Sissy Boy

[Sissyleslie]

Although I like to dress up and behave like a sissy girl, I originally started by wanting to be a sissy boy. This would have meant wearing clothes such as sailor suits and Fauntleroy suits.

Sailor suits became (and still are) an obsession with me. I wanted to dress up as a Victorian boy in a sailor suit, sat on my rocking-horse whilst my Nanny looked on.

It wasn't until much later, when I purchased a uniform from an Army & Navy store that I was able to indulge myself. It was this sailor suit that I wore when I visited 'Auntie ', who caned me. Whilst the caning was not enjoyable, being dressed in a sailor suit, under female domination and being treated like a sissy boy was.

Fauntleroy suits are also a passion, as they bring a strong sissy aspect with the lace and frills.

I intend to revisit this side of my sissy nature-
I would like to dress up and act like a sissy boy. Perhaps wear a sailor suit, play with toy cars or a train set. I will let you know how things turn out.

 

[PaigeCherubiel]

I understand. I was AMAB and have no sisters, so I don't really know anything about playing with what were considered "girls toys" when I was a kid; and these "dolls" I'm collecting are actually ceramic piggy banks, ceramic S&P shakers, papier-mache "good luck charms", and wooden figurines. Mass-produced Japanese folk art, not actual "dollies". To be continued . . .

 

[PaigeCherubiel]

I'd either want to be either a petticoated man or a brolita. Someone would have to teach me how to do my hair, nails, and makeup to pass for a girl although I love earrings and lipstick. I'd rather be a well-crossdressed man in a nice dress, petticoat, nylons, and pumps than have to worry about "passing". Which, I guess, is why my "Fred Flintstone in drag" avatar suits me.

 

[BabyTheleste]

Although I like to dress up and behave like a sissy girl, I originally started by wanting to be a sissy boy. This would have meant wearing clothes such as sailor suits and Fauntleroy suits.


Fauntleroy suits are also a passion, as they bring a strong sissy aspect with the lace and frills.

Have you managed to find a decent Fauntleroy suit? I would love to wear one to bring a new dimension to my sissyness, but I’ve not been able to find one.

 

[BuddyBoy]

Although I like to dress up and behave like a sissy girl, I originally started by wanting to be a sissy boy. This would have meant wearing clothes such as sailor suits and Fauntleroy suits.

Sailor suits became (and still are) an obsession with me. I wanted to dress up as a Victorian boy in a sailor suit, sat on my rocking-horse whilst my Nanny looked on.

It wasn't until much later, when I purchased a uniform from an Army & Navy store that I was able to indulge myself. It was this sailor suit that I wore when I visited 'Auntie ', who caned me. Whilst the caning was not enjoyable, being dressed in a sailor suit, under female domination and being treated like a sissy boy was.

Fauntleroy suits are also a passion, as they bring a strong sissy aspect with the lace and frills.

I intend to revisit this side of my sissy nature-
I would like to dress up and act like a sissy boy. Perhaps wear a sailor suit, play with toy cars or a train set. I will let you know how things turn out.

Leslie, I too have an affection for that type of clothing. I am drawn to the image of the feminized boy, even to wearing kilts and other girls clothes. But not to the extent that he would be mistaken for a girl-that is another culture. Best of luck in your quest.

 

[PaigeCherubiel]

I hope this isn't too off-topic. I am drawn to the idea of "accidental girls" - the brother of the bride who just happens to fit in the dress of a bridesmaid who can't make it. The male new hire at a theme park who fits in the Alice-in-Wonderland costume. The brother "volunteered" to be a Princess at a little girl's birthday party.

 

[Sissyleslie]

Leslie, I too have an affection for that type of clothing. I am drawn to the image of the feminized boy, even to wearing kilts and other girls clothes. But not to the extent that he would be mistaken for a girl-that is another culture. Best of luck in your quest.

Thank you. I will see how this quest turns out.

 

[Sissyleslie]

Have you managed to find a decent Fauntleroy suit? I would love to wear one to bring a new dimension to my sissyness, but I’ve not been able to find one.

They are not the easiest thing to find. When I first visited 'Auntie ', I wore a makeshift Fauntleroy suit. It consisted of a a frilly blouse, black cycling shorts made a substitute pair of knickerbockers, instead of tights, I wore dark, knee-length socks and finally, a blue velvet jacket.
I still have the frilly women's blouse-

Getting tights wouldn't be a problem. Knickerbockers I might be able to get on Amazon or Etsy (Possibly also a velvet jacket). A blonde wig with ringlets would be a finishing touch, along with a sash and Mary-Jane shoes.
Back in the early 1990's, I did try a Fancy Dress shop. I hired out this outfit-

(I apologise for the poor quality of the photo and having to 'censor' it! ).
Interestingly, back in the late 1970's and early 1980's, there was a woman's knickerbocker suit that resembled a Fauntleroy suit. (I used to drool over a photo of it in my sister's mail-order catalogue! ).
I will see if I can come up with at least an approximation of a Fauntleroy suit. It should probably be an interesting challenge.

 

[babylock1]

Have you managed to find a decent Fauntleroy suit? I would love to wear one to bring a new dimension to my sissyness, but I’ve not been able to find one.

Go on eBay or browse thrift charity stores for blouses with frilly lace edging and button placket details (especially left-side closing with
i.e. multiple buttons flashy pearl type) Look for short waisted hem to show diapers if worn.
Pants (ugh the dreaded pants - why does it have to be pants !) look for flyless flat front with multiple side button closing (sailor pants) or
side or rear zip closing - - - push the limits of clothing not usually worn by males - you should get the idea message here.

 

[Sissyleslie]

Thank you for your advice, BabyTheleste.I will certainly keep these things in mind when I am considering my outfit.

 

[Deleted member 73292]

Although I like to dress up and behave like a sissy girl, I originally started by wanting to be a sissy boy. This would have meant wearing clothes such as sailor suits and Fauntleroy suits.

Sailor suits became (and still are) an obsession with me. I wanted to dress up as a Victorian boy in a sailor suit, sat on my rocking-horse whilst my Nanny looked on.

It wasn't until much later, when I purchased a uniform from an Army & Navy store that I was able to indulge myself. It was this sailor suit that I wore when I visited 'Auntie ', who caned me. Whilst the caning was not enjoyable, being dressed in a sailor suit, under female domination and being treated like a sissy boy was.

Fauntleroy suits are also a passion, as they bring a strong sissy aspect with the lace and frills.

I intend to revisit this side of my sissy nature-
I would like to dress up and act like a sissy boy. Perhaps wear a sailor suit, play with toy cars or a train set. I will let you know how things turn out.

Thank you, Sissyleslie, for another lovely post. I'm afraid I have never seen a Fauntleroy suit, for a child or an adult. But Eton suits are still popular for little boys, and I think they make adorable sissy wear, especially with a lace-trimmed collar, mary jane shoes, frilly socks, and other sissyish refinements. An American variant on the Fauntleroy suit was the Buster Brown suit, after an early-20th century comic strip. https://en.wikipedia.org/wiki/Buster_Brown I remember seeing that comic strip years later as a little girl, and thinking Buster Brown was no sissy, but many boys thought the outfit was very sissyish. I guess they were right! I imagine you would look very sweet in one.

 

[Sissyleslie]

Thank you for your kind words. Yes, I guess that a Buster Brown outfit is 'sissyish' - looking.

 

[RppcB]

Leslie, I too have an affection for that type of clothing. I am drawn to the image of the feminized boy, even to wearing kilts and other girls clothes. But not to the extent that he would be mistaken for a girl-that is another culture. Best of luck in your quest.

Hi! I am trying to explore some previous threads and so when I write to you I'm somewhat assured that I'm not assuming anything or making untoward statements. I can relate to these gosh it's taking me so long to write three words, these God this is really beneath my ability to express myself but observations

 

[Sissyleslie]

That's a wonderful outfit. I love the collar.

 

[littlecolo]

Loved this posting I just came across since,I a very much also a sissy/pansy boy and thus had a very elaborate Faintleroy outfit made about a few years ago by a costumer on Etsy.

 

[BuddyBoy]

Loved this posting I just came across since,I a very much also a sissy/pansy boy and thus had a very elaborate Faintleroy outfit made about a few years ago by a costumer on Etsy.

Could we see it or better yet, you in it?

 

[Tom1066]

Like most of us, I gather, I started as a bit of a sissyish boi. But it wasn't long before I made the transition to femininity. I'm now a complete sissy, preferring to be with men and to play the slut baby girl role. It's easy to be a sissy, dressing in panties, camisoles and a whole variety of sexy feminine clothing. I like to combine my sissy inclination with my DL fascination. But the it comes diaper changing time, I prefer a man's hands and fingers, and as often as possible a simple diaper change ends up in one or more sexual acts--which I love.

 

[Shannon1024]

Like most of us, I gather, I started as a bit of a sissyish boi. But it wasn't long before I made the transition to femininity. I'm now a complete sissy, preferring to be with men and to play the slut baby girl role. It's easy to be a sissy, dressing in panties, camisoles and a whole variety of sexy feminine clothing. I like to combine my sissy inclination with my DL fascination. But the it comes diaper changing time, I prefer a man's hands and fingers, and as often as possible a simple diaper change ends up in one or more sexual acts--which I love.

I couldn’t agree more !

 

[Tom1066]

I couldn’t agree more !

Shannon, you sound like my kinda gurl! Hope you're having a pleasant day.

 

[littlecolo]

For the custom made fauntleroy outfit I had made I am not able to show wearing it since I am in California for the winter but here are two pics, one showing the Victorian inspiration picture in light blue and pictures of the completed adult version made for me. Unfortunately the seamstress who made it a few years ago is no longer on etsy.