Kyle Meets… Key West Bear 2019 Pepa Mahogany, talks diversity and bear mindset

“Diversity” and “inclusion” are words that we hear a lot of in the LGBTQ community. It has always seemed a bit strange that, for a community that was built as a safe space for the outcasts and underdogs of society would have a problem understanding that all people, regardless of race, age, size, orientation, etc., should be welcome.

In the bear community, the standards by which one is considered a bear are often challenged. Sometimes, men who are not large, men who are not hairy, or men who do not have beards, may still feel most comfortable in bear spaces. They may still consider themselves bears even though some of these boxes may not be checked. Being a bear is more a state of mind than a set of physical standards.

Recently, I had a chance to speak with Pepa Mahogany, the winner of the 2019 Mr. Key West Bear title, to discuss diversity, inclusion, and when he discovered that being a bear was a mindset, not a set of physical attributes.

KJ: Hi, Pepa! Can you tell our readers a bit about yourself? 

PM: Well, hello everyone, and big bear hugs! My name is Floyd, AKA Pepa. I was born and raised in Flint, Michigan. I’m named after my father, Floyd, Sr. He was from Detroit and my mom, Shirley, was originally from Alabama, so I was raised with southern charm and manners along with Midwestern swing. 

When I was 6, we moved to a suburb of Flint called Grand Blanc. I definitely stood out like a sore thumb, because, at that time, the town was predominantly white. I was considered  “different” because of my brown skin, and the fact I liked rainbows and unicorns instead of the typical boys stuff. 

I was teased and called “gay/faggot/nigger” before I even knew what any of those words meant. I just didn’t understand why guys couldn’t be expressive and play with whatever toy they wanted to play with no matter what gender it was made for. I dealt with it from elementary to middle school, and when I got to High School, during my freshmen year, I came out, and was like, “Yeah, I’m gay. So…” 

Suddenly, everything changed. I went from being the kid constantly bullied to the “cool” kid. The messed up thing was that I never officially came out to my mom. My dad had passed by then, but I was trying to work up the courage to tell my mom. Everytime I tried, I just couldn’t get the words out. 

One day she found a letter I wrote to a crush and… Yeah, that didn’t go over very well. When I graduated, it was made crystal clear that I should find a new home. So, that’s what I did. And I never looked back. I worked and figured out adulting pretty much by myself, independently navigating through life. 

I always knew I wanted to live somewhere warm, do some great things, and be somewhere I could truly be myself. One day I said to myself, “If you don’t do this now, you’ll never do it”. So, I sold everything, packed only what I needed, and moved to Key West, Florida in 2007. This has been my home ever since. 

I consider Key West the city that raised me. Living here has taught me so much about myself and different cultures, and has taught me a lot about people from all over the world. I truly love embracing everyone’s uniqueness and differences as a strength, instead of fear! I love this island! 

Fast forward to today – I’m happily married to my husband, Joey. We met here on the island in 2011, and married in 2016. He has a beautiful daughter from a previous marriage, Victoria, who is now my daughter, and I love her dearly! We also are proud cat dads to our adopted Sphinx cat named Zuki. I work in healthcare, and when I’m not working, you can find me watching movies, playing video games, volunteering my time helping out with different causes, and hanging with friends. 

KJ: Wow! Your journey has been quite amazing. When did you begin identifying as a Bear? Can you tell us a little bit about your journey as a Bear? 

PM: I started identifying as a Bear about 3 years ago, but it took me a while to get there. I have always been attracted to men with thicker builds and facial hair. I remember when I was a teenager, when the group N’SYNC was popular, and all my friends were pining for Justin. I was into Joey because he looked so different from the clean cut shaven guys. He had facial hair, a bigger body, and was hairy.

Ironically, I have dated lots of guys that had similar builds and features. It was really after I started going to bear events and joining online communities that I realized that bears actually come in all shapes, sizes and colors. It’s also a mindset. What I was seeing was what is typically shown in popular gay media – It’s a one dimensional image, and I had based my own identity within the community by that stereotype presented to me. 

I thought for the longest you could only be white, hairy and big to be a bear, which is furthest from the truth. I always had a thin frame and an athletic build growing up, and although the bear community still accepted me and showed love, I wasn’t sure if I could claim to be a bear even though I felt most comfortable within the community. I learned it’s not only about your physical attributes, but again, it’s a mindset. There’s plenty of bigger guys that don’t identify as bears. In fact, many larger guys may get offended if you call them a bear. 

As time went on, I got older and my metabolism changed. My body also changed, and suddenly I was able to grow a beard, and my hips, thighs and belly started to fill out. People’s reactions to me and their perceptions of me changed. I started hearing the words “Bear” and “Daddy” thrown my way when I was being described by folks. I was like, “Okay, it looks like I have a seat at the table now, but now I’ve got some work to do.” 

KJ: What made you enter the competition? 

PM: I wanted to fill a void and voice the things I don’t think have always been seen or heard. This community, despite certain stereotypes, is actually very multidimensional. I love the bear community, but I wasn’t seeing many people of color at events, especially ones like myself who enjoys the hypermasculinity, but also enjoys sexy cosplay/fantasy and all things fun and geeky. 

I represent those not afraid to explore certain parts of themselves that break gender norms – the more forward thinking generation of bears that play with ALL the colors of the rainbow, while still being authentically themselves. 

KJ: What was your favorite part about taking part in the competition?

PM: I loved the whole experience. But if I had to narrow it down to one thing, I would say it was the sexy/fetish underwear part of the competition. I love dressing up, and any excuse to wear something flirty, sexy and fun I’m all about.

KJ: What is your platform? 

PM: My platform is gonna touch on several things, but I plan to use my visibility and voice to encourage more inclusivity and diversity in the bear community. I want to offer my services and talents to my community to bring awareness to issues that affect people living in the Keys and outside of the Keys. 

I don’t want to just parade around in dark bars with my sash and message. This beautiful leather sash, made by Leather Master Key West, will see the light of day, and will be out in the community in order to show that your Mr. Key West Bear 2019 is your neighbor, friend, coworker, lover, father and more. 

Being true to yourself along with the freedom/empowerment it gives you is at the heart of my platform. 

KJ: In what ways do you think you can help to promote growth or change in the leather and/or bear/cub communities? 

PM: I think my win alone is a positive step towards the growth and change in the community. My face, who I am as a person, what I represent, and what I plan to do is helping to show others you don’t have to fit into a particular box to be a bear. 

The outpouring of love and support I’ve received has been amazing, and people that haven’t  always felt like they had a seat at the table are feeling like they are now being represented, and that’s so important to me.

KJ: What is the most important thing about the bear/cub community for you? 

PM: The sense of love and family I feel within our community. It’s definitely our strength. Every year when I attend bear/cub events, I meet so many beautiful people from all over that I’m blessed to call my friends. Those bonds have just been getting stronger and stronger.

KJ: What are your plans for your title year? 

PM: I have a wish list of things that I want to do going forward for the rest of the year. I want to do something every month of my title year. November is already covered because I’ve been raising funds all year while training for the SMART Ride. 

SMART Ride is a 2 day event for individuals who will ride their bicycles on November 16th and 17th 165-miles from Miami to Key West to raise money for AIDS organizations in Florida. I’m part of the Key West Mile Markers and I couldn’t be more proud and excited to do it! I also plan to bring awareness to the reefs here in the Keys, fundraising for more causes, and putting a spotlight on depression and how it affects our brothers & sisters.                                                                                                       

I also want to put together events that bring awareness to the importance of reading and donating books for children, putting together more fun bear events, and working with animals that need good, loving homes. I want to travel with my title and promote what makes Key West unique and special, while helping my fellow title holders and the bear community, and so much more. 

KJ: Will you go on to enter other competitions once your title year is done? 

PM: Absolutely! I’ll continue doing other bear competitions, and I would like to further explore the world of leather and rubber! 

KJ: Finally, what’s your advice for anyone entering the competition next year? 

PM: Have fun and be yourself. Definitely do your homework and learn from others. Come prepared. Be nice and get to know the other contestants you’re competing with. You’re going to spend a considerable amount of time with them backstage, you might as well make a new friend! And, lastly, breathe.

Follow Pepa Mahogany, Mr. Key West Bear 2019, on Facebook and Instagram.

The Mr. Key West Bear Contest is was sponsored by Leather Master Key West, the providers of the beautiful new Mr. Key West Bear sash, and Growling Grooming, who provided a $100 gift certificate.

For over 40 years, Leather Master Key West has been Key West’s Only Adult Entertainment retail shop for sex toys, adult novelties, sexy wear, fetish accessories, leather gear, handmade masquerade masks and professional stage makeup. To find out more information, and to shop more of their products, please visit their website at

Growling Grooming provides all natural and sustainable beard care products made for bears by bears. To find out more information, and to shop more of their products, please visit their website at

Kyle Jackson

Kyle Jackson (He/Him) is Senior Staff Writer at Gray Jones Media, and additionally works as a writer, editor and theatre artist/actor. A native of New Orleans, Louisiana, he studied at Dillard University, received a BA in Theatre from Morgan State University, an MS in Arts Administration from Drexel University, and completed the British American Drama Academy’s Midsummer in Oxford Programme in 2017. Having lived in Baltimore, the Washington, DC area, Philadelphia and New York City, he now resides and works in London, United Kingdom.

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