[Author's note: a collection of my writings on cross-dressing and erotic humiliation are available on Amazon, under the title: "A Treatise on the Sissy." -- Baloardo Gratiano.]
Sissy and Wimp
1
Now the common belief is that any man who wants to wear women's clothes is gay, and that the heterosexual crossdressers who claim to be straight but "just like the feel" of silk panties and so forth, are being, well, less than candid. Be that as it may, heterosexual and homosexual crossdressers are in fact distinct psychological types.
To be sure, there is a homosexual element in all crossdressing. but it is not necessarily a vital and structural one. We may legitimately distinguish between the male-focused and the female-focused crossdresser, whom we shall call the sissy and the wimp.
The crossdresser who dreams of being a dominant man's sissy wants to achieve a "womanhood" which is little more than a reflection of the most rudimentary male desires. He wants to be a whore, an erotic plaything, a simple sex object. The persona the sissy constructs for himself, though female so far as it goes, falls very far short of being a woman. And in fact the inner life of woman, her psychological being, is of little interest to the sissy. He aspires be nothing more than a cunt, and so his erotic focus is entirely on cock. He is a devout worshipper of the phallus, and caters in every way to masculine lust.
The crossdresser who wants to belong to a woman, the wimp, has rather a different psychological composition. His yearnings are rather closer to heterosexual desire -- he does, after all, want to be with a woman. For him the desire to wear women's clothes is not for the sake of attracting a dominant male, but rather to eliminate males and masculinity entirely from the erotic vista.
This kind of crossdresser is in a sense a lesbian, at least in his rejection of the masculine and his uncritical enthusiasm for all things female.
For the wimp, the thrill of being penetrated by his wife's strap-on doesn't depend on pretending she has a penis, but on using this experience to more vividly imagine that he himself does not. Above all he is excited by his own emasculation. A sissy will want to be told by the man that he has a tight little cunt, that he is a good bitch, &c., but the wimp will be thrilled more by being told by the woman who reams him that this is what he deserves for having a little dick. The wimp has no interest in pretending that the woman is actually a man. What matters is that he is dickless and that she owns his unmanly self. He wants to be a deballed by a woman, dildo fucked, kept in panties, trained to do humbling housework and obey -- he wants to be figuratively castrated.
While the sissy wants to be a woman degraded by a man; the wimp wants to be a man degraded by a woman. For the wimp, the trappings of femininity are prized as proofs that he is utterly pussy-whipped.
2
For the dominant woman, the keenest pleasure in pegging her submissive wimp will be that of controlling him, asserting ownership, putting him in his place -- under her. The knowledge that she can penetrate him when she pleases, and shall often do so without letting him orgasm, makes it very clear who is in charge.
When she does allow him to cum, he is being penetrated, in the most unmistakable assertion of her ownership. Taking his ass, mounting him like a bitch, makes him pathetically whimper and squirt into his rubber -- an emission which she will be sure to have him swallow so there can be no doubt that this ritual is all about humiliating him.
Forcibly neutered by being made to assume the female role in all sexual activity, nothing remains for him but the dominant woman's now all-powerful and unchallenged cunt, which he worships with his eyes, his tongue, and his ceaseless longings.
Because emasculation is the essential precondition of his pleasure, the wimp will be obsessively interested in having his penis size belittled. He will wish it to be measured with a ruler and then have his ass whipped with that very inch-reckoning instrument, to drive more poignantly home his lacks. He will want to be made to wear panties in acknowledgment of his want of a penis. He will tuck and tape his genitals and wear tight pants, so that the flat front showcases his loss.
Having so little liking for his own cock, it is not surprising that he as no interest in anyone else's. But he will surf the net to gaze, with unspeakable longing, on mere images of cunt, with a contemplative intensity that borders on religious ecstasy.
While the sissy wishes to finally, so far as is feasible, become a woman, if not through surgery, then at least by dressing so as to be passable, the wimp with be well content with such minor feminizations of his appearance as suffice to undercut masculinity. His ideal self-image is not female, but androgynous.
It might be asked, why does he desire the trappings of femininity? If the object is to be neutered, to have his own gender annihilated before the majesty of cunt, wouldn't he wish to be a eunuch rather than a woman?
The status of a castrato will indeed appeal to some, but the gruesome mechanics, and the lack of any positive identity, make this in general a repellent prospect. The assumption of femininity, however, is an extremely pleasing option, both for the intrinsic aesthetic interest of self-adornment, and for the opportunity to identify with an adored womanhood.
We need not here enter into the Freudian theory that explains the male crossdresser's need to make oblique his unconscious attraction to women. Suffice it to say, the sissy resolves his unconscious anxieties by becoming a woman. The wimp makes a more advantageous bargain with his unconscious by making himself a non-male, thus allowing himself untroubled possession of a woman -- since after all, he never physically possesses her. Rather she takes him.
The study of the sissy and the wimp is particularly revelatory of the infrastructure of male homosexuality, for it offers as it were missing links between homosexuality and heterosexuality, reveals their interconnectedness -- which is part of the reason crossdressers are viewed with such disquiet by both the straight and gay communities.
3
The wimp is of course pantied at all times when he is at home (that is to say, in the woman's house.) And he should be expected to put on some makeup and a wig (if he is short haired) to present a properly androgynous appearance.
There are times however when a wimp should be fully dressed in female clothing: when he is doing the humbling housework that falls to the lot of the inferior member of a couple. Particularly when he cleans the bathroom or does the laundry, he should be dressed as fully as is practical. Particularly to be recommended are panty-hose or, better still, a panty girdle, which will keep him tightly tucked and allow him to fully feel like the pussy he is.
The wimp hand-washes all the delicates. It is always salutary for him to carefully tend to the underwear of his superior, as it is to for him to contemplate his own pastel colored underthings and confront afresh the facts of his life.
Gone are the y-fronts and jockstraps. No one need look on these dispiriting reminders of the days when he still thought he was a man and she pretended to be believe it.
4
By a curious irony, it is precisely the humbling and humiliating treatment that men dealt out to women in the 1950's that is most appropriate for men themselves, and most conducive to male happiness and the health of a marriage -- at least when the male is a wimp and the wife means to keep him in his place.
The wimp should be completely dependent on the dominant woman for sexual release. Masturbation must be punished severely. First, because all the wimp's sexual energy and interest should be focused on the woman who owns him. To touch himself for private pleasure is both to cheat on her and to steal from her. His entire sexual being is her property. When he is not serving her, he should be allowed no sexual being at all -- except perhaps a constant unsatisfied craving, a painful sense of his own incompleteness without the woman.
The wimp should be made to understand that all his sexual urges are shameful and deserving of punishment. The woman's sexual needs, on the other hand, are to be regarded as a natural right, a splendid show of wholesome energy. Even while obeying the woman's explicit commands and servicing her, the male's actions are low and whorish.
What is the meaning of this paradox. If sex itself were shameful, the woman would be compromised as well. No, it is not the sex but the submission that is humiliating. It is the desire to be used by another, to identify so completely with someone else that their pleasure supersedes and replaces one's own -- that is what makes the submissive male a whore, a slave, a thing to be used. The wimp male ecstatically accepts sex on these terms, which match so well his obvious inadequacies.
The wimp is trained to take his owner's strapon. At first it should be a small one, exactly the size of his own, until he becomes adept at accepting it into his throat and can take the hardest fucking she can pound him with. Once this goal is achieved, the wimp should be made to admit that such a little cock (and implicitly, such a little cock as his) isn't adequate even for him. He is made to understand that a woman can feel submissive towards a masculine man with a normal sized cock, but a little thing like this -- like his --just isn't enough.
The wimp agrees and begs her for a larger cock. Finally she trains him with one. The object here is not to give him a gay experience, or turn him towards men, but to complete his humiliation and subjection. He will come to accept that he has no control over how, when, or how often his mouth or ass are violated, and will finally come to regard her strapon with a certain amount of apprehension. He is only allowed to cum with her strapon (or a buttplug) in him, and of course he always swallows his own sperm. Again we come to the paradigm of the nineteen-fifties submissive wife, who has been trained to believe she can only cum when penetrated by her husband. The woman who accepts that sex ordinarily ends with her swallowing a mouthful of sperm before the eyes of a gloating partner.
The wimp is still occasionally used for "normal" sex, at the woman's pleasure. But usually this ends rapidly -- with him being pushed back down between her knees to use his mouth -- with the observation she'd forgotten how small his thing was. If he is allowed to ejaculate in her, he of course cleans her afterwards with his tongue.
The wimp realizes that he really has nothing between his legs until the woman penetrates him. Only her strapon relieves his sense of sexual inadequacy. And inadequate he is, except as a housemaid, and sexual servant. She and only she completes him. He has long since ceased to feel anything but shame about the little thing in his panties, but he exults in the marks on his punished buttocks, as he does in his humiliating penetration. It allows him to feel what he knows -- that he is owned.
5
Although nature made the mistake of giving the wimp a penis at all, it means very little. He knows he can't pretend to be a husband. He is only happy being a wife
He wants to feel exactly what an obedient wife would. He wants to be fucked hard with a strapon and told that this is what happens to submissive women, to just put his face in the pillow and take it. He wants to be made to swallow the contents of his rubber after he has "squirted like a girl" from being taken by the dominant woman. She reminds him that his need to cum is pathetic, she observes that perhaps he won't be so eager to if he has to swallow it every time, as a submissive wife is expected to.
He is eager to clean the toilet and hand-wash the woman's panties. Usually he'll wear a skirt and a bra while he performs these services. It's not to make him a woman but to humiliate him as a man. As exciting as it is for him to wear a skirt, it's just as exciting to have her remind him, while she paddles his ass, that he belongs in one, with his little dick and his natural submission to female authority. He doesn't wear the pants in the home, figuratively or literally. The panties he now has on under his clothes are a daily reminder, as is the hairless little dick he hides in them.
Such wholesome sensations may be reinforced verbally:
"If you had a real cock, women would have sensed it, and not just by seeing a bulge in your pants. But you were small-framed, shy, and everyone figured you were gay, though they didn't say anything, at least not to you. No girl who looked like me ever showed an interest in you, because you didn't have a dick like this (indicating the strap-on.) But men who did have cocks were interested in a weak boy like you, and you probably let a number of them use you like a girl while you tried to figure out what was wrong with you.
"But you couldn't admit what the problem was. You knew you weren't hung, but you thought you were at least average. A girl wants a cock that's big enough to fill her mouth, she wants a guy who's masculine enough to make her feel like a woman. And a girl wants a cock that's wide enough to really rub her clit while she's getting fucked.
"There's no thrill of submission in licking your little cocktail sausage.
"You never looked down and saw a girl like you turned out to be, licking your dominant cock. Because you never had the girl. Because you never had the cock.
"Other guys got their cocks sucked like this. But you were the kind of guy girls think of as 'really nice.'
"Sometimes girls would toy with the idea of using you for sex. It was flattering to have you follow them around with your little stiffy in your pants. But then they went for a masculine guy with a real cock who knew how to make the first move.
"Then finally you found a woman who knew how to treat a boy like you. A woman who didn't want her face fucked or her ass spanked or her cunt pounded. A woman who wanted her pussy worshiped and her ass licked.
"The kind of woman who didn't want a man. She wanted a little-dicked wimp she could spank when he got out of line. And you knew you belonged on your knees in front of a woman like that.
"You loved it when I put you in panties, didn't you? What an exhilarating relief to know you would never be expected to be a man. To find that you finally could please a woman, albeit like a girl, with your tongue
"At last you were actually glad your dick was so small: it fit in your girly underthings
"You accepted your place as the one who gets penetrated. You finally understood that you don't get pussy if you are a pussy.
"And that's how this story ends. With you as a strong woman's wife, with a cunt shoved in your face, gratefully jerking off after she's cum in your mouth and you've licked her clean."
6
The wimp is already and always sexually desperate, unable to actively satisfy himself with the dominant woman and denied the release of masturbation.
For the most part, his ugly little penis remains untouched, tucked and taped inside his panties. The wimp's ass is the appropriate object of petting and caressing. This is where the wimp receives his beatings, so any kindness lavished there will have a special meaning. And more importantly, the wimp is being trained to think of himself as dickless. His sexual organs are his mouth, which services the dominant woman, and his ass, which he offers to her whip and her strapon. Patting his ass, making him take his pants down to show his panties and give access, holding him by the hips to teasingly dry hump him from behind -- this kind of play humiliates him and exalts the woman. It reduces the wimp to the status of a pet. And of course he is never allowed similar liberties with her.
At times however the woman may enjoy cock-teasing her wimp -- particularly when he is bound. His little dick is caressed while the woman asks him if he would like to have her kneel and suck it for him? Would he like her to put on a short skirt and feminine panties, then bend over to offer him her pussy? Would he like to cum in her and have her lick his cock clean after? Doesn't he wish he had a thick cock, the kind that makes women weak and submissive? Does he dream of having a big cock and training her to swallow his cum?
(As a variation on this theme, the owner may actually allow the wimp to cum, and then have him lick up his little mess while she laughs at him)
These forbidden fantasies, suggested in a low purring voice while his little dick is stroked, will make him as hard as he gets -- and then he is in the perfect state to have his ass whipped severely enough to reduce his penis to its proper humbled state. This is a good time to remind him that if he really did have a normal sized penis, he would never have ended up in panties. He would have satisfied her and she would have been glad to be submissive to his dick. But he failed. He was inadequate. And he frustrated her over and over with his little dick, expecting her to pretend it gave her pleasure. And that is why he is being beaten now. That's what men with little dicks deserve. It is well to know the exact size of his cock, and remind him of it. Six inches is the uninspiring average. Anything less than that is small. If the wimp is well endowed, well, this was one of nature's mistakes, and he can be upbraided for not deserving a man's member. Whatever the size (and it's probably not much) it will be small and properly submissive by the time the wimp's ass-whipping is done.
This game may be repeated as often as is amusing, and at the end the wimp is put back in his panties, his little thing tucked, his buttocks sore, and in just the right frame of mind to service his owner.
7
A male with an undersized penis, let us say five inches in length and of unimpressive girth, needs to be continually reminded of his failure. Despite all evidence, the underendowed man always comes back to the idea that he actually has something in their pants. It is a strong woman's job to remind him that this is not the case.
One of the most effective ways of putting a male in his place is to make him confront the fact that his penis is the size of a little boy's. (making him shave himself there will reinforce this concept ).
For this lesson it is best if the woman wears a skirt, to emphasize her femaleness. and so the male's humiliation in front of a woman. He should be required to take down his pants and underwear so she, fully dressed, can inspect his "little thing." She will express surprise at the small size, hairlessness, unimpressive balls. She will conclude aloud: "that explains so much, doesn't it?" His submissiveness, his willingness to do housework, his relinquishment of a husband's right to penetrate. At this point the woman should hold her strapon dildo next to his little dick, to force a yet more heartfelt acknowledgment of his shortcomings.
Then, since he is nothing more than a boy in the genital department, it's only right that he should acknowledge female authority. He must now bend over for a spanking. If he has the dick of a little boy, then he needs someone in a skirt to tell him what to do and paddle his ass to be sure he does it.
After his punishment, he may be required to stand in the corner with his pants down and his red ass on display. Or he may have to thank his wife for letting him wear nice panties that fit his little nub just right. And no, he doesn't deserve boy's underwear, he's too small for it.
Finally he should be made to kneel in front of her as she raises her skirt to let him kiss the panties that cover her triumphant vulva. Then he will be allowed to lick her -- the only way a tiny dicked man can serve a woman.
"Good boy. Lick mommy nicely."
8
After the wimp has brought her to orgasm and licked her pussy clean, perhaps even licked her ass and drunk her piss, it's time to let him cum. A particularly good way of managing this is to have the woman, fully dressed, in her skirt, jerk his little thing off for him into a waste basket or into the toilet, while telling him how cute it is.
"Go on, make it squirt. It's so funny, that little thing."