Shows / Jennifer's Tale: My Life as a Crossdresser
Jennifer's Tale: My Life as a Crossdresser
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!
Episodes
Jennifer's Tale: My Life as a CrossdresserEpisode 119 Does Crossdressing Make You Gay?
We all know crossdressing is a way to express your feminine side. But does how you feel when you dress dictate your sexuality? In this episode I talk about…
- Jennifer's Tale: My Life as a Crossdresser
Episode 118 Male Validation
For many crossdressers getting a smile, nod or compliment about their appearance is a wonderful thing. For others, having a man doing the complimenting means…
- Jennifer's Tale: My Life as a Crossdresser
Episode 117 Authenticity
Many followers have complimented how genuine and authentic I am on my podcast. But how authentic can a crossdresser truly Be? From our outside appearance to…
- Jennifer's Tale: My Life as a Crossdresser
Episode 116 I Love My Cis-ters!
Since I became comfortable with being a crossdresser I have shared this side of myself with many friends and family. Most of the women I have told have been…
- Jennifer's Tale: My Life as a Crossdresser
Episode 115 Baby Steps
Every crossdresser starts out be dressing within their four walls. But the urge to go outside is strong. In this episode I discuss how I began my journey to go…
- Jennifer's Tale: My Life as a Crossdresser
Episode 114 Pride vs Everyday
Pride Month has come and gone for this year. It was great to see so many people out and proud, being themselves. But do some people take it a little too far in…
- Jennifer's Tale: My Life as a Crossdresser
Episode 113 Regrets, I've Had a Few
Everyone has regrets. In this episode I talk about some of my regrets I have regarding my crossdressing - from missed opportunities to dress more over the…
- Jennifer's Tale: My Life as a Crossdresser
Episode 112 For the Wives
If you're like me and have a wife or girlfriend, it can be really tough to discuss your crossdressing, feelings and thoughts with them. In this episode I talk…
- Jennifer's Tale: My Life as a Crossdresser
Jennifer's Tale Twice a Week?!
If you follow me on social media you may know that Jennifer's Tale is an audio and video podcast. The video feed (which can be found on Youtube) is a few…
- Jennifer's Tale: My Life as a Crossdresser
Episode 111 Courage in Dressing
Courage comes in all forms. Whether it's courage under fire, standing up to a bully or facing a fear of flying it takes something special to be courageous. But…
- Jennifer's Tale: My Life as a Crossdresser
Episode 110 Crossdressing and Other Hobbies
I've discovered over the years that if you want to get someone talking, ask them about their kids (if they have any) or what they enjoy doing in their free…
- Jennifer's Tale: My Life as a Crossdresser
Episode 109 Writing a Letter
Sometimes putting words down on paper helps. Whether its a post-it of encouragement to yourself, a note to a friend thanking them for being there for you or a…
- Jennifer's Tale: My Life as a Crossdresser
Episode 108 Retail Therapy
Summer is here and while there are benefits of vacation and other things, having your kids home for three months can cut into crossdressing time. What can you…
- Jennifer's Tale: My Life as a Crossdresser
Episode 107 Why Be Ashamed?
It's a feeling every crossdresser has - being ashamed of who they are and why they have the desire to wear women's clothing. Coping with this can range from…
- Jennifer's Tale: My Life as a Crossdresser
Episode 106 Am I Trans Enough?
Some trans girls don't feel that crossdressers are a part of their "group" for whatever reason - maybe it's because they aren't women 24 hours a day or maybe…
- Jennifer's Tale: My Life as a Crossdresser
Episode 105 Finding the Middle Ground - In Your Mind
There are times when I realize that, even though I may not be dressed as Jennifer, I'm spending a lot of time thinking about my femme self and girl things. Is…
- Jennifer's Tale: My Life as a Crossdresser
Episode 104 In Case of My Death...
Are you a crossdresser that keeps your feminine side a secret? Do you have a storage locker or somewhere you keep your makeup and clothes? What would happen if…
- Jennifer's Tale: My Life as a Crossdresser
Episode 103 Pantyhose and Why I Love Them
For many crossdressers, sensory stimulation is one of the perks of dressing. From the smell of perfume to the gentle pull of dangly earrings, having the sense…
- Jennifer's Tale: My Life as a Crossdresser
Episode 102 Is It Really Worth It?
For some girls, getting ready to be their femme selves takes hours. Is it worth all the time and effort to feel your feminine best? In this episode I discuss…
- Jennifer's Tale: My Life as a Crossdresser
Episode 101 Finding Your Tribe
Whether you're a gamer, sci-fi fan or a crossdresser, finding others like yourself makes you feel better about who you are. Hear how I found my tribes…
- Jennifer's Tale: My Life as a Crossdresser
Episode 100 Sex and the Single/Married Crossdresser
Time to celebrate! In this anniversary episode I break the barrier and chat about crossdressers' sex lives - from what they say they like to their secret…
- Jennifer's Tale: My Life as a Crossdresser
Episode 99 Don't Be Afraid of Change
Over the years you may have worked hard to develop your look. But should you stop experimenting with your appearance? In this episode I talk about why it's a…
- Jennifer's Tale: My Life as a Crossdresser
Episode 98 Different Shapes and Sizes
If you pay attention, you will notice that women come in all shapes and sizes. You may think you need padding, cinchers and forms in order to make you look…
- Jennifer's Tale: My Life as a Crossdresser
Episode 97 Oops!
Have you ever accidentally left out a pair of pantyhose after you've dressed? Maybe posted a pic of your femme self on your male Facebook page? Here are some…
- Jennifer's Tale: My Life as a Crossdresser
Episode 96 Don't Embarrass Me
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 95 Let's Be Casual
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 94 Julie Does It Again!
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 93 How Much is Too Much?
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 92 Another Jennifer Day
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...
- Jennifer's Tale: My Life as a Crossdresser
Episode 91 Dealing With the Negative
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 90 A Little Spicy
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!
- Jennifer's Tale: My Life as a Crossdresser
Episode 89 Lack of Support (And I Don't Mean a Bra)
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 88 An Admiring Glance
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 87 What's in a Name?
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 86 Julie the Barista
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 85 Dressing Around My Wife
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 84 To Tuck Or Not to Tuck
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 83 Lunch With a Friend
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 82 I Have Questions!
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!
- Jennifer's Tale: My Life as a Crossdresser
Episode 81 What the Critics Say
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 80 Christmas Shopping with Jennifer
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.
- Jennifer's Tale: My Life as a Crossdresser
Episode 79 My Day Out in the Cold
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!
- Jennifer's Tale: My Life as a Crossdresser
Episode 78 My Friend Tracy
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 77 Looking Back
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 76 Day-to-Day Mentality
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 75 A Grand Day Out
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 74 I'm a Hypocrite
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.
- Jennifer's Tale: My Life as a Crossdresser
Episode 73 Sexy Soccer Mom
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 72 A Cold Day in November
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's Tale: My Life as a Crossdresser
Episode 71 How I Feel Feminine
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 70 Wearing Women's Clothing as a Guy
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 69 Finding Friendship
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 68 Flirting
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 67 Gene Simmons is Wrong
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 66 A Trip to the Grocery Store
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.
- Jennifer's Tale: My Life as a Crossdresser
Episode 65 Happy Halloween
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.
- Jennifer's Tale: My Life as a Crossdresser
Episode 64 Sex Sells
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 63 My Feminine Desires
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?…
- Jennifer's Tale: My Life as a Crossdresser
Episode 62 She's Got Legs
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…
- Jennifer's Tale: My Life as a Crossdresser
Episode 61 Meeting Other Crossdressers
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…