6 Best Dating And Relationship Tips For Crossdressers and Transgender Women

6 Best Dating And Relationship Tips For Crossdressers and Transgender Women

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6 Best Dating And Relationship Tips For Crossdressers and Transgender Women

Note from Lucille: This is a guest post by Leanne of Leseda, a MTF makeover service located in London, Ontario, Canada. 

While Leseda is no longer open for business, I wanted to leave this post up as it offers valuable advice on dating and relationships for crossdressers or transgender women.

Relationships are an important (and complex) topic, so I’m excited to bring you Leanne’s perspective. I’d love to hear your thoughts in the comments below!



Out Of The Closet: Dating And Relationship Tips for Crossdressers and Transgender Women

Dresses, skirts, lingerie and shoes – where do you put all the shoes?! It doesn’t take long for a closet to fill up. The more cluttered it gets, the harder it is to tell what’s there and what fits beautifully on you.

The same can be said for the metaphorical closet. The longer you keep yourself hidden, the harder it is to see who you really are. That is a great loss to yourself and to your partner. 

Hiding who you are takes a lot of energy that is better spent on keeping the sparkle in your relationship and enriching your experiences in life. It also causes a lot of stress and unnecessary strain on you and your relationships.

If you are concerned that your secret life will hurt someone you care about, or that they will think less of you, consider instead that they are missing the opportunity of knowing the truly beautiful person you are. You are actually robbing them of the opportunity to love you completely.

The exciting thing about being in love is wanting to know everything you can about the person who makes your heart sing. You want to know their private intimacies, how they think, what turns them on, their history and story that made them who they are. Why would they not want the same of you?

I encourage you to love yourself first. Loving who you are, without shame, loving the whole you, frees your spirit so you can grow to be all that you are meant to be. What a gift to give yourself! What a gift to give your partner!

There are far too many crossdressers and transgender women in the closet. I have heard enough stories about secrets, but I have also heard many stories of success. Secrets hurt and indicate shame. 

Being yourself is not shameful. It’s time to come out of the closet, clear the clutter and make room for more shoes!

Leanne’s Relationship Tips for Crossdressers and Transgender Women

Here are some tips from couples on how to incorporate your feminine side into a successful, loving relationship:

1. Start small

If you have a huge fantasy of being a woman, full time with your wife, but you haven’t told her yet, start small! 

Do little things to gradually work up to your goal. Start by painting each other’s toe nails for example. Baby steps, baby steps.

2. Tell her you love her

Assure her that you love her as well as yourself, and that you will be a better partner to her if you don’t have secrets. Let her know that she is still the love of your life.

3. Compromise

Don’t push your partner to go beyond what she is willing to do. This may take a lot of getting used to on her part, especially if you’ve been the same in the relationship for many years.

4. Make it fun

People continue to do things when they are having fun, so be playful and loving while she discovers this new side of you. 

Maybe she could dress up and be someone different as well while you are en femme. Private secrets between just the two of you can be very fun!

5. Find friends 

Join groups online, attend events or conferences that are non-sexual in nature so she can be assured that you aren’t deviating from your relationship with her.

Encourage her to seek out friends who are also in crossdressing / transgender relationships. Here are a couple helpful resources to start the search:

6. Get support

Seek a coach or mediator to guide you through this new phase of your relationship

About Leanne

Leanne, Transformation Maven of Lesada, located in London, Ontario Canada, is a coach and beauty consultant who specializes in empowering crossdressers and transgender women. 

Lesada offers full feminization services through makeovers, cosmetics & comportment lessons, wig & breast form fittings, style consulting, life and health coaching, shopping excursions and more! 

Leanne also coaches and supports couples who want to welcome crossdressing into their relationships. 

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