Sissy Boy Stories

107,893 results
Orientation
Length
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Infinite Scroll

Goddess Rules Ch. 02

by sub_boi on Sep 17, 2017
BDSM

I take him into my mouth and suck him with My soft, wet lips. When he is near coming, I grab his balls and pull down hard, letting his little cock slip out of My mouth. He moans in pain as My hand squeezes harder on his balls. "Now, My little slut, I have a surprise for you." I go to the closet and pull out a sexy little pink camisole. "Put this on, slu...

Stevie's Journey Ch. 02

by gbr2004 on Oct 7, 2019
Fetish

I sleep soundly but finally wake up and realize it's almost nine o'clock. I get up and take a shower. The hot water feels so good. I get dried off and go over to the dresser and open the top drawer and there are several pairs of panties in the drawer. I pick out a red pair and slip them up my legs. They feel so soft as I pull them up. I reach in and tuck my...

The 70's Weren't All Care Free

by Stillherer on Sep 16, 2017
Transsexuals & Crossdressers

It was the 70's. Young, carefree, long-haired hippie, away from home, traveling around the country - having a ball. A couple guys I met and I decided to go for some beers. The local Y was in a sleazy part of town. So we ended up a pretty seedy bar which was hosting a rather bizarre strip show. At another table was an older guy that had been at the Y that aft...

An Obsession

by Marcus_Cicero on Jul 30, 2019
Transgender & Crossdressers

It would have been after that documentary. The one with a feature on online dominance-submission relationships on Fetlife. Because before that moment in time life had been so vanilla. Marcus had been queer and had had a boyfriend or two... or three since turning 18. Well, hell, he'd been to the bathhouses since turning 20. He'd even gone as far as to create...

Maid on Boxing Day

by Belongs2Beth on Sep 14, 2017
BDSM

Authors note: This story is an immediate sequel to my first story "Carol's Christmas". The events of this story deal with the younger man named Marcus who Mrs. Carson initiated into the mysteries of sex and submission in "Carol's Christmas". * Marcus was sweating bullets as he rang the door. He burned for Mrs. Carson...Mistress Carol...and needed to be wi...

Panty Posers Ch. 02

by EROTICbearscribe on Jul 6, 2020
Transgender & Crossdressers

NOTE: This is a work of fiction. The characters appearing in this series are consenting adults over the age of 18. Any reference to past experiences by any character appearing in this story are intended to define that character. * It was almost 3 when I woke up in my roommate's double bed. Sunlight streamed between the broken slats of his plastic blinds...

Snap! to it Divina

by DivinaTellsAll on Feb 12, 2019
BDSM

Writer's note: The following story is 100% true THE DRIVE The drive to Austin was 8 hours in good weather. Today it had been raining, and it was going to be 11 hours in the car, by arrival time. I was acutely aware of how long the car ride had been so far, for several reasons. The biggest of which was the overly-tight pair of pink sissy panties, curren...

Being a Sissy for Viv Ch. 01

by Caron on Sep 25, 2017
Transsexuals & Crossdressers

"Even I had to tell my daughter off for looking at a sex site on the internet yesterday. A shame, it did look rather interesting. But even if she is nearly twenty, I really couldn't tell her now could I." "Oh, what was so interesting about it?" I asked. Viv paused for a moment, her eyes on the wine glass in her hands. "It was about turning men into maids....

From Husband to Man's Sissy Wife

by Pantypansy on Jul 8, 2019
Transgender & Crossdressers

I was pulling up my white panties and smoothing the tops of my stockings when I heard the doorbell, and my wife welcoming somebody at the door. He had a deep, Scottish voice. Lucy welcomed him into the living room, then closed the door and came into the stairwell and beckoned for me to come down. I felt a chill of fear, but tottered down the stairs in my...

College Misery Ch. 01

by newauthor19 on Sep 16, 2017
Fetish

Ever since words got out that James has some femboy porn hidden in his laptop it has been a nightmare for the 19 year old poor boy standing 5'8" and weighs merely 122lbs. His classmates have totally lost all respect for him. He was admired before for his friendly attire and kind hearted nature but now he is admired for his feminine body. He lives in a boy's...