Mature Anal Grandma Tales Stories

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Little Red Riding Hood

by gatorman on Sep 26, 2017
NonHuman

(A story by Bros. Grimm, slightly altered by Gatorman) I know . . . You've already heard the story of Little Red Riding-hood, when you were a little boy or girl yourself. Only remember: THAT story was translated to English from the German story compiled by the Brothers Grimm, along with a LOT of other similar German "Fairy Tales." When they compiled t...

Further Training as Sissy Lesbian

by maturesubmale_for_F on Apr 22, 2020
Transgender & Crossdressers

Dear readers, This is a continuation of my story 'Miss Johnstone's Lesbian Sissy Slut' and I sincerely recommend reading that story first as it provides background for this one. Enjoy and please take time to give me some feedback! Theo 3. Intermission: Further training Following the loss of my sissy virginity just after I had turned eighteen years old,...

My Grandmother Teaches Me About “Life" Ch. 03

by kingswede on Sep 17, 2017
Mature

This is the third in a series of chapters of how my grandmother instructed me on the ways of PLEASURING ladies. All people / charters in these stories are older than 18 and younger than 75. Any resemblance between real people and ones in these stories is just a coincidence. NOTE: Maybe I should digress a little here and tell you how Grandma came to be livi...

White Grandma Strapons Black Guy

by Samuelx on Sep 16, 2017
Interracial Love

Doris Wilkinson, suburban dominatrix extraordinaire, smiled to herself as she whipped Jamal Louis-Pierre. The young Black man squealed as the bossy older White lady whipped and berated him, deep inside her basement in the town of Nepean, Ontario. How she loved that sound. The blonde-haired, big-bottomed, fifty-something White woman smiled at her latest submi...

Anne & Walt: Grandma Smith's Decision

by Edwin on Sep 12, 2017
Mature

Interesting crowd of people assembled. Anne made a mental note to come back one night when she hadn't any plans. She filled the empty stool next to a couple of bickering lesbians and ordered a beer after being told it would be another ten minutes for the lasagna dinner she'd phoned in. The elfin mulatto girl, with the long braids, platinum jewelry and a gauz...

Old Man's Fancy

by scorpio00155 on Sep 11, 2017
Mature

At eighty-three Geoff Weetman was still active, admittedly not as spry as in his youth and with a lot of curses for the stiffness of his joints, but active nevertheless. Although a member of a number of social clubs and groups, he was lonely and had been for the past fifteen years following the death of his wife, he smiled at the memory of her. Their time to...

Red Riding Hood

by gauchecritic on Sep 12, 2017
Humor & Satire

In a land far away and long. long ago there in a small village close by the great wood there lived a girl called Elaine. She lived with her step mother who was surprisingly, and against all the odds in a fairy tale, not wicked. Elaine, and many of the local woodcutters did notice however that her step mother had a wicked grin and equally wicked curves whic...

Anna

by JustLikeEwe on Aug 31, 2017
First Time

This story involves a young man who is a virgin, and a woman over three times his age. Therefore, this is both a "first time" story and a "mature" tale. * This wasn't the way that most guys my age want to spend the summer before heading off to college, I recall thinking as I looked out the kitchen window to the tiny yard and the postage stamp lawn that mig...

Family Secrets

by Benny_Blank on Sep 16, 2017
Mature

To really understand the secrets, you've got to understand the background, so bear with me as I recount the family history before I get to the family secrets. Dad passed away years ago, killed while working on a construction job. He was literally hit by a ton of bricks that were dropped by a drunken crane operator. Mom got all of the Worker's Compensation b...

The Shoe Store

by Honda629 on Sep 13, 2017
Fetish

I woke up disoriented. I was extremely confused. I wasn't totally awake at the moment. I was still half asleep. The place smelled like raunchy feet. My pole became so stiff, I felt someone gyrating on top of it. A contraction squeezed hard. I felt hot flesh over my 22 year old face. I couldn't see. Sweat dripped over my face. I started to sniff uncontrolla...