Sasha The Babysitter - Ch. 01

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Sasha babysits Jack when his wife is away, knowing he has to.
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Part 1 of the 2 part series

Updated 11/11/2023
Created 10/23/2023
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Peter242
Peter242
79 Followers

Sasha was very annoyed with Jack when he got home.

Sasha was eighteen and effectively babysitting Jack, who was thirty-seven. Jack was married to Laura and was one of those men who had no idea how to look after themselves at home. He was a workaholic and left everything in the home to his wife. He had no idea how to cook, nor operate the washing machine or iron, and literally could just about operate the central heating system.

Therefore, whenever Laura was away on business, as she was now for two weeks, Sasha came to act as a housekeeper but effectively the babysitter.

However, what Sasha found was that Jack was not the best at timekeeping. Today was the third time that she had made dinner, but Jack turned up an hour later than he was supposed to. Each time there was an excuse, and today's was that he went out for a drink with work colleagues and forgot the time.

Sasha was really fed up with this, and demanded, "Are you this bad at timekeeping with Laura?"

Jack swallowed hard and clearly didn't know exactly what to say, which Sasha took as an admission that he wasn't this bad with Laura.

Sasha then demanded, "So why do you think it's okay to be better at timekeeping with Laura when you are so bad with me? I know that I am being paid to babysit you, but surely you should be showing me an element of respect. So, I ask again, why do you keep better timekeeping with Laura than you do with me?"

Jack still didn't answer the question clearly and just said, "Well I suppose I do, Sasha. Sorry."

Sasha was still very annoyed and said, "If I'm not going to get an answer from you, I think I will phone Laura and tell her that I am really annoyed with you and ask what I should do about that"

As Sasha made the statement, she took out her phone and was already dialing Laura before Jack could really object.

In the event, Laura answered her phone almost immediately and asked what the problem was.

Sasha explained, "Today is the third time that Jack has come home late and his dinner has been spoilt. I really am frustrated about this, and as much as I want the job, I am finding it so frustrating."

Laura tried to calm Sasha down and said, "I know, he used to be like that with me, but we sorted that out. Would it help if I spoke to him and told him to be more thoughtful?"

Sasha asked, "Does just telling him work? Is that all you had to do to make him come home on time? After all, that's almost the only thing that he has to do because I do everything else."

Laura could tell that Sasha really was on the verge of resigning, and she certainly didn't want that.

Laura enjoyed her job but knew that she couldn't be away doing it if Jack didn't have anyone looking after him at home. She, therefore, made a very quick decision and explained, "Well, Sasha, it wasn't just telling him to be on time that made him do that."

Sasha's phone was on speaker and so Jack heard what Laura was saying and he intervened in a very worried tone, "Please, Laura, don't tell her. I'll do my best. Really I will."

Sasha could hear the panic in Jack's voice and was now certainly intrigued to know what Laura did to make him obey her. So, pressing Laura, she said, "I do need to know, Laura, because, quite frankly, if Jack is late just one more time, I won't just give you notice but I will literally walk out there and then."

Sasha was looking at Jack as she said it and saw the increasing panic on his face. It made it even more interesting for her to know what Laura did.

Laura also wanted to ensure that Jack got home on time in the future and took the threat that Sasha would leave the house immediately and therefore not even be there when she got home, very seriously. She, therefore, decided to tell Sasha what she did and simply said, " I understand, Sasha, and will therefore tell you what I did. Whenever he was late, I make him get totally undressed and put him across my lap, and give his bare bottom a very long and hard spanking with my hand and a wooden hairbrush. Even now I still do it from time to time, but his timekeeping really did improve."

Sasha was wide-eyed and, trying hard not to smile, was picturing Jack across Laura's lap having his bottom spanked. How cool was that? A man of thirty-seven being spanked by his wife was mind-blowing. She then thought to herself that if the wife spanked the husband, why not the babysitter giving him a spanking as well?

It was as though Laura was thinking the same because she announced, "Actually, Sasha, I can see how it would make sense if you had the right to spank Jack if he didn't get home reasonably within the time that he said that he would come home, or that you told him that he must."

Sasha replied immediately, "Absolutely." As she did, she was looking at Jack who was clearly even more horrified than before.

Sasha then reasoned with Laura, "If Jack knew that he would be spanked if he had been late for you, and he has been late for me three times, doesn't that mean that I should give him a spanking now and again whenever he is late in the future?"

Sasha heard Jack gasp and fully expected him to protest, but, before he could, Laura replied, "I think that is absolutely right." Laura added for Jack's benefit, "Jack, that has to be far better than losing Sasha altogether and will be your incentive to get home in a timely fashion going forward."

Sasha then saw Jack wince, but in a way that told her that he was not going to contest what Laura had said.

Laura must have realised that Jack was accepting her instructions because he wasn't objecting, and ordered, "Jack, you will follow every instruction given to you by Sasha, who will now give you a spanking. It will be on your bare bottom, and she will use both her hand and also the wooden hairbrush. If you object or resist or do anything at all to stop or impede her, I will have to come straight back home and give you a thrashing like never before. Is that understood?"

Sasha saw that Jack was conceding, and he replied, dolefully, "Yes, Laura. Sasha will give me a spanking, and I will not resist or impede her."

Laura then said to Sasha, "Just make sure you put him across your bare legs. Whilst Jack doesn't like being spanked, he does seem to get turned on and will leak his cum and we don't want him to stain your clothes."

Sasha was wearing what she often wore, which was a tight vest top with a bare midriff and cotton shorts. She was sure that Laura would have known that but maybe it was to humiliate Jack into submission, which looked like it worked. Sasha was looking at Jack as Laura was explaining this to her and could see his embarrassment and humiliation, and once again he wasn't objecting. She now began to wonder whether he was simply totally submissive, maybe only at home and not at the office, but either way, she was certainly going to enjoy herself giving him a thrashing.

Jack was still in his office clothes of a jacket, open-necked shirt, and trousers. Sasha smirked as she instructed, "Right, Jack, let's have you totally undressed"

Laura was now encouraging Sasha by saying, "Too right, Sasha, as naughty men should be spanked when fully undressed."

Again, Jack didn't argue and quickly slipped his jacket down his arms, caught it, and put it on a chair. He followed this with his shirt which he quickly slid down his arms. Then he undid his trousers and pushed them downwards, catching his underpants on the way, scooped them up, and put them with his other clothes. He then took each of his socks off. Finally, he was standing there fully naked and just automatically put his hands on his head, which again told Sasha that Jack was one very submissive and obedient husband and clearly Laura was an authoritative and dominant wife.

Well, Sasha told herself that she wanted to be much more like Laura than she wanted to be like Jack, and today she was going to be.

Sasha demanded, "Where are the hairbrushes, Jack?"

Jack was quite sheepish as he replied, "In the top drawer of the side cabinet." He pointed towards the cabinet in question.

Sasha thought about telling Jack to go and get the hairbrush but decided she wanted to see what else might be in the drawer. She went over, opened it, and smiled as she saw six wooden-backed hairbrushes which told her that Jack being thrashed by Laura was not something that only just started or happened so irregularly. As she picked up one of the hairbrushes, she saw quite a thick leather strap and supposed that that was also used. However, Laura had specifically mentioned the hairbrush and so Sasha decided to go with that.

As she closed the drawer, Sasha wondered whether she was being too submissive herself by simply doing as Laura was telling her. She had had fantasies in the past about being spanked and was worried that maybe Laura would judge she was also a sub if she did everything she was told to, but she decided to stay with the hairbrush and risk it.

Sasha then went to the dining table and turned a chair into the room and sat down. She put the hairbrush on the table behind her, turned and glared at Jack, and instructed, "Right, Jack, come here and get across my lap."

As she was saying it, she saw that Jack already had an erection which he couldn't cover because his

hands were still on top of his head. She just smiled herself, although also noticed that her knickers were now feeling damp, and rather hoped that was because she was getting excited at the thought of spanking Jack rather than the thought, which she was also still having strangely enough, of being spanked by Laura.

Jack did as he was told and walked across the room and stood by Sasha and only then lowered his hands from his head. He eased himself down across her lap, ending up with his hands on the floor and his feet dangling on the other side of the chair, with his bottom perfectly positioned for Sasha to spank him.

Sasha found it exciting that Jack was so obviously turned on by the experience of going across her lap given that his erection was ever so stiff by the time he lowered himself across her lap.

Sasha then said to the back of Jack's head although intending it to be heard by Laura, "Right then, Jack, you make sure you don't move off my lap until I have finished spanking you. I hope that is understood."

Jack immediately responded, "Yes, Miss Sasha, I understand."

Sasha took the ever so respectful way that Jack was calling her as further proof that he was submissive and was going to be obedient. She rubbed Jack's bottom a few times, raised her hand, and then brought it down as hard as she could on Jack's far bottom cheek. She loved the way that his bottom cheek surrendered to her hand, swirled around a bit, and settled down just as she spanked his other bottom cheek. She then proceeded to spank alternate bottom cheeks time and again, happily turning both bottom cheeks darker and darker shades of red.

The spanking continued and Sasha felt that she was managing to spank Jack's bottom cheeks harder and harder as she watched him squirm around on her lap which was confirmation of his reaction that this wasn't just something he could easily cope with. Sasha supposed that Laura would spank even harder than her given her age, compared to her own, but then said even teenage girls like herself could give a good thrashing, and felt she was doing so.

As Sasha continued to spank Jack, she started to hear his gasps of pain which told her that his bottom must be stinging, so she was giving him a good hard spanking after all and felt really pleased with herself at that.

It turned out that Laura had stayed on the phone and was listening to the spanking, and started to encourage Sasha by saying, "Keep going with your hand until he sobs, Sasha. Then use the hairbrush because that is when the real punishment starts."

Sasha kept on spanking Jack as she registered the comment and could see how that made sense. She had always understood that a spanking shouldn't just last until the person being spanked started to cry, but should keep going until they were crying uncontrollably, and then some more. It was then she realised that that was exactly how she had imagined herself being spanked so often as she lay in bed fingering herself, but then she told herself this was far more exciting than that.

Laura then said, "Don't forget his legs, Sasha. You only spank them with your hand, but he will struggle more than you would expect."

Sasha followed Laura's advice and started to spank the back of each leg, turning them redder and redder, and she heard Jack let out louder and louder gasps.

Once Sasha heard Jack sobbing and saw that he wasn't squirming around on her lap so much and so he was just conceding to her authority over him, so she turned and picked up the hairbrush, turned back, and then started to thrash his bottom with the wooden-backed hairbrush. She immediately heard the gasps getting louder and louder and could see him tensing his legs and even his arms as he was clearly struggling yet staying obediently in position across her lap. In fact, he was being totally obedient and submissive, just as she imagined she would have to be when being spanked for fear of the spanking taking longer and being harder as the penalty for disobedience.

Sasha assumed that Jack was so obedient because Laura had taught him to be, and if that was the case then she certainly was a good teacher. So, knowing this was about teaching Jack a lesson, she continued to thrash him really hard with the hairbrush even though he had been crying uncontrollably for quite some time.

Eventually, though, Sasha reluctantly decided that she had spanked Jack long and hard enough to teach him to be on time in future for her. So, she stopped spanking him but left him there across her lap still crying, and again she congratulated herself on giving such a hard spanking.

However, as she looked down on Jack, she wondered again what it must be like to be spanked like he had been spanked. After all, a man his age had to be cooperative to accept being thrashed by his wife, and probably even more so to follow her instructions to be thrashed by his babysitter. That's when she thought once again about all the times she lay in bed fingering herself to a huge orgasm imagining herself being spanked by a woman who she may have seen on the bus or train but was now already picturing herself across Laura's lap.

Sasha put those thoughts to one side as she saw that Jack was recovering, and so instructed, "Okay, Jack, you can get up now. However, stand in front of me with your hands on your head so we can discuss what will earn you another spanking."

Jack eased himself off Sasha's lap and obediently stood looking down at her with his hands on his head. He did admit to himself, albeit silently, how he relished being obedient and submissive to authoritative women, and while so far the only woman to have spanked him, before today, was Laura, he could see that Sasha was just as capable of giving him a really hard thrashing.

Once Jack was standing facing her with his hands on his head, Sasha glanced at his penis and saw that even now he was getting an erection back. Was this so unusual, she now asked herself? After all, she knew that just as there were those who enjoyed giving a spanking or the cane or the like, there were those who enjoyed submitting and receiving it. She knew that she had enjoyed spanking Jack, but still couldn't get it out of her head whether she would enjoy being spanked by Laura, more or less than spanking Jack.

Sasha again put those thoughts to one side as she glared at Jack and said, "You now understand, Jack, that if you are late for dinner again you will be spanked just as hard and maybe even harder each and every time. Understood?"

Jack was sniffing back tears as he replied, "Yes, Miss Sasha, I fully understand. I am so sorry for being late all these times and I will make sure that I am on time every time in future."

As Jack said it, Sasha supposed that she was hoping that Jack would be late again, although maybe she could introduce other reasons for spanking him. Maybe she would discuss those with Laura at another time.

As though reading her thoughts again, Laura was still on the phone and said, "Sasha, you have my full

authority to spank Jack for any reason that he disobeys you. By that, I mean he has to do what you say immediately, or else you can tell him to get undressed and give him another thrashing. We don't even have to get Jack to agree to that, because he knows he has no choice."

Sasha glanced at Jack and saw that he was looking at the floor, clearly totally submissive and giving no objection whatsoever.

As it turned out, Sasha spanked Jack four more times before Laura came back, and on each occasion Jack did cry uncontrollably, kept addressing her as Miss Sasha, even thanking her once he had calmed back down after the spanking. Sasha noticed that it even did him some good because he was always happy and friendly as soon as he had calmed down from each spanking, although clearly his bottom was still stinging judging from the way he grimaced as he sat down on anything other than a thick cushion. It didn't stop Sasha from spanking him, and in fact encouraged her to do so, and it was as though she was giving Jack a reset each time.

When Laura came back, she, first of all, glared at Jack and then looked at Sasha and said, " I am sorry that you had to spank Jack so often, but I am pleased that you did and that you spanked him so well."

Sasha smiled and replied, "That's okay, Laura. I can see how spanking Jack actually did him a lot of good."

Laura smiled back and asked, "I hope that means that she will babysit Jack again."

Sasha was still smiling as she replied, "Of course I will, Laura."

Sasha knew that she would certainly babysit Jack in future, but still couldn't get out of her mind what it might be like to be subject to being spanked by Laura. Maybe she would find out in the future, she mused.

Peter242
Peter242
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AnonymousAnonymous6 months ago

After "Headmistress", great start for a new story.

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