EPISODE · Jun 27, 2025 · 1H 5M
1154 - FETISH FRIDAY: Jack is a Fluid Crossdresser who is Totally Into Prostate Play
from Strictly Anonymous Confessions · host Kathy Kay
Jack is a fluid crossdresser who is totally into prostate play and he called in to talk all about it. Tune in to hear him discuss all the details including how and when he realized he was into wearing female clothing and what he enjoyed about it at first, when he got into trans porn and exploring anal play, his first hook-up he had with another crossdresser and exactly what went down, his stash he was accumulating and where he gets everything from, how he told one of his girlfriends that he was into pegging and how she reacted, the first guy he hooked up with and exactly what went down between them, how he brought up his crossdressing and his interest in guys to his last girlfriend and how she reacted and what followed including him getting pegged by her while he is dressed, how and why they broke up and how she threw his fetish in his face at the end, the prostate orgasms he has had and how they feel, the anal toys he enjoys the most and the ones he recommends to start out with, how he got a throat infection from deep throating a toy one time and how long it lasted plus a whole lot more. **To see anonymous a pics of JACK 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://butterwellness.com/ Use the code “STRICTLY” at checkout for 20% off your entire order https://vb.health To get 10% off Drive AND LOAD Boost by VB Health use code: STRICTLY https://bluechew.com Get your first month of the new Blewchew Max FREE! use code: STRICTLYANON https://beducate.me/pd2516-anonymous Use code anonymous to get 50% off your yearly pass plus get a 14 day money back guarantee 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
Jack is a fluid crossdresser who is totally into prostate play and he called in to talk all about it. Tune in to hear him discuss all the details including how and when he realized he was into wearing female clothing and what he enjoyed about it at first, when he got into trans porn and exploring anal play, his first hook-up he had with another crossdresser and exactly what went down, his stash he was accumulating and where he gets everything from, how he told one of his girlfriends that he was into pegging and how she reacted, the first guy he hooked up with and exactly what went down between them, how he brought up his crossdressing and his interest in guys to his last girlfriend and how she reacted and what followed including him getting pegged by her while he is dressed, how and why they broke up and how she threw his fetish in his face at the end, the prostate orgasms he has had and how they feel, the anal toys he enjoys the most and the ones he recommends to start out with, how he got a throat infection from deep throating a toy one time and how long it lasted plus a whole lot more. **To see anonymous a pics of JACK 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://butterwellness.com/ Use the code “STRICTLY” at checkout for 20% off your entire order https://vb.health To get 10% off Drive AND LOAD Boost by VB Health use code: STRICTLY https://bluechew.com Get your first month of the new Blewchew Max FREE! use code: STRICTLYANON https://beducate.me/pd2516-anonymous Use code anonymous to get 50% off your yearly pass plus get a 14 day money back guarantee 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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1154 - FETISH FRIDAY: Jack is a Fluid Crossdresser who is Totally Into Prostate Play
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