Jennifer's Tale: My Life as a Crossdresser

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.

Summertime means warm weather and as a crossdresser I've learned that heat, makeup and padding don't mix well. In this episode I talk about how I cope with summer heat as Jennifer, what I do to enjoy my time outside and how to beat the heat!

Over the years women are expected to be smaller, thin and petite. Most crossdressers - myself included - have a body type that doesn't fit that mold. In this episode I talk about how I feel about my body size, what I do to try and fit into the world as a larger woman and what you can do to feel better about yourself.

If you're a crossdresser chances at least once in your life you vowed to stop and have purged your wardrobe. Hear about the times I have done it and the reasons why, as well as what to do if you decide to purge to help save yourself lots of money!

Fancy dress vs casual? Revealing vs everyday? From day to day my mood tends to determine what I want to wear as Jennifer. In this episode I talk about the reasons why I dress like I do as well as why sometimes casual is better than sexy.