Coffee Tea Or Chastity Ch 03

She picked up the car right where he said he left it. She had told him that she was only in town for a short lay over. However, she didn't say how short. She'd do what she needed to do and leave, but she would be in town for three days. Three productive days.

She checked into her hotel room and cleaned up and got changed. One look in the mirror and she was satisfied. Oh, how she enjoyed this stop. Before she knew it she was on her way. It was close enough to walk, but she didn't want to leave a clue as to how close she was or how long she'd be staying.

Number 19 was some banking executive, but it turned out he was as pious as he was deviant and preferred to stay anonymous. Which suited her.

It had been three weeks since her last visit, which didn't end as he'd hoped. Which meant he'd been pent up for almost 2 months. Her instructions were clear and she had no doubt he'd follow them to the letter.

In no time she was at his door. She smoothed her suit out as she waited for him. Her hair was pulled back and tucked into her shirt. Her suit was a mens business suit. She wore no jewelry or make-up and her only accessory was a briefcase. In passing she looked the part of some hipster business man, but would never pass upon closer inspection. Her ample bosom made sure of that.

He opened the door. "Hello." he said trying desperately to control his excitement. "Please come in." He took her case and took off her coat. Her boobs still prominent, despite the tight sports bra she put on.

She turned to him and gave him quick kiss on the lips. "I've missed you 19. Let me see." she said stepping back holding his hands, looking him over. "Very nice. You could almost pass. Let's call you Nina for tonight. "

The two inch heels put him eye to eye with her. Sheer stockings, a knee length pleated skirt with a tight blouse, complete with breast forms and a bullet bra. A string of pearls around his neck matched the earrings he had. His hair and make up just right. He looked like a 1950's housewife come to life. "I like what you've done with yourself."

She pulled him close and grabbed his ass. "A pearl necklace. Something you want to tell me?" she said with an evil grin. "Fetch me a drink and meet me on the balcony."

"Yes, Sir." he said turning away. She smacked his ass and he jumped and squealed as they parted.

The balcony was fairly large and was only lit by the glow of the lights inside. The clicking of heels and clanking of ice announced Nina's arrival to her. She turned and took the glass, but holding his hand on it. She stared deep into his eyes for a moment. They burned with a wicked gleam. "Did you miss me Nina?" She ran her free hand through his hair and toyed with his ear.

"Yes, Sir." He could feel his caged member growing to its limit. He was certain he was leaking already. His heart was pounding, wondering what his mistress had planned for her 'pleasure attendant'. A nervous energy surged through his body. What ever it was he was excited for it.

She took the drink, letting his hand go and sipped it. Never taking her eyes from his. Toying with his ear and hair. She took another sip and as she put the drink down on the ledge she pushed him down gently with her other hand. "Let's find out how much."

He found himself squatting down in front of her crotch and he looked up to her. She looked down and blew him a kiss. "Go on be a good girl and open your surprise."

He fumbled with her belt and trousers as she put her hands in her pockets.

He gasped as a seven inch life like dildo flopped down in front of his face. She tugged at the straps in her pockets, that she cut holes into, to tighten it up. As she did she felt the wearable vibrator nestled inside her press into her tighter.

The vibrator was about the size of a small hand with a short bulb sticking out of the palm. Where the fingers should be were a series of nubs pointing in the same direction as the bulb. Once inserted in her the nubs pressed against her clit and the surrounding area. She hoped it worked as well as advertised.

Their eyes were locked on each other as he slowly moved to her and kissed the tip of the phallus. He slid his lips over the tip, then kissed the tip all over. Gently and sensually. His submissive eyes looking for approval.

"That's it; show Master how much you missed him." she whispered.

She let her head fall back as he slowly impaled himself on her cock. "Oh yes. That's it. . . Such a good girl." she cooed. One hand ran through his hair as the other found a small remote for her vibrator in her back pocket. Her vagina buzzed to life on the softest setting. "Oh my. . Yes. . . You enjoy my cock don't you?"

He let out a muffled yes as he slowly slid it in and out of his mouth. He then pulled out and then ran his lips up and down the sides of her shaft. After a few times, the tip found its way back into his mouth and he swirled his tongue around it.

He felt the slight hum of her vibrator as he slowly took more and more of her in his mouth. He paid it no mind though. She had realized his fantasy. His was transfixed with the dildo he was worshiping. Transfixed on the fact he was dressed as a she and she as a he. Transfixed on the fact that he was squatting in front of her, performing a most debasing act. His hands found her hips as his mouth worked with a seductive purpose.

She scrolled through the settings of her vibe and found one whose pulsed matched the speed of his bobbing head. She'd never used this before and wondered if this is was a blow job was really like as she felt an orgasm welling inside her.

She found the next setting to increase the pace. Her hands grabbed his hair to make sure his was in rhythm with her. His muffled sounds were interrupted only by the slurping sounds his mouth made.

"Yes, yes, suck it" she hissed. "Oh fuck yes, suck my cock." He moaned and gagged with each bob, but she kept him moving to the beat inside of her. "Suck it, suck it, suck it. Suck it!"

She felt all her energy tingle and burn inside her. Then it all flooded towards here groin like a nuclear implosion. He moved his hands to grab her ass, but in doing so accidentally hit her remote and changed it to the next setting. Fortunately, for his sake it wasn't off, but rather it changed to the strongest steadiest pulse.

It was more than she could bear and her body convulsed with paralyzing shudder. Unfortunately for him she pushed in and pulled him towards her as she climaxed. He tried to push off as she gagged him. To no avail. Her muscles were locked and her legs quivered as her head fell back. Her eyes fluttered and she let out a guttural moan from her slackening jaw. He was stuck, the entire shaft stuffed into his mouth. He tried to breath, fighting his gag reflex.

When she did finally let go he fell backwards to the ground. Choking and gasping for air. Spit dripping from his chin. One of her hands found the off button on the remote and her other found her drink. "Holy shit Nina!" she said gulping down her drink and leaning on the ledge, half out of breath. "You were amazing. That's quite a talent you've been hiding."

After a few minutes she composed herself. "Let's eat." she said as she walked past him.

Her words sank in as he pulled himself up and went inside. He was so, so horny and wanted desperately to finally get unlocked and shoot his load. Tonight's events only made it worse. He trotted inside and got her another drink. Then hurriedly got dinner and set the table.

They sat and enjoyed a nice meal. She made pleasant conversation about investing and banking, which he was more than happy to answer. He was always surprised at how versed she was on the topic. Yet, as they spoke, each were playing the events of the balcony over and over in their heads.

He felt so liberated by tonight's events. He thought back to when he first told her about his kink to be feminized. How he was sucked into her controlling vortex. Every visit he would have to prove to her how much progress he'd made. More and more. Little by little. Eventually, just to be unlocked and maybe teased, he would be made to beg to show her how well his mouth could work over her dildo or how well he could ride one suction cupped to the wall or floor. To which she would want to see before teasing him. He thought about she would cruelly test him, asking if he'd rather play with his 'clit' or her cocks. The few times he was allowed to cum, ruined orgasms mostly, she made sure his mouth and ass were well stuffed. Always having to clean up his mess. He remembered how he would beg to be a true sissy slut for her, always on the slim hope he'd be rewarded with a full orgasm.

She, on the other hand, was no stranger to what she'd done to him. 'Locked and Laced' is what she called his type. She'd denied them, dressed them, then conditioned them while teasing them to want to realize their own fantasy. She'd taken a few others further. However, tonight was a first thanks to that new contraption she'd picked up a few days ago. Now violating and degrading one of her 'pleasure attendants' was not just her going through the motions; it was proving to be a very satisfying endeavor.

A wicked grin flashed across her face as she thought about what she still had in store for him. If he didn't then he was dense. And if he didn't follow her instructions. . . Well, then he was going to be very sore tomorrow. Despite having an orgasm that was one for the ages only a short time ago, she was wet and tingly at the road ahead.

Soon enough dinner was done and he cleared off the table. He came back and refilled her drink and asked if she'd like some coffee instead. She reached behind him, up his skirt and ran her hand up his inner thigh stopping only when he reached his sensitive testicles. "I thought we'd have dessert first." she cooed. Her hand finding his cage and her fingers teased him through the metal bars that confined him.

He inhaled deeply and bent forward over the table. His eyes closed and his jaw went slack. He slid his other leg out, locking his knees and arched his back. "Please." was the only word that escaped his lips.

"Please what Nina?" she asked coyly.

"Please. . . Fuck me." he said. More of a soft surrender than a demand.

"I don't believe you Nina." she replied playing with a calm authority while his dripping cock straining for more for relief than release. "I think you're hoping to be unlocked tonight. . .perhaps even. . . rewarded."

"No Master! I want you to pleasure yourself with me." he was almost whiny and nearly bent over the table as if to offer himself to her.

She stood up and fumbled around with something for a bit, he couldn't tell what. Then he felt both her hands between his legs fondling him. He prayed she was unlocking him. It was not the case. She then ran a hand back to the crack of his ass. He lifted his ass and bent over further. Her finger found his hole and pushed in without resistance. "Oh my look at how wet you are. How eager and ready. So pretty and dressed up. Your crotch less panties making it so easy." she said as she worked her finger in and out.

"Is that was you are? An easy slut?. . . A cock hungry sissy?" she asked as she pulled her finger out and flipped his skirt up. She slapped his ass hard. "Well?"

"Yes." he replied. "That's what I am."

"Mmmm. . . Your going to have to prove it to me Nina." She kicked one of his legs out, spreading them further.

He felt something press against his sphincter. Then a key ring with a small key landed on the table in front of him. "Which do you really want?"

He was sure it was a test. He knew what she wanted him to do, but he knew what he really wanted. Wanted more than anything right now.

He reached up and took the key and moved it away as he pushed back towards her. He moaned softly, passionately as he slowly impaled himself on her. Once he took it to the hilt he worked back to the tip and filled himself again. "Oh Master. . .Please. . ."

She switched on the vibe and smacked his ass. She then grabbed his hips and worked hers in unison with his slow thrusts. "Yes. You like that; don't you? Bending over and wanting to be taken. Taken and used. Used for the pleasure of cocks. Let's see if my cock likes your pussy as much it liked your mouth."

She fought the urge to just pound away at him as her wet and dripping vagina buzzed away, fueling her passion. "Well, Nina? Tell me. . . Tell me what you're thinking."

Long slow thrusts found their way into him, again and again. He let out a feminine moan each time his prostate was brushed. He felt it building inside him as his hands clenched the table cloth. Slower than normal. So slow. Too slow. Each slap of her hips into his ass and each one of her thrusts moved him only a bit closer. He let out a squeal. "Fuck. . .Me. . . Hard. . .er. . . Mmm. . . Mmmm. . . Pleaseeee!"

She was all too happy to indulge his request and found a good two tone setting to match her new pace. She felt her own orgasm swelling in her. She glanced over and looked at the reflection of them on the glass patio door. Their eyes met. "You like this, right?" she hissed with a sharp tone. "Is this what you wanted? Huh, you like getting your tight pussy stuffed with cock!?!"

"Yes. . . Yes. . . Yes!!" he moaned between her thrusts. He was overwhelmed at how good it felt, at how being violated by her felt so right. The slapping sound of her hips into his ass and her grunting echoed in the room. He felt flush and his nerves tingled with an energy that signaled the start of an orgasm. "Fuck. . .me. . .fas. . .ter!. . .Fuck. . .fuck. . . fuck!. . . Yes. . .yes. . . cum. . . in. . . side. . . me!!" His confined member needed only the slightest touch to make him explode. It needed the one thing she wouldn't allow to happen.

"Take it sissy!" she growled. "Take my cock." She smacked his ass hard; so hard her own hand stung. She then turned the vibe to its highest, fastest setting and began plowing into him with total abandon.

"I'm gonna cum. . . I'm gonna cum. . . Let me cum!!" he whispered over and over again. As if to will himself over the edge that he'd been teetering on for some time now. He felt it. He was right there. He bucked and shivered trying desperately to gain the slightest of friction on his dick. There was no to be had.

Her pace was a blur as her fingers dug into his flesh. She let out an animalistic groan that slowly became a slow drawn out 'Oh fuck yes'.

He too began to shudder and twitch as she collapsed on top of him, but his sensation was different. His mind was trying to slip over that edge. He felt his cock pulse, he quivered and shook. His nerves were energized, bubbling and ready to take that lightning quick trip to his groin and explode. All the physical signals of an orgasm, but mentally he was waiting for the nerves in his penis to send word to him that it was ready. That signal never arrived. He was caught in some orgasm purgatory. Instead of one gigantic penile induced explosion that would drain him of months of pent up sexuality he was racked with a million micro explosions throughout his body that left him only wanting more.

She lay on top of him for a moment. Catching her breath.

He made a heavy sigh as she pushed off him and a feeling of emptiness passed over him as the dildo slid out of him. He wanted to break character and ask to be released, but he thought better of it. He lay there instead watching her reflection fix herself up. He was physically drained and mentally frustrated. Spent from an orgasm that he didn't have. His mind was spinning.

She had loosened the straps and tucked her penis up and fixed her shirt and pants over it. She made her way to the front door. Still without a word she put her suit jacket on and buttoned it. She picked up the thick envelope and put it in her briefcase. She did want to stay and have her way with him all night, but she needed to stick to her plan. Her plan to push him a little further.

He got up from the table and made his way to her. There was something odd stuck between his legs, not stuck but hanging there. However, he first needed to figure out what to say in order to get her to stay. "Master. . . I" he stuttered and stalled, though sticking with his roll of the woman.

"Sorry, I've gotta run, Nina." she said pulling him in with one arm around his waist. She kissed his lips and grabbed his ass. "Thanks for a great evening. Maybe next time I'll be able to stay for breakfast."

Without another word she turned and walked out of the door. As it was closing she heard him plead. "Call me?!?"

She chuckled as she made her way to the elevator. He could not see her Cheshire cat grin. Not only did she make him into the chastised sissy he yearned to be, but she made him feel cheap and used on top of it. Plus she found out he didn't care and he wanted more. "Locked and Laced. Works every time." she whispered as the elevator door closed.

He stood looking at his door for minutes. One arm wrapped across his waist, the other toying with his string of pearls. His mind still trying to process what he'd felt when she came. He shifted his weight and felt the odd object again. He reached under his skirt and felt a warm squishy sack.

He waddled in to his bathroom and lifted his skirt in front of the mirror. There was a condom over his cage and it was filled with a load of his cum. His mind thought back to when she was behind him, fondling him. That's what she done, she knew what was going to happen.

He pulled the condom off and reflexively he poured the contents into his mouth. He took a selfie in the mirror of his cum filled mouth and empty rubber. Knowing full well she'd asked for proof eventually.

He was still confused to his own feelings. It was the closest he'd had to an orgasm in a long time. Yet, it was the most powerful orgasm he could ever remember having. At the same time he was still hornier than ever. No post-climactic blissful relaxation or no need to sleep. No; he was a bundle of sexual energy. And with no way to release it.

She got in his car and parked it back at the airport. She got out and walked over two rows and got in another car. "Now let's deal with you number 6."