School Sissy Stories

109,522 results
Orientation
Length
Source
Infinite Scroll

Truth or Dare Takes a Turn Pt. 01

by Cutiepie183 on Sep 14, 2020
Transgender & Crossdressers

I'm sitting at home on summer break, just a few weeks after graduating high school. I hear my phone buzz and glance over to take a look. I can't believe what I'm reading! "Luke Elwood has invited you to his event: graduation celebration party tonight at 8pm." You see I was never really one of the cool kids in high school - I never really had any friends but...

One Step Too Far

by SatinDreamGirl on Sep 16, 2017
Fetish

The clock on the bedside table clicked loudly in the otherwise quiet room. A soft buzz of cicadas outside drifted in through the small gap in the raised window. The room seemed to glow with pink from the afternoon sun. The room hadn't changed much since Rachel had begun her fashion phase in high school. Her closet (and the closet of the guest room) were stu...

Master and Four Subs

by totk6432 on Apr 17, 2018
Fetish

This is a fantasy written by myself for fun. It contains spanking, humiliation and fetish; if this bothers you please seek other authors. All characters are 25 years old or older. ======= The rule is simple: I ring the doorbell and let myself into Master Daddy's house. Susan, my 25 year old personal assistant, is with me. She is in charge of me at work. Sh...

Mommy's Boy? Ch. 02

by yr_sissy_toy on Sep 13, 2017
Transsexuals & Crossdressers

I skipped home from school, an expression of the giddy joy I'd felt for the last week. I'd gone from a pansy boy who got teased after school to my mommy's special sissy, who was swathed in the finest femininity the moment I got home. It was delicious, intoxicating even, and I was almost bursting with joy. I'd learned so much in the last week! I could slip i...

If Women Ruled The World Ch. 02

by chronoxxx on Sep 15, 2017
Fetish

I arrived at the bottom of the stairs of Sulihall College of Etiquette for the final time with my luggage, ready to meet my new Mistress. Nothing seemed real as I headed for the reception desk where 3 Ladies stood talking to each other, their towering high heeled silhouettes casting a shadow from the bright, unknown world outside. My mind was in a fug when I...

Maid on Boxing Day

by Belongs2Beth on Sep 14, 2017
BDSM

Authors note: This story is an immediate sequel to my first story "Carol's Christmas". The events of this story deal with the younger man named Marcus who Mrs. Carson initiated into the mysteries of sex and submission in "Carol's Christmas". * Marcus was sweating bullets as he rang the door. He burned for Mrs. Carson...Mistress Carol...and needed to be wi...

Sissy Pool Wager Pt. 01

by maxy007 on Sep 14, 2017
Transsexuals & Crossdressers

My name is Max, and I'm your typical high school graduate. White, short brown hair, blue eyes, skinny, and 6'4. I never had muscles or any masculine traits other than my lanky height. I had just finished high school, and had 4 months off before university to myself! As you could imagine, an 18-year-old horny boy like myself really got into my porn, which f...

Sammi Starts Camming

by Sissy_Sammi_ on Dec 3, 2017
Transsexuals & Crossdressers

Sam had always been rather small and feminine. As a guy puberty seemed to have missed him which left him in the rather uncomfortable position of being very girly. He was only about 5'8" with a womanly rounded face, smaller waist, and slightly larger hips. He had brunette hair, which for a guy was on the longer end. His lightly tanned white skin pieced with...

Becoming Marc's Sissy

by grizzley123 on Jun 19, 2018
Transsexuals & Crossdressers

This is a story with themes some may not like. If that is you, read it, don't read it, your call. But if you are going to comment, keep in mind that no one required you to read it, and no one requires you to like the themes. Writing nasty comments only makes you look foolish. For others, I would love to hear your comments. And I hope you enjoy the story....

How Friday Got A Reputation

by alice247 on May 11, 2020
Erotic Couplings

How Friday got a reputation "Oh, my fucking God!" Sissy McDowell gasped as she reached into my boxer shorts. "That's all you?" I pulled my face back from her neck and straightened up. "Yes. What's the matter?" I responded defensively, certainly unsure of myself and her reaction now that I had my hand on first base. "You're fucking huge!" She exclaimed wit...