‘crossdresser’ stories

Shemale mother makes son a sissy.

Never fall asleep at parties!

Babysitter guy becomes babysitter girl.

Sissy watches as his son screws his wife.

Sparks fly when father sees his college son in lingerie.

The pretty 18-year-old sitter has a special surprise.

He's feminized by his wife and her boyfriend.

Steven becomes transformed to Stacy.

Man becomes his wife's fucktoy.

All dolled up and dancing.

Gay incest! Dad lets son fuck mom, for a price.

Straight man is forced to crossdress and suck cock.

He's changed by a handsome hunk.

His dark secret is discovered by his beautiful sister.

White boy meets black man.

Shemale & others gangbang straight crossdressing anal virgin.

Son dresses in stepmom's lingerie.

Sydd's escapades with her client, Binaca Trevors.

Caught wearing panties.

Sissy Alex is feminized by his boss.

Tommy plays dress-up and gets caught by his neighbor.

Feminised by his dad's shemale mistress.

Feminine man is swept off his feet by aggressive woman.

Jessup loses a bet.

Father-in-law continues son-in-law's bridal training.

Dianne is cuckholded and dominated by his wife and her lover.

Grad School hipster is forced to play female porn lead.

He dresses as a girl, then meets a guy

Young man experiences the ultimate feminine act.

He's caught in sis's lingerie.

A last minute errand leads to a whole new life.

Teacher becomes schoolgirl for experimental couple.

He's dressed up like Mom.

Freddy's wife convinces him to dress up and go clubbing.

Crossdresser experiences being a woman.

Alex's girlfriend continues his humiliation.

Two sisters, one son, & one daughter share a wild week.

He dresses up for night on the town.

Crossdresser is forced to go a lot further than he intended.

submissive Asian man and a Dominant woman.

After a car crash, a guy wakes up not so much a guy.

A trip to San Francisco descends into the drag queen world.

A college kid undergoes a transformation at his new job.

A sissy is turned into a gang bang cum slut for the night.

Photos of a date with a man.

A Gift of Humiliation.

When two bad girls find out about Max's sissy fetishes.

Suitcase mix-up means Paul must become Anne.

Young man gets caught by neighbor and leads to sex!

Pretty panties is all it takes.

His wife finds phonesex bill, makes him do it with pool guy.

He's caught dressing and taken far beyond his dreams.

Forced to serve married men as a wife substitute.

Candi learns how to be a real slut.

Staying in a dive motel can be hazardous to one's ass.

Sister abuses her cross-dressing step-brother.

Alex is teased into putting on panties for David.

Sister fucks cross-dressing brother.

Cross-dresser drinks cum from sister's mouth.

Secret crossdresser gets discovered by his wife.

Candi is the party bitch.

I lose a bet that ends me up on the other side.

Cross-dresser is punished for raiding panty drawer.

Crossdresser is used by wife and her sisters.

Wife helps daddy with bride's new training.

Used by the plumber.

A night out results in triggers unleashed for this sissy.

Closet crossdresser finally has first experience with a hunk.

Get the girl... or become a girl for BBC.

Wearing lingerie to work under a suit can be a dangerous.

Father-in-Law continues his training.

He goes to the wrong bar and forgets his wallet.

A man awakes to find a surprise at his door.

Stripper joke leads to straight guy being used as a girl.

A cuckolded sissy husband is happy watching her.

When your luggage goes missing, you wear a dress.

Tough cheating husband meets tough wife.

Wife discovers her transvestite hubby likes cocks.

Man realizes he enjoys playing the part of a woman.

Pictures of me becoming a girl.

A crossdressers first time, explored.

Young man gets more than he bargained for.

Caught crossdressing and Daddy takes advantage and control.

Is the husband tricked or treated?

My very first time getting sex from a man.

Hubby's curiosity backfires on vacation.

A sissy husband gets roped into interracial sex by his wife.

I visited my sister in-law and got a naughty surprise.

Twin siblings' joke backfires in a big way.

The sissy boy gets a new bikini & endures more humiliation.

A crossdresser's awakening.

The school crossdresser gets an A+.

Black drug dealer makes offer he can't refuse.

Three kinky daughters compete at fucking their dads.

He gets blackmailed into being a slut.

A chance encounter turns him into a cock worshipping sissy.

Crossdresser goes out to find big dark meat.

Jamie gets the urge after a business dinner to suck cock.

A Halloween to remember.

Femboy has his first male on male encounter.