Discovering Mistress Sarah’s World – Part 4

Special thanks to Mistress Sarah and Miss May and Miss Mill who are my motivation for this story.  Thank you for your guidance and wisdom and for the privilege of serving you and writing about you.

Chapter 11 Discovering the Girl in Him 

For the first time since he arrived at Mistress Sarah’s house, Josie was left alone in silence.  His cock was still throbbing from all the attention from the girls.  It continued to throb as he thought about his exciting assignments for the night.  He picked up the journal with his feminine name on it and opened it.  

Written in pink ink on the first page was, ‘‘When I first saw Mistress Sarah I felt….”  The remainder of the page was left blank for Josie to fill in.

Immediately Josie’s thoughts went into action.  He picked up the pink pen and started writing how exciting and nervous he was earlier in the day.  He easily filled up the blank page.  It was good that only 1 page was left blank. Otherwise Josie would have gotten carried away and filled the whole journal on the first entry.

On page two purple ink spelled out, “Today Mistress Sarah and Miss May dressed me as a sissy.  I wore….”   Several lines were left blank and then it read “My favorite part about being a sissy is…”

Josie thought it would be cute to match the ink colors on each page.  He put down the pink pen and picked up the purple one.  He described his sissy dress and sexy lingerie. Then he described how exciting it was to show off his pretty clothes to the girls.  He admitted to loving all the attention as well as being covered in silky soft clothes.

Josie found that he was completely aroused at writing his thoughts in his journal.  Reliving the erotic fun earlier in the day caused his cock to swell and throb in his panties.  It was like Mistress Sarah was teasing him without even being there.

The next page had the sentence about trying on Mistress Sarah’s panties.  Josie could not wait to do this. Suddenly he remembered that Mistress Sarah ordered him to take a bath before he began.  Realizing he was already disobedient by first writing in his journal, he quickly put the journal down and headed upstairs to the bathroom so that he could get back on track.

Josie was enthused about his assignments and really wanted to please Mistress Sarah by diving into the feminine world.  Her words echoed in his head, ‘you need to discover and experiment with girly things….a women’s world is full of pretty scents…you need to submerse yourself in this secret dreamy world.”

With her words of motivation, Josie was eager to experiment.  He turned on the water to fill the bathtub and then explored the bathroom.  He discovered bath salts and many scents of bubble bath.  There were fragrances of Cucumber, Sweet Pea, Cherry Blossom and Sea Island Cotton.  Josie smelled each one.  Each scent that he inhaled softened his mind and melted him further into the feminine world.  He loved the Cherry Blossom fragrance and decided to use this for his bath.

As the water filled and the bubbles foamed, Josie lit all the candles that Mistress Sarah had placed around the bathroom.  He turned off the lights and stripped out of his bra, stockings, and panties.  Finally he eased himself into the bath.  

The hot water surrounded and soothed him.  The soft glow of the candles and the pretty scent from the bubble bath relaxed him.  ‘I could get use to this,’ he thought.  His manly traits drifted farther and farther away.

To his surprise, as he relaxed and his mind cleared, his arousal grew.  There was so much arousal pent up inside that his cock hardened beneath the suds and beckoned for him to stroke it.  He played with his cock and thought about how much fun he was having as a sissy. This was something he could never admit to his friends.  It challenged his own principles but he was undoubtedly enjoying what was happening.  Josie knew that he was deeply entangled in Mistress Sarah’s seductive web and would not be able to escape.  For reasons unknown to him her power and dominance fueled his arousal.

Soon Josie realized that soaking in the tub would lead to his demise as he would surely stroke himself to an orgasm.  He made the hard decision to stop and move on with his assignment.  After his bath he went right for Mistress Sarah’s panty drawer and lingerie chest.  Even though he had her permission, he felt naughty and perverted going through her panties and bras.  

Josie admired the many varieties of panties.  He tried on silk, cotton, lace, and even mesh panties.   There were boy shorts, thongs and French cut styles.  Each time he slid on a new pair of panties his cock throbbed.  He took his time, paying attention to their feel and look.  The silk panties felt smooth and wonderful against his cock.  Her thong panties tickled his ass.  He loved how they felt when he walked and pranced around the room in them.  Mistress Sarah had quite a selection of fur panties, which he enjoyed.  The fur was on the outside of the panties but Josie could not resist turning one pair inside out and sliding them on.  The fur felt amazing around his cock balls, and ass.  

He was horny and in a rare mood and was really enjoying the fur.  Josie lay on his stomach on Mistress Sarah’s bed and slowly began to hump the bed.  The soft fluffiness all around his sensitive areas was mind blowing. His entire body shivered with pleasure as his cock and balls rubbed over the fur.  It only took a few seconds to bring himself to the edge.  It was hard for Josie to stop.  He was desperate to cum and knew it would be amazing to orgasm with his cock buried on the soft fur. 

For a moment Josie thought he went too far.  He could feel an orgasm coming on.  He quickly raised himself up to his hands and knees to relieve the pressure on his cock.  Josie struggled and concentrated on not cumming.  He did not want to be disobedient.  It took all his energy and focus to hold back and fortunately he was able to stop his orgasm.  He slid off the fur panties and made a note in his journal about how much he loved them.

Next Josie moved onto bras.  His shoulders were broad and so he could not fit into Mistress Sarah’s bras and night gowns but he held them up to his body and admired them.  He managed to slip into one long red silk nightgown that was obviously over-sized for Mistress Sarah.  He enjoyed how the silk fabric contoured with his body.  

Josie made notes and comments in his journal while he played dress-up with Mistress Sarah’s lingerie.  He noted his favorite colors and styles.  He commented at how sexy Mistress Sarah’s red corset was.  He even admitted that the thong panties felt nice rubbing along his ass.

The girls had laid out a roadmap for Josie to follow in his exploration into womanhood.  The next few pages were presented like a self interview.

	‘My favorite perfume is….’
	‘My favorite nail polish is…’
	‘I thought I looked sexy in the following outfits….’
	‘I experimented with Mistress Sarah’s make-up.  I really liked….’
	‘I think my lips look sexiest when they are the color…’  
	‘When I go to the night clubs I want to wear….

Josie continued through the journal, experimenting with all the girly things and completing the sentences.  Josie felt naughty and excited exploring all the girly things.  His cock continually swelled and contracted as he played with Mistress Sarah’s belongings.

He loved the fire red nail polish and glossy red lipstick.  Although he could not squeeze into her clothes, he imagined himself as a sexy girl and thought about how much fun and sexy it would be to wear some of her skirts and low cut tops.  As he immersed himself into her things, his mind transformed further into the feminine world.  It had a brainwashing effect on Josie.  Mentally he was starting to think as a female.  He even convinced himself to start losing weight so that he would look sexy in Mistress Sarah’s clothes.

Josie was having so much fun that he barely noticed the time go by.  His cell phone rang and he was thrilled to see that it was Mistress Sarah. Josie answered it quickly.

“His Mistress Sarah.”  He could hear music and dancing in the background.

“Hello princess.  Are you a woman yet?”

Josie blushed even though he was alone.  “Getting there I guess.”

“Yes you are doll.  You’re almost past the sissy phase of your training.  Are you excited about that?”

“Yes Mistress,” admitted Josie, not even sure what to expect next.

“Miss May needs to pop your little cherry for you to graduate to the next level of your training.  Are you ready to be fucked by her strap-on sissy?”

Josie’s cock swelled harder than he ever imagined as he realized the moment of his deflowering was approaching fast.  “Yes, I can’t wait.”

“Neither can May.   I made her wear a strap-on under her skirt so that all night she would be thinking about fucking you. I even let her fuck Mill in the back of the car on the way to the club, which got May even more horned up.  She’s been begging to leave all night so she can peg you.”

The image of Miss May fucking Mill aroused Joe even more.  The only words that came to mind were, “That’s hot!”

Mistress Sarah laughed at his response and then gave a few orders.  “We’ll be coming home soon slut.  Clean-up all my things that you played with. Make sure the place is nice and tidy and then pick out a pair of my furry panties to wear along with your kitty bell and garters and stockings.  Be kneeling by the door waiting for us, o.k. Kitty?”

“Yes Mistress.”

Joe heard Miss May’s voice in the background yell, “Put a fresh coat of glossy lipstick on sissy.  I want to see pretty blow-job lips on my cock.”

“Yes Miss May,” replied Joe.  Then he heard giggles and the phone went dead.

Chapter 12: Josie’s Deflowering

Josie kneeled by the door anxious for the arrival of his Mistresses.   He could feel his ass pulsing around the butt plug in anticipation of what was to come.  As he kneeled and waited he could smell the pretty floral scent of the perfume that he had sprayed on his neck earlier.  He felt soft and girly from all the day’s events.  His was in a prime mode to be fucked like a sissy.  Even though he was not touching his cock, it was pulsing and hard with arousal.  He was both excited and nervous about being pegged.  

Josie heard faint voices outside.  He tensed wondering if it was Mistress Sarah, Miss May, and Mill.  The voices grew louder and he heard laughter and footsteps approaching the door.  Josie’s heart pounded in his chest and his cock pounded with its own heartbeat inside his furry panties. When the door pushed open and Mistress Sarah and Miss May walked in.  His excitement and submissiveness suddenly intensified like a blazing inferno.

Miss May was also burning with lust.  She burst into the room and sought out her kitty-kat immediately.  ‘Where’s my fuck bitch?  I’ve got a nice big cock for you!”

Before Josie could even think to respond, Miss May pulled up her skirt and pushed her strap-on towards Josie’s lips.  She grabbed the back of his head and ordered, “Suck my cock bitch-boy!”   

Her strap-on pushed into his mouth and she started fucking him. Having no experience with sucking a strap-on, Josie struggled to keep up and gagged.  Miss May was full of lust and she was in a semi-drunken state from a night of fun.  She was in no mood for patience.  She continued fucking her slut, ordering him to keep up.

“Come on bitch.  You can do it!  I fucked Mill earlier.  Suck off all her juices slut.”

This was not how Josie imagined his night starting.  Everything was happening so fast and furious.   It was not the slow gentle introduction to a strap-on that he fantasized about. To his surprise Miss May’s forcefulness and commanding words took him into a heightened state of arousal and submission.  His cock was fully erect and throbbing.  His tight furry panties pressed the hot flesh of h is hard cock against his stomach.  He could feel his ass muscles pulsing against the plug in ass his ass.  He felt like a total whore and he loved it.

As soon as Josie was able to keep up with his Mistress’ rhythm Miss May increased her pace.  To get more leverage she placed her left foot up on a chair that was next to Josie, held the back of his head firmly and fucked him hard.  His kitty bell jingled in rhythm with the hard oral pounding.

“Good bitch.  Your pretty red lips look sexy around my cock.  Keep sucking sissy.  Get my cock nice and wet for you sissy ass.”

Josie felt completely used and at her mercy.  Sucking her cock and keeping up with her rhythm was the only thing his simple mind could focus on at the moment.  He was nothing but a fuck-toy.  Josie was so focused on keeping up with Miss May that he did not notice that Mistress Sarah had left the room and then returned wearing nothing but a strap-on.

Mistress Sarah could see the lust and hunger in May’s face and body language.  Her pussy tingled at the sight of Josie’s helplessness and arousal.  To see May powerfully man-handle him was remarkable and exciting.  She wanted to join in on the fun 

Mistress Sarah hugged May from behind, gently kissed her neck and pulled her back.  She whispered to May just loud enough for Josie to hear. “It’s so sexy to see you fuck kitty like that.  Let’s move her into the bedroom.”

May was on the verge of an orgasm from the pure erotic pleasure of the power exchange with Josie.  It was hard for her to pull away but she knew that was best.  She did not want to wear out Josie to early. May was thankful that Mistress Sarah intervened when she did.  May grabbed a collar and leash that was stowed away in a nearby closet.  She quickly snapped the collar around Josie’s neck, attached the leash, and led him into the bedroom.

Josie was made to kneel on hands and knees in the center of the bed.  While May slid out of her skirt and top, Mistress Sarah reached beneath Josie and squeezed his cock through the panties.  Then she asked, “Enjoying my furry panties slut?”

“Yes Mistress.  They are very soft and smooth.  I had fun with then earlier.”

Mistress Sarah continued to tease his cock.  She inhaled deeply and observed, “You smell very pretty kitty.  You must have enjoyed my perfume.  How was your night of girl indulgence?”

“Incredible Mistress.  I had so much fun.  Thank you for letting me go through all your things.”

“A girl has to learn somewhere, right? Isn’t our girl world so much more exciting and fun than the boring guy world?”

“Yes Mistress.”

“I only play with soft pretty girls Josie.  You will be that for me right Josie?  You want to play with me and please me don’t you?”

Josie was completely aroused and entranced by Mistress Sarah. His mind was mush and he wanted to do whatever pleased her and Miss May.  “Yes Mistress.  I want you so bad.  I am a soft pretty girl ready to play with you.”

Mistress Sarah’s hands slid down to his balls.  She squeezed his balls firmly causing Josie to gasp. Her tone became firmer when she spoke.  “You’re not a pretty girl just yet.  You’re still our sissy bitch Josie.” 

Mistress Sarah laughed and then stood to the side of the bed so that her strap-on was right at Josie’s lips.  “Time to suck my cock sissy,” announced Mistress Sarah.  “Come on slut, show me what you got.”

Josie obeyed and went down on Mistress Sarah’s strap-on.  Little-by-little he took the cock into his mouth.  It was a much different experience than the hard fucking from Miss May.  He had to think about what he was doing. All the day’s events had mentally put him into a girl frame of mind.  He became a whore.  He wanted to be a good cock sucker.  He licked and sucked the strap-on as sexily as he could.

“That’s good sissy,” complimented Mistress Sarah. Her compliment encouraged Josie on.  Mistress Sarah ordered, “look at me while you are sucking my cock.”

Josie looked up. He felt slutty staring into her eyes.  She had a look of arrogance and smugness that brought out the whore in Josie.  Mistress Sarah started to slowly fuck Josie’s mouth while he sucked.  

“That’s a good bitch.  You’ll make a good fuck toy Josie.”

Miss May joined Josie on the bed.  She kneeled behind him and slid his panties down off his ass.  Josie felt the plug in his ass sliding out.  His heart started pounding in his chest knowing that one of his most sought after fantasies was about to happen.  His cock throbbed with excitement.  He wanted to stop sucking Mistress Sarah’s cock and prepare for Miss May’s entry into his boy pussy, but that was not an option.  Mistress Sarah was not going to stop.

Josie heard Miss May declare, “I’m going to enjoy pegging this tight little sissy pussy.”

Then he felt her strap-on push into his ass.  Wearing the plug all day, kept his ass stretched so that her initial entry was not too startling. However, as she pushed in deeper it stretched his insides and he tensed and moaned.  His moan was muffled by Mistress Sarah’s strap-on.

“Relax bitch,” instructed Miss May.  “Take it like a good sissy.”

Miss May rested for a moment with her strap-on about 1/3 the way into her sissy’s boy pussy allowing him to get used to the fullness.  Then she pulled back and then pushed in again going deeper than the last time. Josie continued to moan in discomfort.

Mistress Sarah pulled her cock from his mouth and coached him with a firm commanding tone.  “Focus Josie….relax and take Miss May’s cock in.  Come on slut, show us what you got.”

Miss May did not ease up.  Josie had no choice but to open up to her and accept her.  Her rhythm picked up just as he was getting used to the fullness.  A new carnal pleasure filled his insides and overtook his mind as she fucked him.  Miss May took his leash in her hands and pulled back on it causing his neck and head to pull upright.  She wrapped the leash around her hand, keeping it taught while she pegged him.

Now fully into the pegging, Miss May yelled in a half moan, “Yes…you are my bitch now Josie.  You belong to me.  You are my fuck toy…This is your life now”

Josie enjoyed being conquered both mentally and physically by Miss May.  He surrendered to her completely.  “Yes Mistress. I am your bitch,” he proclaimed between deep breaths of pleasure.

“You’re just getting started bitch boy,’ added Mistress Sarah.  She pushed her strap-on back into his mouth and began fucking him.  Mistress Sarah and Miss May altered their rhythms.  At first they alternated thrusts, with one going in while the other went out.  Then they switched so that they were both thrusting in and out of Josie at the same time.

Josie felt so dirty and twisted and whorish being fucked from both sides.  The innocent man that existed many months a go was nowhere to be found.  His altered image was feminine, slutty, submissive and desperate to be used. ‘She’ was their slave, their bitch, their sex toy to be played with as they desired.  Josie urges were raw and primal and ‘she’ was turned on by every desecration and was eager for more.  

The fast and continuous fucking and verbal torment from both Miss May and Mistress Sarah left Josie in a mindless state.  There was no opportunity to think.  He just kneeled, opened himself up for their pounding and surrendered to the dark pleasures. After several minutes of the raping, Miss May ordered Josie to roll over onto his back.

Once on his back, Miss May grabbed his legs and forcefully pulled him towards the edge of the bed.  Josie felt powerless.  Miss May ordered, “Spread your legs whore.  I’m going to fuck you just like a girl.”

Josie did not speak.  He just obeyed.  He spread his legs, opening himself up for Miss May.  Miss May grabbed his ankles, held his legs wide and thrust her strap-on into his ass.  Mistress Sarah placed her hand on the back of Josie’s head and tilted his head forward so that he was looking at Miss May fucking him.  

Mistress Sarah whispered to Josie, “Look at your Mistress Josie.  Isn’t she sexy?  She’s fucking you like a slutty bitch.  Your are sissy bitch, aren’t you?””

“Yes Mistress,” moaned Josie.  Mistress Sarah was right.  May looked powerful and sexy, completely naked and thrusting between his legs. The erotic image of the pleasure on her face and her hard nipples and firm tits bouncing was burned into Josie’s mind.

Mistress Sarah reached down and squeezed his cock and said, “Your clittie is very hard.”  Mistress Sarah stroked his cock while Miss May fucked him.

The pleasure was intense.  Josie’s insides were full of erotic fire as Miss May’s cock pushed in and out of his boy pussy. The thought of being fucked on his back never occurred to him before.  This strange twist thrilled him.   He became a girl with his legs spread, his pussy filled, and his clittie throbbing.   

The mental domination as well as the pleasure in his ass and the stroking of his cock were too much for Josie to handle.  An orgasm was building fast.  Josie pleaded with breathless moans, “This is incredible.   Please may I cum?”

Mistress Sarah released her grip on his cock so that he would not be sent over the edge.  “Beg like a girl,” she demanded. “Beg for Miss May to MAKE you cum.”

“Please make me cum Miss May. I want to cum so bad!  I want to cum like a girl!”

Miss May continued pounding his ass and demanded, “beg like a girl Josie.  You sounded like a sissy boy not my bitch girl.  Beg me with a pretty girl’s voice.”

Josie was so close to exploding.  He did not want to hold back.  In his desperation he simply obeyed without thinking. With a high pitched tone he begged, “Please make me cum like a girl.  I am so close!”

Both Miss May and Mistress Sarah burst out in laughter at the silly voice that came from Josie.  Miss May laughed so hard that she had to stop pegging Josie.  She rested with her strap-on pushed deep inside Josie.  While the girls found humor in the situation, Josie was still completely aroused and turned on and so close to cumming.  Miss May’s strap-on resting deep in his boy pussy, did not make things easier for Josie. His insides were hot with pleasure and cum was dripping out of his ‘clittie.’ Josie felt like a total whore wanting nothing but to cum while the girls laughed.

“Please don’t stop,” he begged in his girl’s voice.

“That was a little better Josie but you need to work on your girly voice,” laughed Mistress Sarah,

Miss May kept her strap-on pressed into her bitch and said, “That was cute slut.  You’ve earned an orgasm.  Cum for me right now!  Tell me you’re my slut!”  

As soon as she gave the command, Miss May started fucking Josie fast and hard.  At the same time Mistress Sarah placed the palm of her hand firmly along the side of Josie’s cock so that as his body jerked from Miss May’s pounding, his cock rubbed against Mistress Sarah’s palm.  The pleasure was intense.  With his granted permission Josie did not hold back.  

Cum spurted from his cock and he moaned, “I am your slut! I am your slut!  I am a sissy slut for you!”

Miss May changed to slower, deeper thrusts.  “Keep cumming bitch!  Cum for your Mistress bitch,” ordered Miss May.  

“Yes Mistress.  Fuck me.  I am your bitch,” moaned Josie.  Miss May’s deep thrusts continued to milk out Josie’s cum.

Miss May moaned as an orgasm surfaced within her.  She felt powerful and sexy fucking her slave with his legs spread like a girl.  The harder she pounded him, the more pleasure she experienced.  She pushed hard, rubbing her pussy against the firm base of the strap-on.  Her bitch was already done cumming but that did not matter.  Her pleasure was all that mattered and so she continued to fuck him enjoying her own pleasure.  Her body shook and tingled and exploded in pure arousal as she pounded her toy.

At the same time Miss May was climaxing, Mistress Sarah scooped up as much cum as she could from Josie’s stomach and chest and forcefully rubbed her cum covered hand over Josie’s lips so that all the cum poured into his mouth.

“Lick up all your cum,” ordered Mistress Sarah. “Mmmm.  I know you love cum princess.  You are such a slut for me.”

The warm creamy cum oozed into Josie’s mouth and coated his throat as he swallowed.  He felt dirty, twisted, and completely submissive being force fed his cum while his ass was being pegged.  Mistress Sarah pushed her fingers into his mouth ensuring he licked up every last drop of cum.  She scooped up more cum and pushed four fingers at once into his mouth. Josie enjoyed the powerful intrusion.  He relished his helpless and submissive state.  He did not want the violations to his body to end.

When Miss May’s orgasm passed she collapsed on the bed breathless.  Josie was left lying on his back, the strong cum taste lingering in his mouth.  Mistress Sarah stood over her two pets excited at what she saw and proud at how Miss May took complete control of her kitty-kat.  She was also thrilled at Josie’s complete surrender.  

Mistress Sarah removed her strap-on.  Then she moved over to Miss May and gently slid off her strap-on.  She dropped them by the door and ordered to Josie, “Go clean them up slave.”

Josie was exhausted and did not want to move, but he knew he had to.  “Yes Mistress,” he replied obediently.

Mistress Sarah’s pussy was still hot and wet with arousal. She locked the door behind Josie and turned back to May.  May had a special glow about her.  She looked sexy and luscious sprawled out naked on the bed. Mistress Sarah crawled overtop of her sexy pet.  It was time for the burning hunger inside Mistress Sarah to be attended to.

End of Part 4