Are You A Sissy?

E-mail Print PDF

SissygirlGrowing up in Brooklyn, New York during the 1960s, the term “sissy” had a much different meaning than it does today.

Where do you fall on that spectrum?

When I was a kid, as a closet cross-dresser, I was all too familiar with the term, and avoided association with it at all costs.  A sissy was often the opposite of a Tom Boy. Back then a sissy was any boy who acted effeminate; any boy who wore clothes deemed girlish in style or color; any boy who did things considered girly; any boy who moved in anyway less than “macho” – God forbid you allowed others to see your wrist hanging limp!

Wikipedia describes a sissy as (derived from sister; also sissy baby, sissy boy, etc.) is a pejorative term for a boy or man who violates or does not meet the traditional male gender role. Generally, sissy implies a lack of courage and stoicism, which are thought important to the male role. A man might also be considered a sissy for being interested in traditionally feminine hobbies or employment (e.g., being fond of fashion, going to meditation sessions, or cooking), for displaying effeminate behavior (e.g., saying "mua mua" before hanging up the phone or using creams), for being un-athletic, or for being homosexual.

This left a lot of sissy quicksand for one to fall into; wear pink, yellow or powder blue anything – shirt, socks, shorts, jacket – and you might as well just adopt a girl’s name right there on the spot and be content to watch the boys play from then on without you -- because you’d never again be allowed to join in boy games.  Get caught by friends playing girl games – like house, fashion show or tea for two -- with sisters or girlfriends or girl cousins --, and you’d be exiled to girls land forever.  And even getting caught doing domestic things – cooking or cleaning, for example --, though you might get a pass because everyone knows that “mom made you do it!”, you’d still be ribbed relentlessly for quite a while.

Oddly the actual closet sissies rarely, if ever, got called on anything because they were always on guard: they never did or said anything that would revealSissy service their private sissy-ness to anyone.

The closest I ever came was when I performed in an Irish Jig dance troupe. After one particular performance, some kid in the audience called me a sissy.  It was a good thing that I concurrently was taking martial arts, and when we scuffled and I flipped him, my “tough guy” image was secured.

While it was an unwritten obligation for any “man” boy to out a sissy when he saw one, he’d often do so with his sole motivation simply to show that he himself wasn’t a sissy.

As boys growing up in the 1960s, we had macho standards to uphold.  They were set decades before our own by the screen actor rebels like James Dean or Marlon Brando, Paul Newman, or even clean-cut but dashing manly-men like Kirk Douglas, Gregory Peck or Cary Grant. In the 1960s Steve McQueen ushered in a new standard: he was the King of Cool.  We had lots of macho roles to emulate.

For many decades the words sissy and homosexual were synonymous.  Any cross-dresser would certainly be deemed a sissy; what “man” would wear women’s clothing and make up?

But things have changed through the decades, both in meaning and vernacular.   Gender has gotten more fluid, especially in clothing styles and colors, the acceptance of men engaging in cooking classes, and generally becoming more domesticated – remember the Metrosexxuals of the 1980s?

There is now an entire sub-culture in the transgender community where men are sissified, which is like feminized, but with more frilly and submissive overtones, and often tied to B&D (bondage and domination) activities.

While some transgender gurlz strive to become more feminine, most envision themselves either as women [trapped in a man’s body), “Two Spirited” – possessing both feminine and masculine components that comprise their gender identity, or simply guys that like to be feminine and pretty occasionally – and what’s wrong with that?

The sissy, however, doesn’t see himself as a women; in fact he is firmly rooted in the reality that he is not a women, nor can he every truly become one, but no longer a man either. In many instances the sissy sees women as the superior species, and is happy to simply elevate themselves to their highest possible feminine representation of female.

To that end, the sissy acts and dresses as frilly and feminine as possible, but never in a mainstream way. They love ruffles, satin, and lace in yellow, white and pink, anything that accentuates femininity – usually garters & stockings, high heels, and costumes.  But it can also include baby girl and little girl attire and actions as well.

Their goal is not to assimilate; thus the frills are both an adoration of feminism, and a reminder that they’re merely emulating that which they can never actually be.

It is then no surprise that most sissies are usually submissive in nature, a soft demeanor that earns to serve.  Often when you come upon social profiles of sissies, they are seeking a “strong master or mistress” to train them. This is yet another way of saying, “bring out the girl in me and suppress the male … PLEASE!”

Is being a sissy then really about being and looking feminine, or is it really – at the root – about power, the lack of, and/or exchange of it?

Being a sissy these days isn’t about dressing up somewhere and getting a little sexual eroticism; it’s a commitment to becoming something not female or male, but highly feminine, regardless of the age play.  No one in the broader transgender community really understands sissies, just like the mainstream – or the gay community for that matter -- doesn’t really get transgender.

So sissies are left to their own devices, or God-willing a master or mistress that can guide, mold and nurture them.  Being a sad sissy is pointless, because according to Quentin Crisp, “their biscuit-baking mothers would tell them that if they’re looking for sympathy, that they’ll find it in the thesaurus between shit and syphilis … and after Sissy.”

Until next time sissies, be happy, be save, and always think pretty!


+6 #22 Guest 2013-09-24 06:53
:D i looking a sissy maid job and they can have fun with me and i am kinky to
+2 #21 Guest 2013-07-11 20:58
I am a sissy, occasionally. I cross-dress and love to dress as a sissy sometimes. I am definitely excited by the B&D connotation, but I love the look and the whole soft-smooth satin and frills look, with all the accessories which go with it.
+5 #20 Guest 2013-07-10 10:34
I guess I am an official sissy now ,since my wifes gay friend ,David Femino of Beverly Ma beat me up ,and now like my wife since she caught me in her panties and bra sucking Davids cock,and made me admit it on this site He wants me to tell how I yelled at him for admitting to my wife that I have been sucking his cock for 3 years ,and went to slap him ,and got my ass kicked and knocked out cold by David a gay ,who I thought would be easy to slap around ,but found out he was a lot tougher then meand I now not only am my wifes cuckold husband ,but Davids sissy bitch ,that now sucks davids cock whenever he orders me to ,So for all you guys that think that gays are weak and cant fight ,You are wrong ,and I and my black eye and fat lip are proof of it ,Sissy Brucie
-1 #19 Guest 2013-07-06 05:30
My now cuckoldress wife wants you to e-mail me ,and tell me you now know Bruce Burke of Beverly ma is really a sissy cocksuckng fag and not the big tough guy masculine guy I have prtended to be for years so she can show everyone your e-mail
+8 #18 Guest 2013-06-05 05:45
Yes it is so true that back in the sixties ,sissies were viewed so badly ,the worse thing you could be called was a queer or sissy ,as I found out when my friends from the neighbor hood when I was 13 ,surprised me by coming down to my fathers cellar to find me and there I was in my sisters panties ,and masterbating my tiny cock .The guys grabbed me and tied my hands with a rope they found in the cellar and called me a little sissy ,and made me suck and masterbate there cocks and used the treat of telling everyone at school how they caught me in panties masterbating if I didnt give them blowjobs any time they wanted one .they even brought over panties and bras for me to wear they stole from there sisters and mothers ,to wear as I sucked off they cocks as they read playboy magizines they took from there dads collections ,
+6 #17 kathyann 2013-06-04 11:30
I too, love being a sissy. I have been one for such a long time, noiw. And, hopefully one day my 2 live in Mistresses will let me finally become a total woman. I am mostly changed but, I still have that ugly worm between my legs. Thankfully, though since they had me castrated that ugly thing has gotten even more smaller & so very much softer. I'm so happy that it no longer gets hard and when my panties are up that nasty male outline is no longer there.
+5 #16 Guest 2013-05-06 14:27
hi brianna,

i grew up in the sixties too, and you were so accurate about your description of society back then and how it looked down upon sissies. i felt everything coming back to me as i read your piece. hugs.

+3 #15 Guest 2013-04-11 09:08
Enjoyed the comments and the gurls being themselves and acceptin it sas they should. Sissy phyll xoxoxoxoxoxoxox o
+2 #14 Guest 2013-03-09 23:18
Dear Brianna, I liked your essay on being a Sissy. I don't know if you remember me or not. You did introduce me to that gender-friendly restaurant, EoE. I was very active with my beloved Tiffany Club. (TCNE). These days, my, now, Mistress/Wife has me pegged. I am Her Housemaid/husba nd. She keeps me around for, "laughs," and to do all the household chores. One of Her Girlfriends, who couldnt remember my name, called me, "Missy." She liked it. I've been, "Missy," ever since. Just are when we were growing-up and your parents called you by your first & middle name, you were in trouble. If She calls me, "Miss Susan," or, "Susan Pauline," I'm in trouble. The only times, that I'm, "Susan-less," is at either of my two part-time job or if we're with our children or grand-children. I think you included my first by-line: "Skirts and Heels in Manhattan. I do hope, that you are doing well.

Sisterly yours,

"Missy," Susan Pauline
+6 #13 Guest 2013-02-18 16:54
I am now in a relationship with a nice man who has trained me to be his woman. I do like to go out and walk as a woman in a park dressed very daringly with a very short skirt or dress and an equally short coat. I do wear an auburn wig, earrings, and makeup. My legs are my best asset so I wear sheer hose and very high heels to sasha back and forth as I walk. I pass and love it when the men slow down and take a good look. If they ever approached me I don't know what I would do. My friend says get in the car, go for it Nancy, you will have fun. What should I do.

Please login to post and read comments