Literotica Gilf Mistress Stories

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Mrs. B.'s Summer Boy Toy

by milfleglover on Sep 14, 2017
Mature

Jeannie Byron is 65, in tremendous shape for her age, a graying-haired GILF of exquisite proportions, standing about 5-6, weighing a very athletic 140 pounds. A lifelong tennis player and teacher, the stunning elderly woman teaches young people at a tennis camp in summer in the seaside community where she lives. She loves working with young people for a var...

2020 - WIC

by Rekki on May 10, 2020
Miscellaneous

WIC, short for „Weekly Image Captions“, is a project I started this year to post an image caption each week. The characters, scenes and kinks are often different from piece to piece but there are some reoccurring themes like Timestop and Mind-Control, since these are my own favorite kinks. Since March, it‘s possible to choose the character for an upcoming we...

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A GILF Wife's Loving Domination

by milfleglover on Sep 11, 2017
Mature

Beth came home from work in her office the same time as always, around 6 p.m., and Jack, her husband was dutifully making dinner and tidying up around the house, having gotten out of work an hour or so before. Theirs was a happy, long marriage, both in their early 60s, their kids grown and gone, both athletic and active. Beth was a vivacious, charming 61, sh...

GILF Bobbie's Brutal Butt Bashing

by milfleglover on Sep 14, 2017
Mature

I met Bobbie on a trip to Jamaica. She was sweet and compassionate, and friendly. Me, I'm 22 years old, was at a wedding, and saw her in the bar one night and chatted her up. Granted, there is the age difference -- Bobbie was 69 years old -- but something about her struck me. I'm drawn to older women; they're easy to bed and eager to please, no questions ask...

Black Journal Ch. 19

by Dhc000333 on Sep 16, 2017
Mature

Duncan Cyrus, age 24, Grocery Store Gilf The market is a place where you can see all kinds of people. I know this because while I have my headphones on and drown out the noise I observe the environment. I go by a set list and routine as I walk through the store. The market is pretty big and looks more like a warehouse really. To be honest it's like my soci...

Mrs. O'Malley's Golden Juices Ch. 02

by milfleglover on Sep 25, 2017
Mature

Susan O'Malley, a beautiful, domineering 65-year-old blonde, had just walked home from the beach, after a long afternoon of sun, sand, drinking her usual wine -- and dominating young Brett Hannigan, a gorgeous young stud of 19, whom she'd caught licking the grass on which she'd pissed moments earlier, pounding his hard cock as he did. Earlier, she'd noticed...

Latina Granny Ch. 02

by BilboMerkin on Sep 15, 2017
Mature

A big thanks to those who made comments. You helped me realize how important Trent is to the story. ***** "I am in control. I know what I'm doing. I am in control." I kept repeating this over and over to myself. It was my mantra. I was in control. I knew what I was doing. I would not lose control. "Then why," I asked myself, "Am I dressed in one of my...

Forced To Worship GILF Legs

by milfleglover on Sep 16, 2017
Mature

I had just finished up my five-mile morning run, when David pulled up, a local young man who does carpentry work in my little town. Being a divorced older woman, I needed such help from time to time and he'd come recommended by others. I watched the young man get out of his truck, a handsome stud to be sure, in his early 20s with shaggy blonde hair and a le...

A Gilf's Cum Slave Ch. 03

by milfleglover on Sep 19, 2017
Mature

(Ongoing series of stories about sexy older women who love using young studs as their cum-fed sex slaves!) * Annabelle and Meredith just came back from their daily morning walk, a ritual the two best friends engaged on daily to keep their hot, GILF bodies in prime muscular shape. Annabelle was 62, a gorgeous silver-haired blonde with lithe, lean legs and...

The Dream Job Pt. 05

by MrWidetool on Apr 1, 2020
Transgender & Crossdressers

It was a considerable drive to get to Jasmine's "little place outside the city" as she had called it. On unfamiliar roads surrounded by lush old growth forest, Paul drove their modest mid-size crossover while Debbie poked at her phone. She was scrolling through image searches of Jasmine's photos online. Mostly social events and red carpet type stuff, but She...