Tim’s Painful Yet Rewarding Journey- Chapter V

"Tim is caned for the first time, but not the last"

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Tim was regularly spanked by his former nanny Diane and had already received his first good over-the-knee spanking from her daughter, Emma, with her hand and the heavy hairbrush. After the spanking, they discussed it and agreed it wasn’t just a one-time thing. It was something that Tim both wanted and needed, and he was happy to have broken the ice with Emma. Being disciplined by her felt so right, and he was looking forward to submitting to her again and again.

Also, after the spanking, Emma confessed her burning desire to use a cane, and he agreed to fulfill her wish. So they ordered a cane and decided that on the day it arrived, they would properly inaugurate it.

Tim was both scared and excited at the prospect of his impending caning. The thought of another spanking, as well as a whole new experience, turned him on, but he was also aware that Emma was a natural when it came to spanking, and she gave him such a hard spanking. She couldn’t be gentler with a cane in her hand, and from what he read, a caning hurt more than a spanking with a hairbrush.

The next two days were uneventful. Emma was in an excellent mood, and Tim was a little more pensive. He kept wondering if he’d made a big mistake. But it helped to see her so excited. At least she was going to live out her biggest fantasy.

On Tuesday, Tim received an email notifying him that the parcel had been dispatched. This news scared him, but at the same time, he felt quite aroused. On Wednesday morning, when he woke up, Tim checked his email, and he found an email from the courier company saying that the parcel would be delivered that day. His heart skipped a beat, and he immediately felt a rush of adrenaline through his body. He tried to calm down a bit and to divert his attention with some work around the house. Emma was out meeting some friends, so he was going to be alone until dinner.

Around noon, the courier arrived at his door and handed him a long, tube-shaped package. Tim quickly took the parcel and went into the house, avoiding spending too much time with the courier. The courier was a man about his age. Tim amused himself by thinking about how the courier would have reacted if he had known what was in the package he delivered or what was going to happen to the recipient of the parcel in just a few hours.

Tim immediately went into the kitchen to get a knife, then rushed to open the box to inspect the dreaded implement. It was much lighter than he had imagined, and for a moment, he doubted that such a light item could cause so much pain. It was very flexible, and when he swished it through the air, it made a sound that sent shivers down his spine. He then tried to slap his palm with it and was surprised at how hard it stung. He tried another swat on one of his thighs and convinced himself that it was no joke. He has already begun to regret his decision to try it. Even the waiting seemed painful. He then went in front of a mirror, holding the cane and pretending to punish someone. Seeing himself with the cane in his hand, he immediately understood why she liked the idea of using one. Even to him, it conferred an authority he wasn’t used to having.

Shortly before dinner, Emma returned home. She had a huge smile on her face and immediately asked Tim, “Hey, you, is there something you’d like to show me?”

“Yes, here it is,” said Tim, not at all as cheerful as she was, and he gave her the cane. She studied it from all sides, bent it, and then whipped it through the air. She enjoyed it like a child who had just received his favorite toy as a gift. Tim had to admit that the cane suited her perfectly. It made her look very dominant and in control. Watching her like that, he felt his erection begin to grow.

Seeing Tim very worried, Emma said, trying to reassure him, “Hey, don’t be so nervous. I’m not going to kill you. Think of all the arguments that convinced you to try the cane. They’re still just as valid, even though it’s almost time for the big event. It’s a new experience, and it’s normal to be a little worried. That’s how you were the first time you were spanked. Then you got used to it.”

“I know you’re right, but I can’t help it.”

They had dinner, and then Emma announced she was going to her room and took her cane with her. Tim already knew what he had to do, so he went for a shower. As he carefully dried his body, he looked in the mirror and saw his bottom without any bruises or marks. The images he had seen a few days ago on the internet were running through his mind. And he knew he would soon be able to add an image to that collection. He saw his erect penis standing proudly, removing any doubt that the whole situation had turned him on. If he was as horny before a caning as he was before a spanking, maybe after it’s over it would be just as good. With this thought in mind, he got dressed and went towards Emma’s room. He stopped in front of the door and took several deep breaths, trying to calm down. He had no idea how long he stood there, but his mind was racing.

In a burst of courage, he managed to knock on the door. After being invited in, Tim found Emma standing with her cane in her hand, slightly bending it. It suited that posture so well and made her look so strong and dominant that Tim couldn’t take his eyes off her. He was at her mercy and was prepared to endure anything to make her happy.

Emma eventually said, “The moment I’ve waited so long for has arrived. Shall we begin?”

“Yes, please,” Tim managed to say.

“Then come closer so I can take your knickers down.”

He obeyed, and in just a few seconds, he was standing naked below his waist in front of Emma. She then told him to bend over her desk, firmly gripping the opposite edge of it. He was in position and tried not to tremble too much. Suddenly Emma said, “You know what? Your T-shirt kind of hangs down, and it’s blocking my view of the target. I want to be able to see your bottom in all its glory, so take it off. ” Tim again complied without protest and took off his shirt, remaining completely naked. Then he resumed his position, bending over the table. Being naked made him feel more vulnerable and turned him on a lot.

Emma said in the same authoritative tone that Tim loved, “I like to be fully clothed and you fully naked when I spank you, so this is how it will be from now on.” She didn’t even ask him. She only informed him of her decision. He loved her attitude. As for being naked when spanked, he already thought about it, and it was something he wished would happen, but he couldn’t ask for it. So it was good news for him.

Emma asked, “How many strokes do you think I should give you?”

“I really don’t know, and I don’t think it’s me who should decide.”

“Who said anything about deciding? I just asked for your opinion. I’ll give you six for starters, and, hopefully, I’ll figure out how hard I have to hit before I finish them. If not, we will test with another set. It’s going to get very painful for you, but try not to move out of position or cover your bottom. However, if you do that, the stroke won’t count, so it’s for your own good to try not to move.”

That being said, Emma tapped his bottom with the cane a few times before giving him his first stroke. It took him by surprise, and it definitely stung, but it was bearable.

“Obviously too soft,” stated Emma, then gave him another stroke. It was harder but not evenly applied to both cheeks. She kept going with increasingly powerful and precise blows, becoming visibly more skilled at handling the cane. After the first six strokes, she announced, “I don’t feel ready yet for a proper caning, so we’ll continue with six more before we move on to the real caning. Besides, I don’t think I’m hitting hard enough yet.”

Tim responded with a groan, too nervous to articulate a word. The first six strokes were clearly painful but bearable. After the immediate sting on the impact area, the pain spread and became quite pleasant. For now, his usual spankings with the hairbrush were more severe, so he agreed with Emma about the severity of the strokes.

The next six steadily increased in severity and precision, and by the end of the second set, he already had tears in his eyes. He was trying very hard to stay in position, and the momentary sting after each blow was very hard to bear. By comparison, the spankings with the hairbrush were beginning to feel more and more like a caress.

Emma seemed pleased with the result and said, “I think I learned enough to know how to deliver a proper caning. So prepare yourself for the real deal. I’ll give you twelve strokes.”

The first shot landed, leaving him breathless. He groaned loudly and gripped the edge of the table tightly, trying to stay in position. The first few seconds after each stroke were terrible. Then he managed to recover a little until the next stroke. He felt his buttocks getting more and more swollen, and the pain seemed to spread throughout his body. He needed enormous strength of will to stay in position. He could feel his ass literally bursting into flames.

There was one stroke left, and Emma announced, “This last one is going to be the hardest. Make sure you stay in position.”

She wasn’t kidding at all. That last stroke was pure pain. Tim never experienced something like that, and he barely managed to stay in position. He was crying and sobbing like a baby, but at least he was pleased that it was finally over. Emma put away the cane, helped him up, and held him tight in her arms.

“It’s over. You took it very well, and I’m so proud of you. We’ll talk more about it tomorrow. For now, I’ll let you calm down. I’m sure you are really tired now. Goodnight, my dear.

“Goodnight,” Tim replied between sobs.

Left alone in the room, Emma was just beginning to realize what had happened. She was so euphoric, she couldn’t believe she had fulfilled such a dream. She was extremely wet between her legs, and without wasting any more time, she began vigorously rubbing her pussy, exploding in the most intense orgasm she had ever had. That experience had been more intense than any sex she had ever had.

It took Tim quite a while to recover—longer than normal after a spanking. He couldn’t believe that he had gone through such a painful experience and freaked out when he saw his butt in the mirror. He could almost count the strokes just by looking at the welts on his bottom. Running his hand over them, he felt they were very swollen. He couldn’t help but admit that he kind of liked the way his bottom looked so marked.

But what intrigued him most was the erection he got after such torture. He was extremely horny, even though he’d just been through hell. Needless to say, the orgasm he had that night was spectacular.

Before falling asleep, Tim was thinking about what he should decide about the caning. It was more severe than the usual hairbrush spanking, but he still managed to resist and felt more vulnerable and out of control than ever. Surely he could, with time, cope with the pain even better as he got used to it. It was the same with spanking. The orgasm afterward seemed more intense than usual, his ass full of marks more photogenic than ever, and the sensation afterward increasingly pleasurable. Apparently, there were enough reasons why he should have agreed to be caned again. Plus, it made Emma extremely happy. However, there was a big downside that weighed so heavily that it tipped the scales in the opposite direction. As he lay across the table, Tim was feeling very lonely. He didn’t feel the connection and closeness he felt when he was over Diane’s or Emma’s knees. With these thoughts in mind, Tim managed to fall asleep. A new day was coming, and he had important decisions to make.

The next morning, Tim was up earlier than Emma and went down to the living room. He was prepared to talk to her about what had happened the night before. He was determined to be honest and tell her exactly how he felt and what he liked and hated about the caning. His bottom was more sore than normal, but he liked that feeling. Every time he sat or squeezed his cheeks, he felt a thrill of excitement run through his body. The after-effects were undoubtedly better than after a spanking. And the fear and anticipation beforehand were more intense than ever. His doubts and uncertainty about how painful it was going to be also contributed, but after going through it, Tim knew that the imminence of a caning would make him more nervous than when waiting for a spanking.

Tim often wondered what the ingredients of a good spanking were. He found that the more severe the spanking, the more satisfying it was for him. But he had no masochistic tendencies and hated the spanking itself. Then he realized that what made him happy and excited him so much was to be submissive, to give up control, and to let himself be dominated by a powerful woman. The spanking was actually just a way for him to accomplish that. He loved and hated being spanked at the same time, and he was sure that this love-hate relationship with spanking was the key to the fulfillment he got from it.

Tim interrupted his meditation when he heard Emma coming down the stairs. Looking at her, he saw that she had the cane in her hand and a playful smile on her face. Tim immediately felt an erection growing and immediately changed his position to try to hide it and get comfortable. Emma noticed immediately and kept herself from laughing. She knew they were going to have a conversation about the caning she had administered to him last night, so she thought she would spice up their chat a bit by bringing the implement in question with her. So far, it has had the desired effect. She put the cane on the table next to them, poured herself a cup of coffee, and after the usual good morning greeting, she got straight to the point.

“How do you feel after last evening?”

“More sore than ever, but I can’t complain. It’s a nice sensation, and more importantly, I survived,” Tim replied, smiling.

“Not only did you survive, but you actually took it very well. I’m so proud of you. And I’m glad you’re okay.”

“I don’t know how well. I remember myself crying, screaming, and sobbing.”

“Yes, that’s normal, but you stayed in position, and I didn’t need to repeat the stroke, not even once.”

“So, did you fulfill your fantasy? Was it as you expected?”

“No, it was nothing like I imagined. It was much more than I imagined and hoped for. It was a dream come true, and I enjoyed every moment of it,” Emma replied enthusiastically.

“Well…we have something in common. For me also, it was more than I imagined, but in terms of pain,” Tim said, trying to make a joke, then added, “You know I want more details. At least I deserve that much.”

“You deserve much more than that. Ever since I saw the email this morning, I have been euphoric. The thought of what was about to happen turned me on, and I couldn’t wait for the hours to pass and the long-awaited moment to arrive. When I got home and saw the implement, I couldn’t believe it was so light and flexible. I was pretty nervous too because I didn’t know how I was going to handle it, but I tried not to let it show.”

“And you did an excellent job hiding it,” Tim interrupted her.

She smiled at his remark and continued, “When I was in my room waiting for you, it seemed like forever before you knocked on the door, but when I looked at the clock, it had barely been twenty minutes. I was glad you didn’t make me wait longer. For the first two sets of six strokes, I was very nervous. All I focused on was where and how hard to hit. It was my learning curve, but after that, I knew I could handle the cane well enough and that it was time to really enjoy the experience. The twelve strokes that followed were pure delight. I really enjoyed watching the welts develop on your bottom. After the stroke, it takes a while for the skin to react, and then you see how the place where the cane landed turns pink, starts to swell, and gradually changes color, going through all the shades to dark red. It’s fascinating. And the feelings—oh, what a great experience! I was in ninth heaven, and I felt more dominant than ever. Watching you struggle to stay in position and still do it gave me power and authority I had never experienced before. I felt that I was really in control over you, and I was making you surrender to me completely. After it was over and I was alone in the room, I won’t tell you what happened. I’ll spare you the details. I’ll just tell you that I found the whole experience of administering a caning highly arousing,” Emma concluded with a broad smile on her face.

Listening to Emma’s story, Tim couldn’t help glancing at the cane on the table from time to time, trying not to be too obvious. Emma didn’t miss that detail, but she didn’t let it show. The whole discussion was really turning Tim on, and he was feeling an increasing need to release the pressure he felt in his pants.

“I’m so happy for you, and I’m glad I could help.”

“It’s your turn now. I need all the details from the beginning.”

“I don’t know if my story is as great as yours, but here it is. You know, I had a lot of doubts and fears before I agreed to try being caned. Even after I decided that I would try it, they didn’t disappear and haunted me all the days that followed. When I saw the email announcing the delivery of the parcel, I initially panicked, and it took me quite a while to recover. I was sure I had made a big mistake. Then I started thinking about all the conversations I had with you, and I calmed down a bit. However, that day was extremely long, and the anticipation and fear were greater than ever.” 

“You seemed very excited about it when you came into my room, and I pulled your underwear down,” Emma said, giggling. 

That comment made Tim blush, but he said, “I’ve already told you that I enjoy the part before the spanking begins. Thinking about spanking and all the anticipation turns me on.”

“So basically, the more scared and nervous you are, the more aroused you get. So it’s a positive aspect,” Emma rushed to conclude. 

“Yes, it’s a good thing,” replied Tim. She was so excited and kept interrupting him, but at the same time, she controlled the whole discussion, and he liked to see her in control. 

“Go on then,” Emma said impatiently. 

“After dinner, I tried not to delay the inevitable, which is why I got to your bedroom pretty quickly, but the walk there wasn’t easy, and I have no idea how much time I spent in front of your door before I plucked up the courage to knock. I struggled to keep my legs from shaking with anticipation, and when I was in position, totally naked, I felt more exposed and vulnerable than ever. The first set of six strokes stung but was quite bearable. I was impressed with the way you were evolving with each stroke, hitting harder and more precisely. The next set of sixes was significantly harder than the first, and I was already struggling to control myself. Then hell came down to earth, and its flames swept over my bottom.” 

“So bad was it?” Emma asked, laughing. 

“I’ll try to explain the feeling as best I can. You were right. The pain is completely different than when spanked with a hairbrush. In the first few seconds after the stroke, the pain and sting were so fierce that I never imagined I would experience something like this. Then it starts to dissipate to the whole bottom and becomes bearable, even a little bit pleasant. When spanked with the hairbrush, the blow itself does not cause as much pain, but because the breaks between spanks are too short, the pain builds up and becomes hard to cope with. So when spanked with the hairbrush, the pain is constant and increasing, and when being caned, the pain fluctuates. You might say that being caned is easier to tolerate than spanking with a hairbrush, but the peaks and the moments after each stroke of the cane are so painful and unbearable that it is overall much harder to endure a caning. I hope my explanation helped you get an idea.” 

“Yes, you were very descriptive,” Emma said, then added, “But you didn’t tell me how you felt, and I’d like to know.” 

When you’re spanked, after the first hit, the others generally follow without much interruption. The only thing that is unknown is how many there will be. But you can’t focus too much on the past or the future. It’s too painful to think about anything but how to gather all your will and energy to cope better. After the spanking starts, the anticipation pretty much disappears. Last night, I knew how many strokes I was going to get, but I didn’t know exactly when each one of them would land on my bottom. So I was in constant tension. I felt more out of control than ever, and in the seconds after each shot, I made a huge effort to stay in position. With each stroke, I was getting further and further into that subspace I told you about. I was totally dominated and defenseless, and I had nothing to do but submit to you. About what I did in my room afterward, I also don’t want to tell you, but I think it’s pretty obvious,” Tim said, laughing.

“So you managed to get exactly the feelings you’re trying to achieve in an intense way, and you also had a great time afterward.” 

“Yes, something like that.” 

“Then what should we do with this cane? Should we make it a permanent guest in our special meetings, or should I hide it in a closet and never mention it? From what I heard, the answer seems obvious, but I need your confirmation,” Emma said, visibly elated. 

“Well, it’s not that simple.” Tim started to explain but was immediately interrupted.

“What am I missing? When you saw me this morning coming downstairs with the cane in my hand, you had an almost instant erection that you tried to hide. The whole time we were talking, you kept peeking at the cane on the table and squirming in your chair, trying to get comfortable and not let the bulge in your pants show. You told me that the moments before and after the caning were more intense and arousing than normal, and that although you found it more severe than the spanking with the hairbrush, you appreciated it more because it helped you experience the feelings you aimed for in a more intense way. 

“Well… If you hadn’t kept interrupting me, I would have gotten to this part. It’s true what you said, though I didn’t expect you to have noticed everything.” Tim said, blushing, then added, “When I’m over your or Diane’s knee getting a spanking, I feel more connected with you. I feel close to you. I feel loved and safe. Last night, when I was bending over that desk, I felt lonely; I didn’t have the same strong connection. Being spanked over the knee is more personal, and I tend to like the domestic aspect of spanking. The hairbrush is definitely a more suitable implement than a cane for domestic spanking. These aspects are very important to me, so of the two options, I definitely choose to be spanked over the knee with the hairbrush.”

“Wait a minute. I think there’s a little bit of confusion here. When I asked you if you wanted to make the cane a guest at our meeting in my bedroom, I never thought we’d replace the over-the-knee spanking. It’s your big fantasy, and I also like having you over my lap too much. All I proposed was to add the caning to our usual routine. More precisely, a good over-the-knee warm-up with my hand, followed by a hard spanking with the hairbrush, then finish with twelve or more strokes of the cane.”

“Ow, I thought I had to choose one.” 

“Yes, I know. But now we’re clear. Look, I know it’s an important decision, and I suggest you take whatever time you need and then tell me what you’ve decided.” 

Tim glanced quickly at the cane and said in a rather determined tone, “I’m in!” 

Emma was surprised by the quick response but immediately smiled broadly and said, “Sooner than I expected. Did I need to tell you that I think you made the right decision?” 

“I know it’s the right decision, although my bottom might disagree.” 

Emma laughed at his remark and replied, “In time, he’ll get used to it. Besides, what I gave you last night was a cold caning, which means applying the cane without a warm-up. From what I’ve read, caning after a good spanking is less severe than cold caning. The latter is particularly recommended when severe corporal punishment is involved. Plus, after a long spanking with a hairbrush, the bottom gets a little numb and will be less sensitive when the cane is applied. At least that’s what I read on the internet.” 

“I suppose we’ll live and see,” Tim concluded. 

Emma got up and, taking the cane in her hand, walked towards the stairs but stopped and said, “I’ll keep the cane in my bedroom. The hairbrush may stay in its usual place. If you miss seeing it, we can always arrange an appointment with it in my room.” Then she started up the stairs, leaving Tim to follow her with his eyes. 

“Have I told you before how well it suits you?” 

“I already know that, but thank you for your compliment,” replied Emma while entering her bedroom. 

The days that followed brought only occasional mentions of spanking into their conversations. Mostly, it was questions about Tim’s bottom healing process. Otherwise, the vibe in the house was very good, and the two got along great.

After about a week had passed since Emma caned Tim, she began to get impatient and started dropping some hints. At one point, when they were in the living room, watching TV, she suddenly said, “I forgot to tell you what happened this morning. As I was sitting in my room looking at the walls, I suddenly heard someone call my name. You can imagine I was scared, especially since it wasn’t your voice. Then I tried to identify the source of the sound and guess who it was. It was the cane, placed proudly on my desk. I couldn’t believe my eyes, but he was actually talking. And you’ll never guess what he told me. He asked me about you and wanted me to tell you that he misses you and would like to meet you as soon as possible. He said he wanted to be your friend. Don’t you miss him too?”

Emma’s story made Tim laugh. He immediately realized where that conversation was going but decided to play along and said, “I’m not sure if I miss him. I don’t know him so well; I only met him once and felt quite intimidated in his presence.”

“He mentioned to me that he was afraid he didn’t leave a good impression on your first meeting. He asks you to forgive him. He tends to screw things up sometimes but promises to try his best to make a better impression, and hopefully, you’ll become friends.”

“I’m not sure, you know what they say: first impressions count.”

“It’s true, but sometimes we make mistakes. And they shouldn’t define us. He just needs a second chance.”

“Ok, since he’s so eager to meet me again, you can set up a meeting this evening.”

“Ow, such great news. I’m so glad. I can’t wait to tell him.”

That conversation left Tim with a bulge in his pants, and Emma’s panties were soaked. For both of them, it was going to be an intense and rewarding evening.

It was almost time for dinner, and Tim was back from a run. He used to walk or run to clear his head and distract himself from a problem. Today, he really needed something to distract him.

He found Emma in the kitchen and asked her very casually, as if nothing had happened, or more precisely, as if nothing was going to happen, “What are we having for dinner?” He was actually pretty nervous, but he was trying to look like he wasn’t.

“I make some pasta with salmon and put a bottle of wine in the fridge. We also have dessert, but you’ll have it in my bedroom.”

“How nice of you,” Tim said, visibly ironic.

Emma said, smiling but in a demanding tone, “Just letting you know that it’s going to be a while before lunch is ready and you’re sweaty and could use a shower first. That way, you don’t waste any more time after dinner.”

“Ok, if you insist…”

“I’m not insisting at all, just suggesting. It’s your choice whether or not to follow my advice, but I assure you it would be for your own good.”

Tim was impressed and turned on by the way Emma was already asserting her authority even before they got to the spanking part. She didn’t do it in an aggressive way, but suggesting that if he didn’t follow her advice, there might be consequences made Tim stop hesitating. When you’re about to get spanked and caned, the consequences seem pretty obvious, and you don’t want to upset the woman wielding the implements.

Tim took a shower and then returned to the living room, where Emma was already bringing dinner. He got busy pouring wine into glasses.

Without knowing about the impending “desert,” it all seemed like a regular family dinner. Emma had even played some music in the background, and the very first song was Stairway to Heaven, a hint that Tim immediately understood and burst out laughing.

In case he didn’t catch the hint at first, Emma had prepared a second rock ballad with an obvious message, and on the chorus, she even started singing “Knock-knock-knockin’ on heaven’s door.”

Tim laughed and gave her credit for her creativity. The plates were already empty when Emma rose from the table and said in a sweet tone, “It’s time for the dessert. Would you be a dear and wash the dishes before you come upstairs?” Again, she had just asked an innocent question, which left no room for refusal. Without waiting for an answer, she added, laughing, “Then, when you’re ready, you take the stairway to heaven, then knock on heaven’s door, and I’ll be ready with your dessert.”

Tim was so turned on by the way she talked to him. She was already in control, and he already felt he was under her power. As he washed the dishes, he thought about that stairway to heaven. He was really going there, but it was a paradise that resembled hell at times. But in the end, it was heaven that he was willingly heading towards, and that gave him great satisfaction and happiness.

After finishing the dishes, Tim sat down for a few minutes. He didn’t want to keep Emma waiting too long, but he needed a few moments to clear his mind of other thoughts and really focus on what was about to happen. He needed to think about all the emotions he felt when he was totally submissive to Emma and how much the idea of being dominated by her and losing all control turned him on. He had to remember exactly why he was willing to go through that painful experience and why, even though he hated the pain of being spanked and caned, he wanted to go through it again and again.

The mindset was very important to him, and that evening he had even managed to calm down and start up those stairs without the fear he usually had. He wasn’t walking like a lamb to the slaughter, but like a man who understood that his place was under the control of a strong woman and that the great pain he was about to suffer was a very small price to pay compared to the fulfillment and joy the experience offered him every time.

He was in no hurry, though, enjoying every moment of that journey to Emma’s bedroom. He liked that part and already felt the transfer of power to her. With each step, the anticipation grew, as did his arousal. He finally reached the door, and after taking a deep breath, he knocked.

Inside, Emma greeted him with a sweet smile on her face, saying, “I’m glad you’re here. Are you ready for dessert?”

“Yes, I’m starving,” Tim replied.

“Oh, you’re cocky tonight. I’m glad you’re hungry because I plan to stuff you with dessert. Let’s see how cheeky you get later,” Emma said in a harsher tone.

Tim didn’t understand why she responded that way, but Emma’s reply put him in his place.

“Sorry,” he said, looking down at the floor.

Emma chose to ignore his apology and decided to impose her authority further by saying, “You have way too many clothes on, so you better do something about it.”

Tim couldn’t disagree with her and started undressing in front of her. Emma said, “I haven’t prepared a suitable song in my playlist for this, but I’m sure you’ll be fine without music.”

He first took off his T-shirt, then unbuckled the belt of his trousers and took them off too. Emma watched him intently, and he felt very vulnerable and embarrassed.

Remaining only in his underwear, Emma said, “Leave them on and come to me so I can finish undressing you.”

He did as he was told, and she reached forward and, putting her fingers under the elastic band of his underwear, pulled them down and then helped him step out of them. Left completely naked, Tim looked down at her toned and inviting lap, waiting for her command to lie across.

He didn’t have long to wait and was soon back in the already familiar position, over the knee, waiting for hell to meet heaven and battle over his naked, unprotected bottom. Tim again took the opportunity to enjoy looking at Emma’s perfect feet and toes, at least until he started crying and the image became blurry. He particularly liked that view. That time her pedicure was bright red, and Tim really liked that color not only on her nails but also on his bottom.

After a few circular rubs on his bottom, designed to increase the tension even more, the first smack landed on his bottom, followed by a rain of well-placed swats. The pain was starting to get more and more intense, and his ass was starting to get hotter and hotter, a heat that was making him warm in other parts as well. For him, the hand spanking was, up to a point, enjoyable. When the pain went beyond a certain level, he no longer found spanking sexually stimulating, but feelings of submission and losing control began to take over, and these ultimately led to an even more sexually stimulating experience.

For Tim, hand-spanking was a very important part. It was very personal, and he felt connected and close to his spanker. At first, he enjoyed the pain, but as he progressed, he gradually began to feel himself losing control and taking the first steps into his subspace, where he felt totally submissive and vulnerable. The pain of a hand spanking was never unbearable for him, but it was meant to prepare the ground and open the gates to that subspace where it rains with endorphins, where pain and pleasure merge in the most formidable way.

The swats continued without pause, and Tim began to gasp softly and squirm across her knees. Not at all impressed, she firmly gripped his waist and kept landing smack after smack, showing without any doubt who was in charge.

Finally, she stopped and said, “Enough with the warm-up. My hand already hurts, and the only one that should hurt is your bottom.” After a pause where Tim thought she was grabbing the hairbrush to continue the spanking, she spoke again: “I think we have a problem. Get up!”

Tim was puzzled, but he obeyed her without saying anything. She then said, “I forgot to take the hairbrush with me. Since it’s my fault and today I’m in a great mood, I’ll give you a choice. You can go now and bring the hairbrush from downstairs and then get over my knee again for a long and hard blistering with it, or we can skip directly to the cane. And I’m not messing with you. The tariff for the cane is the same no matter what choice you make.”

Tim couldn’t believe it. What a choice Emma had given him… He could skip the dreaded hairbrush and get the same caning he would have gotten anyway. The answer was obvious, so Tim hurried to reply, “I’ll go get the brush,” then headed towards the living room.

Emma was smiling and felt her panties get even damper. She already knew the choice Tim would make, but she wanted to give him the opportunity to once again show his willingness to submit to her. She was prepared to skip the hairbrush, but she knew for sure it wasn’t what Tim would have wanted.

On the way downstairs, Tim thought about his choice and was convinced it was the right one. He wanted to fully obey Emma’s authority, and he really appreciated the opportunity that was offered to him. For him, true submission was not being told what to do and doing it, but being given a choice and willingly choosing the more painful and complicated option. Exactly as it had just happened.

That unexpected turn of events really turned Tim on. He was holding the brush and preparing to take the stairway to heaven for the second time in a single day, totally naked and with a red bottom. His already spanked bum was sending an intensely pleasurable and erotic warmth throughout his body, and he had a full erection again.

He returned to Emma’s bedroom, holding the hairbrush. and handing it to her, waited obediently to be told what to do. Emma said, pointing at his erection, “You’re really looking forward to this.”

Tim blushed and replied, “It’s more about the idea of it.”

“Nonsense. You had a choice. Don’t tell me you’re already starting to regret it.”

“No, not at all.”

“Then get back over my lap and enjoy it. I told you it would be long and hard, and I intend to keep my word. Plus, you told me you’re starving.”

Without waiting any longer, she started landing the hairbrush hard on his bottom, and she did it countless times, almost without pause. Tim was in so much pain, and it was harder and harder for him to cope with the spanking. She was holding him tightly by his waist and didn’t hold back at all.

Tim was more powerless and felt more out of control by the minute, and he reached his subspace, where he was able to enjoy her dominance and power. He was lying across her knees, taking stroke after stroke, and his bottom hurt so bad, but inside he felt peaceful and happy. It was as if his soul was separating from his body because he no longer felt the same excruciating pain.

Emma stopped spanking him with her hairbrush, but he only noticed after a while that the strokes had turned into rubs. She let him stay over her knee for a little longer, then told him to stand up and bend over the desk for the caning.

“You’ll get twelve strokes this time. You know the rules. If you move from your position, the stroke doesn’t count. Are you ready?”

“Yes,” Tim said, trying to appear as confident as possible given the circumstances.

Emma tapped the cane a few times on his bottom, then pulled her arm back and, with a swish, brought the cane hard on his bottom, causing him to grind his teeth and let out a low, muffled scream. He squeezed hard against the edge of the desk and managed to stay in position. After a few seconds, the burn became more bearable, and he managed to catch his breath. The second stroke was harder than the first one because it landed exactly on his sit spots. Tim was howling in pain but stayed obediently bent over the desk.

Although he struggled to cope with the pain and stay in position, Tim had to admit that Emma had been right when she told him that a caning after a spanking might be easier to take. On the one hand, he felt his bottom a little numb, and that definitely helped, and on the other hand, after a hard spanking with hand and hairbrush, he was already in his happy place, being able to focus on more than just pain. He was able to enjoy the feeling of submission and was more prepared to endure the caning than before.

After the first three strokes, he lost the count. He simply didn’t care how many more strokes were left. Emma made him wait quite a long time for the next stroke, which on the one hand allowed him to recover but on the other hand made him feel even more nervous, even though he knew he couldn’t change anything. He loved that feeling of total loss of control.

Eventually, Emma announced, “Last one. It will be harder than the others, so be prepared.”

He gripped the edge of the desk tightly and told himself he wouldn’t let go, even if the end of the world came. The stroke was indeed very forceful and placed right in the sitting area. Tim screamed loudly and started swinging his legs through the air, but he remained with his hands on the edge of the desk and his chest pressed against the table. Even Emma was impressed by his determination.

Emma let him lean over the table for a while to recover, then helped him up and held him tightly in her arms, kissing his tear-stained cheeks.

“It’s over, my darling. You did great, as usual. We’ll talk tomorrow morning over coffee. Right now, I think we both have more important things to do. Good night,” Emma said, smiling.

“Good night.. And thank you for tonight. I mean it,” Tim said, looking sincere.

Being in their own rooms, they both knew that evening had been the most intense they had ever had. Emma was wetter than ever between her legs, and she felt her vagina throbbing with every heartbeat. She immediately began fingering herself, and it didn’t take long before she was moaning, and she experienced the most intense orgasm she’d ever had before. She would never have imagined that spanking could give her so much satisfaction.

Tim was still in pain, and it took a little longer for the pain to dissipate and turn into a really pleasant and erotic sensation. That made his erection grow bigger and bigger, like it was going to explode. It was the hardest, but at the same time, the most intense and rewarding spanking of his life. And he was aroused as never before. He rolled on his back, still naked, and started to gently stroke his penis. Then he rubbed it harder and harder as vivid memories of the spanking and caning he had just received played in his mind. He came heavily all over his belly and chest. It was amazing.

Until he managed to fall asleep, he could think of nothing else but spanking. He felt so grateful that the two most important people in his life understood his need and helped him live the most intense and beautiful moments of his life.

He was also thinking about how being caned was a game-changer for him. At first, he had been so reticent about it, but he was so glad that he let Emma talk him into trying it. He knew that without it, he wouldn’t have experienced such intense thrills.

Being spanked and dominated in that way was becoming increasingly addictive for Tim. He was sore like never before, but he was so happy and grateful. He already started picturing himself over Emma’s knee being spanked, then bending over the table for the dreaded caning, and he can’t wait to live that dream again. But he knew his bottom would be sore for days, and he needed time to heal. Unfortunately…

Published 8 months ago

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