Schoolgirl Anal Stories

51,261 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Man Pleaser

by staricide89 on Jul 31, 2019
Celebrities & Fan Fiction

This story is based in the world of CyberRun. ***** The cold alley air chilled her as the smooth shiny vinyl of her minidress was rolled up over the curve of her ass, the slick fabric dragged teasingly over her skin before finally popping up to her waist, baring her naked, round rear and the string of the tiny little v-string that she wore. She heard the m...

Return to "Weekend School" Ch. 14

by cynthiablaine7 on Oct 26, 2020
Transgender & Crossdressers

[This story involves bodily functions and sometimes severe disciplining, including caning and spanking, as well as crossdressing. If reading about those offends you, read no further. These stories may be read separately but do gain from being read in sequence.] Laura Franklin wasn't sure what kind of response she would receive when she sent out notices by m...

Navy Blue

by Shakestare on Sep 15, 2017
Anal

Sally McMichael was sitting in the back row half asleep, the affect of listening to Billy Goats, a high school, legend twenty-two years ago, babble on and on about his boring life. He talked about his playing days Upover High, his great football career and his baseball career and his tracking career. He went to deep conversation about drug abuse and how he c...

School's Out

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Steve asked me if I'd like to come to our school reunion. We were both twenty and being schoolmates seemed a long time ago. I agreed before he told me it was fancy dress. 'Your girlfriend, Sally's ok about this?' I ask dubiously. I knew Sally well, not that we got on particularly and she was phenomenally jealous. She would spin into a rage if Steve merely...

Her Ass is Used by Friends Ch. 02

by Alex_likes_Butts on Sep 12, 2017
BDSM

I tied the white lace blindfold securely around my girlfriend Ashley's gleaming eyes. Damn did my sweet 32-year-old girlfriend look hot! She was dressed in a sexy pleated mini skirt, semi-transparent white blouse, stockings and high heels, a basic highly stylized slutty schoolgirl outfit. Ashley had again agreed to one of my typically crazy wild dares! In...

Seduction of a Japanese Wife Pt. 02

by ElderDirt on Jan 15, 2019
Erotic Couplings

Author's note: If you have not read the previous story of this tale, please do so. You will better understand the characters of this tale, their way of speaking, and some of the mannerisms and customs unique to Japan. Forgive me if there are parts of this story that differ from your knowledge and understanding of Japan and its people. The standard disclose...

Allison's Schoolgirl Adventures Ch. 1

by CherryLicious on Sep 12, 2017
Toys & Masturbation

Allison woke to the sound of her alarm buzzing in her ear. She rolled over and turned it off, squinting to make out the time. 5:45 am…why so early? And then she remembered…today was her "play" day. She planned to have as many orgasms as possible throughout the day…starting right now. Just thinking about all the nasty things she planned to do today was gettin...

Schoolgirls and Schoolboys

by JDBDS on Sep 16, 2017
Transsexuals & Crossdressers

(Disclaimer: This is a true story.) This is a story about myself, my girlfriend Shannon, and one really, really hot crossdressing dude. Or girl. A note--I would describe myself as a straight guy, while she would describe herself as 75% straight or so. The story begins back in December or so. Shannon and I are both in our early twenties, we've been dating f...

3X DVD Review Issue 1

by a_scoundrel2000 on Sep 16, 2017
Reviews & Essays

3X DVD Review Issue 1 Genre: Sex addiction therapy featuring: “Maya’s Addiction” “Sessions” Maya's Addiction (VCA Interactive) Starring: Wendy Divine (a.k.a. Maya Divine) Is she Maya or Cassie, who cares? Wendy Divine, even with her large breasts gives her best try to act wholesome as a modest wife with a porn star’s body. Her husband is a habitual ma...

Ms. Morgan's Dilemma

by bhanover on Jan 14, 2018
Anal

I looked down at my paper and sighed. It had come back from my professor all covered in red ink. A B! I would never get into University of Chicago Law with these kinds of grades! But, drastic times called for drastic measures. Fortunately, my Classics of Political Thought professor was kind of cute, in a dorky sort of way. I could do this, I thought. I looke...