All Episodes
Jennifer's Tale: My Life as a Crossdresser — 165 episodes
Episode 164 What the Haters Think
Episode 163 Getting Older
Episode 162 To All the Naysayers
Episode 161 When Compromise Becomes Conflict
Episode 160 Pride Month
Episode 159 Life is Just a Fantasy
Episode 158 Be Careful What You Wish For
Episode 157 The Value of Someone's Trust
Episode 156 Tales From the Car
Episode 155 AI vs Reality
Episode 154 Deal With the Hand That's Dealt to You
Episode 153 What My Wife Knows (But Doesn't Say)
Episode 152 Makeup Tips and Simplicity
Episode 151 Friendship
Episode 150 My Biggest Challenge
Episode 149 What is Two-Spirit? CORRECTED
Episode 148 What to Wear
Episode 147 My Trip to Hooters
Episode 146 The Best of Both Worlds
Episode 145 Pantyhose Secrets
Episode 144 Do We Need Labels?
Episode 143 My Trip to the Mall
Episode 142 Getting My Geek On!
Episode 141 This One's for the Men
Episode 140 Disrespect
Episode 139 Is HRT for Me?
Episode 138 Being Safe While Dressed
Episode 137 Finding Sisterhood
Episode 136 Otokonoko
Episode 135 Crossdressing Injuries
Episode 134 Boobs as Medicine
Episode 133 Thinking Like a Woman
Episode 132 Buckets of Confidence!
Episode 131 The Cat's Out of the Bag... Sort of
Episode 130 Fitting Into a Woman's World
Episode 129 Can Crossdressing Ruin Your Career?
Episode 128 Finding Your Lane
Episode 127 Halloween Hijinks
Episode 126 How I Spent My Wife's Vacation
Episode 125 Crossdressing and Politics
Episode 124 All About Music
Episode 123 Emotional Support
Episode 122 Emergency!
Episode 121 Restroom Etiquette
Episode 120 It's All About the Face
Episode 119 Does Crossdressing Make You Gay?
Episode 118 Male Validation
Episode 117 Authenticity
Episode 116 I Love My Cis-ters!
Episode 115 Baby Steps
Episode 114 Pride vs Everyday
Episode 113 Regrets, I've Had a Few
Episode 112 For the Wives
Jennifer's Tale Twice a Week?!
Episode 111 Courage in Dressing
Episode 110 Crossdressing and Other Hobbies
Episode 109 Writing a Letter
Episode 108 Retail Therapy
Episode 107 Why Be Ashamed?
Episode 106 Am I Trans Enough?
Episode 105 Finding the Middle Ground - In Your Mind
Episode 104 In Case of My Death...
Episode 103 Pantyhose and Why I Love Them
Episode 102 Is It Really Worth It?
Episode 101 Finding Your Tribe
Episode 100 Sex and the Single/Married Crossdresser
Episode 99 Don't Be Afraid of Change
Episode 98 Different Shapes and Sizes
Episode 97 Oops!
Episode 96 Don't Embarrass Me
Episode 95 Let's Be Casual
Episode 94 Julie Does It Again!
Episode 93 How Much is Too Much?
Episode 92 Another Jennifer Day
Episode 91 Dealing With the Negative
Episode 90 A Little Spicy
Episode 89 Lack of Support (And I Don't Mean a Bra)
Episode 88 An Admiring Glance
Episode 87 What's in a Name?
Episode 86 Julie the Barista
Episode 85 Dressing Around My Wife
Episode 84 To Tuck Or Not to Tuck
Episode 83 Lunch With a Friend
Episode 82 I Have Questions!
Episode 81 What the Critics Say
Episode 80 Christmas Shopping with Jennifer
Episode 79 My Day Out in the Cold
Episode 78 My Friend Tracy
Episode 77 Looking Back
Episode 76 Day-to-Day Mentality
Episode 75 A Grand Day Out
Episode 74 I'm a Hypocrite
Episode 73 Sexy Soccer Mom
Episode 72 A Cold Day in November
Episode 71 How I Feel Feminine
Episode 70 Wearing Women's Clothing as a Guy
Episode 69 Finding Friendship
Episode 68 Flirting
Episode 67 Gene Simmons is Wrong
Episode 66 A Trip to the Grocery Store
Episode 65 Happy Halloween
Episode 64 Sex Sells
Episode 63 My Feminine Desires
Episode 62 She's Got Legs
Episode 61 Meeting Other Crossdressers
Episode 60 Things to Learn
Episode 59 Shopping for a Girl as a Guy
Episode 58 Wanting Attention
Episode 57 Dress for Sex-Cess
Episode 56 The Boobs Have It
Episode 55 Courage
Episode 54 Musings
Episode 53 Where Do I Go?
Episode 52 Dressing on a Limited Wardrobe
Episode 51 The Eyes Have It
Episode 50 Is Crossdressing an Addiction?
Episode 49 Getting a Pedicure
Episode 48 An Adventure with My Girlfriend
Episode 47 Competing Woman to Woman
Episode 46 Are Crossdressers Trans?
Episode 45 Getting the Girl Mojo Back
Episode 44 What Are the Odds?
Episode 43 Gender Fluidity
Episode 42 The Future
Episode 41 Underdressing
Episode 40 Early Influences
Episode 39 Self Confidence
Episode 38 Nature vs Nurture
Episode 37 More About My Boobs
Episode 36 Don't Be Afraid
Episode 35 What Covid Did to Me
Episode 34 Kids Are Too Smart
Episode 33 My Makeup Routine
Episode 32 Real Life Obstacles
Episode 31 Summertime
Episode 30 Body Type
Episode 29 Purging Your Wardrobe
Episode 28 Dare to Wear vs Don't Care
Episode 27 Thank You Sir
Episode 26 The Great Depression
Episode 25 The Benefits of Coming Out
Episode 24 My Dear Friend
Episode 23 Leading Two Lives
Episode 22 Voice Lessons
Episode 21 To Pad or Not to Pad
Episode 20 Taking the Perfect Selfie
Episode 19 My Mom Finds Out
Episode 18 My First Date
Episode 17 Manic Depression
Episode 16 My Secret Identity
Episode 15 My Boobs and Me
Episode 14 Dress for the Occasion
Episode 13 Escapism
Episode 12 My Sexuality Part 2
Episode 11 My Sexuality
Episode 10 My Son Finds Out
Episode 9 Traveling Small Town Iowa
Episode 8 First Time Meeting
Episode 7 Listener Feedback and More
Episode 6 Self Expression and Wellness
Episode 5 Close Encounter with a Friend
Episode 4 My Wife Finds Out
Episode 3 My Love of Pantyhose
Episode 2 My Fat Chest
Episode 1 All About Me