Jack knew it had been wrong. It was just that he had been taken by surprise. He had stood looking at the girls playing in the park and as usual he had his hand inside his trouser pocket and was playing with his penis. His now erect penis.

Jack was fifty-two, single, and worked at the local shopping centre in the department store. He was a manager in the men’s clothing department.

As he stood watching the girls Hayley saw him and went over to have a chat. Hayley was eighteen-years-old and lived next door to Jack with her parents. She was skimpily dressed wearing a vest top and a very short skirt with bare legs.

As Hayley got closer she smiled as she saw the bulge in Jack’s trousers. She had seen it so often before. Jack seemed to get an erection so easily, particularly when her friends were around.

“Hi Jack,” Hayley said with a smile.

Jack jolted at the sound of his name as he was miles away thinking about the girls he was looking at. They were mainly eighteen or nineteen he knew and he was fantasising about what he would like them to do to him. Being given a hand job by a girl their age was a major fantasy for him. To be fair he had two fantasies. Having a hand job was one, but being spanked was another. In fact he probably fantasised more about being spanked than having a hand job.

“Hi, Hayley,” Jack stuttered, taking his hand out of his trouser pocket. He saw Hayley wasn’t wearing a bra and the vest top was a tight one, so her nipples were pressing the vest top outwards in a very sexy way. He stared for several at her breasts, or at least the outline of them, before forcing himself to look at Hayley’s eyes.

Hayley saw Jack staring at her breasts. He did whenever they met and she didn’t mind at all. It empowered her, she reckoned. “Whatya doing?” Hayley asked although she knew really. He was ogling some of her friends.

“Just stuff,” Jack replied, but was still blushing.

Hayley loved to embarrass Jack. Even though he was far older than her parents. It was just the way she was. “I’m off home, Jack. Fancy walking with me?” Hayley asked.

“Sure,” Jack replied in an off-hand tone but he was more than happy to chat with Hayley.

So Hayley and Jack walked off towards the park exit, chatting happily. Hayley said where she had been and what she had done, all the time looking at Jack who kept staring at any young girls who passed them by.

Hayley had a motive for talking to Jack today. It was only yesterday that she discovered he had a secret. His desire to be spanked. She had only found out by chance. He had been at the newsagents and was looking at magazines on the top shelf. He didn’t spot her as he picked out a spanking magazine and looked at pictures of women spanking adult men. She could see how he lingered over the photographs before buying the magazine.

They got back and Hayley could see no one was at home. She had a key but thought now might be just the opportunity she needed to show Jack she knew his secret. However, she didn’t want to start something at home and find her parents got home. “Drat,” she said. “No one’s home.”

Jack didn’t even stop to think. “Come in to mine, Hayley. You can wait with me until your Mum gets back.”

Ah yes, my Mum, thought Hayley. Jack fancied her as well, she knew.

“Great,” Hayley replied happily.

Jack opened the door and led Hayley in to the kitchen. “A fruit juice?” Jack asked.

“Great. Orange juice please,” Hayley replied.

Jack busied himself pouring two orange juices and handed one of the glasses to Hayley.

Hayley sipped her drink before saying, “I’ve got some pictures of me at the swimming pool last weekend, Jack. Want to see them?”

“Sure,” Jack replied in an almost dis-interested tone of voice although his mind was racing. He knew Hayley wore a bikini and she was slim and gorgeous and he so wanted to see the photos of her and her friends.

Hayley could see what Jack was thinking of as she got out her phone. She found the directory she was looking for connected the phone to his TV and started flicking through the photos. Huge photos on the 85 inch TV screen. There were plenty of selfies of her in her bikini but also lots of other photos of her girlfriends posing around in the pool.

Jack was lost in his own thoughts as he watched the young girls on the screen. It was like the porn he watched but better as he knew several of the girls.

Hayley watched as Jack’s penis grew and the bulge again appeared in the front of his trousers. Hayley was really enjoying herself. After a while she said, “Hey, that’s Mandy. She has a boyfriend who likes to be spanked, you know.”

“Does he?” Jack asked trying to sound as though he didn’t really care.

Hayley looked at Jack’s bulge and was sure it had grown at the comment. She turned back to the TV and watched as the photos changed every three seconds.

“Have you ever been spanked, Jack?” Hayley asked casually.

Jack bit his lip. No he hadn’t but he had thought about it so often. His big dream was to be spanked by a dominant woman with a strong sexy voice who ordered him around and punished him when he needed it. Not just needed it but whenever he wanted to be spanked. Quietly he replied, “No. My parents didn’t believe in it.”

“Really?” Hayley said trying to sound incredulous. “So they just let you get away with whatever you did?”

Jack lied. “Yes.” In fact he got grounded and that was worse in a way. At least a spanking was over with quickly enough. Lots of his friends got spanked so he had discussed it often enough. Even so he had never experienced it himself.

Hayley looked at the screen. “That’s Mandy again.”

Jack replied only half focussing, “The one who spanks her boyfriend?” Jack asked.

“Yup,” Hayley replied again seeing Jack’s bulge extend.

The phots kept turning and Jack’s breathing got deeper and deeper as he was turned on by the often voluptuous young girls who paraded across the screen.

Hayley tried to appear absent minded as she put her hand on Jack’s thigh.

Jack froze as he felt the teenagers’ hand. His breathing stuttered. Hayley was one of his fantasies. He mainly pictured himself across the lap of one of his school teachers but sometimes, well reasonably often he supposed, he pictured himself across Hayley’s lap. He breathed even more deeply as he tried hard to focus on the TV screen.

Hayley could feel Jack becoming more awkward. She loved the control she was having over him. Just eighteen-years-old but she really felt as though she was in charge. She wanted to be more in charge. Having seen how Jack liked the pictures of men being spanked by a woman she wanted to see if she could work it that she spanked Jack.

“Maybe you should have been spanked, Jack?” Hayley asked casually.

Jack caught his breath and still looking at the screen and replied self-consciously, “Probably.”

Hayley decided now was the time to get Jack really thinking. “Mandy’s boyfriend is your age,” she lied. She added, “Well not a proper boyfriend. Just someone she knows who likes being spanked by her.”

Jack jolted at the comment. “Really?” he asked in a surprised tone. After a moment he added, “You say that she spanks him?”

“Yeah,” Hayley replied. She felt Jack was getting hooked.

Jack was silent for a few moments. Silent but thinking madly. So Mandy, who was Hayley’s age, had a boyfriend his own age. Not just that but she spanked him. He thought hard about it. He just knew it sounded cool.

Hayley glanced sideways at Jack as his mind worked. He looked blankly at the TV screen but the bulge in his trousers grew even more. Hayley wondered how much more it might grow.

Jack was giving some serious thought about the teenager spanking a man his age. Sure he had always reckoned he might be spanked by a woman his own age. Mind you he reminded himself how he had often pictured Hayley spanking him. Quite often actually he suddenly realised. He told himself he mustn’t give any indication to Hayley about that though.

“I envy Mandy actually,” Hayley said after a few moments.

“Do you?” Jack asked in a surprised tone.

“Mandy told me that lots of men think about being spanked.”

“Do they?” Jack asked almost absent-mindedly. This teenager seemed knowledgeable beyond her years, he thought.

Hayley really wanted to spank Jack and decided the time was right to make her play. She turned towards Jack and said sternly, “Look, Jack. You already admitted you should have been spanked and looking at that bulge in your trousers I reckon you know that and want it.”

Jack blushed as he looked submissively at Hayley. He was now quite shaken at just how right the teenager was. Her wisdom belied her age. He also realised he was turned on by her dominant voice and nature. So maybe he could submit to his long felt desire, albeit he would be spanked by an eighteen-year-old? He swallowed hard and licking his lips decided and nodded saying submissively, “OK, Hayley.”

“Okay Miss Hayley,” Hayley demanded.

“Yes, erm, right. okay Miss Hayley,” Jack replied nervously. He was taken aback by her snappy response, but found it erotic as well. However, he felt the resistance drain from him and control over their conversation passed wholly to Hayley. For some unknown reason though he felt relaxed about it. He hoped Hayley wanted to spank him just as much as he wanted to be spanked. He waited anxiously for Hayley to decide what should happen next.

Hayley saw Jack was becoming indecisive and wanted her to make the decisions. She was ready to. “Stand up Jack and stand right in front of me,” Hayley ordered pointing to the floor by her feet. “I know just how to deal with naughty boys, Jack. Even naughty boys your age.”

Jack stood up and faced Hayley, looking down at her but instead of feeling dominant he felt particularly submissive. After all he was taking instructions from an eighteen-year-old. Mind you, he reflected, the same eighteen-year-old who he had pictured being spanked by on more than one occasion. Far more in fact.

Hayley’s initial command drew even greater concern on Jack’s face. “I’m going to put you across my lap and give your naughty bare bottom a long and hard spanking. However, I need something to spank you with, Jack. Not just my hand. What do you have?”

Jack looked shocked and concerned at the same time. Flustered though he told the truth. “I have a wooden backed hairbrush, Miss,” he replied.

Hayley thought that would be exactly what she needed.

“Go get it then, Jack. Quickly,” she snapped.

Jack left the room and Hayley heard him go quickly upstairs. He re-appeared just a couple of minutes later and handed Hayley a rather heavy wooden backed hairbrush. “Here, Miss,” he said holding out the hairbrush.

Hayley took the hairbrush saying, “Thank you, Jack.” After a moment she continued, “Get your trousers and pants off, Jack. I will be spanking you on your bare bottom,” Hayley snapped.

Jack licked his lips again as he obediently undid his trousers and pushed them down to his knees. He followed that with his underpants catching the elastic with his thumbs and pushing them down to his trousers.

Hayley tried to look firm but as she watched Jack lower his clothing she was finding it hard not to smile. Somehow she did though, with maybe a smirk showing.

Jack looked down at Hayley again now aware that his penis was on show. Worse, for him, was that it was erect still, maybe even more erect now the spanking was imminent. Even worse was that he saw Hayley’s skirt had ridden up and most of her thighs were bare. He would be lying directly on her bare skin. In fact, just as he had imagined all of those times but now the reality scared him.

Hayley didn’t know why she did it but her hand just went straight for Jack’s penis, grabbing it and squeezing it, licking her lips as Jack groaned. She tugged slightly and Jack reacted immediately moving even closer to her. So she guided him to her side, finding this added power almost intoxicating. What she was certain about though was how much she was enjoying dominating her neighbour. She was sure she could get very used to it.

Jack saw Hayley stretch her hand out but never expected her to grab and squeeze his erect penis. When she did he groaned as he found it so erotic. His breathing shortened and deepened as he fought the urge to cum.

Hayley had given boys her own age hand jobs before now, although to be frank preferred it when she cuddled up to girls and they fingered each other deep inside their vaginas and flicked each-others clit. Nevertheless, she had experience of a penis and could feel the throbbing of Jack’s up and down his stiffness. So looking up and glaring at Jack she squeezed harder and by her eyes dared him not to cum.

Jack saw the firmness in Hayley’s eyes and knew she was in control. He didn’t mind though. In fact if anything he found it a real turn-on.

Hayley squeezed Jack’s erection for several seconds before he let out a gasp he couldn’t contain and his cum sprayed out of his penis, landing on the floor by the side of Hayley’s chair.

After several seconds the embarrassment took a hold and Jack blushed and said a regretful sounding, “Sorry, Miss.”

Actually Hayley had to fight to stop herself laughing. She succeeded and ordered, “Too bad, Jack. You will still be getting your spanking. Now.”

Jack nodded and replied, “Yes, Miss.”

Hayley gave Jack’s now limper penis a tug and watched as he obediently followed her lead and bent down across her lap.

Jack felt the tug and as all of his resistance had long gone he obediently followed the direction of the tug and manoeuvred himself across Hayley’s lap. His hands caught his weight on the floor and as his face lowered towards the floor he saw the stain from his cum inches from his face. A further humiliation for him to suffer he knew, whilst at the same time he realised the adrenalin of sexual anticipation had also been drained from him. Now he lay across Hayley’s lap feeling far from aroused and more, much more in fact, like a naughty boy about to get his bottom spanked by an annoyed superior lady.

Hayley held her arms away as Jack bent across her lap. His face passed close to hers and whilst she knew that she was feeling very confident about her position she could see the worry on Jack’s face. No doubt the worry about the pain he was about to receive.

As Jack’s weight pressed down on Hayley’s lap she felt his penis press on to her bare thighs. She saw Jack wriggle slightly no doubt to get himself comfortable, or maybe in embarrassment because his penis was pressing on her bare thighs. Either way Hayley looked at the back of Jack’s head and she became even more focussed on teaching the naughty man a painful lesson.

Jack felt Hayley’s hand rubbing his bottom. It was just as he had imagined it, except it was a million times more erotic. Sure it was tinged with the fact he was about to suffer something that would be humiliating and painful, but that was his choice. A choice he happily made. So as he lay there he felt aroused again and his penis hardened.

Even when the first spank landed Jack felt more turned on. Yes it hurt. Slightly. On the other hand he found the upended position sensual. The fact his bare tummy was lying across Hayley’s bare thighs was exciting. All he had to do was glance backwards and he saw Hayley’s bare legs. The backs of them anyway, and the position of submission he found exhilarating as well as embarrassing. The mixture of emotions he now realised had given him back his erection. Partially anyway but thickening by the second.

Hayley landed the first spank and revelled in the way Jack’s bottom cheeks buckled and swayed under her open palm. She heard Jack gasp but ignored it. It was a natural reaction. After all she had seen enough of her friends spanked by their Mum’s, just as she had had her own bottom spanked by her Mum. So without any hesitation or concern for Jack’s increasing discomfort she raised her hand again and brought it down just as firmly on his other bare bottom cheek. She even thought she could feel Jack’s penis hardening. Could it, she wondered? With all that pain? Maybe, she told herself as she spanked Jack’s bottom even harder. Spank after spank all over his bottom.

Jack felt the stinging extend around his bottom as the spanks continued to fall. The pain increased but he had expected it to. He was a bit surprised that an eighteen-year-old could spank him quite so hard; maybe though he should have expected it. Either way he was going to stay across Hayley’s lap and take whatever spanking she deemed was necessary. That was a given.

Hayley focussed on the bare bottom across her lap enjoying how it was being turned a darker and darker shade of red. Again just like the bottoms she had watched being spanked. Just as she knew her own bottom had reddened when she was spanked. It didn’t matter that every other bottom she had ever seen spanked was someone closer to her own age and not an adult. However, this adult’s bottom was being turned red in the very same way. Even so her hand was hurting a bit and she eyed the hairbrush. She was so looking forward to using it on Jack’s bottom and to make his pain far more intense without her own hand stinging.

Jack never even noticed that Hayley had picked up the hairbrush. Even when she gave him a couple of light taps with the wooden implement. Not until the first spank with the hairbrush. That was when he howled both in pain and surprise. He felt like twisting around and grabbing the implement but after a couple more spanks he relaxed. Yes it hurt but he believed that didn’t matter. He had read that the stinging sensation after a spanking would turn him on. He knew he would find sitting down afterwards challenging because of the pain but knew he needed the pain to get the stinging sensation and so was eager for Hayley to keep on spanking him to increase the sensation that was flooding through his bottom. That sensation was a stinging pain that he hated and loved at the same time. Maybe hated it more than loved it right now but he knew he would be able to savour the pain later on; when he lay on his tummy he told himself.

Hayley looked at the now very red seemingly glowing red bottom. She saw Jack’s shoulders heave and knew he was crying. An adult crying from his spanking. How cool was that she told herself. Cool enough to make her own pussy damp. Anyway, Hayley told herself that Jack would rue the day he submitted to her for punishment. She was sure that he would have learned not to mess with her. Considering the likelihood of spanking Jack again she rubbed Jack’s bottom again as she waited for him to calm down.

Jack hadn’t been aware that he had been crying. He thought he had coped, until the spanks stopped and he realised his vision was blurred and he was sobbing. On the other hand he knew his erection was still firm and as he felt Hayley’s almost sensuous hand rubbing he felt himself getting aroused again. What he quickly assessed was that he had found the whole experience far more painful than expected, but also much more erotic as well.

“Up you get, Jack,” Hayley ordered once she reckoned Jack was recovering.

Jack had recovered enough to ease himself up from Hayley’s lap. As he stood his hands flew to his bottom and he rubbed as fast as he could, hoping to rub away the pain as he stepped from foot to foot.

Hayley sat back with her legs and arms crossed, smiling happily as she watched the outcome of the spanking. A crying adult who stepped from foot to foot as he rubbed his bottom; his erect penis swaying from side to side. She still wondered if the opportunity might present itself to spank Jack again. She certainly had the taste for it. She uncrossed her legs and squeezed her thighs together happily which told her how turned on she was, just as she felt her nipples pushing her vest top outwards.

Jack couldn’t stop stepping from foot to foot as he struggled to cope with the pain. He looked at Hayley through tear-filled eyes and found her smiling stare as sensual as he had hoped. She might only be eighteen-years-old but he felt he could subject himself to another spanking from her very easily.

Jack calmed down and still rubbing his bottom stood almost still. He looked at Hayley and said, “Thank you for spanking me, Miss.”

Hayley took the continued respect as a sign Jack did indeed want to be spanked again and tested her thoughts. “Have you learnt your lesson, Jack?”

“Yes, Miss,” Jack replied eagerly. He wondered if Hayley would ever spank him again and hoped that by addressing her as though she were superior to him that maybe she would.

Hayley kept a stern tone. “What if you are naughty again, Jack? What if you need your bottom spanked again? I might have to, you know.”

Jack remained respectful. “Then you should, Miss. In fact I would want you to, Miss; either because you heard I was naughty, or if I do anything directly to you that earns me a spanking.”

Hayley looked thoughtfully before replying, “Than I shall, Jack. Expect me to deal with you strictly.”

Jack was still rubbing his bottom and knew he wouldn’t be sitting down comfortably for quite a while but at the same time was delighted that Hayley would most likely spank him again. It was only going to be a matter of time.