tagGay MaleImprisonment Ch. 01

Imprisonment Ch. 01


Rottenrow Prison, Glasgow, Scotland, 1876

Andrew Fairfax sat at his desk, grinning as he pondered his good fortune. Only recently it had occurred to him that he really ought to check up on the practices of his secretary, Justin MacDowell, who handled the clearing and selling of prisoner's belongings. When someone was imprisoned for life or for an indeterminate amount of time and had lived alone, his belongings were often cleared from his dwelling and sold to auction houses as a service for the family. Young MacDowell handled the selling of the items and handed the money over to the family members, and Fairfax had always trusted him to do so. After all, he had always been a dependable sort in other respects, handling the paychecks of the various prison staff and keeping the administration running smoothly. But there had been times that Fairfax had observed the young man exhibiting a shifty manner as he left work for the day, and on an impulse he decided to check up after him. A check of the books, and comparing of them with figures obtained from the auction houses, revealed significant discrepancies. The amounts turned over to the families never matched the amounts MacDowell collected from the auction houses. They were always smaller. There could be little doubt where the excess was going.

Of course, MacDowell could lose his job for this. He could even find himself an inmate of the very prison in which he worked. But that wasn't really what Fairfax wanted. No, he'd rather correct the lad's behavior in rather more...unconventional ways. So with a view to doing so, he called his young secretary to his office shortly before the end of the day's work.

Justin showed up at Fairfax's door with a casual smile, sitting down in front of his desk. He was slender and boyish, appearing even younger than his twenty-six years. His indoor occupation and lack of physical labour contributed to a smooth, pale complexion. His hair was long, falling to the middle of his back, and he usually kept it tied back with a ribbon. It was straight and red, with a fringe falling across his forehead to his eyebrows. While working the books he usually wore reading glasses with oval silver frames, adding to his bookish appearance. He usually dressed in a crisp tailored shirt and waistcoat above neatly ironed trousers. He was the complete opposite, really, of someone you'd expect to see working in a prison. He looked more like a university professor -- or a student.

"So, what can I do for you, sir?" he asked affably.

The older man smirked. "Oh, it's more about what you've already done, young MacDowell."

The boy looked confused, tilting his head. "Sir?"

"I've recently been to visit some of the auction houses. They gave me the figures they paid you for some recent sales. Then when you were out, I checked your books for the amounts you paid out. Not a one of them matched."

Justin grew pale, and after a moment opened his mouth to speak.

"Oh, don't bother trying to come up with excuses. I'm perfectly sure of what it is you've done. But luckily for you, I'm willing to let you keep your job -- and keep yourself out of a cell -- if you'll simply do me a favor once a week."

MacDowell eagerly responded, his face flushed with relief. "Oh, yes sir, of course, anything..."

Fairfax leaned back in his chair, smiling and folding his arms. "Good, good. Well, from now until I decide, every Friday when your work is done, you'll come here. Then I'll lead you to a room where there will be two guards, and four of the prisoners whose families you've swindled. I'll provide them with some things -- straps, paddles, rope, petroleum jelly..." the man leered at his now terrified secretary. "I'll tell them what you did. And I'll let them do as they like with you for an hour."

Justin gaped, his face pale again, at his superior. "But...sir...some of those men are...they're animals! There's no telling what they'll do..."

"Oh, I have a basic idea. Don't worry so much. Myself and the guards will be there to make sure they don't kill or maim you. I want you to be able to work, after all. I won't even let them mess up your pretty little face." He grinned. "But you fucked over their families, so I think it's only fair I let them fuck you. Or whip you. Or paddle you until your little backside is black and blue. After all, you'll get to keep your job. And you won't end up in there with them full time -- heaven knows you wouldn't last long."

Justin blushed hotly, his eyes lowered, and wrung his hands. He couldn't think of anything to say. The consequences of his misdeeds were just beginning -- and he was absolutely terrified.

Report Story

byAgentK© 6 comments/ 13628 views/ 8 favorites

Share the love

Similar stories

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartmallardandcoot, jakx and 6 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous12/09/17

Great Start

You're off to a wonderful beginning. You set the scene and add intrigue. The story shows a good eye for detail and pacing.
Keep on writing. You have my attention.

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by AgentK11/09/17

Um, anon, the plot is in the further chapters. This was a brief introduction, nothing more.

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous11/08/17


Not good. I thinks its written by an 8 yo boy.
Charecters weren't develope..plot missing.

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 6 User Comments  or
Click here to leave your own comment on this submission!

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: