Monica arrived at Jeff’s house to do her normal twice a week cleaning job for him. Monica was nineteen years old, and Jeff was forty-eight years old and divorced. Monica had cleaned for Jeff for several months already and he enjoyed having the teenager around the house.
Monica wore her usual skimpy vest top with a bare midriff and tight cotton shorts. She always found that they were the most appropriate clothes for cleaning so that none of her better clothes got stained. She knew that Jeff tended to gawk at her as she carried out her work, but she never minded that, and rather liked the attention.
Things did change slightly when, one day, Monica was making Jeff’s bed and she saw quite a large stain on the sheet. She knew that it meant Jeff had masturbated in bed, and she joked to herself wondering what he fantasised about.
After that first time, Monica saw a similar stain each time she made Jeff’s bed. Soon after that, she discovered a second secret when putting a jumper away in one of Jeff’s drawers. She saw the corner of a magazine, and, shifting the clothes almost hiding it, she saw that it was actually a magazine about people being spanked. The third secret she discovered was when tidying up Jeff’s cupboard. She saw, right at the back of the top shelf and having to stand on a chair to see it, a long cane. Putting all these things together, she was now pretty sure that Jeff fantasised about discipline when masturbating.
What Monica didn’t know was whether Jeff was into disciplining others, or having someone else discipline him. She certainly didn’t want to ask any questions until she knew the answers to those questions, because there was no way that she was going to have Jeff, or indeed anyone, discipline her.
On the other hand, Monica quite liked the idea of disciplining Jeff. She did like him, and if he was looking for someone to discipline him, she joked to herself that she could always add that into the work she was doing for him. Still, she didn’t suppose it would go anywhere but was aware of how she felt flutters flying around her vagina at the thought of using that cane on Jeff, and she also felt her taut nipples pushing at her bra.
After a few more visits and Monica noticing that he had bought a new magazine regularly, Monica worked out a plan to at least establish if he was a submissive or a dom. She was still not expecting it to go anywhere but it was a bit of fun for her. She wore a particularly tight vest top and made a point of walking into the room where Jeff was on as many occasions as she could. She noticed that he was definitely gawking at her more than usual, no doubt because the shorts were even shorter than usual and didn’t quite cover her bottom cheeks.
However, after an hour, she asked Jeff, “Do you want a coffee? I really do fancy one.“
Jeff happily said, “Oh, yes please, Monica.“
A few minutes later Monica and Jeff were both sitting at the kitchen table enjoying a cup of coffee. After a couple of minutes, Monica blushed as she said, “ I’m sorry I was a few minutes late today, but my mum asked me to give my younger brother a spanking. He is eighteen years old and still gets spanked, but mum was out, and he needed one urgently. I didn’t mind, and have spanked him several times already.”
Of course, it was all a lie, as whilst her brother was really eighteen years old and was still spanked, it was only their mum who spanked him, but she was trying to find out which direction Jeff was taking so far as discipline was concerned.
As Monica gave the explanation she glanced at Jeff and saw that he was blushing and looking down at his hands and swallowing hard. She still wasn’t sure what Jeff was thinking and so she told another lie. “The women are definitely in charge in our house. Mum doesn’t just spank my brother but also spanks my dad. In fact, he gets spanked even more often than my brother. I get to watch her spank them both, but I haven’t yet spanked my dad myself.“
Jeff eventually asked in what he tried to make an innocent sounding tone, “Does your brother cry when you spank him?”
Monica replied in a purposely stern tone, “Isn’t that the point?”
Jeff stuttered, “Erm err, well, yes, I suppose so.”
Monica then demanded but in a less stern tone, “Have you ever been spanked?”
Jeff blushed again and was obviously embarrassed as he squirmed around on his chair, but replied, “Only once, and that was at sixth form college by my form teacher and I never told my parents.”
Monica asked, “What was the teacher's name?”
Jeff was still blushing but looked like he was picturing his teacher in his mind as he said whimsically, “Miss Watson.”
When Monica saw Jeff licking his lips and still blushing, she asked, “A woman, eh? I don’t suppose you like women being in charge of men?”
Jeff was still blushing as he answered, tentatively, “Well, I’ve never seen what’s wrong with a woman being in charge. Miss Watson was strict but fair. My wife had a dominant personality and I never minded that.”
Monica pressed Jeff, letting out a short laugh first, and then asked, “How come your wife never spanked you?”
Monica saw Jeff swallow hard again before he replied, “She wouldn’t.” After a second it was as though he realised what he had said, and tried to retract it by saying, in a stuttering tone, “I mean, erm, not that,” but his voice trailed off as he blushed even more deeply.
Monica was smiling as she watched Jeff struggle with his answer. She knew she shouldn’t really do this to her employer, but she was into it now and was enjoying herself too much. Anyway, Jeff could stop the discussion at any time if he wanted to. So, she pressed again by saying, “I made my brother’s bed today and saw that there was the same kind of stain on the sheet that you have. I phoned my mum to tell her and that’s when she told me to give him a spanking. So, why shouldn’t I give you a spanking for staining your sheet?”
Jeff was wide-eyed as he asked in a very surprised tone, “You spanked him for masturbating?”
Monica kept a stern look on her face but found it quite funny that here she was, just nineteen years old, and discussing masturbation with a man in his forties. However, she was having too much fun to stop and replied, sternly, “My brother knew if he stained the sheet he would get a spanking. It was one of the rules. It’s because he also stains the mattress and those stains don’t come out.”
Jeff was looking down at the table as he replied, “My wife never set any rules for me.“
Monica said in an even sterner tone, “Well, I’m guessing from the way you are looking you would’ve been quite happy if she had set that as a rule, and probably several others, and spanked you whenever you broke a rule. Is that correct? Answer me now."
Jeff never could deal well with women in authority and he was floundering as he replied submissively, “I guess so.”
Monica then demanded, “So are you telling me she never used that cane in your cupboard on you?”
Jeff really wasn’t handling it at all well as he replied, “No, I’ve only used it on myself.”
Monica almost gasped seeing that Jeff winced as though regretting giving that answer as well, but held her stony stern look as she replied, “I think I should use it on you now to teach you not to stain your sheets and your mattress.” After a pause, she added, “Presumably you are imagining yourself being spanked and caned as you are doing yourself in bed?”
Jeff winced again as he replied, “That’s right.”
Monica then demanded to know, “How many strokes do you give yourself when you are doing yourself in bed?”
Jeff blushed an even deeper red as he said, “I don’t count. I just keep going until I have cum.”
Monica then pressed with, “Well, I think that I should give you a very hard bare bottom spanking first and then twelve even harder strokes of the cane. That should stop you needing to fantasise about it in future."
Jeff saw the sense of Monica’s suggestion and, looking at her with a smile, asked, “Would you really do that for me?”
Monica liked the idea of punishing someone Jeff’s age and said, “Of course. Mind you, it will add at least half an hour to the time I need to spend here. Therefore, I won’t have time to finish everything.”
Jeff was immediately cooperative and replied, “That’s no problem at all.”
With everything settled, Monica stood up and turned her chair away from the table and into the room, and sat down again. She glared at Jeff and ordered, “Take your trousers and underpants off.”
Jeff licked his lips at the thought of undressing in front of such a young woman. However, he really did want to experience what he fantasised about and could hardly expect Monica to spank him over his jeans. He, therefore, took a deep breath and then proceeded to undo his jeans and push them down towards the floor, catching his underpants on the way, pushing both down to the floor and stepping out of them, scooping up both, and then placed them on another chair. He was blushing, he knew, by the time he turned around and looked down at the very strict looking Monica.
Monica had seen plenty of girls undress before but hardly any men and found it arousing to watch Jeff undress, knowing that his penis would be resting on her thighs. In fact, she did get a bit of a surprise to see that Jeff’s penis was now erect, confirming--if confirmation was needed--that he really was aroused by the thought of being disciplined by her.
Monica allowed herself a few moments lingering at the sight of Jeff's erection before ordering, “Now get across my lap.”
Jeff had so many different emotions as he went to stand by Monica’s side and looked down at her lap and then eased himself down. On the one hand, he had fantasised about being spanked, but that would always be by an older woman and so was concerned that Monica was still a teenager. He reconciled though that, as he got older, he pictured that woman being closer and closer to his own age, and finally settled on his wife spanking him even though she was two years younger than him. Once she left him, he started to picture himself across the lap of a lady who lived across the road, and she was a similar age to his wife.
Admittedly, from time to time, he also pictured himself across the lap of the daughter of another neighbour who he reckoned was about twenty-five years old. So, whilst he was concerned about Monica’s age, his fantasy women were getting closer and closer to her age, and so by the time his full weight was across her lap he wasn’t so concerned at the age difference between himself and Monica.
What he also knew was that he did respect, and was emotionally a little scared of, women who had, “Do as I say or else,“ tones of voice; and Monica certainly had one of those. It was very similar to Miss Watson’s voice, the teacher he thought about so often who spanked him when at college. Both before and after that he had had a schoolboy crush on her and was worried about the same thing happening with Monica. He would certainly have relished an affair with her, but he was concerned that she would not want an affair with someone of his age. Mind you, as she had now told him that she had spanked both her younger brother and her dad, maybe that was the route through for them, with her in charge of him when here to do the cleaning?
As Jeff lowered his weight onto Monica’s lap he realised that his erection was pressing down on her bare thighs. He had to admit that he did like the feeling but hopefully wouldn’t cum whilst he was across her lap. Once the whole of his weight was lowered onto her thighs, and his hands were resting on the floor, he also liked the upside-down view he had of Monica’s bare legs. He looked up and saw the underside of her thighs as well and had an immediate desire to kiss them. However, all of that stopped when he felt Monica’s hand rubbing his bottom in circles.
Monica enjoyed watching Jeff lower himself across her lap, and, in particular, the feel of his stiff penis pressing down onto her thighs. She loved to give her boyfriends blowjobs, and so enjoyed the feel of an erect penis in her mouth, as well as the taste of her boyfriend's cum filling her mouth. Of course, she also enjoyed her boyfriends giving her tongue sex and was always complimented on the taste of her own sex juice. She could even feel flutters flying around her vagina as she rubbed Jeff’s bottom, and knew that she was getting more and more aroused by the prospect of giving him a spanking.
Monica put all of those thoughts to the back of her mind as she focused on Jeff’s bottom and was now more concerned about giving him an effective spanking. She did have to face the fact that she had never actually spanked anyone but had promised Jeff a hard spanking. Therefore, pursing her lips, she raised her hand and brought her flat palm down as hard as she could on Jeff’s far bottom cheek.
She did like the way that his cheek surrendered to her hand and then bounced back and wobbled around, although she didn’t stop and immediately landed another spank on Jeff’s near bottom cheek. Having watched the same reaction as from the first spank, she then proceeded to land spank after spank on alternate bottom cheeks, enjoying how they surrendered to her hand, wobbled afterwards, and turned darker and darker shades of red.
Monica was concerned that Jeff was just lying across her lap and not seeming to react even though she thought she was spanking him very hard. Her first thought was that she still wasn’t spanking him hard enough, and so she landed harder and harder spanks. She did get the occasional gasp, which encouraged her, but she found that her hand was starting to sting and wondered how much longer she could continue to spank him.
However, she was surprised, but also delighted, to find that as she continued to spank his bottom and turn it darker and darker shades of red, her hand seemed to sting less. She wondered if that was because her hand was becoming immune to the stinging, or just that she was coping better than she thought. Nevertheless, she now happily continued to spank Jeff on alternate bottom cheeks.
Monica did remember from watching one of her friends being spanked that her mum started to spank the same bottom cheek time and again for a while. That seemed to cause her friend greater and greater stress. So, using that memory, which was less than a year ago as her friend was eighteen years old at the time, she proceeded to land several spanks in a row on Jeff‘s far bottom cheek and, for the first time, saw that he was starting to squirm around on her lap.
After about a dozen spanks she then changed cheeks and landed a further dozen spanks on his near bottom cheek and, once again, Jeff continued to squirm around on her lap and even seemed to tense his legs and arms. She now reckoned that she was actually having more of an effect on Jeff than she had thought.
Jeff loved the fact that Monica was spanking him, having reconciled both her age and the fact it was his long-held fantasy. So, as the spanks continued, he looked at the back of Monica’s legs and saw that her muscles tensed and, in his mind, became even more kissable. He didn’t think the spanks were particularly hard, though, but put that down to the fact that Monica was just nineteen years old and maybe didn’t have the strength of an adult. However, once the spanks started to land time and again on the same bottom cheek, he realised that probably wasn’t true, and the successive spanks on the same bottom cheek meant the spanking was more intense.
He was certainly struggling a bit more as he was finding it increasingly painful. However, it wasn’t so painful that he wanted Monica to stop, and was more and more enjoying his submissive role with a woman who was well under half his age.
Once Monica had turned Jeff’s bottom cheeks a nice deep red, she then remembered what the mum of her friend did, which was to spank the backs of her legs. She only spanked them a few times, but, after each spank, her friend let out a wail that told her that those spanks were more painful than when her mum spanked her bottom. Therefore, she proceeded to spank the backs of Jeff’s legs alternately and saw that he was squirming around more than he did when she was spanking his bottom. He was definitely tensing his legs and letting out a gasp which told her that he was certainly struggling more with these spanks then when she spanked his bottom, just as her friend had done.