Naive Milf Stories

10,838 results
Orientation
Length
Source
Infinite Scroll

Shane and Carmen: The Novelization Ch. 22

by O_G_Salli on Sep 16, 2017
Novels and Novellas

Chapter 22 When It All Goes to Hell the First Time It took Mattie Shepherd nearly two weeks to confer with Bernie McFadden, perform her due diligence research, draw up all the necessary paperwork, get Shane's signatures, and get a check cut for $50,000 out of Shane's trust fund. This suited Shane perfectly, because on the following Monday she went in to wor...

Cuckold Chronicles: Damon

by deltonaman2man on Sep 14, 2017
BDSM

Prologue This is the third part in the continuing adventures of Heather and Dave. A couple very much in love, playing out their fantasies. It has been 3 weeks since Heather took me to Todd's house for an evening of wild unbridled sex (for her and Todd ) and humiliation ( for me ). { See Cuckold Chronicles: Todd } We left there riding high on the excitemen...

My Best Friend's Mother

by Many Feathers on Sep 19, 2017
First Time

Danny would kill me if he ever knew, ever found out...I had watched his mom pleasure herself. Bad enough that, but that I had in turn, jerked off watching her do that, though of course no one would ever know. Certainly never my best friend Danny, though we had years ago sworn to one another as kids growing up together, we'd never lie to one another, or keep...

The Gulf Coast Move

by HStoner on Mar 26, 2019
Exhibitionist & Voyeur

While this story draws on some real experiences, it is a work of fiction. Any resemblance to any real person or institution is coincidental and unintentional. ***** It was one of those moments when you think "yes, things have worked out pretty well." My wife, Carol, my daughter Gwendolyn, and I were standing outside our newly-built home on a barrier island...

Ku Ku Ka Choo Mrs. Robinson Ch. 01

by R410a on Mar 25, 2019
Mature

There they were again, the three young boys thinking they're hiding in the bushes while they watch me. I can hear them snicker and chuckle, stupid shit only boys in the early stages of puberty think of and do. It happens every so often, typically every two or three weeks if the weather is nice enough to sit on the patio and read. I'm blessed to have a posi...

When Angels Cum Ch. 14

by CapDragon121 on Apr 8, 2019
Sci-Fi & Fantasy

Obligatory Warning: 1. Only one sex scene in this chapter, but it's quite long. 2. Response to comments has been moved to the end of the chapter. Editors: Dankmemez/AC Lawrence & DrasticXplorer. I think they've done an excellent job of editing my story. Special thanks to Curtis, Bradley, Joshua, FlyPenguin, RandomTask, RogueXVII, Tristan, Vibrant, Woot...

Summer Boy Ch. 01

by TrueNorth1969 on Sep 12, 2017
Erotic Couplings

"Out Adam!" Lynn pointed her finger sternly to the other side of the reception desk. Adam sat on the top of the desk belonging to Cassie, a young, very buxom, brunette receptionist. The girl didn't seem to mind much judging by her wide, sparkling grin. He offered an innocent glance towards his supervisor. "Now!" Lynn insisted, "Stop hanging around receptio...

Unexpected Find

by Overhill63 on Sep 14, 2017
Erotic Couplings

So there he was sitting at his computer, horny as always, scanning the sites looking for something interesting. Every now and then he would go to the escort sites to see if anyone interesting was coming to town. Over the last few years, he had visited with a few 'traveling' girls in addition to one local girl who, unfortunately, had retired on him. You see...

A Secret Revealed Pt. 06

by pregnantex on Sep 26, 2017
Exhibitionist & Voyeur

The words hung in the air. "I love you." I guess I did still, despite all of the aggravation over the years. Beth apparently sensed it during our infrequent interaction and used it against me. Gaining compromises when I shouldn't offer any. Making it clear how happy she was with our divorce, knowing that I was not. I did love her, feeling it as my penis la...

A Boiled Frog Pt. 02

by noobdude on Sep 18, 2017
Transsexuals & Crossdressers

Part Two -- Simmering in Las Vegas Author's Note: I was literally blown away by the positive comments I got from my first part. This is my first story attempt and I am enjoying the process. Any constructive criticism would be appreciated. I can only get better if I know what I did wrong. Chapter 1 Tuesday I woke up with all 12 coins in my possession. This...