Mature Women First Time Wearing Stockings Stories

353,852 results
Orientation
Length
Source
Infinite Scroll

40 Yrs, In an Open Marriage, Pt. 09

by PassionForPleasure on Aug 21, 2018
Loving Wives

Chapter 9 Natalie's punishment Jean tells me she got a phone call from Natalie, the club was having a special night the next month and wanted to know if we would be attending. "What's going on that's special? "She really didn't say, just it would be a lot of fun and hot. How about we take Annette?" "Sounds great, let her know we'll be there." Saunterin...

The Funeral

by VeryDark11 on Sep 19, 2017
Loving Wives

It has been said that the sex you have after going to a funeral is always the best sex. Maybe because we lose our feeling of immortality, maybe a desire to be wanted, to be held. I don't know. I had left an appointment Tuesday afternoon, and was headed back to my hotel to get some work done on another project, when my rental car just stopped. I was fortunat...

DeLuca's Pleasure Pt. 04

by FHH69 on Sep 25, 2017
Mature

It's my twenty-fourth birthday today. My birthday present should be arriving anytime. My brother-in-law Marco doesn't realize it, but he is my present this year. Unconventional I know, but everything about my relationship with Tony DeLuca is unconventional, including the way we met. I'd been having a week-long affair with his older brother Nick while Nick's...

Andee Loses Another Bet

by AndeeLicious on Sep 12, 2017
Loving Wives

It had been a long time in coming. Andee wasn't sure if having to "pay up" for losing a friendly bet with her co-worker was just a passing joke in the hallway, or if he was serious about collecting on it. As a 38-year old mom of two very active boys and career woman, she enjoyed a bit of adventure in her life and this was the second time in a year she had fo...

My First Infidelity

by Mag58 on Aug 31, 2017
Exhibitionist & Voyeur

Fourteen years ago, at the age of 18, I became pregnant, and got married, three months before the birth. Two years later, I had my second son. Six months after I had my second baby, my elder sister, Jenny, told me that, instead of sitting around, looking like an old woman, I needed a few nights out. I knew that she went, with five or six friends to the lo...

Fucking Anal or Anal Fucking

by blondechristine2012 on Sep 25, 2017
Anal

I suppose it had to happen sometime. I guess it was an inevitability; something that only time and opportunity had prevented occurring before; an event just waiting to come about; an action that was pre-ordained. I mean a forty-plus-year old divorcee with a number of affairs behind her, a free woman with a high sex drive, a female now unshackled from a fifte...

Panties, Panties, Panties

by chuckp7860 on Sep 13, 2017
Fetish

I am not sure when I first thought about girl's underwear. At one time in my life I had a next door neighbor that after staying over their house one night while goofing around as friends I was talked into wearing her hose with my tidy whiteys over them to play Superman. I found my cock getting hard underneath. I never knew whether she noticed but at the age...

Closet Sissy Son Made Into Daughter

by JD2100 on Nov 18, 2019
Transgender & Crossdressers

Why was I on all fours with my dad's cock in my ass and my sister's pussy in my face? Well little did I know that my mom knew about my secret. She knew that I had been wearing her and my sister's lingerie. It started when one day I was home alone and wandered down to the garage to play around on the air hockey table. I got bored and looked around as we had...

Freeing Kirsty

by Egmont Grigor on Sep 14, 2017
Romance

NOTE: For the month of October my wife and I exchanged our home in New Zealand with a couple living on Long Island, New York. This tale arose from that visit; I scribbled down the opening when sitting in the art gallery herein named. Enjoy. – Author. * An autumn chill in the breeze under overcast skies persuaded Merrick to choose an indoor activity on his...

Jenni's Senseless Delight Ch. 02

by herrhook on Sep 17, 2017
Loving Wives

Round two! Will the contenders please take several deep breaths...pardon me if I concentrate on two very special chests...and rejoin the Game. Nearly at the point of collapse, the four had rolled onto their backs, side-by-side, chests heaving, and with very, very satisfied looks on all faces. Round one seemed to be over, with Lee checking off three items o...