DiscoverJennifer's Tale: My Life as a Crossdresser
Jennifer's Tale: My Life as a Crossdresser
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Jennifer's Tale: My Life as a Crossdresser

Author: Jennifer

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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!
28 Episodes
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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 reasons why I dress like I do as well as why sometimes casual is better than sexy.
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 you) can do if this happens to you.
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 set in when you don't have a chance to express your feminine side and tips to help you make it through.
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 and cared about. In this episode I talk about how doing this benefitted me, made me feel better about myself and improved my outlook on who I am.
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 helped me with advice, compassion and most of all helped me come out of my shell.
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 from friends and family. In this episode I talk about how I have managed to have two lives and what you can do to make things easier.
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 and tricks that may help you with your feminine voice.
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 what may work for you!
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!
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 continue to deal with it.
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.
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 have coped with not being able to crossdress and what I have done to deal with the depression that happens from not being able to dress.
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 episode I talk about my secret identity, how I have tried to keep my crossdressing a secret over the years and why I finally opted to reveal my secret identity to close friends and family.
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 figured out what size to be, why I like to show my cleavage and more!
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 for where you are going will help you blend in and not draw attention to yourself.
Episode 13 Escapism

Episode 13 Escapism

2024-02-2106:56

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 not only lets me express myself but also helps me forget my troubles and be someone else for a while!
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 learn more about myself - and you will too in this episode!
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 questions and in the process maybe help others who have the same thoughts about themselves. Let me know what you think by email at jenniferstalepodcast@gmail.com
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 episode!
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 steps out into the big world of Iowa.
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