As neighbors, Carol, Karen and I regularly met up on weekends during school term and more often during the holidays. We played many games together, and I happily joined in, despite their girly nature; I even played with dolls. Of course, the kids at school found out about this, and I was bullied mercilessly for being a sissy. I tried to explain that no boys were living nearby to play with, but in truth, I didn’t relate to macho boys while I was happy and comfortable with Carol and Karen.
Our repertoire of games changed with time. When we were sixteen, we added a forfeit card game in which the person who lost five times had to do a task set by the one with the most wins at the time. The allocated challenge was usually quite minor; being a servant for the others, singing a song, telling a story or doing an awkward dance or trick, generally making a fool of yourself, but there was always the risk of a more significant penalty.
One day, the unexpected happened. Karen won five games in a row, leaving both Carol and me due to forfeit at the same time. This event hadn't happened before, and later I found out that it wasn’t by chance; I had been set up.
My head was spinning, trying to think of what challenge I would have to perform, when Karen said, “I’m going to set a joint dare. You and Carol will exchange clothes and wear them for the rest of the day.”
“But, I’m a boy, I can’t wear a dress. Can’t I do something else?”
“You have to pay the set forfeit. Anyway, you’re more girly than many females I know. The clothing will suit you.”
I was dumbfounded at this turn of events but didn’t argue and followed the girls into the house and through to their bedroom. I was already into the forbidden territory. A boy shouldn’t be in this female sanctum.
“We don’t have all day. Get on with it.”
The first problem was how to undress in front of these two girls but still preserve some modesty; exchanging clothing one piece at a time wasn’t practical. Of course, it would also have defeated one aim for both girls: to see a naked boy for the first time. I decided to bite the bullet and stripped off completely. I was bright red, and Carol and Karen were goggle-eyed and open-mouthed by the time I hooked my thumbs into my underpants and pulled them down to expose my boyhood. After ogling me for a couple of minutes, Karen picked up my clothes and put them down beside Carol.
Her bluff called, Carol then undressed. I tried not to stare, but those pert little boobs and the dark triangle of hair down below drew my attention. Sadly, Carol put on my vest and shirt, quickly hiding those treasures again.
Karen picked up Carol’s clothes, put them down beside me and handed me the panties.
“Start with these.”
For the first time, I stepped into a pair of knickers and pulled them up around my bottom. I tremored at the sensations as the elastic clasped my legs and waist and pulled the soft cloth tightly around me; My jewels now safely and sensually covered.
Karen then handed me a bra. It was a complete mystery for me; I had no idea how to put it on, and Karen took great delight in fitting it onto me and packing the cups with socks to give the appearance of breasts. Next, Karen gave me a full slip, followed by a knee-length Gingham dress.
Carol was fully dressed in my clothes by now and sitting, watching me as I was putting on, ankle socks and a pair of flats.
“Keep your legs together. Your knickers are showing.”
My first of many faux pas in girl’s clothes. Carol took me over to a full-length mirror. At first, I felt ashamed to be dressed as a girl but, to my astonishment, steadily became at ease with my appearance. The other surprise was the delighted smile on Carol’s face. Clearly, wearing my boy clothes wasn't a punishment for her, and she also had the bonus of seeing me in her dress.
Carol and Karen took me outside, and we spent the rest of the morning playing. They teased me mercilessly, "We see your panties, we see your panties" whenever my dress blew up, or I bent over to picked up things. From then, I appreciated the many risks girls face when wearing a dress or skirt. Fortunately, Carol and Karen taught me ways to avoid these indiscretions, and I was soon enjoying being a girl.
We lost track of time, and the inevitable happened; Carol and Karen’s mum caught us. Betty had come home early in the afternoon and spotted us in the garden.
She went ballistic, “What is going on here? Why are you wearing each other’s clothes? Get into the house right now.”
She pushed us inside. Betty put me in her bedroom and told me to stay there. She then took Carol and Karen through to their bedroom and shut the door. There was a lot of shouting, a period of silence, and then the sound of four very hard smacks. Karen ran through to the living room crying. After another spell of heated discussion, I heard four and then five very hard spanks, and Carol was sobbing her eyes out.
I was shaking like jelly. It was apparent what I was about to face, only confirmed when Betty came through with a large plimsoll in her hand.
“Right young man. I’ve got the story from Carol and Karen. I know they tricked you into exchanging clothes, but as a well brought up boy, you should have refused to undress in front of my girls and stopped Carol from disrobing before you.”
So, this was the critical sin; not that I dressed as a girl nor Carol as a boy but that we had seen each other naked.
“But we were only playing a game. Nothing happened, it was harmless fun.”
“You would say that but what you did was wrong, and I must punish you for it. I can tell your mother about what happened today or discipline you myself. It's your choice."
“Please don’t tell mom. I’ll take my punishment from you.”
“Good. I spanked Karen and Carol four times on their panties for setting you up and Carol another five times on the bare for revealing herself. As a boy I expect higher standards from you; It’ll be double their punishment or eighteen all on the bare. You choose.”
Believe it or not, I had never had a spanking before, so had no way to gauge this. Naively, I assumed that fewer spanks would mean less pain. I mean how much protection could those thin panties give my butt.
“I’ll take eighteen on the bare.”
“You’re sure.”
“Yes.”
“Okay, kneel beside the bed and bend over on to it.”
As soon as I had done this, Betty folded the skirt over my back and pulled my knickers down to my knees. My bottom chilled with the sudden exposure to air, but the bliss didn’t last.
“Every smack you are about to get is a simple message; Never get naked with my girls or allow them to strip in front of you again.”
Before I realized, I felt this excruciating pain in my bum as the first smack of the heavy plimsoll hit home on my previously pristine cheeks. I screamed, but Betty kept up a steady pace through ten. My butt was on fire, and I was begging Betty for forgiveness. She stopped for a few seconds probably to regain her strength because the final eight were harder than before; The pain in my bum was unbearable, and I was screaming and sobbing uncontrollably.
“It’s over. Now lie on the bed and compose yourself.”
If I thought that this would bring relief, I was wrong. The severe pain continued to course through my butt as I lay there. How I wished that the cold air would quickly do its magic and drain the heat from my bum. Eventually, my agony subsided.
I’m not sure how long I lay there before Betty came back. “Stand up.”
I did so, and she then gently pulled my knickers up back over my bottom and readjusted the dress. I was relieved but found it very unsettling to have these strange hands under my dress. No wonder girls get so upset when boys flip their skirts or touch their legs. Another lesson learned.
Betty took me to the kitchen and gave me a glass of cold milk, which I drank gratefully.
“The girls are outside, go and play with them while I prepare a meal.”
We were a sad and somber girly trio.
Carol was now back in a dress. “I suppose this means we’ll never do dress up again.”
“I wouldn’t say that. It was fun. We’ll just have to be careful in the future.”
The delighted look on both girl’s faces was precious. We hugged and before long started to play again and, despite the pain in our butts, enjoyed the rest of the afternoon.
We had tea with Betty in the evening, and then, with some unexpected sadness, I went to her room and changed back into my boy clothes.
Betty came through and sat beside me.
“Stephen, I couldn't help noticing this afternoon how happy you were as a girl and that Carol and Karen were pleased with their new sister. Do you want to do it again?"
This offer caught me on the hop, but I said, “Yes, I would like that.”
“Well, I’ll be glad to have another daughter to look after occasionally, but there are requirements. You will tell me when you want to visit so that I can select your girl clothes. You will undress and dress alone in my room. My girls are not allowed to watch you undress or try on your boy clothes. Finally, you will do as I say while in my care. Any disobedience or misbehavior will be dealt with as swiftly and painfully as today.”
My butt cheeks winced a little at this last statement, but I said, "Thank you for being so understanding. I accept the rules and will try to be a well-behaved girl.”
Carol and Karen overslept the following Saturday morning so were surprised to find me there, en femme: complete with a long wig. I now looked like a girl rather than a boy in a dress. They were thrilled to have a new sister to train in girlhood. Over the following weeks, my walk, deportment, and voice became more feminine, and I learned of the arts of hairstyle and makeup. I preferred a ponytail while Carol and Karen preferred braids, but with enthusiasm, they tried out many styles on me, and I then did their hair in the ways they liked. It wasn't all fun; I also had to learn the chores that a girl must do around the home: cleaning, cooking, baking, washing, ironing, knitting, and sewing, etc. Boys would appreciate girls more if they knew how hard they worked, but of course, their teaching was that housework is easy and menial. I was usually exhausted at the end of a girly day, but I enjoyed the experiences which were all part of being a girl of that time.
The downside to my increasingly feminine manner was that boys at school noticed and they took great pleasure in continually hounding and harassing the sissy. Eventually, I couldn’t go into the boy’s cloakroom or playground without being abused or punched. Fortunately, the senior schoolgirls took pity on me and suggested to the headmaster that I could spend break-times in their cloakroom, provided I had a chaperone. For the first few days, it was mostly only me and my chaperone, the school secretary, that were in there. Having a senior member of staff present in their cloakroom was quite intimidating for the girls, so some of the seniors became my chaperones. This change helped, but there was still an air of unease.
I talked with my chaperone one day, “The girls are still uncomfortable with me around because I am a boy invading their safe space. Would it help if I dressed like them? How would they react, would the boys get to know?”
“You would be willing to do that?”
“Yes, you girls have been so kind to me, it’s the least I could try.”
I watched as my chaperone talked to several of the senior girls.
“It’s agreed. We have a spare uniform and shoes that will fit you. Unfortunately, there are no underclothes available.”
“No problem, I am already wearing a camisole and panties.”
I unbuttoned the top of my shirt to reveal the camisole.
"Wow. You should’ve have told us. The girls would have appreciated that you took that risk and been less apprehensive about having you in here.”
“I was going to mention it, but saying ‘by the way I’m wearing girl’s underwear’ is not something that’s easy to drop into the conversation.”
"That’s true, but that information makes things easier. You can switch straight away if you want. There are still three-quarters of an hour of break time left."
They handed me the uniform, and I went to the restroom to change. As I was doing so, I could hear a build-up of chatter in the cloakroom. The jungle telegraph had worked; almost every girl in the school was there to see me emerge.
There were gasps, "Is it Stephen?"
“It is, in all female attire.”
“Even panties? Let’s see.”
I blushed bright red as I lifted my skirt to reveal my knickers. To my relief, the girls didn’t ridicule me, but just nodded in approval; so different to how boorish boys would have reacted.
The noise was subsiding when I heard a loud voice.
“What is the meaning of this, what is going on here?”
It was the deputy headmistress who had come to find out why there was a commotion in the cloakroom. The girls parted leaving me facing the headmistress, in all my glory.
“My, my, what do we have here?”
The senior girls explained, and the headmistress said, “Wait here until I come back.”
I was sure I was going to get the belt but no, the headmistress came with a wig and fitted it on to me.
“Now, Stephanie you look the part. Enjoy being a girl. Ladies, this must be a secret amongst us, no-one can tell.”
Once the headmistress had gone, I was surrounded by girls all wanting to know how it felt to dress as a female."
“Scary, but nice.”
I spent the remainder of the break chatting with the girls. They realized I was no threat and could talk sensibly about things of interest to them. They accepted me. From then, I often found myself with girls wanting advice on clothes and makeup that might help them attract the eye of their crushes. In those days, boys and girls were kept apart while growing up and were a mystery to each other. My unique girl-boy perspective seemed useful.
Within a few days, the girls were confident enough to take me out to their playground, which was out of sight of the boy’s one. I was now able to mingle freely, enjoy the sun and play during break time; many new games and girly skills to learn. I was happy in school for the first time, and it paid off. I began to study hard, and my grades went from the worst in class to amongst the best.
The boys knew that I spent break times in the girl's cloakroom accompanied by a chaperone, but had no idea about anything else. Nobody blabbed. The fact that the girls took me under their wing further infuriated the bullies, and they continued to intimidate me, but with less and less effect on me. I realized that while they were outside playing macho males and bragging about their fictional girlfriends and conquests, I was in here surrounded by real females, beginning to understand a little of what makes girls tick, far more than the alpha males would ever learn in their lifetimes. I appreciated the differing feminine characteristics, behaviors, and styles and importantly recognized their abilities and high hopes for the future. They weren’t the airheads portrayed by the boys; these girls were smart and motivated. If encouraged and supported they could outshine most, if not all, boys. Sadly, to prevent this threat to machismo, girls were denigrated and trivialized and taught only to be skivvies and housewives. I did my best during this period to encourage and help girls pursue higher studies, even when most around were doing their best to stop them. Thankfully, several girls that I mentored, including Carol and Karen, left school with high grades. Even better was the fact that they achieved top marks in subjects usually available only to boys, considered too hard for soppy girls.
These arrangements at school did not change my relationship with Betty, Carol, and Karen. At weekends and during holidays, I continued to be the third sister; even occasionally staying with them for a couple of days en femme. I was always disappointed to have to change back to boyhood.
Over the first few weeks of my sisterhood, Betty kept an eagle eye on all of us; To be sure we did our chores and didn’t get up to mischief. In general, we were well behaved, but as with all teenagers, there were occasions when each of us crossed the line and had the plimsoll vigorously applied to our bottoms. However, in time, Betty had the confidence to leave us unsupervised. This change gave me the chance to fulfill my pledge to Carol: that she and I could exchange clothes again.
One day, Betty was away in town. As soon as I arrived, Carol and Karen led me through to their bedroom. There were no doubts about what they had in mind, and we were quickly recreating the events of the previous occasion. I still blushed, and the girls were as goggle-eyed and open-mouthed as before when I took off my underpants. Carol’s breasts and mound looked more developed but sadly, as previously, were quickly hidden by my vest and shirt. Karen passed the clothes between us and delighted in helping me put on Carol’s lingerie and dress. We spent the day doing our allocated chores and playing. I hadn’t seen Carol look so happy in a long time. She was reluctant to change back into her girl attire but accepted that we mustn’t get caught. I undressed in Betty’s bedroom and put on the girl's clothes that she had set out for me that morning while Karen took Carol’s clothes back to her and brought my boy clothes to Betty’s room. Everything was now as it should be and not a moment too soon; Betty arrived back half an hour later.
“By the smiles on your faces, you must have had a good day. What mischief have you been up to? Are your chores all done?”
"Everything is done. It has just been one of those happy days."
Betty gave a wry smile but just said, "Fine, let's have our tea. I need to refuel. I'm exhausted from my day of shopping.”
After our meal, I changed into my boy clothes to allow Betty to get into her room to rest.
Carol came with me as I was leaving. She kissed me on the cheek and whispered, “Thank you for making this a wonderful day. Can we do it again?”
“Certainly, but not too often. We don’t want your mum to become suspicious.”
Carol and I did indeed exchange clothes again several times, and by good fortune were never caught. Each time Carol was thrilled and happy with the experience. At the time, I couldn’t understand why she liked to wear my rough boy clothes instead of her soft feminine ones. It never dawned on me that she was my opposite, a boyish-girl to my girlish-boy.
Karen didn’t show any interest in cross-dressing until one day when Betty and Carol were away in town.
“Can we exchange clothes? I want to try to understand Carol’s fascination for boy clothes.”
We went to Karen’s bedroom, and I stripped off as before, picked up my clothes and put them beside her.
Karen undressed and put on my vest and shirt, but then said, “You’ve shown me yours, it’s only fair I show you mine.”
Karen lay back on the bed and opened her legs. For the first time in my life, I got sight of that precious female gem peeking out of its nest of black fuzz. I gazed at Karen’s fanny for quite some time. I couldn't take my eyes off it. The picture remains in my memories to this day. That was all that happened. We then got dressed and got on with the rest of our day. As it was, Karen didn’t enjoy the boy clothes; too heavy and course. So, around mid-day, she asked if we could change back. I could see she was unhappy and agreed, but suggested I would switch to my girl clothes first. Karen followed me through to Betty's room and watched as I undressed. Then, she very slowly and carefully gave me my girls clothes and helped me put them on. She looked so happy while doing this. She enjoyed dressing me up as a girl. I stayed in the room while Karen went to her bedroom, changed into her clothes and brought my boy clothes back. Now Karen looked content.
“I still don’t know why Carol is enthralled by boy clothes but glad I’ve tried them at least once.”
“It’s a mystery to me as well. I’m also happy we exchanged today because I noticed how much you enjoyed dressing me as a girl. Do you want to do it again, sometime?”
Karen’s eyes lit up. “Can I? There are so many clothes I would like to try out to see which give the best appearances.”
“Yes, we can do it when we're alone like today.”
The opportunities were rare, but when they occurred Karen happily used me as her live mannequin to try out many clothes combinations. There were so many beautiful feminine things. I could see that Karen preferred blouses, midi-skirts, and frilly underwear, which I know Carol hated; she was a cover-up with long loose dresses or slacks type and would never have agreed to model the things Karen liked. Maybe that is why Karen used me.
One day, we three girls had finished our chores and were playing in the garden when Betty called us into the house. To my shock and horror, my mum, Jean, was there with Betty.
At that moment I wished the ground would open beneath me. I was going to be in deep doo-doo but to my surprise mum just smiled.
“So, Stephen you like being a girl. No wonder you’re now respectful and well behaved.”
Mum kissed Carol and Mary on the cheek and hugged me tightly, “You girls have done an excellent job with my little ruffian: no longer a rowdy boy, instead he is now a gentle girl-boy."
I was quiet for the rest of the afternoon and during our meal. I was afraid my mother was putting on a front and that there would be hell to pay when we got home. After tea, I got up to go to Betty’s bedroom.
“What are you doing?”
“I’m going to get changed.”
“Don’t do that. You look pretty. I want to walk home hand in hand with my new daughter," and that's what we did.
As we were walking, mom said, "I met Betty a few days ago and remarked how much your behavior had improved of late and that I couldn't understand why. She then told me about the dressing as a girl and developing your feminine side. I could hardly believe it until seen with my own eyes."
“You’re not angry.”
“No, it’s wonderful. I now have a sweet fem-boy. The pity is that it didn’t happen sooner. We might have avoided those years of teen tantrums.”
“I am sorry. I know I was unruly back then but now I want to make you proud.”
At home, we sat together drinking our evening cocoa when mum said, “What do you want to be in the future: do you want to become a girl or stay as a boy?”
“I haven’t thought about that. At present, I’m just enjoying the girly side that I never knew existed. I don’t think I want to be a girl full time, but I would like to be girly now and then."
“I’m glad you’ve uncovered your feminine characteristics. They are repressed in most boys, considered a sign of weakness, but you’re already a better person for finding and embracing them. Keep with it. I'll support you. These female experiences will stand you in good stead.”
Mum went through to her room and came back with a pink nylon nightie.
"This more appropriate nightwear for you now. Get a good night's rest. Tomorrow, Betty and I are taking our girls shopping.”
I tossed and turned for a long time before falling asleep, still taking in everything my mom had said and how supportive she was. I’d expected to be branded a pansy and punished. Also, to date I had been en femme only with girls and women who knew me; Now, I was to be in town amongst strangers, including shock-horror boys and men. Could I carry this off or would I be caught out and humiliated?
In the morning, I found that mum had left clean underwear and knee-high socks, so I put these on along with the slip and dress from the day before. Mom was very taken when she spotted me tidying my hair and applying a little makeup.
“My, my, the girls have taught you well.”
After breakfast we headed off, hand in hand as the day before. Betty met us as we arrived at her house.
“I’ve set out some things for you to wear today. Your mum can help you with them.”
Lying on the bed was a pink slip and a floral summer dress. There was also a bra, but not like the one I had on; it was shaped and heavy.
I was studying it when mom said, “There are breast forms in the cups, we thought it would look better than just a padded-out bra.”
Mum helped me put the bra on and immediately, I felt the extra weight drag me forward. Also, the breast forms hid my feet and jiggled as I walked.
I mentioned this to mum, and she said, "Now, you've found another difficulty of girlhood but will get used to them in time.”
I put on the slip and dress and mum zipped up the back. Looking in the mirror, I saw that the breasts were well covered but oh my, did they stick out. So much for trying to be inconspicuous.
Betty drove us all to town, and we started walking around the shops. I was very nervous, to begin with; scared, that people would realize I was a boy in a dress. But no, folk just saw three girls out shopping with their mothers. I soon realized that the boys were all staring at my chest rather than looking at my face. They were distracted by my less feminine features which helped to maintain my disguise, but I found this male ogling disconcerting and demeaning. They looked at me as boobs-on-legs rather than as a person. Was it like this for all girls?
I was so engrossed in everything going on around us that I was inside the ladies clothing store before realizing it. This cocoon of femininity suddenly engulfed me. Row upon row and counter upon counter of beautiful clothes, and lingerie. How do you choose?
Mum was a woman on a mission and was soon holding dresses, skirts, and blouses in front of me. Then, having selected a few, we were off to the changing room to try each one. Although this was a ladies’ shop, it was still unnerving for me to strip down to my bra and panties in the changing area. Would a stranger accidentally look in and see me in my undies? I was shaking as I put on and pranced around in the various items selected by my mum. Often, she would tut and say, “No, that’s not right for you,” but occasionally she took a liking to an item, which was then set aside for me to try on yet again.
After what seemed to be forever, we were down to three dresses and three skirt and blouse sets. It was while trying these on that I noticed my mother’s reflection in the mirror. She was smiling, enjoying every moment, and positively beaming with delight. It dawned on me that like all other moms, she must have longed for a daughter to nurture and fuss over and now her girly-boy was helping fulfill some of those feminine dreams. I was pleased to make her happy but worried about how far she would want to go down this path.
I was smoothing down a tight-fitting blouse and skirt when Carol and Karen peered around the entrance curtain.
“Wow, you look gorgeous. That top catches the eye."
The girls meant that the cleavage would attract males. I was sad that they were already conditioned to this pandering approach rather than trying to feel good about themselves but only said, “Yes, it is nice.”
“Mum sent us through with some bras.”
Karen was in her element. She soon had my blouse and bra off and was fitting me with various new styles, taking obvious pleasure in slipping the breast forms into the cups and settling the cleavage into place.
Mum and Carol sat transfixed at these events.
“Interesting, I’m going to have to keep an eye on you, Karen. Steph is putty in your hands.”
Mum chose three bras that she and the girls agreed suited to me.
Next, it was off to look for knickers. This part was the most embarrassing for me as the excited girls held up umpteen panties for me to view, all the while the many young girls and women circulating in the shop were happily smiling at this scene. Although I didn’t need to be, I was mortified and blushing profusely.
Fortunately, a young sales assistant came to the rescue and took me aside.
"Don't be embarrassed. Looking through knickers is unsettling for all girls. They are our most intimate and personal item of clothing, and none of us wants the world to know what panties we wear to keep our pussy snug and safe. Just remember: we’re all girls here, we all wear panties, and we've all gone through this distress. "
If she only knew the truth.
Then she said, “What style of knickers are you wearing? Do you like them?”
“White cotton full briefs and yes, they are comfortable.”
“I suggest you stick with that style for now but be a little more adventurous. Look, we have them in all these pastels and prints.”
Having only ever worn white panties my heart skipped a beat at the thought of these beautiful colors and patterns.
"They are lovely. I can hardly wait.”
"I can see that Stephanie is entranced with those. I'll buy a pack of seven pastels and seven prints for her."
Everything was packed up, and Carol, Karen and I left the shop each carrying bags of new clothes. We visited other stores, where our mums bought clothes for themselves. Strangely, we girls weren’t allowed into the changing rooms while they were trying on various items. We had to wait outside.
We had a light meal in a small restaurant and then headed off to find the car. I was tired from carrying the bags of clothes and unfortunately let my guard down. There was a sudden gust of wind as we turned a corner and before I knew what had happened my skirt and slip were up around my waist, revealing my white knickers to all and sundry. Of course, there were hordes of boys and men around to witness my wardrobe fail. They whistled and hollered loudly, but soon quietened down under the evil stare of my mums.
I felt so ashamed of this gaffe that I began to cry. Jean and Betty both cuddled me. “Shush, it’s happened to all of us. Given the slightest chance nature conspires to reveal a girl’s underwear and always when there are males around. We must at all times keep control over our skirts.” Carol and Karen nodded in agreement.
From that day, my mother encouraged me to spend more and more time being her daughter. Soon, I dressed full-time as a girl during the weekends and holidays, culminating in a six-week continuous period during the summer break. Initially, I was uncomfortable with this but didn't want to disappoint my mum and eventually, with the support of Carol and Karen, I came to accept and enjoy that I was now more girl than a boy. I soon had the confidence to go shopping without the protective shield of our mums.
My seventeen-birthday was at the start of the summer holidays, and this triggered further changes to my feminine life. Mom presented me with a pussy prosthesis.
“It’ll cover all those nasty boy bits. Make you look female, and prevent any unsightly bulges showing through your skirt.”
Once tied in place, the prosthesis hid my boyhood leaving only a visible triangle of hair. My penis tucked into a sheath with an opening between my legs; Meaning that I now had no option but to pee like a girl.
As soon as I told Carol and Karen, they wanted to see how I looked down there. "Well, well, now you have a fuzzy fanny just like us.”
Mom also bought me a clincher to give me a narrower waist and started to put me into miniskirts, which were the new fashion of the time. Carol and Karen wore knee length or longer skirts, but mine reached down only to mid-thigh.
I tried to argue with mum but was told, "To be a girl of today, you have to blend in with modern styles, and it lets you show off those lovely legs.”
Wearing a skirt is challenging, but preserving your modesty in a miniskirt is neigh impossible. Your legs are bare, and any stumble or misstep is likely to reveal your undies. Males turn their attention from the boobs to further down. They watch you like hawks, trying to spot even the slightest hint of pantie, presumably in the hope that one day, the unfortunate girl will be going commando. I struggled to wear the minis and begged my mum to let me go back to longer skirts, but to no avail. However, she did allow me to wear tights for the first time to preserve my dignity.
In later life, I asked mum why she had insisted that I wear the miniskirts.
“At the time, all girls were under great pressure to be fashionable and wear shorter and shorter skirts. I knew that girls came to you for advice and I wanted you to tell them about the risks of very short skirts, to deter the girls from trying them or at least to let them know how to manage miniskirts safely. I knew that the girls would listen to my girl-boy once they realized that you had first-hand knowledge of the perils of minis.”
Karen wanted to try a miniskirt, but Betty forbade her. Being the kind sister, I loaned Karen one of mine in secret, to wear when we went shopping in town together. As it turned out, while Karen liked above the knee skirts, she was never comfortable in minis. She felt too exposed and soon gave up on them. This decision was a pity because they suited her. Even a fem-boy could see how they highlighted those beautiful legs. Karen happily settled for comfort rather than suffering for fashion. She was no less girly for that. Her real femininity was there for all to see.
Unfortunately, I didn’t have a choice. Mum continued to insist that I wear a miniskirt whenever possible. I confided in Betty about my unhappiness with this situation.
“You must obey your mum, but a longer, free-flowing skirt is better when you are here with the girls and me, more appropriate while doing your chores. I’ll let you change into a midi skirt while you are with us and explain this to your mom if she finds out.”
“Oh, thank you for understanding.”
“It’s the least I can do to make my daughter happy. Anyway, I owe you. It’s thanks to you that Karen decided against miniskirts.”
“How do you know what I did? You’re not angry with me?”
“Karen told me when I asked her why she was no longer begging me for a miniskirt. I know you disobeyed me, but you were just a good sister, and it worked out for the best.”
From then on, I wore a miniskirt only at home, going between our houses and when we all went out shopping or on day-trips together. At other times, I wore knee-length skirts - more comfortable and easier to manage. I think that my mother suspected about this arrangement, but she never said anything. Mom was always happiest when she was out and about with her mini-skirted fem-boy.
The following year, our last at school, was stressful for all three of us. We had to get high grades to have a chance of going to university. So, in the main, it was work and more work with very little time for play. Carol, Karen and I helped, tutored, and encouraged each other throughout and we all succeeded in gaining entry to the city university.
Through friends of friends, my mom found us a flat to rent nearby the university. It was ideal except for a condition of tenancy: the owners had significant problems with male students and mixed occupancy in the past, so they now let the flat only to girls. Carol and Karen thought this would be okay as I could be girl number three. Jean and Betty also agreed. I was less sure. I was now comfortable as a girl amongst my friends, but in the city, I’d be away from this comfort zone - many new people to meet and a high risk of discovery. Further, I would have to live most of the time as a female but attend the university as a male. How could I do that? Was I to be a superhero and change persona in a phone box? Nevertheless, Carol and Karen were so happy with the idea of us sharing that I didn’t want to disappoint either them or our mums, so I agreed. Where there’s a will there’s always a way.
We moved into the flat one week before the start of the first semester. It was exciting but also stressful at first. Carol, Karen and I had been close friends for so long, but never alone, living hand in glove with each other, without the supportive shield of our mums. In the first few weeks, we routinely bickered and fought about trivial but necessary things: failure to restock the fridge or do the washing, ironing, cleaning, etc., often storming off to our separate bedrooms to cool down. Eventually, as all girls do, we worked out a routine and rota for the flat, and our lives began to run relatively smoothly and peacefully.
I bought a woman’s hooded tracksuit. It was not too unlike a man’s one. Before the start of term, I went out running every morning, hair flying in the air so that people got used to the sight of the mad jogger that lived in the flat. In the interim, Carol and Karen arranged for lockers for us at the university and put some boy clothes in mine. So, every day, a hooded female figure left the flat and jogged off to the college where I changed in the locker room before meeting up with Carol and Karen. I reversed the process in the evenings. No one seemed to suspect this ruse and to reinforce my girly image. I always wore very feminine clothing when out and about locally or in the city center. Although it pained me to pander to males, I made sure my clothes were always eye-catching and left no doubt that I was a female.
Socialising was much more difficult for me. I could go on girl’s nights out, but attending mixed events were more problematic. I had no interest in boys and couldn't take the risk of being found out by some hands-everywhere oaf. There were plenty of them around and even with all my care I had a few close calls. So, I tended to stay in the background, people watching while Carol and Karen enjoyed themselves. Since my educative time with the schoolgirls, I was now fascinated by people in general; Trying to visualize what characteristics attracted couples to each other and what made them compatible or unsuited.
It was during the spring semester that I noticed a tension building between Carol and Karen. They had always been close but now seemed to be drifting apart. Both girls now had their own sets of friends, but while Karen tried to spread her time between her friends and her sister, Carol spent more and more of her time with her friends at the exclusion of Karen. While this was all part of growing up and having a new life, Karen took her isolation from Carol very severely. I would occasionally come home late after lectures to find her alone and crying. I did my best to comfort and reassure her, often talking late into the night about anything and everything of interest to us. Thankfully, Karen was usually much chirpier in the days after our one-on-one chats.
Things came to a head one evening when I came home to find Karen passed out on the couch. It was apparent why: Karen usually drank no more than a glass of wine at any time but had now emptied a full bottle. First things first, I checked that I could get her awake and responsive. I then carried Karen through to her room and changed her into her pajamas - no easy feat in the circumstances.
I tucked her up in bed, kissed her on the cheek and said, “You’re safe now, sleep tight.”
I was in a daze at this point. What had happened to Karen?
In the living room, I found a letter from Carol to Karen.
‘Penny and I have fallen in love and have now decided to seal the deal. I am moving in with her from today. I'm sorry not to warn you, but I didn't know how. A sudden break is probably the best way. I hope you understand and we can both go forward in our respective futures. Yours always, Carol.’
No wonder Karen was upset; Her sister has gone, and worse, it was to live with another girl.
Penny was a postdoctoral researcher and about four years older than Carol. I had seen them together but never noticed anything intimate in their relationship. So much for my people watching skills.
Suddenly feeling quite tired, I was heading off to my room when I realized I should keep an eye on Karen, in case something happened, or she needed to get up during the night. I changed into my pajamas, found a couple of duvets and curled up on the floor of her room.
I was awakened in the morning by Karen’s voice, “Oh my, what have I done? my head is throbbing, and I'm feeling sick."
This statement was followed by, "Why are you sleeping down there?"
“I wanted to be sure you were okay during the night.”
"You did that for me? You care more for me than Carol ever did."
“Let’s not get into that now. Is there anything you need?”
“I would like some coffee.”
Karen tried to get up to go to the loo but was very unsteady, so I helped her through, and later put her back to bed. I sat on the edge of the bed, and we chatted while having our coffee.
“How could Carol do that with a girl? It’s disgusting.”
I was shocked. I knew that Karen was angry, but did she believe that the only acceptable love was between alpha males and females?
"I'm as surprised as you at what has happened, but love comes in many shapes and forms, and this is one of them."
Karen shouted at me, “Are you saying that you approve of them getting it together?”
“I’m sad that Carol has gone, but if she’s found love with her new partner that is all that matters. Carol will have agonized for a long time before taking such a radical step. We should be happy for her and be there for her if needed.”
“I’m sorry that I snapped at you. I’m still upset, but you’re spot on. Carol has every right to find love in any way she wants. In truth, I’ve known for a while that she preferred women to men, but didn’t realize how deep and all-consuming her feelings were. I’m sad that Carol couldn’t confide in me, but I understand how difficult that would’ve been for her. Girl-girl couples are still considered taboo. I only wish I could’ve shown Carol my support.”
“I do hope Carol has found true love. There’s nothing else we can do but move forward from here. Now, you look all in. Get some rest today.”
"Okay, mom. Will do!" I tucked Karen in, and she soon fell asleep.
Betty and Jean arrived at our flat while I was preparing an evening meal. Carol and Penny had been to see Betty that morning, and our mums were here to check that we were okay.
“Where’s Karen?”
“Karen’s sleeping. She took the news very badly and didn’t settle last night. We chatted this morning, and that seemed to relax her. She’s been snoozing since then. Maybe I bored her to sleep.”
I didn’t see any point in telling our mums the worst details of the night before but did explain what I now knew and how Karen had been affected.
"Poor dear, poor you. This revelation is a surprise for all of us. I'd no inkling of Carol's relationship with Penny until I met them today. I should disapprove, but it's clear to me that Carol and Penny are deeply in love and a happy couple. They, therefore, have my blessings.” My mum nodded in agreement.
I hugged both. “I’m so proud of you for being so understanding and free-thinking. Carol and Penny are bound to face prejudice for their girl-girl choice and will need our support always. The important thing is that they are happy as a couple.”
A little later, Karen joined us. We group hugged, had tea and sat chatting into the early hours about the events of the last few days. Realising how late it was, I suggested that Betty and Jean stay overnight rather than travel home.
"Betty, you can use Carol's room, mum can use mine, and I’ll crash out on the sofa.”
“That would be great if it’s okay for you? We're both exhausted.”
“Certainly, it’ll be fine. You will find everything you need in the dressers in each room.”
After having hot cocoa, everyone went off to bed, and I started to make up the sofa. As I was doing this, Karen came through and kissed me on the cheek.
“Thank you for everything. Come with me. I need you.”
We went through to Karen’s room, she got into bed and said, “Come on, get in, you can look after me and at least sleep comfortably tonight.”
I slipped in beside Karen; We snuggled up together and soon fell asleep in each other’s arms.
Karen woke me early in the morning, “Thanks for comforting me. With everything that has happened, I couldn’t bear the thought of being alone all night.”
"The pleasure was mine. We need to support each other.”
“We’d better get up before our mums catch us together.”
“Yes, you’re right. That would be difficult to explain and confuse things even more. I think we should ask our mums to stay for a couple of days. We can do some family stuff together and get back on a more even keel. What do you think?”
Karen kissed me on the lips. “I think that’s an excellent idea. Mmm, some retail therapy would be nice, and maybe I also get to cozy down with you at night.”
Betty and Jean joined us for breakfast, and I took that opportunity to suggest that we have some family time together.
“That’s a brilliant plan. We want to be with our daughters, not at home alone. How about going clothes shopping today, just like we did that first time you went to town as a girl?”
A lot of water had passed under the bridge since that occasion. Being in a women’s clothing store no longer stressed me out, but two things still made me uncomfortable: stripping down to my undies in a changing room with only a curtain for a door and examining sets of knickers in public. We were laden down with bags of new attire by the time we got back to the flat that evening and contentedly retired for the night after an evening meal.
The following day was mainly taken up with sight-seeing in and around the city. I also had my first experience of walking along a Northern beach in a miniskirt. Feeling that cold salty air chilling my legs and nether regions. Panties and tights gave me little protection against the icy blast. I didn’t feel very alluring and envied the protection Betty, Jean, and Karen had from their longer supposedly less sexy skirts.
The day was long and enjoyable but also exhausting; We slept through to the middle of the next day. In the afternoon, there were tearful farewells as our mums set off back home, leaving Karen and me at the flat. This last two days had brought her, and I closer than ever before and had begun to kindle within me new exciting feelings for her - certainly not those of sister for a sister.
I found out that this was the same for Karen. As soon as we were alone, she took my head in her hands and kissed me on the lips. Needing no further prompting, I embraced Karen, and we shared long passionate kisses that took our breath away. I began stroking her hair and caressing her neck. Karen sighed and positively purred as my hands worked on her breasts and down near her pussy. This heavy petting continued for a considerable time until we were both hot, randy, and desperate to go all the way. Although I was en femme, it was not my feminine side that was coming to the fore.
Karen took me through to the bedroom and started to undress. I stopped her and took her in my arms. “Are you sure about this?”
“Why, don’t you want me?”
"I'm struggling to keep myself in check, but I want to be certain. I don't want this to be about either you or me. I want us to share our love, two halves of a passionate whole."
"You talk too much. I've wanted this for a long, long time."
Karen practically ripped off my skirt, blouse and underwear and my not so little man sprung to attention as soon as released from its prosthetic sheath. I must admit I then took my time undressing Karen; partly to tease her but also to allow me to appreciate every curve and feature of her beautiful body.
As we lay on the bed, I kissed Karen's neck and shoulders, placed my hands on her firm breasts and massaged them gently. She sighed and quivered as I kissed them and sucked on the nipples. I could feel Karen getting hot and bothered, so I started to work my way down to the belly button and then to her pussy. Karen spread her legs as I stroked her inner thighs and soon I was kissing the lips of that fuzz-encased feminine gem that I first sighted many years ago. I began to lick the pussy lips while stroking the clitoris with my finger. Karen’s fud became hot and moist, so I pushed my tongue as deep as I could inside it and licked for all I was worth. Karen began to shudder, then moaned loudly as her sweet juices burst forth.
I pulled myself up the bed beside her, kissed her on the lips and proceeded to work my way down that luscious body again. Karen was now hypersensitive to every stroke, and touch. Her pussy was practically begging for it as I teased the entrance with the head of my cock. Karen gasped as I pushed the head between the lips and into her vagina. She was moaning intently as my cock slowly plowed deeper and deeper into her. I stopped when my full length was inside and allowed her love tunnel to adjust and clamp itself around my shaft. I started to move back and forth within that tight, hot snatch. As my speed increased, Karen began to squirm and shudder and soon her warm cum juices flooded around my cock. That pushed me over the edge. After a further three rapid and deep thrusts, I climaxed and shot my load into that hungry fanny.
Karen and I remained coupled for some time, enjoying all the fantastic post-coital sensations passing between us before we kissed, slipped between the sheets and cuddled up together again.
“That was unbelievable. What a wonderful way to lose my cherry. How do you know so much about turning on a girl? I thought that this was your first time."
"You are my first. Not all those senior girls that I spent time with were as chaste as they pretended. They dared not say anything to other girls but were happy to tell the sissy in graphic detail what they did with their beaus and what they found arousing. I memorized every piece of information, for the future."
"You certainly put that knowledge to satisfying use on me. I look forward to the encores.”
“By the way, is this the end for Stephanie? That would be a pity.”
“No, I’m happy to continue as Stephanie so long as Stephen can come out to play every now and again.”
“Good, I can have the best of both: Stephanie as my sister and Stephen as my playmate.”
“My, my, you are a little minx. I can see that Stephen may be around quite often.”
