Gilf Anal Stories

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Young Greg Ch. 02: Roger and the GILF

by StrattonChambers on Sep 28, 2020
Group Sex

After our first meeting, I saw Roger got often, usually once or twice a week. We spent a lot of time exploring mutual masturbation, touching, oral and rubbing our bodies together. I loved feeling my cock moving against all parts of Roger's body: his crotch, face, asscrack, armpits. We would suck each other's cock and finger each other's asshole, but neither...

The Book Signing Pt. 04

by FOUNTAINPEN67 on Nov 6, 2018
Group Sex

Without any further ceremony the assertive black woman hoisted her skirt high, seating her ass down on the edge of the pool stairs, careful not to get any of her hotel uniform in the water below. She then lay back on the concrete decking, parting her thighs as she worked the front of her blouse open. I didn't need any coaching as to what to do next. I'm a...

Mature Bliss Ch. 01

by MarcusWoolf on Sep 14, 2017
Fetish

I hated it. I had just turned eighteen, but still my mother and my stepfather insisted that I accompany them on their summer vacation to this summer resort by the sea; an old, crappy beach hotel that had seen better days. The only nice part was that I had got my own room, whilst my mother and stepfather slept in a family room together with my two younger, ir...

The Transformation Ch. 01

by BE1953 on Feb 6, 2018
Loving Wives

This is a story of an amazing transformation that my wife of over 30 years undertook. My wife Jessie is a 51 year old mother of 3 and we have 2 grandkids (and yes, she is a GILF). Jessie has always been very beautiful in my eyes, although nothing jumps out at you when you see her. She is 5' 1" and 128 pounds. Her breasts are a very small B cup (borderline A)...

Hot GILF Wife Ch. 03

by shoguy on Oct 19, 2020
Mature

76 yr old GILF seals another deal for hubby with thug black rap star. DARCELL One other time I helped my husband secure a lucrative contract was with an up-and-coming rap artist. His name was Darcell Roberts, but went by the name of 'The BIG Hook.' My husband was not fond of rap artists, because he has prejudice towards minorities, largely people of color...

The GILF Next Door

by naughtymdguy on Sep 19, 2017
Mature

Note: This is purely fiction. All characters are over the age of 18. This is my first story. All feedback, pro or con, will be most welcome! ***** Chapter 1 A couple of years after I got out of college, I got lucky and landed a well-paying job with a great company. Secure in the knowledge that my job wasn't going to disappear (and I could afford it!), I...

Cumming Into The New Ch. 01

by blqlite on Sep 14, 2017
Erotic Couplings

*The fictional story of an everyday mature white woman who wants to feel really sexually alive for the first time before it gets too late as told by the one who she eventually turns to for help. Her first and most likely last Lover. A Black Man. CHAPTER ONE - CUM TO THINK OF IT I remember when I first met Linda. She was a frequent guest at the casino whe...

You Bet! Ch. 02

by Charkas on Feb 6, 2018
First Time

In the previous chapter, Thomas the tripe shop owner agreed the bet TC proposed him: to find a virgin prostitute around the red light district of Athens in order to save his business. Since TC was a Tax Collector, and Thomas did not make his tax declaration for the last three years, he would either have to pay 1 million euros, or take the bet. Thomas chose t...

The Games the GILF Plays Ch. 03

by milfleglover on Sep 13, 2017
Mature

(NOTE: This is another in an ongoing series of stories involving horny older women playing devious sexual games with younger men and/or women. These won't be connected, though some may be, and are meant to stand-alone individual stories in a themed series. This is a shorter one, quick and to the sexy point. Thanks and enjoy.) Tommy was bored out of his m...

Massaging Mrs. Lindsay’s GILF Feet

by milfleglover on Sep 12, 2017
Fetish

Caroline Lindsay came home from a long day at work, tired. The short-haired, 60-year-old divorced blonde with a lean, sinewy body had just poured herself a glass of wine when the bell rang. At the door was Kevin, her best friend's 19-year-old son from down the street. "Hi, honey, come on in, what's up?" Caroline asked, ushering the strapping young man in th...