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 most 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.
(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 will often do so without letting him orgasm, makes it very clear who is in charge. And of course when she does allow him to cum, penetrated, it is supremely gratifying that this most unmistakable assertion of her ownership, the taking of 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 the pleasure he takes in pussy, 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 acknowledgement of his lack of a penis. He will want to tuck and tape his genitals and wear tight pants that show the flat front which 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 ecstacy.
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 associations, 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 mechanism that underlies 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 possesse 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.