Jack was upset with himself as he walked in from college. He was sixteen years old and had got his first-ever detention. He knew that would get him grounded for three days which would mean he would miss two football games and a party he was looking forward to going to. As he was one house away from his own, Olivia, their neighbour, called out to him, “Hey, Jack, hold on a minute.”
Olivia was twenty-eight years old and lived alone. She was friendly with his parents, and Jack found himself daydreaming about her quite a lot because she always dressed in such sexually skimpy clothes whilst at the same time having rather a haughty voice.
She came down the path and was smiling as she said, “Your mum had to go out so she asked me if I could take you in and give you your tea here and she brought me your PJs and a change of clothes so you could sleepover as well. She won’t be back until tomorrow afternoon, but before you get back from college.”
Jack rather liked the idea and happily followed Olivia up the path. Once inside Olivia led Jack into the dining room where he saw she had already laid out biscuits and his favourite sandwiches, and when she asked him, “What do you want to drink?”
He replied, “Orange juice would be great.”
As they sat down and chatted, Olivia made the point, “You are back later than I expected, Jack, and I was a bit worried.”
Jack replied, blushing, “I got a detention so had to stay behind at school. The problem is I’m going to be grounded for three days.” He looked tentatively at Olivia and asked, “Any chance you might not tell that I was late coming back?”
Olivia replied, “I have to say I’m not so happy about lying. Anyway, when I got a detention, I would get a spanking when I got home, which hurt, of course, but was over and done with and still a very good lesson.”
Jack could see that Olivia was smiling as he told him, and he had in the past thought that a spanking would be an easier punishment to deal with than being grounded, which Olivia confirmed. He bit his lip as he glanced at Olivia‘s so sexy bare arms and wondered how hard she would spank him.
~~~
Olivia could see that Jack was thinking and reckoned it was about whether to ask her to spank him. She had only said it as a joke as she knew that he fancied her from the way that he had looked at her in the past and made flippant comments to her so had thought it would be fun to tease him for a change.
She had fantasied for a long time about spanking a young man but didn’t think Jack would come close to asking for a spanking, but because of his body language she pressed Jack and asked, “I guess if I gave you a spanking then you would at least be punished, and I wouldn’t feel so bad about not telling.”
Jack was taken by surprise by the offer and could feel that he was actually getting an erection, although didn’t understand why because he was pretty sure that a spanking would really hurt. Maybe it was the thought of being spanked by his fantasy girlfriend, though, and as he had that thought his erection got even stiffer.
Olivia could see how Jack was thinking about what she had said, maybe even seriously, so she then pressed with, “Please don’t put me in a difficult position, Jack, as I will have to tell on you that you had a detention unless I discipline you myself.” She was still going to be surprised if he fell for it.
Jack knew that Olivia had made it pretty clear what she meant by disciplining him but still supposed that a spanking was better than being grounded, particularly over the next three days, and it really wouldn’t make so much difference that it was Olivia who was going to spank him. So, blushing, he asked, “Would you be spanking me just with your hand, Olivia?”
Olivia was still surprised when Jack asked the question, but kept a stern look on her face as she said, “It will certainly start with my hand, but I will also be using a wooden-backed paddle hairbrush just to make sure it was an effective punishment.”
Jack swallowed hard as he was pretty sure that a hairbrush would really hurt, and certainly much more than Olivia‘s hand, but still reckoned that he was left with very little choice. After all, he was staying the night and so would have time to recover and that would also hide the fact he had been spanked. So, he quickly came to a decision and replied, “Okay, Olivia, as I had a detention, please will you discipline me.”
Olivia didn’t want to give Jack any time to reconsider and so ordered, “Right, Jack, follow me and stand by the dining chair and take your trousers and underpants off.”
Olivia led Jack towards the dining table, and she turned a chair into the room, sat down, and eased her already short dress up her legs leaving her thighs bare, thinking it would be cool to have Jack’s penis flattened onto her thighs.
However, when Jack had stepped out of his trousers and underpants, she saw his erection and knew he could easily ejaculate over her thighs and onto the carpet, so she ordered, “Go to the kitchen and get three pieces of kitchen roll and come back here straight away.”
Jack saw why he was being told that and as he went towards the kitchen, he was sure she would tell him to jerk off into the kitchen roll. He didn’t mind as he didn’t want to spray his stuff onto the carpet anyway, so, as he walked back into the living room with three pieces of kitchen roll he was not surprised when he heard the order, “Now jerk off into it.”
Luckily for Jack, this wasn’t something that was so unusual to him, albeit more often than not he masturbated in bed and his pyjama bottoms were where his cum ended up. He wasn’t used to doing it in front of anyone else, and especially not a woman who was about to spank him, but he focused as he clasped hold of his erection and squeezed and rubbed his penis, but he was relieved as his cum squirted into the toilet roll.
Olivia hadn’t watched anyone jerk off in front of her before although she was quite happy to take a man’s cum into her mouth, but she did enjoy watching Jack, grimacing under pressure, and she could see he was embarrassed. However, it was done, and she nodded towards the kitchen. Jack rolled up the paper and took it back into the kitchen and put it in the bin before returning to the living room and saw Olivia point to her lap.
As Jack walked across to Olivia, he thought again how he found her so attractive and had fantasied about going on a date with her. He never thought it could happen, but he always pictured her in a slinky sleeveless low-cut dress and with bare legs, and what she was wearing was close enough to that, although of course what she was about to do to him wasn’t. He had also always imagined them kissing and cuddling, with him sucking her breasts and her taking his penis into her mouth. He hoped that some of that might still happen but doubted it.
Olivia kept a stern look on her face as she watched Jack come over and stand by her, look down at her lap, and of course her cleavage, and then eased himself downwards until his full weight was resting across her thighs. She saw that even though he had just jerked off he already had the signs of another erection, but she was pretty sure that that would go well before the end of the spanking.
Jack eased himself down across Olivia’s lap and had to admit to liking the close-up view he had of her painted toenails and upside-down legs
Olivia made a threat, saying “Jack, if you get up partway through then all bets are off and I will have to tell about your detention. Understood?”
Jack thought that was fair and replied to the floor, “Yes, Olivia, I do.”
Olivia then happily placed her palm on Jack’s bare bottom and rubbed in circles, thinking that whilst she had never spanked anyone herself before, she had a fair idea what to do as she had watched a few spanking videos on her computer. After a few more rubs, enjoying the feel of his bare skin and even rubbing her hand a few times up and down the backs of his thighs, Olivia raised her hand and brought her palm down really hard on Jack’s far bottom cheek, and as she watched it flattening and bounce back up, so she happily brought her palm down just as hard on Jack’s other bottom cheek.
She then proceeded to spank Jack on alternate bottom cheeks, fully intending to do so for several minutes because she had to admit to herself that she had quite a thing about giving someone a spanking, playing out in her mind that it was going to be a naughty young man, and so, what better than the fact that she had that naughty young man across her lap right now.
Jack wasn’t expecting the spanking to hurt quite so much but soon realised that the stinging pain was intensifying as the spanks continued to land without any gaps to speak of. He had watched as one friend was spanked by his teacher just last week at the front of the class, but in comparison that was literally playing, and wasn’t on his bare bottom either.
Now he realised it was more of a scolding that the teacher had given rather than a spanking. Still, he supposed that he still had to thank Olivia for spanking him rather than telling on that that he had got the detention. However, as the stinging intensified even more, he supposed that the thank you would be represented by the tears that were soon bound to flow down his face.
As Olivia continued spanking Jack, she really was enthralled by the way that he was staying obediently across her lap when he certainly had the strength to force himself up. Of course, every punishment was an incentive of some kind, and she had given the incentive here to keep the spanking between her and him, without the need to tell on him. So, as she intensified the spanking by landing several spanks in a row on the same bottom cheek and then several spanks in a row on the other bottom cheek, she knew she was experiencing what she wanted to by giving a spanking, which was every bit as great as she thought it would be and knew that her pussy was already so wet.
Jack hadn’t expected to struggle quite so much as he was but with his increasingly stinging bottom, and then the same happening to the backs of his legs, he found it harder and harder to cope and even knew that he was going to have the embarrassment of crying. How could a man cry when a woman spanked him, he asked himself, but there was no doubt that his eyes were filling with tears because everything around him was now blurred including Olivia’s sexy upside-down bare legs.
Of course, he kept in mind Olivia’s threat that if he got up at any time during the spanking then the deal was off, so he knew he had no choice but to stay where he was and accept spank after spank for as long as Olivia decided to spank him. Mind you, what wasn’t so expected was that he started to like the idea of submitting to a woman like Olivia, maybe not to be spanked again but to be under her authoritative control and to be spoken down to, which seemed to be such a turn-on. That soon changed to him accepting that actually being spanked would be a good incentive for him to behave better if under Olivia’s control.
Olivia could see how Jack was struggling, but even so, she turned and picked up the hairbrush that she had placed on the table, tapped it on his bottom a couple of times, and then started to spank him really hard with it. She could see how he was struggling even more, but how his bottom flattened under the hairbrush so much more effectively than when she spanked with her hand, so that made sense. Still, what she knew was that if she gave Jack a hard spanking that he couldn’t cope with, firstly that was much more effective than being grounded, and secondly, it was a short albeit very painful lesson, but one which was at least over for her so quickly and it was Jack who would have to suffer from this stinging bottom.
Olivia also smiled as she realised that her hand didn’t hurt either when using the hairbrush which was another plus for her.
Jack yelped as each spank with the hairbrush landed, and still, he knew he had to stay there because it really wasn’t worth getting up now if the whole of the spanking so far was going to be for nothing. Mind you, he was likely to be staying with Olivia again because he wasn’t trusted to be in the house by himself given some of the experiences he had had already, what with nearly setting the house on fire, and general irresponsibility.
That was why Olivia was asked if she could look after Jack today and overnight, and so Jack saw every likelihood of it being repeated. Of course, if it was, then there was every likelihood that this exact punishment would be repeated. However, his thinking ended there as he dissolved into crying because of the pain, and still, the spanks continued to land.
Olivia felt really good being in control, and it had satisfied so many desires that she had had to do just this. She had even daydreamed about spanking Jack in the recent past because he had made some particularly flippant comments to her which he thought were funny, but she knew were humiliating. Whilst today she had threatened to spank Jack, it was to make him feel uncomfortable rather than actually spank him, but it was all too easy to get him across her lap and to make him stay there.
Therefore, she knew that she would be able to do this again and would definitely be offering to look after him and let him sleep overnight with the intent of doing this again. That would teach him not to be so flippant with her, she reckoned. Anyway, it would be fun for her as well.
Eventually, Olivia knew she had spanked Jack for long enough and put the hairbrush down but left Jack across her lap as he continued to cry. She also knew her pussy was so wet and that she would have to deal with that and give herself what she knew would be huge orgasms.
Once Jack had calmed down, she ordered, “Okay, Jack, your spanking is over and so I won’t be telling on you. Better get up, now, and go and wash your face and then come back down.”
Jack did as he was told and as he stood up he clutched his stinging bottom and stepped from foot to foot. That was when Olivia saw his erection return and so was pretty sure he would jerk himself off again when he got to the bathroom. She didn’t say anything but hoped he would remember to jerk off into some toilet paper. On the other hand, she now intended doing herself when Jack was upstairs, and so be sorted by the time he got back downstairs. That would work for both of them, she reckoned, and it made it even more certain that she would find a reason to spank Jack again.
