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On being a sissy.
#1
A friend of mine recently asked me what it's like being a sissy, and whether I considered myself to be a sissy.

I do consider myself a sissy. But, of course, it isn’t as simple as that.

I grew up in an environment where I was regularly punished by being made to wear my little sister’s clothes, including her underwear. The first time it happened I was six years old, and told to go and ask to borrow a pair of my little sister’s knickers to put on for a spanking. I then had to bend over my mother’s lap, wearing knickers, and receive a spanking. It was utterly humiliating.

From then on I was made to wear her clothes, and, when she protested about me wearing her clothes, I was bought my own. My sister is two years younger than me, so it wasn’t just being made to wear girls’ clothes, but clothes that were two years too young for me. From there it lead to being dressed younger and younger until I was dressed as a baby, in nappies.

By the time I was going through puberty I was regularly dressed as a little girl or a baby. The first time I had a ‘wet dream’ was in a nappy. I think this had a big influence on me.

But as I had to wear girls’ clothes more and more, my mother started to let me wear clothes more appropriate for my age.

And then I started to find them more and more comfortable. When she gave me the choice of wearing little girls’ clothes, or wearing girls’ clothes more appropriate for my age, I chose the more age appropriate ones. And enjoyed wearing them more and more.

I had this strange dynamic of feeling humiliated about being dressed in clothes too young for me – short dresses or skirts, frilly underwear, sometimes baby clothes – but quite enjoying wearing girls’ clothes that were appropriate for my age.

From quite an early age I had a different view of wearing sissy clothes to wearing girls’ clothes. To me, ‘sissy’ clothes were clothes that were humiliating, not the sort of clothes someone of my age would normally wear. And because my sissy clothes often involved being put to bed in them, I came to associate them with the kind of things most teenage boys experience in bed. Whereas wearing girls’ clothes was just something that I found more comfortable.

So, now I'm 33 I regularly wear women’s clothes. I don’t go to work dressed, but I have no male underwear, and I dress in women’s clothes most of the time I'm not at work. I just feel more comfortable that way. Pretty much all of my friends know me as a cross-dresser.

My sissy side comes out in private. Most people accept me dressed as a woman. Only a few of them know that I'm also a sissy. To me humiliation is quite a thrill (not always sexual). To me the difference between being a cross dresser and a sissy is that as a cross dresser I wear what a woman would typically wear, but as a sissy I wear what most women either wouldn’t (like baby clothes or little girls’ clothes), or would only wear in private with someone they totally trust (like a schoolgirl or maid’s uniform).

I guess it’s like any ‘kink’ – close friends might know, but not everyone.

Over the years I've been lucky enough to have a few friends who also enjoy that kind of ‘kink’. I have a friend who visits me about once a month who likes me to dress as a schoolgirl. He enjoys spanking and caning me, and I enjoy him doing it. It’s exquisitely humiliating.

I have another couple of friends who are lesbians, and enjoy me dressing as their maid. There’s nothing at all sexual between us. I feel humiliated wearing my little maid’s uniform and serving them (which I love), and they carry on as if it’s quite normal to have a maid bringing them drinks and cooking for them.

I have another friend who enjoys dressing me and treating me like her baby. It’s incredibly humiliating, and so I love it.

One of the things with the Petticoated forum is that it’s an anonymous place to enjoy ones fantasies. I love sharing my experiences, and sometimes exaggerating them a little bit when I write my stories.

I can see on the forum that there are quite varying levels of actual experience of being a sissy. Some are clearly entirely fictional, some are obviously real. It’s all fine. It’s a chance for fantasies and escapism. If I can share some of my own actual experiences and it encourages some other people, or even if they just enjoy reading about them, then that’s all good.

As long as what we enjoy doesn’t hurt anyone else then what’s the harm?
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#2
I can't see any harm in it . In fact it has probably saved me from going mad at times . Having that secret world to escape to in times of stress . The thrill of sharing your secrets with friends and family and the support they give you if you are lucky .
Angel A little bit of hanky panky does you good .  Angel
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#3
Always enjoy your posts, Ali. This is no exception, and i agree that this is a wonderful place to feel free to explore fantasies and in some cases help make them realities.
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#4
(11-18-2018, 11:40 PM)Ali Wrote: A friend of mine recently asked me what it's like being a sissy, and whether I considered myself to be a sissy.

I do consider myself a sissy. But, of course, it isn’t as simple as that.

I grew up in an environment where I was regularly punished by being made to wear my little sister’s clothes, including her underwear. The first time it happened I was six years old, and told to go and ask to borrow a pair of my little sister’s knickers to put on for a spanking. I then had to bend over my mother’s lap, wearing knickers, and receive a spanking. It was utterly humiliating.

From then on I was made to wear her clothes, and, when she protested about me wearing her clothes, I was bought my own. My sister is two years younger than me, so it wasn’t just being made to wear girls’ clothes, but clothes that were two years too young for me. From there it lead to being dressed younger and younger until I was dressed as a baby, in nappies.

By the time I was going through puberty I was regularly dressed as a little girl or a baby. The first time I had a ‘wet dream’ was in a nappy. I think this had a big influence on me.

But as I had to wear girls’ clothes more and more, my mother started to let me wear clothes more appropriate for my age.

And then I started to find them more and more comfortable. When she gave me the choice of wearing little girls’ clothes, or wearing girls’ clothes more appropriate for my age, I chose the more age appropriate ones. And enjoyed wearing them more and more.

I had this strange dynamic of feeling humiliated about being dressed in clothes too young for me – short dresses or skirts, frilly underwear, sometimes baby clothes – but quite enjoying wearing girls’ clothes that were appropriate for my age.

From quite an early age I had a different view of wearing sissy clothes to wearing girls’ clothes. To me, ‘sissy’ clothes were clothes that were humiliating, not the sort of clothes someone of my age would normally wear. And because my sissy clothes often involved being put to bed in them, I came to associate them with the kind of things most teenage boys experience in bed. Whereas wearing girls’ clothes was just something that I found more comfortable.

So, now I'm 33 I regularly wear women’s clothes. I don’t go to work dressed, but I have no male underwear, and I dress in women’s clothes most of the time I'm not at work. I just feel more comfortable that way. Pretty much all of my friends know me as a cross-dresser.

My sissy side comes out in private. Most people accept me dressed as a woman. Only a few of them know that I'm also a sissy. To me humiliation is quite a thrill (not always sexual). To me the difference between being a cross dresser and a sissy is that as a cross dresser I wear what a woman would typically wear, but as a sissy I wear what most women either wouldn’t (like baby clothes or little girls’ clothes), or would only wear in private with someone they totally trust (like a schoolgirl or maid’s uniform).

I guess it’s like any ‘kink’ – close friends might know, but not everyone.

Over the years I've been lucky enough to have a few friends who also enjoy that kind of ‘kink’. I have a friend who visits me about once a month who likes me to dress as a schoolgirl. He enjoys spanking and caning me, and I enjoy him doing it. It’s exquisitely humiliating.

I have another couple of friends who are lesbians, and enjoy me dressing as their maid. There’s nothing at all sexual between us. I feel humiliated wearing my little maid’s uniform and serving them (which I love), and they carry on as if it’s quite normal to have a maid bringing them drinks and cooking for them.

I have another friend who enjoys dressing me and treating me like her baby. It’s incredibly humiliating, and so I love it.

One of the things with the Petticoated forum is that it’s an anonymous place to enjoy ones fantasies. I love sharing my experiences, and sometimes exaggerating them a little bit when I write my stories.

I can see on the forum that there are quite varying levels of actual experience of being a sissy. Some are clearly entirely fictional, some are obviously real. It’s all fine. It’s a chance for fantasies and escapism. If I can share some of my own actual experiences and it encourages some other people, or even if they just enjoy reading about them, then that’s all good.

As long as what we enjoy doesn’t hurt anyone else then what’s the harm?
hi ali

loved the post and yes theres a difference between sissy and crossdresser being sissy is def more humiliating love the fact your mother made u wear them before she spanked u over her knee how long did that carry on for? im glad u have had your fantasies fullfilled by a guy that likes to spank u in sissy wear, do u go out as a woman at all?
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#5
Hiya Mummy Sissy,
The punishments from my mother lasted until I left home when I was sixteen. I had started to enjoy cross dressing from around the age of fourteen, but being put into sissyish clothes like nappies and baby knickers, and little girls' dresses and underwear was incredibly humiliating as a teenager.

When I go out it's mostly dressed as a woman now, except when I go to work. I do have male clothes, but they're mostly for work. I don't have any male underwear.

I love dressing as a woman most of the time. Dresses and skirts are SO much more comfortable. And, practically speaking, I find tights much warmer than trousers in the winter, although I must admit I love the feel of stockings and suspenders sometimes.
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#6
For me, the most exquisite humiliation is in clothes that are male, but not quite. Trousers with a feminine cut or that button up the back or sides . Shirts that have the buttons on the wrong side. Materials that are a bit too feminine, like satins and silks, or ornate like ruffs or lace sleeves. Too many buttons. In short, not Female clothing, but male clothing that has been feminised or emasculated. Demaled.

Think Lord Fauntleroy.
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#7
I know what you mean, Bonzodoug. Clothes that at a first glance could be male, but on any closer inspection clearly aren’t.

As a child my mother once bought me a pair of shorts, which she said I was to be allowed to wear when we were visiting family one day. I felt hugely relieved as I was suffering a week of having to wear panties as a punishment, and had up until then also had to wear a skirt or dress.

When she gave me the shorts to put on, however, they were white towelling, with red edging and an elasticated waist. And they were so high cut at the sides that you could see the trim of my knickers.

I spent all day trying to keep them pulled down enough to not reveal my underwear, but even for the short time that was successful, it was quite obvious they were girls’ shorts.
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#8
I hated wearing shorts at school, which my mother insisted I did even when my contemporaries had moved on to trousers.

My sister smuggled a pair of trousers to school for me at the beginning of term (we boarded), but they were hers.

A dilemma.
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#9
Oh wow. So what did you do? Did you wear your sister's trousers at school? Were they side zip ones?
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#10
(11-26-2018, 12:05 PM)Ali Wrote: Oh wow. So what did you do? Did you wear your sister's trousers at school? Were they side zip ones?

I wore the trousers. 
I was a big sporty chap, even then, so could get away with it. 

They were high waisted, quite flared, grey (so uniform colour). Don’t remember the zip arrangement, but they were quite tight around the bum!
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