Discovering Mistress Sarah’s World Pt. 02

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Chapter 4 : Introducing Miss May!

Miss May’s arrival seemed sudden and quick to Joe. He heard the door close downstairs. Then there was the sound of somebody running up the steps. The bedroom door flung open and before Joe could look up to see anything, he heard an excited voice exclaim, “kitty-kat!”

“I think someone is excited to see you,” laughed Mistress Sarah.

Miss May quickly approached the bed. “Stand up kitty-kat and let me see you.”

Mistress Sarah had put Joe into a calm and placid state of mind. It took him a few seconds to adjust to the rush of excitement that had entered the room. He slowly rose from the bed. Miss May instantly hugged him.

Joe enjoyed the warm welcome. For a moment he felt like he was hanging out with an old friend. However, when her embrace ended and he was aware that she was fully clothed and he was standing before her in a teddy and stockings and sporting a hard cock, he reverted back into submissiveness. He wanted to come out with confident and suave greeting, but instead he shyly said, “hi,” to Miss May while his cheeks blushed slightly and his eyes darted downward.

Miss May stood back and took in the sight. “Look at you kitty. You’re so pretty in your pink teddy and stockings. Such a cute little kitty-kat bell too.” Miss May jingled the bell around his neck with her fingers. Then she looked down at his hard cock and said, “….and your clitty is so big. Excited to see me are, you?”

Miss May reached out and firmly squeezed his cock a few times. It was a welcome sensation that reverberated though his entire body. Before Joe could respond, she ordered, “Turn around kitty-kat. Let me see that ass of yours.”

Ever since he met Miss May online, she had talked about pegging him in this ass. Joe had never experienced this before but over the past few months, Miss May had nurtured a strong desire within Joe to be taken by her strap-on and so it was thrill for him to turn and show her his ass.

Joe felt a push on the center of his back. “Bend over slave,” ordered Miss May.

Joe’s hands braced on the bed as he fell forward so that he was bent forward, with his ass on display. Mistress Sarah sat to the side of him on the bed and watched with amusement. Miss May kicked her foot against the inside’s of his ankles and ordered, “Spread ’em slut.”

Miss May pulled the fabric of the teddy to the side and gazed at his ass. “Yummy. Such a tight pussy Josie. I can’t wait to peg you bitch. I bought a nice new strap-on just for you kitty-kat.”

Joe’s ass was tingling and ready for her strap-on. This was a moment he dreamed about for months. Joe begged, “Please fuck me with it Miss May!”

Mistress Sarah interjected, “Calm down you two. We’ve got some more work to do on you Josie. You want to be nice and pretty for your first fuck date don’t you?”

“Yes Mistress.”

“Of course you do slut.” Mistress Sarah turned her attention to May. “May, there’s a sexy outfit for you in the other room. Hurry and put it on so you can help me transform Josie.”

“You got it Miss S,” replied May happily. Then she quickly headed off to get dressed.

Joe endured more teasing of his cock until Miss May returned. Miss May entered the room dressed in a black latex mini skirt, latex halter top, and high heels. A thin latex collar wrapped around her neck. Her hair was pulled back into a tight bun. One glance at her dominant and sexy look and Joe felt himself becoming weaker and more submissive.

“This is not fair,” commented Joe in a light hearted tone. “You know how excited I get from seeing you in latex. You both look amazing. I don’t think I can handle two beautiful dominant women at one time.”

Mistress Sarah gave Joe’s cock a hard squeeze and said, “That’s the point slut.”

May confidently walked over to the bed. “Thank you for the compliment kitty-kat. This outfit is very sexy. A good choice Miss Sarah. Thank you.”

Mistress Sarah stood up and walked toward May. Talking to Joe she said, “She does look hot.”

Then Mistress Sarah leaned in and gave May a kiss. It started as a simple peck on the lips but quickly turned into a deep tongue kiss. Each of their hands rubbed each others bodies as they kissed.

Joe sat up on the bed and watched his two Mistresses. He loved what he saw. He was completely enthralled in the action. He could not help but stroke his cock as he watched the two beautiful dominant women kiss and fondle each other in front of him.

Mistress Sarah slid behind May. Both girls were facing Joe. May’s skirt was so short it barely covered her pussy. In one smooth motion, Mistress Sarah pushed up the bottom of May’s skirt and dipped her fingers into her pussy.

Joe rubbed his cock through the teddy and excitedly watched Mistress Sarah’s fingers slowly move in and out of Miss May. He saw Miss May’s head lean back against Mistress Sarah’s shoulder and her eyes close from the pleasure. He could see lust in Mistress Sarah’s eyes. All this erotic imagery trabzon escort fueled Joe’s arousal and desire to want more. He was glad to be where he was.

While Mistress Sarah slowly pleasured Miss May, she looked at Joe and said, “This is all part of my plan Josie. I am letting you into my world. My world is full of sex, kinkiness, and excitement. It’s what you want isn’t it? It’s what you dream about. The more you obey me and the more you let the pretty girl in you surface……the more I will let you into my world.”

Mistress Sarah was quite the sales person because at that moment all Joe cared about was being in her world. He wanted it bad and he let Mistress Sarah know. Almost begging Joe said, “I want to be in your world. This is where I want to be Mistress.”

“Good pet. Tell me what you need to do.”

“I need to obey you and bring out the pretty girl in me.”

“Yes. Now tell me you will do it.”

“I will obey you and I will bring out the pretty girl in me.”

“Say it again Josie.”

Joe repeated, “I will obey you and I will bring out the pretty girl in me.”

By now Mistress Sarah’s fingers were glistening with May’s juices and May was moaning softly from the slow continuous teasing of her pussy. Mistress Sarah brought her fingers to May’s lips. Her seductive eyes never left Joe’s. They captivated and controlled Joe. The second she looked down at Miss May, Joe’s eyes followed. His cock throbbed in his hand at the sight of Miss May licking her own juices off Mistress Sarah’s fingers.

“Good girl,” whispered Mistress Sarah into May’s ear. Then she gave May a kiss on the lips. Mistress Sarah looked at Joe and said, “The pretty girl is already here isn’t she? You are pretty Josie right now aren’t you?”

“Yes,” replied Joe.

“That’s right Josie. We just need to give you a make-over and teach you to be prim and proper. There’s quite a bit of work to do on you. Are you ready?”

“Yes Mistress. I am ready. I want to be a pretty girl for you.”

“Good. Let’s start with your legs. May, go get the Nair out of the closet,” ordered Mistress Sarah.

While May left to get the hair removal cream Joe panicked, “I thought we weren’t going to do anything permanent.”

“Permanent,” questioned Mistress. “There’s nothing permanent about hair removal. It grows back.”

Mistress Sarah savored the hesitant and concerned look on her pet’s face. This was the game she loved to play. She loved to tease and toy with her pets. She knew that her beauty and feminine power could persuade a boy to do things he would never imagine doing on his own. This control is what filled her with lust to feminize boys. Her pussy quivered and dampened knowing she was challenging his will and pushing his limits. Mistress had already decided that his legs would be shaved but she let him think he had a say. She liked to tease him this way and get him to convince himself that that it was o.k.

“But what about the time it takes to grow back,” protested Joe, already sensing his argument was in vain.

Miss May returned to the room. She had heard the whole conversation from the hallway. She quickly chimed in, “Don’t be such a ‘wuss’ kitty-kat. Swimmers shave their legs. Even body builders do.”

Then Mistress Sarah threw in a zinger. “Besides, you don’t want the hair on your legs to show through your stockings when were out in public, do you? Then everyone would know you were a sissy.”

Joe’s heart skipped a beat. He questioned with alarm, “In public?”

Mistress Sarah replied sweetly, “Why yes my pretty little Josie. I’ve got to show off my new princess slave to all the girls. You didn’t think I’d make you come all the way down here and then hide you away, did you?”

“I guess not,” replied Joe. He knew that a public appearance in full femme gear was inevitable. It was on his mind the whole trip down. It was just a scary thought at the moment.

Mistress Sarah reassured him, “Don’t worry kitty, your big debut is not until tomorrow night and May and I are going to transform you into a pretty girl. When you walk by people are going to look twice. Not because they think you’re a guy but because they just saw the cutest, hottest girl in the place.”

While the words were still sinking in, Mistress Sarah took Joe’s hand and led him into the bathroom. Joe followed with no resistance. He did not have the will or courage to resist. He was completely under her control.

Chapter 5: The Sissy Phase

In the bathroom, Mistress Sarah and Miss May stripped Joe out of his teddy and stockings and had him stand in the center of the bath tub. The garter belt was left on as a reminder of his femme state. Mistress Sarah supervised as Miss May spread the hair removal cream all over Joe’s legs.

As May covered his legs she commented, “Your legs are going to look so smooth and sexy Josie.”

Joe stood in the tub confused at how hard his cock was. He was being emasculated, escort trabzon yet he was aroused and excited. He knew he could not stop what was happening and it excited him. He was also thrilled to be in the presence of two beautiful dominant women. Their shiny black latex outfits looked amazing against their bronzed skin and the outfits left little to the imagination. Joe had a perfect view of Miss May’s firm tits while she was leaning over, covering his legs with the Nair. All the sexuality around him was a fantasy come true.

While the cream tingled on his legs and worked it’s magic, May tugged on his cock and played with it, keeping Joe aroused. Then she washed away the cream and Joe was left standing with hairless legs. Miss May then moved to his chest. “We are going to be showing off your cleavage tomorrow Josie. We can’t have any hair here.”

She quickly covered his chest and stomach with the cream. Joe just stood and let it happen. When his hair was removed, Mistress Sarah and May massaged a Cherry Blossom scented lotion all over his body, taking every opportunity to tease his cock and play with his nipples. Joe enjoyed the attention and soon his knees were weak, his breathes were deep, and he was on the brink of orgasm.

The girls giggled, knowing how aroused they made him. May leaned in and licked his earlobe and whispered seductively, “mmm. See how fun it is being one of the girls. You smell like a pretty cherry Josie, and your body is so smooth and girly now. I can’t wait to rub my naked body all of yours.”

Then Mistress Sarah scooped up some of the cum that was leaking out of his hard cock and put it up to his lips and said, “Have a taste of Joe’s cum Josie.”

Joe obediently sucked his cream off her fingers. The way Mistress Sarah presented it to him as ‘Joe’s’ cum was mind blowing. It made him feel slutty and like he really was Josie.”

“Good girl,” replied Mistress Sarah. “I’m so proud of you,” she added like a caring mother.

With his smooth chest and legs, the girls could not wait to dress up Joe again. He was led back to the bedroom. Mistress Sarah pulled a large white box from under the bed and placed it on top of the bed.

“This is special sissy lingerie for you Josie. I know you want to be transformed into a pretty girl, but tonight you will be just a sissy. This is a necessary step in your training pet. You need to experience all the moments of becoming a sissy so that it will shape who you are and prepare you for the next exciting step of being completely feminized.”

While Mistress Sarah unpacked the box, May squeezed Joe’s cock and said, “That’s right sissy boy. This cock will always be a reminder that you are not good enough to be a girl.” She reached up and rubbed her hand across the stubble on his face. “and we purposely left your face unshaven today so that everyone will know that you are a boy dressed as a girl.”

As Mistress Sarah laid each item on the bed, Joe could see that it was truly sissy lingerie. There was lots of shiny satin, frilly fabric, and silky bows. Joe imagined the silk would feel incredible against his smooth skin.

It felt surreal to Joe to be standing there completely aroused and submissive while the girls dressed him as a sissy. He was dressed in pink frilly satin panties, white stockings, and a white lacey garter belt. The white stockings had large silk bows at the top.

May admired his legs. The stocking enhanced his smooth well toned and muscular legs. She rubbed her hands along the stockings and commented, “Josie, your legs look so smooth and sexy in those stockings. You put other girls to shame.”

Joe blushed but was actually proud of the compliment. He looked down at his legs and agreed with Miss May. They looked very sexy. “Thank you Miss May,” he replied.

Next Mistress Sarah approached him with pink satin bra in her hands. In an excited voice she said, “Here’s your first bra sissy. Put your arms out princess and I’ll help you put it on.”

Like a puppet, Joe obeyed. Butterflies filled his stomach and his cock twitched as Mistress Sarah strapped secured the bra. He felt completely emasculated and feminized with the bra on. He was nervous and excited from crossing over this threshold into the feminine world. The tightness of the bra, felt like bondage to Joe. He felt as if he was being locked into the feminine world and pushed deeper under Mistress Sarah and Miss May’s control.

“Oh that is so pretty,” commented Mistress Sarah as she admired her pet.

His muscles contrasted beautifully against the pretty delicate fabric. Mistress Sarah’s body shivered in excitement to see this strong man dressed so feminine and pretty and to see him so docile and submissive to her.

“My pretty little slave girl,” she said with delight and accomplishment.

Mistress Sarah reached down and squeezed his cock through the panties and teased it a bit. She wanted to ensure he remained fully aroused and close trabzon escort bayan to orgasm during his feminization. She knew keeping him aroused allowed him to be easily manipulated and trained to be her obedient feminine slave.

Mistress Sarah continued to play with his cock and asked Miss May, “Why don’t you get the special sissy dress for our slave May.”

“My pleasure,” responded May.

Miss May pulled a large satin dress from the closet and displayed it for everyone to see. The dress was the most feminine and sissy looking dress that Joe had ever seen. It was made of high quality pink and white bridal satin. A white satin apron with pink ribbons was embroidered on the front of the dress. White shimmery lace trimmed the bottom of the dress and the sleeves.

May asked, “Isn’t this so pretty Josie. You are going to look so adorable in this.”

Joe was very aroused and extremely excited to please Mistress Sarah and Miss May. He could not wait to try the dress on. He knew his thoughts and desires at that moment broke all the rules he was taught about being a man but he didn’t care. Mistress Sarah had unleashed a new feminine desire in him that he could not hold back. He accepted his new fate to be a sissy and he eagerly slipped into the dress with the help of Miss May.

Miss May pulled the dress down around Joe and straightened the hems, while Mistress Sarah slowly walked around her new dress-up toy and admired ‘her.’ She commented, “What a lovely sight. You are so pretty and cute Josie. Mistress is very pleased with her sissy. Come look at yourself in the mirror.”

Joe walked over to the mirror with Mistress Sarah. As he walked he was aware of many feminine sensations. The tightness of the bra against his chest, the silky stockings rubbing over his legs and stretching against his toes, and the dress rubbing along his thighs and legs as he walked were all wonderful new sensations that reminded him of his feminine state. His arousal grew stronger knowing that Mistress Sarah was purposely bringing out the girl inside him.

Joe never imagined he would be staring at himself in a mirror, dressed as a sissy. He never would have predicted or comprehended how exciting the moment would be. Beneath the pink shiny dress and underneath his satin frilly panties his cock throbbed harder than ever. He wanted to touch it stroke it desperately but he knew that was forbidden. Instead he flexed his PC muscle, causing his cock to pulse against the silky sissy panties. He felt completely submissive dressed as a sissy and surrounded by his two Mistresses who were dressed in tight sexy latex outfits.

Joe gazed into the mirror like a deer in headlights. He thought he looked silly but he knew Mistress Sarah and Miss May were pleased with his look and he knew that their pussies were dripping from his obedience and from his sissy look. This alone, made it worthwhile. He would not want to be caught dead dressed as he was, in front of his friends but in Mistress Sarah’s world, he was thrilled, aroused, and excited to experience his sissy state.

Miss May and Mistress Sarah showered him with compliments. “You are so pretty princess,” cooed Mistress Sarah.

Miss May added, “Pink is your color sweetie. We’re going to have to paint your nails a nice pretty pink to match you dress.”

“I have the perfect shade,” said Mistress Sarah.

Everything happened so quickly. The girls had Joe sit on stool and each took a hand and went to work. In just a few minutes he had shiny pink finger nails. Miss May added a wig with long straight black hair while Mistress Sarah applied glossy red lipstick to his lips. Mistress Sarah brought a hand mirror up to Joe’s face so he could see the results.

Joe had a good amount of razor stubble on his face. The wig and lipstick alone did not create a pretty picture. He simply looked like a man wearing a wig and lipstick. Joe asked, “Can I shave Mistress? Will you put more make-up on me so I look more like a girl?”

Miss May giggled at his requests. Mistress Sarah responded, “Josie, it’s good that you notice these things sweetie. Wanting to make your face pretty and girly shows me how well you are progressing in your training and moving along your journey to girlhood. I am so proud of you for that but we will save the make-up and shaving for tomorrow. Remember you are sissy tonight and this is what sissies look like. You make a perfect sissy sweetie.”

“Yes Mistress,” replied Joe.

Miss May commented, “You are quite a sissy boy Josie and tonight you are going to be my little bitch aren’t you? Tell me what sissy bitch you are going to be for me.”

Joe knew what she wanted to hear. “I’m going to be your sissy bitch tonight Miss May. I’m going to suck your strap-on and I’m going to let you fuck me with it.”

Miss May laughed and questioned his last words, “let me fuck you? There’s not ‘let’ sissy bitch. I AM going to fuck you. You have no choice. Now say it again slut. Tell me you are going to be fucked.”

Miss May’s words were stern and unforgiving, but Joe loved it. It pushed him further into subspace. Joe replied, “I am your sissy bitch and I am going to be fucked by you tonight.”

“That’s my slut,” laughed Miss May. “Now show me your sissy panties. Lift up that cute dress of yours and show me your pretty panties.”

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