Note: No parrots were harmed – purely fictional scenario

Chapter 1

Randy had been laid off for months now. The recession had kept Randy unemployed and he spent of his time looking for work and looking at internet porn. There was a point in his time of unemployment where he hurt his wrist and his masturbation had dropped off significantly. He found that he liked to wait many days before having an orgasm and, when he prolonged the orgasms, he found they were much more pleasurable. He found that he had a desire to eat his semen that he had been saving up but after he came, those desires left him.

Over the months of his lack of work, he eventually stumbled upon chastity websites and he was exposed to the world of female domination, chastity belts and male slavery. This new world intrigued Randy and he started conversing with some of the people on the site. He talked to chastised men and even one chastised woman as well as dominating women and men. He liked to dream about being chastised but after an orgasm, he wondered why he was even into all of that.

Eventually, (via chat room) one of the dominating women wondered why he didn’t have a chastity belt of his own. He said that he didn’t have the money to buy one and he didn’t have anyone to hold his keys. He had been with a handful of women in his life and, to his knowledge, none of them would even have any idea what chastity was all about just as he wasn’t apprised of the chastity world in the past. Randy saw that the woman resided in the NYC metro area as he did. They chatted back and forth over the next few days. Randy had not came in the last seven days and he was beginning to think about meeting with the woman, who went by Mistress Judith.

They met at a Dunkin’ Donuts in Hoboken and both parties were pleased with the person on the other side of the orange table. Judith was beautiful, with stunning black hair, luscious 38C breasts and a delicate yet graceful figure that was led around by long, milky legs. Randy was a stout, handsome lad himself. Dominating women usually don’t have much use for the looks of a man but he was more handsome than the usual men who submit themselves to chastity.

They talked about their lives, accomplishments and such. Eventually, they arrived at the subject that brought them there in the first place. Randy had a good idea about what he might experience in submission to a Mistress. He didn’t know what it felt like. He said he wanted to try it out before he jumped into anything long term. Judith remained silent, acknowledging his interests and quips.

She broke her silence by laying out how she goes about being a Mistress. “Of course there would be a trial period. I can’t just imprison someone without their consent. A servant will like some of the misery that comes with servitude but there should be some misery that he may not like yet not too much as to make his life miserable. It’s a delicate balance and that is why I want you to lay out how you want me to dominate you. Some things you request I will be forced….wrong choice of words….choose to ignore and others that I will keep in mind. However, once you agree to be my servant, there is no going back.

Randy told about how he wanted to lick pussy on a regular basis. He didn’t want to dress up as a woman or anything but he was alright with slight feminization. He didn’t want to be humiliated in public, have contact with men in a sexual way (though Judith said she would have lovers over to have sex with her),

“Alright, then. It’s all out in the open. What I want you to do is go home, masturbate (but only once) and think about how you want to be dominated. When I am ready for you, I will let you know where I live and you will stay with me for one week. I will give you a taste of how it is to be my servant.”

“Thank you, Mistress Judith. I’ll go home and think it over.”

Chapter 2

He mulled it over in his head again and again. The idle days of futilely searching for employment and trying to stay in shape left him a lot of time to think of Mistress Judith and his possible submission. She sent for him ten days after they had met. He received a round-trip Acela ticket in the mail and he made his way to Judith’s house. When he got there, she fitted him with a chastity belt. He was awed at the experience of trying one on for the first time. He was told to stay in his tighty-whiteys as that would be his uniform for the week. He was given some cleaning supplies and told to get to work.

Mistress Judith kept him busy working long hours but she was rather easy on him overall. He owned one butt plug, a small one that he brought with him and she had him wear it on the fifth day. He was paddled a few times for missing some spots and not fully drying Mistress’ laundry. He slept in Mistress’ bed the first two nights yet she barely touched him expect for deliberate, teasing rubs and he was instructed not to reciprocate unless she said. The sixth day, Randy was eager to lick Judith’s pussy and she had him do so for two hours, well after his neck and his tongue got tired. He took his place for rest on the floor where he had slept the past few days.

As Randy was ready to leave Judith’s abode, he was unsure of what would happen next. He liked being her servant but he liked his life and had hope he would land a job at some point. She told him to think about being her servant and she would give him a call in the next few days. He still had the CB-6000 on and asked if it could be removed.

“I will send the key in the mail, Randy.”

He got the leys in the mail five days after he left Judith’s house. He scrambled to get the key out of the envelope and he unlocked his cock prison and masturbated fast and furiously, expelling more semen than he had ever seen come out of his dick. After he had refracted, he looked at the contract Judith had sent in the mail along with the key. It seemed pretty straightforward. It said Randy would be her slave and would have to do whatever Mistress said. For Randy, it just seemed like it would be too much. He had a lot of doubts and, when Judith rang, he was prepared to turn down the offer.

“Oh, I see. Well, Randy, that is your choice. If you ever change your mind, give me a call.”

The short phone call ended and Randy was prepared to get on with his life and he sent the CB-6000 back to Judith. Two weeks later, he found out that he would no longer be receiving unemployment insurance payments. He didn’t have much family as his parents were killed on 9/11. He had a sister in Connecticut but he didn’t want to live there. He was an insurance salesman who made a decent amount of money when he was working but the job market was such garbage and he really didn’t want to stoop down to working at Starbucks or some menial job. He was now considering calling Judith back.

His only concerns were that after the year of being a servant, he would have to go back to work if he chose to do so. Also, he wanted to make sure he got orgasms at least some of the time. Judith assured him that he would be devoting some of his time towards his continuance as an insurance salesman as she ran a business out of her home and had the set-up to facilitate his working needs. “I may need some time but I might be able to scrape together a position where you can once again be an insurance agent or something similar.” Judith said over the phone. “Now, about your orgasms, you will ejaculate once every two to three weeks I assure you. It’s not healthy for you to go without expelling semen. Do you have any concerns? I pride myself on being a Mistress that cares for my servants and you will be no exception.

“Mistress Judith, I believe I want to go through with this. Allow me to take one week to arrange things and I will be over to start being your servant.”

“Splendid, Randy. You should take two weeks, though, while you have the time. I want to make sure you are good and ready to serve me.”

Chapter 3

Randy took care of moving out of his apartment, drowned his parent, sold his car and put his things in storage. He jacked off twice a day, eagerly thinking of his future life as a servant for a Mistress. He liked the way her pussy tasted and he was hungry for more. When he arrived, he expected to get started on cleaning his Mistress’ house but she had a black teddy on and she led him to bed. She began seductively kissing his neck and they made love that afternoon. They lied there afterwards looking at each other. They had eventually caught their breath when Judith got up and got the paperwork for Randy to sign. Randy read the contract over and it was the same as the one Judith sent to him before. “Simple enough, Judith. I am your servant.”

“Good then. Put the chastity belt on and get cleaned up. Meet me downstairs in 20 minutes. I will go and make copies of this.”

Randy had put the familiar CB-6000 on again and was in his underwear when he met Judith downstairs. Judith had a list of cleaning chores and other tasks but she wasn’t ready for him to start cleaning just yet.

“Randy, I want you to bend over and grab your ankles.”

“OK, Mistress Judith.” He did so and it was silent.

“Slave, did you know what you did wrong?”

Randy’s heart was pounding. He answered after a few seconds. “No, ma’am, I don’t.”

“You didn’t call me Mistress upstairs and you failed to do so just now. No, Ma’am, no Judith. You will call me Mistress or Goddess from now on. You were good about it before today but you got a little bit too comfortable. Now, you will be taught a lesson.”

She whacked him in the buttocks five times with a meter stick. “You’re training begins today. You will find that life will be a little bit harder than the first week you were here. For the first week, I don’t think I will be giving you a chance to make another mistake with your mouth.”

She handed him a ball gag and he put it on. She put a lock on the hinge and told him to spread his legs. She swiftly slapped him with the stick in his ball sack that the chastity belt so easily exposes. He doubled over in pain.

“Now, let me show you to your quarters.”

There was a small room on the same floor as her bedroom where he would stay. The room contained just a thin mattress on the ground and a dresser full of white underwear and various sundries.

“I would ask you how I feel now but I really don’t think it is a concern of mine. You shall begin your cleaning duties. I want the entire list completed before you go to bed. If things are not done to my satisfaction, I will give you a beating and your orgasm will be postponed. Right now, you are due for an ejaculation in two weeks. Go now, slave.”

The list took him all night to complete and at 9:30 the next day, he finished the list and was ready to go to bed. Five minutes later, Judith came in and woke Randy up.

“Come with me, slave. Let’s discuss your work.” His eyes emoted that he wanted to sleep and he was hungry as well but he could communicate neither request.

“Well done, slave. You accomplished most of the chores but there were a few things that you missed. I’ll decide the punishment later but your orgasm will be postponed a month. Now, here is some rice and beans for you to eat. It’s not the food you are accustomed to but I don’t have the expense account to feed both you and I gourmet meals. Plus, as a slave, you only need a basic meal and it’s better than half of the world’s population average meal, so I don’t want to hear any complaining.”

Randy ate his meal quickly and retired back to his mattress and got some due rest.

Chapter 4

It was the day of Randy’s ejaculation and since he would not be getting an orgasm, he was curious as to how he would expel semen.

“Slave, this is a prostate stimulator. I will put this in your anus and you will bend over this chair and wait while this thing does its work. I will put a condom over your CB-6000 and you will eat the contents of it when it has been expelled. Have you ever eaten your own semen?”

“No, I haven’t.” Randy said. Mistress had taken the ball gag out of his mouth three days ago and it was about to go back in again. Randy was really eager to eat his own semen as he had not had an orgasm since he had sex with Judith upon his arrival. He had that same urge that he had before where he wanted to eat it. He had a bit of trepidation in his mind because he had never tried it and when he did come, he wondered if he would lose the urge to eat it. At this point it didn’t really matter.

In forty minutes, he was thoroughly milked but it was another 20 minutes after that before Judith came around and turned off the stimulator. “That’s quite a load, slave. I am going to pour it on the floor, take off your ball gag. You will eat it, thank me and start cleaning the bathrooms. They are filthy and I have some company coming.” She did what she said and he wasted no time as she had a paddle in her hand if he were to lollygag. “Get this place tidy and, when the door bell rings, I want you to be out of sight. I don’t need the help around when I host a wine and cheese party. In sometime, you will help out with my parties but I have some other things to fill your time tonight.

Randy cleaned up with the taste of semen in his mouth. He didn’t like it overall but there was something arousing about it to him. He got the house fully cleaned and in order and the doorbell rang. Judith’s heels clicked in the foyer and she told Randy to get in the garage and sit quietly. An hour later, she entered the garage and found Randy sitting as he was told. Randy noticed that there was a cage in the garage and Judith informed Randy that he would be spending the rest of the evening in the cage. He had moved towards the cage when Judith dug a big butt plug out of her purse and told him to put it in. “If it is not in two minutes from now, you will be hurting ten times as much as it will hurt your anus to shove it in there.”

He lubed it up with his mouth and got it in there in time. He was in great pain but it would subside. The sensation of having a large object in his butt, an arousing and painful sensation, would not subside. She cuffed his hands behind his back, put his ball gag in and put him into the cage. “I’ll come and get you when the party is over.”

Randy was left with his thoughts of his Mistress, his evolving situation and, most prominently, the butt plug stuck in his behind.

Chapter 5

Mistress Judith informed her slave that his training was over. She would no longer give him regular random beatings, cold showers and the cleaning lists will be reduced as well. “However, your equipment will be changing, slave. I’m taking off your CB-6000 and you will be wearing this Neosteel chastity belt. Also, you will be wearing this butt plug and accompanying belt that holds it in at all times until further notice.”

“Mistress Judith, I am supposed to have a release today and you have not pushed back my time for orgasm beyond today as well.” Randy meekly protested.

“Slave, I remind you that you are under my control and, as eager as you are to cum, it’s not your job to inform me of your orgasm schedule! For this, I am postponing your orgasm two weeks. Now, put this new gear on!”

He donned the gear and was shaking as his new medium sized butt plug had his tucked penis in his new “gender-bending” belt. Judith revealed a Greek fraternity style paddle and told Randy to bend over. He did so and she began to wail on his ass. She wasn’t hitting him hard but with swift, firm strokes, she was making his ass red and swollen. She was pounding that butt plug in as it was subtly bulging out from the belt that was keeping it in. Back and forth went the plug, as in a tennis match, beating it in again and again. Ten minutes later, his belt was leaking semen and he was curled on the ground, frustrated, sobbing and sore.

"You will always get to cum, you may never enjoy it again."

“Slave, we are going out tonight. I am taking you to a buffet because you haven’t diverted from your diet of rice and beans for the past two months. When we get there, I want you to eat a little bit of everything from the salad bar only. You will try everything on the menu.” Randy thought this was odd but he was eager to get out in society once again.

Judith dined on prime rib and Randy was munching on various vegetables. He ate everything he put on his plate and his Mistress took mental note of what he didn’t like. She was in a good mood and offered to buy him a glass of wine. Randy got the nerve to ask his Mistress a question.

“Mistress, why did you allow me to enter and cum in your vagina on the first day? You are a wonderful Mistress and I am your slave – why would you have sex with me?”

“Well, bitch, if you had never slept with me, you wouldn’t serve me as well if I denied you everything. I upped your intrigue level. That is the key to my Dominance; one time is all it takes and you’ll remember it forever. It was good, was it not? The memory of something wonderful occurring will be in me in your mind every time you perform an act of servitude. There will be a point in time where you never get to lick my pussy anymore and another where you won’t even see a woman naked. Think of all the things you have done and as they are systematically removed from your experience, you are left with memories and a hopeful imagination”

They drank their wine and left the Old Country Buffet. They went to the store and picked up some supply and food. When Randy got home, he put everything away. When he was putting away the food, he noticed that he was putting away a lot of cauliflower, olives and peas. He hated those three foods the worst and it must have shown on his face because the Mistress apparently picked out things that he didn’t like. One of those three foods ended up on his plate of rice and beans. He had to choke those foods down but eventually got used to it.

A week later, Mistress Judith took his belt off and announced that he would get a real orgasm. He had to use hot sauce as lube. He was instructed to sit down on the ground and slowly stroke his penis, in silent pain, while she talked.  She took her time but this is an abridged version of the soliloquy.

“Do not cum until I am done talking or you will have forgotten this day by the time you touch your penis again. Anyways, I was able to find you some work as an insurance agent. You will have an office here in this house but you will also go to the branch office nearby. I have purchased some clothes for you that you will only wear when you are there or when clients come over here. I have also arranged for you to enter another line of work. Your other job will be revealed to you later. Your client will be over in a few minutes. Now, you have permission to finish.”

He began to stroke harder and seconds later, he shot semen feet away from his body then futilely tried to quell the fire that was burning on his penis, balls and hand.

“You know what to do.” He was already licking it up when she told him to go into the room that is his new office. He waited for an hour with his belt on but his butt plug was replaced in his anus. A man then entered the room and he smiled and undid his zipper. The man was showing an erect penis with his hands on his hips. “Boy, are you ready to give me a suck job to Daddy?” Randy, supremely caught off-guard, wasn’t prepared to suck him off but he knew that he had to finish this guy off or he would face strict consequences.  The man came in his mouth and he said that he paid extra money for Randy to show the semen in his mouth and then swallow it. Randy reluctantly did so.

The man left the room and came back and fetched his paperwork. “I came here to transfer my insurance plan as well.” Randy realized two things: he was an insurance agent and he was also a gay hooker for his Mistress.

Chapter 6

The office welcomed Randy but they all interacted with him differently than he had ever experienced. He was given a hefty caseload and was a fellow employee but the whole office knew of his chaste state and he was hit on as if he were a female secretary in the 1950’s. Men and women would slap his ass and he would be cornered opportunistically by anyone who needed a little morning oral service. Randy complained early on but it was clear that the powers that be didn’t care about how the office treated him and he would have to service those that requested his services to keep his job.

He was semi-regularly sucking off a male employee here or under a female employee’s desk there. Most notably, the 73-year old vice president had requested that he lick her ancient vagina and once, after-hours, Randy was cornered by a female employee who was good friends with Mistress Judith and she reamed his ass with a strap-on.

When he got home, he still had to clean the house and pamper his Mistress before retiring to his bed. Mistress informed him during a pussy-licking session in her bed that he would be sleeping in cage located the garage until further notice. She also got him some gifts. He opened up a present that held the biggest butt plug he had ever seen, an enema bag and she led him to the garage where there was a hole cut into the wall by his cage. On the other side of the wall is the outside. “From now on, your clients will be able to ring a bell and stick some money in the slot before you service them. In essence, you are a 24 hour whore. I would ask you if you liked your two jobs but I don’t care whether or not you do. It has been months since your last orgasm, so I presume it only adds to your arousal. Come upstairs again…well, go upstairs with me as you won’t actually be coming upstairs unless I say so and you can put on your new presents!”

He inserted the massive butt plug after many attempts. His ass has been trained to take things near this size for months but he really was stretched at this point and he was rolling on the ground in a mixture of arousal, pain and distension that the butt plug provided. Mistress had came back with a full enema bag and told him to go downstairs with her. She administered an enema and she replaced the large butt plug, ensuring that no spillage would occur. “I will be back in a few hours when your clients have all came, I mean stopped by,” giggling as she walked away.

Chapter 7

It was Christmastime and the office Christmas party was to take place tomorrow (Randy was Jewish but that’s not important here). Mistress Judith had Randy on her bed, with all four appendages shackled to a different bedpost. She had his belt off and she had been teasing his erect penis for hours, bringing him to the edge and backing off which had brought him to tears since he or no one else had touched his penis in three months and his mouth had produced countless orgasms for his colleagues, client, mistresses and a horse.

“Tomorrow, I have a surprise for you at the party. You have to trust that I am doing the right thing. You can refuse this orgasm if you don’t want to go through with my surprise but, if you give me consent, I will finish. Will you let me surprise you?”

“Yes, Mistress, I will.”

She finished what she started but she managed to edge him for another hour. He came and she spooned the semen into his mouth. “Very good, then! It’s time to go to your cage. You are spreading Christmas cheer tonight for a few clients.”

The party started the next night and, by that time, Randy’s role in the company had changed. His workload was reduced as he was doing more cleaning and errands for his colleagues than actual insurance cases. His only clients were the ones buying two services from him. Since his role had changed, it wasn’t odd that he was helping the interns run the logistics of the party. When it was time to hand out gifts, Mistress Judith was given the floor and she called Randy up to the front.

“I have an announcement. There will be a drawing. The winner will take Randy home for two weeks. You will be free to put him to work as you see fit. He is not afraid to get dirty while getting your house clean and keeping you and your significant other satisfied.”

Randy had expected something like this to happen. What he didn’t expect was how mean the winner of the drawing was. It so happened that the winner was the woman who had worked his ass with the strap-on in the office. Randy was hoping for a break during this 2-week vacation, yet these people who were not experienced dominants were just as mean as Mistress Judith and even worse.

They worked him like a rented donkey and it really got weird and raunchy when it came to sexual favors. The winner’s husband had Randy give him a blumpkin and Randy, though he’d been through a lot, couldn’t stand the smell of feces, so he was in misery within misery. The couple’s daughter was home from college and her and her friends would spend hours teasing him with their bodies, causing his penis to swell inside his belt. When he returned to his Mistress at the start of the New Year, he was relieved to be back to what he considered a familiar situation.

“How did it go?” Mistress Judith coyly asked.

There was no real good answer to her question. He answered how she wanted him to.

“They were very nice people, Goddess.”

“Good. They regaled me about your amazing service. Well done. I know they were rough on you and I think you’ve had enough. I have a proposition for you. This treatment will end if you agree to my terms. You will have some dignity back and you won’t be abused by your co-workers unless you allow it. If you refuse my proposition, things will be status quo for you. Understand?”

“Yes, Mistress.”

“So, here it goes. I have the resources and the desire to make you a real maid. You will become a woman. Well, mostly. The sex change may be some time but you will start on hormones, start growing breasts and you will be groomed to be dressed as a lady. Do you want to do this?”

“Mistress, I..I…”

“Think about it. It’s real simple, though. If you say, yes, you will only be a maid and an insurance agent that will operate from home unless you want to be a secretary at the office. You will get a bed and will only be in a cage if you are bad. If not, the gloryhole in your cage remains open and you will be a fixture at the office. You keep your manhood in that case but still stand to lose a lot. Think it over.”

In the next couple of days, Randy had decided that he would become a woman. Things went as she said. Mistress started Randi (his new legal name) on hormones, received DD breast implants, got a makeover and continued to wear the Neosteel belt, which effectively tucks in any bulge that the male genitals makes. She was going to be a real woman soon, except with a penis.

“Mistress, what are you going to do about my penis?”

“Eventually, sweetheart, it will be removed. For the moment, it will be kept locked up. From now on, you, I and everyone else will not acknowledge that you have a penis. That means that you will receive no release unless I decide to stimulate your prostate. We all know that girls don’t have penises and you are a girl now. So no more penis talk unless you are talking with a cute guy you want to service.”

When Judith left the room, Randi cried softly into her hands. Maybe it was the hormones she was taking, the fact that she would never have another orgasm again from her penis or that all of this was happening too fast. What kept her assured was the fact that she was starting to look like a real woman and she was going to be a great one.

Epilogue

Randi never got a vagina. At some point, she was begging Mistress to start ordering clients for her to service as she was getting stir crazy and man-hungry.

“No my dear, you are a real woman now. When I give you your two off nights a month, you can go out and find men on your own. I can’t have my help sleeping with guys when you have so much housework and insurance deals to take care of.”

As difficult as this was to achieve, Randi was about as wet as a woman with a penis and no vagina could be.

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Ten years later, Randi developed breast cancer. It spread quickly through her body and she was bed-ridden at the end of her life. She was on her last days and was being cared for at home with Mistress Judith tending to her.

Judith knew what she had to do. When it was clear that Randi was about ready to pass, Judith removed Randi’s belt and wanked her off, sending her home. Randi gasped in orgasmic delight and passed on.

THE END

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