Mature Friend Stories

155,711 results
Orientation
Length
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Infinite Scroll

A Sweet Gift From a Friend's Mom

by saketii on Sep 12, 2017
Mature

I got my first taste of pussy when I was 19. It was also the first time I ever came. I mean I jacked-off many times because it really felt good but I never came. My lover at the time was my 45 year old Arun's Mom. Arun was my best friend for some time now. We kinda seduced each other seeing hot older moms around us. The whole thing happened something like th...

Birthday Delight Ch. 01

by rcwilliams on Sep 13, 2017
Mature

Author's Note: This is a special birthday story dedicated to a good friend of mine. No infringement is intended. Everyone involved is over the age of consent. (18) ***** It's 9am, August 30th and here I am working on my 26th birthday for someone that didn't show up. I'm Aaron Kinkle and my stats are not important right now, but if you must know, I have dir...

Black Journal Ch. 11

by Dhc000333 on Sep 13, 2017
Erotic Couplings

Duncan Cyrus, age 21, Mom's Bestie Maxine Griffin. My mother's best friend and one of the thickest, well-shaped, mature, African American women I have laid my eyes upon. She's the same height as my mom, which is about 5'4". She had two daughters, and they got their sizes from her as well. She would always bring her kids with her and I would pretend to be t...

Eleanor of Penkhull Ch. 02

by Sputnik57 on Mar 2, 2020
BDSM

Violet Preston scoffed at the timid and slightly younger male's impromptu advances toward her, guarded though they were, but his impertinence excited her in a strange way; his gestures feigned a certain obedience toward her femininity, before he blushed and cut the spur of the moment conversation short, bringing a welcome but unsatisfied tingling to her cunt...

Rachael Ray Nympho Queen of Mean Ch. 04

by DickThePimp on Aug 8, 2018
Celebrities & Fan Fiction

This is a parody... It is not real It was a bright sunny day in The Hamptons. Rachael Ray was having a pool party, for some famous and not famous, friends, at her new beach house, she and husband John had recently bought. Everyone was in swimsuits, drinking, eating and having a great time. Just another normal party amongst friends, right? Not quite. It was...

Cleaning Janice's Windows for Free

by alexcarr on Sep 14, 2017
Mature

Cleaning Janice's windows for free... Feeling her suck took away all the notions that I wouldn't get any satisfaction from a sixty year old. I would never have entered into the situation had it not been for my good nature - although I say it myself. I just felt sorry for Janice that's all - and even though she was old enough to be my mother I had to conten...

I'm A Very Bad Girl

by Dublin2009 on Sep 16, 2017
Transsexuals & Crossdressers

That Monday afternoon I felt something change inside me, no more would I be satisfied with mere fantasy masturbation, I now wanted more. All that morning I had been playing in my girlfriends closet, we were on the verge of breaking-up for a multitude of reasons, and had slept in separate beds, like a long married couple, for months, so I had no inner confli...

Haitian Voodoo Femdom Rocks

by Samuelx on Oct 6, 2020
Erotic Couplings

Meet Dennis Pierrot, a big and tall black man living in the City of Cap-Haitien, Haiti. A maintenance man at College Notre Dame Du Perpetuel Secours, Dennis is a hard working brother with an embarrassing problem of a personal nature. Simply put, Dennis is constantly constipated, and he has tried just about everything to cure his affliction. What's a brother...

The Wonderful Aunty Rachel

by Stonemarten on Sep 14, 2020
Mature

At the time of this story, I was about 30 years old and at the peak of my virility; I had recently broken-up from a long-term relationship and feeling a little bruised by the experience, though I never felt lonely, as I've always had good mates around me, both male and female. My mum used to take short holidays out-of-season at a quiet beach resort in Spain...

Fuzzy Flight Pt. 02

by MarcusWoolf on Sep 14, 2017
Fetish

This story is part 2 of my first story, "Fuzzy Flight". I recommend reading that first. After we had landed and had docked at the appropriate boarding bridge, there was a general rush to leave the plane. On my arm I carried the lovely thick and heavy knitted coat for my mature blonde travel-mate on her suggestion. That was a good thing, as it hid the big we...