Jennifer's Tale: My Life as a Crossdresser
Episodes
Episode 55 Courage
14 Oct 2024
Contributed by Lukas
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 ti...
Episode 54 Musings
10 Oct 2024
Contributed by Lukas
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...
Episode 53 Where Do I Go?
07 Oct 2024
Contributed by Lukas
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 ou...
Episode 52 Dressing on a Limited Wardrobe
03 Oct 2024
Contributed by Lukas
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...
Episode 51 The Eyes Have It
30 Sep 2024
Contributed by Lukas
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 t...
Episode 50 Is Crossdressing an Addiction?
26 Sep 2024
Contributed by Lukas
Many people suffer from an addiction, whether it be smoking, alcohol or drugs. Could crossdressing be considered an addiction? In this episode I take ...
Episode 49 Getting a Pedicure
23 Sep 2024
Contributed by Lukas
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 ...
Episode 48 An Adventure with My Girlfriend
19 Sep 2024
Contributed by Lukas
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 we...
Episode 47 Competing Woman to Woman
16 Sep 2024
Contributed by Lukas
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...
Episode 46 Are Crossdressers Trans?
12 Sep 2024
Contributed by Lukas
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, de...
Episode 45 Getting the Girl Mojo Back
09 Sep 2024
Contributed by Lukas
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 mo...
Episode 44 What Are the Odds?
25 Jul 2024
Contributed by Lukas
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 ...
Episode 43 Gender Fluidity
22 Jul 2024
Contributed by Lukas
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 bo...
Episode 42 The Future
18 Jul 2024
Contributed by Lukas
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 ba...
Episode 41 Underdressing
15 Jul 2024
Contributed by Lukas
What can a crossdresser do when you don't have an opportunity to fully express yourself? Underdressing, or wearing women's clothing under your...
Episode 40 Early Influences
08 Jul 2024
Contributed by Lukas
As a crossdresser figuring myself out in the early 1990s, there were many talk show episodes that featured crossdressers and female impersonators. In ...
Episode 39 Self Confidence
04 Jul 2024
Contributed by Lukas
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 o...
Episode 38 Nature vs Nurture
01 Jul 2024
Contributed by Lukas
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...
Episode 37 More About My Boobs
27 Jun 2024
Contributed by Lukas
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 mo...
Episode 36 Don't Be Afraid
24 Jun 2024
Contributed by Lukas
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 f...
Episode 35 What Covid Did to Me
20 Jun 2024
Contributed by Lukas
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 epi...
Episode 34 Kids Are Too Smart
17 Jun 2024
Contributed by Lukas
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 o...
Episode 33 My Makeup Routine
13 Jun 2024
Contributed by Lukas
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 t...
Episode 32 Real Life Obstacles
10 Jun 2024
Contributed by Lukas
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, neighbo...
Episode 31 Summertime
06 Jun 2024
Contributed by Lukas
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 ho...
Episode 30 Body Type
03 Jun 2024
Contributed by Lukas
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 mo...
Episode 29 Purging Your Wardrobe
30 May 2024
Contributed by Lukas
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 a...
Episode 28 Dare to Wear vs Don't Care
27 May 2024
Contributed by Lukas
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...
Episode 27 Thank You Sir
23 May 2024
Contributed by Lukas
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 f...
Episode 26 The Great Depression
20 May 2024
Contributed by Lukas
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 d...
Episode 25 The Benefits of Coming Out
19 Apr 2024
Contributed by Lukas
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 peopl...
Episode 24 My Dear Friend
16 Apr 2024
Contributed by Lukas
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 ...
Episode 23 Leading Two Lives
12 Apr 2024
Contributed by Lukas
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 an...
Episode 22 Voice Lessons
09 Apr 2024
Contributed by Lukas
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 so...
Episode 21 To Pad or Not to Pad
04 Apr 2024
Contributed by Lukas
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 m...
Episode 20 Taking the Perfect Selfie
01 Apr 2024
Contributed by Lukas
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!
Episode 19 My Mom Finds Out
28 Mar 2024
Contributed by Lukas
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 crossdr...
Episode 18 My First Date
25 Mar 2024
Contributed by Lukas
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&...
Episode 17 Manic Depression
19 Mar 2024
Contributed by Lukas
Many times crossdressers have to wait weeks, months, or even years between opportunities to express their feminine side. In this episode I chat about ...
Episode 16 My Secret Identity
16 Mar 2024
Contributed by Lukas
Superheroes always have a secret identity. They keep their two personas separate to protect their loved ones. Crossdressers are kind of the same. In t...
Episode 15 My Boobs and Me
26 Feb 2024
Contributed by Lukas
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 ab...
Episode 14 Dress for the Occasion
23 Feb 2024
Contributed by Lukas
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 ...
Episode 13 Escapism
21 Feb 2024
Contributed by Lukas
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 cro...
Episode 12 My Sexuality Part 2
01 Feb 2024
Contributed by Lukas
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 caus...
Episode 11 My Sexuality
29 Jan 2024
Contributed by Lukas
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 ...
Episode 10 My Son Finds Out
26 Jan 2024
Contributed by Lukas
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 outcom...
Episode 9 Traveling Small Town Iowa
16 Jan 2024
Contributed by Lukas
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 b...
Episode 8 First Time Meeting
12 Jan 2024
Contributed by Lukas
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...
Episode 7 Listener Feedback and More
10 Jan 2024
Contributed by Lukas
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. :)...
Episode 6 Self Expression and Wellness
22 Dec 2023
Contributed by Lukas
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 b...
Episode 5 Close Encounter with a Friend
19 Dec 2023
Contributed by Lukas
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!
Episode 4 My Wife Finds Out
09 Dec 2023
Contributed by Lukas
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 stor...
Episode 3 My Love of Pantyhose
01 Dec 2023
Contributed by Lukas
Most crossdressers out there have a favorite article of women's clothing, something that symbolizes femininity to them and makes them feel that wa...
Episode 2 My Fat Chest
27 Nov 2023
Contributed by Lukas
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 - an...
Episode 1 All About Me
20 Nov 2023
Contributed by Lukas
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...