EXTRA-MARITAL CHERRYHi! I’m Jill, the subject of this story. It’s my extra-marital cherry that we are talking about. There are different kinds of firsts. Losing your cherry refers to first sexual intercourse. But there is also your anal cherry and your extramarital cherry referring to having sex with someone other than your spouse after you’ve
The Lamb of London
Author’s Note: This is a substantial reworking of one of the first stories I published on Literotica under the original title of ‘All Three Holes’ in the Anal category. That was more of a simple stroke piece, but this version adds more context to the story and, hopefully, fixes some rookie mistakes I made.1.Katie stood
#10: Monday Morning
This is a work of fiction. Names, characters, events, and incidents are the products of the author’s imagination. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. All characters are consenting adults over the age of 18. ———— While the girls were attending home-room, the Headmaster took the opportunity to
Discovery Ch. 06
*** Authors Note: Any similarity to real persons or places described within this story is probably not an accident, although I’ve made the effort not to expose anybody too much. The story circulates around a girl I met once, who told me some of her story. I will always regret not having spent more time
World’s Biggest Harem Ch. 12
Celeste ended up giving me a massage that night. She had never done it completely naked before, but I enjoyed the feeling of her bare knees on my back. “Don’t ask me to do this for Crystal.” Celeste said, as she tugged at my arms. “I don’t think she would like it much.” “She liked
Friend Asks Me for a Big Favor
I had known Judy for five years or so. We were good friends despite her being ten years older than me. I knew she had an eighteen year old son (Pete) who I hadn’t met and a husband (Jim) who I had met three or four times. I was thirty-one at the time of this
Sally: My Slutty School VP
Hi all, its Ali here!I’m here with another exciting adventure. Today, I want to describe how Sally Parera, my sexy ex-school vice-principal. She is one of the sexiest mature women I’ve had the luck to fuck. Growing up, she was the focus of many students’ Stylish-MILF fantasies, including mine. Though she was an extremely strict
The Pretty Men of the Harem Pt. 02
Second part of my role reversal universe. Read the first part, be a dear and pay attention to the tags listed. All characters are 18+. Feedbacks are appreciated! 2. Surrender and Obedience Elias woke up with a new resolve, sharp and feral. He wouldn’t be some plaything discarded at the end of the week. No
Our Town
Amanda’s red heels flash brightly as she walks purposefully down the quaint, high street of this archetypally English seaside town. Today she wears a calve-length denim dress with the lower front buttons undone to reveal flashes of shapely legs, an entrancing hint of smooth inner thighs and just a hint of cleavage. As she proceeds
The Business of Bukkake
Hi readers! A bit of a change of direction from long character building affairs, just a quick and fun one-off story, hope you like it! Samantha Sloan was nervous. This was unusual. She’d made her reputation on the back of her steely resolve, her unyielding strength of will, and her ferocious negotiating skills. In short
Virgin Date in the Woods (Pt 2)
“My turn now.” Answered Mark as Mason nodded approvingly knowing he would be looking to score with Gail as well. Mark had been kissing and stroking Gails leg, even brushing his pinky lightly along her pussy during their time waiting. It was now time to test her. “Ok Gail, lets go down the path.” Mark
Virgin Temptation in the woods
Gail was really excited looking forward to meeting up with and going out with her best friend Patsy tonight Friday after a hectic school week. Finally 18, both girls were finally allowed to go out if escorting each other. Young ladies in highly religious conservative families weren’t permitted to do many things others of their
Tables Turned on Miss De Rossi
Punishing Miss De Rossi The Sting Derek’s shoulders, knees and lower back ached as he knelt while holding the textbooks in his outstretched arms. It was an infamous punishment that Danielle De Rossi, an English teacher at Jefferson High School, rather enjoyed dishing out. Miss De Rossi was a very attractive woman in her late
Teacher Reunion
This is a work of fiction. Everyone named IS real and the location, names, ages and dates have not been changed, I did attend this school when I said I did but to protect my identity I have not named myself in the story.”Why don’t you come back to my place?” How long had I
My Dream Job
After high school, I attended a tech school, learning about CAD — Computer Aided Design, and also CNC — Computer Numerical Control, which takes the CAD information and actually manufactures the object, following the CAD instructions. I did very well in my training, if I say so myself. The various teachers praised my quick mind
The New Girl Pt. 03
A change in perspective. Kimmie learns her true self. Submission is an art. Afforded only to those who deserve it. **** ‘Fuck, fuck, fuck fuck.’ Were the only words screaming through my mind. For the entire journey back in the Uber I had my legs crossed as tightly as possible while trying to keep my
Clothing Challenged
This is based on a true story from my life. The characters are of course changed in case any of them might still recognize themselves and object. It’s true… up until it isn’t. (My roommates actually challenged me to this, but I didn’t ‘accept the challenge. And that’s where my fantasy kicks in. It could
QT: Aisling’s Antics (Ch. 7)
Part Seven – “The surface of the sun” December 12 th , 2020 When Fiona woke in the morning, most of the other women had gotten out of bed already, everyone sleeping around Andy without sleeping touching him. That had been a lot harder for some of them than others, and several of them had
Waking up to Maia
This story is inspired by and dedicated to my one and only owner. The gorgeous, divine and perfect Mistress Maia Redhood. This story involves topics of female domination, cuckcoldry, male chastity and light cbt. If you are interested in these topics, I hope you enjoy reading it as much as I enjoyed writing it. ————————————–
Miss Pamela Eleven
When Gloria and I entered Mistress’ apartment we encountered a wild scene. Mistress and Desiree were seated on the sofa with Genevieve’s two subs eagerly feeding on their pussies. Genevieve was similarly hosting Lisa’s voracious attention.”Join the fun,” Mistress called out and beckoned us with the crook of her index finger. She handed Gloria the
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