Jennifer's Tale: My Life as a Crossdresser

Episode 153 What My Wife Knows (But Doesn't Say)

08 May 2026

Contributed by Lukas

My wife knows about my crossdressing but prefers not to know where I go or what I do. However, there are hints and questions she says that makes me wo...

Episode 152 Makeup Tips and Simplicity

01 May 2026

Contributed by Lukas

Many crossdressers have a tough time learning how to do makeup. While it's not an easy feat, it can be a lot simpler than most girls think. In thi...

Episode 151 Friendship

24 Apr 2026

Contributed by Lukas

There are times when life can be bad. Really bad. When times take a turn for the worst sometimes you need a reminder or a blessing to show you how luc...

Episode 150 My Biggest Challenge

17 Apr 2026

Contributed by Lukas

For my 150th episode, listener Julie Shaw asked me a doozie of a question! What has been my biggest challenge as a crossdresser? Find out my answer in...

Episode 149 What is Two-Spirit? CORRECTED

14 Apr 2026

Contributed by Lukas

The term "two-spirit" is something I found out about relatively recently. As a crossdresser you may find this idea fits you like I think it ...

Episode 149 What is Two-Spirit?

10 Apr 2026

Contributed by Lukas

The term "two-spirit" is something I found out about relatively recently. As a crossdresser you may find this idea fits you like I think it ...

Episode 148 What to Wear

03 Apr 2026

Contributed by Lukas

You just got a brand new dress that looks stunning and want to wear it right immediately. The thrift store waits for no one. Wait, what? There's a...

Episode 147 My Trip to Hooters

27 Mar 2026

Contributed by Lukas

The Hooters restaurant at the Mall of America is closing which caused me to make a pilgrimage to visit it one last time. What happened when I got ther...

Episode 146 The Best of Both Worlds

20 Mar 2026

Contributed by Lukas

We all have lots of various interests and things that we enjoy doing. It could be a sport, a hobby or an activity. What if you could combine one of yo...

Episode 145 Pantyhose Secrets

13 Mar 2026

Contributed by Lukas

For the majority of us, pantyhose are a staple of our feminine wardrobe. In this episode I discuss recent brands that I have tried, which ones I like ...

Episode 144 Do We Need Labels?

06 Mar 2026

Contributed by Lukas

Crossdresser, trans individual, bisexual, gay - all these are labels that we tend to put on people to differentiate them in our society. But do we rea...

Episode 143 My Trip to the Mall

27 Feb 2026

Contributed by Lukas

Recently I made a trip to the Mall of America. Although my goal of getting a bra fitting fell a little short what happened instead made my day! Hear a...

Episode 142 Getting My Geek On!

20 Feb 2026

Contributed by Lukas

Even though you may be a girl who has dressed for years there are always new challenges to face. In this episode I talk about doing something I have n...

Episode 141 This One's for the Men

13 Feb 2026

Contributed by Lukas

I sometimes get questions from other girls that I enjoy answering on my podcast. However I realized that I also get questions from men as well. In thi...

Episode 140 Disrespect

06 Feb 2026

Contributed by Lukas

I have always felt that the trans community is a huge umbrella that covers a lot of people. However, some trans women feel that crossdressers are not ...

Episode 139 Is HRT for Me?

30 Jan 2026

Contributed by Lukas

It's a question that all crossdressers - myself included - ask themselves. In this episode I discuss my thoughts on HRT and whether it's in Je...

Episode 138 Being Safe While Dressed

23 Jan 2026

Contributed by Lukas

Women have an advantage when it comes to safety while out in public - they have had years of practice and education to protect themselves from unwante...

Episode 137 Finding Sisterhood

16 Jan 2026

Contributed by Lukas

Many crossdressers find friends online to chat with, share experiences and interests and become "sisters" with. But is that enough? How to f...

Episode 136 Otokonoko

09 Jan 2026

Contributed by Lukas

In Japanese culture men who dress as women or transform into women have been very popular in manga and anime. Recently otokonoko or "men with a f...

Episode 135 Crossdressing Injuries

02 Jan 2026

Contributed by Lukas

Sprained ankles from high heels, blisters from taping, telltale marks on earlobes from clip-on earrings - there are many injuries that you could get w...

Episode 134 Boobs as Medicine

26 Dec 2025

Contributed by Lukas

According to a report, if a man stares at a woman's boobs for 10 minutes a day or longer it can act as medicine and improve his health. In this ep...

Episode 133 Thinking Like a Woman

19 Dec 2025

Contributed by Lukas

The more I enjoy being Jennifer the more I think about things that I can do to improve my appearance or make me feel better about myself. Coincidental...

Episode 132 Buckets of Confidence!

12 Dec 2025

Contributed by Lukas

Many crossdressers are afraid to be their true selves and go out in public. But have you ever considered how courageous you are just by being a crossd...

Episode 131 The Cat's Out of the Bag... Sort of

05 Dec 2025

Contributed by Lukas

Sometimes it takes a long time to realize something that you knew all along. In this episode I talk about how years of messages and clues should have ...

Episode 130 Fitting Into a Woman's World

28 Nov 2025

Contributed by Lukas

As a crossdresser, we are more comfortable and connected to our feminine self. In this episode I talk about connecting with other women that way but a...

Episode 129 Can Crossdressing Ruin Your Career?

21 Nov 2025

Contributed by Lukas

If you get outed as a crossdresser to your employer whether by a coworker or by accident it can be an issue. In this episode I discuss the potential r...

Episode 128 Finding Your Lane

14 Nov 2025

Contributed by Lukas

As most of us know, crossdressing can range from wearing a particular item of women's clothing to completely dressing head-to-toe. What works best...

Episode 127 Halloween Hijinks

07 Nov 2025

Contributed by Lukas

Halloween has come and gone and this year I got to enjoy it for a bit! In this episode hear about what I did while enjoying "Crossdresser's C...

Episode 126 How I Spent My Wife's Vacation

31 Oct 2025

Contributed by Lukas

A couple weeks ago my wife went on a trip, leaving me with a few Jennifer days. In this special episode on location find out what I did and how much I...

Episode 125 Crossdressing and Politics

24 Oct 2025

Contributed by Lukas

Politics are a touchy subject for most people. Even I normally keep my views to myself. In this episode I cover this area and express my views on the ...

Episode 124 All About Music

17 Oct 2025

Contributed by Lukas

Music does many things to us. It can spur memories, conjure feelings and even help you to fall into your feminine persona more easily. In this episode...

Episode 123 Emotional Support

10 Oct 2025

Contributed by Lukas

Emotional support can come from all places - spouses, significant others, family members or friends. As a crossdresser it can be a challenge to get th...

Episode 122 Emergency!

03 Oct 2025

Contributed by Lukas

Every crossdresser enjoys being out in public. But have you ever thought about what you would do if your car broke down? What if you had a medical eme...

Episode 121 Restroom Etiquette

29 Sep 2025

Contributed by Lukas

If you spend any time out as your femme self, chances are at some point you'll need to "do your business." In this episode I discuss whe...

Episode 120 It's All About the Face

29 Sep 2025

Contributed by Lukas

Many crossdressers reach out to me asking how to find other girls in their area and how to connect with them. Thankfully it's a lot easier now to ...

Episode 119 Does Crossdressing Make You Gay?

29 Sep 2025

Contributed by Lukas

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 ...

Episode 118 Male Validation

15 Sep 2025

Contributed by Lukas

For many crossdressers getting a smile, nod or compliment about their appearance is a wonderful thing. For others, having a man doing the complimentin...

Episode 117 Authenticity

11 Sep 2025

Contributed by Lukas

Many followers have complimented how genuine and authentic I am on my podcast. But how authentic can a crossdresser truly Be? From our outside appeara...

Episode 116 I Love My Cis-ters!

08 Sep 2025

Contributed by Lukas

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 hav...

Episode 115 Baby Steps

04 Sep 2025

Contributed by Lukas

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 jour...

Episode 114 Pride vs Everyday

01 Sep 2025

Contributed by Lukas

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 t...

Episode 113 Regrets, I've Had a Few

28 Aug 2025

Contributed by Lukas

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...

Episode 112 For the Wives

25 Aug 2025

Contributed by Lukas

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 ep...

Jennifer's Tale Twice a Week?!

23 Aug 2025

Contributed by Lukas

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) i...

Episode 111 Courage in Dressing

21 Aug 2025

Contributed by Lukas

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 co...

Episode 110 Crossdressing and Other Hobbies

18 Aug 2025

Contributed by Lukas

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 t...

Episode 109 Writing a Letter

11 Aug 2025

Contributed by Lukas

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 ...

Episode 108 Retail Therapy

04 Aug 2025

Contributed by Lukas

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...

Episode 107 Why Be Ashamed?

28 Jul 2025

Contributed by Lukas

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 ...

Episode 106 Am I Trans Enough?

21 Jul 2025

Contributed by Lukas

Some trans girls don't feel that crossdressers are a part of their "group" for whatever reason - maybe it's because they aren't ...

Episode 105 Finding the Middle Ground - In Your Mind

14 Jul 2025

Contributed by Lukas

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 gir...

Episode 104 In Case of My Death...

07 Jul 2025

Contributed by Lukas

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 ...

Episode 103 Pantyhose and Why I Love Them

30 Jun 2025

Contributed by Lukas

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 t...

Episode 102 Is It Really Worth It?

23 Jun 2025

Contributed by Lukas

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 ...

Episode 101 Finding Your Tribe

16 Jun 2025

Contributed by Lukas

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 tr...

Episode 100 Sex and the Single/Married Crossdresser

09 Jun 2025

Contributed by Lukas

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...

Episode 99 Don't Be Afraid of Change

02 Jun 2025

Contributed by Lukas

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...

Episode 98 Different Shapes and Sizes

26 May 2025

Contributed by Lukas

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...

Episode 97 Oops!

19 May 2025

Contributed by Lukas

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? He...

Episode 96 Don't Embarrass Me

12 May 2025

Contributed by Lukas

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&...

Episode 95 Let's Be Casual

05 May 2025

Contributed by Lukas

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 ...

Episode 94 Julie Does It Again!

28 Apr 2025

Contributed by Lukas

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 w...

Episode 93 How Much is Too Much?

21 Apr 2025

Contributed by Lukas

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 th...

Episode 92 Another Jennifer Day

14 Apr 2025

Contributed by Lukas

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......

Episode 91 Dealing With the Negative

07 Apr 2025

Contributed by Lukas

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 thou...

Episode 90 A Little Spicy

31 Mar 2025

Contributed by Lukas

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!

Episode 89 Lack of Support (And I Don't Mean a Bra)

24 Mar 2025

Contributed by Lukas

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 so...

Episode 88 An Admiring Glance

17 Mar 2025

Contributed by Lukas

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 v...

Episode 87 What's in a Name?

10 Mar 2025

Contributed by Lukas

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 f...

Episode 86 Julie the Barista

03 Mar 2025

Contributed by Lukas

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...

Episode 85 Dressing Around My Wife

24 Feb 2025

Contributed by Lukas

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 wif...

Episode 84 To Tuck Or Not to Tuck

17 Feb 2025

Contributed by Lukas

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...

Episode 83 Lunch With a Friend

10 Feb 2025

Contributed by Lukas

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 ...

Episode 82 I Have Questions!

03 Feb 2025

Contributed by Lukas

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!

Episode 81 What the Critics Say

27 Jan 2025

Contributed by Lukas

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 rece...

Episode 80 Christmas Shopping with Jennifer

20 Jan 2025

Contributed by Lukas

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 experi...

Episode 79 My Day Out in the Cold

13 Jan 2025

Contributed by Lukas

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!

Episode 78 My Friend Tracy

06 Jan 2025

Contributed by Lukas

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 p...

Episode 77 Looking Back

30 Dec 2024

Contributed by Lukas

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 a...

Episode 76 Day-to-Day Mentality

26 Dec 2024

Contributed by Lukas

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...

Episode 75 A Grand Day Out

23 Dec 2024

Contributed by Lukas

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. I...

Episode 74 I'm a Hypocrite

19 Dec 2024

Contributed by Lukas

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 m...

Episode 73 Sexy Soccer Mom

16 Dec 2024

Contributed by Lukas

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...

Episode 72 A Cold Day in November

12 Dec 2024

Contributed by Lukas

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 ...

Episode 71 How I Feel Feminine

09 Dec 2024

Contributed by Lukas

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) bounc...

Episode 70 Wearing Women's Clothing as a Guy

05 Dec 2024

Contributed by Lukas

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 whethe...

Episode 69 Finding Friendship

02 Dec 2024

Contributed by Lukas

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...

Episode 68 Flirting

28 Nov 2024

Contributed by Lukas

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 thi...

Episode 67 Gene Simmons is Wrong

25 Nov 2024

Contributed by Lukas

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 h...

Episode 66 A Trip to the Grocery Store

21 Nov 2024

Contributed by Lukas

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.

Episode 65 Happy Halloween

18 Nov 2024

Contributed by Lukas

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.

Episode 64 Sex Sells

14 Nov 2024

Contributed by Lukas

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 ...

Episode 63 My Feminine Desires

11 Nov 2024

Contributed by Lukas

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 at...

Episode 62 She's Got Legs

07 Nov 2024

Contributed by Lukas

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 ...

Episode 61 Meeting Other Crossdressers

04 Nov 2024

Contributed by Lukas

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 ...

Episode 60 Things to Learn

31 Oct 2024

Contributed by Lukas

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 ...

Episode 59 Shopping for a Girl as a Guy

28 Oct 2024

Contributed by Lukas

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 t...

Episode 58 Wanting Attention

24 Oct 2024

Contributed by Lukas

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 cro...

Episode 57 Dress for Sex-Cess

21 Oct 2024

Contributed by Lukas

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...

Episode 56 The Boobs Have It

17 Oct 2024

Contributed by Lukas

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 b...