Sissy Teacher Stories

30,749 results
Orientation
Length
Source
Infinite Scroll

Por que

by Ssrd33 on Apr 22, 2019
Transsexual

We're all super, for some reason my mouth felt tired and had a taste, my ass hurt, the other night we were having a great time on a record. It's the only thing I remembered from the other night. Suddenly the teacher said that a new student was going to enter. We were excited by a new student, fresh meat. The teacher said that his name was Melany, for some re...

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Black Femdom For Black Sissy

by Samuelx on Sep 11, 2017
Fetish

Sitting comfortably in her basement/dungeon, Ottawa's premier dominatrix Madame Whitley looked at her submissive, Shane Johnson, as the big and tall, formerly masculine Black dude stepped out. Clad in a pink Tutu, blonde wig, crimson pantyhose and high heels, the brother was finally letting out his inner slut. For years, Madame Whitley struggled to help Shan...

Madame Jenoix

by Candour on Sep 26, 2017
Transsexuals & Crossdressers

Chapter 1 --------- A young looking and slight 18-year-old boy sits outside the Headmistress's room, obviously feeling anxious. His legs kick back and forth under the chair and he keeps looking up at the door. His uniform looks unkempt, like he has just thrown it on after Games. After some long, countless minutes elapse, he hears a loud, slow "Come!" from...

Chronicles of Heather Maureen Ch. 09

by HeatherMaureen on Sep 16, 2017
Transsexuals & Crossdressers

Final Exam While I was waiting in bed last night for George to join me he had gathered up my clothes and purse then locked them in my car to make sure I'd spend the day with him. His clothes would fit me like a tent and his wife's merely like a pup tent so they were no help. I resigned myself to staying here and inside for the day. He made breakfast for...

Big Black Cock: A Sissy Surprise

by silkstockingslover on Feb 13, 2018
Illustrated

Summary: A wife joins her husband as a slut for a teen BBC. Note: This is a 2018 Valentine's Day story so please vote. Note 2: Thanks to Tex Beethoven, thor_p, Robert and Wayne for editing this story. WARNING: If you hate gay stories, interracial submission, sissification (not a word I know) or cuckolding please don't read. If you do like those themes.....

Marcia Goes Back to School

by Belongs2Beth on Sep 12, 2017
Transsexuals & Crossdressers

Authors Note: This story continues the adventures of eighteen year old Marcia (nee Marcus) Cicero. The tale opens a week after the events related in "Carol's Gifts". Marcia has shown visible signs of blossoming in the wake of Mistress Carol's injection of powerful hormones and is anticipating returning to her school for the first time as a girl. To answer an...

Mommy and Goddess

by force_transitioned on Sep 12, 2017
Transsexuals & Crossdressers

Andrew never saw the noose. He was uncomfortable around his new mother in law - his wife's new step mom. And rightly so - he was, after all, going through the woman's intimates since the day she entered their lives, some two years ago, shortly after the marriage. Had he overcome his guilty reaction, he may have noticed a recurring theme in their conversa...

Keith's Caught in a Costume Pt. 03

by gaildaniels84 on Dec 24, 2019
Transgender & Crossdressers

Keith's alarm went off and he silently reached out a hand and silenced it. He'd hardly been able to sleep at all, tossing and turning with worries about what school would be like today. It had been less than a day since his life had turned into a nightmare - his incredible teacher had caught him rubbing himself in a cheer uniform and then he'd had to buy pan...

Panty Posers Ch. 06

by EROTICbearscribe on Oct 19, 2020
Transgender & Crossdressers

We entered our building and bumped into our downstairs neighbor Jerry. He was taking his trashcan back to his apartment. He set it down at the landing and gave us each a good look. He wasn't at all phased by our appearances. "Little early for Halloween, isn't it...boys?" he asked. We both were fully aware Jerry knew we were sissies. It was fairly obvious...

Neighbourhood Terror to Sissy Pt. 10

by Fibaro on Jun 10, 2019
Transgender & Crossdressers

Chapter 12 Mark had just about time to put his dildo down before the door to his room opened. His hand was still wrapped around the base, and well there was no real way he could ever hide anything of what had been going on. He was caught red-handed and could only really look at his girlfriend, or rather his ex-girlfriend in horror. After all, why else than...