Author's Note: First story ever! Much like my unlucky protagonist, I'm a 26 year old submissive male from Brooklyn. I've been reading BDSM stories most of my life and finally sat down to write one, please let me know what you think!


Part One: The Trap

Well this certainly throws a wrench into things, Mark thought. He had just found out that his roommate was moving in with his girlfriend, leaving him all alone in a Brooklyn apartment that he could no longer afford. He had only just moved to the city two months ago, after his girlfriend of three years had left him, and he was finally starting to attract some clients as a freelance web developer. Despite being educated and working all through college, he barely had two dollars to rub together after paying for food, rent, insurance, and student loans. Everything else he wound up spending on Vanessa, who seemed to be the only person capable of bringing a smile to his face at the moment.

Mark had always had a predilection for a certain type of woman. Throughout his life he had developed crushes on various babysitters, teachers, and older cousins; essentially anyone who was any kind of authority figure in his life. Although Vanessa didn't have any kind of direct, institutional authority over him, her demeanor and tone made Mark weak at the knees since the first moment he had met her. She was the kind of woman who made Mark both nervous and excited whenever he was in her presence. At 38, a full thirteen years older than Mark, she was a successful partner at a small law firm, but she would have been a catch even without being so professionally accomplished. With her 5'6", 120lb frame, long auburn hair, trim figure and voracious sexual appetite she was almost more than Mark could handle! Despite being smaller than Mark she was slightly stronger thanks to her long hours at the gym, and she was not afraid to physically overpower him when she wanted to. The best part about her though was that she was willing to indulge some of Mark's kinkier fantasies.

Part of the reason his previous relationship hadn't worked out was his ex thought he was a bit of a freak. They had gotten along well for years before Mark saw some porn on the internet that had infected his mind like a drug, awakening new desires he never even knew he had. All he had asked initially was to be spanked now and then, maybe have her be a little more forceful in the bedroom. She had clearly been put off when Mark told her, and a few days later she said it wasn't going to work out between them. Mark was distraught for weeks before he decided to move to New York and start over.

When he found Vanessa on the website and she not only replied to his message but agreed to meet, Mark was ecstatic! Here was a woman who knew what she wanted and wasn't afraid to take it. They had started off perfectly, with light spanking and bondage, a little humiliation. But in the weeks since Vanessa had kept pushing him, and each time Mark had left her apartment recently he had felt an unsettling mixture of shame and arousal. Of course he would always go home to jerk off afterwards, but that just made him feel more conflicted and ashamed afterwards.

Thinking of the last time he visited her made his cock swell in his new cage. As soon as they arrived in her apartment she had made him take off all of his clothes and serve her wine before she pushed him under her skirt toward her smooth, slick pussy. After she came he had stood up and started to press his hard cock towards her, but she slapped it away and grabbed his balls, twisting him around and pulling them up between his legs. She then pulled out a pair of handcuffs and linked his hands behind his back. Completely in control, she walked him over to the other side of the couch and bent him over the back before retrieving a leather strap and going to work on his ass, furious that he had tried to fuck her. Welted and begging, she finally decided he had had enough.

She pulled out a small chastity device and fitted it on him before pulling a pair of pink panties up his legs. He spent the rest of the night cleaning her apartment like that; sore, horny and humiliated; before she sent him home that evening still wearing the cage and panties.

Mark was a bit scared by how thoroughly she had dominated him that night, all he had really wanted was some light spanking and bondage, maybe a finger up the ass at some point. He would just have to be a little more assertive in the future. He would let her know tonight to take it down a notch. Still, he thought, it had been one of the most erotic experiences of his life, and it hit Mark like a sledgehammer when he realized he might have to leave her for good if he couldn't work out a new living arrangement.

Mark laid down on his bed and thought about his options. Couch surfing wasn't an option, he had only been in New York two months and didn't know anyone besides his current roommate and Vanessa, and he knew it was way too soon to ask to move in with her.

Moving home was out of the question, his parents lived all the way in Arizona, and he didn't exactly leave on the best of terms with them. Besides, there was no real work in his field in that area, and he wasn't eager to go back to bartending.

Mark began looking online to see if he could find a spot for himself, but everywhere he saw was completely out of his price range, especially with the housing rush as all of the college students were snatching up anything remotely affordable.

The third option was to try and find someone on craigslist, but he had heard so many horror stories that he considered that a last resort.

After wracking his brain for the better part of an hour, he came to and realized he was going to be late if he didn't hurry. Mark rushed to the bathroom to clean up. Looking at himself in the mirror, he wondered again how he had gotten so lucky with dating Vanessa. While he was reasonably attractive, with his clean shaven face and long dark hair, he had always been self conscience about his 5'7", 140lb frame, and his lack of body hair. Vanessa didn't overtly flirt with other men when they were out, but she did always seem to be a little extra friendly around larger, more masculine men. He finished getting dressed and rushed out the door to meet her at the restaurant.

Vanessa stepped out of the shower and slipped on her blue silk bathrobe as she started preparing for her date with Mark. She adored spending time with Mark, aside from being clever and interesting, he was also a naïve little boy, and she was enjoying leading him down the rabbit hole. They had met a month ago on a BDSM contact site, and although she wasn't very excited to meet at first, she became much more intrigued when she discovered Mark had only had one girlfriend previously, one who was never dominant. She found herself becoming thrilled at the idea of capturing this naïve little boy who just wanted to try out a bit of bondage and spanking. Mark may think he's just dipping his toes into the water, but I'll be sure to drag him into the deep end, she thought.

She had found there was a fine line to walk when finding and molding the perfect slave. There were lots of men who would willingly debase themselves completely, but without offering any resistance Vanessa found little sport in dominating them. Mark was currently a willing sub, but she knew he would bolt if she pushed him much further, and she was growing impatient. She fed off that look in a boys face when he realizes that she has complete control; the look that knew it was too late to back out. She usually saw it when she informed her desperate, panicking slave that his safeword no longer applied.

She knew that Mark was already infatuated with her. What she needed now was leverage. While she could always try going the photo/video route she wouldn't even know where to send the evidence should Mark revolt. He had no friends in town, no full time employment, and no social media presence. Since that fucking 50 Shades of Grey book had come out everyone seemed to be getting into BDSM, so a few indiscriminate photos weren't necessarily the deathblow they once were.

While she had always had the body and personality to secure the necessary infatuation, it was only recently that she had gained the means to fully fund her lifestyle and obtain the necessarily leverage.

Vanessa had graduated summa cum laude from Princeton and now worked as a partner at a small law firm specializing in intellectual property. While she was sharp as a whip and very good at what she did, many of her colleagues had speculated that maybe she had slept her way to the partnership. She grinned when she thought about it.

While she had no doubts that she would have made partner eventually, she had quite a head start over her peers thanks to her domme friend Sarah, who had been seeing a senior partner at her law firm for a few years professionally. Vanessa was confused when she saw the photos of her boss, David Ludwig Jr, partner at a multi million dollar law firm, married with two kids. The photos showed him dressed in a frilly pink maid's outfit cleaning Sarah's apartment, but after Sarah explained the ins and outs of both her profession and her relationship with David, Vanessa started to come around to the idea of having a slave. The following night they arranged to get together and have David serve them. Obviously they declined to warn David, and he was shocked when Vanessa walked in to find him gagged, plugged, chastised, and kneeling in the corner. Vanessa played her part perfectly, feigning outrage and disgust. After that Vanessa moved up the corporate ladder quite quickly.

Vanessa stepped out of the bathroom to get dressed, going through her closet. She selected a pair of black jeans, fitted white tee shirt and a black leather jacket, with a pair of clean white designer sneakers. She looked sexy but not trashy, and totally comfortable. As she hopped in the cab to meet up with Mark, she lamented things weren't moving faster. She was eager to train him as a real slave and really bind him to her, but she was at a loss as to how to do that without scaring him off.

" So that's pretty much the situation. Looks like unless I land a major client I'll have to leave the city by the end of the week. I just wanted to let you know in case things.... you know... don't work out."

Vanessa struggled to hear the end of Mark's sentence, stunned by the gift he had inadvertently laid in her lap. They had just finished a nice dinner at a favorite Chelsea bistro, and she was about to pay the check before taking Mark back home for some fun. Her mind raced as she thought of the possibilities, while this would certainly accelerate her usual timetable, it was too good to pass up. Leave the city?! She knew if she played this right she would have him utterly dependent on her by the end of the week.

"I'm... I'm so sorry to hear that Mark!" she said, sympathetically. "If there is anything I can do let me know, I'll try and think of something, I couldn't bear to give you up." She reached across the table to hold his hand, he was clearly embarrassed by his situation. "Why don't we go home and I can take your mind off of things?" She said, with a wicked grin.

Mark simply couldn't refuse an offer like that, and after returning to her apartment, he quickly found himself wearing only the panties and chastity device again, which was shortly followed by a pink leather collar. After an hour of serving her while she bathed, tidying up her apartment, and giving her a long, deep massage, she finally lead him to the bedroom and tied him firmly spread eagled to the bed.

Reaching into the nightstand she quickly found the 2" red ball gag and fastened it securely around Marks head. Vanessa slowly removed Mark's tight chastity cage, clipping the individually numbered plastic padlock to slide the tube off of Mark's desperate cock. She wondered faintly if he had cheated and slid his cock out of the back for some fun. She hated knowing that he could potentially get it off if he wanted to. Oh well, she thought. She'd remedy that problem soon enough.

Vanessa smiled at her tightly bound toy, looking forward to springing her trap. She found the tube of lube, squeezing some out onto her right palm. She laid next to Mark with her thigh draped over his own leg, head propped up off the bed, her full crimson lips just inches from Mark's ears. She slowly reached down and started to very softly rub her lubed hand up and down Mark's aching, denied cock.

After softly stroking Mark bringing him to the edge a few times she was ready. She leaned down and purred into Mark's ear "So I've been doing some thinking about your little problem. It seems to me that you only need a place to stay while you get back on your feet, until you can drum up some more work and find a new apartment, right?"

Mark moaned and nodded, barely hearing what she was saying, completely lost in the soft, warm sensation of her hand on his cock. He hadn't cum in almost a week, and he was desperate to do so.

"Maybe we could work out a little quid pro quo? I'll allow you to live here with me for a time, just until you find another place. I'll let you use my storage unit to keep all your stuff, you can just bring your laptop here for work. I'll even let you live rent free and I'll cover your food so you can save up. Does that sound good?" she whispered into his ear.

Mark was nearly delirious with pleasure at this point, and he nodded eagerly at the prospect of moving in, that would solve all his problems, and he would get closer to Vanessa!

Vanessa grinned like a cat who had just got the cream seeing Mark nodding franticly. She increased the speed at which her hand slid up and down Mark's quivering shaft, touching it softly to keep him on the edge, before continuing with her proposition.

"Of course, since I'm being so generous offering you room and board, I'll expect something in return. You will defer to me in all things, what you wear, how you act, how you spend your time. I'll insist you take care of all the little domestic tasks while I'm at work, and when I return you will serve me as needed."

"Like a butler?" Mark grunted through the gag.

Vanessa giggled thinking of the maid's outfit and high heels she had stored away and replied "Yes, I suppose you could say it would be like you were my butler. It's important that you understand thought that this wouldn't be all play like it's been so far. I'm offering you a way to get your life back on track, and as such I expect a serious commitment from you. You will cook and clean, take care of my laundry, and focus all your time outside of work on making me happy. At times it may be tedious, unpleasant and boring, and I reserve the right to discipline you however I see fit for unsatisfactory work or behavior. But I can assure you that we will have plenty of time to fool around as well, and I think this will be quite rewarding for you. Why, you may even get more attention than you can handle!"

Mark nodded thoughtfully as he reviewed the offer. He knew Vanessa could be demanding already, and the thought of her in this new dynamic was intimidating to say the least! But on the other hand Vanessa was gorgeous, wealthy, powerful and interesting. He was totally infatuated with her and the thought of being her slave was something he had spent many nights fantasizing about. Besides, if he didn't agree he would probably have to leave the city for lack of a place to stay anyway.

Vanessa leaned close and whispered in his ear as she swirled her hand around the head of Marks cock "So what do you think? Are you ready to be my slave?"

Mark grunted in agreement, nodding frantically, lost in passion.

Vanessa smiled and slowly slid her hand from his cock, leaving him twitching and straining against his bonds. "Good boy! God now you've gotten me all worked up. Why don't you take care of your owner while I fit this chastity back on you. I think we'll save your satisfaction after we see how well you perform as my new slave."

With that she removed Mark's gag, ignoring his protestations, swung around on the bed, lifted up her skirt, and lowered her glistening lips down onto Marks outstretched tongue. She gasped as she felt his tongue slide between her lips up to her clit, thinking of all the fun she was going to have with this unsuspecting, naïve little boy.


Part Two: Leverage (added: 2016/03/09)

Two days later Mark was sitting on the curb outside of his apartment next to the boxes that contained all his worldly possessions, praying he had made the right decision. While he was excited to move in with Vanessa, he was also a little nervous as well. But he had known her for months, and had loved seeing her and serving her. How many men actually get the chance to live their fantasy? Worst case scenario he would be out in a month and they could go back to normal.

He thought back to two nights ago, when he had left Vanessa's apartment. After servicing her, she had double checked the chastity device imprisoning Mark's aching manhood and given him his instructions. He had followed them to the letter, wanting to start off on the right foot. He had spent the next two days tying up loose ends and packing what little he had. All his stuff was in boxes with the exception of his laptop and charger. He was also bringing the jeans and t shirt she had picked out, and carrying his wallet, cellphone and toothbrush. Vanessa said she would provide his new wardrobe when he arrived. Shortly after nine oclock an SUV pulled around the corner, driven by an older man Mark had never met, with Vanessa in the passenger seat. As they pulled up Vanessa rolled down the window and spoke to Mark.

"Good morning boy! This is my colleague David, I borrowed him for the day to help us out" she giggled.

"Go ahead and help him get loaded up and we can get this over to the storage unit and get you all settled in."

Mark thanked her and walked around the back to where David was already loading boxes, nodding a quick greeting. Mark thought it was a little odd that this well dressed, distinguished man was helping him move, but he shrugged it off thinking maybe he owed her a favor. The two of them quickly loaded the car and were off to the storage space.

They got there and loaded everything onto a cart, and the three of them rode the elevator up to the space after Vanessa showed her ID to the front desk. After they got everything in Vanessa grabbed a large rolling suitcase out of the unit and wheeled it out, handing it to David. She then closed the steel roller gate before attaching a heavy padlock.

"Do you think I can get a copy of that key so I can get my stuff when I need to?" Mark inquired.

Vanessa smiled "Of course dear, just leave it to me, I'll take care of it"

David then drove the three of them back to Vanessa's apartment, where Vanessa instructed Mark to grab her suitcase and his laptop bag.

Vanessa turned to David and said "Bye David! Tell Sarah I said thanks for letting me borrow you. Don't forget to tell her that you were five minutes late picking me up, I know how important punctuality is for her and I wouldn't want you thinking you could be tardy in the future" She turned and got out of the car, speaking through the open window "The four of us should get together next weekend, I'm sure we could have all kinds of fun" she winked as she tapped on the roof. David grimaced as he eased the car into gear, dreading what Mistress Sarah would do when he told her he was late.

After a short, tense elevator ride, they finally arrived in Vanessa's apartment, where she immediately instructed Mark to put the bags in the bedroom, strip and put his clothes in the corner, and then to get in the shower and shave everything besides his head and eyebrows. Mark mumbled a soft agreement, not really looking forward to shaving, but not wanting to screw things up immediately. After he left, Vanessa got to work, knowing she had at least twenty minutes until he finished up shaving.

She opened his bag and retrieved his laptop. Popping a small dongle into the usb she ran a quick program she had a PI from her law firm show her how to use. After a few minutes she had all his passwords as well as total remote control of his laptop and cell phone. All of his work emails now went through her first. She grinned at the knowledge that she now controlled his business. She took a look at his bank account and smiled seeing he had a little under four hundred dollars to his name. Good luck paying first and last months rent, plus security deposit on that. She would let him keep just enough clients to keep up on his student loans and pay off his credit card debt, but he wasn't going to be moving out anytime soon. She grabbed his phone and wallet, checking that all his cards and ID were in there, and put it in her safe along with the key to the storage unit. Mark now only had access to his laptop, which she controlled.

She could feel herself getting wet at the knowledge that she could now hold Mark captive indefinitely. She was tempted to head to the bathroom and push her new slave down to his knees and bury his face in her pussy, but she restrained herself, knowing she still had work to do. She opened up the suitcase she had brought back from the storage unit and started pulling items out, smiling as she thought of the fun she was going to have now that she didn't have to worry about scaring him off. She tossed a blanket over the items, not wanting to spoil the surprise.

Vanessa strode into the bathroom and pulled back the curtain, causing Mark to instinctively flinch and try and cover himself. "Is that how slaves stand?" Vanessa enquired. Mark lowered his eyes and cross his hands behind his back. "Legs spread now! A little more. Tummy in, chest out, back arched! Good boy! This is how you will stand at attention whenever I address you from now on." She smiled and reached in with her scissors and clipped the plastic lock on his chastity. "Shave that too, then rub this cream in everywhere, it will keep the hair from growing back for a few months. I expect you out in the bedroom in ten minutes." Vanessa turned and walked out, leaving Mark standing at attention, stunned at the way she had steamrolled him and thought of depilating himself.

She walked out and checked her reflection in the full length mirror, admiring her appearance. A tight black skirt, low cut white blouse, and modest high heels gave her an authoritative appearance, without looking like some cheap Halloween fantasy costume. She reapplied her mascara and lipstick while she waited for Mark.

He soon joined her, his now hairless body wrapped in a towel. She cleared her throat loudly and gave him a look, and he went and replaced the towel on the rack before standing at attention before her. Vanessa made a few adjustments to his stance and gave him a warning before she grabbed his usual black leather cuffs and attached them to his wrists and ankles, but this time she applied small padlocks to each to ensure they stayed on. She then clipped a new 4" black leather posture collar around his neck, preventing him from moving his head, before attaching a padlock there as well.

I suppose I should go over the rules with him she thought. She reached up and grabbed his ear, pulling him down level to her hips before hauling him to kneel by the side of the bed. She walks around and calmly sits in front of him.

Vanessa pauses looking at the frightened boy at her feet, savoring the moment. She thinks briefly about her strategy for the rest of the day, knowing that the first day with a new slave is crucial to achieve the desired household dynamic. She knows she needs to totally establish her control and instill a decent amount of fear in him, while still leaving his infatuation for her intact. She's a little surprised that he actually came this far, and wonders if he has any idea what he's in for.

She started off with a quick slap in the face. "Now I just taught you how to stand at attention, don't you think you should do the same for kneeling?" She watched as Mark slowly recovered from the slap and adjusted his stance, hands crossed high behind his back, knees apart, feet together, chest out, stomach in, back arched, eyes lowered. She gave him a smile and stretched out her foot, gently tapping his chastity device, making his straining manhood swing back and forth.

"Now that you're officially moved in and my slave, we're going to have to set a few ground rules. First of all I've read your limits and I promise to respect them. Secondly, I promise not to "out" you to any friends or family, post pictures or video, etc. Thirdly, you will be allowed time to work on any projects you have that come up, after all you need to save money so that you can move out when you're able."

Mark thinks to himself this seems fair, it's not too different from what they had going previously.

"However, since I am letting you live here rent free, as well as storing all your stuff, not to mention feeding you, I will expect you to take care of certain duties as we agreed. You are to dress the way I require, keep my apartment spotless, have meals prepared as necessary, keep your body toned and groomed, and of course, serve me in any way I desire. Do you understand?"

Mark nods, knowing this was what he agreed to in principal, but he was beginning to wonder what it would actually be like in practice. She had already ramped up her level of control to unknown levels, and he had been here less than an hour.

"Any problems and I will punish you, and it won't be a punishment you will like, I promise you that. Understood?"

Mark nodded again, a little worried, but also undeniably excited at the prospect of being held as a real slave.

"Good, since we're in agreement please read and sign this contract, just so we have something to reference in case of any disagreements down the road. Check over the limits you've listed, any changes should be made now. Going forward this is what we will refer to, not the old rules we used to play by.

Mark reads through, not seeing anything amiss. She would let him stay in her apartment and securely store his possessions until he signed a lease to a new apartment. It said he would be allowed to live there as long as he preformed as her slave, and gave her authority to punish him in any way she saw fit within his limits. It stated his limits and that she would not break them, wouldn't out him, and would allow him to continue working. He signed and handed it back to her. "Good boy" she cooed at him. She walked behind Mark and deposited the signed contract in her safe, sealing it up behind her.

She walked around behind him and joined his wrists behind his back, clipping them together with a padlock, then wrapping a leather strap above his elbows to pull his arms tighter. He grunted as he felt the strain in his shoulders and chest.

"Please Mistress, can you loosen it just a little bit?"

"No" she replied curtly, before pulling back a blanket on the bed and grabbing a panel gag with a 3" fake cock on the inside. She could see Mark's eyes widen with fear at not only the denial of his simple request, but also at the sight of the gag. Before he could voice any protest she had pushed the gag to the back of his throat, securing the strap behind his head. As an extra precaution, this gag also had a strap that went around the nose and over the top of his head before attaching in back. As she pulled the gag tighter Mark felt the cock head pressing further back towards his throat, getting near his gag reflex.

Vanessa smiles looking at her trussed up new slave, seeing the apprehension in his eyes, wondering if he knows that he's already way past the point of no return. She grabs his ear and roughly pulls him to his feet, leading him to the foot of the bed. She bends him over the bedframe, forcing him up onto his tiptoes with his face on the mattress. She attaches a three foot spreader bar to his ankles, keeping his legs spread. She then grabs a rope and ties one end to his cuffed hands before pulling the other end up toward the headboard. She pulls the rope tighter, pulling his bound hands further and further straight back, tying off the rope leaving him in a strict strappado.

Marks is already aching all over, feeling his calves quivering, his shoulders straining, with the harsh metal bar of the footboard digging into his waist. He hears the click of her heels as she walks out of the room, shortly afterwards he hears her softly speaking to someone on the phone. Mark is sweating now, worried that he's made a terrible mistake. This level of bondage is way more intense than anything she had used in the past. The lack of hair made him feel very vulnerable, especially the soft breeze on his smooth exposed ass.

Ever since he got here her whole demeanor has been scary, and now that he had put all of his stuff in her storage unit and given up the keys to his old apartment he had no where else to even go if he wanted to leave! He would just have to talk to her and explain that it was a little too much, that this was more than he could handle. He heard her approaching again, but he was unable to turn his head due to the posture collar.

Vanessa smirked as she saw the bound, trembling boy bent over the bed. She was looking forward to the rest of the afternoon. She walked up behind him and softly fondled his balls, seeing his cock start to grow. She slowly stroked him for a moment until she could hear him mewing through the gag.

"Ok boy, I know you're excited by all this, but that's enough for now. We've got some errands to run, and I don't want any trouble out of you, so this is what's going to happen. I'm going to give you a little preemptive punishment so you mind your manners while we're out. If you give me any grief while we're out you can expect triple the amount when we get home. I know you don't have any experience with the cane, so I'm going to give you a little taste now. I think ten strokes ought to do the trick, don't you?"

Mark tried to shake his head no and beg her through the gag, but a moment later felt the first cruel stripe cut across the lower end of both of his cheeks. His eyes went wide as he felt the burn of the cane and he screamed into his gag, wiggling around trying to find any way to escape the next stroke, bouncing up and down on his toes. Vanessa was unsympathetic; in fact his screaming was music to her ears. She had held back for so long not wanting to scare him off, and now she was excited to do things her way. Besides she thought, it would be best to instill a certain degree of respect and fear in him before taking him out.

The next stroke was even harder, landing just below where the skin was already red and swollen from the first stroke. She landed another five before she heard him urgently shouting his safeword into the gag. She sighed and walked around into his field of vision. She could see he was truly distressed, big salty tears rolling down his face underneath the panel gag. She calmly watched him for a second as he shook and sobbed, savoring the moment, anticipating what was about to come.

"Are you using your safeword?"

Mark nodded, absurdly grateful that she had stopped.

"That's fine, that is your right. But let me explain to you what happens. The contract you just signed says in exchange for your room and board I have the right to discipline you however I see fit for any reason. By using your safeword you are ending our session and refusing to fulfill your end of the deal. That means I'm going to untie you, take off your cuffs and gag, and then you're going straight out the door. Your stuff will remain in my possession until you sign a new lease. That includes your clothes, laptop, phone, wallet, and whatever is in storage. You just go out the door naked and we don't speak until you can present me with a lease as the contract stipulated. Now is that what you want?"

Mark's mind was racing and his heart was pounding. She couldn't be serious, could she? He thought for a moment about the contract he had signed and realized she would be within her rights to kick him out. Couples split up all the time all over the world, but in this case he had nowhere to go, no money, and no friends. As bad as this was, he had nothing better to escape to!

"So, I asked you a question, is that what you want? Or do you want to take the rest of your caning like a good little bitch?"

Mark shook slightly in disbelief. He sucked it up and took the only option he really had, and muffled a soft "caning" through the gag.

Vanessa swiftly brought the cane down on Marks ass. "I think you meant to say 'Caning please Mistress', didn't you? After all, I am the one doing you a favor here, right?"

Defeated, Mark choked back a sob and replied "Yes Mistress, please cane me" through the gag.

"So you're going to take the remaining three strokes, plus another five for trying to stop me. Understand?"

Mark sobbed softly and nodded, muffling a "Yes Mistress" through his gag. Vanessa smiled broadly, knowing she had him broken. He wouldn't safeword again. Sure he would beg, try to reason with her, but it wouldn't matter. They both knew who was in charge.

Vanessa walked back and delivered the remaining eight cane strokes while Mark shook and sobbed in his bonds. She could hear him yelling things like "please Mistress" and "I'm sorry, please!" through the gag, but she was pleased he did not attempt to use his safeword again.

She waited a moment, then laid the cane across his ass again.

"What do you say?!"

Mark shook his head, not believing the position he was in, but he managed to muffle out a soft "Thank you Mistress", much to Vanessa's satisfaction.

She left him standing there bound while she retrieved his new chastity device. Unlike his old CB 3000, this was a much more secure stainless steel model, a little bit tighter in every way. He would be uncomfortable for a few days getting used to the tighter fit, but in her opinion that was even better.

She was happy to see that that his previously hard cock was shriveled and pathetic looking from the caning. Even so, the chastity device was a tight fit, but she finally managed to pull it shut and get the padlock through the hasp. She then lubed him up and inserted a medium plug into his ass before wrapping a locking leather harness around his waist between his legs, sealing in the plug until she decided to remove it. She then untied his hands and legs turning him around to face her.

Vanessa looked him in the eyes and had him kneel before her with a glance. She smiled at how obedient he was becoming already as he dropped to attention in front of her. Leaning down she removed his gag and started stroking his tear-streaked face softly.

"Now hopefully you understand how seriously I'm taking this. If you pay attention, do what I tell you and give this your all you can probably avoid having to experience that too often, and you'll probably even enjoy aspects of it once we get you trained. But I want to make it clear to you that I have no qualms with hurting you. I know you won't break, you're not going to be injured, and those marks will be gone in a day. So believe me when I tell you that you really don't want me to actually have to punish you. I'm living up to my end of the agreement, and I'm going to make damn sure you do the same."

"Yes Mistress, I'll be a good boy for you, I promise" Mark replied, utterly broken.

Vanessa smiled and leaned down and softly stroked his hair behind his ear before tenderly kissing his forehead. "Good boy. Now we have about half an hour before we need to go, so you can attend to me here before we get you dressed." With that she pulled off her bright red, lace panties and tossed them on the floor. She cupped her hand around the back of Mark's head and pulled him in between her thighs, shuddering with pleasure as her slave went to work worshiping her.


Part Three: Preparations(added: 2016/03/09)

Mark had never felt so confused or conflicted in his life. As he knelt next to the bed, slowly running his tongue up and down between Vanessa's ass cheeks as instructed while she recovered from her second orgasm, he took the moment of peace to consider what was happening.

When the day had started Mark had felt grateful that she was stepping in to save him from having to leave the city. He didn't know where he would be without her, but he knew he would be starting from scratch again. He was also excited to take things with Vanessa to the next level. She was gorgeous, kinky, wealthy and exciting, Mark was elated that she gave him the time of day; when she suggested he move in he thought he had hit the jackpot.

But as the day went on and he saw the way things were taking shape he felt deceived by Vanessa. She was taking things far past where he was comfortable and what he was expecting. He considered himself submissive, but she was clearly more experienced, demanding and intense than he was ready for. Her use of the cane a moment ago had cemented that in his mind, and he genuinely felt afraid of her. The fact that he had no way out was something he hadn't considered, and losing his safeword terrified him. She didn't even have a reason to punish him, what happened if he actually pissed her off?!

As Vanessa rolled over and grabbed his hair to pull his face into her slick pussy, Mark felt his cock pressing urgently into the tight cage. He knew he was in deeper than he could handle, but he hadn't came in almost a week now, and he was helplessly desperate for this Goddess that now controlled his sex. As Mark pushed his tongue between her soft folds he felt his anger with her starting to dissipate, replaced instead by the memory of the soft words and kiss she had given him after she finished caning him. While he was scared and angry, he knew a part of him was also undeniably excited, and seeing as he now had no choice in the matter, he thought maybe his best course of action would be to let things play out and do his best to avoid her bad side. In the meantime he would step up his business and start going after bigger clients. With any luck he would only be here a month or two. But that could wait until Monday when the workweek started back up and they both went back to a more typical schedule. For now, the best thing he could do was to focus on the task at hand.

Vanessa was, for the first time ever, feeling content. She had had submissives before, sure, but not like this. Her previous subs were always too willing and easy to conquer, or else they had bolted when things began to move outside their comfort zone. Mark on the other hand was completely under her control until he was able to leave her, and thanks to her quick computer hacking his business would slowly stagnate and eventually die. The fact that he had no children, no close family or friends, and no real job that he had to show up for every day made him perfect. She realized with a rush that she no longer had to hunt, that Mark belonged to her for as long as she chose to keep him. She shuddered as the thought in combination with Mark's well motivated tongue brought her to a third shattering orgasm. She slowly rolled over and offered her ass to Mark, mewling with pleasure as he obeyed the unspoken command and started with long slow strokes, just the way she liked.

After she regathered her wits, she decided it was time to get moving. "Get up boy, we need to get ready, we've got some errands to run! I'm going to take a shower and freshen up, but first let's get you situated first."

She recuffed Mark's hands behind his back and led him by the ear over to the corner of the room. Positioning him kneeling at attention facing the wall, she pressed his nose to a dime she held against the wall. Then she leaned down until her lips were just inches from his ear and spoke to him softly.

"Now I'm not going to tell you what will happen if you drop this coin while I'm in the shower, because I much prefer the thought of you imagining all kinds of nasty punishments on your own. In fact, when I get out in half an hour I want you to tell me what you think I would do. If I'm not sufficiently impressed by your creativity and the severity of the punishment, you'll get twenty with the cane. And god help you if you actually drop that coin. Be good!"

With that she turned and walked to the shower, leaving her slave frozen with panic as he racked his mind thinking of all the terrible punishments he had seen online.

Fifty minutes later she stepped out of the bathroom, hair straightened and cascading down to her shoulders. She had taken her time applying her foundation, light eyeshadow and mascara, before capping it off with a dark lipstick. She slipped into her black lace boyshorts and matching black bra before she approached her now trembling slave. Remarkably, he was still holding the coin to the wall. 'He must have a good punishment ready for me, he's obviously petrified' she thought to herself.

"Ok boy, you can drop that coin now, then crawl over here and kneel while you tell me what you came up with."

Mark let out a huge sigh of relief as he let the coin drop, stretching out his aching neck and back. He crawled over, praying that Vanessa would be satisfied with his answer. He knelt before her, looking up as she slid her stockings up her long smooth legs. "Well?! Are you going to gawk at me or are you going to do what I asked?"

Mark jumped at the sudden change of tone before he remembered what he was there for. "I was thinking that if I dropped the coin you should give me sixty strokes of the cane and piss in my mouth." He sat quietly, eyes cast down at her feet, in the longest silence he could remember while he awaited her reaction. His heart dropped when he heard her let out a small sigh.

"Well I have to say I had hoped for more. Sixty strokes is fairly severe, but I specifically asked you for creativity! Picking out a number isn't creative at all. And drinking my piss, are you kidding!? That's not a punishment, that's part of your duty, starting soon." She paused while she caught her breath and drank in his reaction, the panicked, shallow breathing, and the beginnings of a tear forming in the corner of his eye.

"I suppose you are inexperienced, and you didn't hold back on severity, so I'll go easy on you and only give you ten strokes. We don't have time for them now, so I want you to remind me at bedtime. I guess I'm just a little disappointed in you. Get dressed, you'll find some new clothes in the bottom drawer in the closet."

Mark was reeling from the rollercoaster of emotions that had just ripped through him. He was scared from the aggressive tone in her voice, and the revelation that he would have to drink her piss. The thought of doing that nauseated him, but he had no doubt that she would get her way one way or another. He could only hope that maybe she was bluffing. But then just as quickly as she had issued him a severe punishment she had shown her mercy and decided to only give him ten strokes instead. In some absurd way he actually felt grateful, even though she was going to cane him later! The most confusing thing though was when she had said she was disappointed in him. Despite all that she had done to him, he still wanted to please her, and for the first time he vowed to try harder, not just to avoid punishment, but to make her happy with him.

He went to the drawer and pulled out the clothing, pleasantly surprised with what he found; a pair of jeans, black sneakers, black belt, and a black hoodie. Not the most fashionable items, but they would work. He got dressed and turned to find Vanessa, looking stunning as always, wearing a fitted grey dress with black stockings and simple leather ankle boots with a three-inch heel. "You look gorgeous Mistress" Mark said nervously.

"Thank you! Now lets finish getting you ready and we'll be on our way." Mark started to ask where they were going but was abruptly cut off. "You'll find out when we get there! Now you've been doing well so far but I will not have you embarrassing me. So, you will speak only when spoken to, address me as Ma'am at all times, and do exactly as I say, understand?"

"Yes Mistress" Mark replied nervously.

"Good! Now lift up your shirt." Mark was puzzled, but knew better than to ask. Vanessa reached up and quickly applied a set of clover clamps to his nipples, causing Mark to wince at the sudden bites. She then attached a length of fishing line to the chain, before threading it though his belt and dropping the sweatshirt down to cover the clamps. She gave the fishing line a quick tug, and Mark felt the tension on his nipples increase as they were pulled down. Vanessa grinned as she saw the look in his eyes realizing they were going out in public like that. She wasn't done yet though. She pulled one of his still cuffed hands all the way through the hand warmer on the front of the hoodie, before clipping a small padlock from it to the opposite wrist cuff. She pulled the two hands back into the hand warmer, hiding his bondage. She then scooped up the bright red panties she had discarded earlier from the floor and pushed them between his lips, closing up his mouth around them, leaving him unable to even open his mouth without exposing the bright red fabric to the world.

"Now you be sure to behave, if you cause me any trouble you will regret it." With that she gave him a quick kiss on the cheek, turned and strode out of the apartment, giving his nipple clamps a quick tug to ensure he was following.


Part Four: Errands(added: 2016/04/14)

As the elevator starting heading down, Mark became acutely aware of the lingering smell of Vanessa's sex still on his face. As if he didn't feel self-conscience enough already. He wanted to protest, to tell her that it was all too much, to at least bargain with her and promise to behave if she would just give him a little scrap of dignity. He was about to open his mouth and beg her but the doors opened and an elderly man got on, nodding hello to Vanessa and him. Vanessa gave the man a smile and when he turned back to the doors she gave Mark a slow, steady pull on the fishing line tied to his nipple clamps. He wanted to beg, to whimper, or at least wipe her juices off of his face, but he was powerless to do even that in his current state.

Finally the elevator arrived at the ground floor; mercifully the old man didn't seem to notice anything amiss. Vanessa gave a quick tug to his aching nipples and led him out of the building north on 7th Avenue. As they walked Mark felt the plug locked in his ass sliding over his prostate with every step, making his cock swell uncomfortably in the cage. When they stopped at a crossing Mark looked out at an unoccupied passing taxi and was paralyzed between two competing desires. The emotional, frightened side of him wanted to spit out the panties and jump in the cab, consequences be damned. This was way more than he had signed on for, and she was taking advantage of his situation. But then the more logical part of him spoke up and reminded him that even if he weren't bound, he had no money, no phone, and no where to go. He felt a sharp tug on his nipples as Vanessa walked out across the street. He took one fleeting look at the now passing cab and meekly followed behind her, praying no one noticed his present situation.

Vanessa was savoring the cool September Day as she walked down the street, glad that the summer heat was finally starting to break. Perfect weather for a perfect day. She gave Mark another tug just for fun as she turned left and ambled down 20th St. toward their destination. She had been to Purple Passion many times before of course, but those had always been quick trips, in and out, no ceremony. She was hoping that the staff would be amenable to a more personalized shopping experience today. After all, it would be Marks first time, and she wanted to make it memorable for him. She glanced back to catch his reaction when they paused in front of the large store window showing several mannequins with tight latex clothes and leather straps restraining them. As expected his eyes widened and he let out a pitiful moan through the panties. She replied with a stern look and a sharp reply.

"Now don't give me any bullshit in there! This is your chance to start things off on the right foot, unless you want to do things the hard way?" Mark shook his head dejectedly and followed her slowly inside, knowing nothing good will come out of this store.

Vanessa pulled her boy through the door, a pleasant chime announcing their presence. She looked over towards the register to find a welcoming sight, and felt a surge of optimism for the day to come.

"Hey, welcome to Purple Passion, I'm Danielle, what can I help you two with today?" asked the young woman sitting behind the counter. She was younger, about 22 Vanessa guessed, probably fresh out of school. She had a lean, lithe figure, skinny but with well defined muscles. Swimming or gymnastics, Vanessa guessed. She was perched on a stool, wearing a loose low cut white tee shirt, black leggings with just a touch of sheen, and black patterned ballet flats. Her long black hair was tied up in a loose bun behind her.

Vanessa led Mark over to the counter and smiled warmly, extending her hand to shake. "Nice to meet you Danielle, I'm Vanessa. I'm here to get my new toy properly outfitted, and I'm sure you can help me find a few new tools to help train him."

Danielle smirked at the boy Vanessa had in tow, making eye contact with him briefly before his eyes shamefully shot down to her feet. "Excellent!" she replied. "What did you have in mind for him? We just got a shipment of maid's outfits that I think he would look adorable in. Of course we can accommodate whatever else you had in mind as well"

"Oh no, I think the sissy maid's outfits will do quite nicely. We'll also need all the accouterments, corset, heels, stockings and so forth. Won't we sweetheart?" she asked with a wicked grin in Mark's direction. Mark was mortified as he contemplated being forced to wear a maid's outfit and nodded weakly towards the two women. Vanessa giggled softly remembering his current state. She held out her hand in front of his mouth. Danielle looked on in confusion until Mark slowly pushed the panties out of his mouth into Vanessa's hand, prompting a bark of laughter from the two women. As Vanessa pulled the soggy panties over Marks head she instructed him "Now be a good boy and ask Miss Danielle politely, or else I may have to find a bigger cane while we're here."

Danielle smirked as she watched the color drain from Marks face at the thought. "Please Miss Danielle will you help Mistress Vanessa make me a sissy maid?" he mumbled. She looked up and caught Vanessa's eye, noticing the subtle wink. While she had only been working here for a few months, she knew an unwilling slave when she saw one. Most of the time she would kick them out and call the cops if she suspected any actual abuse, but this was the first time the unwilling party had been male. She knew it was wrong, but she couldn't help how wet she was getting at the sight of this pitiful boy under the thumb of this strong, assertive woman. I'm sure it's ok, she thought. Surely he could leave if he really wanted to, the fucking pervert was probably even enjoying it at some level. She decided the opportunity was too good to pass up, and she gave Vanessa a sly smile in return.

As took in Vanessa's lovely figure and demeanor she noticed the designer boots and handbag she was carrying. Figuring she might as well commit having come this far, she decided to up the ante a bit. "Well it sounds like we've got quite a bit of work to do! I was about to close up for my lunch break, but I can order delivery and eat a little later. Why don't I close up and we can have the place to ourselves to shop for an hour or so?"

Vanessa beamed at the gracious offer, this day was proceeding better than she had dared to hope! "That would be wonderful!" she gleefully replied to her new accomplice. "I'll get my boy all situated in one of the dressing rooms if that's alright and we can start picking things out."

As Danielle went to lock the door and flip the sign to closed, Vanessa lead Mark back to the dressing room by the tether. Once there she quickly uncuffed his hands and told him to strip everything off and fold it on the shelf. Once he was done she quickly relocked the cuffs behind his back, leaning in close and whispering in his ear from behind, "You're being such a good boy sweetheart" she cooed. She reached down and wrapped her hand around his caged cock, softly running her fingers over his swollen balls.

"I'm so proud of you for behaving for me. Now I want you to keep quiet while we're shopping, understand? Not a peep now." With that she lead Mark over to the coat hook hung at about neck height on the wall. His eyes widened in panic and he frantically shook his head as she reached up to grasp the chain still hanging from his nipples and pulled it up over the coat hook, leaving him straining to stay upright on his tiptoes.

Vanessa stepped back to survey her handiwork as Danielle returned from locking up. "Wow!" Danielle gasped as she saw the trembling boy in front of her. "You've really got him under your thumb haven't you? He must be a total slut to get off on this kind of stuff. I don't think I've ever seen a slave so thoroughly cowed." "Oh yeah, he loves this stuff. Don't you sweetheart?" Mark barely managed to eek out a weak "Yes Mistress" as he was currently focusing all his attention on keeping his weight off of his poor nipples.


Part Five: Shopping (added: 2016/05/18)

Vanessa looked over at Danielle with a wide grin on her face. As she pulled the dressing room curtain shut she turned and asked pleasantly, “shall we start with some stockings?”

As they picked out an assortment of stockings in different colors and patterns, along with a few garter belts to support them, Vanessa found herself enjoying Danielle’s company more and more. “So what’s your story? I’m surprised to find you working here, you obviously have a knack for this kind of thing. You could make a lot more money as a professional dominatrix.”

Danielle smiled at the compliment. “Well I did do the whole ProDom thing for a while in college, but it was killing me to just be a fetish dispenser to a bunch of anonymous old men. I love Femdom, but it needs to be on my terms, or else it just doesn’t work for me. I just finished up my degree at FIT a few months ago, but unfortunately the job market is shit right now. I figured if I was going to have to work retail to make ends meet I might as well stay in the BDSM world. They pay is alright, but it does give me some interesting opportunities; take right now for instance” she said with a smirk.

Vanessa chuckled softly, “Well I can certainly see the logic in that. You must never have a dull moment working here. Shall we look for some shoes?”

Danielle turned to the next rack and began searching, “Well it’s not all this exciting, but you do meet some interesting people every now and then. But it’s stuff like this that I really enjoy. Unfortunately I have a roommate so having a personal sissy maid is out for me at the moment. How high do you want the heels to be? Three inches?”

“Let’s start with two pairs of four inchers, and a pair of five inch shoes for special occasions and punishment. I like this black pair, and these pale pink ones are adorable as well. They’ll go so well with the white stockings we picked out!”

“Excellent!” Danielle replied, grabbing the shoes in his size and setting them on the counter. “If you’re going to be leaving him unsupervised for any amount of time I highly recommend some shoe locks as well.” She said, gesturing towards a pair of small leather harnesses. “These wrap around the ankle and under the heel, preventing him from taking them off. Of course they serve as ankle cuffs as well in case you need to restrain him. Personally, I enjoy attaching bells to them as well.”

Vanessa chuckled at the thought, “sounds great, I’ll take a pair! I’m sure the little bitch will be so grateful. I think it’s time to look for a corset next.”

“Oh I’ve got the perfect one! Hang on just a moment!” Danielle rushed to the back as Vanessa wandered over to check on Mark. She drew back the curtain and looked at her slave, taking in his misery.

Mark was barely aware that his Mistress had returned he was so overwhelmed by his situation. His calves were shaking and his nipples were visibly stretched and bright red. He saw Vanessa approaching through his tear blurred eyes and felt the sharp pain as she lifted his nipple chain off of the hook. Mark collapsed to the floor, catching his breath as his calves began to cramp up from the sudden change in position.

Vanessa saw his calves twitching and realized she may have pushed him too far. An injured slave would not do her any good, she needed him ready to work tomorrow, and they still had a long day ahead of them. “Take a moment and compose yourself. When you’re ready, I expect you to come out and find Miss Danielle and I, we have some things for you to try on.” She turned and walked out, finding Danielle opening a box on the front counter.

“This one is just right, I think he’ll look so cute and feminine in it.” She pulled the tissue paper off the top, revealing a gorgeous pale pink leather discipline corset. Vanessa’s eyes widened, this was exceptional craftsmanship. The front was simple but elegant, starting just below the chest and pushing down towards his sex before flaring up around the hips. The back had a subtle zippered panel to cover the laces. She approvingly nodded noticing the small post that the zipper would padlock onto, preventing it from being removed or loosened without a key. The leather was supple, but clearly very strong. “Danielle, this is perfect! How far will this lace down?”

“This one goes all the way down to twenty inches. I’d say your boy is around twenty eight right now, so it should be a remarkable difference once he’s properly trained. The only catch is that this is a size smaller than what I think will be comfortable, but I figured you wouldn’t mind” she said with a wink, having intentionally picked out a smaller size.

“Oh no this is perfect, we wouldn’t want my little maid getting too relaxed now would we? Hes always had a thing for seeing women in corsets and heels, but he has no idea how uncomfortable they actually are. I just can’t wait to educate him. Ahh, and here he is now!” she said with a grin as she watched Mark approach. She heard Danielle let out a soft chuckle as Mark knelt in front of her, his hands still bound behind his back, panties over his face, little cock tightly caged, and clamps still biting cruelly into his nipples. “Lets try some of this on! I’m sure Mark will be a very cooperative model, won’t you?”

Mark squeezed his eyes shut tightly knowing he had no way to escape the coming humiliation. “Yes Mistress I’ll do anything you ask, I promise you. I only ask, no beg, Please Mistress, will you please take off the nipple clamps?”

Vanessa grinned, having planned to remove them any way. “Well I suppose we can do that, Danielle, you’ve been very helpful, would you like to do the honors?”

Danielle descended on Mark slowly, eager to have some fun. “I would be happy to help the poor slut out” she said, gently tugging the chain, tossing it up and down. “Ask me nicely.”

Mark winced at the pain and begged “Oh, oh please Miss Danielle, please remove my nipple clamps, please Miss!!”

“Very well then” she slowly started to release the left clamp, pressing just hard enough to relieve some of the pressure before changing her mind and switching to the other clamp, leaving Mark howling in pain. She pulled the other clamp straight out, tugging his nipple before pressing down the release, letting his tormented nipple escape. She then removed the other clamp, leaving Mark gasping for air.

Vanessa watched the sadistic display with glee, feeling moisture starting to build in between her legs. She knew that Danielle was special, and resolved then and there to see her again, and soon.

“What do you say!” Danielle barked at the panting slave. He struggled to his knees and thanked her, kissing her shoes as he did so. Danielle smiled at the groveling slave, wishing she had her own.

As much as she was enjoying the scene, Vanessa knew they had to move on. “Alright slut, stand up, lets get you all dressed. Here, put these on, we’ll help you with the corset” she said, unlocking his cuffs before passing Mark some white stockings, a pink garter belt, and the pink 4” heels.

Mark reluctantly got dressed, uncomfortably aroused by the feeling of the soft nylon stockings sliding up his now hairless legs. He clipped the stockings into the garter belt, making sure the seams were straight, before he slipped on the heels. He wobbled slightly at the unusual position as he struggled to find his balance on the stilettos, feeling his aching calves starting to strain again.

Danielle approached him with the corset, unlocking his plug harness before she wrapped the corset around him. She had to strain simply to close it around him, and she hadn’t even begun lacing it yet! As she began to tighten the laces, Vanessa walked up in front of him and gently took his cheek in her hand.

“You’re being a very good boy for me, I want you to know that” she smiled. “If you keep it up then I may give you a little treat when we get home. Now, hold still.” She reached into her purse and pulled out a small makeup kit. Not wanting to attract attention outside the store, she decided on a subtle look to start, but since he would only see it for a second the effect would be the same. She began with a little light foundation, before some light mascara and a neutral lipstick, eager to see how her little sissy would look once she was done.

Mark had never felt more humiliated or powerless in his life. Here he was, being dressed as a girl, with makeup for god’s sake! It would have been bad enough at home with just Vanessa, but Danielle seemed to delight in it as well, and not only did he not know her, she seemed younger as well! He gasped as she pulled the corset even tighter, fighting against the unyielding leather to fill his lungs. He finally felt her tie off the laces, before zipping up a back panel. He shivered as he saw her grab a small padlock and click it in place locking his corset on, before pulling up the plug harness and locking that as well.

Danielle stepped around to look at Mark’s face, eager to see what Vanessa had done to him. She was impressed, the makeup was tastefully done, and subtle. It was apparent only on close inspection, it certainly didn’t scream “drag queen”.

“Ok slut” said Vanessa, “let’s see you walk down the aisle, turn, walk back and then give us a nice curtsy.”

Stunned, Mark did as he was told, not seeing any other options. As he began to walk back he caught a glimpse of himself in the full length mirror next to the changing rooms. He stumbled, then stared at the feminine figure looking back at him. Unable to believe what he had been turned into, he felt tears forming up in his eyes. A sharp command from Vanessa refocused him, and he walked back and gave a small curtsy, fighting back the tears.

“That’s a pathetic curtsy” Vanessa sighed before turning to Danielle. “As you can see he’s got a long way to go before he’s properly trained, I’m thinking of taking some time off this week so I can accelerate his training, would you be interested in giving me a hand?” She asked Danielle. As Danielle responded with a nod and a grin, Mark faded out of their conversation, the reality of his situation sinking in another notch, and felt tears running down his cheeks.

Vanessa glanced over at him and stopped mid sentence “What the fuck?! I just did your makeup and you’re already crying and messing it all up? Look at you, you’ve got mascara running all down your cheeks! You want something to cry about?! Fine!” she said before she stormed around the corner.

Terrified, Mark glanced up at Danielle, who was chuckling softly to herself. “You’re really in over your head, aren’t you sweety? Let me give you some advice. Don’t fight it, you’ll only make things harder on yourself. Just be a good little girl for your Mistress and you may even start to enjoy yourself. You two obviously care for each other, she’s just strict because she wants you to be the best slave you possibly can be.”

Mark absorbed this, trying to sniff back his tears, thinking about what Danielle had said. Maybe she was right. It was clearly no good fighting, the best he could do was to try and behave and get out of there as soon as possible. Again, he vowed to redouble his efforts at his work so that he could afford to move out.

His revere broke as Vanessa returned, tapping a medium wooden paddle against her thigh. It was a dark polished oak, about 9” long and 4” thick. When Mark noticed the rows of holes drilled through the paddle he gave a slight whimper and felt his knees buckle.

“You want to know when it’s appropriate to cry? I’m about to show you. I don’t appreciate you ruining all my hard work. Now what do you have to say for yourself?” Vanessa sat down on a stiff wooden chair as she listened, spreading her legs slightly.

“I’m so sorry I ruined the make up you gave me Mistress! I know you wanted me to look pretty and I won’t do it again!”

Vanessa was pleasantly surprised by the sincerity of his answer and the way he had humiliated himself. She knew though that she had to follow through with the punishment she had started.

“Good girl. Now bend over my left knee with your left hand and both feet on the floor, right hand behind your back.”

Mark awkwardly got in position, well aware of Danielle watching and enjoying every moment of his shame. Hell she might as well have been eating a tub of popcorn. He felt Vanessa grab his right arm and pull it back with her left, as she wrapped her right leg overtop of his. At this point Mark knew he was really fucked.

“Since you like crying like a little girl so much, I thought I would give you the chance to do so. But only if you ask me nicely”

Mark swallowed, and thinking he had better get it over with he said to her “Please make me cry like a little girl Mistress” he said as he heard a snorted laugh from Danielle.

“Very well, don’t forget to thank me when we’re done.” Vanessa said.

With that she gently laid the paddle on Mark’s still welted ass, savoring the moment. She could feel the juices running down her legs she was so turned on my his humiliation and coming pain. She knew she would have to have him attend to her desire as soon as they both were home. She lifted the paddle and began.

The first strike brought a startled gasp from Mark as his cheeks absorbed the tremendous force of the paddle. Vanessa did not relent though, nor give him a chance to recover. The second followed barely a second later, bringing a choked “Please” from Mark, before the third strike landed and his words turned to incoherent sobbing and wailing.

Danielle watched in awe as Vanessa laid into Mark’s ass. For such a small woman, her strength and endurance was impressive. She kept up a pace of about a swat a second for well over a minute. Mark was struggling to squirm away, legs kicking, arms jerking, begging and whining and sobbing as his ass turned a deep red, with blistered white spots in the center.

Finally, Vanessa released him from her grasp, pushing him down to kneel in front of her. She looked down at Mark and saw the tears flowing freely down his cheeks, making a mess of his mascara, bits of snot dripping out of his nose, brow covered with sweat, and red all over. “What do you say?”

Mark gulped and tried to regain his composure before looking up and replying “Thank you Mistress for making me cry like a little girl.”


Part Six(added: 2016/06/20)

Mark's cheeks were blistered and burning, this had been even worse than the caning he had taken just a few hours before. And it wasn't just the physical pain of it, the fact that he had been reduced to this whimpering, crying little sissy in front of a woman even younger than he was added an additional dimension to the anguish he felt. Mark felt as though he would never be the same again, any shred of self-respect he had possessed was gone. He looked down at his Mistress's feet, wanting to melt into the floor and disappear off of the face of the earth.

Vanessa on the other hand was elated. She sat in her chair, basking in the power she felt over the sniveling boy at her feet, knowing he was completely at her mercy. Twisting the knife, she looked down and said "Look me in the eye". She watched as Mark looked up, terrified, into her relaxed, radiant face. She wanted to be sure the lesson would sink in. Not that he wasn't allowed to cry, Vanessa could hardly blame him under the circumstances. No, the lesson she wanted him to learn was that she enjoyed every second of his misery, and that he would be best not to give her any excuse to punish him. She looked on as Mark trembled and whimpered, but never broke eye contact. Satisfied, she dismissed him and told him to put on the pants and shirt he wore to the store, but to leave everything he was currently wearing on underneath. As he got up, she added "And don't even think of wiping your face!"

Vanessa turned to see a beaming Danielle, giving her a slow clap. "Wow!! That was... inspiring. I'm really jealous; it's been too long for me. I really need to get back in the game."

As she walked to the register to pay for their purchases, Vanessa replied "Well we'll be busy tomorrow, but if you're free at all during the week I'm sure little Marcia back there could benefit from some training while I'm at work."

"Seriously? I'd love to babysit. I'm sure he would appreciate it too." Danielle laughed.

"Perfect, here's my number" Vanessa said, handing Danielle her contact information along with her credit card. As Danielle rang her up, Mark came out of the dressing room. The tips of his heels were poking out from the bottoms of the pants, and the mascara was still obviously smeared all over his face, but there was nothing there that would draw too much attention.

"Alright Marcia" Vanessa smiled, noticing the cringe in his face as he heard his new name for the first time, "grab those bags and lets go home. I don't want people associating me with a slut like you, so give me at least a twenty foot buffer while we walk. Stay within twenty five though, you don't want me to have to wait on you. Danielle, thank you so much for your assistance, I'll see you soon I hope!"

Mark paled as he gathered the shopping bags from off of the counter, trying not to notice Danielle's interest. As he turned to leave he heard her condescendingly say "Bye Marcia, see you soon!" He turned and politely said goodbye, not knowing what else to do. Mark approached the doorway, took a deep breath, and tottered out onto the street in his heels, praying there wouldn't be too many people out and about.

Half an hour later they were safely back at Vanessa's apartment. The walk hadn't been too terrible, he definitely received a few stares, but for the most part he had been able to keep a low profile. Vanessa seemed to be in a hurry on the way from the elevator to the apartment. As soon as they got in and shut the door she told Mark to take off his "outside clothes." Mark blushed and did so, thinking again of his humiliating new nickname.

"Alright Marcia, lets get you to work!" said Vanessa as she grabbed his hair and led him over to the couch. She pushed him down to his knees before hiking up her dress and falling back onto the couch, forcing his head down between her already glistening thighs. As she felt his tongue getting to work just the way she liked, she gasped in pleasure, remembering the frightened, crying little sissy-boy she had seen in the shop, thanking her for his paddling. With that mental image fueling her desire her first orgasm came quickly; her second took longer, but was even more intense when it came, leaving her quivering with her thighs tightly clamped around Mark's head. Eventually, she released him and pushed him back off of her sex, telling him to go get cleaned up.

Mark staggered off to the bathroom, still catching his breath after being nearly smothered in her juices. Despite the circumstances, or perhaps because of them, he felt a familiar ache in his manhood, not only his cock pressing against the cage but also the dull, constant pressure of blueballs setting in.

As he washed his face Vanessa popped into the bathroom, setting a laptop on the counter. "Here is a great youtube tutorial, you need to learn to do this yourself. Follow the lesson and do your best, I don't like sloppy work. You'll find everything you need in the bottom drawer. Be back out in half an hour. And just so you know Marcia, in your case at least, heavier makeup is better than lighter" she said with a condescending wink. Mark let out a resigned sigh as he remembered the advice Danielle had given him. He took a deep breath and started the video, pulling out the makeup.

Vanessa laid back on the couch while Mark got to work on his makeup. She felt quite well about how the day had gone so far. Marcia still had quite a way to go with her training, but she was behaving well so far, and not rebelling nearly as much as she had expected. She decided to give him a taste of the carrot instead of the stick when he finished up.

She pulled up her phone and checked in on Mark's email account. Mostly junk, but he did have someone who seemed to be a college friend asking if he was interested in doing some part time work for a new startup they needed help with. Vanessa knew that Mark only had one small job he was working on at the moment, and he was nearly finished with that. This would be a great opportunity for him to save up some money, Vanessa mused. She took a peek at his bank account, and after some quick calculations she decided he would have enough to pay his current bills for the month without any extra income. She deleted the email and got up to pour a glass of wine, feeling extremely satisfied that her plan was working out so well.

Vanessa was lying on the bed, catching up on facebook when she heard Marcia tentatively knock on her closed door. "Come in" she chimed. Vanessa grinned upon seeing the freshly made up sissy mincing towards her. She had done a good job on her makeup overall, and she had the right bone structure to pull it off. She loved seeing him like this, full red lips, long eyelashes, deep blue eyeshadow, and rosy pink cheeks. While he definitely wouldn't pass on the street, she enjoyed leaving him hanging in between like this, not quite a woman, but certainly not a man.

Below the neck was another story though. The combination of his recently depilated skin and the feminine garb locked onto him had really accentuated his already girlish figure. She was sure the tight corset and high heels were causing him considerable discomfort at this point, which made her happy that she had sprang for the locking options for both. The only things betraying that Marcia had formerly been a man were her lack of breasts, and of course the small steel chastity tube poking out between his garters.

Marcia tottered up to the bed and stood at attention, bringing a smile to Vanessa's lips. "I want you to know that despite the spanking I had to give you at the shop I'm actually quite pleased with how you've behaved today. I know this must be quite an adjustment for you, and you're doing great so far. This is going to be so much fun for both of us once you're fully trained, and I thought I would give you a little taste of what happens when you behave like a good little girl the way I want. Hop up on the bed, face up, spread eagle"

Mark warily got onto the bed, anxious about what was going to happen. He was tentatively excited for his "reward", but he had been through too much today without feeling a little nervous. Vanessa reached over him and began fixing his wrist cuffs to the corners of the bed, her breasts and the key to his chastity dangling enticingly above his face. He could feel his cock starting to harden against the unyielding steel. His balls were achingly full, it had been so long since he had last cum, but he knew by now that that was unlikely to happen without some kind of tradeoff. Still, he was hopeful though.

Vanessa turned to begin strapping his ankles down to the far corner, rubbing her toes along Marcia's face, smiling as she felt him gently sniffing her feet. Once he was secure, she reached off to the side and grabbed a stiff cylindrical throw pillow, about ten inches around. She patted Marcia on the hips, encouraging her to lift up so she could slide the pillow underneath her hips. This had the dual effect of raising up Marcia's cock for easier access, and pulling her taut against the bed, muscles stretched and straining. Once she had Marcia positioned perfectly, and after ensuring everything was secure, Vanessa pulled out the key to the chastity device from against her cleavage and gently freed the aching cock from it's prison.

"Ohhhh thank you Mistress" Mark said, feeling his cock springing forth and immediately becoming hard. He looked over and saw her pulling some lube and a complex leather harness from the bedside table.

"Sissies like you only speak when spoken to" Vanessa gently reminded him with a soft smile as she began fitting the leather harness around his swollen cock and balls. "And I think from now on I would like to hear you talk like the little sissy you are, instead of pretending to be a real man. This means you need to speak in a higher pitch, just like a little girl. Do you understand?"

Mark flushed with embarrassment, but not wanting to end his reward before it had even begun he swallowed his pride and squeaked out a small "Yes Mistress" in his best little girl's voice. Vanessa beamed and gave him a quick kiss on the cheek, whispering "good girl" in his ear, before she finished tightening the leather cock harness.

Vanessa wanted the harness tight, not painfully tight, but enough that it would keep him from going soft, greatly increase his sensitivity, and remind him who owned his cock. It also had the added effect of stretching and presenting his balls, just in case he decided he wanted to act up she could quickly remind him who was in charge. When she had it just the way she wanted it, she reached over and squirted a generous amount of lube onto her hand. She rolled back over and slowly, softly began running her greased up hand over Marcia's bound, engorged manhood, hearing the low moan coming from her new slave.

"What do you think of your new look Marcia? You can answer honestly." Vanessa said as she softly stroked the base of his shaft, wanting to save the more pleasurable areas for later.

Cautiously, Mark replied "Thank you for the new clo-"

"How do sissies talk?" Vanessa interjected with an edge of warning in her voice.

"Thank you for the new clothes Mistress. I'm glad I can dress in a way that you like. I only ask you to please, please loosen the corset and take off the heels just for a little while. I can barely breathe, and my feet are so, so sore from walking back from the store."

"Well I'm certainly glad you like the clothes, and I am very happy with the way you look. But the corset and heels stay I'm afraid. We women have dressed this way for men for centuries, you're not going to get any sympathy after a couple of hours. The shoe is on the other foot, so to speak" Vanessa smiled at her own joke, but also at her slave's obvious misery and subjugation. He clearly hated everything about the way he looked, but he was so powerless he had thanked her anyway.

She idly ran her fingers over his cock, thinking about how things were going. She knew she had total control over him in several ways already; the email hack, him not having anywhere else to go, and her controlling his access to his phone, wallet, clothing and possessions. In her opinion though the key was to use not just the stick, but also the carrot. Even though he couldn't leave even if he wanted to, he still probably wanted to run away at the first opportunity. She wanted more from her new slave. She needed not just obedience, but devotion.

"Besides," she said, stroking slightly faster now, grazing up against the head of his cock, "you'll come to like it. I know it's uncomfortable, but you look so sexy to me. Seeing you all made up en femme is such a turn on for me. I can't wait to see you in your new maid's uniform tomorrow. Today has been a bit of an outlier, call It an orientation day if you want. Your typical day won't be this exciting. It may be boring and painful for you at times, but it will make me so happy knowing that you're suffering it all for me. Besides, now that you've experienced all this, do you really think you'll ever be satisfied with plain old vanilla sex again? I've certainly never seen you this hard before...you must be desperate to cum."

Mark groaned, feeling conflicted. He was feeling trapped, he hated being sissified like this, and his feet and chest were aching terribly. The thought of being dressed and used like this every day terrified him. At the same time, he was undeniably turned on, and the sight of Vanessa sliding her fingers up and down his shaft had him almost ready to cum. He was moving his hips as much as he possibly could in his bonds, but he was too tightly restrained. He realized with a shock that this was probably the most aroused he had ever been, despite all the punishments and humiliation he had suffered today. He knew that if she chose to make him cum, it would be without a doubt the most powerful orgasm of his life. Conversely, he thought, if she denied him the blue balls would ache for hours. Swallowing his pride, he began to beg.

"Please Mistress, please let me cum. I promise to be good, I'll do whatever you want, please!"

Vanessa giggled, pleased with the way Marcia had remembered to use her sissy voice. She ran her palm over the sensitive head, ever so gently, careful not to push him over the edge. "Hmm.... Well you have behaved pretty well today. Of course you'll have to lick up whatever you squirt, you know that don't you sweety? Do you want to lick up your cum like a good little sissy?"

Miserably, Mark looked up at her, unable to believe what he was hearing. "Well? Do you want to lick your cum out of my hand like a good girl, or maybe you want me to lock you back up instead?"

Mark's stomach turned at the thought of having to lick up his cum, but he was so desperate to cum he knew he couldn't bear to be put back in the cage.

"Ple.. Please let me lick up my cum Mistress. I want to be a good girl for you."

Vanessa beamed down at him, knowing she had him completely wrapped around her finger. Slowly twisting her fingers around the head, she brought him right to the edge, listening to his breathing and whimpering. Time to twist the knife, she thought. "Hmm... I don't think so Marcia, not yet. We'll see how you do with your chores and duties this first week, then maybe I'll let you squirt, but only if you're a very, very good little girl. I know how much you want to taste cum, after all, you're actually begging for it you little slut" she said playfully.

Vanessa stood up and looked down at her bound, struggling little sissy, cock desperately pumping up and down in the air, precum glistening on the tip. Marcia was still begging, but Vanessa just let it wash over her as she basked in the power she was feeling. Her reflection was cut short by a short vibration from her phone on the nightstand. She picked it up and unlocked it, opening the texting app and reading the message.

Downstairs, looking forward to taking care of the new girl for you! - Sarah

She felt herself getting wet again, looking forward to what was coming. She reached across the nightstand to get the penis gag she had used earlier and ignoring Marcia's begging turned to push it between her bright red lips. As she fastened the leather straps in back, she bent down and whispered in Marcia's ear "Don't go anywhere bitch, we're just getting started!" before she turned and left the room to let her best friend in.