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."