The Virgin Dating Game

by Sky Corgan

  “So, anymore hard limits?” he asked.

  I suddenly felt confused. “I don't think so. Could you give me some examples of what other peoples' hard limits are?”

  “Well, a lot of people don't like pain. They might be against being whipped or paddled.”

  The thought of being paddled sent an aching need straight to my pussy. I had never met anyone who would be willing to do it. All of my past boyfriends were strictly vanilla. Or so I had assumed, considering I hadn't slept with any of them. Damien seemed like a kinky freak by comparison. Then again, he was a lot older, a lot more mature, and he taught this strange sex class.

  I shrugged before saying, “I'll try almost anything once.”

  “Except anal sex,” he noted.

  “Yes. Except anal sex.” I nodded.

  “What do you have against anal sex?”

  I felt embarrassed to say it, but I couldn't come up with a good enough lie that didn't sound stupid. “I think it's mostly for gay men.”

  He let out a short laugh. “Anal sex is not just for gay men.”

  “I still don't think I'd want to try it. It sounds kind of gross to me.”

  The grin stayed on his face. “Okay then. Well, that pretty much covers everything, except that you left the ultimate sexual fantasy question blank.”

  “I wasn't sure if you meant a realistic fantasy or one of those fantasies you have that you'd never actually live out.”

  “It doesn't really matter. I just ask this question, so I can get a better idea of what you're actually into, or perhaps the things that you'd like to try.”

  A blush came to my cheeks as I opened my mouth to speak. “Well, I kind of would like to be spanked.”

  I expected him to say that my fantasy was tame, but he didn't say anything. Instead, he pulled a pen out of his pocket and filled in the blank spot on my questionnaire.

  “Anything else?” he asked.

  “No.” I shook my head.

  “Alright. Well, I'm sure you'll come up with more as we progress through our lessons. These classes are very much about sexual awakening, figuring out what you like and don't like.”

  That sounded absolutely blissful. Anything that Damien did to me, I would probably like . . . a lot.

  “How many other students do you have?” I inquired, and then wanted to slap myself for it, knowing the answer would depress me.

  “Just you, for right now.”

  Relief flooded through me. He's mine. All mine. At least, for now. The thought gave me a strange sense of satisfaction. Part of me wanted to ask him if he had a girlfriend, but I didn't want to press my luck. I would hold onto the fantasy that he belonged to me exclusively, for as long as I could.

  “Do you have any other questions for me?” He set the questionnaire down on the table and relaxed back into the couch, crossing his ankle on top of his knee.

  “No. I don't think so.”

  It felt so strange having his complete attention. I wanted to look at him, but I couldn't, knowing I'd meet those deep dark eyes. They always seemed like they were burning right into me, making me feel exposed and vulnerable. I loved that about him, but I also hated it.

  “Tell me about yourself,” he said.

  “What do you want to know?”

  “Anything you want to tell me. Perhaps you could start with letting me know a little about how life was for you growing up. How was your family dynamic? Did you suffer any traumas in the past?”

  “No. No traumas.” I shook my head, leaning back against the sofa and trying to relax. “I suppose my childhood was fairly normal. My parents stayed together until I started high school. When they got divorced, I ended up living with my mother. My father is a truck driver, so I couldn't really stay with him.”

  “So, you live with your mother right now?”

  “No. I recently moved in with my father since he lives close to campus. He's rarely at home though, so I have the house to myself most of the time.”

  “And siblings? Do you have any?”

  “No. It's just me.”

  “I see.”

  I half expected him to ask if I liked being an only child. It seemed to be the standard question as soon as I told people I was one. Damien didn't seem interested beyond that point though. He just sat there, looking at me, making me feel a bit uncomfortable.

  “And you?” I asked. “What about your family?”

  “Nothing out of the ordinary. My parents are still married, though they're living in Washington right now. My father is a politician. My mother is a house wife. She was a stay at home mom for me and my brother when we were growing up.”

  “So, you've always been pretty well off?”

  “Yup. Spoiled little rich kid.” He smiled. “Though, don't get me wrong. I had to work for the things I wanted. Nothing ever came free. My father was a very strict man, and my mother was a perfectionist. They were good parents, but a bit overbearing. I think that's one reason why my brother and I both moved away as soon as we could. He moved away right out of high school. I waited until after college, when I was offered the job here.”

  Maybe his parentage explained why he was such a neat freak. Just glancing around his house, everything seemed too clean—too perfect.

  “Are you ready to get started?” Damien asked, noticing my eyes drifting.

  My attention snapped back to him, and I felt my heart flutter. Was I ready? I had no idea what was coming next. Hopefully, he would want to have sex. Or maybe, hopefully, he wouldn't. I didn't want to freak out like last time, though I was pretty sure that I was more mentally prepared for everything now.

  I took a deep breath. “I think I'm ready.”

  “Good. If you'll follow me, I'll take you to my classroom.” He made quotation marks with his fingers as he said the word classroom.

  I stood, allowing Damien to lead me toward a hallway. My imagination shuffled ideas of what the classroom was going to look like. The image that came to mind was his classroom at college. I imagined there would be a desk for me to sit at while he lectured me, and probably a whiteboard for him to jot notes down on. Now, I was beginning to wonder if I should have brought a pen and paper. He hadn't told me I would need supplies, but it kind of made sense if this was going to be a class. With my luck, the entire thing would be lecture, and I wouldn't get any hands-on training at all. The thought was disappointing, but maybe it was for the best.

  My next guess was completely at the other end of the spectrum. I pictured a kinky BDSM room like I had read about in so many popular erotica stories. There would be a Saint Andrews Cross, a stockade, manacles suspended from the ceiling. It would be a dungeon. Damien certainly looked like he could afford to build one.

  The room he led me into was neither of the two though. It looked like a typical guest bedroom with a bit more seating. There was a queen-size platform bed in the middle of the room with an immaculate white comforter and pillows. Comfortable looking chairs were placed in all four corners of the room. The only other piece of furniture was a chest of drawers. It all looked so perfect that I was scared to touch anything in fear of leaving smudges on the wood or wrinkles on the fabric.

  Damien gestured to the bed, and I lowered my weight onto it slowly. While I glanced around the room, he went to the chest of drawers, opening up the first drawer and pulling out a clipboard and a . . . lollipop? I stared at the red round plastic-wrapped candy, feeling like it was the only thing, aside from my outfit, that was adding any color to the room.

  “This weekend is going to be all about assessing your confidence level,” Damien said as he closed the drawer and turned around to face me with items in hand. “It's also going to be an evaluation to see if you're emotionally mature enough to handle these lessons.”

  I gulped hard, wondering what that meant. Already, I was beginning to perspire from a mix of fear and excitement. If I hadn't been worried about grossing him out, I might have wiped my palms on my skirt. The room felt especially hot, but I was pretty sure it was just my
nerves getting the better of me.

  “If at any time you feel that these lessons aren't for you, let me know, and we'll stop. You can expect to feel a certain level of discomfort. This is completely natural and comes from having never experienced these types of things before. As you get more comfortable with me and yourself, those feelings will fade away. Eventually, I'd like you be completely confident in yourself as a sexual being. That is pretty much the point of these lessons,” he told me, extending his hand for me to take the lollipop.

  “Today's lesson has two parts. For part one, I want you to seduce me using only that lollipop and your body. You are not to touch me sexually in any way. I will not be giving you pointers or direction. This is all about you and what you already know and are comfortable doing.”

  I shifted my weight on the bed. In truth, I wasn't comfortable with any of this. The whole situation was completely awkward. The only thing keeping me focused was my desire for Damien Reed. More than anything, I didn't want to disappoint him.

  As he went to sit down in one of the chairs, I began peeling the wrapper off the lollipop. It was probably strawberry or cherry flavored. I would find out soon enough, though I hoped that it was strawberry. Cherry was a bit too tart for me.

  Damien crossed his ankle over his knee and rested the clipboard on his thigh. I could feel his eyes upon me, watching my every move, which only made me feel more vulnerable.

  I forced myself to look at him, allowing our eyes to lock. Eye contract was important. That was seduction 101. His gaze was so dominant though that my instinct was to cower away from it.

  No, I chastised myself. This will never work if you can't even look at him. He needs to be able to see that you fully mean the things you do.

  My small pink tongue flicked out of my mouth, tasting the lollipop. Cherry. Damn. No matter. Focus, Chey. Focus. You have to make him . . . hard. The very thought brought a blush to my cheeks. I could still picture Damien's cock, perfect and straight, hanging out of his jeans in his office at college. I wanted to stroke it, to take him into my mouth. But everything had gone by so fast. One minute, I was terrified that he would threaten to have me expelled. The next minute, I was sitting on his desk with my skirt hiked up to my hips and my legs spread. The memory made my face grow warmer, and my clit twitch with sensation.

  Now, I could take things slow—show Damien how much I really wanted him. He said I wasn't allowed to touch him sexually, but I could pretend. Couldn't I? This moment wasn't so much about expressing myself as it was about expressing my desire for him. And oh how I desired him.

  In my mind's eye, the lollipop became Damien's thick phallus. I stared at it longingly, lapping at its red candy coating with the utmost care. My only knowledge about how to give a proper blow job came from pornos I had watched. I tried to mimic them as best I could, giving the lollipop feathery strokes with my tongue before I stuck the entire thing in my mouth, sucking on it gently for a while and then plunging it to the back of my throat, moaning as I went along. All the while, the sensitive parts of my body began to heat up from the eroticism of the moment. Who knew that a person could get so aroused just from sucking on a lollipop? I must be doing a bang-up job if I'm already starting to get myself off, I thought. But then I looked back up at Damien and realized he wasn't sharing my sentiment. My eyes sunk between his legs, to the absence of the bulge there, and it took everything in me to suppress a frown. Not good enough, Cheyenne. You're going to have to try harder.

  Warmed up and feeling bolder by the minute, I crossed the distance between us to stand in front of Damien. It was time that I showed him I meant business. I would give him an erection if it killed me.

  Feeling a strange surge of confidence, I used my free hand to take the clipboard off his lap and set it on the chest of drawers. When I returned to him, I grabbed his crossed foot and pulling it over his knee so that it was forced on the floor. Then I stepped between his legs, making sure they were spread nice and wide for me.

  Now I had his full attention. He was staring up at me, trying to make me cower with those powerful dark eyes of his, and I was giving it right back to him, burning down into him with the fury of my desire.

  I let go of the lollipop stick and grabbed the bottom of my blouse. My heart pounded fiercely in my chest. I was about to do something I had never done before, and the angel on my shoulder shook her finger at me. This was dirty and wrong, but if I stopped now, then I might never get up the courage to do it again.

  As slowly and seductively as I could, I pulled the blouse up, exposing my pale skin and blue lace bra for Damien to see. When the blouse cleared my head, I shook my long red hair and tossed the garment over Damien's shoulder. His expression was deadpan, and there was still no bulge in his pants. Geez, this guy is a hard sell. I hope he's not broken. Then I remembered his sizable cock trying to force its way inside of me. No, definitely not broken. Maybe he just has some strange tantric willpower. It doesn't matter. I said I won't stop until I pass this test, and I'm not going to.

  My hands fumbled behind my back, working to unclasp my bra. The stress of the situation made me clumsy, and I worried that I might crumble at any moment, both emotionally and physically. Negative thoughts attacked me from all sides. What if he doesn't find me attractive? Do I look stupid? Am I really doing the right thing?

  The bra finally gave way, and I shrugged it off my shoulders, taking a deep breath. My nipples were hard pink pebbles against my smooth skin. The feel of the material of my bra rubbing over them sent a wanton twitch straight to my clit, helping to stabilize my mood. Even if he wasn't enjoying this, a large part of me was. It was exciting to be doing these horribly naughty things—things I had never done before.

  I cupped my hands against the sides of my breasts, squeezing them together and rolling my nipples between my thumbs and index fingers. It felt absolutely exquisite, sending wave after wave of pleasure coursing through my nether region. A soft moan left my throat, though it was partially muffled thanks to the lollipop occupying my mouth.

  I looked down. Still, no erection.

  Today's skirt was held in place by a simple elastic waistband. I dug my thumbs into my sides, pulling it down to my ankles. As I did so, I leaned forward, my head only inches away from Damien, my breasts kissing the top of his right thigh. For a moment, my face was close to his crotch, and I took a second to inhale his scent. There was nothing there but the smell of cologne and fabric softener. Not quite close enough, I thought with a twinge of disappointment.

  I kicked the skirt aside and straddled his right knee, looking down as if I was the one doing the dominating. I wanted him to touch me, to give me some sign of approval—to do anything, but he just sat there, gazing up at me, his cock unwaveringly flaccid.

  My well of ideas was quickly running dry. There wasn't much left I could do to elicit a response from him. If showing my tits hadn't done it, I highly doubted that exposing my cunt would produce different results. Still, it was the only card I had that hadn't been played yet.

  Stifling a sigh, I hooked my fingers into the waistband of my blue lace panties and slid them over my ass with the same deliberately slow motion I had used when I took off my skirt. Cool air flowed between my legs, sending a chill down my spine as it kissed my warm wet parts. My mound had been shaven hairless, which I hoped Damien would like. I wasn't sure of his preference, but most men seemed to prefer the shaven look nowadays.

  With my panties dropped to the floor, I stood in front of Damien Reed completely naked, more exposed than I had ever been in front of a man. I had expected to feel shy and vulnerable, but somehow, I felt empowered, like I had just accomplished something great. It seemed stupid, but being naked in front of a man was a big step for me.

  I dropped to my knees between Damien's legs, returning my attention to the lollipop, which had been sucked down to about half its original size by that point. I swirled it around in my mouth, moaning and gazing up into his brown eyes. For a moment, I thought about pulling it out of my mou
th and trailing it down my body, but I didn't want to get sticky. Seducing Damien Reed was starting to feel like an impossible task.

  I took the lollipop out and held it in front of my face, rubbing it across my lips. Eventually, my creative well ran dry, and I ended up just staring at the thing.

  Damien reached forward and took it from me, bringing it up to his mouth. My eyes followed it like snipers on a target. It was so close to his lips, those beautiful lips that had kissed me tenderly in his office. How I wanted to taste them again.

  In a matter of seconds, the tables were turned. I was watching him, my eyes hooded and wanton with desire. His breath steamed on the red candy coating of the lollipop, and then it disappeared into his mouth. He sucked on it for a moment, then pulled it back out, his tongue making a soft swirling motion over the back of it. The peaks of my nipples grew harder, imagining that warm wet mouth ravaging them. He was an insatiable tease, and it was about to drive me absolutely insane.

  “Are you ready for part two?” he asked.

  My eyes were hooded, captivated by his seductive spell. It blew my mind and pissed me off that I had been working for close to fifteen minutes to give him an erection, and in the span of only two seconds, he already had me silently begging for him to take me. All he had to do was ask, and I'd be spreading my legs for him shamelessly, ready to take his thick cock into my wet folds.

  “Part two,” I murmured, still staring at the lollipop as it rolled around inside his mouth.

  “You look very ready for part two.”

  “What's part two?”

  “I want you to masturbate for me.”

  My breath hitched in shock, my mind suddenly drawn back to reality. Masturbate for him? I had just gotten done being proud of myself for getting naked, and now he wanted to push the envelope even further.

  “I'm shy,” I muttered.

  “You don't seem very shy to me.” He leaned back, killing the sensual moment by cracking the lollipop with his teeth.

  “It took a lot of courage for me to even do this much,” I confessed.

  “And I commend you for it. You did a good job.”