The Sissies are Coming!

I’ve mentioned before that the difference between a freestyler and a crossdresser is that a freestyler just wants the option to wear the clothes associated with the opposite sex. Without judgement about their sexuality or sanity. Even mix up the clothing. Blending a style that is both male and female from time to time. It’s all about the fashion freedom to wear what you like.

A crossdresser is more about playing the part of the opposite sex. This may involve wearing a wig or breast forms. It may involve trying to be passable as the opposite sex. Using a name that is different from their own while dressed as the opposite sex. In some instances acting as if they are two different people, one male and one female inhabiting the same body and called to the front depending on which attire they are wearing.

A freestyler isn’t concerned about these things. A freestyler is just a guy (usually – since women already have multiple clothing types available to them) that wants to wear a skirt or some nail polish or other traditionally feminine things, but also a pair of cargo shorts and a polo shirt. It all depends on how they feel that day. It’s not about bringing out their feminine side, it’s just about wearing what they like. It’s all about the fashion.

To a freestyler, it’s not about there being male and female sides to your personality, it’s about embracing the idea that males have a wide personality range based on the traits they embrace. Just like females.
It’s more about personality traits than sides. A male can like pretty pink frilly things without having to call forth a feminine persona to embrace and justify it. Just like man can be passive or silly or giggly or submissive or caring or nurturing without having to embrace a female persona.
We’re all humans, and these traits are available to all of us.
While it’s true that males and females tend to default to certain traits that encompass what we stereotypically describe as masculine or feminine, these are just defaults. They aren’t set in stone. There is variation among individuals. Either naturally or through conscious acceptance.
A freestyler accepts the fact that they can be a male and like stereotypically female things without having to invoke a stereotypical female to do it.

So what are Sissies?
I should probably take a moment to talk about this group since I never have before.
Sissies are a certain breed of male to female crossdresser. Like crossdressers, sissies aim to dress and play a feminine role. The difference is that sissies do it for the kink. They play a specific type of submissive and sexual female role. Men who like to be feminized or force feminized by a mistress or a master and submit to said mistress or master as a form of sexual arousal. To the point of even being a sexual lifestyle for some. Where they come home from work as a man and then go into full sissy mode.
There are crossdressers who may be sissy-like from time to time. Especially during sex. Through not always. Crossdressing is more about releasing a feminine side, not as a sexual kink, but as an expression of one’s personality.

I learned many years ago that I was neither of these things. I started out by crossdressing because I thought that’s what you had to do. And always felt strange about it. Why was I wearing a wig? Why was I trying to make it look like I had breasts when I didn’t? Why was I trying to hide my dick? It all felt fake to me. I soon realized I wasn’t into crossdressing, I was into what I called casual crossdressing at the time and later freestyling (as in freestyle fashion). What I desired was really just to wear clothing I liked the look of. Whether it was something made for a man or a woman. It wasn’t a sexual kink and it wasn’t about releasing some female trapped inside of me. It was really just about wearing a dress or a pink lace thong.
Was there an initial rush of feeling like I was getting away with something I shouldn’t be doing? Yes. That’s society fucking with you boy! But that quickly subsided and these clothing items just became mine.

If I were to look in my underwear drawer right now, I would see a mix of boxer briefs, men’s bikini briefs and a variety of women’s panties that range from cotton and lace thongs to boy shorts and women’s casual briefs. It’s all just my underwear and it’s all mixed together. It’s not an event. Putting them on doesn’t transform my personality. And while I can recognize that some are sexier than others, the women’s panties aren’t automatically sexier than the men’s or vice versa. I have some men’s underwear that are sexier than women’s underwear. But neither are men’s or women’s anymore. They’re all just mine. That’s how I see them. I don’t associate them with a sex or gender.

While I have nothing against crossdressers, it just wasn’t for me. Is that to say that I don’t have similar traits to other crossdressers? Traits that many would consider stereotypically feminine. Of course not. My personality is like some strange cross between a crass frat boy, a nerdy artist type who is big into sci-fi, the Roman empire, Indiana Jones and Uncharted, and a teenage girl who is into anime and pink sparkly stuff. I’m kind of all over the place and I like that about me.

So what about the sissies?
I’ve got nothing against sissies either. At least in a perfect world. They will do what they will do. Though it does feel like there has been an uptick in sissies lately. I blame porn for that.
Porn does affect our greater culture. It influences people, for better or worse. You be the judge of that. But I do attribute a lot of sissy culture lately with porn. I think what happened is that a lot of straight guys found themselves watching straight porn, and then found themselves curious about transgender porn. Transgender porn then lead to sissy porn. I could be wrong of course. This is just a best guess.

It doesn’t really help the freestylers out there. It’s another stigma to have to overcome if you’re just a guy who wants to wear a dress. Now we’re not just contending with “oh so you want to be a woman” but also with “you just want to be bent over and fucked by a big black cock, don’t you? You little freak.” Among other things men say to other people when they have their dick in their hand and use it to do their thinking.
Not really. I just want to wear a dress because I think they are nice looking and free feeling. I have no desire to be labeled a female or take a big cock up my ass. Thank you very much! Likewise I have no desire to be lead around by a dominate female like some kind of whipping boy. I have a girlfriend, and I’m the dominate one in bed. Typically.

Others may wonder what the point is to freestyling. Like, where is the fun in it? This comes mostly from people who see crossdressing as a kink. Freestyling is not a kink. It’s a freedom. Fashion freedom to be more specific. I’m sure there are male freestylers who want to take a big cock up their ass or be lead around by a mistress. But that’s a separate thing from freestyling. In the same way you don’t associate a button up dress shirt with eating out a woman’s tailpipe, you don’t associate a guy in a skirt and nail polish with getting his balls stepped on my a mistress. These are separate things.

The problem is, they aren’t really separate things for sissies, and therein lies the problem. A problem even good old fashioned crossdressers can also relate to. Since they also don’t want to be associated with a sexual kink either. Even if they may dress to feel sexy sometimes. But hey so do freestylers sometimes and so do regular people who dress according to their gender. Everyone wants to feel sexy sometimes. But for sissies, it seems to be one-in-the-same. And that, as I said, can hurt the public perception for crossdressers and certainly freestylers.

Of course, what does public perception really matter right? After all, the public is nothing but a mob with terrible comprehension skills. You can’t explained nuanced detail to a mob. They only read headlines and pick out certain words in articles that scare them. They fly over everything else. Like they’re on a trip from New York City to Los Angeles and everything in between is of no consequence or importance. They’ll never really understand what a fashion freestyler is, or even a crossdresser. Sure as shit they know what a sissy is though, because a sissy is everything they always thought the other two were anyway. And a sissy is nothing but confirmation they were right. So we’re all sissies now. Even if we aren’t. Better make way. The sissies are coming!

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One Comment

  1. Well written and researched! The one thing I would add is there also seems to be a bit of ageplay in the sissy subculture – a crossdresser who does not just dress in an overtly feminine way and crave humiliation by a dominatrix, but specifically favours styles associated with young girls. When I include crossdressing groups in my search for other men who wear clothes from across the aisle, I frequently end up drowning in posts by fetishists. The sissy and baby groups have a large overlap!

    One other comment: It took me a while to realise what the word conveys nowadays. In my youth when I was first discovering that I was “not like other boys”, I heard that term a lot. But in the 50’s and 60’s – I daresay up into the 90’s – it only meant a boy (or man) who failed to meet society’s expectations of manliness. Small, weak, intellectual, unable or unwilling to fight… I was all of those, and wore the label “sissy” many times to the jeering of other children. At no point did it have anything to do with clothing, except as a taunt after the label was applied: “You’re such a sissy, you ought to wear a dress!”

    Ah, if only they knew that’s exactly what I ended up doing!

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