Discovering Mistress Sarah's World Pt. 03

The dressing up seemed fun until Josie saw himself in the mirror. He thought he looked silly. With more make-up he might at least pass as a girl. He lightly protested, "I'd rather have the pretty girl look."

Miss May giggled at his embarrassment. It was the reaction she hoped for. "Aww. That's so cute princess. I know how bad you want to be a girl but you've got to grow into that. Right now you're just a sissy. Be the best sissy that you can be and then maybe you can progress to the next stage of your training. Understand?"

"Yes," replied Josie.

Josie understood what she was saying but his mind was swirling from all the mind games that Miss May and Mistress Sarah were playing with him. He wanted to progress to the next stage of training because he was having fun and he was in heaven being under their control. What made his mind flip was when Miss May said how much he wanted to be a girl. Josie questioned himself; did he really want to be a girl or was being a girl just better than being a sissy and that's why he wanted to be a girl?

His mind was both confused and excited. He enjoyed wearing the lingerie and silky dress. He actually felt sexy in his lingerie. He was even impressed at how good his legs looked when they were shaved. Deep down Josie was looking forward to being completely feminized. These thoughts would have never occurred to him prior to meeting Mistress Sarah. In a matter of months she had changed who he was.

Even his fantasies had changed. His fantasies were now all centered around being feminized and being Mistress Sarah and Miss May's play toy and servant. As Josie contemplated all this and realized how much he had succumbed to the power and control of his Mistresses, a strong wave of arousal washed through his mind and body. He was in a great place.

Josie's thoughts were interrupted by a wet sensation on his neck. Miss May sprayed a small amount of perfume on Josie and then herself.

"Now you smell nice and pretty Josie," announced Miss May.

Chapter 9: Meeting Mill and Ayla

May took Josie's hand and led him downstairs to the living room. Mistress Sarah was just finishing a conversation on her cell phone. She hung up and said, "Perfect timing girls. Millicent and Ayla will be here any minute."

Mistress Sarah and May sat down in the living and ordered Josie to get each of them a glass of wine. A chilled bottle of white wine and several wine glasses were already set out on the kitchen counter. Josie uncorked the bottle, filled two glasses half full and carefully brought them over to the girls.

Before sipping her wine, Mistress Sarah commented, "You make a good sissy maid even though you are not in a maid's outfit. That day will come soon though."

"You'll look so cute as a French maid," added May.

"Thank you," replied Josie, doing a small curtsey for the girls. The thought of dressing as a French maid sent an exciting chill through his body.

"You can practice tonight princess. Be a good little maid for my friends o.k.," ordered Mistress Sarah.

"Yes Mistress. I will be glad to serve them. I will make you proud."

"I know you will dear."

A knock at the door interrupted their conversation.

May smiled and said, "Let's see what you got Josie. Go see who's at the door pretty maid."

Josie's heart beat quickened. He nervously looked over at Mistress Sarah, almost hoping she would over-rule May's order. He was not ready to show his sissy side to the outside world. Mistress Sarah enjoyed the scared look on her pet's fast. It was fun toying with him and pushing his limits.

She was quick to respond to his questioning look. "Go on slave. Do not hesitate when given an order. Hurry now. Don't keep my friends waiting."

Josie headed toward the door nervously. In the grand scheme of things, what he was doing was not a big deal. After all Ayla and Millicent were expecting to see a sissy. It was all the unknowns that frightened Josie. Many thoughts ran through his mind. What if it was someone else at the door? What if there were other people walking by? Would Ayla and Millicent laugh at him?

He had little time to ponder the consequences. He opened the door blushing and nervous. Two beautiful girls stood before him, smiling and taking in the sight of a sissy dressed in a pink and white dress, a brunette wig, and a touch of make-up. Josie quickly introduced himself, saying whatever came to mind.

Shyly he said, "Hi I'm Josie. Welcome to Mistress Sarah's house. Please come in." His nervousness was evident in his wavering voice.

Both girls could not help but giggle but their giggles were followed by a warm welcome.

"Hi Josie. I'm Ayla. Sarah has told us all about it you. It's so nice to finally you meet you in person." Ayla was tall with a golden-brown skin tone. She had a beautiful exotic look.

The other girl looked several years younger than Ayla.. "I'm Mill," she said cheerily. Her eyes lit up as she stared at Josie. "I just love your pretty dress Josie. The lacing around the hem and sleeves is the cutest!"

Mistress Sarah and May joined the group just inside the doorway. Mistress Sarah beamed like a proud owner, "Isn't she adorable in her sissy dress. The shiny silk is so sexy and pink really suits her well."

Ayla leaned forward and placed a hand on the apron that was embroidered in white silk. "I love this apron. The bows around the bottom are so pretty."

"Turn around princess. Model your dress for Mill and Ayla," ordered Mistress Sarah.

Josie turned slowly in his dress. He did not expect this much attention from the girls. His nervousness and embarrassment washed away as they showered him with pretty feminine compliments. Josie noticed that the girls did not acknowledge him as a male in any sense. Right from the start they referred to him as 'her' or 'she' and this excited him for some unknown reason.

Josie's senses and erotic nerves suddenly came alive. As he slowly circled, he felt his stockings rubbing over his skin and he felt his cock straining against his soft frilly panties. His arousal grew making him more aware of the plug in his ass. Once his mind re-connected to the wonderful sensation of the fullness in his ass, it sent his arousal into overdrive. Josie was amazed at how quickly he became fully aroused simply from showing off his dress.

After Josie did a complete circle, May said to Ayla and Mill, "We did her nails also. Show them Josie."

Josie held up his hands, showing off his pink nails through the white lace clothes. Both girls admired them and complimented Josie on how well the pink color looked on him. When all the fawning and admiring finally came to an end, Mistress Sarah ordered Josie to pour two glasses of wine for the new guests. Josie walked away feeling more confident and excited about his sissy state. He was eager to please all the girls.

Josie obediently delivered the wine to the girls, who were now seated at the dining room table. They were chatting, giggling and working on some type of craft. The girls kept Josie busy with various tasks such as retrieving scissors and glue, refilling wine glasses, and bring out snacks. When he was not carrying out a task he was made to stand by the side of the table, hands behind his back, attentive and waiting for the next order.

With a few glasses of wine in them, the girls became giddy and playful. After some giggling, Mill said, "Josie pretty, come over here. May told me you've got some cute undergarments on. I want to see them."

"Yes Miss Mill." Josie walked over unsure what to do. He looked at Miss May for direction.

"Go ahead pretty. Take off your dress."

Mill jumped to her feet taking an interest in Josie. "I'll help you," she said with a smile.

Mill unzipped the dress and helped Josie pull it over his head. The whole night was such an erotic tease for Josie that he could not control his arousal. His hard cock was clearly visible in the frilly panties.

"See what a horny bitch she is," commented Miss May. "She just loves being all pretty and prissy."

Mill reached around and squeezed his cock. Josie's body tensed with pleasure at the unexpected thrill. She rubbed it lightly though the panties. "What a nice big clitty you have, cooed Mill."

Joe sensed a deep lust in her voice. His eyes closed as he sank into oblivious pleasure.

"Carful Mill," warned Mistress Sarah. "She might just explode. Josie's new to all this and is very weak."

Mill whispered so that only Josie could hear her, "You are weak. Mmmmm. I like that." Then she gave his cock one last squeeze.

Josie was standing close to Ayla so she got a good view of him. She focused her attention on his stockings. "You have very sexy legs Josie. I'm jealous."

Miss May said to Ayla, "Aren't the big bows at the top of her stockings so sexy?"

"Yes, they are adorable and very bridal. We have a blushing bride," giggled Ayla.

"She's my bride," laughed May. "My little bride is going to get her first good fucking tonight. Show them your tight ass Josie."

Josie turned around. The girls commented on how nice his ass was and they could not resist touching it. Josie felt their hands rubbing and cupping his ass cheeks. Mill's hand slid between his legs rubbing his balls and the slid up the underside of his cock. All the touching and teasing was driving him wild.

Josie could sense that both girls were excited and turned on from admiring and touching him. This fueled his arousal even more. Mistress Sarah and May joined in on the fun. Mistress Sarah pulled Josie's panties down to his thighs, exposing his ass. "Isn't that beautiful," she announced.

Mill pressed on the plug that was in his ass, sending an erotic spark through his body. "You didn't tell us that her pussy was full. No wonder why she's all horned up."

May reached around and started playing with the plug in his ass. She gently fucked him with the plug. "We're getting the slut warmed up for later tonight."

Josie moaned at the pleasure. He was sinking deeper into an aroused and feminine state. "That's feels incredible Miss May." His cock was twitching and dripping, which did not go unnoticed by Ayla.

Ayla rubbed her hand over the top of his cock and then massaged the dripping cum along his shaft. In just a few seconds his cock was shiny and wet all over. For a moment all four girls had their hands on Josie, caressing his ass, balls, and cock. It felt amazing and Josie did not want it to stop but he knew he could not last and he knew he was not allowed to cum.

"Please stop," he moaned. "I'm not going to last much longer."

The girls giggled and their hand slowly retreated from his cock. Mill's finger lingered a few seconds. She was the last to touch him and she pulled away not a moment too soon. Another second and Josie would have surely exploded. He was teetering on the edge of orgasm. The girls watched with delight as his cock twitched. His eyes were closed and it was clear that he was concentrating hard to not go over the edge.

There was not a dry pussy in the room. Josie's struggle was what brought all the girls together. Mill, Ayla and even May were drawn to Mistress Sarah because of her natural ability to craft situations that exploded with pure arousal and kink. To see Josie enveloped in uncontrollable stimulation and teetering on the edge was sheer ecstasy for the girls.

With the smell of sex in the air and with four pussies getting wetter by the second, the situation was on the verge of bursting into a sex-fest. Mistress Sarah was not ready for that yet. She had a plan for Josie and she wanted to stick to it. It was hard for her to not get carried away herself but she mustered up the strength to take control of the situation.

Chapter 9: Sissy Assignments After Josie's cock stopped twitching and his breathing became less laborious Mistress Sarah announced, "Well I think that's enough teasing for our pet now. We've got to hit the clubs so Josie can get started on her assignments."

"Assignment," questioned Josie.

"Yes precious," replied Mistress Sarah. "The girls and I have come up with some wonderful assignments for you to help with your femme training."

"We even made you a cute diary for you to track your progress and express your feelings through the transformation," said May. "Take a look."

May held up a small book. On the cover, in pink glitter, it said Josie's Diary. A silver princess crown and wand accented the cover. Josie looked at it and realized the diary was the craft that the girls were working on. Seeing his female name on the cover added a new sense of reality to what was happening to him.

Ayla questioned, "Isn't it cute Josie?"

"Yes, thank you. It's very pretty." Josie was impressed at their thoughtfulness.

Mistress Sarah then explained his assignment. "Josie sweetie, on the first few pages of your diary we have started a few entries in your diary. While we are out tonight I want you to finish the thoughts that we started. Be sure to fill all the blank pages in between entries, o.k. princess?"

"Yes Mistress," replied Josie.

"Some of the items you can start on right away. For example, the first page in your diary says 'When I first saw Mistress Sarah I felt....'

You need to write a paragraph to complete that thought. You already know enough to do that. However a few pages back the entry says

'I went through Mistress Sarah's panties and tried them on. My three favorite pairs are....'

Now you have not done that yet so obviously you can not complete this page yet. What do you think you need to do to complete this page?"

Josie said the obvious answer , "I need to go through your panty drawer and try on your panties."

"You got it! That is your assignment tonight Josie. Tonight is all about discovering the feminine world and the girl within you. I want you to explore through all my stuff while we are out. In order for you to blossom into womanhood you need to discover and experiment with girly things."

"Girls don't become women overnight," added May. "The same applies to sissies. Mistress Sarah and I have nurtured the feminine desires within you. Now you need to let Josie run wild with those desires and discover the wonderful world of womanhood. We are much more sensual then men. A woman's world is full of pretty scents, and soft fabrics...."

Ayla giggled and jumped into the conversation, "....and shades of lipstick and make-up.."

"...and let's not forget about pedicures, manicures, and pampering," chuckled Mill.

Everyone was smiling and having fun, including Josie. He was already starting to blend in as one of the girls.

Mistress Sarah continued explaining the assignment. "I want you to explore all those wonderful things. Go through my make-up, experiment with my lipstick and glosses and try on my panties, bras lingerie, skirts, dresses, and anything you can fit into."

Josie was becoming excited and aroused from his assignment. All these things seemed fun and exciting to do.

May added, "Don't forget about perfumes and lotions. I want you smelling pretty for me later. Fresh like a virgin for your fucking. O.k. Hun?"

"Of course," replied Josie in an erotic daze.

Mistress Sarah continued. "Nothing is off limits Josie. Explore it all. Take your time as your explore and discover these things Josie. Think only of your senses. Pay attention to the scents, pretty colors and delicate fabrics. Submerse yourself in this secret dreamy world one step at a time. Make notes in your journal. What things do you like? What appeals to you? What makes your nervous or uncertain?" Mistress Sarah smartly questioned, "Can you handle it princess?"

"Yes. Thank you for this wonderful assignment. This is going to be fun."

"Of course it will be dear. Everything about being a girl is fun. Once you enter our world you are not going to want to turn back."

"I'm already starting to feel that way," admitted Josie, somewhat surprised.

Each girl gave Josie a kiss on the cheek before walking out the door. Before Mistress Sarah left she gave Josie one final order, "Start with a bubble bath Josie. Spend 20 minutes soaking and thinking about how wonderful everything is right now. Then clean yourself up and go have fun."

End of Part 3