Large families were common in the North East of Scotland. I was one of seven siblings, four girls, and three boys. We were poor but still had a good upbringing. As the eldest, I helped my mother to look after my brothers and sisters and with the running of the house. I started work as a kitchen maid as soon as I could leave school. I was not good looking, and despite my best efforts, I found myself on the shelf. I, therefore, decided to try to get a more rewarding job; domestic service was not for me. I did evening classes and after a couple of years took up a junior administrator post in a city-based company. I continued to study at college part-time and worked my way up within the company to become their Production Manager. I had a successful, albeit solitary, life.

Life changed four years ago. My youngest sister became seriously ill and hospitalized. Brian, her eighteen-year-old son, needed a home. He was a rough and disruptive kid, always getting into trouble. None of our family could cope with him, so he finally ended up living with me, a fifty-year-old spinster.

Brian had been doing his own thing at home, acting up, mixing with a wrong crowd and getting away with everything. He was rude and tried to play the macho man with me. I decided to stamp on this behavior immediately and set out clear ground rules for him. He seemed to take this on board and for the first few days, other than being untidy around the house, he was well behaved, punctual and quite polite.

This situation came to an end on Friday night. He did not appear for dinner and was still not home by early evening. He eventually sauntered in around nine o’clock. When I asked him where he had been, he was very lippy and rude.

“You should have been here hours ago or at least have let me know where you were. I have been worried sick.”

“I’ve been out with my mates. If you were worrying that is your problem.”

I was exasperated but tried to be reasonable. “It is okay to meet up with your friends, but you must always tell me where you are, who you are with and when you will be home. Those are the ground rules.”

That just triggered a height of abuse and swearing. Essentially, Brian would do as he pleased.

“What can you do? Are you going to ground me? Mother did that, and I just ignored her. So, there!”

That was the final straw. I remembered what my parents did when we broke the rules.

“No, I’ll not ground you, I have a much better remedy."

Before Brian knew what was happening, I grabbed him, undid his belt and pulled his jeans down. You cannot run away when they are around your ankles. My mum had used the same trick with me. I told him to bend over the sofa.

“You can’t be serious. I’m too old. I’ll have the social services on you if you lay a finger on me.”

“I don’t intend to use my fingers. There is no discussion here. Bend over.”

He finally realized that I meant it and that he had no way out. I picked up a slipper: "From now on, this is what will happen every time you misbehave or break the rules."

I spanked him again and again until he was begging me to stop.

“I will stop when I think you have got the message.”

I pulled down his underpants and kept swatting his bare bottom until it was dark red and he broke down sobbing and wailing. Then I stopped and told him to stand up. I pulled him towards me and hugged him.

“I do care and will always look out for you, but you must learn to behave and obey the rules. Go to bed, and we’ll talk in the morning.”

I did not sleep much. I felt guilty. I had lost it and spanked Brian without thinking of the severity or consequences. However, he needed bringing in line, and maybe this very sharp shock would do it.

Brian came down to breakfast. He sat down quite gingerly. His behind was very tender. He was very apologetic about what he had done and promised never to it again. Nice to hear, but I was not so naïve as to think it would last.

“Let’s just start with a clean slate from today.”

When he had finished his breakfast, Brian helped me with the dishes. A first as far as I knew.

“I want you to put your laundry in the basket and tidy your room, but once done, you can go meet up with your friends.”

Surprisingly, he said that he would stay in his room and watch television. Again, this was a first for the weekend. Later, I realized that having to explain to his mates that his Auntie had spanked him would do nothing for his street cred.

Later in the day, I found myself outside Brian’s bedroom. The door was partly open, and I glanced in. He was busy doing what teenage boys often do. He was horrified to see me standing there and desperately tried to cover himself. I did not say anything and continued through to my room.

I prepared the evening meal and called for Brian to come down. He was very hesitant and apologetic. “I am sorry for being disgusting. It won’t do it again. Please don’t spank me.”

“What do you think you’ve done wrong? Is it that you were jacking-off?”

He looked shocked that I knew the expression: “Yes. I know it is bad, but sometimes I cannot help myself.” 

“You were not doing anything wrong; you were doing what all boys do at times.”

He looked flabbergasted. “You mean that you are not upset. You don’t think of me as weird.”

“Where did you get that idea from?”

“My mates.”

“Let me guess, they are having regular sex with girls, and you are the strange one because you are not.”

“Yes.”

“Few girls of your age have even kissed a boy, let alone have gone all the way. Boys always brag about how much sex they are getting, but most are just jacking-off alone, like you. Masturbating is normal. You are growing and trying to learn about your body. It is good for you, and you must admit it is very satisfying.”

He looked at me quizzically. “How do you know?”

“Boys are not the only ones who masturbate.”

I could see there were all sorts of questions whirling around in his head.

“Enjoy it, but don’t overdo it and be discrete. Keep your bedroom door shut when you are busy.”

“You are the first adult, to be frank with me. I tried to ask my mum about the changes that have been happening to me, but she just refused to talk about such disgusting stuff.”

I was shocked by this, but not entirely phased: my sister is a prude and probably too embarrassed to talk to her son about anything intimate. The result is that Brian has been trying to understand what was happening to him during the roller coaster years of puberty, with his mates as the only source of half-truths. Not good. I wonder if this is a big part his problems.

“If you want to ask or talk about anything, please come to me no matter how small, personal or intimate the question. I will give you the best help I can, and I promise I will not get upset or too embarrassed.”

“I have loads of questions.”

“Let’s start tomorrow and take it from there.”

After watching television for a couple of hours, we went off to bed. As we were going upstairs, I cheekily said to Brian, "Try to get plenty of rest tonight, don't exhaust yourself." 

He blushed.

We were having breakfast next morning when the first question came. I was in for a shock because I expected that it would be on basic birds and bees stuff, but no, it was far more fundamental.

“What does an undressed girl look like?”

At first, I thought he was winding me up. In the innocent times when I grew up, it was common for children to run around and play together partly dressed or even nude, particularly during the hot summers. Most kids, therefore, knew the basics of boys and girls from an early age, but this was not the case with Brian. In all his life, he had only ever seen girls or women fully clothed. His mother had made sure of that. To prevent lustful thoughts, I presume. Remember also that there was no internet then and magazines and catalogs were rare, so Brian hadn't even seen images. No wonder he was confused. Girls could just as well have been an alien species. What did he think when his mates talked about boobs, pussy, and sex? This lack of knowledge could be dangerous. He might try to find out with a random girl.

“I want to give you a proper answer. I will think about it, and we can talk after lunch.”

We did the washing up, and he went off to his room, I think a little disappointed.

I puzzled for a few hours on how to deal with this until I finally concluded that the only answer was for him to see for real. After lunch, we went up to my bedroom, and I told him to take off all his clothes and sit in the chair. He was hesitant but did so. I noticed that his bottom still looked nicely tanned.

I then undressed. Brian’s eyes looked like they were out on stalks and he was struggling to hide an erection. I chuckled. For the first time in my life, I watched a penis become engorged and stiff, in the flesh so to speak. I motioned him to come over in front of the of the full-length mirrors.

“This is a look but not touch. Point out what body parts are different between you and me.”

The first thing he pointed to on the mirror were my breasts. “They are my boobs, and the red area on each are the nipples. You have breasts as well, just small.” I pointed out where his nipples were. “Boys, men and little girls have these tiny breasts, but they start to enlarge and become pronounced when girls are in their teens.”

I thought I knew where we go to next, but no.

“Your hips are wider and curvier than mine, and your bottom is much bigger.”

Flattering or what. “The hips and bum are similar size and shape in young girls and boys but become more prominent in maturing girls as their body rearranges itself.”

Then we got to the point about which I was apprehensive. Brian indicated my mound.

“I have balls and a penis. You have just a triangle of hair. Why are you blushing?”

“You urinate through your prick and release spunk when you jack off.  As a girl, my vagina or pussy as you have heard it called is the nearest equivalent. It is below that mound of fuzz.”

 “Can I see?”

I went the brightest shade of red possible, but I knew this was inevitable: “yes.”

I drew up a chair, sat down in front of the mirror, leaned back and spread my legs. It shocked me to realize that no man had ever seen my pussy before, but here I was showing it in all its glory to my nephew. Again, his eyes were out on stalks. I pulled the lips slightly apart and pointed to the clitoris, urethra, and vagina. “I urinate through my urethra.”

“So, that is why girls always have to sit on the loo.”

“Yes.” I wonder what he thought before. “The vagina is essential for making babies. It is the equivalent of a USB port for a boy’s memory stick or penis.” I thought this a good analogy but may just have confused him. Thankfully, at this stage, he seemed to be okay with this. I was worried he would want more detail. I sat up in the chair and closed my legs to feel a bit less exposed.

"But you didn't say anything about the clitoris."

“You become aroused when you rub your prick. Massaging the clitoris has the same effect in girls.”

“Is that what you do?”

I must have been glowing fire-red by then but managed to give a flustered, “Yes.”

“Is there anything else you want to ask?”

“No, not now.”

I told him to sit down and watch while I redressed. I wanted him to become familiar with the female form and clothes. He looked intently but was less goggle-eyed than before. When I told Brian to redress, I noticed that his little man was erect yet again. This response must be automatic in teenage boys.

“You cannot talk about this afternoon to anyone. If your mates question your new knowledge, just say that you and your Auntie watched a film together for you to learn some basics.”

“The other thing is that what you have seen are my privates. The private parts of any girl or boy are not to be seen or touched by anyone else without permission. You maybe want to cop a feel or be egged on by our mates to do so, but you must not. You are breaking the law if you force a person to reveal their privates or touch them without their consent. You must understand this.”

“Yes, I do. Thank you for teaching me.”

We had an evening meal, rested and watched television before going off to bed. Monday morning came around. Brian was up early, dressed and ready for the school bus in plenty of time. Unheard of before, maybe he was turning over a new leaf.

I went to work. The day was uneventful, and I arrived home at the same time as Brian. He came straight from school instead of hanging out for a while. He was positively buoyant. I made dinner, and we ate it together.

“How did your day go?”

“My mates were boasting about their weekend. They all had sex multiple times, so they said.”

“What did you do? “

“I listened, smiled and said nothing. I thought it the best approach.”

“You were correct. Where did the guys locate all these girls so desperate to be shagged and how did they find the time?”

 “They were just wanking or bragging.”

I was pleased with Brian. It was amazing the change in him when he had a few real facts at his disposal. Things went well for the rest of the week. He was keen to do his schoolwork and happy to ask for help when he was struggling.  Friday came around, and he asked if he could go to the mall with his mates to hang out after school.

“You have worked hard all week, that will be okay provided you are back by eight in the evening.” He went off to school, and I went to work. 

I had a rough and tiring day, and I fell asleep on the sofa soon after arriving home. I awakened with a start when I felt something touch my leg. Brian was trying to put his hand up my skirt.

I slapped him away, “What the hell are you doing?”

“Sorry, sorry. The boys were speaking about what it was like to feel a girl's pussy, and when I saw you sleeping, I could not help myself.

“After everything we’ve discussed, you still did that?”

“Yeah, I’ve been stupid.”

“What did I tell you about people’s privates?”

“Not to touch without consent.”

“I was asleep. How or when did I give permission? You broke the rules, and you know what happens next. Bend over!”

 He knew he was in the wrong and did not argue. He pulled down his trousers and underpants and bent over the sofa. I was so angry with him. I grabbed a wooden hair brush and spanked his bare bottom again and again until it was almost glowing and he was crying and begging for forgiveness.

“Go to bed. You need to think clearly about what you did and why. We will talk about this tomorrow.”  

I felt angry and betrayed, but surprisingly also relieved that at least he tried it on me and not a stranger. It prevented problems with the law and gave me the chance to get through to him that this was unacceptable, even if it means tanning his ass black and blue every day until he gets the message.

Brian came down late for breakfast. Putting off meeting me face to face for as long as possible, but also because he was very sore and stiff. After breakfast in silence, I asked, “Why did you do it? Didn’t you listen to anything I said about people’s privates?”

"I did but was embarrassed in front of my mates by the one that is the big-I-am. The boy boasted about putting his hand up my friend’s skirt and goosing her. He said she enjoyed it.”

“After all we have talked about, you still believed this rubbish? If he was busy shagging girls, why would he need to put his hand up this poor girl's skirt? He has not done it. He said it to make you react because it was your friend. You fell into his trap, and you then made it worse by trying to feel me up to see what it was really like.”

“I do not know why but when I saw you sleeping there I could not stop myself.”

“Well, maybe the memory of your very sore behind and the thought that it will be my response anytime you try anything like that with me or anyone else again will stop you from stepping over that line in future. Be sure; I will reinforce the message if need be. I am most disappointed that you did not ask about it. I told you that we could talk about anything. I will not be angry or too embarrassed to answer or find a solution.

"I am so ashamed of myself." He was crying.

I can hardly believe what I said next. “If you still want to put your hand up my skirt, then ask me? I may refuse, agree or suggest alternatives, but that will be my choice.”

He spluttered something, but I persisted: “Ask me if you want to do it.”

“May I put my hand up your skirt."

“Yes, come over here and sit down beside me.”

 He did so, and I put his hand between my knees. He tried to push inwards, but I kept my legs tight together. He could go no further without forcing my legs apart, which I would not allow, so he stopped.

“What did you find out?”

“I couldn't get in because your legs were together.”

“That is how a girl will react if she does not consent. The only way to overcome that would be to force her legs apart. That would be a crime, sexual assault. So, if the big-I-am insists that he goosed a girl against her will, he can be arrested. Now, see what happens when it is consenting.”

I could hardly believe that I separated my legs and told him to try again. I felt his hand touching my stocking. It slid along the inside of my leg, touched the bare skin above my hold-up and then reached the target zone. He ran his hand over my pantied mound, down the camel toe, thoroughly explored around my vagina and then slowly slid his hand out along the other leg.

“Thank you, I have learned so much. Pussy feels lovely and nothing like what the big-I-am described. That guy is just a mouth.”

“The pussy of a girl your age is less developed but is basically like mine. Your mates have probably glimpsed a sister's pussy at a distance, so most of what they think and say are imagination and wishful thinking. Think about the implications of that. Don’t be messed up or get into trouble because of your so-called mates. What would have happened if you tried to feel up a stranger? In future, don’t act on impulse. Come and ask me if you’re unsure."

"I am so sorry; I won’t do anything like that again.”

He hesitated for a moment. “There is something I want to ask.”

Oh no, what next?

“The big shot said he twanged my friend’s bra so hard that she screamed. I was angry that he could hurt her, but did not understand what he had done.”

“More imagination and exaggeration. Do you remember what I put my breasts into when I was redressing last week?

“Yes.”

“That was my bra. All mature girls wear one to support and protect their breasts. The shoulder straps and the strap across the back hold it in place. A boy twangs a girl's bra by pulling on that back strap.”

I turned my back to Brian and pointed to where the back strap was under my blouse.

“Take hold of it with your fingers and pull it backward.” I could feel the band tighten around my chest as he did so. “Let it go.” There was a sharp thwack as it hit my back and I gave a slight gasp. “Do it again, but pull it back as far as you can.” It was far tighter this time and gave a very loud thwack when he released. I did shudder and gasped a little as it hit my back. I turned around.

“So, what did you learn.”

“Twanging your bra strap had little effect on you. The boy could not have done what he said, just more hot air from him.”

“Exactly. Twanging a bra strap causes discomfort and some guys think it is great fun. It is not funny for the girls. They feel violated and embarrassed, just as they do if they have their skirt flipped, or a hand put up it. How would you like it if a stranger pulled down your jeans in public? It would be just as bad. Such things are only acceptable, in the unlikely circumstance, that the other has agreed and continued to give consent to it. There are no if or buts on this. You have a lot to think about, go and rest for a couple of hours and then come and give me a hand with the weekend chores.”

I know that letting my nephew feel me up seems perverted, but it was not sexual. He was trying to find out more about girls and put the exaggerated stories his mates were telling him into a context. It was better he learned in a safe, controlled environment instead of finding himself in trouble by trying it on some unfortunate girl. Also, I wanted to show him that he could safely ask me about anything, but he must ask. 

I was doing the laundry when Brian came back down stairs. I had washed and dried all his clothes. So, I showed him how to iron and fold them up. He busied himself, while I did my clothes, including hand-washing my knickers. It was clear that this distracted him because he kept looking in my direction and managed to scald his finger on the iron.

“Come here; you seem to be fascinated by my undies."

"No, I'm not. Well, your panties do look so different from my underpants. They are so soft and delicate. In fact, all your clothes are lovely.”

“Females are complicated as you will find out in time. We wear beautiful figure-hugging clothes and underwear to show off and emphasize our femininity. Girls need to feel different, special and girly. I'm sure all those in your class don’t dress the same?”

“No, they don’t. The girls did up to last year, but the school uniform is not compulsory for final year pupils. Most have been changing to more eye-catching styles. Shorter skirts and tighter fitting blouses. Officially, the school disapproves but the male teachers aren't upset.”

I could see he was intrigued so; an idea came to mind. Brian is a macho guy, but an appreciation of feminine things could make him a more rounded person.

 “Why don’t you find out what they feel like You can try on some of my clothes, they are about your size. I will help you."

“No, I am a boy. I can’t wear girl’s clothes.”

Nonetheless, I could see an interest in his eyes. After lunch, I went to my room and sorted out some things. I called Brian.

“You are interested in what we girls wear and how our clothes feel. There will be no-one else around here over the weekend. Why don’t you dress as a girl and experience it, for real? You will get many shocks, good and bad.”

At first, he said, “Absolutely no way," but finally I persuaded him.

“If you can have a sensible conversation with girls about clothes, you will be way ahead of any other boy. Girls will flock to you. Just don't admit you wear them.” 

“Take your clothes off.”

I picked up a pair of floral panties and got him to step into them. He shivered a little as I pulled them over his bottom. I then fitted him with the smallest bra I had and padded it out with some socks. Then, a pair of black hold-ups. I told him to stand and hold his hands up. I put a knee length slip and a pretty-pink summer dress on him and zipped up the back.

“Look in the mirror.”

He almost ran across but seemed disappointed. “I look just like a boy in a dress.”

"Sit down at my dressing table; I have more to do.” I applied makeup particularly around his eyes and lips and then fitted a small blonde wig. I finished off by giving him a pair of stylish flat shoes.

Brian looked in the mirror amazed, “I appear to be a girl.”

“There are a few things you need to know. Turn the chair around and face the full-length mirror. What do you see?”

“I look girly. Oh, I can see my panties under the dress.”

“Yes, you need to keep your knees together when sitting, just like me this morning, to be sure that boys do not see them. Also, you must kneel to pick things up. If you bend down, you can reveal your panties. The other thing is that as a boy you take big steps when walking. As a girl, you take small steps, putting one foot in front of the other and no more. I am just telling you this to be sure you realize some of the problems with this clothing. Come and give me a hand with the chores and get used to your new clothes.

He was happy and almost had a skip in his step. All was going well, but then he started to look distressed.

“What is the matter?”

“I need to go to the loo, but how do I do it dressed like this.”

I would never have thought of this problem, but apparently, it was confusing if you had never been en femme before. I took Brian's hand, led him to the bathroom and told him to stand next to the toilet facing me. I lifted the dress and underskirt, pulled the panties below his knees and told him to sit down, while I kept the clothes out of the way. Once he had finished, I told him to dry himself, pull his panties up and straighten out his dress and slip.

 As we washed our hands, Brian said, "When you put your hands under my dress to take down the panties I felt so exposed and vulnerable, with no control of what was happening to me. Is that how it was for you when I first tried to put my hand up your skirt?”

“Yes. It was scary.”

I hadn’t planned it, but Brian had learned a valuable lesson today.

We spend the afternoon doing jobs about the house. I will admit to having set him up a few times, getting him to pick up things and show his knickers. He got better at avoiding the trap, but the best was when he was in front of the hall mirrors. He bent down in front of one and saw the full moon of his exposed bottom and panties in the other. He was shocked how easy it was to reveal yourself inadvertently. We finished off the chores and prepared dinner.

“Brian, you need to watch me.” I ran my hand over the back of my skirt to smooth it out as I sat down. “You need to do the same to stop your dress creasing when sitting.”

We finished our dinner and tidied up. “Let’s go for a walk in the garden.”

“You mean outside, dressed like this.”

“Sure, there is no one around, and the fresh air will do us good.”

He hesitantly stepped out of the door with me. It was breezy, and as I had expected with the first gust, the dress and slip were up around his waist, revealing everything. He tried desperately to cover himself, but all to no avail. The next gust had the same effect. I took pity and explained how to keep the dress down with his hands. I thought it was a perfect lesson on the perils of skirts and dresses and would make him appreciate what girls go through for appearance.

When we got back into the house, I got Brian to change into a pair of pink silk pajamas and house coat. I dressed the same, and we sat and watched the television, cuddled together like mother and daughter. He kissed me on the cheek.

“This has been the most enjoyable afternoon. I love the clothes but also appreciate the difficulties they pose for the girls. You knew the dress would blow up a soon as we left the house, didn't you.”

“Yes, you needed to experience the problem to appreciate how difficult it can be. A girl can never relax in a loose dress or skirt. One sudden gust and your knickers and bum are in full view, and there will always be guys around to see it.” 

“Now, I understand why that young girl at school ran off crying when it happened to her. Needless-to-say, the boys around her very sympathetic, not.”

“It has been a fascinating day. Can I dress up again tomorrow?"

My bedroom became a changing-room for most of the next morning as Brian tried various combinations of my clothes, before settling on a white blouse and black pencil skirt. They suited him well. He had learned from yesterday but was about to find out that this skirt-type has its difficulties. I fitted a wig, did his makeup and gave him a pair of court two-inch heel shoes. I will admit he looked good and girly, but he did struggle with the restricted movement and keeping his balance on heels. He slowly got the hang of things and was easily getting around by afternoon, so we went for a walk along the coast. I could see he got nervous when anyone approached but held him close: "Don't worry they only see a mother and her daughter out for a walk."

We had finished our evening meal when Brian said, "The last two days have been so right for me. I have learned so much about girl’s clothing. I love its feel and femininity, but I also grasp some of the difficulties faced in keeping up that look. Heck, even my ankles are hurting tonight.”

“Don’t agonize too much. Girls love to dress up beautifully, no matter these discomforts. Just appreciate the effort they make and make sure to tell them they look gorgeous and sexy. That will melt their hearts.”

Brian was up early next morning, ready for school and back to his macho style. However, there was a skip in his step, a smile and happiness I hadn’t seen before. The last few weeks had been a roller coaster but had allowed a bond to build between us. Brian was confident enough to discuss even the most intimate and delicate things with me. He would make me blush many times, but I always found a way to get him the information he needed. His behavior and manner were significantly improved. That does not mean he became perfect. We still had occasions when he strayed, and his bottom was tanned, but not that many.

Brian now had more real knowledge of the female form and femininity than most other boys of his age. The question now is how well he uses it in the future and how many times will he make me go red asking advice on dating, petting, and love.