Mature Anal In Stockings Stories

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Mature Lady Takes a Young Guy

by babswalker on Mar 25, 2019
Anal

Mature lady has a great end to the year and more to look forward to in the New Year. BOB Babs usually finds the golf club dinners quite boring because by the time the dinner and presentations are over the guys are usually well 'lubricated' and retire to the bar, the young people retire to a pub up the road and as she said "We older ladies and I sit about o...

The Door to Door Stocking Salesman Ch. 02

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

Michele was thought about her first sexual encounter with the door to door stocking salesman; she had certainly enjoyed giving him a footjob and she would like to explore their burgeoning relationship further. She particularly liked it when he had kissed and cuddled her just before he left. Of course the dilemma was how to explain to him that she was a trans...

An Old Flame and a New Experience with His Wife

by babswalker on Sep 16, 2017
Anal

Shortly after our recent adventure we were meeting some friends for dinner and had decided to drop into the Filling Station for drink. As Tom ushered me in to the bar I did a double take because sitting at a table at the back I thought I saw a 'ghost' from the past, Carl. When I looked again it was definitely him, a bit heavier and obviously older but still...

A sissy visits the Headmistress

by maturesubmale_for_F on May 12, 2020
Transgender & Crossdressers

1. Miss Stern delivers both punishment and pleasure I knocked timidly on the heavy door and heard Miss Stern's voice from within, commanding me to enter. I slowly opened the door and walked into the presence of my Headmistress. She was in her mid-fifties and sat behind her massive oaken desk as I came in, studying a heavy file. I stood still just inside the...

SoundTek Systems Inc. Ch. 05

by claretwine on Sep 17, 2017
Mature

Edited by angel love * As Gary and Angel took the cab from the Tower of the Americas to the famed San Antonio River Walk, he held her closely in the backseat of the car. Then they walked along the winding path passing shop after shop till they reached the lower river entrance to the hotel. When Angel's floor sounded in the elevator, she turned to Gary and...

Arabian Nights Pt. 04

by MicheleNylons on Sep 26, 2017
Transsexuals & Crossdressers

Back in her cell Sarina helps Michele undress. "That suit isn't too bad; you can just brush it and hang it up. That blouse will need a soak to get the come out of it. Check out your lingerie and stockings and if they have any rips or tears just ditch them. You get an allowance for lingerie and hosiery; the boys are always tearing them because they are so ro...

Surprising Old(er) Lady Ch. 06

by Learningfast on Nov 2, 2020
Mature

They had breakfast. Dee made the scrambled eggs on toast and Andy made the coffee. They sat across the little kitchen table and smiled at each other as their feet stroked and intertwined with each other. She was dressed only in her firm classical underwear, nylon stockings and shiny satin knickers; and he just in his shorts and shirt. Andy kept his look on h...

A Porn Star is Born

by rufun2001 on Sep 16, 2017
Mature

My ex-wife's older sister, Lorna, is a ravishingly beautiful woman in her 50s. I'm 27, but her classic female lines are a turn on for any man who appreciates big breasts, broad hips, long legs, blonde hair and a flirty disposition. She keeps her body in great shape and it's not uncommon to see her dressed up; in spike heels and sexy skirt. While I had always...

Honeymoon at Home Ch. 01

by Beejayne on Sep 13, 2017
Erotic Couplings

The alarm went off and Lenny got up quickly and went to look in on little Carlos. He was still fast asleep for a change, so she ran downstairs to start the coffee. Karl stirred, rolled over but found Lenny gone. Time to get up and get to work. He didn't mind working, the fun part at least. The fun part was the actual mining, finding new ways to extract mate...

Reconnecting with Rene Pt. 02

by dpingjessie on Sep 25, 2017
Group Sex

About three months after I fulfilled one of my wildest fantasies by fucking Rene, the older woman who had been my boss for almost three years, I had the courage to share with her an even wilder fantasy of mine, albeit indirectly. I had posted a story that depicted my dream of having sex with my older supervisor in her office more than a year before we actual...