Fucked By The Headmaster Literotica Stories

369,517 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Detention Pt. 02

by Croony on Sep 15, 2017
Fetish

Susie Johnson had a sip of her chilled white wine as she got ready for a night out with a couple of her friends. She'd finished her make up and had chosen her sexiest black underwear with black hold up stockings. She had decided to wear her favourite little black dress. She remembered the last time she wore it. She would never forget the day when she was rav...

A Headmaster's Lesson Pt. 02

by LittleKay on Nov 20, 2018
BDSM

Sadie sat in the dining hall on Friday morning, thoroughly distracted from her grapefruit. She spent the rest of that Saturday night in Headmaster Davis' bed. After his bath, he'd taken her twice more. He fucked her like it was a punishment, as Headmaster Davis said it should feel, but she secretly reveled in the way he stretched her body. The first time hur...

Token of Appreciation

by LOAnnie2 on Sep 13, 2017
Fetish

"Finally, happy eighteenth birthday to Jason Jones and Valerie Arians. Have a wonderful day Albright Academy." Ashleigh Miller lifted her hand from the mic cue and sighed. She took a step back and walked over to the table holding twin bingo machines that sat in the corner of the school office. Kneeling down, she opened the cabinet tucked underneath and pulle...

Spank Me

by Goldeniangel on Apr 3, 2019
Fetish

Authors' Note: This is a rough spanking story involving anal sex. Enjoy! ---------------------------- Hannah shivered as she walked down the hallway to the Headmaster's office. She was a horny little slut and she often got in trouble... ever since the very first day that she'd arrived at the all girl's school at the tender age of 18. That day she'd gotten...

Mrs. White Gets Promoted

by mikey5001 on Sep 17, 2017
Group Sex

At 3:40 pm Mrs. Carol White began the walk from her mobile classroom down to the headmaster's office. She was going to be interviewed for the newly vacated position of the head of the English department. It was between her and Mrs. Cox. Secretly she knew she had the disadvantage. Mrs. Cox had been teaching for ten years long than her, and the head of the Eng...

Class Rules Ch. 03

by 0131aj on Sep 17, 2017
Fetish

Shirley thought that the Headmaster would now agree to retaining both her husband, Julian, and herself in their teaching posts at the all girls school. She had allowed him to spank her over his lap, had held his large cock (much larger than Julian's) in her hand and had not tried to escape when he started to shoot his spunk all over her face. Julian had neve...

Yes Please, Headmaster

by Stripemoff on Dec 21, 2017
Mature

Charles, my husband, hadn't left me much to do when he left for the U.S.A. on a business trip. That was because he was such a brilliant organiser. He planned everything down to the last detail covering the weeks he was away. But, he did leave me one thing to do. "Just make sure that William's entry form to St. Leonard's school gets there before the 20th of...

Naughty School Girl Ch. 03

by Maddisyn on Aug 27, 2019
Erotic Couplings

Natalie's in trouble again! A coincidence introduced Natalie to the Practice and a new doctor in her first story. She sought assistance for her concerns about a long-held intimate secret effecting her teaching career and personal relationships. Doctor Love's sexual therapy was too tempting for the young teacher, fulfilling her favourite fantasies in her s...

Clover Watches Jed fuck Miss Akin

by clovermoffatt on Sep 14, 2017
Erotic Couplings

He was waiting for me with a glint in his eye when I went into his office, and a bowl of ice on his table. 'Clover," he said. "What were you doing in the music store cupboard with Kevin?" "Nothing, Sir." He licked his lips. "I thought I saw him licking your little titties, Clover." "No sir, he was just checking them for... a medical problem." "And the c...

School Daze

by Croony on Dec 29, 2017
Fetish

Abbottsford College, situated in the City of London, was a prestigious all boys finishing school that catered for teenagers from the age of sixteen to eighteen. The pupils were mainly from rich and titled families who wanted their sons to experience the strict regime and make them into better adults. David Bryden was the headmaster that dealt with disciplin...