Shows / 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
- Jennifer's Tale: My Life as a Crossdresser
Episode 179 Telling Your Friends and Family
For many crossdressers being able to share their secret with friends and family is something they would love to do. Hear about how I've done this with numerous…
- Jennifer's Tale: My Life as a Crossdresser
Episode 178 My Hometown
Once or twice a year I make a trip back to where I was born and raised. The past few times I have done so as Jennifer. As I sti in my car in front of where my…
- Jennifer's Tale: My Life as a Crossdresser
Episode 177 Did You Ever Notice...?
After being on social media as a crossdresser you're bound to attract some trolls. I started taking a closer look at some of the frequent comments made as well…
- Jennifer's Tale: My Life as a Crossdresser
Episode 176 Sex Sells Part 2
Many crossdressers are afraid to talk about how they really feel or what they are into when it comes to sex. Should you be ashamed or afraid of who you're…
- Jennifer's Tale: My Life as a Crossdresser
Episode 175 Looking Back at My Younger Self
I discovered pictures I posted on Flickr way back when I was single and a lot younger. Having forgotten they were there, seeing these photos caused me to…
- Jennifer's Tale: My Life as a Crossdresser
Episode 174 Passable vs Presentable
For some crossdressers, passing as a normal woman and blending in is the goal when going out in public. For others who feel they cannot truly pass as a woman…
- Jennifer's Tale: My Life as a Crossdresser
Episode 173 Why I Post on Facebook
Facebook is my preferred social media platform and I post comments and pictures there frequently and maybe you do too. Some haters and other outspoken people…
- Jennifer's Tale: My Life as a Crossdresser
Episode 172 Separating the Two Personas
How easy or tough is it to keep your two personas separate? Do you reserve your feminine side and crossdressing specifically for special times? Or do you find…
- Jennifer's Tale: My Life as a Crossdresser
Episode 171 Shopping Tips
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 170 Sharing My Secret in Person
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 169 This One's About God
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 168 Don't Be Afraid to Be You
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 167 Looking Back
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 166 The Bathroom Debate
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 165 What's Your Jam?
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 164 What the Haters Think
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 163 Getting Older
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 162 To All the Naysayers
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 161 When Compromise Becomes Conflict
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 160 Pride Month
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 159 Life is Just a Fantasy
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 158 Be Careful What You Wish For
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 157 The Value of Someone's Trust
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 156 Tales From the Car
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 155 AI vs Reality
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 154 Deal With the Hand That's Dealt to You
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 153 What My Wife Knows (But Doesn't Say)
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 152 Makeup Tips and Simplicity
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 151 Friendship
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 150 My Biggest Challenge
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 149 What is Two-Spirit? CORRECTED
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 148 What to Wear
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 147 My Trip to Hooters
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 146 The Best of Both Worlds
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 145 Pantyhose Secrets
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 144 Do We Need Labels?
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 143 My Trip to the Mall
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 142 Getting My Geek On!
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 141 This One's for the Men
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 140 Disrespect
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 139 Is HRT for Me?
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 138 Being Safe While Dressed
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 137 Finding Sisterhood
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 136 Otokonoko
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 135 Crossdressing Injuries
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 134 Boobs as Medicine
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 133 Thinking Like a Woman
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 132 Buckets of Confidence!
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?…
- Jennifer's Tale: My Life as a Crossdresser
Episode 131 The Cat's Out of the Bag... Sort of
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 130 Fitting Into a Woman's World
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 129 Can Crossdressing Ruin Your Career?
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 128 Finding Your Lane
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 127 Halloween Hijinks
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 126 How I Spent My Wife's Vacation
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 125 Crossdressing and Politics
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…
Jennifer's Tale: My Life as a CrossdresserEpisode 124 All About Music
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 123 Emotional Support
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…
Jennifer's Tale: My Life as a CrossdresserEpisode 122 Emergency!
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?…
- Jennifer's Tale: My Life as a Crossdresser
Episode 121 Restroom Etiquette
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…
Jennifer's Tale: My Life as a CrossdresserEpisode 120 It's All About the Face
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…