Gay Dilf Stories

18 results
Infinite Scroll

For My First Time, I Find a DILF Ch. 01

by jlondon89 on Jul 15, 2020
Gay Male

I'd first seen him on a gay dating app a couple of months before. I must admit I didn't find many men attractive, but he'd really stood out. The stereotypical classic - tall, dark and handsome. Finally I understood what women always went on about. His profile simply said "47. 1km away." He was a little over two decades older than me which was an age gap tha...

For My First Time, I Find a DILF Ch. 02

by jlondon89 on Jul 27, 2020
Gay Male

My heart thumped in my chest as the lift crept up towards the second floor and flat number 52. It had only been a 10 minute walk from my own flat to his but it felt like I'd arrived within seconds, despite the million thoughts buzzing around in my head on the way. I walked dizzily through the corridor, feeling like I was in a surreal dream, but I was glad o...

Bachelor Party Mishap

by vikkihawe000 on Jul 14, 2020
Gay Male

Arthur had just returned to his Las Vegas hotel room after a night at the blackjack table. His friends had organized the whole trip for his bachelor party as one last hurrah before marriage. He asked his friends for a tame weekend, just some drinks and some cards in Vegas. So far, his friends had cooperated. He loved Jessica and she made him promise that the...

Making Tech U Proud

by maxwelldymes on Sep 1, 2017
Gay Male

A few weeks ago I was asked by my alma matter if they could do an interview on me about my career for the "Alumni Spotlight" feature of the newsletter. What the fuck I thought. Why not? If it wasn't' for good ole Tech U, I wouldn't have this job. Let them send their little geeky college student or some old hag from the Career Services over to interview m...

Sharing a bed for one night

by Mac0075 on Apr 20, 2020
Gay Male

Sharing a bed for one night It was a balmy mid-summer's Friday evening, and a local band booked to play at the pub down the road meant the place was packed. My partner, Tom, and I had gone to meet up with a few friends, some girls I knew from work and a guy called David, who originally was an old friend of Tom's who we'd recently reconnected with. The drin...

Ant Pt. 02

by kwchancellor on May 9, 2018
Gay Male

Ant lay naked and satiated on the bed, watching Cal leave the room. His anus was sore, feeling both full and empty from the thorough fucking he had just received. Having had very little sleep the night before, then cumming three times under Cal's skillful manipulations, his eyes were heavy, his limbs weak. He fought against it, not wanting to disappoint Cal'...

The Mechanic

by Connermt on Oct 6, 2020
Gay Male

About five hours in to my drive a gasket blew on my car causing me an unexpected detour to my closest dealership. I pulled in to the bay obviously annoyed and was met by a pleasant service advisor names JC. As I explained my issue and frustration, he smiled. Normally that would have made me more irate but, somehow, his smile did the opposite. He talked wit...

Salt and Pepper

by kerrymcboyd on Sep 14, 2017
Gay Male

I never actually really liked beaches. Sand would find its way into places on my body that I didn't know was possible to even get sand in, and it wasn't like I rolled around on the beach or volunteered to have my cousins bury me in the ground and build a curvaceous bikini-worthy model on top, like those cheesy photos where the idiots are grinning just above...

Lending a Hand to the Neighbor

by JackRain2020 on Mar 16, 2020
Gay Male

Author's Note: this story is fiction. Safe play is smart play! *** Sometimes you just get lucky. But luck isn't all of it, sometimes there are benefits to noticing the little things in our daily lives. This is a story about how noticing my neighbor led to a dream come true for me. I'm sorry, I should at least introduce myself a little. I'm Jack, a regular...


by Connermt on Oct 5, 2020
Gay Male

I've only been going to the gym for a few weeks, but I really enjoyed it. I particularly liked how my middle aged body was firming up. It's been a few months since I last worked out, but with the move and new job, it took a while for me to get in to a routine. I'm not a gym rat by any means. I've been called a DILF by many and I'm okay with that. I was twent...