Crime and Sexual Punishment(closed thread for Kililia)

[justspitballing]

Nathan came into Mateo's ass, strand after strand of white cum went into the young man. Nathan panted a bit, smiled, and gave his son another good lick on the face.

"Now you're thinking right. Good job. I think the second one is best. It costs just a little bit more. Now we just have to pick a proper course for you. Better get on that, I can cum a second time, but I'm going to have to fuck you pretty fucking hard to pull it off. It could hurt really bad if you don't speed this up," Nathan instructed.

He got up, bending Mateo over, and started to fuck him all the harder while still stroking off the man's cock with one hand and guiding the other hand over the mouse.

 

[Kililia]

Mateo gasps feeling Nathan shoot his huge load in his asshole, blushing as Nathan licked his face making his nipple hard: " Thank...you....daddy..."

Mateo paled knowing Nathan was far from done with his asshole: " Daddy...I'm ...tired...my ass hurts..." * He winced as Nathan sat up, lifting him on the tip of his toes before pushed down on the desk: " Arrrggghhh, daddy...it hurts..." *screaming as Nathan began thrust hard without mercy, tears streaming down his face. His thrust met with screams as he did not notice Nathan guide his hand. He try concentrate on the screen, but the more he concentrated, it felt like Nathan ram violently harder: " mercy, daddy!!"

 

[justspitballing]

Nathan fucked Mateo hard, his dick going in and out of the man at a quick pace. His balls smacking against the young man's body. He went in all the way to his base, pulled out, and went in all over again. He was like a jackhammer.

"No mercy. This is going to be happening to you every night, including when you are studying. You have to be able to focus if you want to get anywhere. Start reading course options. I want something that will make you smarter, something I can brag about you having. Something that can make us both look good. I have some fellow gangster bosses, fine men, I wouldn't mind marrying you off to. So you are going to have to impress them. It would get my foot in the door and help me expand, and they are going to fuck you just as hard and they wont care that you're not gay either. So you better get used to all of this. Now read!" Nathan ordered.

He squeezed Mateo's balls tightly to hammer his point home.

 

[Kililia]

Mateo screamed in agony as Nathan raped his asshole cry, his face was red from tears and pain. Nathan cock thrusts felt like sandpaper rubbing in his dry asshole. Shaking his head, begging to stop as he felt he was gonna be split in two. He try properly reading but kept messing up. Force reread his sentences in tears as Nathan raped his asshole in anger. The color drained from his face as he mention marry him off to a gangster boss. He wasn't gay and did not wanna get married to a man. He started reading while crying like a baby, it was hard to read as tear blurred his vision and Nathan was raping his asshole. He screamed as he came again for Nathan.

 

[justspitballing]

Mateo started to read off the courses before him, though he was in such a state you could hardly understand him. He came a second time for Nathan. It really didn't matter what Mateo wanted, his body was under Nathan's control now. Strand after thick strand shot out of Mateo's shaft. The boys dick was very impressive. It could be counted on to keep getting hard even when Mateo prayed for Nathan to stop.

Nathan was well pleased. He let his son know.

"That one, the one you just started reading, I think that will work well. Nicely done Mateo," Nathan let Mateo know.

"You're such a good son when you try to be. I'm about to shoot off my second load just like you have. You want to drink it up? You've earned it."

 

[Kililia]

Mateo could not stop cumming for Nathan, sobbing between reading the pamphlet one at a time. Relieved that Nathan chose one that was to his liking. He gasps as he came again in Nathan skillful hands.

He hated drinking his load as it was to humiliating: " Please...cum in my ass, daddy..."

 

[justspitballing]

"Declining a gift from me is as good as insulting me. When I offer you something, you take it, you beg for it," Nathan growled as he pushed Mateo's face slowly down into just resting over the desk. He held the young man down with a forceful might.

He slid his cock out of Mateo's ass and then stuck it right into Mateo's face. He came onto the man's face, covering it. White, thick, creamy cum covered the young man. Then he slapped the man's young ass once, twice, three, and four times. He put a lot of force into his hand and you could hear the echo of the slap throughout the home.

"I have no idea why I've been taking it so easy on you. Best behave better tomorrow, I wont be taking it nearly as easy on you," Nathan stated.

He then pulled up his pants, got dressed, and stormed out. The door closed violently behind him.

 

[Kililia]

Mateo turned white as a sheet as Nathan replied: "Declining a gift from me is as good as insulting me. When I offer you something, you take it, you beg for it," He winced as he was force on the desk, he heard and felt Nathan huge cock slip out of his asshole. He closed his eyes as Nathan came hard on his face, howled as he was being spank hard: " I'm sorry daddy...please I behave better...i promise" *he whimpered knowing Nathan would be brutal tomorrow for not performing well today.

He crumbled on the floor in tears , cum dripping down his face and his raw asshole that felt on fire. He stumbled on his way to the washroom to puke hard as he hated having sex with Nathan. He crawled in the tub and crumb himself till he was red as a lobster and felt clean. Then took a long boiling bath as he screamed. he hated his cock harden as he remember feeling Nathan soft voice in his ear while groping him. He found himself jerking off his hard cock imagining Nathan huge cock force up his dry ass and raping his asshole. He cried out as he jerked and came hard in the tub. He hated himself for getting hard remembering getting dry fuck by Nathan amazing huge cock, he came a few more times before crawling in bed crying as he hated himself.

Camelia on the other hand was living well though locked into the bedroom in a night gown. She was well fed, examined, relaxed in her daily routine. She was confused by the fact that Nathan had not arrived to greet her, she hated idea of being his wife as he expected specific things. It was made clean that her husband wanted a very large family of his own. The doctor made it clear she be able bare him healthy children , she would be denied birth control as her main wifely duty was to give him children. It was made very clear that she was expected have a full involved relationship with her husband and kids.

 

[justspitballing]

The next day at 5:30 am Nathan got up and had a quick shower. Today was going to be an important day in Mateo's training. If he wanted to marry off his new found son to other mobsters he had to make sure his son would be up to it. He had heard stories about how Jefferson, a fellow mob boss, was very well endowed. The stories were so outrages that Nathan felt they had to be untrue, but he felt he better play it safe instead of sorry.

As such today would be all about stretching out Mateo's asshole. Making it spread as wide as it could. Seeing just how much the young man could take and still cum. He was very good at cuming hard, but the kid likely had limits. It was time to find out what they were and then break through them.

He got out of the shower, dried off, but didn't bother to get dressed. He went and grabbed what he needed from the closet. He smiled to himself as he grabbed it. He walked up to his sons room and slowly opened the door.

"Wake up Mateo, your next day of training has arrived," Nathan said, holding the wooden baseball bat tightly in his hand. He smiled broadly about the idea of cramming it up his son's butt.

 

[Kililia]

Mateo turn and woke up at the sound of Nathan voice. He practically jumps off the bed as his eyes adjusted. He realized that he was holding a baseball bat. He fell back and back away from. Nathan:" please no ! Don't kill me! " he honestly believed that Nathan was gonna beet him to death for failing his performance. " daddy... please... I do anything...please don't beat me...I won't defy you again daddy... I know my ass belong to you ! " * he back up against the wall, sobbing as he closed the distance.

He crawl the distance left between them and began suck Nathan cock like his life depended on it. He sucked hard and started deep throat while gagging. He looked up terrified with sucking on Nathan hard cock*

 

[justspitballing]

Mateo started to deep throat Nathan's cock. Taking the full length of Nathan's manhood into his mouth and sucking it hard. Mateo was a natural, skilled at this task beyond words.

Nathan was already starting to feel light headed. Poor Mateo, the baseball bat may have seemed cruel, but it would have prepared the young man for what was to come. Instead Nathan found he wasn't up to using it on the kid. He hoped Jefferson liked Mateo being ridiculously tight. If only Mateo knew what was coming.

"I wouldn't beat such a well behaved boy," Nathan said, smiling to himself, glad that he had so greatly broken his son's will.

"I.... I’m going to..." Nathan had to pause out his words, Mateo was to skilled, taking in the man's cock deep into his mouth.

Nathan coughed and then tried his best to go on.

"I'm going to get my men to bring in some clothing for you today. See about getting you dressed well. I want to be able to make you look presentable," Nathan said.

Yes, he would have some suits and ties brought in, but more importantly, some women panties and maybe even a skirt for Mateo to try out. Jefferson, word had it, had some interesting tastes. Nathan would have to get Mateo used to wearing panties and used to being raped. He knew Jefferson would expect such things.

Before Nathan could think out his plans some more he came hard and grabbed onto Mateo's head and crammed the man's face into his crotch, making him drink every last drop of cum.

 

[Kililia]

Mateo hated how he knew how to suck Nathan cock as he was thought by Nathan. He started wonder if that made him gay, he had never fantasies of men and only got hard for girls. Well except for Nathan mouth, hand and cock, he told himself. He was actually confused and just wanted to survive.

His eyes bulged as he felt Nathan slam in the back if his throat and came hard. He looked up helplessly as he swallowed every drop of cum. He felt so full of cum and made sure to lick Nathan cock clean and harden with again.

He pulls his lips off his cock and looks up at Nathan hard erection:" I swear be a good boy...please don't hurt me with the bat....I know my asshole only belong for your cock, daddy.... does my daddy.... wish used my asshole dry, now? "

He hated everything that came out of his mouth. He kept telling himself that he was not gay and after he was free, he would only fuck girls. He fear he live on Nathan cock for life.*

 

[justspitballing]

Mateo really was under Nathan's beck and call in everyway. He had to admire his own handy work, he had without much effort turned the man into such a willing slave. He was going to greatly enjoy doing the same to Camelia. She had stood up to him with such venom to her, he would enjoy breaking her most of all.

"Get on your hands and knees," Nathan instructed. He could not refuse his son's wishes, he was a caring father after all.

Once Mateo did as told Nathan tossed the baseball bat away and let it clatter onto the floor in the other room. He then slowly slid his well endowed cock into Mateo's ass.

"I wasn't going to harm you. I have a business associate, I'm going to want you to meet him. His cock is supposedly a bit bigger then mine. I just wanted to get you well prepared. He's likely going to be fucking your brains out after your training is done," Nathan said, starting to pick up his speed while thrusting into Mateo. His dick going in deep, being pulled out, then going in deep again.

"So your asshole wont belong to just me, it will belong to whoever I think it should and you are going to have to get used to having it spread wide open. But we wont use the bat, we'll get you ready the old fashioned way."

 

[Kililia]

Mateo hated when Nathan used his asshole but knew better than defy the man. He jumped at the baseball bat clattered on the floor. He reluctantly got on all four and spread his legs, hissing painfully as Nathan pushed up his asshole. He cursed as Nathan's cock was so huge and dry cock and he never seem get used to it in his ass.

He feared at the idea be lose up by a bat by Nathan, he shook his head: " I just want your huge dry cock, daddy in my asshole" *He whimpered at the idea of being passed around to other men. He let out sharp cries as Nathan began thrusting deep in his tight ass. He shut his eyes trying bare it but found himself letting helpless cries. He hated the idea of being fucked by many men: " Daddy...i don't wanna be whore around to men, please...i be a good boy"

 

[justspitballing]

"A good little boy wouldn't disobey his father," Nathan pointed out the facts as he fucked Mateo hard in the ass.

"I said I was going to have a business associate fuck your brains out, and that's what is going to happen. If I say you must submit to him, then you must. If I say you must be married to him, then you must. If I say you are to always cum repeatedly from being ass fucked and always beg for more, then that's what you are going to do."

Nathan started fucking Mateo hard, letting his displeasure of Mateo's suggestions be known. He grabbed onto Mateo's cock and started to stroke it. He grabbed it firmly, making sure it was enjoyable, but also making it clear he could really hurt Mateo at any moment if he decided to.

"You will be with who I say you will be with, and that's finale."

 

[Kililia]

Mateo paled at his statement, he did not want to fuck other men. It was already so hard to accept the fact Nathan was fucking him daily. He kept telling himself that he was a straight man and this did not make him gay. He howled in pain as nathan drill his asshole, the olor drain from his face at idea marrying another man.How would he be able convince others that he was straight if he was married to a man.

Sobbing hard as Nathan drill his asshole felt on fire, he hated when Nathan used his asshole. He gasps feeling Nathan play with his cock, it didc onfuse him when he got gard: " aarrrgghghhhhh....ooowww....yes...yes...daddy...anything you say, daddy...." *whimpers as each time his cock was in Nathan hands. He fear the pain Nathan. He hated how he got hard in Nathan's hand*

 

[justspitballing]

Mateo buckled under Nathan's harsh fucking and started calling out how he would do anything for his daddy. Such words, coupled with the still tightness of Mateo's ass, had an instant impact. Nathan came hard as a result, shooting strand after strand into the young man. His head went light as he let himself cum fully.

He still held onto Mateo's cock as he came and as a result he squeezed the shaft tightly in his grip. He stroke it harshly, much more so then he had been doing, likely sending both great amounts of pain and pleasure through his slave of a son.

"Good God your ass is amazing," Nathan complemented Mateo.

 

[Kililia]

Mateo was crying as Nathan harshy dry fucked his asshole without mercy with his massive cock.he cried out;" daddy...I be good!" * He hissed painfully as he felt Nathan cum deep in his asshole after drilly his raw asshole. Sobbing as Nathan cuts over and over again filling up his bowels.

He cries out painfully as Nathan stroke his cock hard. He shook his head and fought the urge but failed and came on Nathan's hand.

He hated that Nathan complemented after using his ass. He felts so full and dirty by Nathan's cum. He whimpered as he hated Cummings for Nathan . He kept telling himself that he was straight and told himself he prove himself it was true.

 

[justspitballing]

Nathan saw that Mateo once again came do to his cock, and came well. White, thick, cum was sprayed out onto Nathan's hand. Nathan then brought his hand up to Mateo's face and put it against his mouth, forcing Mateo to drink down his own seed. Nathan slid his cock out and with his current job done went back to his bedroom.

He found his cell and called up his men and quickly instructed them to bring in some clothing for Mateo to wear. He told them that when they got here just to put it all out on the floor by the front door. Nathan would see about getting his son dressed.

They did as told and within two hours a few bags full of clothing were dropped off. After the men left Nathan looked through the clothing and then put it all on the floor for Mateo to wear. It of course included some women's panties.

"Mateo, come out here. I want you to get dressed and be presentable and I've gotten some clothing for you to do just that," Nathan instructed.

 

[Kililia]

Mateo was exhausted as he came, gagging as he was fed his own cum. Hissing painfully as Nathan massive cock slid out of his raw ass. He left to wash himself after Nathan powerful fucking. He was tired and curse under his breathe as he was summon.

He made his way to Nathan side and looked at the clothe:" I did not think, I be allowed leave this room....what is this all about? Am I being allowed go see my friends?"

 

[justspitballing]

Before Nathan was several sets of clothing. They rested in a line on the floor. In the first set was a standard suit and tie, much like what Nathan wore.

"This is for your schooling coming up and for working at my operations. Also for family advents like seeing your sister," Nathan stated coldly, pointing out the first set, ignoring Mateo's question completely about leaving.

The second set of clothing included a very small, black dress, with a skirt that would hardly cover Mateo's butt. It had with it pantyhose and a garter belt, in the same matching black colour. Lastly there was a black set of panties that had written on the front of them in dark red fuck me and on the back of them was written the word hard.

"And this is what you will wear for me when you go to my private parties. More outfits will be gotten for you in time for these advents, but I want to see how you look in this for now," Nathan nodded towards the second set of clothing. He then pulled out from the bag a makeup kit and some lipstick. He rested it on the second set.

He then nodded towards the third pile. It included some lingerie and a garter belt and some pantyhose of its own. Only here the panties had a cut put into their back for easy access and no writing.

"And this is going to be for our bedroom," Nathan said.

"Now don't fight me or you know what will happen. We are going to be getting you dressed in your party clothing."

 

[Kililia]

Mateo smiled noticing the school uniform as it was real nice but the expression changed quickly. He was horrified at the sight of the second row and especially the underwear. He paled at the mention of " private parties" He did not want to wear women clothing and especially make up, he was a fucking guy.

He looked at the last pile and it was lingerie for women for woman again, ones to turn him off to be fucked hard by Nathan. He felt sick at the idea of wearing women clothing to turn Nathan on, he dry fucked like a madman when he was aroused. He wanted to scream that he was not a woman but knew it only get anally raped till he couldn't walk for days.

He reluctantly grabs from the second row and went to the washroom to dress up. He end up puking and cursing as he reluctantly got dressed for Nathan. Staring himself in the mirror now in sexy lingerie and a dress trying put make up. He look at himself in the mirror as he almost look like the perfect girl except his hair was not long enough. he hated this as he kept telling himself he was a straight man. He would fuck lots of girls at school and even knock up a few to prove himself. It took a while before he had courage to step out of the washroom looking like a girl, all that was missing were heels and longer hair.

 

[justspitballing]

Nathan looked over Mateo for a quick moment as he walked back into the main room. The skirt wasn't even fully covering down below, you could see the bottom of the panties under it, you could see the bulge from Mateo's cock. The garter belt and the pantyhose were all on Mateo's body and they fit snuggly. The dress was eye catching even if it was ridiculously small.

Nathan though did not respond. He walked right past Mateo, found the makeup kit in the bathroom, and came back along with it and a bit of toilet paper. At this point he was still naked, having never bothered to get dressed, not seeing the point of it today. His cock was starting to get hard again. It was hard to put on a tough face when his body made it clear how aroused he was, but he managed.

When he returned he put the toilet paper to Mateo's face and started to wipe the makeup off.

"You look like a five dollar slut. Let me do it," he stated.

He grabbed Mateo by the cheeks and reapplied the lipstick and makeup. He jerked the young man's face around as he forced the new covering over it.

"There you go. I want Jefferson, I want ever man, straight, gay, it doesn't matter, to want to fuck you raw the moment they see you. You can look that way son, you can be my little fuck princess, but you have to put your all into it," Nathan explained.

"Now you look good," Nathan stated and then slapped Mateo's ass with a sudden harshness that could knock someone off their feet.

 

[Kililia]

Mateo winced as Nathan cleaned his face and put on the make up perfectly, he felt sick at the name Jefferson. He hated the idea of looking like a girl ready to be fucked by everyone. He glance at a mirror and he indeed look like a girl and hated it. The idea being fuckable looking make him sick but did not dare defy Nathan as he was already hard. He hissed and lost his balance when Nathan slap his ass hard and landed on all four.

Just then a man walked in the room and it was the driver, the man helped up Mateo and looked at Nathan: " The car is ready, sir...its best we go as you did not care be late..." * He turned and motioned Mateo to follow him as he headed out to the car. It was the first time Mateo was allowed to leave the property and he looked like a girl. During the whole car trip, the driver glance at Mateo as he found him pretty. The driver smiled: " Sir, Mr. Jefferson told us to inform you that he reserved a private room. He will greet you at the party to see his purchase, he asked us to inform you that he has all the document signed and after plan take a personal long examine. He reserve the room for a week and might stay there a week for a thorough examination" *The driver concentrated on the road once he informed Nathan of the situation. Of course during all that Nathan cell would inform him of the transfer of cash.*

**The main room was huge and in circle, young male and female sex slave were serving food to the guests. The room was lit red with black massive couches and pillow, they all nodding to their arrival. On their right side was a heavy set man that was made man that was having his fat cock by a female slave. There was a commotion and Mateo witness a man slap a slave across the face calling him a whore for dropping a drink. He force the young man against the wall undo his pants and rape the sobbing young slave till he came early. A old woman in a tight blue dress walk over and bowed to Nathan: " We are honored by your presence...*glance at Mateo* " Jeffersson is at the table and waiting for his prize to sign the papers..." *She motion upsetairs where were hundreds of rooms* " He reserve the penthouse room and stay for a week..." *She guided Nathan and Mateo to the center of the room , where was a huge round table and couch seat in half a moon. Champagne and appetizers were already served, and there stood Jefferson, a tall (6'4) black man in a very expensive suit. The crowd looked at Nathan with envy, some slave getting fucked harder to get Mateo attention. Jefferson looked a Mateo with lust in his eyes: " Did you pop his cherry already? *licked his lips* "His more beautiful than you described...please sit...I want to speed this up and examine my prize..." Jefferson had specific idea in mind, he plan have Mateo after their first examen, reconstructive surgery before marry him publicly and deflower on their wedding night.***

Mateo eyes widen as Jefferson stood up and was shocked at his sight, he was quite tall, fit and loaded. The look in Jefferson eyes made him wanna run away but knew Nathan would punish him severely for humiliating him. He obedientely sat down between the two men, gulp feeling Jefferson : " open your legs, baby...." *Mateo paled and glance at Nathan not knowing what to do*

 

[justspitballing]

Nathan was for once gotten off guard. He hurriedly got dressed as Mateo was brought out to the car and he fallowed behind. He had mentioned to his men to inform Jefferson that he had found a good pet for him to have. But he had completely forgotten he had set up a meeting with the man two weeks ago for tonight at Eden. The meeting had been originally to go over the proper price they should be selling some fire arms for and how they would be splitting up some of their territories.

Jefferson must have felt the meeting was now all about Mateo and that he was going to be part of the deal. Yes, Nathan was more then glad to sell off his son, and now he would be getting some actual money for it.

When they got to Eden you would never know it was such a night club from the outside. The house it was under was long since abandoned and falling apart. Inside, hidden behind a false wall, was an elevator that went well down into the Earth. The hidden area it came into was massive with multiple floors and a main circle like room that was huge in nature.

The place was covered with blue neon lights and it had an active dance floor, with many a people just openly fucking without a care. The sex slaves were marked as such, all having to wear collars that ranged in quality from being clearly just taken from an actual pet store, to being very expensive. And they all wore the exact same dress that Mateo found himself in. Many of them though did not bother to wear any panties. Their skirts hardly covered them and their wet pussies and hard cocks were often on display.

One man raped his slave harshly against the wall while people around him cheered him on and some jerked off to the sight.

Then Mateo was introduced to Jefferson and Nathan, Jefferson and Mateo sat down together. Mateo was forced into sitting between Nathan and Jefferson. Several other people sat around the huge table with them. All leading crime bosses.

There was, Jefferson Harris, the leading man in the arms industry.

Lisa Hackel, the one that ran most of the drug businesses. She had on a red, scarlet, dress and had short blond hair. Her slaves, she had three women who hung around her at all times, were the only slaves in the building with skirts that covered them and they wore little buttons on their dresses that said please, only cuddle. It was rumored that Lisa could never bring herself to seduce anyone into being a sexual toy. Ironically in this place she was seen as the sexual deviant.

Then there was Kathy Hade, the woman in the blue dress that had led them to the table. She ran this building and her main job was bribing off cops to keep a lot of the crimes unknown. She had two male sex slaves and as she sat down she ordered them to start to fuck each other to entertain everyone. They nodded and quickly got to work doing exactly that, getting up on the table, undressing one another, and then started to fuck like animals.

And then lastly there was Andrew Bach, an old man that had a lot of land connected to his name. Nathan hoped to kill him some day and take everything that was his as his own, but he would need Jefferson to do that, which is why having Jefferson marrying Mateo would work so well for everyone.

Jefferson really liked showing off his wealth. He wore several golden rings, along with nice looking earrings and several golden necklaces. His suit was a dark blue and he had very short, black hair. He was built large and Nathan had no doubt that Jefferson could kill him in a fight. He had his own cuts just like Nathan did, part of his right ear was missing and he had a small scar on his cheek.

As they sat Jefferson told Mateo to open up his legs. Nathan quickly nodded at Mateo.

"Jefferson should be able to examine what he is buying," Nathan stated

Jefferson didn't wait for more permission. He yanked Mateo's legs open and put his hand between them. He jammed his hand into Mateo's panties and squeezed his cock tightly, so tightly it had to hurt.

"A nice size to him," Jefferson complemented.

"For a white kid of course," he then joked.

The two men fucking on the table before them all then came, screaming out in intense pleasure. One of them squirted out thick cum into their partner, but said partner came hard before the people sitting around him. His cum shot out of his meaty cock right into Mateo's face. It dripped over him, coming onto his face thick and strong.