Gay Dilf Stories

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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...

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...

Thin Resolve Ch. 01

by ladynina23 on Apr 20, 2020
Gay Male

Lane "So how long have you been a nanny?" The most beautiful man in the world had just asked me. I really shouldn't be thinking of Mr. Jones like that right now. This man, albeit extremely beautiful, could be my future boss. The man who's children I would be paid to take care of. I need to keep my dick out of this. I had applied to become his nanny last w...

Ian

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...

8 O'Clock

by Connermt on Oct 5, 2020
Gay Male

I'm usually all about jocks. You know: tall, fit, muscles, smooth, young, etc. I never thought about DILFs until I met Scott. Scott was a guy that lived on the other side of my complex. I ran in to him one day while he was walking his dog and I was running. It was a hot summer Friday evening after work and I wanted to blow off some steam. Rounding the bend,...

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...

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...

Summer Afternoon

by traggot on Oct 19, 2020
Gay Male

It was a beautiful summer afternoon, and Peter laid in the hammock. The breeze swung him lightly, and puffy clouds protected him from the sun. Peter was sleepy, and when he got sleepy, he got horny. The fence around the backyard was about six feet high, preventing anyone from peeking over. All the windows in his home and his neighbors' were shaded except fo...

Efrain and Cory Ch. 28

by dayne on Sep 25, 2017
Gay Male

Chapter 28 – Gagging For It Indie refused to acknowledge the stack of bills Laurel slapped into his hand. "Why do I have to go?" he asked. "You were supposed to bring alcohol, not send me to buy it two nights before." "You always get the good stuff." She shrugged. "We thought it would be better if we just collected the money we would have spent and had...