Petticoat Discipline Quarterly Forum
Panty Lines - Chapter 5-1 Monday - Printable Version

+- Petticoat Discipline Quarterly Forum (https://petticoated.com/forum)
+-- Forum: The Nursery (https://petticoated.com/forum/forumdisplay.php?fid=20)
+--- Forum: Adult and Sissy Baby Fiction (https://petticoated.com/forum/forumdisplay.php?fid=24)
+--- Thread: Panty Lines - Chapter 5-1 Monday (/showthread.php?tid=3966)

Pages: 1 2


Panty Lines - Chapter 5-1 Monday - Cindy - 01-24-2021

Here is the start of Cian's week. I'll try not to make the rest of the week too repetitive, but his day to day routine is naturally similar.

Chapter 5 – Cian’s First Week in Panties
 
On Monday morning Cian woke up early. He looked at the clock and realized he was awake well over an hour before he normally got up. He rolled over and tried to get back to sleep, but couldn’t. He had to pee and there was no way he could ignore it. He wanted to call for his mommy, but she had made it quite clear that he wasn’t to make a sound until she came in to get him up. Cian squirmed for a while and tried to cross his legs but the thick diapers prevented it. Finally, he had no choice, he had to use his diapers.
 
Cian tried to relax and use his diapers but it was harder to let go than he thought. He finally managed a little spurt and followed by fully relaxing and soaking his diapers.
 
Just as well, he thought. This will cover the mess I made last night. He rolled over and did fall back to sleep.
 
“Wake up, Cindy. It’s morning and time to go to school.”
 
Cian awoke as his mommy gently shook him by the shoulder. He sat up and yawned. He wondered if wetting his diapers had been a dream until he felt the cooling wet diapers.
 
“Good morning, mommy.”
 
“Are you wet?”
 
Cian blushed, but didn’t answer.
 
“I can tell by that blush that you are. It seems that you really are a bed wetter now.”
 
Cian blushed even deeper.
 
“Okay, Cindy, out of bed and lie down so I can take off that wet diaper.”
 
As Cian got out of bed, mommy put a plastic changing mat down on the floor. She patted it and Cian laid down on top of it. It only took mommy a couple of minutes to remove the wet diaper and wipe him down.
 
“Go and have a quick shower and I’ll lay out your clothes. You don’t have gym today, do you?”
 
“No, mommy, not today.”
 
“Good. That means today will be your first day in panties at school. You will have to be careful to keep your shirt tucked in so they don’t show. It’s very naughty for a little girl to let anyone see her panties.”
 
Once again Cian was shocked to hear the same warning. It must be one of those secret universal rules for girls that boys are never told.
 
Cian had a quick shower then completed his morning routine in the bathroom and returned to his bedroom. Mommy was not there but his clothes were laid out on the bed. His eyes were immediately drawn to the panties on top of everything else. They were white cotton briefs with little red roses. Cian picked them up and pulled them on. He immediately got excited at the look and feel of the little panties. His peeny throbbed with excitement and he wondered how he could make it through the day wearing forbidden panties. He finished getting dressed and he was sure to tuck in his shirt.
 
Cian went downstairs and entered the kitchen. He curtseyed. “What’s for breakfast, mommy?”
 
“Just cereal today, Cian. Sit down and pour the milk.”
 
Cian curtseyed, “Yes, mommy.”
 
“Cian I know this might be difficult to keep straight, but do not curtsey when you are dressed as a boy.”
 
“Okay, mommy. I’ll remember.”
 
Cian sat down and ate his breakfast. Once he was done he put the dishes in the sink. He was about to leave for school when he remembered his schoolbag was at Mrs. Kerry’s house.
 
“Mommy, I left my schoolbag at Mrs. Kerry’s house and I need it.”
 
“I know, Cian. Mrs. Kerry and I planned for this. You cut through her yard on the way to school every day. Just stop and knock on the door. She’s expecting you.”
 
“Okay, mommy.”
 
Cian walked towards school and when he got to Mrs. Kerry’s house he knocked. She must have been close by because she answered the door quickly.
 
“Come in for a minute.”
 
“Yes, Mrs. Kerry.”
 
As they stepped in the door Mrs. Kerry continued. “I see your mommy explained that you don’t curtsey when you are dressed as a boy.”
 
“Yes, ma’am.”
 
“That’s good. It’s important that you remember when you should and when you shouldn’t curtsey. We do not want you to be embarrassed or get teased because you’re different. Hopefully, it won’t be a problem for too long.”
 
Cian followed Mrs. Kerry into the kitchen. His schoolbag was on the floor where he left it.
 
“Cian, we used your schoolbag today as an excuse to make sure that you had to stop here on your way to school. However, you will stop here on your way to school everyday. Sometimes I will tell you to stop here again on your way home. Understand?”
 
“Yes, ma’am.”
 
“Now, the reason you stop here every morning is so that I can check your panties. Panty check!”
 
Cian hesitated for a fraction of a second before he quickly pulled down his pants. He pulled his panties down inside out around his knees, spread his legs, bent over and put his hands on his knees.
 
“Well done, Cindy. I’m very glad that you remembered and obeyed so quickly. I’m sure your bottom is sore enough already without getting spanked again by me.”
 
Mrs. Kerry checked the panties and wiped Cian’s bottom deeply with a tissue. She examined the tissue and tossed it in the garbage. As she washed her hands she spoke.
 
“Nice and clean, young lady. Now you may get dressed again.”
 
Cian pulled up his panties and then his pants. Once again he carefully tucked in his shirt.
 
“Okay, Cindy, you better get your schoolbag and get to school. You wouldn’t want to be late, would you?”
 
“No, ma’am.”
 
Cian squatted down and picked up the schoolbag.
 
“That’s fine, Cindy. Even little boys are allowed to squat down to pick things up.”
 
“Yes, ma’am.”
 
“You are to stop here on your way home today for a panty check. Now you better run along.”
 
“Yes, ma’am. I’ll see you later. Bye.”
 
“Bye, Cindy.”
 
Cian made it to school with time to spare. When the bell rang he made his way inside. He noticed how all of the girls held the back of their dresses and skirts in close as they climbed the stairs. Cian got to his desk and hesitated before he sat down. His bottom was still very sore and the idea of sitting all day on that hard wooden seat made him cringe. He knew he had no choice and it wouldn’t be nearly as painful as sitting on the stool with a bare bottom right after a spanking. He eased himself into his desk.
 
Cian squirmed in his seat all day long. There was no way he could get comfortable. His bum was just too sore. What made it even worse is that Cian knew this would be the same everyday all week.
 
Cian was also uncomfortable in another way. The soft cotton panties rubbed against his little peeny each time he shifted position. It throbbed with excitement and the lack of relief made him sore there too. He could hardly wait for the mid-morning break.
 
Once his class was dismissed for the mid-morning break he headed straight for the boys’ room. He went into the stall at the far end and carefully locked the door. He pulled his pants down to his ankles but was careful only to pull his panties down to mid-thigh. He didn’t want anyone to notice his panties below the stall door. He grabbed a handful of toilet paper in his left hand and started stroking his erect peeny with his right. It didn’t take long before he spurted into the toilet paper. He put it between his legs and dropped it into the toilet. As his erection subsided he was able to pee. He used a square of toilet paper to wipe the tip when he was done. He knew he was in for a panty check on the way home and wanted to be sure there would be nothing for Mrs. Kerry to find.
 
Cian repeated this bathroom routine at lunch and at the mid-afternoon break. His little peeny was red and sore by the end of the day but it was still erect whenever the thought or feel of his panties came to his attention. It was wonderful and terrible at the same time.
 
On the way home Cian stopped at Mrs. Kerry’s house as he was told. She invited him in and did the panty check.
 
“Well, Cindy, it seems there are a couple of spots on the front of your panties. They are not pee stains so they must be something else. Do you still get aroused by the panties?”
 
“Yes, ma’am. They still excite me all the time.”
 
“That must be very painful after a while. It’s a good thing you’re so young and full of energy.”
 
“Yes, ma’am. I’m sore there and in my bum too. It makes it hard to sit down.”
 
“I remember when I was a girl, Cindy. My parents used to say, ‘I’ll spank you so hard you won’t be able to sit down for a week.’ Now you can understand what they meant, can’t you?”
 
“Yes, ma’am. I will get another spanking every night for the next four nights. I will be really sore by Friday.”
 
“Yes you will, young lady. That’s the way it should be for little pantywaists like you. You should be getting spanked at least two or three times every week. If you do come to stay with me for the summer you can count on that as a minimum.”
 
Cian gulped and felt a horrible sinking feeling in the pit of his stomach. Mrs. Kerry was so strict, demanding and punished severely and yet she was also so pretty that he wanted to please her.
 
“Yes, Mrs. Kerry. I understand.”
 
“Very well, Cindy. You better be on your way home now. I’ll see you tomorrow morning.”
 
“Yes, ma’am. Bye for now.”
 
“Bye, Cindy. Hurry home. Mommy is waiting.”
 
“Yes, ma’am.”
 
Cian hurried home. Mommy was waiting in the kitchen when he came through the door.
 
“Hello, Cindy. How was your day?”
 
“School was fine, mommy, but it sure hurt to sit down all day.”
 
“I’m sure it did, but that’s part of the punishment and if you don’t want to be spanked then all you have to do is behave yourself.”
 
“Yes, mommy. I’ll behave.”
 
“I’m sure you will, but you still are getting spanked tonight for getting detention last Friday. Those spankings can’t be avoided.”
 
“Yes, mommy. I understand.”
 
“Good girl! Now, go and change into the clothes on your bed. Hang up your pants so you can wear them again tomorrow.”
 
“Yes, mommy.”
 
“Remember, young lady, the curtsey rules always apply when you are dressed as a girl.”
 
“I will, mommy.”
 
“Good. Now scoot!”
 
Mommy gave Cian’s bottom a gentle swat to send him on his way.
 
He hurried to his room to see what mommy had left for him to wear. He saw a white blouse with short puffy sleeves and a wide collar, a red plaid jumper, and red knee socks on the bed and a pair of red and white saddle shoes on the floor.
 
Cian was surprised that his first reaction was disappointment. It wasn’t that there was a girls’ outfit waiting for him. He knew that. His disappointment was that the outfit was not as girly and frilly as what he had been wearing all weekend. It seemed too plain. He stopped with a gasp as those thoughts ran through his head. What is the matter with me? I don’t want any of this so why would I be disappointed that the clothes aren’t girly enough? Cian’s feelings were still all over the place. He didn’t know what he wanted.
 
As soon as he changed he went back downstairs to find his mommy. He went into the kitchen and curtseyed.
 
“You look very nice, Cindy.”
 
“Thank you mommy.”
 
“You look like something’s wrong, Cindy. What is it?”
 
“I don’t know mommy, this dress just was unexpected.”
 
“You knew you were changing into girls’ clothes after school. So what was unexpected?”
 
“I don’t know how to explain it, mommy. It just feels wrong.”
 
“Oh, wait a second. I think I see the problem. It’s not as pretty as the pink party dress and petticoat you were wearing yesterday. That’s it, isn’t it, Cindy?”
 
“Maybe, mommy.”
 
“Well, you need to know that little girls don’t wear fancy party dresses everyday. You will wear them much more than most little girls, but you’ll also wear more everyday clothes too.”
 
“Yes, mommy.”
 
“Now turn around slowly so I can see you.”
 
Cian curtseyed, “Yes mommy” and slowly turned around.
 
“That’s fine, Cindy, even your socks are straight. You’re becoming a proper little girl, but there is one more thing for you. Panty check!”
 
Almost without thinking Cian spun around in place, hiked up his jumper and pulled his panties down inside out around his knees. Mommy checked him the same way that Mrs. Kerry did.
 
“You may pull up your panties and let down your dress, Cindy.”
 
Cian pulled up his panties and rearranged the jumper so that it hung properly.
 
“Okay, Cindy. Go to your room and do your homework. Call me when you’re finished.”
 
Cian curtseyed, “Yes, mommy” and trotted up the stairs to his room. He sat at the table and started his homework. It didn’t take him long to complete it. Once he was done he got up and went to the door and called out, “Mommy, I finished my homework.”
 
“Be right there, Cindy.”
 
Mommy entered Cian’s room a few minutes later. He curtseyed and waited quietly.
 
“Show me your homework, Cindy,”
 
Cian curtseyed, “Yes, mommy” and pointed out the work that he had done.
 
Mommy looked over the work. “The math is fine, but you did this question wrong. Your paragraph for language arts is fine except the writing is sloppy. Correct the math question and rewrite the paragraph using your best handwriting. Slow down and do it properly this time or I’ll make you write it out twenty extra times to improve your handwriting.”
 
Cian automatically curtseyed, “Yes, mommy” and sat down to make the corrections.
 
“Call me when you’re done, Cindy.”
 
“Yes, mommy.”
 
Cian was a little taken aback. Mommy had made sure he did his homework before but she never checked it or made him do anything over again. Cian realized his whole world was changing and he felt out of control.
 
Cian corrected the math problem and rewrote the paragraph. He did it slowly and carefully and it took him longer to copy it than it did to write it the first time. Mommy’s standard was a lot higher than he knew.
 
“Mommy, I’m done.”
 
Cian stood up and curtseyed when mommy came back. He stood with his hands behind his back almost instinctively covering his bottom as mommy checked his work.
 
“The math problem is now correct and the handwriting is much better. I will expect all of your written work to be at least as neatly written as this from now on. I will expect your writing to get better over time. Since I expect that you’ll have lots of lines to write you’ll get plenty of practice. Now, go wash up for dinner.”
 
Cian curtseyed, “Yes, mommy” and went and washed his hands. He soon entered the kitchen, curtseyed again and sat at his place at the table.
 
Cian and his mommy had a lovely dinner together and afterwards Cian helped with the dishes. Once they were done mommy spoke.
 
“You may go and watch some TV or something, Cindy. I’ll expect you in your room by 7:00 to get ready for bed.”
 
“Why so early, mommy? My bedtime is 9:00 isn’t it?”
 
“Yes it is, but remember that you have a spanking and corner time to do before bed too and I want you in bed, lights out by 9:00.”
 
“Yes, mommy.”
 
Cian curtseyed and left the kitchen. He went into the living room and turned on the TV. He kind of sprawled in an armchair as he watched.
 
Cian had watched a couple of his favorite programs before mommy stopped in the doorway. Cian looked up.
 
“I see England. I see France. I see Cindy’s underpants!”
 
Cian realized that he’d flopped all over the chair with one leg over the arm and the other hanging off the seat. His dress had ridden up his legs almost to his waist.
 
Cian stood up and curtseyed as mommy came into the room.
 
“Panty check.”
 
Cian got into position quickly. Mommy checked the panties and then wiped Cian to check him.
 
“You’re still clean, but you showed off your cute little panties. Only naughty little girls let their panties show by accident. I’ll continue the way Mrs. Kerry started.”
 
Mommy smacked Cian’s bare bottom very hard with her hand six times; three on each cheek.
 
“If this keeps up things will get a lot worse fast so you better start remembering not to show off your panties.”
 
“Yes, mommy. I’ll be careful.”
 
“I hope so. Now, go to your room and undress. Hang up the dress and the blouse but put the socks and panties in the laundry. Meet me in the bathroom when you’re ready.”
 
Cindy curtseyed, “Yes, mommy” and went to his room. He did as he was told and joined his mommy in the bathroom. He curtseyed as he entered and waited for directions.
 
Mommy had him get into the bathtub and washed him like she had the night before. Once he was out of the tub and dry she led him by the hand back to his room.
 
Cian stood quietly as mommy put a white cotton nightie with yellow daffodils on it on him. He started to sniffle as she did since he knew what was next.
 
“Okay, young lady, you are due for a spanking. Bring me the hairbrush.”
 
Cian curtseyed, “Yes, mommy.”
 
Mommy sat in the armless chair as he fetched the nasty hairbrush. He handed it to mommy. She guided him over her knees and pushed up the nightie.
 
“Now, young lady, why are you getting spanked?”
 
“I got a detention at school for being late on Friday.”
 
“Yes you did. Why were you late? You left the house in plenty of time.”
 
Cian blushed as he had to admit, “I stopped to stare at the clotheslines full of panties in Mrs. Kerry’s back yard.”
 
As he said it, Cian’s peeny started to swell with excitement. He couldn’t believe it. He was about to get spanked and still he was aroused by the thought and mental image of those panty filled clotheslines.
 
“Yes you did, Cindy, but now if you want to see panties all you have to do is lift up your dress and you can see your own panties. Of course the panties on those clotheslines were your panties even though you didn’t know it at the time.”
 
Mommy raised the hairbrush.
 
“Now, this spanking is for being late and getting a detention at school. You know you get a spanking for any trouble at school that gets you a detention or worse.”
 
Mommy smacked the hairbrush down briskly to the base of Cian’s right bottom cheek. He squealed like a little girl and mommy had to smirk a little. He was changing into a little girl very easily.
 
Mommy continued to spank him briskly alternating cheek to cheek. It only took a few smacks to cause Cian to howl and sob. By the end of the spanking his face was covered in tears and snot and he hung limply over mommy’s knees.
 
Once the spanking was over mommy stood Cian up and led him to the stool in the corner. She lifted him easily and set his sore, red, bare bum down on the hard wooden seat. It was a bad spanking but not as bad as the night before. To Cian it seemed terrible but he got himself under control a lot quicker than the night before.
 
“I want you to think of two things while you’re sitting in the corner tonight. I want you to think of why you got this spanking and I want you to think about the spanking you’re going to get tomorrow. Remember why you’re getting it tomorrow and why it will be a lot worse than this one. I will question you after your corner time to see if you’ve thought things through.”
 
Mommy left Cian to his sniffling and squirming for an hour. When mommy came back Cian wasn’t crying anymore and all she could hear was an occasional sniffle. She stood him up facing her as she started to question him.
 
“Why were you spanked tonight?”
 
“For being late and getting a detention at school.”
 
“How will you avoid that in the future?”
 
“I’ll be careful to follow all of the school rules and make sure that I leave early enough to stop and see Mrs. Kerry and still be on time.”
 
“Very good. Now, why are you going to be spanked tomorrow?”
 
“I was disobedient, mommy.”
 
“That’s true, but there is a little more reason than that isn’t there?”
 
“Yes, mommy. I was disobedient more than once in just a weekend.”
 
“Very good, Cindy. So you can expect a very hard spanking tomorrow; very hard.”
 
Cian started to cry in anticipation as mommy led him to the bed and had him lie down. She got the diapering supplies and soon had him double diapered and in a pair of pink plastic panties.
 
Mommy raised the covers and Cian crawled into bed and laid face down. Mommy hugged and kissed him goodnight.
 
“I love you, Cindy. I know you’re going to try to be a very good little girl from now on.”
 
“I love you too, mommy and I’ll try my best.”
 
“Sleep well, Cindy.”
 
“Goodnight, mommy.”
 
Mommy went to the doorway and turned off the lights.
 
“Goodnight, Cindy.”
 
She closed the door leaving Cian in the dark.
 
Cian sobbed into his pillow for a while and thought about his day and the spanking he had coming tomorrow. As he sobbed he moved around a bit and the friction rubbed the soft diaper against his peeny. It responded by getting erect and throbbing. Cian felt it and his attention turned from the pain in his sore bum to the throbbing need in the front of his diapers. Once again, Cian was happy his hands weren’t strapped down and he took full advantage rubbing himself to an orgasm that left him panting and exhausted. Moments later he was fast asleep despite his fears and pain.
 
 



RE: Panty Lines - Chapter 5-1 Monday - Satin Jessie - 01-24-2021

Fabulous, each episode of this series just gets better and better. You're really spoiling us Cindy, thank you xx


RE: Panty Lines - Chapter 5-1 Monday - afp - 01-25-2021

(01-24-2021, 11:44 PM)Satin Jessie Wrote: Fabulous, each episode of this series just gets better and better. You're really spoiling us Cindy, thank you xx

Exactly what I also say.


RE: Panty Lines - Chapter 5-1 Monday - Cindy - 01-25-2021

Thank you. It's nice to be appreciated. Feeding my ego makes me creative. LOL


RE: Panty Lines - Chapter 5-1 Monday - Girlygirl - 01-25-2021

What a great routine - certainly plenty of motivation not only for Cian to behave but also to be very careful to avoid displaying his secrets at school. It is very clear though that Cian is becoming very on board with much of his treatment and is starting to enjoy his waltz with femininity. 

If his school friends were to learn of his treatment a big part of the reason for him presenting as a male at school would be diminished so that could well be the route to full time femininity (though of course that is coming anyway, the act to delay this moment - however futile - will be quite keenly felt.).  Wink


RE: Panty Lines - Chapter 5-1 Monday - Cindy - 01-25-2021

In my mind this story takes place in the late 50s or early 60s. At that time things were far different than today. There was no internet and "adult" magazines were not available. To boys of Cian's age, about 12, girls really were a mystery. That would have been a big part of his fascination with panties. The were no TV ads for underwear of any kind. There were no stores like Victoria's Secret. The only place to see panties would be in a catalog or in person.

I'm sure you've noticed that I have all of the girls wearing skirts or dresses to school as they did at that time. It's important because in those days I don't think that if anyone at school found out about Cian/Cindy they would be accepting at all. At that time Cian would have been the subject of ridicule by everyone, probably including the teachers. It's even possible his mother would have been investigated as a possible child abuser. There would be tremendous pressure to keep it secret.

Cian is going to gradually understand and accept what he is, but it won't be easy.


RE: Panty Lines - Chapter 5-1 Monday - afp - 01-26-2021

Had an idea the years the story was set in were about that. It is a perfect dynamic and like allot of secrets and stereotypes in those times I bet there was a Mrs Kerry. I loved when Cian was told all those panties he admired are his. I can imagine his jaw dropping in shock and awe at that revelation. I’m not a fan of spanking but him squealing like a girl says allot. The slow but not easy approach for Cian to Cindy is the right path for the story, in my humble opinion. You write it very well, also I’m sure Mommy is struggling too, it must be very difficult to have administer discipline, same too for Mrs. Kerry and maybe somewhere in the story more about their chats, possibly.


RE: Panty Lines - Chapter 5-1 Monday - BABYLOCK - 01-26-2021

(01-25-2021, 11:37 PM)Cindy Wrote: In my mind this story takes place in the late 50s or early 60s. At that time things were far different than today. There was no internet and "adult" magazines were not available. To boys of Cian's age, about 12, girls really were a mystery. That would have been a big part of his fascination with panties. The were no TV ads for underwear of any kind. There were no stores like Victoria's Secret. The only place to see panties would be in a catalog or in person.

I'm sure you've noticed that I have all of the girls wearing skirts or dresses to school as they did at that time. It's important because in those days I don't think that if anyone at school found out about Cian/Cindy they would be accepting at all. At that time Cian would have been the subject of ridicule by everyone, probably including the teachers. It's even possible his mother would have been investigated as a possible child abuser. There would be tremendous pressure to keep it secret.

Cian is going to gradually understand and accept what he is, but it won't be easy.

How very true !

And all those scarlett "RED" marks would certainly need an explanation - exposed or uncovered while changing clothes before/after phy-ed.
The least slip up and Cian (Cindy) would be the talk of the moment and the rumor mill in overdrive - - -
How did you get those marks ?
Does it hurt ?
What did you do to get them ?
Explains why you are NOT sitting except in class ?

Fortunate these days with the covid virus 19 restrictions in play the exposure would be very limited due to home schooling.

And as for searching for PANTIES one doesn't have far to go with fingers on the keyboard spelling spilling everything out in 1080 4k ultra vivid High Definition !
Victoria's Secret is no longer a secret but a full fledged come on in for a test drive (fitting) !
Fredericks of Hollywood used to be the clandestine fantasy shop - now you find a fantasy shop in just about every other mall.


RE: Panty Lines - Chapter 5-1 Monday - Cindy - 01-26-2021

The signs of a spanking always attracted questions even in those days when spanking was the standard means of discipline both at home and at school. I remember hearing rumors about a kid that didn't get spanked and we were all really surprised. The general reaction from the adults was that he must be a real brat.


RE: Panty Lines - Chapter 5-1 Monday - mikki - 01-28-2021

(01-25-2021, 11:37 PM)Cindy Wrote: In my mind this story takes place in the late 50s or early 60s. At that time things were far different than today. There was no internet and "adult" magazines were not available. To boys of Cian's age, about 12, girls really were a mystery. That would have been a big part of his fascination with panties. The were no TV ads for underwear of any kind. There were no stores like Victoria's Secret. The only place to see panties would be in a catalog or in person.

I'm sure you've noticed that I have all of the girls wearing skirts or dresses to school as they did at that time. It's important because in those days I don't think that if anyone at school found out about Cian/Cindy they would be accepting at all. At that time Cian would have been the subject of ridicule by everyone, probably including the teachers. It's even possible his mother would have been investigated as a possible child abuser. There would be tremendous pressure to keep it secret.

Cian is going to gradually understand and accept what he is, but it won't be easy.

Maybe there was no internet in the 1960s, but there certainly WERE catalogs, like Sears, Roebucks, Montgomery Wards and J.C. Penney's.  These merchandisers regularly put out catalogs that were compendiums of almost everything a householder could want or desire, including comprehensive sections devoted to women's and girl's clothing, lingerie included.  Many were the lads who perused these sections, in private, with great fascination.  

Likewise, the popular ladies' magazines of the day, like Redbook, Ladies Home Journal, and even Cosmopolitan, to name just a few, were replete with lingerie ads, profusely illustrated.  There were also occasional ads for childhood incontinence products as well, such as the infamous Sta-Dri panties, the shameful bane of many a boy passing through puberty after his second or third wet dream.  

Parents were still considered gods on earth in the 1960s, when it came to their children. Few adults dared interfere with another's parenting.  Parents were generally free to raise their own children according to their own lights.  "Spare the rod..." was a generally-accepted disciplinary approach, as was gratuitous humiliation of children.  Indeed, many noted child-rearing "authorities" promoted humiliation as a way of "breaking a child's spirit" so s/he would be docile, obedient and biddable.  Parents who eschewed this approach were often considered to be negligent in their parenting, and might be shunned, along with their unhumiliated offspring, by the neighbors.  Much of what passed for "good parenting" during those years would likely be considered criminal conduct in today's milieu.