It can be a huge issue for many of us to give into crossdressing while we are away from home and family on business trips. This has not been an issue for me as I don’t travel alone but am usually with other pastors. For me, it was a bigger problem to be home alone with my computer. But if you travel a lot you need to be prepared, know your limitations, and take whatever steps are necessary so that you do not go off and buy women’s clothing, or take a secret stash with you, or fail on your computer in a hotel. I know from talking to many of you men that it brings great temptation to crossdress and revert to old habits when you are alone at a hotel away from home.
Notify your accountability partner before you even leave on the trip. Don’t wait until the last minute to tell him or your excitement at planning to sin will prevent you from calling him. Tell him a week in advance. Then arrange times with him to periodically call you to check up what you are doing.
Plan for yourself some other fun things to do while you are away. Maybe bring some good movies with you. Make sure you pack your favorite novel. Have your favorite computer game installed, and maybe even plan a multiplayer session with a friend while you are at the hotel in the evening. Or intentionally spend time with other men who are with you on the business trip in the evenings. Get to know them, and share about your faith with them.
It’s also a good idea to make sure to talk to your wife each day by phone and email. Just hearing her voice will hopefully make you think twice about failing. Tell her you love her, and think about the wonderful reunion you will have with her when you get back home (after not failing). And remind yourself of how crappy and awkward it would feel to go home and reunite after failing.
It might be advisable to leave the cash at home and only take credit cards with you, especially credit cards that your wife has access to online so you would not be able to hide any purchases.
If you know you are going to be tempted to shop, then maybe consider purposely having fun shopping for men’s clothing for yourself. Enjoy looking good as a man. Treat yourself to something nice.
Take life seriously. You don’t want to fail and give in. Be prepared for trips.