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sailor suits & fauntleroy suits
#1
Hi everyone,

Although I currently dress as a sissy girl, it was sissy boy's clothing that got me on the road to becoming a sissy.

When I was at Primary school, our class had to watch a programme about the Victorian Era. It featured a Nursery, and a boy who was riding a rocking-horse. He was wearing a white sailor suit complete with a straw boater-style hat, with a dark blue silk hatband and ribbon attached to it. A Nanny stood nearby. As I watched I thought "I'd be embarrassed to wear such a sissy outfit", but also secretly nursing a desire to be forced to wear one.

As I grew up, any book, film or T.V. show which featured a boy dressed in a sailor suit would make me envious.  I longed to be made to wear one. It wasn't until I was an adult and in my thirties that I got my wish. I used to visit a strict, mature 'Auntie'. As part of our age Regression/Role-play, she would dress me up in sissy clothing. On a particular boiling-hot Summer's day, it was too hot to do anything much. So I ended up being dressed in a short-sleeved top with a sailor collar, along with a pair of toddler training-pants. (I did not wear anything on my feet). Because she wanted to rest, Auntie left me sitting a desk in the sailor-top & pants, contentedly sucking a dummy whilst filling in a colouring-book.

On another visit, I was once again dressed in a sailor suit, but this time for punishment. This was a white sailor suit, but a more adult version with jacket and bell-bottomed trousers. Auntie made me lean over a desk with the bell-bottomed trousers pulled down and  around my ankles. She then preceded to give a sound caning which soon had me yelping with pain. Afterwards, she made me stand in a corner of the room facing the wall with my hands behind my back.  (Auntie was determined to make me be a good little boy).

Another sissy outfit which became the centre of childhood jealousy, was the Fauntleroy suit. What a wonderful sissy, girly outfit! During the 1970s, the B.B.C. broadcast an adaptation of "Little Lord Fauntleroy". In my favourite scene, a scheming woman (who is trying to pass her son off as Cedric, Lord Fauntleroy) is making her son put on a Fauntleroy suit. He doesn't want to, and is struggling and protesting about having to wear it. A wonderful scene.

To leap forward several years, my sister used to have a mail-order catalogue. Out of curiosity, I looked through it. On one page, there was a photograph of a woman modelling a knickerbocker suit, which looked very similar to a Fauntleroy one. As I looked at it, my manhood stirred and I longed for my sister to buy it for me. (At the time, she didn't know about my cross-dressing. But she does today, and I am happy to say that she is okay about it.)

I did get to wear a Fauntleroy suit (of sorts). It was during my very first visit to Auntie mentioned earlier. She made  me put on knickers and a frilly white blouse with lace collar. A pair of black cycling-shorts  substituted for knickerbockers, whilst long black socks stood in for tights. A black velvet jacket completed my outfit. After donning a pair of disposal  rubber surgical gloves, Auntie called me a "Pansy" and a "Milksop". She then gave  me a medical-style examination of my private parts and also my rectum. I felt totally humiliated and degraded, which was enjoyable.

Nowadays, I tend to dress as a sissy girl, in fact as I am typing this ,I am wearing a pair of floral-print knickers. However, from time-to-time, I think about sailor suits and Fauntleroy suits, hoping  that one day I will be able to enjoy wearing these wonderful sissy outfits. (Hopefully whilst under Female domination). Blush
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#2
I have had Nancy Edwina make herself a navy sailor dress. She looks such a child when wearing it with a pair of grey woollen knee socks and a white arran cardigan. Imstead of thinking about these things your Mistress should compel you not just to wear such clothing but have to make it for yourself. In this way you will learn a valuable skill of sewing and dress making which you can use to fulfill your future role in making your own clothes and not wasting your Mistress's money in buying things for you.
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#3
That's a lovely story, Sissy Leslie.

Being made to wear something that is, in theory, male, but in practice very sissyish can be exquisitely humiliating.

You might like the pics I posted under the heading 'Shorts' in the 'Female Dominant Visual Arts' section.
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#4
(07-28-2017, 12:25 PM)minisissyboy Wrote: Certainly these days boys in sailor suits would be thought of as wearing sissy clothing, but when sailor suits were first worn, they were quite standard boys clothing particularly worn by middle and upper class boys. I think most boys have disliked wearing Lord Fauntleroy outfits though mothers used to quite like them.

Sailor suits are not something I ever wore, though I have often as an adult wondered about wearing Japanese style sailor Fuku's (A sailor suit with a skirt) at least in private.
Thats a bit like the one i had . Little blue anchors embroidered on my skirt and little sailor hat .
Angel A little bit of hanky panky does you good .  Angel
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#5
(07-27-2017, 01:49 PM)Sissy Leslie Wrote: Hi everyone,

Although I currently dress as a sissy girl, it was sissy boy's clothing that got me on the road to becoming a sissy.

When I was at Primary school, our class had to watch a programme about the Victorian Era. It featured a Nursery, and a boy who was riding a rocking-horse. He was wearing a white sailor suit complete with a straw boater-style hat, with a dark blue silk hatband and ribbon attached to it. A Nanny stood nearby. As I watched I thought "I'd be embarrassed to wear such a sissy outfit", but also secretly nursing a desire to be forced to wear one.

As I grew up, any book, film or T.V. show which featured a boy dressed in a sailor suit would make me envious.  I longed to be made to wear one. It wasn't until I was an adult and in my thirties that I got my wish. I used to visit a strict, mature 'Auntie'. As part of our age Regression/Role-play, she would dress me up in sissy clothing. On a particular boiling-hot Summer's day, it was too hot to do anything much. So I ended up being dressed in a short-sleeved top with a sailor collar, along with a pair of toddler training-pants. (I did not wear anything on my feet). Because she wanted to rest, Auntie left me sitting a desk in the sailor-top & pants, contentedly sucking a dummy whilst filling in a colouring-book.

On another visit, I was once again dressed in a sailor suit, but this time for punishment. This was a white sailor suit, but a more adult version with jacket and bell-bottomed trousers. Auntie made me lean over a desk with the bell-bottomed trousers pulled down and  around my ankles. She then preceded to give a sound caning which soon had me yelping with pain. Afterwards, she made me stand in a corner of the room facing the wall with my hands behind my back.  (Auntie was determined to make me be a good little boy).

Another sissy outfit which became the centre of childhood jealousy, was the Fauntleroy suit. What a wonderful sissy, girly outfit! During the 1970s, the B.B.C. broadcast an adaptation of "Little Lord Fauntleroy". In my favourite scene, a scheming woman (who is trying to pass her son off as Cedric, Lord Fauntleroy) is making her son put on a Fauntleroy suit. He doesn't want to, and is struggling and protesting about having to wear it. A wonderful scene.

To leap forward several years, my sister used to have a mail-order catalogue. Out of curiosity, I looked through it. On one page, there was a photograph of a woman modelling a knickerbocker suit, which looked very similar to a Fauntleroy one. As I looked at it, my manhood stirred and I longed for my sister to buy it for me. (At the time, she didn't know about my cross-dressing. But she does today, and I am happy to say that she is okay about it.)

I did get to wear a Fauntleroy suit (of sorts). It was during my very first visit to Auntie mentioned earlier. She made  me put on knickers and a frilly white blouse with lace collar. A pair of black cycling-shorts  substituted for knickerbockers, whilst long black socks stood in for tights. A black velvet jacket completed my outfit. After donning a pair of disposal  rubber surgical gloves, Auntie called me a "Pansy" and a "Milksop". She then gave  me a medical-style examination of my private parts and also my rectum. I felt totally humiliated and degraded, which was enjoyable.

Nowadays, I tend to dress as a sissy girl, in fact as I am typing this ,I am wearing a pair of floral-print knickers. However, from time-to-time, I think about sailor suits and Fauntleroy suits, hoping  that one day I will be able to enjoy wearing these wonderful sissy outfits. (Hopefully whilst under Female domination). Blush

Quote:When I was at Primary school, our class had to watch a programme about the Victorian Era. It featured a Nursery, and a boy who was riding a rocking-horse. He was wearing a white sailor suit complete with a straw boater-style hat, with a dark blue silk hatband and ribbon attached to it. A Nanny stood nearby. As I watched I thought "I'd be embarrassed to wear such a sissy outfit", but also secretly nursing a desire to be forced to wear one.

Could it have been something like the two attached images?


Attached Files Thumbnail(s)
       
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#6
(09-05-2017, 02:21 PM)Julian Robinson Wrote:
(07-27-2017, 01:49 PM)Sissy Leslie Wrote: Hi everyone,

Although I currently dress as a sissy girl, it was sissy boy's clothing that got me on the road to becoming a sissy.

When I was at Primary school, our class had to watch a programme about the Victorian Era. It featured a Nursery, and a boy who was riding a rocking-horse. He was wearing a white sailor suit complete with a straw boater-style hat, with a dark blue silk hatband and ribbon attached to it. A Nanny stood nearby. As I watched I thought "I'd be embarrassed to wear such a sissy outfit", but also secretly nursing a desire to be forced to wear one.

As I grew up, any book, film or T.V. show which featured a boy dressed in a sailor suit would make me envious.  I longed to be made to wear one. It wasn't until I was an adult and in my thirties that I got my wish. I used to visit a strict, mature 'Auntie'. As part of our age Regression/Role-play, she would dress me up in sissy clothing. On a particular boiling-hot Summer's day, it was too hot to do anything much. So I ended up being dressed in a short-sleeved top with a sailor collar, along with a pair of toddler training-pants. (I did not wear anything on my feet). Because she wanted to rest, Auntie left me sitting a desk in the sailor-top & pants, contentedly sucking a dummy whilst filling in a colouring-book.

On another visit, I was once again dressed in a sailor suit, but this time for punishment. This was a white sailor suit, but a more adult version with jacket and bell-bottomed trousers. Auntie made me lean over a desk with the bell-bottomed trousers pulled down and  around my ankles. She then preceded to give a sound caning which soon had me yelping with pain. Afterwards, she made me stand in a corner of the room facing the wall with my hands behind my back.  (Auntie was determined to make me be a good little boy).

Another sissy outfit which became the centre of childhood jealousy, was the Fauntleroy suit. What a wonderful sissy, girly outfit! During the 1970s, the B.B.C. broadcast an adaptation of "Little Lord Fauntleroy". In my favourite scene, a scheming woman (who is trying to pass her son off as Cedric, Lord Fauntleroy) is making her son put on a Fauntleroy suit. He doesn't want to, and is struggling and protesting about having to wear it. A wonderful scene.

To leap forward several years, my sister used to have a mail-order catalogue. Out of curiosity, I looked through it. On one page, there was a photograph of a woman modelling a knickerbocker suit, which looked very similar to a Fauntleroy one. As I looked at it, my manhood stirred and I longed for my sister to buy it for me. (At the time, she didn't know about my cross-dressing. But she does today, and I am happy to say that she is okay about it.)

I did get to wear a Fauntleroy suit (of sorts). It was during my very first visit to Auntie mentioned earlier. She made  me put on knickers and a frilly white blouse with lace collar. A pair of black cycling-shorts  substituted for knickerbockers, whilst long black socks stood in for tights. A black velvet jacket completed my outfit. After donning a pair of disposal  rubber surgical gloves, Auntie called me a "Pansy" and a "Milksop". She then gave  me a medical-style examination of my private parts and also my rectum. I felt totally humiliated and degraded, which was enjoyable.

Nowadays, I tend to dress as a sissy girl, in fact as I am typing this ,I am wearing a pair of floral-print knickers. However, from time-to-time, I think about sailor suits and Fauntleroy suits, hoping  that one day I will be able to enjoy wearing these wonderful sissy outfits. (Hopefully whilst under Female domination). Blush

Quote:When I was at Primary school, our class had to watch a programme about the Victorian Era. It featured a Nursery, and a boy who was riding a rocking-horse. He was wearing a white sailor suit complete with a straw boater-style hat, with a dark blue silk hatband and ribbon attached to it. A Nanny stood nearby. As I watched I thought "I'd be embarrassed to wear such a sissy outfit", but also secretly nursing a desire to be forced to wear one.

Could it have been something like the two attached images?

Not quite. He wore trousers and a long-sleeved jacket. Nice pictures though!
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