An adult stories – Jimmy and the Spanking Gauntlet by MaxTwilight,MaxTwilight …………………………………………………….
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 the third story in the series following: “Jimmy Learns a Lesson about Teasing” and “Jimmy the Tease has Another Lesson”. If you like CFNM and spankings deserved, you may want to look back at them. Spoiler alert: there is a happy ending to this one!
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Jimmy scurried up the stairs of the beachside resort condo building with only a white beach towel wrapped around his waist. He could still hear the cheers and whistles of the women on their balconies who witnessed him from above being stripped and spanked by Brenda in the condo pool. Brenda had discovered 25-yr old Jimmy’s tendency to be a tease and took delight in exposing him to her friends the night before and today to her entire middle-aged yoga class in broad daylight!
Jimmy’s face was almost as red as his butt when he grabbed the towel Brenda allowed him to have with instructions to get up to her condo on the third floor for “an afternoon he would not forget.” Jimmy was looking forward because he found Brenda, the athletic yoga instructor he met just yesterday to be irresistible. She understood his need for exhibition, and it gave her great satisfaction to deliver it. In fact, Brenda got so aroused and carried away, she had just literally em-bare-assed Jimmy in public. Not that he didn’t deserve it!
It was Brenda’s students Gladys and Janie who coaxed Brenda to give Jimmy a very public lesson about teasing women. It was also Gladys who assembled all the other bored golf-widows on their balconies by group texting them for some entertainment while their husbands were gone. What an entertaining sight it was for them; Jimmy down to his speedo, and Brenda ripping it from him in the pool for all to see! They cheered as he was openly spanked, splashing naked in the pool in Brenda’s able grasp.
Now, unbeknownst to Jimmy, Gladys quickly group texted from the poolside, “Girls, Jimmy is coming your way! He’s trying to get to Brenda’s condo at the end of the third-floor walkway. Brenda says he deserves more, and you all deserve to give it to him!”
Jimmy turned the corner of the walk and stopped stone cold. He clutched his towel at the waist. Gladys’ message was more than enough for nearly a dozen women to gather on the walkway outside the third-floor condos and there, in his way, was the barrage of middle-aged women.
Sharon, a sensual tall and slinky blonde in front of the group first caught Jimmy’s eye and said, “Hey big fella, that was quite a diving exhibition you gave us.” Her smile told Jimmy all he needed to know. He was in big trouble!
Sylvia, a shorter buxom brunette who followed closely behind Sharon added, “Yeah, honey, especially the wardrobe malfunction.”
The women behind Sylvia snickered. A few of them looked embarrassed themselves at Jimmy’s predicament. But then their eyes widened seriously at what was going on behind him.
Jimmy turned around for a possible retreat, only to find that several of the women from the upper floors had come down the stairs and were now gathered behind him blocking any retreat. He was trapped on the walk!
Carla, a particularly large woman, had led the charge down the stairs to cut off Jimmy’s escape. Carla was an avid softball player and just proved she was as fast as she was large. She commandingly reached one of her arms to the railing and the other to the opposite wall easily covering the five-foot span walk, and said casually, “My girls, what have we here? Is this the tease we’ve all heard about?”
Behind Big Carla, a woman named Marie with a stylish hourglass figure younger than her age responded, “Of course he is! We saw it with our own eyes!” That broke the ice and all the women burst out laughing.
Jimmy thought his only defense was to try to bluff through it and calm thing down. He said to Sharon and the women in front of him as casually as he could, “I’m just trying to get down to Brenda’s condo. I think you all know Brenda.”
Jimmy took a step forward but was met squarely by Sharon who put her hand gently up to his bare chest and said in a slow and sultry voice, “Not so fast. Not so fast. There’s a toll to pay if you want to get through here.” There was silence as she slid her hand slowly down his chest to his abdomen and touched her fingers to the top of his towel. Continuing her alluring smile she said, “Do you have anything you can pay with? Hmmm?”
A collective “oooooOOOOO…” chorused up from all the women.
Sylvia added crassly, “Yeah, Jimmy. There must be something under that towel.”
The women behind Sharon and Sylvia giggled.
All that separated Jimmy from a close-up display of his manhood was the fluffy white condo towel. Now he was at the mercy of all these women who had just seen him flopping naked in the pool. He held the knot in front tightly with one hand. But thinking about his nakedness got him aroused and his erection started to tent the towel.
Sylvia was now peering over Sharon’s shoulder and gaped, “Oh yeah. He’s got something under there!”
Meanwhile, Big Carla had snuck up behind Jimmy and slipped her hand in the top of the towel grasping it strongly at the back. She proclaimed loudly, “Let’s see!” and gave an overhand tug so forceful that the towel yanked from Jimmy’s one hand grip, from Sharon’s tentative grasp and soared backwards up in the air into the upward-stretched hands of the women behind her. Jimmy was instantly naked and stunned.
The women hooted! “Whoa!!! Yesss…….!!!!”
Sylvia pointed at Jimmy’s seven-inch salute exclaiming the obvious, “This boy is hard!!” with her eyes fixed in wonderment.
Sharon kept her hand pressed softly to Jimmy’s abdomen, but let her eyes drop to the obvious and said breathlessly, “Jimmy, you are a very very naughty boy.”
Marie, a dark brunette right behind Big Carla, secretly had a fetish for male spanking. She couldn’t help it anymore and burst out with a near baritone vibrato, “yeah, baby, bend over!” The women roared at the strip club inflection of her voice!
Jimmy blushed and tried to cover up his crotch, but that was woefully impossible with his rock-hard boner.
Sharon’s hand slipped gently to his hardness, took a grasp and with her eyes fixed on his said, “We all know you like this, Jimmy.” With a sly smile she added “and besides, Brenda told us you have to pay.”
Big Carla had a vicelike grip now on Jimmy’s shoulders sandwiching him between her and Sharon.
Marie crouched behind Carla spying Jimmy’s naked butt and said, “Looks to me like he could use a little more color on that thing.”
Jimmy’s ass tingled at the mere mention of more spanking! But before he could object, Carla started moving her pitching arm back in circles like the seasoned softball player she was, round and round and round.
Marie took a deep breath following the motion with obvious glee and unintentionally gasped out a whispered, “Oh do it Carla! Do it!”
In swift delivery, Big Carla landed her open palm underhand style with considerable follow-through on Jimmy’s bare right cheek! (Smack!!!)
Jimmy winced as the force of the blow that put him up onto his toes yelping, “YeeeOwwww!!!”
Carla answered his outcry, “You’ve (Smack!!) …. been (Smack!!) …Very (Smack!!) ….. Very (Smack!!…. Bad (Smack!)” landing a blow with each word.
Jimmy had to reach back and grab his butt with both hands to relieve some of the pain and fend off more punishment. This of course exposed his entire equipment freely to all the women. The women were staring wildly at Jimmy with some of them jumping up in back to see more! A few of them gasped at the unbridled punishment just rendered from Big Carla.
A few patrons walking on the street in front of the condo building looked up hearing Jimmy’s yelp but fortunately for him they couldn’t see behind the walkway railing. The women had a truly up close and private show!
Sharon leaned forward, clutching Jimmy’s hardness and consoled him, “We’ll let you through Jimmy” but you’ll let the girls have their way with you, won’t you?” And then before he answered she confirmed for all to hear, “You all get to have your way with him girls!”
The women hooted “Whoa yeah!!” and, “I’ve got something for him,” and “Come on down here honey!”
Jimmy was resigned to succumb to the “spanking gauntlet” Brenda had destined him.
Sharon tugged Jimmy along by his “handle” as each of the women took turns… some of them massaging his butt tenderly just to feel the heat and a cute ass, two of them whacking his butt several times and one of them giving him an appreciative kiss on the cheek as she cupped and felt his balls lovingly. Marie jumped ahead of Carla, caught up to Jimmy and gave him several whacks out of turn. No one objected.
When they got to Brenda’s condo at the end of the walk, Sharon politely turned him, pinned him against the wall and said, “Now Jimmy, you be sure to show our Brenda a very good time, won’t you?”
The women cooed at the thought of what Brenda would do to him. Jimmy was just relieved to feel the cool wall now on his burning bum. His erection was still in full view in Sharon’s grasp.
While all this was going on, down at the pool, Brenda could barely keep her self-control. After she got Jimmy naked and spanked him in the pool, she was wet in more ways than one. After giving Jimmy the towel and scooting him off into the hands of her students, she stood there a moment composing herself. She re-wrapped her waist with her sweatshirt to hide her swollen and dripping nether lips. Nothing could hide her erect nipples poking through her swimsuit.
She could hear the shrieks of joy rise up from the other side of the condo building where the walkway was. She knew the women were enjoying and taunting Jimmy. She loved her new yoga friends, and they absolutely loved the show she just gave them in the pool.
She took her time even though her heart was pounding. She arrived at the end of the third floor walk just at the moment Sharon was holding Jimmy against the wall by his appendage and the crowd of women fixated on the action.
Seeing that Jimmy was totally naked and suspecting a gauntlet of spankers had been satisfied, she called down the walk, “So ladies, I hope Jimmy hasn’t been too much trouble?”
The gang of women turned to Brenda grinning widely. Big Carla, who was closest to her said, “Nothing we couldn’t handle.” She playfully bounced Jimmy’s towel up and down in her hand. Several of the women laughed out loud at that!
The women parted so that Brenda could walked down towards her condo door where Jimmy was pinned. Before loosening the grip Sharon had on his manhood and yielding to Brenda, she said loudly… “definitely something that SHOULD be handled though.” The women shrieked again.
As Brenda faced Jimmy, she pouted playfully, “tsk, tsk, tsk, darling. It seems you’ve lost the towel I gave you. When are you going to learn to stop teasing all of us? Hmmm?”
All Jimmy could do was stammer, as Brenda reached around him and pushed open her condo unit door. Her nipples of her breasts pressed into his chest. She whispered, now go on in and I’ll be there in a minute.” She patted the side of his butt gently.
Jimmy slinked inside the condo. But he could hear Brenda address all the women outside, “Thank you ladies for taking care of Jimmy for me. But he obviously needs some ‘relief’.” Brenda made quotations in the air on “relief”.
The women all nodded in gleeful agreement. Marie chimed in “You’re just the woman to do it Brenda!” and they all cheered.
Sylvia added “Go get him Brenda!”
Brenda gave a wink to Sharon and a silent “thank you” left her lips as she slipped into the condo unit.
Sharon spoke her farewell through the closing gap of the door. “He’s all yours dear.”
Inside the condo unit…
Brenda’s chest was already heaving with excitement as she saw Jimmy emerge from the bathroom naked but for another towel around his waist and rubbing his sore butt. He pointed at Brenda and said in an accusing but not so serious tone, “You left me to the wolves.”
Brenda approached Jimmy mustering all the confidence she could, grazed his chest with her hand, sashayed to the center room of the condo and wistfully gave him a “come hither” look over her shoulder with a big smile.
Jimmy grinned despite the burning sensation of his buns and followed.
Brenda dropped down on the sofa, clicked on the music from the end table console, and said to Jimmy, “Now baby… what did you go and put that towel on for? Don’t I deserve a little strip dance too?”
Jimmy knew Brenda wanted him. Her trembling smile gave that away. He confidently walked up close to Brenda with his mid-section at her eye level as she sat there on the sofa. She could see his member throbbing for her beneath the towel. He let it loose to fall along with all pretenses and said, “How’s that for a strip?” His eyes pierced through her.
Brenda backed up into the corner of the sofa staring at Jimmy’s erect seven inches thick and hard. All she could get out was “not bad.”
Jimmy knelt on the sofa leaned into Brenda and gave a sultry and pressing kiss on her lips. She clutched his back pulling him to her. Jimmy pulled Brenda’s swim straps down peeling her suit to reveal her firm B-cup breasts and extended nipples. He could feel her heat rising. For all her toned muscles, in this moment her strength would leave her. She gasped as she felt the firm caress on her sides slinking her suit down. He brought his lips to her breast suckling sweetly while caressing her body and pushing her swimsuit to her thighs. Brenda arched her back willingly and lifted up to give in spreading her thighs as her suit rolled lower. She kicked it off completely. She wanted to be naked in his arms and now to be the vulnerable one.
Jimmy raised her arms up over her head, grasped her hands in his and rested his hips between Brenda’s thighs. His pulsing rod needed no coaxing to find his desire and hers. She lifted one thigh wrapping her leg around him in anticipation. As he pushed into her, Brenda gasped admitting her inevitable submission. Her hands releasing his, swung down, clutching his butt in desperation one last time, then pulling him into her over and over. Her juices flowed without regret, until finally her world exploded. She was now simply his. Or maybe, he was hers.