My name is Steph. I am a 57 year old male who has now been dressing fem
since just before Halloween. It all started as silly play with me putting on her panties and she said it looked hot.  I began getting my own things and she continued to tell me it looked hot.  Soon I had a few outfits and we had decided to switch roles for Halloween.  The big night rolled around and I had been practicing. I think she was even shocked how well I looked, I know I was.  We went out and I felt I actually was passing as a female.  After Halloween I asked my girlfriend how she would feel if I did not want to stop dressing as a female.
She said it would require some adjustment, but that she loved who I am on the inside and the rest was just a shell. 

We now go shopping, out to eat and plan to golf together as two girls.  I have shared it with some of my closest friends, some of my customers and even a few people of authority in the community.  My sister knows but at this point chooses not to talk about it.  I think she is hopping it is a fad that will go away.
When I was young I experimented with a same sex relationship, which felt just completely wrong for me. I love women and know I am not a gay man. 

I do most of my shopping as a female and nobody knows unless I choose for them to know.  I do want to pass as a female to the public in general. Those who I share this with want to know why.  Because I feel free, as some have said. I am free to talk about feelings and free to cry if I choose. I am able to express myself in ways I never could.  I am an addict and an alcoholic. But clean for 10 years now.  I was in trouble many times when I was young.  I always felt like I was searching for something.  Today I am free of so many things that held me down. I wish I could share the feeling of freedom I have found.  People say they love how I smile now.  I love looking in the mirror.  What I do today hurts nobody, but does make for a better me.  A softer  more gentle form of the old me.  One who really cares about things that he was indifferent to in the past. I don’t care if the whole world knows. I am truely happy for the first time in my life.

Hugs and Kisses
Steph

I have a huge collection of clothes and underwear and I dress when its convenient to do so. Going out in a nice new outfit is an amazing feeling and I become a completely different person.

I think the reason I dress up is nothing more than a challenge to do it nicely and well.

Mens clothing is nothing short of boring and drab. Women’s clothes are exciting and beautiful. The range of styles and different fabrics are wonderful, and I just like the opportunity to wear such lovely things and create a beautiful woman. The kind of woman ”I myself” would like as a companion or partner.

By the way. Sex is furthest from my mind, and the horror of someone thinking or suggesting that I might be gay is my biggest fear. FOR ME IT IS AN ART FORM. NOTHING ELSE.