Jenny and John Ch. 02

***** This is a continuation of Jenny and John Chapter 1. If you have not read that, I would recommend returning to that chapter before reading this. *****

Walking over to Jenny's Porsche Cayenne she asked John, "Is your car here?" "No, Mistress. I take the train most days." "Wonderful, no silly logistics to worry about then. Come on, get in. You'll be spending the night at my place." Eager to please and excited to spend more time with Jenny, John quickly got into the passenger seat.

Jenny's house was about 25 minutes away. An apparently modest home set back from the road with ample tree coverage supplying lots of privacy. That is until they reached the garage. From here John could see that while the front of the house appeared rather normal, the back of the house extended quite some ways and was much larger than it first appeared. Entering through the garage Jenny hung up her keys and pointed to a shoe rack, "Shoes. Keel." She ordered coldly.

John complied immediately while responding in affirmation. He remained knelt by the door as Jenny continued deeper into the house. Moments later her heels could be heard clicking on the tile as she emerged from the other room. "You know, normally this would be your job." Jenny held a glass of white wine up. "But it is your first day so I'll cut you some slack."

"Yes, Mistress. Of course." John uttered, his voice weak but stable. In Jenny's other hand she held something black with a metal chain. As she grew nearer John could make out that it was a collar and leash. John swallowed trying to clear the pit he now felt in his throat. "Shh shh shh. No need to worry. Be a good boy for me and I promise you'll have a great time." This put John at ease. Looking up at her, Jenny held out her wine glass for John to hold. Taking the collar in both hands she fastened the simple piece of black leather securely but not overly tightly around John's neck.

Taking the leash in one hand and her wine in the other gave a small tug on the chain to indicate John should follow. John began to rise from his knees and Jenny, expecting this, quickly snapped, "No, on your hands and knees." "Yes Mistress." John said, his voice now slightly stronger than before. Jenny took note that John was adjusting to his new role well.

Jenny led John from the elegantly decorated entry room to a lounge. Complete with a pair of leather couches, a bookshelf and various house plants it was quite the cozy room. Jenny sat on one of the couches and pointed, "Hands and knees." John moved into position and Jenny put her legs up on his back as if he were an ottoman. Placing her glass on the end table she grabs the leather bound notebook that has been waiting there. "Now John, we have been playing this by ear so far but I would like to get to know you a little better. Over the next while we will make a list of your interests and limits. I'll start the list of your interests with: chastity, butt plugs, exposure, collaring, 'forced' cum eating. Would you agree?"

John hesitated, just yesterday he was jerking off to run of the mill straight porn. Was he really interested in having his dick caged and ass plugged? Stuttering, John replied, "Yes, Mistress, I suppose so." "Great! Now, really think hard and tell me what else you might be interested in."

Wracking his mind John had no idea how far this rabbit hole goes. Unsure of himself he muttered, "I'm not sure Mistress. Maybe spanking?" "Wonderful! That is one of my favorites!" Jenny exclaimed cheerfully. But Jenny could tell that John was out of his element, "Would it help if I listed some topics and you answered 'yes' for interest, 'unsure' for maybe you'd try it and 'no' for hard limit?" John, relieved at Jenny's offer for help, agreed that it would be helpful.

"Wonderful, let's begin." John in a personal effort to make Jenny happy vowed silently that he would say yes to everything except piercings and shaving his head. John felt good about the decision not realizing the depth of Jenny's interests.

"Bondage - ropes and cuffs?"

"Yes, Mistress."

"Bondage - furniture to include St. Andrew's Cross or a bench?"

"Yes, Mistress."

"Imprisonment/Caging?"

"Yes, Mistress."

"Face sitting?"

"Yes, Mistress."

"Analingus?"

"Yes, Mistress."

"Orgasm control?"

"Yes, Mistress."

"Cuckolding?"

John paused, he knew what that meant. He's seen porn revolving around that here and there but never paid much attention to the plot. Finally he gave in, wanting to please Jenny.

"Yes, Mistress."

"Sissification?"

Again a pause, John had only heard this mentioned a few times from passing customers. To his knowledge it was mostly just chastity and butt plug play but he was unsure. Not wanting to keep Jenny waiting he blurted,

"Yes, Mistress."

"Threesomes?"

"Yes, Mistress."

"Role playing?"

"Yes, Mistress."

"Very good John, I think we can pause there for now. The rest get pretty deep and honestly I think they are more mess than they are worth. Now John, we have covered most pertinent limits, tell me about some of your fantasies. You may speak freely."

John thought for a moment, while his girlfriends in the past had been interested in sex none had ever asked about his fantasies. Immediately John's mind went to porn, after a few years of dating his hand surely there were a few videos that stuck out in his memory. "Mistress, I think I have a few if that's ok." Jenny, eager to hear, responded, "Of course John, tell me all of them. I would love to learn what interests you."

"Well, I think the classic school girl and teacher fantasy is certainly on the list. You know, a girl needs to get her grades up and will do anything to make it happen. Short pleated skirt, skimpy white top, little Mary Jane heels, maybe some stockings, hair in braids."

Jenny wrote as quickly as she could while encouraging John to continue. "Ummm, I guess there is always the fantasy of a threesome. Your wife brings home her hot friend and you all go to town."

"I also really fantasize about total submission and free use. Someone entirely there for sexual pleasure and nothing else."

"Then there's the girl that can't pay her debt so she has to find another way. You know, rent, gambling, a cab fare so she sucks the guy off."

"That's all that comes to mind right now Mistress, I can try to think of more if you'd like." Setting her notes down Jenny had a pleasant smile on her face as she looked down at John. "No need, this is plenty to start with. Now there is another room in this house I'd like to show you."

Jenny finished off her glass of wine and rose to her feet. Again her heels clicking on the tile she led John through the entry hall to what appeared to be a closet door. Jenney passively stated, "You may stand when going up or down stairs." Opening the door John saw stairs that descended to a room that was softly lit but not necessarily dim. Upon reaching the bottom of the stairs he saw that this was a full on sex dungeon. Very finely furnished with yet another leather couch, rubber padded floors a St. Andrew's Cross, a paddling bench, a pillory, a bed with a cage underneath, a sybian mounted atop a sturdy metal frame, a wall covered in various whips, paddles, crops and canes, another wall covered with shelves of any kind of dildo you could imagine and to top it all off, a throne.

Jenny led John over to the throne taking her seat. John, knelt in front of her, could now see that there was a sort of hinging cuff built in. Without looking at him, Jenny said "It is meant to hold your head in place while you worship my pussy." John, growing excited at that thought, almost shouted "Of course, Mistress."

Jenny gazed around the room, admiring all that she had collected here before addressing John. "Everything you see in this room is mine, including yourself. When I am in this room, I do what I want, when I want. Even more so than my day to day life."

Jenny paused before continuing, "John by now you realize that this will not be a normal, vanilla relationship. You'll be pushed to limits you didn't know you had. So I'll ask you this once more." Another pause as she held up the end of the lead, bending over and uncrossing her legs to give John a glimpse of her panties. "Do you want to do this?"

John took his time to think. Admittedly, he was nervous of what might happen but not afraid. In the past few hours he had experienced more excitement than in all of his past sexual encounters combined. That made his mind up. "Yes, Mistress."

"Wonderful John, I am delighted to hear that. Follow me. Now that we are on the same page let's show you a bit of what our 'typical' sex life might look like." John's heart beat so hard he could hear it in his ear canal. He hurried after Jenny as she led him to the spanking bench. "Undress, then up." John complied immediately.

The bench was designed so that one's torso would lay on top and their limbs would rest on cushioned bondage points on either side.

With John buckled in, Jenny moved in John's blind spot to one wall then the other. "We are going to start you off with some impact play tonight. I have here a leather paddle, a wooden paddle, a crop, and a flogger. You'll take 10 strokes per ass cheek per implement. Understood?" John nodded his head as Jenny bent down and whispered, "I know you can take it but if you ever need to stop simply say 'emergency.'"

John nodded, confident he would not need to use the safeword. Jenny stepped back then suddenly, WACK. The flogger landed on his right ass cheek. John was surprised, there was certainly the sensation of an impact but it was broad and dull rather than sharp. Except for the ends where there was the tiniest sensation of a sharp pain from the many tips of the flogger. Jenny continued, each time increasing the strength of the blow. John now felt more of the impact sensation he expected and just as he was starting to feel uncomfortable he heard Jenny, "Good boy John, let's move onto the next."

Jenny grabbed the leather paddle and again starting gently, struck John. This time the pain was a bit sharper but dissipating quickly. Discomfort built quicker this time around but John was determined to take whatever his Mistress dealt. By the last stroke John felt a warmth on his ass like never before. He was sure his cheeks were red and would be for some time.

Jenny again, prasing John, grabbed the wooden paddle. This time she kept her swing strength up from one implement to the next. With one swoop through the air John felt a heavy, dull pain. Almost like a massage this feeling lasted for some time after each strike. Biting his lip he wanted to keep quiet and keep up the facade of a high pain tolerance. Jenny knew, she could hear his breathing become short and labored. Easing up toward the end John made it to 20.

"How was that John? Are you enjoying yourself?" In truth, John was. While there was physical discomfort the pleasure of mindlessly being at the mercy of another was bliss. "Yes, Mistress. Please may I feel your crop?"

"Well of course you can." Jenny landed a stinging blow that subsided quickly. As she wound up for another strike she began to explain, "You know John, this crop is rather special. You'll be taking 10 hits in addition to the 20 on your ass."

John with eyes squeezed shut braving the pain asked, "Where, Mistress?" Jenny let out a cynical chuckle, "On your locked up little balls, of course."

John's eyes flew open. He couldn't believe it. As if the now raging fire on his ass cheeks weren't enough he would have to endure 10 slaps to his balls. Instinctively he tugged at the restraints but he knew there was no escape. Jenny, having finished tenderizing John's ass, picked up one additional item. "John, how are you doing?" John thought carefully about his response, "I am okay Mistress. My ass hurts but I can tell you are enjoying this and that is more than enough motivation for me."

Jenny laughed, "Oh John, I appreciate the flattery but that will get you no mercy. Now open your mouth." Before he knew it, a ball gag was in his mouth and fastened behind his head. "Now John, if you really need this to stop while the gag is in your mouth, shake your head back and forth shouting 'no' through the gag as loud as you can." John nodded in understanding as Jenny returned to her position behind him.

SLAP. The sharpest pain John had ever felt rushed through his balls and into his abdomen. He couldn't help but yelp through the gag. To John's surprise, the pain quickly diminished. However, something else was even more shocking. John could feel his cock straining against the chastity cage.

"Wait, do I like this? How could I? She is beating me senseless yet my dick is trying to get hard? But the power she has over me, it's intoxicating. If I just take the rest of these strokes I bet she'll reward me by unlocking me."

John's thoughts were interrupted by yet another swat. Jenny, knowing full well to take it easy on John was in reality only flicking the crop a few inches each time. Strike after strike John's balls became more engulfed in pain yet his caged stroll bounced as blood pumped to his dick. John was confused by the sensation of being aroused with his imprisoned member. An odd feeling of security and a tightness that you would desire from a hole but discomfort as the ring tugged on his balls.

As John focused on the sensations in his cock Jenny stepped in front of him and crouched down. With her hand under his chin, Jenny lifted John's head to meet her gaze. "You did wonderfully John, I'm so proud of you." John mumbled something that you could only guess was "Thank you, Mistress."

Jenny stood up, leaving John in euphoria of submission. Returning to him, Jenny placed a hand softly on John's ass. "You have one more test. If you do well I'll unlock you for a reward." John perked up, elated by this news. Jenny stepped in front of him and John's excitement quickly turned to concern.

There she stood, in her black patent leather heels, black seamed stockings and red garterbelt and bra matching set with her hands on her hips. Centered in John's view and replacing her panties, was an addition to her look, a pink strapon dildo.

The dildo was moderate size, about five or six inches and rather thin. Perfect for a beginner. What John couldn't see was that the dildo continued through the heavy duty leather harness into Jenny's pussy where a vibrating end of the dildo was seated. "Now John, I know it looks scary but I promise, if you take deep breaths and trust me, I'll make you feel amazing."

John reluctantly nodded his head, the only thing going through his mind was the thought of Jenny taking the cage off so they could fuck.

John felt Jenny's fingers wrap around his butt plug she'd inserted back at the sex shop. With some pressure and a quick pop the plug was out. In a night full of surprises and new experiences John found yet another. Without the plug in his ass there was a somewhat empty feeling. Before he could process this any further a cool, slippery sensation struck. Jenny, now using a finger, massaged lube into and around John's asshole.

"Breathe deep for me. Be a good boy for me and relax your hole." Jenny pressed the tip of the strapon against John's virgin hole. Slowly he put more and more of her weight onto him as the head slipped inside of him.

John felt the head press into him with a good bit of discomfort but once the head once in that discomfort began to ease. John began to wonder how many guys Jenny had pegged as she knowingly held the strapon still with just the head inside him.

Before he knew it the discomfort passed and the feeling of fullness returned to his hole. Jenny expertly slid another inch into John before pausing again to give him a chance to adjust.

There was certainly less pain with this push but John needed time to adapt to this new sensation. Unlike the buttplug that felt rather comfortable and filling, the dildo continued to stretch him even after insertion. John needed to make a conscious effort not to clench his ass on the dildo whereas the buttplug was necked down before flaring out at the entrance of his ass for a more forgiving fit.

John was provided some welcomed help in adjusting to the intruder when Jenny turned on the vibrator embedded in the strapon. Waves of pleasure radiated through his asshole as well as somewhere deeper inside him. Again, John felt his cock strain against the chastity.

As the strapon seemed to massage his hole Jenny pushed further into him. John was engulfed in a mixture of new sensations, pleasure and confusion until he felt it. Jenny's stocking covered legs press against the back of his thighs.

She was all the way in. John melted in a heap of submission as he felt Jenny's smooth upper thighs against his ass checks and her stockings and garter clips midway down his thighs. Running her fingers through John's hair, Jenny whispered, "That's my good boy."

As if he weren't before John strained even harder against his cage now. His cock fighting for escape, for a hole to enter. That's when he felt it, another addition atop a night of sensations he'd never experience. A warmth passed through the center of his cock. Jenny laughed, "Looks like someone is enjoying themselves. If I got you to leak precum this easily, I imagine it won't take much training to make you cum from pegging."

John was at a loss for words. Laying there he slipped deeper into a mindless state. Jenny began to pull the dildo out of John. Just as the tip reached his asshole Jenny stopped. "Please, please." John mumbled through his gag. He couldn't believe it, he was begging for her to push it back in! John couldn't bear the empty feeling that was left behind when the dildo was withdrawn. Jenny happily obliged, shoving the dildo back in. She continued fucking him, slowly as he was still a beginner but she could feel his grip react to her thrusts.

John was in heaven. The dildo's motion in and out expertly guided by Jenny was now nothing but pleasure. In fact John was so lost in how his was was being fucked that he has forgotten the discomfort he felt on initial penetration.

The dildo has the slightest bit of texture to it stretching and relaxing John's hole. As the dildo slid smoothly across his hole John could feel a pit in his stomach grow. Rather than a sick feeling it was more of a build up, like how butterflies in your stomach would feel. All the while precum leaking from John's cock in a mostly constant stream now.

"Good boy. That's it, be a good bitch and take it." Jenny's voice dominated the room, sending John's butterflies into flight. From his lower abdomen the pit suddenly grew much stronger and John uncontrollably began to squeeze his ass. Over and over as waves of pleasure ran over him. "Am I cumming? I'm not quite sure, it didn't feel all the way like it." John couldn't help but wonder if that's what it was when suddenly he started squeezing again. "But how? I've never cum twice in such rapid succession before." John decided it was best not to think about it too much and enjoy the sensations Jenny was giving him.

Jenny now fucking John at a moderate pace, felt her stocking tops start to dampen. Little aroused Jenny more than breaking in a new sissy. John had a ways to go but Jenny's mind raced at the possibilities. Playing out scenarios in her head she could feel the strapon moving in her pussy and rubbing up against her clit with every thrust. Finally, as she thought of the fantasy of prostituting out John as a sissy she exploded.

Jenny's fantastic juices ran down her leg as her knees buckled. One of the few times she was uneasy in heels, she grabbed John's waist for support as she rubbed her clit on the end of the strapon. Now her motions were more for her own gain rather than his pleasure or anal training.

Through deep breaths Jenny withdrew the strapon. Discarding it to the side she undid John's gag. "Oh John, you made me feel so good." Admittedly, she did not believe this. She had fucked him bringing herself to orgasm through using him. However, she needed John to think he had value in her sexual pleasure beyond just a hole.