Claire's Dreadful Misadventures Ch. 01

Claire nodded.

"Normally, objecting like that would get you extras, but I'm not going to punish you for that because I know you are still getting used to things. So, for now, I'm just going to give you three swats, which is really not much. It really isn't. But if there is any more disobedient behavior, I'm going to have to stop being so forgiving, and that number of swats is going to increase, or the severity of the punishment is going to be increased somehow.

Okay, so let's do it this way. We are gonna say that the conversation piece is now over. And I want you to explain back to me what is going to happen to you. So, that way I know you understand."

"Okay, I..." Claire drifted off, wrestling with her own emotions and the decision of how to respond. "I... I will be p-p-paddled three t-times... with the quarter inch paddle."

"Almost correct. Three times under what conditions?"

"Oh, well okay. I will be paddled three times if I follow all the rules, but I will get extras if I disobey."

"Alright, and what are you going to do before the spanking?"

"I'm... going to take off my skirt and my underwear."

"Right. Let's have you do that now, and then we can talk about the position you are going to maintain for this punishment."

Claire's cheeks were blushing. Her eyes were watery. She was breathing a little bit faster than normal. She slowly removed her skirt. She glanced pleadingly at Dr. Thorton one last time, and then took off her panties. She immediately covered herself. She thought it felt strange to feel the cold air of the room directly on her naked bottom.

"Claire, you need to put your clothes on the couch like I said before."

Claire quickly did as she was told and then covered herself again.

"Now, we are going to get you in position. Go and ahead and grab that chair you were sitting on and place it in front of the desk so that the back of the chair is almost touching the desk."

"Like this?" Claire asked.

"That's acceptable, yes. Now, just hop up there on your knees. Then, bend over with your elbows touching the desk." Claire kneeled on the chair. It was a little uncomfortable because the chair was wooden with no padding. Then, she bent over the desk.

Dr. Thorton walked around the desk so that he was facing Claire and picked up the paddle.

"Ok, good. But can you get your arms up off the desk, please?"

Claire looked at him confused. "I don't understand."

"Remember to call me sir."

"I don't understand, sir."

"Yeah, that's actually been an issue in your last few responses. Yeah... But I said put your elbows on the desk, not your hands. Your hands need to stay in the air. I actually really don't want you touching anything on the desk or the desk itself, except you can just use your elbows to support yourself, okay?"

"Like this?" Claire tried to follow his directions, but it was a bit difficult to balance and painful to put that much pressure on her elbows.

She got the position on her second try, and Dr. Thorton said, "Yup, there you go. Stay just like that. And I hate to do this to you, but we really should do an extra for the 'sir' issue. I am really not that strict about it most of the time. It's just during punishments that I think it is actually really important. Because I need to know that you are learning. So, if you are being disrespectful or challenging my authority even in little ways like that, we just really need to address that in a situation like this. So, I don't know if you agree with that decision, but do you at least understand the reason why you are being punished with an extra?"

"Yes, sir. It's because I... didn't call you sir. And it's very important for me to respect you, especially during a punishment."

"Exactly. Yeah, that's it. Okay, so let's start with the extra. As you take this... and you'll see what I mean about the sting on your skin in a moment... as you take this, think about why using the word 'sir' is important, okay?"

"Yes, sir."

"Alright, are you ready Claire?"

"Yes, sir."

"Keep that bottom very still for me."

Claire felt him gently touch paddle to her naked skin. He tapped once, lining up. The paddle left her bottom and there was an excruciating moment of anticipation. Then... WACK! The sting was terrible, and Claire couldn't help but cry out a little. Claire wiggled around as the pain settled in.

"Owww, oww, oww. Okay. One, sir. Thank you... um can I have another?"

"You need to say 'sir' at the end of every sentence, Claire. Every time in a situation like this."

"Okay, okay. Yes, sir. I'm sorry, sir."

"But the bigger thing is that you need to say 'one extra' for an extra. We talked about this remember?"

"I'm sorry, sir. Please, I'm trying my best."

"Well, this is the second time you have made an official mistake. Do you remember what I said we would need to do in a situation like this?"

"You would... I mean... I would receive two extra swats with the paddle. Um... Is that right, sir?"

"It is. And this would probably be a good time to talk about what would happen after a third transgression. Do you remember what I said about that?"

"I would get... like a whole different punishment? Is that what we are going to do, sir?"

"Well, right now you are on your second transgression, but if anything else happens, yes. Did the girls tell you what happens when we need something a little more than a spanking?"

"No, sir."

"Generally, I move on to a breast punishment, and that's usually pretty intense for girls. So, you would have to take off your shirt and bra. And then, I would give you strokes with the ruler. Like basically right on your nipple. Or maybe a little higher and lower too, depending. That generally hurts a little more than a regular spanking. Well, it definitely will hurt more than this light paddle. And then there's the fact that you'll lose the privilege of having a shirt. And you'll have to take the bra off as well. So, just keep that in mind. We aren't there yet. But... I just don't want you to have to go through all that if we can avoid it. But unfortunately, you still have a long way to go. So, you know... we might have to do that."

"Oh, please sir. I mean... That's so embarrassing. I'm not a young girl anymore. My breasts are... you know... private."

"Claire," Dr. Thorton said in a low and serious, warning tone.

"I'm sorry. I'm sorry, sir!"

"You have one chance to say what I want to hear right now. Otherwise, we can just go ahead and move to the breast punishment."

"No, please! I'll do whatever you say. It's just..."

"Did you say 'no'?" Dr. Thorton raised his voice a little.

"Please..."

"Claire, that was very defiant. I think we are going to have to do that breast punishment after all."

"No, wait! I understand. I'll obey. I won't object anymore. If you say that I need a punishment, I will accept it very respectfully. You can hit me, and I'll count how you want me to and say sir."

"That's good Claire. But unfortunately because you said 'no,' that does count as a third transgression. And that means you will have to go through a breast punishment. So, what I'm gonna have you do is stand back up and take off the rest of your clothes. Once you are fully naked, I'm gonna have you step outside and get the quarter inch ruler. Actually, get the half inch ruler too. Just so I can show you that as well."

Claire cried as she took off her shirt. The doctor admired her breasts as the bra fell away. They were a good size for her body type.

Swirling with embarrassment, Claire went back to the fireplace room, crying. Ms. Thorton saw her and immediately gave her a strong hug.

"Oh sweetie. It must not be going very well. What happened?"

"He says that I have to do a breast punishment," Claire said crying.

"So, you got three transgressions then?"

"Yeah..."

"Are you at least almost done with the spanking? How many strokes did you get through?"

"No... I mean I don't know."

"What number were you on?"

"Just number one."

"Number one? Well, that's unfortunate. You still have a couple more then."

"Or... actually it was one extra."

"So, the last one you counted you said one extra?"

"I was supposed to but I..."

"Ohh... I see. Okay, okay." Ms. Thorton caressed Claire's head and tried to calm her down.

"You can spend a minute recovering with me. It's okay. I don't think he will mind that."

Claire cried for a moment and then when she started to calm down, she asked, "So, how many more do I have? Do you know?"

"How many more if you don't get any extras?"

"Yeah."

"Well, for the spanking, unfortunately it sounds like you didn't count your extra properly. You still need to do all of your extras. And then how many regular strokes did you take."

"We were gonna do the extra first."

"So, you still have all your regular strokes coming too. I'm so sorry Claire. It looks like this isn't going to be such a gentle warm up after all."

"How many is that?"

"Sounds like you have three strokes and three extras left."

"And the breast punishment... How many?"

"Well, that's something that Dr. Thorton will let you know about. It isn't a set number with breast punishments. He might tell you when you go back in. Or he might actually not tell you ahead of time, and just continue until... you know what I mean? Until he feels that you've gotten the message."

Claire started to cry again.

"Honey, you're gonna have to be strong for me, alright?" Claire kept crying.

"You know since you are in a pretty bad place. You might want to be a little more than simply obedient now."

"What do you mean?" Claire sniffled.

"Well, try telling him that you understand why you are being punished and that you are grateful for the lesson. Really show him that you respect his authority."

"Okay... I guess I can do that."

"We don't want to keep him waiting. So, what implement did he say that you need to be hit with? Which one for the punishment on your breasts?"

"The quarter inch ruler."

"Okay. The one you picked up before?"

"Mmhmm."

"Now, you'd better hurry back in there, okay? The girls' cousins -- Tyler and William -- will be over soon, along with a few other guests. Why don't you head back before they arrive?"

"But... he also said to get the half inch ruler, too?"

"Oh okay. That's this one here sweetie. I hate to tell you, but this one is probably gonna be a bit worse. Did he say that he was going to punish you with both?"

"I'm not sure. I... I think he just said he wanted to show me the half inch one?"

"Alright, I'm guessing he will mostly give you the lighter one then. Go on and hurry back now."

Claire walked back to the study with the two rulers in hand. She decided to focus on doing exactly what Dr. Thorton said like Ms. Thorton told her to. She was realizing that she needed to stop getting extras if this punishment was ever going to end.

Claire knocked on the door, but there was no answer. In a rush of anxiety, she remembered what Ms. Thorton said about the guests. She waited for a minute, then knocked again.

"Come in," came the reply.

With tremendous relief, Claire quickly went through the door. She hurried over to Dr. Thorton and handed him the rulers. Dr. Thorton checked the rulers, and they seemed to meet with his approval.

"Okay, we will just do a few on each side. These count as extras. So, count appropriately. And... my thinking is that after the third transgression the position should get a little worse just like the strokes are getting a little worse. So, I'll show you what we can do for that. Can you grab your chair and turn it around so that it is facing away from the desk now?"

"Of course, sir. And um... just let me know how I should make the position worse, as you say. I know that I deserve additional punishment. I know that it needs to hurt more than what we did before. And I'm grateful for whatever you decide. Thank you for teaching me this lesson, sir."

"That's very good of you, Claire. Very good indeed. In fact, I think I will only give you one on each side."

"Thank you, sir."

"Did it hurt much before on your knees? To put them on the wood like that?"

"Yes, it did hurt a bit."

"But not too much?"

"Well, the spanking hurt more I guess."

"Okay. Well, what we are going to do this time is to put a pencil underneath each knee. So, that way there's more pressure on a smaller area. That'll make it a little more uncomfortable. Do you think that will give you the kind of punishment you need?"

"Yes, sir. Thank you, sir. That's um... a very creative idea, sir."

"Very good. So, why don't you begin kneeling on the chair then? And if you wouldn't mind, put your hands above your head and then grab the opposing elbow. Just so your arms are not in the way of your breasts, you know? Very good. Now, just lift up that left knee for me. And here's the pencil. There we go. And the other side. And back down. How does that feel Claire?"

"It hurts, sir."

"Good, good. The other thing that's helpful about this arrangement is that we can both tell if you are moving around, which you should already know is forbidden while you are being punished, right? So, what I want you to do is tell me if you feel either pencil move on to another side. And then I'll give you an extra or two, okay?"

Claire tensed at the thought.

Quietly she said, "Yes, sir."

"There is one last thing to cover for breast punishments in particular. When a girl's nipple is perky or erect, it becomes much more sensitive. Rather than strike you harder, which would cause more damage, I would much rather maximize your sensitivity to the pain. So, we have a rule here that breast punishments are always done on an erect nipple. We have a process that forces the nipple to respond appropriately. Ice is very stimulating and quickly makes the nipple hard and erect. However, it can also be a bit numbing, and I'm sure you can see why that would be counterproductive for our intentions here. Therefore, we will use some heat and friction to complete the procedure. So, you will need to go through this procedure now before I strike you with the ruler. Do you prefer to start on the left or the right, Claire?"

"Whatever you think is best, sir."

"Alright, then. Let's start with the left. Though, in the future Claire, if I ask your opinion please provide a bit more of an answer. If I needed to make the decision, I would have told you how to proceed instead of asking for your opinion."

"Yes, sir. I'm sorry."

Dr. Thorton went over to the phone and dialed something: "Hi Nancy, can you bring a bucket of ice to the study as soon as possible? Mmhmm. Oh, and some warm towels. Thanks, bye."

"It'll just be a few minutes, Claire. Remember to be as still as you can, okay?"

After several minutes of waiting in the painful kneeling position, Claire could not stop herself from speaking up any longer.

"Sir, I'm so sorry to bother you."

"It's not a bother Claire. What's on your mind?"

"Okay... I... I really, really don't mean to disrespect your authority or anything but I was just noticing that it has been a long time since you asked for the ice. And my knees are really starting to hurt. I know you said that would be part of the punishment... to make the position more painful. But I don't know if you intended for me to wait like this. I could even... like get the ice for you... just so that it would be faster for you..."

She looked at Dr. Thorton pleadingly.

"Claire you were doing so well. I thought perhaps I was getting through to you, and now you surprise me. I am administering a punishment for you right now. You do understand what that means, right? If I were to let you decide that a certain level of pain was enough then it would not be much of a punishment, would it? You need to let me decide such things. You may ask for additional punishments, but goodness please do not ask for anything less than what I expect."

"I'm s-s-sorry--" Claire was cut off by a knock and the entrance of Nancy with a rolling cart, which carried a pitcher of ice and a set of hot towels.

"Here you are Dr. Thorton. Is this the new girl?"

"Yes. Her name is Claire."

"She's a pretty one."

"Indeed, but still rather disobedient."

"I'm sure she'll learn."

"Quite right."

"Anything else, sir?"

"That'll be all for now Nancy."

"Claire we will have to talk about this attitude problem of yours later. For now, we need to move forward."

Dr. Thorton grabbed a piece of ice and walked over to where Claire was kneeling. Claire was breathing quickly.

"Just relax for this part. The ice will not hurt you. It may be a bit of a shock to the system at first, but that will pass in a moment. Okay, here we go..."

Claire's nipple perked up in response to the ice as if it had a mind of its own.

"That looks about right. Do your nipples generally get any more erect than this or is this about the limit generally?"

"That's definitely the limit, sir," Claire said while breathing heavily.

"Good, good. So, that means we can warm you up now. I'm going to touch your breast with my hand, okay? This is not a punishment. It's just to increase the sensitivity. Are you ready?"

"Please proceed, sir."

"Okay, take a deep breath. Just relax."

Dr. Thorton caressed Claire's left breast. Then, he squeezed it more firmly. Then, he began to gently rub Claire's nipple back and forth. Claire thought her nipples were very sensitive when he touched her like that. It was sort of uncomfortable at first, but then she started to like the sensations. Though, she tried -- not very successfully -- to hide it. Dr. Thorton then placed a warm towel on her breast, and she liked that as well. He ran his finger over her nipple intently a few more times.

"Is that feeling pretty sensitive now?"

Claire nodded quickly.

"If we've done the procedure successfully, and it looks like we have, then you should feel the ruler really intensely. It's actually a very different experience."

"I can imagine, sir."

"We are gonna go with the thinner ruler here. Stay very still, okay? Actually, can you arch forward just a little? Right there. And here we go."

Dr. Thorton swiftly struck the ruler against her breast right over the nipple. Claire tensed and cried out, but she made sure not to move. The pencils stayed in place.

"One extra, sir. Thank you, sir. May I please have another, sir?"

"Yes, you may, but first we need to prepare the right side."

Claire felt more scared now that she knew what the ruler would feel like. It was quite a shock after the doctor's preparation.

Despite Claire's anxiety, she still felt a bit comforted as Dr. Thorton worked on her right side until her nipple was as erect and sensitive as he wanted it to be. When he had finished, Dr. Thorton picked up the thicker ruler.

"Now, let's do the half inch on the right. The reason that I asked you to get this one..." he explained while setting up, "...is that the thicker implements feel a little different. And I just wanted you to get acquainted with something in the half inch territory. Pay attention to how this feels, and I think you'll understand the difference."

"Yes, sir. I'll pay attention to that, sir."

Dr. Thorton struck Claire's right breast and the weight of the ruler was clearly greater. Claire was a little off balance from the blow. Time went into slow motion for Claire. She wasn't allowed to move her hands to help stabilize herself. No! she thought. Was that a pencil shifting under her left knee? It was. There was a quiet clicking sound when it happened. But Dr. Thorton didn't seem to notice. Claire couldn't decide whether she should speak up. Her nipples were hurting, and she was hiding a lot of shame and resentment. She couldn't bear the thought of asking for more.

"Two extra, sir. Thank you, sir."

Nervously, she waited.