Why crossdress? Questions to ponder

Why Crossdress? Sami’s Week

As a crossdresser myself, I have had a number of questions about myself and others in the crossdressing community. The questions for others were more to satisfy my curiosity and to gain knowledge. Perhaps these are some of the same reasons why you read my blog. As for the questions I have for myself, they look into my motivations, reasons, and dreams. Why crossdress? I answer some of these questions in this post. Don’t you have some of the same questions for yourself?

Why Be Afraid of a Sandwich? Sami’s Week

As a crossdresser, I have overcome several of my fears. My biggest struggle is direct contact with strangers. I have no problem walking among people while dressed, driving, etc. What I do fear is one-on-one interaction. Overcoming crossdressing fear is one of my main goals of this year. This week a sandwich came to my rescue!

Sami's Week: Churchill & Overcoming Fear!

Overcoming Fear & Churchill: Sami’s Week

I didn’t know until Tuesday night that Winston Churchill, the leader of the United Kingdom during World War II, and I, a somewhat timid crossdresser, have something in common. That something is overcoming fear.

Quarterly Review

Limited Crossdressing Opportunities
Sami’s Week

For all of us crossdressers, we have our share of ups and downs on our crossdressing journey. The past few months were an up for me, but I’ve had a setback. I now have more limited crossdressing opportunities.

Quarterly Review

Crossdresser Shopping Trip with a New Friend
Sami’s Week

I got to do something last week that I never thought I could do in this rural part of America! No, it wasn’t tipping over a cow, nor was it waiting to pass a slow-moving tractor. No, my friends, it was better than that! I was going on a crossdresser shopping trip with a nearby crossdressing friend.