Underdressed In Public For The First Time

I'm 41 year old who is just beginning to understand and enjoy crossdressing. I have been wearing my wife's clothes at every opportunity for a few years but this week I bought a pair of panties that are my very own. They are a cute pair of black nylon lace thongs with a little rhinestone heart on them and they are so cute, I LOVE them.

I had to do some Christmas shopping today and I had been wearing my new panties and one of my wife's bras (stuffed to fill it out a bit) around the house. As I got ready to leave I couldn't bear the thought of leaving the bra behind. In a last minute decision I left the bra on (stuffed and all) and headed out to do my shopping. I pulled on a shirt and blazer and headed out.

I'm sure that no one could tell through the blazer what I was wearing but I felt so conspicuous walking the isles with my bra strap slipping and the thong ridding my a** crack. It was wonderful.

I wish I had the money and talent to go out in full femme gear and pass.

Still, today was a fantastic day.
Rosso70 Rosso70
41-45, T
3 Responses Dec 5, 2012

I look forward to the day when I will just say fuckit and do what did in a similiar fashion. Each experience I read I become more emboldened hoping soon I will take that first step. Thanks for sharing, there is something about a thong that makes this man feel very sexy

Good for you the first couple of times I was so self conscious also. You should do it again and it will get easier

Thanks cdralph. I appreciate the comments and the advice. To be honest I don't know what will happen but I don't feel like my wife would accept it under any circumstances right now. So I feel like I'm torn between not getting caught and/or ruining my marriage. As far as the assumptions go I don't fully know where I stand, which doesn't help at all. I wish I could transform myself into a woman to the point that I could pass any test but a ***** search. I wish I had been/could become a woman. As to whether or not I'm gay I just can't say; I have experimented with men and enjoyed it, but I'm not attracted to men. You might say the thing that best describes me is a lesbian trapped in a mans body. : ).