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This conversation breaks down outdated ideas around masculinity and underwear.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 – https://bsky.app/profile/playsbothsides.bsky.social
• Reddit – https://www.reddit.com/user/No-Economy-1361/
• FetLife
He’s friendly, approachable, and always happy to talk underwear, fit, brands, and style.
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Feedback & Questions
Have thoughts on the episode or questions for the show?
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