The Virgin Dating Game

by Sky Corgan

“It's fine. Let's get you all tied up. Go lay down on the bed.” He stood, approaching the chest of drawers.

  I placed my hand on it, looking up at him. “No. You offered, and I'm going to take you up on it. Does this mean I get to be your Domme tonight?”

  He let out a short laugh. “You're pressing your luck, little girl.”

  “That's Mistress Little Girl to you, slave.” I grinned wickedly.

  “Slave now, is it? You're already taking this too far.” He took a step away, though his words were playful.

  I grabbed the flogger out of the drawer and gave him a hard smack on the hip, which elicited no reaction. The thing felt heavy in my hand, unnatural, though I supposed that I'd get used to it soon enough.

  “Get undressed,” I told him, flopping down into the chair with flogger in hand.

  Damien reached for the bottom hem of his T-shirt to pull it over his head. I lashed out at him with the flogger again, making him stop and give me a quizzical look.

  “Slowly. Like a stripper,” I instructed.

  “Do you want me to dance for you too?” he asked, though I was pretty sure he wouldn't actually do it.

  “Nope. Just undress slowly, facing me. I want to see all of you.”

  Damien rolled his eyes, and I smacked him again. Though he didn't react to it, I rather enjoyed hitting him with the flogger. It seemed more like a toy to me than a device to inflict punishment with.

  Damien revealed an inch of skin at a time, now moving at a more desirable pace. I soaked him in, trying to picture him from the perspective of a Domme instead of a lover. This man belonged to me, and tonight I could use him for my pleasure, however I saw fit. It was an exciting thought, though I felt absolutely clueless about what to do with him once I got him naked. A thousand different scenarios had played through my mind after watching Danica with her client, and yet now my brain stood completely empty, as if my entire memory bank of perverted thoughts of domination had been erased. All I could do was sit back, enjoy the show, lick my lips at the delicious man flesh before me, and grasp at straws of what I thought I was supposed to do to him.

  Soon, Damien was naked in front of me. I had seen him naked dozens of times before, but never quite like this. He assumed the Stand position as soon as he had finished placing his clothing on the chest of drawers beside mine, now waiting obediently for my next command.

  “You don't have anything I could chain you up with? I'd really like you restrained standing,” I said.

  “You could use the cuffs to put my hands behind my back, Mistress.”

  “That's not what I meant. I want your hands above your head.”

  “I could hold them in place, Mistress.”

  “Still, not what I meant,” I grumbled.

  “Hang on for a moment. I'll be right back.”

  Damien broke position and left the room. For a moment, I thought about chastising him. He hadn't requested permission to leave, which was bad behavior for a submissive. He'd be racking up punishment time if this were real.

  A minute or two later, he returned with a strange bar in his hand. It wasn't until he fastened it to the door frame that I realized what it was.

  “Can you even do a pull-up?” I asked, then felt bad for sounding so rude.

  He gave me a look of offense, then gripped the bar and did a pull-up facing away from me. The muscles in his back flexed beautifully, as did other muscles down his body. My eyes washed over him hungrily, and I was suddenly unsure if restraining him was actually what I wanted. Fucking him would have been a lot more to my needs, but I knew I had to clear my mind of that for now if I wanted to make the most of this little session.

  “My big strong man,” I said with a grin, setting the flogger down and taking the restraints from the chest of drawers.

  When I flanked Damien's side, he turned and held out his wrists to me. I put the first cuff in place, then made him lift his arms, so I could hook the chain over the pull-up bar before fastening the second cuff around his wrist. He didn't look the least bit uncomfortable bound, which I found surprising. To be honest, I had expected him to argue the entire time, or at least put up some kind of a fight, though I was admittedly thankful that he hadn't. I probably would have caved under pressure, something he didn't need to know.

  By the time he was positioned in the doorway, I still had no clue what I planned to do with him. Looking at him was nice, but it would get awkward soon enough. Briefly, I thought about grabbing the nipple clamps, but ended up taking the flogger in hand again instead. Not knowing what I was going to do was beginning to cause me anxiety, mainly because I worried about Damien growing impatient.

  I approached him, mustering up as much confidence as I could fake. The flogger slapped lightly against my palm as I paced back and forth in front of him, trying to seem intimidating.

  “Now that I have you, what should I do to you?” I asked, honestly hoping for some form of suggestion.

  “Whatever you desire, Mistress.”

  You between my legs is what I desire. As sexy as this is, it's just making me nervous.

  Feeling like I needed to make some kind of move, I stepped up to Damien, running the flogger up between his legs and staring deeply into his eyes. His entire body tensed, and I saw the first signs of fear. My heart skipped a beat as I thought about all the different things I could do to him, the realization that he was at my mercy finally setting in.

  “Are you afraid, slave?”

  The word had a nice ring to it, and it oddly didn't sound too foreign on my tongue. What if I enjoyed this more than I expected? It was a strange thought, and one that brought a tremor of apprehension with it. I didn't want to end up losing Damien as Danica had, but I couldn't pass up this opportunity, not when it was likely the only one I would get. This is what I had asked for, and this is what he was giving me. It was a gift I would not see wasted.

  “No, Mistress.” Damien's eyes betrayed his words.

  “Maybe you should be. You're all tied up, and I can do whatever I want with you. Cause you pleasure or pain.”

  “I trust that Mistress will be gentle with me, as we had agreed upon.” His expression turned stern, pulling me out of the fantasy for a moment. It was a lot harder to maintain my dominant stance than I had imagined.

  “Me being gentle will depend entirely on you.” I poked his chest for effect.

  Damien's jaw clenched, and I could sense he wanted to say something, but knew better. His gorgeous cock was flaccid, obviously taking no enjoyment in what was going on. I couldn't help but wonder if whipping him would change that, or if I could expect him to remain unaroused through the entire scene. That wouldn't be fun at all. If he wasn't getting off to it, then what was the point. Sure, I liked him bound and under my control, but half of the pleasure came from him enjoying it. I wanted to see his cock hard, pointing out like a spear, twitching and dripping like Danica's submissive's had been. This wouldn't do at all.

  I sneaked around him, so he couldn't see me. Very lightly, I trailed the flogger between his legs again, watching his ass muscles flex. Taking a deep breath, I wound the flogger back and laid the first lash across Damien's back. His body jolted a bit, and I heard a hiss of discomfort fall from his lips. To be honest, the whole display made me feel guilty. While the idea of flogging him had once been fun, I was liking it a lot less in action.

  No. You started this. You can't back out now. This was what you wanted, isn't it?

  “You will count and thank me for each lash,” I told him, though my voice was trembling as I spoke. Hopefully, it sounded more like wrath than fear.

  “Yes, Mistress,” Damien replied in a dull tone.

  The second strike landed across his ass. Again, he winced and hissed in pain, counting and thanking my afterward. And again, I felt horrible for it. After the third blow, I realized I could go no further. I wasn't enjoying this. We would have to try something different.

  When I squeezed around Damien, I found his cock still flaccid. He's not enjoying this eith
er. He looked at me with nothing but respect, but said nothing.

  Timidly, I returned to the chest of drawers, placing the flogger back inside and looking at the contents desperately. I'm being an epic fail as a Domme. I should be making him grovel and submit. But if neither one of us likes it, then what's the point?

  Frustration was overwhelming me. This wasn't going anywhere near how I had envisioned it. In my mind, I had been powerful and assertive, and he had cowered beneath me, enjoying the abuse I bestowed upon him and begging for more. We were different people in reality though. Fantasizing couldn't change that I was submissive by nature, and he was dominant.

  With a sigh, I surrendered, walking back over to Damien to unfasten his wrist cuffs. If he was confused, it didn't show in his eyes. He simply watched me.

  “Have you had enough already?” he asked, not sounding surprised in the least. The fact that he didn't call me Mistress was enough to let me know he thought our little scene was over.

  “You're not reacting to anything I do to you,” I grumbled.

  “How would you like for me to react?”

  “I don't know.”

  “You hadn't thought about that either?”

  “I didn't really have a lot of time to plan.”

  “I don't think that's the case.” He towered over me, his gaze darkening, the balance of control shifting as we spoke.

  “Meh,” I grunted.

  “I recall there being something else that you wanted, something we would both enjoy.”

  “What's that?” My mood was soured, but I was open for suggestions.

  “No is not a safe word,” Damien said.

  Before I could even think, he was grabbing me and throwing me back toward the bed. I stumbled, nearly missing the mark, landing awkwardly on the side of it, having to use every muscle in my body to keep from falling to the floor, my mind utterly baffled. He came at me, looking angry. When he reached me, his hands were rough, pulling me up onto the bed, absent care of whether or not he was hurting me. Part of me thought to struggle, but I knew what was coming next, and it was something I definitely wanted. He stood over me, looking dangerous, all naked muscle and tousled hair.

  “I'm going to rape you now,” he told me.

  “You can't rape the willing,” I quipped.

  “No. You can't. That's why I don't want you to be willing. I had hoped telling you that no isn't a safe word would have been enough. You wanted to do a play rape scene, did you not? If I remember correctly, it was on your contract.”

  “Oh.” I blushed, feeling a bit stupid. That's what he meant. That's why he looked so angry and scary. “I do.” I nodded.

  His expression was dead serious. “Know that once I start, I won't stop. No amount of screaming or telling me that I'm hurting you will gain my sympathy. No isn't a safety word. And I won't accept yellow either. The only word that will make me stop is red.

  “During this session, I will do whatever I want to you. Whether it's something you enjoy or not will be of no concern to me. I will fuck you as hard and as violently as I like. And you will submit, because you'll have no choice.

  “You're more than welcome to try to fight me off. Hit me as you would an attacker. Try to get away. But know that there are repercussions for your actions. If we play this game, I play it rough.”

  I trembled, more out of lust than fear. That was the hottest thing he had said to me in a long time, though I was a bit scared of the truth behind his words. By the way that he made it sound, things could get really violent.

  You have your safety word. If he gets too out of hand, you can always say it.

  “Are you sure you want to do this?” he asked.

  I thought about it a moment longer before responding. “Yes, Sir.”

  My heart beat so fiercely that I feared it would rip through my chest. I wasn't sure what to expect. But this was something I definitely wanted to experience.

  “Are you ready?”

  I nodded.

  Damien took a deep breath, and then he advanced on me again. We were a tangle of grappling hands as he pushed me down on the bed, easily overtaking me. I kicked at him for good measure, nearly landing a blow between his legs, though my knee ended up digging into his inner thigh instead. You would have thought the injury was the same. In retaliation, I received a sharp slap across the face, which shocked me to the point that I stopped struggling long enough for him to capture my wrists and force them above my head. A tear ran down the cheek he had struck, more from the sting of the blow than fear.

  When I had regained my senses, I tried biting at his arms, though it was a pointless effort. They were too high above my head for me to reach. By that point, Damien was trying to get between my legs. I decided to give him a bit of help by wrapping my thighs around his waist and squeezing the shit out of him. He gasped, cursing and letting go of my wrists to try to pry me off. It only made me squeeze harder. For a while, I thought I had the advantage. If anyone looked like they needed to use a safety word, it was him. Then he turned the tides by grabbing me by the throat. The pressure he used scared me into submission. It wasn't a gentle squeeze. My life flashed before my eyes, and I thought I would choke to death on my safety word before I would get to say it. Thankfully, before I had a chance to die, Damien let up, though he still kept his hands on my neck. By that time, tears were streaming down my face from fear and mixed emotions. I wasn't sure if this was such a good idea after all. It was mimicking the real thing far too closely. This was the point where I would stop struggling in fear for my life, and so I did, letting him have full control.

  Damien forcefully pressed inside of me, though I was so used to his girth that there was little pain from it. He kept a hand on my throat as he thrust, putting his whole body into it. I stared up at him, watching a stranger move on top of me. It was the oddest thing to see him like this, far removed from the man I knew.

  While I was a bit traumatized from the realistic role play, I decided not to let it ruin my mood. If there was one thing that I loved, it was Damien being rough in the bedroom, and this was about as rough as it got. As long as I didn't defy him, I should be able to enjoy the rest of the ride.

  For the remainder of our coupling, I felt like a rag doll. My pussy ached from the intense pounding he gave it, fucking me as if it was the last time he'd ever get laid. I was bent and repositioned, struggling briefly every once in a while for sport, though I gave up the second that he started to get too violent.

  Damien put me on all fours, and I tried to crawl away, though he pulled me back easily enough, giving me a hard slap across the ass and warning me not to move again. My pussy throbbed in response. If not for the memory of my punishment spanking, I might have tried again. The first strike had been a playful warning though. I would not be so lucky the second time around.

  He tunneled inside my slick cunt, placing a hand on the small of my back as he jack hammered into me. Tiny contractions rolled through my clit, though I still hadn't had a full-on orgasm. For it being my birthday, the sex was all about his pleasure. Though I supposed if I was actually being raped, that's how it would go.

  When Damien was done with my pussy, he pulled his cock out, rubbing it on top of my ass. Tired of holding up my weight, I rested my head on the pillow, shoving my butt up into the air. Hopefully, he'd eat me out. My cunt was so hot it felt like it might spontaneously combust. A good tonguing would sooth it a bit. I had a good dicking, now I need a good licking. I smirked at my silent little joke.

  Damien was still rubbing his glans over my ass. He'd pause occasionally to spank me with his cock. I was just happy my pussy was getting a rest. There's no way I would be walking normal tomorrow.

  My body tensed when Damien grabbed his shaft and started rubbing his dick between my ass cheeks. Instinctively, I looked back at him and said, “No.”

  He grinned wickedly at me. “I don't recall you having a choice.”

  “No, Damien,” my voice was stern.

  He repositioned himself, lean
ing forward so his tip poked at the doorway of my pucker. “Don't move or it might hurt more.”

  “What part of no don't you understand?” I straightened myself, but Damien just pushed me back down.

  “No is not a safe word,” he reminded me, and I knew he was giving me my final chance to escape.

  I licked my lips, thinking. Anal sex had never been something I wanted to do. This was an interesting scenario though. He had already done so many horrible things to me. My jaw was swollen from him slapping me. My neck was likely bruised. My pussy was on fire from overuse. This would be the icing on the cake of our play rape scenario, a scenario I honestly never wanted repeated. He could fuck me roughly as much as he wanted, but not like this. Never again like this.

  “No,” I said finally, wondering what had gotten into me.

  “Try to relax,” Damien told me, his voice suddenly a lot softer than before. “It will hurt a lot less if you relax.”

  “Lube?”

  “Yes, lube.”

  He crawled off of the bed and went to the chest of drawers, opening up the second drawer and pulling out a bottle of lube. By the time he returned to me, his cock was well lathered with it. I winced as I felt the first dab on my asshole. A warm blush crept up my face as he massaged it in, pushing a finger inside of me. I grunted at the uncomfortable intruder. This was not going to be something I enjoyed, I could already tell.

  After a few minutes of prodding and rubbing, a second finger came to join the first. The pressure of the two fingers together was almost painful, and I wondered how I'd ever be able to take a cock back there. Damien was patient though, fingering the tight muscles of my backside into submission until he was able to glide effortlessly in and out.

  “Are you ready?” he asked.

  I could only assume our play rape session was over. He was being far too gentle and considerate. Perhaps it was because I was finally giving him what he had wanted for so long, and on my birthday, no less. The bastard better enjoy this.

  Damien gave his cock another coating of lube for good measure and then tossed the bottle to the side. My entire body tensed as he lined himself up between my legs. I can't believe I'm going to let him do this to me.