Jennifer's Tale: My Life as a Crossdresser

Back in the pre-internet days it was difficult to shop for women's things when you were a crossdresser. Today with online shopping it's easier than ever but can still be tough if you have to do it in secret. Here are some tips that may help you in this area.

Most of the time I've used messaging or an email to reveal my crossdressing to my friends and family. Recently the opportunity came up to share Jennifer with a friend of mine in person. Hear how it went in this episode!

Does being a crossdresser offend God? This is what someone proposed to me recently. "A man is a man and a woman is a woman as God intended." Everyone has their thoughts on religion and how crossdressing fit together. Here is my view on this subject.

Sometimes it takes a while to both be honest with yourself and also be at peace with who you are. After a lifetime of soul searching I'm finally happy with the person that I am. Hear about how I'm no longer afraid to be me in this new episode.

Facebook likes to show your memories from the past. Recently I had an important one pop up from my journey. Hear how this memory caused me to reflect on my past and see how it influenced my future in this episode.

Everyone seems to have an opinion on this topic and it's time for me to chime in. Should crossdressers be allowed to use the women's restroom? I share my thoughts in this episode.

Time for me to ask you, the viewers and listeners, a question? I want to know what you enjoy doing when you're dressed. Do you like going out by yourself? Are you a party girl hanging out with your friends? Or are you content just to dress at home? Everyone is different. Hear what I enjoy most about dressing and let me know yours!

I had a Facebook post go viral and got numerous mean, vicious and hateful comments. In this episode I share some of these comments not so you can see how cruel some people can be but also hear about the friends and strangers that came to my defense.

Time marches on for all of us. I remember how easy it used to be to walk in high heels and how much younger I looked years ago. Getting older is something that we all have to deal with and how we approach it makes a big difference for ladies like us. Hear my thought on the topic in this episode!

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!

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.

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.

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!

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.

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.

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!

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.

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.

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.

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!

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.

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!

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.

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!

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.

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.