Brief Talk Podcast – Brief Tale featuring Playsbothsides

Brief Talk Podcast — Brief Tale with Jason (“Plays Both Sides”) In this episode of Brief Talk, Tim sits down with Jason—known online as Plays Both Sides —for an open, honest, and refreshingly candid conversation about underwear, masculinity, sexuality, and self-expression. Jason is a straight guy who discovered thongs, jockstraps, and cheeky underwear later in life—and never looked back. What began as curiosity turned into confidence, community, and a full-on underwear lifestyle. Together, Tim and Jason unpack what it really means to feel sexy, why underwear doesn’t define sexuality, and how exploring personal style can unlock self-acceptance, better health, and deeper connections with others. Episode Highlights • Jason’s late-in-life discovery of thongs and jocks after years of wearing boxer briefs • The moment he realized underwear could make him feel sexy, not just be functional • How curiosity turned into collecting, researching brands, and engaging with the underwear community • Why underwear choice has nothing to do with sexual orientation • Navigating underwear exploration while in a long-term straight relationship • Support, openness, and humor from Jason’s girlfriend—and where she draws the line • Finding confidence, motivation, and improved health through feeling good in what you wear • The surprising role of Jason’s gay brother and the Houston leather and kink community in his journey • From Reddit friendships to in-person meetups—and even being gifted a bag of underwear • Favorite brands, styles, colors, and the move from thongs into classic jockstraps • Curiosity about lingerie, lace, corsets, and pushing past traditional ideas of masculinity • Why more straight men are openly embracing underwear, jocks, and swimwear today • Advice for guys who are curious but hesitant: try it—your underwear doesn’t define you Why This Episode Matters This conversation breaks down outdated ideas around masculinity and underwear. Jason’s story shows that exploring what makes you feel good—whether that’s thongs, jocks, or lingerie—is about confidence, not labels. It’s about doing something for yourself and finding community along the way. Follow Jason You can find Jason online under the handle Plays Both Sides on: • BlueSky – • Reddit  – • FetLife He’s friendly, approachable, and always happy to talk underwear, fit, brands, and style. ⸻ Support UNB If you enjoy the podcast and want to help support Underwear News Briefs and the Brief Talk Podcast, there are several ways to get involved: Ongoing Support • Join our Patreon: You can now join for free, with optional paid tiers for additional support. One-Time Support • Visit our support page: Donate via Ko-fi or PayPal. Shop & Support • Shop the UNB Store: • Gift us something from our wish list: Support Our Partners • Buy Amoresy: • Buy BodyAware: • Buy Xdress: • Buy Real Men Apparel: ⸻ Find Out More • Read more at: unbblog.com Follow UNB • Twitter: • Instagram: • Reddit: ⸻ Follow Tim • Twitter: • Instagram: • Facebook: • BlueSky: • Spandex Party: ⸻ Feedback & Questions Have thoughts on the episode or questions for the show? Email us at feedback@brieftalkpodcast.com

You can listen to Brief Talk Podcast – Brief Tale featuring Playsbothsides online on Radio and Podcast. Open the player on this page to stream the available audio.

Brief Talk Podcast – Brief Tale featuring Playsbothsides is an episode from Brief Talk Podcast by Underwear News Briefs by UNB Blog.

This episode is 53:44 long.

This episode was published on Jan 9, 2026.

Yes. Use the heart button on the episode page to add it to your favorite episodes list.

Yes. This page shows related episodes from Brief Talk Podcast by Underwear News Briefs when more episodes are available from the podcast feed.