I’ve always been interested in cross-dress but never tried it I’m afraid, not sure why and I don’t think it was out of fear, but in recent years my anxiety issues have really been debilitating at times and it’s effecting my quality of life. Im sure there’s still some stigma to cross-dressing and I want to be respectable to people who cross-dress so Im wondering if you know if this can be a way to manage stress and anxiety? And if it is what do you recommend for the “novice”? Oh and I’m on a tight budget atm 😦 is some sort of under garment appropriate or is that a waist of time. Very interested in makeup as well!
I am not a therapist, but I would encourage you to seek out counseling when it comes to managing your stress and anxiety. Your mental health is at the root of everything in your life and it must be a priority, especially these days. I know that my medication and therapy has improved my life a zillion percent and I would recommend you consider it. Before I learned how to live with my anxiety and treat it I was a wreck (almost) all the time. It impacted my work, my family, even relaxing. It was horrible.
There’s always always always always always always going to be a stigma when it comes to going this side of us. It will never be okay. Society is never ever going to say “hey, it’s okay to crossdress” so stop waiting for that moment. No one is going to give you permission and you don’t need it.
As for you being a novice, we were all novices at one time. You may find this helpful. When it comes to crossdressing it all comes down to what you want to wear. Panties? Nail polish? Stockings? A nightgown? Stilettos? Crossdressing is anything that is outside of the societal norms of the gender binary.
While it is true that crossdressing takes time, money, and patience, you don’t have to go broke when it comes to starting out. True, a really good wig can cost hundreds of dollars and a pair of heels can get pricey, but you can get a pair of panties for just a few dollars at Target.
Makeup is something you learn by doing. Start off with some inexpensive makeup and learn about technique, your colors, what works, what doesn’t, how to blend, how to apply that perfect cupid’s bow… If you want to crossdress, you need to be ready to commit to it. This is an investment of time and money. As much as I would like it to be true, there is no fairy godmother who will drop by and transform us into the princess many of us long to be. Watching makeup tutorials on Youtube is about as free as it gets, so perhaps start there.
Love, Hannah
Have a question for me? Oh yes you do. Ask me here!
Hannah McKnight 
Good and comprehensive answer, Hannah. Sue x
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good for you. you are a force for good in the world, evident in your kindness and honest straight talk to this sincere novice.
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love your answer. althoug true it is hard to understand ” It will never be okay. Society is never ever going to say “hey, it’s okay to crossdress” so stop waiting for that moment. “
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Hannah, much of your answer is true. You state that crossdressing is expensive. It doesn’t have to be. It’s no different than drab dressing … it all depends on the look you go for and where you want (need) to go to feel good about yourself. You can get wonderful women’s outfits at thrift stores for very modest prices. In the end, my advice, wear what makes you feel good and safe. If it’s just panties and a bra … Great! If it’s formal ball gowns you may need to be a bit selective where you go. And counselling is definitely a good investment in yourself.
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Thank Hannah and thank you all for your replies. It all made a lot of sense. I should of been more clear I have and do counselling and I do have a psychiatrist and I do take medication for my anxiety but maybe I need to try a different type of therapy. Been researching this a lot and think this might be outlet of expression I have been looking for. Sender of the original questions for Hannah Knight.
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