tagTranssexuals & CrossdressersDiscovering Mistress Sarah's World Pt. 09

Discovering Mistress Sarah's World Pt. 09


Part 9 -- The Final Part

Chapter 23 Leaving Work

Josie's last week at work and concluding week of his normal life went quick. At work he spent time getting things in order for the next unlucky person to take over his job. Mentally he was already checked out of work. All he cared about was getting on with his new life.

Miss May played a big part in ensuring his sissy life remained intact while he was back at work. Each day she sent him to work more feminized and enslaved. It started with the usual panties and stockings under his clothes but soon progressed to him wearing eye liner and a small amount of blush. On Wednesday she had him wear a pink dress shirt and by Thursday he was wearing women's business clothes. The clothes looked gender neutral but the labels were women's brand.

Miss May also announced to Josie's that it was his time of the month. She sent him to the store Wednesday night to purchase tampons. It was a simple task but Josie found it to be extremely embarrassing. Two women were in the tampon aisle when he first entered the store. He cold not get up the nerve to walk down the aisle while they were there. Instead he milled around the store until the aisle cleared. When it was empty, he quickly walked into it and scanned the products. There were many choices of pads and tampons. After a few uncomfortable minutes of analyzing different boxes, he settled on a pink box with 10 tampons. Before picking the box up he glanced to the left and right to make sure no one was looking. Then he quickly swiped it form the shelf and headed to the cashier.

His heart pounded as he walked through the store. He was already feeling embarrassed. He wanted to buy a few other things to make the tampons seems less conspicuous but Miss May made it clear that he was to only buy tampons. Josie tried to reason with himself that it was not a big deal and that guys bought tampons all the time for their wives and girlfriends. As much as he tried, these thoughts did not calm down his nervousness. What if one of his friends or neighbors came into the store, he thought. They knew he was not married. Josie was also very conscious that he was wearing eyeliner and a little bit of blush.

He walked to the register trying to look calm and relaxed but he could feel the redness on his face. The cashier acted normal when he put the tampons on the counter but Josie could barely look into her eyes. He quietly paid and then left the store. Josie was certain the cashier was laughing at him under her breath.

Thursday morning before work, Miss May had Josie bend over while she inserted the shell of the tampon just inside his boy pussy. It hurt at first, but then Miss May held the shell and pushed the "tail" forward forcing the firm cotton tampon out of the shell and deep into his ass. Josie felt a twinge of embarrassment at how good the cotton felt inside his ass. When his mind cleared of the sinful pleasure, he noticed the pretty feminine scent from the tampon package, which filled the small bathroom. The feminine scent combined with the feeling of the tampon inside him, mentally put Josie into a girly mood.

Miss May had him dress in pink panties, pink stockings, and a garter belt. She allowed him to wear socks to cover the stockings, but the socks had frilly lace at the top. Josie worried that if he sat down at work, his pants legs would ride up just enough for someone to see the lace.

Concerned he said to Miss May, "What if someone sees the lace on my socks?"

Miss May laughed. "Well then they'll know you are a sissy. I'm sure they've figured it out already sweetie. Your feminine side is really showing this week."

Josie remained quiet. He knew there was no arguing with Miss May. She was enjoying putting him in these awkward situations. Miss May also dressed him in women's pants and a woman's blouse. Then she penciled in a thin line of eyeliner above his lashes and dabbed a hint of blush on his cheeks.

Miss May handed him an individual tampon which was still in the pink plastic wrapping. "You're going to need this princess, just in case you have your period and need a fresh tampon."

The notion of him having a period was silly but it made his confined clitty twitch in his panties. Josie would be thinking about his period all day. He took the tampon and dropped it in his work bag. The tampon fell next to his small purse, which was filled with red lipstick, a small bottle of perfume, and a few make-up items. Josie was not allowed to leave the house without his purse on hand. He was thankful that Miss May allowed him to keep it inside his work bag and not in plain view.

On his way into work, Josie wondered how much truth there was to Miss May's comment that his work associates probably figured out he was a sissy. Miss May had kept him in an aroused daze all week and his feminine side was still a fantasy world to him. All week he was living under the pretense that no one at work would notice the changes in his clothes and looks. Now he wondered whether he was living under a false pretense the last two weeks.

He looked into his rear-view mirror and did a reality check. The eyeliner was barely noticeable. The blush was a natural beige, but it was noticeable and gave his cheeks a natural feminine glow. Josie felt embarrassed, realizing that some people must have noticed the blush. He rubbed his hands over his cheeks, doing his best to blend the blush into his skin and make it less noticeable. Then there were his clothes. He was literally dressed head to toe in woman's clothes. His top and pants were neutral but they were still woman's clothes. Josie could not believe he let things go this far. He had wanted to keep his feminine life out of his work life. He hoped that he could resign with no hint of the life that he was going to embark on. Now he realized that this hope was compromised. He wondered what his co-workers thought of him now.

As he parked his car in the parking lot, he thought about abandoning work. He could come up with an excuse to not show up for the last two days. The more he thought about it, the more he knew it was not an option. It was not the proper way to leave the people he worked with for many years. He also knew that Miss May and Mistress Sarah would never approve of it. He was sure this was all part of their plan with him. He knew they got off on controlling and embarrassing him. It was exciting for him to know that his humiliation fueled their desires. The excitement motivated him to finish his day at work.

Josie was full of emotions during the day. On the surface he did the best he could to maintain his male identity. However, the tampon inside his boy pussy was weighing heavily on his emotional state. Feeling the intimate womanly item inside him all day created a stronger bond with his girl personality. The soft firmness inside him could not be ignored. Josie enjoyed this connection with womanhood that he was feeling.

Friday Josie returned to work wearing another tampon and dressed similarly except for one change. His chastity device was removed. Mistress Sarah had sent a message the night before that Miss May could remove his chastity device for the day as a reward for his obedience during the week. Josie was thrilled at the news and was excited Friday morning when Miss May unlocked the device and removed it.

At first Josie thought it was a great reward. However, he quickly discovered it was pure torture. His pent-up arousal escaped the moment Miss May removed the tube from his cock. He drove to work hard as rock. He spent several minutes sitting in his car in the parking lot, willing his cock to shrink. When he finally calmed down he reached into his pants and pushed his cock back between his legs and pulled his panties tightly up around his waist to keep his cock in place. He figured this would be the only way to keep him from walking around all day with an embarrassing hard-on.

About mid-way thought the morning, Joe received a call on his cell phone from Mistress Sarah.

"I miss you a lot slut. How's your morning going," asked Mistress Sarah.

Josie's cock twitched in his panties at the sound of his Mistress' voice. He replied, "I miss you too Mistress. Thank you for letting me out of my chastity device."

Mistress Sarah corrected him with the quickness and firmness of a drill sergeant , "It's not a chastity device Josie. It is a clitty cover. You will refer to it as a clitty cover from now on, understand?"

"Yes Mistress."

"Good girl. Are you enjoying your freedom?"

"It's nice but I am super horny. I had to tuck my clitty between my legs to keep calm."

Mistress Sarah laughed in amusement. "It's nice to see you are reverting to your natural state. It does feel so natural to be tucked away in clitty form doesn't it princess?"

"Yes Mistress," admitted Josie.

"I am proud of you for realizing how you should be but I think Joe needs to make an appearance for his last day of work. Take him out for me now."

Mistress Sarah's voice and commanding tone were hypnotic to Josie. He almost forgot where he was. He was ready to obey without thinking. Thankfully he came to his senses for a brief moment and closed his office door. Then he unzipped his pants and pulled out his cock. It immediately swelled in his hands.

"I have Joe's cock in my hand," he replied into the phone.

"Mmm, that's my girl. Stroke him for me Josie. Make your man happy on his last day of work."

Josie obeyed. It only took a few strokes before precum was dripping out the tip. Mistress Sarah made him rub the stickiness all over Joe's cock until an audible squishing sound could be heard from the wetness.

"Can I make him cum?"

Mistress Sarah laughed at how quick the request came. "No silly. You are a desperate slut. That's how I like you to be and how I want you to feel the rest of the day. Lick your hand clean for me."

"Yes Mistress," replied Josie. He licked the stickiness from the palm of his hand.

Mistress Sarah encouraged him through the phone, "That's it princess....lick up Joe's stickiness. I know you love it. I know you want to taste his cum. That will be your treat when you return home to me."

Josie loved how Mistress Sarah made him feel overly slutty and horny. "I can't wait to see you again Mistress. I already miss you."

"I know pet. You will be with me soon enough. I have lots of training to do with you. Now put Joe's cock away sweetie and get back to work."

Josie was disappointed for the fun to end but he obeyed. He zipped up his pants and started cleaning up his office. The afternoon went by quick for Josie. When he was ready to leave for the day he sent Mistress Sarah and Miss May a text indicating that he would be leaving in about 10 minutes. His phone rang immediately after the text was sent. It was Mistress Sarah.

Mistress Sarah's said, "Pet, another chapter in your life is ending. Are you sad?"

"A little sad, but I'm very excited about the next chapter."

"Me to princess. This is where the story starts to get fun."

Josie's cock was already swelling in his pants from hearing Mistress's voice. He sensed that she was not calling just for condolences. He knew there would be some task or assignment coming. His instincts were exactly right. Mistress Sarah ordered him to pull out 'Joe's' cock again. Josie shut his office door one last time and obeyed. He started stroking on her command.

Following Mistress Sarah's instructions, he brought himself to the edge several times. When Mistress Sarah was convinced that he was in a complete state of arousal she said, "Josie, I want you to have nice pretty glossy lips when you walk out of work today. My princess needs to leave with a great impression, don't you think so slut?"

"Yes Mistress," he replied obediently.

"That right pretty. You know what to do. Squeeze a bit of cum from Joe's cock and make your lips nice and shiny for me."

With all the edging, it was an easy task to do. A few squeezes on the tip of his cock caused a small gooey string of cum to ooze out. Josie let it drip onto his fingers. Then he rubbed the cream over his lips. He updated Mistress, "My lips are nice a shiny now."

"One more time pretty pet. Put another coating of cum on your lips. Don't be shy about it."

"Yes Mistress." Josie obeyed her command. Now his lips felt wet and sticky.

"Good girl. Now walk out of there nice and proud Josie. I will see you soon."

Josie said his goodbye to Mistress Sarah and then headed out of his office. He did not have a mirror so he did not know what his lips looked like. He hoped the cum blended in well. It was his goal to get to his car as soon as possible without drawing attention to himself. This proved to be an impossible feat on his last day of work. The first few people he passed did not bother him and did not make any strange faces at him so he assumed that either the cum blended in well or that they just did not notice.

Before he reached the elevator one of his female co-workers intercepted him to say her good-bye's. She hugged him and even gave him a kiss on the cheek. Josie was paranoid about his cum covered lips. While his co-worker hugged him he quickly licked his lips. A naughty and embarrassed feeling filled his body. He could not wait to get home to Miss May.

He endured a few more good-bye's before finally getting to his car and heading home. An almost empty apartment greeted him. With the exception of a few shopping bags on the living room floor, the place was empty. Whatever was not sold at the sale had been packed in the moving truck or taken to the local Goodwill store. Miss May had proudly informed Josie that she went on a shopping spree with all the money earned from the sale.

She was excited to show off her new items. She immediately ordered him to strip to his panties and bra and kneel before her. Before she started the show Miss May ordered, "stroke your clitty for me sissy. I want you to be excited from all the things I bought with your money."

Josie slowly rubbed his clitty through the soft panties. It swelled instantly. He was happy to be out of his chastity and able to play with himself. Miss May modeled dresses, sexy club wear, and lingerie. She looked amazing in each outfit. Josie enjoyed seeing her wearing the different lingerie and tight sexy outfits. Miss May made it a point to emphasize how she used his money to buy the clothes. Then she thanked him mockingly at how his submission was giving her a better life. In between outfits she made him kiss and lick her feet and her ass. While he licked her ass, she teased, "This is your place in life slut...beneath a woman, worshipping me, worshipping Mistress Sarah, and giving us whatever we want."

Josie continued to lightly stroke his clitty while he worshipped Miss May with his tongue. His arousal was high and still growing. Miss May's words were hypnotic visions for Josie. His mind absorbed them and held on to them. With no job and all his possessions sold or given away, he easily bought into Miss May's visions. He was happy with his new place in life.

Miss May showed off more than just clothes. She modeled bracelets, necklaces, rings, earrings, and shoes. She even bough herself a new camera. Miss May also showed Josie bags of expensive clothes and accessories that she bought for Mistress Sarah. She showed no restraint with spending all the money. All Josie's possessions had been sold off and the money used for a lavish spending spree for his Mistresses.

She saved this best for last. With a gleaming smile she produced two sets of diamond jewelry. Both were complete sets that included diamond studded rings, diamond pendant necklaces and matching earrings. The diamonds glowed with magnificent brilliance in the lights of the apartment.

"Aren't they beautiful," beamed Miss May.

"Yes, they look amazing."

Miss May picked up the diamond pendent on the left. "This set is mine. The other set is for Mistress Sarah," she said as she secured the necklace around her neck. Her fingers toyed with the pendent and it shimmered in the light.

"It's beautiful," complimented Josie.

"Much nicer than your car don't you think," teased Miss May.

"Yes Mistress," replied Josie submissively..

Josie was keenly aware that Miss May's excitement was about more than just the shopping spree. The shopping spree represented complete dominance over Josie. Josie had heard about financial domination before but he never understood it. He never imagined how a guy could let that happen to him or even enjoy it. Yet, he was in that very spot right now. He was stroking his cock while Miss May deliberately showed off every item she bought with his money.

His cock was raging hard. Miss May was pushing him into a deeper, newer submission. He could not stop it. The thrill he was experiencing at the moment had a strong hold on him and he did not want to let it go. He lived in the moment, not caring about what would happen next, and not even thinking that Miss May could just walk away anytime leaving him with nothing.

Chapter 24 Returning to Mistress Sarah

Josie's heartbeat quickened when he turned the moving truck onto to Mistress Sarah's road. A new life awaited him at the end of the road. He was both excited and scared about his future. He knew Mistress Sarah would open his eyes to a whole new world. She had already taken him into a wonderland full of pleasure that he never new existed. He was excited to experience pure sexual bliss with her.

Josie was also aware that once he set foot inside her door, his freedom and identity would disappear. He knew that her presence alone rendered him weak and helpless. He could not resist her beauty and commanding power. She was clever and manipulative and could read him like an open book. He would be putty in her hands and do anything she wanted. It scared him at how her desires and the need to please her were wired straight to his brain.

Even with the risk of losing everything and being completely emasculated and humiliated, he could not stay away from her. The pleasure and excitement that he experienced with her far outweighed the risks. Josie followed Miss May up to the door. He was so excited and nervous about seeing Mistress Sarah again that he did not even think twice about the fact that he was completely feminized in public. In the morning, Miss May had ensured he was in full feminine attire, including his wig, false tits, and 6 inch heels. At the last rest stop, she spent time touching up his make-up and lipstick. She wanted him to look perfect for Mistress Sarah.

The skirt she had picked out for him was so short and tight, that he could only walk in short steps. Josie was proud of himself at how easily he could walk in the heels. It took some practice but he mastered the right step and balance. Miss May walked inside without knocking and Josie followed behind her. They were immediately greeted with big hugs from Mistress Sarah.

Mistress Sarah beamed, "I missed you girls. How is my pet?"

"Very good Mistress. I missed you a lot," replied Josie in his girl voice.

"You look stunning princess. Miss May did a fabulous job with you."

"Thank You," replied Josie. His face blushed at the compliment. His cock started to swell. He was excited and aroused to be around Mistress Sarah again. It only took a second or two before his cock was bulging against the hard chastity device, trying to break free. The hard plastic held firm. Josie grimaced and waited for his cock to retreat.

Mistress Sarah gave Miss May a big hug and deep tongue kiss. When they broke the kiss, they looked at each other with hunger in their eyes. They had been away too long. Josie thought for sure they were going to strip down in front of him. Instead, Mistress Sarah dismissed Miss May saying, "Go find Nellie. Have him call some of his boyfriends to unload the truck. I have catching up to do with Josie."

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