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On Tuesday morning Cian woke before mommy came to get him. Once again he awoke needing to pee and once again he knew he couldn’t get up on his own or call mommy. Rather than fight it he decided to just relieve himself so he could get back to sleep for a while. It was easier this morning to just let go. He felt the diaper get warm and wet. It wasn’t that bad, in fact, it felt pretty good. Cian rolled over and fell back asleep.
 
Mommy came into Cian’s room and rolled up the window blind. The spring sunshine flooded the room and woke Cian.
 
“Good morning, Cindy.”
 
“Good morning, mommy.”
 
“How do you feel this morning, Cindy?”
 
“I’m okay, mommy, but my bum is still really sore.”
 
“I’m sure it is, young lady, but that is the result of your own misbehavior. If you don’t want to be spanked, behave yourself.”
 
“Yes, mommy. I’m sorry.”
 
“I’m sure you are sorry. Now, I thought I smelled something as I came into the room. Did you wet your diapers?”
 
“Yes, mommy. I couldn’t help it.”
 
“It seems that you have used that excuse before. I think you’re really just becoming a bed wetter.”
 
“I’m not, mommy. Really I’m not. I wake up knowing I need to pee but I am not allowed to get up or call you so I have no choice.”
 
“Well, it doesn’t matter one way or the other. You’ll be in night diapers until September no matter what.”
 
Mommy spread out the changing mat on the floor and got the wipes from the dresser.
 
“Lie down, Cindy. I’ll get you out of those wet diapers and clean you up enough for you to take your shower.”
 
“Yes, mommy.”
 
Cian laid down on the changing mat. Mommy removed his diapers and cleaned him up.
 
“When do you have gym this week?”
 
“Only, Friday, mommy.”
 
“That’s good. That will give you almost a whole week in panties.”
 
Cian’s little peeny twitched as mommy said panties. She looked down with a smile.
 
“I’ll lay out your clothes while you shower. Come down for breakfast once you’re dressed.”
 
“Yes, mommy.”
 
Once Cian was finished in the bathroom he returned to his room. His eyes were immediately drawn to a pair of bright red nylon panties on top of the rest of his clothes. He was puzzled because he knew that he didn’t have red panties. Something odd was going on.
 
Cian pulled on the red panties and noticed they seemed very snug. They forced his little member up against his body. He immediately started to react to the soft silky feel. The tight panties wouldn’t allow his little peeny to erect until he reached inside and adjusted things to take off the pressure. As he moved to put the rest of his clothes on the silky red panties rubbed against his swollen member. It felt wonderful and Cian knew he’d feel this all day. It also was snug across his sore bum and that made it feel worse. Cian knew it was going to be a long day.
 
Cian could smell cooking bacon so he hurried down for breakfast. As he was eating, his mommy spoke to him.
 
“Did you notice something new this morning, Cindy?”
 
Cian paused for a second. “Oh, do you mean the new red ones?”
 
“The red what, Cindy?”
 
Cian blushed at the thought of saying it out loud.
 
“Say it, Cindy. Say, ‘my red panties’.”
 
“My … my red … p … pan … panties.”
 
Cian blushed even deeper and mommy smiled.
 
“Pretty soon you’ll be able to say that easily, Cindy. Now, those panties are special. Have you noticed they are tight?”
 
“Yes, mommy. They are really tight.”
 
“They are size eights and too small for you on purpose. I want you to really feel them all day so you’ll think about them. The color is no accident either.”
 
“I don’t understand, mommy.”
 
“These are what I’m going to call your spanking panties. You will wear them on any day when you’re going to get an especially hard spanking. They will make you think about what’s coming all day.”
 
Cian sniffled, “Yes, mommy.”
 
“So just remember that you’re getting spanked for repeated disobedience this evening and it’s a spanking you won’t forget.”
 
“Yes, mommy.”
 
“Now you better get going and don’t forget to stop and talk to Mrs. Kerry for a few minutes.”
 
“I will, mommy.”
 
Cian grabbed his schoolbag and hurried off to school. On the way, he stopped and knocked on Mrs. Kerry’s door.  She opened it for him.
 
“Good morning, Cindy. Come in, please.”
 
“Good morning, Mrs. Kerry. Yes, ma’am.”
 
“I won’t keep you long this morning. Panty check!”
 
It took Cian a little longer than usual to get into position because of the tight panties.
 
“That was close, young lady. You almost took too long. Why were you slower than usual, Cindy?”
 
“These new panties are extra tight, ma’am.”
 
“Spanking panties are supposed to be tight. I like the color too. I think mommy’s plan is to make your bottom match by the end of your spanking.”
 
“I guess so, ma’am.”
 
“You will find out. I’m sure. Now run along to school and stop back on your way home. I have something for you to take to your mommy.”
 
“Yes, ma’am.”
 
Cian pulled up his red panties and his pants. He made sure to tuck in his shirt.
 
“I’ll see you after school, ma’am.”
 
“Have a good day, Cindy. Try not to think of the spanking you’re getting tonight.”
 
Mrs. Kerry smirked as Cian let himself out.
 
As Cian sat in class he was constantly aware of the tight panties. As sore as he felt sitting yesterday, this was worse. What really made it worse was the constant stimulation of his little member.
 
Cian used his breaks to go to the bathroom to relieve himself in every way. Just getting the tight panties off of his sore bottom felt good and jerking himself off felt great. By the end of the day he was a bundle of nerves. The thought of his impending spanking hung over him like a dark cloud. He just wanted the week to be over and it was only Tuesday.
 
On the way home Cian slowly walked up to Mrs. Kerry’s door and knocked. She opened the door and gestured for him to come in. Cian entered the house. Mrs. Kerry put him through another humiliating panty check. As Cian pulled up his panties and pants Mrs. Kerry washed her hands. Afterwards she turned to Cian and spoke.
 
“I have a special present for you to take home. Please give it to your mommy. It’s your present, but mommy will take care of it for you.”
 
“Yes, ma’am.”
 
Somehow Cian knew this was not going to be a present he would enjoy. Mrs. Kerry opened a paper bag on the table, reached in and pulled out a wooden paddle.
 
Cian gasped as Mrs. Kerry handed him the paddle.
 
“I had a friend of mine make this just for you. It’s been carefully made as you can see. It’s made of oak and should last for a lifetime.”
 
Cian shuddered and reluctantly took the paddle like it was red hot. He held it out at arm’s length with his fingertips as he examined it. The paddle was sixteen inches long including the four inch handle. The paddle part was three inches wide and three eighths of an inch thick with rounded corners and edges. It had three neat rows of holes. Everything including the holes was sanded very smooth. At least he wouldn’t get splinters. The handle was wrapped in red leather and there was a small metal screw eye at the end of the handle. It was painted a glossy bright pink. There was dark red lettering too. One side read, “Cindy’s Spanking Paddle”, and the other side read, “For Naughty Cindy.” Cian stood in silence wondering how much this was going to hurt.
 
Mrs. Kerry put her hands on her hips and tapped her foot impatiently.
 
“Young lady, I’m waiting.”
 
It took Cian a moment to understand.
 
“Thank you, Mrs. Kerry.”
 
“That’s better. You’re welcome, Cindy. As you can see it’s just like my own paddle and it is made to cause a nasty sting in the bare bum of a naughty little pantywaist. It’s light enough so that it won’t bruise very much so it can be used often. I am sure you’ll come to dread it  and I hope your mommy uses it frequently.”
 
Cian started to sniffle as Mrs. Kerry was speaking. This paddle was really scary and Cian already hated it. He knew that he’d be getting this tonight and the thought almost made him pee his panties.
 
“You can see the screw eye in the handle. That’s used to hang it up, of course. I’m sure your mommy will find a good place to hang it up where you can see it often. Maybe in a nice place like your bedroom or maybe the living room or kitchen where visitors can see it too. That screw eye has another use too.”
 
Mrs. Kerry reached into the paper bag again and pulled out a loop of red ribbon with a snap hook on the end. she stretched it out in her hands.
 
“With this, the paddle can be hung around your neck too. That will keep it nice and close and ready for instant use.”
 
As Mrs. Kerry was explaining all of this, Cian’s sniffles turned into soft crying. This was awful. How could his life have changed so much in less than a week? Cian squirmed and once again felt the soft silky panties slide over his little peeny. In a way, that was really the answer to his question. All he had to have done was ignore those clotheslines and none of this would have happened. It was his own fault. He wondered what he would have done if he had known at the time. What confused him is that he didn’t know the answer to that question.
 
“Now, young lady, it’s time for you to get home.”
 
Mrs. Kerry ran the lanyard ribbon through her fingers while Cian stared in horror.
 
“Cindy, I can see you’re wondering if I’m going to make you wear your paddle home hanging around your neck.”
 
“Please don’t make me do that, Mrs. Kerry. Anyone who sees me will make fun of me and they will tell everyone else.”
 
“That is true, Cindy, and we don’t want you to be teased for what you are. Some humiliation is part of a punishment, but you shouldn’t feel humiliated at any other time. You may carry the paddle and the lanyard home in the paper bag.”
 
“Thank you, ma’am.”
 
Cian was confused again. Mrs. Kerry was so strict and demanding but she was also protecting him from the ridicule he’d get if anyone found out. It was like she cared about his feelings. He was very grateful that she understood how he felt. She was still very intimidating but she also had a warm side.
 
Mrs. Kerry put the lanyard into the bag and Cian laid the paddle in too. He picked up his schoolbag and Mrs. Kerry handed him the paper bag with the paddle.
 
“Okay, Cindy, straight home now.”
 
“Yes, ma’am, and thank you again for not making me wear the paddle home.”
 
Cian hugged Mrs. Kerry.
 
“Oh my goodness, Cindy. You’re welcome. Now, run along.”
 
“Yes, ma’am.”
 
Cian stepped outside as Mrs. Kerry closed the door behind him. He looked up at the empty clotheslines and smiled at the memory.
 
It didn’t take long for Cian to walk home. He entered the kitchen and called out.
 
“Mommy, I’m home and I have something from Mrs. Kerry.”
 
Mommy walked into the kitchen and kissed Cian on the forehead.
 
“Welcome home, Cindy. Did you have a good day?”
 
“No, mommy, not really. It hurt to sit all day and I kept thinking about tonight.”
 
“I’m sure that you were sore and I know those snug panties were a reminder to you all day.”
 
“Yes, mommy.”
 
“So let’s see what Mrs. Kerry gave you.”
 
“Yes, mommy.”
 
Cian slipped the schoolbag off of his shoulder and set it on the floor. He held out the paper bag and mommy took it from him. She reached in and pulled out the paddle.
 
“Oh my, Cindy. This is beautiful.”
 
She ran her hands over all of it.
 
“It’s so smooth and the rounded edges and corners mean it won’t break your skin. Even the edges of the holes are smooth. That means they won’t blister but the holes will make sure it hurts a lot. It’s perfect for you and it even has your name on it.”
 
Cian looked down at the floor while his mommy gushed over something made to deliberately cause him pain.
 
Mommy reached into the bag and brought out the red lanyard. She smiled at Cian. She used her index finger to lift up his chin until their eyes met.
 
“I won’t use this outside of the house. Even in the house I’ll only use it if you are in major trouble and need it as a reminder to behave.”
 
“Thank you, mommy.”
 
“I put up hooks in here, the living room, your bedroom and the bathroom. I want you to put your paddle and the lanyard on the hook in your bedroom. Change into the clothes laid out for you on your bed and come back for an inspection.”
 
Cian took the paddle and lanyard to his room. He looked around for the hook and saw it on the wall beside the dresser. He hung the lanyard and paddle on the hook. He turned towards the bed and saw the same outfit as yesterday, a white blouse, a red plaid jumper, red knee socks and the red and white saddle shoes were on the floor.
 
Cian changed into the girls’ clothes and took care of the boys’ clothes he had been wearing. He couldn’t help looking at the paddle hanging on the wall. He could feel his bottom twitch as he looked at it. He knew without doubt that it was going to really hurt and the words embarrassed him.
 
Cian went downstairs and walked into the kitchen. He curtseyed and stood silently waiting for his mommy to acknowledge him.
 
“Okay, Cindy. Please turn around slowly.”
 
Cian curtseyed, “Yes, mommy” and turned slowly in place.
 
“Very nice, Cindy. Now, go do your homework and call me when you’re finished. Remember to write carefully so you don’t have to rewrite your work.”
 
Cian curtseyed again, “Yes, mommy.” and took his schoolbag up to his room.
 
He sat at the table and did his homework. He kept looking up at the paddle hanging on the wall. He decided he’d rather have the side that said, ‘Cindy’s Paddle’ showing instead of ‘For Naughty Cindy’ so he got up and turned the paddle the other way around. It didn’t really help.
 
Cian finished his homework and called mommy to come and check it. It didn’t take long for her to respond. Cian stood and curtseyed as mommy came into the room.
 
“Show me the homework, Cindy.”
 
Cian pointed out the work he’d done today and stood as mommy looked it over.
 
“You’re math is all correct today and I see that your handwriting is much better than your older work. I can see that checking your homework is going to help your grades. I should have been doing this all along. I certainly will from this day forward. I also want you to tell me when you have tests or projects coming up.”
 
Cian curtseyed, “Yes, mommy. I’ll tell you.”
 
“That’s good. It’s time for dinner. Please go and wash up and come down to the kitchen.
 
Cian curtseyed, “Yes, mommy.”
 
As mommy left to go downstairs Cian noticed how automatic his curtsey had become. It was getting harder to remember not to curtsey when he was dressed as a boy than it was to curtsey when he was dressed as a girl. It made him realize that he was changing, but he still wasn’t sure how he felt about it.
 
Cian entered the kitchen, curtseyed and sat at the table. Mommy brought over two plates of dinner.
 
“Cindy, I notice how easily you sit down now in a dress. You’re becoming a proper young lady.”
 
Cian blushed and then blushed deeper when he realized that he’d taken that as a compliment.
 
After dinner Cian helped clean up the kitchen. Once that was done he expected mommy to let him have some free time, but not tonight.
 
“Panty check!”
 
Cian spun around, hiked up his jumper and pulled his panties down to his knees. He stood with his legs apart and his hands on his knees.
 
Mommy examined his panties carefully. She noticed some spots on the front that showed easily on the red nylon of the panties. They were certainly not pee stains. She smirked knowingly.
 
“Hold up your dress in the back and leave your panties around your knees. Go to your room, Cindy, and wait for me standing in the corner. Get your nose right in and stay still.”
 
 Cindy stood up, turned and curtseyed, “Yes, mommy.”
 
He waddled out of the kitchen. He had to go slowly as he climbed the stairs. All too soon he was standing in the corner. He couldn’t tell how long he stood there but it felt like forever.
 
Eventually mommy came into the room.
 
“Turn around, young lady.”
 
Cian turned from the corner and curtseyed.
 
“It’s time for your bath so let’s get those clothes off. but don’t put the panties in the laundry. You’ll be wearing them again tomorrow so bring them to the bathroom so you can wash them.”
 
Cian curtseyed, “Yes, mommy” and started to undress. He felt a deep sinking feeling in his stomach as he took off the tight red panties. Wearing them tomorrow after tonight’s spanking was going to be extra miserable.
 
Cian carried the little red panties into the bathroom, curtseyed and waited for mommy.
 
“Start by washing out the panties in the sink. I left a bar of Sunlight laundry soap on the vanity so use that.”
 
Cian curtseyed, “Yes, mommy” and went to the sink. He filled the sink with warm water and rinsed the panties. As he picked up the Sunlight soap he remembered what Mrs. Kerry had said about its taste. He just hoped that mommy didn’t know.
 
Cian lathered up the panties with the soap and rinsed them out several times until he was sure that they were clean. He gave them a final rinse under warm water and turned to see mommy sitting on a chair by the bathtub.
 
“Hang them on the towel rack and get into the bath.”
 
Cian curtseyed, “Yes, mommy” and got into the tub. Mommy washed him from head to toe. She gave his bottom a particularly thorough washing that aggravated his already sore bottom. She toweled him off until his skin glowed a healthy pink. Mommy hung up the towel and took Cian by the hand. She led him back to his room.
 
Mommy sat in the chair.
 
“Fetch your new paddle, Cindy.”
 
Cian curtseyed, “Yes, mommy” and went to get the paddle. As he took it down from its hook he started to cry. He knew this was going to really hurt and he was scared.
 
Mommy took the paddle from Cian and turned him over her knees. Cian couldn’t help but notice how strong mommy was and how easily she just lifted him into the spanking position.
 
“Why are you going to be spanked, Cindy?”
 
“I was disobedient, mommy, more than once.”
 
“You certainly were, young lady. You are going to learn to be obedient instantly, completely and without question or your little bum will match your punishment panties all the time. Understand?”
 
“Yes, mommy.”
 
“I hope so, young lady, because I hate to do this as much as you do. I don’t want to spank you, but I will until you learn to behave. Now, put your right hand behind your back.”
 
Cian reached up and put his right hand behind his back. Mommy took hold of his wrist. Cian could feel her shift her weight as she raised the paddle. She brought it down right across the middle of Cian’s soft bum.
 
Cian squealed like a little girl and his crying instantly turned into helpless sobbing. He had been spanked before many times but this was a whole new level of pain. It hurt even more than the paddling Mrs. Kerry gave him. Getting spanked right after a bath made it far worse.
 
Mommy paddled on and on while Cian screamed and cried. In moments his face was covered in tears, snot and drool. His world was reduced to his bum and his paddle. He couldn’t believe how painfully mommy was spanking him. He felt like he’d never sit down again.
 
After what seemed like hours mommy stopped the spanking. It took Cian a while to realize that it had stopped. He was crying uncontrollably when mommy stood him up. She held him by his wrists to make sure that he didn’t try to rub his sore bum. She held him like that long enough for him to regain some control.
 
“No rubbing, young lady.”
 
Cian nodded because he couldn’t speak yet. With mommy holding his wrists he couldn’t curtsey either.
 
“Now, it’s straight to bed, Cindy. No corner time tonight. You did some before the spanking and I want you crying yourself to sleep tonight. Let’s get you diapered and into bed.”
 
Mommy got the diapers from the drawer and led Cian to the bed. She helped him lie down on on his back on the bed. He squealed as his sore bum met the soft bedding. He was still crying when mommy finished diapering him. She stood him up again and got a pink one piece footed sleeper from the dresser. She held them open as Cian stepped into the legs. Mommy lifted the top and Cian worked his arms into the top. Finally mommy zipped up the back. The sleepers were made of a fleece material and Cian noticed how warm they were. Between the diapers and the sleeper Cian’s bum would not cool off for a long time.
 
Mommy turned back the covers and helped Cian get into bed. He laid face down and was sobbing into his pillow.
 
“I hope that I don’t have to do this again for a long time, Cindy. I love you, but I will make you behave no matter what it takes.”
 
She leaned over and brushed Cian’s hair back from his forehead. She hugged and kissed him. Cian just lay still and sobbed.
 
Mommy went to the doorway.
 
“Goodnight, Cindy. See you in the morning.”
 
She turned out the light and closed the door behind her.
 
Cian laid in bed crying for a long time. His bum was so sore he couldn’t sleep. In a strange way he liked that his mommy had changed. Mommy was now so strict and he knew he’d never get away with anything ever again. It made him feel very secure.
 
As Cian writhed with the pain in his bum he also rubbed his peeny into the diapers against the bed. I wasn’t long before Cian’s peeny reacted and engorged. His whole body heaved when he reached climax.
 
He finally felt like he could sleep. He turned over the tear soaked pillow and laid his head on the cool side. He was still trickling tears as he drifted off to sleep.
What a day. It will be interesting to see how things progress for Cian. As tortuous an experience as that was for him, you feel he could almost adapt if that was to be a daily routine... but there are sure to be new experiences added in and Ms Kerry is something of a live wire. 

She was somewhat merciful today in some respects but one gets the impression it might be a tougher ride if he catches her on a bad day.  Big Grin
Wow, Cian/Cindy-Mommy-MrsKerry are all getting along exquisitely.
(01-27-2021, 06:49 PM)afp Wrote: [ -> ]Wow, Cian/Cindy-Mommy-MrsKerry are all getting along exquisitely.

Wow exactly!! What a wonderful story! I felt like I was living every moment along with poor little Cindy.
I think part of the transition process is when Cian/Cindy starts to see that Mrs. Kerry and his mommy are helping him to become what he wants to be. Cindy will always need strict discipline, but in time she'll come to accept it as a necessary part of her life. So she'll fear the punishment not the one doing it.

I don't want things to get too repetitive so I'm thinking of writing Wednesday and Thursday as a single installment with less detail than usual, but I may end up on a roll. I'll try to get it written in the next few days.
Cindy, I share your vision on Cindy’s transition process.
I’m looking forward to reading more.
So absolutely beautiful! This is a lovely tale of a strict but caring Mommy and her sissy son. Cindy is so lucky to be raised in a strict disciplinary regime and she realizes this truth! Strict discipline, petticoating, rules and chores will help her to grow up responsibly and avoid all of those things that cause teenagers such angst and trouble...A line that struck me as so very true..."Mommy was now so strict and he knew he’d never get away with anything ever again. It made him feel very secure"...there is such security in knowing that you will be held accountable and exceptions will never be granted for poor behavior. I love, love, love this story...the single best story in its genre I have ever read! I love Cindy's special paddle...I loved the detailed description of it...and I love the spanking panties...every sissy should own a pair! Thank you!
Something that might be lurking in Cindy's future .
Bill that’s a great picture. I hope the naughty boys Mommies give them a little of what’s good for them too.
That is a good picture! I have no personal experience with enemas but I may work one into the story. I know that it's a big plus for a lot of people.
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