Hello, Horny Readers! The title is deceptive, I suppose. This post is about more than just wigs. But wigs, as it turns out, are a means for Me to talk about crossdressing, and what it means.
More and more crossdressers have been coming to Me to confess, and for advice. Crossdressers are different than sissies, for among other reasons, that their affinity for crossdressing often isn’t related to a sexual kink. It can be. It can also be a means of gender exploration, or simply a means of self-care. That makes the guidance I will provide somewhat different than that which I would give to a sissy.
One of My more recent consultations involved wigs. Specifically, whether or not crossdressing necessitated wearing them.
Spoiler alert: I said no.
I thought I would share My reasons why.
I definitely encourage (if not demand) My sissies get themselves more feminine hair. Often that means at least one nice wig, because even If they have enough hair to grow and style, circumstances (professional, relationship, etc.) don’t allow it.
But why don’t I think crossdressing requires wigging?
Because the only requirements of crossdressing are those imposed by the crossdresser themselves.
Keep reading, and I’ll attempt to explain further.
Crossdressing and Sissyhood are Not the Same.
The best person to tell you what crossdressing means to them is the crossdresser themselves. Given that sissyhood is somewhat imposed on a submissive by a dominant as part of kink play, many of the decisions are made by the dominant.
In short, I give sissies rules and assignments. I give crossdressers suggestions and encouragement.
Sissies are submissive by nature, in addition to the trigger of feminization. Crossdressers, in My experience, don’t tend to be submissive, and do tend to acquire their affinity for feminization as part of a quest for something else.
Sissyhood has an element of humiliation to it, whether nurturing and sweet or hard-core and emasculating. The fact that a man crossdresses tells you little to nothing else about their sexual tastes.
Sissyhood is a kink identity. Crossdressing can be an activity, a gender exploration, a gender identity, or all three.
If a sissy comes to Me to be owned and trained, eventually I am going to demand that they feminize their hair as well as everything else. Ideally, they will completely discard everything that ever signified to them that they could count themselves among men, at least in session.
Crossdressers can, and do, experience self-directed feminization, and do so a la carte, depending on their motivations. Guided feminization might be something they undertake, but not from a submissive point of view.
Why Would a Crossdresser Wear a Wig?
I remark on this because the conversation that inspired this post contained the question, “well, should I?”
My reply was, “do you want to?”
My reply to those reading who may be interested in crossdressing is the same. If the answer is “yes”, then of course you should. That’s the beauty of it, crossdressing. You can and should express and explore your feminine side however you see fit.
If you are crossdressing because it’s an activity you enjoy, then why not?
If you are crossdressing because you are exploring your gender identity, then sure. Women don’t have to have long hair, but maybe the woman within you that you’re trying to unearth, does. Maybe you won’t see her until you see her hair.
If you are crossdressing because it arouses you, then try it and see if a wig makes you tingle.
If you are crossdressing because it’s an escape, a means of relaxation or comfort, then see how it makes you feel.
A question I asked during this conversation was, how high do you want to get?
Let’s return to the idea that, unlike sissies, for whom feminization is a form of degradation of their masculinity and a sexual kink, crossdressers don’t always, or even often, crossdress for the purposes of sexual gratification.
As I remarked before, for many, crossdressing is a vacation. A stress relief. A way to get even closer to something they already admire. A way to engage with the artistry of fashion, which for them is much more interesting on the traditionally female side of the rack.
Further, women’s garments and grooming rituals allow them to access parts of themselves it’s otherwise hard to do. For example, the behavior society approves of in women but discourages in men (softness, grace, sentimentality, vulnerability) might be easier for a man to allow himself while crossdressing.
Sleeping in a nightie may be enough to provide this stress release and comfort. Stockings and heels may be the key for another. For some crossdressing men, the more femme they appear when looking in the mirror, the more free they feel. Therefore, if all else is glamazon except for the sideburns or buzz cut, a quality wig may just shoot him straight up into the euphoric stratosphere.
Are you a crossdresser struggling for the key to your individual lock?
Maybe the answer is to bump your feminization up a notch. Feminizing can be like a drug, though a harmless one. For a while, a single garment may be enough. Then it’s hair removal. Then makeup. But they don’t call a woman’s hair her crowning glory throughout history and across cultures for no reason. If you’ve explored other things, or are loath to do so in the quest for your feminine side because of the restrictions of your male life and relationships, try something that you can put on and take off as the obligations of “real life” require–a good, silky wig.
I am available for confession, conversation, virtual window shopping, style consultation, and yes, wig consultations, too.
Crossdressers don’t form a large part of My callers, but perhaps that’s because they’re not sure where they fit in. They might feel even more secretive or scared of sharing their femme selves than those who pursue it in a sexual way. Gentlemen, gender-questioning, or gender neutral, if you’re reading this, you are more than welcome. Whether you want to wear a wig or not.
Goddess Rachel, Coiffeur of Crossdressers
Mistress Rachel, this is Sissy Slut Samantha. Thanks for this blog post. As you know, I am a sissy and a slut. I love to dress up in lingerie but I have limited interest in dresses and other feminine clothing other than lingerie. Wearing panties, garter belts and hose, corsets with garters, camisoles, and spike “fuck me” heels is very exciting for me and very helpful conveying to others my strong desire to be used as a fuck toy and whore. The “kink” factor is driven up when I dress like this to visit adult bookstores and porn theaters to be a slut and I walk from the car to the bookstore or theater in nothing but my lingerie and then either shop or watch porn while other patrons look me over. To horny men, the invitation is clear. Wearing a dress or something to cover up my lingerie would defeat the purpose. I do so only when absolutely necessary to move about in public. So, I am a good example of your dichotomy between cross dressers and sissies.
As for wigs, I often wear a short black wig with my lingerie simply because it adds to my streetwalker look and some men seem to like it. I use a short wig so that my “hair” does not interfere with my main activities.
When time permits, I really enjoy completing my lingerie, heels, and wig-supported femme presentation with makeup and nails done at a professional salon. The salon technicians have always been supportive, including when I make clear to them that I need my makeup to be heavy on the street walking whore look. It drives the guys wild.
Sissy Slut Samantha
Thanks for taking the time to reply to this post, Samantha! Of course I know all about your cock-seeking, sissy slut m.o., but I’m sure My readers will find it intriguing to read all about the “method” to your “cock-madness”. I like how you related your clothing choices, including your choice to wig or not to wig, in terms of how well it assists in your goal-oriented excursions. I’m sure it also has a helpful effect on your mindset too, getting you in the right frame of mind to show those stud cocks how much you long to please them.
Yes, Mistress Rachel. It is all about the cocks. I want to attract their attention, communicate clearly that they can have whatever they want, and then enhance the fuck service they get in every kinky way possible.
To drive home the point, when I don’t have the opportunity to “dress up”, I still go to the porn theater but I immediately strip down completely naked. Same reason. Make clear my submission, my desire to be used as a fucktoy, and enhance their experience in every kinky way possible.
But we are wandering a bit away from the topic of your blog post. That was not my intention. I do love your blog posts.
Sissy Slut Samantha
Thanks for reading, Samantha!
I have wigs Ms Rachel along with bras/panties/dresses/slips/leggings/yoga pants/blouses/makeup and lipstick. To have you dress turn and keep me as your sissy girl with lipstick kisses on my cheeks would be great!!!
Awww, good for you, Carli!
I wig but nowadays . I just stay home with no place to go Poo poo pandemic
Better safe than sorry, April!