Mature Crossdressing Stories

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Tea with Dottie

by ColinPleasant on Oct 6, 2020
Group Sex

Dottie never dressed in a flattering way, but that made no difference to me. I wanted to reach into those khaki slacks to rub her flabby belly. I wanted to peel off her polo shirt and suck her sagging tits while running my hands through her short, grey hair. We sat across her kitchen table from each other sipping tea. She was 20 years my senior, but I could...

Teenage Haven Ch. 01

by AnAmericanDarling on Nov 16, 2020
Mature

Part One: Introduction Anna unrolled her hair. Last group of tresses, last curler. Her beautiful red hair was warm and wavy now, long and lustrous. She sat at her vanity putting the last touches of make-up on, make-up that would soon be mussed. Her smooth, young legs (she had just turned nineteen) led up to her pretty, shaved, panty-clad crotch, and from th...

Surprising Old(er) Lady Ch. 07

by Learningfast on Nov 16, 2020
Mature

Lunch at the apartment was delivered by a boy on a motorbike, after a quick phone call. Dee and Andy ate sitting together on the sofa, with a low table in front of them, and dressed only in their underwear. Andy passed plates and food and glasses of white wine to her because she was unable to bend sufficiently in her corsetry; although it was not hard-laced...

Sex in the Sun

by historyandherstory on Nov 16, 2020
Erotic Couplings

Marie and I were on holiday in Western France. We'd rented an apartment for three weeks and driven down to the Royan area, after crossing the Channel from Dover to Calais. Marie is a petite, sexy, auburn haired beauty, with a great 34, 25, 35, figure! We have been married for fifteen years, have a great sex life together, and have both had a number of sexu...

North to Alaska

by komrad1156 on Sep 15, 2017
Mature

"A sense of adventure is one thing. You could go scuba diving in the Keys or zip lining in Costa Rica. Moving to Alaska is...insane! Somewhere along the way you must have seen episodes from the '90s TV show, Northern Exposure. You know, the Jewish doctor from New York who goes to Alaska to pay back the state for paying his medical school tuition and ends up...

Loosening Up Bk. 08 Ch. 11-15

by SteveWallace on Mar 2, 2020
Group Sex

Chapter 11 -- The Producer The informal meeting took place in Dave's spacious living room. Those in attendance consisted of Dave's ten wives, Dave, several other Circle members, and two of the producers of the reality TV series to which Dave and others in the Circle had agreed. Al Berker with Spring Garden Productions took the lead. First off, I want to th...

Bablee Ch. 01

by StoryTeller07 on Sep 14, 2017
Fetish

A Pakistani woman goes to school Bablee's husband was working in the US as an architect, on a major building site. He didn't think she could cope with such a different culture, so left her at home while he was working. Unfortunately an accident on the building site left him in hospital, with a spinal injury. The corporation picked up the hospital bills, a...

Ravenswood Sluts

by TLMorgan on Sep 26, 2017
Erotic Couplings

Frank Spellman pounded a barely just turned 18 year old girl into the bed with his huge cock. He towed over her back with his skinny yet muscularly lean body, pulling at her long strands of blonde hair as he drilled his cock deep inside her. The 18 year old blonde was face down into a pillow with sweat flowing down her gorgeous face. Her wet pussy was set on...

Condominium Ch. 11

by SteveWallace on Sep 18, 2017
Group Sex

Chapter 11 Diane came to our apartment at lunch a few days after a party. Penny was in school, and Amber was off working with a client. I escorted her in. She looked succulent, and I wondered if she had a sexual agenda or why she was there. "Jon, I'm here for two things. First, I met a nice man who I think would like our party group. He lives in 1402 - rig...

Ella's House of The Way Forward Ch. 04

by Sputnik57 on Sep 18, 2017
BDSM

Gray's cock was rigid with excitement as he was led naked and on all fours for the first time, by the naturally dominant Rosie; though he yearned to be put in his place by Ella, being put down by the youthful Rosie was a delicious bonus. The submissive thrill of being dominated so thoroughly by a barely adult girl, magnified his sense of humiliation beautifu...