Jennifer's Tale: My Life as a Crossdresser

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.

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!

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!

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.

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.

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!

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.

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.

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.

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.

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.

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!

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!

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!

Sometimes putting words down on paper helps. Whether its a post-it of encouragement to yourself, a note to a friend thanking them for being there for you or a letter to a loved one who has passed on telling them about your feminine side being able to express yourself does wonders. In this episode I talk about letter writing!

Summer is here and while there are benefits of vacation and other things, having your kids home for three months can cut into crossdressing time. What can you do to get some time for your femme self? The title to this episode says it all!

It's a feeling every crossdresser has - being ashamed of who they are and why they have the desire to wear women's clothing. Coping with this can range from guilt to purging. In this episode I discuss how I've dealt with shame and why you shouldn't be afraid of who you are.

Some trans girls don't feel that crossdressers are a part of their "group" for whatever reason - maybe it's because they aren't women 24 hours a day or maybe because they don't have the desire to be a woman full time. But does a crossdresser qualify as a trans individual? Here are my thoughts.

There are times when I realize that, even though I may not be dressed as Jennifer, I'm spending a lot of time thinking about my femme self and girl things. Is there such a thing as not having enough "guy time" or thinking more about your crossdressing than your real life? It's something that many girls have an issue with and I discuss it in this episode.