The Virgin Dating Game

by Sky Corgan

  “But you didn't. . . I mean. . .” My cheeks burned. Why was it so hard for me to say erection? He hadn't gotten an erection. It wasn't particularly difficult to say, and yet my words got all jumbled up in immature embarrassment.

  “I didn't what?” he smirked, and I hated him for it. He was going to force me to say it.

  “You're not hard.”

  “So you've been looking,” he teased.

  “Well, yeah. I figured that would be a sign that I had done a good job.”

  “You did a great job. I just have a lot of self-control. It's not often my body does things I don't want it to, excluding when I'm sick.”

  Is that even possible, I thought, or was he just saying that to be nice. Sure, he wasn't some teenage boy who was going to pop a boner at every boob he saw, but still. I had given him a very intimate one-on-one strip show. Few guys could see something like that without getting hard.

  “Masturbate for me. You're warmed up as it is. It's important for me to see you pleasure yourself, for future lessons. Now, I know it might be a bit awkward, since you've never done it in front of anyone before. Just try to pretend I'm not here. You don't need to do any fake moaning or try to impress me, or drag it out longer than necessary. Do what you normally do.”

  I thought about opening my mouth to argue, but instead, I found myself crawling onto the bed and rolling onto my back. Damien had one thing right; I was definitely warmed up and ready to go. My mind was still stuck on the image of him sucking on the lollipop, teasing it with his tongue.

  The sensitive nerves in my clit tingled as my fingers found their way between my legs. Normally, it only took me about five minutes to rub one out. That wouldn't be the case this time though. Despite the fire burning between my legs, my mind kept getting distracted. No matter how much I tried to pretend I was alone, I knew that Damien Reed was sitting a few feet away watching me without a tent in his pants. It was a discouraging thought.

  This is for you, not for him, I had to remind myself. You're doing this so that you can be more sexually secure.

  One hand worked back and forth in heated circles over my clit while the other teased one of my erect nipples. I tried to keep the picture of Damien sucking the lollipop in my head. My thoughts kept drifting deeper though, moving further back to when we were in his office. The head of his cock had pressed against my passageway, nudging to the point of pain. It hadn't bucked all the way inside, but that feeling when he was there, when we were so close to coupling. At the time, I was a bit afraid. Now, the memory brought back nothing but excitement.

  My finger worked with energized fervor, massaging while my toes curled, and I pressed my hips forward, practically writhing on the bed as I rubbed out my pleasure. All the while, I imagined Damien's glorious tip at my entrance, threatening to break through and invade my virgin tunnel. It would have felt exquisite, I was sure. Maybe a bit painful, but that would have gone away once I got used to his girth. The thought of Damien Reed between my legs was enough to send me over the edge, drowning me in a fit of blissful contractions. My lips parted to moan, but I swallowed the sound, not wanting to seem fake or flaky. The contractions rolled through me in rapid succession, firing off my sensitive nerve endings, and soon I found myself spent and breathing ragged on the bed.

  When I finally turned to look at Damien Reed, there was a tent in his pants.

  CHAPTER FIVE

  I got dressed while Damien jotted notes down on the clipboard. Hearing the pen scratch against paper was a bit unnerving, as if I was being graded on my performance. Curiosity made me want to ask what he was writing, but I was too shy and embarrassed, and part of me feared it wasn't something I wanted to know anyway.

  With me dressed and his notes taken, the session was over. Like the professional that he was, Damien walked me to the door, going over what time he'd like me to come over the following day. My brain went wild, trying to imagine my next lesson. Apparently, I had used up all of my boldness during the striptease and self-pleasure session, because I could barely utter out more than a few words before I found myself standing outside of his house, staring at my Miata, my mind replaying the afternoon's events while my body automatically walked to my car and got inside.

  I picked up my cell phone and realized I was shaking. Adrenaline was still pumping through me, and I wondered how long it would be before I calmed down. The session had been so intense; the memory of it would stick with me for a while.

  With unsteady fingers, I dialed Tanya's number. Everything in me wanted to blab about what had happened. She was my best friend, and I told her everything. Yet this felt somehow forbidden. I had to keep it to myself. Or maybe I could lie and tell her I had met some wonderful boy, just so I could get this off my chest.

  We met up at a local restaurant, and she seemed to be beaming with excitement as much as I was. She wiggled as we waited for the host to show us to our seats, going on about having big news, though she refused to tell me what it was until we were seated.

  I slid into the booth opposite her. Before we even had a chance to say a word to each other, our waiter was at the table, taking our drink order. The ear to ear grin on Tanya's face told me that she had probably just gotten laid. She always smiled like that after sex. Sometimes, she reminded me more of a guy than a girl. She was so promiscuous, practically a nymphet. If she could have a different boy every night of the week, she would.

  “Oh. Oh. Oh.” She patted the top of the table in excitement as soon as the waiter walked away.

  “You go first,” I told her, as if I had a choice.

  “I met a boy,” she said and then squealed afterward.

  “I kind of figured.” I tried not to sound too unsurprised.

  “No. No. Not just any boy. This boy is dreamy and smart and rich. Did I mention that he's hot? Because he's really really hot.”

  “Dreamy usually implies hot.” I grinned at her.

  “And his dick.” She held her hands almost a foot apart and then mouthed the words, “this big.”

  I couldn't help but laugh. “Sounds like the total package. I'm guessing that you two—”

  “Of course we did,” she giggled like a school girl. “You know me better than that, Chey. Why'd you even ask?”

  I wanted to roll my eyes, imagining a bedpost full of notches that went all the way down to the floor. “Why'd I even ask? Oh, by the way, how's the sugar daddy going?”

  “I don't want to talk about him. He's old news. I'm going to cut ties. I just don't have time for him anymore with college and all of these new boys.”

  “I'm sure he'll be disappointed.”

  “Wouldn't be the first time I left a guy heartbroken.”

  Tanya was the quintessential Asian dream. She was petite, with long silky dark hair that hung down to her lower back, a round tan face, and almond eyes. There weren't many guys who didn't lust over her small frame and perky tits. She knew how to work them too, always wearing something to accentuate her body. Today it was a skintight mini dress, black with soft white flowers crawling up the side.

  “So what about your news?” she asked.

  “I met a boy too.”

  “Oh really now?” She arched an eyebrow, giving me a strangely sleazy looking expression that made me giggle.

  “Yes.”

  “What's his name?”

  It was a question I hadn't expected her to ask. Usually, her mind was completely sex focused. Why'd she have to ask a question that made me think . . . and hesitate.

  “James,” I fumbled, cringing after I said it. Damien Reed looked nothing like a James. I didn't even like the name James. Why had I said it?

  She wrinkled her nose, mirroring my thought. “I don't like that name.”

  “Me neither, but he's pretty dreamy too.”

  “So, what does he look like?”

  “He's tall, with dark hair and dark eyes.”

  “Sounds yummy. Is he chubby?”

  “No. He's very fit. He wears . . . really tight clothes.”
I wanted to drool, thinking about the tent in Damien Reed's jeans. It reminded me of the saying about love. Stop looking and you'll find it. I had been working on giving him an erection for what felt like forever, and when I finally stopped concentrating on him and started thinking about myself, that was when it happened.

  “He's not one of those emo kids, is he? Cause I don't like them.” She shook her head in distaste.

  “Does it matter? It's not about whether you like him or not. All that matters is that I like him.”

  “Ew. He is an emo kid. Chey, they're so immature. You can do better than that.”

  “No. He's not emo,” I laughed. “He's very . . . serious, and smart, and . . .” Distant. And not really yours.

  “Does he have a big dick?”

  “Tanya!” I wanted to reach across the table and slap at her. Then I grinned, realizing for the first time ever that I could actually answer that question with honesty. “Yes, he does,” I said.

  Tanya gasped, putting her hands over her mouth. “Chey! You've actually seen it? Did you? Did you?!” She bounced in her chair, her tits staying oddly in place. If I had done that, my back would have ached.

  “No, we didn't. But, I got undressed for him, and masturbated.”

  Her expression sulked. “You masturbated for him but you didn't make him give me the D.”

  “We're waiting, since I'm a virgin. You know, until the right moment.”

  “Ohhh, so this guy is your boyfriend now? Damn, girl. You move fast. We've only been back in school for two weeks, and you've already landed a hot boyfriend.”

  “We're taking things slow.”

  “You know I have to meet this guy now.”

  “You will, eventually,” I lied.

  “He must be something special if he could get the morally high Cheyenne Grear naked on the first date.”

  “He is special.” I smiled. “He's . . . different. Not like the boys from high school. You were right. College guys are different.”

  “Well, not all of them. I've met more duds than studs. I'd say most of them brought their high school mentality with them,” she huffed in disgust, and then went on a rant about the various guys she had talked to who weren't what she considered to be college material.

  For the remainder of our time together, we talked and laughed and joked. My happiness level was at all-time high thanks to good company, a strangely heightened level of confidence, and memories of my amazing afternoon with Damien Reed. I could hardly wait for my next lesson.

  As all good things must come to an end, once we finished eating and ran out of things to say, Tanya and I parted ways. I laid in bed that night and rubbed out another one, thinking of the bulge in Damien Reed's pants and all the naughty things I wanted to do to it. My sexual awakening had begun, and there would be no stopping it now.

  The next day went by gruelingly slow. It felt like every minute, my mind was fixated on getting to Damien's house. I even decided to leave early, more out of impatience than anything else. Hopefully, he wouldn't be upset if I showed up fifteen or twenty minutes early. Punctuality was better than lateness, right?

  I knocked on the door, trying not to seem too enthusiastic when he opened it. He smiled warmly at me, sending the butterflies in my heart into a flighted frenzy. How could a man look so beautiful when he smiled?

  “Come on in.” He gestured inside. “We'll head straight back to the classroom today.”

  “Alright.” I nodded, waiting for him to close the door and lead the way.

  When we were back inside the classroom, he took a seat in one of the chairs. I could only assume that he wanted me to sit on the bed, and so I did.

  “How did you feel about yesterday's lesson?” he asked.

  “I was a bit nervous at first, but it was fine.”

  I found myself fidgeting, my palms already beginning to sweat. It felt like we were back to square one. All the confidence I had mustered up the previous day was gone, and I was silently cowering under the weight of Damien's dominant eyes.

  “Good. Today, we're going to get a little more intimate,” he told me.

  The word 'intimate' sent a shock of yearning straight to my clit. There were so many meanings the word could have. Intimate covered a broad spectrum, from touching to sex. Was I ready for sex with Damien yet? I thought I was, but I still wasn't sure. Perhaps I wouldn't truly know until we got down to it, until his thick cock was nudging against my hole, threatening to claim me. Just the thought set my body on fire. My nipples pressed restlessly against my blouse, and I blushed, hoping he couldn't see them but knowing better.

  “Okay,” I muttered sheepishly.

  “This is still an exercise about your self-confidence level and finding out what you already know.”

  I nodded shyly.

  “Have you ever touched a penis before?”

  I shook my head.

  It looked like Damien was about to sigh, but he didn't. “For today's assignment, I want you to make me come without touching my cock.”

  My eyes grew wide in surprise, my heart drumming faster in my chest. “How am I supposed to do that? If I can't touch you, then I wouldn't think I'd be able to stimulate you to that point.”

  “You can touch me on top of the clothes, just no skin to skin contact. Are you . . . comfortable with the idea of touching me?”

  Oh God, yes. It's all I dream about. Me touching you. You touching me. Us touching each other. Your cock touching my. . . I felt my clit throb in response, my lower muscles clenching in need of him.

  “I'm okay with it,” I admitted. The idea of giving Damien Reed an orgasm made me more than a little aroused. To see that magnificent tool spewing out its pleasure juices just for me. My panties were already growing moist from the thought.

  “If you can do it, then I'll give you a reward,” he told me, though his expression didn't make it seem like it would be anything exciting.

  “What kind of reward?”

  “There's really no point in telling you. Since I've been teaching this class, I've only ever had one student who's been able to do it. Though, don't get me wrong, there's really no passing or failing. This is purely for observation.”

  I scowled in disappointment. Why did he bother telling me I would get a reward for completing this task if it was an impossible one? I didn't doubt for one minute he was telling the truth. It had taken me forever to give him an erection. Besides, he had already told me that his body didn't do things he didn't want it to. That meant he could probably suppress his orgasm. I would literally have to force it out of him if I wanted the reward. My lack of experience gave me almost no chance in hell of that happening.

  “We can begin whenever you're ready. You have an hour. If you want to give up before that time, just let me know.”

  I won't give up, I insisted. Besides, if I didn't use my whole hour, he'd probably send me home early, and I definitely didn't want that.

  “I'm ready,” I said, taking a deep breath and trying to gather some leftover confidence from the night before.

  Damien looked at his wristwatch and marked the time on his clipboard. “Begin,” he told me, setting the clipboard and pen down and then leaning back in his chair with his legs spread.

  I stood up and closed the distance between us, towering over him, though my mind was completely blank as to what I should do to make him come. My first instinct was to strip, but that hadn't even worked to give him an erection the day before. What would be the point of doing it now?

  We stared at each other awkwardly for a moment before I began to unbutton my blouse. My fingers were trembling, not a good indication of self-confidence. In truth, I felt like I had already lost. More than likely, he wouldn't even get an erection. . . unless I masturbated for him. But how would that make him come? It wouldn't.

  I could feel the veins in my forehead bulging with stress. Not very sexy. In fact, the more I stood there, the less sexy I felt, my confidence quickly dripping away. How to make him come? How to make him come?
/>   I shed my shirt and bra, then shimmied out of the rest of my clothing until I was naked before him. Not surprisingly, my exposed flesh did little to entice the monster in his pants. Whatever bulge was there was all flaccid man-meat, no more excited than if I was bundled up in ten layers of clothing.

  I sank to my knees, swallowing hard as I got a closer look at the hot spot between his legs. In all honesty, I was a bit scared to touch it. My hands had caressed a clothed cock before, but those had belonged to men who had their hands all over me—men who actually wanted in my pants. Their members were stiff for me already, requiring no stimulation other than holding me in their arms.

  Reluctantly, I reached out my hand, pausing before I let it rest on the heat of his sex, rubbing back and forth clumsily. To my surprise and excitement, it wasn't long before I felt it growing, plumping beneath my rigid fingertips. With only a few minutes of gentle stimulation, Damien Reed's cock was fully engorged, pressing hard against his jeans. My clit twitched with satisfaction, my body's own personal reward.

  For some reason, just touching him turned me on. My nipples were taut peaks, rubbing against the leg of his jeans, my mound a heated mess of wanton sensation. I wanted to sneak a hand between my legs and give myself a bit of pleasure, but I needed to focus. Yesterday had been about me. Today was about him. Or, at least, that's what I told myself. To hear it from Damien's mouth, today was about me too, but I had my doubts.

  I glanced up and saw that his eyes were hooded, staring down at me with lust. He was gorgeously desirable, and I longed to hear him moan from my touch. Almost instinctively, I rubbed harder, feeling the outline of his stiff manhood beneath my hand. It wasn't until he winced that I knew to back off a bit, though he never chastised me for my actions.

  I rubbed and rubbed and rubbed, caressing hardened flesh and thick jean alike. This wasn't working. The material of his jeans stifled the level of stimulation my hand could give. I needed to come up with another plan.

  My mind searched for a solution, but nothing seemed good enough. I thought about grinding my cunt on his cock, but I was worried my wetness might get on his jeans, and I didn't want to embarrass myself by making a mess. The only other option I could come up with was taking his jeans off. If he went commando, I'd be fucked. But if he had boxers or briefs on underneath, the material wouldn't be so thick, and I'd still be adhering to the rules.