Gay Dress Stories

3,413 results
Orientation
Length
Source
Infinite Scroll

First Time With A Guy

by girlboybootsie on Sep 16, 2017
Gay Male

One Saturday morning I awake to find the sun shining through my bedroom window. It looks as if it will be a beautiful day and I feel wonderful as I remember the dream I was having just before I woke up. In it, I was being fucked deeply up my ass on all fours by a beautiful blond hunk with a lovely long and hard cock while sucking on the cock of his twin! I w...

The Reluctant Bear Hunter Ch. 02

by newpaulman on Jul 9, 2019
Gay Male

Following our Sunday afternoon session - big, burly, hairy man-next-door Clive and I - we composed ourselves and awaited the arrival of his friends. As we ate ham sandwiches and drank tea, Clive began to set the scene. "So there's Harry and Bruce. Harry's a bank manager, tall, thick-set, smooth skin. Quite dominant when he gets going. Bruce is short and chu...

Learning to Surrender Pt. 06

by miked1983 on Jan 22, 2018
Gay Male

Rick spent the next day wondering what would come next. He realized he was never going to be able to anticipate such an experienced older man like Jack. But he did find himself hoping that he was the best Jack ever had. What if Jack still saw other personals? What if he tried out some other young partners for sex? Rick couldn't blame him - the man was so vir...

Don't Kill the Messenger

by LoveIsUniversal on Nov 19, 2018
Gay Male

The things he had seen at the strip mall could not be undone. Noel had recognized his female neighbor, and he couldn't forget what he had just witnessed. And now, he had to tell her husband the absolute truth. Noel couldn't evade a smart decision, even if he had a little trouble at the beginning of it. The eighteen-year-old man made sure that he brought his...

He Knew It Was Wrong Pt. 02

by LoveIsUniversal on Sep 14, 2020
Gay Male

The text message was short and to the point. Bridget wanted him to be with her tonight. It sounded like a fun time, but Zack already had other plans. His text message was also short and concise. He wrote that he had other plans for tonight. He issued an apology in the same text message, though he reassured Bridget that the two of them would get together agai...

A New Burn

by dingdongdiablo on Dec 25, 2019
Gay Male

A New Burn When I woke up that day, there was no reason to think it wouldn’t be normal. As I got ready to leave for work, I had no idea that the day would end with me between a man’s powerful thighs, looking up at him as he stroked into my mouth. There was zero hint on the subway that I would soon be doing a lap dance for a man trying to tug my panties off....

Make Your Motions

by LoveIsUniversal on Dec 3, 2019
Gay Male

Caleb waited until his wife would leave. He stayed in the living room and pretended to watch something on TV. It was an ordinary Saturday afternoon, with no idiosyncrasies that interfered with human routines. The city of Sacramento was treated with a moderately cool weekend. A partially cloudy sky and a gentle breeze from the Pacific had spread across quiet...

Seduce Me

by ChasBozwell30 on Jul 6, 2020
Gay Male

My last master only wanted to humiliate me, so I let him. But it wasn't what I wanted, what I needed. He wanted me to be an object, an empty one. Why didn't people try to fill you up any more, why were they all queuing up to pour you out? But he was different. I wore my favourite dress, not one he picked out, he just asked me to wear something that would ma...

Daydreams Ch. 02

by YaoiIsMyAntiDrug on Oct 13, 2017
Gay Male

Dylan smiles at Sam while they talk about the song blasting through their headphones. He noticed that Sam's eyes are a very light sexy blue and his face is extremely thin. If he shaved off the peach fuzz and waxed his eye brows he could pass as a girl. Dylan has come to terms with the sexual desires he has for Sam so thoughts of taking Sam were fairly under...

The Caretaker's Dress

by newpaulman on Aug 30, 2017
Gay Male

Albert was the caretaker of the house full of flats where I was living. He was a big, burly, hairy man; not a great intellect or conversationalist, just an ordinary middle-aged working class guy who presumably got his little apartment free or reduced in return for collecting the rent and doing work on the property. I had been having a bad time with depressi...