Dominating Ken Part VI - The Erotic Journey to His Mistress  


Thursday morning Ken was awoken from the sound of his alarm.  He rolled over and felt the tightness of the bra around his chest and was quickly reminded that he was dressed like a whore.  He looked down at his garter belt and stockings and was impressed at how sexy they looked.  His cock began to stir and swell until it pressed against the chastity device.  Ken groaned in pain.  The realization that he was wearing a chastity device sunk in.  He was horny and knew that controlling his urges was going to be hard.

Half asleep he wandered into the bathroom.  In the mirror he noticed his chest hair was matted down from all the dried up cum. His left stocking had a large runner that went the length of his calf muscle.  Ken chuckled at himself with dollar bills hanging out of his bra and panties.  He even turned around to admire the one stuck in between his ass and thong strap.  Mistress Kareena's words echoed in his head, "I want you to feel like a cheap whore when you wake up."

Ken did feel like a cheap whore and the thought caused his cock to swell again.  Once again he grimaced with pain until his erection gave away to the solid chastity device.  Ken was about to pee standing up, but then he stared at the curved tube over his penis and realized that it would be impossible to do without making a mess.  Like a girl he sat down and peed.  He was surprised at how easy it was to pee with the device and how well he slept with it on all night.  It was very snug and maybe a little too tight.  Ken realized that he probably should have chosen the larger clasp to go around the base of his cock.  He decided to keep the smaller one on until the evening.  He did not want to disobey his Mistress by unlocking his chastity device.

As instructed he pressed a thick layer of pink glossy lipstick on his lips and pulled out his cock dildo.  He stared at the dildo and thought about how crazy things had gotten with him.  He thought about putting the dildo away and not sucking it as instructed by his mistress.  Ken kneeled in front the full length mirror on his door.  He stared at his slutty image and his caged cock.  The thought of stopping all the craziness and perverseness lingered in his mind.  As he stared at himself a strange power seemed to invade his thoughts.  Maybe just one lick won't be bad, he thought.  Slowly he raised the cock to his lips.  He kissed the tip of the cock, pressing his lips into the rubbery flesh so that his lipstick would transfer onto the cock.  He stared at the pink oval and thought that it looked vulgar and a bit erotic.  Again he firmly kissed the cock head.  He imagined it was Miss Kareena that was wearing it.  Her magic was overpowering him and he stared at himself in the mirror and tried to be as sexy as possible by giving slow firm kisses.  After 5 minutes Ken's thoughts were a distant memory.  He was Kimmee the whore....Kareena's dirty little whore.  In 5 minutes the cock was covered in pink butterfly patterns and his cock was fighting the chastity device.  He ignored the pain and began to lick off his lipstick.  

Ken licked around the head and took the whole shaft into his mouth.  He imagined himself as Kimmee the whore who wanted to please her mistress.  Kimmee closed her eyes and sucked on the fleshy balls and licked the veiny shaft.  It was so vulgar and so wrong, yet he enjoyed the perverseness of it all.  Before he knew it five minutes was done. He reapplied his lipstick and began the routine again.  When a 1/2 hour had passed, Ken's mouth was tired and his cock was sore.  He had a new respect for all the women that had sucked his cock.  He was also satisfied with his new routine.  He wished Mistress Kareena were there to see him.  He knew she would be proud of Kimmee.

Next Ken showered and headed to work.  The chastity device was perfect for preventing erections and keeping his mind on work.  However, a few times, just the knowledge of him wearing the chastity device excited him resulting in quite a few painful moments. Sometimes when he would stand up or walk he could hear the padlock jiggle against the cock tube.  It was a subtle reminder of his imprisonment.

Going to the bathroom was also easier with the device.  There was no saran wrap to deal with and since he couldn't get an erection, he did not have to hideout in the stall until his erections subsided.  Ken was equally impressed at how well the device conformed to his natural body.  It was not noticeable under his pants.  All-in-all Ken liked the chastity device and he was able to be more productive at work.

When he arrived at home that night he instantly e-mailed Miss Kareena.  His e-mail read,
"Hello Mistress.  Thank you so much for my present. I was in quite a bit of pain from all the 'potential erections' but I am learning to control my urges.  I was able to get a lot of work done tonight.  However, I am afraid I was a little too eager to please you and so I chose the smaller cusp for my cock.  It is too tight.  May I switch it to the larger one?"

Mistress Kareena was waiting for his e-mail.  She replied, "Poor baby.  Is your cocky poo all sore?  Your eagerness pleases me.  You have been very good for me slut.  Would you like to cum?"

"Yes!  May I cum, please may I cum!"

Kareena's pussy was already getting damp.  She could almost feel Ken's excitement.  He was on edge and was thinking that he would be allowed to cum.  The teasing was soo much fun for Kareena.

"Yes my pet, you may cum. Unlock your chastity device and start stroking your girl cock.  Do not cum until I say so.  Let me know when you are stroking."

Kareena giggled to herself when she sent the e-mail.   She began to finger herself furiously as she thought about Ken trying to unlock the lock.  His cock was probably swelling and trying to break free.  The pain and pleasure combination was sure to be torturous for Ken.  Kareena's  pussy was so wet that her fingers glided in and out, making squishing sounds.  Her sexual aroma filled the room from the erotic foreplay.  She needed to be fucked hard.  Kareena grabbed a large dildo and shoved it into her throbbing pussy.  She imagined that Ken was fumbling with the keys and starting to panic.

A few minutes went by with no response from Ken.  Oh what a confused little girl he is right now, thought Kareena.  She was now using two hands on her dildo. She stared at the screen waiting for his response.  She pushed the dildo in and out of her pussy.  Her pussy muscles flexed and squeezed the rubbery flesh.  Finally the message came through.  It was marked priority and the subject line read HELP!  These four letters sent Kareena over the edge.  Her victim was trapped and he knew it.  Ken was dependent on her for release.  This power and control put Kareena into an erotic high.  She screamed and rammed her dildo deep into her throbbing hole.  Her eyes closed, her back arched, and waves of pleasure rippled through her body. 

With sticky fingers Kareena opened his e-mail.  She was insanely aroused at his pleading

"Mistress Kareena, something is wrong!  I can't get the lock open!! The key is not working.  What should I do?  Please help!!!"

She had already crafted a response in her mind, but she waited a few minutes before typing.  She liked the idea of Ken waiting in anticipation for her e-mail.  Finally she sent him an IM.

MK> "ooops.  I must have sent the wrong key.  Sorry."

KEN>  "Are you serious?? What should I do?"

MK> "Maybe I can mail it to you. Can you make it through the weekend?"

KEN> "(*panicking*)  I don't know Mistress.  I'm sooo horny and my cock is sore.  I don't know what to do."

MK> "Well then we can meet so I can give the key to you.  It just so happens that I am in the Atlanta area.  We will meet tonight, okay?"

Ken's heart began racing.  This was so sudden.  He never intended for this relationship to go as far as it did.  He never intended for a face-to-face meeting with his mistress.  Part of him wanted to meet his mistress but part of him was scared to meet her.  He was scared about what could happen between his mistress and him. He was scared for what he really wanted.  Deep down he wanted the meeting to happen and he knew his life would not be the same if he did meet his mistress in person.  He did not know what to do.  His fingers aimlessly typed a reply.

KEN> "I don't.  I guess.  I'm a little unsure about this."

MK> "Unsure?  Why?"

KEN> "Well...I don't know.  Just nervous I guess.  A little afraid of what could happen.  Afraid of where this could lead."

MK> "You're such a sissy.  You like what's happened so far, haven't you?  I've brought you pleasure that you never thought existed, l haven't I?  You're my little slut and you love it.  Admit it!!!"

Ken's heart thumped hard in his chest as he read her words.  His cock swelled reminding him of how much he was enjoying his relationship with Mistress Kareena and reminding him of how much he needed relief from the cock tube.  He was quickly seceding to her plan.

Suddenly pic after pic of Ken was being sent to him.  Ken pulled up the images of him dressed as a slut, a sissy, and a dog boy.  He had forgotten how many pictures he sent her.  Then a message came through from Kareena.

MK> "See what a slut you are for me.  You are mine and this is proof!!!  This will lead where I want it to lead.  I control you.  I own you.  You are my slut and you love it.  Admit it sissy boy."

Ken seemed to get more aroused at Kareena's bold statements and implied consequences of not obeying her.  She had him by the balls and he loved it.  In a short few minutes she convinced him that it was time to meet.

 KEN> "Yes.  You are right.  I am your slut.  I can't help it.  I want to obey you and 
I want to meet you.  Where shall we meet?"

Her dominance and manipulation over Ken was exhilarating.  Mistress Kareena. was pleased that her plan was coming together.  She decided to keep him in suspense for a while.

MK> "mmmm. Yes sissy boy.  I'm glad you came around.  I knew you would because you are such an obedient boy.  You need me slut.  I like that.  Tomorrow wear pretty panties to work for me.  Also pack a bag with all your slutty toys and clothes.  I want everything in there...panties, lipstick, dildo, collar and leash, etc..  Got it?"

KEN> "Yes, mistress.  Thank you."

MK> "Good girl.  Check your e-mail tomorrow afternoon for more instructions.  Now get some rest slut.  You're going to need it.  And don't forget to suck cock tomorrow sissy.  Lol.  Practice nice and good for me."

KEN> "Yes, Mistress. Good night."

MK> "Good night Kimmee."

The next day was a blurr for Ken.  He woke up and sucked the dildo according to Mistress Kareena's orders.  He picked out pretty purple panties to wear and he packed all his items into a small black gym bag.  At work he could barely concentrate because he was too nervous and excited about meeting his mistress.  He checked his e-mail every 10 minutes in hopes of getting Kareena's instructions.  Finally at 3:00 the instructions arrived.  Ken read them to himself.

"Alright sweet slut...Just a few more hours and your cock will be free from its imprisonment.  I bet you can't wait, huh?  After work, go check your PO Box.  You will find a package there.  Open it and follow the instructions.  I know you are excited about this...but do not act prematurely by leaving work early.  Lol.   You must wait until 5:00 before you leave work.  See you soon sweetie."        

 
5:00 seemed to take forever to arrive.  Finally the hour came and Ken rushed out of work and went right to the post office.  On the ride to the post office his body and mind were in emotional havoc.  He was nervous and unsure of whether or not he should meet his mistress.  At the same time he was excited and thrilled about meeting her.  He had always fantasized about being dominated.  The online relationship was fun and Ken was surprised at how far he had gone with it.  The control Miss Kareena had over him was amazing.  Ken knew that a real life situation would be incredibly more exciting.  His experience with Miss Jen and Miss D were proof of that.  In the past Ken never knew how to get involved with a real Mistress.  He thought about paying for a professional Mistress but it was expensive and he never could get up the nerve to do it.  Now he was being forced into a real situation and deep down he was glad that it was happening.  This is what he wanted. 

He parked at the post office and nervously went in.  Inside his box was a padded yellow envelope addressed to him.  He scanned the package for a return address but there was none.  He laughed too himself thinking that would have been too easy.  Ken also noticed the postmark was from his post office.  He realized that she must have dropped it off in person earlier in the day.  His heart thudded with excitement, knowing that his owner was close by.  Ken tore open the package as he walked to his car.  Inside was a tape cassette a pair of white silky panties in a ziplock bag and a typed letter from his Mistress.

Ken sat in his car and read the letter for Mistress Kareena.  

"Hello princess.  Get ready for some fun.  Put the tape into your tape player and follow the directions exactly!."

Ken pushed the tape into the player and for the first time heard Miss Kareena's voice.  It was soft, slow and sexy.  Ken's cock swelled against the cock cage from the sweet melody of her voice.  Soft and subtle background music complemented her voice.  It was a classical melody that enhanced her sensual voice.  

"Hello slut! Hello Kimmee.  By know your cockypoo must be pushing against its prison, desperate for freedom.  Don't worry it will be free in just a little while.  Follow my orders and you have nothing to worry about.  First, take the white panties I left for you as a gift and hold them in front of your face...."

Ken immediately reached for the panties. He looked around to make sure no one was watching and then he held them in front of his face.  He could tell they were expensive.  They were silky and lacey.  Very pretty.  "....While you're doing that, let me tell you a secret.  I am actually wearing those panties right now sweetie.  Mmmm. that's right princess.  When I recorded this tape earlier today I had on those pretty panties that you are holding in your hands right now....."

Ken couldn't control his excitement, knowing that his Mistress was wearing the panties earlier.  He endured the pain of his cock pressing against its cage as Mistress continued the teasing.  "....Spread open the crotch and take a look at the wet spot..  Mmmmm (*moans and deep breathing*). That's  a sign of how much fun we are going to have.  I'm going to have a few orgasms by the tine this tape is through, but your not (*laughter*). 

Now put my panties up to your nose and smell me.  Mmmm.  Smell my strong woman odor.  It's nice and fresh...from just a few hours ago.  O.k. panty boy open your mouth and put them in.  Come on now....hurry up darling.  Taste my wetness.  Taste my excitement.  Mmmm. I taste so good don't I?.."

Ken was following all her orders.  Her smell was strong and delicious.  The panties were soaked and he easily sucked in some of her juices.  He could not wait to taste her pussy in person.. 

"...Alright my little pervert princess.  Keep those panties in your mouth and start-up your car.  Let's go for a fun erotic ride (*laughter*)."

For the next hour Mistress Kareena teased Ken in his car.  She teased and verbally abused him.  It was obvious that she was playing with herself because there was constant moaning and groaning in between her orders.  Sometimes she just instructed Ken to drive and listen and she would moan and play with herself and describe what she was doing.  Ken could hear the squishy sounds of her fingers plunging in and out of her slick pussy.  This was driving him completely insane with erotic excitement.  Throughout the drive she instructed him to do various tasks such as pick up a case of beer, buy dog treats for her puppyslut, and buy a bottle of wine.

While Ken was on his mission, Miss Kareena decided to stop by the adult store where Ken had done all his shopping. At first she wanted to follow Ken around and make sure he was doing everything as ordered.  However, she thought it would be more fun to visit the adult store and try to meet the salesgirl he had been dealing with.  She also thought it would be fun to have her princess boy stop by the store and pick up a butt plug while she was there.  She could check him out without him even knowing it.  Mistress Kareena chuckled to herself as she thought how twisted and fun the idea was.  She entered the store figuring she had about 45 minutes before her princess slut boy would be coming.

In the store, Kareena suddenly felt nervous.  When she planned everything it was thrilling and in her mind she was the confident mistress playing with her toyboy.  Reality was that she had never done anything like this before.  She was about to meet the salesgirl who knew about Ken.  It would be her first in-person conversation with someone about her sissy boy.

Kareena's thoughts were interrupted by words from a beautiful young sales girl, "...hi may I help you find something."

"uh.  Hi.  Well, yes. Actually,  I'm looking for Jen."

"That's me.  What can I help you with?"

Kareena stuttered a bit but managed to inform Jen who she was and that she had sent Ken into the store a few times to buy slutty items.

Jen's listened patiently and then confidently responded, "Oh yes.  Kenny the sissy boy.  He's such a great sissy boy.  You've done well with him."

"Thank you.  He is great.  I'm glad to hear he's been following my orders."

"Oh yes. He even told us he couldn't cum.  The poor boy. I thought he was going to explode when we dressed him up the other day."

A look of surprise crossed Kareena's face. "Dressed him up?  What do you mean?"

Jen knew that Ken had not told his mistress everything that occurred.  She was a cunning and conniving seductress. She was enjoying getting him into trouble.  She explained everything to Kareena.

"When you sent him in to buy panties and stockings he was like a lost puppy trying to figure out what to get.  It was so cute.  My assistant and I gave him a little help.  We took his measurements and then I helped him find the lingerie that you ordered him to buy.  I also picked out several other slutty outfits for him to try on.  You would have been proud of him.  He looked so cute dressed like a sissy and he was so aroused from it all.  You're lucky to have such an obedient sissy boy."

Kareena was unsure how to react.  Several different emotions filled her.  She was angry that he had not told her everything that went on in the store.  She was a bit jealous at how much Jen had done with Ken.  She was also thrilled the Jen had played along with the game and teased Ken and treated him like a sissy.  Jen could sense the confusion within Kareena.  Kareena was in a vulnerable state and it pleased Jen to know this.  To Jen, everything was about control and she had to control everything and everyone.  Establishing this control was an art and Kareena was already becoming one of Jen's masterpieces.  Before Kareena could react, Jen jumped in and reassured her.

"Don't worry Kareena.  Your sissy was very loyal to you.  He told us that he was not allowed to cum and we honored that.  He speaks very highly of you and is very obedient.  I could tell that you already had him in an aroused state and submissive state.  It was your power over him that made him so obedient for us.  You should be proud of yourself."

Jen's words were comforting to Kareena.  She was new to all this and it helped to have someone else reassure her.  Jen was young but very confident and sure of herself.  Her presence was very domineering and commanding.  Kareena could tell that she was experienced with domination.  Kareena realized that Jen would be a great ally to have and a great teacher for her.  "Thank you Jen.  It's good to hear that.  I guess I'm just upset that he didn't tell me everything."

"And you should be.  A sissy should be open with his mistress.  Perhaps a punishment is in order."  Jen giggled.

"Yes, a punishment would be good.  This is perfect timing.  I am actually meeting him tonight.  In fact he'll probably be coming into the store in about 1/2 hour, unaware that I am here."

Jen smiled. "Really!  That is great.  Does he know what you look like?"

"No.  I thought it would be fun to have him shop for a butt plug and not even know that his mistress was watching."

"Great idea Kareena.  You are getting good at this."  Jen grabbed Kareena's hand and pulled her towards the back of the store. "Come with me.  We must devise a plan to punish sissy boy."

Kareena followed Jen thinking it was odd at how things were turning out.  She had imagined herself talking to Jen and complimenting her for playing along with Ken. She imagined herself as a confident mistress talking to a shy salesgirl. The reality was that Jen had quickly taken control of the situation and had dominated the conversation.  Kareena's pussy tingled as she held Jen's hand and followed her up a long set of stairs.  She was excited at connecting with an experienced person.  She was excited at the prospect of learning new things. The pecking order was established and Kareena was happy to be at the bottom. 

Jen led Kareena into an office that was above the store.  It was furnished with leather couches and plush leather chairs.  An oversized Mahogany desk sat along one wall.  Erotic pictures and drawings lined the walls.  Most were of a dominant nature.  One particular picture caught Kareena's attention. It was a drawing of a woman standing with her legs apart.  A man was kneeling in front of her, facing away from her. His head was arched backward and was buried in her pussy.  Her hand was firmly placed on the back of his head, pushing him deep into her pussy.

Jen noticed Kareena's attention on the picture and she walked over to the picture. "Ah.  You like this one. It's one of my favorites.  This is the way every man should be.  On his knees and pleasuring his mistress.  Wouldn't you agree?"

Kareena's pussy dampened as she stared at the image.  It definitely radiated a sense of control and superiority for women.  She imagined Ken in the same position and her body shuddered.  "Yes.  I can't wait to get Ken like that."

Jen motioned to a round mahogany table surrounded by brown leather chairs.  "Have a seat."   

Kareena sat down and surveyed the room.  It was decorated very eloquently and very expensively.  It was not what she expected from such a young girl. "Is this your office?"

"Yes it is.  You like it?"

"It's very nice.  You must be doing very well for yourself.  Do you own the store?"

"Thank you and yes this is my store.  You seem a little surprised at all this?"

Kareena was surprised.  She didn't want to offend Jen but she was curious at her success.  "Sorry.  It's just that...well...you're so young.  How did you get all this?"

Jen giggled.  She chose to sit behind her desk instead of at the table with Kareena.  It was a power move that was effective.  "It's all about control my dear.  I learned at an early age that people could easily be influenced and manipulated through a little charm and wit.  It's amazing the things men will do for you just from a little flirting and teasing.  Just look at what sissy Ken has done for you and you haven't even met him in person." 

Both girls laughed.  Jen continued, "My biggest power move was against my dad.  He owned this store and I've always worked here to help him out.  He was a real jerk to my mother.  He cheated on her constantly.  With the help of a video camera I caught him in some very compromising, illegal, and embarrassing situations.  I used this evidence to control him.  I forced him to divorce my mom.  I forced him to sign the store over to me and leave town.  When it was all done I felt so great."

"Wow.  That's an amazing story."

"There's more.  After my dad I began to go after other men.  You would be surprised at how many men crave to be dominated and controlled. I even enlisted my friend Dee to help me out.  Together we have several sissies and slaves that shop here regularly.  They buy whatever we want them to buy no matter the price.  The sales in my store keep going up and up.  Your sissy is a perfect example.  He came in just to buy one outfit for you.  Instead he walked out with hundreds of dollars of merchandise."

Kareena listened with fascination and envy.  Jen could see that she was drawing Kareena in.  Jen was taking a liking to Kareena.  She felt the need to take Kareena under her wing.  She stood up and walked over to the table and sat down next to Kareena.  "Kareena, I can tell you're new at this and you are eager to learn.  This is the way to go.  I have a lot and I don't work hard for it.  I have a sissy maid that cleans my office and my home.  He has not cum in two months (*laughter*).  I have a BMW, diamond rings, and lots of other expensive stuff.  I didn't pay for any of them.  They were all gifts from my slaves and sluts."

Kareena was nodding her head in agreement.  Her eyes were wide with excitement, like a kid in a candy store. She wanted to learn more about controlling men.  She wanted this lifestyle. "Wow. Jen.  You have an incredible life.  The more I learn about this lifestyle the more I love it."

"Great!  You're doing well.  Now let's talk about sissy Ken's punishment and how you can take full control of him."

For the next 20 minutes Jen and Kareena hammered out a plan for the weekend. It was seductive, cunning, and devious.  It was sure to change Ken and Kareena's life forever.  Just as they were wrapping up, Dee's voice projected through a speaker on Jen's desk, "Miss Jen, sissy Ken is here."

Kareena hurried downstairs.  Jen purposely stayed back for a few minutes to give Kareena a chance to observe her slut.  Jen pulled open a cabinet in her office, which held a TV.  The TV was on and the screen was divided into 4 blocks.  Two blocks showed different angles of the store and two blocks had images of her dressing rooms.  It was a state of the art security system she had installed. Although it was designed for security, Jen used it for her own perverted purposes.  In fact she had a tape full of nothing but Ken being a slut.  All his perverted experiences in the store had been recorded.  It was a tape that would be revealed to Ken  over the weekend. 

In the store, Ken made his way to the butt plug section.  He wondered if Miss Jen was working.  He greeted Miss D when he walked in and he noticed one woman browsing some merchandise on the other side of the store.  By now he was comfortable shopping in the adult store, but he still wished no one was there but him.  The fact that he was buying a butt plug was a little embarrassing.  

He stared at the selection on the shelf.  There were small, medium, and large sizes.  His instructions were to buy a small one and a large one.  The small one was to start is anal training and the large one was so he could see his final goal.  He couldn't ever imagine the large one fitting into his ass. He cringed thinking about it.  He was still looking at the package when the woman in the store came over to where he was.  She smiled at him and said "Hi."

Ken blushed, embarrassed at what he had in his hands.  Meekly he replied, "hi," and walked away

Kareena chuckled to herself at his embarrassment.  Her panties were dripping wet from her excitement.  Being next to her pet was so exhilarating.  Hearing his voice and seeing his embarrassment sent a sexual charge through her.  She watched him head toward the counter.  Just then Jen came out from the back.

Jen's voice was purposely loud, "Look who it is, Sissy Ken.  How are you today?

Ken's body language and expressions instantly went submissive. He was aware of the woman in the store glancing over at him and he felt a bit humiliated from being called a sissy in front of her. "ah.  Good Miss Jen.  Thank you."

"What brings you in today.  What slutty things are you up to?"

He was a little uncomfortable talking with Miss Jen with another customer in the store.  She obviously liked humiliating him like this and he knew better than to question her about it. "Well...ah....mistress wants me to buy butt plugs."

"Ooohhhh.  How nice.  Now you'll really be a sissy.  Perhaps you should have a nice sissy name?"  
"Well, actually Miss Jen, I already have a sissy name."

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.

To be Continued

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