by Alyssa Clark
“If you say anything other than that outside of answering my questions you will be punished, you understand?” I got a nod, silence began now. I pulled on a rubber glove and smoothed a generous amount of lube onto my fingers and then onto the little bulb of the butt plug. I didn’t wait or give him any other warning, I rubbed my fingers against his anus, liberally spreading the lubricant before I pressed my fingers into him. This was sexual, I could lie to myself all I wanted, but he got some sexual gratification from this. I didn’t, but this wasn’t for me. I had begun to overlook my wants in favor of the men I saw when I started this.
I worked my fingers in and out of him, teasing little whimpers from him that I chose to ignore for now. I spread my fingers apart, watching his face for any telltale signs that he was going to break. I received another whimper, but nothing further. I picked up the plug and removed my fingers so that I could press it into him.
He gasped, and his hands began to open and close minutely. As soon as the plug was in place, he released a low moan. “You did so good,” I said though we both knew he wouldn’t have been able to maintain silence during the insertion. “But,” I clicked on the plug so that it began to vibrate. “You made noise, my dear Mr. Middleton.”
His hips rocked, and he swayed in the air. “I’m sorry, Mistress!” his voice was desperate and his eyes wild as he bucked. I pulled the blindfold off the tray that I kept for this because I knew this would happen, as he did. I shifted from between his legs and wrapped the silk blindfold around his face then secured it. He grunted and moaned as I stepped away from him. I let him settle into the restraints and get comfortable with the vibrating plug before I began any sort of punishment. It would be twenty minutes before his heavy breathing would settle, though the whimpers and moans would still persist. I picked up a leather flogger and got closer to him to do a quick check of his pulse. It was accelerated, but not at an alarming rate. With his reaction and the cage, he didn’t have an erection even with his obvious arousal.
I stepped back, making sure the heels of my shoes made noise. He was blind to me and unexpecting when the actual punishment would come. The anticipation added to with the vibrations of the butt plug and likely had every nerve screaming for contact. I’d start from below, though the blows wouldn’t be painful. I swung the flogger upward to hit his back. I didn’t use a lot of force with Mr. Middleton, he was older than Mr. Franklin, and I often worried what would be too much, so I went on the side of caution more than anything.
Despite the lack of force I used, each time the flogger connected he gasped out. I shifted around to start flogging his chest and stomach, using a tad bit more force with the downward swing. I was admiring the strips of red skin that started to flare up on his pasty chest when I heard a noise. I paused mid-swing and listened.
Was that a phone ringing? I felt anger well up in me, and I fisted my hand in what little hair Mr. Middleton had left, “Is that your phone?”
He gasped out and tensed though he didn’t resist, “N-no! I left mine in the car!”
I released a breath and started to smooth out the tangled hair that had been in my hand. I kept petting him, soothing out my rage as the ringing of what had to be my phone stopped. Mr. Franklin had taken to calling me regularly, eager to get back into my good graces. But, he was a man that was predictable in the means that he liked to keep a schedule. He usually called me during lunch. I would let it go to voicemail like I usually did and returned my attention to Mr. Middleton.
I had managed two more strikes before my phone started to ring again. I cursed, something I refrained from doing in front of my clients but I found my patience running thin. Mr. Middleton tensed but didn’t make a noise at my obvious anger. “You will have to forgive me. Apparently, there is someone striving to get my attention. Wait here,” like he had a choice.
I stalked to where I kept my bag and tore through it with an ire I hadn’t felt since after I sent Mr. Clarke on his way. I didn’t bother to check the number I just answered with a clipped tone that I knew Mr. Franklin would respond to, “I am currently preoccupied, and your persistence is not going to garner you any affection. I will contact you on my time and not yours.”
“Miss Winters,” Allen Franklin’s voice didn’t greet me, and I immediately pulled the phone away to look at the number. It wasn’t pre-programmed into my phone, and it was unfamiliar. The caller began again, “I’m sorry. I was unaware you were ... preoccupied.” It took me a minute to register it was Mr. Clarke that had called me. I remained silent, prompting him to continue. “I was hoping to schedule an appointment with you.”
Really? He wanted to see me again? Something in my chest fluttered, and I immediately clamped that down. I wouldn’t get excited over the prospect, “When?”
“I-I was hoping as soon as possible,” he said, sounding unsure and maybe excited. “I am at your office now.”
I drew my brows together and took a cautious look over at Mr. Middleton, he swayed, and his hips bucked, but he didn’t make a noise. I walked over to the door that separated the front from the back and opened it. I didn’t have a care that I was dressed in nothing but a lace bustier, pretty thong, and matching garter belt. But, when I saw Mr. Clarke waiting outside the glass door to the front part of my office I thought maybe I should have put on a robe first. His eyes widened, and his mouth dropped open. “As I said before,” I spoke looking him hard in the eye. “I am currently preoccupied. If you wish to make an appointment, you will have to wait. And you will not be waiting in my office.”
“Yes,” he breathed, sounding like he wasn’t about to argue. He looked mesmerized as he took in my state of dress.
“I will contact you when I am available to see you,” I said sternly before hanging up the phone and turning to close the door. I went back to Mr. Middleton, trying to keep from growling out my frustration or allowing the hunger I felt get to me. But, I felt it pooling between my thighs now. I wanted to string up Mr. Clarke as I had the man before me.
I started stroking my hands over Mr. Middleton, petting his face and hair, going over all the little red stripes that I had beaten into his skin. His face turned towards me, and he relaxed visibly. I found myself checking his pulse to be sure that it didn’t feel erratic. “You behave so well for me,” I murmured. “I am torn with whether or not I should continue to punish you.” I went to start stimulating him, shifting the plug in his rectum in and out minutely. “What do I give you for a reward?”
“Stalemate,” he moaned, and I tried not to feel disappointed.
I immediately switched off the butt plug and gently pulled it out of him. I reached up to pluck off the blindfold, “Are you okay?”
He nodded, “I need the cage to come off.”
I understood and deftly unlocked it and began removing the pieces carefully. As soon as his cock was free, he moaned out in relief. I continued to carefully lower him to the floor so I could free him from the restraints. As soon as he was free I held onto his wrists to make sure he was steady on his feet. “Are you okay?” I asked again, watching his eyes for any kind of distress that wasn’t normal.
He gave me the most charming smile, I imagine if I had been twenty years older I might have felt something less platonic for him. “I am fine, Mistress,” he grasped my hands. “You are too good to me. I need to end our appointment early,” he said steadily.
I looked down and spied the erection he had. I knew what he was going to go do. “Let’s get you dressed so you can take that home to enjoy it then,” I hated to end an appointment early. But with someone like Mr. Middleton that suffered like he did, I wouldn’t complain. I helped him dress and walked him to the door, hoping that he would be able to maintain it long enough to get home.
Unfortunately, for the both of us, Mr. Clarke was waiting outside the office. He saw Mr. Middleton and gave the other man a nervous nod once he was out the door. It made my blood boil in a way I wasn’t prepared for. As soon as Mr. Middleton was out of sight, I let go of the affection I fe
lt and glowered at the man that stood in my doorway now.
He looked back at me, and it was easy to see the lust that seemed to radiate from him. The last time he saw me I had been fully dressed. Now I was in nothing but lingerie. “May I come in?” he asked distractedly.
The fact that he asked gave me pause, he must’ve done some research since I last saw him. Intrigued, I nodded. I watched as he stepped in then closed the door, not allowing it to fall closed on its own. He even went as far as to lock it. “What can I do for you, Mr. Clarke?”
He fidgeted for a moment like he was trying to figure out what to do from here. I could see indecision and something else warring with one another. “I would like to make an arrangement to see you on a regular basis,” he said at last.
I told myself I wouldn’t see him again. I told myself he couldn’t be a client. But here he was, wanting to make arrangements. “I won’t be fucking you, Mr. Clarke,” though I wasn’t sure if I was just telling him that or if I was reminding myself. “That won’t be apart of the arrangement.”
“Of course not,” he straightened up then, pulling at a cuff, looking all business. I got the feeling I was now being presented with the lawyer. “I remember the conversation we had the last time we met. That isn’t what I am trying to arrange.”
“Alright,” I gesture to one of the couches. “You can wait while I clean up. I will see you after.” I turn and close the door behind me. I force myself to clean up at an average pace and not rush through it. I would not rush for a man.
After I placed the plug and cage to soak and sanitize I found a robe to wrap myself in. I took a few deep breaths, trying to rein myself in and not appear as excited as I was. I shouldn’t even be excited. I should be angry. I should be upset that he was here. I should demand that he leave. But, I wouldn’t, I couldn’t. I went to the door and opened it, head held high. If he was going to accept my fee and terms, then I would gladly accept the duty to torment this man.
He was seated on one of the couches, had a knee bouncing and from the look of him, he was a ball of nerves. He was afraid. It’s likely he didn’t know what to expect. It made me deflate, and I went to my desk, found a clipboard and pen then found the checklist I kept. I came to sit beside him, though not too close. But I did turn to look at him, my knees brushed against his bouncing one.
“Mr. Clarke, before we begin any sort of fun we need to have an important conversation,” I began.
“I’m clean,” he said without me asking. “I get a yearly checkup and the last time I had sex was probably six months ago. I used protection, and I expect us to continue to use protection.”
I put my hand on his knee and immediately halted it’s bouncing, I gave him a hard look. “You will not talk unless I speak to you and request an answer. Do not assume what I am about to ask, do not assume you know what I want. Assuming will lead you down the wrong road. We don’t know each other, you have no right to assume what I want. Do it again, and it will lead you to punishment, do you understand?”
He stared at me, eyes wide. “Yes ma’am,” his voice had gone quiet, and I could see that despite the fact that he wasn’t someone that would usually take the submissive role, I had his undivided attention.
“First things, first,” I began again, releasing his knee. “Sexually, what sort of experience do you have?”
He blinked slowly at me, as he registered my question as if he hadn’t provided me with the answer beforehand. “I’m not a virgin,” he said simply.
“Not the question, Mr. Clarke,” I tried not to get frustrated. He was vanilla. Completely. “Let’s make this simpler, shall we?” I released a breath and consulted my list, “Have you had anal sex before?”
He made a soft noise, “No.”
“Have you been penetrated before?”
He balked and stared at me as if I had just asked him something offensive. “No,” his voice had risen an octave.
I sighed, knowing that answer would add more dust to my damn strap on. It looked like the only way I’d get to use it is if I started seeing women, which, was starting to look like a good idea. I tried my best to hide my disappointment and continued, “Oral sex?”
“Yes,” he cleared his throat, looking decidedly uncomfortable with this conversation. “I’m not entirely sure why you asking all these questions. Are they really all that important?”
“Do you give oral sex?” I asked immediately after and I saw him get intrigued when I did. “These questions give me an idea of just what you’ve experienced and what you may not be willing to experiment in. I can already tell that you are pretty much a standard man. You probably prefer missionary or doggy style. You enjoy oral sex, but I’m not quite sure if you’re willing to go down on a lady. So far I’m under the impression that you take more than you give. Am I wrong?”
He frowned at me and leaned forward, “I would go down on a lady. Give me the opportunity to, and I would bury my face between your legs and I would stay there until you were begging me to stop.” He then rolled a shoulder and looked away, “As for the other part. Yea. I don’t mind experimenting with different positions and usually shift as the mood strikes me, looking for the best angle that gets the most reaction.”
“The blunt approach I will take then,” I tilted my head until I heard my neck pop. “Do you object to anal play?”
“On me?” his voice rose again, and he looked at me like I was crazy.
“I will take that as a yes,” I pointedly sighed as I crossed that off the list. “Nipple clamps?”
“What about them?” I was given a confused look.
“Would you like to experiment with them?”
“On me?” he asked me again.
I put the pen down and tried to keep from getting irritated with him. “Mr. Clarke, why are you here?” I looked at him again and saw a lost little lamb, “None of what I do has an interest to you. If it’s just sexual interest, I’ve already told you that it won’t happen.”
He sat forward, propping his elbows upon his spread knees, “Mr. Franklin wanted me to come and apologize for my behavior.” He paused and pulled out a check from his suit pocket, he offered it to me. It was blank save for the signature. “He said to use it as a means to get back in your good graces. I figured I’d take advantage of it. I just didn’t realize what I was really getting into. Anal? Really?”
“Don’t judge people or something you don’t have an understanding of,” I said lightly as I eyed the check. Mr. Franklin must be desperate. “Did he at least speak with you?”
“He did,” he rubbed his jaw, and I could feel his eyes on me. “If you don’t have sex with your clients, why dress like that?”
“What I do, Mr. Clarke,” I started, ignoring his gaze. “Is I provide an outlet for people’s darkest fantasies. I don’t have intercourse with the people I see. The man that left before enjoys seeing me in lacy things, details like this is something of a reward. Like when I allowed you to cum the last time you were here. A reward for your accepted your punishment,” I turned to eye him. “You didn’t tell me to stop, you didn’t curse me. You accepted it even though you were afraid and that was deserving of a reward.”
He leaned close to me, his voice going low. “What do you want to do to me?” His hazel eyes had darkened, and I felt like this was some sort of a test. Would I fall for it?
I fell for it, I set my clipboard aside, and I shifted to close the distance, my arm going around his shoulders as I did. “I would strip you, then chain you to my bed,” I lowered my voice, and I saw his eyes dilate and I knew I had him. “I would turn your skin the most perfect shade of pink, I would beat you until you couldn’t take more.” Warning bells were going off in my head as I pressed my lips to his ear, “If you took your punishment like a good boy, I might consider allowing you to cum. I just can’t decide whether or not I would use my hand or my mouth.” He released a breath, it was shaky, “But if you want something like that, Mr. Clarke, you have to be willing to submit to me.” I didn’t resis
t the urge to take his ear into my mouth, my teeth grazed the lobe, and I sucked on it lightly.
He groaned, and it vibrated through me, one of his hands was on my knee. It flexed, and I knew he wanted to move it up my thigh. “What do you get out of it?” his fingers squeezed my knee. I think he was testing me or maybe trying to tease me as I was him.
The throb, the one I felt the last time I had seen him was back, and so far all I had done was suck on his ear. I ran my fingers through his hair, scrapping my fingernails along his scalp. “I enjoy it,” because I did on some level otherwise I wouldn’t do this. I liked being in control.
His fingers toyed with the edge of my robe, it was short and fell just above the knee. “Do you get to cum?”
I pulled back and looked at him, he looked serious, and he had a bad case of bedroom eyes. “That’s not your business,” I decided.
“I don’t know what I want you to do to me,” he said after a length, his eyes seemed to still be dilated and his judgment sense fogged by lust. “But, I don’t want to walk out of here.”