Discovering Mistress Sarah’s World – Part 3

Chapter 7: A Brief Digression 

Mistress Sarah sat naked, in a stiff padded chair in front of a large vanity.  She waited patiently for her two sex pets to return.  It was time for Joe to learn how to properly dress her for a night out and she wanted him in full sissy attire for the event.   May had been charged with the task of getting him back into his dress.  In the reflection of the mirror Mistress Sarah watched May help Joe into his sissy dress.  May slowly circled Joe and pulled down on the pink silky fabric, ensuring the shiny dress cascaded around his legs smoothly and wrinkle free.

Mistress Sarah’s fingers leisurely caressed her own breasts as she watched the show.  Her thumbs rubbed over her nipples causing a brief shiver through her body.  It was an arousing sight to see May naked and dressing her sissy.  May’s body was slender and tight.  Each time she leaned forward, Mistress Sarah was rewarded with the sexy image of her round tits dangling beneath her slim body.  

May moved behind Joe, which gave Mistress Sarah a clear view of him.  Mistress Sarah teased her nipples as she took in the sight.  It was her chance to admire Joe without him being aware.  He was caught up in the moment with May and did not notice Mistress Sarah staring at him through the mirror.

To Mistress Sarah, Joe did not exist anymore; at least not on the surface.  He was tucked away deep inside Josie.  That’s where he belonged and Mistress Sarah intended on keeping him tucked away as long as possible.   Josie was her creation and she needed to thrive and be free.  

Mistress Sarah’s pussy began to dampen as she admired her silk covered sissy.  He looked pretty and docile draped in pink and white satin.  The pretty silk bows all over the dress looked cute.  May even added white lace gloves to his ensemble that matched perfectly with his white stockings.  Aside from his face and neck, the only skin showing was from his wrists to the top of his arms.  Mistress Sarah loved this image.  The image of his strong and muscular arms disappearing into soft silk and lacy fabric hit an erotic nerve within her that caused her pussy to quiver in pleasure.
 
Needing to satisfy the heat between her legs, Mistress Sarah’s right hand slid down to her pussy.  She lightly traced her fingers over her soft pussy lips as she reminisced about her first days with Josie.  She remembered how unwilling he was to being feminized.  He admitted he was a panty boy, as most boys do, but was resistant to go much further.  However with carefully planned teasing and seduction, his panty boy days were a thing of the past.  

Mistress Sarah’s fingers grew wetter as she played with herself and thought back to the first time she convinced him to buy tampons.  He was nervous and shy but he could not disobey her orders.  He bought tampons and he inserted one into his ass and wore it all day at work.  This was an exciting moment for both Mistress Sarah and him as it proved he had the courage to move down the path of feminization.  
 
Now the once defiant boy stood behind Mistress Sarah dressed in complete sissy attire.  Tampons were a monthly routine for him.  He had grown fond of butt plugs and dildos in his ass.  Standing up to pee, never crossed his mind anymore.   Mistress Sarah took great pleasure in knowing that her power and sex appeal were the reason for all this. Josie was her creation and her property.  She would continue to mold and shape his mind and body into a pretty submissive femme boy.  This is what she enjoyed doing and it was the only way boys were allowed into her world.

With her excitement building her patience grew short.  “Hurry pets.  Come to me,” she demanded.

May and Josie hurried over to Mistress Sarah and stood on each side of her. 

“Kneel at my feet,” ordered Mistress Sarah. 

Josie kneeled down in front of his Mistress.  His kitty bell jingled around his neck.

Mistress Sarah looked over at May and in a gentler voice said, “You to May.  Kneel next to Josie.”

With both her pets at her feet, Mistress Sarah spread open her knees revealing her wet and swollen pussy.  The smell of her sex was strong and delicious. 

“You two have been naughty getting me exciting like this.  You need to take of this problem…quickly so we can get ready,” ordered Mistress Sarah.

Mistress Sarah guided May’s head between her legs.  Josie watched her tongue lick up and down the length of Mistress Sarah’s shaven pussy several times.  Then her tongue disappeared into the hot wetness.  Mistress Sarah held May’s head against her sex and moaned in delight as May’s tongue probed deep insider her.  

Josie was entranced at the sight of May’s pussy lips peaking out at him while she kneeled and serviced Mistress Sarah.  He grew hungry for her.  He wanted to taste her. Josie leaned forward and followed his craving.  He licked May’s pussy lips with his needy tongue.  Her lips felt velvety against his tongue.  She tasted delicious and naughty.  May opened her knees slightly and pushed back onto Josie’s tongue.  A two-way tongue fuck ensued.

May pleasured Mistress Sarah while Josie pleasured May.  Josie’s cock hung below him hard, throbbing, and untouched.  This did not bother Josie for he knew his purpose was to serve and please woman.  That in itself was rewarding for him.  Josie also received pleasure from the plug that was still pressed tightly into his ass.  He rocked slightly on his knees as he tongued May’s pussy causing the plug to press against his panties and push deeper into his ass.  Josie savored this simulated fucking sensation in his boy pussy.

Soon Mistress Sarah erupted into orgasm.  Like electricity, it only took seconds to flow through to May. May reached one hand back and pressed Josie’s head into her pulsing pussy.  Josie pressed his mouth and nose into her tight wet hole and used his tongue as best he could to satisfy her orgasm.  May moaned into Mistress Sarah’s pussy as her orgasm took hold.  Josie kept licking and licking until May finally pushed him away.

Josie was left kneeling and aroused, facing the two girls.  Both girls looked satisfied and relaxed. Josie on the other hand was horny, and attentive.  Although his cock was hidden beneath the sissy dress the expression on his face was filled with arousal.  May wanted to have a little fun and so she ordered, “Lift up your dress princess.  I want to see your sissy cock.  I bet it’s so hard right now.”

“Yes…very hard Miss May,” admitted Josie as he slowly lifted the hem of the dress.  

His cock was twitching on its own from all the excitement. May moved her foot to his cock and gently rubbed the underside with her toes.  She teased,  “Aww.  Look how excited our little bitch is.  Poor kitty didn’t get to cum.”

Josie pushed his cock forward, humping her foot. 

May held her foot firm and said, “That’s it slut. Hump my foot.  You are so desperate to cum aren’t you?”

“Yes Miss May.  Please may I cum,” begged Josie.  He rubbed his cock up and down the underside of her foot.

Mistress Sarah crossed her legs and sat back and watched.  She was delighted at how May was maintaining control and power over Josie while teasing him.  May’s other foot joined in on the teasing.  Both her feet cupped Josie’s cock as he humped away.  Josie was amazed at how skillful May was with her feet.

Again Josie begged, “Please Miss May can I cum?  I’m so close!”

May quickly pulled her feet away and laughed.  “You’ve already had an orgasm once today Josie.  I think that’s enough.  I want you to stay hot and horny all night.  That way you will be begging me to fuck you with my strap-on later tonight.”

Mistress Sarah smiled and petted May’s head. She complimented, “Nicely done.  Good girl.”

May smiled both inside and out, from the compliment.  She was happy to please Mistress Sarah and also thrilled at her power over Josie.

Chapter 8: Dressing The Girls

For the next half-hour all attention was on Mistress Sarah.  May was already well trained on getting Mistress Sarah ready for a night out so she knew what had to be done.  She ordered Josie to pick out 4 or 5 panty and bra sets from Mistress Sarah’s lingerie drawer.  While Josie gathered these items, May worked on blow-drying and brushing Mistress Sarah’s hair.  Just as May was finishing with the hair dryer, Josie returned with a handful of panties and bras. 

“Let’s see what you picked out princess,” said May as she stood behind Mistress Sarah, brushing her long blond hair.  “Hold them up one at a time for Mistress to see.”

Mistress Sarah had a large collection of bras and panties.  Josie tried to pick a variety of styles and colors, hoping that at least one set would satisfy her.  He started with a purple lace bra and matching thong.

“Mmm. I love that set,” cooed Mistress Sarah.  “Sexy choice kitten, but let’s see what else you have.”

Josie held up each panty and bra.  Mistress Sarah and May giggled a few times and complimented on how cute Josie would look in some of the items.  Mistress Sarah finally settled on a black lace bra with black silk boy shorts. 

May had Josie bring the items over to Mistress Sarah and ordered him to dress her.  He knelt before Mistress Sarah and slid the panties up her legs.  She lifted her ass slightly off the chair allowing Josie to pull the panties all the way up.  Next Josie picked up the bra.  He had taken many bras off girls before but had never put one on a girl and so he felt awkward with the bra in his hands.

May noticed his uncertainty and hesitation.  She joked, “don’t be scared Josie.  It’s just a bra.  You can do it.”

Mistress Sarah added, “Soon you’ll be a pro with bras dear.  They will become a regular part of your wardrobe pretty.  We don’t want your titties getting saggy do we?” 

Josie’s cock twitched at the comment. He did not know how serious Mistress Sarah was about him wearing bras all the time.  For some mysterious reason the idea excited him.  He could not imagine how it would be possible but at the moment it seemed thrilling.

Mistress Sarah stood-up and put her arms out for Josie.  Josie slid the straps up her arms.  It almost seemed cruel to be covering up such beautiful tits.  Before the bra covered her tits, Mistress Sarah ordered, “Kiss them.”

Josie gladly leaned down and gave each of her nipples a soft kiss and gentle tongue licking.  Josie cock was raging hard beneath his sissy dress.

“Mmmm.  So nice,” moaned Mistress Sarah.

After enjoying her tits for a few brief seconds, Josie moved behind Mistress Sarah and pulled her bra up.  To his surprise, he managed to clasp the bra shut with only a slight bit of fumbling.  

Even May was impressed. “Good girl,” she said in a complimentary tone.

Next Josie was ordered to fetch a pair of panties from May’s overnight bag.  She would go topless for now because that was the way Mistress Sarah preferred her.  He fished through the bag and found a pair of cotton leopard print panties.  Josie quickly brought them over to May and kneeled before her.  May stepped into the panties and Josie slid them up her legs. On a whim, he gave her pussy a kiss and a flick off his tongue before pulling the panties all the way up.

“Very nice,” cooed May.  “Now let’s get you started on Mistress Sarah’s hair.”

May handed him a brush and stood back to watch. Josie lightly brushed Mistress Sarah’s hair. 

Immediately May ordered, “Harder!  Don’t be such a sissy!”

Both May and Mistress Sarah laughed at the unintended pun.  “Oh, that’s right… you are a sissy,” said May, amused.  “Try to be more like a man when you brush her hair.  I know it will be hard for you pretty, but just try.”

Josie blushed at the humiliating remarks and giggles.  His red face seemed to be a visual gauge on his arousal and submission.  The deeper he blushed the more his cock swelled and the more submissive he became. Obediently he firmly brushed Mistress Sarah’s long golden hair.  He felt like a slave worshipping a Goddess.

May went to work on Mistress Sarah’s make-up while Josie continued with her hair.  Mistress Sarah relaxed and enjoyed the pampering from her pets.  It was blissful for her to not have to give out any orders.  She reveled in her Goddess state as her pets gave 100% of their attention to her.

In between brushing hair, Josie had to fetch various make-up items for May.  Although most of the items were within reach of May, she still required Josie to fetch them.  This served two purposes. First, it was a learning experience for him and second, it reinforced his obedience and slave status with May.  

May applied most of the make-up.  While she worked she explained to Josie what she was she was doing.  She even let Josie help apply some of Mistress Sarah’s foundation, blush, and lipstick.  Josie found the experience to be very gratifying.  He enjoyed pampering his Mistress and was eager to learn about make-up.

After Mistress Sarah’s hair and make-up were done, Josie followed May to the closet.  She sorted through the large selection of clothes looking for a sexy outfit for Mistress Sarah.  She finally settled on a simple black tank top with spaghetti straps and a pair of white denim shorts. 

“Here you go sissy slave,” said May as she handed the items to Josie.  “Now run along and dress your Mistress.”

“Yes Miss May,” replied Josie submissively.

Joe dressed Mistress Sarah in the tight fitting clothes.  The top clung nicely to here large breasts and provided a breathtaking view of her cleavage.  The shorts were made of stretchy denim that hugged her round ass perfectly.  Joe felt a bit jealous, knowing that Mistress Sarah would be hitting the clubs in such a sexy outfit without him.

Next he helped her into a pair of dressy sandals that were both sexy and comfortable.  Finally, May laid out a necklace, ear rings, and bracelets for Josie to put on Mistress Sarah.  

Mistress Sarah admired herself in the mirror and said,  “Nicely done girls.  It will be fun teasing all the boys and girls in my sexy outfit tonight.  Maybe I’ll bring one of them home to play with.  Wouldn’t that be fun Josie?”

“Yes, very fun,” admitted Josie, hoping she would bring home a girl and not a boy.  He knew anything was possible with Mistress Sarah.

“I’m sure they would love to watch Miss May pop your cherry sweetie.”

Seductively May added, “I would love to put on a show.”

Mistress Sarah said, “Well then Josie, you better make Miss May look nice and pretty for the show.  I’ll meet you two downstairs when you are done.”

Upon Mistress Sarah’s exit, May sat in the chair in front of the vanity.  “O.K. Josie.  Start with my hair.”

“Yes Miss May.”

Josie dried and brushed Miss May’s hair.  Then he was instructed on how to apply her make-up.  This time Josie did most of the application himself.  Putting on her foundation and blush was easy and fun for Josie.  When it came to the finer things like mascara and eye shadow, Josie was awkward and clumsy.  Often times Miss May had to touch up his mistakes.  

Miss May was always firm, but understanding with her criticism.  When she was not satisfied with her eye shadow she criticized, “Too much Josie.  I want subtleness to attract the boys, not clown eyes.”

“Yes Miss May. Sorry,” apologized Josie as he watched her wipe some away and touch it up.

It took two tries with the lipstick before Josie could get her lips to look acceptable to Miss May.  Josie thought the brown glossy color was a sexy and glamorous accent to her lighter colored skin.

After the make-up was done, Josie retrieved a leopard print bra from her overnight bag. Wanting to treat her just as special as Mistress Sarah, Josie spent a few minutes attending to Miss May’s nipples before pulling the bra all the way up.  Her breasts were smaller than Mistress Sarah’s but they were perfect for her body size.  Josie loved their firmness and perkiness.  He could not resist cupping her tits in his hands while he teased her nipples with his tongue.

Miss May took pleasure in the attention.  His soft lips against her sensitive nipples caused an exquisite burst of pleasure .  She could feel her nipples swell with arousal.  She arched her back and lightly held the back of his head encouraging him to continue.

A soft moan escaped her lips, “ooohh, kitty-kat.”

Miss May was sinking into a sea of pleasure.  Her pussy came alive and slowly she was being swept away. She did not want it to stop but she knew Mistress Sarah was waiting and would be upset if they took too long.  It took all her strength to fight her sexual urges.
Miss May pushed his head away and said, “enough kitty-kat.  You’re going to get me in trouble.  Mistress Sarah is waiting.  Hurry and dress me.”      

“Yes Miss May.”

Josie pulled up her bra cups and secured the bra.  Next he helped Miss May into a white tank top and a gray pleated skirt.  Finally, he kneeled before her with a pair of heels.  Miss May slid each foot into the shoes and Josie secured the straps around her ankles.

Josie thought Miss May looked sexy and flirty.  “You look incredible Miss May.”

“Thanks slave.  I bet I’ll make a few cocks hard tonight. What do you think Josie?  Will the guys being dreaming of fucking me tonight?”

“Most definitely Miss May.  I would want to.”

Miss May laughed and looked into Josie eyes.  “Silly Josie, you’re just a sissy boy.  I know your little clitty is all hard and swollen underneath that pretty dress but when I’m at the clubs I flirt with real men who have real cocks.”

Josie blushed with embarrassment.  For a brief moment, he wanted to show that he could be a real man but part of him was excited at his predicament.  There was a strange thrill in being humiliated and knowing that he was her servant, preparing her for a night of flirting and possible sex.

Josie was confused at these emotions.  Before he could get his thoughts together Miss May continued, “Don’t worry Josie.  Sissies are special to me too.  You don’t get to fuck me but I get to fuck you and I am so looking forward to it tonight.”

Josie’s cock throbbed in his panties.  “Me too Miss May.  I can’t wait.”

“I know sissy.  You are a slut aren’t you?  Tell me that Josie.  Tell me how bad you want me to fuck you.”

Miss May’s orders energized Josie with lust and excitement.  “I want you to fuck me real bad Miss May.  I want to be your slut.”

“Mmm.  Are you my bitch?”

“Yes, I am your bitch. Pleas fuck your bitch,” begged Josie, his cock throbbing harder by the minute.

“I’m going to peg you hard bitch!  That’s what you want isn’t it?”

Josie hesitated.  He had never been pegged in the ass before and was nervous about a hard fucking.  His hesitation was noticed by Miss May.

Miss May scolded, “Say yes Josie!”

Overcome by her authority Josie, replied, “Yes.  Please fuck me hard!  Fuck me anyway you want too.”

Miss May’s tone softened, “That’s a good bitch. Come here sissy.  Let me touch you up before our guests arrive.”

“Guests,” questioned Josie with nervousness as he walked over to Miss May.

Miss May began to reapply red lipstick onto Josie’s lips.  “Yes darling.  Mistress wanted everyone to meet at her house so that she could show you off.”

Josie’s heart pounded in his chest.  He was nervous about meeting other people while dressed as a sissy.

“It’s just a few friends.  They have all seen Nellie prettied up before.  They are going to fawn all over you in your pretty dress.”

Miss May’s words calmed Josie.  He knew that Nellie was a reference to Mistress Sarah’s boyfriend, Neil.  Knowing that the girls were into sissies changed the scenario a bit.  The thought actually became exciting to Josie.  He was looking forward to the attention.

Miss May picked up a blush brush and said, “A little blush with your red lipstick will give you the perfect sissy look kitty-kat.”

She brushed the blush onto each cheek and inspected her work.  “Perfect,” she said. 

Miss May made Josie look into the mirror. “You look like a boy in a wig who has been playing with make-up…a sissy boy.  Any more make-up and you would start to look like a pretty girl.” 

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

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