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 →
Two skinny ladyboys oil each other up then take turns buggering their tight asses.
Two hot shemales in their late twenties tease and gangbang eager 24-year-old guys in a wild anal, oral, and double-penetration orgy.
Kiara, a dominant trans woman, catches her eager neighbor and gives him his first intense sissy training session.
Simone the crossdresser in lingerie gets double BBC pounded by two hung Black guys while his trans girlfriend watches.
A wife brews a potion that turns her chauvinistic husband into a woman for one wild night.
A straight businessman hooks up with a hot trans executive in her hotel room.
Stepdad catches his trans stepdaughter’s filthy dom videos and they fuck.
Manager's steamy after-hours transsexual orgy with four eager 20-something performers.
Afterparty tease: software engineer Liam dresses in lingerie for his best man and gets eagerly fucked.
Sissy CEO Petra begs her dominant master Andre to fuck her aching locked clitty.
Two nervous goth femboys finally meet and drown each other in lube and cum.
A sadistic lord buys a eager trans ladyboy slave for cruel sex.
Small-dicked newhalf Leilani gets her ass lubed with Vaseline and pounded hard by her huge-cocked newhalf neighbor.
Curious straight man’s first time taking a crossdresser bare.
A shy crossdressing regular finally seduces his favorite waitress.
A man becomes his wife's eager feminine slave, dressed and fucked nightly by her cock.
Grant soaps and stretches his tgirl girlfriend Camila's tight ass in the shower.
Wife watches her husband eagerly suck two hung trans women's cocks.
The sheikh finally claims all three eager 22-year-old ladyboys in a hot group fuck.
Two 24- and Japanese ladyboys meet up and eagerly fuck each other.
Wife Tamara turns her eager husband into her silky sissy sex slave.
Sissy stepson Lorenzo finally gets bent over and fucked hard by his muscular stepdad Nikolai.
A shy office sissy in a pink maid dress finally gets fucked by her online daddy.
A wife gets wildly turned on and fucks her crossdressing husband while he stays fully dressed in her lingerie.
I arranged for eight hung sissy boys to gangbang my husband and me.
Girlfriend gives her boyfriend a full sissy makeover then takes him out to suck his first cock.
Wife Tamara watches her husband Everett fuck eager femboy Simone.