Mature Women First Time Wearing Stockings Stories

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Infinite Scroll

Nita Takes Risks

by OpenMouth on Dec 23, 2017
Group Sex

We'd fantasized about it for months. 'The risk has to be real...' every time one of us said those words it would start a discussion; it was crazy, we agreed, but our hearts would start beating as we talked, and we'd become more and more aroused. Great sex would follow. We made a pact. We would go through with it; not some watered-down version, but the real...

Nurse Ann

by lilguy on Sep 13, 2017
Mature

I been a while sense Pete moved in with Ann as her love slave. He had be controlled and under her wing ever sense. He was treated a kid and pet over there. He was intimidated by her and scared of her but he loved her. He loved being her slave. When he obeyed she was sweet and motherly. Her smile warm the coldest of heart. When he was naughty she would punish...

Tim & Peggy Ch. 02

by sparktj on Sep 16, 2017
Mature

Note - In the first part of this story I described meeting Peggy, a 60yo married woman, at a social function with our respective partners. If you haven't read that story, I recommend you do before continuing with this one. ------------------------ Looking back to that Friday evening in the restaurant with Peggy, several months ago now, it's hard to belie...

Mom's Best Friends Ch. 03

by flim62 on Sep 26, 2017
Mature

It was about 5 months after I had come back from my trip to Boston and my sex adventure with Carol. I had just rolled into bed. I was working as a security guard and I often had to work third shift. I had gotten home Saturday morning at about 8, had a quick shower, and I was just getting ready to fall asleep when the phone rang. I groaned. I didn't really wa...

Eau de Toilette

by uksnowy on Sep 16, 2017
Exhibitionist & Voyeur

Oh the Toilet, the title? - a skillful play on words - or not A voyeur driven fantasy following many viewing of hidden cameras, ingeniously designed and positioned. Where is he taking me this time? In his hand and warm, voices young and old. Some excited, some just chatting, a female one very close to me and constantly talking to him and he responds. His s...

Specimens of Gender

by darkheathyr on Sep 14, 2017
Sci-Fi & Fantasy

"Hmm. One more chapter?" I rested the thick, hardcover book on my chest and turned my head to check the clock. It was only 11:47 - late, but not as late as some of the nights I'd put in lately. Still, I did have to be up at 5:00 in the morning. "Better not," I decided with a sigh. Since it was too big for the nightstand, I reluctantly dropped the book on fl...

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...

Going Dogging?

by TomW50 on Sep 15, 2017
Illustrated

As I went to get us a nightcap I saw the barman glance across to Eileen and smile. I followed his gaze to see that Eileen had apparently carelessly allowed her skirt to ride up over her stocking tops and as she uncrossed her legs was giving him and I a good stretch of creamy thigh and a flash of her newly shaven pussy. She smiled when she saw us glancing acr...

The Cougar and the Cub

by Intercontinental on Apr 22, 2020
Mature

Jane looked at Robert. He smiled back. The moment of truth had arrived. After three large gin and tonics which he had so generously bought for her, the moment of truth had arrived. He had pestered her for months on the dating site. The age difference had bothered her, she was 40 years old, he was 20. But she was staying overnight in a Birmingham hotel after...

Don't Fancy Yours, Mate!

by nortythorts on Sep 25, 2017
Mature

He made his way across the bar, nodding and chatting a few times to fellow conference delegates as he went to the table where Jane was sitting. She was wearing a smartly tailored blue blouse and black skirt, and looked good without being flashy. Her blouse fitted quite loosely over her matronly breasts, partly masking their DD size, and her skirt reached h...