Back in the day, crossdressing used to be a hugely popular comedic act. Whether we’re talking about classic movies like Tootsie or throwaway man-in-a-dress gags in sitcoms, most of us got a laugh or two from the idea. What we also got, though, was the question why do men crossdress?
Now, society has come a long way since then. Traditionally gender-associated items such as clothing, makeup, and haircuts are commonly considered gender-neutral these days. However, despite those changes, crossdressers still exist.
Why? Because crossdressers tend to push the stereotype associated with the opposite gender to its limits. Whether we’re talking clothing, appearance, or mannerisms, they go all the way to the base. And — surprise, surprise — most crossdressers are men who put up extremely womanly personas.
So, why do men crossdress? What makes them put on extravagant dresses and striking makeup? Keep reading to find out!
Let’s start by cracking open a cold one — the impersonal, psychological angle. Namely, the reason why do men crossdress is to simply express and play around with their feminine side. In fact, you’ll find many men who normally present as very masculine, doing just that.
Given the practice’s mainstream roots in comedy, many men were often ashamed of being caught indulging in it. As such, countless crossdressers made it a private passtime and kept it at that. Recently, though, femboys and traps are all the rage, and more and more men are opening up about their crossdressing habits.
And to set things straight (pun intended), most crossdressing men are just that. After all, gay guys are often comfortable with their masculinity to the point of not seeing women’s clothing as taboo, demeaning, or arousing. The lion’s share of the appeal is lost to them — unless we’re talking drag queens.
After the detached, psychological angle, let’s turn up the heat.
A number of men are turned on by crossdressing. For them, getting dressed and pampered is a big (and sometimes necessary) part of sex. The bedside variant of crossdressing comes in two flavors, which we’ll cover below.
First off, we’ve got the classic paraphilia. In short, men who get into the mood by the act (or idea) of putting on women’s clothing and makeup are said to have paraphilia, and the centerpiece of that fetish is the clothing or makeup. It may sound strange if you’re not into it, but this is actually as basic as crossdressing gets.
The second (and absolutely huge at the moment) kind of crossdressing is forced feminization or sissification. The idea here is that the subject (the sissy) is made (or forced) to crossdress by a dominant partner. Femboys (crossdressing young men) have pushed this kink to the internet’s forefront, and it’s not going away anytime soon.
To start with, you should rid yourself of your preconceptions and taboos. You only live once, and you might as well enjoy what you like.
Next, what we suggest doing will heavily depend on whether you’re in it for emotional or sexual fulfilment.
In case of the former, you should try opening up to your friends and partner. There are plenty of stories of people whose partners and friends have accepted crossdresses the way they are — and even elevated their relationships in the process.
Now, if crossdressing arouses you, you’ll absolutely want to share it with your significant other (if you have one). Trust is a major part of sex, and few things are better shows of trust than indulging a so-called forbidden kink that no one else knows about. Most people want to please their partners, and you’ll both discover new depths of pleasure and attachment.
To summarize, crossdressing — as a form of expression or a kink — is now more mainstream than ever, and having sissification and femboys pop up in casual conversation has gotten pretty common.
That is why there’s no reason for you to be ashamed of your kink — if you have it — or keep asking yourself, why do men crossdress? If it feels good, you should do it, and be comfortable doing so!
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