It was a beautiful Saturday morning. Tim was still in bed, rubbing his sore bottom. The night before, he had again a painful but very rewarding encounter with Emma, a meeting that included a wooden-backed hairbrush and a senior cane. When his bottom was sore, Tim enjoyed squeezing it or sitting on hard surfaces to feel the pain. It was a sensation he found stimulating and helped him remember and relive the spanking he had received, which turned him on. That day was one of those days when he had a very sore bottom and was enjoying that feeling.

Diane had been away for almost a month to visit her mother, but would be back in six days. Before she left, at Tim's request, she used to put him over her knees and spank him with her palm and hairbrush about once a week. They both appreciated the connection that spanking gave them. Tim needed to be spanked regularly, and Diane loved being in control over someone, so they really enjoyed their weekly routine. Last night, he got the last spanking from Emma before Diane's return.

When he finally decided to go downstairs to the living room, Emma had already been there for a long time. She'd even half-finished her coffee. She greeted him with a warm smile and said, "Good morning, sleepyhead. Are you all right? I thought something had happened to you."

"Good morning, sis. I'm fine; I just overslept."

"How do you feel after last night?"

"Sore…"

"That's an understatement," Emma interrupted him.

"Happy, satisfied, and euphoric. Should I continue?" Tim asked, smiling.

"No, no, I think I get the idea. You took a hell of a spanking last night."

"And a hell of a caning. Have I told you before that you're getting better and better at handling the cane?"

"Let's just say I've been practicing a little bit lately," Emma said, smiling, then added, "Speaking of the cane, I hope you didn't get mad that I raised the rate last night."

"Do I look mad to you?" Tim replied, smiling.

"The thing is, I was probably a bit selfish in deciding to give you eighteen strokes instead of twelve as it was before. Mom's coming back in a few days, and I probably won't get a chance to spank or cane you anytime soon. And I decided to take advantage of it a little more."

"Hey, you don’t have to feel bad about it. You are in charge, and you get to decide how hard and long my spanking should be or how many cane strokes I should receive. I just have to obey and accept everything you throw at me. That's my role as a submissive. Besides, I never took the twelve strokes for granted. I always waited for you to tell me how many there would be, and I always expected that one day that number would change. Yes, last night's caning was more severe, and I struggled harder to deal with it, but at the same time, it made me feel even more helpless, and you seemed even more dominant, so it was worth it. I was in my happy place and enjoyed the intense feeling of submission."

"Thank you, you are the best. I'm so sad that we won't have our usual evening meetings in my room. I can’t describe to you how much I enjoyed them."

"I know, I’m sad too, but unfortunately, I have only one bottom and I need time to heal between spankings, and you know how into it Diane is. I bet she can’t wait to get home and put me over her knee. But our sessions were really fun, and I hope we get the chance to do it again from time to time."

"By the way, did you tell her I spanked you?"

"No, we hadn't discussed it between us, and I decided to stay out of it, not knowing if you wanted her to know or not. You didn't tell her either, I assume."

"No. But I don’t have a problem telling her."

"Me neither. I’ll tell her when she comes back home," Tim replied.

"Just so you know, before she left, she encouraged me to try to get you to agree to let me spank you."

Tim laughed and reported, "What a coincidence, and she suggested to me that you would be the best alternative while she's gone. So surely she'll be glad her plan succeeded."

"What about the cane? Do you want to tell her about it, or should it remain our little secret?" Emma asked.

"Why should it remain our secret? I'd like to tell her."

"Well, she may also want to use it if you tell her about it."

"I hope she will," Tim said, smiling.

"You're really into the cane, aren't you?"

"I enjoy being caned. Well, maybe 'enjoy' isn’t the right word because it hurts like hell. But it makes the spanking more meaningful and helps me feel more submissive and out of control. It helps by enhancing all those feelings that make me happy and fulfilled. So if I reflect on it, yes, we can say I enjoy being caned. And if Diane decides to use it on me, she may need a practical demonstration and someone to teach her how to do it properly, so maybe you get to cane me again sooner than you expected."

Emma cheered up at Tim's words and said, "I really hope so."

The days that followed were quiet and uneventful. Tim's bottom wasn't sore anymore, but it probably wasn't going to stay that way for long because Diane was just about to return from visiting her mother, and she was certainly eager to put him over her knee again and blister his bottom. Frankly, he was waiting for that moment too. He didn't lack the spankings while she was gone because Emma took care of them, but he wanted to be again under her authority and to be spanked by her. They had a great connection because of it, and he was waiting to reestablish it.

Tim was in the living room when Diane walked through the door.

"Hi, honey. I'm home."

"Ow, hi. Welcome back," Tim replied as he went to give her a hug.

"I’m so glad to be back home. I’ve missed you. Where is Emma?"

"She went out for a bit, but she should return soon."

"Would you like to help me unpack and, in the meantime, tell me what happened here while I was away?"

"Sure."

They started unpacking, and after a few general questions about how the two had managed in Diana's absence, the topic of discussion shifted to spanking. Tim was expecting it and was actually surprised that it took Diana so long to bring it up.

She asked, "So, tell me, Tim, how did you manage to resist without our spanking routine? Did you spank yourself often?"

"Just once," Tim said, without giving any other details.

Diane looked very surprised at him and asked, "How so? Only once in a full month? But what happened?"

"Emma spanked me," Tim replied, again without giving further details. He liked this game.

"Don't make me pick the words out of your mouth. Come on, tell me all about it. How did it happen?"

"After you left, for a few days it was quiet, then I felt the urge to spank myself, and one day when Emma wasn't home, I used the hairbrush. What I didn't know was that Emma had put it in a certain position, and when I put it back, I didn't take that into account, so she noticed it had been moved and confronted me. Then we had a discussion where she brought up a lot of arguments about why I should let her spank me, so I agreed."

"Wow, smart girl. And how did she handle it?"

"She's a natural. She's been very dominant and confident all the time, and I can tell she knows how to deliver a very hard spanking, just like you. I guess she had a good teacher," Tim replied, smiling.

"And what happened next? You started asking her to spank you?"

"Yes, but next time she actually caned me."

"Wait, what?" Diane asked, looking shocked.

"Yes. She wanted it, and she convinced me to try it. Again, she used her best arguments, and you know how convincing she can be. So I accepted. Plus, I thought, as a spanko, I should try it once in my life to see what it's like."

"It seems very painful."

"I'll just say that experience took the pain to a whole new level."

"Go on. I feel this story is not over yet."

"After that, we had a chat, and we decided that I should be caned again in the future."

"Wait. You mean after that experience, she convinced you to go through it again?"

"No. Actually, I pretty much convinced myself. Despite the fact that it hurts a lot, it helps me in many ways. It makes spanking more authentic; it helps me feel more submissive because I have to work harder to endure the pain; and it gives more authority to the one wielding the cane. It helps me get to my happy place more easily, and overall, I enjoy the experience more. Albeit at the moment, I hate it because of the pain."

"So from what I understand, you've basically replaced spanking with caning?"

"No. No. First, I'd go over her knee, and she'd spank me with her hand and hairbrush, then I would bend over the desk and receive a caning."

"Wow, it seems so harsh."

"Yes, trust me, it is, but I enjoy being spanked and caned like that. Well, I hate the actual pain, but as I said before, it has so many benefits, and I’m happier and fulfilled."

"So basically, you're now suggesting that I should introduce the cane into our routine?"

"I would love that."

"I've never seen anything like this, and I haven't watched it in a movie either, but I'm very curious. I hope you're sure you want this because I might like it and then not want to give it up."

"I’m sure, and I hope you’ll like it. And I bet Emma is eager to show it to you and give a practical demonstration."

"I'm glad Emma took care of your needs, and it sounds like she did an excellent job. I have to admit I'm a little disappointed, though. I expected to find you eager for a trip over my knee and with the chair and hairbrush already in place, but instead, you've been taking your medicine on a regular basis, and you don't need me like you used to."

"No, that's not true. I look forward to resuming our regular meetings," Tim said, blushing slightly, then added, "I just assumed you'd be tired from the road."

"I’m never too tired for this," she interrupted him in a determined tone.

"Then let me correct that," Tim said as he got up and went to get a chair and put it in the middle of the room, then walked over to where the hairbrush was, picked it up, and placed it on the chair.

Diane cheered when she saw all the movement. She was really looking forward to spanking Tim.

"Better now?" Tim asked with a smile.

"Yeah, it's clearly better, but I still think I should give you some extras for your mistake. Plus, we've got a lot of catching up to do."

Tim felt a wave of fear and excitement through his whole body and responded submissively, "You're probably right."

"Of course I'm right. Tell me, when do you suggest we do it?"

"I've made plans with friends, and I should probably go, but if you want now, I can tell them I'll be late. If not, we could do it tonight."

"Tonight sounds good," decided Diane, then added, "And maybe by then I can learn more about the cane, and maybe I'll even use it on you."

Tim felt a shiver down his spine, thinking about being caned by Diane. It was going to be an extremely painful experience, but he was looking forward to submitting to her.

"Thank you! I'm off now. See you soon."

"Have fun, honey," Diane said, watching Tim walk out the door.

Shortly after Tim left, Emma returned home, and the two women enjoyed seeing each other again. They chatted for a while about Diane's trip and how things had gone in her absence, and then Emma's eyes fell on the chair in the middle of the room. She exclaimed, "Already, Mom?"

"Yes, honey. Are you surprised? Tim thought I was too tired, but I convinced him not to spare me. And I'm certainly not going to go easy on him either. Speaking of which, Tim told me about the spanking you gave him in my absence, and he also mentioned the caning. He wants me to use it on him in the future, and I think you could help me with that."

"Oh, yes, of course I can help you. I'll go get it, and then I'll teach you how to use it in no time. I'm sure you'll love it," Emma answered enthusiastically.

Emma quickly went up to her room and returned with the cane. At first, Diane was surprised at how light it seemed and found it a much less frightening implement than she imagined, but after hitting her palm with it and feeling how hard it stung even after a light stroke, she understood that it was the real deal.

Emma then put a pillow on the back of the chair already placed in the middle of the room and began to show her how to hit and how to position herself to evenly hit both cheeks and avoid the tip bending over the hip. She then showed her how hard she should hit, and Diane took the cane and started practicing.

She spent a lot of time practicing on the pillow, becoming more and more confident. Emma kept an eye on her and gave her a few pointers from time to time. Diane was already looking forward to having Tim's bottom as a target for the cane. Wielding the cane gave her a sense of superiority and control, which aroused her more and more.

During that time, Tim was having fun with his friends. He was a little tense but managed to keep it under wraps. He kept thinking about the upcoming spanking and wondered if it would be followed by a caning. He realized that not knowing made him feel even more vulnerable and out of control, which increased his submissiveness. On the way home, he was thinking about what was next. He felt so alive and aroused. Of course, he was a little scared, but he knew that was an important part of the experience. He was very happy with his life and wouldn't change a thing. He knew that in a few minutes, he was going to be crying and squirming over Diana's lap with his bottom on fire, but he was very happy because of it.

Arriving home, Tim found Diane in the living room. She greeted him with a warm smile and said, "How was the meeting with your friends? Did you eat anything?"

"It was nice. We walked around for a while, then went into a local to watch the game and have a pizza."

While speaking, Tim kept looking around the room for the cane. Diane immediately noticed the gesture and felt like laughing, but refrained. She then added, "I’m glad. We also had dinner, so I propose that we not postpone the long-awaited moment." She went and sat on the chair, holding the hairbrush, and said, "You may go and get ready and use the downstairs bathroom if you need to. I'll be waiting here with our little friend," Diane said, starting to tap her palm with the hairbrush. Tim bit his lip, impressed by how powerful and in control she was. Without further thought, Tim went into the bathroom and took a few moments to calm down and get into the mindset of what was about to happen. He looked in the mirror and remembered how much he needed and wanted to be spanked and how good his life was because of that. He remembered how lucky he was to have two such wonderful women in his life. He felt ready to submit again to his dominant former nanny, and after taking a deep breath, he took off his pants and walked to the living room.

He went straight to Diane, who was sitting in a chair in the middle of the living room. She looked at him, smiling, and said, "Before we get started, we should call Emma. It would be a shame if she didn't attend. Sweetie, it's spanking time!" she shouted.

"I'll be right down," Emma replied.

Within moments, Emma's door was heard closing, and at the top of the stairs, she appeared, holding the cane. She slowly descended each step, seemingly wanting to prolong the moment. Tim watched her, fascinated, and felt himself getting more and more aroused. He could feel his penis throbbing in rhythm with his heartbeat. She was so confident and dominant that Tim felt extremely powerless. Without a doubt, he would get the cane. But it was still unclear from whom. He would undoubtedly be extremely sore, but surely not sorry.

After Emma took her seat, Diane looked into Tim's eyes, smiling warmly, and, sliding her fingers into the elastic of his underwear, began to pull them off. Tim didn't protest at all, but sat obediently and bit his lip in anticipation of what was about to happen.

He remained naked from the waist down, with a fully erect penis. Anyone already knew that Tim was always aroused before receiving a spanking.

He was then guided across Diane’s knee, and after some minor adjustments, he was in the perfect position for his spanking. He looked at Diana's feet and noticed they were tanner than usual. She had a fresh white pedicure that enhanced the contrast. He'd always been drawn to feet, and the position he was in gave him the opportunity to observe them more closely. In addition, both Diane and Emma had gorgeous and always well-groomed feet.

The spanking eventually started, and Tim set off on the long and painful road to his special heaven, a heaven only for the truly submissive. The hand spanking was pretty intense and stingy, but manageable. He loved the skin-to-skin contact, and the hand spanking always seemed so personal. He felt very close to the person administering the spanking, whether it was Emma or Diane. He wanted that part to continue for as long as possible, but he knew that the hand spanking was not severe enough for his needs, and it was also painful for the spanker, so at some point, it had to be replaced with the wicked hairbrush. When that moment finally came, the pain reached a new level, and Tim found it increasingly difficult to cope. But for him, the effort to accept and cope with the pain was a form of respect and obedience, and the greater the effort, the deeper he went into his special heaven.

When the rain of hairbrush smacks stopped, Tim was crying loudly and had already lost all control. While at the beginning of the spanking, he was struggling and kicking his legs, trying hard to resist; after a certain point, he surrendered and stood helplessly over Diana's lap. Except for the crying and groaning, which were constantly intensifying.

Diane rubbed his bottom for a while, waiting for him to calm down a bit, then helped him up and said, "Now it’s time for a good dose of the cane. Emma will do the honors for the first part, but then I'll take over. After you told me how important caning is to you and that you would like to include it in our routine, I put a lot of effort into learning how to handle the cane, and I hope I won't disappoint you. I can guarantee that there is not a speck of dust in the cushions in the house," Diane said, laughing, then added, "I just need to understand how hard the strokes need to be, and Emma will help me with that. Go and bend over the table, and let’s begin."

Tim took his position and was glad that Emma was involved in his spanking because he knew how much she loved to use the cane on him. Emma positioned herself by his side and began to slowly tap his bottom with the cane, preparing herself for the first stroke and increasing his anticipation. Before she began, however, she said in a warm but authoritative tone, "I like to see my target better, so take off your T-shirt, please."

Tim immediately obeyed, but Diane was surprised, so Emma said, "I like to have him naked when spanking him, especially for the caning part. I also feel that being fully clothed and spanking someone who’s naked gives me more power and control."

"I like that, so dear Tim, I want to let you know that from now on you'll be naked for our sessions," Diane said, smiling.

Tim liked the idea because it made him feel even more vulnerable, so he had no objection and even hoped it would come to that topic.

Tim resumed his position and waited tensely for the first stroke. Emma took her time, wanting to let him anticipate and dread the pain a little more. Eventually, the first stroke reached its target, making Tim clutch the edge of the table tightly and howl in pain. A trail of tears began to reappear on his cheeks.

Diane exclaimed, "Wow, impressive. I didn't think the strokes had to be so hard."

Emma replied, "It has to be meaningful, and I'm sure Tim feels the same way."

Tim was sobbing and was unable to speak. He knew Emma was right, though.

Stroke after stroke followed, each one very painful and well-placed. Emma allowed enough time between blows to give Tim time to metabolize the pain of each stroke and to increase tension and anticipation. Diane was impressed by her daughter’s technique and set out to follow in her footsteps. Tim was in great pain, but at the same time, he felt so alive and grateful. Pain and pleasure were so harmoniously blended in those moments that the whole experience was cathartic.

After the twelfth stroke, Emma handed Diana the cane. Diane was a little nervous, but she didn't let it show, and remembering Emma's actions, she began to slowly tap the cane against Tim's buttocks, preparing the stroke and making sure she hit her target correctly. Finally, she pulled back her hand with the cane, and after two seconds, Tim heard the swishing sound of the cane through the air, then felt a sharp pain across the center of his buttocks and made serious efforts to stay in position. He was impressed with how well-placed and hard Diane’s stroke was. She was definitely a fast learner, and he already knew he was in very capable hands. The next strokes were just as severe, and Tim could feel Diane getting more and more confident.

The strokes followed one after another, with a long enough pause between them for Tim to recover and navigate through the pain.

The twelfth stroke was the most powerful but also the last. It took Tim a while to recover, and Diane waited for him to calm down before telling him to get up. He took a hell of a spanking from both Diane and Emma. It was the most intense and meaningful session he has ever had, and he was so grateful despite the fact that he was still sobbing like a baby.

Diane told him to go upstairs until he fully recovered. Tim was glad to have a little time to himself, especially as, after each spanking, when the pain became less intense and he got aroused again, he felt a strong urge to masturbate. That day was no exception, and the orgasm was more intense than ever.

Walking down to the living room, Tim could hear Diane and Emma chatting happily. He was greeted with warm smiles and responded the same way. He went straight to the two women and hugged them, saying, "Thank you both for taking care of me. I feel so lucky and grateful."

"It was our pleasure, honey," Diane said, then added, "I take it there are no complaints regarding our session?"

"No. No complaints at all. You were marvelous with that cane," Tim replied.

"Aww, thank you! I was a little bit concerned about the severity of the caning, but I see you have no objection regarding this matter, so I’ll keep it that way," Diane said with a determined tone.

It took Tim a few seconds to realize that Diane had made a statement, and it hadn't been a proposition at all. He loved the way she imposed her authority. He still had a proposal to make, so without hesitation, he said, "I liked our family time. It was more meaningful to me, and I was wondering if Emma could attend our sessions in the future, when she’s at home, of course."

Diane laughed and replied, "Family time. I like it. This could be our secret code for spanking. I think it’s a good idea to make it a family thing when Emma is around. Of course, if she wants to attend."

"Of course I want. It gives me great pleasure to blister that round bottom of yours. And after high school, if you decide to come to the same city for college, you can count on me to have as many trips across my lap as you need," Emma said, smiling.

"And to make things clear and for you to know what to expect for our next 'family time,'  Emma will also put you over her knee for a spanking. She should be fully involved. No half-measures," Diane said.

"I love you both," Tim said, visibly emotional.

Both women enjoyed spanking Tim and were looking forward to much family time together. They knew that spanking brought them closer as a family and became an important part of their relationship. Tim knew he was in a good place, and he was living the best part of his life so far. His life wasn't easy, and his parents weren't around for very long, but he felt extremely lucky that his former nanny, Diane, and her daughter, Emma, had practically become his family and filled the void left by his parents.

What Emma told him about college really made him consider the idea. It was clear that he needed to be spanked regularly, and being close to her and getting all the attention he needed seemed very appealing to him. Tim knew he would have his family by his side for many years to fulfill his needs. Maybe one day he will find his soul mate. He was in no hurry to look for her, but one thing was certain: there had to be a woman who spanked. Hard and proper. Just like Diane and Emma did.

THE END