Milf Virgin Stories

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Dating Site Sex - His Story

by KissedMany on Sep 13, 2017
Erotic Couplings

My name is Richard. I'm an eighteen-year-old high school senior. I have been having great fun trolling the dating websites for a lonely MILF that will hook up for sex. I can't believe how easy it was to start having sexy messaging with these ladies. It's like a candy shop. All types of horny ladies message with me while they play with their pussies. We trade...

Rory's 18 Birthday Wishes

by MTL17 on Sep 11, 2017
Celebrities & Fan Fiction

Author's note: This story is co-written with another author called LL. It's based on Gilmore girls and is a Rory/Lorelai pairing so if you don't like mother/daughter stories you should read no further. * "Sweet eighteen and never been..." sang Lorelai Gilmore as threw herself on the bed like it was a trampoline and it was her Eighteenth Birthday, not her...

I Don’t Need Clothes

by Quazar on Apr 22, 2025

Throughout history clothes have been a symbol of power and strength. Without them you are viewed as powerless, ****, afraid. Well not these people they set out to prove that even without clothes they can be just as strong just as proud. The reasons why they do this are many and varied but at the end of the day it’s always their choice.What's next?...

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Shemale Stories: A MILF Fucked

by silkstockingslover on Sep 25, 2017
Illustrated

Summary: Lonely MILF walks in on teen girl masturbating and.... Note 1: Thanks to Hernandez for doing the photos for this story as well as the plot bunny that led to the final story. Note 2: This is a 2017 April Fool's Day Contest story so please vote. Note 3: Thanks Tex Beethoven, Robert, goamz, With my daughter Simone away at band camp as a counsello...

Wedding Day in the Closet Phone Sex

by SusanJillParker on Dec 12, 2018
Erotic Couplings

Brett leaves his promised to be bride standing at the altar for his mother-in-law. Brett gave his credit card information to an operator before being allowed to speak with one of the women on call. Ring... Ring... "Hello. Welcome to Cassandra's telephone sex line. This is Cassandra," said Cassandra with her sugary voice so sultry sweet. "What's your name...

A Courtesan Becomes My Confidant

by TheBusinessMan on Oct 6, 2020
Erotic Couplings

August, 2020 Here is my preamble to this story and my comments as I get near the end of the series. Generally, readers seem to enjoy my stories and I am grateful for the views, votes and comments. Actually, some of the comments I didn't appreciate and I deleted those as soon as I read them. I started writing these stories in the summer of 2017 to see if...

The Metro Experience

by Voicee on Aug 19, 2017
Exhibitionist & Voyeur

Andrew was going for his school, he usually took the metro and today was no different. It took him 45mins only to reach his station. But it seemed very long when compared to rush that happens every other day. But today was a mother of rush that too early in the morning. Andrew's eyes wide opened when he saw the metro coming, the number of people astounded h...

Doing A MILF

by kornslayer1 on Apr 22, 2025

"Hey, Amy," I said, walking into her room. "Hey, Ben," she responded, turning to me. "How have you been?" she pondered before kissing me. I failed to answer and just checked her out for a moment in silence. "Does that mean you like the top, Ben? Is it all the colors?" "And the black pants too, they perfectly match...

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"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...

Three Models in a Vegas Hotel Room

by TheBusinessMan on Nov 22, 2017
Erotic Couplings

My stories are in generally in chronological order. I encourage you to follow along and read these stories in this order as a prelude to this one: I Hire Monica The Maid Monica's First Day as My Maid Monica the Maid's Three Hole Day I Partner with Linda, A Salon Owner I Massage Monica the Maid Hot and Sexy Business Opportunities I Become a Therapeut...