‘cross dresser’ stories

He had a secret, though he never thought of coming out.

A different shade of pink...

CD gets a fresh start after breakup - 750 Word Challenge

A look in a mirror reveals a face Scott's never seen before.

A woman in black drags Scott into self-exploration.

A Valentines Date turns to lots more for this whore.

Straight man meets and falls for crossdresser!

Riley gets invited to a club by Daddy.

Old lovers re-unite.

Stevie, the sex slave to his wife and mother in law expends.

Pete worries if Monica is angry but she actually needs help.

Sissy maid gives blowjobs and receives new rules to live by.

Turned into a sissy slut by the older neighbors.

College student forced to be their roommate's sissy maid.

College crossdresser finally goes through with it.

A favour for a friend, where could it lead?

A crossdresser spends their final night with new lover.

My weekend away with my lover.

Returning to single life after Anne.

Another night of fun in a hotel for a crossdresser.

A gradual transformation from boy to woman.

My first Valentine's Day spent "alone" in five years..?

Frank/Francine and his wife have launch a new strap-on.

A crossdresser gets more than they bargain for in a hotel.

The binbofication of a cum and cock slut addicted to both.

A straight white guy continues his journey.

pretty sissy cuckold takes a lover of her own.

You do meet some beautiful people out on the open road.

My best friend came out to me as being gay.

The second part of the photoshoot.

My domme ex girlfriend finishes what she started.

Playtime with a friend.

A fright.

A dinner date with a difference.

It's thenight of Michelle's graduation party.

Embracing the change, going further down the rabbit hole.

A return to the house of dreams.

Emma finally gets her just desserts from David.

Chrisofer explores his feelings for Jezebel differently.

Burnie’s Dark Side.

The beginnings of my transition to a gay cross dresser.

Michelle returns to the office after a very busy weekend.

A new city, a new life, a new start and now a new job.

Divorced male seeks masculine man for marriage.

Halloween cleaner arrives in a rabbit mask: OPEN SEASON.

The night of the bachelorette party arrives!

Dress shopping, flirting, party plans & in bed with Babette.

FANTASY is so much better than REALITY!

Michelle is falling for Brenda, but Ms. Allison has plans.

A cross dressing short story.

Michelle continues with Brenda and spends time in the office.

David is convinced to dress up for Halloween.

Michelle has an intense training session and date w/ Brenda.

Shylo learns more as a Sexual Therapist than Stripper.

Brandi takes charge.

Michelle learns a valuable lesson and progresses in her job.

A weekend with Babette brings a new level of closeness.

Young man recalls his first time as a cum slut.

It happened, finally...

An older man fondly remembers his first man to man sex.

Michelles training steps into high gear.

18th Century Murder, Mystery . . and Sex.

Start the new year in a winter parking lot.

Quarantine can get a bit lonely.

The world is starting to look a little dark.

I found a surprise under my neighbor's 'pesky' skirt.

Jenn's big night out with the girls continues.

Jamie gets ready for her date.

One 24 hour period that define their relationship.

Sex, Madness, and the cults of Cthulhu.

Girlfriend takes revenge on boyfriend for cheating on her.

Jennifer's night out with the girls continues.

Jennifer enjoys a night out with the girls.

Interludes, plus Anneka gets to fuck with Dean.

Intern goes undercover as a cross dressing spy.

Hair stylists have a fetish to debauch married men.

Fraternity pledge coed cross dresser dances sexy for men.

Cute cross dresser waitress with enticing perfume whispers.

Frisky coed exhibitionist crossdresser gets first time anal.

Sissy CD takes care of Sir's needs.

I meet Chad and he begins my journey down the rabbit hole.

Chris continues to use me and breaks in new toy and his sling.

An afternoon with my crossdressing slave.

College age Trans girl finds love with Silver Fox.

Becoming a Wife to a Man.

Jade learns a very difficult and very valuable lesson...

I continue to tell of my college thong and sissy experiences.

A new city, a new me, a new friend.

College boy experience in girl's thongs.

Corey's adventures as Cora continue...

This is my first time of buying thongs.

I return to the bar, and pick up a surprise.

A make over from man to sissy.

Blackmailing my twin sister.

A little experimenting never hurt anyone.

My descent continues.

You never really know what to expect from your first BBC.

Likely transcript of our divorce proceedings.

I met a crossdresser online.

Marsha forces me to do some very uncomfortable things.