EPISODE · Jan 9, 2026 · 53 MIN
1331 - Sissy is into Men, Dressing up and Being Sissified
from Strictly Anonymous Confessions · host Kathy Kay
Sissy is into dressing up and being sissified and he called in to talk all about it. Tune in to hear all the details including when he started hooking up with his male high school friend and how he felt about it at first, when the whole being a sissy and dressing up started for him, what he started wearing first and how progressed, when he got caught hooking up with his guy friend while dressed up when he was younger, when he started fully dressing up and why he didnt tell his girlfriend, when he got caught hooking up with his guy friend by his current girlfriend and how that led her into sissifing him, when she started buying him toys and using them on him whole he was with his guy friend and what exactly would go down, why the relationship with his girlfriend ended plus a whole lot more. To see anonymous a pics of my guests + get TONS of exclusive CROSSDRESSER and or HOSER episodes and content + hear all the anonymous confessions, join my Patreon Crossdresser tier it's only $8 a month for Hosers and $10 a month for crossdressers (you get also get Hoser episodes too!) and you can cancel at any time. You can sign up here: https://www.patreon.com/StrictlyAnonymousPodcast GET A COPY OF THE STRICTLY ANONYMOUS BOOK! Strictly Anonymous Confessions: Secret Sex Lives of Total Strangers. A bunch of short, super sexy, TRUE stories. GET YOUR COPY HERE: https://amzn.to/4i7hBCd To join SDC and get a FREE Trial! click here: https://www.sdc.com/?ref=37712 or go to SDC.com and use my code 37712 Want to be on the show? Email me at [email protected] or go to http://www.strictlyanonymouspodcast.com and click on "Be on the Show." Want to confess while remaining anonymous? Call the CONFESSIONS hotline at 347-420-3579. All voices are changed. Sponsors: https://vb.health — To get 10% off DRIVE Boost by VB Health use code: STRICTLY https://www.quince.com/strictlyanon — For premium quality Quince clothing plus FREE shipping and 365 day returns! https://butterwellness.com/ — Use the code STRICTLY at checkout for 20% OFF your entire order https://beducate.me/pd2540-anonymous— Click here to take the quiz and get your personalized roadmap to sexual happiness https://bluechew.com — Get 10% OFF your first month of Bluechew GOLD! Use code: STRICTLYANON https://motorbunny.com/strictly — Click to get $50 off! Follow me! Instagram https://www.instagram.com/strictanonymous/ X https://twitter.com/strictanonymous?lang=en Website http://www.strictlyanonymouspodcast.com/ Everything else: https://linktr.ee/Strictlyanonymouspodcast Learn more about your ad choices. Visit megaphone.fm/adchoices
What this episode covers
Sissy is into dressing up and being sissified and he called in to talk all about it. Tune in to hear all the details including when he started hooking up with his male high school friend and how he felt about it at first, when the whole being a sissy and dressing up started for him, what he started wearing first and how progressed, when he got caught hooking up with his guy friend while dressed up when he was younger, when he started fully dressing up and why he didnt tell his girlfriend, when he got caught hooking up with his guy friend by his current girlfriend and how that led her into sissifing him, when she started buying him toys and using them on him whole he was with his guy friend and what exactly would go down, why the relationship with his girlfriend ended plus a whole lot more. To see anonymous a pics of my guests + get TONS of exclusive CROSSDRESSER and or HOSER episodes and content + hear all the anonymous confessions, join my Patreon Crossdresser tier it's only $8 a month for Hosers and $10 a month for crossdressers (you get also get Hoser episodes too!) and you can cancel at any time. You can sign up here: https://www.patreon.com/StrictlyAnonymousPodcast GET A COPY OF THE STRICTLY ANONYMOUS BOOK! Strictly Anonymous Confessions: Secret Sex Lives of Total Strangers. A bunch of short, super sexy, TRUE stories. GET YOUR COPY HERE: https://amzn.to/4i7hBCd To join SDC and get a FREE Trial! click here: https://www.sdc.com/?ref=37712 or go to SDC.com and use my code 37712 Want to be on the show? Email me at [email protected] or go to http://www.strictlyanonymouspodcast.com and click on "Be on the Show." Want to confess while remaining anonymous? Call the CONFESSIONS hotline at 347-420-3579. All voices are changed. Sponsors: https://vb.health — To get 10% off DRIVE Boost by VB Health use code: STRICTLY https://www.quince.com/strictlyanon — For premium quality Quince clothing plus FREE shipping and 365 day returns! https://butterwellness.com/ — Use the code STRICTLY at checkout for 20% OFF your entire order https://beducate.me/pd2540-anonymous— Click here to take the quiz and get your personalized roadmap to sexual happiness https://bluechew.com — Get 10% OFF your first month of Bluechew GOLD! Use code: STRICTLYANON https://motorbunny.com/strictly — Click to get $50 off! Follow me! Instagram https://www.instagram.com/strictanonymous/ X https://twitter.com/strictanonymous?lang=en Website http://www.strictlyanonymouspodcast.com/ Everything else: https://linktr.ee/Strictlyanonymouspodcast Learn more about your ad choices. Visit megaphone.fm/adchoices
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1331 - Sissy is into Men, Dressing up and Being Sissified
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