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.
Apr 24, 2026•13 min
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.
Apr 17, 2026•14 min
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.
Apr 14, 2026•11 min
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.
Apr 03, 2026•10 min
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.
Mar 27, 2026•12 min
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!
Mar 20, 2026•11 min
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.
Mar 13, 2026•9 min
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.
Mar 06, 2026•12 min
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.
Feb 27, 2026•13 min
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!
Feb 20, 2026•11 min
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!
Feb 13, 2026•20 min
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.
Feb 06, 2026•14 min
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.
Jan 30, 2026•12 min
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!
Jan 23, 2026•8 min
Many crossdressers find friends online to chat with, share experiences and interests and become "sisters" with. But is that enough? How to find sisterhood in real life and in your area is the topic of this episode.
Jan 16, 2026•9 min
In Japanese culture men who dress as women or transform into women have been very popular in manga and anime. Recently otokonoko or "men with a feminine appearance" or crossdressers have made a huge surge in popularity. I explain what otokonoko is and show a recent manga I found in this episode.
Jan 09, 2026•9 min
Sprained ankles from high heels, blisters from taping, telltale marks on earlobes from clip-on earrings - there are many injuries that you could get while you're dressed. How to avoid hurting yourself is the topic of this episode!
Jan 02, 2026•9 min
According to a report, if a man stares at a woman's boobs for 10 minutes a day or longer it can act as medicine and improve his health. In this episode I discuss if this could be true or not... and what side of the staring I prefer to be on.
Dec 26, 2025•7 min
The more I enjoy being Jennifer the more I think about things that I can do to improve my appearance or make me feel better about myself. Coincidentally, many of these thoughts are ones that women think about. In this episode I talk about how my feminine mindset influences my everyday life.
Dec 19, 2025•13 min
Many crossdressers are afraid to be their true selves and go out in public. But have you ever considered how courageous you are just by being a crossdresser? Confidence is something we all have but sometimes forget we do. Hear how you can use this to your benefit!
Dec 12, 2025•14 min
Sometimes it takes a long time to realize something that you knew all along. In this episode I talk about how years of messages and clues should have told me what I finally figured out about myself and now share with you.
Dec 05, 2025•24 min
As a crossdresser, we are more comfortable and connected to our feminine self. In this episode I talk about connecting with other women that way but as my male self. Having conversations with women, relating to their views and other topics are discussed.
Nov 28, 2025•11 min
If you get outed as a crossdresser to your employer whether by a coworker or by accident it can be an issue. In this episode I discuss the potential repercussions of someone finding out about your lifestyle and how it can affect your work.
Nov 21, 2025•14 min
As most of us know, crossdressing can range from wearing a particular item of women's clothing to completely dressing head-to-toe. What works best for you and what do you enjoy? I answer a listener question about what lane is right for you!
Nov 14, 2025•15 min
Halloween has come and gone and this year I got to enjoy it for a bit! In this episode hear about what I did while enjoying "Crossdresser's Christmas" for the first time.
Nov 07, 2025•11 min
A couple weeks ago my wife went on a trip, leaving me with a few Jennifer days. In this special episode on location find out what I did and how much I enjoyed having extended time out!
Oct 31, 2025•19 min
Politics are a touchy subject for most people. Even I normally keep my views to myself. In this episode I cover this area and express my views on the world today. PLEASE NOTE: If you are someone who is offended by people's political opinions please skip this episode.
Oct 24, 2025•14 min
Music does many things to us. It can spur memories, conjure feelings and even help you to fall into your feminine persona more easily. In this episode I discuss how music helps me to feel more feminine and how my music tastes change when I'm Jennifer!
Oct 17, 2025•10 min
Emotional support can come from all places - spouses, significant others, family members or friends. As a crossdresser it can be a challenge to get the emotional support you need to make you feel secure, loved and wanted. Here are some different ways I have found emotional support and what you can do to find the same.
Oct 10, 2025•11 min
Every crossdresser enjoys being out in public. But have you ever thought about what you would do if your car broke down? What if you had a medical emergency? In this episode I cover these scenarios and more about how to deal with emergencies.
Oct 03, 2025•13 min