Sissy Fantasy Stories

87,403 results
Orientation
Length
Source
Infinite Scroll

The Assignment Ch. 2

by curious2c on Sep 18, 2017
Loving Wives

Well, to bring you up to date on my wife Kate and I. You should be aware that we have been living apart now for about three months. I have been forced to change schools, and Kate decided to remain in our old town for now. We see each other on weekends, for a little bit. We just have a dinner or something, and we haven't had sex of any type since the night sh...

Intimate Fantasy

by MrMikelobe1952 on Sep 11, 2017
Anal

After several weeks of flirting and sharing sexual fantasies on Lit, the Massachusetts lawyer had become obsessed with the sexy young nursing assistant from the deep South. They had shared one of his deepest fantasies, the fantasy of having his ass opened by a strong, firm yet gentle woman. The more they discussed it, the more his urge to live out the fantas...

Summer Hire Ch. 18

by brentaden on Sep 15, 2017
BDSM

Back to the Grind Melissa scooted inside the door, putting her hand out behind her to ease the screen door shut, rather than letting it bang loudly against the door frame. She was drenched from the short walk across the entry courtyard. A summer thunderstorm was blowing sheets of rain through the screen door, drenching the rug and flagstones in the entry ar...

For the Weekend

by missuscooper on Sep 13, 2017
Loving Wives

(Author's Note: I recently started writing this story for my husband Rich—a blend of his fantasies and mine. I will leave it to the reader to decide whose fantasies are whose. When he travels on business, I send a chapter along with him to read while he is away. We talk about it when he calls in—what he likes about it and where we would like the story to go...

Japanese Neighbor

by ubslim on Sep 19, 2017
Interracial Love

I decided to pick up some extra cash during the summer after finishing my first year of college by doing yard work around the neighborhood. One day I stopped by a neighbors house to ask if they needed any work done. A petite Japanese woman answered the door and after negotiating a price, I agreed to cut her lawn every week. I went back on a Sunday afternoon...

The Arrangement Ch. 02

by Mr Robert on Sep 14, 2017
Loving Wives

WARNING!!! This story is about cuckolding and humiliation. If this offends you, please do not read it. * The following morning, Saturday, I wakened, and, as if in a dream, I dressed quickly and made my way to the kitchen. I was painfully aware that I was about to carry out Margaret's instruction to serve Tina breakfast in bed. I wondered why I had neve...

Vicky's Pink Diary 03

by LeggyVicky on Sep 12, 2017
Transsexuals & Crossdressers

So here I am waiting for my Uncle to come home for his tea, wearing Donna's knickers! Vicky's wardrobe is quite sparse, due to having just one locked suitcase hidden under my bed. I'm lucky that my stepmother is roughly the same size as me, and a total slut! Probably the only thing I like about Jenny is her clothes, she dresses like a girl half her age, and...

The Concert Ch. 05

by petitmort on Sep 13, 2017
Erotic Couplings

Jason lounged in the Eames chair, a towel draped loosely over his sinewy legs, watching the two women, laying naked on the bed, grinding their bodies together. He had been told unambiguously (if silently) to sit and watch rather than to join in. He was happy to do so. Amanda and Danielle were kissing passionately, with a fervor that caused Jason's heart to...

Adam's Journey Pt. 19

by stormdog on Sep 15, 2017
Loving Wives

I turned the radio on low, to a soft jazz station that we both liked, then slid into the bed while Kristi went into the bathroom to clean up a little. I propped a couple of pillows up and leaned back to wait, but was getting pretty drowsy by the time she emerged several minutes later. She had washed her face, taking off all the makeup, and standing there na...

Naughty Naomi

by toocold on Sep 19, 2017
Fetish

When people asked Naomi what her job was, she told them that she was a school secretary, which was mostly true. She was a secretary, and it was a sort of school, though in actuality it was the sort of school that she previously assumed only existed in sexy fantasies -- an all-girl institution for ladies aged 18 to 21 who, with complex legal paperwork being s...