Lesbian Grandma Stories

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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,...

Alien Flashlight Hypnotizes Women Ch. 04

by SusanJillParker on Sep 26, 2017
Sci-Fi & Fantasy

Brian hypnotizes Donna, Kathy, and grandma too After hypnotizing Grandma, Donna and Kathy's mother and Irene's grandmother with the alien flashlight, Brian led her to the bedroom where her daughters, Donna and Kathy were already naked and ready and waiting for him to give them hot sex. Unfortunately, Brian didn't even have a chance to strip grandma naked. N...

"Moms & Daughters": A Family Affair

by silkstockingslover on Dec 9, 2019
Illustrated

CREDIT & THANKS: A super special thanks to legendary artist Rebecca (of the Housewives at Play series and many more) for giving me permission to use a few of her plethora of illustrations for this story. We collaborated in 2014 on Straight Housewife Blackmailed. Also, this lengthy story is a HOMAGE to the many works of Rebecca, particularly her Housewive...

Detroit City - DGH Ch. 02

by DG Hear on Sep 12, 2017
Romance

You need to read part one to understand this story. I wrote it in two parts because of the length. Thank you for reading it and for your comments. DG Chapter 2: On Thursday, I mentioned to Sam that I was going to go see my uncle and his family on Friday and asked her if she wanted to go along and meet them. We were already going to another Tiger game on S...

Happy Nude Day Ch. 08

by BOSTONFICTIONWRITER on Sep 25, 2017
Humor & Satire

Jason's Mom and Grandmother stood naked in the archway between the kitchen and the living room with their arms folded. Sensing the seething synergy coming from the woman of the house, the room went suddenly silent while one by one, but for Susan, they all looked towards the archway and her. Still poised on her knees in front of her father, Susan hung her hea...

Easing Back Into Sex

by egmontgrigor2012 on Aug 19, 2017
Erotic Couplings

Morgan Fletcher fled to the south of England to seek revival, staying with his maternal grandmother and husband. He'd been squeezed dry by his demanding job as new business manager for an ailing firm manufacturing sanitary disposal units for workplace toilets while socially attempting to anally satisfy his new stepmother as well as performing like a stallio...

Felicity Ch. 63

by jjcolejr on Sep 12, 2017
Novels and Novellas

Chapter 63: Clara and the Aliens Several years had passed since Clara's return to Felicity and her marriage to Fiona. The years had been happy until recently. Clara found herself grieving for family members that had ceased to be. Clara was disconsolate from the death of her Aunt Martha and her Uncle Jim, she knew they should not have died. Clara had given...

Maiden Voyage

by jessicaj64 on Sep 16, 2017
Transsexuals & Crossdressers

Note to the reader – this is not a work of fiction. It is the story of how one woman found herself, in spite of the odds, and in spite of being born with a male body. It is entirely autobiographical, sometimes painfully so. But having read many tales of transsexuals, which end up being, in most cases, little more than tales about the cross-dressing fetish, a...

My Fall and Rise Ch. 11

by MelissaBaby on Oct 14, 2017
Novels and Novellas

Sugar Pie, Honey Bunch I was surprised to find out that I liked being a waitress, and after a few days of fumbling trays and screwing up orders, I got to be pretty good at it. My new place of employment was a large motel, restaurant and banquet complex named The Colonial Inn. It didn't seem very colonial through a New Englander's eyes, but it was a nice p...

Naughty, Naughty, You've Been Bad

by PositiveThinker on Sep 17, 2017
Mature

After not having seen my Stepmom, Carol, in eleven years, I not only bumped into her yesterday, Christmas Eve, I also had sex with her. I couldn't believe it. After lusting over the woman for all those years, after finding out that she was purposely flashing me and knew that I was purposely flashing her, I still can't believe we had sex. Pinch me. Then, as...