What can a crossdresser do when you don't have an opportunity to fully express yourself? Underdressing, or wearing women's clothing under your regular male clothes, is an option many use. In this episode I talk about underdressing, the pros and cons and how it's a viable option for many people.

As a crossdresser figuring myself out in the early 1990s, there were many talk show episodes that featured crossdressers and female impersonators. In this episode, I talk about three women from this era who helped me to feel better about myself as Jennifer and made me more confident in who I am now.

One of the most important parts of being a crossdresser - and sometimes the hardest - is having confidence. Whether it be confidence in how you look or faith in yourself to be out in public, being confident helps any crossdresser not only enjoy your time out but also will help you feel better about who you are. Learn all about it in this episode!

In having a conversation with a family member I was reminded of my childhood. Certain aspects and memories could be looked at as possible causes of my crossdressing. Is dressing like a woman inherent to some girls? Are some girls created? Or can both circumstances hold true?

Ever since Episode 15, many people have asked questions about my cleavage and my boobs. In this episode, I answer questions about my chest and talk more about what having boobs means to me.

It's my first episode on location! During one of my ventures out as Jennifer, I talk about summoning up the courage and confidence to leave your four walls and go out in public.

In 2020 covid caused many of us to change our lifestyles. For me, it caused me to reconsider my crossdressing and how I felt about myself. In this episode, I talk about how covid brought Jennifer out in a new way and helped me to look at myself in a new light.

If you have kids, you know that sometimes they are too smart for their own good. My own kids have been overly observant as my crossdressing has gone on and there have been times when my secret was noticed. How would you deal with your kids noticing clues to your feminine self? Here are some ideas of my own.

Many crossdressers find doing their makeup to be a challenge. Starting out, it can be hard knowing what to do to make yourself look like a woman. In this episode, I go through my process for doing my makeup and offer some tips and tricks.

As a crossdresser most girls have real life obstacles that prevent them from dressing as often as they would like. Whether it be family, work, neighbors or time the opportunities aren't always there. In this episode I talk about what obstacles I face in dressing as Jennifer as well as things you can do to help make it through the rough times.