Jennifer's Tale: My Life as a Crossdresser

Due to a Facebook post on mine going viral I've received a lot of negative comments from random people lately. This episode is for all the naysayers and people who may try and suppress the positivity, happiness and joy I bring to the table as a crossdresser making my way through life and connecting with others.

A friend of mine had a relationship end because both parties reached a point where compromise threatened both people's wellbeing. Likewise, compromise can turn into conflict between both people as they try to navigate things. In this episode I discuss how compromise can turn into conflict.

June is Pride Month for the LGBTQ community. It may be the end of the month but let's take time to celebrate our wonderful friends and family and what makes us special!

My wife accused me of living in a fantasy world and to a degree she is correct. In this episode I discuss why crossdressing can be thought of as living in a fantasy world and why for some people it's an escape from real life.

One of the hazards of being a crossdresser on social media is the possibility of someone you know finding out. That happened to me recently with someone from my past. Hear how I dealt with it and what you can do if it happens to you.

As I've done my podcast I'm proud to say I've developed a trust with my viewers and listeners as I share aspects of my life with you. Hear about how this came back to me recently in this episode.

Sometimes whatever can go wrong will go wrong. In this episode hear how my usual plans for a Jennifer morning go astray and what happens by the end of it. Do I have a good day or bad?

In today's world AI-generated art is getting more and more prevalent. For many crossdressers using AI pictures and videos is an easy way to represent who they wish they were or desire to be. Here is where I stand on this hot topic.

Life can be compared to many things - a marathon, a race, a game et. For many life is like a poker game and you have to play with the hand you're dealt. In this episode (and thanks to my friend Michelle) I discuss how this saying affects myself and perhaps you.

My wife knows about my crossdressing but prefers not to know where I go or what I do. However, there are hints and questions she says that makes me wonder. What secrets do you keep and what do you reveal?

Many crossdressers have a tough time learning how to do makeup. While it's not an easy feat, it can be a lot simpler than most girls think. In this episode I share some of my secrets for making your makeup routine a simple, streamlined process.

There are times when life can be bad. Really bad. When times take a turn for the worst sometimes you need a reminder or a blessing to show you how lucky you are. Here's an example of how that happened to me along with a lesson everyone can benefit from.

For my 150th episode, listener Julie Shaw asked me a doozie of a question! What has been my biggest challenge as a crossdresser? Find out my answer in this anniversary episode.

The term "two-spirit" is something I found out about relatively recently. As a crossdresser you may find this idea fits you like I think it does me. Learn more about it in this episode.

You just got a brand new dress that looks stunning and want to wear it right immediately. The thrift store waits for no one. Wait, what? There's a time and place for everything and in this episode I discuss how important this is to fitting in.

The Hooters restaurant at the Mall of America is closing which caused me to make a pilgrimage to visit it one last time. What happened when I got there? Find out in this episode.

We all have lots of various interests and things that we enjoy doing. It could be a sport, a hobby or an activity. What if you could combine one of your interests with your crossdressing? I did just that not too long ago!

For the majority of us, pantyhose are a staple of our feminine wardrobe. In this episode I discuss recent brands that I have tried, which ones I like and how wearing pantyhose still makes me feel wonderful.

Crossdresser, trans individual, bisexual, gay - all these are labels that we tend to put on people to differentiate them in our society. But do we really need to? Here is my opinion about what labels are and how they affect us as a group.

Recently I made a trip to the Mall of America. Although my goal of getting a bra fitting fell a little short what happened instead made my day! Hear all about it in this episode.

Even though you may be a girl who has dressed for years there are always new challenges to face. In this episode I talk about doing something I have never done before - attend a Doctor Who convention as Jennifer where people know me as my male self!

I sometimes get questions from other girls that I enjoy answering on my podcast. However I realized that I also get questions from men as well. In this episode I asked men to send in their questions for me to answer and here are the results!

I have always felt that the trans community is a huge umbrella that covers a lot of people. However, some trans women feel that crossdressers are not included in this term. Some trans women feel that crossdressers are disrespectful to them. I discuss whether or not I feel I am disrespectful to this community.

It's a question that all crossdressers - myself included - ask themselves. In this episode I discuss my thoughts on HRT and whether it's in Jennifer's future or not and how this discussion may help you as well.

Women have an advantage when it comes to safety while out in public - they have had years of practice and education to protect themselves from unwanted advances, predators, unkind comments and more. For crossdressers we haven't had the time to learn how to be safe. Things to remember when you're out as your femme self is what is covered here!