The Virgin Dating Game

by Sky Corgan

  I turned on him, agitated. “Do you want me in the corner or not?”

  “Punishment Knees.”

  Oh crap. I finally pissed him off, I realized. Now I would get to taste what one of his real punishments felt like.

  While I was still upset, curiosity made me assume the position. I knelt in front of him, naked on the carpet, with my head down and my hands near my face. My ass was up in the air like a beacon, just asking for a nice delicious spanking. Oh, please be a spanking. Please, I silently begged, my anger melting away into perverted thoughts.

  As if Damien was reading my mind, he said, “I bet you're hoping I'll spank you.” When I didn't respond, he asked, “Well, are you?”

  “Yes, Sir,” I admitted, feeling my body heating up.

  “Not all spankings are pleasurable.” The darkness in his voice sent a shiver down my spine.

  I couldn't imagine a spanking not being pleasurable. If he thought that he could turn a spanking into a punishment, the joke was on him.

  “I want you to thank me after every strike, do you understand?” he said.

  “Yes, Sir.” My clit tingled from the order.

  Perhaps I would disobey more often. What he was teaching me was the opposite of what he had hoped. If spankings were to be my punishment, then I would be bad all the time. A lecherous grin crossed my lips as I heard him move behind me, and it took everything in me not to wiggle my butt.

  My smile melted when his hand came down with the full weight of his body. Searing agony raged through my backside, pushing past the point of pleasure and tumbling into unexpected pain. I choked on my own breath, gasping in disbelief at the force of the blow.

  “Do you have something to say to me?” Damien asked.

  “Thank you, Sir,” I was barely able to stutter out before another crack of torment landed across my backside. The skin already felt swollen and burning, like the sting of a thousand angry fire ants. “Thank you, Sir,” I echoed the words with tears in my eyes. By the third slap, I didn't think my body could take anymore. My safety word was on my lips, threatening to spill out, but instead, I said, “Thank you, Sir.”

  I squeezed my eyes shut, trembling, waiting for the next blow. Part of me didn't think I could handle it, but I knew I had to. When Damien's hand touched my ass again, it wasn't to spank me, but to rub against the welt. My pulse moved to my ass, beating against his hand. It felt like I might melt his skin right off from the heat.

  “Why were you punished?” he asked, running his fingers delicately over the welts.

  “Because I showed you attitude, Sir,” I said, suppressing the urge to whimper and cry.

  “That hurt me more than it hurt you, and I never want to have to do it again. Next time, just stand in the damn corner.” He climbed to his feet and sat back in the chair. I hadn't even realized he had been kneeling beside me the whole time. “Examination,” he ordered, and I found myself crawling onto the bed and assuming the position with my legs spread wide and my hands above my head.

  Even the feel of the comforter against my swollen backside sent pain shooting through me. Never again would I purposely piss off Damien Reed.

  Once I was in position, Damien came to stand over me, assessing me with emotionless eyes. He bent slightly to grab my breasts and lift them up, examining underneath them. The whole thing made me feel incredibly uncomfortable, but I laid there anyway, suppressing my sniffles.

  Even though I knew I deserved the punishment, it still upset me. My mind was a tangle of negative emotions. If he loved me then how could he hurt me like that? It's not that he doesn't love me. He's just trying to discipline me. He told me what would happen if I continued to disobey. I should have listened. Stupid, stupid Chey. Now he's mad at me. I don't want him to be mad at me. I was a good girl. I took my punishment and didn't complain.

  “Why are you crying?” he asked, watching as tears cascaded down my face.

  “Because you hurt me,” I whimpered.

  “I gave you more than enough chances to listen.”

  “I know. I just didn't expect . . .”

  “That a spanking could hurt?” he paused. “Despite what you probably think, I didn't enjoy doing that anymore than you enjoyed receiving it. I don't get off to the thought of hurting you. In fact, I use physical force as the last effective measure of punishment. Obviously, you were going to continue to give me attitude if I kept sending you to the corner. It wasn't working, so I needed to modify my approach. Now that you know what it feels like for me to have to modify my approach, you'll be more apt to listen to me next time I issue you a punishment. Do you understand?”

  “Yes, Sir,” I squeaked.

  “Don't just tell me 'Yes, Sir' blindly. I want to know you actually understand my reasoning. So I'm going to ask you again, do you understand?”

  “Yes, Sir,” I replied, more clearly this time.

  “Good. Now dry your eyes and assume the Examination Front position.”

  After wiping my eyes, I rolled over onto my stomach, keeping everything else about the position the same. My body tensed as Damien's hand rubbed over my ass again. Even though it had been several minutes since the intense spanking, I could still feel pain through my backside. It would probably bruise.

  “Examination Cunt,” he told me, and I rolled back around, bringing my knees up to my chest and spreading them slightly to expose my feminine folds to him.

  Damien crawled up onto the bed, and for a moment, I thought he meant to fuck me. Instead, he spread my pussy lips. For the first time ever, I wasn't sopping wet for him. In fact, my mind was too emotionally wrecked to be thinking much about sex. All I could think about, aside from the spanking, was the discomfort from being so vulnerable. Damien was looking inside of me, quite literally examining me in a very non-sexual way, kind of like how a gynecologist does.

  It wasn't until he pressed two fingers inside of me that my body finally responded, relaxing into its more wanton state. Need pulsed through my clit, and I grew angry at myself for desiring him so much after what he had just done. I should be pissed off at him, not craving him between my legs. Stupid body.

  The moment didn't last. Soon, Damien was withdrawing and telling me to assume the final position, which was Examination Anal. This position was reminiscent of the Punishment Knees position. The only difference was I had to spread my ass cheeks for him with my hands. My face flushed pink as I did this. It was the most embarrassing and degrading position of all, letting him look at my asshole. I thought about contesting it, as one of my hard limits, but what grounds did I have to say that under. He wasn't hurting me. Hell, he wasn't even touching me. I was just uncomfortable.

  Throughout the examination process, I found myself holding in my breath and emotions. Tonight was a night I would never forget—the night I truly felt like we had taken our relationship to a different level—a very dark level I wasn't sure I liked. Being vulnerable was one thing, but this felt like something else entirely—a complete mind fuck.

  When the examination was over, Damien gave me the Lay Down command. As quickly as possible, I laid on my back, trying to remember the placement for my arms. I wavered for a moment in uncertainty, but Damien had crawled off the bed to return to the chest of drawers, and by the time he turned around, I had remembered and corrected myself. He returned to me with two small objects, holding them up in his hands. One looked like a blue eye shadow compact. The other was a small tube, probably containing some kind of lube.

  “Right hand or left hand?” he asked.

  I gave him a quizzical look, worried it was a trick. “What are they?”

  “That's not what I asked you. Right hand or left hand?”

  Fearing further punishment, I decided to shut up and choose. The blue compact was interesting looking, but the tube was definitely more familiar.

  “Left hand,” I said finally, indicating the tube.

  Damien put the compact back in the chest of drawers before he returned to me. “Assume the Examination Cunt position,”
he commanded.

  With a nervous sigh, I brought my knees back up to my chest, parting my legs slightly. I watched Damien as he twisted the cap off the tube and squeezed a dab of clear gel onto his finger. Then he rubbed the gel directly on my clit.

  It didn't feel like anything special at first. He gave my nub a good dousing, igniting my pleasure core with the touch of his finger. Then he put some more gel on his finger and rubbed my pussy lips with it. By the time he was done, I began feeling the effects of the lube on my pleasure button. It was heating up quickly, causing a tingling sensation. When Damien put the cap back on the tube and leaned between my legs to blow on my folds, I gasped from the strange sensation that ran through me. Within seconds, my clit was throbbing, my labia fully engorged with seething desire.

  “What was that?” I asked.

  “It's called WOW gel.” He grinned.

  Wow was right. It felt amazing, both hot and cold at the same time, tingling and pleasurable. I could feel my nerve endings coming to life and my pussy beginning to moisten.

  “It's clitoral arousing gel,” he explained. “How does it feel?”

  “Good. I like it.”

  “Good. Shall I take things up a notch?”

  I was scared what that meant, but I nodded anyway.

  Damien licked two of his fingers and pressed them into my exposed cunt. He slid them inside gently at first, scissoring and exploring. It felt exquisite coupled with the throbbing of my clit. When his fingers were fully inside, he arched them and began thrusting slowly. I groaned shamelessly, feeling like I might drool on myself from pleasure. Already, his fingers were squelching inside of me, proof of my arousal.

  He pulled out, opened the tube again, and gave my clit another rubdown with the gel. This time, he pressed his index finger hard over my nub. Fire shot through me, consuming me with lust and desire. It felt like my pussy was absolutely drooling.

  “Damien, I'm going to,” I warned.

  He buried his face between my legs, flicking his tongue across my clit. If he had wanted me to stop, this wasn't a good way to show it. Almost the second he sucked my sensitive bits up into his mouth, I came, contracting and squirming and panting. Damien showed no signs of letting up, devouring my cunt until no gel or wetness remained. When he did finally come up for air, all I could think about was how much I wanted his cock inside of me.

  “Fuck me,” I whispered.

  “I want to, but you've been bad,” he said.

  “You taught me a lesson. I won't be bad again.”

  For a moment, I was hopeful, but then he crawled off of the bed and sat back down in the chair, filling me with disappointment. I wasn't sure if I was allowed to move or not, so I just laid there, staring at him, praying he would return.

  “I like you like that,” he told me, though his expression was blank.

  “I want you inside of me. I think I might stay like this until you come stick it in me.”

  “You'll be staying like that all night then.” He smirked.

  “If it's what you want.”

  “You become so compliant when you want to be fucked.”

  “I can't help it. I want to be fucked.” I grinned back at him.

  “I'm glad you're not upset anymore.”

  Had I ever been upset? It seemed like a distant dream now. The welts on my ass had finally cooled. Only the hand impression lingered behind.

  “You're not allowed to pleasure yourself anymore,” he said, turning my grin into a frown. “And you can relax now.”

  I lowered my legs to the bed and rolled over onto my side, looking at him. “Why not? What did I do to earn punishment this time?”

  “It's not a punishment. I want all of your orgasms to belong to me. Every time you come, I want it to be because I allowed it. That would give me great pleasure.”

  My clit throbbed from his words, but my brain knew my body shouldn't be happy about it. Masturbating was an integral part of my life. I did it at least once a day. The thought of being denied made me discontent.

  “I don't like that rule,” I told him.

  “Why not?”

  “Do you have any idea how much I masturbate?”

  “I do. You put it on the questionnaire, remember?”

  “Oh yeah. I forgot about that,” I huffed. “Well, if you're going to do that to me, then I need to see you more.”

  “Neither one of our schedules will allow that.”

  “Then we need to compromise.”

  “Fine. I won't masturbate either.”

  It wasn't the kind of compromise I had expected, but the thought was very arousing. I tried to imagine a pent-up sexually frustrated Damien Reed. He would probably be absolutely ravaging in the sack. My thighs wanted to rub together from the thought.

  “Wouldn't that be difficult for you too?” I asked.

  “It's all about self-control, Cheyenne. I have a lot of it. You, on the other hand, don't.”

  How rude? I sat up and crossed my arms over my chest.

  “If you're not going to fuck me, then I'd like to get dressed,” I told him grumpily.

  “Fine.”

  As I began to put on my clothes, he continued, “I won't be able to see you tomorrow. I have a teachers dinner to attend.”

  While I knew I should have been upset, I honestly felt relieved. At least now I wouldn't have to feel bad about not being able to see him because of my father coming home. Still, shouldn't this be even more reason for us to have sex.

  “Are you sure you don't want to fuck?” I asked, feeling a bit sleazy for it.

  He laughed, “You're insatiable. But no. You'll survive for a week.”

  Would I? I wasn't quite sure. To be honest, I hadn't gone without masturbating for more than a night or two since I discovered the pleasures of my own body. The thought of going a whole week was almost incomprehensible. I would probably rape Damien the next time we were together. A silly mental image played in my head of him opening the door and me ripping off his pants and jumping on his dick right in the doorway. It was funny to think about now, but who knew how accurate it could be by the end of the week.

  “I don't like this,” I grumbled.

  “It's not your job to like it. It's your job to accept it.”

  “Doesn't being a submissive mean some things are up for debate?” I eyed him wearily. “I could have sworn you said that at some point.”

  “Some things are. Not everything. If you don't like it, you can always decide not to move on to training when your trial is over.”

  I groaned. Why did he have to be such a hard-head?

  “Fine,” I relented.

  Damien stood to dig through the chest of drawers again. “Before you go, I need to give you your packet on the submissive positions. There's also another list of keywords in here. Don't forget to bring me your homework, the definition for age play written down on a piece of paper in your own handwriting ten times.”

  I thought about giving him attitude, but refrained. The corner did not look appealing, and I doubted my ass could handle another round of brute force smacks. Instead, I took the paperwork from him and simply said, “Yes, Sir,” before following him to the door.

  In the car, I took off my collar and reflected on everything that had happened. It had been an odd night, and things were definitely getting a lot more intense. While I loved the kink play, I was still having a hard time adapting to the idea of being a submissive. There was so much to remember, and Damien was strict in Dom mode. A large part of me wished we could go back to the way things were, but I feared there was no going back now. I could only look forward and hope I could conform to the harsh standards—to be everything Damien wanted and needed.

  CHAPTER FIVE

  As soon as I got home, I did my definitions. It was annoying, but at least it didn't take too much time. I found it funny that the term I failed was age play. Wasn't what Damien and I doing kind of like that, except our age difference was very real? It wasn't something I liked to think about often. Ho
w would my parents feel if they knew I was seeing a man so much older than me? My mother probably wouldn't approve. My father probably wouldn't care, as long as I said Damien was treating me right. Still, the idea of talking to them about him made me feel awkward. Would he ever meet them? Would we ever have a normal enough relationship where he'd want to meet them? I was beginning to doubt it. How exactly did that work in BDSM relationships? Did you bring your Dom home to meet your parents?

  You're putting waaay too much thought into this, Chey. With a groan, I changed my clothes and climbed into bed, reaching over to turn my lamp off.

  The following day was spent cleaning the house in preparation for my father's homecoming. It's amazing how much a single person can dirty a house. As I mopped the tile in the kitchen, I thought about what a slob I had become since starting college. It wasn't as bad as Chase's apartment had been, with empty boxes of pizza on the counter and dirty clothing everywhere, but it was below my normal standards of cleanliness.

  Thankfully, Dad didn't arrive home until shortly after I had finished. When I opened the door, I was greeted by his warm weathered smile. My father looked older than the last time I had seen him. His face had more lines, and the stubble on his chin was more salt than pepper. He outstretched his arms to me, and I jumped into his embrace like a small child, squealing, and squeezing him, and inhaling his familiar scent.

  “How ya doin', kiddo?” he said.

  “I'm good,” I replied as I pulled away and stepped aside so he could come in.

  The duffle bag he carried looked as worn down as he did. There was no telling how old it was, but he'd had it for as long as I could remember. A small tear in the side revealed some garment beneath, no doubt in need of a good washing.

  “How was your trip?” I asked, following him into the living room.

  “Same old, same old.”

  My father was a man of few words, which made holding a conversation with him awkward at times. Sometimes I wondered how he and my mom had ever gotten together. They were different people back then though. A different time; a different place; a different life.