New to Crossdressing? A Beginners Guide to Exploring Crossdressing and What I Would Buy.

New to Crossdressing? Start Here

Last week I had a wonderful session with a client that has visited me a few times for sissy training and he wants to cross-dress at home but he hasn't a clue where to start or what it all means. After the session, I sent him some links to items that I would buy if I was starting out today and I decided to turn it into a blog post for those that are new to crossdressing.

If you're reading this because you've recently started crossdressing, or you're thinking about trying it for the first time, there's a good chance you're experiencing a mixture of feelings.

You might be excited or you may be a mixture of curious, nervous, turned on, confused. embarrassed and or relieved. You might even be asking yourself questions that feel much bigger than the clothes themselves.

What does this say about me? Am I gay? Am I transgender? Is this just a fantasy? Why do I enjoy it so much? Should I tell someone?

First of all, take a breath. You don't have to have all the answers. You're not weird

One of the first things I would want anyone starting to cross-dress to understand is that enjoying clothing traditionally associated with another gender doesn't make you weird, broken or somehow less of a man. Some of the most masculine men I know cross-dress.

In fact, when I first starting dating, I met a solider online when he was out of the country. We chatted for weeks and when he came home he visited my apartment in Ancoats in his full uniform... I honestly thought it was Christmas. What I didn't know and what he failed to tell me before hand was that under his solider attire he was wearing full red lingerie, basque and stockings... the rest if the story can wait for another post.

There can be an enormous amount of shame surrounding crossdressing, particularly when you've spent years believing that men are supposed to behave, dress and express themselves in a particular way.

I want to make one thing very clear from the start if this conversation. Cross-dressing doesn't automatically tell you your sexual orientation or your gender identity. A man who enjoys wearing women's clothing isn't automatically gay. He isn't automatically bisexual.

And he isn't automatically transgender. For some people, crossdressing is simply an enjoyable form of self-expression. For others, it may be connected to sexuality, fantasy, relaxation, confidence or a desire to explore a different side of themselves.

You don't have to choose a label just because you've discovered something new about yourself.

You can simply say:

"I enjoy this."

And, for now, let that be enough. Give yourself permission to explore. If you're just beginning, you don't have to suddenly transform yourself into somebody else.

Start Wherever Feels Comfortable.

It might be something as simple as wearing underwear that you wouldn't normally wear. It might be trying on a dress in private, experimenting with makeup, buying a wig or simply looking at yourself differently in the mirror.

There is no correct starting point and there is certainly no requirement to keep going.

You are allowed to explore something and decide that it's not for you.

You are also allowed to discover that you absolutely love it.

The important thing is that the decision comes from curiosity rather than pressure.

Don't be frightened by your emotions. Something that can catch people by surprise is just how emotional the experience can be.

• You might feel incredibly excited the first time you put on an outfit.

• You might feel liberated.

• You might feel more confident.

• You might experience sexual arousal.

And afterwards, you might suddenly feel embarrassed or guilty.

That emotional swing can be confusing.

"Why did I feel so good five minutes ago and now I feel terrible?"

Try not to judge yourself too harshly.

When something has been hidden from us or when we've been taught that something is unacceptable, our emotions don't always behave logically.

Feeling guilty doesn't necessarily mean you've done something wrong. Sometimes it simply means you've spent a long time believing that you shouldn't be doing it.

Be careful about letting the internet define you. The internet can be both incredibly useful and incredibly confusing. When you first discover crossdressing, you may search for photographs, stories, forums, videos or pornography and suddenly you are presented with thousands of other people's experiences.

Questions That May Come Up

"People will think I'm weird."

"What kind of man does this?"

"I shouldn't enjoy this."

Those thoughts can become incredibly powerful when repeated for years but authenticity isn't about fitting yourself neatly into somebody else's expectations.

It's about becoming comfortable enough with yourself to acknowledge what is actually true for you and perhaps that's the most important thing I can say to anyone beginning this journey:

You don't have to hate a part of yourself simply because you don't understand it yet.

What I Would Buy... If I Was Starting To Cross-Dress Today

Firstly, I personally think it has never been easier to explore cross-dressing as Amazon deliver everything to a private locker where you can pick it up without fear of sales assistants or judgemental staff. Here are some of my fave finds on Amazon:

Stockings

Tights/Pantyhose

Mini Skirt

High Heels

Bra

Panties

Suspenders

Wigs

Sheer Bodysuit

Now when it comes to sizes, you are going to have to see where you are at personally.

Final Thought

If you're at the very beginning of exploring crossdressing, you may be looking for somebody to tell you exactly what you are. I can't do that and neither can anyone else.

Only you can discover that. What I can tell you is that you don't need to be frightened by your own curiosity. You don't need to have a label and you don't need to know what happens next. You certainly don't need to feel ashamed for discovering that there is a part of you that enjoys something you never expected. You don't have to figure yourself out before you give yourself permission to explore. Sometimes authenticity begins with something as simple as standing in front of a mirror and finally allowing yourself to say:

"This is something I enjoy. And that's okay.”

About The Author

Sasha Paige is a trans escort with years of experience supporting clients from all walks of life. Through first hand experience, she shares practical advice to help people approach booking an escort with confidence, respect, and realistic expectations.

A note from Sasha: My blog articles are for general information and reflection and aren't a substitute for professional medical, psychological or relationship advice.