The Virgin Dating Game

by Sky Corgan

  “Sexy naughty kitty,” he said, smiling like an idiot.

  “Your sexy naughty kitty,” I told him as I crawled up onto his lap.

  To my surprise, he gave my bottom a good slap, and I gasped at the pleasurable twitch it caused between my thighs.

  “I'm a little disappointed it didn't come with a cat tail,” I admitted.

  “You look gorgeous.”

  “I know, but a cat costume should come with a cat tail, even if it is just lingerie.”

  “Count yourself as a sexy little Manx.” He growled at me again, and I giggled.

  His hands wandered my body, his eyes taking in the sexy lingerie. Chase twisted a finger into the Marabou, examining it. Then he gripped the front of my collar and pulled me down for a kiss. I moaned against his mouth, quickly becoming aroused by his forcefulness.

  He reached a hand between my legs, petting at my folds over the thin lingerie. The fabric moistened at his very touch, speaking volumes about my desire for him.

  I broke free from the kiss, leaning over to whisper in his ear, “Put your fingers inside of me.”

  Almost instantly, I felt the bulge in his pants grow even larger, my lusty words quickly swelling his impressive cock. His hands groped me with no real haste, moving over my breasts, down my sides, around to my back. He gripped my ass and pulled me tighter against him. Then he reached around to fumble with the clasp on my top, apparently forgetting my request to be fingered. It didn't matter though. I was just happy to be touched by loving hands—hands that would never do me any harm.

  When the top of my lingerie slipped down over my breasts, Chase quickly took a nipple into his mouth, sucking fervently as he ground his thick member up between my legs. I groaned, the friction of it causing my pussy to throb with want. He was being a dirty rotten tease, and I loved it.

  When he was done sucking my right nipple, he moved on to the left, giving it equal attention. His hands kneaded my breasts as he sucked, his fingers pressing deep into their pillowy softness, almost to the point of pain. I licked my bottom lip as he moved back to the first nipple, flicking his tongue across the taut peak and then biting it gently, sending a jolt of electric pleasure straight to my clit.

  Almost involuntarily, I began grinding myself against him, my hips writhing from intense arousal. He took my hand, guiding it down between his legs. The bulge in his pants felt painfully tight, and I worked with haste to unleash the monster within. His tool pulsed in my hand when I took hold of it. I had forgotten what my grinding did to him. The tip was slick with pre-seed, glistening and yummy looking.

  My hand grasped his shaft, feeling the velvety smoothness of his skin as I worked it back and forth over his hard meat stick. Chase buried his face between my breasts, moaning.

  “Chey, I can't wait much longer,” he warned.

  “Good, because neither can I.”

  I crawled off of his lap to pull off the rest of my lingerie, leaving on the collar and cat ears. He licked his lips as he watched, picking up where I left off stroking his cock.

  “Aren't you worried your dad might come home?” he asked, though his expression showed little concern.

  “Not really. He's going to be out on the road for a while still.”

  “I'm not sure I'm too comfortable screwing in your dad's living room. Sorry, I'm just a bit paranoid.”

  “Fine,” I sighed. “We can go to my room, but you better be naked by the time we get there.”

  “You want me to strip as I walk?” he laughed incredulously.

  “You better, or I won't give you any of this kitty,” I lied, rubbing my hands down my body for effect.

  “Stripping it is,” he said, standing and unbuttoning his shirt as he followed me toward my room.

  We had to stop a few times so that he wouldn't fall over when he was taking off his shoes. It was a bit comical, tainting the sexy mood with laughter. I didn't mind though. Being with Chase was fun. He knew how to laugh and have a good time, unlike some other man I knew.

  By the time we got to my room, Chase and I were both butt naked. He backed me up toward the bed, looking especially sexy as he towered over me. Then he pushed me, causing me to gasp as my ass hit the mattress and bounced. Before I could recompose myself, he was lifting my legs over his shoulders and burying his face between them. This time when I gasped, it was from pure pleasure.

  His tongue worked skillfully on my button, rubbing back and forth, over, and under, and around. My mouth was a permanent O as his tongue plowed into my hole, then licked all the way up over my nub. Soon, he had me arching my back and grasping at the comforter, my breath absolutely ragged.

  “Finger me,” I begged, and he was happy to oblige, stuffing two thick fingers into my waiting cunt at once.

  My tunnel squeezed around them, my body firing off into a delicious orgasm. I tried not to wiggle too much as the contractions rolled through me, wondering if he could feel them under his tongue. It sure felt like he could.

  When he finally sat up, detaching his mouth from my sensitive bits, I grabbed at his shoulders, working to pull him on top and inside of me. His cock plunged into my depths, causing me to cry out in pleasure. The way it hammered into me made feel full and satisfied. I wrapped my arms around Chase's shoulders, and then squealed as he began to lift me up.

  It took me a few minutes to realize what he was doing. My grip tightened around his shoulders as he held me up, impaling me on his cock. Each reckless thrust caused me to whimper as he reached impossible depths within me. Never before had I been so stuffed full of cock, my body weight helping to make his penetration as deep as it could get. I worried the entire neighborhood would hear me as he speared into me, bouncing me on his thick rod until I felt absolutely drilled.

  It wasn't long before his strength waned, and I was set back down onto the bed. Despite the both of us struggling for breath, Chase didn't seem like he needed a break. He turned me around, then stepped up between my legs to take me doggy style. My body welcomed his cock past my folds and back inside, and I squeezed around him teasingly. That was met with a slap across the ass, and my cunt tingled from the painful stimulation.

  “More,” I begged. “Spank me as you fuck me.”

  His hand slapped across my ass repeatedly, sending that delicious stinging through my backside while his swollen cock worked to fill me up and set my body on fire. The sensation of everything was almost more than I could bear, and with a few extra thrusts, I found myself falling over the edge again, sinking into the blissful ocean of sexual insanity. Wave after wave pulsed through my pussy, milking Chase's cock. Almost before my own orgasm had ebbed, he was pulling out, grunting and moaning as his manhood released its seed onto my back.

  I sighed contently, resting my face on the comforter with my ass still sticking up in the air. My warm center felt absolutely delightful; my body was completely satisfied.

  Once we had cleaned up, Chase pulled me into his arms, nuzzling me affectionately. “Can I stay the night tonight? We've been having sex for a while now, but I still don't know what it feels like to sleep beside you.”

  It was an incredibly sweet thing to say and made my heart flutter with warm feelings. How could I possibly deny him?

  Not everything was rainbows and butterflies though. In the stillness of the night, as we lie together with his arms wrapped protectively around me, my mind thought of another man. Damien Reed. To think about him after just intimately being with Chase made me feel like a horrible person. He was always in the back of my mind though, seducing me.

  Chase was a good man—a sweet, loving, caring, wonderful man. And sex with him was incredible. But he still didn't entice the arousal that Damien did. All I had to do was look at the man and my clit would start throbbing with want. The sight of him was like a powerful aphrodisiac. And when we were together . . . it was all sparks.

  I lay in bed for several hours more, thinking about what my next lesson with Damien would be and feeling incredibly guilty for allowing my mind to wander e
lsewhere when it should have been focused on Chase. He was asleep now though, snoring loudly into my ear. It was part of the reason I was still awake, but I dare not stir him.

  Be content, Chey. You're having your cake and eating it too. But cake only lasts for so long.

  CHAPTER ELEVEN

  The week went on as boring and uneventful as usual. It was a bit different not taking Art Appreciation class anymore, but a good kind of different. I was happy not to have to sit under Damien Reed's emotionless gaze every day. He had a poker face most professionals would kill for. You could never tell when he was happy or sad or having a bad day. Once he stepped inside the classroom, he was strictly business.

  The other good thing about not having to see him every day was that my emotions had stabilized somewhat. Out of sight, out of mind. I could concentrate more on my studies and less on the twisted love triangle I had built. Some days, I felt almost normal.

  Don't get me wrong though. The weekends were still the icing on my cake. I looked forward to seeing Damien more than anything else. It was just nice not to be obsessing over him all the time because I was forced to be in his presence daily.

  Saturday rolled around, and I pulled up in front of his house at the usual time. Starting today, things were supposed to be getting a bit more intense between us, taking it to the next level, he had called it.

  He opened the door with the same level of enthusiasm, or lack thereof, and led to me to his classroom, which was really just a guest bedroom he called a classroom. Once I was seated on the bed, he handed me a notepad and pen, then took his place in the corner of the room, crossing his foot over his knee and setting his clipboard on top of his thigh.

  I stared down at the notepad blankly. This was new. Usually, our lessons were hands-on. What could he possibly have to teach me that would require me to take notes?

  “How was your week?” he asked, shocking me yet again. We very rarely discussed anything besides lessons during these brief one-on-one encounters.

  “It was fine.”

  “Are you getting good grades in school?”

  “Yes.”

  “Good.”

  If he was nervous, I couldn't tell. But there was definitely something different about the way he was acting.

  He took a deep breath before speaking, “Last time we were together, I talked about wanting to teach you about BDSM.”

  “I remember.” Boy did I ever remember. He had fucked me up against the glass in the cheer studio. It was the first time we had ever had sex, and good lord was it hot. The memory had replayed in my mind almost every time I had pleasured myself since. I doubted I would be forgetting it anytime soon.

  “I told you that because you seem to have some very submissive qualities. You mind fairly well, and I think you would make a good submissive or slave for a Master. But I don't want to pressure you into it, and I don't want you to take the lessons lightly. Learning about BDSM is going to take a very big commitment on your part. It's not just about kink and bondage and paddles. It's about learning to obey and giving yourself to someone completely, body, mind, and soul.”

  I shivered at his words. Giving myself to someone completely. That is what I felt like I had been trying to avoid. Chase wanted all of me, but I wasn't ready to stop seeing Damien yet. Was the time approaching when I really would have to choose between them?

  “I want you to fully understand what BDSM is before you decide if this is something you really want. Also, you should know that this isn't a class I teach very often. It's included on the questionnaire I originally made you fill out, and oftentimes I'll teach some of the kink involved in BDSM, but it's not often that I take the time to really teach someone the proper ways of the lifestyle. You have to display really submissive or dominant qualities for me to even bring it up.”

  That made me feel special somehow, but I wasn't quite sure why. Maybe it was because he saw something different in me than he had in most of his other students, even if it was something bizarre.

  “Alright,” I said.

  “Half of today is going to be a lecture. I gave you a notepad and paper so you can take notes. Just jot down the key points you want to remember. Things that sound like fun to you, or things that don't sound like much fun at all. Keep in mind though that this particular class is all in. You can't have some bits without the others. You should also know there will be homework, certain things you'll have to do for me to prove you're staying in line.”

  That meant more contact with Damien Reed. The thought gave me a giddy feeling inside, but it also partially filled me with dread. I had just got done thinking about how happy I was not to have to see him in class every day. Having contact with him more frequently might stir up the pot of emotions I had just now started to get settled. I wasn't sure how much I liked that idea.

  “Okay,” I responded, waiting for him to continue.

  “The other half of the class will be more in line with what we usually do. I know you get enough lecture during the week, and we both know that's not what you're really here for.” A devious smile played across his perfect lips, and my cunt ached needily, hoping the lesson for the second half of class involved parts of his body going into parts of mine.

  Stop it, Chey, you big pervert, I chastised myself. I couldn't help it though. He was just so damn beautiful.

  “How much do you know about BDSM?” Damien asked.

  “I read that one really popular BDSM book. You know, the one everyone is talking about,” I told him, proud I wasn't completely out of the loop.

  “Forget everything you learned from that book.”

  “Why?” I frowned.

  “Because most of it is bullshit.”

  “Which parts?”

  “For starters, the part where people who are into BDSM are portrayed as mentally damaged individuals. Most people who like BDSM are normal everyday people. They've led trauma free lives, have never been sexually abused, and are free of mental illness. They're your doctors and lawyers and mechanics—”

  “and college professors,” I broke in with a grin.

  “Yes. And college professors.” He nodded.

  “Alright. So, most people who are into BDSM are normal. I've got that. What else?”

  “Punishment isn't always about pain. In fact, most good Doms refrain from using pain as a form of punishment. I personally only use physical punishment for extreme cases, like when a submissive or slave knowingly disobeys an order I've given.”

  Now I was confused. “So, why do they market floggers and paddles as punishment devices in sex stores?”

  “They really don't. They're mostly used for scene play, which both parties enjoy. People unfamiliar with the lifestyle usually mistake the intent of the devices. Now, I'm not saying they're never used for punishment. Obviously, some of them are. It's really to each his or her own. But for the most part, paddles and cat-o-nine tails are used more for scene play than anything else.”

  “Hm. That is interesting. How do you usually punish people?”

  “By making the submissive do things they don't like.”

  “Like what?”

  “Oh, I have a variety of methods.” He smiled, and I could almost see the memories playing inside his head. “I make them stand in the corner or write lines on paper or other things.”

  “Very teacherly of you,” I teased.

  “Indeed. People hate it though.”

  “I imagine so. Being treated like you're a child when you're an adult isn't fun at all.”

  “That's the whole point of it. It's a punishment. It's not supposed to be fun. Those are just some examples though. I have a variety of other ways. I just wanted you to know that the vast majority of them aren't horrifying, so you really don't have much to fear besides boredom and frustration.”

  “So what do I have to look forward to then?”

  “Plenty. There are so many kinks in this world, and I'll explore all of them with you.”

  Now that sounded like fun. My sex life was pretty v
anilla in exception for my little voyeurism stunt at the cheer studio. I was so ready for more. Sex had become an exciting adventure for me, and I wanted to explore every facet it had to offer.

  “Like what?” I asked eagerly.

  “The variety is even more numerous than my list of minor punishments. There's the typical bondage, pain play, hot wax, lots of other stuff. We'll experiment to find out what you like and don't like.”

  “Sounds exciting,” I admitted.

  “That's half of the fun.” He grinned wolfishly.

  “So when do we get started?”

  “Oh, I have a lot more to tell you, and then I want you to take the night to really think about this. I know it sounds like fun and games right now, but it's not something to enter into lightly. I am a very strict teacher, and you need to be emotionally prepared for the things you'll have to do and freedoms you'll have to give up.”

  Now it was starting to sound scary again. I decided to shut my mouth and listen for the rest of the lesson, letting Damien have the floor completely.

  He continued, “As I've told you before, BDSM is the acronym for Bondage and Discipline, Dominance and Submission, and Sadism and Masochism. Bondage is obviously the use of ropes and restraints. Discipline can mean either one of two things. The first is the ability to follow orders. The second meaning is the actual act of discipline for bad behavior, which is also known as punishment. Dominance refers to Masters and Doms and the roles they play to take ownership of their submissives, slaves, or pets. Submission is the art of giving oneself over to the Dominant's will completely. This happens on many levels. Physically, emotionally, sexually, sometimes even financially, depending on the dynamic of the relationship. Sadism is the act of deriving sexual pleasure from inflicting physical pain on others. And Masochism is the act of deriving sexual pleasure from having pain inflicted on oneself. Typically, but not always, Master and Doms fall on the sadistic end of the spectrum, while submissives fall into the masochistic side.

  “It's important to remember that BDSM is not all about kink play. A true Master and submissive relationship has a lot more to do with control outside of the bedroom. Being a submissive means to give yourself to someone completely, to follow their every rule, and to take punishment whenever you disobey.