tagTranssexuals & CrossdressersDiscovering Mistress Sarah's World Pt. 05

Discovering Mistress Sarah's World Pt. 05


Chapter 13 Sinking Deeper Into The Feminine World

*** Prologue - Joe has made a trip down south to visit for the first time, his online Mistress. Over the past few years she has slowly feminized him with the help of Miss May. Upon his arrival at Mistress Sarah's house, she puts his feminization into full speed. He spends his first day is sissy clothes and receives his first strap-on fucking by Miss May. Part 5 starts the morning after his fucking. ***

Josie awoke in the morning wrapped up in a pink comforter. It was soft and comforting despite the fact that he had been sleeping on the floor in the hallway. He had been banished from the bedroom by the girls. After he had cleaned their strap-ons, he was told that it was girl-time in the bedroom and that he was still a sissy. He was sent to the hallway but he stayed close to the door listening to the sexual tones of Miss May and Mistress Sarah. However, exhaustion took over quickly. It had been a long day and the pegging by Miss May followed by his explosive orgasm had drained all his energy. There were several orgasms that occurred behind the closed door but Josie did not hear them because he had quickly drifted into a sound sleep.

When Josie awoke in the morning he unraveled himself from the comforter and admired the red silk night gown that covered him. The girls had dressed him in the gown before sending him to bed. It was a short and simple gown. Josie thought the shiny material looked incredibly sexy and feminine. He loved the feel of the smooth silk rubbing all around his body. His clitty started to swell as he became more aware of the soft sensation on his skin.

Josie remembered Mistress Sarah telling him that in the morning he was allowed to crawl into the bedroom and kneel by the bedside. If he was lucky, the girls would play with him. Not wanting to miss out on any fun, he crawled toward the door. The gown draped around his body as he quietly pushed through the door. He could feel a slight soreness in his ass, which served as a wonderful reminder of the pleasures that took place jut several hours earlier.

Josie crept towards the bed on his hands and knees in the quiet room. Mistress Sarah rolled over and in a hushed tone said, "...ahhh here comes our kitty." She beckoned him on. "Here kitty, kitty. Come on pretty kitty....hop up on the bed."

Josie hopped up and snuggled between Miss May and Mistress Sarah and greeted them. "Good Morning Mistress Sarah and Miss May."

They were both naked. He enjoyed the morning warmth of their bodies under the covers. He moved into a spooning position, facing Mistress Sarah. He was excited to be sandwiched between two naked bodies and he could not control his cock. It grew fully erect and pressed against Mistress Sarah's ass.

Mistress Sarah immediately turned and pushed Josie onto his back. She firmly grasped his hard cock and said, "This is not the feel of a pretty girl. It's getting in the way. We will have to something about it."

"Sorry Mistress," apologized Josie.

Then May reprimanded, "And what happened to that pretty girl voice? Greet us again with your pretty girl voice."

Josie hesitated for a moment, remembering how they laughed at him the night before. He wanted to sound more like a girl. He concentrated and with a raised pitch said, "Good morning Mistress Sarah and Miss May."

To his relief the girls did not laugh. Miss May said, "Better Josie, but it still needs work."

Mistress Sarah lightly stroked his cock through the silk nightgown and said, "Yes princess. You need to practice your girl voice. That's the only voice I want to hear from now on. Only prettiness comes out of those girly lips of yours, got it?"

"Yes Mistress," replied Josie with his girl voice. His cock throbbed in pleasure not only from Mistress Sarah's stroking but also from knowing that another part of his maleness was being wiped away by Mistress Sarah.

Miss May's hands rubbed over Josie's chest and found his nipples hidden beneath the silk. She rubbed and pinched them until they formed pointy tents in the night gown. Josie was not used to having his nipples played with. A new wonderful sensation tingled inside him. Mistress Sarah's words from the day before about taking his time and experiencing the sensations of womanhood echoed in his mind. He loved the womanly sensations he was feeling from his nipples.

"Very sexy nipples," complimented Miss May.

"Thank you," moaned Josie.

The girls continued teasing Josie's body, putting him a state of complete arousal.

Mistress Sarah asked Josie, "How is your pussy feeling? May gave you quite a fucking last night. Your inner slut was on full display."

"I am a slut," admitted Josie. "My pussy is a little achy, but it's fine. I had so much fun yesterday."

Mistress Sarah continued to lightly stroke his cock and explained, "It always hurts the first time your cherry is popped. That's part of being a girl. Tonight it's my turn to fuck you Josie. It will hurt again but eventually your body will learn to accept our strap-ons with full pleasure. Soon your pussy will be molded into a perfect fuck hole to be used solely for our pleasure. That is its ideal state, don't you agree?"

The future state which Mistress Sarah talked about excited Josie. Her words made him feel submissive and feminine. He wanted to be their fuck toy and slut. It was hard to maintain his female voice with all the pleasure running through his mind and body, but he managed to squeak out a girly sounding "yes Mistress."

For his compliance Josie was rewarded with Miss May's tits. She lowered her tits to Josie's lips. He took her nipple into his mouth and flicked his tongue over it. He could almost feel Miss May's body shudder with pleasure. "Good Girl," moaned Miss May.

Miss May moved her other nipple to his mouth and Josie enjoyed licking and sucking it just as much as the first one. He was in heaven being nestled between two beautiful girls, enjoying their bodies while they teased him. Mistress Sarah was playing with his cock with a combination of light strokes and long slow pulls. It was the perfect mix to keep him fully aroused without sending him over the edge.

When Mistress Sarah was certain that Josie was awash in arousal she commented, "This is what girls do in the morning. Isn't it fun? Aren't you glad to be one of us Josie?"

Josie could not argue with that statement. Everything that he had done since he arrived at Mistress Sarah's house was full of fun and pleasure. He did not want it to stop. Mistress Sarah and Miss May were showing him a whole new world and he was loving it. Joe was a long lost soul now. Only Josie existed and 'she' was one of the girls.

Josie's entire body shivered with pleasure from the confession he was about to make. His body tensed and his back arched as he fought off an orgasm. Josie confessed, "Yes I am glad to be one of the girls. This is so much fun. Thank your for bringing out the girl in me. You two are amazing."

Mistress Sarah and Miss May's eyes met and they both smiled calculatingly. There was so much emotion, arousal, and conviction in Josie's confession that they new their slave had mentally transformed into their slutty bitch. At that moment both girls shared a special thrill of knowing they had completely conquered him. He was not just a feminized boy anymore. They had much bigger plans for Josie. He was a toy for them to play with anyway they wanted. He was a slave willing to do anything they wanted.

Knowing that their slave had reached a perfect state of arousal and obedience, the girls stopped teasing his body. Miss May said, "We have so much more girl to bring out in you Josie. Today you will be completely transformed. Are you excited about it?"

"Yes Miss May."

"Well then we must get our day started. Mistress Sarah and I could go for a nice breakfast." Miss May instructed Josie to make bagels and cream cheese for Mistress Sarah and her.

Mistress Sarah slapped his cock and said, "and get rid of this too kitty. Tuck it between your legs so it doesn't get in the way. You can use a pair of my panties to keep it in place."

"Yes Mistress," replied Josie. He went over to her panty drawer and selected a pair of red silk panties.

As he walked out of the bedroom to get started on his breakfast duties, Miss May said to Josie, "Practice your girly voice too. While you prepare our breakfast say out loud over and over again, 'I am a pretty obedient girl slave.' Make your voice as girly as you can. I want to be greeted with a pretty voice when you serve my breakfast."

"Yes, Miss May. I am a pretty obedient girl slave," replied Josie with his feminine voice.

"Good girl," complimented Miss May with a small giggle. Then she kissed Mistress Sarah and said, "This is so much fun. Thank you for letting me play with Josie with you."

"There is much more fun to come my pet," said Mistress Sarah as she gently brushed her hand through May's hair and enjoyed the warmth of May's naked body pressed against hers.

In the kitchen, Josie was preparing breakfast and repeating 'I am a pretty obedient girl slave' over and over again. Each time he said the words out loud, he experimented with the pitch of his voice until he finally found a pitch that seemed naturally feminine.

Practicing his girl voice and getting the bagels ready distracted his mind enough for his cock to soften and shrink. Josie took the opportunity to tuck his cock back between his legs and pull on Mistress Sarah's panties to hold it in place. At that moment he felt a deep sense of submission and arousal. Having his manhood molded and forced into a pussy shape stirred up a strange pleasurable arousal inside him. His 'clitty' began to swell but was held back by the soft panties. He could feel its heat against his inner thighs. It was a wonderful new sensation. He wondered if girls experienced a similar sensation when they were aroused.

Josie heard footsteps coming down the stairs. He had planned on serving the girls in bed but they had decided otherwise. Mistress Sarah sat at the kitchen table in nothing but a pair of black boy shorts and Miss May wore only a white g-string. Josie was thrilled at how free-spirited the girls were by walking around the house almost naked. He could get used to this life quickly. He thought to himself, if this was how girls lived together, then being a girl was much more fun than a guy.

In his practiced girl voice he said, "Good morning beautiful Mistresses. Enjoy your bagels." He served them bagels and poured them glasses of orange juice.

Mistress Sarah complimented, "What a beautiful voice Josie. Come here darling and lift your gown for me."

Josie walked over to Mistress Sarah and lifted his gown up to his waist. Mistress Sarah rubbed her hands between his legs and said proudly, "Just like a girl Josie. Now I can play with your clitty the same way I play with May's. You are turning out to be a wonderful addition to our family Josie."

"Thank you Mistress," said Josie. He was excited and thrilled to be accepted by Mistress Sarah. He was also excited about having his clitty rubbed. It was very kinky and perverse to have his cock shaped in the form of a clitty and for Mistress Sarah to finger him like a girl. Lately it seemed that the more kinky and perverse things were, the more Josie like it. In Mistress Sarah's world, Josie was quickly discovering how much fun it was to be feminized.

Miss May was sitting across from Mistress Sarah at the table and was sipping on hot tea while reading Josie's journal. Josie blushed when he noticed her reading it. He could not recall everything he wrote the night before but he knew that in the height of his arousal, he wrote many embarrassing thoughts about himself; Thoughts that would make him ashamed and humiliated if anyone in his 'real' world read them.

Miss May giggled as she read entry after entry in the journal. "Josie, it sounds like you had a great time playing with all Mistress Sarah's girly stuff last night."

"Yes, it was fun," admitted Josie in a shy voice.

"Better hide your furry stuff Mistress Sarah. Josie has taken a liking to your fur panties."

"That's my girl," exclaimed Mistress Sarah. "We'll have lots of fun with fur Josie. It really makes your clitty tingle, doesn't it?"

"Yes Mistress. I love the soft feel of it."

"Mmmm. I love have it feels to princess. We'll have to buy you a nice set of furry lingerie princess."

Miss May read several other passages from the journal, out loud to Mistress Sarah. Hearing his words read out loud about how he liked panties and what his favorite lipstick and perfume were, made Josie blush. When he wrote those things, he was aroused and in submissive and feminine state of mind. His thoughts seemed sexy and fun at the time. Now, a day later, hearing someone else read them, embarrassed Josie. Knowing that those feminine thoughts came from him made it seem so silly. He felt like a pervert and a sissy. It was something that he would have never fathomed doing prior to meeting Mistress Sarah and Miss May.

As much as it embarrassed and ashamed Josie, he knew he would continue to do these things. He knew that Mistress Sarah and Miss May were systematically feminizing him. Little-by-little his manhood was being stripped away and he was being molded into a feminine slave. Josie had never wanted to be feminized but over time Mistress Sarah helped him discover a deep arousal and pleasure from this transformation. Being controlled and manipulated through Mistress Sarah and Miss May's seductive powers was thrilling for Josie. He was addicted to their control and he knew that he would continue down the path that they had planned out for him.

One of the greatest powers of Mistress Sarah was her ability to wash away the embarrassment and make it exciting for Josie. "I am so proud of you Josie," she said with pride. "Your journal entries are so honest, open, and thoughtful. It is exhilarating to read about your wonderful transformation. I can see that your training is working and that pleases me very much."

Josie smiled at Mistress Sarah's compliment. He was glad that she was pleased.

Mistress Sarah encouraged him on. "Josie, it's important that you continue to write about what you are experiencing. It will help you discover more about yourself and will provide a great history of your transformation. I want you to write about last night. Describe how exciting it was to have Miss May fuck you for the first time in your pussy."

Miss May smiled devilishly from across the table. She slid the journal towards Josie. "Yes, it was very intense and exciting Josie. Write lots of good things."

Josie sat down at the table. "Thank you," he said. "I will write all about it."

The girls excused themselves from the table, leaving Josie alone to write in his journal. Josie's clitty was already starting to throb in its tucked away position as he began to re-live in his mind, Miss May's wonderful pegging. He put pen to paper and wrote all about it in his journal.

Chapter 14 Blowing Josie's Mind

It was late Saturday morning when Josie descended the steps of Mistress Sarah's house wearing red satin panties, black fishnets stockings, and red heels. Josie was still getting used to heels. He had to hold onto the rail of the steps and walk slowly. He was fresh from the shower and clean-shaven. His lips were painted a bright glossy red.

Miss May had gone off to work for a few hours so it was only Mistress Sarah who waited for him in the living room. She sat on the couch with her legs crossed, waiting for Josie to approach. Mistress Sarah was dressed in a simple summer outfit that consisted of a low-cut tank top and short skirt.

As Josie approached, she smiled with delight. "The lingerie I picked out for you looks amazing Josie. The red really brings out your inner-slut. Feeling slutty, aren't you princess?"

Simply dressing in the soft feminine items had an arousing effect on Josie. Mistress Sarah's words ignited more arousal. Josie's cock was still tucked between his legs beneath the sating panties. He was wearing a thong and the thin string barely held his cock in place as it swelled as much as possible in its bent position.

"Yes Mistress. I am in a slutty mood. I want to be slutty for you," said Josie with complete conviction. He was looking forward to being her slut.

"Good girl. We will have lots of slutty fun." Mistress Sarah admired his lips. "You did a nice job with your lipstick princess. Your lips look so sexy and kissable. They are a nice slutty color to. It looks good on you."

"Thank you Mistress."

Mistress Sarah uncrossed her legs and leaned forward. She grasped his panties and pulled them down to his knees. Josie's cock came free and Mistress Sarah watched with amusement as his cock quickly straightened and grew erect right in front of her, without being touched at all.

Mistress Sarah leaned back again and crossed her legs. She smiled up at Josie and said, "That's what I love about you pretty. You're always so horny and eager to please." Mistress Sarah patted the couch cushion next to her and said, "Come sit Josie."

Josie sat next to her, his panties dangled at the top of his knees, his cock was fully erect. Mistress Sarah instructed, "Look between your legs Josie. What do you see?"

Josie looked down and saw his hard cock pointing up at him. He was in feminine mode and so he said, "My clitty Mistress."

"No..no..dear," said Mistress Sarah with a tone of laughter. "That is much too big and vulgar looking to be a clitty. Tell me what it really is Josie."

Josie was a bit confused. "My cock," he said.

Mistress Sarah corrected him, "It is a cock Josie, but not your cock. Understand?"

Josie giggled a little embarrassed, "ah..yes Mistress."

"Stare at it Josie," instructed Mistress Sarah. "Look out it and see it as not your cock. It is foreign to you."

Josie looked down as his cock and imagined that is was not his. It was a strange thought.

"Who's cock is it Josie," asked Mistress Sarah.

"Your cock Mistress," replied Josie.

"Well, I do control and own it Josie but it is not my cock. It is your silly man's cock Josie."

Josie looked over at Mistress Sarah with a confused look. She continued, "The silly man that you brought with you. It is Joe's cock, right Josie?"

"Yes Mistress," replied Josie, still trying to fully understand where she was going with it.

"Look at your pretty fingers," ordered Mistress Sarah. "Whose hands are they?"

Josie held is hands up. The pink nail polish that was put on the night before still shined like new. They were definitely feminine looking. He thought he understood this game that Mistress Sarah was playing but he was not sure. "Josie's hands," he said with uncertainty.

Mistress Sarah confirmed his answer, "That is right Josie. I want you to take your man's cock into your hands Josie. Squeeze it and tell me how it feels. Go on dear."

Josie gripped his cock as instructed. He had touched his cock many times before, but this time was much different. He was now paying close attention to what if felt like. "It is warm and hard Mistress. It's hard, yet a bit supple."

That's right Josie. Your man's cock is so hard and warm. Rub his balls Josie."

Josie rubbed his hand along his balls. It sent chills through his body. "His balls are very smooth," observed Josie.

"Yes. It's good that you noticed that Josie." Mistress Sarah was also pleased that he spoke about it in the third person. He was already disassociating himself from his cock. "Now stroke Joe's cock Josie. I think that will make him very happy, don't you."

"Yes," replied Josie. He started stroking his cock slowly up and down.

"Good girl. You are my pretty little girl slut right now, aren't you dear? You are dressed in slutty stockings and a naughty red thong. You have fuck-me pumps on and your lips are a slutty red color. Your pretty girl voice is even sounding more feminine and natural. Stare at your pink fingernails as you stroke that cock Josie. See how your pretty fingers are stoking that strange man's cock."

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