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Turned Sissy by Girly Girl Best Friend
(12-17-2019, 11:01 PM)Kimmi Wrote: A life of purses and skirts, and being turned into a girlfriend, would make most any boy shudder in horror.

Why do I anticipate that Sissy Nicole is not "most any boy?"

Speak for yourself; My story is similar to this in some ways which I conveniently posted a couple of days back; see below  Rolleyes

Endless curtsies 


When I was in the early part of my high school period (around year 7 & 8) I had to go round to my friend Gabrielle’s house to do my homework (as we finished school long before my mother finished work). Her mother believed in homework being part of the school day and therefore staying in uniform to do it whilst at the same time believing in equality of gender experiences. I think therefore she saw a bit of an opportunity in me and we would have to wear each other’s school uniform to do the homework.

So we had about twenty minutes from arriving home for Gabrielle to change into my trousers, shirt, shoes, tie and blazer and at the same time for me to don her knee length socks, dolly pumps, pleated skirt, blouse and blazer and for Gabrielle to then apply a replication of her makeup onto my face.

If we finished the homework before my mum finished work we got to change back, but if not we had to keep each other’s uniform for the night (and I would be provided with a set of Gabrielle’s underwear - you will see why shortly).

Taking this scenario of having gone home as Gabrielle, the following morning I would obviously have to put her uniform back on, but this time complete with underwear. My mum would then do my makeup and plait my hair (which she had taken to keeping long). 

On arriving back at Gabrielle’s house we had around an hour before we had to set off for school (and therefore around half an hour to complete our homework). In the event that we did not finish in time the penalty was perhaps obvious and happened maybe half a dozen times; Gabrielle would have to attend school as a boy and I as a girl (note that this was Gabrielle’s mum’s policy, my own mum always stopped short of sending me to school in such attire when filing out her own petticoating regime). I remember one of these occasions was on a particularly blowy day and I spent most of the trip to school trying to avoid my hemline rising and showing my knickers. Having to explain to our teachers why we were dressed in such a manner was an interesting experience. 

This was made worse by two factors; firstly, that almost none of the girls wore skirts, almost all voting for the trouser option, which made me particularly stand out (my sister having to wear a skirt and nappy to school under our mother’s petticoat punishment would eventually trump this). The other factor was that in the event of a PE lesson taking place on such a day, Gabrielle was the only girl to opt for the PE skirt rather than shorts. Consequently I had to go with girls to play netball, hockey etc while the boys played football and rugby. So basically, I was the only boy in the girls group and also the only one wearing a skirt.

What is more, at school break a lot of the girls used to play that game where a number of girls jump over a long rope and on a couple of these occasions while in a school skirt I was required to join in. I must have been flashing my knickers to anyone within sight.

Years later, Gabrielle became my main confidante during my permanent secretary punishment just before I left home and while she had become a much more independent woman by then, choosing generally to wear jeans, she always made sure she was similarly dolled up if she knew we were going to meet up. I remember one time she came over to stay at our’s for the night and in an act of unparalleled solidarity she drank six cans of fizzy drink and went to sleep in a wet nappy the same as both myself and my sister.

When we all met at the breakfast table the following morning in our similarly drooping nappies, I think she came to realise that I had encountered far harsher petticoating than she had.

We still meet up from time to time. She is a banker based out of Frankfurt do on the occasions when I am in the city as a stewardess we will meet up.

We are totally opposite ends of the spectrum now; she wears quite a masculine pant suit and I rock up in a flight stewardess uniform wearing a Knee length pencil skirt (or at least it was while I was on probation; after probation we are required to raise the hem to show more leg) high heels and makeup. So I suppose in a way although it is the line I have gone into, I still am institutionally petticoated
Hi Nicole,

Love this story. Is there anymore, I would love it if there was.

Thanks in advance

(05-23-2020, 06:48 AM)Dancer4Fun Wrote: Hi Nicole,

Love this story. Is there anymore, I would love it if there was.

Thanks in advance


Yes there will be more. I seemed to have over extended myself with stories but when my pink passenger takes over I never know where she will take me.
(11-21-2019, 04:06 PM)Kimmi Wrote: This is so intriguing.  First boner not until age 16?

And while wearing panties and a girl caressing you?

How intense that would be.  

And your boner is tiny.  

I can't wait to hear what Amy says next!

Miss Kimmi

I find that HARD to believe   Big Grin Big Grin Big Grin Big Grin Big Grin Big Grin
Chapter 12

I don’t want my life to be purses and skirts. I don’t want to be your girl friend! “Like I said you’ve always been my girlfriend all the feminine things will just solidify it.” I stood there in my panties and skirt dumbfounded as Amy seemed deadest on this. Amy give me another test and I’ll prove it to you that I’m not a sissy. “Why would I do that? You’ve already failed a sissy test and you willing put on panties and a skirt. Honestly we should just keep moving along and do your hair, nails, and make up.” Why don’t need to do all that. “I think we should! Remember you’re under my control now.” I’m not under your control! We are friends I’m not your sissy! “We are girlfriends and we always have been. You’ve already done whatever I say! I hate to tell you but you have always been my sissy!” I again stood there dumbfounded and even though I hated what she was saying. I again had another deep feeling of attachment too Amy.

“So let me tell you how things are going to go from now on. You are now my girly girl bestie and you will do all the things that go along with that. You will wear dresses and skirts and other outfits even to school, and yes even at home.” My mother would never allow any of this! “Oh yes she will! After I’m done convincing her of course. Now let’s fast forward a bit. After high school we will go to the same college which will be some sort of fashion design program. We will both graduate with flying colors and then whichever ever job I take you will be my assistant.” Amy’s plans were very ambitious and it’s clearly obvious that she has thought about this before. Amy this is insane! There’s no way that this will happen! “Oh it will it’s already started!”
A very exciting pitch there from Amy; it will be interesting to see what methods she has at her disposal to put the outcome into practice.
Chapter 13
Amy please I beg you not do this. “It’s too late for begging! I’ve made up my mind. Now sit down! We are going to do your hair, make up, and nails. Then we will get you dressed and introduce the new you to your mother!” No! My mother won’t let this happen! “She won’t? Because I’ve been convincing her for years!” What do you mean? “I mean what I mean. I’ve been slowly convincing her when we have had moments alone that you have confided in me more then once that you want to be a girl.” Why would you have done that? “Because I wanted a girly girl bestie and now my plan is almost finished. Honestly I can’t believe that you have never noticed! Remember your last birthday when your mom bought you a purse and told you it was a gag gift. Well that was because i convinced her that you wanted one.” I was mortified! But Amy I never even used it! “Well that’s not what I told her. I told her that you always carry it around the house when you hang out at my place. I told her that you even limp your wrist and everything!” Amy how could you do that? “Oh and just wait till you get home tonight! Your room is going to be so girly!” Oh no what have you done?

“Oh not what I’ve done but what your mother has done. She’s having some re modeling done to your room as we speak! We’ve been planning this for so long. Although your mom has no idea about my motives anyway.” What makes you think that I’m going to go along with this? “Ha! You think that you can stand up to me? Your beloved Amy? Think again!” After she was done talking she then reached down and grabbed my balls and twisted them tightly. I screamed out in pain! “Are you ready to obey?” She squeezed and twisted more! Omg omg okay okay I’ll do whatever you say! “A great idea Nicole!”
Good chapter, though I’m not surprised Amy has been planning and scheming for a long time. Nick is in for allot of changes. Looking forward to reading more.
Nick might be protesting now but in retrospect he will be grateful. There are a few changes in store and doubtless a lot to learn, but it is a path once walked down on which he will never look back.
Chapter 14
“A wise choice and you have nothing to fear. As long as you do what I say then you will have no problems being my girly bestie.” But Amy I’m a boy I’m your best friend that’s a boy! “Not anymore you’re not! Do I need to remind you again.” Amy made the motion too grab my crotch and I jumped back. No of course not Amy. “Perfect! Now let’s get you all made up and dressing the way you should be. Your mom sent over one of the newest dresses she bought for you and we have a stylist coming.” Dresses? A stylist? “Of course your mom really went all out and got you a brand new wardrobe and she paid for a stylist to do your hair and nails.” Hair and nails? Amy what about school? I can’t go to school like this! “Oh don’t worry! The school has already been notified about your transition.” Amy what have you done? “I believe the question is what haven’t i done? I believe I have succeeded in getting a girly girl bestie.” Amy walked to her close and grabbed a blue floral summer dress. “This is what your mom sent over as well as a pair of pink pumps and a new pink purse. Strip and put the dress on.” No I’m not doing this! Amy sighed and walked over grab my crotch and twisted it and I screamed out in pain! “What are you gonna do?” The pain was too much to bear. Be your girly girl bestie I said. “Good now put on the dress.”

The blue floral dressed flounced above my knees and Amy zipped me up. She put down the pink pumps and said “Go on step into them and begin to walk. Let’s see how good you are.”. Remembering the pain I just experienced I stepped into them and began to walk. I stumbled at first but got better slowly. “Perfect I knew that you would be a natural! Let’s add the purse!” Amy put my new purse around my shoulders and I had to get used too carrying it. It wasn’t as easy as it looked that was for sure. I began to keep practice walking around Amy’s room when the doorbell suddenly went off. “That’s must be Jenny the stylist!” She’s here already? “Yes she is! Now you better act like you want this or else you’ll find out just how much more painful things can get for you. Understand?” Yes Amy i said. “Good now let’s go down stairs!”

Chapter 15
I had never see so much hair and nail equipment be brought into a house ever. It was like Jenny had brought over a whole salon with her. “You must be Nicole! I think that it’s so great that you want to be a girl.” I was about to tell her that this was all being forced upon me by my former best friend but Amy had a look in her face that told me I better not say that. Instead I said yeah I love being a girl it’s what I’ve always wanted. I love wearing dresses and getting my hair and nails done. I looked over at Any and she looked pleased. “Well you found the right girl. So, what are we doing the works?” Yes Jenny that would be great I said. “Perfect! Luckily your hair is long and blond already so I just need to give it a feminine touch. Your make up nails on the other hand well they need a lot of work. You better sit down and make your self comfortable because this is going to take a while.”

I sat down and I must have fallen asleep because before I knew it Jenny was telling me that I was all done. Already I thought to myself. I looked down at my finger nails that had a girly pastel colored pattern on them and my toes were painted bright pink. The biggest surprise however was my hair and make up. It was done so well that I couldn’t even tell who I was. “Wow Jenny you really put did yourself! How much do we owe you?” “Oh I can’t charge for this Amy! I love turning submissive boys into pretty girls! It’s so freeing for me and them!” “You’re so sweet!” “Oh you are too Amy and good luck with everything that you’re trying to accomplish!” With that Jenny left and took all of her equipment with her! “Perfect now it’s time to go show your mom!”

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