Gay Progression Chastity Stories

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Progression Ch. 01: Finally

by klapperz on Oct 15, 2017
Gay Male

Nathan paced around the shop for a few minutes while building up the courage to purchase the chastity device. This was his first time inside a sex shop, and he was very uncomfortable. He saw shelves full of different toys, each one exiting his mind with sexual thoughts. He noticed the device he wanted was behind the counter, but in order to seem less awkward...

Progression Ch. 02: Regret

by klapperz on Mar 6, 2018
Gay Male

The next few weeks Nathan went back to normal. Wake up, Work, Wank, Sleep. Almost forgetting about his encounter with Ryan. It wasn't until a month later that his urges to lock up his cock would come back. He started to remember Nathan and his offer. "He did say I didn't have to show my face" he thought to himself trying to ease his shyness. He pulled open...

Progression Ch. 10: Prison

by klapperz on May 1, 2018
Gay Male

Nathan looked around the room for something to do, but it was empty. There was only the bed, which was just a mattress laid out on the floor and a door leading to the toilet. The was a dim light that allowed him to see, but no windows or view from the door as he was in the basement after all. He thought about what he could do to entertain himself, and quick...

Progression Ch. 13: Unboxed

by klapperz on Jul 3, 2018
Gay Male

Nathan woke up and as usual, removed his t-shirt and briefs then made his way to the bathroom. On his knees, he waited for Kevin to arrive to prepare him for the day. Kevin was frequently late, and today was no exception. Nathan waited patiently for twenty minutes until Kevin finally opened the door and with his phone angled to take a picture. "Smile for y...

Progression Ch. 04: A Real Fitting

by klapperz on Mar 6, 2018
Gay Male

Nathan hung out with Jeff and his other flatmates for the day. He had been so focused on Ryan and Jack that it was nice to have a break and be normal for the day. They went to the pub for lunch and then watched some films. Before he knew it, the day was over and everyone was heading for bed. The next morning Nathan woke up for work. He panicked, remembering...

Progression Ch. 06: Confession

by klapperz on Mar 27, 2018
Gay Male

When Nathan arrived home and entered through the front door, he instantly heard Jeff shout out from the living room "So the lucky boy returns?" Nathan walked into the living room to join Jeff who was sat with Kevin who was playing on his phone. "So who was he? Anyone we know?" asked Kevin who glanced up from his phone. "What, I've stayed out all night bef...

Progression Ch. 05: Overnight

by klapperz on Mar 27, 2018
Gay Male

Nathan got showered, making sure to use his syringe only two times. He dried himself off and got changed into his leather locking pants. He put on some tracksuit pants and a t-shirt, before heading out the door almost running to Ryan and Jacks. Finally, he was standing outside their house knocking on the door. "Well aren't you eager?" said Ryan. Maybe it w...

Progression Ch. 07: Decision

by klapperz on Mar 28, 2018
Gay Male

The next few days went pretty slow as Nathan counted the minutes until he could see Jack and Ryan again. It didn't help his frustration than Kevin, who was now sleeping in his bed, had quite a high sex drive. He was always demanding handjobs and blowjobs, which kept Nathan in a constant state of arousal. "I'm off to see the guy I told you about," said Natha...

Progression Ch. 11: Goodbye

by klapperz on Jun 18, 2018
Gay Male

"Welcome home," said Kevin as Nathan pulled the car into the driveway of his home. "It feels like I've been away longer than a week," said Nathan. Nathan opened the door and let Kevin into the house. "Welcome back, how was the holiday?" said Jeff calling out from the living room. "Oh yeah, I told Jeff we went away for a week holiday. Just play along. Or...

Progression Ch. 03: The Show

by klapperz on Mar 6, 2018
Gay Male

Nathan turned and looked at his clock. It was barely 3am and he was just lying there looking at the ceiling. No matter how hard he tried he couldn't stop thinking about his session with Ryan and Jack. He put his hands under the blanket to feel his cocks prison and attempt to get some relief, but it was useless. When he tried to play with himself his cock jus...