Long Transgender Sex Stories
The longest transgender sex stories on the site — slow-burn reads of 2,500+ words for when a quickie isn't enough. Browse all Transgender stories →
Every story we've published, in one quiet list. New ones land at midnight.
Two Skinny Short-Haired Ladyboys Oil and Bugger Each Other
Two skinny ladyboys oil each other up then take turns buggering their tight asses.
Shemale Tease Squad: Anal, Oral & Sandwich Orgy
Two hot shemales in their late twenties tease and gangbang eager 24-year-old guys in a wild anal, oral, and double-penetration orgy.
My Boxing Partner's Stocking Cock
Alex's boxing partner reveals her stocking cock.
Sissy Training by Neighbor
Kiara, a dominant trans woman, catches her eager neighbor and gives him his first intense sissy training session.
Double BBC Pound for Crossdresser in Lingerie
Simone the crossdresser in lingerie gets double BBC pounded by two hung Black guys while his trans girlfriend watches.
Business Trip Encounter
A straight businessman hooks up with a hot trans executive in her hotel room.
Studio Couch Swap
Ravi transforms shy crossdresser friend in lace.
Stepdad's Filthy TGirl Secret
Stepdad catches his trans stepdaughter’s filthy dom videos and they fuck.
Manager's Private After-Hours Transsexual Orgy
Manager's steamy after-hours transsexual orgy with four eager 20-something performers.
Afterparty Tease: His Best Man’s Secret Craving
Afterparty tease: software engineer Liam dresses in lingerie for his best man and gets eagerly fucked.
Sissy CEO's Tight Chastity Lock
Sissy CEO Petra begs her dominant master Andre to fuck her aching locked clitty.
Goth Femboys PuppygirlXO and Soapy Fate
Two goth femboy trans guys meet up and drown each other in KY jelly for a messy anal fuckfest.
Sadistic Young Lord Buys Ladyboy Slave
A sadistic lord buys a eager trans ladyboy slave for cruel sex.
Small Dick Newhalf Lubed With Vaseline and Assfucked by Huge Dicked Newhalf
Small-dicked newhalf Leilani gets her ass lubed with Vaseline and pounded hard by her huge-cocked newhalf neighbor.
First Time with a CD in Cumberland
A curious guy has passionate first-time sex with a crossdresser in a Cumberland motel.
The Waitress and Her Crossdresser
After closing, waitress Lucy eagerly fucks her regular crossdresser Jamie in the empty restaurant.
Steamy Stepfamily Cabin Swap
Trans woman Imani and her stepdad finally give in and fuck all weekend.
My Wife's Cock: Forced Feminine Slave
A man becomes his wife's eager feminine slave, dressed and fucked nightly by her cock.
Ass-Stretching a Tgirl in the Shower
Grant soaps and stretches his tgirl girlfriend Camila's tight ass in the shower.
Wife Watches Husband Suck Transsexual Cock
Wife watches her husband eagerly suck two hung trans women's cocks.
The Sheikh's Harem of Ladyboys
The sheikh finally claims all three eager 22-year-old ladyboys in a hot group fuck.
Two Japanese Ladyboys Fuck Each Other
Two 24- and Japanese ladyboys meet up and eagerly fuck each other.
My Wife's Silky Sissy Husband
Wife Tamara turns her eager husband into her silky sissy sex slave.
Sissy Guy Gets Fucked by His Stepdad
Sissy stepson Lorenzo finally gets bent over and fucked hard by his muscular stepdad Nikolai.
Cross-Dressing Sissy Meets Her First Man
A shy office sissy in a pink maid dress finally gets fucked by her online daddy.
Crossdressing Husband Makes Love to His Wife
A wife gets wildly turned on and fucks her crossdressing husband while he stays fully dressed in her lingerie.
Last Night In The Studio
Dante catches his feminine assistant dressed.
Wife Watches Her Husband Fuck a Cute Femboy
Wife Tamara watches her husband Everett fuck eager femboy Simone.
Stormy Beach House Swap
Shy crossdresser and trans neighbor swap beach house during hurricane.
Couple's Ladyboy Brothel Adventure
A married couple explores a Bangkok ladyboy brothel and enjoys hot group sex with two trans women.