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 60 Things to Learn
For many of us girls, we have been dressing for years and years. Throughout our journey we have learned tips and tricks to becoming a woman from head to toe…
- Jennifer's Tale: My Life as a Crossdresser
Episode 59 Shopping for a Girl as a Guy
If you're just starting out on your feminine journey, you'll need to go shopping for makeup, clothes, shoes and more. Can it be embarrassing to shop for…
- Jennifer's Tale: My Life as a Crossdresser
Episode 58 Wanting Attention
Sometimes when women go out, they dress provocatively in hopes of attracting attention from the opposite sex (or the same sex in some cases.) As a crossdresser…
- Jennifer's Tale: My Life as a Crossdresser
Episode 57 Dress for Sex-Cess
One day while I was out as Jennifer wearing a low-cut top and fairly short skirt, I started wondering if how I dressed was a disservice for real women. Am I…
- Jennifer's Tale: My Life as a Crossdresser
Episode 56 The Boobs Have It
Most crossdressers would say that having boobs is one of the important parts of their dressing. I think most biological women would agree that their breasts…
- Jennifer's Tale: My Life as a Crossdresser
Episode 55 Courage
Guts, intestinal fortitude, courage - it takes a lot of all these for a crossdresser to get dolled up and go out in public. Even veteran girls have times when…
- Jennifer's Tale: My Life as a Crossdresser
Episode 54 Musings
Do you ever wonder what I think about when I'm out as Jennifer? In this episode I discuss a couple of random topics I thought about recently while I was…
- Jennifer's Tale: My Life as a Crossdresser
Episode 53 Where Do I Go?
So you're finally ready to leave your home all dressed up en femme for the first time. Where do you go? What are some good locations to venture out to and…
- Jennifer's Tale: My Life as a Crossdresser
Episode 52 Dressing on a Limited Wardrobe
For many girls out there a wardrobe can be rather limited due to finances or space to store it. What are essential items to have in your closet if you can't…
- Jennifer's Tale: My Life as a Crossdresser
Episode 51 The Eyes Have It
The eyes are the windows to the soul, and for most people making eye contact is one of the first things they do when meeting you. In this episode, I talk about…
- Jennifer's Tale: My Life as a Crossdresser
Episode 50 Is Crossdressing an Addiction?
Many people suffer from an addiction, whether it be smoking, alcohol or drugs. Could crossdressing be considered an addiction? In this episode I take a look at…
- Jennifer's Tale: My Life as a Crossdresser
Episode 49 Getting a Pedicure
Many crossdressers who don't have the opportunity to dress are always looking for a way to feel feminine. Getting a pedicure - even as a guy - is a great way…
- Jennifer's Tale: My Life as a Crossdresser
Episode 48 An Adventure with My Girlfriend
Many years ago I had a girlfriend who helped encourage my crossdressing along with my desire to be out in public. Hear a story about a time when we went out on…
- Jennifer's Tale: My Life as a Crossdresser
Episode 47 Competing Woman to Woman
In my wife's attempt to accept my crossdressing, she said that she felt that I was more feminine than she is because she normally doesn't wear makeup or enjoy…
- Jennifer's Tale: My Life as a Crossdresser
Episode 46 Are Crossdressers Trans?
The term trans is often used to encompass a variety of people in the LGBTQ+ spectrum. As to whether a crossdresser falls into that category varies, depending…
- Jennifer's Tale: My Life as a Crossdresser
Episode 45 Getting the Girl Mojo Back
Sometimes after not dressing for a while, it can be a challenge "getting back into the swing of things." Since I myself have had a couple months of downtime…
Jennifer's Tale: My Life as a CrossdresserEpisode 44 What Are the Odds?
Do you believe in fate or coincidence? In this episode, I tell a story about my best friend growing up, how our lives kept crossing paths and how two people…
Jennifer's Tale: My Life as a CrossdresserEpisode 43 Gender Fluidity
Gender fluidity is a term that wasn't around years ago. Boy George and David Bowie would fit that category - someone who exhibits or dresses as both sexes -…
Jennifer's Tale: My Life as a CrossdresserEpisode 42 The Future
A listener wrote in with a question for me: Where do you see yourself in 25 years? Would you be Jennifer fulltime? In this episode I send a message back to my…
Jennifer's Tale: My Life as a CrossdresserEpisode 41 Underdressing
What can a crossdresser do when you don't have an opportunity to fully express yourself? Underdressing, or wearing women's clothing under your regular male…
- Jennifer's Tale: My Life as a Crossdresser
Episode 40 Early Influences
As a crossdresser figuring myself out in the early 1990s, there were many talk show episodes that featured crossdressers and female impersonators. In this…
- Jennifer's Tale: My Life as a Crossdresser
Episode 39 Self Confidence
One of the most important parts of being a crossdresser - and sometimes the hardest - is having confidence. Whether it be confidence in how you look or faith…
- Jennifer's Tale: My Life as a Crossdresser
Episode 38 Nature vs Nurture
In having a conversation with a family member I was reminded of my childhood. Certain aspects and memories could be looked at as possible causes of my…
- Jennifer's Tale: My Life as a Crossdresser
Episode 37 More About My Boobs
Ever since Episode 15, many people have asked questions about my cleavage and my boobs. In this episode, I answer questions about my chest and talk more about…
- Jennifer's Tale: My Life as a Crossdresser
Episode 36 Don't Be Afraid
It's my first episode on location! During one of my ventures out as Jennifer, I talk about summoning up the courage and confidence to leave your four walls and…
- Jennifer's Tale: My Life as a Crossdresser
Episode 35 What Covid Did to Me
In 2020 covid caused many of us to change our lifestyles. For me, it caused me to reconsider my crossdressing and how I felt about myself. In this episode, I…
- Jennifer's Tale: My Life as a Crossdresser
Episode 34 Kids Are Too Smart
If you have kids, you know that sometimes they are too smart for their own good. My own kids have been overly observant as my crossdressing has gone on and…
- Jennifer's Tale: My Life as a Crossdresser
Episode 33 My Makeup Routine
Many crossdressers find doing their makeup to be a challenge. Starting out, it can be hard knowing what to do to make yourself look like a woman. In this…
- Jennifer's Tale: My Life as a Crossdresser
Episode 32 Real Life Obstacles
As a crossdresser most girls have real life obstacles that prevent them from dressing as often as they would like. Whether it be family, work, neighbors or…
- Jennifer's Tale: My Life as a Crossdresser
Episode 31 Summertime
Summertime means warm weather and as a crossdresser I've learned that heat, makeup and padding don't mix well. In this episode I talk about how I cope with…
- Jennifer's Tale: My Life as a Crossdresser
Episode 30 Body Type
Over the years women are expected to be smaller, thin and petite. Most crossdressers - myself included - have a body type that doesn't fit that mold. In this…
- Jennifer's Tale: My Life as a Crossdresser
Episode 29 Purging Your Wardrobe
If you're a crossdresser chances at least once in your life you vowed to stop and have purged your wardrobe. Hear about the times I have done it and the…
- Jennifer's Tale: My Life as a Crossdresser
Episode 28 Dare to Wear vs Don't Care
Fancy dress vs casual? Revealing vs everyday? From day to day my mood tends to determine what I want to wear as Jennifer. In this episode I talk about the…
- Jennifer's Tale: My Life as a Crossdresser
Episode 27 Thank You Sir
On a recent excursion I was identified as "Sir" despite looking like a woman. In this episode I talk about this experience, how it made me feel and what I (or…
- Jennifer's Tale: My Life as a Crossdresser
Episode 26 The Great Depression
Many crossdressers have times when they don't have the chance to dress. In fact this happened to this recently. In this episode I talk about how depression can…
- Jennifer's Tale: My Life as a Crossdresser
Episode 25 The Benefits of Coming Out
A few years ago I decided to let certain friends and family members know about my crossdressing and my feminine side. I wanted to be honest with people I knew…
- Jennifer's Tale: My Life as a Crossdresser
Episode 24 My Dear Friend
During Covid I started my Facebook page and began reaching out to other girls in hopes of making friends. Here's the story of one such friend and how she has…
- Jennifer's Tale: My Life as a Crossdresser
Episode 23 Leading Two Lives
Most crossdressers lead two lives - their normal male life and their feminine one they keep secret. It can be really tough to keep your secret safe and hidden…
- Jennifer's Tale: My Life as a Crossdresser
Episode 22 Voice Lessons
For some girls, sounding like a woman is more difficult than looking like one. Over the years I have worked on my voice to sound passable. Here are some tips…
- Jennifer's Tale: My Life as a Crossdresser
Episode 21 To Pad or Not to Pad
Many crossdressers use padding to enhance their bust, hips and backside. In this episode I discuss the pros and cons of padding, what works best for me and…
- Jennifer's Tale: My Life as a Crossdresser
Episode 20 Taking the Perfect Selfie
For a lot of girls, taking a selfie is no easy feat. Here are some tips and tricks I've discovered to help you take the best picture of yourself!
- Jennifer's Tale: My Life as a Crossdresser
Episode 19 My Mom Finds Out
A crossdresser's fear is that someone close to you will find out your secret. Here's the story of how my mother confronted me about my crossdressing and how I…
- Jennifer's Tale: My Life as a Crossdresser
Episode 18 My First Date
As a crossdresser, going out alone can be nerve-wracking. Here's the story of the first time I went on a "date" with a friend so I wasn't alone.
- Jennifer's Tale: My Life as a Crossdresser
Episode 17 Manic Depression
Many times crossdressers have to wait weeks, months, or even years between opportunities to express their feminine side. In this episode I chat about how I…
- Jennifer's Tale: My Life as a Crossdresser
Episode 16 My Secret Identity
Superheroes always have a secret identity. They keep their two personas separate to protect their loved ones. Crossdressers are kind of the same. In this…
- Jennifer's Tale: My Life as a Crossdresser
Episode 15 My Boobs and Me
You can see by my pictures that I love my boobs. Having boobs is one of the things that makes me feel feminine and shows that I'm a woman. Hear about how I…
- Jennifer's Tale: My Life as a Crossdresser
Episode 14 Dress for the Occasion
Should you wear an evening gown to the grocery store? How about a cocktail dress to the Goodwill? In this episode I talk about how choosing the right clothes…
- Jennifer's Tale: My Life as a Crossdresser
Episode 13 Escapism
Do you ever wish you could not be you for a while? To be able to escape your job, family or life in general? In this episode I explain why being a crossdresser…
- Jennifer's Tale: My Life as a Crossdresser
Episode 12 My Sexuality Part 2
Last episode I discussed what led me to my declaration that I was bisexual three years ago. Now I talk about what has happened since that further causes me to…
- Jennifer's Tale: My Life as a Crossdresser
Episode 11 My Sexuality
Over the years of being a crossdresser I have always questioned my sexuality. Am I straight? Am I gay? What am I? In this episode I attempt to answer these…
- Jennifer's Tale: My Life as a Crossdresser
Episode 10 My Son Finds Out
Due to me not paying attention, a sent pic turned into an opportunity to tell my son about my crossdressing. Find out how this happened and the outcome on this…
- Jennifer's Tale: My Life as a Crossdresser
Episode 9 Traveling Small Town Iowa
When you're a crossdresser your biggest goal is to exist and enjoy your feminine side. Here's how I was able to begin my journey to Jennifer by taking small…
- Jennifer's Tale: My Life as a Crossdresser
Episode 8 First Time Meeting
Back in the pre-internet days it was tough to meet other crossdressers. Here's the story of how I found another local girl, had my first in-person meeting and…
- Jennifer's Tale: My Life as a Crossdresser
Episode 7 Listener Feedback and More
Thanks to all of you who have checked out my podcast! In this episode I read some viewer feedback and share a bit more about myself in the process. :)
- Jennifer's Tale: My Life as a Crossdresser
Episode 6 Self Expression and Wellness
Have you ever thought about how self expression is a way to help your physical and emotional wellness? After a week in which I got three evenings to be my…
- Jennifer's Tale: My Life as a Crossdresser
Episode 5 Close Encounter with a Friend
Have you ever been out dressed and run into someone you know? Here's a story of almost running into my best friend while out as Jennifer!
- Jennifer's Tale: My Life as a Crossdresser
Episode 4 My Wife Finds Out
How do you tell someone close to you that you have another side? Everyone has their way of letting others know they have a secret. Here's the story of how my…
- Jennifer's Tale: My Life as a Crossdresser
Episode 3 My Love of Pantyhose
Most crossdressers out there have a favorite article of women's clothing, something that symbolizes femininity to them and makes them feel that way whenever…
- Jennifer's Tale: My Life as a Crossdresser
Episode 2 My Fat Chest
If you look at a picture of me, chances are you will notice my cleavage. Find out how life as been for me with a big chest - the good and the bad - and what I…
Jennifer's Tale: My Life as a CrossdresserEpisode 1 All About Me
Welcome to my new podcast! If you're a crossdresser like myself I hope you find this podcast of interest. In this episode you learn a bit about me and my life…