Sissy Scool Porn Caption Story Imagefap Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

CFnm Adventure - 2nd Visit

by lovelicker99 on Sep 13, 2017
Fetish

Note: This is the second story involving encounters between me as a submissive male and a Dominant BBW who responded to an ad I ran online. These stories are fantasies, but some of the specific acts are things I have done and enjoy doing. If you are a woman or a couple that enjoys doing any of these things I would like to hear from you regardless of where yo...

Isabella's Reversion Pt. 05

by silverbackteddy on Sep 16, 2017
Fetish

Note from the Author: This is a story about ABDL. The first word being Adult. All sexual encounters center around Adults, above the age of 18. This story also contains BDSM, plushophilia, watersports, and various other fetishes. For those that are grammar freaks, please don't comment on my improper grammar use. I could care less. At least it doesn't have L...

A Latex Crossdresser's Dream Pt. 05

by shinyglove on Nov 18, 2019
Fetish

Please read A Crossdressers Dream parts 1-2-3& 4 before moving on to this story. *** The party was certainly in full swing as we had all seen some sort of action. The room smelled entirely of sex and latex, I was very happy with this as the aroma of rubber turned me on. Every time I opened the bag where I kept my latex collection the smell coming from it w...

Lilly

by CumSlurpingCuckold on Sep 16, 2017
Loving Wives

My name is Louis. I'm White and I love my Vietnamese wife so much, but Lilly calls me "Daisy Lou, a Dick-sucker" nowadays, and she's 8 months pregnant from a Nigger-man named Jerome. She keeps me in her panties; it makes me feel good, feminine and servile. Since she doesn't wear panties anymore, now that she's a Nigger-loving wife, she told me I should wear...

Pilot Training

by nadia603000 on Mar 30, 2020
BDSM

It's a Friday evening and I'm just finishing supper, served by my personal slave Sophie when my phone rings. Like a good slave, Sophie instantly jumps to her feet and all but runs to the few feet to the living room to get my phone. She brings it over, kneels down beside me and holds my ringing phone out atop her upturned palms. "Here is your phone, Mistress....

Loosening Up Bk. 01 Ch. 01-10

by SteveWallace on May 14, 2018
Group Sex

Book 1 -- Loosening Up: Initial Journey Chapter 1 -- A Crack In The Façade Alice sedately drove her seven-year old silver Honda Civic into the parking lot of the company she worked for -- Knightsbridge Manufacturing. She looked around, but only a few cars were present. Along the back side of the lot four cars were already parked in the spaces under the tre...

Sissification 101: Ch. 01

by silkstockingslover on May 4, 2020
Fetish

Summary: Straight guy is caught watching sissy porn and...Note 1: Thanks to Eric who requested and helped plot this lengthy story. Note 2: Thanks to Tex Beethoven and Robert for editing. Note 3: All characters are at least 18 years old. Sissification 101: Ch. 01 1. MY SISSY CURIOSITY I've always liked nylons. I grew up when they were still popular and...

Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

I Was a Teenaged Metahuman Ch. 03

by DickMarks on Apr 1, 2020
Sci-Fi & Fantasy

Welcome back to the story! I'd tell you to check the previous chapters if you haven't already read them, but you're smart enough to figure that out, and I believe in you. Everyone doing sex in the story is eighteen or older. Many thanks to icedragonmo3 for excellent beta-reading and proofing. Any mistakes are mine, because I just can't leave it alone. * *...

Work Husband

by edrider73 on Mar 20, 2018
Loving Wives

My amazing editors knew I had written my last story, so this special project both caught them by surprise and gave them little time to work their wonders. I was accustomed to their talents, but they surprised and touched me by their loyalty, and I can't thank them enough. SueDanym suggested surgery, but I hesitated until a second opinion proved the good doc...