#cross-dressing
57 stories tagged with this.
A dominant Black man takes an average white man and transforms him into a cross-dressing sissy slut for Black cock.
A husband enjoys his wife's nightly drinking habit because it makes her eager for vigorous, experimental sex.
A sissy crossdresser is punished by his Mistress after being caught having sex with the repairman.
A cross-dressing husband secretly explores his submissive and lingerie fantasies at home while hoping his dominant wife will one day discover and embrace his true nature.
A 13-year-old boy is forced into degrading servitude, wearing girls' underwear, and subjected to corporal punishment and sexual domination by another boy.
A young man finally acts on his lifelong fantasy of being dominated and feminized by a group of women after meeting a stripper.
A lonely young man revisits his cross-dressing desires and devises a scheme to seduce the handsome delivery worker who has captured his attention.
Cody secretly borrows his sister’s clothes and makeup before spending the night with Garet, where he can embrace his female identity as Sadi.
A young sissy boy's anal initiation continues through encounters with his great-uncle, school prefect Rob, and Rob's divorced father who shares a panty-fetish and takes a keen interest in training the feminized boy.
A cross-dressing home help finds unexpected pleasure and employment with an older man.
A husband's honeymoon turns into a cuckolding and breeding fantasy when his wife finds a new lover.
A cross-dresser enjoys a tea party with a twist, exploring their feminine side while flirting and playing games with their host.
A newly divorced man meets a beautiful woman at a conference, only to discover she's a shemale with a surprise for him.
A college student's cross-dressing camping trip takes an unexpected turn when a fellow camper joins him by the fire.
A cross-dressing camper gets more than he bargained for when two unexpected visitors join him at his campsite.
A shy boy discovers his first girl in panties and bra, leading to an unexpected encounter.
A man meets a cross-dressing stranger online and discovers an intense sexual connection.
A middle-aged man is blackmailed into sucking his teenage neighbor's cock after being caught dressed in drag.
A bisexual man explores a swingers club's LGBT night and finds unexpected pleasure with a trans woman.