The Heroines of My Life: Interview with Allison Annalora

It is always a rare pleasure to return to a conversation with someone whose story continues to inspire and evolve. My first interview with Allison Lenore Annalora took place in 2013, and at that time I was struck by her warmth, honesty, and courage in sharing the many layers of her journey. Today, several years later, I am delighted to meet her again at a very special moment in her life. Allison has just published her long-awaited autobiography, Late Blooming: My Gender Journey, a candid and heartfelt account of her path toward authenticity. Allison is a woman of many talents and passions. She is a gifted singer, admired for her vibrant performances in cabaret and her ability to capture the glamour and spirit of the greats, including her beloved Barbra Streisand. She is also a creative hairstylist and make-up artist who has helped countless people feel beautiful and confident. Beyond her artistry, Allison is a woman who has lived through challenges that shaped her resilience, including a difficult childhood with adoptive parents who struggled with alcoholism, years of navigating gender identity in times when acceptance was far less visible, and heartbreaking personal losses that tested her strength.

What makes Allison’s story so compelling is her determination to live truthfully, even when doing so required sacrifice. She left behind a twenty-year-long relationship to pursue her transition, yet she found love again and built a life in which honesty and openness became her guiding principles. In her book she reflects on her early attempts to transition in the 1970s, the limitations she faced in that era, and the decades that followed before she was finally able to fulfill her dream of womanhood. She also recounts her journey to Trinidad, Colorado, where she met the renowned surgeon Dr. Marci Bowers, whose compassion and expertise played an important role in her story. Late Blooming is more than a personal memoir; it is a testimony of courage, resilience, and the search for authenticity. It resonates deeply with transgender women who see their own struggles reflected in its pages, but it also speaks to anyone who has ever longed to live a life aligned with their true self. The feedback from both transgender readers and cisgender allies highlights how Allison’s story opens minds and hearts, creating space for understanding and empathy.

As we begin this conversation, I feel honored to reintroduce Allison to my readers, not only as the vibrant performer and admired woman she has always been, but now also as an author who has gifted us with her life story in her own words. It is my joy to welcome her back and to invite you to discover the reflections, wisdom, and light she so generously shares.

Available via Amazon.

Monika: Allison, I am truly delighted to have the chance to speak with you again.

Allison: Thank you, Monika, for asking me to be interviewed! I always enjoy our conversations.

Monika: You look wonderful. It has been four years since our first interview, so I am curious, what changes have taken place in your life during this time?

Allison: Well, my boyfriend of six years moved in with me four years ago, and we’re still going strong. I appeared a second time at The McCallum Theatre, in their annual talent contest in 2015, as one of 25 finalists in front of an audience of 1,200. I didn’t win, but I sure had fun! I star in my own cabaret show, “Call Me Diva,” every other month at a local restaurant. It has been a joyful period filled with both personal and professional growth.

Monika: What inspired you to write your autobiography and share your story with the world?

Allison: I started a journal about finding my biological family in 1992. Both of my adoptive parents had passed, and I hoped for closure. As my life evolved and I transitioned, lots of friends and family encouraged me to tell my own unique story. After two years of rewrites and professional editing, I accomplished the second thing on my bucket list, which was explaining to the world how I achieved the first thing on my list: being my true self. Writing the book was both healing and empowering.

Monika: In your memoir, you devote significant space to your difficult childhood, growing up with alcoholic adoptive parents, struggling with gender identity issues, and being shunned by peers. What made you decide to revisit those painful memories in such detail?

Allison: It’s what shaped me into the person I am today, and I wouldn’t be who I am if those things had not happened. By reflecting on them, I found strength and a deeper appreciation for the resilience I discovered within myself.

Monika: Early in your life, you chose to present yourself openly as a feminine gay man at a time when the AIDS epidemic was emerging. Could you tell me more about what led you to that decision?

Allison: Actually, it was before we knew about AIDS. I started to transition in 1973 and 1974, however, my only choice back then was to live stealth. My compulsive truth-telling was not a trait that was compatible with living stealth. So, I chose to live as a feminine gay male and to do drag. I was unhappy with that life, but times changed and now I can have both, being my true self and being open about it. Those years were tough, but they taught me valuable lessons about courage and honesty.

Monika: One of the most heartbreaking moments of your life was the loss of your biological half-sister, Leslie Shawn. How did her passing affect you and your family?

Allison: She was murdered, and it’s something that none of us in my biological family will ever get over, especially our mother, Gail. You just learn to cope. Her absence is always felt, and keeping her memory alive helps us heal in small ways.

Monika: To live authentically, you made the difficult decision to end a twenty-year relationship. That must have been an enormous sacrifice.

Allison: And I got so much back in return. My ex, Bill, is my best friend now and even better, my boyfriend Ron and he are like brothers. It’s heartwarming to watch the two of them bond. They met because of me, but their friendship is something totally separate from me too. I feel blessed that what could have been a painful ending has turned into a new kind of family.

Monika: Your journey toward womanhood stretched over many years. Your first attempt at transition at the age of nineteen was unsuccessful, and you had to wait another thirty-five years before fulfilling your dream. How do you look back on that long delay?

Allison: As I explained earlier, that was not the path chosen until I was ready. I’ve come to see that the timing unfolded in exactly the way it was meant to.

Monika: In your book, you share the story of traveling to Trinidad, Colorado to meet Dr. Marci Bowers, one of the most respected gender confirmation surgeons in the United States. What was that experience like for you?

Allison: Yes, she had practiced in Seattle as an OB/GYN before and after her personal transition. I knew of her and we had a mutual client and patient that we were both fond of. That being said, and her sterling reputation, is why I traveled to Trinidad months before she moved her practice to California where I live. She is a wonderful person, and if she’s reading this: I love you! Meeting her gave me confidence that I was in the very best hands.

Monika: When other transgender women read your book, what do you hope they will take away from your story?

Allison: The trans women I’ve communicated with that have read my book have found many things they identified with. Generally, we all have similar struggles. My hope is to help encourage my community and to educate the general population also. The feedback from the cisgender readers has been a very fulfilling thing too. Read some of my reviews on Amazon.com where my book is available exclusively. Opening minds! Knowing that my story resonates with so many people makes me feel that writing it was truly worth it.

Monika: Allison, thank you so much for sharing your story with me today. I believe your book will inspire not only other transgender women but also many readers outside the community.

Allison: And hoping everyone else reads my book as well! Thank you for asking! You are doing great work yourself, Monika! It means a lot to have your support in helping me spread my message.

Monika: Thank you so much, Allison!