Sissy boy John was petticoated at Secondary School after falling foul of Jenny Tough, a school bully. During his week of penance, John found that he was more at ease and happier amongst girls than with boys. John decided, therefore, to explore his feminine side by trying to live as a girl. John’s Mum was shocked when he first arrived at home wearing a schoolgirl’s uniform but calmly listened to his story.

“Well, sweetie, this is a bombshell. You’ve always been a sensitive boy, but I never realized that your feminine side was so strong or maybe even dominant. Are you sure that you want to do this?”

“Yes and no. I feel at peace as a girl, but I still have to find out if this is the real me.”

“Okay, so I now have a daughter.”

“Thanks, Mum, I won’t let you down.”

 “Just remember that life for girls isn’t all sweetness and light. Their behavior must always be above reproach so you won’t get the same leeway that you did as a boy. I will be strict, so you may not always enjoy being my daughter.”

Mum led me through to her room. She selected out some clothes and soon had me dressed like a teen girl. We were heading to the kitchen to have supper when I noticed that Mum was frowning.

“Your gait is a problem. You’re like a rampaging animal, not graceful young lady.”

After our meal, I spent the evening perfecting my walk; slow pace, small steps and eventually dainty steps in front of each other. Mum was unrelenting, and once I’d mastered that part, she introduced the complication of heels. Although only one and a half inch high, the heels disturbed me. I couldn’t be sure when my feet were firmly on the ground. There were many trips and falls often accompanied by profanities, which immediately earned me a swift smack on the bum.

“Shush, well-mannered girls don’t use filthy language.”

Eventually, I was able to walk satisfactorily in heels. By then, I’d aches and pains in joints that I never knew existed so was mightily relieved when Mum said, “Good, I think that’s enough for tonight.”

After our night-time cocoa, Mum led me through to my bedroom and undressed me just as though I was a little girl. Soon, she had me clothed in a pair of cozy pink pajamas and tucked into bed.

Mum kissed me on the cheek. “Good night sweetie, sleep tight, we’ve got a busy day tomorrow."

Mom was up and about before I woke. "Wake up lazy bones, you need to get ready. Go have a shower.”

I’d just finished my shower when Mum came into the bathroom. She set about shaving off all my body hair.  “From now on you have to remove any unladylike hair. It is time-consuming but vital for your appearance.”  This was a revelation. I’d never realized that girls had to shave.

"Now, have quick rinse to get rid of any fluff and then I'll towel you down.” Once dried off she wrapped me in a large bath towel, not boy style around the waist but girl style around my chest, covering both my upper and lower privates. We went through to Mum’s bedroom. She watched in amazement as I hid my boyhood inside my mock pussy and then donned a pair of figure-hugging panties.

“Wow, you look smooth and feminine. No-one would ever guess.”

After I’d put on my bra, Mum led me to her vanity table, fitted my wig, combed it out and then began to apply some makeup.

“This is another essential task that you have to learn.”

Soon, the face in the mirror was unmistakably female. Once dressed, I would pass as a girl even on close inspection. I just had to remember to behave in a feminine manner to carry it off.

Mum and I had breakfast and then set off to catch the bus to town. I was a little unsteady in the heels and unnerved when strong breezes threated to lift my skirt. But Mum, Beth, and Mandy had taught me well, so there were no mishaps.

After a journey of about an hour, we got off in the high street and began window shopping. I gave positive remarks when Mum mentioned something that she liked but, in truth, I wasn’t paying much attention. I was too preoccupied with my posture and gait; scared that I’d make one false step and reveal myself as a boy. Fortunately, people didn’t give a second glance to a mother and daughter out shopping together.

We entered a lady’s clothes store. The austere woman behind the counter said, “Good morning, madam. How may we help you today?”

My jaw dropped like a stone when Mum said, “My nephew is staying with me for a few months and needs some outfits. This list covers what’s needed."

At these words, two girls of about my age look round from the end of the aisle.

"Is he being punished for bad behavior?"

“No, he wants to find out what it’s like to be a girl and I’m helping him.”

“How wonderful. More boys should do the same. Life would be much more peaceful. Jennifer and Samantha, please come here.”

“The two girls came to the counter. This young lady needs several items of clothing. Please help her find what she needs. Her Mum will be waiting in the changing room.”

“Happy to be of assistance. What’s your name?”

“Joan.”

I cringed when they asked me, “Why do you dress as a girl?”

I stuttered at first but then said, “I’ve recently found my feminine side and want to develop it.”

I expected to be ridiculed but no. “That’s cool. We’re glad to help you. Let’s go find some nice things. Have you anything specific in mind?”

“I want to be fashionable but not to stand out.”

“Very wise. We can do that.”

I was overwhelmed by the choices, but with much cajoling from Jennifer and Samantha, I settled on a set of dresses, skirts, and blouses to try on. Next, came the most embarrassing part for me, selecting lingerie. I became flustered while being shown a seemingly endless array of bras, panties and other underwear.

“Sorry, we shouldn’t have done that. Your reaction’s normal. No girl wants the world to know what undies they wear.”

“No problem, you were just having a bit of fun.”

We gathered up the clothes and lingerie that I had picked out and headed to the changing room. Mom was already there, a cup of tea in hand. She’d already made some purchases.

 "Joan, you try on the clothes that we've collected. Decide with your Mum which ones you want while we go find the school wear that you need."

By now I’d no problem stripping down to my bra and knickers in front of Mum but to do so in a glorified cupboard with a curtain as a door was a different matter. I took forever to get changed because I kept checking that no-one was looking in. The girls were back with the school items before I had tried on even two of the dresses.

"My little flower is nervous. Will you help Joan with the clothes?"

Jennifer and Samantha didn’t need to be asked twice. I mean which girl would refuse the chance to dress up a boy. They moved in with enthusiasm and soon I had tried on everything that had been picked out. Mum approved three of the dresses and three blouse and skirt sets. I finally redressed in my original clothes, with Jennifer and Samantha’s eager help. Those selected by Mum were taken through to the sales counter, paid for and wrapped.

Jennifer and Samantha handed me a pack of beautiful panties. “Just a memento of your first visit here. Please do come again soon.”

I blushed. "Oh, you are kind, thank you for your help."

Now laden down with bags of clothes and other purchases, Mum and I headed to a shoe shop where Mum bought me some casual shoes and sandals. We then went to a small café for a light snack. All was going well until I noticed two boys at the table across the way. They were very quiet and staring intendedly in my direction. Oh no, I'd slipped into a boy spread, and they were getting the full view. They looked very disappointed when I closed my knees.  Mum noticed. “That’s a perfect lesson, you must be more careful, a girl can never let her guard down.”

Worse was to come. We were walking along the main street towards the bus stop. A sudden gust of wind blew up my skirt and slip, to reveal my knickers. With my hands full of bags there was nothing I could do to stop it or quickly restore decorum. The ladies around looked on in dismay while the myriad of boys and men whooped in great delight. By the time I had set down the bags and got my slip and skirt back in place, I’d burst into tears.

An elderly lady came over and dabbed my eyes with a handkerchief. “There, there, don’t fret lassie. You’re not alone. We’ve all have been caught out like that. It’s a pity that males don’t suffer the same humiliation. Then, they wouldn’t think it such a hoot.”

Hmm, how true.

Mum and I eventually caught the bus and headed home.

"Have today's travails affected your wish to be a girl?"

"No, in fact, they've made me more determined. I want to experience the bad as well as the good. One thing, why did you tell the ladies in the store that I was a boy? Surely, they didn’t need to know.”

"Girls are competitive in their own ways. They are happy to see others well dressed but never better than themselves. As a girl, you’d be competition, but as a boy, you weren’t. I knew that they’d do their best to find clothes that really suited you.”

“Well, that is something that I would never have imagined, but it's true that the girls were keen to get me to try on the most beautiful things. My only niggle is why did they pick skirts for me that are shorter than they wear themselves."

"That I did notice and asked. Jennifer and Samantha said that girls learn to manage their skirts and preserve their modesty from an early age, but you’ve not had that experience and may forget to be careful. The girls thought that the added dangers of a shorter skirt would keep reminding you of the need for control.”

“Today’s traumas emphasized those necessities, but I suppose a little more risk will keep me focussed.”     

We arrived home late in the afternoon. I was exhausted, not only with carrying all the bags but also the extra stresses of walking in heels and coping with the weighty appendages on my chest. But as is usual for girls, there was no respite. I was told to put our purchases safely away in the cupboard and drawer unit in my room. To my astonishment, I found there was no longer any boy’s clothes in them, only girl’s things. Mum must've removed the boyswear while I was asleep. I had just finished putting my things away when Mum came through with new bedclothes. Together we stripped down my bed and remade it with a girly pink bedding set, which Mum must have bought while I was looking at clothes in the shop. She was obviously intent on encouraging my journey in femininity.

Mum and I then prepared an evening meal and shared it. I did the washing up while Mum tidied the kitchen. Only then did we stop to relax. We sat together on the sofa for a short time, but I was so tired that I was soon nodding off.

"You've had a stressful day; you’d better have an early night. We have a lot to do tomorrow.”

I followed Mum to my room and was instantly struck by the sweet fragrances now wafting in the air. I undressed, and Mum handed me a pink nylon nightie. As I slipped into bed, I realized that the nightie and bedding had a hint of perfume. So, that night, I slept in a sea of femininity.

The following morning was spent learning the basics of makeup. I made countless mistakes. Art was never my forte, but I mastered enough that I could top up and maintain my now female appearance. In the afternoon, Mum and I went for a walk in the park. We met several neighbors and family friends and as expected all asked who I was. They all fussed over me when told that I was her niece and staying with her for a few months.

“How wonderful. Bringing up a boy is okay but raising a girl is more enjoyable. To be able to guide them to womanhood is wonderful. Enjoy your time together."

As we walked in the park, I asked Mum about this. “Is it true that girls are more fun to bring up than boys.”

“Yes and no. The dream of every mother is to have a daughter to raise in their own image. Mothers and daughters form close emotional bonds while boys tend to be independent and difficult. Unfortunately, that is what society expects. So, although I’ve long known that you were different, I couldn’t risk getting too close in case you became a mumsy-boy. What a stupid mistake. I should've recognized your feminine side and helped you with it. At least I can now help you find your real self.”

I hugged my Mum. “Don’t beat yourself up. Even a week ago I didn’t recognize my female instincts. Let's explore them together as mother and daughter and see where it takes us." We walked home hand in hand, something I'd never done as a boy. The first steps in the bond between my Mom and me.

That evening Mandy phoned. “Beth and I will collect you for school tomorrow morning.”

“Thank you very much.”

Next morning, Mum and I met Beth and Mandy at the gate. Mum kissed each of us on the cheek. “I’m glad that my girl has such good friends. Have a nice day.”

“I’m pleased that you came today. I didn’t really want to go on my own.”

“You and your Mum have done a great job. No-one would imagine that you aren’t a girl.”

We headed off to school and entered by the girl’s gate. There was no fuss. We greeted a few girls in the cloakroom, hung our coats and went into class. I sat with Beth and Mandy and got down to work, very mindful of keeping my knees together and avoiding distractions for the boys. At breaktimes, I mingled with the girls. I was accepted as just another girl amongst the many. The day passed smoothly, and I went home with Beth and Mandy. They stayed with me for about an hour teaching me the basics of secretarial studies, our first class of the following day. I prepared a light meal which we all shared.”

“This is delicious. You’re going to have no problems with domestic science. You’re already as good a cook as most girls.”

“Joan’s helped me with cooking and around the house for a long time. I always thought it strange for a boy, but now it’s clear that Joan’s long had the desire for a mother-daughter relationship. Thankfully, we now have the fun of building that bond.”

Next day I had my first book-keeping class. This course wasn’t rocket science. If you had a grounding in sums and mathematics, it was common sense. Since most girls were never given a chance to be comfortable with numbers, they toiled with accounting and had to learn it by rote. Poor quality teaching further hindered their progress. Even on my first day, I could see that the teacher wasn't comfortable with her course, so what chance had her pupils.

This early experience of schooling for girls was very unsettling. I already knew that the teaching in school was selective. Only fifteen percent of boys, the best academically and those with influential families, were given the intensive instruction and support they needed to shine. The remainder received limited training and encouragement. After all, why waste precious teaching time on boys that were destined to be muscle power in the factories and farms. Despite knowing this, it came as a terrible shock to find that girls were even further down the academic food chain; basically, treated as air-heads no matter their abilities. This travesty was further cemented by making the domestic sciences, home economics and secretarial studies necessary components of girl’s schooling. While these topics were suitable for many, the emphasis upon them significantly limited the options for able girls to tackle more demanding academic studies.

I was by no means intellectually gifted, but I did work very hard at my studies. So, I was lucky enough to be within the upper academic echelon of the boys. This status disappeared as soon as I became a schoolgirl. I was invisible to even my favorite teachers. Apparently, the simple act of wearing a blouse and skirt wiped out all vestiges of intelligence. This revelation explained one mystery; why so few of the highly talented girls who started at the Secondary School went on to do advanced scholarly studies. They'd just been worn down by the system and slipped back into the general morass.

One day during lunch break I was chatting with three girls and found that they were struggling with the mathematics course. I offered to tutor them. It seemed the least that I could do given the advantages that I’d enjoyed in the past. As the year went on several others came to me for additional instruction and much to the astonishment of the chosen few these girls did as well as the best boys in the class. They only needed a little support and encouragement.

A further horror that I faced was one that has blighted schoolgirls for decades, PE in gym knickers. These skivvies along with the standard vest or Aertex shirt gave little protection against the elements and did nothing to enhance the self-esteem of gangly appearance-conscious teenagers. It was bad enough to be so skimpily dressed within the girl’s gym but far worse when outside at the girl’s playing fields. There the audience composed not only of other girls but also hordes of boys doing PE in the adjacent sports fields. The rare sight of scantily-clad pubescent girls always caused male hormones to surge and unleashed a wave of loud behavior. I daren’t repeat the words of encouragement that rang in our ears while we plodded around the racetrack or played sports. Suffice it to say that the lewd comments mostly involved our barely hidden girly bits. The fact that most of the boys had visible tenting of their shorts heightened the distress caused by this mockery. To top off this humiliation, girls had to change for PE in school and then file to and from the sports fields under the ogling eyes of passers-by. Given the anguish felt by any female that accidentally reveals their panties, why was it ever considered appropriate to force girls to parade in public in gym knickers? Like so many before, the experience added to my hatred of sports.

Before and after PE girls got changed together in a room at the entrance to the gym. Not wishing to cause them any embarrassment or discomfort I went into a separate small side room to put on my kit for my first session of PE. By the second time around, having already seen me prancing around in gym knickers, the girls would have none of it.

“No need to hide, join us, we’re all girls together.”

This ready acceptance was humbling. The girls were a still little apprehensive as I undressed with them for the first time but once they saw that I had girly bits, albeit falsies, like them they relaxed. After PE, we usually changed as quickly as possible before heading off to our next class, but we occasionally stayed and chatted together when there was no rush to be elsewhere. We had no airs and graces, so the conversations often became personal and intimate. I learned how the girls were developing, thinking and coping as puberty came to its height. Boys were often the topic of discussion, and the minxes sometimes had me blushing with their observations. I was astounded to find out that many were attracted to the bad boys, because of their masculinity. I tried my best to moderate this view, admittedly to little avail.

We had a History teacher who made no secret of his dislike of teaching girls. The boys got all his attention while the girls were ignored or belittled. This teacher took an intense disliking to me. Who could be worse in his mind than a boy that’s chosen to be a girl? I guess that he saw it as his challenge to make a man of me. So, in my first class, I found myself called up to his desk for some trivial infraction. He gave me two strikes of the belt on each hand, and he didn’t hold back. I burst into tears.

"Stop sniveling, I've no time for cry-babies. Get back to your seat.”

My hands were sore and tingling. I could hardly hold my pen, let alone write legibly but I managed to keep it together for the rest of the lesson. As we left class, the pain resurfaced, and I started to cry again, much to the amusement of the boys. In contrast, the girls were supportive and caring. They comforted me and helped me to tidy up and retouch my makeup.

“That was so unfair. You must make a complaint.”

“No that’s what he wants. The chance to ridicule me even more. I’ll just tough it out and try not to give him a reason to punish me.”

Naturally, the teacher didn’t need an excuse. So, I got three strikes of the belt on each hand in the second week and four swats on each with the heavy Tawse, the one used only for boys, on the third week. I was in agony but kept reassuring myself that the teacher was the weaker individual.

I was on tenterhooks during my next class with that teacher. I was quivering throughout and struggling to concentrate. Miraculously, I didn’t get the belt. What had happened? Had he given up? No, while copying notes from the blackboard, I noticed that the teacher was looking intently in my direction, not at me but under my desk. In my distressed state, I’d forgotten the cardinal rule and had slipped into the full spread. Like a laser beam, my white knickers had attracted the teacher, who was now mesmerized by my crotch. My first instinct was to close my knees, but I resisted. I knew that the teacher would leave me alone for as long as he could gaze at my panties. I didn’t like this intrusion but decided that it was a price worth paying just to keep him at bay.

Afterward, several of the girls commented on the teachers improved demeanor, and they laughed out loud when I told them of the reason.

“Wow, this is going to be fun. The chance to use female charms on a male. He doesn't stand a chance. He’ll soon be putty in our hands.”

From then, the girls on the front row took it in turns to provide a lovely view of their panties. Occasionally, two or three of us would do so on the same day. That really unsettled him because he couldn’t concentrate on just one view. On the final day, the teacher almost went into meltdown as we all put on the show for him. The girls in the back rows didn’t have the same opportunities, but many now left their blouses open low enough to reveal a hint of bra. This proved equally distracting for the teacher. On reflection, he must have known that he was being played, but the poor lad just couldn’t help himself. He now spent more time coaching us and, much to the dismay of the boys stopped giving us the belt. After all, he didn't want to risk losing this on-going show. History became fun, and at the end of the year, the girls did as well in the exams as the boys. We spread the word to girls in the other classes, and many successfully used feminine guiles to moderate this teacher’s conduct. Looking back, we were wrong to pander to the teacher’s sexist attitudes, but it taught us valuable lessons; males weren't all-powerful, they had weaknesses that could be exploited. Girls didn’t always have to be the subordinate sex.

Jenny and her gang continued lording it over the girls. As with most bullies, they believed that they were untouchable, but a breach of school rules was to be their downfall. Fraternising with boys was frowned upon at any time but was an absolute no-no during the school day. Most girls knew that Jenny and her followers regularly met with their boyfriends at lunchtimes but were too scared to speak out. It’s unknown who plucked up enough courage to tip the wink to the Deputy Headmistress, Miss Abernathy but Jenny and compatriots were caught by a group of teachers sent to look for them. With incontrovertible evidence of guilt, the sentence for Jenny and her followers was swift and painful.  

At the end of the lunch break, all girls in school were told to assemble in the gym. At first, there was a buzz of speculation over why we were there, but then the hall fell into silence as Miss Abernathy, and two PE teachers led Jenny and her gang, now dressed as for PE, to the front.

Miss Abernathy faced the crowd. “These girls broke the school rules. They knew the risks in defying the school’s authority and are now going to reap the appropriate reward.”

The first girl was led by a PE teacher to a table in front of the hall and told to bend over. Any hope the girl had that the Gym knickers would give protection soon evaporated as the teacher, a hockey coach, struck her bum with the heavy Tawse. She was howling as the fourth whip-crack sounded throughout the gym and in floods of tears as the sixth and final strike found its mark. Between them, the PE teachers dealt with each of Jenny’s gang in the same robust manner.

Jenny was stoic throughout, almost sneering as these events occurred. She was then led by Miss Abernathy to the table and assumed the position. Miss Abernathy had saved herself and had plenty of pent-up frustration to vent on Jenny’s behind. Thunderclaps resounded around the hall as six strikes of the heavy belt did their business. Unlike, the others, Jenny didn’t scream or shout. She said not a word but then gasped loudly when her knickers were pulled down, and Miss Abernathy picked up an extra-heavy three-tailed belt.

A murmur of appreciation spread around the room when Miss Abernathy said, “This is a special gift on behalf of every school girl that you’ve bullied.”

Jenny squealed as her bare bum felt the first fiery kiss of that hardy belt and was begging for mercy by the eighth.”

“Quiet girl, you’re getting the Baker’s dozen that you deserve.”

Jenny was howling and crying uncontrollably as Miss Abernathy unleashed a further five hefty strikes on Jenny's already tenderized bottom.

Jenny moved to get up. “Stay where you are. Savor the pain. If you break the rules again, you will suffer far, far worse.”

Jenny’s agony was compounded as girls filed out of the gym. She couldn’t hide, her glowing behind and broken resolve were there for all to see. She would never instill fear again. In fact, this public thrashing was Jenny’s epiphany. During the rest of her time at school, she was almost the model pupil.  

Despite some bad experiences, I was enjoying life as a girl. I’d bonded with my mother and now had an array of friends on whom I could trust and rely. My school days were happy. Mum went to great lengths to train me in the skills that a girl needed for running a home, so even the domestic sciences and home economics classes now had relevance for me. As with most girl's subjects, the teaching was unimaginative. The teachers concentrated on their star pupils, leaving the majority to their own devices. Luckily, Mum trained me well, so I was able to help girls struggling with these household studies. As it turned out, given this extra backing, all the girls in my class excelled.

On Saturdays or Sundays, there were usually several girls in our house for tutoring in mathematics, the sciences, and even history. I found it rewarding to guide these highly intelligent and motivated girls. They weren’t only sponges for information but also wanted to tease out every vestige of meaning from new data. While I started out as their tutor, I soon began to learn from them. Teaching for boys was very black and white; these are the facts, don’t question them. The girls had no such impediments. They would probe any assumptions that had been made and often as not found flaws. The girls challenged me and drove my analytical skills to higher levels. It was win-win all around. I found it utterly frustrating that the school still stuck to the attitude that girls were only homemakers and didn't merit any mentoring.

Girls were kept on a short leash at that time. They were always expected to behave impeccably, while disobedience by boys was in part tolerated. If a girl disappointed her mother the retribution was usually swift and painful. Boys knew this and played to it, as I found out to my cost. One day in the park a boy was harassing me and calling me names. I pushed him, and he fell over. Mum’s reaction was immediate. The boy was laughing his head off as I was dragged home despite my protests.

"You’ve embarrassed me once again. You acted like a slob, not a lady. You’re about to get a sharp lesson in manners."

“But it wasn’t my fault. The boy goaded me. Besides I’m too old to be spanked.”

“No excuses my girl, you misbehaved and will pay the price no matter your age."

Mum was very adept with the hairbrush and rigorously applied it on the bare. My bottom was sore, but the disgrace was even worse. All in the neighborhood would know that I'd let down my Mum and got my just desserts. I kept a low profile for the next few days, spending the time helping Mum with her chores. She didn’t let any ill feelings linger. We shared a mother-daughter hug soon after her last swat hit my bum.

“Be a good girl, let’s have no reason to repeat this again.”

 “I’m sorry. I promise I won’t disappoint you again.” 

Girls had little choice but to accept the strict chaperoning of their lives. A few rebelled against the restrictions, but most girls kept the line. Since I was still trying to find my way as a girl, I found it reassuring to have an adult around. Mum and I went shopping together, to the park and to visit her friends, who were generally surprised but pleased that Mum had brought along her sweet niece rather than her son. Occasionally, I accompanied Beth, Mandy, Isobel and Jane and their Mums on excursions and on a few occasions, we all went on day trips to the seaside. 

For me these outings were invaluable. Not only did they help build up my confidence as a girl, but they gave me the chance to study how girls interacted out-with the disciplined school environment. Their bearing, mannerisms, and speech were so much more expressive and distinctive. Mum, Beth, Mandy, Isobel, and Jane each had their own styles and traits. Beth and Isobel accentuated mainly using their hands, while Jane did the same through pronunciation, voice intonation and pitch and Mum and Mandy used a combination of these methods. I watched and copied traits that I liked and tried to use them, with greater or lesser success. Unsurprisingly, mannerisms adopted by my Mum eventually became integral to me.

My new female manner brought about an unexpected turn of events. Jenny Tough, of all people, came and sat beside me in the girl's cloakroom and began chatting.

"I can't apologize enough for the hell that I put you through in the past. I’ll understand if you don’t want to talk to me, but I have a question that I think only you can answer."

I was apprehensive despite knowing that Jenny was reformed. “Apology accepted. How can I help?”

“You’ve always been quite girly, but over the last few months, you've developed a very female manner. Outwardly, you’re now as feminine as most girls. How have you done it?”

“Thank you, that is kind but why do you ask?”

“I’m physically female but can in no way be described as feminine. That’s to be expected as I’m the only girl in a family of six and raised by my father. We have a loving home, but not one that is conducive with femininity. Can you help me?”

I realized immediately that this was the likely root of Jenny’s behavioral problems. At home, she probably had to be tough and dominant to survive and didn’t know any other forms of behavior. Jenny now wanted to be more feminine, to change her persona and be accepted.

“Sure, I can help, and give you pointers but the hard work has to be done by you. You need to girl-watch, see how they behave together, select traits you like and try them out.”

By now, Beth, Mandy, Isobel, and Jane had spotted Jenny and me sitting together and come over to check that I was okay. I explained what Jenny and I were discussing. Given the history, the girls could've been forgiven for not wanting to have anything to do with Jenny, but no. A girl needed their help, and they were comfortable to support her. We didn’t become close friends with Jenny, but we did regularly chat together. Jenny steadily developed a more feminine manner, she was clearly happier in herself and soon had her own group of close female friends.

Word of my meeting with Jenny reached Miss Abernethy, and I was called to her office.

“I’ve been told that Jenny Tough talked with you yesterday. I just wanted to be sure that she isn’t bullying you again. If so, I want to nip things in the bud.”

“No, nothing like that. Jenny asked about ways to enhance her feminine manner.”

“Oh, that is good. Jenny has changed, a good example of the re-educative properties of belt vigorously applied to the bottom."

“I’ve thought quite a bit about Jenny’s punishment. Do you mind if I ask you a personal question about it?”

“No, you may ask, but I won’t answer your query if it’s inappropriate.”

I blushed. “You had a strong reaction when you gave me the belt for the first time. To put not too fine a point on it, you were turned on and climaxed. When you punished Jenny, there was no reaction. You did the job, and that was it."

“What are you insinuating?”

“I’m not inferring anything, but I have been thinking of how to thank you for helping me find my female side. I have an offer for you; to re-enact the events of that day.”

 I knew that I’d hit the correct note when her frown disappeared, and she broke into a smile.

“Are you sure about this?”

“Yes, I owe you so much.”

"Okay, after classes go see Mrs. Jones, the school nurse."

I was on tenterhooks for the remainder of the day, and Beth and Mandy were perplexed when I said that I’d to stay on after school. Being good friends, they didn't quiz too much.

I went to Mrs. Jones room.

“This is a turn-up for the book Miss Smith, but I have everything ready.”

Soon, I was dressed in boy’s clothing and Mrs. Jones was leading me to Miss Abernathy’s office. Miss Smythe, the school secretary was already there.

Miss Abernathy looked very business-like and somber. “Well, well, Mr. Smith, I hear that you’ve been disruptive again. You’ve obviously forgotten the painful lesson that I gave you for previous misbehavior. Now, I see that I need to remind you of the simple message: troublemaking on your part leads to the vigorous application of the belt on my part and agonizing pain in the posterior for you. Now bend over my desk."

As I did so, Miss Smythe and Mrs. Jones grabbed my hands and pinned them down. Miss Abernathy walked behind me, undid my belt and pulled down my pants. As before, Miss Abernathy hesitate before hooking her thumbs into the waistband of my underpants and pushing them down to my ankles.

I shivered when Miss. Abernathy stroked my now bare bottom. “Mm, lovely buttocks, pert and firm. This is going to be sweet, but unfortunately not for you Mr. Smith.”

My tension heightened further while Miss Abernathy strolled over to a drawer at the front of her desk and picked out the same extra-heavy three-tailed Lochgelly Tawse that she’d used on Jenny.

“Miss Tough merited the maximum that I’ve ever given a girl. You are to get the same tariff, Mr. Smith.”

I had an immediate flashback to Jenny’s punishment. Now, I was afraid and regretting my stupidity. ‘I'm nowhere near as tough as Jenny, and she was broken by the punishment. I knew that my ass was going to suffer, but I had to try to be resolute. I could only hope that Miss Abernathy meant to give me a Baker’s dozen on the bare since that was what Jenny received with that fearsome belt.”

I knew better than to ask and was still mulling things over as those vicious tails made their first fiery strikes on my buttocks. The combined action of the three tails triggered a wave of agonizing pain, which was further ratcheted up by hit after hit. I was sobbing and begging for mercy as Miss Abernathy reached the Baker's dozen, but there was no respite. My bottom was blazing like a furnace, and I was weeping buckets after strike nineteen. I was broken just as Jenny had been.

Through the tears, I watched as Miss Abernathy put away her belt and then sat down. I was disappointed to see that she was flushed but not ecstatic. Strangely, Miss Smythe and Mrs. Jones seemed to be more aroused than her. I’d expected that Miss Abernathy would orgasm like she did when belting me before. That was to be my reward for her. I’d failed, all my pain was for naught.

I couldn’t let things end in this unfortunate way, so got down on my hands and knees and crawled over to Miss Abernathy. Before she could say a word, I’d lifted the front of her long skirt and placed it over her knees. With her Directoire Knickers now on full view, I slipped my fingers under the leg elastic and slowly moved my hand under the cloth. Miss Abernathy didn't object, in fact, she was sighing as I stroked my way up her thigh and gasped with delight as my fingers found her mound of Venus and tousled the hair. My fingers tingled when they located and stroked pussy lips for the very first time, and Miss Abernathy moaned steadily while I slowly massaged her slightly moist jewel.

I saw a look of sadness on Miss Abernathy’s face when I withdrew my hand. But it was quickly replaced with a broad smile once I hooked my fingers around the waist elastic of her passion killers and pulled them off to reveal her beautiful fud. I was now into unknown territory. What best to do next? Memories of the intimate conversations shared after PE came to mind and gave me an unambiguous message; don't dawdle, go straight for your target. So, I pushed Miss Abernathy's knees apart and slipped my head under her skirt. In the darkness, I felt her thighs rub my cheeks as I closed in on her precious gem. Miss Abernathy gasped with pleasure as my lips found hers and latched onto them.

“Oh my, oh my, you’re a very naughty boy, but I like it.”

Miss Abernathy’s hands clasped and stroked my still glowing bum as my lips caressed hers. My tongue worked its way between the folds, revealing many secrets including her well-hidden magic button. Miss Abernathy was purring like a cat while my tongue and lips enchanted the entrance of her love tunnel. She began to shudder as I licked hard on her clitoris.

“Wow, my pussy’s going berserk.”

After another strong tremor, her twat flooded with juice, and she meowed gently as I then lapped out every drop of her love honey.

When I peeked out from under her skirt, Miss Abernathy was slumped but smiling with intense satisfaction.

"Young man, I need to recover now, but you have more joy to give. Miss Smythe and Mrs. Jones are awaiting. So, having just successfully gone down on my first pussy I then went on to drive two more to climax that afternoon. Each was unique. Miss Smythe’s clit was particularly sensitive; needing only gentle touches from my tongue to push her over the edge.

Later, while still recovering my calm Mrs. Jones said, "I'll take Mr. Smith back to my room so that he can get changed to go home.”

Miss Abernathy and Miss Smythe smiled as I pulled up my undies and trousers and tidied myself.

"Thank you, Mrs.  Jones, that is kind of you and thank you for an enjoyable afternoon young man."

Mrs. Jones led me along to her office, we went in, and she locked the door behind her.

“Get undressed, you’ve got more work to do.”

I dropped my pants and undies to my ankles, but Mrs. Jones said, "No, everything off.” She then picked up all my clothes, put them in a cupboard and locked it. Great, I’ve no way out. I can’t go home in the buff, and my girl clothes are locked in the room next door.

Mrs. Jones slipped off her panties, sat down on the sofa and pushed my head under her skirt.

“You know what to do, get on with it.”

To be sure that I couldn’t back away she hooked her hands around my buttocks and pulled me in.  

Mrs. Jones’ pussy was more bulbous than that of Miss Abernathy or Miss Smythe. The lips were more prominent and had many folds and sub-folds. I took my time exploring their every nook and cranny with my tongue, so Mrs. Jones soon became highly aroused. Her breathing became erratic while my tongue plundered the entrance of her love tunnel and she went wild when I forcefully sucked her magic button. She bucked and meowed as the love juices flooded from her fanny and I licked her out.

I'd only just finished when Mrs. Jones clasped my head between her thighs. “Stay where you are. Get back to work. I want to cum again.”

I went back down on Mrs. Jones fud. This time my tongue got deeper into the entrance of her love hole, and I must have hit some new sweet spots. In a surprisingly short time, Mrs. Jones was rearing and moaning with pleasure as she climaxed. Again, I supped her sweet juices to the full.  

Mrs. Jones still wouldn’t let me go. “Stay there. Go down on me again.”

By now I was dizzy from the mix of sexual aromas and scents trapped under Mrs. Jones' skirt but still enjoying the novelty of lip service. This time she took far longer to come to the boil but after much raiding of her love hole by my tongue and fingers and enthusiastic suckling of the magic button Mrs. Jones orgasmed again and juice flooded from her twat. I struggled to cope with the flow but eventually lapped out every drop.

Mrs. Jones now settled, her breathing returned to normal, and she released me. Then, she French kissed me and hoovered up the last vestiges of her love honey from my lips and tongue. “Thank you so much. I haven't been so satisfied in a long time.”

Mrs. Jones then led me through to her room, where I had a shower, re-dressed and did my hair and makeup. In the meantime, she had also showered in the girl’s gym and put on a new set of clothes. I wondered why, but then realized that her others would be infused with the unmistakable aromas of our exertions. No need for her to risk giving the game away at home.

Mrs. Jones then handed me a pair of her used panties. "Keep these as a souvenir, I’m going to keep your boy pants.

“Thank you, I’ll keep them safe.” What else could I say?

We looked for Miss Abernathy and Miss Smythe but found they’d already gone. As I was about to leave Miss Abernathy’s empty office, Mrs. Jones clasped me in a tight embrace and kissed me. While rooted in the throes of a French kiss, Mrs. Jones grabbed my hand and maneuvered it inside her knickers until my fingers were touching her wet twat. I got the message, and soon her fanny was twitching with excitement while I worked two fingers deep into its tunnel and probed and stroked every possible sweet spot that I could find. It wasn’t long before my hand was doused in love juice, and her knickers were soaked.

“Thank you for rekindling my desires. I’ve been celibate for years. Not out of choice. My husband lost interest in sex, and that was it. Whenever I raised the issue, he would tell me that I was a sick and shameless hussy for still having sexual thoughts. So, eventually, I accepted a loveless fate. Today, you’ve shown me that I'm not sick. I'm a healthy woman with normal sensual needs. You’ve made me a living sexual being again, not just a house-keeping skivvy. I can hardly contain myself. I’d love you to stoke my fire again and again, but unfortunately, I must head off home to someone who has no idea what he’s missing. Maybe we can do the muff dance again sometime. There are many kinks that I could teach you.”

“Always happy to please,” was all I could say. Hand in hand we walked out to the girl’s gate before going our separate ways.

The wind was quite strong and gusty, which should’ve scared me, but the wafts of cold air sweeping over my still hot bum were bliss, so I walked home more slowly than usual. This allowed me time to mull over an extraordinary afternoon and to reach the realization that today’s events hadn’t happened by chance. Miss Abernathy, Miss Smythe, and Mrs. Jones had all been in the office for only one reason; to have an orgasm. When the excitement of my belting didn’t have the desired effect, they didn’t give the slightest objection to my switch to plan B. In fact, it’s almost sure that they’d discussed how to encourage me in that direction if need be. The knowing glances I saw exchanged that afternoon were a sure sign that I fulfilled the plan.

I owed the ladies so much for their guidance along my female path that it pleased me to have the chance to help them discover and enjoy their own sensuality. Would they want to do it again? Of course, they did; the genie was now out of the bottle. About once a month I’d be called to Miss Abernathy’s office to hone my muff diving skills on all three of them. This was fine for Miss Abernathy and Miss Smythe, but Mrs. Jones sometimes required additional attention. Miss Abernathy and Miss Smythe were never as hungry as her, but their demands did increase with time. True to her word Mrs. Jones taught me many ways to make a girl happy and Miss Abernathy and Miss Smythe reaped the benefits.

As a reward for my ministrations, Mrs. Jones bought me a set of pussy prostheses. They were quite realistic, held in place with adhesive and melded seamlessly with my body; even the lips were soft and tactile. I liked being free of the straps and waistband of my previous mock fud. A bonus was that my panties no longer had straplines. Each faux pussy had a pronounced mound of Venus which just added to my sense of femininity. The downside was that this mound was clearly apparent when I wore gym knickers and proved to be a new delight for any boys watching as I labored my way around the race track. Fortunately, now more tolerant of male weaknesses I just said to myself, “Ah well, at least I’ve made their day.”   

 Miss Abernathy, Miss Smythe, and Mrs. Jones all wanted their erotic fun but didn’t want things to go out of their control, so our sensual encounters never strayed beyond smooching and avid pussy eating. Interestingly, they were never intimate with each other. To them, that would be wrong, but being muff dived by a girl-boy was okay and certainly much safer than exposing themselves to a feral male. I did sometimes wonder when this had become part of the ladies’ plans for me. In fact, I even began to consider whether my female journey had been initiated and directed by them all along. Mind you, I wasn’t complaining.

These erotic events had an unexpected effect at the school. Girls were soon saying to me that Miss Abernathy, Miss Smythe, and Mrs. Jones had changed completely. They’d become sympathetic, almost friendly with their charges.

“We can’t understand what has happened.” Of course, I couldn’t enlighten them as to the wonderous side-effects of sexual satisfaction. 

Miss Smythe was reserved and shy. She was quite restrained when I first went down on her, but like many a quiet one, she quickly threw off all inhibitions and became an enthusiastic and hungry partner. One time we were warming up in her office and deep into a tongue tango when her hands began to wander. She reached into my panties and found my new pussy. In her excitement, she tweaked the lips, pushed a finger between them, located what she thought was my clit and began nuzzling it with her fingertip. What she’d found was the tip of my cock, and it reacted to the stimulation. I began to feel uncomfortable, my glans came to life and started twitching moments before I felt a wave of pleasure and my gusset became wet.

Had I peed myself? No, Miss Smythe was positively beaming as she showed me the clear juice on her fingers. “You’ve just squirted young lady.”

I kissed Miss Smythe with a passion. I was over the moon. I’d never thought it possible for me to experience a girl-like climax and this sweetheart had made it happen. Just as I’d done for her, Miss Smythe took up the challenge of finding how best to stimulate my ‘clit.' Over time, she found that massaging the skin around the prosthesis, particularly in my inner thighs heightened my sensitivity. The spasm, ecstasy, and flow of juice when she then licked my ‘clit’ was remarkable. This was our special secret. We didn’t overdo it but occasionally shared the joys of a sixty-nine. Miss Smythe also had the bonus that I went the extra mile to ensure that she had the most enthralling of times.

I was enjoying my time as a girl, but also aware of a possible dark cloud on the horizon. I’d soon have to decide how to live once I'd left school. Would I revert to being male or continue with a female persona? There were definite pros and cons for either option. Two events were to influence my final decision.

A fear of being discovered as a boy in a dress always hung over me, despite my care to be ultra-girly. Strangely, although I knew how badly males would react if I was discovered, they weren’t a big concern. After all, they only needed a nice pair of tits, long legs, short skirt and the occasional flash of knickers to be convinced of womanhood. In contrast, females weren’t blinded by appearance. The slightest hint of non-female behavior, speech or manner would be a giveaway. How would they respond to finding a girl-boy in their midst? I assumed that such an intrusion would provoke fury, but I was pleasantly surprised when my secret was exposed.

Mum, Beth, Martha and I visited the lady's clothing store where Mum and I’d first shopped together for girl’s wear. As soon as we entered the shop, the lady behind the counter recognized me.

“My, my young man you’re the picture of femininity. You obviously enjoy being a girl.”

There was a collective gasp of disbelief amongst the women and girls near the counter.

“Why did you say that? She’s obviously a girl.”

Whispered conversation spread throughout the shop, and soon Jennifer and Samantha appeared. “No, she isn’t. John’s a boy who wanted to find out what it was like to be a girl. By the looks of things, he’s happy as Joan.”

Much chattering between mothers and daughters ensued before they gathered around me. A couple of adventurous youngsters felt the need to check that I was en femme.

“Oh, what pretty panties. Mum, can I get ones like those?”

That broke the ice, a chuckle rippled around the crowd and one by one they began to quiz me about my time as a girl. The fact that I’d experienced the bad, as well as the good of being a girl, struck a chord with them. "Wow, this isn’t a game for you. You're really encompassing girlhood.” I was astonished to find that there was no hint of criticism, only acceptance, and enthusiastic encouragement.

“If I had my way, all boys would be forced to do the same. They’d soon learn to behave.”

Young and old in the gathering expressed similar sentiments.

An elderly lady asked, “Are you planning to live as a woman after you leave school?”

“I don’t know what will be for the best. For now, I’m just enjoying girlhood.”

"I know that the choices are difficult, but you're obviously happy and confident as a girl. I think that you should be the real you and enjoy life to the full.” There were mutterings of agreement from the crowd.

Fortunately, Beth and Mandy appeared with bundles of clothes to try on so I could escape to the changing room without giving a definitive answer.  

The second event was at a party held in the house of my friend Isobel. It was an all-girl affair, with Isobel's Mum and Aunt at hand to keep an eye on the proceedings. Isobel's cousin Phil was staying with the family for the Easter holidays, but he stayed well out of the way, not wanting to be involved in any soppy girl’s night.

I was relaxed and enjoying the evening when I went through to the kitchen to get a glass of juice. On my way back I bumped into Phil, and before I realized what was happening, he’d slipped his arm around my waist, pulled me in and planted a kiss on my lips. I should've struggled but was mesmerized by the sweet sensations that began to flow between us. Lips locked together I was entranced by my first snog with a boy.

Phil led me through to his room, and we resumed smooching. Consumed by passion, I failed to notice that Phil’s hands had begun to wander. He’d got under my skirt and was already moving towards my pussy when alarms started ringing in my head. I knew that I had to stop him but equally couldn’t risk causing a scene. Luckily, I spotted the bulge in Phil’s trousers. I quickly unzipped his fly, got into his drawers and clasped his roused shaft in my hand. Phil’s willy reacted immediately; it twitched with excitement and engorged rapidly in my tight grasp. The flood of urgent messages from Phil’s cock must have overwhelmed his poor brain because he froze, lay back on the bed and withdrew his hand from under my skirt; not a moment too soon as his fingertips were already at my knicker elastic. Phil’s eyes glazed and he began cooing like a dove while I vigorously beat his meat. He then grunted animal-fashion as his cock tremored, spasmed wildly and shot its load of spunk. Once Phil had dozed off, I listened at the door to be sure all was clear and then went across the corridor to the loo. I tidied myself, let my racing heart settle and then headed back to the party.

“Oh, there you are Joan. I was worried when you didn’t come back. I was about to come looking for you.” 

“I felt faint and had to sit down for a while to recover. I'm fine now.”

I re-joined the party.  Still high on adrenalin, I enjoyed the rest of the evening as though nothing had happened. My good mood continued while I walked home with Beth and Mandy and went off to bed.

When I woke up the next day, the realities of the previous evening hit home. I was obviously upset that Phil had tried it on with me but even angrier with myself for so easily losing control of the situation. I’d succumbed almost immediately to Phil’s charms. What did this mean for my future as a girl? On further consideration, I realized that events had uncovered another serious issue. At first, I assumed that my intense panic when Phil got his hand up my skirt was due to my fear of discovery, but this was only part of the story. My bad experiences with boys in the past had left an indelible mark. The prospect of a male touching or pawing my privates was deeply repugnant; even just the thought triggered a deep disgust.

At this point, I’d almost decided that I would continue life as a female, but these new revelations raised doubts. At that time, female-female partnerships were still considered shocking, and now the prospect of boy-girl/boy relationship seemed out of the question for me. If I chose womanhood, I faced the possibility of life alone. To have a long-term partner, I'd either have to hide my distaste for boys or revert to be a male.

Beth and Mandy visited me a few days later and immediately sensed that I was troubled. “What’s wrong?”

I let it all flow out.

Beth and Mandy both hugged me tight and kissed me.

“Be the girl you want to be. Things have a habit of working themselves out. Remember that we’ll always be here for you. Besties are forever.”