Ben stood obediently with his hands on his head, his nose pressed against the wall, and his bare bottom on show, knowing he was about to be caned by his girlfriend, Natalie. Ben was twenty-years-old and was wearing a light blue short-sleeved shirt with dark blue jeans, albeit his jeans were already pushed down to his knees, as were his dark blue underpants.

Natalie, Ben’s girlfriend of six months, was swishing a cane that she had just taken out of the sideboard. Natalie was forty-two-years-old and she had always liked younger men so she could mother them. 

Ben had started, about a year ago, to lean towards older women when he discovered he loved their maturity and decision making, whilst he was happy to do as he was told. In fact, he loved to be told what to do by women old enough to be his mum and who were, in effect, chummy mummy’s, and to suffer pain-filled consequences if he didn’t. 

Natalie was a very confident woman who used to be a headmistress at the local sixth form college before moving into management where she helped run the business side of the school. She used to think she just liked being in charge of students, but after she left the college, she found a desire to mother men in their early twenty’s. Ben was an ideal candidate as he was the right age and wanted to be mothered. 

Ben and Natalie had met at a party given by one of Ben’s friends, Ella who he met at sixth form college, and Ella’s mum. Ella and her mum each invited their friends. Hence, both Natalie and Ben were invited, as Natalie was a friend of Ella’s mum. Ben and Natalie chatted over a glass of wine and found several matching likes and dislikes and whilst neither actually registered at the time that they had similar needs to a mum and her son, that became clearer when they had their first date a few days later.  

That first date was dinner at a local restaurant. Natalie got there a few minutes early and sat at the table waiting for Ben, who, as it turned out, was twenty minutes late. He did apologise when he arrived, but Natalie wasn’t impressed by the excuse. Ben said, blushing, “Sorry I’m late, but I was watching the football and forgot the time.” 

Natalie simply said, “When I was the headmistress being late would have earned you a caning in my study.” In fact, Natalie was testing Ben to see his reaction, and smiled as she saw him blush and shuffle around on his chair, as though he had some experience of being caned. However, she tucked the thought away and chatted away happily during dinner. 

Ben was thrilled with having Natalie as his date and thought she looked both gorgeous and sexy in her low cut sleeveless floral dress which showed off her full breasts and cleavage, but also her bare arms which Ben always loved to see and also found sexy. He even loved to see, and found sexy, bare arms with bat wings and saw the start of fleshy arms on Natalie which only added to his desire for her. Even Natalie’s shoulder-length hair with a few grey strands made her more attractive in Ben’s eyes. 

Natalie had a glass of wine but Ben said he preferred beer, and the conversation flowed. As Ben took a sip of beer during the main course, Natalie reverted to her earlier interest and asked, “Have you ever been caned, Ben?” 

Ben almost spluttered, but recovered. He had already decided he liked Natalie and she was the type of chummy mummy he would love to have as a girlfriend. He had even pictured her telling him off as he listened to her stern sounding voice, but the question was still so unexpected. He stuttered, “Well, erm, err, yeah, like, once or twice.” 

When Ben fell silent Natalie smiled but demanded in her strict Headmistress voice, “Is that once, twice, or several times, Ben?” 

Ben swallowed hard as he was quite taken by the strict, ‘Don’t lie to me, boy,’ tone of voice, but then seeing Natalie’s smile he relaxed and replied more seriously, “Only at sixth form college. The rules were really strict there and several of my friends got caned, and, yes, I got caned a few times.” 

Natalie asked, “What for, in the main?” She was enjoying the discussion, for sure, and intended using her headmistress tone again as Ben looked like he was turned on by it. 

Ben blushed as he replied, “The usual. Not doing homework got a detention, and doubles got you the cane. I got caned by the headmistress, Mrs Scott, a few times, for doubles,” he admitted. 

Natalie was surprised. “I can understand once or twice, but you are at Uni now so you must have done your homework.” Natalie suspected the answer. 

Ben admitted, “I did, after those canings. In fact, they really got me working, as they did for my friends and other classmates.” 

Natalie smiled. That was what she had expected, and, indeed, it was increasingly common that the introduction of caning again had led many students to buck up their ideas about learning, and get to Uni and achieve much more than in the pre-cane years. She gave Ben a stern look and asked, “So, getting caned paid off for you and your mates?” 

Ben again blushed. “Yes, it made me work harder than ever before, but then it got much easier and I never looked back.” 

Natalie explained, “I used the cane a lot when I was the headmistress and our results motored.” Natalie let the comment hang for a few moments, then added, “Mind you, I think a few of the boys saw me as a bit of a boss lady judging from the way their trousers bulged as I scolded them before making them bend over for the cane.” 

Ben remembered his own feelings when he was about to be caned. His headmistress, Mrs Scott, was rather like Natalie, and he remembered he had a crush on her which was similar to how he knew he felt about Natalie. He thought it strange at the time, but maybe it wasn’t so unusual, he now thought, as he listened to Natalie’s comments. 

Natalie and Ben felt an increasing bond as the discussion progressed. Natalie knew she wanted to see Ben again, but on her terms, and thought that Ben felt the same in reverse. She said, “So how did you feel about Mrs Scott?” 

Ben replied, “I dreamed about her, and, erm, well,” his voice trailed off. 

Natalie smiled as she asked, “Did that include masturbating as you dreamed?” 

Ben looked shocked but again saw Natalie smiling at him. “Well, yes,” he admitted, blushing. 

Natalie laughed. “You aren’t alone, Ben. When I taught at the sixth form college, I had both boys and girls with crushes on me. I never reacted to them, but I could tell from the bulges in the boys’ trousers, and sometimes the taut nipples in the girls' bras when I saw them in their gym gear.” 

Ben felt even better about his crush on Mrs Scott, but was focussing again on what he hoped might be a relationship with Natalie. Certainly, he could see why anyone would have a crush on her. 

After dinner, they went back to Natalie’s house for another glass or two of wine.  Natalie chose red wine, and Ben took a glass even though he preferred beer, which was what he had had at the restaurant. Natalie knew that Ben was already enjoying being submissive to her and, although she knew he was a beer drinker, only offered him the wine, and saw he swallowed hard fighting the request for beer, and accepted the wine for the rest of the evening before agreeing to go out on another date. 

Ben felt relaxed in Natalie’s company and as they went out together again he was happy that she made the decisions for him on their dates, including wine rather than beer. She even started to tell him what clothes he should wear, and he happily followed her suggestions. 

It was on the third date that Ben argued with Natalie. He didn’t like her decision on what he should have for supper when they were at her house. He wasn’t rude or anything like that, but he did question Natalie’s decision.  

Natalie took a stern stance. “I don’t do arguing, Ben, as it is too time consuming.” 

Ben retorted with, “What do you do then?” As he replied so he looked at Natalie’s bare arms and thought again about how he had pictured her spanking him when he masturbated in bed just last night. That was his fantasy, though, and doubted two adults really did that to each other. 

Natalie was matter-of-fact. “I spank and I cane. That way you see my point of view and your stinging bottom reminds you to accept my decisions.” 

Natalie knew she was lying as she had never spanked or caned any of her boyfriends. For her it was a fantasy she wanted to play out. The canes she had were ones she had taken from college and she had still practised using them on cushions as she no longer had any students’ bottoms to cane. She had also given herself the most fabulous orgasms when fingering herself in bed, but now, just maybe, Ben would help her play out her fantasy of caning her boyfriend, just as he might be playing out his own fantasy. 

Ben gasped and was silenced by the threat and wasn’t sure if Natalie was serious or just testing him. Could two adults be like that after all, he now asked himself? Should he actually be as concerned as he felt if Natalie did spank or cane him, or was the reality likely to be just painful and humiliating? One thing for sure was that he loved Natalie talking to him like this, as though she was in charge and he had to do what she said, just like the chummy mummy he so often thought about. 

Natalie saw the concern on Ben’s face but loved the way he seemed worried about her authority. After keeping a stern look on her face for a few moments she said with a smirk, “Of course, after spanking and caning you, we would have to make up. We would both be naked and give each other multiple orgasms.” Natalie then watched as Ben struggled with what she was saying until the realisation spread across his face, and she saw the bulge in his trousers. 

Ben knew he was aroused by the prospect of Natalie disciplining him, but now she made it clear that afterwards, they would make love together. How cool was that, he asked himself? He licked his lips as he replied, “If I have been naughty then I will accept your decision to discipline me.” 

Natalie felt flutters flying around her vagina when Ben agreed to be spanked and caned. She discovered after stopping as headmistress that it was more common than generally thought that being spanked and caned was as much a turn-on for those who loved pain and humiliation as it was for those who enjoyed giving the pain and causing humiliation. Accordingly, Natalie could see a relationship with Ben would give them the sexual arousal both would savour. 

A few minutes later both Natalie and Ben were upstairs in Natalie’s bedroom. Natalie sat on the bed and watched Ben undress. He undid the buttons of his shirt, slipping the sleeves down his arms and putting the shirt on the dressing table. He then undid his trousers and pushed them down, catching his underpants on the way, and stepped out of both. He put both items on the dressing table with his shirt. He finally slipped off both of his socks, and stood fully naked looking at the still clothed Natalie. He saw Natalie looking at his tummy but, when he looked down, he realised that she was, in fact, looking at his very stiff erection. He initially blushed, but then relaxed as his erection confirmed his desire to be disciplined if it was foreplay to sex with his chummy mummy. 

Natalie smirked when she saw Ben’s erection before saying, “Good boy discipline is given with us both naked if by ourselves, and just your trousers and underpants down if watched. Naughty boy discipline is with your trousers and underpants down only as well. Understood?” 

Ben just wanted to get on with it and wasn’t too concerned about Natalie’s reference to naughty boy discipline, so he replied respectfully, “Yes, okay.” 

Natalie knew she was taking advantage of Ben’s eagerness to experience both discipline and sex with her, and that she would have to remind him of his agreement later on, but right now happily stood up and got undressed. She turned and asked Ben to unzip her dress which he did quickly. She turned back looking at Ben as she slipped her dress down her arms and then pushed it down to the floor and stepped out of it. She then put their hands behind her back and unclipped her bra, sliding the straps down her arms, catching them, and putting her bra with her dress. She shook her shoulders knowing her full breasts would sway from side to side and smiled as she saw Ben staring wide-eyed at her breasts. Finally, she edged her thumbs into the elastic of her knickers, pushed them downwards and stepped out of them, placing her knickers with her dress and bra. When she stood back up, she saw Ben gazing at her pussy mound and was licking his lips. She was happy he really did think she was sexy. 

Natalie let Ben gaze longingly at her for a few more moments before turning the dressing table chair into the room and then sitting down. She glared up at the still-standing Ben and ordered, “Get across my lap, Ben.” 

Ben was breathing heavily as he stepped to Natalie’s side and looked down at her bare lap. He bit his lip as he lowered himself down and across Natalie’s lap and loved how his erect penis was squashed on to her bare thighs. Ben balanced himself with his hands on the floor as he looked under the chair and saw his legs dangling on the far side and then gasped as he felt Natalie’s palm on his bare bottom rubbing in circles.  

Natalie loved how Ben was so obedient as he bent across her lap. She had caned lots of students at the college but never spanked any, but knew that spanking was more intimate. She rubbed Ben’s bare bottom several times and heard him sigh erotically which set her flutters flying again and those flutters increased as she raised her hand and brought her open palm down onto his far bottom cheek. When she heard the slap of the spank and Ben’s gasp she thought she might cum, but controlled herself and focussed on continuing to spank Ben, initially on alternate bottom cheeks, and then several times on the same bare bottom cheek. 

Ben was looking at Natalie’s painted toenails and upside-down legs, both of which he found sexy, and more so because he was across her lap, when he saw her calf muscles tense and knew she was about to land the first spank. When he felt Natalie’s palm land on his bare bottom he gasped and thought it hurt more than he expected, and as the spanks continued, he wondered how come he used to get aroused as he imagined being spanked by a series of women he fancied. Yet he had been on so many forums where men kept saying that when they were being spanked by a woman they were aroused during the spanking evidenced by full erections which they gloated about, yet Ben knew that, whilst he had an erection as he went across Natalie’s lap, he didn’t have an erection now. 

Natalie was continuing to enjoy landing harder and harder spanks on alternate bottom cheeks and smiled as she saw Ben’s bottom cheeks being turned deeper and deeper shades of red as he squirmed around on her lap and gasped as each spank landed. Once she was happy his bottom was a deep enough shade of red, she started to spank the backs of his legs and watched him squirm even faster and heard him gasp even louder.  

Once Natalie was happy with the deep red glow, she had turned Ben’s bottom cheeks and the backs of his legs she ordered, “Get up, Ben, for three strokes of the cane.” 

Ben was struggling to hold back the tears as he wanted to show Natalie he could take her spanking, but gasped when he heard he was going to get the cane. Even so, he forced himself up as he still wanted to go out with Natalie and, as he did, Natalie stood up and pointed to the chair. Ben knew to bend over as he sensed Natalie open a cupboard and then heard the swish of the cane. He knew the cane would hurt as he had been caned at college, but there he had his trousers up whereas now he was naked and already had a stinging bottom from the very hard spanking he had been given already. He glanced at the floor to see Natalie’s legs and was surprised that he had another erection. How come, with all the pain he had suffered, and was going to suffer, he wondered, but there it was? Was this what the men on the forums meant by having an erection during their punishment, he wondered?  

Natalie positioned herself and rubbed the cane back and forth across Ben’s reddened bottom and saw his erection and smiled. She knew her pussy lips were damp and was so pleased that Ben was aroused as well. She knew to cane him quickly, though, just in case he came before they could make out, and so pulled her arm back and whipped the cane downwards, just as she did to the students at college. This time, because his bottom was bare, she saw the cane cut in to Ben’s bottom cheeks and the red welt appear, which she never saw at college, although heard Ben’s pain-filled cry, which she did always hear. 

Ben cried out with the searing pain of the first stroke which, just as he had expected, hurt much more than when he was caned at college. He closed his eyes and shook his head as he gasped loudly, but held on to the seat of the chair to ensure he stayed bent over for his chummy mummy girlfriend. He felt the cane rubbed across his bottom again as he opened his eyes and saw Natalie’s calf muscles tense again and knew the second stroke was on its way. He cried out even more loudly and threw his head back as he struggled with the pain, and once again questioned how anyone could be turned on by being caned. 

Natalie saw the second welt appear and rubbed the cane across Ben’s bottom again to give him the third and final stroke. At college six tended to be the minimum, and she would build up to that with Ben, but she thought she should start off with less, just in case he hated it too much. When she pulled her arm back, and whipped the cane back down onto Ben’s waiting bottom, she told herself it was still a very good start, and hoped that Ben would find the benefits too good to miss just for a caning. 

Ben cried out even more loudly and shook his head with his eyes wide open and was shocked by the pain, but within a few moments remembered he was going to get three strokes and so the caning was over. He stayed bent over, wanting to remain obedient, but was breathing deeply as he managed to open his eyes and saw Natalie’s albeit blurred sexy legs close behind him. 

Natalie put the cane on the bed and immediately rubbed Ben’s bottom, loving the feel of the raised welts, but focussing on getting Ben nicely aroused. She rubbed his bottom first a few times, and then the backs of his legs, and then rubbed the inside of his thighs. As she did, she ran her fingers along his ball sac before gently clutching it in her hand and knew he was erect again. 

Ben loved the feel of Natalie rubbing his bottom cheeks, then his legs, and even more as she rubbed his inner thighs. He felt himself getting erect again and as Natalie took his ball sac in her hand he gasped erotically. He wasn’t worried that she would squeeze him too hard because he could sense she was being sensual, and as she was far more experienced than he was at lovemaking he let her do what she wanted, knowing he was getting more and more aroused by her tender caressing. 

Natalie slowly edged her hand around the front of Ben’s thigh and clasped hold of his ball sac and tugged lightly and ordered softly, “Get on the bed. You are a good boy again, now.” 

Ben allowed himself to be led by Natalie to the bed where she turned him around and eased him down so he was sitting on the bed.  

In one movement Natalie knelt down and leaned forward and took his erect penis into her mouth and gently sucked and licked him.  

Ben was getting closer and closer to an orgasm and in a panic said, “I’m going to cum.” 

Natalie stopped sucking and licking long enough to say, “Do, and give me a mouthful,” before taking his penis back into her mouth and sucked and licked with even more intensity. 

Ben threw his head back as he came and could feel his juice squirting into Natalie’s mouth for what was the best orgasm he had ever had.  

Natalie took gush after gush of Ben’s cum into her mouth and felt that he was still breathing heavily as she kept him inside her mouth but she wanted to make sure that he found being spanked and caned worthwhile. 

Ben slowly recovered and sat upright and looked down at a smiling Natalie who had dribbles of his cum on her face. Even so, he leaned down and kissed Natalie on the lips and felt her kiss him back. 

Natalie knew kissing on the lips was okay, but without tongues, until she cleaned her mouth. So, after a few moments, she pulled herself away and swallowed the cum in her mouth and wiped what was outside with her hands. Once happy she had dealt with his cum, she said, “Your turn?” 

Ben had never licked a woman’s pussy before but was happy to do it and so said eagerly, “Sure, let's swap places.” 

Natalie had other ideas and gently pushed Ben back until he lay fully on the bed. She then lay next to him, except head to toe so her head was close to his penis and his was close to her pussy, and took his hand and put it between her legs. “Get me going and then use your tongue.” 

A short while later Ben was licking and sucking Natalie’s wet pussy lips as she had his erect again penis back in her mouth, and they slowly brought each other to an intense orgasm. Afterwards Natalie changed positions so they were face to face and kissing happily. After several minutes she felt Ben was relaxed again and, looking closely into his eyes, asked, “So you are happy obeying me?” 

Ben smiled, knowing that he found the stinging pain of the spanking and caning so arousing. “Sure thing,” he replied eagerly. 

Natalie then told him, “Well this was a good boy spanking, and a bad boy spanking doesn’t end the same way, as you will find out when you are naughty.” 

Ben wasn’t sure what Natalie meant and didn’t get the chance to ask as she kissed him again, inviting his tongue inside her mouth. Well he knew he agreed to obey her and suffer the consequences if he didn’t, so he supposed he would find out soon enough, anyway. Right then he didn’t care. 

Natalie made the comment and kissed Ben without letting him ask any questions about a bad boy spanking. She fully intended to show him at the first opportunity, and reckoned that wouldn’t be very far away. 

As it happened, it didn’t take long at all, which was why Ben was standing with his nose pressed against the wall and with his hands on his head, listening to Natalie swish a cane through the air. He was tense as he knew this was a naughty boy spanking and caning, but was now going to see what that was like. At least he still had an erection, although suspected that would be gone soon. Still, his chummy mummy was in charge and he had to do as he was told.