Teen Sissy Stories

16,707 results
Orientation
Length
Source
Infinite Scroll

Xander’s Nocturnal Adventure Ch. 02

by neverless on Sep 16, 2017
Celebrities & Fan Fiction

I do not own BtVS or, its characters, they belong to others. I am not making any money from this story. All the characters are over eighteen. * It was past noon when Xander Harris awoke. That wasn't a surprise as it had been past four when he finally drifted off too sleep, happy in the strong arms of Angel. Xander wasn't sure how many times they'd fuck; it...

Sexy

by SweetOblivion on Sep 16, 2017
Transsexuals & Crossdressers

"Hi sexy," he grinned impishly out at her, blinking his eyes to adjust them to the bright sun, as he opened the front door to greet her. "Is Dora...?" She began and then did a double take: "What do you look like, Marcus?" "Don't you love the ice blue?" Lindsey looked the young man up and down and, smiled, despite the initial shock. He was wearing a pale...

A Tale of Two Sissies Ch. 01

by SatinSlip on Mar 26, 2019
Transgender & Crossdressers

Author's Note- this story is a work of fiction. All the characters are eighteen or older unless noted otherwise. This story contains scenes of non-consensual sex, incest, interracial sex, gay sex, forced feminization, abuse, and rough sex. I hope you enjoy reading it as much as I enjoyed writing it. - ***** SMACK! My cheek stings from the big black te...

The Photographers Assistant Pt. 02

by panty_wearing_sissy on Nov 13, 2017
Transsexuals & Crossdressers

If you are under 18, please stop reading and delete this document immediately. This story is pure fantasy. It does not relate to any real events, either past, present or future, and is only suitable for persons over the age of 18 mature enough to understand, and distinguish the difference between fantasy fiction and real-life. ***** Jake didn't remember e...

Tom and Friends Adventures

by Mobman1 on Oct 25, 2020
Exhibitionist & Voyeur

In the night of Falmon, we come to see over the house of the young characters of the Story.What's next? Lisa Emma Sori Paige Tom (sissy) Ethan (sissy) What's next? Lisa Emma Sori Paige Tom (sissy) Ethan (sissy)...

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Trapslut

by Alexia Wright on Aug 20, 2015
Fetish

Today is the day. Your erotic crossdressing blog videos have earned you your first practical job as an escort. Being the famous online sissy slut Annie, you used to pay the bills selling your horny pictures and masturbation videos to guys on the Internet. You got out of bed, still in your pink babydoll nightie complete with a baby blue thong and head for the...

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Classroom suprise

by william125 on Mar 10, 2015
Transsexual

A recently qualified teacher, today is your first day at Tower sixth form college. You stand at 6' 2" and keep your self in good shape. On your way in this morning you saw a group of girls giggling and looking at you. Obviously talking about the new teacher. The bell rings and a little nervous you welcome in your 18 and 19 year old students. Note to r...

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Two Hot Blondes Get Burgled Ch. 07

by scatwoman on Jun 15, 2020
Interracial Love

Chapter 7: "Repercussions" "SMACK!" "RRGH!!" "SMACK!" "MRRGLFM!" "SMACK!" "CRFFT!" "Heh, whatsa matter whiteboy?" Donk chuckled as he stood behind Todd and alternated slapping the left and right side of the bound quarterback's face with his flaccid 20-inch dick, "doncha like big black dick as much as yo girl over there?! I thought ALL white bitches lo...

Neighbourhood Sissy

by Abusedbyfuta on Feb 7, 2019
Fetish

Your a young man in his late teens. Average build, average height, brown hair, green eyes. You know the type never stood out in a crowd for your good looks but never scared children when you went to the store either. Having just finished high school ou decide to start doing odd jobs around the neighbourhood to raise some money. Maybe it was college, maybe it...

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Sissifying Addictions

by Sissyhalo on Nov 25, 2017
Transsexuals & Crossdressers

They say you're born gay, they say you can't catch gay, that you can't be made into something you don't want to. That somewhere deep, deep down you really want it. It's somewhere in between and none of it either. It's actually so much like dominatingly slick, sinking, drowning...so very like that first time you sink into sweet sissy ass. It started for me...