Gaping Hole Stories

122,731 results
Orientation
Length
Source
Infinite Scroll

EXcess

by Joshua Barron on Sep 13, 2017
Group Sex

I’ve been divorced from Nellie for about 5 years. She has custodial care of our kids, so I still see her often, every other Friday when I go to pick them up for the weekend. Last Friday, when I arrived at her house, nobody answered the door when I rang the bell. Sometimes, my daughters are in their rooms getting ready when I get there and don’t hear me at...

Suddenly Single Steffie Ch. 04

by opels on Sep 12, 2017
BDSM

Jack pushed her into the room and unfastened the cuffs at her wrists. "Turn around and bending from the waist, pull down the thong, slowly," he ordered. Trembling, she turned and did as he asked. "Spread your legs and grab your ankles," he commanded once she was fully bent over. She stepped out of the thong and spread her legs, wrapping her hands around her...

Sharing Her Creamy Quim

by Corkskrew on Sep 16, 2017
Group Sex

I unlocked the door and stepped inside. As I took off my coat, I heard her voice say, I'm up here....her voice sounding warm and yet excited. I climbed the stairs and went into her bedroom which was lighted by a small night light. As I approached the bed, I could tell she was naked, her nipples standing erect under the covers. You took a long time; I've been...

A Dog's Life Ch. 06

by Compliant1 on Sep 19, 2017
BDSM

I took my time walking down the row of port-a-potties slowly and rapping on the door of each one. I gave two an extra rap, just to increase his anxiety. I finally got to the last one with the Out of Order sign and gave the door a good rap. I heard a plaintive voice. "This one's occupied!" "How can it be occupied? The sign say's, Out of Order." "Well, it i...

Fisting Cheryl

by Ravisher71 on Sep 26, 2017
BDSM

First impressions whether they be online or in person are not always accurate. I had posted online a thoroughly debauched tale of fisting and stretching – one of many. It is always good to get feedback and I often get asked if the stories are real or 100% fiction. The answer is a mix of the two. One of the stories elicited a response along those lines from a...

The Party

by HerLittlePiggy on Sep 13, 2017
Loving Wives

"No," Jess said as she pushed him away but he persisted. His hands rested on her hips and she did nothing to move them. Her heart raced and her knees grew weak. She knew what she should do but her body was at odds with her mind. Her husband, David, was watching. What would he think? His face was close and she could feel his warm breath on her neck. It sent...

Ally Ch. 01

by BadJ on Sep 16, 2017
Anal

Thursday was Todd's Birthday. He had special plans for Ally. Ally was the one to be surprised. Ally was an 18 year old senior in high school. She had gone unnoticed by the guys until she "blossomed" over the summer. Now she was 5'8", 36-24-36, with soft B cup breasts. Her dirty blonde hair was shoulder length and curly. Her all over tan made for an amazing...

Satisfying Samantha Ch. 07

by grafexguy on Sep 19, 2017
Anal

It wasn't long before I made good on my statement and was back inside Samantha again. Since it was Sunday and the end of the weekend, I knew that our time together was winding down; especially since Mark would be home from his trip later today. I had to fuck Sammy at least one more time before making myself scarce. Needless to say, even though I was exhauste...

What I Saw

by OhPossum on Sep 1, 2017
Group Sex

I was on my way to matins, leaving early so that I could drop off the first draft of my opening argument that you had requested. The door to your cell was unlocked, as if you were expecting someone, though you couldn't have known that I would be dropping by. From the open doorway, I could make out the motion of bodies in your bathroom. As my eyes adjusted to...

Jack and Jill Pt. 06: Jean

by candyflosslover on Jul 13, 2020
Transgender & Crossdressers

They had been trying for a baby for some time and had come to the sad realisation that it wasn't going to happen without some intervention. The doctors wanted them to use donated sperm and have insemination, but it seemed so clinical. Jean had told them about a breeding club that she had worked in and they both liked the sound of it, but as she was walking t...