Jennifer's Tale: My Life as a Crossdresser

One of the greatest fears a spouse or significant other of a crossdresser has is someone finding out who they are in real life. They love you but don't want to be embarrassed by your crossdressing. In this episode I discuss this topic and what you can do to help avoid these situations.

We all enjoy dressing up and looking sexy in sparkly dresses, short skirts and dazzling outfits. But many times we are better served by toning things down. It's time to discuss how you can dress "casual" and still feel sexy and feminine in this episode.

I told Julie, the friendly lady at my local coffee shop, about Jennifer and wanted to stop by and have her meet me in person. What happened that day was wonderful and almost magical! Hear what happened and how there are caring people out there for us to meet in this episode.

Can you have too much of a good thing? Can dressing as your femme self harm your marriage or relationship? I discuss the trials and tribulations of the fine line between success and excess in this episode.

A day off means another Jennifer Day! Hear about my trip out and about - including a stop at my favorite coffee shop and possibly being figured out...

How do you deal with a negative interaction or comment when you're out as your femme self? In this episode I discuss this matter and share my thoughts and tips on how to handle such a situation.

In honor of Valentine's Day, here's a story of a first-time meeting I had with a lovely gentleman that proved to be a little spicy!

For many crossdressers, not having family or friends to share their secret with can be an issue. It's hard to hold in something so special that some may see as bad. In this episode I talk about what you can do to find that support we all need to make it through life.

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.

It's time to come clean about my feminine thoughts and desires. When I dress as a woman, what desires do I have? Do I hope to get more than a guy's attention? Find out in this episode!

Most crossdressers - myself included - love the feeling of wearing a skirt or dress and showing off our legs. It's one of the highlights of being a woman. Why do we find having smooth legs and wearing a skirt so appealing? I attempt to explain why going out in a miniskirt makes me feel so feminine in this episode.

One of the worst things about being a crossdresser is the feeling that you're alone. Many girls think they are the only one who feels this way or enjoys dressing as a woman. Finding others that feel the same way used to be very hard but has gotten easier over time. Listen to me talk about ways I have found other girls and sisters and how you can do the same thing!

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. However, it's impossible to learn everything or be an expert on it all. Here are some areas that I could develop more and become better at.

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 women's items when you're a guy? Are there ways to get everything you need without revealing that your items are for you? Hear about my experiences shopping as a guy for women's clothes, as well as tips to help make the experience easier right here!

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 most times you don't want to draw attention to yourself, but there are times when you do want to experience what a real woman does. Why do I sometimes want attention from men when I go out? Find out in this episode.

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 demeaning women if I dress sexy or somewhat slutty? This question turned into a discussion with a female friend of mine - as well as this episode!

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 are symbols of the power they have in a male-dominated world. For me, having boobs when I go out as Jennifer is both a turn-on and important to have and show. Hear me discuss why this is and more in this episode.

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 they feel frightened when going out. In this episode, I talk about what I do to chase these fears away and enjoy being out in the world as Jennifer.

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 enjoying a girl day.

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 experience being out as your feminine self and not be afraid? Here are some places I enjoy going and other ideas to make those times out not so frightening.

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 have 20 pair of shoes, 50 dresses and 75 outfits? I give you some ideas and tips of what are must-haves in this episode.

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 why getting your eye makeup on point is important to your overall appearance and one of my top things to do when dressing.

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 addiction and debate if the desire to dress as a woman can be looked at as an addiction or not.

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 to indulge yourself, feel feminine and not have to worry about what others think. Hear me discuss why this is a great option!

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 a journey, my apprehension to do so and the lesson I learned from this adventure.

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 dresses. In this episode, I discuss whether or not there is a competition between a crossdresser and a significant other to be more feminine and how I feel about this topic.

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 on who you talk to. In this episode, I talk about my interpretation of the word trans and how I feel I land in this broad word.