The Virgin Dating Game

by Sky Corgan

  “Likewise,” was all I could think of to say.

  “Looks like you're doing some major cradle robbing,” the woman told Damien while she looked me up and down. “Has she even bled yet?”

  A blush crept up my neck, though I wasn't sure if it was from embarrassment or anger at her bold words.

  “She's perfectly legal, I assure you. Cheyenne, this is Danica. She was my submissive before you. I'm sure you remember her from—”

  “The video. Yes, I remember,” I cut him off.

  “Now she's a Dominatrix,” the word hissed off his lips with a smile—a smile I didn't like.

  “How does that happen?” I asked. “Going from a submissive to a Dominatrix?”

  “Ol' Reed here couldn't tame me.” She took a step forward and poked his stomach.

  Don't touch him. He's not yours anymore. That ship has sailed. Stay away.

  “It had nothing to do with me not being able to tame you. You didn't want to be a submissive.” His smile sank into a frown.

  “And now I'm not,” she told him and then went to find a seat. Thankfully, the only two left were a good distance away from us. I didn't want her anywhere near him.

  We ordered food, and eventually the conversation turned from casual everyday things to the lifestyle. One of the men asked how Damien and I had met. When he told the story, they all hooted with laughter, teasing him about how he needed to stop fucking his students. That didn't sit well with me either. Was he really such a whore? Had my lust for him blinded me of his true nature? It was a good reminder that there was so much about him that I still didn't know, like what he did during his free time when I wasn't around. I wondered if the blonde woman knew.

  For the most part, I remained quiet, listening to everyone around me. Occasionally, someone would try to engage me in conversation, asking me how I liked the lifestyle or how Damien was treating me. I liked it well enough, I told them, though I was still trying to adapt to a lot of things. And my relationship with Damien was as good as it could be, given the circumstances. Or was it? I didn't know anymore. Mixed emotions were blurring rational thinking.

  Throughout the entire munch, I continuously caught the blonde woman staring at Damien. It was like I wasn't even there. She flirted with him when she could. At least, it seemed like she was trying to flirt with him.

  The most provocatively dressed person in the room, I could see why he had gone for her. She was beautiful, with honey blonde hair, blue eyes, pale skin, and breasts that could rival my own. They were displayed proudly in a tight-fitting leather corset, showing more skin than what was left to the imagination. Her cleavage went on for miles, seducing every man in the room. Even Damien wasn't immune to it. I saw him glance over once or twice, though he tried not to be obvious. It never ceased to amaze me the spell that breasts could place on a man. He had even had those breasts before. Why he felt the need to look at them now was beyond me?

  The munch couldn't be over soon enough. While everyone had been pleasant, being in the presence of the blonde woman was about to drive me insane. I couldn't help but feel like there was still something between them, though I knew I was probably just being paranoid.

  “Did you have a good time?” Damien asked as we walked back out to his car.

  “It was interesting,” I replied shortly.

  He gave me a quizzical look, taking note of my awkwardness. Thankfully, he didn't press any further.

  “They're good people,” he told me on the drive home and then went on to regale me with stories of how he'd met most of them. Surprisingly, he left out the blonde woman. I couldn't help but wonder if he had done it on purpose.

  By the time we had returned to his mansion, my mood had improved somewhat. Out of her poisonous presence, I could almost forget the way Danica had looked at Damien, and the way he had glanced crudely at her breasts. Just the memory made my blood boil.

  Interestingly enough, Damien's planned kink lesson for the night was focused on cooling my heat. I laid naked on the bed in the classroom while he held a champagne glass with ice cubes in it over my body, working to scoop one out with his fingers. Without even touching me, my skin had already prickled with goosebumps in anticipation of the freezing wetness.

  I held my breath as the first cold drops of water landed on my nipple. They had perked before he had begun, but grew even firmer from the icy stimulation. Then he followed through by rubbing the ice cube around each nipple until they were about as erect as they had ever been. I tried not to squirm away, feeling more curious than aroused. My body heat quickly melted the ice, and while Damien dipped down to catch the cascading droplets with his tongue, he wasn't fast enough. They rolled over my side, meeting with the comforter below. His mouth felt better than the ice, but my mind was so distracted with the happenings of the evening that I was having a hard time enjoying it.

  Down the ice cube moved, running over my chest and stomach, followed by a trail of kisses from Damien's cold lips. When he stopped at my mound and popped the ice cube into his mouth, I sighed in relief. I thought I knew where it was meant to go next, but instead, Damien crawled back up my body for a kiss, our tongues fighting for possession of the ice cube. The kiss was sensual and cold, and I tried not to giggle as we passed the ice cube back and forth until it was no more, the combined heat of our breath too much for it to handle. A trickle of water streamed from the corner of my mouth, running down into my hair. Damien licked up the side of my cheek, and I shivered, playfully pushing at his chest.

  “Too much for you?” he asked with a smile.

  “It's different,” I admitted. Not as erotic as I had hoped, though I didn't want him to stop.

  The next ice cube was held precariously over my spread pussy lips. As Damien's fingers worked to melt the ice, I pressed my head against the pillow, awaiting the feel of it against my sensitive nerve endings. When the first few drops hit my clit, I couldn't help but squirm. It was far more intense than it had been on my nipples. My breath hitched when Damien pressed the ice cube against my nub. After only a second of contact, it was more than I could handle, the tingling cold turning into a painful burning sensation.

  “Yellow. Red! Get it off!” I told him, thankful he obeyed without delay.

  “Too intense?” He popped the ice cube into his mouth, sucking the salt of my skin off of it.

  “That felt horrible,” I said, slipping a hand between my legs to rub some warmth back into my sensitive clit. Any sense of pleasure had receded deep down inside, not to return until it felt the coast was clear. The ice cube was now my enemy.

  “Looks like this would make a better punishment for you than a pleasure tool,” Damien commented, mirroring my thoughts.

  “If that's to ever be a punishment, then I'll never disobey again.” I tried to relax against the pillow, realizing that all of my muscles had tensed from the overwhelming icy burn.

  “I'm fairly convinced at this point I'm never going to have you trained to call me Sir all the time,” he sighed and then crunched the ice cube between his teeth, devouring it.

  “Do I have to say it after every little thing I say?” I gave him a quizzical look.

  “It would please me.”

  “That sounds so awkward though.”

  “Give it a try.”

  I frowned. Am I untrainable . . . like her? Or . . . untamable? “Couldn't tame me.” That's how she had put it. If I couldn't get this right, did that mean I wasn't cut out to be a submissive either? Would I end up disregarded only to be replaced by a more cooperative subject?

  Why are you thinking about this? You have a long time in training, and there's definitely room for improvement. Besides, you should be focusing on pleasure right now, not some stupid blonde bimbo.

  Damien took another ice cube from the glass. “I'm going to try something else. Don't worry, it won't be so intense.”

  I huffed, trying not to linger on my negative thoughts.

  “If you can't handle it, just let me know. Say your safety word, and I'll
stop,” he continued.

  “Yes, Sir,” I replied, trying to draw myself back into the moment.

  Damien held onto the ice cube with two fingers and ran it down my slit. The intensity of it lasted for a fraction of a second, not long enough to cause pain, but enough to make me squirm from the cold. Unfortunately, it still wasn't pleasurable, but I appreciated his willingness to experiment with me and let me experience a variety of different things. For as lusty as my body was, I couldn't realistically expect to enjoy everything we tried.

  He made the pass a few more times, pressing deeper and deeper until the ice cube was engulfed in my soft swollen folds. Each time, I squirmed a bit, making a face that I was certain told him how I felt. When too much wetness would pool, Damien would bend to lick it up. This, I enjoyed far more, though his mouth was unpleasantly cold from sucking on the ice cubes.

  “I'm going to put one of these inside you now,” he told me, holding up the last of the ice cubes.

  “No way. That's going to hurt too much. What if you can't get it out?”

  “I'm fairly certain it will be fine. Trust me, it's not like I've never done this before.”

  Not what I needed to hear. Now I was left wondering if he had done this with the blonde woman. Probably. Even if he hadn't, he had just admitted to having done it with some other woman, maybe even other women. Plural. That made it feel somehow dirty and wrong.

  He pressed the ice cube to my opening, then pushed it inside. To my astonishment, the searing pain did not follow it into my hole. Instead, it was like the thing had simply disappeared. There was no sense of coldness, no sense of anything. All I could feel was Damien's finger and a cool trickle of water as it streamed from my pussy.

  “You're melting it quickly.” He smirked.

  Before I had a chance to respond, he was dipping down between my legs, drinking from me like an overfilled cup. I blushed, listening to the crude sounds his mouth made. His technique was messy, and I could feel the water causing a wet stain on the comforter.

  Damien wiggled his finger inside of me, presumably poking around for the ice cube. If it was still there, I didn't know. His mouth had finally stopped the trickle of wetness, and I wasn't feeling any discomfort. I simply laid there, trying to relax enough to enjoy it. Even when he moved back up to kiss and lick my clit, the coolness of his tongue was keeping my orgasm at bay, as if my entire body was frozen from the inside out.

  He grabbed me by the hips, pulling me so that his mouth was buried between my legs. Eventually, the heat returned to my body, and my pleasure sensors began waking up from hibernation. Out of all the times that he had performed cunnilingus on me, this was by far the longest it had taken for me to get off. I wasn't quite sure if it was because the ice just wasn't my thing, or that I was too infatuated with thoughts of the blonde woman to be able to concentrate. Either way, I didn't like it, and my orgasm was far less than amazing.

  “You didn't tell me you were going to come,” Damien said as he emerged breathlessly.

  “I'm sorry, Sir. My mind was elsewhere.”

  The look of displeasure on his face was apparent. “Is there something you need to talk about?”

  For a moment, I thought of telling him no. That would have been dishonest though, and I was already failing as a submissive on so many different levels. My need to hide my true feelings was overwhelming my subservient behavior. How could I possibly tell him I was jealous without sounding stupid or overbearing or suspicious? The evening had already been awkward enough as it was without me causing more tension.

  “Am I a good submissive?” I asked finally. “I mean, for someone who is in training? I feel like I keep messing up so much.”

  He gazed down at me thoughtfully. “I think you're doing your best.”

  It was not enough. Far from what I needed to hear.

  There was no sex that night, only a vocabulary quiz, another set of vocabulary words, and punishment for forgetting to call him Sir again. I missed half the meaning of one of my vocabulary words, so Damien added five more minutes to the thirty minutes of punishment that he had already assigned me. To the wall I went to serve my time, secretly loathing him for it, though I knew I had done this to myself. Instead of holding a ping-pong ball with my nose, Damien gave me a penny, which was considerably easier. If there was one thing that I was learning from all of my punishments it was that my memory sucked.

  After my punishment was over, I thanked Damien for it, recited why I had been punished, handed in my definitions from the night before, had him unlock the padlock from my public collar, and took my leave. The drive back home was filled with thoughts of the blonde woman and the sex video. Their bodies had moved together so perfectly—looked so natural together. I decided that I hated her. Even if it wasn't for the right reasons, I hated her for ever having him, for me ever having to meet her.

  CHAPTER EIGHT

  The last week of the semester was filled with stress that helped to block out thoughts of the blonde woman. Finals were keeping me busy, and there were several nights I was so tired from studying I almost forgot to text Damien before I went to sleep. It was odd to think that over four months had passed already. In just one semester, I had managed to lose my virginity, have two love interests, sleep with one of my professors, and now I was his submissive. I could only hope the following semester wouldn't be so crazy.

  Friday couldn't come soon enough. With my last final over, I sighed in relief, a grin of accomplishment spreading across my lips. Now it was time to celebrate.

  Despite my dislike of Vinny, I went out with him and Tanya and a few other classmates for burgers and chitchat. It was nice to spend time with a college crowd, even though I didn't know many of the people who were there. One of the guys was even a bit of a hottie, and I could sense some interest as he stole glances of me while we ate and conversed.

  What it would be like to date a guy my own age, I thought as I watched Tanya and Vinny together, laughing and cuddling and kissing and being normal. Then I found myself stealing a few of my own glances at the dark stranger. His name was Colton, and I could have sworn I had seen him around campus before, though I couldn't say where. He was tall and lanky, with dark-brown hair and eerie green gray eyes. I had never seen any shade like them before. They were soft and almost hypnotizing, complemented by his olive skin. My gaze lingered a bit too long, and when he caught me looking at him, my face grew warm from embarrassment.

  Tanya and Vinny dominated the conversation, though that was to be expected. They both had larger than life personalities. We all went along with it, laughing and contributing where we could until our food was eaten, and it was time to part ways. I gave Colton a final glance as I walked out to my car, and blushed a second time when I noticed he was doing the same. Oh well, it was nice to look, but there would be no touching. My heart belonged to Damien—my body as well.

  The next day, I celebrated the beginning of holiday vacation by lazying around and eating copious amounts of junk food. By the time I had to leave to go to Damien's house, I felt like a whale. Hopefully, he wouldn't want to do anything too strenuous, I thought, a bit peeved at myself for killing my sex drive with carbohydrates.

  When I arrived on his doorstep with my definitions in hand, he didn't look as happy as usual, which was to say that he appeared to be downright miserable. I kept forgetting that though the end of the semester was a celebratory time for me, it signaled the end of his career teaching as a professor at the college that I attended. For him, the end of the semester meant the end of a paycheck.

  “How'd your finals go?” he asked, taking the paper from me and leading me back to the classroom.

  “I think they went pretty well,” I replied, trying to keep a positive attitude despite his gloomy demeanor.

  “Good. Hopefully, my forcing you to get to bed on time served some purpose in helping to you to focus better.”

  While I hadn't really had issues sleeping before Damien enforced that rule, I decided to agree with him. It was obv
ious he wasn't in the best of moods, and I didn't want to make it any worse by arguing with him.

  When we got to the classroom, he sat in his usual spot, staring up at me with no sense of warmth. I went to sit on the bed, but he stopped me in my tracks by saying, “Stand.”

  Reflexively, I assumed the position, locking my fingers behind my back and placing my legs shoulder-width apart. Damien stood up to circle me, making sure that my posture and body placement was to his liking.

  “You have on last final to take this weekend,” he told me, making me groan internally. “This final will include ten positions and ten vocabulary words. If you get them all right, I'll reward you by giving you the night to relax. No calling me Sir, for a full twenty-four hours. We'll go out to dinner and have a nice evening. Then, I'll do whatever you want me to to you in the bedroom.”

  My clit twitched at the thought, and I fought back the urge to rub my thighs together. That was quite a reward. No stuffy BDSM crap, an actual date, and Damien Reed under my control in the bedroom. My mind raced with the possibilities—my body hungered for the reward.

  He continued, “If you get them wrong though, the rewards will diminish with each wrong answer. The first reward you'll lose is not having to call me Sir. The second will be the bedroom benefit. The third will be dinner. For all that you get wrong after that, you'll earn punishment.”

  My face fought back a scowl. I knew there had to be a catch. There was always a flip side to the coin. Never an option for pleasure without the chance of punishment.

  “Which test would you prefer to take first, the vocabulary words or the positions?” Damien asked me.

  A ball of nervousness quickly formed in my stomach. For as poorly as I had done on every other test he had given me, I wasn't feeling too confident about this one either. Not to mention the fact that I hadn't been studying any of the old vocabulary words Damien had given me. If he only quizzed me on the last list, I might have more of a chance.