Petticoating days with gran - Final

Dear Auntie Helga,

I felt a touch sad as I prepared to send you this letter - the last installment of my more detailed retelling of my petticoating days with gran, as I have enjoyed reminiscing and writing about what I can remember from that time. Once I had started to think hard back over those times, for the first time really since then, I was surprised how much I did actually remember. I would have liked to have sent you my rewritten tale in one letter, but due to the length I thought that would have been unwise, but by breaking the story down into three separate parts has given me the chance to polish each one. I hope you and the readers enjoy the final part of my transformation into Caroline, as it describes the final stage of my enforced feminization at my grandmother's hands and my eventual change of heart from my previous letter. I also hope my story has served as an inspiration to women to petticoat or even completely feminize their effeminate or unruly male family members, as my gran wisely did to me.

I will conclude my tale from where my last letter left off.

The following month I arrived at my gran's full of apprehension. This was the weekend she would finally complete my transformation into Caroline, her new granddaughter. I wasn't so much worried about becoming a girl in all but body-form, as I'd more or less accepted my fate at that point. I was worried about how things would go on from there and what my new life as a girl would lead to. But I tried to put those thoughts to the make of my mind for the moment, as they were something for the future. I had yet to completely become Caroline after all.

As previously, my gran didn't begin the next and final stage of my transformation until Saturday morning. That morning, she came into my room first thing, and after waking me, she excitedly told me today was the big day. I think she couldn't wait to complete my transformation into her granddaughter. It was as good as Christmas Day for her, if not better. Once I had gotten out of my bed in my nightie, though, she told me she wouldn't be dressing me just yet, as she thought I better have some breakfast first, as it was going to be a long morning. She told me to just put on my pink dressing gown over my nightie for now and to join her in the kitchen once I'd freshened-up in the bathroom.

After having a bowl of cereal and a glass of orange juice for my breakfast, she dressed me in a brand new white panty and bra set, which I must say were a bit more risqué than I was used to wearing. They weren't see-through or anything like that, but they were a lot more lacey and sensuous than I was used to wearing. But that day I think she just wanted me to feel as feminine as possible.

Unusually, once she had put them on me, she didn't continue to dress me in the rest of my clothes, but instead she led me into the bathroom by my hand. Where she made me sit on the edge of the bath while she put on some strange, fowl smelling cream on my legs and feet. After five minutes or so she washed it off with the showerhead. As she did so, I looked down at my legs and saw to my surprise all the hair on them was washing off with the cream. I never knew up to that point a cream could do that. I thought she was moisturizing my legs or something ready for them to be shaved. Once she had finished washing all the cream off my legs and had dried them with a towel, I ran my hands over my legs. To my surprise, they were as smooth and as soft as a woman's legs (I presumed). Next she sat me down on the toilet and had me lift up my arms in turn and shaved-off all the hair under my armpits. She didn't shave my face, as I hadn't really begun to grow stubble yet. Instead she gave me a quick manicure and pedicure, before painting my nails and toenails a light pink shade. Before we exited the toilet, she gently washed my face all over with a flannel and then exfoliated and moisturized it. I can remember my face feeling all tingly and refreshed afterwards.

For the next stage of makeover, my gran led me into her bedroom; a room I'd been forbidden to go into since the beginning of my trips to hers four years ago and had only seen glimpses of. When I looked around it there was nothing special or different about it. There was just her double bed, a wardrobe, some bedside chests of draws, a larger chest of draws and a dressing table. My gran wasn't hiding anything for sure, like I'd sometimes naughtily thought, but in my defense I did have the imagination of a teen. I think she just valued her privacy, and there was nothing wrong in that.

She had me sit down on a fluffy pink stool in front of her dressing table, which had a selection of beauty products, perfumes, brushes and make-ups sitting on it. I gulped looking at them, realizing she would be using some of them on me. I nearly had second thoughts at that moment, but I worked through them the best I could, as I still didn't want to find out what the alternative was. I kept repeating in my head, "I'm going to be a girl now", "I'm going to be a girl now", "I'm going to love being a girl", "I'm going to love being a girl".

Once I'd calmed myself down, I noticed my gran had covered up the mirror on the back of the dressing table. I think she didn't want me to see myself until my transformation was complete. She wanted it to be a surprise. I could understand that.

As I got accustomed to my new surroundings and tried to control my feelings, I noticed my gran was standing with her hands on her hips, wondering what to do next or simply what order to do things in. Then it dawned on her. She would spray some perfume on me, before finishing off dressing me. She picked up a bottle of expensive looking perfume off her dressing table in front of me and sprayed some on the top of my chest above my bra and on my shoulders and neck. I tried to hold my breath when she did, as I did want to breath any in and have the taste of the stuff for the rest of the day in my mouth. Once the perfume settled, I smelt it. It had a strong feminine smell to it (surprise, surprise), but it did smell nice nonetheless, and I would say almost classy. Then she went about dressing me. The first item she put on me, as I was already wearing some knickers and a bra, was a fresh pair of black tights straight out of the packet. My eyes opened wide when she did, as they now felt so soft, smooth and silky against my legs since I'd had all the hair removed from them. I thought at that moment I could definitely get used to being a real girl. My gran noticed the look of surprise and then pleasure on my face and smiled. She finished dressing me in a black flared knee-length skirt, my favourite slinky pink top and a pair of my indoor shoes.

Then she got on with my makeover. But instead of applying my make-up first, she combed my hair flat against my head as best she could before putting some sort of cap on my head, so my own hair would be as flat as possible against my head. I didn't see it myself until later, but I presumed I must have looked bald. I also presumed it was because of the wig she was going to put on my head, but I hadn't noticed a wig anywhere in room. Again, I think she wanted to keep it as a surprise for as long as possible. I then wondered what it was like, the colour, the length, the shape, etc.

But that was for later, as my gran was going to apply my make-up first. She started off by using some concealer to cover up any spots or blemishes on my face. Once she was satisfied my face looked smooth and even, she moved onto my eyes. She applied a blue-gray eye shadow to my eyes as I held them gently closed, as requested. Then she lightly applied some mascara to my eyelashes. She moved down to my lips next, applying a light shade of pink lipstick to them. Once she had finished, she told to rub my lips together and then bite with just my lips on a piece of tissue to get rid of any excess lipstick. She told me to try and avoid licking my lips, as the lipstick itself would keep my lips lubricated, and so she wouldn't have to keep reapplying them. I tried, but it was hard, as it was new, but I got better at not doing it over time. Finally, she applied some blusher to my cheeks. My new feminine face was now complete.

Once she was finished, she toke a step back from me and admired her handiwork. She smiled as she did so, which came as a relief to me, as I didn't want to end up looking silly. She then asked me if I would like my new hair now. I smiled and said, yes. She turned away from me and walked over to her wardrobe, where she produced what I can only describe at first glance as a beautiful wig. It was a full-bodied over shoulder length brunette hairpiece with lovely thick waves in it. As soon as I saw it, I couldn't wait for my gran to put it on me. As she walked over to me with it, I told her it was lovely, and that it must have cost her a small fortune. She replied by saying nothing was too expensive for her pretty little girl. As she put it on me I felt a comforting and warm sensation go through me, to sort of tell me everything was going to be all right. All my fears and worries evaporated at that moment.

After she had positioned it on my head so it was perfect, I moved my head side to side to get a feel for it. I must say it did feel wonderful and sensuous. It did add some weight to my head, but nothing I couldn't adapt to. I didn't care about that anyway, as I quickly fell in love with it.

My gran smiled at me when she saw I was finally enjoying my newfound femininity and all the new wonderful sensations she was giving me. She then said all I needed now was some jewellery and my transformation would be complete. She clipped some earrings to my ears, as they hadn't been pierced, unsurprisingly. Put a lovely looking gold necklace around my neck, an equally lovely looking matching bracelet on one of my wrists with an exquisite, very expensive looking lady's watch on the other. I told her I couldn't accept the jewellery she had bought for me, as they were clearly very expensive. But she simply told me to hush, as I was her only granddaughter. She wanted only the best for me no matter how expensive they were. Not wanting to seem ungrateful, I thanked her very much for buying them for me, even though she certainly didn't have to.

Once I'd finished thanking her, she smiled broadly at me and asked if I was ready to see myself now my transformation into a girl was now complete. I slowly nodded and told her I was ready, even though I don't think I was. I was very nervous at that moment.

She told me to face her dressing table mirror, as she walked over to it, which I did. The butterflies in my stomach started to multiply as she toke hold of the sheet covering the mirror. She paused for a couple of seconds, teasing me, but then she whipped it off.

It toke me a second to focus my eyes on my reflection, and for my mind to process what it was seeing, as I was in a bit of a tizz at that point. But when I did, I was literally shocked at what I saw in the mirror, as I hardly recognized myself. I looked more like a girl than I ever thought possible. Okay, I admit I wasn't beautiful, but I would have said I could have passed for an average looking girl. I realized then my gran had completed her goal of at least making me look like a girl rather than a boy. In a way I was relived the final stage of my transformation had gone so well, as I was really worried about ending up looking like a drag queen, but my gran had done a really good job, and my soft features had really helped. Okay, I have to admit at close scrutiny, I think most people would notice I was a boy dressed up as a girl, but it would have to be close scrutiny, even if I did say so myself. What I think really completed the illusion, though, was my truly gorgeous wig. It gave my head and face a truly feminine look and shape. Without it I wouldn't have looked anywhere near as good, even with the make-up. No wonder my gran had sent so much money on it.

As I continued to look at myself in the mirror, I felt a strong, truly wonderful wave of femininity go through me. I realized then I had been silly in not really wanting to be completely transformed into a girl. Of all the things that could happen to me in the world and of all the fates that could befall me during my life, becoming a girl was hardly a terrible one. I think most women would think it was a lovely fate, and I was starting to think that way myself. At that moment, I became Caroline in mind, body and spirit, and Paul died. I was now a girl, I felt like a girl, and best of all I wanted to be a girl! My gran's conditioning, light touch and patience had born fruit. I felt like a beautiful butterfly after being an ugly caterpillar. My feminization was complete, at hers at least. As for the rest of the world, who knew? That was one for the future. My gran didn't want to rush me after all.

I turned around to see tears in my gran's eyes. She said that I looked beautiful, before breaking down in tears of joy. I rushed over to comfort her. As I hugged her, I thanked her so much for turning me into the granddaughter she had always wanted. And that I thought I looked beautiful as well, and that she couldn't have done a better job in making me look like a girl than the make-up artists on a Hollywood movie. I then told her I was wrong to tell her I really didn't want to be a girl six months ago. That last remark made her sob even more. As she sobbed, I told her my name was Caroline and I wanted to be her for at least as long as she lived, and I wasn't just saying that because that was what she wanted to hear. I apologized to her more than once. Those remarks also didn't help my gran's waterworks. It was a good five minutes before she calmed down enough to let go of me.

A little while later, she came to me with her camera and asked if she could take a few pictures of me now I was Caroline. I agreed. She toke several, and placed some in one of her photo albums and another one she framed and placed it, ironically, next to one of me dressed as my male self on her mantelpiece above her fireplace. That was also the time she stopped dressing and undressing me, letting me do it myself, but only because she was doing my make-up now instead. I wouldn't say I missed her dressing me as such, as I always thought I could do it myself, but she always did it with such care that it did make me feel special and loved. But she did carry out the odd inspection now and then to make sure everything was in order.

After my transition into Caroline was now complete, it wasn't long until my grandmother was encouraging me to go out into the outside world with her, so she could show her new granddaughter off; at first around her village and then eventually into the local town, presumably on a bus, as my gran couldn't drive. Even though I did think of myself as a girl now at my gran's, and was as comfortable wearing girl's clothes and make-up as any real girl, I was still very weary about venturing outside the security of her bungalow. It wasn't because I was worried about people looking at me and realizing I was a boy made up to look like a girl, as I think I would have fooled most people, especially if I kept my lovely wig in my face as much as possible. It was because I was worried somebody at my school recognizing me even in spite of transformation. If somebody who I actually knew me saw me they would be more likely to see through my new look than any stranger. If I did venture out into the outside world I was terrified somebody from my school would recognize me and tell the rest of the school what they saw. As you might imagine, my school life after that would be a living hell. I just couldn't take the chance, even just in her village, as somebody from my school might have lived there. I explained all that to my gran during one of my visits and she understood. She told me she wouldn't push me into anything I didn't want to do now I'd become what she had originally wanted, a granddaughter. I thanked her for her understanding, and I promised her I would venture outside with her as Caroline as soon as I'd graduated. She thanked me, and said that would give her something to look forward to. I smiled and nodded.

Those who read my original letter are probably wondering about the two straight weeks I spent at my gran's during one summer holiday. Well, it came about the summer after I'd become Caroline. I was due to fly out to Italy with my parents on a Monday afternoon for a two-week holiday. The weekend before we were due to fly out, we went about packing all our clothes and other bits and pieces, which went without a hitch. But when we came to check our passports were in order, mine was missing. My parents and I searched high and low and in every nook and cranny for what must have been hours, but to no avail. Once we had searched everywhere, my parents faced a stark choice: either leave me at home on my own (a teenager, remember) while they went off anyway or forget about the holiday altogether. As they thought about it, I came up with a third option. I could go and stay with my gran for the two weeks while they went on holiday. My dad was all for that option as soon as I'd mentioned it, as I think he had really been looking forward to the holiday, but my mum wasn't so sure. She said I could, but only if my gran agreed. She phoned her up to ask, and it turned out my gran was only too delighted to look after me during that time. So, it was settled. I would be spending two straight weeks at my gran's as Caroline. The first time I'd ever been her for more than a weekend. My gran would no doubt be over the moon about the proposition. And to tell the truth, I was looking forward to making her the happiest grandmother alive for two-weeks, and on a personal level, I was looking forward to experiencing being a girl for an extended period of time.

Instead of biking over to my gran's as I usually did, my mum drove me over to hers first thing Monday morning, as I would need extra clothes and other supplies for a two week stay at my gran's rather than a weekend one. Little did she know I wouldn't be needing extra clothes, boy ones anyway.

Once my mum had driven off after having a quick chat with my gran and had kissed me goodbye, I went off and got changed into Caroline. Once I had, I joined my gran in her bedroom, so she could do my hair and make-up. As she did, I can remember us having a joke about the two suitcases of clothes I had brought with me. Nothing I don't think anybody else would have found funny, it was joke very much of the situation and of the time.

After dinner that day, my gran told me I couldn't just sit and watch TV, chat with her and play board games for the entire two weeks I would be staying with her. So, she thought she would teach me everything she knew about running and looking after a house, or bungalow in her case, including the garden and any other miscellaneous chores. She would teach me how to be a housewife in other words. Thinking about it, it thought it was good idea, incase one day I did end up living on my own, or ended-up serving as a maid or housekeeper for somebody as Caroline. I wanted as nice or make as nice a property as my gran's if I ever did. Perhaps I had become more feminine than I thought I had.

Over the next 14 days, my gran taught me how to prepare and cook various meals, including Sunday roasts. In the same vain, she also taught me how to bake cakes and make other various desserts. Away from food, she showed me how to do the laundry, washing clothes, including delicates, at the right temperatures and keeping different coloured clothes separate, etc. She went on to teach me how to dust, polish, clean and vacuum until everything and every room was spotless. And she showed me how to keep a garden in order, including the lawn, borders, trees and shrubs. It didn't feel much like a holiday, but at the end of the two weeks, I felt like I knew everything I needed to know if I did come to serve someone as Caroline one day or ended living on my own as myself or Caroline. I was very grateful to my gran for that, as the knowledge she gave me did come in useful in my life.

But one of the bad side effects of being a girl for two straight weeks, though, was going back to being a boy again. After those two weeks, the last thing I wanted to do was give up my lovely clothes and feminine lifestyle to go back to being just Paul again. I hated wearing trousers, y-fronts, socks, etc., again after being in silky bliss for so long. For the first few days afterwards I really missed being dressed as a girl. To a point where I badly wanted to tell my mum everything, just so I could carry on being Caroline. But unfortunately that was impossible for reasons I write about later. I just looked forward to my next wonderful weekend with my gran instead.

Very sadly, I never did venture out into the outside world on my grandmother's arm as Caroline, as she died not long before I finished school. In-between one of my visits, she suffered a very bad stroke and was hospitalized. She passed away two weeks later after showing no signs of recovery.

I was truly devastated when she died, not just because she was my grandmother who I had grown very close to over years as Paul and Caroline and dearly loved, but also because any possible future I had as Caroline died along with her.

Thinking back, I don't really know what would have happened if my gran hadn't suffered that terrible stroke and had lived for at least a few more years. All I can really do is speculate. I think once I was truly confident venturing out into the outside world not just with my gran but also on my own as Caroline, I think the next step would have been telling my mum, so she could carry on my enforced feminization full-time if she was so willing, but only if my dad had separated from her first of course. With my dad still in the picture at the time I don't think either my gran or me would have told her about my transformation into a girl. He wasn't an overly butch man, but he was still a masculine one, who thought men should be men and women should women and there were no gray areas. If he ever saw me as Caroline he would have probably thought I was a sissy or something similar. Not that I wasn't, but I don't think I could have lived with the embarrassment. Things might have been different if my parents split and I went to live with mum or, dare I say it, my dad had died. But I never wished for such a thing to happen just to become Caroline full-time, as I am not a bad person. If things had been different, even with my gran's death, and I had lived my mum on my own, I think that would have been the time I gave up my masculine clothes and ways to fully become Caroline for probably the rest of my life. I'm really sad that never came about as I thought that was destiny once I had completely accepted and had given my blessing to my transformation. Ironically, my mum and dad finally did finally split up, but not until several years after my gran's death. My dad went on to marry somebody else, and I have little contact with him now, and my mum now lives on her own still in the family home.

But, on the other hand, even with my dad still around, if my gran had lived for a few more years, I think once I had finished school, she would have wanted me to move in with her as Caroline to look after her and her property in her later years when she was unable to do it properly by herself. I think that was what the two-weeks training she gave me that summer was all about. Maybe that had been her plan all, to transform me into a girl, so I could serve as her maid, housekeeper and gardener and maybe even nurse in her last few years of life. If that was her last wish, I would have been more than happy to grant it after she had given me the wonderful gift of femininity. If I had lived for just a few years as my gran's carer as Caroline, I don't think I could have ever gone back to being Paul. It was hard enough going back to being a boy after just two-weeks of being a girl, let alone years. I would have missed the clothes, make-up, hair, etc., too much to ever go back, even with my dad still around. I think I would have contacted my mum to tell her everything thing and to arrange something, if we hadn't already.

The closest I ever got to going outside dressed as a girl was sitting out in my gran's back garden during the summer in one of my lovely flowing summer dresses, and putting on a pair of my mum's black knickers and tights under my suit at my gran's funeral. To this day I regret not granting my gran's wish of going outside with her, but I just couldn't take the risk, no matter how slight, and I wasn't to know she would die before I'd finished school.

I comforted myself in the fact that I did grant her dearest wish, very willingly in the end, of becoming her only granddaughter.

As I mentioned in my original letter, I do still dress up from time to time as Caroline, but only very occasionally on special dates. Like my gran's birthday, the day I was first petticoated and the day I become Caroline at my gran's. I don't do it any more than that, as it just doesn't feel the same without my grandmother or anybody else for that matter enforcing it or at least seeing dressed as a pretty, dutiful girl.

Paul aka Caroline


Thank you for your letter Paul. We really appreciate your taking the time to walk down memory lane with us. You gran must have loved you so much, I'm sure you miss her terribly.

Auntie Helga

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