For most of us who crossdressed in the past, there was some conditioning going on. We desired to crossdress, but the more we engaged in it, the more we desired it. We got some sexual pleasure from crossdressing at first, but the more we crossdressed, the more pleasure we got. We conditioned our bodies to be used to it. We trained our bodies to respond to the stimuli in a certain way. My friend, Ikthys, has a wonderfully helpful post about it that you can read – “Conditioning.” He describes the conditioning process really well, so I won’t spend time on that, because you should read what he wrote.

What I’d like to talk about is trying to undo the conditioning in our attempt to fight against our crossdressing addictions or desires. There are many ways one could tried to uncondition the feelings and pleasures that we have learned to associate and experience with crossdressing. We could do so through punishments, rewards, through working on our thought processes, and I’m sure there are many other ways. I think there is a place for these self-treatments.

But what I want to briefly comment on is one idea of unconditioning that in my opinion is dangerous and counterproductive. This is the idea of purposely still engaging in crossdressing but refusing to give in to masturbation. The theory behind this would be to disassociate crossdressing from sexual pleasure and therefore diminish the desires to crossdress as a whole. When I was younger, I tried doing this. But ultimately those endeavors ended in failure. I would rationalize that I was crossdressing in order to try this type of unconditioning, so that ultimately I could stop crossdressing. Really I knew that it was wrong and unhealthy for me, but I clearly suppressed those thoughts. Since I was trying to disconnect crossdressing from sexual pleasure I would crossdress and then try to do normal work, daily activities, or video games. The plan was to not let myself look in the mirror or masturbate. But let me tell you, you can still have sexual pleasure without masturbating, and I did every time. In fact, because I was holding off on the masturbation, I ended up crossdressing for even longer periods and having even more pleasure. And then I would get to a breaking point and masturbate by the end of the session anyway.

So what was supposedly a way to fight crossdressing turned into something that poured gasoline on my addiction. It was extremely pleasurable. Please don’t give in to the same rationalizations that I did. This is not how to approach unconditioning. I’d also like to add that even if you somehow disassociated your crossdressing from sexual pleasure, it could still just as easily remain or turn into an addiction not based on sexual pleasure, and that can still be just as sinful and problematic as the sexual addiction. There are plenty of men crossdressing out there that are addicted to crossdressing, even though it is not based on sexual pleasure and masturbation. And there are plenty of men who started out crossdressing as a sexual addiction, and now the sexual component seems to be gone but they are still addicted to crossdressing.

As I’ve written about before, the important thing is to resist the temptations, not to eliminate the temptations. Sure, it’s good to work on ways to lessen the temptations, and work on ways to uncondition ourselves to crossdressing, but overall the most important thing is to resist the temptations. So I would highly suggest quitting crossdressing cold-turkey, completely. Doing so will lessen the strength of crossdressing, and the temptation to crossdress, slowly month by month year by year. And if you are having sex with your spouse, your body will be learning to associate sexual pleasure with your spouse more and more, and less and less with crossdressing. This is the best approach to unconditioning.

At times many years ago I also experimented with rewards and punishments, given to myself. This was done through guidance and discussion with accountability partners. It can be as simple as going without video games each time you fail, or getting a gift certificate to your favorite restaurant after three months of no failures. These techniques are not a dramatic solution to addiction, but they don’t hurt either. They can be a little piece of the unconditioning process.

I can testify that unconditioning will happen as a passive process over the years if you continue to resist crossdressing and stop giving in. But the unconditioning process may never be complete. Such a strong history of sexual pleasure connected to one activity is hard to undo. We might have periodic sexual desire for crossdressing until we die. Yet we should not be without hope. Just because unconditioning will not happen perfectly and completely, it does not entail that there will be no change at all. Porn addicts have to go through the same process of unconditioning their mind and body to porn. It’s a tough process because our brains have already wired themselves to our addictions, but our brains can also change again as we recover from addiction. Many have testified to this!

Don’t take my word for it. Read more about brain studies here – Your Brain on Porn Relevant Research and Your Brain on Porn Rebooting Basics

And read these amazing testimonies of people who have experienced change in their conditioning, leaning to desire porn less, and their wives instead – Rebooting Accounts