Sissy Stories

6,529 results
Orientation
Length
Source
Infinite Scroll

From Russia with Love Part DVA 02

by pellucidbard on Jul 17, 2018
Loving Wives

Author's ed. notes: This story is part 2 of 3 and does not stand alone. Please read part 1, "From Russia with Love, Part Dva, 1 of 3." For the best read, go back to the first story in this series, "From Russia with Love." I strongly recommend you read that first. The primary characters and story theme are developed there. This is one of my longest stories...

Swipe Right Ch. 02

by amb_anonymous on Jul 23, 2018
Transsexuals & Crossdressers

If you haven't read part 1, I'd recommend it since that is the start of the transformation, but this story could pretty much stand on its own. This story contains interracial, dom/sub, t-girls, crossdressing/sissification and bondage. This story is fantasy. I like to stretch the limits of what's possible, so don't expect pure realism. For clarity: In m...

Jake and Audrey Ch. 02

by jsmangis on Mar 6, 2018
Loving Wives

In this Chapter, the story of the young couple's exploits continue, as they share their love and passion with a whole new group of 'friends'. * Chapter Two, More Friends and Lovers. When Audrey and Kaci pulled up in front of the beach house, they saw Jake and Staci relaxing in the spa. They each grabbed a bag of groceries, and as they reached the top of t...

Private Eye

by PastPresentFuture on Oct 15, 2017
First Time

Part One: Virgins Need Not Apply Kimi sent me the Craigslist ad over Facebook. 'Photographer needed for private investigation firm. Must own camera and working car. Virgins need not apply.' I wrote her back after checking out the ad and the rather generous hourly wage. -Ha ha, looks like just the job for me.- -Are you going to apply Matt? You have a camer...

The Man Inside Her

by tre34harr on Sep 16, 2017
Transsexuals & Crossdressers

"I had finally done it, completed what I had first started all those months ago... I had done it through the power of mere suggestion; making her see, making her feel that this is something that she alone had wanted all the time... I had made her take and welcome every last change. Yes it was a slow and steady process, but in the end it all work and oh how w...

Five Into Three Does Not Go

by scribbledehobble on Sep 14, 2017
Transsexuals & Crossdressers

Note to reader – This story has both transgendered and lesbian themes. It arose from an extraordinary story I once heard that quite illustrated the difference between smut and erotica. There are two groups of lovers, one group makes love, the other has wild sex. Not for the faint hearted! Note – The story is told from the perspective of five people – Jim...

Chance Encounter Ch. 09

by Miguel59 on Sep 13, 2017
Loving Wives

C sat all alone. He took a sip of his cappuccino thinking it was the best he ever tasted. He immediately wondered if its delicious taste was because of its link to their unique marriage and the very enjoyable evening he was having with his queen, Jean. He muttered aloud, "For a cuckold, it doesn't get any better than this." Each time he moved, no matter...

Chasity

by SlaveJ on Sep 17, 2017
BDSM

I had followed Her instructions to the letter, purchased the toys and gifts She had specified, booked the time off from work and told my wife that I was going to a conference for a few days. I had booked the hotel room She had requested and arrived there at the pre-defined hour, arranged for a key to be left for Her arrival at the front desk and walked shaki...

Guarded Ep. 05

by GCStargazer on Dec 16, 2019
NonHuman

"So, if you call me a sheep again, I'm leaving you." Leo spoke the words playfully into the wolf's large white ears while rubbing at them. Tracey flicked her ears just below his chin, not bothering to raise her head from his chest, content to continue to lay against him. "Your ultimatum has been received and the high council has unanimously rejected it as t...

Midlife Fallout Ch. 02

by BarryJames1952 on Nov 4, 2019
Mature

This is the second half of a short story born from experiences several of my friends suffered through. How you chose to read is up to you, but reading the first half will help this make more sense. The story and characters are fictitious, but the circumstances are real. No one under 18 is involved in any sex in this story. In fact, fair warning, there's not...