EPISODE · May 30, 2025 · 1H 9M
1128 - FETISH FRIDAY: Lilly is a Sissy Crossdresser
from Strictly Anonymous Confessions · host Kathy Kay
Lilly is a sissy crossdresser and he called in to talk all about it. Tune in to hear all the details including how and why he started being into panties and how that led to fully dressing, how he got caught dressing by his mom and how she reacted, how he told some friends in high school and how they reacted and the difference between the guys’ vs. the girls reactions, how and when he realized he’s a crossdresser and not trans, the relationship he currently has with a girl who treats him as her sissy, how and when she copped to being into his crossdressing and his sissy side, their first hook up and how it quickly progressed to pegging and more, the tasks she makes him do for her, the sissy he met who he now Doms and what he enjoys about that relationship, what they do together online, how often he dresses up now that he lives alone, how he likes to dress and how passable he is, what he’s looking for in his future plus a whole lot more. **To see anonymous a pics of LILLY'S STASH plus see pics my other female 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 MY BOOK IS NOW OUT FOR PRE-ORDER!!!! Strictly Anonymous Confessions: Secret Sex Lives of Total Strangers. A bunch of short, super sexy, TRUE stories. GET YOUR COPY NOW: 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" Have something quick you want to confess while remaining anonymous? Call the CONFESSIONS hotline at 347-420-3579. You can call 24/7. All voices are changed. Sponsors: https://viia.co/STRICTLYANON Try VIIA and use code STRICTLYANON for great SEX and sleep https://www.dipseastories.com/strictlyanon Hear the hottest stories on Dipsea and get a 30-day FREE trial PLUS 25% off your subscription https://butterwellness.com/ Use the code “STRICTLY” at checkout for 20% off your entire order https://bluechew.com Get your first month of the new Blewchew Max FREE! use code: STRICTLYANON https://beducate.me/pd2512-anonymous Use code anonymous to get an additional 10% off the campaign’s current discount - that’s 60% off https://shamelesscare.sjv.io/xLQ3Jv Get $10 off Shameless Care’s female viagra cream, just click on the link and use code: Strictly Follow me! Instagram https://www.instagram.com/strictanonymous/ Twitter https://twitter.com/strictanonymous?lang=en Website: http://www.strictlyanonymouspodcast.com/ Everything else https://linktr.ee/Strictlyanonymouspodcas Learn more about your ad choices. Visit megaphone.fm/adchoices
What this episode covers
Lilly is a sissy crossdresser and he called in to talk all about it. Tune in to hear all the details including how and why he started being into panties and how that led to fully dressing, how he got caught dressing by his mom and how she reacted, how he told some friends in high school and how they reacted and the difference between the guys’ vs. the girls reactions, how and when he realized he’s a crossdresser and not trans, the relationship he currently has with a girl who treats him as her sissy, how and when she copped to being into his crossdressing and his sissy side, their first hook up and how it quickly progressed to pegging and more, the tasks she makes him do for her, the sissy he met who he now Doms and what he enjoys about that relationship, what they do together online, how often he dresses up now that he lives alone, how he likes to dress and how passable he is, what he’s looking for in his future plus a whole lot more. **To see anonymous a pics of LILLY'S STASH plus see pics my other female 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 MY BOOK IS NOW OUT FOR PRE-ORDER!!!! Strictly Anonymous Confessions: Secret Sex Lives of Total Strangers. A bunch of short, super sexy, TRUE stories. GET YOUR COPY NOW: 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" Have something quick you want to confess while remaining anonymous? Call the CONFESSIONS hotline at 347-420-3579. You can call 24/7. All voices are changed. Sponsors: https://viia.co/STRICTLYANON Try VIIA and use code STRICTLYANON for great SEX and sleep https://www.dipseastories.com/strictlyanon Hear the hottest stories on Dipsea and get a 30-day FREE trial PLUS 25% off your subscription https://butterwellness.com/ Use the code “STRICTLY” at checkout for 20% off your entire order https://bluechew.com Get your first month of the new Blewchew Max FREE! use code: STRICTLYANON https://beducate.me/pd2512-anonymous Use code anonymous to get an additional 10% off the campaign’s current discount - that’s 60% off https://shamelesscare.sjv.io/xLQ3Jv Get $10 off Shameless Care’s female viagra cream, just click on the link and use code: Strictly Follow me! Instagram https://www.instagram.com/strictanonymous/ Twitter https://twitter.com/strictanonymous?lang=en Website: http://www.strictlyanonymouspodcast.com/ Everything else https://linktr.ee/Strictlyanonymouspodcas Learn more about your ad choices. Visit megaphone.fm/adchoices
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1128 - FETISH FRIDAY: Lilly is a Sissy Crossdresser
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