Discovering Mistress Sarah's World Pt. 08

Josie repeated the words. As soon as he finished Miss May ordered him to say it again. She did this four more times. The sentence became a mantra to Josie and put him into a completely submissive mode. After the fifth time, Miss May said, "It's time to seal your fate." Then she slowly slid back onto Josie's cock. She let it penetrate her completely. Once his cock was fully engulfed she sat upright on Josie's stomach and began to slowly ride his cock up and down.

Her pussy was hot and wet and it felt spectacular rubbing over his hard and sensitive cock. He could feel her pussy muscles clenching his cock and pulling on it each time she lifted herself up. His mind went blank and he saw fireworks each time the full weight of her body pushed down onto his cock. He wanted to thrust into her, but he knew that she expected him to remain still. She was on top, and she was the one doing the fucking. He was not going to cum into her but rather she was going to take his cum. Josie understood all this and obeyed.

Miss May deliberately fucked him slow to show her power and control and to tease him unmercifully. Josie's hands gripped tightly around the ropes that went from his wrists to the head board. His back arched and his toes curled in pleasure. He was keenly aware of the soft stretchiness of the stockings around his toes and of the dildo pushing deep into his ass each time Miss May pushed down onto him. These were reminders of who he was now. He thought of Miss May's earlier words, 'This may be the last time your cock will be in a real pussy.' The words should have frightened him but instead they thrilled him. He knew he would long for this moment again, but to know that he would be denied this ultimate pleasure by two beautiful goddesses was exciting.

The gift in itself was twisted and perverse. At first Josie thought it was their way of letting him have his last male orgasm, the last experience of sex as a man. However, he felt nothing like a man. He was tied down beneath Miss May and forced to remain still while Miss May rode his cock. He was wearing panties and stockings and he had a dildo pushing into his ass. This was not the way a man would have sex. This was how a sissy slave experiences sex. At that moment it was clear to Josie that he would never again experience sex as a man. His new life had already begun. It had started the day he met Mistress Sarah, he just did not know it then.

All these revelations flashed through his mind in seconds and they excited and aroused him even more. He was glad at what he had become. He savored the feeling of fullness in his ass. He loved the stretchiness of the stockings against his legs and he could barely handle the sizzling pleasure from Miss May's pussy.

Then it happened. Miss May looked directly into his eyes and commanded, "Give me all of your cum Josie."

On command, Josie let go and for the first time in months experienced a full blown orgasm. He moaned loudly from the rare pleasure. Miss May timed her orgasm to be in synch with Josie. She bounced up and down and her pussy convulsed and gripped tightly around his throbbing cock. She moaned, "That's right Josie. Give it to me. Give me all your cum."

The orgasm seemed to last for ever. Even after Josie though he was done, Miss May continued to ride his cock. She pressed her hands onto his wrists and squeezed her pussy muscles as she lifted up. In a firm tone she said "Feel my pussy milk out all your man cum. I want every last drop of it."

When Miss May was finished, she leaned forward and kissed Josie on the cheek. "You are all ours now Josie," she whispered into his ear.

Miss May laid on top of Josie for a few minutes with his cock still in her pussy. Her body felt warm and comforting. Josie was exhausted and drifted in and out of sleep. He expected Miss May to slide up onto his face and make him lick the cum out of her pussy but she never did. She took his cum. It was the last of his 'man' cum and she was going to keep it.

Eventually Miss May moved off of Josie. Josie was drifting deeper into sleep so he barely moved. He vaguely remembered her wiping his cock off with a wet cloth. It seemed like she was doing something else with his cock but he was tired and he did not pay much attention. The last thing he remembered was her untying his hands and sliding into bed with him.

Chapter 22 Selling Off His Life and "Manhood"

Josie woke before his alarm clock went off. His awakening was gradual like waves slowly edging up onto the beach. He was in a sleepy dreamy state, reliving his magical night with Miss May. The sex was incredible but what was even more fantastic was how perfect she played the dominant role. Every move she made, everything she said, and even the firmness in her tone had put Josie into a euphoric state of submission. That night would live in his memories forever.

These thoughts and images aroused Josie. His arousal grew but something was not right. Something was pressing into his 'clitty' and keeping it from swelling. Everything felt tight. Josie lifted the covers and could see something around his clittie. It was hard to make out in the dark. 'It couldn't be,' he thought.

Josie slipped out of bed and confirmed what he thought. He was wearing a chastity device and it was locked on with a padlock. It was meant to keep him from getting aroused but the discovery of it had the opposite effect. His arousal intensified at the realization that he was locked up. He truly was a slave. Miss May was right. Mistress Sarah and Miss May owned him now.

Josie's movement caused May to wake up. In a sleepy voice she whispered, "Like your new clitty cover?"

"Yes...I guess," answered Josie unsure if this was a good thing or bad thing.

"You better learn to love it," replied May amusingly. "You're going to be wearing it all of the time now. You'll only be allowed out when we want to play with you or when you're ready for your milking."

"Milking?" Josie questioned this but he already knew the answer.

"Yes princess. Last night was your last full orgasm. That is unless you get Mistress Sarah in a very generous mood but I can tell you those times will be rare. From here on out you will be milked of your cum every few months."

It was another moment where Josie thought the he should be scared and running away, but instead he was aroused and excited at what Miss May was telling him. Mistress Sarah and Miss May's power and control were squeezing tighter and tighter around him and he loved it. Being milked like an animal by a beautiful Mistress was thrilling to Josie in some perverted and twisted way.

Josie was excited and confused. All he could think to do was respond, "Yes Mistress."

May was still tired. She closed her eyes and enjoyed the comfort of the warm covers. Before drifting back into sleep she commanded, "Shower yourself slave and then bring me some breakfast. We have a busy day so don't keep me waiting long."

Josie immediately obeyed. After breakfast, May had him dress in pink panties, pink stockings, and a matching pink bra. That was his work outfit for the day. May on the other hand was dressed comfortably in jean shorts and a t-shirt.

May was spot on about the day being busy. It started with a phone call from Mistress Sarah. Miss May put her on the speaker phone so the Josie and her could hear the instructions together. When the phone call was over they were clear on what had to be done. The main task was to get everything in Josie's apartment either packed-up and ready to move or put out ready to sell.

Josie was allowed to pack one medium size suitcase with his silly man clothes. Mistress Sarah emphasized, that this suitcase would be locked away at her house and would only be brought out if necessary, if he was visiting friends or family. He was also allowed to fill two boxes full of personal items that he wanted to keep. Everything else had to go. All furniture, clothes, pictures, appliances, plates, and other items were to be put up for sale. Anything that was not sold would be donated or trashed.

Josie's whole weekend was spent packing and getting ready for the moving sale. While he sorted through things, Miss May set-up tables and put prices on the items for sale. Everything was priced to go. It was a bit disheartening to see his dining room table priced at $400 when he bought it for over $1,000 just a few months earlier. Josie mentioned this to Miss May and she simply shrugged her shoulders and said, "We need to sell if fast Josie. Besides, this is all Mistress Sarah's property now, so your opinion does not matter slave."

She was right of course. There was nothing Josie could do about it. A few items were tagged with Miss May and Mistress Sarah's name. It didn't take much for Josie to figure out that these items were being claimed by his two Mistresses. Miss May wanted his flat screen TV, stereo system, and a few crystal vases. Mistress Sarah's name was attached to a beautiful china cabinet, and his kitchen set.

By the end of the weekend almost everything in the apartment was marked and ready for sale. On Sunday night Miss May had Josie hang 'Moving Sale' posters around the neighborhood. Unknown to Josie, an ad had already been placed in the paper. Mistress Sarah and Miss May planned for a big turn-out for the sale. The less they had to give away at the end meant more money for them.

People were already showing up for the sale on Monday morning when Josie left for work. Miss May greeted them with smiles and dollar signs in her eyes. As Josie drove off to work, he wondered how much of his life would be sold off while he was away.

Word spread quickly at work of Josie's resignation. Most of his day was spent fielding calls and visitors inquiring about his resignation and wishing him good luck. Although he was paranoid about wearing the chastity device, with all the visitors he had little time to think about it during the day. Occasionally he would glance down at his crotch to make sure it was not noticeable. He was impressed at how easily it was to go to the bathroom with it on. He had to sit down to pee, but that was expected of him anyway. At least now Mistress Sarah could be certain that he was not standing like a man. It gave new meaning to the idea of forced feminization.

Josie did not get much work done, nor did he care about getting work done. Mentally he was already checked out and he couldn't wait to get started on his new life with Mistress Sarah and Miss May. The end of the work day came quick and he hurried home to see how the sale went.

When he arrived at home, Josie could see a few men loading into a pick-up truck, what used to be his couch and loveseat. A young woman was exiting his apartment carrying brass lamps that he had owned for over 10 years. Apparently the sale was going well. The inside of his apartment was filled with strangers. Josie was surprised at how much of his stuff was gone. It took him a few minutes to find Miss May.

When Miss May spotted him, she exclaimed, "Kitty Kat!" and she ran up and hugged and kissed him. Josie blushed as a few people looked their way. "The sale is going great!"

"I can see that," said Josie.

For the next hour Josie helped with the sale. At 7 pm they shut the door so they could unwind and relax. The sale would resume again first thing it the morning. Miss May's first order to Josie was to strip down to his panties and prepare dinner. Josie baked a full meal of chicken, potatoes, and corn. He served it wearing nothing but the white cotton panties that he had worn under his work clothes all day. After dinner Miss May insisted that Josie freshen up with a bubble bath and by shaving the stubble that had grown in on his face during the day.

After his bath, Miss May adored his chastity device. She tapped on the hard clear cover with her nails and giggled. "It's such a cute clitty cover." She even leaned down and kissed it. "I bet you wish you could feel my lips against your clittie Josie."

"Yes I do Mistress. Please let me out," begged Josie. He voice was filled with pleasure and pain. His arousal was growing causing his cock to swell against the hard tube.

Miss May put her lips over the clear tube and rubbed her tongue over the tip. Josie could barely feel her tongue on his slit. He moaned. "Please let me out."

Miss May was enjoying torturing Josie. "Aww. What's the matter princess? Does your little clitty want to be all big and swollen? Do you want to feel your clitty in my mouth?"

"Yes, please," begged Josie.

Miss May's hands tickled and teased his balls. Josie felt like his cock was going to burst the chastity device but it held firm. He had only been in the device one day and already he was desperate to be free.

"Well we did have a good sale today Josie. Maybe as a reward I can let you free for a bit. I made almost $2,000 today. I should be able to buy some nice clothes and jewelry for myself with that money. Maybe if you're good, I'll buy you a pretty bracelet and necklace. Would you like that princess?"

"Yes I would like that," replied Josie feeling even more submissive. Josie figured he would not see a dime of the money from the sale of his things, especially after Miss May had indicated earlier that all his possessions belonged to Mistress Sarah. He also knew that Miss May purposefully mentioned spending the money as way of reinforcing her control over him and perhaps to test him to see if he would challenge her.

Josie of course did not challenge her. He accepted defeat and his future as a slave to her and Mistress Sarah. He agreed to what she said and awaited her next words. Miss May teased his locked up cock a bit more. Then she disappeared from the room and returned with the key. She held the key up and smiled. "I will unlock you as a special treat but there will be no cumming for you sissy, understand?"

"Yes Mistress."

"Good sissy. I want all your attention on me tonight. I've had a tiresome day selling all this stuff. I need some pampering and then the cover goes right back on, got it?"

"Yes Mistress. Thank you Mistress!"

Miss May unlocked the padlock and slowly removed the hard tube and ring that held it secure around the base of his cock. Josie's cock immediately grew hard. Josie was happy to be free. "Thank you," he said again to Miss May.

"Your welcome pet. Now start rubbing and licking my feet."

Josie went to work on her feet. He spent the next 30 minutes slowly undressing and massaging Miss May's body. His cock remained hard the entire time he worshipped her body. He loved seeing her completely naked. Her body was slender and delicious looking. Miss May let him spend extra time massaging her breasts and nipples.

Miss May pushed him down to her pussy and he eagerly lapped at her wetness until she came with a tremendous force. The minute her orgasm hit she squeezed her thighs tightly around his head holding him tight against her pussy. Her hands pressed into the back of his head forcing him deeper into her pussy. Josie was weak and helpless between her legs. She used him selfishly for her pleasure. Even after her orgasm passed, her thighs remained clenched around his head, holding him close to her pussy.

Miss May could feel his deep breaths blowing across her pussy lips. His face was only inches from her hot sex. For several minutes he was forced to stare at her pussy and breathe in her scent. This was his place in life. He was at the mercy of her pussy.

"Thank You Miss May. That was great," complimented Josie. He did not have an orgasm but he truly enjoyed pleasuring his Goddess and it was thrilling to bring her pleasure while being denied.

"Why don't you thank my pussy while your down there," ordered Miss May smugly.

Josie stared into her pussy and said, "Thank You."

Josie felt her thighs squeeze tightly around his head and then release slightly. "Who are you thanking slave?"

"Your pussy," replied Josie feeling somewhat silly.

"Then address it properly slave."

Josie replied, "Thank you Miss May's pussy."

Miss May laughed arrogantly. "That's good. Say it again."

Even though it was just him and Miss May in the room Josie felt a twinge of humiliation at talking to her pussy. He repeated. "Thank You Miss May's pussy."

Miss May was having fun. She released his head and rolled over slightly so that her ass was in front of his face. "Now thank my ass Josie. Give it a big kiss first."

Josie kissed her right on the pucker hole and said "thank you Miss May's ass."

Miss May laughed again and said. "It's amazing what you slaves do. Get up on your hands and knees dirty slut!"

Josie did as instructed. Miss May slipped on a strap-on, lubed up his ass and went right to work fucking him. Josie was quickly getting used to being fucked in the ass. Each time it was becoming more enjoyable. The fullness inside him was naughty and delicious.

Tonight she pounded him hard and fast. There was no orgasm waiting for him and there was no orgasm for her. It was all about him being a fuck toy and Miss May proving her dominance over him. As she fucked him hard, she pulled his hair, forcing his head to look up. "That's right slut, tonight you are all mine! I own you. I'm taking your possessions and I'm keeping every dollar earned from this sale! Isn't that right slave?"

"Yes Mistress!"

Miss May's fucking slowed but she penetrated deeper into his boy pussy. "Mmmm. You are my bitch! I'm going to fuck your sissy pussy every night and you are going to enjoy it! I'm going to keep you locked up and dress you like a pretty sissy! You are so weak slave! My weak little sissy slave!"

Miss May repeated these words over and over again while she fucked Josie. Finally she dismounted him and pushed him away. She threw him the strap-on on and ordered him to clean it and then lock his chastity device back on.

The rest of the week went in a similar manner. Each day he went to work and then came home and helped with the sale. He would then shave, take a bubble bath, pretty himself up and spend the rest of the night serving and pampering Miss May. Each night Miss May pegged him in the ass with a strap-on. By the end of the week she had moved up to a larger strap-on, congratulating Josie on how well his boy pussy was molding into the perfect fuck toy.

The only thing that remained different from his Monday routine was the Miss May did not let him out of his chastity device. She took great pleasure in pegging him and demeaning him while his cock remained locked-up.

Josie's apartment cleared out quickly during the week. Miss May ended the sale on Saturday evening. That night Miss May allowed Josie to drink champagne with her to celebrate how successful the sale was and how much money she made on the sale.

On Sunday, Miss May had Josie dress in completely feminine attire. He wore a plain shirt with a black skirt. Underneath he wore pantyhose and a lace bra that was filled with his false tits. Miss May require him to put on his blond wig and a full face of make-up with glossy red lipstick. He was also required to wear his black heels. It was not the most comfortable outfit for working around the house, but comfort was not Miss May's concern.

When Josie was dressed, Miss May informed him that someone would be coming soon to look at his car and he was to be on his best behavior. At this news Josie gave her a calm and obedient 'Yes Mistress.' However, on the inside he was shocked and panicking. It was shocking because he did not even know she was going to sell his car. He was panicking because he was going to meet someone while dressed as a girl. He did this at Mistress Sarah's house but this was much different. He was in his home. He was in his hometown. What if he knew the person? What if the neighbors saw him?

There was a knock on the door and Miss May looked over at Josie with an amusing smile on her face. "Get the door for me slave."