Grandma Spanking Stories

26,794 results
Orientation
Length
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Infinite Scroll

A Baptist Life

by DonBrown on Jul 3, 2018
BDSM

An account of the early life when Don got married and lived under Pa and Grandpa's roof. My Baptist Life - Don Brown There was a lot of activity in the Brown homestead in the late 40s early 50s as 3 healthy children were born to Jacob and Janet Brown. I was in the middle so had plenty of female support growing up, sometimes painful but always loving. We...

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,...

Letter to Santa - A Holiday Story

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

Every year Grandpa answers the question, "Why did you and grandma get married on Christmas Day?" This year, gramps gives the true answer Almost all erotic content in this short story is implied, not explicit. It is very mild, but somewhat romantic and filled with Christmas magic. If this is the first of my stories you have read, be aware before you look at...

Serving a Dominant Couple Pt. 08

by davetoyboy on Sep 26, 2017
BDSM

This is the eight part of the series and takes place after the last part. I suggest you read the previous parts to understand the people and how they got to this part of the story. ***** Karla and I walked into the dining holding hands. Anne, Bob, Mistress Emma, and Hans were sitting at a table and they waved us over to join them. Karla and I were naked. W...

Playtime Just Got Serious

by Annie1031 on Sep 12, 2017
BDSM

SMACK! What the HELL? I am instantly wide awake but totally and thoroughly disoriented, my entire body in fight / flight mode as I see my husband's waist at the side of our bed just before he places a mask over my eyes and I feel the sheets being yanked down and a pair of hands (not his?) grab my ankles and pull my legs down and apart while he pins my right...

Timmy's Talented Tongue Ch. 04

by milfleglover on Sep 25, 2017
Mature

My Fourth of July had been fruitful. At my usual gathering of friends at my house, Timmy, a shy, handsome 18-year-old friend of the family, had come by. Quite unexpectedly, and delightedly so, I, and then later my sexy old girlfriend Linda, drained the young stud dry, between us milking six gorgeous loads from him, all the while enjoying his talented tongue,...

Modern Family S4E6: Haley's Party

by Stories_From_the_TV on Sep 12, 2017
Celebrities & Fan Fiction

This, and all my other stories, are planned to be standalone stories set during episodes of TV shows. Any events or situations from other stories do not roll over unless stated. The set up for these stories may be ridiculous, so if super realism is your thing, I apologize. If you have any story ideas based on this show or others, that you can explain don't...

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...

Skunk Ruins the Camping Weekend

by chrisberg on Sep 26, 2017
Exhibitionist & Voyeur

As long as I can remember, my parents owned a cabin up in the mountains. It was a nice size cabin but the best part was we had a huge yard, about 25 acres, near the river. As a family, we would spend many weekends camping. I am the oldest child in the family, one sister in the middle, and one brother who is the youngest. We get along most of the time but we...

Sugar Daddy

by Suzanne on Sep 12, 2017
Humor & Satire

The summer before my senior year of college I spent the third week of August with my roommate Karen. She had kept begging me to come and hang out with her. "More fun than you can possibly imagine," Karen nagged, “please come for a visit. You’ll love it, I promise.” "What's up with that?" is what I usually responded whenever she went on about her family an...