Gay Cigar Stories

260 results
Orientation
Length
Source
Infinite Scroll

Sex, Drugs and My Neighbour Daddy

by sissymaffy on Aug 30, 2017
Gay Male

I was 18 years old at the time of this story. ***** I was a very horny boy throughout my teenage years and despite being straight, I always had fantasies about getting fucked by older, straight and MARRIED men. I am an average sized guy with a really small dick (like 3 inches) but a big bubbly ass (lots of people mistake it for a women's) and I fulfil my...

Leather Sir Pt. 01

by LthrBndBy on Jun 8, 2020
Gay Male

Our First Meeting I had a highly sensitive job which kept me from exploring my personal fetishes for years, but I couldn't take it anymore. I changed careers and found something I could do that was much less public and could be free to explore. I found myself on a fetish site, had an account, and took pictures of myself, no faces of course, in my favor...

Good Afternoon Ch. 16

by Dionyus on Sep 14, 2017
Gay Male

The three story red brick building looked old, but was fairly well kept. Manicured shrubs were trimmed to just below the first row of windows along the front face of the hotel. The main entrance had a large covered porch where you could drive up and drop off your luggage then turn your keys over to an attendant who would park your car for you. The attendant...

Inside Mark's Jockstrap

by cutandhorny on Aug 18, 2017
Gay Male

I hadn't seen my pal Mark since graduating from high school five years ago. I figured we could reconnect at our 5th year reunion. He practically had to be there, having been the student body president for our senior year. I spotted Mark across the room when I walked in. We both continued circulating, and while our eyes met once in a while, it almost seemed...

Gettysburgh Alone

by whoisboss on Aug 18, 2017
Gay Male

I was vacationing alone in Gettysburg Pa. I am 34 and unhappily married. At 6 foot and 210 lbs. I can find women but I have been curious. I decided to stop at 8 p.m. At the local cigar shop just as it was closing. I talked to the older men who work there he was about 60 and I was about 35 at the time. He was over 6 foot and thin. He had a beard and a mean l...

Doctor's Orders Ch. 2

by cigarstud on Sep 14, 2017
Gay Male

Please read original story first so this will make sense. I didn't hear from Red Gibbons for nearly two weeks, but I had not forgotten him. How could you forget someone like Red? I could still taste the musky cheese of his uncircumcised, fat cock. He had awakened something in me that I had previously thought was hidden for good. Until Red, I had enjoyed the...

Shattered Boundaries Ch. 03

by Humilifuck on Sep 14, 2017
Gay Male

A black leather gloved hand crawls like a spider up my leg, leaving in it's wake a trail of tingling flesh. It lingers to caress the muscles of my inside thigh before a single leather finger slips between my ass cheeks, stealing softly towards my asshole. A dark figure leans in close, his hot breath scorches my skin as he whispers, "Who owns your ass?" My...

The Second Oldest Profession

by Marchpane on Aug 18, 2017
Gay Male

I I'm not saying older guys can't be pretty, but WhiteStallion10 wasn't. He was sort of tough-looking, with a narrow face, flat cheeks; a lean, strong jaw; a wide, red mouth with a slightly crooked upperlip that seemed inclined to sneer; and sandyblond hair, cut military short with a pronounced widow's peak. His cobaltblue eyes were intense and vibrant. I...

Under The Table

by TheNakedGinger on Dec 12, 2018
Gay Male

I sat down at the conference table opposite this new client and tried not to focus on my nerves. This was my first solo contract at the law firm I've been working at for a few years now and I needed it to go well. If it did, it meant a salary bump and one step closer to making partner. "You're late." The older man said gruffly. I wasn't. I was actually 1...

My Sweet Bitch Ch. 02

by JasonClearwater on Jun 18, 2018
Gay Male

Author's note: [For 'Carl'] Okay, there might be a couple more stories in this vein, since people seem to like them. And yes, Jaspar's a bit of a prick, who needs an urgent wake-up call. But for those of you who deeply dislike him, stick with it... I promise, it'll be worth it. Go into it with a dark sense of humour, and trust me to sort him out. ;-) ***...