Slave Shorts: Rich Boy, Poor Boy

Story Info
Set in a New World Order universe.
1.7k words
4.71
6.9k
7

Part 5 of the 24 part series

Updated 12/22/2023
Created 01/26/2023
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

They were best friends growing up. Having met in elementary school, Steven and Stephen became fast friends. Sadly, Steven's family were killed in a car accident when he was on the cusp of high school, and he was then raised by an aunt who squandered his inheritance money on herself over the years. Instead of finding independence from this, he seemed to regress, doing her bidding and being at her beck and call without hesitation. The other boy, Stephen, was born into excessive wealth, never knowing what the term "budget" was. He was taught to indulge in anything his heart desired, considering his family had money.

Eventually when he reached high school his mother ran off with another wealthy business mogul and his father passed away, leaving his entire fortune to Stephen.

Both boys having dealt with family loss at a crucial development age meant their brother-like bond was strengthened through the trauma. However, as time passed both boys grew into young men and eventually went their separate ways once they graduated from high school. They both became busy trying to set their lives up as independent adults and barely messaged one another as time went on.

Stephen developed a thing for attractive slave boys as he began to invest in and take control of small independent slave farms across the country that needed financial support. This investment proved beneficial for the young man as it meant he could have any slave from the farms he was backing. The owners and Stephen held a healthy relationship, with the owners happy to be financially supported if it meant a sliver of their profits were sent to Stephen, and what's a few slaves for his personal use here and there.

Unfortunately, Steven got himself into large debt trying to set up a business as he had been coaxed by his psychologist to get out from his aunt's authority. The business didn't last more than a few months, and the debt would continue to pile up. He knew that if he didn't start paying back his debts that he would have to apply for bankruptcy. He would be charged by the courts and his punishment would be enslavement to pay back whatever money he owed, and then some. There is no escape from slavery, once a slave always a slave.

Steven saw the notices of final payments due piling up on his desk. With a sinking feeling he wasn't going to get out of this without help he decided to approach his childhood best friend.

Steven arranged a meeting with Stephen through the latter's twinky secretary for one cold and rainy Monday morning. The boys, now 21 years old, met like old friends do and both were happy to see one another. However, Stephen did not suffer fools and asked his old friend to get straight to business. What he didn't tell his old friend was that he knew why he was there, he knew Steven wanted money from him. He knew what would happen if he didn't get that money. And Stephen saw an opportunity.

Steven detailed his problem and requested financial help from Stephen. The poor boy shuffled his feet and stammered his way through asking for help, something he never did growing up, only ever doing what he was told under his aunt's rule.

Stephen took what his old friend had stated into quick consideration and provided a flat refusal to help. The ensuing fireworks from Steven could be heard from the heavy oak doors of Stephen's office. His secretary listening intently to the cries and begging of Steven. The secretary called Stephen's bodyguards to escort Steven from the office, and from the building.

Soon enough he was watching with interest as two burly beefcake guards from the security team held Steven in their arms and frogmarched him from the office.

Clearly Steven and Stephen's friendship was over.

One week later the slave police arrested Steven. On the day of the boy's enslavement Stephen purchased the boy privately. He did not wish to wait for an auction date as he wanted the boy's virgin fuck hole for himself. Paying the higher premium was worth it.

In the eyes of the law Steven was no longer seen as a male human but a subhuman animal.

He was marched through the town from the slavery to Stephen's mansion naked. All the boy had on was a slave collar and a metal chastity device. It had its head shaven in a crop two and its nipples pierced with one inch tit rings. Its feet were bare, but Stephen was not cruel and would eventually give him slave shoes for outside use. Stephen saw the importance of slaves not wearing shoes on their first few days of slavery to ensure they know they won't be given privilege of Freemen and male humans. Many will tell you that even if a slave does not have a collar on you can tell it is a slave. How many freemen do you see walking around without shoes?

Steven had been made aware that he had been privately bought. But it did not know by whom. However, it became obvious as he was marched to his ex-friend's mansion what had happened.

Once it had arrived, it was escorted through the slave entrance and introduced to the household staff. It was told that it would be the lowest slave there. To work himself up ranking would take training and discipline and obeying every command given, no matter how humiliating or degrading it was. It would first undergo training to be taught how to keep the house looking perfect the way Stephen liked it.

The most humiliating event happened that first evening. It had to serve its new master his dinner naked in front of an old school friend of both itself and its master. The friend was gay and always had the hots for Steven as a Freeman.

The old school friend's hands explored the new slave's body as its new owner openly explained how it would be trained sexually. Its master went into graphic detail and the slave could see the bulges of both its master and the freeman engorge as they spoke as though the slave were not there. The Freemans' hands longingly stroked the balls of the slave and groped its full chastity device. He felt up the slave's peachy butt cheeks and his fingers explored the tight pucker between the cheeks.

The Freeman's fingers exploring the slave's pucker withdrew to then be inserted into the slaves' mouth. The slave was told to suck and lube up the Freeman's fingers. The slave did so with tears in its eyes. The two fingers then went back to the slave's pretty pink hole and inserted using its own spit as lube.

The slave's master and the Freeman continued to talk explicit detail as to the slave's upcoming sexual training as the slave stood there being fingered in its pussy. It was ignored except for its hole while the two men discussed how best to sexually humiliate and degrade the new slave. The slave continued to have to stand and allow the spit-lubed fingers to explore its nether regions. Soon the chastity device began to leak, the Freeman having found its g-spot and pushing the button with expertise to get this reaction.

The slave wanted to make a sound, to moan, to scream, to do anything, but it knew if it did, there would be severe consequence. The Freeman eventually stopped the fingering and made the slave clean his fingers once more.

The two men then shared their meal as the slave was ordered to stay standing, its cage dripping on to its foot. During dinner the Freeman discussed with if he could have sex with the boy. Stephen refused. He had other plans. Steven always thought the freeman was a closeted fag.

Later that evening the new slave was escorted up to its new master's bedroom. It entered nervously knowing what would happen. Stephen ordered the boy on its hands and knees, in front of the mirrored wardrobe. He aligned his cock up behind the slave's butt hole and ordered him to watch the fuck. He penetrated the slave harshly, with no lube, making it scream. Stephen slapped him for making such a noise and he gave no respite.

With each pound the slave would moan "fuck".

Although Stephen could have punished his slave for this, he did not. It was the one generous thing he would do for the slave ever. Stephen was taking something that he saw belonged to himself, from the slave. He believed he should have taken it from Steven years prior in high school, but this was worth the wait.

Stephen shot his load up the slave's tight hole. He then ordered the slave to arch its back upwards, continuing to kneel in front of the mirror. Steven went to a set of drawers near his bedside table and returned to his slave holding a thick glass butt plug. The slave's hole stretched around the plug as it was inserted, using the cum as lube. The whole plug eventually did fit inside, and Steven looked at the stretched pussy hole with lust.

After the plug was inserted, he ordered the slave to kneel before him. He placed his cock in front of the slave and ordered it to clean his cock. With a clean cock still throbbing from the fuck Stephen placed his cock just inside the slave's lips. He began to piss, ordering the slave to drink it all down.

Whispering softly in the most humiliating of ways he told the slave how a slave should drink its owners piss and clean his cock no matter where it had been. Stephen told his slave how it would learn how to do it in the most expert way in the next few months. The slave was beginning to understand how far it had fallen.

That day, Stephen not only took Steven's virginity but his dignity too. Afterall, what has a slave got to use dignity or self-respect for.

The two best friends had become a Master and Slave. Eventually, Stephen trained Steven in the art of sex, and in time, the slave was shared amongst its new master's friends, and old high school friends. Steven the man was no more, he had been replaced by the cock-hungry slave slut who became the best fuck slave on its master's estate, eventually earning its new name: Fuck

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
AbdelkaoolomocroAbdelkaoolomocro5 months ago

This was really so hot.

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Room and Board Ch. 01 Robb plays maid to two alpha freshmen.in Gay Male
Friendly Turnout Pt. 01 Femboy gets invited to cabin and turned into sissy sex slave.in Gay Male
Prison Wife Femboy in prison, gets turned into a Black Man's wife.in Gay Male
Homeless and Desperate Femboy is homeless and forced to submit to a man for a bed.in Gay Male
Bottom For The Night: A New Job Lee starts a new job and learns the hierarchy of the company.in Gay Male
More Stories