In the realm of LGBTQ and civil rights politics, there are few people more experienced than the rightfully esteemed Cleve Jones. We’ve interviewed Cleve before, but in light of the upcoming election and the onslaught of anti-LGBTQ legislation and sentiment coming from the conservative side of the political spectrum, we wanted to have Cleve back on our show to give us his thoughts on how we as queer, kinky, and otherwise marginalized people can rally the vote in November and maintain our freedoms and move our causes forward.

On Guard Cigar Salon has been producing content for more than 2 years. Often when we finish recording an episode, one of us suddenly thinks "I forgot to say this" or "I wish I had covered that." So, in this Shoulda Coulda Woulda episode we look back at the first 2 years of On Guard and critique ourselves, what did we get right, what did we get wrong, and what we wish we would have said instead.

Gay leather and drag cultures have been intertwined for decades. Within gay communities, leather and drag have often formed strong alliances and been considered outsiders, mavericks, and rebels. Leather and drag community members have also often been part of the vanguard of LGBTQ activism. That's why On Guard wanted to interview someone from the drag community to discuss our shared commonalities as well as the recent anti-drag sentiment that echoes the anti-LGBTQ and anti-leather/kink forces with which many of us have had to deal with our entire lives.

Music is such an important part of our culture and that includes queer, leather, and kink culture. The On Guard crew has had their gay and kinkster journeys influenced by music throughout the years. In this episode, each of us talks about the music that has had the most impact on us and why.

Bootblacks. What do they do, and why? What are some of the ins and outs of bootblacking itself? How do bootblacks fit into the fabric of kink and leather culture. These are just some of the questions we asked one of the country's preeminent bootblacks, Buck Harder. You'll find Buck teaching or practicing his craft on his social media channels, at leather events, or on most Sundays at the Barracks bar in Palm Springs.

For 40 years the Tom of Finland Foundation has been dedicated to protecting, preserving, and promoting the erotic arts. The On Guard crew was lucky enough to interview Durk Dehner, Co-Founder of the TOF Foundation, while we were in Palm Springs Live at the Tool Shed bar during Palm Springs Leather Pride weekend. Durk tells us stories about Tom, his art, and other erotic artists that you'll only hear about on this episode.

We're living in a time when trans issues are front and center in the social discussion, both within kink communities and elsewhere. But what is being kinky and trans really like? What was it like to transition decades ago and how does it differ today? How does a trans man best navigate within gay men's spaces? How can event producers, groups, and individuals within the kink scene be useful allies and inclusive of trans men?

These are just some of the topics covered in this lively conversation with well-known leatherman and kinkster, Mike Hernandez. And there’s some very funny stories told that had the entire On Guard crew laughing a lot.