Sign up!

How to Deal With Life Changes on Your Crossdressing Journey

Sometimes life throws us a curveball.  It’s guaranteed that at some point in our lives, we all have to deal with surprises or big changes.  Sometimes anticipated and sometimes not.  It’s how we deal with these unexpected or vast changes that make us who we are.  I’ve dealt with several big life changes; breakups with partners, losing or changing jobs, and even moving halfway around the world.


How to Deal With Life Changes on Your Crossdressing Journey


This article isn’t about how to best deal with these changes, but how they can affect your crossdressing in attitude or practice.  After all, being a crossdresser is part of who we are, and despite changes happening in our lives, this part of us remains.


How to Deal With Life Changes on Your Crossdressing Journey hide


A breakup


How to Deal With Life Changes on Your Crossdressing Journey


Breaking up with a partner is tough.  It’s always tough, no matter the reason.  The pain and introspection that occurs around a breakup obviously depends on which party did the breaking.  Having been on both ends of this, I can tell you that either one isn’t easy.


As crossdressers, we are likely more in touch with our feminine or emotional side than the typical guy.  If we’ve felt dumped, there might be some anxiety. Something like why and whether or not being a crossdresser has something to do with it.  Obsessing the reasons for feeling dumped isn’t healthy, especially if you are worried that your dressing has had something to do with it.


How to Deal With Life Changes on Your Crossdressing Journey


From my experience and talking to other crossdressers, there seem to be 2 basic reactions.  Dressing a lot more or completing a purge.  The first one can be a reaction to whatever you’re feeling deep inside, and dressing up is a way to escape the pain.  Also, it can be liberating to dress how and when you like without worrying about being caught or judged.  I’ve heard some of my crossdressing friends express the such joy that they’ve been dumped and the euphoria of being able to be femme whenever they want.


Guilt over feeling dumped because of your crossdressing habit can also leave us depressed and questioning our dressing. Despair and depression can lead anyone to do irrational things. For crossdressers, that usually means a big purge and a vow to never come back.  This is also completely unproductive and unhealthy.  Any of us can tell you that once crossdressing becomes part of your life, it becomes part of who you are and is unlikely to ever disappear.  Taking a break to take stock and regroup is a good idea.  But throwing out dresses, lingerie, or what have you is a waste.  I cannot think of any other habit or hobby where someone would try to erase all aspects of it from their life if their wife or girlfriend left them.


 How to Deal With Life Changes on Your Crossdressing Journey


If you’ve lost a partner recently, I feel for you.  Try to use your dressing in a constructive way to distract or lessen the pain you’re feeling.  Spend some time improving your make up skills, learn a new look or style maybe.  The best idea is to resolve to find a new partner with whom you can be more open.


Lost your Job


How to Deal With Life Changes on Your Crossdressing Journey


Losing a job is a really traumatic thing that can happen to anyone.  Sometimes it’s not a just a loss of income, but a loss of identity.  This comes a massive jolt to anyone.  Depending on your age, level of experience and salary; the reaction to losing your job is different.  For most people of working age, the typical reaction of losing their job is to take some time off, engage a bit more with their hobbies and then begin to look for work.  As a crossdresser, this could mean more time to dress up and improve your skills.


 How to Deal With Life Changes on Your Crossdressing Journey


Losing your job nowadays is almost more of an opportunity than a burden. Post covid, the number of online or work-from-home vacancies has skyrocketed.  These jobs are obviously crossdresser friendly, as they allow us to work when and how we want, in the clothes we like.


Moving house


How to Deal With Life Changes on Your Crossdressing Journey


Moving isn’t a traumatic experience like the previous two, but it does present a bunch of unique challenges and opportunities for crossdressers.  Generally, I quite look forward to moving to new places every so often.  It’s a chance to start out somewhere with a clean slate and a new environment.  I’ve got some advice about the practicalities of moving, as well as some of the greater concerns in life.


I’ll start with the more abstract concerns.  Do some google searches about where you’re planning on moving to.  What’s the culture like?  If you’re planning on being open with your dressing, what is the attitude generally going to be like?  I’ve made the mistake before of moving to a place thinking that the atmosphere would be quite accepting, not realizing that I was going to a very traditional part of a more open-minded country.  Do your research, cause finding a community to be a part of is important.


How to Deal With Life Changes on Your Crossdressing Journey


Also, the practicalities of travelling and moving your femme supplies is something to think about.  Depending on how open you are about your crossdressing, you’re going to want to ensure that your stash isn’t discovered.  Anytime I’ve moved, I make sure to pack my girly things myself and I always know where they are in my bags.  I’m especially careful with my silicone supplies.  Clothes might be easily explained away, but a set of silicone D cup boobs isn’t.  Also, depending on how far and the method of transport, items like silicone breast forms or hip pads will set off red flags.  They will show up as suspicious items during a security scan.  I’ve looked on in fear as my breast forms showed up bright orange on the airport Xray machine.




Change is a part of life, and how we deal with change can tell us a lot about who we are.  As crossdressers, we can often look to being feminine or ‘abnormal’ as a justification for the bad things that could happen to us.  It’s likely that your crossdressing will be impacted by whatever changes are thrust upon us in our lives.  However, the important thing is to not feel flustered.  In many cases, being more in touch with our femininity will help us deal with difficult situations.

Tagged With: ,

Leave a Reply

Required fields are marked *

  +  83  =  92