The Virgin Dating Game

by Sky Corgan

  “I think you've punished yourself enough as it is. Besides, that sex was so good, it made up for anything bad you could have done,” he replied, kissing me gently on the lips.

  “The sex was really good,” I agreed. “So tomorrow, we go back to normal, right?”

  “If that's what you want.”

  “Mmm. I'm really starting to like this 'if that's what you want' mentality you've got going on.”

  “Don't count on it lasting.” He smirked.

  “Oh, I won't. You're too stubborn and set in your ways.”

  We were silent for a few minutes before he spoke again, “So, I guess this means you're not turning in your training collar.”

  “No,” I said thoughtfully. “I think I'll hang onto it for a while longer.”

  “Good, because I have so much more to teach you.”

  CHAPTER TWELVE

  For a while, everything was rainbows and butterflies. I settled back into my submissive role, my determination to succeed fueled by Damien's declaration of love. There were still times when I had issues calling him Sir, but he rarely bothered to correct me about it anymore. Punishments were at an all-time low, and my happiness was at a high from the compromises we had made.

  My affections for Colton Caldwell had faded like the setting sun, and we had settled into a playfully flirtatious friendship, though I let it be known I had no intentions of leaving Damien. He had assumed the title of boyfriend, whether he liked it or not. I didn't know what else to call him that wouldn't sound weird, and there was no way I was going to explain he was my Dominant to people.

  Weeks went by without incident. We followed each other's rules and found a happy medium to our relationship. Since we were spending more time together, my suspicions about him cheating were almost eradicated. That is, until the weekend I came over and Mistress Danica was at his house.

  I should have known something was up. As soon as Damien opened the door to me, the first thing he said was, “You're to get undressed and serve my guest. I trust you to remember how to act from the dinner party.”

  I nodded, quickly retreating to the classroom. (What Damien considered his classroom was actually just a bedroom with extra seating where most of our kink sessions took place.) When I passed by the living room, I glanced at the sofa in my peripheral vision. There was no one there.

  As soon as I rounded the corner, my breath hitched. Danica was standing near the bed in all her blonde glory, running a finger over the comforter.

  When she turned to me, I bowed my head, fumbling for polite words. “I'm sorry, Miss. I was coming to undress and get ready to serve you. I was unaware you were in this room, otherwise I would have requested permission to enter.”

  “It's fine.” Her ruby-red lips drew up into a pleasant smile; her eyes looked nostalgic. “I was just taking a walk down memory lane. Damien and I did so many things in this room. Things I'm sure he's taught you too.”

  I didn't need to hear that—didn't want to hear that. Just the thought of it absolutely infuriated me. She had no business being in this room. It belonged to me now.

  “I'll leave you to change," Danica continued. “We wouldn't want to incite Sir Reed's wrath, now, would we?”

  When she brushed past me to leave, I cringed as our arms touched. Was she purposely trying to get under my skin? Did she know that talking like that upset me?

  There was nothing that could be done or said about it. All I could do was continue with my duties.

  I tried not to let my mind wander as I took off my clothes. It was almost impossible not to think about Danica though. She looked sexy as usual, in a black corset and leather pencil skirt. I couldn't help but wonder if she always dressed like that. Every time I had seen her, she'd been in kink wear. Had she worn it to seduce Damien?

  Stop thinking about it. You have a duty to perform. Besides, you promised you wouldn't get jealous if he didn't get jealous. You have to learn to trust Damien.

  When I finished stripping down, I checked the chest of drawers for the collar I had served in during the dinner party. It wasn't there. In fact, all the drawers were empty except for the top one, and the only thing it had in it was a pair of clamps attached to some type of controller. These likely had something to do with my upcoming kink session, and I felt a bit guilty for having looked at them. Damien liked for my sessions to be a surprise. This would be the first time I had ruined that for him. Hopefully, he wouldn't punish me for it. After all, my reasoning for looking in the drawer was good.

  Setting thoughts of punishment aside, I took long strides to the living room to attend Damien and his guest. It was nice not to have to walk like a penguin. The last time I had to serve guests, Damien had placed ankle cuffs on me. Six inches of chain had separated the cuffs, and my restricted movements had made it take forever to do anything. Since I hadn't found ankle cuffs in the chest of drawers today, I figured it would be alright for me to do without them.

  Both Damien and Danica already had beverages, so I found myself parked in the corner for the majority of her visit. It made me feel like a piece of furniture to have to stand there so still and silent, but I was happy I at least got the privilege of being in the room with them and listening to their conversation.

  “And that's when he threw up,” Danica said, finishing a story about a scene gone horribly wrong.

  Damien sniggered, “I imagine I would throw up too. Getting your balls stepped on isn't very fun.”

  “You're not as soft as he was. Besides, I think you'd know not to eat before a CBT scene.” She sighed, “It looks like I'll have to start adding that to my contracts. No eating for at least an hour before your scene. That way, I'll be less likely to get vomited on.”

  “So, he actually vomited on you?”

  “No.” She shook her head. “He was laying down on my table, so he basically vomited on himself. I've never undone bondage faster in all of my life. The idiot could have choked to death.”

  “That's disgusting.”

  “He's lucky I didn't make him lick it all back up. I did make him clean it though, on his hands and knees, while I caned him.”

  “You're definitely not one to piss off.” Damien smirked.

  “No, I'm not.” She sipped her bottle of water, then spoke again, “So, will you be attending Sir Martin's play party this weekend?”

  “I'll be there. Hopefully, we'll be there.” He glanced back at me.

  “Well, if your little cherub can't come, then I'd be glad to partner up with you.” She placed a hand on his knee, causing the fires of jealousy to race through me.

  It took everything I had not to say something. My jaw clenched as I zeroed in on her hand, watching it for any sign of movement. If she tried to slide it up his thigh, I didn't know if I'd be able to stop myself from attacking.

  Damien huffed, “I didn't think you'd be interested in being a submissive again?”

  “Would it please you if I was?” She grinned wickedly. “I bet you'd love plowing us both. Lining us up next to each other and popping into us one at a time.”

  My mouth fell open in shock, but I quickly regained composure. Damien was absolutely speechless.

  “No, Sir Damien, I think not,” she continued. “I'd much rather have you on the receiving end. It's not that bad, you know? And I think you have a greater pleasure for pain than you realize. If I recall, you rather enjoy being bitten and clawed. I could probably make you come from pain alone.”

  “I'll take a pass,” Damien said quickly, sounding as uncomfortable as I felt.

  “Too bad. If you ever change your mind, you have my number.”

  I was never happier to see her stand up to leave. As I escorted her to the door, all I could think about was how much I wanted to strangle the life out of her. How dare she say those things right in front of me?

  When she walked outside, she waved dismissively at me, not even bothering to look back. I stabbed her with my dagger eyes, though it did no real harm. All I could do was glare and hope I never had to
see her again. That was wishful thinking though. Obviously, she was going to be at the play party. And there was no way in hell that I'd let Damien go alone after the comments she had made.

  When I returned to the living room, Damien was lounging on the sectional sofa watching television. I bowed respectfully at the entryway, requesting permission to enter before I came to his side and sat down.

  “Do you have a lot of homework tonight?” he asked. Damien always asked that when I came over on a school night. It had become redundant and annoying, but I never said anything about it. At least he was allowing me to come over on school nights now.

  “No, Sir.” I shook my head, wanting to add that I wouldn't be there if I did have a lot of homework. That was our agreement.

  “Good.” He turned off the television. “Did you hear what Danica said about the play party?”

  “Yes, Sir.”

  “And will you be able to attend with me?”

  “Yes, Sir.”

  “Excellent. Then shall we take this to the classroom?”

  “Yes, Sir.”

  Damien stood and walked me back to the classroom. I sat on the bed, and he went to the chest of drawers to extract the clamps.

  “Do you know what these are?” he asked, holding them up to me.

  “They're nipple clamps, Sir.”

  “Yes. They are. And I assume you know what I'm going to do with them?”

  “Yes, Sir.”

  He approached me with the nipple clamps in hand, pausing to adjust a small silver knob on each one. “I think we're going to experiment with pressure first. These knobs control the bite of the teeth. I'll put them on their gentlest setting, then turn the knobs to tighten them. Say yellow when it starts getting too intense, and that's where I'll stop.”

  “Yes, Sir.”

  Damien delicately placed a clamp on one of my nipples. The pressure was so loose that it slipped right off, falling onto my lap.

  “That won't do.” He shook his head, picking it back up and adjusting the knob again. This time, it stayed.

  The more he adjusted, the tighter the clamp became. Thanks to a thick plastic coating on it, there wasn't much of a bite, but the pressure quickly got intense. I tried to bear as much of it as I could before I said my safety word. Then Damien moved onto the other nipple and repeated the process.

  “How does that feel?” he asked when both clamps were in place.

  “Not bad,” but not very arousing either.

  When he first placed the clamps on my nipples, there was a familiar sensation of pleasure. My nipples were extra sensitive and loved being teased. But as soon as the pressure had been adjusted, and his hands had moved away, my body had reverted from pleasure to pain.

  Damien rubbed his fingertips across my crushed peaks. Pleasurable spasms coursed between my legs as he did this, and I moaned softly. When he grabbed the cord attached to the nipple clamps and gave it a good tug, I hissed in pain, but found that I enjoyed this stimulation as well.

  I stared at Damien's crotch as he grabbed the remote and played with the dials. The clamps began to vibrate, but I didn't find anything particularly arousing about it. My mind was stuck on that thick piece of flesh between his legs, how I wanted it inside of me—needed it inside of me. Since we had been having sex regularly, I was turning into a nympho. My cunt hungered for his cock like my belly hungered for food. And it needed to be fed.

  I let Damien have his way for a while, making me crawl on all fours so the weight of the nipple clamps pulled on my breasts. Then he rolled me over on my back and teased the tips of my nipples with his tongue while the clamps vibrated away. It took everything in me not to tangle my hands in his hair and suffocate him in my cleavage. My body was becoming too needy too fast.

  “Sex,” I said abruptly.

  “Hm?” He looked up from my chest.

  “This would feel a lot better if you were fucking me.”

  “Would it, now?” He grinned, kneeling on the bed to unfasten his belt.

  I sat up, moving his hands away to undress him faster. When I pulled his flaccid cock out, I wrapped my palm around the base to flick my tongue across the tip, practically burrowing it into his pretty little slit. Damien moaned, reaching down to take the cords attached to the nipple clamps. As I began to suck him off, he gave them a little tug, causing me to hiss around his manhood. The clamps were really starting to hurt, the pain growing more intense with each passing minute. Pulling on them only made it worse. I matched the pain by applying more pressure to his cock. There was no way I would use teeth, but if I could give him a taste of the pain that I was feeling, then maybe he'd know to back off.

  That didn't seem to be the case though. The more I pressed down around his throbbing member, the more he tugged. My chest was on fire, and his cock was leaking. Maybe he did have a bit of a pain fetish after all. I wasn't going to test it any further though.

  Surrendering, I let his phallus slip from my lips, licking off all of his pre-seed before whispering, “Fuck me, Sir.”

  It was all the queue Damien needed.

  He put me on all fours and entered me from behind, causing the nipple clamps to swing beneath me with every thrust. It was painful, but a pleasurable kind of pain when mixed in with the fullness of his cock tunneling into my wanton pussy. I moaned and pressed back against him, my body a shameless slave to his fucking.

  When Damien tired of pounding me from behind, he laid down on the bed, guiding me up onto him in reverse cowgirl. His cock slid in easily enough at first, but then he pulled me back, and the pressure became incredible. I held myself up while he thrust into me. My muscles ached from it, but my cunt was satisfied, and that's all that mattered.

  Damien reached a hand around me and spanked my clit, sending fireworks shooting off between my legs. It only took a dozen good slaps before contractions were rolling through me so intense that I had to rest on top of him. He dug his fingers into my sensitive little pleasure nub, milking out what was left of my orgasm until I was completely breathless. Then he turned me onto my side and fucked me until he came. I watched as he pulled out, his glorious member spilling its seed onto my stomach and tits.

  Damien hadn't come inside of me since the night that he had professed his love. It was probably better that he always pulled out. The last thing I needed was to wind up pregnant. Still, I would love a good cream pie every once in a while. He had been so fucking sexy, the expression on his face when he pressed deep into me. I hadn't felt his semen spray inside of me, but I had known that it was, and that was enough. Not to mention the aftermath when he pulled out. So deliciously sticky.

  Damien went to the bathroom to get a towel to clean me off with, then he laid down beside me for a few minutes, pulling me into his arms. He had been a lot better with the aftercare since I made all of my demands. Cuddling hadn't been one of them, but I was happy that he figured out it would have been if I thought of it at the time.

  “Did you like it?” he asked.

  “I always like it,” I replied. “But could you take these nipple clamps off of me? My nipples feel like they're on fire.”

  He gave a short laugh, leaning over me to remove the clamps. “I had almost forgotten they were there.”

  “It's good I said something then.” I frowned, though my expression contorted the second the pressure was off of the first nipple. Dear God, it hurt. Who would have thought that taking them off would hurt more than having them on?

  As the blood rushed back to my abused nipples, Damien sucked on them, though the sensitivity they once held had been nearly destroyed from the crushing pressure. Still, it was a nice gesture, and I enjoyed having Damien's mouth on me whenever I could get it. Lovingly, I stroked his hair until he finished, then pulled him up for a series of gentle kisses. Mmm Romantic Damien.

  CHAPTER THIRTEEN

  When Damien opened the door to me on the evening of the play party, I almost couldn't believe my eyes. My mouth fell open as I took him in from top to bottom. His dark hair was
neatly combed; his typical five o'clock shadow was almost invisible. He was wearing a skin-tight black graphic T-shirt with a set of silver handcuffs going down the torso and a pair of black vinyl pants that were complemented by a studded belt and nice black leather boots. I wanted to rape him.

  “Sex, now,” I said, feeling almost robotic about it.

  Damien grinned. “No, Chey. We don't have time for that.”

  “Why do you look like that, if not to make me want sex?” I quirked my head to the side.

  “Because Sir Martin has a dress code for his play party. Come inside. I have something for you too.”

  He moved away from the door to let me in, but I just stood there, staring at him, tugging at one of his belt loops. “Can't wait. Sex now.”

  “Behave.” He gave me a stern look, and I knew better than to press my luck.

  When we walked back to the classroom, I found my outfit laid out across the bed, if you could call it an outfit. It looked more like a few pieces of vinyl pieced together to resemble a skimpy bathing suit, barely enough to cover anything. I was thankful that there was a large vinyl trench coat right next to it, which I could only assume I would be wearing to cover myself up until we got to the party. On the floor were the evil six-inch stilettos I had worn at the dinner party. I scowled at them, anticipating another night of pain.

  “Get dressed and meet me in the living room,” Damien said, giving me a soft slap on the ass before taking his leave.

  I quickly shimmied out of my blouse and skirt, then folded them and placed them on the chest of drawers. Trying to figure out how my new outfit worked took a minute, but I finally got it on, and when I went to admire myself in the closet mirror, I was rather impressed. Damien had good taste. The halter teddy accentuated my assets perfectly. While the cups were big enough to hold my generously sized boobs, they didn't cover everything. Laces across my chest offered more support, giving my breasts that sexy pushed up look. A small strip of corset laced vinyl connected the top to the bottoms, which were just an arrow-shaped patch of fabric covering my mound and pussy. There was a string that went around my hips, but I figured it was more of aesthetic purposes than anything else. All in all, it was a sexy little number.