Jack loved to ogle forty-eight-year-old Jean Sinclair who lived two doors away. Jack was eighteen-years-old and had this fantasy about going out with a yummy mummy and Jean was the right age for Jack.
He was not sure why he fancied a woman Jean Sinclair’s age but thought it might have been because his own mother had not been particularly maternal and failed to guide him properly, and he was looking for someone to give him the experience of what he had missed.
Jack would bump into Jean whenever he could, and, with a smile, try to engage her in conversation. He wasn’t sure why, but Jean generally gave very short answers and moved on pretty much as quickly as she could.
It had happened quite by chance that Jack was at the pub with his mates, and saw that Jean was there with her friends. Jack caught Jean’s eye and smiled, and was thinking of going over and speaking with her. However, Jean gave a very forced smile and quickly looked away and started chatting to one of her friends.
Partway through the evening, Jack got up and went to the men’s toilet. He was more than a little disappointed that Jean didn’t give him any encouragement to be friendly. When Jack walked back out of the men’s toilet and was about to make his way back to his friends, a woman going towards the ladies toilet bumped into him. Jack saw that the woman was, in fact, one of the friends sitting with Jean. He blushed and said, “Sorry.”
The lady friend of Jean smiled at Jack and said, “No problem, Jack.” After a moment she added, “I’m Lesley by the way.”
Jack looked surprised that Lesley knew his name.
Lesley saw the look of surprise on Jack’s face and informed him, “Jean has been telling us all about you. She says how you want to be friendly and are always trying to chat her up. The thing is though, Jean is a lesbo and you are a bloke, so the two don’t exactly match, do they?”
Jack blushed at the explanation and hadn’t even thought Jean was a lesbian.
Lesley seemed to be enjoying Jack’s discomfort, and continued, “I don’t mind being friends with young men your age, though. Do you fancy a fling with me, Jack?“
Jack looked more closely at Lesley in her sleeveless floral dress with a hem halfway down her thighs. He liked her friendly maternal smile, the low cut dress that showed off her full breasts but not in an, ‘in your face way,’ her reasonably well-toned arms, slight tummy, and slim-ish legs.
He liked her haughty tone of voice as well, and, all in all, reckoned that Lesley could well be the maternal chummy mummy that he was looking for, and so replied, “That sounds like it would be fun.”
Lesley invited Jack to hers for dinner the following day. “We do need to set out the ground rules, Jack, but let’s not spoil this evening.”
Jack agreed, and they both went and sat back with their own friends and looked forward to seeing each other again.
The following evening Jack arrived at Lesley’s and they sat at the table and chatted for a while, discussing what they had done that day.
Lesley was again wearing a sleeveless dress and had bare legs. She looked sexy but maternal at the same time to Jack. Jack wore light blue denims and a short-sleeved shirt, and Lesley thought he looked a typical teenager. They sat and chatted for a while, and Jack was all ears and still liked Lesley’s authoritative tone of voice.
After a while, Lesley started to set out how she saw what should happen. “I think we both want the same thing. Jack,” she said as a statement rather than a question, which made Jack smirk. Lesley continued, “Although we will be girlfriend and boyfriend, it will be on the basis of chummy mummy and chummy son. That means you can state your opinion but not aggressively. If I put my finger to my lips it means the discussion is over and I will then make the decision which you cannot question. That way, you will be respecting my maternal authority. Is that agreed, Jack?”
Jack couldn’t see any reason to object, and, in fact, liked the idea. After all, his mum had wanted to discuss everything and try to reach an agreement rather than impose decisions. It tended to be more like she wanted to be his best friend rather than the person who should be guiding him. So, he happily agreed.” Sounds good to me.”
Lesley smiled and then said, “So, now we discuss consequences.” Lesley saw that Jack was still attentive as she continued, “Any arguments or dissent after I have made my decision will mean naughty spot time for you to consider your misbehaviour, and then you will get a bare bottom spanking.”
Lesley saw Jack swallow hard, but he stayed silent, so she continued. “I won’t be setting any rules or boundaries because it will be my decision every time. All you have to do is respect me and think carefully before you speak.”
Jack was so taken by Lesley. His own mum had never come close to spanking him, nor giving him timeout or taking away his electronics and the like, and he used to get away with so much. Many of his friends, on the other hand, often had to cancel going out because they were grounded.
Of course, that affected him as well, because he sometimes had to cancel because of that, but he always laughed at his friends as he was still free to go outside. So, although pretty sure he would be able to avoid being spanked, but otherwise wanting to be subjected to the maternal authority that Lesley was describing, he readily agreed. He asked with a smile, “Shall I call you, ‘mum,’ as well?”
Lesley took the question seriously. “I don’t mind if you do, Jack. After all, you could be the son that I never had. Of course, not getting married rather stymied my desire to have children. I always felt I had natural maternal instincts, but never got the chance to prove that. However, if you are up for it, and I believe that you are looking for a girlfriend with maternal instincts, then I’m certainly up for it as well.“
Jack swallowed hard as he listened to Lesley make her startling offer, but as it was something that he had dreamed of for so long, he happily jumped at the offer. “Yes please, mum.“
Lesley gave a loving smile and replied, “That’s settled then. I am your mum and you are my son.“
Dinner went extremely well, with Lesley asking about Jack’s lifestyle and then offering what Jack thought was good maternal advice. Indeed, it was the type of advice that he had never received to date and he became more and more enamoured by the role play.
After a few dates things settled down. Lesley and Jack kissed and cuddled and Jack had given Lesley finger sex a few times, and she had given Jack a few hand jobs. However, also, Lesley started to impose her maternal authority. One time, for instance, Jack had got into a bit of a state watching a football match and swore at the TV.
To calm him down, she ordered him to take a timeout standing in the corner. Jack accepted Lesley’s decision because he always felt discipline was something that he had missed out on. He wasn’t a natural submissive but he did enjoy it when Leslie snapped at him as though she really was his mum and he really was being naughty.
On another occasion, Leslie had smacked the back of Jack’s hand when he reached for a plate having been told by Lesley not to. That was extended to a light tap on the bottom when he didn’t react quickly enough to an instruction from Lesley to stop looking in a shop window and to come with her, and more so when she scolded him when in a restaurant when Jack spoke curtly to the waitress.
However, all in all, Jack found being disciplined in this way was something that he was growing readily to accept. So, as well as having a girlfriend he adored, Jack found the additional disciplinary maternal element exciting. He recalled several of his friends going out with girls who were haughty and took charge of their relationship but thought that with Lesley in charge of him that was even sexier.
It did become awkward the first time that Leslie and Jack were a couple and went to Jean’s for coffee. In fact, Jean had suggested it to Leslie so that there wouldn’t be any awkward moments in public. However, Jack was more tense than he had expected to be and, when one particular discussion became heated, he snapped at Jean.
Lesley immediately slapped Jack down by ordering, “I will not have you speaking to one of my friends like that, Jack. Time out. Go and face the wall and I will decide what punishment to give you.”
Jack tried a contrite, “I’m really sorry to have snapped at you, Jean.”
Lesley wasn’t having any of it and ordered, “You know that sorry doesn’t work until after your punishment. Now go and face the wall.”
Jack never really minded doing timeout with his nose pressed against the wall and, as always, found the maternal discipline something that he enjoyed. He did feel bad that he had snapped at Jean because of his long-held fancying of her, but then supposed it wasn’t unusual for parents to use timeout as a calming feature.
Jack was a little concerned that Lesley had made the point that she had yet to decide what his punishment was, and smiled to himself as he thought about the times that he had watched his friends siblings being spanked for doing much the same thing that he had just done. He reckoned that Lesley would give him a finger-wagging and scolding, and the warning not to argue with her friends anymore.
However, he was aware that Lesley had become increasingly strict with him, so he wasn’t absolutely sure, and she had threatened him with a spanking a few times now, but more as a threat not to misbehave rather than after he had done wrong in her eyes. Time would tell, of course, he told himself, as these various thoughts passed through his mind as he had nothing else to do with the blank wall at the end of his nose stopping him from seeing anything else.
Jack did get more concerned as he heard Lesley and Jean discussing, in rather upset and annoyed tones of voice, that Jack really did need to behave better with Lesley’s friends. By the end of the discussion, it had become clear Lesley had made her decision on what punishment to give Jack. It also became clear that Lesley was not going to be dealing with Jack in an adult way.
Lesley glared at Jack’s back as she berated him to Jean and knew it was time to give Jack a punishment more in line with his position as her chummy son and so a more severe punishment than usual. When she had made the decision, “Okay, Jack, come and stand in front of me.”
Jack turned to see Lesley pointing at the floor directly in front of her and he licked his lips as he stepped across the room and stood exactly where Lesley had ordered. He glanced at Jean who had a smirk on her face, pretty much as he had on his face when a friends sibling was being told off. He realised, though, that this was much worse for him than that.
Lesley scolded Jake, “I have warned you, Jack, that being rude is not nice but you don’t seem to listen to me. Jean is one of my closest friends and yet you have been rude to her in the way that you have answered her back. I, therefore, have no alternative but to deal with you like the naughty boy that you are. Therefore, take off your trousers and your underpants and get across my lap.”
Jack’s mouth dropped open with the realisation that he was going to be spanked. He wanted to argue that at his age he was far too old to be spanked. But, as he had agreed, and wanted to, he had to accept Lesley’s decisions, even when in such a strict maternal way, and he supposed that by being rude he was almost egging Lesley on to give him this long-feared punishment. He was also sure that if he argued then Lesley would most likely dump him as his girlfriend, which was something that he certainly didn’t want.