Jenny and John Ch. 01

Jenny is a tall, blonde, former stock broker. In her days at the firm she took advantage of her slim figure and medium breasts to get ahead in the company. Always dressed in an elegant manner, heels, red lipstick, a classy dress, stockings and a garter belt to attract the attention of men in just the right way. She was now self-employed as a day trader, keeping her elevated fashion ever present. Her business was mostly automated at this point leaving ample time to explore other hobbies. In her private life, Jenny had another side...femdom dominatrix clad in latex and thigh-high heeled boots.

When Jenny takes on her role as mistress she is always ready to dominate a new sissy boy by locking up his cock in chastity and using her strapon to remind him of his place. If Mistress Jenny needs a more persuasive reminder of her power she would dress up her chastity slut like a sissy girl and pimp him out to any men that want their turn.

One day, Jenny was at the local sex shop buying some toys in anticipation of her next sissy encounter when she met a 'man' that fit the bill. He was about 5'4" with dark hair, blue eyes and a slim build.

"Hi, how can I help you?" he said shyly. "Hi there!" replied Jenny. "I'm Jenny, may I ask your name?" "I'm John." "Well John, I am looking for something to help me with training a sissy. Do you have anything that might help?"

"Sure do, what kind of things are you looking for?" he replied. Jenny pondered for a moment before responding, "I really don't know, maybe a cock cage, a butt plug, or something like that." John recalled they had just got a new shipment of chastity cages in, "We have some cages in the back room, let me go grab one." "Oh perfect!" Jenny said as she followed John. It was store policy that customers were not allowed in the storage room but John could not resist Jenny's beauty and confidence.

John grabbed a chastity cage and butt plug trainer set off the shelf and laid them out on the table for Jenny. Jenny was quite pleased with selection and with that her trap was set. Jenny explained, "John, this looks like a great selection. However, I am not quite familiar with these models. Do you mind if we take them out of the package to get a closer look?"

John was hesitant at first but Jenny was stunningly beautiful and he could not resist her request. Towering over him in her black heels and seamed black stockings, you could barely make out the garter clips pressed against her fitted mid thigh pencil skirt. Her red satin top fit rather loosely and draped nicely between her breasts. A sight that surely had John distracted. Mindlessly, John opened the boxes for the chastity cage and butt plugs.

Jenny took the cage from him and examined it closely. The cage was made of metal with a small padlock and lock key. The cage itself was very sturdy and heavy but had quite a feminine appearance. The metal was coated in a sparkly pink finish with a little silk bow that sat on top near the lock.

As Jenny examined the cage she couldn't help but notice how small it was. Surly it could only fit a cock that was about an inch and a half flaccid. She was also intrigued that John had selected such a feminine cage unprompted. Seeing that John was very obviously enamored with her looks she decided to roll the dice. Jenny purposely dropped the chastity cage allowing it to tumble some ways away. Feigning kindness she exclaimed, "Oh, I'm so sorry! Let me get that! I can be so clumsy sometimes."

Jenny sauntered over to the cage, taking slow steps. With her heels clicking each time she set her foot. She finally made her way to the cage, very purposefully bent at the waist while retrieving it. Bending just far enough that John could see her bright red garter straps and just a small glimpse of her matching panties. She returned to the shelf where the butt plugs were laid out knowing full well nobody would interrupt them in the back room. She asked John "Please, would you show me how it works? I would hate to drop it again."

John was still mesmerized by her beauty and the fact that she seemed to be playing with him. His cock was hardening quickly and he knew that he would need release soon. Without hesitation he agreed.

John showed the cage to Jenny explaining how there were two portions. One portion sat around the balls and the other over the cock. John demonstrated how it locked and unlocked, finally setting the cage back down on the table. Jenny watched this demonstration intently, being sure that John knew she wanted to know everything there was to know about the chastity cage. When John was done Jenny continued her devious plan, "John that was a wonderful demonstration..." Placing her hand on his she knew he had fallen for the trap. "I'm just not sure I'm fully understanding how it works. I know this sounds crazy but would you show me on a real cock how it works?" Jenny pushed. John was visibly surprised at this request. "Well, I've never actually used one of these, I'm not sure." John stuttered.

Jenny bent over revealing a wonderful view down her blouse. That was all the convincing John needed. John, with a little less stutter in his voice now, said "I guess I could show you. What's the worst that can happen?" John then unbuckled his belt and slid his pants down to his knees. Jenny in one swooping motion yanked his pants down to his ankles. "I want a good view of this if you don't mind." Licking her lips ever so subtly. John's fully hard dick stood straight out. Jenny guessed it measured about 7&1/2 maybe 8 inches. Jenny then crossed her arms and tapped her foot. "Well? Let's see it." John slid the ring over his cock and down to his balls. With quite a bit of effort and rather uncomfortably, he got his balls through the ring as well.

John, looking at the portion of the chastity cage meant to cover his cock and said "Jenny, I'm sorry but this will never fit. I'm so hard right now it will take forever for this erection to just go away." All according to Jenny's plan. Jenny pressed herself up against John. With her tits against him, through her glossy red lips she whispered, "Let me help you with that."

She reached down and cupped his balls with her hand. Slowly she began to massage his balls. John moaned slightly as she did so. Jenny then leaned forward and took his cock into her mouth.

She sucked on his head slowly, licking up and down the shaft. She then took his entire length down her throat without so much as a gag, sucking and bobbing her head up and down. John was completely lost in the moment.

He had never felt anything like this before. Jenny was sucking his cock with such passion and skill. Jenny pulled her mouth off his cock and looked up at him, her eyes burning with desire.

Jenny then asked "John, would you please fuck me? It's been so long since I've had a nice big cock in me." Without hesitation John agreed. Jenny stood back up and hiked up her skirt. She put one stocking clad leg up on the table and reached back to move her panties to the side. She then grabbed John's hard cock and slid it slowly inside her.

Jenny let out a soft moan as John filled her. Jenny leaned forward, placing her hands on the table. She started to rock back and forth on John. Her tits swayed under her blouse with each thrust.

As John picked up the pace of his thrusting he grabbed Jenny by the waist. Pulling her back onto his cock harder and harder every time, he could feel her grip tighten. Jenny reached back and began rubbing her clit as she was enjoying herself almost to the point of forgetting her plan. As John's balls slapped away at Jenny's dripping hole he almost nervously said "Jenny, I'm going to cum. Where do you want it?"

Jenny quickly responded by saying, "I want it deep inside me. Cum for me John." John felt the pressure building up in his balls. He knew he couldn't hold out much longer.

With just a few more thrusts John emptied his balls deem in Jenny. On weak knees John remained deep in Jenny's warm hole for some time after then withdrew himself. Jenny quickly moved her panties back into place to help keep John's cum inside her. She knew his cum would be crucial to her plan later.

John stood there in post orgasmic bliss. Jenny saw her opportunity and suggested John take a seat. Without his knowledge, Jenny grabbed the other half of the chastity cage. As John sat there panting, his dick began to deflate. Jenny took the other half of the cage and fit it around John's cock. Surprised at how easily it fit after having just been 8 inches hard she clicked the lock into place. John immediately snapped out of his mindless post-fuck haze. "What?? Jenny, I thought you didn't know how to use this??"

Jenny replied, "Oh John, your innocence is so adorable. You don't get it do you? I knew as soon as I saw you that you would be putty in my hand." Waiving the key to his cage she tucked it inside her bra. Smoothing out her outfit she continued, "John, the way I see it you have two options. One, tell me to fuck off and never see me or this key again. Or two, you'll meet Mistress Jenny, and you'll have some of the most amazing experiences of your life." As she said this she adjusted her bra, pushing her tits up for even more cleavage. John was lost in her radiance. He could only think of one thing to ask, "Will I get to fuck you again?" Jenny paused, "Maybe if you're a good boy."

John hesitated. Sensing this Jenny stepped over and put her hand on his chest. "After all, what's the worst that could happen John?"

John looked at Jenny, still in shock from her words. He realized that he wanted this more than anything. He loved the feeling of being dominated. He loved being used. And he loved the idea of fucking Jenny.

"Yes." Jenny had a puzzled look on her face. "That is how you are going to address your new mistress? No, we are going to start this right." Jenny grabbed John by his caged cock and brought him to his knees. As he looked up at her Jenny said, "repeat after me, 'Mistress Jenny, it would be an honor to serve you in any manner you see fit.'" As John repeated this vow Jenny stepped one foot back. Jenny pointed to her shoe, "Kiss." John immediately went to bend down to kiss, "Yes, Jenny, of course." Wack! With a flick of her ankle Jenny lightly kicked John in the cage. "That is yes, Mistress. The name Jenny wil never leave your lips again. And consider yourself lucky I'm not particularly fond of ball busting or that could have been a lot harder... Now kiss." Extending her foot again John whimpered, "Yes Mistress." and began kissing her patent leather high heel.

Jenny smiled. She was pleased with herself. She had successfully broken John and so quickly too. John, however, was oblivious to the fact. He was lost in her presence. As he kissed the top of her shoe he felt Jenny move her leg.

He quickly moved to the top of her foot as it peaked out of the heel and kissed it. Jenny giggled. This was fun. John kept kissing all over her exposed, stockinged foot. As he did so Jenny pulled her foot away. John looked up at her, confused.

Jenny began to walk toward the table that still had the butt plugs on it. Speaking as if addressing nobody important she said, "I have rules John, one of them as you have already heard is that you will refer to me only as Mistress. Another is that my play things stay caged and plugged at my discretion. Come over here John. Be a good boy for your new Mistress and bend over the table."

John quickly hobbled to the table, pants still around his ankles. He bent over the table as Jenny selected the second smallest butt plug from the shelf. "John you are getting the hang of this rather quickly so I think I can push you a bit. We are starting with the second plug. Now be a good boy and open your mouth. Jenny slid the butt plug into John's mouth as she remarked, "you'll want to get that nice and wet...trust me." John lay there with a butt plug in his mouth and his mind racing. Had he really gotten himself into this? What could possibly be instore for him? Jenny snapped him out of his interior monologue with the sudden sensation of spit on John's asshole. She took one of her manicured nails, red with black crosses kept short for...obvious reasons, and began to slide it into John's seemingly virgin asshole. John let our a moan half way between pleasure and discomfort.

After working her finger into John's asshole, she removed it and took the plug from his mouth. Gently she pressed the metal head against his still tight hole. Working the plug in just a bit then back out she eventually got the plug seated in his ass. With a smack on the ass she barked "Pants on! Then kneel." John was quick to obey but Jenny had a different lesson in mind. For the next few minutes she ignored him entirely, checking her makeup, reapplying lipstick, smoothing her clothes. Finally she said, "John, you know why you're locked up right?" John, fearful of the answer, replied, "No, Mistress." "Clearly John, you are a waste of a man. Even with a respectable sized dick you couldn't make me cum. That's very disappointing." John could barely squeak out, "I'm sorry, Mistress." Jenny, knowing this would be the final test to see if John has what it takes to be her chastity sub asked one final question, "Would you like another chance?" John, believing he would get to fuck Jenny again immediately responded, "Yes Mistress. Nothing would make me happier! I'll do anything to get that chance" A smile crawled across Jenny's face, "I'm so happy you feel that way. You'll have one more chance to make my pussy feel good."

Jenny walked over to the table, moved two chairs into place and once again hiked up her skirt. However, this time she dropped her panties entirely. "Here. Crawl." Jenny commanded, pointing to the floor between her legs. John quickly moved into place looking up at here, patiently awaiting instruction.

As soon as he was in position Jenny set her heels on the chair and spread her legs. Grabbing the back ofJohn's head, she pulled him down until his lips met her pussy.

The first thing John noticed was how warm and wet she was. He lapped up her juices hungrily, licking every inch of her pussy. Jenny groaned loudly as he did. He worked his tongue in circles around her clit and then plunged it deep inside her.

That's when Jenny felt it. A slight pause. This is the moment of the final test, the moment John tastes his own cum still inside her. "How do you like the taste of yourself?" Pulling John's head away he said, "Mistress, worshiping your pussy is such a privilege that I would eat cum out of it any day." John, not having realized the extent of what he agreed to was pushed back into Jenny's pussy to continue her licking her.

She moaned loudly, biting her bottom lip as he licked. After several minutes she could feel herself building to orgasm. With one final plunge of John's tongue into her pussy she exploded, flooding his mouth with her sweet nectar as well as his load. John swallowed every drop, savoring her flavor and tolerating his own. He continued to lick until Jenny pushed his head away.

Jenny looked down at John, who was still kneeling before her. She smiled and said, "That's my good boy." John knew exactly what that meant. It meant he had passed the test. Jenny then told him to stand up.

Jenny smoothed out her outfit again, adjusting her cleavage and fixing her hair. John stood before her now fully dressed with his caged cock securely behind the zipper of his pants. Jenny instructed John to collect up the packaging for the cage and plug set. "If my watch is right the store is about to close up. Is your shift ending soon?" John replied, "Yes mistress, our other store associate Ashley is closing up today so I'm off in 5." Jenny cheerfully exclaimed, "Perfect, let's go down to the front desk then. I believe you have some items to pay for."

Jenny and John exited the back storage room and made their way through the absent store to the checkout counter. "Hey! There you are. Where have you been this whole time?" Ashley inquired. " Jenny quickly responded before John could, "John was showing me some specialty items in the back that I was looking for. He really helped me make the right decision." Puzzled by the somewhat odd response Ashley said, "Well great, plop them here on the counter and I'll get you checked out." John put the packaging for the chastity cage and the buttplugs on the counter.

"John, these packages are open. You know policy, packages stay closed, floor models are for display." Ashley rolled her eyes then froze. "John. Where are the items that belong in these boxes?...John?" John now red in his checks couldn't muster any response. Jenny stepped in to explain, "John, show Ashley where the items are." John's expression turned from embarrassment to pure shock. Any color that had been present, now gone. "You can't be serious," John whispered to Jenny. With a quick slap across the face Jenny uttered a stern reminder, "That is Mistress to you. Now show Ashley where the cage is." John, unable to look either lady in the eye muttered "Yes, Mistress." and unzipped his pants.

John had spent hours upon hours fantasizing about being with Ashley but never thought they would have an encounter like this. He had hoped that the short brunette would ask him out one day. Maybe to a concert, it was obvious from her 'hot topic' aesthetic that she enjoyed many genres of music. What John had always been attracted to but never thought much about was her platform black Demonia boots. She seemed to have a pair that went perfectly with every outfit, making her almost the same height as John. He figured he loved the boots because it allowed him to more easily glance at her cleavage, bringing her huge DDD tits closer to eye level. Today she wore a pair of said Demonia boots, knee high with buckles all the way down to her ankle with a wedged platform. Fishnets up to her thighs with a pleated black skirt. To top it off a rather low cut black lace top with a waist cincher to accentuate her already prominent tits. Ashley was a goth dream.

As John pulled his caged cock out of his pants Ashley's jaw dropped. "Are you serious right now! A bow and everything! How adorable!" Adorable. That stung John, he could feel for any chance he had to sleep with Ashley dwindling by the moment. Nevertheless he could feel his cock strain against the cage. Trying, practically begging to be let out of the cage and be erect.

Chuckling to herself Ashley turned to Jenny, "Surely you have the key right?" Jenny dipped two fingers into her cleavage retrieving the key from her bra. Dangling the key as is to tease John she said, "Sure enough. I think he and I are going to be having fun for the foreseeable future."

Ashley still with her mouth agape blurted, "That is so freaking cool! So do you do this with many guys? I wish I had your confidence to try this with one of my hookups." The two ladies laughed. Jenny thinking a mentee would be fun replied, "A lady never cages and tells. But if you are actually interested learning more, give me a call some time." Jenny slipped Ashley a business card as John swiped his card. Exchanging pleasantries and a knowing look from Ashley to John the couple left the store.