Sissy Interactive Stories

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The Sissy Grade

by BigDaddy4u2 on Sep 14, 2017
Transsexuals & Crossdressers

"OK, that's all for today. Have a good weekend, and remember to do the reading for next week. Oh, and Sam...please stay if you can." The students filed out, some of them had that 'ooh, he's in trouble' look on their face. I was in my tenth year teaching History at a small college. It was fairly satisfying, and gave me time to work on my books. Some student...

The Visitor Ch. 10

by Leanne_sissy on Sep 26, 2017
Transsexuals & Crossdressers

I don't know how long I slept for, how long my poor battered mind floated in the warm sea of mindless contentment, before I came to. I stretched yawning, my body feeling stiff and strangely aching. All the memories of those things that I'd been subjected to were still a distant dream, until the realisation that I was still dressed in that horrible adult baby...

The Office Sissy XX

by pennyjonestv on Sep 15, 2017
Transsexuals & Crossdressers

It had been one of those days where you wish you had chosen flats and support tights. But no, that wouldn't have felt appropriate for the new head of human resources. Impressions are everything in this business. Back to back meetings from nine am to seven pm had taken its toll on my calves, my back and for that matter my mood. It was one of those days I get...

Natural Escalation

by WatchingAndWaiting on Aug 18, 2017
Fetish

Tim looked over at Lisa. Her eyes were half closed, but she noticed him looking, and her lips curved into a lascivious smile before the pressure from behind surprised her and she shut her eyes in ecstasy, pushing back and raising her ass a little to meet the massive cock burying itself inside her rectum. Tim felt his cock twitch a little, pressed against the...

Sugar & Spice

by AngelCherysse on Sep 16, 2017
Transsexuals & Crossdressers

This is my most difficult story to date; difficult to write, difficult to read. The sex is intense; the violence, more so. Most men will not have the patience to sit through it; it takes too long to get to "the good parts". Most women will not have the stomach for it; in places, it hits too close to home. I don't know whom that might leave as an audience, bu...

Darla's Dilemma

by soldierboy50401 on Sep 12, 2017
Loving Wives

For more background on many of the characters in this story, please read the following: What Mother-in-Law Wants Badge of Betrayal Clarissa Gets Served Grab Life by the Balls The Ghost of Red River Falls This story also contains some graphic descriptions of domestic abuse. If you or someone you know is currently in an abusive relationship, please...

The Recording Studio

by Mark2 on Sep 16, 2017
Sci-Fi & Fantasy

It's Friday morning, her eighth. Casual Friday, which she hates. She hates wearing jeans, prefers slacks, something looser, more feminine. She usually wears dresses. She had to buy the danged jeans just to fit in at work, and being so tall the only pair she could find were men's. Too narrow at the hip, too low a rise, they press against her sex when she si...

The Slave Trade

by Grey Eagle 286 on Sep 13, 2017
Loving Wives

Thomas Burke Rockwell III sat at his desk and watched the latitude and longitude change as he ran the cursor across the satellite picture of the area. He looked at the next coordinates for a corner of the property he was interested in. It was a 1244-acre parcel of land; it was planted in pine trees now. He wanted to determine how much pine was harvestable ri...

Cynthia's Joy

by sinisterout on Sep 13, 2017
Transsexuals & Crossdressers

Many thanks to CKQuail for editorial input and proofreading. ***** In the beginning I knew her by her screen name, Goddess4u2serve. Later I learned her name was Cynthia, but I usually called her 'My Goddess'. She knew I was a cuckold before we'd even met. She'd read the stories I'd posted here on Literotica where I explored my dark fantasies. I can't e...

Total Drama Transformation/Fetish

by Sojaxx on Apr 22, 2025

(Originally written by Dustin https://www.writing.com/main/interactive-story/item_id/1708471-Total-Drama-TransformationFetish-Story/map/1 ) The lights flickered on, shining down on the stage as a peppy tune blared out of the speakers. "Hey there, Total Drama fans!" Blaineley said to the cameras, "Blaineley Stacey Andrews O'Halloran here to bri...

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