• Home
  • /
  • Stories Hub
  • /
  • BDSM
  • /
  • Dominating Ken Pt. 05-08

Dominating Ken Pt. 05-08

123456...10

PART V TEASED AND ENTRAPPED!

Monday evening Kareena logged on and was delighted to see an e-mail from Ken. She had instructed him not to write until her present arrived and she knew that it had not arrived. She was curious as to what he had to say. She wasn't even halfway through the e-mail and her pussy was hot and beginning to dampen. It was obvious that Ken was excited and even proud at completing her assignment. His e-mail rambled on like a giddy girl. He seemed to be getting increasingly aroused from her assignments of dressing like a girl. The fact the he skipped work because he could not concentrate indicated to Kareena that his thoughts were being consumed by her and that he was losing control of reality. The fact the he almost lost control of his cock when he was dressed in pretty lingerie and staring at himself in the mirror, indicated that he was more accepting of being a girl. She knew this change in attitude was a direct result of her control and continued teasing and manipulation of his mind and body. He was willing to do anything for her and this power thrilled her and aroused her.

Kareena unzipped her pants and snaked a finger into her needy pussy. Slowly she played with the folds of her pussy while she read Ken's e-mail. He described Jen as "young, brunette, and average height." He guessed her bra size to be a 36C. Kareena laughed out loud when she read how Jen called him a sissy boy when she figured out he was shopping for himself. Kareena was glad that Jen was a good sport and played along with the assignment. She imagined that Ken must have been totally humiliated at being caught red handed by a young girl. Her pussy gushed with excitement. Kareena imagined the scenario and pushed three fingers into her wet hole. Her fingers found her hard and swollen nub and she teased it. Soon she was humping her hand with deep thrusts. Her shirt was off and she was squeezing her nipples. She thought about how she was turning into a goddess to Ken and that he was her boy toy. She controlled his thoughts, emotions, and his cock. She could not wait for the weekend to come because that was when she planned to take stronger control of his life. She was carefully weaving a web that Ken would not be able to escape. By Friday night her prey would be entrapped and at her mercy. Kareena moaned in wild abandon as a powerful orgasm shook her body and mind.

After a few minutes Kareena's mind cleared and she returned to her e-mail. There was plenty of toying she could do with Ken from the information he provided. Kareena couldn't wait to talk to him online but she did not want to waver from her original orders.. She sent an e-mail.

"Hi sissy. I know you're checking your e-mail every 5 minutes awaiting my reply. I know your pulse quickened and your little cock twitched when you saw my name in your inbox. You are excited for me aren't you slut? Well listen up sissy. I said no e-mails until you receive my gift. Do you have problems with instructions??? Maybe I should punish you?

I guess you were too excited from dressing up in all those pretty things and you just had to tell me about it. You are turning into quite a whore. I must see a picture. Send me a picture right away! No words, no messages. Just send me the picture. I'm waiting...."

Within 10 minutes Kareena received Ken's pic. She smiled to herself at how well she knew Ken. She figured he was waiting to hear from her. Kareena viewed the pic and at first laughed at the sight of a grown man dressed like a pretty slut with glossy pink lipstick. His hard cock protruded obscenely from the red panties. As she stared at her slutboy her pussy tingled and she became overwhelmed with horniness. She realized that she had taken an ordinary guy and taken control of him to the point that he was willing to do anything for her. She had eased into his mind and controlled not only his thoughts, but also his wants and desires. Kareena had taken Ken's natural desires for sex and orgasm and played with them, teased them, and manipulated them to the point that Ken wanted to do anything to please her. Whatever Kareena desired, Ken wanted to do and that is why Ken wanted to dress like a girl. This was true power and domination. Kareena was surprised and delighted at how intensely aroused she became.

This strange new arousal took a hold of Kareena and fueled her need for more control. It took all her strength to hold back from playing with him. She had to be strong and let him know that he must follow orders. She decided to end the conversation, but not without a little fun. "Well darling, I did say no e-mails until my present arrived and I did mean that. I will forgive you since you did such a great job at buying the lingerie. Tonight I want you to sleep in your new whore outfit. I want you to feel like a cheap whore when you wake up tomorrow. I bet your pussy will be swollen and needy in the morning. You may remove the bra for work but you must wear the garter belt, stocking and panties, got it? Are you sorry that you e-mailed me now slut? Can you handle it? Don't answer whore....just do it! Go to bed now and e-mail when my present arrives.

Ken's cock twitched at the thought of being a cheap whore. He was disappointed that Miss Kareena did not want to talk but he did not dare to reply. Ken logged off and went to bed as ordered. He did not sleep much because he was extremely aroused from the lingerie he was wearing. He stroked his cock off and on through the night. When he awoke he the morning his panties were damp from precum and his boy pussy was swollen and needy just like Mistress Kareena said it would be. He didn't know how he was going to make it through a day at work.

Ken was not sure if the garter belt was visible through his clothes. He didn't think it was visible, but he wore a sport coat just in case. Anytime he got up and walked at work he could feel the garters tugging on the stocking and he could feel the stocking rubbing against his legs. He was a walking erection for most of the day. On his way home he checked his PO box and was disappointed to find it empty.

Wednesday was just as torturous for Ken. He was starting to fall behind on his work because he could not concentrate. He even found himself feeling submissive to other female managers. When he was questioned by one female about a design that was due to her, he instinctively diverted his eyes downward and replied, "Sorry ma'am. I'll get it done right away ma'am." The manger looked at him strangely and walked away amused and feeling somewhat empowered from his response.

On his way home he checked his PO Box and his heart leaped in his chest when he saw the package from Mistress Kareena. It was a small brown box. He stared at it for a minute, thinking that this package would probably bring him great pleasure. It would bring him closer to his Mistress. Ken flipped the package over to look for a return address, but none could be found. Mistress Kareena was too clever. Ken quickly walked out of the post office with a raging hard-on. He rushed home to his computer and logged on.

His heart pounded and his cock twitched as he typed. "Hi Mistress. It's here! Your package has arrived!"

Kareena had been waiting for his e-mail. She too was excited and she knew the package would be there on Wednesday. Kareena had left work early to prepare for this moment. While she waited, she had been looking over the pics of Ken in his panties and lingerie. She viewed the video clips of her puppyslut and she read some of his past e-mails. By the time his e-mail arrived she had already brought herself to an orgasm. It would not be the last orgasm for the night

Kareena was ready for a little fun with her slut. It was time to exert her power and show who owned him. She wrote back. "Mmmm. you looked so pretty in your slutty lingerie darling...and your cock was so hard. You're enjoying this aren't you?"

Ken was excited and looking forward to some fun. He wasted no time to reply, "Thank you. Mistress. I am enjoying this. I'm really horny and want to cum so bad. I am wearing my new outfit right now."

"So you like your new lingerie, don't you? It's so pretty and feminine. It's fun shopping for lingerie for yourself isn't?"

Ken was dying to see what was in the box. He wanted Mistress Kareena to tell him to open it right away. She was teasing him and building up his anticipation. Ken thought about her question. He was still threatened at losing his masculinity but he was beyond denying his feeling with Kareena. "Yes. It is fun. There are so many pretty things to choose from."

"That's good princess. Now you are starting to realize how great it is to be a woman aren't you?"

"Yes. You are lucky."

"I know princess and you are lucky to have me here to teach you about being a woman. I mean that's what you want isn't it?"

"I...I don't know. I just want to please you."

Kareena replied back with a copy of the picture he sent on Monday. "Come now princess. See how hard your cock is in this picture. I could tell you were so excited from your shopping trip. You can admit it to me darling. You like being like a woman, don't you? Don't worry, it will be our little secret. Say it out loud, write it back to me in an e-mail - Women are superior and I wish I was a woman."

Ken was under Kareena's spell. He stroked his cock while he said the words. He replied, "Women are superior and I wish I was a woman."

"That's good princess. You're getting there. Even the sales clerk could tell you were a sissy. You must be a natural. You must have been so excited to have someone there to share your dirty secret with. It was exciting having her there to help you pick out girlie things, wasn't it."

Ken's mind was reeling with erotic thoughts and excitement. He was amazed at how well Kareena knew his emotions. It was as if she had been there on the shopping trip. He confirmed her assumptions. "Yes it was very exciting. She had me try on the lingerie before I purchased it and she made me wear it home. I felt so horny and naughty wearing it."

"You are naughty dear. I like that about you. You look so pretty. I think we need a more feminine name for you. Wouldn't you like it if I came up with a nice pretty name for you?"

Ken was feeling very girlish and submissive. The idea of having a girl name from his mistress seemed so perverse and kinky. He knew she wanted him to have a girl name and that made him excited. "Yes mistress please give me a pretty girl name."

"I think Kimmee sounds cute don't you? Are you my little Kimmee?"

Ken's body shivered in delight at his new girl name. A special name given to him by his mistress. "Yes, if that is what you want mistress. I am your little Kimmee. Kimmee wants to please you."

"Kimmee, are you stroking your girl cock for me?"

"Yes. I am so horny and I really want to cum. My balls are swollen and they ache. Please let me cum mistress. I'll do anything to cum!"

"Your balls are full of cum? It's only been a few days since you last had release. Prove it to me darling. Send me a picture.....and make sure you're wearing my cock and ball strap. I just love to see my name attached to MY cock and balls. They are mine to do with as I please. Hurry now Kimmee... I'm waiting..."

Ken did not have the harness on at the moment so he rushed to put it on. He fumbled with the straps for a few minutes, trying to get it on. It was difficult because his cock and balls were swollen from the prolonged teasing and excitement he had been experiencing over the last few days. The harness created a wonderful tightness feeling to his balls and made his cock feel extra hard and sensitive. His cock was already dripping cum. Ken quickly took a close-up picture of his crotch, ensuring the nametag was clearly visible. He emailed the photo and received a quick reply.

"Switch to Instant Messaging dear. Hurry now."

Ken logged into IM and was immediately greeted by Miss Kareena.

MK> "My...my they do look full of cum. You are such a horny girl. I suppose you do need some relief. Are you ready to be slutty for me Kimmee?"

KEN> "Yes. I will be slutty for you. "

MK> "Well then I'll give you some relief. Don't get too excited because you're not allowed to cum...at least not from an orgasm <*devilish smile*>. I want you to save that pleasure for a special occasion sweetie. Tonight I'm feeling playful. I'm going to tease you and milk out your cum little by little. Can you handle it?"

Ken's cock was already twitching from excitement. He was ready to play and do whatever she wanted.

KEN> "Yes. I can. I'll be a good slut for you."

MK> "Of course you will. Go get your cock shaped dildo. Let me know when you are ready."

Ken was nervous about what he was getting into but he was too horny to think about it. He rushed into his room and grabbed the dildo.

KEN> "I'm ready"

MK> "Good. Put it to the side for now. You may open my present and take out the bag. Do not open the inside box. Tell me what's in the bag slut. Start stroking your cock. Tonight you are my whore. You will do as I say and no cumming. Got it?"

KEN> "Yes. Ma'am"

Ken couldn't move fast enough. He ripped open the box and pulled out the plastic zip lock bag from Kareena.

KEN> "It's a pair of panties. Are they yours?"

MK> "Yes they are slut and I wore them one night when you were being nice and naughty for me. Take them out of the bag and feel how damp they are sweetie. Smell them....inhale your mistress's scent."

The zip lock bag had sealed in Kareena's juices. Ken's fingers traced the damp silk. He imagined Kareena's pussy pressed against the crotch. He stroked his cock and moved the panties to his nose. Her scent was strong and pungent. Ken was close to loosing control. His computer beeped and pulled him out of his erotic trance.

The incoming message contained two pictures of a woman dressed in a leather half bra and a leather corset. She had a whip in her hand. The first pic showed her standing with her tits and pussy exposed and she had a dominating expression on her face. The second pic showed her bent over with a close-up of her ass.

MK> "These are pics of a beautiful mistress. For the purpose of tonight consider it me. Put my panties on your face. Make sure the crotch is right at your nose. Stare at me and give me slow and firm hand over hand strokes from the top of your cock down to the base. Do this for 1 minute and await further orders."

Ken did as instructed. It felt incredible. The fact the he was wearing his mistresses damp panties on his face added to his excitement. He had to fight hard to control his urge to cum. As he stroked more messages came through from Miss Kareena

MK> "That's good..stroke it for me baby. Stare at my tits..."

MK> "My pussy is hot and wet knowing that you are my little whore. I'm fingering myself just thinking about it. Too bad you're not here to help me."

Kareena's words heightened Ken's arousal. He was having a hard time concentrating. When his minute was just about up another message came through..

MK> "Okay Kimmee, my naughty whore. Stroke just your cockhead with just your forefinger and thumb. Short quick pulls. Keep doing it until I tell you to stop.

Ken did as instructed. Cum started to leak out. He was getting worried that he wouldn't be able to make it without cumming.

MK> Use your forefinger and rub the tip of your cock. Use it to massage your precum into your cock head. Get it nice and shiny for me.

After about 30 seconds of this Ken felt like he was going to explode. He was thankful for the next message. It was as if Miss Kareena knew his limits.

MK> Hands of now slut! Is your cock head nice and shiny. How aroused are you Kimmee? 1 = not all and 10 = ready to orgasm. Where are you on the scale.

KEN> My cockhead is very shiny. This is great but I don't think I can last much longer. Can I please cum? Please! Please! I'd say I'm at a 9.5.

Kareena chuckled. She knew he was on edge. She was close to orgasm herself. She was enjoying the sexual torture.

MK> "We have a long way to go princess. We better get your mind off that silly cock of yours. I want you to suck the cock dildo. Suck it nice and hard for me. Imagine that it is strapped to me and you are sucking me off like a good little whore."

Normally Ken would protest having to suck a fake cock because it was a big blow to his masculinity. However, he was so charged up and aroused and he needed to calm down. Miss Kareena was right that it would take his mind off his cock. At least that's how Ken justified the need to suck cock. Slowly he pushed the rubber cock into his mouth. He was surprised at how flesh like it felt. He could feel the veiny texture slide across his lips and his tongue. More messages poured through

MK> "Suck that cock Kimmee.... Push it all the way down darling. If you're a good whore I might let you cum tonight."

Ken obeyed her in hopes that he would be able to cum. He pushed the dildo deep into his mouth

MK> "That's it sweetie. Suck it hard...I like noisy blow jobs...are you slurping? That's what I like to hear darling."

Ken acted as if Miss Kareena was in the room with him. He slurped and sucked at the cock. He felt slutty and submissive

MK> "How's your cock Kimmee? Soft yet? Where are you on the scale?"

Ken calmed down but his cock was still hard. Acting like a whore for Miss Kareena was keeping him hot.

KEN> "I'm still hard but not as aroused. About an 8."

MK> "I guess you like sucking that cock darling. It makes me so hot knowing that you are being such a whore for me. You may put the cock down for now. I want you to sit in your chair and put your feet up on the desk. Spread them wide and pull your thong to the side so that your pussy hole is facing my picture. I want to see that pussyhole. Let me know when you are ready."

Ken's heart pounded hard. He did not know what to expect. He got into position. His asshole seemed to tingle with anticipation.

KEN> "I'm ready"

MK> "Such a tight virgin hole. Take your left forefinger and lightly trace the rim of your ass. Feels good doesn't it slut?"

Ken traced his asshole and the sensation sent shivers through his spine.

KEN> "Yes. It's incredible."

MK> "Stare at my picture and keep teasing your pussyhole like a good little whore. I'm watching you slut. Stroke your girlcock with your right hand. If any cum leaks out, I want you to rub on your belly."

Ken felt naughty and dirty from playing with his ass and cock. He imagined it was Miss Kareena that was there licking his pussyhole. The combination of sensations were mind blowing.

KEN> "I think I'm going to cum! Please let me cum!"

MK> "NO! Stop stroking. Stand up, bend over and stare out my ass. Finger your asshole while you do this. If any cum leaks out rub it on your chest or stomach. Do this for 2 minutes. That should calm you down."

Ken was so close to the edge and he could not think straight. He was completely under Miss Kareena's control. Like a mindless robot he bent forward, stared at his computer screen and carried out her commands. He imagined Miss Kareena being right there in front of him. Ken pushed his finger gently into his ass. His hole was hot and tight. Slowly he fingered his ass. As he did this cum started dribbling out of his cock. He used his other hand to catch it and rub it on his belly. After 2 minutes another message popped up.

MK> "Sit back down slut and stroke your cock fast for me. Bring yourself to the edge and let me know when you are there. Rub any leaky cum onto your chest"

For the next 20 minutes this scenario occurred over and over again. Miss Kareena made Ken stand up and finger his ass then sit down and stroke his cock. She was essentially making him milk his cum out. Cum continually oozed out of his cock and Ken collected it in his hand and rubbed all over his body. She ordered him to rub cum on his chest, nipples, stomach, and inner thighs. After 20 minutes his body was covered in sticky cum. The whole room smelled of cum.

123456...10
  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • BDSM
  • /
  • Dominating Ken Pt. 05-08

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 18 milliseconds