My sister Helen and I lived with our mum Margaret on the outskirts of a small Scottish village. Kate, Hazel and their mother Isobel were our neighbors. The girls were very alike, enjoyed each other's company and quickly became inseparable friends. I, on the other hand, was a loner. I was effete and in no way interested in the usual boyish rough and tumble pursuits. So, I didn't fit in with any of the local crowd and was shunned and often bullied for being a Jessie.
Mum urged me to join some local clubs, but this didn't work out too well. I was useless at sport and was usually left out when sides were picked. Even more, macho kids didn't want to be associated with a sissy. Determined that I should have some friends my age, Mum and Isobel decided to encourage the girls and me to become pals. In today's world, this arrangement may seem an obvious one, but for the 1950s it was radical. Back then, boys and girls were kept apart while growing up. Ostensibly, the aim was to keep them pure and free of wicked thoughts, but, it was a pillar of the chauvinist status quo. Gender separation allowed boys to be trained and ingrained in macho superiority while girls were discouraged from free thought and conditioned for a role of subservience and unquestioning obedience to their male masters. This practice was preached and strictly enforced on the lower orders by the authoritarian busybodies or supposed betters of the time.
This ethos had been ingrained in me from an early age, so, despite my loneliness, I was very apprehensive when Mum announced that I was going to spend buddy-time with Kate and Hazel. However, ever obedient, I agreed to try Mum's plan. Next morning, she, Helen and I walked hand in hand to Isobel's home. After the initial pleasantries, Helen led me through to the girl's room. Kate and Hazel jumped with joy and hugged me. To my astonishment, they were glad to have a new playmate even if it was, horror of horrors, a boy. The girls quickly included me in all their play and antics. In return, I suppressed any boyish instincts and took my full part in their girly games, including playing with dolls. For the first time, I felt comfortable with kids of my own age. The girls didn't judge or belittle me, they just wanted to be friends and share their playful fun. These uplifting interactions gave me the boost that I needed and in time helped me become confident and outgoing.
The difficulty with this arrangement was that we could only be together while indoors. All sorts of moral alarms would've been set off if I was seen outside with the girls in the absence of an adult chaperone. While this situation was acceptable during the dark and cold days of winter, I began to feel guilty that the girls were trapped indoors with me when the warm days of spring made their appearance. So, one day I said, "Girls, it's a warm sunny day. Why don't you go and play outside? I'll be okay in here?"
"No way, you're our pal. We are a unit. We won't leave you here on your own."
I was astounded by this feminine empathy. No way would boys have been so considerate. So, despite my best efforts we played indoors for the rest of that lovely spring day.
The relationship between Helen and me changed because of our ongoing camaraderie. No longer were we the fractious brother and sister. Instead, we bonded and acted in many ways like sisters who shared their thoughts and secrets. So, it came to be that Helen broached me with a novel solution to our problem of being outdoors.
"Believe me, I'm not cheeky or rude in what I'm about to say. You're quite feminine in appearance and manner, more so than some girls that I know. That's the main reason why other boys look down on you and treat you as effeminate. Kate, Hazel and I have talked about this and think that you could pass as a girl if you wore the appropriate clothes. Would you try that? We'll all help and take care of you. Then, we can all play outside in the fresh air and sunshine."
My first flustered reaction was the obvious one. "Are you suggesting that I dress up as a girl? No way, I can't do that. I'm a boy."
"Are you really? We wouldn't be having this conversation if you were a boysy boy. I think that hidden under those male clothes, there's a sweet lassie that wants to break out."
I went bright red in shock. Helen had put into words the very thing I'd begun to consider. Was I a girl in a boy's body? That circumstance would explain why I was at ease with the girls and detested all things boyish. But, if this was the case how was I to deal with it. After all, there were only two accepted genders: male or female, with no in-betweens.
"You look pensive. What are you thinking?"
"I owe you girls so much. It's unfair that you must stay inside because of me. I'm scared, but I'll give dress-up a try. Who knows, I might get to like it."
Helen ushered Kate, Hazel and me through to the living room where Mum and Isobel were chatting. Helen explained the plan.
"Are you happy to do this? The girls aren't forcing you?"
"No, it is my choice to give it a try."
Mum and Isobel were smiling as both kissed me on the cheek. "It's going to be fun having another girl to fuss over."
I was unsure what was meant when they said, "you'll have to be completely en femme and look and act like a girl, not just be a boy in a dress" but was soon to find out.
Isobel told Kate, Hazel and Helen to go outside to the lawn. I was taken through to Isobel's bedroom and told to take off all my clothes. Soon, I was standing there in my birthday suit, trying to cover my little boyhood with my hands.
My discomfort didn't lessen when Mum and Isobel both said, "don't fret, we've seen it all before."
On the bed, there was a collection of girl's clothes. Mom held up a pair of pink panties, told me to step into them and then pulled them up around my bottom. I never forget those incredible first-time sensations as the elastic dug in and pulled the knickers into a comfy cocoon around me. The sense of femininity was further heightened when Mom put me in a training bra; my boyhood now hidden, my girlhood was coming to the surface. Isobel then fitted me with a full slip and an above-the-knee summer dress, which she then zipped up at the back. Next, Mom sat me down at the dressing table, and I watched in the mirror as she fitted a wig, combed out the hair and applied some light makeup and lipstick. It was astounding to see my transformation from a boy in a dress to a girl. I was still agog when Isobel slipped my feet into socks and a pair of court shoes.
"Come, look at yourself in the full-length mirror."
Unused to the small heels, I hobbled over to the mirror. Looking back at me was a young girl. I loved the look but was shocked at how uncovered I was. I hadn't shown this much bare leg since I was in short trousers and even then, the essentials had been more securely covered. My disquiet was heightened even more when Mum and Isobel led me outside, and for the first time, I felt the wind blowing around my legs and skirt.
"Girl's, meet Bobbie, the newest member of our family. Enjoy the day."
The girls gazed at me, mouths open, for a while before they cheered and rushed over to me. They hugged and kissed me. "We girls are going to have so much fun together."
We played together for the whole afternoon, and I soon experienced the challenges of a dress. My knickers were often on show as the wind flipped the skirt up or I bent down to pick up things. Of course, the three imps had a great time conning me into revealing more than I should.
"Oh, what lovely panties. Oh, what lovely panties."
I was caught out so often that my face was almost a permanent red, but at least I now appreciated why girls got so distressed if they accidentally revealed their panties nearby leering non-sympathetic boys. To be fair to the Kate, Hazel and Helen, after they had their fun with me they began to teach how to move about without revealing my undies.
We were laughing and giggling together when a couple peered over the hedge at the end of the garden. The lady said, "You seem to be enjoying the sunshine girls?"
"Yes, mam. Being outdoors is nice. Are you enjoying your stroll?"
"Absolutely, it's good to get out of the house and feel the sun again." With that, the couple wandered off.
"Phew, that was close. The couple just saw four girls in the distance, but they might have spotted you if they'd been nearer or looked harder. You're still acting like a boy. You're gait, and mannerisms need to be more feminine if you're to carry this off."
Kate, Hazel, and Helen were now on a mission. By that evening, they had dressers of clothes and other necessities set up for me at both houses. They could now train me whenever time permitted. Helen had most opportunity and was the hardest taskmaster, picking up on any deviation from a female deportment and demeanor. Helen was determined to make me a daughter of whom Mum could be proud. She also enjoyed bossing me around. Soon, with thorough tuition, I began to have a more feminine persona.
One thing that bothered me was that my skirts and dresses were much shorter than those worn by the others. When I asked Helen said, "we've worn skirts all our lives and have had plenty of time to learn how to keep them under control. You needed to gain the same knowledge quickly, and we thought that wearing a shorter skirt would help you focus on the issue."
"Finding out how easy it is to reveal my knickers has made me very careful. Can't I wear longer skirts now?"
"What and hide those lovely legs. No, no, you'll stay in short skirts and dresses until we say otherwise." I blushed profusely but accepted my fate.
One day we were playing on the lawn as usual when our ball rolled away down the garden path. Without thinking, I ran after it. I'd just picked the ball up from beside the fence when I was wolf-whistled by a boy standing at the gate. "Hey sweetie, why haven't I seen you before, where have you been hiding?"
I went bright red, didn't say a word and ran back to Kate, Hazel, and Helen. They were laughing their heads off but then said, "you've cracked it. That boy saw only a pretty young girl that he quite fancied. Now, we can be sure it's safe for us to be outside together."
Mum and Isobel came rushing out of the house to see what the commotion was about, and we had a group hug when the girls told them of what had happened.
Kate, Hazel, Helen and I continued to play together on weekends and during the school holidays. We always tried to be good, but like all boisterous pre-teens, we occasionally crossed the line. The retribution was swift and painful. Over the knee, knickers down, and a hairbrush applied vigorously to our bottoms. It was an added shock to find that Mum punished me more severely as a girl than ever as a boy. Bobbie was always spanked harder and longer and reduced to tears. It seemed unfair at first, but of course, girls are expected to adhere to higher standards than boys. They must be sweet, well-behaved and courteous always. Any deviations from this ideal reflect poorly on their mother and inevitably result in a sharp and sore remedial lesson. Although I would've gladly done without this aspect of girlhood, it did strike me as somewhat fairer that Helen and I were now punished to the same extent for the same misdemeanor.
During the summer holidays, I spent most of my time as a girl. This experience wasn't all fun and play. The girls regularly helped their mums with household chores, and I began to do my share; both to pay my dues and learn more about the demands of girlhood. Mum and Isobel were both over the moon to have an extra pair of hands and happily trained me to clean, cook, wash and iron and sew. I soon appreciated how hard the girls worked behind the scenes, how much in the home depended on them. Although I was usually exhausted after a day of chores, I did enjoy doing them and found my forte in cooking and baking.
The best times were while we were outdoors working in the garden, but this was also when I was caught out again. On the first day, the girls sent me to tidy some flower beds at the far end of the garden. All was going well until I heard some wolf-whistling and shouting. "Oh, what a lovely show. Those pink panties are sexy. Let's see the full moon."
Here was I busy pulling out weeds from the flower bed utterly oblivious to the fact that these actions would cause my skirt to ride up and reveal my knickers. I was working at a place close to the fence, and naturally, there had to be a passing group of boys to see my shining glory. I went beetroot red but didn't move. I pulled my skirt down to cover my dignity and continued to work, not wanting the boys to get the satisfaction of scaring me off. I looked around to see Kate, Hazel, and Helen laughing hysterically at my predicament and noticed that they'd changed into slacks before coming out to work in the garden. I'd been well and truly stitched up.
Late into the summer holidays, Kate came to me. "You've not set foot outside this garden as a girl. I dare you to come with us to the village shop. It'll be a real test for you."
Thinking that Mum and Isobel would never allow it, I accepted the dare, unaware that the girls had already got approval but only if I agreed. So, they'd trapped me again, and soon a very nervous Bobbie was walking between Kate, Hazel, and Helen towards the center of the village. Many people were milling around, but luckily none took more than a cursory glance at four girls together. I walked past two boys from my class at school, they leered at me but gave no hint of recognition. Despite this, I was so scared of being recognized that my nerves were jangling all the time until we had been to the baker's shop, bought our goods and got back home. I needed time to settle but was now surer that I could carry off being a girl.
On my second trip to the village we walked together to the shop and bought our goods as before, but as soon as we exited the store Kate, Hazel and Helen ran off leaving me alone.
"See you back at the house."
I was walking through the village when the inevitable happened. Four scruffy looking boys spotted me on my own and sauntered over.
"Well, well, who's the newbie. Show us your knickers darling." I tried to go around them, but they trapped me and started to lift my skirt. I was shaking and beginning to cry when I heard a woman's voice.
"What's going on here, what are you doing to this poor girl?"
The boys ran off, and I looked around to see my rescuer. I was relieved to find that it was Miss Marshall, the school secretary. I'd never dealt with her directly, so there was little likelihood I would be recognized.
"Why are you out here on your own?" I explained about the girls.
"That was very naughty of them. Come, I'll make sure you get home safely."
Mum and Isobel were so glad to see me coming home with Miss Marshall and grateful for her kindness.
"Happy to help, I'm glad I came along when I did."
Kate, Hazel, and Helen were very contrite. "We're sorry. We shouldn't have played that stupid prank on you. We'll never do it again."
I accepted their apologies, but this wasn't enough for Mum and Isobel. Three crestfallen girls appeared later after having been reminded of the error of their ways in the traditional fashion.
From then on, we girls regularly went into the village and to the shops together. I even built up enough confidence to visit some of their friends in their homes. I took on the guise of a girly girl, to leave no one in any doubt of my femininity. The girls always kept a close eye on me and very occasionally had to give me a nudge when I let my guard down and risked revealing more than I should. In turn, I found a warning sign of my own. If any boys or men in the room suddenly went quiet, it was wise to check that my knees were together. Nothing transfixes the male of the species as much a slight hint of panties. Of course, I would later in life realize that a quick flash was also a way of distracting males. The poor souls can't help themselves.
I occasionally attended parties held by friends of the girls. I thought that these events were safe for me because they were all-girl and always strictly chaperoned. Despite this, I had my closest call at one of these shindigs. The evening was going smoothly, and we were all listening intently to a record when I suddenly felt a hand moving up my inner thigh. Luckily, I was able to grab the arm and pull it away just as the fingertips touched the leg elastic of my panties. So, the invading hand never reached to its target zone.
I spun around to find that I was clasping the arm of our host's six-year-old son. He'd wandered into the room while everyone was pre-occupied and tried to feel me up.
"You little brat, why did you put your hand up my skirt.
"I'm sorry, I couldn't help myself. A friend was bragging that he'd goosed a girl and I just wanted to find what it was like."
I tousled his hair. "I should smack you, but I won't. I accept your apology. You were led astray by that boy's feeble boasts. Remember this day and never again try to cop a feel of a girl, it's degrading and frightening. How would you like if some stranger groped your crotch?"
"I've never thought of it that way; it would be terrible. I promise never to do it again."
The boy and I sat together for the remainder of the evening while I bent his ear. "Girls aren't just playthings for a boy, they are as clever and able as boys and must be treated as equals and with respect."
I was sad that a boy so young already had chauvinist traits but relieved that I had the opportunity to at least try to stop the rot. His mum apologized profusely to me afterward and later reinforced my message by making the boy's bottom a fiery red color.
My last years at primary school were difficult, not academically but socially. Because of my increasingly female mannerisms, I was picked on and bullied mercilessly by other boys. I became a complete no-friends and just concentrated on my studies. This strategy didn't stop the hassle but did make it bearable, and out of school, I still had my good girly times with Kate, Hazel, and Helen. In honesty, I was now more comfortable as a girl than a boy.
Kate, Hazel, Helen, and I all passed the eleven-plus examinations, which meant that we could go to a Senior Secondary School rather than to the educational graveyard of Junior Secondary. Kate, Hazel, and Helen would attend an all-girls school while I had to go to an all-boys one. Both ran `get-to-know-us-days' where newbies got the chance to visit the school, meet and talk with staff and pupils before starting there after the summer holidays.
As things turned out, the training days at my new school came first. They passed okay, but I found the teaching to be very regimented and strict; repeat parrot-fashion what taught, don't think for yourself and don't question. Also, every aspect of school life was geared toward encouraging the macho, competitive and emotionless male stereotype. I realized that it would be hard for me to succeed in that environment but to achieve my aim of going to the university I had to find a way.
Helen and Hazel were both recovering from bouts of the measles when their `get-to-know-us-days' came around, and Kate refused to visit the new school on her own.
"You must attend so that at least one of you girls knows their way around."
"No, I won't go alone. There's no-one else from our school going to be there. Can't Bobbie come with me? She can accompany me as a friend."
"That wouldn't be fair to Bobbie."
"I'll only go if she does, please ask her."
Isobel explained the situation. She didn't pressure me but asked me to consider it. I must admit that even the thought of playing a girl in an all-female school terrified me. One hint that I was a boy and I'd be mincemeat. But, my friend Kate looked so sad, so I agreed to do it.
Mum then piped up. "You don't need to go as Bobbie, you can be Helen. You're very much alike, her uniform will fit you, and with an appropriate wig and cosmetics, you'll be indistinguishable from her. Helen is entitled to be there so you won't have to deal with awkward questions about who you are, where you're from, and why you're attending."
Who would've imagined it, me impersonating my sister? Kate was delighted with the plan, and Helen perked up and chuckled when I told her that I would take her place.
Two days before our trip mum called me through to her room and told me to undress. After doing so, she set about fitting me with a thong-like garment. She slipped my willy into a sheath which was then pulled down between my legs and held in place by two straps that went up over my buttocks and attached to a waist belt. I looked down; my boyhood had disappeared, now replaced by a triangle of brown fuzz.
"Good, that's much better. Put on this new pair of panties and then look in the mirror. You'll see that your boy bulges are hidden. You now have a smooth feminine outline with the hint of a girly mound. Even if you accidentally reveal all, there's nothing to indicate you're anything but female."
"Thank you, Mum. I'm sure that all the school newbies will be heavily scrutinized. The more girly I am, the lower the risk of being found out."
"No need for thanks. I'm so proud that you're willing to do this for your friend. Now, let's get you a small padded bra and then fit your sister's school uniform. It's more restrictive and formal than the girl's clothes that you've had to date, so you need to get accustomed to it."
I was soon walking around the room trying to adjust to the additional restrictions that these clothes, particularly the bra, now placed on me. Mum was correct. The uniform was so different and dare I say it, felt less feminine.
"Why are you looking so worried, what is it, surely not a problem with the uniform?"
"No, I'm thinking about the undergarment you fitted on me. What happens when I need to, you know, go to the loo."
"Oh dear, I should've said. There is a small opening between your legs. Now you must sit and pee exactly like a girl. Just always remember to dry well afterward."
Unsure about this, I held it in until distress forced me to go to the loo. To my relief, things worked as mum said they would. Although I had been peeing sitting down for some time, it still felt strange to have liquid trickling out beneath me rather than out of my willy.
That evening while undressing Mum told me to keep the undergarment on day and night for the next few days to get at ease with it. "You don't want to find yourself getting uncomfortable once you're in school."
Being ever-inquisitive, I wanted to know how I now looked down there. So, before going to bed, I got a mirror and checked myself out. At the base of the hairy triangle, there was a small fuzzy mound around where my balls should have been. Where had they gone? There was also hair in my crotch which partly hid and encased a lipped gash. This site must be where the pee comes out and what I felt while drying myself off. Did all girls look like this down there? It was to be many more years before I found out.
I spent two days getting used Helen's school uniform. One thing I did like was the skirt. It went down to my knees, so I felt less exposed than I did in the short ones which the girls made me wear. Helen took delight in teasing her sissy brother but also went to great lengths to be sure that I acted and behaved like a young schoolgirl. She also taught me to curtsy, which was a trial for me but expected of all the girls at her new school.
Mum got me up early the next day and had me washed, dressed and made up before seven-thirty. She did an excellent job; even Helen was impressed with her doppelganger.
Kate and I caught the town bus to get to the new school. We were met by prefects at the entrance gate, asked for our details and shepherded into a room where at least one hundred girls of our age mingled around. There were many different uniforms, and all the girls were standing in pairs or groups of three or four, presumably friends together.
A group of very stern looking ladies came into the room; the headmistress, and her staff. Kate and I were the only ones who curtsied to them, prompting sniggers from many of the other girls.
"Quiet, these two girls are well mannered. In this school, you're all required to show respect to your elders so curtsy now and at any time meet a staff member."
All the girls then curtsied, as did Kate and me. We weren't sure if we were expected to do so but played it safe."
"Good, now this morning you girls will be taken on a tour of the school to familiarise you with the layout; classroom areas, the assembly hall, the cloakrooms and school offices. This afternoon you will gather the assembly hall and be told about the school rules on appearance and behavior, class subjects, class scheduling and how to keep track of where you should be at any time of the day and other general house-keeping matters. Prefects will now come and take groups around the school."
We all curtsied before she and the teachers left.
"The school prefect said, "relax, you don't have to be formal with me but be on your best behavior, they don't tolerate mischief here even amongst guest pupils."
The day passed smoothly. The most daunting part for me came during the lunch break when I found myself in the cloakrooms, separated from Kate and lost in an ocean of females. There were hundreds of girls of all ages there, from enthusiastic first years through to mature final years. They were bouncy and happy, demonstrative, vocal and openly emotional and affectionate, so different from the oppressive sometimes threatening atmosphere in a boy's cloakroom. Yes, there was segregation amongst year groups, and yes, I could see that there were occasional arguments between girls, but the overall ambiance was of togetherness, a willingness to look out for and support each other.
I noticed a young girl close to tears. From her uniform, I could see that she was a visitor like me.
"Have you lost your friends?"
"Yes, one moment they were there, and then they'd disappeared into the crowd."
"Don't fret, it's the same for me. Why don't we look for our friends together? I'm Helen, what's your name?"
"Elizabeth."
"What a lovely name. Let's go look for our chums."
Hand in hand we wandered around the cloakroom until we eventually found Kate and then Elizabeth's friends. After greeting and hugging them, Elizabeth rushed over, gave me a girly hug and planted kisses on both my cheeks.
"Thank you for taking care of me."
"No need to thank me, good girls look out for each other."
At the end of the day as we were leaving Kate said, "I'm amazed. I thought that you'd struggle to cope amongst all these flighty females, but you blended in and were positively girly. Elizabeth was gushing in praise of her new pal."
"I was terrified at first, but while we were waiting in the hall this morning, I noticed that many girls spoke, gestured and reacted to each other in the same way. I didn't want to stand out, so I copied them to fit in with the majority. I'm glad it worked well."
"It's not just about the mannerisms. You embraced femininity, in the way you acted with others and the empathy you had for Elizabeth. You have strong female instincts."
"Now you're making me blush, but funnily enough I was more at ease mingling with all these mischievous schoolgirls than I've ever been as a boy amongst schoolboys."
This revelation had a profound effect on me. Kate chatted away as we made our way home on the bus, but other than nodding occasionally I took in very little of the conversation. I was deep in thought. Until then, I'd only been out and about as a girl along with Kate, Hazel, and Helen. Now, for the first time, I'd spent most of the day in the company of strangers and not only had I carried it off as a girl, but I'd started to reveal depths of femininity and female empathy that even I never knew were there. Was this the real me? Did I dare investigate these instincts further? These were hypothetical questions. Of course, I did. I'd never felt so safe and at home than I did that day. This seemed to be my calling, and from then I knew that when the time was right, I would become a girl full-time.