tagTranssexuals & CrossdressersDiscovering Mistress Sarah's World Pt. 08

Discovering Mistress Sarah's World Pt. 08


Part 8 -- Complete Surrender

Chapter 21 Leaving Behind Joe's Life

Mistress Sarah was very pleased with Josie's training and feminization. She was anxious to have complete reign over him so she sent him home a day early to pack up his things and prepare to leave behind his life in the Philadelphia suburbs.

"I'm sending May with you Josie," announced Mistress. "She will look after you and make sure things are done according to plan."

"Yes Mistress." Josie's heart pounded hard in his chest. His immediate thought was, 'this is really happening.' He was scared about the future but he was also extremely excited. His cock was rock hard as knowing that he would soon be fully dependent on Mistress Sarah.

May was thrilled to take time off work and be given ownership of Josie. Mistress Sarah gave them just over two weeks to take care of business and return home. Back in Philadelphia things happened fast as a blur for Josie. Although he had already taken off work for the remainder of the week, May insisted that he go to work on Friday and hand in his resignation letter.

Friday morning May gave him the envelope with his resignation letter and instructed, "Give your boss the letter and then text me and Mistress Sarah the moment you walk out of his office."

She was kind enough to let him dress in normal boy work clothes. However, underneath the clothes Miss May dressed him in a white silk thong and white stockings. His toes nails were painted a bright shiny red and his finger nails were coated in clear polish. It was enough to keep his new feminine side close by, without creating a scene at work.

Josie felt strange walking into work. Being immersed in a complete feminine world for almost a week had changed his frame of mind and it seemed odd being back to his normal routine. Josie was nervous about resigning. He was nervous about how his boss would react. It was a silly reason to be nervous. Josie had no commitment to work and there was nothing his boss could do about the resignation, but nonetheless Josie's stomach churned uncomfortably.

He wanted to get the resignation over as soon as possible. He went into his boss's office early in the morning and handed him the envelope with his resignation letter.

"This is not what I think it is," said his boss in a surprised tone.

Josie laughed uneasily. Managers always seemed to have a mysterious ability to know when they were being handed a resignation letter.

"Yes Dan, it is. I am resigning." Josie felt the need to apologize. He worked for Dan for over 8 years and it seemed like a crime to be leaving. "Sorry Dan. I have really enjoyed working here and working with you. It's just for personal reasons."

By now Dan was reading the letter. "This is a joke right," he said.

Dan's word's made Josie's stomach tighten into a knot and his face blushed red. It suddenly occurred to Josie that he did not know which letter Miss May had given him. He did not know if it was the serious letter that he wrote or the playful letter about how he was leaving to serve a Mistress and worship women.

Josie's knees weakened. He was starting to panic when Dan said, "I mean I can't believe you are actually resigning. We are really going to miss you around here."

"oh...ah...yeah...Thanks Dan. I'm going to miss working here," said Josie. He could tell from Dan's reaction and tone that he was reading the normal letter. Josie's panic disappeared as quickly as it came.

Josie spent the next half hour in Dan's office answering questions and discussing the resignation. Finally Dan conceded, "Well I guess if you've already made up your mind about moving away, there is nothing I can do here to make you stay. I'll just have to wish you good luck."

Josie felt relieved when he walked out of Dan's office. He went right to his own office and texted Miss May and Mistress Sarah, "Just left my bosses office. The resignation is official."

Miss May responded immediately. "Way to go kitty-kat! Feels great doesn't it? I will have a nice reward for you when you get home. For now your treat will be to stroke Joe's cock. Go into the bathroom, pull your pants down and play with your man's cock. Get Joe right to the edge and then stop. Wait one minute and do it again. This time when Joe is on the edge, squeeze out some cum and lick it up. Enjoy the creamy treat pretty kitty. I know it's what you want."

Josie's 'clittie' throbbed between his legs just from reading the text. He immediately went to the bathroom and followed May's orders. Someone was at the sink washing their hands but Josie did not care. He went into a stall and quietly stroked Joe's cock, getting himself right to the edge. Josie's urgency to follow May's orders and lack of nervousness in doing a perverted act in a public bathroom with others around were proof that Mistress Sarah's training and conditioning were effective. A serious transformation had already occurred within him.

After a short rest, Josie took himself to the edge again. He squeezed out a few dribbles of cum onto his fingers and licked them up. The taste was all too familiar. He felt dirty and slutty. These emotions were comforting to him. The resignation of his job was starting to sink in. Another connection to his normal life was being severed and he was excited by it. He was standing in his work's bathroom in panties and stockings, with 'Joe's' cock in his hands and he felt good about.

A strong desire was quickly growing inside to want to be dirty and slutty. He wanted Miss May to make him do all sorts of perverted things. He was unprepared for this strange emotion. He wanted to cum bad. He texted Miss May, 'I want to be your dirty slut. Please make me do slutty things. Please let me cum!"

Miss May texted back, "Calm down slut. Control yourself. See you tonight. Hurry home."

Josie was disappointed that Miss May did not want to play. He pulled himself together and went back to work. The end of the day could not come soon enough. At 5:00 sharp he raced for the door and headed home.

Miss May greeted Josie at the door and she was a glamorous sight. She spent the day at the salon and went all out. Her short hair was styled in waves to give her a cute and sassy look. Her face was painted to perfection and shined with beauty and her pink nails matched her pink glossy lipstick. She wore a tight black dress with foil highlights that added a shimmery wet look. The dress hugged her curves in all the right places and stopped at her mid-thighs. A small triangle of see-thru lace went from above her bust to her neck, with two straps that tied around her neck. The dress was glamorous and bordering provocative.

Josie practically drooled at the sight of her. "You look breathtaking," he said.

Miss May could not contain her smile. She glowed as she said, "Thank you Josie. This is a day to celebrate. Let's go have dinner."

Josie was already dressed in a suit so there was no need to change. Miss May had made reservations at the Devone Seafood Grille, an upscale restaurant in the city. Miss May and Josie both enjoyed a delicious meal and expensive wine as they celebrated Josie's resignation. After dinner, they headed to a nearby nightclub to enjoy drinks and dancing. Miss May was a bartender and knew her drinks well. She had fun ordering different variations of drinks for Josie to try. She was careful not to give him too much as she did not want him to be drunk for her planned evening event.

All-in-all it was a fun night for Josie. He enjoyed dancing and spending time with Miss May. While they danced, Miss May enjoyed sneaking her hand down to his cock and rubbing it until he got an erection. Then she would tease him further by rubbing her ass against his hard cock. Josie was enjoying the fun and was a bit surprised at how normal the night was. Miss May had maintained a dominant role with Josie, but other than that it was almost like a date. They even kissed a few times on the dance floor. He wondered if this was part of his gift. Perhaps this was his last night to spend time with a woman as 'Joe', even though he was wearing panties and stocking underneath his suit.

When they arrive back at Josie's apartment, Josie, thanked Miss May for a wonderful night.

"The night is not over sexy," she said with a devilish smile. "Come with me."

May grabbed both his wrists and pulled him back to the bedroom. In the bedroom she stripped him down. At the sight of his panties and stockings she smiled and said, "mmm. So sexy Josie." She rubbed her hands over the silk triangle that barely covered his hard cock. Through the silk, her fingers traced the outline of his cock up and down and up and down. Josie's body shuddered at the wonderful feeling.

"Does that feel good princess," said Miss May in a seductive and teasing tone.

"Yes Mistress," replied Josie.

"I bet you already want to cum, don't you?"

She was right of course. All the teasing and torment over the last few days had turned Josie into a weak ball of horniness. After just a few strokes of her fingers he was feeling the urge to cum. "Yes Mistress. You're making me feel so good."

Miss May laughed and ordered him onto the bed. She commented, "We'll leave your lingerie on. You look so sexy in them."

Miss May then proceeded to tie Josie down. His wrists were tied to the head board and his ankles were tied to the base of the bed. She did not tie him spread-eagle. She preferred to have him in a more relaxed pose with his hands straight above his head and his legs just about shoulder width apart.

Josie's eyes followed Miss May as she slowly walked around the bed admiring him. The click of her heels on the wood floor echoed in the room. Her hand traced across his chest and stomach, which sent chills through his body and caused his hard cock to twitch against the panties. Miss May was not pleased with the confinement of his cock. She pulled the panties down to his thighs, freeing his hard cock.

"Much better," she said as she stared at his throbbing cock.

She looked incredibly sexy in the tight shimmering dress. "You look amazing Mistress," complimented Josie.

Miss May smiled on the inside. To Josie she maintained a firm controlling image. "Of course I do slave." She laughed seductively. "You're in love with my body, aren't you slave?" Miss May swayed her hips side to side in a slow and sensual rhythm. She slid her hands from her waist up to her breasts. "You want to suck on my perfect breasts don't you?"

"Yes Mistress."

Miss May stood on the bed above Josie's head giving him a perfect view of he black satin thong panties. Then she teased, "Do you like what you see Josie? Do you want to taste my sweet pussy? Do you want to lick my beautiful ass?"

"Yes Mistress."

Miss May laughed at his response. She sat down on his chest and nonchalantly sighed, "Of course you do slave."

Josie was staring right at her crotch. Her dress was so short that it cinched up to her waist when she sat on his chest. She managed to wriggle out of her panties. She slid them off her legs and dropped them onto his face. Josie inhaled, trying to take in as much as her scent as possible.

Miss May laughed. "You're pathetic," she mused. "Here let me help you." She spread open the panties and pressed the crotch against his face. "There you go slut. Get a nice big whiff."

Josie inhaled deeply. The smell of her pussy was much stronger now and he loved it. Miss May held the panties firmly over his nose. "That's it slave. Smell it. You are so easily aroused slave. Just smelling my panties all day would make you happy wouldn't it?"

"Yes Miss May," mumbled Josie into the panties.

"such a slut," laughed Miss May.

Miss May let Josie continue to smell her panties while she retrieved a dildo. "I've got something special for you slave. It's part of your gift tonight." She waved the dildo over his face. "I know how much you've love to have your pussy filled."

Miss May lubed up the dildo and slowly pushed it into his ass. As the dildo filled his ass the thoughts of a normal night that entered his mind earlier in the evening drifted away. No normal man would be lying in bed in panties, stockings, and a garter belt, with a dildo in his ass. This didn't bother Josie at all. In fact he loved that it was not normal. The fullness in his ass was a welcome pleasure.

Miss May pulled her panties away from his face and looked into his eyes. "How are you doing slut?"

"Very good. This is a wonderful gift."

Miss May smiled. Her hand lightly caressed Josie's cock. "Oh, this is not the gift Josie. You are going to really love the gift." The light stroking was putting Josie into a wonderful erotic trance. He wanted to know what his gift was but Miss May changed the subject. "Such a big clitty you have darling. Let's rub our clitties together, shall we?"

Miss May sat with her pussy on top of Josie's cock, pressing it against his stomach. Her pussy was cleanly shaven for the special night and Josie could see that her swollen lips were molded around the sides of his cock. Her pussy was hot and wet and it felt incredible pressed against his cock. Miss May slowly moved forward so that her wet pussy glided along the under-side of his cock all the way up to the tip. Josie let out a moan.

Miss May teased, "Did that feel good princess? Do you like when I rub my pussy over your clittie?"

"It feels incredible," moaned Josie.

Miss May slowly slid backwards all the way down to his balls. Josie let out another moan. Miss May giggled. She paused for a few seconds and the slowly slid up to the tip again. Miss May repeated this again but at a faster pace. Josie could not stop moaning. It felt so good that his natural instincts kicked in and he thrust his cock against Miss May. This proved to be a big mistake. Miss May instantly slapped his face hard. The sting to his check shocked him. He forgot how cruel she could be.

"Do not thrust slave," she yelled harshly. "Remain still!"

"Sorry Mistress," apologized Josie. Her slap was harsh and somewhat cruel but Josie loved it. It put him in his place and made him feel even more helpless and submissive. There was something strangely erotic and sexy about the way she instantly subdued him.

Miss May started sliding up and down his cock again. Josie focused on remaining still. Miss May's voice changed back to sweet and seductive. "Feels so good, doesn't it princess? It feels good for me too. I bet you want to cum right now. I bet you want to feel your cock inside my pussy, don't you?"

"Yes Mistress," whispered Josie.

"I want to feel it too Josie. Maybe just a little."

Josie could not believe her words. He was surprised that she used the word cock instead of clitty. He was even more surprised that she might actually let his cock inside her. For a second he thought she was just teasing him but then she lifted herself up and held his cock straight up so that the tip was positioned just below her swollen pussy.

Josie watched the tip of his cock disappear into her hot pussy. The tight warn wetness around the most sensitive part of his cock sent waves of pleasure through his body. Her pussy was inviting and he wanted to thrust in deeper so bad but the warmness on his cheek was a reminder to remain still.

Miss May could see the struggle on his face. She lifted herself up and let his cock fall onto his stomach. She laughed cruelly. "You know it's a rare privilege to let a sissy's cock inside the pussy of a Goddess, don't you?"

"Yes," whispered Josie. "Thank You Miss May."

"Let's try it again sweetheart."

This time Miss May pushed down further allowing almost half his cock inside her. She paused for a second or two and then slowly lifted herself up. Josie's cock was so sensitive he could feel her pussy lips sliding along his cock as she raised herself up. It had been months since his cock had felt the inside of a pussy. The feeling was incredible.

"That feels so good Miss May," moaned Josie.

"This is your gift sweetie. Tonight I will allow your cock inside of me. Do you think you can handle it?"

"Not without cumming," admitted Josie.

The words were honest but Josie regretted saying them as soon as they came out of his mouth. He thought he blew his opportunity. However, Miss May just laughed. "You are so weak sissy. Let's let your cock rest for a moment. It may be the last time your cock is allowed inside a real pussy so I want you to at least last a minute or two"

Miss May moved forward and sat on his stomach. She undid the strap to her dress and let her top fall. Josie enjoyed the sight of her perky breasts and hard nipples. She leaned forward and Josie eagerly licked and sucked her nipples. Josie's lips were warm. The combination of his warmth and his wet tongue caused sparks of pleasure to shoot through May's body.

Miss May was enjoying her powerful position. It was a thrill to have Josie beneath her, tied up, helpless, and on the brink of orgasm. It was a thrill to see him struggle to maintain control and to not orgasm. She knew that she could send him over the edge at any time and that he was so weak that she could make him cum on command. This was a thrilling and arousing power. Soon it was Miss May who was struggling not to orgasm. Her pussy grew wetter and hotter. She could orgasm if she wanted to, but she chose not too. She wanted to save her orgasm for just the right moment.

Miss May raised her tits a few inches out of reach of Josie's mouth. In doing so, her body edged backward just enough that her pussy rubbed the tip of his cock. Josie moaned. Miss May teased, "awww...does my pussy feel good? You want to cum so bad don't you sissy? Do you want you cock inside me again? I bet you want to cum in me. Do you think I'll let you cum in me?"

Josie was so aroused and confused from the teasing. He loved everything that was happening to him. He did not know what to say. He did not know how to answer, afraid that he might say the wrong thing and upset Miss May.

Miss May pushed backward and the tip of Josie's cock pushed into her sopping wet pussy. Instantly his eyes closed and a moan escaped his lips. Miss May moved forward again and giggled as her pussy released his cock. Then she said in a seductive but commanding tone, "Pretty Josie, the next time your cock is in my pussy I am going to take all your cum."

Josie's eyes opened in surprise and delight. 'Was she really going to let him cum inside her,' he thought.

Miss May read his thoughts, "That's right slave, you are going to cum inside me. My pussy is going to milk every last drop of man cum out of you. That is your gift slave. When I take the last drop, you will forever be a sissy slave to Mistress Sarah and me, do you understand?"

"Yes Mistress," replied Josie. He completely understood and he loved it. Josie loved that his gift was a ritual signifying his new life. He knew that although Mistress Sarah was not there in person, she was the one who orchestrated the whole night and the ritual that was taking place. Mistress Sarah was a natural genius at the mental aspects of seduction and domination, which was why Josie could not escape her power. It was the same power that kept Miss May, Mill, Nellie, and Julie drawn to her. It is a wonderful power that no one wants to escape once they experience it.

Josie was completely under Miss May's spell but just like Josie, May was a pawn in Mistress Sarah's game, following her orders, carrying out her supreme plan. She used very specific words to emotionally dominate Josie. Josie's mind clung to these triggers - 'I am going take your cum,' 'My pussy is going to milk every last drop of man cum out of you,' 'you will forever be a sissy slave.'

Although Josie acknowledged that he understood all this, Miss May said, "Repeat it for me slave. I want to hear you say it. Say 'Miss May is going to take all my cum and when my last drop of cum is milked out I will forever be a sissy slave to Mistress Sarah and Miss May.' Say it now slave!"

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