Crossdressing Stories Literotica
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Curcky's entry into Fila Thai is rejected.
Part 2: Is Nick (Melissa) in over her high heels?
A naughty headmaster ensnares a delicate pupil.
The morning after, and the heat is still on. End of Book 1.
Going deeper into crossdressing with my girlfriend.
How far will Nick go to help his childhood friend?
Trisha learns to make love, and to love herself.
T & D shower and get ready for bed, maybe...
My perfect sissy housewife life and how it started!
Trisha accepts him inside, and their lust deepens.
Trisha is ready for Daddy's special training.
My first panty boi encounter with sexy Daddy... Part 3.
Trisha changes outfits for more fun, but something's wrong.
Trisha gets to experience something she's dreamed of.
T & D decide to stay the night and see where it takes them.
After being sissified by Ethan, I go back for more...
Trisha's training is in full effect now.
A lost bet to a friend leads to a humiliating sissification.
After months of chatting online, Trisha and Daddy first meet.
My first panty boi encounter with sexy Daddy... Part 2.
My time in the sauna was just the beginning.
Costume fun, then to a bar and bookstore.
Michael begins to settle into Mishel.
A closet crossdresser's stepbrother needs a prom date...
My working solo weekend proposal requires approval.
Revenge is best served cold with gravy.
Love between two friends in a nightclub.
How a hairstyle can influence behaviour...
2 Thief's had some fun with a surprise crossdresser.
1st part - wife's sexuality is revitalised by my boobs.
I did something naughty and Valerie decides on sissification.
A few brief and mostly unsatisfying encounters.
After being outed, I'm still caught.
My first panty boi encounter with sexy Daddy...
Tricked into dressing as a woman to advance my career.
Widow helps son cross dress for Halloween, and….
Secret sissy plans a fun night in, & it doesn't disappoint.
Stacy's girlfriend takes her out for a birthday surprise.
What’s next after being caught out by my girlfriend?
A boy is given away as a bride to his Father's coworker.
Steve is caught and tricked in pleasing an older man.
Rick and his boyfriend were on the downlow and are caught.
Eric gets fucked by BBC for 1st time; Joan gets black pussy.
Why am I always caught in women’s lingerie?
Grandma & Grandson trust and explore fantasies.
Our adventurous deckhand has a secret, eventually shared...
We go bikini shopping to find a matching set.
How Jennifer and Patrick got to the point of their new games.
Tom learns his new duties as a chastity maid.
Pandemic leads to housewife opportunity.
I visit a sex shop and make some new friends.
Tom caught cheating on wife. May not like wife’s solution.
Paula's new life begins after she fell for Louise's Trap.
Desiree embraces her new life working for the Russia Mob!
Jamie has to decide if he will crossdress for sex.
Man decides to create a transsexual GF.
A reward of sorts... but one that comes with strings.
A new client of Alexis has a familiar face.
Back on the boat, and some time to talk.
Emily finds strangeness on a ferry that needs investigating.
A scavenger hunt around San Francisco.
John blossoms into Jenny...against his own will...
Crossdresser hooks up with people using LGBT club.
Gay teen continues relationship with his dad.
Wife planned a visitor who caught me out as a sissy cuckold.
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Bisexual crossdressing husband coming clean with his wife.
A crossdresser is controlled by his wife and her sisters.
A new city, a new life and a new experience.
Bisexual crossdressing husband coming clean with his wife.
Bisexual crossdressing husband coming clean with his wife.
T & D get where they are going, and the going is good.
Bisexual crossdressing husband coming clean with his wife.
A transvestite allows herself to be pleasured by her Dommes.
A crossdressing exhibitionist gets caught and blackmailed!
A crossdresser at Disney World with his wife and friends.
A first time male-male handjob turns into much more.
Evy and June continue the night but, what about the weekend?
I dress up as a woman and snort cocaine with two sexy men.
Michelle's training intensifies while Babette is away.
Part 2: Is Nick (Melissa) in over her high heels?
Crossdressing and snorting cocaine with a handsome man.
June decides to take the plunge, a text begins it all.
Sara is loved and accepted for who she is.
Amy's sissy journey clashes with her real life.
GF helps me dress as b'day gift for her BF.
A manipulative wife dominates her crossdressing husband.
Ruby learns how to become a true bitch for her new master.
Going deeper into crossdressing with my girlfriend.
How far will Nick go to help his childhood friend?
Week 2 at work, Michelle's transformation intensifies.
It's so much more fun to give in to your urges than resist.
I come face to face with my future as a sissy.
June and Evy wake up to the morning after with raw emotions.
Simple crossdressing advice - watch out for the addiction!
Dealing with heartbreak, life takes a turn for Mark.
Mike returns to start his new job and faces new challenges.
A casual cross dressing session turns very hard.
Can a crossdressed Secret Service Agent change history?
My first panty boi encounter with sexy Daddy... Part 3.
Sometimes a fantasy can come to fruition.
Danny finds magic that transforms him into a hot girl.
Two bi males make due while their female lover is away.
Dan listens in on Ex-wife's fun with a BBC.
Trisha's training is in full effect now.
A sweater can make sisters even more cuddly.
After months of chatting online, Trisha and Daddy first meet.
My buddy tells me I should try something new...
The story of a closet sissy's coming out for her Daddy.
Amie & Steve Continue Their Training.
Sissy with construction worker - Part 1 of 3.
A trans top in her thirties helps me explore sex en femme.
Mike finds a job, which may be much more than he expected.
My first panty boi encounter with sexy Daddy... Part 2.
Bryan faces his test, and Becky finds somebody.
Brie gets a new wig and Suzie gets new nylons.
My experience in a gay sauna changed the way I have sex.
Raquel & the girls bring out Mike's inner girl.
A man embraces his feminine side when encouraged by his wife.
Don Altieri indulges in his forbidden fetish.
A closet crossdresser's stepbrother needs a prom date...
An encounter I had while in lockdown.
An actor becomes more versatile, on and off set.
Dan sees his ex wife again, she has a charm on her anklet.
Dan measures his penis, and compares to statistics.
Day 2 of cd and her online bf in NYC.
Dan's BBC Porn addiction develops while Ex dates black man.
Warm up exercises and Training the team.
Shop attendant discovers a secret about a pregnant customer.
Divorcée finds a new friend with a secret.
Dan's addiction deepens, Ex finds a black man.
Playhouse broken in by a pain slut gurl.
Dan gets a divorce and falls into crossdressing.
First time in public this T-Girl gets a secret pounding.
Scared boy learns a painful truth about himself.
Gina finishes slut trading by getting a bbc gangbang.
Sally meets Carla and they both learn something new.
Man tricked me into letting him have his way with me.
The transition, thoughts and feelings of a crossdresser.
Thursday with Suzie before Friday night at work.
A sissy gets more than bargained for after accepting a gift.
A sissy plans an action-packed weekend.
Raquel meets Mike, a fledgling panty wearer.
"Two roads diverged and I took the one less traveled."
Chris is exposed and used as Christine through a dice game.
More feminizing exploits for Sammi. It's getting wild!
Separate tags with commas. More info in the FAQ
All contents © Copyright 1996-2021. Literotica is a registered trademark.
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