Jennifer's Tale: My Life as a Crossdresser

Want to know how easy it can be to have someone make you feel amazing? Hear how I had a wonderful Jennifer Day and how one little thing made me feel validated and special.

For some crossdressers choosing your feminine name is an easy task. For others it takes time and thought to capture who you are. Hear how I chose my feminine name here!

It was a chilly day out but that didn't stop me! Hear about how I spent the morning recently as Jennifer - including going to my local coffee shop (which may not have been the best idea...)

A listener asked me "What's it like to dress around your wife?" In this episode, I talk about the history of my crossdressing and my wife - from telling her my secret and how she reacted to seeing Jennifer for the first time to how things are today.

It's a question every crossdresser has and a question everyone asks a crossdresser... Do you tuck? Where does "it" go? In this episode I answer this from my perspective.

It may only be 14 degrees out but that's not stopping me from having a Jen Day! Here's the story of how I had lunch with a friend and the lesson that I, and maybe you, can learn from it.

Many girls ask me for advice and have questions. In this episode I ask questions of my own in hopes of getting answers from you out there!

Four years ago I fully accepted my crossdressing and started sharing this part of myself with friends and family. Here are some of the comments I received which have helped to boost my confidence and make me a more fulfilled person.

It's the holiday season with last-minute shopping to do! Hear about my time out as Jennifer including what I did and what you can learn from my experience.

It was in the 20s today but that didn't stop me from having a girl day. Hear about my adventure out as Jennifer - including a stop at Jiffy Lube!

Everyone likes real life stories right? In this episode I talk about Tracy, a friend I came out to years ago who helped to encourage me to go out in public and not be scared of who I am.

Not too long ago, I found some old pics of myself as Jennifer. This caused me to look back at how far I have come as a crossdresser since those days and how everyone should take time to see how much they have grown as a person over time.

If you're a crossdresser, chances are you will notice that you have a different mentality or state of mind when you're en femme. Does this affect your regular thoughts or mental state on a daily basis? Find out what I've discovered about myself in this episode!

How did I spend a day out as Jennifer? In this episode, hear what I wore from head to toe and hear about my adventure enjoying a morning as a woman. If you enjoy hearing about being out in public, this one's for you!

In this episode, hear me explain why I think I'm a hypocrite and don't always practice what I preach. It's a shameful confession I wanted to get off my chest.

In this episode, I talk about dressing not only to fit the occasion but also to fit the weather conditions. Sometimes it's better to be practical than glamourous.

What is a girl to do when you have a day planned only to have it be chilly and rainy? In this episode, find out how my day was made special as I went out for a Jennifer Day!

For some wearing pantyhose is what it takes to put the icing on the cake of feeling feminine. For others it may be high heels, a wig or (for me) bouncing boobs. I talk about what triggers the ultimate feminine feeling in me and why each of us is different.

A listener wanted to know if I ever wear clothing made for women while I'm in guy mode. In this episode I answer that question and also discuss whether sneaking a feminine article of clothing into your everyday male wardrobe is for everyone.

Recently I had a nice sit-down first meeting with another crossdresser I met online. How I make friends via social media and why face-to-face meetings are so much more fulfilling are the topics of this episode!

A crossdresser recently said that a woman needs to be actively flirting in order to get hit on by a guy. In this episode, I talk about why I don't think this is necessarily the case.

Dancing With the Stars had Kiss' Gene Simmons as a guest judge recently and his comments caused quite a stir. Here I discuss why he is wrong in what he had to say.

For those of you who enjoy real life stories, here's one about one of the first times I braved people - by going to a small grocery store in Iowa.

Halloween is like Christmas for crossdressers! In this episode, I chat about Halloween and how even just going out en femme is okay on this holiday.

In this follow-up to Episode 63, I spend a bit more time discussing my sex life - from my first attraction to someone through present day and how sex factors into my crossdressing.