Milf And Boy Stories

359,832 results
Orientation
Length
Source
Infinite Scroll

One Final Summer

by Subby72 on Sep 16, 2017
NonHuman

She hit the snooze button for the third time. Usually she was up and moving the first time her alarm went off. But not this day. She has been dreading this day for a year. She had met Shane in High School. The hit it off very well. Everyone called them the perfect couple. They continued their relationship through college and married the day after graduation....

Caught By My Mother-In-law

by mingeeter on Sep 19, 2017
Fetish

OH my god I have just been so humiliated by my 73 year old very strict mother in-law who was an ex magistrate for 20 years. I had seen her undressed but only over the last year when she had stayed with us her very heavy saggy tits and her very hairy untrimmed bright grey pussy shown accidently to me but no rush to hide that hairy bush from my obvious stare...

Sehnsucht Ch. 07: Horace

by ladythisbe on May 14, 2018
Novels and Novellas

That night after retiring to my rooms I discovered something frightfully troubling. My former underclothes had gone missing. The big dilemma being that my menses had arrived and I had no undergarments appropriate for the occasion. Clothilde was constantly busy in the kitchen but I always found her to be the most approachable of the lot. Therefore, I decided...

Madder Max Ch. 02

by markedas on Sep 15, 2017
Novels and Novellas

***Please note that all characters in this story are over 18. Also, this is one of my first stories that I have submitted to literotica so if you like it please comment! This is the SECOND part of a ten part series so you may want to read Part 1 first. Tina left the cage behind her despite the roar from the crowd. She had heard the cars. Perhaps that uppi...

Don't Lie

by Gethelred on Sep 17, 2017
BDSM

I tell you to kneel, running my nails across the bare skin of your chest. It's freshly waxed; you know how I don't like your chest hairy. You break out in goosebumps, and I press harder. I remind you that you are not to move, you are not to make a sound until I say so. You think about disobeying me, but you don't. Don't lie. I saw the thought flash across...

Zodiac Girls Ch. 06

by Bakeboss on Sep 11, 2017
Chain Stories

I swear that if you look up Gemini in a book on horoscopes, you'll find a picture of my girlfriend Judy there. She is such a Gemini she even has a twin brother. They are so much alike it's two sides of the same coin, just one is a girl, and the other is a boy. Judy's figure could almost be called boy -like except for the large c-cup breasts sticking out from...

Young Love the Best Way Possible

by Shammzilla on Sep 16, 2017
Romance

Walking down the hallway of this small town high school is starting to get to me. All these boys the same, country boys with their sun bleached, dirt stained jeans, mud caked cowboy boots even though they've only dreamed of being cowboys, and the dip can rings in their back pockets. Except for one boy who really stood out to me. Long black hair, chin peppere...

The Good Student

by GingerM on Sep 13, 2017
Transsexuals & Crossdressers

[NOTE: This is more of a vignette than a story, and was written in response to a "write a story to go with this picture" challenge. The picture was from an anime or manga, and the subject was a futanari girl taking a boy from behind in a gymnasium. Naoki is a boy's name meaning 'honest tree' in Japanese; Izumi is a unisex name but more commonly used by girls...

It Used to be Good Ch. 01

by _contortionist_ on Sep 13, 2017
Romance

Part I: There's no telling how I fell in love with him, I just did. Blake, the one boy I couldn't stay away from. In high school we had our ups and downs, ones we could laugh about, and ones to this day we still don't want to mention. We got back together, as friends, when I got back from travelling around Canada. Then when I got a cell phone we began tex...

Swingers Torture

by StarCrossed on Aug 30, 2017
Fetish

I was busy playing a card game when they drove up to a local coffee shop that we hung out at: Ana, Damien, and my sweet Eddie. I was a bit too engrossed in my game to notice the mischief in their eyes. Ana dropped hints about how her and her husband Damien were cold and wanted to go back to their house and change into something more comfortable and asked if...