Jennifer's Tale: My Life as a Crossdresser

Jennifer's Tale: My Life as a Crossdresser

If you're a crossdresser please join me as I journey through my life - my thoughts, feelings, experiences and more - as I try to figure out why I'm this way, why I'm okay with who I am and why I enjoy spending time as Jennifer!

Episodes

November 14, 2025 14 mins

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!

Mark as Played

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.

Mark as Played
October 31, 2025 19 mins

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!

Mark as Played
October 24, 2025 13 mins

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.

Mark as Played
October 17, 2025 10 mins

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!

Mark as Played
October 10, 2025 11 mins

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.

Mark as Played
October 3, 2025 13 mins

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.

Mark as Played
September 29, 2025 13 mins

If you spend any time out as your femme self, chances are at some point you'll need to "do your business." In this episode I discuss where, how and why it's okay for you to use the restroom while you're out in public!

Mark as Played
September 29, 2025 10 mins

Many crossdressers reach out to me asking how to find other girls in their area and how to connect with them. Thankfully it's a lot easier now to find friends and other CDs due to social media. Hear about how Facebook changed my life as Jennifer and how you can use it to help you!

Mark as Played
September 29, 2025 10 mins

We all know crossdressing is a way to express your feminine side. But does how you feel when you dress dictate your sexuality? In this episode I talk about whether or not being a crossdresser classifies you as being gay or bisexual.

Mark as Played
September 15, 2025 10 mins

For many crossdressers getting a smile, nod or compliment about their appearance is a wonderful thing. For others, having a man doing the complimenting means more. In this episode I talk about "male validation" or having a guy compliment how I look makes me feel and why it's something that I enjoy.

Mark as Played
September 11, 2025 12 mins

Many followers have complimented how genuine and authentic I am on my podcast. But how authentic can a crossdresser truly Be? From our outside appearance to how secretive we are about our dressing, it can be tough to be your true self. In this episode I tackle this big subject and try to dissect it a bit!

Mark as Played
September 8, 2025 13 mins

Since I became comfortable with being a crossdresser I have shared this side of myself with many friends and family. Most of the women I have told have been supportive of me, but there are several who have become closer friends because of it. In this episode I personally thank several girls who have gone above and beyond to make me feel loved and show you that you probably have the same type of people in your life.

Mark as Played
September 4, 2025 8 mins

Every crossdresser starts out be dressing within their four walls. But the urge to go outside is strong. In this episode I discuss how I began my journey to go out in public and how you can take "baby steps" on your way to a more fulfilling life.

Mark as Played
September 1, 2025 12 mins

Pride Month has come and gone for this year. It was great to see so many people out and proud, being themselves. But do some people take it a little too far in their appearance and flamboyant dress? In this episode I ask which is better for representing ourselves, being loud and proud or more subdued and everyday.

Mark as Played
August 28, 2025 13 mins

Everyone has regrets. In this episode I talk about some of my regrets I have regarding my crossdressing - from missed opportunities to dress more over the years to people I wish I would have come out to in the past.

Mark as Played
August 25, 2025 12 mins

If you're like me and have a wife or girlfriend, it can be really tough to discuss your crossdressing, feelings and thoughts with them. In this episode I talk to the wives and significant others out there and try to help you tell them how much you appreciate them.

Mark as Played
August 23, 2025 1 min

If you follow me on social media you may know that Jennifer's Tale is an audio and video podcast. The video feed (which can be found on Youtube) is a few episodes ahead of the audio feed so I'm going to give my audio listeners an extra episode every week until both feeds sink up! Thanks for listening and hope you enjoy!

Mark as Played
August 21, 2025 9 mins

Courage comes in all forms. Whether it's courage under fire, standing up to a bully or facing a fear of flying it takes something special to be courageous. But have you ever thought about how courageous it is to be a guy who dresses as a woman? In this episode I remind myself and you how courageous you are!

Mark as Played

I've discovered over the years that if you want to get someone talking, ask them about their kids (if they have any) or what they enjoy doing in their free time. I've shared a lot about myself during my podcast. This time around I talk about my hobbies and where my passions lie. Hopefully you will share yours with me!

Mark as Played

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