How to Date as a Cross Dresser

Dating in the world of waist trainers, wigs and breasts forms is quite an experience. And well, classic dating is complicated enough as it is, so adding a bit of cross dressing to the mix, certainly adds on a bit of fun sprinkles to it wink*

The first thing you need to get in mind in order to date as a cross dressing person, is to really come to terms with yourself. This means you need to be 100% confident with this aspect of your life and personality. If you are still struggling with it, that is fine! Just take your time, spend some time on yourself, and when you are finally ready, go out and take a dip in the dating pool.

It doesn’t matter if you are a heterosexual cross dresser or a gay cross dresser, the most central aspect of the whole thing, is to be upfront and honest since the very beginning. Every single person in this world is special and has something to bring to the table, so you owe it to yourself and others to be very open and respectful.

It may be this is your favorite thing in the world or you may not be so keen on it, but nether less, and whether you like it or not, you will need to have the cross dressing conversation. And hey, I’m not saying you need to proclaim it to the world and everyone you meet (unless you want to!) but you will need to talk about it with potential romantic partners.

When you bring it up, it will probably be normal for the potential partner in question to ask some things… or even be really confused. And that is ok; there can be some misconception about this activity. That is why you will need to be open, don’t get offended and offer to answer any doubts this person may have. This whole process goes two ways! Is a learning experience for all of those involved.

Probably the biggest myth is that cross dressers are all gay, and this (as I’m sure you know) is simply not true. So you may want to start with that; take your time explaining your reasons and particularly how cross dressing plays a role in your life. Keep in mind basically everyone is different, so every individual has his or her own reasons, don’t be afraid to open up and set the table up for a discussion about the subject.

You partner will probably want to know a lot of things about you, your gender identity, your sexuality, etc. Try to address them as honestly as you can (and besides, this is a two way street, so you should expect the same thing in return) If there is something you are not sure about, just tell them you are still trying to figure it out…no shame in the constant learning process it is to learn about ourselves wink*

If cross dressing is something you enjoy doing and plays a big part in your life, it’s important to be upfront and honest since the start of the relationship. Nobody likes to feel like they were being lied to or even manipulated, so honesty is the best choice here. If you feel the relationship has potential, is definitely one of the very first things you should discuss; just like people who actively practice BDSM and have to disclose it early on in the relationship, this is no different. Don’t wait until you’re practically engaged to bring the subject!

Just approach the subject with confidence. Being confident in one self and one’s decisions is important to lead happy and healthy lives. Besides, this confidence shows! And there is something very attractive about it as well.

After your potential partner informs you they are comfortable with this, then the fun can really begin. And if they are not, it’s ok, there are plenty of sea in the fish and you just need to look a bit more to find the perfect one for you, kiss*