Dominating Ken Pt. 05-08

Even though Jen knew this from her conversation with Kareena, she acted surprised "you do? What is it dear?"

"It's Kimmee."

"Kimmee. How cute!! It fits you perfectly. Is Kimmee excited about having her ass filled with a plug. Mmmm baby, it will be just like a pussy. Aren't you excited Kimmee?"

Hearing Miss Jen say his feminine name was so strange. It was the first time he heard anyone actually say it. It sent an erotic charge through his body and made him feel very girlish. His cock swelled against the cock tube. His slight grimace from the pain was noticed by Kareena from across the room. She chuckled to herself knowing that he was suffering as a result of her.

Ken replied, "I don't know Miss Jen. I've never had anything in my ass before. I don't know if I'll like it."

"Of course you'll like it sweetie. You are such a sissy slut. You'll probably be dying to cum once you feel the fullness in your ass. Weren't you begging me to fuck you up the ass last time your were here (*laugh*)."

Ken had forgotten about that. "Yes. I guess I was, but I was so horny. I couldn't help it."

"See what I mean darling. You are a slut. You want it bad don't you. Don't worry all sissies are the same. I know your little pee-pee is trying to grow hard just thinking about it. Still have it tucked between your legs like a little pussy?"

Ken's face started to flush red. He was hoping Miss Jen would not mention his cock. He didn't want to admit that he was in a chastity device. It was pointless to try and hide it now. "Well....not exactly. My mistress has me in a chastity device the keeps me from getting hard."

Ken braced himself for laughter. He was surprised at Miss Jen's reaction. She was smiling and interested. "Well, your mistress is very smart. She knows how to control a sissy. In a bit of pain are you?"

"Yes. It's has helped me stay calm and I do like wearing it for her but I've had it on for a few days and I am so horny! I'm dying to take it off but she has the keys." Ken expected to see a look of surprise on Miss Jen's face but she remained interested and un-phased at his revelation. He continued. "I'm extra horny today because I am going to meet her in person. I can't wait!!"

His last revelation caused an reaction from Miss Jen "That's fabulous!! She will be so proud of her Kimmee! So you can't wait to get that thing off, huh?"

"Yes. I'm just soo horny and my cock keeps trying to get hard but this device is so tight around my cock that my cock can't get hard."

Miss Jen reached down and squeezed his crotch area. She could feel the hardness of the cock tube in his pants. This gesture excited Ken and his cock swelled and he grimaced in pain. Miss Jen giggled at his predicament. She leaned in and whispered in his ear, "such erotic torture. It's nice to see a boy suffer for his mistress. You are very loyal and obedient. "

Ken took a few deep breaths. He was surprised by the next words that were whispered in his ears, "I have a surprise for your obedience. A gift from Mistress Kareena."

His body tensed at the sound of his mistress's name. He stepped back a few steps and stared at Miss Jen with curiosity and astonishment.

Miss Jen was reveling in the full attention that she was commanding from Ken. She knew he was focused on every word that she said. She reached into her bra and produced a key and held it upright between her forefinger and thumb like a carrot in front of the horse; A prize for Ken to claim. "It just so happens that your mistress stopped by for a visit today. We had a lovely chat about you Kimmee. You're in for quite an adventurous weekend. I would be excited too if I were you. Would you like me to free that little pee-pee of yours?"

It took Ken a few seconds to respond. He was in a daze. His Mistress had actually come into the store and met Miss Jen. Ken's pulse quickened. A million thoughts rushed through his mind. What did they talk about? Did she know about Miss D? Did Miss Jen tell her about how Ken played 'dress-up' in the store and the he begged like a little sissy to be fucked up the ass? Ken wondered whether Mistress Kareena would be mad or excited from everything she learned. He didn't know what to do. He just had to take it one step at a time. His eyes focused on the key and it finally sunk in that freedom was right in front of him. Miss Jen held the key to his chastity device. Excitedly he replied, "Yes! Yes! Please unlock the device."

Miss Jen thought about toying with him a bit, but she figured he had been through enough torture. "Follow me," ordered Miss Jen. She walked to one of the dressing rooms and Ken hurried after her.

By now Mistress Kareena had made her way back up to Miss Jen's office. She sat in front of the large television and watched with intense interest and arousal at the scene taking place in the dressing room below.

She watched Ken unzip his pants and drop them to the floor. She could see a large wet spot on the front of his purple panties. Miss Jen stared at it and ran her finger over the wet spot. "Hmmmm. It seems that even with a chastity device you still wet your panties. Such a naughty little girl.." Miss Jen used both hands to pull down Ken's panties. His cock was swelling against the cock tube. He could not control himself. Being talked to like a little girl was sexually exhilarating. Ken felt submissive and girlish.

On the TV monitor Mistress Kareena stared at the chastity device on Ken. She clicked a few keys on a keyboard in front of her and zoomed the camera in on the device. Her pussy quivered and pulsed at the sight of it.

Jen inserted the key into the lock and turned it. Ken's heart skipped with excitement at the clicking sound. Miss Jen removed the lock. She tugged at the cock tube. It did not come off easy since Ken's cock was swelling. Slowly she managed to work it off his cock. His cock instantly swelled to its full size. Precum oozed out the tip. The feeling was heavenly and Ken gasped at the fullness of his cock.

Miss Jen reached down and rubbed the precum over the tip of Ken's cock. She commented. "Mmmm. Yes. Your little pee-pee is happy to be free."

Ken's entire body shuddered. It had been over two days since his cock had been able to grow to its full length. The freedom was a welcome feeling. He was grateful to Miss Jen. "Thank you for freeing my pee-pee Miss Jen."

"Well you should thank your Mistress when you see her. She was nice enough to stop by, introduce herself and give me the key." Miss Jen continued stroking Ken's cock and massaging the leaking cum over his cock head and shaft. With her other hand she grasped his balls and gave them a firm but gentle squeeze. Ken's knees weakened and he moaned at the pleasure. With one hand firmly on his shaft and one hand firmly squeezing his balls, Jen had Ken's undivided attention. His mind was blank. All he could think about was the pleasure between his legs. Miss Jen was enjoying the game. She continued to speak to Ken.

"Your mistress also gave me a few instructions to prepare you for her visit. I know you're going to be a good girl and listen to me, right Kimmee?"

Ken did not have to think twice about the answer to her question. He just nodded his head in agreement. Miss Jen giggled and squeezed his balls and cock once more before letting go. Ken's cock seemed to pulse a few times by itself and then he was left with any empty feeling....a need for more attention to his cock. He wanted Miss Jen to continue playing with him. His urges were strong. He wanted Miss Jen to fuck him hard. This thought was another sign of Ken's transition into feminine submissiveness. Prior to meeting his mistress he always thought about fucking girls. Now it was instinctive for him to want to be fucked by the girl. This was a subtle but significant difference in his mindset.

Miss Jen instructed Ken to open the package that contained the smaller butt plug. Ken did as instructed, his heart pounding harder knowing where this was going to lead. He pulled the plug out of the package. It was flesh colored and rubbery. It was about 6 inches long and narrow at the top. Towards the bottom the plug bulged out a few inches and then narrowed again. At the bottom of the plug was a flat base.

Miss Jen took the plug from Ken and then opened a small packet of lubrication and began rubbing the lube on the plug. She took her time greasing up the plug, knowing that Ken was staring and thinking hard about what was about to happen. Ken's cock seemed to twitch at the perverseness of the situation. Although the plug was narrow, Ken still could not imagine it fitting inside his ass. His ass tingled as he thought about it. Part of him was excited at having his ass filled. It was so perverted and he knew he would feel like a true sissy with his ass filled. On the other hand, Ken knew that having his ass filled would take away almost all the masculinity he had left. He had come a long way into being feminized but he saw this as a big step forward. He knew it would be hard for him to turn back after the night was over. The thought of protesting entered his mind but quickly retreated at the sound of Miss Jen's commanding voice.

"O.K. slutty girl. Bend over and show me that boy pussy."

Miss Jen radiated control and dominance. Her presence alone was intimidating to Ken. He obeyed her order with out hesitation. Ken had figured eventually his Mistress would fill his ass with something. However nothing could ever prepare him for the sensations that he was about to experience.

First he felt her slick fingers slide up and down his ass crack. His body shuddered at the strange sensation. Slowly she worked a finger in and out his asshole. At first the intrusion felt awkward and weird. However, as her fingers probed his ass and the lubrication coated his insides, an erotic warm feeling rose up through Ken. It was like nothing he ever felt before. Just as he was beginning to get used to the pleasure Miss Jen removed her fingers. Then he felt the tip of the plug at his ass. His ass seemed to contract and tighten and the new intrusion.

Miss Jen coached him. "Relax darling. You're going to love this. Your going to love having your pussy filled."

Her words relaxed and excited Ken. Her reference to his ass as a pussy heightened his arousal. He felt the tip push in slightly and then back out. It was slick and rubbery. Miss Jen pushed the plug in and out of his ass again. She continued to do this, working the plug in deeper with each push. Each push was a shot of pleasure to Ken and each push was milking cum out of his cock. A small pool of cum was forming on the tile floor beneath Ken. At the moment no one seemed to care about the pool of cum but Jen had plans for the when all was said and done.

Finally Jen was able to get the wide part of the plug into Ken's ass. Once the bulge passed the opening of Ken's ass, his ass closed around the plug and held it in place. The fullness inside Ken was mind blowing. Ken had never experienced such intense and focused pleasure before. His ass was full and tingling. His cock was twitching and dripping cum. Ken's mind was on emotional overload. He almost began to cry at the intense pleasure. All he could do was stand there and take deep breaths and moan, "oh my god.....oh my god....this is incredible!!"

If Miss Jen's hands were on his cock now he would have cum. If there was a hole in the wall Ken would have run over and fucked it. However with no pressure on his cock he could not cum. He wanted to desperately cum but he could not. Miss Jen's voice slowly penetrated all the crazed emotions that were filling Ken's head. "Don't you cum Kimmee....hold that nasty cum inside.....concentrate and hold it in....Don't disappoint your mistress!!" Ken's eyes were closed and he focused in on her voice. He began to take deep breaths and try to calm himself down. Finally his head cleared and he opened his eyes to see Miss Jen grinning at him.

She smiled. "That was a close one Kimmee. You did good but you still made a mess on my floor with that leaky thing of yours.." Miss Jen pointed at the pool of cum on the tile floor. Get down there and clean it up."

Ken knew exactly what she meant and he obediently got down on his hands and knees and licked up his sticky cum off the floor. As he bent down he could feel the butt plug sliding out if his ass. He reached around with one hand and held it in. Miss Jen giggled at his awkward position.

When Ken was finished, the spot on the floor was cleaner than it had been all day. Next Miss Jen ordered him to stand up and then she walked over and held out his purple panties for him to step into. She slid them up his legs and said, "these should help keep that plug in your ass." Ken finished getting dressed. The plug seemed to want to slide out of his ass but as Miss Jen had indicated, his tight panties held it in.

Ken was not the only one who made a mess. Upstairs in Miss Jen's office, Kareena had watched and heard the whole scene on the TV in Miss Jen's office. Her fingers probed and pulled at her pussy during the entire ordeal. Kareena was in awe at the power and control that Miss Jen commanded over Ken. Jealousy had quickly given away to fascination and arousal. She could see that Ken hung on Miss Jen's every word. She could see that Miss Jen had driven Ken to the point that he was a mindless robot willing to do anything she wanted. She watched a young and devious girl manipulate, humiliate, and control a grown man. Kareena was grateful that Miss Jen had aroused and softened Ken up for her. He was going to be puddy in her hands later that night.

Watching Miss Jen manipulate Ken was an extremely erotic experience for Kareena. Seeing her work the butt plug into her little slutgirl was too much for Kareena. While her little Kimmee was lost in an emotional hurricane, Kareena was pushing her fingers deep into her pulsing hole and bucking like a crazed woman in the plush leather chair. She imagined herself fucking Kimmee with a long strap-on. Kareena's pussy tightened and pulled her fingers deep into her hole. She arched her back and enjoyed the rush of pleasure that coursed through her body. By the time Miss Jen slid Kimmee's panties on, another orgasm slammed Kareena. This time she screamed out with pleasure. Out of the corner of her eye, she was certain she saw Kimmee look up towards the camera and give a knowing smile.

When Kareena was done she stood up and straightened her clothes. The room smelled heavily of her sex and she could see a large damp spot on the leather chair where she had been sitting. Although she was alone her face flushed with embarrassment at her mark. She quickly made her way back down to the store.

When Kareena walked into the store, she positioned herself in a spot where she could easily overhear the conversation between Ken and Miss Jen.. Miss Jen was commenting about the meeting that was going to take place that night between Ken and Mistress Kareena.

"your mistress is going to be proud of her Kimmee. I just know it. Did you buy her a gift?"

Ken's body tensed. He didn't think about that. "A gift. Uhh..no .she didn't tell me to."

"Naughty girl. She shouldn't have to tell you. She's your mistress. You need to take care of her!"

Panic started to set in with Ken. Amused, Jen jumped in to save the day for him. She gently rubbed his shoulder and talked down to him like he was a little girl. "Awww. Don't worry Kimmee. Miss Jen is going to help you out. We'll pick out a nice set of lingerie for her. Would you like that Kimmee?"

"Yes...but...I have no idea what size she is?"

"Let me worry about that. I'll find something that will fit just about anybody."

Jen actually had an outfit in mind. Before Ken even walked into the store, Jen knew that he would be walking out with a black mini dress for his Mistress. It was what Jen wanted and it was just a matter of manipulating him into buying it. Everything Jen said to Ken had a purpose. Her conversations were always purposely leading him in a specific direction. She knew he had a sissy name and she made him want to tell her it. She knew he was going to meet his Mistress that night and she manipulated him into admitting that to her. Manipulation and influence were skills that Jen had mastered and had made a natural part of her every day life. Every move she made was calculated. She was beautiful, intelligent, and cunning. An attractive and dangerous combination that put guys and girls under her spell..

The outfit she had in mind would fit Kareena perfectly. Out of habit she had sized up Kareena pretty quickly when she first walked into the store. She figured her breasts to be a 36C and everything else to be a small or medium size. Over the years Jen had become a pro at sizing up people's measurements just from a quick look over. Jen walked over to a rack along the wall and pulled off a simple black mini dress. It was a dress the Jen knew would cling to Kareena and accentuate all her curves perfectly. The thin spaghetti straps would look sexy on her shoulders. Jen pictured one strap inadvertently sliding off a shoulder, providing an inviting view of Kareena's firm breasts. The thought caused Jen to shudder. She could not wait to see it on Kareena. She glanced over at Kareena and gave a quick wink before returning to Ken.

Kareena's heart fluttered for a second from the playful flirtation. It was strange but she was becoming infatuated with Jen. She was not into girls, at least she never was before, and so the slight tingling and pulsing feeling in her pussy was confusing to Kareena. She shook it off as arousal form the strange situation she was in. Kareena was a little unsure about the dress. It was a little provocative for her tastes. Then again it's probably perfect for the occasion, thought Kareena.

Jen held the dress up for Ken. "This will be perfect. I guarantee she'll look sexy in this and your mouth will be watering." Jen walked over to the cash register. She wanted to usher Ken out of the store quickly so that Kareena could get back to her plan. This as also Mistress Kareena's cue to leave. Quietly she disappeared out of the store and headed to her hotel to prepare for Ken's arrival.

Miss Jen rang up the order. She smiled at the total amount of $175. Ken was easy money to her now. She figured that going forward he would be worth at least $150 a visit. "No need for your credit card Kimmee. I have it on file." Miss Jen printed out the receipt and handed it over to Ken to sign.

Looking at the total amount, his stomach tensed. Financially he was feeling the impact of this new lifestyle. He was enjoying it too much to argue. Somehow he would figure out how to pay for it all. Ken signed the receipt and handed over to Miss Jen. Miss Jen walked around the counter and handed him his bag. "Now then, we have just one more order of business. I have instructions for you from Mistress Kareena. However, you must give me the cassette tape from your car in order to get them."

This was a departure from Kareena's original plan. She had never anticipated that Miss Jen would take control of the situation and talk her into allowing Ken's cock to be freed from the chastity device. The whole ordeal with the butt plug was Jen's idea. Therefore, the rest of the tape recording was irrelevant at this point so Kareena wrote a note and asked Jen to exchange it for the tape.

Ken ran out to the car and returned with the tape. Miss Jen smiled and handed him the note. It read:

You're doing great slut! Now go directly to the Marriott Hotel, room 372. I'll be waiting for you!"

Ken's pulse quickened. He was finally going to meet his mistress. Jen patted him on the ass and said, "How fun tonight Kimmee. Be sure to stop back and let us know how everything went."

"Thanks. I'm a little nervous. It should be fun though." Ken walked out to his car aroused and excited at what waited for him.