Learning His Lesson

Rebecca looked down at her watch. He was late. She hated it when they were late. It was disrespectful, and the last thing she wanted to deal with when starting a session was disrespect. She heard what she assumed was his car in the driveway. This one was new, so she wasn’t exactly sure what to expect. She looked out the curtains. “Oh great.” She thought. An oversized truck. We were starting with a need to overcompensate. He might take some work. He knocked on the door.

As she opened the door, he tipped his hat but didn’t take it off. “You’re late.” She snipped. “And I don’t like hats,” she snarled, as she knocked the fedora off his head. “Let’s see if you’re overcompensating as much as I think you are. Step inside and take off your clothes.”

He looked at her icy stare and wondered if he had made a mistake. She seemed to be looking for a bone to pick and was pretty sure that bone was gonna be his. He moved inside the door and waited for her to close it.

“I said to strip!” Rebecca said, half yelling at this point. He really did have her a bit pissed at this point.

“But the door is open,” he noted. “The neighbors.”

“I don’t care about the neighbors, and you need to learn who is in charge here.” She was yelling by the end, and grabbed both sides of his flannel, ripping them apart and off his chest. A couple of the buttons went flying, and it hurt. He decided he probably shouldn’t say anything about it and continued to quickly shed the rest of his clothes himself. He was very aware of his erect member, that he absolutely was overcompensating for. He could see the anger in his eyes and decided that pushing the limits wasn’t a good idea at this point. Once he was nude, he quickly dropped to his knees and hung his head down. It was only then that she closed the door.

“It’s about time you showed a little respect.” She commented, as she circled him like a vulture stalking their prey. “Why exactly are you here today LITTLE man.”

He hesitated. He wasn’t exactly sure what to say. I mean, he knew why he was here, but to say it out loud was a completely different thing. “I need you to take care of me.” He decided on. Wrong choice.

“Oh, you want me to do your laundry and wipe your ass?” She spat.

“No mam.” He responded. He figured being straightforward was a good choice at this point. “I am here because I need you to provide me direction and ph…ph…ph…physical correction.” He stammered. He couldn’t believe he was saying it out loud.

“So, you’re saying you want me to command and punish you?” It was then that he saw it. She was filming with her phone. Him, naked and kneeling on her living room floor, saying these things. There was no turning back now.

“Yes, I want you to command and punish me mam.” He replied. “Please. I need it. I’ve been l…l…lost.”

“You said in your email you’ve been drinking, smoking, and just, to sum it up, being an asshole to everyone.” Rebecca summarized.

“Yes mam, that is correct. Please help me. I don’t want to live like this.”

Rebecca smiled. She liked this part. As much as she loved inflicting pain, she did enjoy helping them. These helpless, worthless men walked out of her house actually worth something. “Good. Then follow me. No need to stand.”

He crawled behind her down the hall and into a large room behind the kitchen. She stopped before she opened the door and put a blindfold on him. She also buckled cuffs around his wrists and ankles. He then felt it, the collar around his neck. It wasn’t padded like the cuffs. It was just rough leather, a little too tight, but not quite tight enough that he had trouble breathing. “Wiggle room” there was not though. He heard the “click” of the leash right before he felt the rough pull on the leash into the new room. It was colder here. He also became acutely aware of his raging hard on. He wasn’t sure if she noticed though, at least until they stopped, and he felt the tip of the crop against the head of his cock. It stung. So much. He fought back tears as she struck his cock four more times.

“Naughty boy. Getting so turned on already.” He could hear the slight smile in her voice this time though. That was somehow more comforting. He was about to open his mouth when he felt it. She forced the gag into his mouth roughly and buckled it behind his head. He felt it, like an intruder. He tried to move it with his tongue and couldn’t. He whimpered a bit. “Oh, little boy likes his gag, huh? It will keep you from screaming too loudly. I know how concerned you were about the neighbors.”

“Stand up now,” Rebecca commanded. He did, as well as he could, and felt himself being bent over something. It was cold and leather. He felt his cock on it first, as she pushed him down. It was uncomfortable under him, but she didn’t seem to care. He heard a click on each ankle and wrist, then two on his collar as she undid the leash and clipped him to this thing. He then felt the straps come across below his knees, and then his elbows. There was then one across his waist. It was at this point that he realized that he couldn’t move, or see, or speak. She already had him helpless.

As he felt her warm hands move away, she spoke. “I’m going to punish you now. You won’t like it.” With that she stepped back and all he could feel was the cool air on his skin, the leather against his belly, the restrains pressing into him, and the feeling of absolute helplessness that comes from being exposed and knowing that you are about to get what you asked for and need so badly.

Rebecca wasn’t going to disappoint and had chosen a light strap to warm him up with. He, of course, wasn't aware that it was just the warm up. The strap didn’t hit deeply, but it stung like fire, and he would have cried out if his mouth wasn’t full of the hard rubber gag. At this point he felt invaded by it. His mouth gaping open, stuffed to the point that he couldn’t even form words with his tongue or lips. He couldn’t cry out, he couldn’t scream, he couldn’t beg for what he had asked for to stop. He had put himself at her mercy, and was not feeling that mercy at the moment, nor would he for a long bit. He couldn’t even bite into the gag for relief. All he could do was drool helplessly, and he realized that was exactly what he was doing. “Ouch.” He would have said if he could have. The strap had found his thighs. Rebecca knew that his thighs would be much more sensitive, but he did not. He wasn’t prepared for the bite when the leather hit his skin. She was steady, methodical. There was a comfort in the method, the resolve she had. This comfort wasn’t doing much to counteract the fire building in his ass and thighs, as she worked the strap back up.

Rebecca knew this was his first time, and knew that he needed the lesson, so she was making sure to warm him up thoroughly for what was to come. She knew that if he didn’t have the gag in he would be screaming, begging her to stop at this point. That wasn’t what he needed though. He needed this. He needed the pain and the release of being helpless beneath her hand. She was taking care to space out the increasing redness. She wanted him ready to endure his punishment and knew it would be easier on him if she made sure his skin was ready for the rougher treatment. She continued her work until the redness was even, a beautiful canvas upon which to begin her work.

He was sure it had to be ending soon. His ass and thighs were on fire. He was sure there was no place untouched by his strap. He pulled at his restraints a bit. He wanted to cry but wouldn’t. He wasn’t going to give her that. In fact, he found his anger at her increasing. When he felt her step away and heard her put the strap down he was ready. Ready to go after her as soon as she let him up.

Rebecca sensed his anger start to grow as she stepped away. She had fully awakened his brat. The brat that was soon to find himself thoroughly tamed. She knew it had to surface to be healed. She watched him struggle for a minute. She slipped her hand down her pants to touch herself for a bit as he strained against the buckles. He wasn’t going anywhere. He thought she was about to let her up even, she could tell it. She stepped around and removed his blindfold. She looked straight into his angry eyes and said, “we aren’t even close to done yet.” She watched his eyes drop and the realization that he was not finished sink in. “You have a lesson to learn and it is my job to teach you. You wouldn’t want me to stop now and you not learn anything, would you?”

He managed to shake his head no. He didn’t want that. He wanted to let it go. He wanted to be someone better. He was here for a reason. It was he who called Rebecca. It was he who asked her to do this.

Rebecca saw this struggle in his eyes. She liked watching them, watching them give in, watching them submit, watching them realize that their life has changed, and nothing will be the same from this day forward. She grabbed the blue paddle from the wall. Pickleball had taken off lately, which was fortunate, because those paddles were perfect. They were light, full of holes, and very nice coverage. She made sure his eyes caught it. She saw that flash of panic and stepped back in front of his face. She put the paddle in front of him, so that is all he could see. She let him look at it for a few seconds before claiming his eyes. “You know you need this. And you are going to be a good boy when I get done with you.” She smiled as she said it. She felt the smile though, felt the happiness. He wanted that. He wanted to see that smile more than anything now. Wanted to hear that “good boy.” The first tear slid down out of his eyes. She wiped it away with her finger, then put the finger in her mouth. Tasting his tear. “There we go, that’s more like it.”

And with that she was gone from his vision. He had never felt anything like that first paddle strike before. It stung, everywhere. She must have been a tennis player with the power behind her swing. It was that first blow that broke through. He gave in to the tears. The second came quickly, on the other cheek. He thought that his ass was going to explode from the pain. She brought the next two down on the same place. Then three on the other cheek, quick and strong. He tried to jump. He tried to get away. He didn’t mean to, it just happened. It didn’t really matter though; he wasn’t going anywhere. The next three came quickly after this revelation. Right at the bottom of his ass and the top of his thighs. The tears turned to weeping. He would have been screaming if the gag wasn’t there. He was thankful it was now.

She set the paddle down. He was so thankful. He had a feeling she wasn’t done yet though. She walked around, bending down to look into his eyes. It was there now. The need. “There you go. Let it go. We’re going to help you be a good boy. You’re getting there. Do you feel it now?”

He nodded his head up and down. He absolutely felt nothing but the fire in his backside. He had even forgotten about his cock, which was still pressing hard against the leather. She stood up in front of him. She was wearing black leggings and a corset style black top. There were skulls, shiny, also black, on the corset. The bottom was trimmed in a lace that drew his eyes. There was something else though. Oh. It was her. He could smell Rebecca’s arousal. She stood right there for a few moments. She wanted him to smell it, to want her. She wanted him to know that this turned her on. A few seconds later she moved away.

“I think we need to teach you a deeper lesson, don’t you think?. I think this should do it. She let him glance at the long handled wooden bath brush for a moment before walking behind him. She knew he needed bruises, and was going to make sure that this lesson went deep. She swung hard, hitting right on his sit spot on the right side. He screamed into his gag as Rebecca brought what he had decided was the most evil of implements down in the same spot on his left side. The blows came quickly now, alternating sides. He didn’t know how many there were in the end. He only knew that he wasn’t going to be sitting comfortably for a long time. He wept. It felt so good, the letting go part. He felt his body relax for the first time in… he didn’t even know when. The tears fell. All he felt was pain. Pain and freedom. It was like the waves of the ocean. Washing him clean. Making him whole again. He didn’t know how long it was.

Rebecca knew she was pushing him, and that was exactly what he needed. She kept going until she knew that the skin was about to break. She didn’t want to make him bleed. She just needed to take him to that edge and push him over, keeping him safe as he fell. “There you go. Isn’t that getting better?”

He nodded his head up and down. It was getting better. Wait? Was there more?

“I have one more surprise to help you behave.” He panicked for a moment, but that moment was all he had to think about it before he heard the “swish.” He knew what that was and tried to pull away again. He didn’t actually move. He couldn’t.

She had saved the skin on his ass just for this. Rebecca took a step back. He was going to have nice pretty cane marks above his bruises. She stepped into it, bringing the cane down hard at the top of his ass. She could hear him scream through the gag. She knew he was reaching his limit. “Two more,” she encouraged. She landed the second right under the first. She was both skilled and practiced. She watched the welt develop while giving him time to recover. “Last one.” She reminded as she took another step back, this one was going right on the meatiest part of his ass. The cane came down fast and hard. She pulled another scream from the deepest parts of him. She hung the cane back up and walked over to him. He felt something cool and soothing on the fire that was consuming him. The aloe was soothing, and her hands heavenly. She started then. “You’re such a good boy. You took that so well.” She unbuckled his legs from the restraints, as he laid there limply. She came around to his arms, unbuckling them before undoing the leather around his torso. “Now we can start fresh and new.” She took the gag out off of his head. He realized how much his jaw hurt now. It had been spread for so long.

“Let’s stand you up now.” She said as she helped him up and to a chair. He winced as he sat down, but he was too wobbly to stand at the moment. He realized what a mess he was. His face was covered in tears and drool. She put her fingers under his chin, lifting his face up to look her in the eyes. “That’s my good boy. Now let’s talk about how you’re going to behave this week.”

She gave him a list of rules. Manners, no drinking, a long talk about kindness. He drank it all in. He wanted it. He wanted the structure. It was what he had been longing for. “You have a long week ahead of you. I want pictures of each room as you clean it. Remember, one room a day, your kitchen first.”

“Yes mam.” He replied.

“And I’m torching the fedora.”

He would do anything to please her at this point. He was coming back to himself now. She brought him water, and he drank it quickly. He was thirstier than he realized. He didn’t even know when the last time he drank water was. At least three glasses a day now.

She started to walk him to the door. She helped him get his clothes back on as she admonished him on his behavior.

“Call me if you need me over the next week. Make sure you follow my directions, and if you start to drop, let me know right away. I’ll see you next week, same time?”

“Yes mam! Thank you.” He gazed into her eyes as he said it. He meant it. She could see it in his soul. See the changes taking place.

“I know you’ll make me proud.” She said as he left. He knew that he would. He had never wanted anything more.