Never Have I Ever

by Clearwing, August

  My stomach knotted while sleep waged war with my psyche. Thus far I hadn’t denied Noah anything he asked of me. The more I stared at the words, however, the more intimidating the whole idea of this assignment sounded. When he warned me that it would push my boundaries he really wasn’t kidding. Regardless, I wanted my boundaries pressed. I even asked for them to be pressed. The entire point of entering into the whole semi-casual-but-not-really-so-casual-because-I-essentially-told-him-I-belonged-to-him-sort-of-relationship was, for my benefit, to break out of my shell and discover the things I never previously considered doing without that extra nudge. I didn’t only want to chip away at the brick dust of those walls of resistance; I craved to smash them down.

  This assignment, of all things, could conceivably shatter a substantial amount of my resistance. Or it could shatter me. The question became a matter of whether the reward outweighed the risk.

  My decision made, I shook away the fuzz of morning from my head and replied: I’m ready. I’ll be there, Sir.

  Noah: Good to know. I look forward to his review of your progress at the end of your day. And, of course, don’t forget to have fun.

  The address was texted to me a minute or so later. I flopped back down on the bed for another instant, content with the warmth of my comforters and the cool pillow beneath my head. I loved lazy Sunday mornings. On the surface I really didn’t at all feel up to leaving the apartment even for a moment today. As I lay there in flux between the dream world and birds chirping outside my window I wondered what Noah could possibly want me to do with this Howard Cartwright fellow. I was not a call girl—that was not at all what I signed up for—and, even as his submissive I figured that if anything sexual was involved he would be right there with me for it. It was still technically a relationship, right? Some form of monogamy had to remain in place.

  I took my time to wake up in the shower and stand under the hot water while I washed my hair and shaved the necessary places: legs, underarms, and even my pubic hair. While I realized that a lot of men liked that, I did it more for my own comfort than anything else. Waxing or shaving every couple of days was preferable to living with an itch I couldn’t publicly scratch should the need arise. As I stepped out of the shower to towel off I caught a glimpse of my backside in the mirror. All of the bruising on my ass from last weekend’s escapades faded completely by then. It sort of saddened me. They were good bruises after all. I’d grown rather attached to the memory of them.

  I chose a pastel green sundress and short summer heels which barely made me an inch taller. Before I left for the day, I decided to not make the same mistake as I did with the piano bar. This time I would know what to expect when I arrived at wherever I was going.

  Google Maps highlighted the location as a dance school. That didn’t make me feel any more confident in my ability to grasp what to expect. An internet search provided little details about Howard Cartwright beyond news articles and art magazines making mention of his success as a teacher and director of a myriad of ballets and musicals. Not so much as a picture of him had been added to any of the reviews. In the end I stood even more confused than prior to looking it up.

  Come noon I was out the door and on my way to the other side of the city for my assignment. This, unfortunately, was not an off day. The vibrator worked with the plug against me. It proved difficult to find a comfortable position in which to drive. By the time I arrived at the address it was closing in on one o’clock.

  The studio was nestled in a strip mall with a sparsely populated parking lot. That was odd for a Sunday afternoon in most places. As I locked my car and approached the building, I saw the wide windows and mirrored walls inside. A small class of what looked to be Jazz dancers finished out their last round of practice with an older female instructor.

  A thin woman maybe a few years older than me sat behind a small desk off to one side. She was a natural blonde with a short pixie cut and deep red lipstick. The tiny ballet slippers dangling from her earrings gave away her passion for dance. In addition to the earrings she wore a thin golden chain with an o-ring at the base of her neck. A pink blouse clung to her small frame. Beyond that I couldn’t see whether she wore a skirt or pants beneath the desk top. The woman busied herself with paperwork and whatever happened to be of interest on the computer screen that I couldn’t glimpse. As the students of varied age began to filter out the door, I stepped up to the desk, trying to cast out the fight or flight butterflies which continuously fluttered in my chest.

  “Hi, excuse me. I’m looking for Howard Cartwright. Is he here by chance?”

  The receptionist glanced up at me and reached for the phone on her desk. “You’re his one o’clock right?” I nodded. She picked up the phone and tapped in an extension. After a moment she said, “Master, Piper is here for her appointment. Yes, sir, I’ll tell her.” She hung up the phone and smiled at me. “He’ll be right out. Feel free to have a look around.”

  So Howard Cartwright was like Noah. That answered that. His submissive even worked for him. However unorthodox the arrangement, she seemed happy to be doing what she loved.

  “Thank you,” I said to the woman. I wondered if she could tell I was filled to bursting with an anal plug and a vibrator that was barely contained by my panties.

  It didn’t take long for the man I was meeting to show himself. He stepped out of a back room which, I now saw through the open door, was another large practice room. He was wrapping up a conversation with two students. Between his low tone and the muddled echoes off the walls I couldn’t understand a single word he was saying.

  Howard Cartwright was at least fifteen years my senior if not more. He had a dancer’s body; the body of a lithe athlete even into his forties. A blue shirt went unchecked down to the third button and his black slacks fit snug against narrow hips. His brown hair, speckled in salt and pepper, was slicked back across his scalp. The same was true for his full goatee. Lively green eyes reached out in a welcoming shine when he finished speaking to his pupils, showed them to the door, and finally turned to face me.

  “You must be Piper,” he said.

  I half smiled at him. “I suppose I must.”

  He crossed the space between us and took my hand in his. He didn’t shake it, but drew mine up to his lips and kissed the back of it. “I’m Master Cartwright, and you look awfully worried, duckling.”

  My eyes trained around the mirrors and open floor of the room. “I’m not really sure what I’m doing at a dance studio is all.”

  Master Cartwright still clutched my hand in his. Once he finished drinking me in with his eyes he released it and turned to the desk to wave the receptionist over. She moved with haste, a stack of papers in her hands. I now saw she was clad in a flared white skirt that barely reached mid thigh.

  “You aren’t here for a dance class,” he said. “You’re here to learn something a little more important. Before we do anything, however, I need you to sign this.”

  I took the papers from the receptionist and thumbed through the ten or so pages. “What is it?”

  “Standard C.Y.A legal documents. Since you don’t belong to me of your own free will this states that you consent to training.”

  “Training?” I asked, more than a little perplexed.

  “He didn’t tell you?” Master Cartwright replied. The look on my face made that perfectly clear, so he explained, “The first few weeks as a submissive are very important. You learn your place during that time. Seeing as I’m the one who introduced Noah to this lifestyle I think it’s rather poetic that he called me to fill in for him in his absence. I know what your Master likes, what he hates and overall how to drive him wild with desire.”

  There it was, clear as day: a contract for training dated for today and today alone. “That’s exactly what I want, actually. There’s only one problem.”

  “Which is?”

  “We’ve only just started this. He’s not my Master, at least not yet. He said he didn’t want me to call him that until he gave m
e a collar.” I looked down at my feet, not quite sure why that one little word mattered so much to me or why it sort of pained me that I couldn’t use it.

  Master Cartwright’s eyes widened with both approval and surprise as he responded with a subtle nod. “Well now that is a switch for him. Count yourself very lucky, little sub. He must be serious about you if you have to earn the privilege.” Upon seeing my face drop he placed a finger beneath my chin to raise it back up. “Take heart. Just because you aren’t able to call him Master yet doesn’t make his position any less true. After I’m finished with you, he’ll be rewarding you with a collar in no time.”

  “Why would he send me to you instead of doing this when he returned? Isn’t that technically his responsibility?”

  “He told me you were sharp and inquisitive. I’d have to agree on both accounts. He sent you to me for several reasons, all of which I will let him explain to you when he returns.”

  I bit my lip and scanned through the documents, weighing the final options.

  The contract stated that the use of sexual implements as well as the act of sex itself with one or more partners may be used in the training. It also contained a page to initial that none of the involved parties knowingly harbored any sexually transmitted diseases. As an act of faith he had attached his own medical records to the end.

  This went against everything I was ever taught when it came to a standard relationship. When I thought about it, though, this was not a standard relationship, not by a long shot. I was no lawyer, but if Noah trusted him then I supposed I should at least give him the benefit of the doubt. New horizons and all that.

  “I wasn’t aware that there would be any actual sex involved with today, Master Cartwright.” Though it wasn’t a total lie, it also wasn’t the whole truth. I didn’t want to expect sex from him is what it truly boiled down to. Not without Noah’s presence to reassure me that nothing would go wrong. “I sort of thought that was reserved—”

  “For your Sir?” he interrupted. I nodded. He smiled and sighed at my naïveté. “Duckling, if this is the sort of thing that you want to keep in your life then you will need to understand that sometimes the one who owns you will instruct you to service others. This is not for my pleasure, but for his. I am doing him a favor in helping educate you, and losing a lot of money by cancelling my afternoon classes in the process. Do you understand?”

  “Yes, sir,” I said. “He didn’t tell me I would need my medical records. If it’s any consolation, I haven’t slept with anyone else in two years.”

  “I’ll accept that,” Master Cartwright said.

  He pulled a pen from his pocket and handed it to me. If ever there came a time to break out of my shell, this was most certainly it.

  {CHAPTER TEN}

  “Have a seat,” Master Cartwright said. He motioned with an open palm to a plush floral chair in the center of the room. It faced the mirrored wall of the studio.

  There were no windows in this back room, only that one mirrored wall and a polished floor for the student dancers. As he closed the door and locked it I walked to the chair. My low heels clacked against the floor, echoing back to me as the only sound in the room save the subtle buzzing of the vibrator inside of me. I took a seat in the chair and crossed my legs. It was the only position wherein I remained comfortable and was able to relieve the slightest bit of tension between my legs.

  He suddenly snapped his fingers. “Sluts don’t sit with their legs crossed. Uncross them. If you do it again you’ll be punished.”

  “Yes, sir.” I adjusted in the chair, trying to find a position in which the toys wouldn’t press into me too hard.

  Only my reflection stared back at me, my legs slightly parted as my dress rode up my thighs some more. Master Cartwright stepped into my line of sight a few feet away. I blinked away the haunting image and looked up at him.

  “At least you have manners going for you,” he said. “Other than that we have a lot of work to do and little time in which to do it since I only have you for the afternoon.”

  I averted my gaze. My muscles tensed and the palms of my hands became clammy. Where was Noah? This was supposed to be his job, I was sure of it. Not the work of a stranger. What little I knew from what I’d read about this lifestyle told me that, with the exception of some, a Dom molded a sub on their own. Whatever training needed to be done should have been done by him.

  Suddenly Master Cartwright walked forward and gripped my jaw roughly in his hand to force my sight back at him. “Never look away from a master when they’re speaking to you. They deserve your undivided attention.”

  “I’m sorry,” I stammered. “I’m just a little nervous.”

  He released my jaw and took a step back. “You know, contrary to popular belief, this lifestyle is an illusion.”

  My brow creased together in a bout of confusion. “How do you mean?”

  He smiled wide and said, “In order to preserve trust a Dom won’t take anything his sub doesn’t want to willingly give. After all, we live in a free society and any real form of slavery is against the law. He’ll push your limits to help you grow, but he won’t cross that fine line and shatter your trust in him. If a Dom ever does that then they don’t have the right to call themselves a Dom. At that point it’s just abuse.”

  But if the submissive could put a stop to it at any point then what was the purpose, I wondered.

  “Then why do any of it?” I asked.

  He crossed his arms in front of him. “You tell me.”

  My fingers found the texture of the chair’s coarse fabric while the reasons poured through me until I found the one most suitable. “I think… I think I just want to live for something more than myself. I like the surrender. I want to put my absolute faith in someone and know I’m safe doing it.”

  Not that I was sure I was at all safe in this situation at the moment. It was one thing to trust Noah. I met him through a mutual friend who had known him for years. I talked a bit with Noah and slipped into a comfortable enough state of mind before I took the leap. Now it transformed into something confusing.

  “You want to exist for the pleasure of another and be cared for in return by that person,” Master Cartwright said.

  In the simplest of terms: yes, I did. Just as Noah said I’d awoken something inside of him, so too did he in me. True, I’d only known him for a couple of weeks, but he tapped into something primal and brought it bubbling to the surface. I was addicted to the idea of being his submissive.

  “Yes, sir,” I said with confidence.

  “Then you’re right where you should be, duckling,” Master Cartwright said. He uncrossed his arms and continued his lecture while he paced back and forth. “Now, the relationship that you’re seeking is a consensual exchange of power. The only things that are higher on your list of priorities will be your religious beliefs, your blood relatives, and your career or education. Everything else is secondary to him. You will eventually learn never to think of your own needs or desires before you think of his. He will take care of yours in return.”

  “I understand, sir.”

  He stopped just off to the side and turned back to me. “Do you own any lingerie?”

  “Nothing fancy, no.”

  Why the hell would I own lingerie? I had no reason for it these past couple of years. There was no one to impress besides cold machinery; and not just as a euphemism, but in the practical application of my job description.

  “Buy some; garters, new stockings, matching underwear, the works. I also suggest wearing skirts and dresses as often as possible. It makes for easier access, it’s a fine enticement when we show you off, and we men do so enjoy ripping your clothing from you.”

  This was getting to be more like a college crash course ever minute. He followed no particular train of thought for too long before jumping tracks to someplace else entirely.

  “May I write all this down?” I asked.

  “Memorize it,” he replied. “You will be reminded swiftly if ever y
ou forget.”

  “Yes, sir.”

  “Come here,” he told me. I stood up and slowly crossed over to him. “Take off your dress.”

  I took a deep breath. Fuck. This was it, the beginning of uncharted territory. The resistance in me wasn’t because Master Cartwright was unattractive. By all accounts he was actually quite the opposite. Even though he was comfortably out of the age-range of someone I’d consider sleeping with, he was still a good looking man. And maybe that worked for some people. Some people were not, however, me.

  He noticed my hesitation. “Now!”

  I tried to reconcile myself to what was happening, tried to hold on to the reassurance that Noah contacted this man and that this man told me he was the one who introduced Noah to the lifestyle. It meant he held a level of experience I couldn’t begin to comprehend.

  There was almost no time to psych myself up for this considering I was already in the moment. It was my fault for not taking a breath in the parking lot to really think things through. I crossed my arms in front of me and hooked my fingers below the hem of the dress. It peeled away from my torso with little resistance, up and over my head until I was holding the bunched up green cloth in my hand at my side. Only my matching white bra and panties covered me now. The base of the vibrator peeked out of me. It bowed the crotch of my underwear slightly. My shoulders were tight and my head bent low. He was looking me over like I was a piece of meat, a lamb to the slaughter. And rightfully so; I signed a document that stated he could do almost anything to me he desired in the span of the next few hours so I only imagined what thoughts were blazing through his mind behind those lusty eyes.

  Master Cartwright glanced between my legs and smirked when he noticed the vibrator straining against my panties. “Remove your underwear. You may take out the toys also.”

  By now my entire body was shaking with subtle tremors of embarrassment at my own naked form with no place to hide in this wide expanse of a dance studio. I cast aside the green summer dress to free my hands. As I pulled my panties off, I slipped the vibrator out of me. I had to pause for a beat before I removed it completely. I loved the feeling of being filled with it. It was like a place-holder for Noah. I regretted every moment it wasn’t in me by the end of that first week. The walls of my pussy gripped it tight until I finally pulled it out. A thin thread of wetness glistened on it in the fluorescent glow of the studio lights until I moved it far enough away to break it. Then, with a little more care, I removed the plug. That was a more welcome sort of emptiness.