The Virgin Dating Game

by Sky Corgan

  When I was done signing, I pushed the contract toward Damien and he signed it as well. And with that, it was done. My first step into BDSM had been taken, and I would have to mind my P's and Q's around him from now on.

  “What happens next?” I asked.

  “Follow me.” He stood, leading me to the classroom.

  What Damien called his classroom was actually just a guest bedroom with extra chairs, but it had served its purpose well enough, which was to accommodate my lessons in sexual nature and fantasy. I had experienced my sexual awakening in this very room, and for that, it would always hold a fondness for me.

  As usual, I took a seat on the bed and waited for instruction. Damien went to the chest of drawers, opened the top drawer, and pulled out an object. When he turned around, I saw that it was a thin leather collar, the kind one might put on a dog. It felt strange having it fastened around my neck, as if I was losing a part of my humanity.

  “I want you to wear this every time you come over,” he told me. “You'll put it on outside before you knock on my door, and you'll not be allowed to take it off without my permission until after you have left here. This is your collar of consideration. When you begin training, I'll give you a different collar. Also, when you begin training, I'll give you a collar to start wearing in public. Don't worry, it's nothing that would be noticeable by the untrained eye. Public collars look a lot more like jewelry than anything else.”

  The idea of wearing a collar in public was odd to me. I hoped it would be a simple chain or a necklace. Anything else would just look strange.

  “From this point on, you will obey my every word,” Damien continued. “You will follow the list of rules I have given you. Failure to do so will result in punishment. Do you understand?”

  “Yes.” I nodded.

  “Yes, Sir,” he corrected me. “I will not tell you again. The next time, you will be punished.”

  “Yes, Sir,” I replied, feeling like my intestines were a nest of snakes slithering around in nervous discontent.

  “Tonight, I figured we would take things easy.” He went to sit in a chair in the corner of the room, admiring me from afar. “Let's play a little game. I'm going to ask you a question, and for every answer you get wrong, you'll have to remove an item of clothing.”

  This sounded like fun. “What about for every answer I get right?” Hopefully you'll have to take off an item of clothing.

  “For every answer you get right, you can take pride in knowing you pleased me.”

  “That's not a very fun reward.”

  “It should be. It will be, in time.”

  I thought about that for a moment. It did please me to know I made him happy. Still, I wanted more. I was a greedy girl with a greedy body. No reward would have been greater than his embrace, to feel the heat of his sex tunneling into me, filling me and making us one.

  “As you say, Sir,” I replied finally.

  “Good. Now, do you remember my rules?”

  “Yes.” I winced at my mistake. “Yes, Sir.”

  Damien smirked. “It will take some getting used to. As long as you correct yourself directly after a slip-up, I won't punish you.”

  “Thank you, Sir,” I sighed in relief.

  “Alright. Let's get started. What's rule number one?”

  My body tensed. Rule number one? I thought he was going to ask me questions about the rules, not which rule went to which number. Oh crap. I had already set myself up for failure. He had never told me I had to memorize them. Then again, I suppose that went without saying.

  The snakes twisted in my stomach as I said, “Sir, I don't remember the rules in numbered order.”

  He frowned. “Take off an item of clothing.”

  I removed one of my heels.

  “Both of them,” he ordered. “Shoes are bought in pairs, are they not?”

  “Yes, Sir.” Off the other shoe came.

  “From now on, Cheyenne, remember that if I give you any type of paperwork, you are expected to memorize it fully.”

  “Yes, Sir.”

  “So, you don't remember the rules by order, but you do remember the rules?”

  I wasn't so sure anymore. “Yes, Sir,” I replied.

  “Name the first one that comes to mind.”

  “I must tell you before I am about to orgasm so you can decide whether or not to allow it.” If there was any rule I would never forget, it was that one. It was so sensual, and I had already broken it twice.

  “Good. If I speak to you, what must you do?”

  “Answer you without hesitation.”

  “And with utmost honesty.” He paused for a moment, thinking, “When can you enter a room?”

  “Only if you are not in the room.”

  “And what if I am in the room?”

  “Then I must request permission before entering.”

  “Good. List the things you must do around company.”

  This question was a bit harder. There were a few rules about being around people, if I remembered correctly.

  I hesitated before answering, “When around company, I must not speak without your permission except to tell whoever is speaking to me that they must ask you first. If I am serving, I must always serve you first. And I think there's something else. . .”

  I glanced up at Damien, but his expression was unwavering. He didn't look pleased or discontent, offering no hint as to whether I was getting the answer right or not.

  “Is that all?” he asked.

  My mind raced with momentary panic. If he was asking, then that couldn't possibly be all. No matter how I tried though, I couldn't remember the rest. I'd read so much paperwork lately, it was hard to recall what had been in his rules and what had been in the extensively long contract.

  “I think the other one was that you're the most important person in the room?” I cowered, though I wasn't sure why. It wasn't like he was going to hit me. Worst-case scenario, I would lose another garment.

  “Take off an item of clothing,” he told me.

  “What did I miss?” I asked as I began unbuttoning my blouse.

  “Rule number nine. I will never disrespect my Master, whether in a public or private setting, whether he is present or absent.”

  That didn't seem very fair. Rule number nine didn't specifically mention being with others. I didn't bother complaining though. His game; his rules.

  “You've retained more than I expected. I'm impressed,” he said.

  “Thank you, Sir.”

  “But I'm getting bored with this game. Undress the rest of the way.”

  I wasn't sure if I should be excited or offended. On one hand, he was totally cheating. According to the rules, since I had answered the questions correctly, I should be allowed to keep my clothing on. Plus, his sudden boredom implied that he had expected me to fail, which was a rather rude assumption. On the other hand, if he wanted me to get naked, then that meant it was time to play, and I did so want to play with him.

  Obediently, I shed the rest of my clothing.

  “Lay in the middle of the bed,” Damien instructed as he stood to approach me.

  I did as I was told, centering myself on the bed so that I was laying straight down the middle. He climbed up onto the side of the bed, took both pillows, and then made me lift my hips, so he could shove the pillows under my butt. With the pillows in place, I was laying in an awkward position, with my back arched at an uncomfortable angle.

  Damien crawled between my legs, grabbed them beneath the knees, and hoisted them over his shoulders, pulling me closer to him. I suppressed a squeal of amused excitement, wondering what he was planning next. When he straightened himself and loosened his grip, my legs threatened to fall off his shoulders, dragging his shirt with them.

  “This isn't going to work,” he said, gently allowing my legs to fall to the sides before grabbing his T-shirt and pulling it over his head.

  My mouth salivated at the sight of him shirtless, that fit body I desired so much. His skin was pale,
contrasting with the manicured hair that covered his chest and stomach. I couldn't help but wonder how fuzzy he'd be if he let the hair grow out, but honestly hoped I'd never know. Body hair was not a turn-on for me. The only thing that made it bearable on Damien Reed was everything else I loved about him, which was literally everything. I could handle this one flaw, if you would even call it that.

  With the shirt tossed to the side, Damien grabbed my legs again, pulling them back over his shoulders. “We're going to practice orgasm control,” he told me. “Or rather, you're going to practice orgasm control. I can't hope for you to follow my rules if you go off without warning all the time.”

  “Orgasm control doesn't sound like much fun.” I pouted.

  “It can be a lot of fun. Don't you like the idea of sustaining your pleasure?”

  When he put it like that, it didn't sound bad at all. Still, the whole point of going to the edge was to fall over. I wasn't sure my body could handle the frustration of holding back.

  “When you first feel your orgasm coming on, I want you to tell me,” he said. “Do you understand?”

  “Yes, Sir.” I tried to nod, but it was a bit difficult since my chin was already so close to my chest from the scrunched up position.

  “Good. If you fire off early, you won't get your reward.”

  Reward? It was a word I was quickly beginning to enjoy. Hopefully, this time, my reward would involve a certain part of him going into a certain part of me, and I wasn't thinking about fingers or his tongue.

  Damien wrapped his arms around my hips, giving me one last tug so my ass was practically up in the air before his mouth began to descend between my legs. I shivered when his first warm breath wafted across my slit. He buried his mouth between my thighs, eliciting a groan from me as his tongue plunged inside, wiggling back and forth to taste my wanton pussy. A blush spread across my cheeks from the vulgarity of the position, thinking about how it looked like he was feasting on my female parts.

  After drinking my initial wetness, Damien withdrew, moving up to tease my clit by flicking his tongue across it. Each tiny movement brought on a throbbing that meant my orgasm was already well on its way to the surface. Should I tell him? Or should I let it play out? It feels so good, but I don't want to disappoint him again.

  “Stop,” I said suddenly, even though I was nowhere near my limit. Better to be safe than sorry.

  Damien's mouth made a wet noise as he pulled away, my moistness leaving a sheen across his lips. He licked them, and my body tingled in response. The look in his eyes was enough to set me on fire, the want in them.

  “You're too easy.” He grinned.

  “Oh, shut it . . . Sir.” I smirked, hoping he could handle a joke. Thankfully, he didn't seem to mind my playful demeanor.

  Before I had time to ask how long he planned on torturing me, my mouth became an O from the contact of his mouth on my feminine parts. His tongue went straight for my clit, picking up where it left off with a nice deep massage that caused the sensitive nerve endings to throb with desire almost the instant he touched them. Perhaps he was right. Maybe my body was too lustful. Already, I could feel the climb happening, and he hadn't even been between my legs for more than two seconds.

  “Stop,” I breathed out again, now feeling more embarrassed than anything else.

  He sat up and looked at me, waiting a moment for my pleasure to subside before diving in again. This time, he moved down to tongue my hole. Though it felt good, my resistance was a lot better with him away from my clit. I moaned, thinking of how hot his mouth was, how soothing his tongue felt, and how I yearned for other parts of him inside of me.

  Then Damien's mouth began to move again, licking downward towards my no-zone. His tongue flicked across my taint, and I held my breath, waiting for it to go back where it belonged. It didn't though. Instead, his tongue kept moving backward, crossing the short distance between my pussy and asshole.

  My entire body tensed, and I quickly and firmly told him, “Stop.”

  He lifted his head, looking innocent. If I hadn't been so upset at him for pushing my boundaries, I might have giggled. This wasn't the time for giggling though.

  “That's a hard limit,” I said, fighting back the urge to scowl.

  “Did I hurt you?”

  “No.”

  “Did it feel bad?”

  “No.”

  It had just felt strange. Not bad. Maybe even a slight bit pleasurable, but I would never tell him that. No matter how it felt, it was still gross.

  “Then why can't it be a soft limit?”

  “What's the difference again?”

  “A hard limit is something you absolutely won't do. A soft limit is something you're not comfortable with but would do under certain circumstances.”

  “It's gross, no matter the circumstance. It's a hard limit, and that's final.” I crossed my arms over my chest and then instantly uncrossed them because it felt like I was choking myself.

  Now he was the one who looked upset. “Cheyenne, it's not dirty. It obviously didn't feel bad, and it wasn't like I was going to stick my tongue inside of you. We can go slow with this, but anal is something I would eventually like for you to learn to enjoy. I enjoy it very much.”

  “Then maybe you should let me shove something up your ass first,” I huffed.

  Damien remained silent for a moment, as if he was actually contemplating it. “I'll think about it,” he said finally.

  “Hey, that wasn't an actual compromise.”

  “You can come now,” he told me before burying his face back between my legs.

  I gasped as he went straight for my clit, showing no mercy while his tongue and mouth worked together to milk out my orgasm. My toes curled, and my mind went blank as he brought me to climax within seconds, sucking and stroking until my nether region was nothing but contractions.

  “Damien,” I moaned his name, loving the sound of it on my lips. It was a sexy name, a name I could say for the rest of my life.

  If we hadn't just gotten into a minor squabble, I would have followed it up with an 'I love you', but it seemed like an embarrassing thing to say, especially since he had never said it to me before. Did he love me? I found myself wondering. There was no point in dwelling on it now though. Pleasure was more important. Just being together was more important. Love could come later.

  Damien grabbed one of the pillows from beneath me, tossing it to me, so I could put it behind my head while he pulled a condom from his pocket and unzipped his pants. His cock came out erect and beautiful. It was a perfect cock—perfect like the rest of him. Straight and long and thick, with a gorgeous round rip and a cute little slit. I wanted to get on my hands and knees and suck on it, but I knew better than to move. Besides, by the time I rolled around, he would have had the condom on already, and I couldn't imagine the condom tasted any good.

  “I want you to go on birth control,” he said as he crawled between my legs.

  “Does that mean we won't use condoms anymore?” I asked.

  He gave me a quizzical look. “Do you not want me to wear a condom?”

  I thought about it for a moment. Chase had never worn a condom when we were together. He always pulled out. As far as I could remember, the only time Damien hadn't worn a condom was when we were in the pool. And he had come inside of me that time—the only time a man had ever come inside of me. My cheeks flushed at the memory of how warm his seed had been.

  Was it wrong not to want him to wear a condom? I yearned to feel his skin against mine, to experience the heightened pleasure of our bodies coupled without boundaries between them. But of course, there was always the fear of getting pregnant. Even birth control didn't prevent it all the time. In fact, my mom once had a friend who had seven kids, five of which she had gotten pregnant with on birth control, and one she had gotten pregnant with even after she had her tubes tied. That woman was probably just freakishly fertile though. Most of the time, birth control worked, didn't it? Otherwise, why would they sell it?
>
  “I, um . . .” I stuttered, “it's up to you.”

  He grunted in acknowledgment and then guided his tip to my hole. My eyes followed it until it was out of sight, pressing between my pussy lips. The cool feel of the condom was soothing against my heated parts.

  Damien paused for a moment. “We're going to do the same thing this time. Whenever you feel your orgasm coming on, I want you to tell me to stop. Do you understand?”

  “Yes, Sir.” I nodded, biting my lip in anticipation.

  This was my reward, what I'd been waiting for so long. Put it inside of me, Damien. Please. I silently begged. Part of me wanted to wiggle, to scoot closer towards him. Hell, I would have impaled myself on his cock if he let me, but I knew I had to wait. He wanted me to wait.

  It slid inside slowly, cresting my entryway and causing that delicious tightness as it pressed against my inner walls. I groaned, lightly bucking my hips. Damien looked nothing but pleased, and as our eyes locked, electricity shot through me. This was the man I loved, the man I desired above all others, and I was never happier than when he was inside of me.

  Within seconds, he was all the way in, claiming my lips as he heatedly thrust into me, filling my body with emotions and sensations that could only be described as euphoric. Every buck of his hips was calculated, slow and dauntingly torturous, but it felt amazing, all the same. I wrapped my arms around his broad shoulders and moaned, kissing him again and again. My pussy pulsed around his member, a response to the feel of him throbbing inside of me.

  When my body didn't threaten to orgasm right away, Damien began picking up the pace. His pubic bone slapped against my clit, hammering out the first signs of my orgasm.

  “Stop,” I breathed, though I continued to cling to him desperately, my body wanting him to do the opposite of my words.

  He pulled out almost all the way, and when I felt his neck straining against my arms, I knew he wanted to sit up. With a sigh, I allowed it, waiting for my pleasure to recede.

  After a few moments, he leaned back over me, easing himself in. The first quick thrust was enough to send me up the climactic hill again, and I practically had to cry out, “Stop,” before his second thrust sent me over the edge.