The Debtor

Joe was seated at his desk when his secretary rang in, and Jim Weasley was here. Joe looked at the clock on his desk. It was 2:40 pm, Jim was 20 minutes early. He let him cool his heals out in the lobby.

The lobby was furnished with metal chairs and no tables on purpose. Joe wanted visitors to be uncomfortable in the lobby and in his office. The girl under his desk was interviewing for a stripper job at the bottom of his 3 clubs.

He had the budget club on the south side, the moderately priced club was in the university district and his high-end club was by invitation only and it took up the entire top floor in a 60-story building downtown. The elevator that accessed it was manned 24/7 by private security.

The building was owned by his boss. 60% of all profits went to the boss. The girl had just turned 18 yesterday. Her mother had a gambling problem along with a drug addiction. She and her husband decided their daughter could work off her debts and pay for the rehab they were both in now.

She had small breasts, if she can dance, he will have his plastic surgeon fix that. He remembered he started Candy this way and she worked her way up to the high-end club.

She was still available for a price; it was a steep price because she knew exactly what Joe wanted and was well trained. This cunt under the desk better hope her pussy is better than her mouth. He pulled her from under the desk by her hair. She whined and her mascara was mostly on her chin from crying.

"You need to quit feeling sorry for yourself. Men and women are going to use you for their pleasure. The better you are at it, the sooner your debts are paid." He spun her around and licked his right hand and shoved two fingers roughly into her pussy. Fuck this girl is still a virgin.

"Stay right where you are. We are selling your cherry for sure. I am going to take your ass cherry though." Joe said.

He opened a drawer in his desk and recovered some lube. He lubed up his cock and poured some over her asshole. Using 2 fingers he rubbed it in past her sphincter. He slowly pushed on her asshole with his erect 9" cock that was as thick as this girl's forearm. His hood past her sphincter and she began screaming. He shoved her bra that was on top of the desk into her mouth.

"Keep that in your fucking mouth or I will beat you after I fuck you." He pulled her hips back hard to his hips.

She was now thrashing under him. He did not need to move, and she was milking his cock. She was so tight when he pulled back and made one stroke it sent him over the top. He emptied his prostate into her asshole.

When he pulled out starting to soften his cock was covered in shit and blood. "Any time you come to this office or go to the club, you will enema yourself 1 hour before you enter.

Now you will clean your shit and blood from my cock with your mouth." He flipped her onto her back on the desk and spun her head to his side of the desk. He pulled her bra from her mouth and shoved his cock down her throat while holding her jaw open with his thumb and index finger.

When he was pulling his clean cock from her mouth, he pulled her off the desk roughly and said, "before you go, lick that blood off my desk."

She hurriedly did and scooped her clothes and left the room carrying them naked to the lobby. Candy met her at the door and whisked her into a private bathroom, behind her desk. She got her into a shower and told her she would be right back.

Jim was surprised when a tiny naked girl came out of Joe's office door. She had blood trickling down her inner thighs and was crying her make up off. He did not look good at her, but she did not look 18.

Candy re-emerged from the door behind her desk and said, "I will go in and talk to Joe and find out when he will see you."

She went in for further direction on the young lady. Joe explained about the virgin status and required her to put on a chastity belt. Jim is going to need one as well. You can send him in.

"Tell him to leave his clothes outside and hand him the cage. He can enter once you have given him the cage." Joe required.

Candy returned to the lobby and Jim was seated in one of the metal chairs, looking at his phone.

"You need to strip and leave your clothes out here." Candy stated, as she moved to her desk. "I need to measure you for a device."

She returned with a string and a ruler. He was standing and staring at her.

"Jim, he will not see you unless you are bare ass naked, you owe him enough money, I think I would start stripping and folding my clothes on that chair."

Jim answered, "You are serious, naked?"

"Yes, I must measure the base of your cock and balls. I will give you a device and a key to take with you."

He stripped and was beet red as she took the string and wrapped it around the base of his balls and over his cock base.

"126mm" she said measuring the string she pinched where it joined. "That would be a small ring, the 40mm one, like 1.5 inches."

If possible, he turned redder. She reached in a drawer and handed him a small stainless device with a key sticking out the side on top. It was a ring with a cupped 1" protrusion out the front. The protrusion was slightly shaped like a circumcised cock head. She opened the door, and he walked into Joe's office.

Joe left the intercom open so Candy could enjoy the conversation. In his ear was an earbud and he could hear her talking to the girl he had just used about how to keep herself clean while wearing the chastity device.

She would not be required to work until her virginity had been sold. But she needed to train, and Trish held class in the basement of this building everyday at 4pm. She was to start attending tomorrow.

The money from her virginity sale would go toward her parents' debt. She needed to go now to the piercing studio on 3^rd street and get "The Joe Standard Set."

Candy then lifted her skirt and showed the girl her piercings. "And both nipples, studs in your tongue." Joe turned the volume down and looked up from his papers to see Jim's bald head, did not extend to the rest of his body. He was covered in brown fur.

"You owe me $130,825 right now with interest. Can you pay?"

Jim replied, "I have been giving you as much as I can each 15^th and 1^st from my paychecks."

"That is just putting you further behind, you can't cover the interest. You or someone in your place will have to work for me going forward. Do you have any daughters?" Joe asked.

Jim answered, "No, my wife and I have been unable to have children. It is just me and her. If she finds out I owe this much it will probably just be me."

Joe replied, "You are going to put on that chastity device, go home to your wife, get naked in front of her. Hand her the key with this note. I will know if you look at it before you give it too her and my deal will be off. If she does not agree to work for me, it will fall back to you. I will have my plastic surgeon convert you to a woman and I will pimp you out to who ever will have a vagina with a cock hanging over it. I will have him remove your nuts, put in a cunt and leave your long clit hanging. Do you understand?"

Jim answered, "How does this go on?" "Pull your nuts through one at a time, then pull the head of your dick through and lock the hood over your cock. Candy will do it for you, get out of my office." Joe said, in dismissal.

As Jim walked out of the office fiddling with the key in the cage a stately older woman, maybe in her 50's was standing at Candy's desk talking to her. Jim again blushed as being naked with two fully clothed women. The woman looked at him and told Candy,

"Let Joe know I'll be in soon. It looks like sissy boy here needs some help with a cock cage. I so love locking little sissies up."

With that she put her palm out for him to give it to her. She deftly took the key, removed the hood from the ring. "Put your hands on top of your head and watch how this is done. If you fuck this up showing your wife, I expect her to swat your sissy ass. In fact, tell your wife that since Mrs. Finley had to show you that you will take 25 with the cane on each cheek tonight. She must report to little Joey that it was done. Candy gives him the cane to borrow for a day. I believe she has an appointment to meet little Joey."

She deftly pulled his left testicle through the hoop then the right. Firmly holding the testicles down her fingers underneath pushed up on the ring and she took a finger and pushed the nail down right behind the head and got the first bit of his cock head under the ring. She pinched the head between two fingers and pulled it through. She then took the hood and placed it over the glans and pushed down and back against his scrotum.

Locking the cylinder his cock and balls now made un upside down heart with the silver hood dotting the bottom end of the heart. She swatted his ass and told Candy. "Duct tape the key between his shoulder blades where he can't reach it. Send the sissy home to grovel to his wife. Joey told me the whole story and the plan."

Jim got dressed and figured out on the way out. He now had to sit to pee. He also had to clean the urine off his ball sack because the cage spread it everywhere over his sack.

He was sure his wife would leave him before she whored for Joe. He had agreed to at least give her the note. He walked through the door to the house and called out for his wife.

"Bess, where are you?"

He heard, "In the kitchen." He stripped his clothes off and left them bunched by the door. He had the cane and was naked except the cage covering his cock. When he walked into the kitchen Bess's head was in the fridge and it looked as though she was chopping vegetables.

He spoke, "Bess, I have a confession and a note." She turned to see her naked husband holding a bamboo rod about 4 feet long palms up with his arms straight out. Not entirely naked, there was a silver metal device covering his cock and his balls were tight in his scrotum.

"What the fuck Jim, is this some kind of perverted joke?"

"No, please take the cane and this note. Behind the duct tape in the center of my back, is the key to this chastity device. Please read the note and I will try to answer any questions you have." With shaking hands, she took the bamboo and leaned it against the island. She told him, "Turn around." She ripped the duct tape off and it came with a wad of his back hair. She tore open the note.

Dear Bess,

Your husband is in deep gambling debt. As of this morning it was $130,825.00 the interest rate is 25% and it is moving fast. He has not been able to keep up. I have an idea on how this can be resolved in just over a year. I need you to meet me in my office at 12pm tomorrow. I will provide lunch and instruction on how this can be resolved. The total I have calculated for you to make the debt in one year will be just under $240,000. If you do not show, you will not see your husband for the next two years and when he returns, he will be a woman. Currently he is not allowed to have sex and that is why I locked him up. You and I will negotiate on how he is treated going forward.

Regards Joe!

Tears were streaming down her face. She looked at him and screamed, "Gambling, you said never again after we cleaned out the retirement 5 years ago. You rotten mother fucker. Get out of my site."

He answered, "I can't until I have received 25 strokes on each cheek with that cane. Mrs. Finley put the cage on for me and said I was to tell you that." He knew now that Mrs. Finley was a set up and his wife might continue to beat him when the 50 were over.

She stopped crying and cocked her head sideways and said, "Get out and bend over the arm of the couch. You will take your 50 there. You can then shower in the basement and sleep in the guest room next to your den. I will be cooking for myself tonight so you will have to figure out your own dinner and breakfast."

She used all her strength on every strike. The bolster on the couch had pushed his ball sack back far enough that 10 of the 25 for each cheek also tagged his balls. After the 4^th strike, he was wailing, and she did not need the neighbors over to check it out.

She stuffed his underwear from the entryway into his mouth. She did not know, but he did, that they were moist with urine. When she finished, she tossed the cane on the couch and left without a word. He could not move.

His body was shaking with pain. Once he could he went to the master bathroom looking for salve for the bleeding welts and cuts raised across his ass and the back of his scrotum. One on his scrotum was 3/8" wide and 2" long.

It was a deep purple color and bleeding. He grabbed some underwear, sweats and a tee shirt to wear downstairs in banishment. He showered and went straight to the liquor cabinet. He could not sit so he lay on the floor and googled everything he could find about sissy, chastity and trans men. He was sure Joe was serious about the plastic surgeon. He woke at 9:30 am and did not hear his wife leave in the morning. She had left at 7:30 am to get ready for her "Meeting" with Joe the loan shark.

Bess had called her stylist and used the family emergency card. She paid the extra for the stylist to do her makeup along with her hair. She also had her upper lip waxed. Eyebrows shaped and waxed and figured since Jim showed up home naked the chance of her ending up naked was pretty good, she had her coochie waxed, just leaving a triangle above the clit.

The stylist cleaned up her roots and did a fill on a manicure and a pedicure. The stylist finished at 10:50 am. Bess did not want to keep Joe waiting. She arrived at the address on the card and the doorman sent her to an elevator attendant.

She had on a summer dress, flats, and a small clutch. She had matched her bra and panties this morning. They were pink lace. She had douched and made sure she had mints.

The elevator operator let her off on a floor with a single door. She walked to it and heard the lock click as she approached. She opened it and stepped into a lobby with a bimbo receptionist and all steel chairs.

The receptionist asked her name. "Bess I am here about this." She handed Candy (According to the name plate on the desk) the note her husband had handed her. It was 11:45 am and she was told to have a seat.

At 11:55 am a couple entered from the office door, and she heard the woman say, "My baby is now a prostitute because of you." He answered, "It is temporary and the only way to save the business. Just shut up until we get out of here."

Candy disappeared into the office and closed the door behind her. When she came back out, she looked flush. "He will see you now." Candy held the door open for Bess and closed it behind her.

"You understand what kind of trouble your husband is in?" was the first thing she heard as the giant man behind the desk was looking down at a ledger.

"He owes you an ass load of money and can't repay you. You want me to work for you to repay this debt. I assume part of my duties would be to sleep with you. I don't know what else you want but I don't want to do that."

Joe looked up and smirked. "One of you is going to turn tricks. I just must decide which one. Get your clothes off and show me what I am buying with $240K. When you decide to do that, I will tell you what will happen to Jimmy if you decide not to.

I will pick him up from your house this afternoon. I will take him directly to my surgeon and his sex change will begin tomorrow. The surgeon will remove his balls and create a vagina for him. I will have him leave his little dick right above the fake vagina as a notice to the fact he was once a man. Jimmy will get a set of 48FF tits molded into his chest with some nipples from a cadaver. His lips will be pumped so full of collagen that he will look like he is sucking cock all the time. His ass will get enormous implants to give him an hourglass figure and I will pimp him to faggots and trannies on the south side of town.

He will have almost $150K worth of work done on him so it will be over $300K for him to pay back with interest. I'll be lucky to get $200 per trick and he will probably only be able to average 3 per night. Friday, Saturday and Tuesday are the only productive days down there. $1800 per week is 167 weeks to pay his debt. 52 weeks and that is 3 years. 3 years from now, your little Jimmy will come home with a pussy, large boobs and a wore out asshole."

Halfway through his story she was standing in front of him naked with her arms across her breasts and her pussy. "Drop your hands, in fact, put them on top of your head. Turn and let me get a good look." She looked like a 10-year older version of Candy when she showed up in payment for her father's debts. Same height, same little titties, her ass was bigger, but firm and nice.

He liked it. $30K in tits and some miscellaneous improvements and she would earn back the $240K in less than a year. Candy could turn over some of her regulars and he could have her pick up part of Trixie's load up town.

"Let's get the preamble out of the way. Do you know how to suck a cock?"

She said, "I don't suck cock."

"Ok I'll pick up Jimmy in 3 hours. You can go."

"I will suck your cock. Just tell me what you want." Bess said, with a tear on her cheek.

He rolled his chair back, stood up and dropped his slacks to his knees. "Crawl over here and learn to worship a mans cock."

He sat back down just as Candy came back in the door. She was wearing a white corset and nothing else. The first thing Bess noticed was the pierced nipples, clit, rings down both sides of her pussy and she did not remember seeing the ring through the septum of her nose.

"Candy, show this new cunt how to worship a mans cock." Joe demanded.

She immediately dropped to all 4's and sensuously crawled across to his feet. Bess dropped to the floor and tried to emulate what Candy had done. It just was not the same without the tits swaying under her body.

Crawling behind the younger woman the next thing she noticed was a large pink glass gem sticking to her asshole. Candy got to Joe's feet and looked up at him and said, "Sir, may I worship your cock like my life depended on you enjoying it?"

He answered, "It may, and yes you may."

Candy raised up on her knees and Bess noticed that she never lost eye contact with Joe. She would blink but her eyes were always up at Joe's eyes. She started with her left index finger and thumb surrounding the base and pulling the foreskin down. She licked the head and put it in her mouth.

Joe said, "You can't see, but she is using the post on the tip of her tongue to excite the bottom of my glans. Her right hand was fondling his balls and rolling his scrotum."

As his cock got semi-erect. Candy began to push her lips down to the base and use her throat to stroke his cock.

"Your turn Bess." Joe required.

She crawled forward and grabbed the base with her left hand.

Joe slapped her hard. "You ask before you touch a mans cock."

Her right cheek stung, and tears came to her eyes, and she tried to remember what Candy had asked. "Sir may I suck your cock like my life depends on it."

"It may and you may try." Joe repeated.

She reached back up and grasped it with her left hand. He was a lot bigger than Jim. She was turned on by the whole situation and could feel the heat in her crotch. She put her mouth at the head and opened as wide as she could.

She tried to get it into her mouth, and he pulled her head back by her hair and said, "Watch the fucking teeth bitch. Stick out your tongue and it will help."

Candy rolled on her back under Bess and began to fondle the older woman's pussy lips. Bess flinched at first and then settled in to trying her best to get this monster cock in her mouth. She was able to get it to the back of her tongue and it would go no further.