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The Sissy Fetish, Part 2: What I've Learned Since (Final Revision 3/24)
by MsOfficeTease
Posted On 03/15/2009 01:30:25

(NOTE: I've decided to revise this post again in response to critical comments from daquiri among others--and also from my sissy sub semon/nissa, whose path both challenges and confirms my analysis so far--rather than just respond to them in a new separate post. I think this is more useful--since what I'm doing is clarifying my views rather than changing them. I'd like this post to be useful to sissies, non-sissy subs, and of course to Dommes, which is why I'm taking the trouble. I totally encourage and welcome comments, critical, adoring, or both. But this is it. Any further discussion will be in comments. )

Flash forward a couple more years. I was working in an office, dating “J” and discovering the wonderful worlds of conscious Female Domination and male fetishism through his gentle but devoted and persistent tutelage (I’ve always wanted to use that word). I’m going to go into this whole topic much more in a future post, but for now what’s relevant is this. “J” made it very clear from the start that (a) stockings (especially gartered stockings) and high heels worn by a sexually confident and assertive woman were the express lane to intense arousal to him; and that (b) the fact that the woman knew about this weakness and was deliberately using it to manipulate and/or control him totally sealed the deal and made him absolutely helpless with submissive excitement. The same was also true of his secondary fetishes, which include satin and lace lingerie, corsets and girdles, latex clothing (especially skirts and stockings, again), cheerleader and tennis skirts, nurse uniforms, lipsticked and glossed lips, polished nails--and above all my feet, legs and butt. From literally our second date “J” invited me—in fact, begged me--to use his fetishes to make him my “love slave,” according to the techniques laid out so well by Georgeann Cross in Sexual Power for Women and by Elise Sutton in several books. Once I got over my Catholic girl qualms I absolutely loved it and still do. The idea of total sexual possession of a man, and through that, complete control of his behavior, is probably the single most erotic idea to me. Just thinking about it, even now writing this, makes me excited.


As I said, I’ll be writing more about the whole process with “J” soon. But what’s important is the understanding and skills I gained in the use of fetishes, particularly clothing fetishes, for erotic domination. And it can even be done at a distance. I can call “J” at work and just say certain trigger words connected to his fetishes in a certain tone I use, and I can hear him dropping into sub space like a stone as his voice thickens with arousal. (I like doing it to him when he’s in a meeting!) So when, a week or two after joining this site, I met a boy here with fetishes very similar to “J”’s, using the same tricks on him was easy and fun. Then I noticed that he was dropping little hints about crossdressing and being feminized. All of a sudden I made the mental connection back to Timmy, and then I just knew what to do. Timmy had been a sissy, I now realized, and this boy was too! He was just older, more sophisticated, and more fixated on specific fetish triggers (but like Timmy, he loved being called a slut!). So I started using the fetish codes to take him deeper and deeper into crossdressing and submission, because I discovered that feminizing a boy--taking away his masculinity and getting him to beg to be girly--was quite a power rush. I found that with someone like this boy, feminization is incredibly easy. Also, after a year of chatting with and dominating several other sissies and reading stuff that sissies have written (oh, and a book by a feminizing Domme called Veronica Vera), I think I have at least partly figured out what sissy-ness is and where it comes from.

First, though, responding to a challenge from one of my readers, I'll say how I define a sissy. To me, a sissy is a submissive, effeminate/hyperfeminine crossdresser who adores Females and fetishes feminine things: clothing, lingerie and hosiery (especially), shoes, makeup and beauty products, hair, perfume and toiletries, behavior and speech patterns, and even women's beauty and fashion magazines. As distinct from transsexuals, sissies don't generally feel they're in the wrong body and crave a complete transition to being women. Also as distinct from transsexuals, they are sexually excited by crossdressing one of the marks of  real TS is that, as for nearly all genetic women and girls, female clothing, while they may find particular items pretty and pleasing to wear, is not in itself sexually stimulating. Unlike with "vanilla" crossdressers, though--of whom I have encountered one or two--the sexual excitement sissies get from crossdressing is bound up with submissive feelings toward actual Females.


The recipe for a sissy is like this: take one sensitive, usually intelligent boy who can’t hack the brutal hierarchical sorting process of early teenage “masculinization” when boys learn the rules of being boys. (The hierarchical sorting process of “feminine-ization” for early teenage girls is equally brutal, but more socially-emotionally and less physically I think.) Often this is because the boy isn’t very interested in “boy stuff” like sports and violent video games. Or it can be because he is physically frail and retiring. Or, even if he has "normal" boy interests and is fairly athletic, it can be because he has a very small penis—this seems to be common. Or, ditto, it can be that he discovers masturbation and develops fetishes for lingerie, stockings, or whatever via porn, being shy around girls. Finally it can be because he is just in general more “femme” psychologically (gentle, timid) without being a transsexual. Very often, when much younger, he has envied little girls their pretty clothes and “soft” forms of play, including dolls and so forth, preferring them to the rough games of boys. Or, as has been suggested in comments on the first version of this post, he just has a femme side that comes out more with age--especially, I would guess, with or soon after puberty.

My guess is that some combination of these "ingredients" will tend to produce either a sissy or a "pantyboy" type submissive with strong fetishistic tendencies. I don't mean to imply that they're all necessary. For instance, I've met sissies who have perfectly respectable-size dicks, sissies who when not kneeling in their frillies enjoy wilderness survival treks, sissies who collect guns, and so forth. Also, as in the case of the first boy I feminized, some sissies mostly repress their natures into their thirties or--I've been told by others I've met--even later.


Typically (but not always) the proto-sissy boy is entirely or anyway mostly heterosexual. His low position on the teenage masculine totem pole means that he is rejected as an object of sexual interest by girls as a teen, even if he is not bad looking. At the same time his brain is being bathed in sex hormones, and girls, especially the very femme girls at the top of the femininity hierarchy, absolutely mesmerize him. Their bodies, their voices, their hair, their mannerisms, and their clothes, all make him crazy with desire and adoration. And so their humiliation at being failed boys and sexually rejected by girls is eroticized. They become submissive, emotionally masochistic to one degree or another, fetishistic about “sexy” female clothing and footwear, and aroused by the humiliation so long as an attractive girl or woman is doing it. I also think that older women concerned with the approaching loss of their attractiveness often spot boys of this type and to one degree or another take advantage by seducing and erotically dominating them, even if it’s no more than teasing. Typically, these women seem to present themselves in classic high femme style, with skirts, heels, nylons, perfume, makeup, and so on. That reinforces (or just triggers for the first time) the fetishism and submissiveness. This has helped me to understand why so many sissies--or just femme-fetishistic subs--love the fantasy of being feminized by a sexy Mature Lady as a teen.


What seems to happen then is very well described by my sissy sub Amber in her incredibly helpful and informative blog post about her history. The boy’s fascination with feminine things, his inability to form “normal” relationships with girls in his mid and late teens, and the intensity of his desires causes him to transform himself into his own ideal sexy, sensual, flirty feminine companion—but in her deeply submissive mirror image. But since he wants to enjoy that companionship as a boy, he doesn’t reject his male genitals—though he may crave continued erotic humiliation about their inadequacy. He yearns for a Dominant Woman to come along and complete him by reinforcing his femininity, compelling him to abandon the failed (as he experiences it) masculine side of him and bringing his adopted femininity and his submissiveness fully together, closing the circuit so to speak. Because the Dominant Woman embodies the Goddess of Femininity, his other side, the sissy worships Her. The result is that the sissy as a type is probably the best submissive to Dominant females.


This will probably be a controversial statement with many Dommes on here as well as many subs. Most heterosexual Dommes I know want a masculine man whom they dominate in the bedroom (or in the rest of daily life too) but who is “strong” in “manly” ways. They are not turned on by feminine men at all, or even by somewhat androgynous ones like my husband. In other words, they are very comfortable inside the existing rules of gender except that the traditional power relationship is reversed. Some are even offended by sissies as “caricatures” of femininity. OK, I mean, if you want the big strong manly guy and get off on dominating his big strong manliness—great! I can totally relate. I enjoy it myself. But I think it’s a mistake not to see that sissies are hyperfemme not because they misunderstand femininity, let alone resent it, but because they love it so much. To sissies, femininity is a way to get close to the Femaleness they adore but feel they can’t possess as males or “real men”—and also therefore want to serve and worship.


Myself, I love how submissive and adoring sissies are. I think they’re sweet and cute and—if the sissy is attractive in that androgynous way—even sexy. And besides, I do enjoy teasing and humiliating them in play and then being sweet and maternal with them afterwards. They bring out both sides of my Dommely personality really nicely. Because they're femme, they have a better intuitive understanding of me and my pleasures and desires than pretty much any masculine male sub I've met. (My husband, who is androgynous in more than just appearance though not a sissy or crossdresser, is an exception, as are some other very sensitive masculine boys I've met.) And I don’t mistake sissies' fluttery, cooing femme-ness for weakness. Nothing is tougher in our culture than being a hyperfeminine male who is submissive to women. I respect their courage in being what they are. You go, girls! Now kiss my toes!


Tags: Sissies Crossdressers Fetish Lingerie Submission Femme


Viewing 1 - 10 out of 11 Comments

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From: DaleFeathers
06/05/2013 02:29:43

Ms Office Tease

The responses seem so complicated, personally I am feeling somewhat subdued. I recognized myself in the recepie for the sissy and felt caught out.  But what about "panty-boys", are there no such fetishists in your world?


From: ColdEyes
01/22/2011 13:44:12

I just came across this and I can only say: Wow, it's so right it's scary. You even got the category I would fall under with this line:

"Some are even offended by sissies as “caricatures” of femininity."

I guess I would be a sissy who is not into sissification, as nearly everything else in this essay applies to me. Crossdressing is a big turn-off for me -- there must be a feminine body to match the clothes, otherwise it doesn't work. Ironically, my body is rather masculine. Perhaps I would try it if I could look convincingly feminine, but that would be a hopeless cause with my body.

The idea that our feminine and masculine sides are at odds is right on. I was always socially androgynous -- I liked all the violent video games, played with toy soldiers, studied historical weaponry, etc. But any real life violence is anathema to me. Sometimes I even cringe when I see a boxing match. When the boys got too rough for me, I would go do arts and crafts or something with the girls. The problem, of course, was that there was a lot of pressure to go one way or the other -- be a "real boy" or a "girlie boy," and I didn't want to choose, so I got ragged on for being girlie anyway.

I skipped over the stage where girls had cooties. Even elementary school, I started developing sexual attraction toward the opposite sex, but it was for women 3,4,5, times my age, grown women. I didn't even know what sex was, I just became obsessed with the mature feminine form out of nowhere really. I recall looking through the TV guide for R-rated movies because I wanted to see all sorts of naked women. At the same time, it wasn't just staring at naked girls -- I also fantasized about being one! Whenever a clothing catalogue would come, I'd flip to the women's section and imagine myself trying on all these outfits, which really excited me. I guess you could call it sexual narcissism -- I liked the idea of looking attractive to myself. (Thinking back, it always reminds me of the line from Silence of the Lambs: "I'd fuck me!") On top of all this, I started having all these humiliation fantasies about enforced nudity. Usually involving a gang of girls tearing my clothes off and then teasing and laughing at me. But I also had a ton of fantasies as my female alter ego, also ending up in humiliating situations where I'd lose my clothes.

That's basically how it started for me. For a number of reasons, my masculine and feminine sides became more compartmentalized and I began to see the masculine side as bad and the feminine side as good. Many of my fantasies reflect that -- when I fantasize as a male, most of them involve femdom, essentially punishment for my masculinity. In most of my romantic candlelit-dinner type fantasies, I am almost always female with a female partner and both of us are very femme, but my partner is usually a little more masculine and aggressive. I guess I am something of a "male lesbian."

From: MsOfficeTease
03/23/2009 13:17:49

amoradox wrote:
Very well-written and thought out, Ms Cindy. I think You have an amazing, intuitive understanding of sissy psychology, which enables You to easily manipulate and control Your sissy subs. Your description of the development of the average sissy sounds very much like my own experience in many ways. I'd like to explore that a bit more when I have more time.

Thanks, amo. Actually from the conversations I've had with you and your little autobiography, you seem a bit different. For example, like semon you were not an early crossdresser at all. The common factors are your adoring relationship to girls and submissive feelings growing as you looked at porn, both in adolescence. And, I think, sexualized shame about your, ummm, private solo behavior. That also seems to be a really typical, though I am not sure how it fits exactly.

From: amoradox
03/21/2009 10:35:57
Very well-written and thought out, Ms Cindy. I think You have an amazing, intuitive understanding of sissy psychology, which enables You to easily manipulate and control Your sissy subs. Your description of the development of the average sissy sounds very much like my own experience in many ways. I'd like to explore that a bit more when I have more time.

From: semon39
03/18/2009 19:07:29

I have read with interest Ms Office Teases posts on feminization and the "making" of a sissy. For me, i have never had feelings of sexual insecurity or a failure to fit in to archtypical masculine roles. i work in a construction company and i have a successful career. My "clitty" is of average size.

However, i have always been a sexual submissive with a strong desire for strong willed assertive and authoratative women. Women possess incredible sexual power over men but so few realise it or use it to their advantage. A dominant woman can sense the effect she has on men and use it to her own ends. I always found that concept mesmorizing. The way a woman can dress to accentuate her assets, her figure, legs, breasts has always held a fascination for me. I guess this is where my fetishes originate. I love clothing and accessories that make a woman look more elgant, sexy and sophisticated. Gowns, suits, dresses, heels and lingerie all accentuate the female form and i love women who appreciate and use these items to their advantage and who are aware of the effect that they have on men.

As time passed, my submissive nature grew and my fantasies became more profound. I could imagine a Mistress dressing in a dominant way and using my fetishes to control me - to make me into her slave. I could imagine her using these items to tease and torment me and i could imagine her controlling my orgasms, denying me and directing when i was allowed  to cum. As part of this, my fetish for silks and satins grew and i started to dress in womens clothes luxuriating in the feel of the fabrics. It turned me on to wear panties and stockings and heels and this, combined with my submissive nature, inevitably led me to seek out a domme who would be able to manipulate me for her amusement.

When i was first dominated in panties, made to face my fetishes in a sexual (online) relationship with another person, something just tripped and i started to long to be dressed, and controlled as a sissy as a fundimental part of my submissive nature. My Mistress picked up on this quickly and used it to enslave me further. It was (and is) heady and intoxicating and the jorney has been incredibly intense.

I am not a woman, and i do not desire to be a woman but I would love to become more passable in the future and will be working on that. I am a sissy because it feels wonderful and it accentuates and emphasises my submissive nature but also becuae there is a slightly shameful and humiliating aspect to it that touches my subby sole. As a sexual being i love all of that, it turns me on.

My experience may not be typical and i have come to all of this relatively late in life (i am in my thirties), but i believe it to be a valuable contribution on the subject and hope that it will provoke discussion accordingly.

Best wishes Mistress Cindy

sissy nissa

From: daquiri
03/17/2009 00:51:38

ok after reading the edited version. i do see that we are fairly close. Plus, some of the additions or maybe just rereading it and combined with some recent eyeopening on my part, it did seem to hit home and almost like you were discussing me. albeit, not quite, but close enough. which does scare me somewhat.

it's scary because it seems to take away my cherished uniqueness, and because, maybe i really am a bigger "sissy" than i thought. of course, maybe not, it may just be a reaction to focusing on only one area? like when someone gets fixated in seeing a pattern in a couple of things and then sees it everywhere, like the movies 23 or Pi. is the pattern really there or is the mind making things fit the pattern?

while we may not agree on the final outcomes of it all thus far, i think we have established some common ground to work from. dont you think? or am i just way off base? and i want to make clear, i agreed with you for the most part and didn't mean to come off sounding critical or harsh.

thank you for starting this discussion, now if they were a few more commenters.... :)

(and i wish they had an editing function! heh.)

From: daquiri
03/17/2009 00:36:40

i don't disagree with most of what you thought. perhaps more a
refinement. although i did get a little lost in my response. i guess
really the only thing i disagreed with was the video games and sports,
and maybe a bit on the relationship with girls. Although i must confess
that going back and rereading both your post and my response, i got
things a bit confused or offtrack on a couple of points (and as i said,
i still have some difficulty in having indepth discussion this way, but
i'm working on that).

i agree there are multiple
combinations of factors, which is why it makes it so tough. i hestiate
to ask you to define what a "sissy" is to you in a shortened
definition, as i think its a term that has a somewhat general
definition that converys the overall concept, but actually defining
what it is cannot be done. just far too many variable and factors. that
is to say one should not try, as while we may never fully get there,
there is a point to striving for closer. but on the other hand, knowing
where you're coming from, regardless of specificty of definition would
be helpful. you kind of lay it out, but i'm not sure it gets all there.

me, a sissy is (and this is still under construction) a male who has
various levels of feminine tendecies, the greater the tendencies the
more the sissy, but never approaching a full desire to completely leave
the male body. a sissy can simply wear toe nail polish or can go full
cross dresser, with plenty of room in between. it's a rather large
spectrum i think. even true on the submission front i think.

feminizing the same as sissifying? or what is the difference.now, does
it cross the equally loose definitions of transgendered, transvestite,
crossdresser, pantyboy, submissive, bottom, vanilla, etc. etc.? yes it
does.  elements of all seem to overlap, the difference of many of the
levels of each "label" intersects and forms the differeing degrees (if
you will) of sissyhood. i guess to me i just have a more inclusive
definition maybe than you do?

part of the problem may be
that i'm just now beginning to accept the role of sissy in my life and
am basing things on older notions and experiences that may not still be
right. i'm not sure on that. i'm also not sure how "sissy" i am, nor
how much of one i was then. was i always on? did i grow into it more? a
bit of both perhaps? but i'm trying to express what i know and what
i've encountered. although, i should probably draw more from my
experience to help in the discussion and not hide behind others
impressions. this i will work on, and i shall ponder some more. you've
got me thinking a lot about this lately and it's all a bit jumbled.

may be having a hard time explaining or defining a sissy, but i know
one when i spot one usually. and i'm beginning to think i can spot them
not only from that premise, but because, i too am becoming one.

(and i just saw the edited note and will give the new post a read, but i still go with what i said above in reply to your comment. although i reserve the right to post again even disagreeing with myself after that. :) )

From: MsOfficeTease
03/16/2009 12:50:55

Daquiri--I think some of your apparent differences with what I wrote in v.1 of this were from misreading and some from were from me not being as clear as I could have been: emphasizing more that there are multiple combinations of factors that produce a sissy, and of course, clearly defining what I at least mean by the term "sissy." You may still have differences, since the impression you leave is that you appreciate my effort and sympathey but disagree with most of what you thought I was saying. I'll be interested to see your next responses.

From: daquiri
03/15/2009 14:27:12

Ok, i will try to explain a more more, I just find it difficult to have an indepth discussion this way.

guess i don't agree with your characterization recipe so much. Granted
this is from personal experiene with the issues, reading about it, and
discussing it. To be honest, i'm not 100% sure where i am right now.
But myself and several others who are or lean to being sissy, did play
sports or violent video games, or were the quintessential boy.
Sometimes the disconnect came later, or there was no disconnect. It was
merely another side, albeit perhaps one suppressed. The two sides are
not mutually exclusive. A duality perhaps?

Also, i'm not sure
about the relationship with females and being sissy. Some of this comes
from reading your post, Amber's, and other things. While it may be true
that there always seems to be an obstacle in moving to the next step
with that chosen female, the very fact of being a sissy may be the
reason. The being sissy may be the reason for the obstacle, or the
obstacle may be the reason for creating the sissy.  A chicken and egg
problem maybe. Either way the two sides seem to reinforce the same

Some say the sissy, like the transgendered/transsexual (i understand
that sissy and tg are not the same, but do have some overlap) wants to
be more like those women. He wants to exude that sex and feminity she

of the problem, like most things kink, is that no one label really fits
well. Some may think simple wearing panties is sissy. Some say it's a
simple wearing of garments and maybe makeup and prancing about. Others
demand that there be more to it, or just simply, a feeling of being
sissy and none of the traditional physical expressions of sissyhood
need be there. We may consider one or the other to be a wannabe, but i
don't think that is fair. Others may not really agree with a
distinction of a sissy being different than a TG/TS. If one believes
they are something for whatever reason and expresses that feeling, then
to me, they are that thing and should be treated so.

i'd agree that the sissy is the ideal for a Domme, at least one who is
into the being worshipped and adored sort. As you point out, some
rather would like to break the "real man". However, some of those real
men have the same feelings that your description fo a sissy would. So
there could be the thrill of breaking through sissifying a real man,
not simply finding an already made sissy and simply encouraging and
nuturing him.

I'm understanding and having trouble dealing with
the concept that there are no right answers with these things, but
getting there more a bit everyday.

I'm not sure i've hit all the
points thus far or stayed to where my mind was last night when making
that post. But i just wanted to make a few points, no matter how
disheveled or not fully expressed. You make a few other points that i'd
like to ponder a bit more as well, and most likely more will be made
from this discussion.

(sorry for any formatting problems, i had to edit the first time with deleting and it seems it might cause some format issues).

From: MsOfficeTease
03/15/2009 04:24:03

Daquiri: Please be specific aboput agreements and disagreements! I want these posts to spark discussion. Then I learn.

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