Sissy Boy Stories

107,893 results
Orientation
Length
Source
Infinite Scroll

The Chess Club

by cahab on Sep 19, 2017
First Time

I guess it was all Christine’s fault. Or rather, I suppose I have her to thank. Christine was a very rebellious girl in my school, with long black hair, overdeveloped breasts for a girl her age and an attitude that made the teachers wince whenever she even walked by. The boys all lusted after her, some secretly, some overtly, and she flirted with all the mal...

Ja'ak and Sarai Ch. 01

by Something_Random1 on Sep 17, 2017
Celebrities & Fan Fiction

None of the Star Wars creatures, species, locations, or names in this story are my property. Ja'ak and Sarai, however, are. Enjoy =P I wonder where she's taking me, thought Ja'ak as he followed Sarai through the alleyway, watching her hips swing to and fro in a mesmerizing manner. He'd met her only hours before in the cantina, and then saw her again in...

Nature or Nurture Ch. 13

by LopendVuur on Sep 15, 2017
Novels and Novellas

Knowing they will have a hard and dangerous night, they sleep late and have a leisurely breakfast. Victor is planning to see the boy again, and they decide to all go, to convince Sir Malcolm to let them in on the raid tonight. As it turns out, he is quite ready to. Last night, when Miss Yves was at the theatre, his house was invaded by another of those cre...

Santa's Milk and Cookies

by PerilEyes on Sep 13, 2017
Erotic Couplings

I tried to dismiss the patter on the rooftop as typical house noises, but the calamity in the living room was unavoidable. My first instincts pointed to a robber. There had to be some pretty sick individuals in the world to want to break into a house on Christmas Eve, but in today's world you had to expect everything, right? I grabbed my bat and discreetly d...

Not So Much a Stable "Boy"

by BootyLaBooty on Sep 14, 2017
Romance

Set in 1800's English countryside. A stable boy finally succumbs to his lust for the spirited young lady of the home he serves during a trip to meet her betrothed, a man whose wealth would save her financially unstable family. (modern language.) ***** Evie shoved the threadbare curtains away from the window of her small stagecoach. Her heart rate quicken...

Restroom Rendezvous

by cutestguy on Sep 14, 2017
Exhibitionist & Voyeur

It was a pleasant surprise to see her at the store that noon. I was on my lunch hour and thought to buy some cookies for the kids. She was there to purchase some odd office stuff. Her office, that is my previous employer, is near to this store. Even though we are still in touch, either on phone or YIM, that day I didn't tell her I am visiting this city since...

Natasha- We Meet Again!

by spikingtheworld on Sep 14, 2017
Erotic Couplings

I am writing this in multiple parts (hopefully), with the main character of the story, Natasha (not her real name) having no idea I am doing this until I let her know about it. * To "Natasha" This is a completely anonymous, safe place to reveal my deepest, darkest, fantasies. A very detailed exercise using fictional and non-fictional elements describing m...

Fem in a Black Leather Jacket

by Transboy on Sep 16, 2017
BDSM

My heart was beating like a jack rabbit, my palms were damp. You could hear the music from down the street. I walked through the bar's front door for the first time, this was where I met him. God, I can't believe it led to this. I moved downstairs into a big loud room, heavy beats penetrated my chest. It was busy, packed, sweat filled the air. I kept to the...

The Dream

by moll65doll on Sep 17, 2017
Non-Erotic

Ananta has a dream. She dreams of romance. Of sex. Of a tall, handsome man quite her opposite making love to her over and over. Alas. Her geekish self cannot manage to obtain a boyfriend. Two graduate degrees and three jobs later she is still single. Her loving, teasing best-friend who is incidentally gay and the closest she's ever been to a man, Ungar,...

Mature Woman Conquest: Beth Ch. 01

by lilguy on Sep 12, 2017
Mature

Beth was part of a group. It was called the mature women Conquest league. It was MWC for short. There were a group of older women that loved to conquer men. It could be physical conquest and physical. Any type really. You get a point for different things. You would take a picture of your conquest and put it in a personal album. It was a fun little club. She...