https://www.freepornflix.com/categories/made-to-crossdress/ Thu, 16 Apr 2026 11:17:14 UTC https://www.freepornflix.com/video/765130/valentines-day-sissy-cuckold/
Both parts of the story for one low price.  over an hour and 15 minutes of feminization, domination, and sissy training.joyce best friend is with the wrong guy.  they share everything and they even experimenting together a decade ago in college, but now joyce is tired of seeing steven brining her friend down, so she comes up with the plan of feminizing him and taking his place.  it's wickedly delicious fun and a valentines day neither of them will forget.  narrated by shayla aspasia. ]]> Thu, 12 Feb 2026 12:06:31 UTC https://www.freepornflix.com/video/765130/valentines-day-sissy-cuckold/ https://www.freepornflix.com/video/729506/lost-bet-sissy-exposed-at-victoria-s-secret-custom-order/
Today's the day where you have to do whatever i say for the entire day. you've been dreading it ever since you lost that bet to me. i asked you to meet me at victoria's secret and you think it's going to be some boring shopping trip but little do you know that it's going to be a life changing event... i show you some lingerie that i found that i love and you don't seem too interested until i tell you that we're sneaking into the dressing rooms. you think that maybe you'll get some but instead you only get to watch me undress and dress in different sets that i found. don't worry, you're here for more than just watching. you're going to be wearing lingerie too! i make you undress and try on the lingerie sets that i picked out for you. you feel embarrassed but you choose to stay and try on the different outfits. i take off the panties from the last set that i tried on and stuff them in your mouth. i grab some pink bondage tape and tape your mouth shut. soon you're completely taped up in nothing but pink tape and pink lingerie. i tell you that i'm getting dressed then i'm going to wheel you out to the sales floor on a cart and pose you for every woman to see. i know you'll never take a stupid bet again after today. ]]> Wed, 28 Jan 2026 09:21:08 UTC https://www.freepornflix.com/video/729506/lost-bet-sissy-exposed-at-victoria-s-secret-custom-order/ https://www.freepornflix.com/video/695628/the-bridesmaid-s-secret/
Trevor thought he was just attending his ex-girlfriend’s wedding rehearsal. madison had moved on, and he wanted to be polite, maybe even nostalgic. what he didn’t realize was that she had been planning something far more personal and far more humiliating. when madison invites him to a private “afterparty” with her bridesmaids, trevor walks straight into a trap. within minutes, he’s informed that he’s about to become part of her wedding in a way he could never have imagined. madison and her friends have a new bridesmaid to prepare, and they intend to make sure “tessa” is perfect in every glittering detail. from makeovers and a glamorous blonde wig to elegant dresses and sequined humiliation, the bridesmaid’s secret follows trevor’s transformation at the hands of a woman who knows exactly how to break him down. each scene of this audio is filled with control, femininity, and the kind of teasing dominance that only shayla aspasia's voice can provide. ]]> Tue, 13 Jan 2026 10:11:03 UTC https://www.freepornflix.com/video/695628/the-bridesmaid-s-secret/ https://www.freepornflix.com/video/695508/feathers-and-consequences/
Step into the glittering danger of cabaret inferno as empress umbra's exciting narration brings mitch granger’s transformation to life with slow, seductive intensity. what begins as a simple accident becomes a night of feathers, secrets, and a role he never meant to play. listen as glamour turns into control and a single performance changes everything in this short audio by candy apple press. ]]> Tue, 13 Jan 2026 10:05:16 UTC https://www.freepornflix.com/video/695508/feathers-and-consequences/ https://www.freepornflix.com/video/691810/tiffany-returns-part-2-written-by-victoria-vaughn-narrated-by-shayla-aspasia/
When they were young, morgan used to love feminizing brandon and calling him tiffany. despite, her love for tormenting him they remain fairly tight into adulthood. now, an impromptu wrestling match after a night out which brandon loses, causes tiffany to return. only this time, morgan has an ally in his fiancée claudette. audio-only; no video part 2 of a 5 part series.   ]]> Sun, 11 Jan 2026 10:41:19 UTC https://www.freepornflix.com/video/691810/tiffany-returns-part-2-written-by-victoria-vaughn-narrated-by-shayla-aspasia/ https://www.freepornflix.com/video/691748/don-t-pick-up-hitchhikers-part-3-written-by-feminization-author-kylie-gable-narrated-by-shayla-aspsia/
Tara's training with annalise is going well. in fact, it's going so well that she takes him out to dinner at a local restaurant. things get complicated very quickly. ]]> Sun, 11 Jan 2026 10:38:17 UTC https://www.freepornflix.com/video/691748/don-t-pick-up-hitchhikers-part-3-written-by-feminization-author-kylie-gable-narrated-by-shayla-aspsia/ https://www.freepornflix.com/video/691734/don-t-pick-up-hitchhikers-part-1-written-by-feminization-author-kylie-gable-narrated-by-shayla-aspasia/
He thought he was doing a good deed picking up a pretty hitchhiker on a lonely stretch of highway. but one wrong turn led to a nightmare of domination, humiliation, and transformation. part one of a four part series, don't pick up hitchhikers written by feminization author kylie gable narrated by shayla aspasia ]]> Sun, 11 Jan 2026 10:37:41 UTC https://www.freepornflix.com/video/691734/don-t-pick-up-hitchhikers-part-1-written-by-feminization-author-kylie-gable-narrated-by-shayla-aspasia/ https://www.freepornflix.com/video/691086/bridesmaid-s-secret-written-by-kylie-gable-narrated-by-shayla-aspasia/
Trevor thought he was just attending his ex-girlfriend’s wedding rehearsal. madison had moved on, and he wanted to be polite, maybe even nostalgic. what he didn’t realize was that she had been planning something far more personal and far more humiliating. when madison invites him to a private “afterparty” with her bridesmaids, trevor walks straight into a trap. within minutes, he’s informed that he’s about to become part of her wedding in a way he could never have imagined. madison and her friends have a new bridesmaid to prepare, and they intend to make sure “tessa” is perfect in every glittering detail. ]]> Sun, 11 Jan 2026 10:06:28 UTC https://www.freepornflix.com/video/691086/bridesmaid-s-secret-written-by-kylie-gable-narrated-by-shayla-aspasia/ https://www.freepornflix.com/video/691037/don-t-pick-up-hitchhikers-part-4-written-by-victoria-vaughn-narrated-by-shayla-aspasia/
Tara semi-willingly returns to annalise, but now she faces another challenge when she meets annalise's best friend--another dominant sissy trainer named angelica. impressing her will be of the utmost importance.  audio-only; no video ]]> Sun, 11 Jan 2026 10:04:04 UTC https://www.freepornflix.com/video/691037/don-t-pick-up-hitchhikers-part-4-written-by-victoria-vaughn-narrated-by-shayla-aspasia/ https://www.freepornflix.com/video/653282/sissy-slut-fucked-and-drained-stage-1-wmv/
I love turning boys in to cute and obedient sissy dolls. clitty locked in chastity and layer by layer, erasing all masculinity...with a feminine gurl as a result.  ]]> Thu, 25 Dec 2025 09:03:25 UTC https://www.freepornflix.com/video/653282/sissy-slut-fucked-and-drained-stage-1-wmv/ https://www.freepornflix.com/video/640126/the-return-of-tiffany/
Brandon thought he had left the humiliations of being made to crossdress behind. but when morgan, his old feminizer, and claudette, his unsuspecting fiancée, start comparing notes, the past comes rushing back with a vengeance. what begins as laughter over old stories quickly turns into a living nightmare of duct tape, dresses, and old secrets brought vividly to life. this collection brings together the full saga of tiffany’s return. from the first shocking night when brandon’s past is exposed, to the unforgettable fashion shows, humiliating makeovers, and games that blur the line between punishment and play, each story dives deeper into the teasing, the struggles, and the relentless transformations. this unmissable candy apple press three-hour audio is perfect for readers who crave stories of feminization, playful cruelty, and the inescapable return of old nicknames, this collection captures every twist, turn, and taunt. ]]> Fri, 19 Dec 2025 10:43:12 UTC https://www.freepornflix.com/video/640126/the-return-of-tiffany/ https://www.freepornflix.com/video/633070/polished-and-powdered/
A terrific short audio story from candy apple press featuring the vocal talents of empress umbra.   ethan grayson is a wall street powerhouse who prides himself on control, precision, and never being rattled. but when a tech founder drags him to studio lévesque—a chic soho boutique run by the sharp-eyed and sharper-tongued tasha lévesque—ethan makes the mistake of dismissing her craft. tasha doesn’t retaliate with anger. she retaliates with an invitation. returning the next day to “model,” ethan expects a harmless joke. instead, tasha transforms him step by step into eva, a stunning, feminine version of himself he barely recognizes. what begins as a dare becomes a weekly ritual. tasha applies the makeup, chooses the outfits, and shapes the persona; ethan follows along because backing out would mean admitting she’s gotten under his skin. soon eva is helping at fittings, joining photoshoots, attending fashion events, even sharing girls’ nights with tasha’s models. the polaroids multiply. the heels feel less foreign. the line between role and identity blurs. through tasha’s guidance, ethan discovers an unexpected truth: the version of himself he’s spent decades building isn’t the only one with power. ]]> Mon, 15 Dec 2025 10:29:25 UTC https://www.freepornflix.com/video/633070/polished-and-powdered/