Emily's First Taste Pt. 05

It was immediately apparent to him when he would ask her.

He felt calm as he dialed the phone, comfortable in his decision.

"Hello Jonathon," she answered. The ringtone she had set for him, "Hysteria", allowed her to answer without waiting for him to speak.

"Baby?" he sounded almost childlike.

"Yes, Jonathon, of course. Did you forget something?"

"Um yes, I did actually. I forgot to ask you something," his voice was different and she could not place why.

"Yes, Jonathon?"

"I have a conference I was asked to speak at in a few weeks, in Chicago. I was wondering; would you like to go with me?"

What! Emily was dumbfounded. Really?! Will this man never let her surprise him? Rapid thoughts flooded her head. If she said no outright he would be hurt, disappointed; though he would pretend not to be. If she said she was busy, it would require a huge lie that she would have to back up. He would ask her about it and she would never be able to lie directly to him; hence the secretary ruse. Emily silently screamed.

"Em? Did you hear me? Are you still there?"

"Yes, baby, I'm here. What weekend exactly?"

"The weekend of the 20th, December."

Yes. Of course it was, why wouldn't it be? She had expected that. He had never asked her to go on a work trip, why is he asking now? He must know and he is playing me?! Emily was furious he had found out the ruse and was playing her game back. Still, if that wasn't the case, maybe she could stall and reconfigure plans.

"Sure baby, I'd love to go. Assuming there are no catastrophes at my work of course." She chuckled. Not likely she thought. But perhaps there could be one?

"Great baby. I'll have something special planned." He eluded.

Shit! He must know! Emily began frantically thinking of ways she could spin this, so she could come out on top, literally. That was the goal after all.

"Ok sweets, looking forward to it. Thank you for asking me." Emily practically whispered.

"Of course baby, I'm excited," his voice dripped with enthusiasm.

"Night love," she purred.

"Night babe"

Chapter 43

"Fuck! Fuck! Fuck!" Emily stormed through her living room.

"He knows. How could he possibly know? That man never lets me do anything for him. He is always one step ahead of me!" she thought aloud.

Her solution was apparent by the time she stepped out her second shower of the day. Standing under the steamy water always cleared her head and as she shaved she realized there was only one way she could surprise Jonathon.

The delicate scent of lily of the valley filled the room as she carefully caressed the custom mixed oil into her damp skin. Satisfied she had not missed any available surface, she set the small bottle on the counter and wiped the steam from the mirror.

She examined her face as she rubbed in moisturizer. Did other women feel they get better with age as she did? Carefully she applied silver shadow to her lids; lining them top and bottom with black liner, a much more dramatic look than she normally employed but she felt the situation required such a response. Lastly, she lined her lips and judiciously applied Bobbi Brown Blackberry lip color. Satisfied she had achieved the look she was going for, she proceeded to the next step.

She lay out her attire on the bed and took care dressing; careful not to snag stockings, and ensuring seams were straight. The image returned from the floor to ceiling mirror on the closet door told her she was just about ready, only her hair to contend with and that, she decided, was an easy solution.

Emily swept her thick hair up into a severe bun and secured it with a vintage silver bun stick; ornately scrolled silver with dark rubies, the color of Emily's lips.

"Perfection," Emily said aloud as she surveyed the mirror one last time before sliding into the ruby-colored, velvet cloak she had spent countless hours searching the internet for. She immediately determined it was worth the small fortune she had paid for it.

She had already packed most of the items she needed in the bag she intended to take with her, as if she subconsciously knew she needed to be prepared for such an occurrence.

She made her way down to the parking garage, garnering appreciative looks from the male counter-part of two couples she encountered in the elevator, their wives were not so appreciative; Emily responded by smiling sweetly to the women. They really should work on their confidence, she thought.

By the time she took her place behind the steering wheel of her car, Emily's own confidence was at an all-time high, and she considered whether or not she could take on the persona permanently.

Chapter 44

Jonathon showered after he spoke with Emily, he was content with his decision and wondered what she would say when he asked her. He was a little curious about her apprehension to attend the conference but brushed it off; he would never understand women.

When the doorbell rang, he had been relaxing on the sofa after his shower, wearing only sweatpants. He grumbled as he grabbed a t-shirt from the drawer and the bell rang a second time; whomever it was, was impatient, he thought to himself. Jonathon immediately began preparing a speech for the unlucky visitor, his annoyance grew as the bell rang a third time when he placed his hand on the knob.

"Do you have any idea how impossibly irritating..." he proclaimed as he swung the door open; never finishing the statement as the sight of Emily at his door took his breath away.

"Good evening Jonathon," Emily responded; all business, as she brushed past him and let herself in.

Jonathon turned and looked at Emily, standing in his foyer. Her velvet cloak open just enough to see the corset underneath. He was dumbstruck; just the effect she was going for.

Emily walked behind him, closed the door, and produced the crop she had been hiding in her sleeve. Slowly she ran it across his ass, as he hadn't turned to watch her, he just stood there. Emily triumphed inside, she had done it; she had surprised him.

"Aren't you going to say hello Jonathon?"

"Hel...Hello Emily."

"Good boy, Jonathon. From here on out you will address me as Ma'am or Mistress. Is that clear?"

"Ye...Yes Ma'am."

"Hmmm...You seem to have developed a stuttering problem. We will have to work on that, in the meantime....On your knees." She parted her cloak, exposing her thigh; stockings peeked out over her boots, her tiny panties barely covering her sex.

Jonathon complied, taking her in, examining very detail. He was enthralled, she was stunning, and he was memorizing the moment.

"Jonathon dear, do you like what you see?" as she removed her cloak.

"Oh yes Ma'am!"

"Much improved, Jonathon, hold out your arms."

He again complied, waiting for what he assumed would come next, but to his surprise, she draped the cloak across his arms. The weight of the velvet surprised him.

"Don't let it touch the floor, it's vintage and will cost a fortune to clean."

His cock stirred as he surveyed her, he doubted that he had ever seen her look so tantalizing.

"You will be calling your secretary, you are ill, you don't know when you will return. Understood?"

"Yes, Ma'am." He smiled at her, she was utterly captivating.

"You may stand, place the cloak over the back of the couch, and take off your clothes."

"Yes, Ma'am." Jonathon's eager reply and quick response to her commands made Emily smile on the inside, though she remained poised as she watched.

Jonathon hadn't noticed but she had brought a velvet satchel with her that she reached into as he finished undressing. She pulled out a pair of black silk boxers and held them in her hand.

"What is going on here Jonathon?" she walked over and flicked the head of his growing cock with her bright red fingernail. He started to speak, until she silenced him, informing it was rhetorical.

"Hands behind your back!"

Emily was taking immense pleasure in watching him obey.

"You have displeased me, though you may not know exactly why. In good time I will tell you, but you are going to be punished. If you thought for one second that the teasing you put me through was a lot, I can assure you dear. I may break you." She stood behind him and whispered into his ear.

"You will not speak, unless spoken to. You'll respond, when appropriate. And it goes without saying that you will not cum, unless I condone it. Understood?"

"Yes, Ma'am."

"Good, now close your eyes."

Emily was testing him, though she doubted he would know that. She picked up the crop she had set down when retrieving the boxers and slid the looped handle over her wrist. Lightly, she brushed the silk boxers down his back, across his perfect ass.

"Spread your legs, shoulder width apart," she hissed.

He obeyed and she reached between them and gently stroked his scrotum from behind. The silk felt exquisite against the delicate skin and he moaned in appreciation.

By the time Emily circled in front of him she half expected his eyes to be open, but they weren't. She was pleased and she stepped back to appreciate him. He really was a fine man. His broad shoulders looked even wider with his hands behind his back. The fine hair covering his chest unable to contain his hardened nipples, small and so sensitive, and utterly irresistible to Emily; she held back from pinching them, though he might not be so lucky for long.

She couldn't be that close to him and not feel the effects, shifting her hips she felt the dampness between her legs; musing how she had gone her whole life without feeling like she did with him.

Emily waited, silently, knowing full well he would open his eyes to see where she was; what she was doing. It took longer than she expected but she was finally rewarded with a peek.

"Tsk, Tsk, Jonathon dear. You failed. Bend over the couch, and hang on."

Begrudgingly, he complied, for he knew what was coming and although they had played this game in similar ways before, he knew Emily could get carried away.

"You look worried dear. I'll not pink you too quickly. We'll just warm up a bit."

She slid the crop up the inside of his left thigh; gently inserting it between his firm cheeks.

"You have such a nice bottom Jonathon" she crooned as she stepped toward him and ran her hand across it, squeezing each cheek, before playfully swatting it with her bare hand; forgoing the crop for the time being.

She knew that he was not quite as accustomed to pain as she, so she eased into it; progressively applying more force with each successive strike. In between each smack she caressed his ass; occasionally brushing his ball sack with her fingertips. By the time she reached ten, his bottom was only slightly pink.

"That was a warning dear, I was generous." In truth Emily was enjoying having complete control of his sweet ass.

Jonathon knew she was not kidding, the first time they had played, she had smacked him harder than he anticipated with a wooden paddle and though he didn't let her know in the moment he eventually let her know she may have been excessive. The spanking she had just given him was entirely pleasing and he was disappointed she had stopped.

"Stand up, put these on, and kneel." She tossed him the silk boxers and waited.

"Yes, Ma'am."

Emily produced a long black scarf from her bag and blinded him with it. When she was certain he could not see, she tied it tighter than necessary, presuming it would slip some on his smooth head.

"Raise your wrists," She ordered.

"Yes, Ma'am." She knew he would select Ma'am over Mistress, just as she preferred Sir to Master when roles were reversed.

Emily secured them with a second black scarf.

"Where are the remote bullets, we'll be needing them."

"Top drawer of the upright dresser Ma'am."

"You may lower your wrists. Do not move."

Emily left to retrieve the required items and when she returned, she ordered him to stand.

"We are going for a little drive"

Jonathon started to protest saying it was cold outside; he wasn't dressed. Emily responded with the crop across the backs of his thighs.

Chapter 45

Emily helped her captive into the passenger seat of her car. She deliberately smeared the tops of her breasts in his face when she reached in to buckle his belt. He moaned with appreciation and on a whim Emily straddled him in the front seat. Jonathon, fully restrained by the seatbelt, had no choice but endure it as she ground her pelvis into him.

"I have to say I am really enjoying having you prisoner," Emily leaned back against the dash and slipped her fingers under her panties, "It's making me incredibly wet." Emily dipped her fingers into her sex and coated them before coating his top lip. He hungrily tried to suck the intruding fingers before she scolded him.

"I don't think so dear, I want you to taste me, to smell me, for the ride."

"And I think I should like to look at you, while we drive," she cooed as she freed his stiff cock from its silk confines, tucking the elastic waistband under his sack.

"Mmmmm, you are so hard, you should probably get used to that, because what I have planned, you might be that way for quite some time," stroking him as she teased, he shrank in the seat; obviously appreciating her touch.

"You like that baby?" She stroked harder, not waiting for his response, before abruptly stopping and stepping out of the car.

When Emily got behind the wheel, she turned the stereo on softly. She wanted him to be able to hear the sounds outside the car as they drove. If she had gone straightaway to their destination he would have immediately known where they were going. Instead, she made winding loops through the busy city, enjoying her lower riding car. Although her windows were tinted, the advantageous lighting around a stop light afforded another vehicle of the proper height a wonderful view of her captive, hard cock exposed, which Emily would stroke for the curious onlooker. Jonathon must have suspected he was on subtle display but never said anything, his heightened senses brought immense pleasure every time Emily touched him.

Jonathon delighted in his submissive role although he was having a little trouble wrapping his brain around the fact that she had taken him captive. She had always threatened it but was never able to surprise him enough to make it effective. Enslaved in her car, his mind reeled that she had pulled it off; bringing his own fantasy to fruition. As he thought about it blood rushed to his cock and the urge to touch it was undeniable. He hoped she wouldn't notice as he brought his wrists back and slid his cock in the cleft between them. The more he thought about his predicament the more blood flowed to it and he couldn't help but touch it.

Notice it, she did. Emily allowed the gesture for a moment until she reached over and pinched his delicate nipple as a warning. Jonathon immediately returned his wrists to their original position closer to his knees. She knew his nipples were his weakness and she fully intended to use them to her benefit; he immediately regretted ever complaining when she had nibbled them.

Emily briefly considered going through the drive through with him so exposed, but decided against it, she didn't know if he was quite ready for such a display, though she tucked the idea in her head for the future.

What should have been a ten minute drive turned out to be closer to an hour and when Emily pulled into her parking garage she was glad she hadn't taken him through the drive through; the journey from parking garage to her apartment could be just as effective. While she would afford him the false security of covering his cock; his arousal was quite evident under the thin silk.

They stepped into the nearly full elevator. Their diverse audience consisted of a few couples their age, an elderly couple, and a single woman. Most of the passengers tried to ignore their presence, at least tried to not to make it obvious, as the women shot glances at Jonathon in his heightened state, and the men appreciated Emily. All except for the elderly woman who could not stop staring at Jonathon's erect cock. When her husband noticed her gawking, he tried to turn her, but it was no use, she craned her neck around his shoulder. She didn't seem particularly concerned with Jonathon's attire, or lack thereof, as she was his member.

Emily stood close behind Jonathon and whispered in his ear as they made their ascent. She slid her hand into the back of his boxers, thrust her hand between his thighs, and caressed his balls. Emily told him he was hers, his cock belonged to her and the women staring at him were obviously jealous of her possession. She told him how she was sure they were thinking about what it would be like to fuck him right there in the elevator.

Jonathon's breathing became rapid in response to her verbal and physical torture. He couldn't believe he was standing in an elevator, he identified as hers immediately by scent, with people surrounding him. He wondered if it had been the same for Emily, walking into Kyle's house, excited, yet apprehensive. He knew, as she must have, that she would never allow harm to come to him.

The elevator came to a halt and Emily escorted Jonathon through the doors and down the hall to her apartment. He couldn't help but imagine what she might have planned for him. He was awed by her, and he wondered if she knew what he truly felt for her. It wasn't until that moment, waiting for her to unlock the door, that he was sure of it himself, but he knew he must figure out a way to tell her; to show her.

Chapter 46

Emily needed a moment to think, she hadn't entirely expected her ruse to work. The weekend in December had been precisely planned; he had derailed that and as a result she was working mostly on impulse.

She paraded him into her room, tied his wrists with the same rope he had hung her from, and secured his arms high above his head. She doubted he had ever been stretched in such a way and didn't want to hurt him; but definitely wanted him stretched. Men tended to much less flexible although she was not quite sure why that was.

Although she wasn't exceptionally concerned his answer, Emily stood behind him, whispered in his ear, "Does that hurt my boy?"

"Nnn...no"

Disappointed, she smacked his ass, not nearly as delicately as she had earlier.

"No Ma'am!"

"Much better." His infraction actually made Emily more confident. She walked in front of him and without warning literally ripped the silk boxers from his body. A physically strong woman by many standards, she didn't know they would rip so easily; she smiled when they did.

Emily walked over to the dresser and ceremoniously removed numerous toys from her special drawer, emptied her velvet satchel, and opened the package she had stopped to pick up before abducting Jonathon. The only item she didn't set out was the one she had hidden in her closet, she had not wanted him to find it before their weekend, and didn't want him to see it yet, on the off chance she removed his blindfold.

Emily tinkered with purpose; allowing his imagination to run as she periodically made things vibrate, clank together, and hum. She knew that he was a patient man. It wasn't hard for him to remain silent. Nor was it difficult for him to wait for whatever came next.

Slipping on elbow length black satin gloves, Emily selected her first toy and strode over to him. She gently caressed the soft skin in the hollow between his shoulder and neck. He moaned as the softness stroked him.

When they had played before Jonathon had liked being blindfolded but hanging there, being kidnapped, waiting for her touch, was so different. She was in complete control and he relished it. He felt the muscles in his arms extending, straining, and he was surprised that it was more pleasing than he anticipated.