The Virgin Dating Game

by Sky Corgan

“Let's start with the positions, Sir,” I said with a sigh.

  “You don't sound too confident,” he noted.

  “I'm not,” I admitted, keeping my eyes to the floor.

  “Perhaps you should have studied harder then.” There was no remorse in his voice. Damien stood in front of me, facing me, assessing my every move. “I'll be kind and count the Stand command as one of your ten positions. That means you only have nine left to get right.”

  It was a small kindness, but I appreciated it. Most of the positions were basic enough. I hoped he'd only give me the ones that he required and not everything that had been on the list he had sent me home with. If Damien was anything though, he wasn't fair in regard to my quizzes and how he graded them. Many times already, I received punishment for getting answers only half right. There was no doubt in my mind that he would take the same approach with this test. I might as well kiss all of those nice rewards goodbye. The thought was depressing, but there was nothing that could be done about it.

  Damien took a few steps away from me. “Your first position command is Come.”

  Of course, it wasn't something from his personal list of requirements. This one was straight from the position packet he had given me, and I had no idea what to do besides to step forward, standing directly in front of him with my hands to my sides and my head bowed respectfully.

  “Good,” he said, to my surprise. I wanted to grin giddily, but didn't want to give him an indication that my getting it right had been a complete fluke.

  Again, Damien stepped back. “Your next command is Crawl.”

  I quickly got down on my hands and knees, keeping my eyes to the ground as I crawled toward him with one steady hand in front of the other. This one also hadn't been on his personal list, but I was pretty sure I remembered it.

  “Good,” he praised me, and suddenly I was beginning to feel hopeful. Maybe I could make it through this after all.

  “Your next command is At Ease.”

  I stood, taking the traditional military at ease stance, with my legs spread shoulder-width apart, my head forward, and my arms clasped loosely behind my back.

  “Excellent.”

  I could hear the pleasure in Damien's voice, and it only elated me more. Four down. Six to go. There was still so much room for error.

  “The next command is Guard,” he said.

  My heart dropped. I had no idea what that position was. Doing my best to fake it, and hopefully redeem myself, I straightened my posture, drawing my arms up so that my hands were in the middle of my back, my elbows jutting out. By the time I had assumed the position, I was less sure of it.

  “This position would be used on command to keep watch over something if Sir requested it, right?” I asked.

  He smirked at me. “Correct. I haven't really specified a stance for it, but I am impressed that you came up with your own.”

  A trick question. I wanted to frown at him, but refrained. Sometimes, I swore he wanted me to fail. Perhaps he enjoyed punishing me more than he let on.

  “You're doing very well, Cheyenne. I must admit I'm impressed.” He walked around me. “Five more to go. Your next position is Humble.”

  Oh great, another one I didn't know. I relaxed my stance, looking towards the floor, having no idea what to do. Being humble made me think of slumped shoulders and sad eyes, though I wasn't sure why. Something told me I couldn't talk my way into making him think I knew this one.

  “I kind of didn't expect you to get this one right,” he admitted, stepping in front of me to grab my arms and outstretch them to the side. “The humble position isn't used very often. You stand with your legs shoulder-width apart and your arms outstretched. I prefer if the submissive keeps her eyes to the floor in this position.”

  “Yes, Sir,” I replied meekly.

  “Moving on. The next position is Whip.”

  I felt myself growing increasingly grumpy the more the test progressed. None of these positions except for the Stand position were ones he normally used. Why should I be expected to memorize them?

  Unsure of what to do, I held the Humble position and simply said, “I would bring you your whip before punishment, then I would stand with my body outstretched so that you would have access to all areas of my body for punishment.”

  “Only the first part of that is correct. I would probably make you retrieve the whip. However, the position is all wrong. There are two positions for the whip command. I would have accepted either one.

  “The first position is the standing position, where you stand against the wall, bracing yourself with your hands. Your back and buttocks remain exposed for whipping. The second position is the kneeling position. That position would put you on all fours. You would keep your head close to the floor and bring your hands beneath your body to protect them.”

  I half expected him to give me two marks off for not knowing either position, but when he didn't say anything about it, I figured I had miraculously gotten off the hook. There was only one reward left to lose before I entered punishment territory. Things were beginning to look more and more bleak.

  “The next position is Sit,” he told me, all hints of being impressed now gone from his voice.

  For a second, I thought about sitting on the edge of the bed. But that was wrong, I realized at the last minute. Instead, I sat Indian style on the floor with my hands on my thighs, my eyes to the ground.

  “Your hand position is wrong,” Damien informed me. “Your palms should be facing up.”

  Damn. I groaned internally. And with that, all of my delicious rewards were stripped away. Anything wrong beyond this would just earn me more misery.

  “The next position is Punishment Knees.”

  I climbed up onto my knees, laying my hands palm down across my lap.

  “Wrong again,” Damien said. “The position is the same as Whip on your knees, except for you'd kneel instead of being on all fours. You've earned your first ten minutes of punishment.”

  It took everything in me not to throw a tantrum. This had gone from exciting and fun to being a nightmare. What horrible punishment would Damien come up with for me this time? If it was between the penny and the ping-pong ball, I hoped he'd be nice enough to give me the penny. At this point, even a hard ass spanking might be better than the ping-pong ball. I had grown to loathe that little thing so much.

  “Your last position is Heel.”

  I climbed back up to my feet and stood at his right side, thinking about how much this made me feel like a dog.

  “Close,” he told me, “but you should be standing a foot back.”

  Damn it. Damn it. Damn it. A half wrong was a whole wrong in Damien's eyes. I couldn't fight back my scowl any longer. Twenty minutes of punishment, I'd earned, and there was still the potential for over an hour more.

  “You may sit on the bed while we go over vocabulary.” Damien took his seat in the corner, and I hesitantly, eased myself onto the bed, wondering if I should be assuming the Teach position. At that point, I was fed up with positions, but I feared more punishment. Better to be safe than sorry, I thought, pressing my knees together and crossing my hands over my lap.

  Damien's gaze was icy cold, showing little expectation of the remainder of my performance. The way he was looking at me made me feel kind of sad, like I had gotten his hopes up only to drop kick them into oblivion with my poor performance. Unfortunately, my self-confidence had fallen with his expectations. I wasn't even sure if I really wanted to try anymore.

  “Are you ready?” he asked.

  As ready as I'm going to be. “Yes, Sir.”

  “Your first term is 24/7.”

  I distinctly remembered the term from my very first list of vocabulary words, though I couldn't quite remember what it meant. Hopefully, my guesswork would be good enough to avoid adding to my punishment.

  “24/7 means being submissive to the Dominant at all times,” I said.

  “That's correct.”

  I sighed in relief.

 
“Your next term is age play.”

  There was no way I had forgotten that one. It had been a term I partially failed last time Damien had quizzed me on it. That made it all the more memorable.

  “Age play is a scene between two people where one takes the mentor role while the other assumes the role of the learner. Different scenarios can be used to accomplish an age play session, though incest themes usually aren't a part of them. It's more about the emotional relationship between the two in regard to the age difference.”

  “That's a bit wordier than I would have put it, but close enough.” Damien nodded in approval. “The next term is auction.”

  “An auction is an event where Dominants auction of their slaves and submissives to other Dominants for a specified period of time.”

  “Yes. Next word is bondage.”

  I was becoming more confident by the minute. Most of these terms he had quizzed me on before. It was a lot easier to remember the ones I had been punished for forgetting.

  “Bondage is the use of ropes, chains, or any other apparatus to restrain a submissive.”

  “Bondage can be used for total restraint, or only to restrain certain parts of the body,” Damien added. For a moment, I worried he was going to count it as a half-right, but thankfully, he pressed on. “Your next word is chastity.”

  “Chastity involves the denying of the ability of a submissive to touch or pleasure themselves via verbal command or a chastity device. The submissive must remain chaste while the command is in place.”

  “Good enough. Next term is consequences.”

  “Consequences are the direct result of a submissive's behavior. If the submissive displays bad behavior, the consequence is punishment. Consequences are often decided by the Dominant beforehand.”

  “You're only half right,” Damien said. “There are two kinds of consequences, natural consequences and logical consequences. Natural consequences occur as a result of our everyday actions and are controlled by our environment. Logical consequences are those that result from purposeful bad behavior as outlined by your Dominant. Having said that, I'm adding five more minutes to your punishment time for not knowing both types.”

  Five minutes wasn't as bad as ten. With only four more vocabulary words remaining, I was doubtful my punishment time would be more than an hour, which was making me oddly happy, considering the dismal situation.

  “Your next word is discipline.”

  This is another two-parter. “Discipline is the act of disciplining a submissive to correct behavior. It is also about having control over oneself.”

  “Discipline is a type of training wherein the submissive is taught to obey through various methods set forth by the Dominant,” Damien corrected me.

  Damn. I was almost certain I had gotten that one right. The punishment toll increased yet again.

  “The next word is dungeon,” Damien said.

  “A dungeon is a place where BDSM furniture is kept and scenes are carried out. Dungeons can be used for both punishment and pleasure.”

  “Good. Only too more left.” He sounded almost as relieved as I was. This was turning into a long game, and I was ready to take my punishment and move on to better things. “Your next term is erotic spanking.” Damien grinned lecherously, causing a blush to spread over my cheeks.

  This was a term I was very familiar with—a term I quite enjoyed.

  “Erotic spankings are those given for pleasure,” I replied confidently, feeling a pulse between my legs from the memory of the erotic spanking Damien had given me a few weeks back.

  “I didn't think you'd forget that one.”

  “No, Sir. I would never forget that one.” I smirked.

  “Your final term is goals.”

  “Goals are planned milestones that a Dominant and submissive come up with in regard to the progression of a submissive's training. They can be set and revised at the Dominant's discretion.”

  “Very good.” Damien smiled at me, and I thought I saw a hint of appreciation in his eyes. Perhaps he didn't think I had done so bad after all. “I think you know what happens next,” he told me.

  “Yes, Sir. I am to be punished for the questions I missed.”

  “You did really well on your definitions. It's the positions you failed on mostly. That's partially my fault for not making you practice them.”

  “If you don't mind me saying so, Sir, most of the positions on the test were not ones you typically require me to use.”

  “No. But I would like for you to learn them, none the less. Perhaps we should try to incorporate them more in our sessions. And just so you know, there will be another test like this one before the end of your training. At that point, you will be expected to have everything memorized. If you don't, your training will be extended.”

  My smile sank, though it didn't quite make it into a frown. Six months was a long time to learn all the positions. If I couldn't retain them by then, then I really would be a fail as a submissive.

  “I believe that's fair, Sir,” I said finally.

  “Good. Have you brought the journal I requested you to keep up with?”

  I cowered slightly at the mention of it. To be honest, after signing the training contract, I had forgotten about the journal completely. The thought of more punishment was daunting though. Should I lie or tell the truth?

  “I forgot it at home,” I replied, opting for the answer that I thought would earn me the least amount of additional punishment. “I'm sorry, Sir.”

  “I'm adding ten more minutes to your punishment time for forgetfulness. Bring it with you tomorrow.”

  “Yes, Sir.” I nodded.

  Though dishonest, it would be easy enough for me to make up journal entries for all the days prior. While Damien might have cameras in his mansion where he could watch my every move, he didn't have them in my house. No matter how good he was at figuring me out, I doubted he would be able to tell that the entries were all created in one afternoon.

  “Now it's time for your punishment,” Damien continued. “Since today should be a day for celebration, I'm not going to be too hard on you. I want you to stand in the closet for the next forty-five minutes. You can assume whatever position you wish while you're in there. However, you have to leave your phone out here and remain completely quiet.”

  “I understand, Sir.”

  I walked over to the closet and opened the door. Inside were a few jackets that I had never seen Damien wear. Carefully, I pushed them aside and squeezed in with them, closing the door behind myself. Damien moved on the other side of the door. Whether he left the room or not, I couldn't tell, but it didn't really matter.

  The next forty-five minutes were spent in dark silence, and I was thankful I wasn't claustrophobic or prone to irrational fears. I slid down the wall, hugging my knees and resting my head, closing my eyes and trying not to fall asleep.

  Eventually, Damien's footsteps returned and the closet door opened. He offered me a hand to help me up. Then he sat me back down on the bed to discuss a few more things before our kink session.

  “What are you to do now?” he asked.

  “Thank you for my punishment, Sir. I earned it for not knowing all of my submissive positions and vocabulary words. Would Sir like for me to write definitions for the words I missed?”

  “Yes.” He seemed genuinely pleased. “Before you leave here today, I want you to write down your schedule for me for the coming week. If anything should change throughout the week, you will text me and let me know. Now, I know this may seem a little invasive, but don't worry. It will be very rare that I disapprove of your activities, if ever. This is more an exercise in trust and learning to give yourself over to me completely.”

  “Yes, Sir.”

  In all honesty, I wasn't really worried about it. I couldn't picture Damien going out of his way to stalk anyone. More than likely, he'd take the schedule, look it over, and not think anything else of it until he received the next one the following week.

  “Remove all
of your clothing and Lay Down,” he said.

  I did as I was told, shedding my garments and folding them neatly before I assumed the position on the bed. While I was doing this, Damien rummaged through the chest of drawers, pulling out a red square pillar candle, a lighter, and a candle holder. He lit the candle and placed it in the holder, waiting for me to finish obeying his commands.

  “Can you guess what we're going to do tonight?” he asked, glancing over at the candle.

  I had an idea. There was only one reason Damien would have brought out a candle, and it wasn't to set a romantic mood. My stomach twisted nervously, watching the flickering flame.

  “We're going to play with wax today,” I replied, making it sound more like a question.

  “Mhm. You forgot to call me Sir again.”

  “Sorry.” I cringed, praying he wouldn't force me into the closet for another round of punishment. “I mean, sorry, Sir.”

  “You're impossible.” He shook his head. “Anyway, have you ever played with candle wax before?”

  “No, Sir, though I've seen it in music videos.”

  It was sexy in music videos. A hot chiseled guy would be laying shirtless, usually the singer, and a gorgeous model would be pouring wax down his chest. Those scenes had always made my pussy throb with excitement. I wasn't sure what it was about seeing it that turned me on, but it was damn appealing.

  The only thing was, I had never seen it done to a woman before. Always, it was a man on the receiving end, wincing and looking yummy and just laying there and taking it. I bit my bottom lip, thinking about it.

  “Chey.” Damien drew my attention back to him.

  “Hm?”

  “You looked like you were spacing out a bit.”

  “Oh, sorry, just thinking.” Thinking deliciously wicked things. How about you let me pour it on you instead, like in the videos? I bet it would look so much better on you.

  He approached me with the candle, and all naughty thoughts melted away, replaced by the fear of pain. My mind scanned back to all the wincing expressions I had seen in those videos. No one kept a straight face when the drops of wax fell, which meant it couldn't possibly be pleasant.

  Damien sat on the side of the bed and held the candle over my chest. Instantly, I sucked in. When he dipped it to let the wax fall, my fear got the better of me, and I squirmed away, forcing him to jerk the candle back up before it spilled its contents.