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Sissy Boy to Sissy Girl
#1
Hello everone.

When I was  growing up, I wanted to be a sissy boy. I used to imagine myself in a Nursery, sitting on a rocking-horse, or being taken to the park with my toy yacht by Nanny whilst dressed in my sailor suit. I also used to fantasize about being made to wear a Fauntleroy Suit  with my Nanny/Auntie doing up the buttons on my frilly blouse, softy whispering "You are my little Sissy-Boy".

If any film or television programme featured as boy dressed in sailor suit or a Fauntleroy Suit, I would take a keen interest. (My parents would be unaware that as I watched it, I was desperately wishing that I could be forcibly dressed in such humiliating outfits).Books on children's costumes also took my fancy.

But it was only when I started to visit Auntie that I became interested in being dressed and treated like a little girl. True, on my first visit, I did wear a makeshift Fauntleroy Suit, and also a Sailor Suit on a couple of occasions. But the majority of the time, I was Auntie's  little feminised "Nephew".

Nowadays, I prefer to dress up as a sissy girl. I like the idea of shedding my male persona behind and embracing the feminine. Not only do I dress as a girl, I like "girly" things. I enjoy playing with my dolls and have developed an interest in things such as Ballet.

Will I ever return to dressing as a sissy boy?- possibly. Sailor suits  and Fauntleroy suits are clothing I still find enjoyable., so who knows? Smile
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#2
(06-23-2018, 09:53 AM)Sissy Leslie Wrote: Hello everone.

When I was  growing up, I wanted to be a sissy boy. I used to imagine myself in a Nursery, sitting on a rocking-horse, or being taken to the park with my toy yacht by Nanny whilst dressed in my sailor suit. I also used to fantasize about being made to wear a Fauntleroy Suit  with my Nanny/Auntie doing up the buttons on my frilly blouse, softy whispering "You are my little Sissy-Boy".

If any film or television programme featured as boy dressed in sailor suit or a Fauntleroy Suit, I would take a keen interest. (My parents would be unaware that as I watched it, I was desperately wishing that I could be forcibly dressed in such humiliating outfits).Books on children's costumes also took my fancy.

But it was only when I started to visit Auntie that I became interested in being dressed and treated like a little girl. True, on my first visit, I did wear a makeshift Fauntleroy Suit, and also a Sailor Suit on a couple of occasions. But the majority of the time, I was Auntie's  little feminised "Nephew".

Nowadays, I prefer to dress up as a sissy girl. I like the idea of shedding my male persona behind and embracing the feminine. Not only do I dress as a girl, I like "girly" things. I enjoy playing with my dolls and have developed an interest in things such as Ballet.

Will I ever return to dressing as a sissy boy?- possibly. Sailor suits  and Fauntleroy suits are clothing I still find enjoyable., so who knows? Smile
Oh yes. The early memories really are fascinating and seem to set the course. For me it was an early programme of 'Popeye The Sailor Man' in the 1950s. Black and white in those days and a boy was featured towards the end. He must have been about seven or eight years old and was wearing the most frilly and lace trimmed satin Lord Fauntleroy suit and with his blond hair in long curly bangs. He was being teased by some older girls. I was watching with one of my older sisters and German Nanny. I was convinced he was a girl, but was sternly corrected. I immediately wondered what it would be like to be dressed like that. Soon after that I saw the famous version of Dicken's 'Great Expectations', with the David Lean direction. The scene where Pip first meets Estelle still amazes me me today! The young Estelle is wearing the most dreamlike white satin frilly dress and ankle length bloomers. I often fantasised about being dressed in the outfit by Estelle herself.
Also at this time I was looking through the family Collins collections dating from the 1900s. There were the most amazing photos of children of the time, and what they wore. Plenty of sailor suits, Fauntleroy suits, Highland suits and satin knickerbocker suits with long silk stockings. I assume that the suspender or garter waists were also commonly worn. Only later on would I experience the Highland suit and Suspender waist.
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#3
(06-23-2018, 09:53 AM)Sissy Leslie Wrote: Hello everone.

When I was  growing up, I wanted to be a sissy boy. I used to imagine myself in a Nursery, sitting on a rocking-horse, or being taken to the park with my toy yacht by Nanny whilst dressed in my sailor suit. I also used to fantasize about being made to wear a Fauntleroy Suit  with my Nanny/Auntie doing up the buttons on my frilly blouse, softy whispering "You are my little Sissy-Boy".

If any film or television programme featured as boy dressed in sailor suit or a Fauntleroy Suit, I would take a keen interest. (My parents would be unaware that as I watched it, I was desperately wishing that I could be forcibly dressed in such humiliating outfits).Books on children's costumes also took my fancy.

But it was only when I started to visit Auntie that I became interested in being dressed and treated like a little girl. True, on my first visit, I did wear a makeshift Fauntleroy Suit, and also a Sailor Suit on a couple of occasions. But the majority of the time, I was Auntie's  little feminised "Nephew".

Nowadays, I prefer to dress up as a sissy girl. I like the idea of shedding my male persona behind and embracing the feminine. Not only do I dress as a girl, I like "girly" things. I enjoy playing with my dolls and have developed an interest in things such as Ballet.

Will I ever return to dressing as a sissy boy?- possibly. Sailor suits  and Fauntleroy suits are clothing I still find enjoyable., so who knows? Smile

 Hello Leslie,

The late Victorian and Edwardian periods must have been a wonderful time for seeing so many boys wearing Fauntleroy and sailor suits. I too have often wished I could have been born then so I  could wear such outfits. Of course, petticoating in those days was widespread and I wouldn't be surprised if you passed a boy wearing a frock while you're walking hand-in-hand in the park with your mother or nanny. 

I dare say many a nanny must have got a thrill of dressing a young lad in his sailor suit or whatever and then spending time with him in the nursery. And I wouldn't mind betting they found it difficult to take their eyes of the youngster.  Don't forget, parents of rich children in those days rarely saw their offspring and were brought downstairs by nanny for an hour or so and then taken back to the nursery. 

Some nannies upon seeing a boy in a fauntleroy suit, must have thought how feminine he looks when wearing it and took to dressing him as a girl for a short time. Then there's the rich mother who wished she could have had a daughter rather than a son. As the child grows up she has her boy feminized by his nanny, not only that, she gives strict instructions that he is to remain in a childlike state even through his teenage years.

   
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#4
The natural extension of the ‚Äúchildlike state‚ÄĚ you mention, and which is shown so clearly in that lovely picture, is to put the poor boy back into nappies.

Those puffed velvet shorts and knickerbockers that nannies used to put their charges into must surely have been very handy in hiding a boy’s bulky nappy-covered bottie.
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#5
(06-24-2018, 11:57 AM)Tiffany Wrote:
(06-23-2018, 09:53 AM)Sissy Leslie Wrote: Hello everyone.   great photoshopped image

When I was  growing up, I wanted to be a sissy boy. I used to imagine myself in a Nursery, sitting on a rocking-horse, or being taken to the park with my toy yacht by Nanny whilst dressed in my sailor suit. I also used to fantasize about being made to wear a Fauntleroy Suit  with my Nanny/Auntie doing up the buttons on my frilly blouse, softy whispering "You are my little Sissy-Boy".

If any film or television program featured as boy dressed in sailor suit or a Fauntleroy Suit, I would take a keen interest. (My parents would be unaware that as I watched it, I was desperately wishing that I could be forcibly dressed in such humiliating outfits).Books on children's costumes also took my fancy.

But it was only when I started to visit Auntie that I became interested in being dressed and treated like a little girl. True, on my first visit, I did wear a makeshift Fauntleroy Suit, and also a Sailor Suit on a couple of occasions. But the majority of the time, I was Auntie's  little feminised "Nephew".

Nowadays, I prefer to dress up as a sissy girl. I like the idea of shedding my male persona behind and embracing the feminine. Not only do I dress as a girl, I like "girly" things. I enjoy playing with my dolls and have developed an interest in things such as Ballet.

Will I ever return to dressing as a sissy boy?- possibly. Sailor suits  and Fauntleroy suits are clothing I still find enjoyable., so who knows? Smile

 Hello Leslie,

The late Victorian and Edwardian periods must have been a wonderful time for seeing so many boys wearing Fauntleroy and sailor suits. I too have often wished I could have been born then so I  could wear such outfits. Of course, petticoating in those days was widespread and I wouldn't be surprised if you passed a boy wearing a frock while you're walking hand-in-hand in the park with your mother or nanny. 

I dare say many a nanny must have got a thrill of dressing a young lad in his sailor suit or whatever and then spending time with him in the nursery. And I wouldn't mind betting they found it difficult to take their eyes of the youngster.  Don't forget, parents of rich children in those days rarely saw their offspring and were brought downstairs by nanny for an hour or so and then taken back to the nursery. 

Some nannies upon seeing a boy in a fauntleroy suit, must have thought how feminine he looks when wearing it and took to dressing him as a girl for a short time. Then there's the rich mother who wished she could have had a daughter rather than a son. As the child grows up she has her boy feminized by his nanny, not only that, she gives strict instructions that he is to remain in a childlike state even through his teenage years.
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#6
(07-01-2020, 12:46 AM)RonnyRemaled Wrote:
(06-24-2018, 11:57 AM)Tiffany Wrote:
(06-23-2018, 09:53 AM)Sissy Leslie Wrote: Hello everyone.   great photoshopped image

When I was  growing up, I wanted to be a sissy boy. I used to imagine myself in a Nursery, sitting on a rocking-horse, or being taken to the park with my toy yacht by Nanny whilst dressed in my sailor suit. I also used to fantasize about being made to wear a Fauntleroy Suit  with my Nanny/Auntie doing up the buttons on my frilly blouse, softy whispering "You are my little Sissy-Boy".

If any film or television program featured as boy dressed in sailor suit or a Fauntleroy Suit, I would take a keen interest. (My parents would be unaware that as I watched it, I was desperately wishing that I could be forcibly dressed in such humiliating outfits).Books on children's costumes also took my fancy.

But it was only when I started to visit Auntie that I became interested in being dressed and treated like a little girl. True, on my first visit, I did wear a makeshift Fauntleroy Suit, and also a Sailor Suit on a couple of occasions. But the majority of the time, I was Auntie's  little feminised "Nephew".

Nowadays, I prefer to dress up as a sissy girl. I like the idea of shedding my male persona behind and embracing the feminine. Not only do I dress as a girl, I like "girly" things. I enjoy playing with my dolls and have developed an interest in things such as Ballet.

Will I ever return to dressing as a sissy boy?- possibly. Sailor suits  and Fauntleroy suits are clothing I still find enjoyable., so who knows? Smile

 Hello Leslie,

The late Victorian and Edwardian periods must have been a wonderful time for seeing so many boys wearing Fauntleroy and sailor suits. I too have often wished I could have been born then so I  could wear such outfits. Of course, petticoating in those days was widespread and I wouldn't be surprised if you passed a boy wearing a frock while you're walking hand-in-hand in the park with your mother or nanny. 

I dare say many a nanny must have got a thrill of dressing a young lad in his sailor suit or whatever and then spending time with him in the nursery. And I wouldn't mind betting they found it difficult to take their eyes of the youngster.  Don't forget, parents of rich children in those days rarely saw their offspring and were brought downstairs by nanny for an hour or so and then taken back to the nursery. 

Some nannies upon seeing a boy in a fauntleroy suit, must have thought how feminine he looks when wearing it and took to dressing him as a girl for a short time. Then there's the rich mother who wished she could have had a daughter rather than a son. As the child grows up she has her boy feminized by his nanny, not only that, she gives strict instructions that he is to remain in a childlike state even through his teenage years.
I agree, Ronny

We can say many things about the victorians but they at least understood the benefit of introducing males to female sensibilities - an art that was unfortunately lost somewhere along the way thereafter. 

I have been lucky in finding it within myself to express my femininity throughout my adulthood and am all the better for it; I only wish boys were afforded the same rights to wear skirts and dresses more widely (whether by impersonating a female as has suited me or just as general day to day wear).

With the many posters on this forum advocating precisely this and at evidence of at least a tentative ‚Äėprogression‚Äô of views in wider society, I am confident that a brighter future is once more in the horizon.
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#7
(06-23-2018, 09:53 AM)Sissy Leslie Wrote: Hello everone.

When I was  growing up, I wanted to be a sissy boy. I used to imagine myself in a Nursery, sitting on a rocking-horse, or being taken to the park with my toy yacht by Nanny whilst dressed in my sailor suit. I also used to fantasize about being made to wear a Fauntleroy Suit  with my Nanny/Auntie doing up the buttons on my frilly blouse, softy whispering "You are my little Sissy-Boy".

If any film or television programme featured as boy dressed in sailor suit or a Fauntleroy Suit, I would take a keen interest. (My parents would be unaware that as I watched it, I was desperately wishing that I could be forcibly dressed in such humiliating outfits).Books on children's costumes also took my fancy.

But it was only when I started to visit Auntie that I became interested in being dressed and treated like a little girl. True, on my first visit, I did wear a makeshift Fauntleroy Suit, and also a Sailor Suit on a couple of occasions. But the majority of the time, I was Auntie's  little feminised "Nephew".

Nowadays, I prefer to dress up as a sissy girl. I like the idea of shedding my male persona behind and embracing the feminine. Not only do I dress as a girl, I like "girly" things. I enjoy playing with my dolls and have developed an interest in things such as Ballet.

Will I ever return to dressing as a sissy boy?- possibly. Sailor suits  and Fauntleroy suits are clothing I still find enjoyable., so who knows? Smile


In some ways, our Victorian and Edwardian forebears were more enlightened than we are today.  They recognised the value of introducing some feminine sensibilities to their male children.  The Fauntleroy suit was remarkably feminine for a boy and it would have given him exposure to fine materials and lace, normally worn by girls.  They also brought in petticoat punishment which turned horrid boys into submissive and gentle girls.

But being dressed and treated as a little girl is the ultimate step from boy to girl.  Personally, I love being a little girl, it is what I was born to be, and I wouldn't go back to boring boyhood for anything!

Love

Lottie
Lottie
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#8
(07-04-2020, 07:48 AM)Lottie Wrote:
(06-23-2018, 09:53 AM)Sissy Leslie Wrote: Hello everone.

When I was  growing up, I wanted to be a sissy boy. I used to imagine myself in a Nursery, sitting on a rocking-horse, or being taken to the park with my toy yacht by Nanny whilst dressed in my sailor suit. I also used to fantasize about being made to wear a Fauntleroy Suit  with my Nanny/Auntie doing up the buttons on my frilly blouse, softy whispering "You are my little Sissy-Boy".

If any film or television programme featured as boy dressed in sailor suit or a Fauntleroy Suit, I would take a keen interest. (My parents would be unaware that as I watched it, I was desperately wishing that I could be forcibly dressed in such humiliating outfits).Books on children's costumes also took my fancy.

But it was only when I started to visit Auntie that I became interested in being dressed and treated like a little girl. True, on my first visit, I did wear a makeshift Fauntleroy Suit, and also a Sailor Suit on a couple of occasions. But the majority of the time, I was Auntie's  little feminised "Nephew".

Nowadays, I prefer to dress up as a sissy girl. I like the idea of shedding my male persona behind and embracing the feminine. Not only do I dress as a girl, I like "girly" things. I enjoy playing with my dolls and have developed an interest in things such as Ballet.

Will I ever return to dressing as a sissy boy?- possibly. Sailor suits  and Fauntleroy suits are clothing I still find enjoyable., so who knows? Smile


In some ways, our Victorian and Edwardian forebears were more enlightened than we are today.  They recognised the value of introducing some feminine sensibilities to their male children.  The Fauntleroy suit was remarkably feminine for a boy and it would have given him exposure to fine materials and lace, normally worn by girls.  They also brought in petticoat punishment which turned horrid boys into submissive and gentle girls.

But being dressed and treated as a little girl is the ultimate step from boy to girl.  Personally, I love being a little girl, it is what I was born to be, and I wouldn't go back to boring boyhood for anything!

Love

Lottie
Lottie
Amen to that, Lottie

I think if most boys could get over the pressure that society places on them to be masculine, they would embrace their feminine side and many would naturally drift towards skirts and dresses (which really would change the face of society).

I know during my own petticoating, the fear of being found out by my ‚Äėmates‚Äô was the main thing preventing me from enjoying most aspects; since¬†I had to wear skirts, heels and makeup full time from 18 and essentially had no choice but to become that person, I have never looked back and continue to dress femininely to this day.
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