‘sissy’ stories

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sissy 

Bikini Boi

Brother's friends make me wear my Sister's Bikini...

Gay Male 09/23/2018

Story of Sissy Submission

Sissy submission.

Transsexuals & Crossdressers 09/23/2018

Stranded, Sissified, Seduced

If she can get him into her underwear can he say no to sex?

NonConsent/Reluctance 09/22/2018

My Visit to the Adult Bookstore

Bookstore visit.

Transsexuals & Crossdressers 09/22/2018

Sissy Academy - The Tour Pt. 01

A tour of the famed Sissy Academy!

Transsexuals & Crossdressers 09/21/2018

Quenching Thirst Ch. 03

BBC on sissy... More.

Transsexuals & Crossdressers 09/21/2018

Schoolboy to Schoolgirl

Ms. M makes a new sissy.

NonConsent/Reluctance 09/21/2018

Sissy Fluffs an Orgy

Continuing autobiography of a sissy slut.

Transsexuals & Crossdressers 09/19/2018

The Rose Diaries Ch. 09

Doll takes center stage!

Transsexuals & Crossdressers 09/18/2018

I Need a Man

Young man needs to experiment.

Transsexuals & Crossdressers 09/17/2018

Shaped by Daddy

A story about the encounter of my feminization at 18.

Transsexuals & Crossdressers 09/15/2018

The Sissy and the Pet

A sissy and a pet submit to their Mistress together.

BDSM 09/15/2018

Involuntary Sissy Pt. 05

She'd never shame him in front of her friends, would she?

NonConsent/Reluctance 09/13/2018

Francie and Graeme's Defloration

She knows what's good for a man.

Erotic Couplings 09/11/2018

Becoming Jacqueline Pt. 01

Jack arouses his emerging feminine self, and likes it...

Transsexuals & Crossdressers 09/11/2018

Candi's Conversion Ch. 02

The new sissy experiences a girl's night in.

Transsexuals & Crossdressers 09/11/2018

The Rabbit Hole Ch. 03

Penny takes Joe on a field trip to test his training.

Mind Control 09/11/2018

The Punishment

Fantasy football punishment leads to feminization, gangbang.

Transsexuals & Crossdressers 09/09/2018

Sissy Dust Pt. 03

Spencer cashes in her sick days and goes deeper.

Transsexuals & Crossdressers 09/08/2018

Sweet Little Snapshots

She gives her boyfriend a surprise while he wears a dress.

Gay Male 09/05/2018

Involuntary Sissy Pt. 04

His stalker moves in, but can she make him admit their love?

NonConsent/Reluctance 09/05/2018

The Massage Away Ch. 05 Pt. 09-10

The story continues and my Queen is thoroughly blackened!

Fetish 09/04/2018

Sissy Manners Classes Ch. 01

Sissy found her master.

Transsexuals & Crossdressers 09/04/2018

Candi's Conversion Ch. 01

Inattentive husband turns into a sissy slut to keep his wife.

Transsexuals & Crossdressers 09/03/2018

Involuntary Sissy Pt. 03

His stalker uses an old flame to deliver total humiliation.

NonConsent/Reluctance 08/31/2018

Cuckolding Mom and Dad Ch. 01

A son discovers his parents' secret.

Incest/Taboo 08/30/2018

Sissy Maid to Be... Ch. 02

Jenny continues to prepare with Mistress's help.

Transsexuals & Crossdressers 08/30/2018

Seduction by Shaving

A sissy boy and his roommate bond over shaved legs.

Gay Male 08/29/2018

Jack's Bully Ch. 04

Jack goes on a date and finally loses his virginity.

Fetish 08/29/2018

Toby

Toby's story on self discovery and life as a sissy.

Transsexuals & Crossdressers 08/28/2018

A Sissy's Awakening Ch. 01

A sissy is awoken.

Transsexuals & Crossdressers 08/27/2018

White Boi Learns his Place Ch. 05

Vacation wraps up for Ashley and Daddy.

Transsexuals & Crossdressers 08/26/2018

Sissy and His Sister

Sister and her friends catch me in her underwear.

Transsexuals & Crossdressers 08/26/2018

Brad's Adventure

A man gets sucked off by a sissy in a video booth.

Transsexuals & Crossdressers 08/25/2018

Sissy Maid to Be... Ch. 01

Married sissy in for the experience of her life.

Transsexuals & Crossdressers 08/24/2018

Sissy's Sexy Strut

A sissy dresses every inch a lady and goes out in public.

Transsexuals & Crossdressers 08/24/2018

The Massage Away Ch. 04 Pt. 07-08

Beyond the massage, beyond one masseuse, beyond expectations.

Fetish 08/22/2018

Sissy PRIDE!

SISSY PRIDE!

Transsexuals & Crossdressers 08/22/2018

Sissy for the Family

An Asian boy becomes a sissy for his white family.

Transsexuals & Crossdressers 08/18/2018

An Evening in Red

An eager sissy's first session with his mistress.

Transsexuals & Crossdressers 08/17/2018

Anthony's Descent Ch. 01: Truth or Dare

Anthony plays a game with his best friend and his girlfriend.

Transsexuals & Crossdressers 08/16/2018

My New Digs Ch. 02

A sissy cuckold husband goes deeper into submission.

Fetish 08/16/2018

Man Disciplines Sissy Ch. 03

Sissy quits crossdressing, purges, reboots, is disciplined.

Transsexuals & Crossdressers 08/15/2018

Sissy Wants Her Wife's Boyfriend Ch. 02

Sissy uses her power to get her way.

Transsexuals & Crossdressers 08/15/2018

Locked

The key to a chastity belt disappears down the drain.

Transsexuals & Crossdressers 08/15/2018

The Inner Slut Ch. 07

Lexi's Training.

Fetish 08/14/2018

OMG My Daddy’s a Sissy (Prequel)

How Rick discovered his love of panties.

Fetish 08/13/2018

AliExpress and Sissy Downfall Pt. 09

The sissy spiral cont. this time with semi permanent results.

Transsexuals & Crossdressers 08/11/2018

Once Upon a Laundry Ch. 03

Jeff, Jessy seek out Kimmy individually for their own ends.

Transsexuals & Crossdressers 08/11/2018

Auntie's Panties Ch. 06

Phoebe hosts a party.

Lesbian Sex 08/10/2018

Involuntary Sissy Pt. 02

Is it really stalking if it's true love? She thinks not.

NonConsent/Reluctance 08/09/2018

Crossing The Line

The night I met Mark. The night I became a sissy.

Transsexuals & Crossdressers 08/09/2018

The Last Time I Blew Matt

Vivid memory of the last time I blew my lover.

Transsexuals & Crossdressers 08/08/2018

The Massage Away Ch. 02 Pt. 03-04

The surprise massage continues.

Fetish 08/07/2018

Sissy Wants Her Wife's Boyfriend Ch. 01

Sissy discovers power over men.

Transsexuals & Crossdressers 08/07/2018

More Than I Bargained For

I answer an ad for a 3some but it wasn't what I thought.

Fetish 08/07/2018

The Massage Away Ch. 01 Pt. 01-02

Arranging a surprise massage for my Queen.

Fetish 08/05/2018

Taking It Up a Notch

A husband succeeds in getting his wife to cuckold him.

Fetish 08/04/2018

White Boi Learns his Place Ch. 04

Black man continues his dominance over sissy boi Ashley.

Transsexuals & Crossdressers 08/03/2018

The Boifriend Ch. 01

His daughter's boyfriend has a secret...

Gay Male 08/02/2018

Locked Up

A cuckold husband gets more than he bargained for...

Fetish 08/01/2018

OMG My Daddy's a Sissy

Ashley discovers her Daddy likes panties & penis.

Incest/Taboo 08/01/2018

College Owned Sissy Ch. 01

Max is transformed into a sissy.

NonConsent/Reluctance 07/31/2018

Blackmailed High School Sissy Ch. 03

The Humiliation Continues.

NonConsent/Reluctance 07/30/2018

Involuntary Sissy

A woman describes her methods for controlling men with satin.

NonConsent/Reluctance 07/30/2018

Sissy's Subservience to Wife Ch. 01

Hotwife transformed me into a sissy cuckold.

Transsexuals & Crossdressers 07/28/2018

Caged and Used

Caged sissy is used as a woman.

Transsexuals & Crossdressers 07/27/2018

Virgin Femboi

A secret sissy is fucked in his sleep by his roommate.

Transsexuals & Crossdressers 07/26/2018

Mommy's Chastity Boy Ch. 01

A mother keeps her boy in chastity with monthly milkings.

Incest/Taboo 07/25/2018

What Every Sissy Knows

A story of my first time.

Transsexuals & Crossdressers 07/24/2018

Cantata (The Organist)

A church woman, a lover & her son have a threesome.

Incest/Taboo 07/24/2018

Best Friends Forever Pt. 06

In the shadows of Brian's mind.

Transsexuals & Crossdressers 07/24/2018

Sluts

Meeting new people can be quite the experience.

Transsexuals & Crossdressers 07/20/2018

Chasing Skirts

Sam's a young man with eyes on Heidi, who has strange tastes.

Transsexuals & Crossdressers 07/20/2018

Dungeons & Desires

After his secret is exposed he seeks out a Goddess.

Transsexuals & Crossdressers 07/19/2018

A Night with Daddy Alpha

A sissy's first time with a dominant male.

Transsexuals & Crossdressers 07/15/2018

Another Sissy Shopping Adventure

Another sissy shopping assignment from a young mistress.

BDSM 07/15/2018

Sissy Maid Son Pt. 02

The sissy maid is getting prepared for her first day.

Transsexuals & Crossdressers 07/14/2018

Sissy Meets Master's Lady Friend

Sissy continues training on becoming a proper girl.

Transsexuals & Crossdressers 07/13/2018

Sissy Maid Son Pt. 01

A son is forced to become his mother's own sissy maid.

Transsexuals & Crossdressers 07/10/2018

Transfixed by Tessa

He knows where a cuckold's place is.

Loving Wives 07/08/2018

The Rose Diaries Ch. 07

Doll's life grows a bit more hectic!

Transsexuals & Crossdressers 07/07/2018

White Boi Learns his Place Ch. 03

White bois descent to BBC slut continues.

Transsexuals & Crossdressers 07/07/2018

Quenching Thirst Ch. 02

Bbc on sissy.

Transsexuals & Crossdressers 07/04/2018

Swinging 60's Cuckold

A couple in the 60's discover cuckolding and embrace it!!

Loving Wives 07/04/2018

My Place in Our New Relationship

Taking things further.

Transsexuals & Crossdressers 07/03/2018

My Aunt's Anniversary Cruise

Cruise leads to sissification and an interracial gangbang.

Transsexuals & Crossdressers 07/01/2018

Marcella Falls in Love

Marcella falls in love with his dominant lesbian lover.

BDSM 06/30/2018

My Mom's a Submissive Slut Pt. 03

And so is my Dad!

Incest/Taboo 06/29/2018

Jack's Bully Ch. 03

Jack's bully and mother get closer.

Incest/Taboo 06/29/2018

King and Queen Cuckold Pt. 01

He serves his wife and her lover.

Loving Wives 06/29/2018

The Rose Diaries Ch. 06

Doll falls head over heels for a new girl!

Transsexuals & Crossdressers 06/27/2018

Becoming His Bitch

The real story of my first time with a much older man.

Gay Male 06/26/2018

Alex becomes Aly

Aly gives his first blow job.

First Time 06/26/2018

Cumming of Age

Young man's transition to a feminine submissive lifestyle.

Interracial Love 06/24/2018

Sissy Meets Daddy

A sissy loses her virginity.

Transsexuals & Crossdressers 06/24/2018

Taken Too Far Pt. 01

A closet sissy meets a master in rush hour.

Transsexuals & Crossdressers 06/23/2018

Adult Trip Pt. 01

Married, Femdom, interracial and cuckold play.

Interracial Love 06/21/2018

Art

A divorced cuckold finds a girlfriend.

Erotic Couplings 06/21/2018

Turning Myself Gay Pt. 04

All types of gay and sissy things are ingrained.

Gay Male 06/21/2018
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