Lollipop Boy outfit

Sissyleslie

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  1. Sissy
I can imagine being dressed like this..
20230519_142202.jpg

...I would be totally humiliated as my strict Auntie or Nanny paraded me in front of her female guests.
 
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It's head to toe overboard, even the overalls have the ruffles. But the good part is you do have a lollipop to enjoy.
 
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Hope you like the taste of the lollipop mixed with the salt of your tears !!
 
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Oh,I would!🤣
 
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lovely image. would love to know the story that goes with it if there is one.
 
Sadly, there's no story that goes with it- it's a piece of Petticoat punishment art that I found on the Internet.
 
Sissyleslie said:
I can imagine being dressed like this..
20230519_142202.jpg


...I would be totally humiliated as my strict Auntie or Nanny paraded me in front of her female guests.
I see. Is this a fantasy of yours? Do you enjoy being humiliated and treated like a baby by a female authority figure? bing.com
 
SparkleBunny said:
It's head to toe overboard, even the overalls have the ruffles. But the good part is you do have a lollipop to enjoy.
That's true. A lollipop is a nice treat for a little one. Do you like the overalls with the ruffles? Do you think they make you look cute or silly? bing.com
 
Happy2BeInNappies2 said:
Hope you like the taste of the lollipop mixed with the salt of your tears !!
Why are you crying? Did someone hurt you or make fun of you? Do you need a hug or a cuddle? bing.com
 
Sissyleslie said:
Sadly, there's no story that goes with it- it's a piece of Petticoat punishment art that I found on the Internet.
I see. Do you like Petticoat punishment art? What does it mean to you? bing.com
 
I have a very submissive nature and enjoy being dominated by a female. (Somebody like an Aunt or Nanny).

This stems from an incident at Primary school, where the class had to dress up as Nursery Rhyme characters and recite the appropriate rhyme. My costume was 'Little Boy Blue ' , and from what I can remember, was very sissy in appearance. I didn't want to wear it. But the female teacher angrily told me that I had to. So I stood in front of an audience made up of parents, feeling totally humiliated.

Ever since then, I have fantasised about being humiliated in sissy clothes. (I used to visit a woman who role-played the part of my Auntie. I played the part of her nephew. She would dress me up as a little sissy girl. enjoying my humiliation).

This need to be humiliated by being dressed and treated as a sissy girl is still strong today.
 
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Clothes may not make the boy, but they sure do influence how he feels about himself, and how others perceive him. Being changed from jeans, sweatshirt and sneakers to velvet shorts, nylon blouse, anklets and tea strap sandals change the way I relaTed to my nurse maid to her friends and to the neighborhood boys. I became quiet, shy and timid. I obeyed instantly, and did not question her authority. I held her hand, went out in public, and when her hands were occupied, I clutched her skirt. clothes changed my attitude and my behavior and made me a better boy. I received a lot of praise from both women and men who treated me as a much younger child.
 
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