Recently I listened to this free sermon online by Pastor Tim Keller. It was a powerful message for any Christian, but for me when thinking about crossdressing it was especially insightful. I highly recommend it – Spiritual Warfare by Tim Keller. If the links do not go right to the sermons, just search their site for “spiritual warfare.”

While I would never say that Satan is the cause of crossdressing in all of us, I would say that at the very least Satan exploits these crossdressing natures/desires in us, and tries to use them to bring us down. We are in a war. We have an enemy. Thankfully our God is infinitely greater and more powerful and is with us and gives us power against Satan’s schemes. But we need to realize what Satan is up to.

Tim Keller brings up several devices Satan uses, that he in turn got from another book. I listed several of the devices that Tim Keller mentioned and I want to examine them in light of our temptations to crossdress. In doing so, we can see the ways Satan is trying to mess with us, and we can be more resistant and overcome temptation.

Keller divides the devices into two types – Temptation and Accusation.



1.  Satan shows you the bait but hides the hook.   How often I’ve been tempted to crossdress or read crossdressing fiction and all I seem to be thinking about it is how pleasurable it will be in that moment. But I forget how awful I will feel afterward, how confused it will make me feel in regards to my gender, how guilty I will feel, how I will get addicted, how much it will mess up my marriage, and how it will distance me from feeling close to God’s presence. And there are other more disastrous consequences my friends have gone through because of crossdressing – losing jobs, losing marriages, alienation from children, etc.

2.  Satan tries to get us to rationalize sin as virtue.   How often we crossdressers have ignored the addictive and distorted and deceptive nature of crossdressing by trying to say, “oh but it’s good for me to be a balanced person showing my feminine side” or “But my wife can better relate to me when I’m crossdressed (because I can’t have real feelings when not pretending to be a woman).”

3.  Satan shows us the sins of Christian leaders.   We regularly see pastors or famous Christians struggling with adultery or pornography or materialism. In comparison, we don’t feel so bad about our crossdressing. If they can do what’s even worse, we can dabble in crossdressing.

4.  Satan tries to get us to over-stress the mercy of God.   This is the one that has got me the most. I have a very good sense of God’s grace and it fills my life daily with joy and gratitude. However, in the moment of temptation, sometimes I use God’s grace and forgiveness as an excuse to give in to sin. But just because God won’t punish me for my sin, does not mean I should give in to it. As the apostle Paul said, do we sin more so that grace will increase? By no means! God’s grace should fuel our desire for gracious obedience, not become an excuse to sin.

5.  Satan tries to make us bitter about our suffering.  In counseling other men struggling with crossdressing, I’ve seen this one many times. So many crossdressers have gone through awful life experiences, divorce, alienation from children, drug addictions, job losses, financial struggles, and many other very difficult issues. Often the despair and the suffering drives these men to rationalize their crossdressing. “I’ve suffered, so I deserve this fleeting pleasure.” Or “life is so hard and difficult, what’s the point? I might as well crossdress.” Instead of turning to God for comfort in suffering, we get confused and turn to fabrics.

6.  Satan shows us how many non-Christians seem to be having great lives.  If we judged crossdressing by the faces that we see on many crossdressing blogs and websites, we might imagine that most non-Christians crossdressers who are embracing crossdressing and not trying to resist it, are all having wonderful lives full of happiness and pleasure. But even if this was true, it doesn’t rationalize sin and addiction. And I don’t think it is true. Just browse the forums about crossdressing to see how much angst and confusion crossdressing causes in crossdressers’ lives. The 200 people every day who find my blog through searches about the destruction crossdressing causes are not a figment of my imagination.

7.  Satan tries to get us to compare one part of our life to another. I’m such a good person in other ways so its okay that I do this one sin.  Keller makes the joke, but serious joke, that mafia hit men rationalize their murdering of people because at least they love their mothers. It’s a strong point. How many of us have argued that in general we are good people, who love our families, work at our jobs, serve in our churches, so really what’s the big deal if we allow one little sin like crossdressing in our private lives?


Satan accuses us (lying to us), making us feel either a lower view of God’s love than we should, or a lower view of God’s holiness than we should.

1.  Satan wants us to look more at our sin than at our Savior.  He wants us to dwell on our past sins and condemn ourselves. I have talked to many crossdressers who cannot imagine how God could still love them or forgive them. And in their despair, they continue to crossdress. But it is not our own righteousness that causes God to love us or forgive us. In Jesus we can be completely forgiven and saved, and so we can live in joy and grace and obedience without despair.

2.  Satan wants us to obsess over past sins that have done damage that can’t be undone.   My crossdressing history has hurt people. I have done some terrible things I’m ashamed of. But Satan is the one who wants me to dwell on the past to keep me stuck there. In Jesus, I am forgiven, and I am a New Creation. I live for the future everlasting joyful life with him. I leave my sin behind me, and push forward towards the goal.

3.  Satan wants us to think that the troubles we are going through must be punishments from God. Satan wants us to ignore the fact that Jesus died to take our punishment. If we look at our suffering now and view it as God punishing us, then we won’t run to God for comfort and help and provision and peace.

4.  Satan wants us to think that our inner struggles can’t possibly be something a true Christian would have.  I used to feel this way myself. With these crossdressing desires and addiction, could I really be a Christian? Am I alone in this? I have found that I am far from alone and that all Christians have deep struggles that they don’t talk about every day! True Christians face temptations of all kinds. But there is victory in Jesus. We don’t have to be afraid.

If we are going to resist Satan’s schemes, we need to be aware of them and understand them.  Please give this sermon a listen.