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 4th 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.
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