Sissy Boy Stories

107,893 results
Orientation
Length
Source
Infinite Scroll

Fawned - A PetPlay Romance Ch. 02

by WinterPior on Mar 3, 2020
Novels and Novellas

He didn't remember the bed feeling as soft as it did when he was on all fours. In that moment, though, it felt like cozying up on a cloud. Wrapped up in a black blanket, Barnaby watched as Gil came back from the bathroom separating his dorm from another. He had a damp washcloth in his hand and that warm smile on his face - one that almost seemed to belong...

A Ski Bunny is Born Ch. 05

by Nikki H on Sep 25, 2017
Fetish

Hi all you Ski Bunny fans! Here is the next chapter in our European tour. This one should have been entitled 'Ski Bunny does Berlin!' Sorry its taken sooo long but hey, a girl's gotta have a life too! Here we go, I really hope you all enjoy it... A huge rainstorm tainted our morning arrival in Berlin, and as the train pulled into Bahnhof Zoo station the...

The Warrior

by twilight_song on Sep 13, 2017
Sci-Fi & Fantasy

CHAPTER 1: The Summoning Violent winds whipped the trees into a frenzied dance, shaking free debris and leaves that swept down from the edge of the forest to swirl around the young woman standing alone on the beach. Allorah looked at the bruised clouds with trepidation. Dark and heavy, they crouched on the horizon, illuminated every few minutes by wicked sp...

Milkmaid at the Back Door

by Cumfusion on Sep 13, 2017
Transsexuals & Crossdressers

This is a sequel to: 'Cherry deflowered at beach party' After all the guys had done me so forcefully I just felt so thoroughly fucked. Once I had been allowed to get back on my feet and take a few steps all I could feel was this slimy stickiness between my bare thighs. The problem was I just couldn't control my bum any more. I tried hard to clasp my anus b...

My Cheating Wife

by DDJetson on Jul 16, 2018
Loving Wives

When I was in my late twenties. I met my future cheating wife in Vancouver Canada. I grew up in the United States. But I have relatives in the Vancouver area. I always liked that city and visited several times per year. There is a high percentage of beautiful women in Vancouver. You can go up and talk to most of them without any rude attitude. I met many y...

A Different View Ch. 02

by kelley_and_tracy on Dec 12, 2018
Exhibitionist & Voyeur

I quickly backed away from the window and Sandy's smiling stare. Humility and dread replaced lust and heat in a matter of a second. I pulled my boxers and pants up quickly fearing Sandy would come bounding up the stairs to confront my spying of her. I sat down on the bed and settled down and realized my fear was not to be. My thoughts were mixed as I wondere...

Tampa Days Ch. 01

by andrea_adores on Sep 14, 2017
Loving Wives

PLEASE don't read if you're too young for filth. Otherwise...enjoy it. As ever, write to me please about my characters, and I WILL write back. -------------- Florida. It was August, mid afternoon and intensely hot and humid in Tampa. Sweltering. Sticky. In that blazing heat, Nikki was fully reclined on a lounger by the pool at the back of her house, her...

Looking Back Ch. 02

by Bluepen451 on Sep 1, 2017
Erotic Couplings

This is the second in a long series of stories in which our heroine, Kate, looks back on some of her more memorable sexual adventures as she tries to decide whether she is a slut. ***** It had been a long day of meetings in Chicago followed by a four hour flight back to San Francisco, so it was late, perhaps 11:00 p.m., when I walked in the door of my ho...

Head Lifted for a Neck Kiss Ch. 03.5

by CuteAndLovelyYetHorny on Jun 19, 2018
Fetish

Alternate ending to chapter 3, followed by 4.5, see below. Chapter one has been updated as of February 2018 Note: This story is a mix between a lovely romance and female domination, it belongs to the "gentle femdom" and "role reversal" category that emerged on reddit and tumblr a few years ago: extremely soft and caring femdom put into idealistic romance...

The Bachelor Auction

by CAP811 on Sep 17, 2017
Mature

I lay in the bathtub, watching steam rise from the warm water. I should have felt relaxed, but I did not. I waited apprehensively. Nothing could calm my nerves. Not the dozen candles that lit the bathroom. Not even the New Age CD that filled the room with the comforting sound of the ocean washing against the shore. The door opened and Mrs. Hanson, my 4th gr...