Jennifer's Tale: My Life as a Crossdresser

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 crossdressing. Is dressing like a woman inherent to some girls? Are some girls created? Or can both circumstances hold true?

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 what having boobs means to me.

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 go out in public.

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 talk about how covid brought Jennifer out in a new way and helped me to look at myself in a new light.

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 there have been times when my secret was noticed. How would you deal with your kids noticing clues to your feminine self? Here are some ideas of my own.

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 episode, I go through my process for doing my makeup and offer some tips and tricks.

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 time the opportunities aren't always there. In this episode I talk about what obstacles I face in dressing as Jennifer as well as things you can do to help make it through the rough times.

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 summer heat as Jennifer, what I do to enjoy my time outside and how to beat the heat!

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 episode I talk about how I feel about my body size, what I do to try and fit into the world as a larger woman and what you can do to feel better about yourself.

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 reasons why, as well as what to do if you decide to purge to help save yourself lots of money!

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.