Gay Grandpa Stories

24,834 results
Orientation
Length
Source
Infinite Scroll

Janet

by OrgasmingLover on Sep 16, 2017
Romance

Disclaimer: I do not own Victoria's Secret, Starbucks, Manhattan, or BMW. I have never even heard of anything called Tugwell Fargos and Company company. So yeah, enjoy. * Janet was browsing through the Victoria's Secret Summer Preview catalog. She was sipping a Starbucks Vanilla Latte she bought earlier when she went out to do some shopping outside of her...

Once Again

by Cuckolding101 on Sep 17, 2017
Loving Wives

I'm know what's on the other side of the door which makes it both difficult to open and impossible not to. She sent me the text, a warning and an invitation, leaving my gut in knots of anticipation and pain. I know why it has to be this way, why nothing is just one thing, but opposite and incompatible things all at once. I can hear her. I need to see her bu...

Jackpot

by puzziboi on Sep 13, 2017
Transsexuals & Crossdressers

Larry pulled a crisp one hundred dollar bill from his shiny gold money clip and tossed it towards the check. "Will you need change, sir," asked the long haired waiter. "Yes please." "I'll be right back," the server offered. Marlene, Larry's wife of 21 years, shifted uncomfortably in her seat. "I need to use the ladies' room. I'll meet you at the car." "...

My First Time Bi

by xxxphoenix72 on Sep 12, 2017
Group Sex

My Girlfriend recently asked me about any gay/bisexual experiences I had and I never really fully answered her question. We were in bed at the time and I was easily distracted. Rather than bring the subject up again, I thought I'd post it on here and send her the link..... It was twenty years ago now, I was seeing a girl by the name of Sarah, who was, argua...

Bar Table Fun

by princess_nicole on Sep 13, 2017
Transsexuals & Crossdressers

Up to Miss Kate's door i walked, then knocked on the door happily. i hadn't been to Mistress's home for a couple weeks, and was thrilled to finally be back to see Her. She opened the door and smiled at me, i smiled back and lowered my eyes. "Come in sissy", She ordered. i quickly scampered inside and set my bag on the floor. She closed the door and came ove...

Wagner Park Ch. 07: Rest Areas

by charlessmythe on Sep 19, 2017
Group Sex

It was Sunday evening and that meant Waggoner Park. As always I rode my bike the half mile to the park and stashed it in the bushes and strolled around the area across the parking lot from the baseball fields. I wasn't there long before I hooked up with guy that said he is married. We met in a wooded area just back from the street light. He was looking for a...

A Romantic Evening

by Greyman01 on Jul 17, 2018
Erotic Couplings

A note to readers: I sometimes write sections of my stories out of sequence or to ensure that a specific idea or scene is captured when I think about it. I hope that when I fit the parts together they appear seamless and the resulting story does not 'jump shift' when the parts are melded together. Below is such an example of a scene that I did not want to...

Don't Open the Door Pt. 02

by MaxwellSpanx on Mar 6, 2018
Loving Wives

It was time for action. I climbed to my feet and, curled my fists then stormed downstairs. "Lads. Out. Now. Game over. Dawn is too pissed to make definite decisions." Jake turned to face me. "Hey, hang on Rocky Big Balls. I wondered where you got to." "I don't want to make a scene." "Er, well you kinda are." "Just leave. You've had your fun. Now fuck off...

Unexpected Beach Reunion Ch. 05

by TJA on Apr 17, 2018
Exhibitionist & Voyeur

Nikki explained to me how once or twice a month she would get what she called a 'special' booking from a lady looking to do a private shoot. She explained that she had only ever taken bookings from ladies and used a website few straight men would use and by word-of-mouth. She got very excited as she told me how she once did 4 shoots in one weekend, three at...

Five Nights at a Conference Pt. 04

by luckyfucker on Apr 3, 2018
Group Sex

Editor's note: this story contains scenes of gay male sexual content. Note to readers: features a transsexual in group sex, and a light degree of domination. If this isn't your thing, please move on to something you'd enjoy more. ***** DAY 4 By this point it was clear to me that she'd do anything for my cock, and I was determined to test it. I did a litt...