Anal Grandma Stories

49,776 results
Orientation
Length
Source
Infinite Scroll

The Male Escort Ch. 02

by DG Hear on Sep 16, 2017
Romance

I have been out of college for almost four years now. After graduating at the top of my class and having saved so much money, I opened up my own computer service business. I did some repairs and installations of new units. My main goal was still teaching. I was afraid to apply in case the solicitation charge showed up again. The summer teaching job I lost du...

A Shared Wet Fetish Ch. 08

by flashgordon562006 on Jun 17, 2019
Fetish

The years passed, surprisingly slowly. Grandma did slow down a bit and was really beginning to look and feel her age, now in her mid 80's., however, when we were together, sex was just as interesting as it had always been. She was still quite agile, no arthritis or rheumatism, or any of the other usual older people's ailments. She still had her weak bladde...

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,...

Three Ages of Woman Ch. 03

by istanbulnoir on Sep 13, 2017
Erotic Couplings

AN EROTIC PICARESQUE A couple of days later I was with Mum and we were getting down to it and her delicious dirty mouth was getting to work on my cock, when she suddenly stopped gobbling me off and got hold of my balls and pulled them and dug her nails in. Yeeouch...she was not just playing around...it fucking hurt! 'What are you doing that for?' I screame...

Grandma's Big Mouth

by Madabouthair on Sep 25, 2017
Mature

Kenny Shea loved his grandmother dearly, which is why he often rode his bike across town to do chores and things the widowed senior citizen could no longer handle easily. That was how he ended up painting her garage during the recess between semesters at college, and while it wasn't really something Kenny was particularly good at or enjoyed doing, he did it...

Alien of the Family

by cwr2000 on Sep 12, 2017
Sci-Fi & Fantasy

The Louisiana bayou was extremely hot and humid, with thick clouds of mosquitoes and gnats swirling around the red sportscar and the two women who emerged from it. Linda was a 36 year old redheaded woman with sexy, rubenesque curves on her 5'6" body, with 36D breasts and hips that flared out to give her an hourglass figure the men she had fucked in her life...

Nina's Night Visitor Ch. 02

by SexyNina071989 on Oct 12, 2020
Romance

This story is pure fiction. This story Is for adults only. Do not read this story if under eighteen years of age, or live somewhere where adult material is illegal. All Characters are eighteen years of age or older. ***** Nina's body continued to tremble post-orgasm. The juice of her sex still dripped, Her cunt still agape. She had mixed emotions. Nina...

Grand Opening Ch. 02

by JimBob44 on Sep 16, 2017
Non-Erotic

Chapter 1 Penny Eastman wasn't a neglectful mother. She wasn't a domineering mother. She wasn't a permissive mother. She tried her best to raise her daughter, Vickie Eastman right, tried to raise her to be respectful of others, conscientious, and courteous. Penny tried to teach her daughter the same morals and principles that her own mother had taught her....

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...

Three Ages of Woman Ch. 01

by istanbulnoir on Sep 12, 2017
Erotic Couplings

AN EROTIC PICARESQUE They were quite a trio. Three generations of one family: daughter, mother and grandmother. They were all three together when I met them. It was in a bar. It was unusual enough that the three of them were out on the town together, but then they were an unusual family. Well, Grandma; we're not talking wizened old hag here. This Grandmothe...