Dominating Ken Pt. 01-04

As Karena became more infatuated with her dominance, her expectations of Ken began to grow exponentially. At first she kept in touch with Ken for mere amusement. Then she began to enjoy controlling him and figured she might eventually try a face-to-face session with him. Now she wanted more than a face-to-face session. She wanted to control him indefinitely. She wanted to make him her slave...her boy toy...her sissy slut. Her plan for this was already in motion.

Over the weekend she purchased a male chastity device which she planned to mail to Ken. His e-mails were desperate and it sounded like his cock was ready to burst so Karena knew that she had to get the chastity device to him immediately to prevent him from losing control. She was sitting at the computer staring at the box when an idea hit her. She decided to give Ken a little treat for his obedience. She pulled off her purple cotton panties, which were drenched with her girl cum. She rubbed them along her pussy to soak up as much of her juices as possible. Then she put them in a Ziploc sandwich bag. The panties were so wet that she could see moisture streaks on the inside of the plastic bag. Karena slid the bag inside the box with the chastity device. At 7:30 that night she logged back on. She knew Ken would be waiting.

"How's my puppslut?"

"Very very horny. Did you get my e-mails mistress? Can I please cum?"

"Naughty dog! Is that anyway to greet your mistress? Didn't I tell you I didn't want to hear from you till tonight? Let's see...first e-mail from dogface arrived at 2:00 pm, second e-mail from pee-pee dog at 3:00 and third e-mail from my pathetic pet at 3:30 pm. Are we a little desperate poochie? Do you need a lesson on following directions?"

"Sorry Mistress. I am desperate. My cock and balls are full of cum. Being your doggie boy has really made me horny. I need release."

"Dogface you are pathetic. A grown man naked and peeing like a dog is so ridiculous. The things men do when they are horny. You enjoyed it too and I have the proof! What would your friends and family think if they knew your dirty little perversion? Don't worry your secret is safe with me. I know how pathetic men really are. You like being my doggie boy don't you? Stroke your cock and tell me how much you like it. Don't forget to lick up any precum that leaks out of that little doggie wiener."

"I am stroking my doggie wiener for your mistress. It is very leaky from being so full of cum. I really need to cum. Please let me cum. I know it's pathetic, but I can't help it. I like being your dog slut. I like peeing for you."

"Of course you do because your are a man and men are dogs. I noticed you peed in the same spot, just like a real dog would. You marked your territory like a true animal.... Like a pathetic man dog. You are a natural. Bark for me dog!"

"BARK! Bark! Bark!"

"Good boy. No cumming just yet. Do you miss your panties slut or would you prefer to be dog boy?"

"Whatever you wish mistress. It excites me to do these slutty things for you."

"Good answer pet. I think its time to get you back in panties. We can't have you wearing a dog collar to work can we? We don't want your co-workers finding about your dirty little secrets do we? Are you ready for big girl panties? Ask me nicely and I might let you wear them.

"Thank you for keeping my secret safe. I am ready for big girl panties. Please Miss Karena, may I wear big girl panties? I will be a good girl."

"How nice. You have been good princess. You may return to your favorite store and buy 5 different pairs of panties. They should all be silk and very feminine and girlish. Buy at least 2 thongs. Since you're going to be a big girl you can start wearing a bra. Pick out a sexy red bra to match one of the panties you are buying. While you're at it get a matching garter belt and white stockings. That should make you look nice and slutty. You know the routine: same clerk and send me the receipt got it?"

Ken was very nervous about this. He was not sure if he liked where this was going. Wearing panties was humiliating but it was also exciting and something had had often fantasized about. He never imagined himself wearing a bra and garter belt and he really did not want to do it. He didn't even know what size or type to get. He did not want to upset his mistress so he simply replied. "Yes mistress. Thank you."

" It seems that you are making quite an impression on your sales clerk. Pay close attention to her at your next visit. I want to know what she looks like. Hair color, eyes, height, body type, etc. I want to know her name and take a guess at her breast size. How's that cock doing? Ready to cum?"

"My cock is so full and leaky. I'm am ready to cum. Please may I cum?"

"Stroke it a little more for me slutboy. Rub your finger across the tip and massage that nasty pre-cum into your shaft. That's right, I want your little clitty nice and wet sissyboy. Bring yourself to the edge and then stop touching your cock and beg me for release. Don't be a wimp either sissyboy. You better last at least 5 minutes before e-mailing me."

Ken was already close to the edge and his hands were already sticky because he had been stroking his cock ever since he logged on. Five minutes was going to seem like an eternity. He concentrated on milking out his precum and rubbing it over his cock head and shaft. He imagined it as his clitty that he was masturbating. The wet lubricated sensation was incredible. He slowed down his stroking and concentrated on not cumming. Ken wanted to go at least 6 minutes to prove to his Mistress that he was not a wimp, but he couldn't make it. As soon as 5 minutes was up he stopped and e-mailed his mistress.

"Please please let me cum. I am right at the edge. My cock is twitching. I need release please mistress!"

Karena was delighted with his begging but she was feeling wicked. She replied "Such pathetic begging sissy. I like the way you plead for my permission like a cheap whore. You have cum a long way slut but I need to take you to the next level. I want you to suffer for me. Will you do that for me slut? Of course you will because I own you and your pathetic cock. No cumming tonight. Suck it up and suffer for me. Can you handle it?"

"I will suffer for you mistress because I know it pleases you. I don't know if I can last much longer without release. How much longer must I wait?"

"Pathetic whore. All you can think about is cumming. Your next cum date is for me to decide. You will get a surprise from me sometime this week. Check your PO Box daily and e-mail me when you get it. Do not open the package without my permission."

Ken was excited to know that a surprise was on the way. "Yes. M'am. Thank you."

"You're welcome slut. Tomorrow I want you back into your little girl panties. Tuck that pee-pee between your legs like a little clittie. Don't forget to do your nails and wear your lipstick on the way to work. You may change into your big girl panties when you purchase them. Follow your daily routines but don't e-mail me until your package arrives."

PART IV KEN'S SHOPPING TRIP ADVENTURE

Monday morning Ken was so horny and nervous about his new assignment that he could not bring himself to go to work. He was not going to be able to calm his nerves until he went to the store and bought his big girl items. He did not want to dress like a girl but the more he thought about it the more excited he became. He did not know why he was experiencing these strange erotic feelings. In his current state of mind he would not be able to concentrate at work. He woke up a 5:00 am and called in sick to work. Then he applied his clear nail polish and his pretty pink toenail polish. He put on a purple pair of little girl panties, size 14. All of this girlish preparation quickly shifted his mind from dogboy mode to little princess mode. He was feeling feminine and girlish. He thought about how this would probably be the last time he wore little girl panties since Miss Kareena was allowing him to move into big girl panties. This made the day seem a little more special and exciting for Ken.

Although Ken was not going to work, he still put on the glossy pink lipstick. He decided that he would wear it while he was at home. Dressed like a cute teenage girl, Ken started his masturbation routine. He was finding it increasingly difficult to stroke himself for a half hour in 5 minute intervals without cumming. About half way through his masturbation session he had to stroke his cock very slowly and lightly in order to prevent himself from cumming. He managed to control himself but not without a lot of cum leaking out. At one point he brought himself so close to the edge that a stream of warn cum poured into his hands. It was a strange moment for Ken because he had no control over the cum that poured out. He had never experienced this loss of control before. He did not orgasm and it was not pleasurable. It was just an overflow of cum building up in his cock and balls. Ken licked it up quickly before any could spill on the floor.

Next Ken logged on to check for messages from Miss Kareena. He was hoping she would allow him to cum today. Ken was disappointed to find that Miss Kareena had not sent him an e-mail. He stayed on line for about 10 minutes hoping that a message would come into his inbox, but nothing came. After that, Ken spent most of the morning online researching bras. He was very nervous about his assignment and he wanted to make sure he at least knew what the different sizes meant. In his aroused state he found himself lingering on the websites which had beautiful women modeling their bras. Instead of having his pee-pee pushed between his legs like a pussy, he had his cock pointing out of his purple panties and he was stroking it.

Ken eventually found a website which explained bras and had instructions for girls on how to determine their bra size. Unfortunately he didn't have a tape measure so he couldn't determine his size. Ken decided that he would just guess.

In the early afternoon Ken headed out on his mission. He figured the store would be empty on a Monday afternoon, thereby eliminating some of his public embarrassment. Ken entered the store and it was empty. Unfortunately Miss Jen was not around so he could not complete his assignment.

One of the sales girls approached him. "Hello may I help you sir."

Ken nervously answered, "I...aahh....is Miss... I mean is Jen working today?"

The young sales girl smirked back at him. Emphasizing the salutation, "MISS Jen is not here today. She'll be into tonight. Is there something I can help you find?"

Ken did not know if she was being sarcastic to him or if everyone referred to her as Miss Jen. From the amusing and somewhat superior tone of her voice Ken sensed that his slip of the tongue clued the sales girl in on his situation with Miss Jen. He quietly mumbled. "um...no thank you ma'am. I'll just stop by tonight."

"Whom may I tell Miss Jen to expect tonight?"

Ken was a little caught of guard at this request. He was hoping to get by without being noticed. "Ken. My name is Ken."

The sales girl smiled and playfully looked into his eyes. Her tone was sensual and teasing. "Well Ken, I'll let her know you stopped by. If there's anything you need in the meantime, let me know. You may call me Miss D." The sales girl turned and walked away.

Although the situation felt a bit awkward for Ken, he was becoming braver in the store. Instead of blushing and rushing out of the store, he decided to browse around. He saw tables full of panties on sale. He saw racks and racks of bra's and lingerie. Even with the research he had done on bras, he was clueless. The huge variety of styles and sizes were overwhelming. He was definitely going to need help, but he was embarrassed to ask. He was in deep thought when Miss D interrupted him.

"Excuse me Ken. As luck would have it, Miss Jen called and I mentioned that you were here looking for her. She would like to speak to you."

Miss D led Ken to the front counter and handed him the phone. Ken picked it up unsure of what to expect. "Hello."

Her voice was sweet, "Hi Kenny. So you're back again. Did you like my little present? Are you wearing the cock ring now?"

Ken was wearing the cock ring. Miss D was standing nearby. He lowered his voice because he did not want her to hear. "Yes I liked your present and I am wearing it now."

"I can barely hear. Please speak louder. How does it feel?"

Ken raised his voice slightly. "It feels great. It makes my cock feel extra hard and sensitive."

"Mmmm. That's what I like to hear. Is your cock hard now?"

Ken's cock was straining hard against his panties from talking to Miss Jen. Had it not been bent back through his legs like a pussy, it would have been hard as a rock. He wasn't sure how he was going to explain this to Miss Jen. "No.. not really."

Miss Jen pressed him for more information, "Not really. What's that supposed to mean. I would think a pervert like you would be hard as a rock right now. I know you came back into the store to buy something slutty. I bet you're somebody's sissy-boy. You are a sissy-boy aren't you? You're wearing panties right now aren't you?"

Ken suddenly felt nervous and embarrassed. Miss Jen had figured him out. He was embarrassed to admit to a younger girl that he was wearing panties. What made it worse was that Miss D was standing next to him listening intently. "Well....uh...yes I am wearing panties. How did you know?"

Ken heard Miss D giggle and his face flushed a deeper shade of red. Miss Jen remained calm and in control. "I may be young, but I've been working at this store for a long time and I can recognize a sissy-boy in training when I see one. Let's see, your nails are coated in clear polish, you always come to me to ring up your order, and you've been back into my store 3 times in less than 2 weeks to buy or do something embarrassing. All that adds up to a sissy-boy who's following orders from his Mistress. So sissy-boy, tell me why you are not hard right now?"

Miss Jen's voice was commanding. Ken found himself feeling very submissive to her. He could have hung up the phone and walked out, but he was enjoying the submissive feeling. "Ummm..my cock is not hard because my cock is pushed back through my legs."

"Poor boy. You have a clitty just like a little girl. Tell me little girl, what are you shopping for today?"

"I need to buy panties, a bra, and stockings."

"And do you need my help?"

"Yes. My mistress has instructed me to have you ring up my order since you have been the person who has always rang up my order."

Ken knew that Miss D was listening to every word he was saying. He felt totally humiliated. His humiliation intensified when a woman walked up to the counter to purchase some lingerie. Ken knew that the woman could hear his conversation.

Miss Jen continued, "Ask me nicely and I may help. Tell me everything that you want me to help you with."

"Please Miss Jen will you help me buy panties and a bra for myself. I need to buy 5 pairs of pretty panties and a red bra. I need at least 2 thong panties and I also need stockings. Please will you help me pick out these items?"

"What sizes do you need dear?"

"I'm not sure Miss Jen. Will you help me pick out the right size?"

"Tell me you'll be a good girl. Tell me you want me to measure your little girl titties."

Ken's heart was pounding in his chest. Everything was happening so fast. He came into the store buy some lingerie and now suddenly he was talking like a little girl to a college age salesgirl and in front of other women. He could see a devilish smirk on Miss D's face and he knew the woman at the counter was glancing at him like he was a freak. To top it off another woman came into the store and stood in line. Miss D purposely rang the order up slow. Ken felt very inferior and submissive with everything that was going on. He did not want to say these girlish words infront of all these women but he needed Miss Jen's help. He did not know what to say.

Miss Jen encouraged him, "Come on darling, be a good girl and tell me."

Ken mumbled the words but Miss Jen would not go for it. She ordered him to say them nice and loud or she would hang up and be done with him. Humiliated, Ken clearly stated, "Will you please measure my little girl titties and help me find the right bra size. I'll be a good girl for you, I promise."

Miss D and the two customers laughed at his expense. Ken cringed and turned red. Although he was humiliated he was aroused and his cock was pushing against his panties trying to grow. Ken could not believe at how aroused he was from the situation.

Miss Jen finally agreed to help Ken. "Since you asked like a good little girl I will help you. I'll be there shortly. In the meantime, have Miss D take all your measurements, okay sweetie?"

"Yes. Miss Jen. Thank you."

Miss D was just finishing up with the last customer when Ken hung up the phone. After the customer walked away, Ken politely asked, "Miss D, could you please do my measurements."

Miss D's devilish smiled returned. "Of course sweetie. I told you I'd be glad to help you with anything. Take your shirt off dear and we'll get started.

Ken was waiting for her to usher him to a backroom but she just stood there and waited. He knew it was going to be a long day. Ken removed his shirt and Miss D came over to him with a long cloth tape measure.

Miss D began to instruct Ken on what to do. She purposely spoke to him like a little girl. "Okay sweetie stand up straight and point those titties outward... Good girl. First we have to measure below your titties. Hold our arms out to the side."

Ken raised his arms and Miss D wrapped the tape measure around him, just below his chest. Ken's attention was focused on Miss D. He figured she was only 18 or 19 years old. Her body was slim and athletic. Her perky tits pressed firmly against her tight white t-shirt. She was about 5ft 7and her hair was dark brown. He could not believe he was being measured for a bra and being talked to like a little girl from a teenager almost half his age. The moment was surreal and exciting. Ken's bent cock pressed hard against the crotch of his panties. He wished he could pull it out and enjoy its fullness.

Miss D moved the tape measure up to his chest. The tape measure was cool. Miss D purposely rubbed it over his nipples a few times causing them to grow hard. "Now we must measure your titties...My, my, they are small little titties. Hold them out nice proud darling so I can get the right measurements. Ken tried to push his chest out far. He was actually ashamed of his small titties. Miss D wrote the measurements on a pad of paper. "Okay honey, I need a few other measurements. Take off your pants."

Ken panicked. "Miss D, don't you think we should do this in the back room."

Miss D's voice was gentle. "Don't worry baby doll, it's just us girls here. We never get men in here during the day. Nothing to be ashamed of. Let me help you."

Ken stood there in disbelief as Miss D unbuttoned his pants and pulled them down revealing his purple pre-teen panties. Miss D commented, "Oh how cute. Little girlie panties. Miss D pressed her hand against his crotch to feel his boypussy. "You really are a baby doll. Is this your first time buying big girl panties?"

"Yes."

"Well let's pull these off and get the right measurements." Miss D pulled his panties down and Ken's cock popped out from between his legs. It instantly grew hard. Miss D stared at the pink bow and saran wrap on his cock head and giggled. "How cute. What's the plastic for?"

"It's so I don't wet my panties."

Miss D giggled again. She reached down and stroked his cock a few times, causing pre-cum to press against the saran wrap. Miss D jumped right into the role playing. "Poor little baby girl wets her panties. Are you sure your ready for big girl panties? Can you hold that cum cum in for mommy?"