A chat with Cub Teddy, the winner of Route 66 Bear 2025!

28th May 2026 Bryce Quartz

We got to chat with Cub Teddy, the Route 66 Bear 2025 titleholder, about how he got into competing, representing for his community, and more!

KINK Weekend is an event that was conceived by the Oklahoma City Boys of Leather in 2011 as a way to celebrate the organizations one-year anniversary, as well as to showcase the different talents and fetishes that are in the community.

In the process of setting the stage for some highly erotic, entertaining and sensual times for visitors to the event, also acted as a community service project by raising money for different charities and organizations throughout Oklahoma City.

Over the years the event changed from a single night show and fundraiser, to a multi-day event with entertainment, education and competition.

In 2013, a new leather contest was started to coincide with the three-day event. This contest was owned and sponsored by the Sisters of Perpetual Indulgence in Oklahoma City. This new contest was titled the Heartland Leather Contest. The sisters retained ownership until selling it to Nate Benner in 2015 with the understanding that the name of the contest was to be relinquished.

Once ownership was changed, Mr. Benner renamed and rebranded it as the Rt. 66 Leather Contest and turned it into a national title. The first contest of Rt. 66 was held in July of 2015 where Russel McDaris, Mr. Heartland Leather 2015, presented the new title to Randal Whiterock-Zotigh, Mr. Rt 66 Leather 2016.

Last year, Cub Teddy became the winner and titleholder of Route 66 Bear for 2025. Cub Teddy is a lovely and nostalgic teddy bear that’s fresh off the shelves who’s always ready to aid anyone on their kink journey. They are here to spread education in a fun and interactive way, specializing in education about Exhibitionism, Outdoor Play, Smutty Media, Roleplay, and Power Struggle.

I had the chance to speak with him about running for the title, his experience in the leather and kink community, and more! Check it out below.

Bryce Quartz: Hey there, Cub Teddy! Thank you so much for taking the time to speak with me today. How have you been doing lately?

Cub Teddy: I have been good! Just got back from Meat in the Middle in Columbia, MO! It was a great event and focused heavily on local community. It was also just good to get out and celebrate being openly queer.

Bryce: Let’s jump right into the good stuff. You recently won the title of Route 66 Bear at KINK Weekend in Oklahoma City, and we’ll get into that, but first, I want to know more about your background. How long have you been in the competitive title landscape within our community, and what initially interested you in competing?

Cub Teddy: I have been in the title sphere for about two years now. On New Years, I had gone to the bar on a whim, and it happened to coincide with their gear night. The local bear title holder at the time flirted with me, so I flirted back. We got to talking and he had mentioned the contest sphere. Specifically, that I would be a good candidate for the bear title if I wanted to try it out. After doing some more research on it, I decided that it was something that I wanted to pursue.

Bryce: Now let’s get into your journey to becoming the Route 66 Bear. What was the process like from applying to compete to preparing your package?

Cub Teddy: Oh wow, it was a lot of prep work. On-stage looks, an auction basket, class, and speech, it was all a lot of pressure. I got the looks done pretty easily with one being my absolute favorite. It was this bear onesie that I had sewed patchwork onto and stuffing placed so I looked like a patchwork teddy bear.

It was for the hot wear portion, and it was definitely HOT. I was drenched in sweat while on-stage then had to chug a bottle of water backstage, but it was worth it. The auction basket and class were trickier. For the basket, I am a big DND nerd, so I focused on it as a theme.

I reached out to my local game stores and sex toy vendors and they donated a good portion of the items to be auctioned off. At the end, I had a full spread: A full DnD campaign and world build ready to go, kinky characters with art and figures, a d20 ball gag, and they were all inside a wooden, nautical chest.

The class focused on smutty media. I like to roleplay in the bedroom, so I used the smutty novels I had read to help elevate my themes and the archetypes of characters I roleplayed. I mixed my two loves and the class “Simply Smutty” was born!

Finally, when it came to my speech, I had to go through many, many, many revisions of what to say on stage. After tons of practicing, I’m very proud of how my speech came out when it came time to deliver.

Bryce: Your kink specialties include exhibitionism, outdoor play, smutty media, roleplay, and power struggle. Can you tell us more about your experience with these kinks and fetishes, and how you educate newcomers?

Cub Teddy: Yeah! Exhibitionism and outdoor play are easy ones to start, but can be a bit dangerous. Cruising is a big one I like as well, but new kinksters should be careful. The kink is common, but it is technically still illegal if you don’t play your cards right.

I suggest trying nude campgrounds because those are a great way to safely participate in these kinks. If you don’t have one nearby, then talk to your local kinksters and community members and they will likely know the places to go and not go in your areas.

The others are much trickier. Roleplay and power struggle require a good chunk of communication to occur before play. These kinks may seem fun in concept, but practice can lead to complications. Say for instance I am doing a wrestling power struggle scene, I need to know the outline of the scene (what we are doing, where and who we are, etc.), areas/past injuries to avoid, safe words, and signals in case my play partner goes nonverbal.

When play starts to get physical and more forceful, it’s important to set up multiple safety nets so that everyone leaves happy, whole, and satisfied with the experience. Smutty media is tied into all of these kinks. I listen to them during car rides (which provides a small sense of exhibitionism) and then use the concepts to help enrich my roleplay experiences.

For new kinksters, I definitely recommend starting with smut to get a concept of what you like and fantasize about, as well as what you definitely don’t want to do.

Bryce: Competing for titles can be high pressure and a bit stressful, but it can also be rewarding in more ways than one. What are some of the highlights you’ve had that came with competing for the title of Route 66 Bear?

Cub Teddy: OMG! 100% it was when our competing bootblack took the stand. Rt 66 bootblack contestants have to do a practical display of their skills. Our bootblack, Atlas, asked if the other contestants and I would sit in his stand.

I do a lot of work in construction and environmental sites, so I had a pair of workboots that were absolutely filthy. I showed him the boots and he looked so excited at the challenge that I just couldn’t resist letting him work on them. He gave me the full spa treatment and revealed that my boots weren’t gray, but actually a reddish-brown color.

The man took care of them so quick, and the judges were very impressed. I felt like a proud papa bear the whole time and was so glad to get to share the experience with him. Highly recommend Atlas to bootblack your gear if you ever catch him on the stand!

Bryce: Do you have any advice for those that have never competed for a title before but are interested in doing so?

Cub Teddy: My biggest piece of advice that I can share is understanding that these titles are leadership positions in the community. You should have a message or platform, something you think people need to hear and understand.

Something that, whether you win, lose, or draw, is still important and worth sharing. The competition is fun, but ultimately these titles are to enrich and better the community. That’s what you should expect to do if you run.

Bryce: If you had to choose a mission statement to represent you as a person and title holder, what would it be and why?

Cub Teddy: I think my message would be: “Body euphoria overcoming body dysmorphia”. Like many others, I suffer with body dysmorphia. Somedays I feel good and others I don’t. On the days I don’t, I try and focus on what I do like about my body.

Changing the narrative to find the joys in myself instead of the pain. It isn’t easy and it takes practice, but soon those good days will outpace the bad ones.

Bryce: Let’s switch it up a bit. I love asking this question to literally everyone. What are some of your favorite foods, dishes, and restaurants?

Cub Teddy: OMG yes! I went to college at Iowa State, and while I was there I loved trying new restaurants and food. My favorite food that I tried is Gan Guo, which is like a dry, braised hot pot.

The restaurant, Szechuan House, had a bunch of different kinds, but I kept coming back to the pork intestines. They have a chewy consistency that reminded me of chicken gizzards growing up. Highly recommend them, but in general you should try new foods. Sometimes they will surprise you!

Bryce: Outside of being a handsome cubby bear and title holder, what are some of your interests and hobbies?

Cub Teddy: I love video games and books (especially the smutty ones). I also like to hike and collect different rocks. I have a big collection of gemstones that I got growing up around gem mines in southern Virginia.

I play a lot of Magic the Gathering, both on arena and at local game stores. Oh! And I enjoy doing burlesque as well! It’s another activity I cant recommend enough! Burlesque performers are the sweetest and most accepting people.

Bryce: Thank you so much for taking the time to speak with me! Is there anything else you’d like to share with our readers today?

Cub Teddy: Absolutely! I had a great time. If you ever see me out and about, come say hello to me and don’t be shy! Also, if you ever want or need a hug, remember to just ask first. Give me a follow on social media too if you want to see more of me! Thank you for taking the time to read about my story.