs to learn AGAIN badly.”
Brenda slid a napkin out from under her drink, held it up and said, “We all know how a tiny teasing speedo could end up. Don’t we ladies?” With that she tenderly and slowly ripped the napkin in two with a sly grin.
Janie put her hand to her mouth, “Brenda, you are wicked!” and then, “But I love it!” and after a pause she added excitedly, “You are just the girl to do it!” She leaned over and admiringly clutched one of Brenda’s formidably toned biceps.
Gladys took a strong gulp of her Margherita and said, “Brenda, are you serious?”
Brenda got up, commenting calmly, “I think Jimmy should at least do us a little diving exhibition.” She turned and walked towards Jimmy’s end of the pool and planted her feet, legs apart with her fists on her hips, right in front of his arms in a commanding stance.
Jimmy first saw her planted feet, gulped, and then looked up. Playing dumb, he said, “Oh, hi Brenda.” He was thankful his erection had finally gone down in the water. He thought he could explain the speedo in any case. “So great to see you. You know I came by and knocked on your door, you know, to get my stuff?”
Brenda cut him off, “Save it big boy! I was just chatting with a few of the other girls here and found out you’ve been teasing again. Did you forget already what I told you last night and what would happen if I caught you again? What do you have to say for yourself?”
Jimmy knew he was busted. He tried to bluster his way through, “Come on Brenda, it’s hot out here and I couldn’t just sit here sweating waiting for you. I had to get down to my… uh… uh… “He didn’t want to say the word for his bathing suit.
Brenda completed his sentence. “Your speedo? Yes, I see that’s all you have on. Jimmy, this is rich.” She taunted him, “I should jump in right now and rip that off you.” She let that sink in.
Jimmy knew she could to it, and it secretly got him aroused. She knew his weakness for showing off and what it does to him. He finally squeaked out with sly courage, “Brenda, let me make it up to you. Maybe we can spend some time together alone talking about it?”
Brenda wanted to get to know Jimmy more intimately. But she knew she had to stay in control for now and the opportunity for some fun at his expense was too easy. She said “hmmm, maybe, but you can start by showing me what you’ve been flaunting around to these women.” She went on, “Tell you what. You get out of the pool so I can see how you look in that speedo. See that diving board over there? I want you to do a dive into the pool for all us ladies. Do a swan dive. And before you do it…. When you’re on the diving board play with your speedo a little. I want to see what a little tease you’ve been too. It’s the least you can do since you’ve been entertaining all the other ladies here anyway, don’t’ you think?” Then she slapped the palm of her hand against the side of the other hand and said, “Or would you rather I jump in now and we get down to business?”
Jimmy knew Brenda was serious. He knew he better do what she asked, or things could go seriously sideways. He wasn’t ready to be spanked out here in public and his speedo was feeling skimpier to him by the minute under Brenda’s steely-eyed stare.
Meanwhile, Gladys was busy group texting all the ladies from the yoga lesson knowing they were probably back in their rooms at the condo. Her basic message was “Ladies, Janie and I are down at the pool, and there is this cute guy our instructor Brenda knows who may be giving a diving exhibition. Oh, and ladies, you may really want to come out on your balconies to see, because there may be more “exhibition” than diving going on!”
Jimmy climbed out of the pool and started to get an erection again thinking about what Brenda told him to do. He walked straight faced to the diving board. It was about ten feet above the water. As he looked up to climb the ladder, he could see the condo building to the side. He hesitated when he saw there were several women coming out on their balconies. He realized there were nearly a dozen older women now just leaning on their balcony railings peering down at the pool or at him!
Brenda walked back to Janie and Gladys and stood behind them, arms folded, so that Jimmy would see her commanding watch of the situation.
Jimmy walked to the edge of the diving board pretending to survey the water. He smoothed his hands down his front and played with the waist band of the speedo. His erection was growing, thinking about the women lounging there looking up at him in anticipation. He turned, paced back, and turned, giving a view all-around of his skimpy speedo hoping that would satisfy Brenda.
Janie was riveted to the action on the diving board but looked up and back at Brenda saying, “What did you say to him? I love it! He’s being such a tease!”
Gladys added “mmm hmmm. I just hope that speedo gives when he hits the water.”
They all giggled, except Brenda who had to cover her mouth for Jimmy not to see her excitement.
With a single step and jump, Jimmy arched and did a perfect swan dive into the water. His speedo inched down a little on impact. He slicked his hair back, pulled up the speedo and waded to the side of the pool. He thought to himself. There… I hope Brenda was happy with that and maybe I can get her to leave with me now.
Gladys remarked when Jimmy hit the water, “Not a bad dive! He’s actually really good.” Then she bit her lip, looked up at the balconies and hoped that she had not oversold the situation. Most of the yoga women had come out to see. She looked over at Brenda and said with concern, “Look honey, most of the class is up there.” She sniggered, “But I told them this might be fun in a little more revealing way.”
Brenda replied, “Oh, we’re not done. I promise.”
Brenda sashayed over to where Jimmy was waiting. She laid down on the apron eye to eye with him and said, “Baby that was a really good dive. I’m impressed.” She went on, “but, the finish could have been more um… “streamlined” don’t you think?”
Jimmy replied, “What do you mean? I thought it was pretty smooth.”
Brenda grinned a very evil grin, “No honey. I mean that speedo didn’t give an inch. We girls need to see a more “natural” finish, understand?”
Jimmy stammered because he knew exactly what Brenda wanted.
Before Jimmy could object, Brenda went on, “You need to do that dive again just like that.” She looked up seeing most of her students from the morning yoga class on the balconies and said “It seems you have an audience baby. So, this time, when you are teasing and adjusting your speedo for the crowd, I want you to roll the top down enough to be… um…. interesting. My friends need a little more entertainment, and don’t say no. You know the alternative.”
Jimmy cringed. His butt was still a little sore from their last encounter. He knew he better do what Brenda said to save some shred of dignity. Brenda walked commandingly back to the other ladies with a confident smile. Gladys and Janie were clutching each other’s arms in excitement dying to know what Brenda told Jimmy.
Brenda told them with a huge grin, “Girls, if I’m right, you’re about to get a much better show!”
Jimmy breathed in nervously tightening his abs as he stood at the middle of the diving board one pace and a jump from going off the end. He pretended to adjust his speedo again and deliberately rolled the lip of it down a couple of rolls just as Brenda said. He rolled it down to the top of his appendage in front and his pubic hair was over the top. In back his butt-crack was exposed.
A piercing whistle rang out from one of the ladies on a balcony.
Then a bolder lady called down, “Push It down a little more honey!”
Another called down to Jimmy “Jump honey! You’re looking good!” followed by chuckles from a few others.
Jimmy bounded forward and made the jump. Arching down and hitting the water rushing around his body within seconds, he knew the rolled speedo had caught the water that pushed it down his butt. His manhood also flopped out underwater. As he glided face down to the edge of the pool, it took him a few moments to reach back and tug it up.
The commotion on the balconies was priceless to Gladys. She could tell the ladies approved as a few clasped their hands happily seeing Jimmy’s butt exposed for halfway across the pool. One of them gave a thumbs up sign down to Gladys. In the meantime, Janie slid down behind her drink hiding her grin after enjoying the prolonged flash of tush.
Brenda leaned over and said quietly to her new friends “I think he can do better than that. Do either of you have a metal nail file?”
Janie eagerly grabbed hers and handed it to Brenda gasping, “What are you going to do with THAT?” but wide eyed, knowing full well.
Gladys was quick to group text: “More to come ladies!”
Brenda walked to where Jimmy was at the side of the pool, laid down on the pool apron and said “Baby, that was nice form, but the result just didn’t fully do it for me. I think you need help.” She leaned in, her lips meeting his in a sultry kiss as her hands caressed and snuck down his back with the nail file and plucked an inch slit at the top of the speedo. “There you go lover, that should work better. Now go on and do your little dive again.”
Jimmy had gotten a full-on kiss from the woman of his dreams. Brenda grinned, looked at him and brought him back to earth reinforcing, “or it ALL happens right here, right now.” She pounded her one fist with the palm of her other hand very firmly, “and I do mean All of it!”
Jimmy got up out of the pool and walked back towards the diving board sensing the looseness of his speedo. With his back to Gladys and Janie, they could see what Brenda had done.
Janie couldn’t help but call out to Jimmy. “Nice dive Jimmy! We want more! Hubba Hubba!” That was loud enough to cause laughter from the other women at the table over at the side who were also rivetted.
Gladys chuckled, and group-texted “Wardrobe malfunction Ladies!” She could see her friends in the balcony eagerly reading her text and then leaning over the balcony in anticipation. A couple of them grouped together stirring in reverie where the balconies were joined.
Jimmy was at the middle of the diving board. Suddenly he could hear many loud cat whistles and cheers from the balconies.
One of the women with a particularly loud and piercing voice screamed out “Come on baby, show us what you got!”
All the ladies were getting into it!
Jimmy looked down at Brenda who gave a nod of approval and a firm diving motion with her hand prompting Jimmy along as a few of the other balcony women cheered again. They could see Brenda was calling the shots!
Jimmy hit the water and knew immediately his speedo was at his ankles!
Gladys jumped out of her lounge chair and called out, “Yesss!! That’s the spirit!”
Janie jumped up, ran to the side of the pool, and made a goal scoring signal with her arms up straight.
One woman on the balcony had gotten a big score pad and comically flashed an Olympic “10” for the dive!
Jimmy scurried around and turned to grasp his speedo. It had ripped a little more from the impact, but he could still pull it up. As he flopped around, his appendage was visible through the water to onlookers from above.
Janie pouted when Jimmy recovered and pointed at him exclaiming loudly, “What a tease!”
Gladys agreed by calling over to Brenda, “Brenda! Are you going to let him keep teasing all your students?”
Everyone on the balcony heard that loud and clear and shifted their view to Brenda.
Brenda called back enthusiastically, “Hell no!” She threw off the sweats around her middle and slid into the pool. She waded quickly towards Jimmy and said, “Baby, you knew this was coming.”
Jimmy started to back away in the hip deep water clutching his speedo. Brenda quickly dove under and overtook him. She pulled his legs out from under him and he had to grab for a nearby float to keep his head from going under.
The ladies in the balconies could see the vulnerable position Brenda already had Jimmy in. They cheered to her, “Go get him Brenda! Woot woot!”
Jimmy tried to twist away but applause rang out from the balconies when Brenda stood up and got an arm around Jimmy’s midsection and the other hand on his speedo!
Janie ran up to the edge of the pool and called out to Brenda, “Brenda, remember this?” and she held the napkin up high and wiggled her hips in a dance for everyone as she tore the napkin in half.
The women on the balcony roared! One of them screamed out “Rip that speedo, Brenda!!! The cheering and jeering was deafening!
Brenda held Jimmy tight as his legs were flailing and he was holding himself up with the float. She said to him,”Now baby you know you did this to yourself. You know they’re coming off one way or another. If you don’t stop struggling things will be worse for you baby. I know you know what I mean.”
Jimmy stopped kicking for a moment in resignation.
Brenda held the back of his speedo tightly and triumphantly in her right fist while he hung there suspended. She raised her left hand in the air and shouted up to all the ladies “What do you say ladies? Should we see what Jimmy’s been flaunting?”
A couple of gals together on a balcony screamed down, “Take it off Brenda!” and “Let’s see that tush!!”
Another woman screamed from a few balconies down “Hell no! Let’s see it all!!”
Brenda held Jimmy close and said softly giggling to him over the shouting women, “Baby, it sounds like the vote is in. All your fans want to see the best parts of you! I can’t blame them, and we can’t disappoint them now, can we?” Brenda slipped her left arm around Jimmy’s waist to hold him up, while she let one side of the tear loosen from her right fist. Jimmy could hear and feel the speedo start to give at once. “Riiiiiiiiiiiiiiip.” Brenda lifted her prize high in the air revealing Jimmy’s seriously untanned naked butt for all to see.
The balconies roared, “whoa yesss!!!,” and “That’s a keeper!!,” and “Brenda, you’re our hero!”
Brenda threw the shredded speedo to Janie who was on the pool apron dancing like a cheerleader.
Gladys had walked up to the side of the pool to get a better view and called out, “Such a white butt!” He needs to put a tan on that thing!”
Janie chortled, “Brenda! Maybe you should put a tan on it for him!”
The crowd on the balconies roared again with laughter!
One of the women screamed, “That tease deserves it, Brenda!”
Jimmy looked back up at Brenda, who almost looked apologetic for his humiliation and said, “Not again Brenda!” He started to struggle and kick to get out of Brenda’s vice like grasp around his waist. Meanwhile he was aroused to the point of exploding right there underneath, thinking… oh nooo! I can’t cum here now!
Brenda easily kept Jimmy’s butt high above the water and rock steady and said “Jimmy, I can’t refuse my students. At least they can only see your butt! You know things could get worse. And really, you do need a tan darling.” Underneath she suddenly felt the extend of Jimmy’s raging hard-on and smiled, knowing he wanted all of this despite his weak objection and his kicking legs. Unannounced, Brenda raised her right hand in the air and landed it on his butt with a resounding SMACK!
Glady’s winced at the sound and force of Brenda’s first blow, but chanted playfully, “Oh that’s going to leave a mark!”
Brenda leaned into Jimmy and said “This can go two ways darling. You can resist and put up a real fight and I’ll hold your cute little ass up high so everyone can see, and it’ll hurt like hell, or… you can splash your legs around and make it look like you’re struggling but I’ll keep your butt a little below the water… lots of splash when I slam the water, but it won’t hurt so bad. But yelp and scream so they think it’s really bad. Do we have a deal baby?” Jimmy didn’t have to think long after that first full force blow. He nodded.
She went on gleefully at full voice to everyone could hear, “You really do need to learn your lesson again for being such a tease!” Then she screamed up to her students, “Ok, Ladies. Let’s get down to business!”
The balcony audience was hi-fiving and jumping up and down. “Go Brenda!”
Brenda did indeed “go” with it, and landed several more blows, Smack! Smack! Smack! Smack! The water splashing in the air with each strike made an exciting image for all, and Jimmy’s legs flailing in the water with each blow added to the joy.
Janie revved up the balcony when she screeched, “Make him pay Brenda!”
All the women got a thrill watching naked Jimmy get his due punishment. Brenda landed thirty or more whacks before letting Jimmy go. Brenda felt powerful from the naked vulnerability she caused to happen. If it weren’t for the waist deep water, her own wetness might have shown. She wanted him.
She said for only Jimmy to hear, “Darling, leave your shorts and t-shirt behind and wrap your waist in a towel and meet me in my unit. You won’t regret it.” Then, as she let him go, she announced in a loud voice with hands on hips, “Don’t let me catch you teasing any of these women again!
Jimmy eagerly did exactly as Brenda said and scurried to head up to her third-floor condo unit wrapped only in a towel.
Glady’s came over and gave Brenda a big hug and asked, “your unit is at the end of the walkway, isn’t it?”
Brenda nodded. Then thinking of all their friends in the units along the way, they both exclaimed simultaneously “Spanking gauntlet!”