Sissy Sailor Suit

Sissyleslie

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Ever since I was a young boy, I have wanted to wear a sailor suit (or to be more accurate, forcibly dressed in one and the sort that Victorian boys wore).

My first encounter with this outfit was when I was at Primary school. Our class watched a tv programme about the Victorian era. It featured a Nursery, with a boy sitting on a rocking-horse dressed in a white sailor suit. A woman dressed as a Nanny was nearby.

As I watched, I thought that the sailor suit would have been embarrassing to wear, but I would have enjoyed the humiliation. My sailor suit fetish was born.

Growing up, any tv or film featuring period costumes with boys dressed in sailor suit would interest me. I would look on with envy, wishing it was me. The following photo is how I imagined myself-
20230207_214723~2.jpg

But it was many years before I got the opportunity to wear one.

I did have a basic one made - a light blue, short-sleeved sailor top with navy blue shorts. Although not great quality, it served its purpose.

It was this one that I wore when I visited 'Auntie' . It was a boiling hot day -so hot in fact, that she just wanted to rest. So she left me sitting at a table dressed in the sailor suit. (The shorts were replaced with toddler training pants and I wore nothing on my feet). I sat sucking my dummy and contentedly filled in a colouring book.

But a later visit to her wasn't so peaceful. This time the sailor suit, a white one, was a uniform purchased from an Army & Navy Surplus  store, with long-sleeved jacket and bell-bottom trousers.

'Auntie' decided that I needed to be disciplined. So she made me pull down my trousers and pants and lean forward, with my hands on a desk. She then caned me, which caused to yelp in pain. Afterwards, she made me stand in corner, pants and trousers pulled down. My reddened buttocks were on display. Eventually she relented and we both had a cup of tea, although she did threaten me with another caning if I spilled any on my sailor suit. (Sadly, the sailor suit became ruined after the place it was stored leaked and let rain in).

That was several years ago. In the past couple of years, I have managed to get some more sailor suits, including this one-
20230114_194540~2.jpg
And this one-
20230114_205216~2.jpg

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My fantasy is to be dominated by a woman dressed in a traditional Nanny's uniform. When she sees me in my adult clothing she angrily says: "Take those ridiculous clothes off. Who told you that you could dress like a grown-up? All your clothing off...NOW!"

She then holds up a sailor suit in front of me - "Put your PROPER clothes on" she orders. I do as I'm told, with the added humiliation of nappy-pants and the threat of them being replaced with a nappy if I misbehave. I am given a teddy-bear, made to suck a dummy. She then grabs my hand and leads me into a Nursery where I undergo the humiliation of enforced age-regression .

Perhaps inevitably, my sailor suit fetish had expanded to include sailor dresses, etc. I will deal with this in another thread.
 
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Good golly none of those outfits have any rank - it is no wonder that age regression has started at the lowest level !
 
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I love sailor suits wearing my cloth nappy and rubbers and my nappy peeking out by side of my shorts
 
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Nice! I have the female version of this, in latex
 

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My sailor suits are from Little-for-Big:

LB-013TL-20200222-1-510x510.jpg

Of course I don't have the attributes to fill it out in the same fashion - but never the less.
Also have it in PINK !
 
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babylock1 said:
My sailor suits are from Little-for-Big:

View attachment 102608

Of course I don't have the attributes to fill it out in the same fashion - but never the less.
Also have it in PINK !
Nice! I have this in pink too.
 
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I got these! 🥰

il_794xN.4275657286_mnu2.jpg il_794xN.4015935858_s72s.jpg
 
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