Jenny and John Ch. 03

***** This is a continuation of the Jenny and John series. If you have not read the previous chapters, I would recommend reading those before reading this chapter. *****

Jenny awoke in a shower of dawn sunlight, well rested after her night of breaking in her new sub, John. She'd met him only yesterday but already had him in her grip. She'd managed to lock him, peg him and get him to eat his own cum, among other things.

Stretching as she sat up, Jenny could hear the soft, rythmic breathing of John still fast asleep. Jenny figured she'd let him sleep, he deserved it after taking everything in stride yesterday.

Jenny did not have a particular desire for a service sub, she was more than happy to take care of things around the house. Although, with a maid that visited daily she didn't need to clean much. Jenny tiptoed her way out of bed with John still restrained in the cage below. Jenny wanted to show John that her intentions were more sexually charged than service or humiliation based so she decided to make breakfast for the two of them.

As Jenny exited the room she grabbed one half of the two way baby monitor she had discreetly placed for just this purpose. As she entered the kitchen she gathered some utensils and ingredients for eggs and sausage.

John awoke from a deep sleep. Immediately he noticed the butt plug still in his ass from the night before and the chastity cage imprisoning his dick. John's cock struggled against the cage in a fight to get hard. As the buttplug had been stimulating John's prostate all throughout the night he found that his thighs were coated in precum. John moved to feel the cage holding his dick hostage but was immediately reminded of the shackles. His thoughts moved to Jenny, was she still asleep? Had she abandoned him?

Just as Jenny finished cooking she heard a stirr on the monitor. "Mistress?" John whispered, "Are you still asleep?" Delighted that John remembered to refer to her as Mistress as he awoke so early in their relationship she picked up the radio. "Hi John, I'll be there in a moment. I was just making some breakfast for us."

Jenny set off for the bedroom, stopping by a hallway closet first. She grabbed a tshirt and pair of gym shorts she thought would fit him. She had a stash of many sizes for instances like this.

"Good morning John, how did you sleep?" Jenny spoke in a soft, almost nurturing voice. "I slept very well, Mistress. But I have to say my ass is rather sore." Jenny chuckled, "Cheeks or hole?" The two laughed together, calming John's nerves.

Jenny unshackled John, still naked from the previous day's activities, and let him out of the cage. "John, I know yesterday I was tough on you but I don't want you to get the wrong idea. I don't want to be some dictator that is all business all the time. When we are eating meals here at my and before breakfast in the morning, we can relax the rules." John let out a sigh of relief, "Thanks Jenny." She grinned, "I said relax, not throw out." John, quick to correct himself, said, "Of course, sorry Mistress."

Jenny went on to explain that unless stated otherwise before breakfast and at meals John could dress how he liked to an extent and could speak freely rather than simply responding to her. He also would not be forced to crawl and on many occasions would not be required to be plugged.

Jenny motioned to the bathroom, "Take a moment to use the bathroom and take the plug out." John was sure not to waste time and returned to Jenny's side within a minute or two.

"How does your ass feel now that the plug is out, John?" John pondered his response for a moment, "Mistress, it is definitely sore after yesterday but I almost feel like something's missing now." Jenny smiled, "I knew you'd turn out to be a butt slut." Again the two laughed as John put on his clothes and they walked to the kitchen.

John felt odd roaming Jenny's house on two feet, without his leash on. The two sat and made small talk while they ate. Still relative strangers despite their fun the previous night, the conversation shifted to their work life and how they wound up where they are today.

As John cleared the plates Jenny couldn't help but admire the natural submission that had already set in. John kept his view downcast, had cleared plates without being asked to and returned to Jenny's side when he was done.

"Well, I think next on the list is getting you cleaned up." Jenny motioned for John to follow her and led him back to the master bath off her bedroom. Jenny gathered two towels sparking excitement in John. "Oh no, my sweet John. We won't be showering together." Jenny seemed to always be one step ahead of him.

In the bathroom, Jenny helped John disrobe and ushered him into the shower. "Now John, we are going to start with a chastity cleaning as we will every day. Now place your hands behind you." Jenny slid a pair of rubbery feeling but very sturdy cuffs over John's wrists. "Very good, now I'll unlock you for cleaning." John's cage twitched as the word 'unlock' passed over Jenny's lips.

Jenny retrieved the key from her cleavage and unlocked John, gathered some soap she began to clean John's penis. John couldn't believe the sensation. He didn't think cleaning could ever be so pleasurable. Once John was clean Jenny decided her fun was not over. Slowly she adjusted her grip until she was practically giving him a handjob. John basked in the attention his cock was receiving but just as his balls tightened, nothing. Jenny had taken her hand away and retrieved the key to John's cage.

Sternly, Jenny explained, "You have two options. One, you have until the count of 20 to lose that pathetic erection. Two, I change the temperature from warm to cold and make that cock soft."

"Mistress, please, count to 20." John begged. He squeezed his eyes and did all he could to distract himself from Jenny.

"...16...17...18..." Jenny counted painfully slowly, knowing John would need all the help he could get. At 18 she could see him start to droop. Being generous, she slowed her count. "...19...20. Time to cage you up." John wasn't quite flaccid but he was soft enough. With some force Jenny could put the cage back on and lock it in place.

"Now John, for the rest of the shower you'll be unattended but I'll be right outside so I'll hear if you try to play with your pathetic little dicklet." John's stomach did a flip. "Do I like humiliation? She doesn't like my dick? Will I be able to satisfy her if she lets me fuck her?" John's mind wouldn't shut up.

Jenny's voice came back to the forefront of his attention, "After you wash yourself you have some tasks before your shower is done. Each day you'll give yourself an enema to ensure you're clean for anything I'd like to do. Each day you'll remove all hair below your eyebrows, it looks like you don't have much to begin with so that's not too much trouble. I have Nair in here to make it easy, plus I don't want any razor burn on you. Finally, each day after your enema you'll douche with this strawberry scented solution. Understood?"

As John washed himself he wondered why Jenny would want him hairless. Considering the possibilities while completing his enema, John ultimately decided to chalk it up to 'a Domme's request' and accept that he is the sub.

John washed away the Nair from his entire body, cheeks and chin, arm pits, chest, legs, pubes and ass crack. With the warm water rushing over him John traced his hands across his legs. They were so smooth that if John closed his eyes he might have mistaken them for a woman's legs.

John stepped out of the shower to find a buttplug and lube on the counter. It didn't take a genius to figure out what Jenny wanted in this case. John quickly dried off and picked up the buttplug. This one was silicone rather than metal like he had yesterday with far more texture to it. Additionally, while the plug was the same width it was far longer, almost resembling the shaft and tip of a penis.

John put a leg up on the toilet seat and lubed his asshole. Recalling that Jenny used a finger to spread the lube in and around, John decided to finger himself. Telling himself he was simply preparing for the plug he chose to ignore the twitch in his cage.

With John's hole lubed he took hold of the buttplug's T-base. He pressed the head against his hole feeling a bit of discomfort, almost to the point of pain. John eased up the pressure then pushed again. This time John got the plug in slightly farther. Repeating this process John finally found the relief of the neck of the plug.

With his asshole now able to relax and his rectum full, John couldn't help but notice the twitch in his cage. Surprised at how pleasurable having his ass full felt, John took a step toward the bathroom door.

He halted when his foot hit the ground. Cautiously he took another. With precum leaking from his dick John thought to himself, "Oh. My. God. This plug is shaped just the right way so that it rubs my prostate every time I take a step. How am I going to focus on anything today?"

John hesitantly continued, consumed by the sensation the plug sent through his abdomen, he was careful not to become distracted and trip. As John made his way back into Jenny's bedroom he presented his naked body to her.

"Let me see you." Jenny remarked, running her hand up and down John's legs. "Perfect! Smooth as a girl's." Jenny jabbed. John was thrown off by this but had no time to respond. "So John, how do you like the plug?" With a new drop of precum starting to leak, John explained, "I love it Mistress. With each step I get a rush of pleasure. It almost feels like I'm being jerked off but from the inside."

"I'm so glad to hear that. I thought this one might do the trick. But we can have you ruining my carpet." Jenny teased as she bent slightly. Reached a finger down to John's cage, she scooped the drop of precum. Bringing it to John's lips she commanded, "Open." John followed orders, allowing Jenny to wipe the precum on John's tongue.

John expected the now familiar, bitter-salty taste from last night. However, this time there was no bitterness. An almost salty-sweet taste spread over John's tongue to the back of his throat. This time around John was in no particular hurry to rid his mouth of this taste.

CLICK, Jenny attached the leash to John's cage and said "Follow me. We have a full day planned."

Jenny, still in her robe, led John back to the dungeon. He found that now the spanking bench had been moved from the center of the room replaced by the Sybian. The Sybian had also been lowered from about waist height to knee height. John put two and two together, figuring he'd be sitting on it.

"Now John, I'd like your help with something." Jenny began, continuing over to the Sybian. "There is a new dinner place that I have been dying to try but I don't know what to wear. I need you to help me pick. But of course that is not much fun for you, sitting around waiting for me to change, so you'll have some entertainment of your own."

Jenny had retrieved a bottle and was lubing the almost dildo-like attachment on the Sybian. "Bend over for me." Jenny barked. John immediately placed his hands on the leather sides of the Sybian and spread his legs. Jenny removed the butt plug from John and placed it on a nearby table.

"John, take it slow but sit on the Sybian for me." John slid down on the Sybian, his ass now malleable from having a buttplug in. Once he was seated Jenny procured two cuffs that were attached to the sides of the Sybian's stand. John knelt, most of his weight resting on the Sybian with balance supplied by his knees and cuffed wrists.

"Here is how it is going to work. I have three outfits in mind for dinner and you'll vote for which I should wear." Jenny explained, as she walked behind John. Returning to his view she had a wrapper in her hand. John couldn't quite make out what it was until Jenny held them in front of his face. "I'll be putting a new condom over your cage before each outfit. With each condom associated with an outfit, whichever is fullest after seeing the outfit wins."

John was certainly excited to see Jenny show off her looks but couldn't help but feel that was an odd way to judge. Jenny grabbed a blindfold and a ball gag from the table and secured them on John. Jenny bent down and whispered, "No peeking before I'm ready."

Suddenly, John felt something moving in his ass. This didn't feel like the strapon felt yesterday, there was no fullness-emptiness cycle. Instead it felt full but as if the dildo was spinning, as if it were tracing the surface of a cone. His asshole was not being stretched but his prostate was being stimulated in a mechanically rhythmic pattern.

Then came the vibration. John doubled over from the shock. Not from pain but rather pleasure. He now had a dildo milking his prostate while vibrating his ass and balls. John couldn't believe the sensation, it was an unreal experience as if floating on a cloud.

Jenny made her way over to the dungeon's bed, similar to the bed in her room in that there was a cage below. Jenny had placed the three outfits there in preparation for the fashion show. Grabbing the first one she slipped it on and smoothed it out before making her way back to John.

"I've got the first outfit on John, let's just get that condom on you before I remove the blindfold." Jenny called from across the room.

John had been sitting there for what felt like an eternity. Nothing went through his mind except the endless bliss that was his anal stimulation. As John heard Jenny's calls he snapped back to the moment. Within a few seconds he felt familiar fingers and manicured nails fondle his cage and balls.

As Jenny slipped the condom over John's chastity she gave it a loving tap, as if to say 'there we go.'

Jenny removed the blindfold of a jaw-dropped John. Jenny stood there in a modelesque pose. The first outfit was a fitted cream dress that came just above Jenny's knee. At the neckline, there was a gold chain supporting the revealing cut of the dress. Several strands of fabric to the outsides of Jenny boobs clung to the chain in an effort to support the seemingly built in bra.

After a few moments John was able to tear away his gaze from Jenny's ample cleavage to see that she wore no stockings but accessorized the dress with a pair of matching cream heels. They were leather platform pumps with symmetric straps starting near Jenny's toes, crossing over top her feet and joining around her ankles.

John was speechless, not only because of the gag but he was submerged in Jenny's beauty. As the Sybian milked his prostate and with such a stunning sight standing in front of him John couldn't help but leak.

That same feeling he felt yesterday of the warmth flowing through the center of his locked dick returned. As Jenny now turned her attention to a nearby mirror, she adjusted her hair and breasts before turning back to John? "Do you like it?" Jenny teased, spinning in a circle to give John a look at how the dress hugged her ass.

John nodded frantically like a mindless brute. His only thoughts were on Jenny and how lucky he would be rip that dress off of her.

"Well I think that about our time with this outfit." Jenny sauntered over to John, exciting his caged cock further. Jenny slowly bent over giving John an up close look at her ample cleavage before replacing the blindfold.

Again John felt Jenny manipulating his cage, presumably removing the condom for comparison later. Despite being locked securely, John's cock strained at the cage. Now with the image of Jenny in a stunning dress burned in his mind as the Sybian continued, John was losing it. He began ever so slightly grinding his asshole back and forth with the motion of the Sybian as he replayed Jenny's modeling over and over.

Jenny returned to John without notice this time. Having changed, it was time for a new condom and the blindfold to come off.

John was again speechless. Jenny stood there in the same pose as before, this time in a little black dress. Again fitted perfectly to every one of Jenny's curves it came to mid thigh with a deep v neckline. This dress came up around Jenny's shoulders and included a piece of fabric around her neck resembling a choker.

With this dress Jenny had paired black stockings and a pair of black leather peep toe heels. They had a slight platform to them with a stiletto heel and a simple ankle strap. What John hadn't seen yet was the garter belt.

As John sat on the Sybian he made every effort not to blink, he vowed not to miss a single moment of the show Jenny was putting on for him. Jenny held various poses, standing, bending forward, pressing her tits together, all the while John leaked and leaked into condom number 2.

Jenny had one last pose in mind. She turned her ass to John and slowly ran her hands down her legs while bending over. Just as her hands met her knees John could start to see the clips on the black garter belt that held up Jenny's stockings.

John doubled over at this sight. The sensation of a pit forming in his stomach as it did the previous night returned. The warmth in John's abdomen was now a bonfire. John couldn't tell how much he was leaking but it sure felt like more than with the last outfit.

As Jenny stood tall again she smoothed the dress down over the garter clips. Again she returned to John to collect the condom and replace the blindfold.

John was taken aback at how much he was enjoying this. How could he receive so much sexual pleasure without cumming. Without even touching his cock? John's mind raced flashing between the two outfits Jenny had showed off.

Just as John began to come off the high of seeing Jenny's little black dress, he felt the condom roll over his cage and the blindfold was removed. Upon seeing the third outfit John immediately strained in his abdomen, the now familiar feeling of leaking precum began as soon as the blindfold was removed.

Jenny stood in front of John in the same modelesque pose as the previous two times. This time she was dressed in a short skirt, white sheer blouse and a blazer-like jacket that matched the skirt.

The skirt was a checker pattern of light, almost whitish pink and a slightly darker but still pastel pink that just barely covered her ass. The jacket matched and while long sleeved to cover her arms, did nothing to obscure the view of the sheer white blouse. John also noticed there was a decorative series of gold chains over the front of the skirt accentuating Jenny's slim stomach.

The neckline of the blouse sat on her clavicles with a v cut in the center. The v appears as if each side was meant to overlap with the other but had no buttons present to do so. Beneath the white blouse you could clearly see the outline and some texture of Jenny's white, lace bra. With the two layers of fabric her boobs were definitively covered but her fit torso was subtly on display.

Jenny paired this outfit with knee high stay-up stockings, leaving some of her smooth thighs exposed. To top off the look she had cream leather platform pump heels. These heels featured an ankle strap and toe strap rather than a more covering peep toe style. Jenny looked like every man's dream of a slutty secretary.

John could feel a near constant flow of precum passing through his twitching dick. The Sybian was acting more as a pump now than anything else spurring on each wave of the clear liquid.

Jenny gave John a full view of the outfit, even bending over to flash her white lace planties that matched her bra. John couldn't believe his eyes, Jenny looked like a porn star taking promotional pictures right before a shoot.

With the tension building even higher in John's abdomen Jenny removed the condom and turned off the Sybian. As John sat there panting Jenny held all three condoms in her hand, each tied off and numbered with a sharpie corresponding to outfit order.