Maestro Ch. 04

Previously:

- Maestro, an experienced dom, agrees to help Katie through her first bondage session.
- Katie's mother begins pressuring her about grandchildren when she knows Katie never wanted kids.
- Katie set up a clever fail-safe incase Maestro does not let her go from their bondage session. It involved Katie lying to her friend Lilly about being interested in Kevin, when she truly despised him.

After what felt like an eternity, the Friday Katie had been waiting for arrived. After years of wondering and longing, she would finally get to experience bondage for the first time. She felt like a little kid on their birthday, just waiting to open a pile of wrapped presents. As soon as she was able to duck out of work, she ran home in order to prepare for her big night.

Katie knew that she would be spending a majority of her evening without clothing, but this did not stop her from taking the time to carefully select an outfit. She thoroughly showered making sure to shave every inch of her body below her neck. She put on a sexy and lacy pink bra with a sheer matching thong. To appear as sexy as possible she chose a navy button up blouse that was very thin and hung off her breasts in a spectacular fashion. Her bra was faintly visible through the shirt. She finally pulled up a short white skirt that highlighted her freshly shaven and slender legs. She spent twice as long working on her platinum blonde hair and applying gala worthy makeup. She wanted to make sure Maestro enjoyed her visually. She realized he was also looking to gain enjoyment from this experience as well. Scanning her closet for shoes she decided on the pair of black heels she had worn on her awful date with Kevin.

Katie made sure her note for Lilly was out and visible on her kitchen counter if she were to enter before Katie returned home the following day. Katie grabbed a small purse and filled it with only the essentials before heading out the door. As Katie descended the stairs to the street below, her skin tingled. The hair on the back of her neck stood on end. She thought she might actually explode, or at least have a heart attack from pure excitement and anticipation.

With each step closer to the hotel, Katie's heart beat increased in intensity. She played in her head over and over how Maestro would kindly usher her though the world of bondage. No longer did her fantasy have to exist in her mind and on a computer screen.

Katie reached the hotel front desk and asked for the key left in her name. The attendant swiftly held out a key.

"Could you leave another copy for a 'Lilly'?" Katie asked, feeling the butterflies in her stomach as this was becoming so real.

"Absolutely. Enjoy your stay with us." The attended quickly returned to other matters.

Katie entered the chrome elevator and looked at the key to see which floor would be housing her desires. The key card simply read "The Penthouse'. From her past stays at this hotel, Katie had heard the penthouse was the entire top floor. She was surprised that he had reserved the most expensive and luxurious room, just for her. Katie pushed the round, silver button labeled "P" and waited as the elevator made its smooth and quiet ascent.

The doors opened in slow motion revealing a small hallway with two white doors. One was on her immediate right and was the emergency staircase. The other, at the very end of a seemingly straight and long hallway were French ivory doors with gold accents. Katie walked towards the impressive doors and swiped her key near the handle. The door gave a small beep and she pushed the door forward, entering the room. The golden lights illuminated a luxurious room with a large king bed in the middle. All around were lights that accented the room's finer details. There were many tables with fresh fruit, chocolates, and wine. Katie closed the door softly behind her. There were floor to ceiling windows on two of the walls that gave a beautiful view of the evening city.

"Welcome Katie."

Katie jumped as her heart skipped a beat.

"Oh my goodness! I had no idea you were here already." Katie looked at Maestro in the corner of the room nearest the bathroom door. Her hand held over her mouth from the shock.

"Great room, isn't it?" Maestro's electric blue eyes seemed to almost glow in the rooms light. He looked casual an calm wearing a simple white oxford shirt that was carefully tucked into a pair of dark blue jeans.

Katie felt a small quiver between her legs as she gazed upon him. "Yes, it is lovely."

"Come. Sit on the bed." Maestro walked towards the bed in the middle of the large room. "Would you like some wine?"

Katie walked over and sat on the edge of the bed. "No thank you. I am good."

"So Katie. Are you ready?"

Katie knew that she was one answer away from her ultimate fantasy. She had waited long enough as was now ready. "Yes, I am ready."

"Take off your clothes and place them on the desk." He held out his hand, pointing to a large oak desk near the door.

Katie walked over and set her purse down next to the illuminated desk lamp. She skillfully slipped off her black shoes and lined them up neatly on the floor.

"Turn and look at me as you undress Katie. Look into my eyes."

As she heard those words, a small fire ignited from within. He knew the words she wanted to hear.

Katie slowly turned towards Maestro. Once her eyes locked onto his , she felt her every inhibitions evacuate the room. Katie slowly unbuttoned her blouse, letting her pink bra emerge. Sliding it off her shoulders, she neatly set it on the desk. She then unzipped her skirt, making sure to not break her eye contact with Maestro, and let it fall to the floor around her ankles. She reached behind her back and unhooked the lacy bra, slowly letting it fall down the length of her sleek and slender arms. Maestro watched with a smile. A tingle ran up Katie's legs once her breasts were fully on display. She pulled down her thong, keeping her legs together and placing it on the desk with the rest of her clothes.

"Very nice Katie, very nice. How are you feeling? Good?"

"Yes. I am good." Katie said wanting nothing more than to get on with the evening.

"Perfect. Now, lie on the bed face up".

Katie walked over to the bed, feeling the growing wetness between her legs. She laid on top of the bed with her arms at her side. Without a word Maestro walked over and powerfully placed a thick leather cuff on each of her wrists. She watched as he attached each one to a bed post, spreading her arms wide. Her anticipation grew as she already liked where this was heading.

"If at any time you need this to end, your safe word will be 'danger'. If you are gagged, simply alternate between a high and low tone moan. I will stop instantly. Do you understand?"

Katie nodded, feeling, almost at home, in the room with Maestro.

Next, he grabbed each ankle and attached a cuff, securing them to the remaining bed posts. Her legs were spread to their limit. She lightly pulled on all the restrains and verified they were tight. There was almost no give.

"Nice and tight or not at all is my motto," Maestro said looking at Katie.

Maestro moved towards a duffle bag that was clearly full of all his bondage gear and returned with a black blind fold. He leaned in towards Katie with a smile. She instinctively lifted her head for him to place it over her eyes. The room became dark as he fastened it tight. Katie heard him move again, returning with something that touched her lips.

"Open", he said.

Katie opened her mouth and felt, what she knew to be a ball gag placed into her mouth and around the back of her head. He began pulling it almost too tight for comfort. The room went silent for a few moments before she heard more shuffling about the room.

Katie's anticipation and eagerness were exponentially growing by the moment. Her brain was buzzing with all the wonderful things Maestro might try with her. With a slight startle, Katie felt Maestro's fingertips lightly grazing her tone stomach. It was almost like a soft tickle. With each brushing of fingers her desire mounted. Slowly, his wispy touch navigated north, with each passing, another inch closer to her breasts. A light swipe to the left and another to the right.

Contact! Every nerve in Katie's body, sparked, for just a fraction of a second and every fiber of a hair she had tingled as Maestro lightly ran his fingers over her little pink nipples. Her body lightly trembled from pure excitement as his touch spiraled around her breasts. Maestro's fingers repeatedly danced over each of her nipples as they became petrified.

The slow shimmering of fingers that found their way to her breasts were now moving down. To her stomach, lower and lower. Again, every fiber in Katie's body was standing at attention. Like a static shock, she felt his fingers connect with her exposed and vulnerable pussy lips. A chilling shiver traveled through Katie's body like a large ocean wave. Her back arched slightly as Maestro slowly began rubbing her clit. Even though it was the most simple of touches, she felt alive like never before. She had never been so turned on in all her life. Feeling his fingers work over her pussy, with almost no control sent her to into blissful ecstasy. If she wasn't wearing a gag she would have been wearing the biggest smile.

"Deep breath," Maestro said in a soft tone.

As Katie inhaled through her nose, she felt a single finger enter her slick hole. Her back arched. Maestro began to move his finger in and out of her, moving deeper into her with each motion. Katie felt his other hand find its way underneath her ass digging into her cheeks . She felt a finger greet the outside of her asshole. Katie had never had anything in her ass before. She didn't know if she was ready, especially in this state. The idea of stopping the session with her safety sounds was in the front of her mind.

"Relax Katie."

With those words, Katie felt comfortable and safe and released every tense muscle in her body. She was ready for Maestro to push her limits. With a little push, she felt the tip of his finger enter her asshole. She tightened up with the new foreign feeling, but as he gently slid his finger in deeper, she was able to relax and discover it was an oddly satisfying feeling. Almost like a back rub. His fingers continued to work her clit and move in and out of her pussy, while his other hand rhythmically started moving a single finger in and out of her newly devirginized ass.

Katie could feel an orgasm starting to build as Maestro worked and controlled her body from within. His fingers played her like a piano. The movements in her pussy accompanied the ones in her ass. Katie began to leak moans of pleasure from behind her gag.

"That's right, cum for me Katie."

The words from Maestro's mouth entered her brain and struck a powerful chord. Her back arched as much as her restraints allowed and she erupted into a full body orgasm, fully testing the limits of her restraints. Tingling fireworks were set off between her legs. Every muscle in her body worked in unison as her eyes rolled back into her head. Her ass and pussy tightened firmly around the fingers inside her.

"Mmmhhh, mmmmh, mmmmh", was the only sound Katie could make.

Maestro slowed the movements of his fingers but continued to massage her insides as Katie slowly came down from one of the most intense orgasms of her life. As the last ember of her orgasmic eruption flickered out, she felt Maestro slowly remove his fingers from both of her holes.

"One down", Maestro said. "Let's try again."

Katie knew they had originally discussed multiple orgasms for the session, but she didn't realize he would work her like this. She had never had orgasms back to back.

"I am going to push your body to experience things you didn't even know were possible."

Katie's wrists and ankles were now sore and raw from her body pulling on them through her first orgasm. She felt Maestro run his hands from her feet, up her legs, sending tingles down her spine. His fingers ran up her side and over her nipples, and gave them a little pinch. Katie was powerless to flinch.

With no break in Maestro's motion, Katie felt a hard, cool buzzing on her clit. It was held against her and Maestro stuck something else on her.Is he taping a vibrator to my clit,she thought. Katie was soon proven correct and the buzzing held firm and both of Maestro's hands continued to lightly dance across every inch of her body.

After a few minutes, the intense buzzing from the vibrator started to approach an uncomfortable state. Again the thought of using her safety sound crossed her mind. This is what lack of control really means,she though.I am here to let him use me.

Maestro's fingers found their way to her nipples and he began to pinch them lightly again. Katie could now feel that her hips were slightly rocking as the vibrator provided a constant buzz on her tender clit. Maestro's pinching became more and more intense with each moment that passed. Soon, he was pinching so hard, she tried to pull away from his hand which only caused him to pinch harder. Without warning, Katie swore she felt the tingling of a second orgasm.So soon?With a slower build, she felt her pussy emit a wave of sparks through her body. As her body pulsated with pleasure, Maestro pulled her nipples away from her body with a new vigor until they slipped from his tight grip and snapped back into place.

"Good girl Katie. That makes two."

Katie came back from the second orgasm quite a bit faster than the first. Her nipples were echoing with pain. Her clit felt raw and was beyond sensitive as the vibrator mindlessly continued vibrating. She began, again, playing with the idea of ending the session.

"Let's go for one more, shall we?"

Katie's attempt at communicating resulted in a single and short moan.

"One more it is.", Maestro said with vigor.

Katie didn't know how she was going to be able to take this. Her entire body felt numb. Her clit was so sensitive she started to have problems forming thoughts. The vibrator increased in intensity.

"That should help", Maestro said.

Katie's body tried to pull away from the buzzing, moving her hips like a belly dancer but the attached vibrator followed her every move. Maestro's fingers circled each of her nipples. She wanted to moan, but all her mind could do was focus on the hard buzzing. She felt Maestros hands as they explored every inch of her vulnerable body. His fingers ran along her cheek and traced her neck. He ran his hands over her arms, down to her breasts, cupping and feeling each one as he passed them. He moved over her stomach and down her legs, making sure to lightly touch her inner thighs. Every movement he made sent chills through Katie's body. Katie's hips began to quiver and shake uncontrollably.

"Are you ready to cum for me?"

The words penetrated Katie and she could feel a tingling rising between her legs. Maestro immediately removed the vibrator and began lightly slapping her swollen clit. The quick and repeated slaps of his fingers on her clit, pulled on a feeling deep inside of her.

Her back arched once more as her tingling clit was slapped.

With a hard smack, Maestro yelled, "CUM NOW!".

Katie body did as it was commanded and was immediately engulfed in a warm sensation, unlike anything she had ever felt. Her entire body shook as he continued to make contact with her clit. She felt only pleasure as her arms and legs uncontrollably pulled on their restraints.

"MMMMMmmmmmmmmmuuuuuuuuuhhh," was the only sound Katie could make with a gag so deep in her mouth.

Katie could have sworn she was on the verge of blacking out. As her third orgasm of the night receded, her chest heaved up and down as she tried to catch her breath from behind the ball gag. She could feel the sweat on her body as her mind began to slowly come back online.

"Three orgasms in one hour. Very good Katie."

Katie never imagined she was capable of three orgasms in a single hour. She could barely have two orgasms in a day on her own if she even had the time.

Katie's breathing returned to normal while she heard Maestro moving about the room. From the sounds, she knew Maestro was rummaging through his bag of toys.

"Katie, now that you have experienced immense pleasure, it is time to contrast with pain."

Katie's body thrashed as she felt the searing crack of a leather crop across her inner thigh. Maestro slowly and steadily continued to lash her tender and exposed things, leaving a light trail of pain as he moved back and forth from each thigh. Katie's entire body remained clenched and tight as she had no sense of when or where the next smack would land.

"Your body must appreciate both ends of the spectrum."

Maestro focused his attention on Katie's nipples which were now hard. The crop came down, smacking each one, slowly changing their color from pink to rose. Her back involuntarily arched, only making her defenseless breasts easier targets. Her wrists and ankles tested the tight restraints that held her body open as she had no way to escape the steadily increasing pain.

Maestro's hits, which seemed to go on forever, became harder, leaving the lingering pain to overlap with his next hit. After what felt like an eternity of whipping, Katie was at the limit of finding the pain unbearable.I can't do this anymore,she thought. Just as she was about to emit her safety sound, a new sensation came over her. Her entire body began to feel cool and warm at the same time while the prickling pain in her nipples started to become muffled. Each hit across her breasts began to feel like a cool breeze with fingernails lightly running over skin. The crop found its way to her still tender pussy. Each slap made sure to find her clit. Instead of the original burning pain, each hit on her clit felt cool, just as it did on her nipples.

"Mmmmmm." Katie let out a pleasurable moan with out even realizing it.

"Good girl," Maestro said. "Keep it up and you will be rewarded."

He continued to whip her clit harder and harder. Where there was once pain was now the pleasing cool sensation as her entire body pulsed with her racing heart. Katie no longer could comprehend what she was feeling, all she knew was her body longed for more.

Each hit, like lightning, and a cooling sensation raced through Katie's nerves. With a final crack of the leather, her clit exploded and her entire body began to vibrate with the tingling of an orgasm. Her entire body felt flush. She felt Maestro's fingers on her nipples, pinching and pulling them to their physical limit. Instead of pain, Katie's tingling doubled in intensity and her body continued to writhe in the pleasures of an orgasm while moan after moan came through her gag.

Katie lost sense of what happened for a moment, but as her orgasm subsided, she was in a state of disbelief. She had no idea how to explain what happened or even what she was feeling.

"Good girl," Maestro said. "Very good."

There was a very long silence where Maestro said nothing and did not make a single noise. Katie began to wonder if he might have left the room. Katie was feeling the exhaustion from 4 orgasms in such a short time, and the room was so warm, she slipped off to sleep hoping Maestro had not abandoned her.