The Virgin Dating Game

by Sky Corgan

  His meaty cock head pressed against my virgin entryway, which tightened from the feel of it. Damien gave me another gentle slap on the ass.

  “Relax,” he told me.

  “Easy for you to say,” I grumbled. “Am I going to give it to you up the butt after this?”

  “No.”

  He pressed forward, and I could feel my resistant muscles spreading. It was more unpleasant than painful. I gasped, realizing I had been holding my breath.

  “Relax,” he said again.

  Inch by inch, his phallus slid inside of me. My muscles went absolutely wild from the new intruder. Damien groaned in response, obviously enjoying it. I was too busy processing the strange new sensation to gain pleasure from it. It felt like an uncomfortable fullness, a bit painful, but nothing unbearable. Losing my frontal virginity had been far worse.

  Finally, Damien was balls deep, and all I could think about was how horrible it must feel for him. He didn't share my sentiment though.

  “This is gross,” I groaned. “I don't understand why you want to do this.”

  “It feels great to me,” he replied. “Nice and tight.”

  Very slowly, he began bucking. Surprisingly, it felt rather pleasant when he was pulling out, though pushing back in brought with it the filling discomfort. I grunted with each thrust, trying to focus on my body's response rather than my mind's disgust. Damien was more gentle than he had been all night, taking things slow and easy, the complete opposite of the man he had been only minutes before.

  I allowed him to ride out his pleasure, amazed that my clit was beginning to respond with approving pulses. No. This is so wrong. You shouldn't be enjoying this. My mind and body were on two different wave lengths, and eventually, my body won over.

  While it didn't feel as good as having him in my cunt, taking Damien's cock up my ass wasn't unpleasant. I rocked beneath him, biting my bottom lip, waiting for him to tire. He didn't tire though. Instead, he picked up the pace, sliding in and out of me until my pussy was a mess of confused contractions. My muscles back there had mostly atrophied, but occasionally they would still tense. Damien moaned in response, absorbed in his own pleasure.

  Finally, when I didn't think that I could take anymore, I felt him push forward, his body stilling, a guttural moan escaping his lips as he pumped me full of his man juice. Does it really feel that good? I wondered. He was panting when he pulled away from me, his cock quickly softening from its expended efforts. Before I even had a chance to say anything, he was drawing me into his arms on the bed.

  “You're not done yet,” I said.

  “I'm not?” He gave me a quizzical look.

  “I've got a muff burger with your name on it.”

  He laughed. “Some of the things that come out of your mouth.”

  “And some of the things I want in your mouth. Now get down there and light the candles on my birthday cake.”

  As he descended between my legs, I could feel his soft breath on my warm folds. My pussy was absolutely swollen from all the abuse it had taken. Only his tongue could soothe it.

  Damien probed a finger inside my opening, and I twisted my fingers into his hair, pulling his face up to look at me. “Tongue,” I told him. “Only tongue.”

  “Yes, Mistress.” He smirked before diving in, engulfing my heated parts with his deliciously wet mouth.

  I groaned in approval, letting go of his hair and falling back against the pillow, sighing contently as his mouth worked skillfully to sooth the burn. My clit throbbed against the weight of his tongue, a bubble of pulsing pleasure waiting to burst and flood my body. Damien was meticulously slow, staying between my legs far longer than ever before. He brought me up the hill of pleasure, only to let me tumble down again, absent goal reached. I hated him for it, and loved him for it at the same time. Everything felt amazing; my body was alive with desire again, and if it wasn't for the soreness between my legs, I might have even wanted to go for round two.

  “Damien, let me come,” I whispered when the torture was more than I could bear. He obliged, flicking his tongue across my engorged pleasure button before baring down on it and massaging until electricity shot through my entire body, and I saw stars.

  When he breathlessly came to my side again, I curled up in his arms, satisfied and content. It was a good orgasm, worthy of my birthday.

  “You did well,” I told him, nodding.

  “Thank you, Mistress Little Girl.” He grinned. “Did you enjoy yourself?”

  “For the most part.”

  “What wasn't to your liking?”

  “I don't think I'm cut out to be a Domme,” I admitted.

  “I'm thankful for that,” he sounded relieved.

  “Me too. I prefer you on top.”

  “What about the anal?”

  I wrinkled my nose, not wanting to admit the truth. “It wasn't horrible.”

  “But you didn't like it either?”

  “It's not something I'd want to do all the time. I still think it's gross.”

  “The more we do it, the less you'll think that.”

  “We'll see.”

  “So, I guess this means I have permission to do it again in the future?”

  “I suppose,” I sighed, relenting.

  “And the play rape? What did you think of that?”

  My blood pressure rose just talking about it. “It's not something I want to do again.”

  “Didn't like it, huh?”

  “I'll just say this. If you ever slap me or choke me again, you'll wake up the next morning without a penis.”

  He winced. “I warned you about what it would be like.”

  “And now I'm warning you.” I snuggled down against him. “I may take your balls too. I haven't decided yet.”

  “Damn. Greedy girl. Leaving me with nothing.”

  “They're mine, as is the rest of you.”

  “I am yours,” he said, giving my hand a gentle squeeze, making everything right again.

  We laid together for a while before Damien finally went to get a towel from the bathroom and clean us off. By that time, his seed had already run out onto the bed, and I was left lying in a sticky mess. It didn't matter though. All that mattered was that we were together. I was with the man I loved, and that made me happy.

  When the mess of sex was mostly cleaned up, he laid back down with me again, gently stroking my hair while I rested my head on his chest. Our bodies fit together perfectly, and I was so relaxed and exhausted that I could feel my eyes growing heavy. I was almost asleep when Damien moved, startling me back awake.

  “I still have a few more things to give you for your birthday,” he said.

  “More presents?” I sat up, smiling at him.

  “I'll be right back.”

  I watched as he walked naked out of the room, that gorgeous ass flexing with every step. Maybe he'd let me bite it. That could be birthday present number five. Why I hadn't thought about it when he was tied up, I didn't know. Probably because my mind had been too consumed with thoughts of sex. Stupid wanton body.

  When Damien returned, he had a small box in his hand. It was wrapped in paper with balloons on it and had a bow on top that was almost as big as the box itself. He sat on the side of the bed and handed the box to me.

  “What is it?” I wondered aloud, holding the box up to my ear and shaking it. It was heavy, but made no sound.

  “Open it, and find out.”

  My hands went to work tearing away the wrapping paper. Beneath it, the box was black. When I opened the box, I was a bit confused, but smiled, none the less. Inside was a solid stainless steel collar.

  Damien took a deep breath, watching my expression. “Do you like it?”

  “It's beautiful. Is it another public collar?”

  “It's your formal collar.”

  My breath caught as I took another look at the collar, realizing what it signified. Now, I was gazing upon it with new-found appreciation. I touched the metal, cool beneath my fingertips.

 
; “It hasn't been six months yet,” I said.

  “No, it hasn't. But I don't think I can wait six months. I love you and want you to be with me forever.”

  My lips were trembling, and I was fighting back tears. It wasn't the same thing as a marriage proposal, but for some reason, it felt like it. To Damien, it was every bit as good.

  “Do you want to take things further and cross the final step to being my submissive?”

  “Yes,” I replied without hesitation, then set the box aside and threw my arms around his neck, hugging him tightly. “Oh, yes. I do.”

  “Good.” I could hear the smile in his voice, and that only made me happier. “I'd also like for you to move in with me at the end of this semester.”

  “What?” I pulled away from him, shocked.

  “I figured, since we're going to be together, you might as well move in. You won't be much farther from the college than you are living with your father. Your parents seem to like me well enough. I'd like to think they know I'll take good care of you. I'd like to think you know I'll take good care of you. Is that something you would want?”

  “Yes. Yes. Yes.” I hugged him again, so tightly that I worried I might be choking him.

  It was hard to imagine living in a giant mansion, tending to Damien's needs night and day, waking up beside him in the morning, having sex with him whenever I wanted. Maybe years in the future I could have imagined it. Not now though. We had known each other for less than a year, and Damien didn't seem like the type of guy who would move so quickly. Was I dreaming this? Everything felt so surreal.

  “Good. It's settled then.” He leaned forward to kiss me on the cheek. “Happy Birthday, Cheyenne.”

  CHAPTER SIXTEEN

  Planning a collaring ceremony is a lot more difficult than one would think. Damien left almost everything up to me. I chose the guest list, the food, and the decorations. The only thing he decided was that we would have it at his house, and that I would walk down the aisle naked except for my training collar. It was a disconcerting thought, but it wasn't like our guests hadn't seen me naked before. Well, everyone except Tanya, Vinny, and Colton, who I made sure to invite. This was a big deal, a huge milestone in my life, and I wanted my friends to be there to witness it.

  The joyous day came on the first Saturday after school let out for summer vacation. Tanya and Danica arrived early to help me get ready, not that it involved much. Basically, Tanya did my hair up in a loose bun while Danica went over the ceremony with me. Despite our rocky beginning, I had grown to like her, for the most part. Every once in a while, she still looked at Damien in a way that displeased me, but I tried to brush it off as best I could. She was his past. I was his future, and his forever.

  Our guest list was small, and only half of the invited people were able to attend. Colton had chosen not to come, Tanya informed me, and I assumed it was because he was feeling a bit butthurt that I hadn't ended up with him instead of Damien. It was fine. I could understand that.

  Sir Martin came to retrieve me when it was time, escorting me into the backyard at the chime of a bell. Danica followed behind with my formal collar on a pillow and our contracts folded up in the pockets of her tight vinyl pants.

  My heart pounded in my chest as we approached the guests. There were nine chairs on each side, forming an aisle down the middle that led up to an archway Damien had rented for the occasion. Beneath the archway sat a single white satin pillow I would be kneeling on later.

  My palms sweated around the leather leash I held in my hands, and my gait was far from graceful as I walked beside Sir Martin, trying to keep my eyes to the floor, though I could see everyone out of my peripheral vision. Our guests sported a mix of formal and kink wear, a reminder that I had forgotten to put the expected attire on our invitations. It made no matter, really. This event wasn't about them. It was about us.

  When we reached the end of the aisle, Danica took her place over by the archway. Sir Martin and I turned to address the crowd, and I felt the butterflies whirling in my stomach as he began to speak.

  “I present to you Cheyenne Grear, submissive in training to Sir Damien Reed. She has shown great character and obedience, meeting all requirements to advance on toward full ownership. I remove this training collar from her neck to show that she is now a free submissive, able to take a Master of her choosing.”

  He moved behind me to unfasten the collar. My neck felt strangely naked without it. When he was done, he stepped away from me, and a second bell rang, signaling Damien's entrance.

  Damien looked absolutely dashing in a black tuxedo with a vest and tie beneath. It was the most dressed up that I had ever seen him, and it took everything in me not to smile. The man cleaned up well—very well, and I couldn't wait to unwrap him like a present after the nuptials were over.

  When he reached the end of the aisle and took his spot beside me, Sir Martin continued, “I present to you Sir Damien Reed. He has shown an interest in taking on Cheyenne Grear as his property. She has met all of his requirements for ownership, and he has removed her training collar to allow her to make this decision freely.” Sir Martin turned to me. “If you would like to take this man as your Master, you may now offer him your leash and your full submission.”

  Sir Martin stepped away from us then, allowing Damien and I to take center stage, facing each other. I was so nervous that I thought I might throw up. This was it. Once I gave myself over to him, there was no going back.

  Taking a deep breath, I lifted the leash up to Damien and spoke the words, “I present you with this leash as a sign of my devotion and submission. It is my desire that you take me as your own, to guide me, shelter me, and train me as you see fit, for this day, and all days that follow. I wish to belong to you and for the privilege to call you Master.”

  Damien took the leash from me, holding it out before me as I had in front of him. He looked down on me with confidence and pride. “I accept this gift of your submission. I promise to care for you, guide you, train you, and discipline you how I see fit. It is my wish that you belong to me, from this day fourth. I bestow upon you the right to call me Master. Will you kneel before me and become mine?”

  “Yes,” I replied, obediently kneeling on the pillow.

  Danica stepped up to present Damien with my formal collar. He took it and gently placed it around my neck. The weight of it felt perfect, and with its placement came a wave of happy emotion.

  “I wear this collar as a sign of my submission to you and my acceptance of your ownership. I will wear it now and from this day forth with pride at what it signifies.”

  “You now belong to me.”

  “You are now my Master.”

  “Stand and let us seal this pact before our family and friends.”

  Danica took the two contracts from her pockets and handed us our appropriate version. We had read them beforehand, so we both knew what they contained. I just hoped Damien hadn't been sneaky and slipped in a modified replacement of my contract, as he had tried to do with my training contract. That seemed like it was ages ago, and I had eventually given him what he wanted, so there was no reason to be deceptive.

  Taking a deep breath, I signed my copy, then Damien's. When we were finished signing each other's contracts, we handed them off to Sir Martin to sign as a witness.

  I turned to Damien and knelt on the pillow again. “I accept this contract and all it entails. From this day forward, I will serve, honor, and obey you in all things. I will love you and care for you, and open my body and mind to all that your heart desires. I now belong to you and give you my submission freely as a gift.”

  Damien attached the leash to my collar. “I accept your gift of submission and will cherish it to the end of my days. I will strive to always make sure you are happy, and will do whatever it takes to keep you content in your decision to give this gift to me. You and I are one now.”

  I bent to kiss Damien's feet, waiting for his first command as my Master.

  “Raise your head,”
he said, and I did as I was told, looking up at him. He leaned over to give me a gentle kiss on the lips before telling me to stand.

  Sir Martin stepped in front of our audience. “These two people are now bound together. This concludes the collaring ceremony.”

  Bells rang to the sound of our union, and Damien embraced me, kissing me with far more passion than he had when I was on my knees. It seemed unrestrained and endless, our mouths moving together with excited fervor, happy that we officially belonged to one another.

  Our guests came up to greet and congratulate us, breaking us free from each other's arms. Tanya and Vinny smiled at me from a distance, but I could tell the whole ordeal had made them a bit uncomfortable. It wasn't long after that they left, though the reception continued on without them.

  Sir Martin had brought a Saint Andrew's cross with him, and for part of the reception, I was strapped to it while each guest got to come give me a flogging. Most were gentle, though Danica and Sir Craig left red welts in their wake.

  The rest of the evening reminded me of a normal wedding reception. We ate cake and socialized and drank and danced. Damien had rented a DJ since he thought hiring a band would be a bit too much. It was always odd bringing strangers into BDSM events, he said. I understood that well enough. The DJ only did slightly less gaping at my nude body than the cook had at Damien's dinner party.

  It wasn't until late in the afternoon that our guests finally began to disperse. Sir Martin was the last to leave. Damien helped him load the Saint Andrew's cross into the back of his truck, and then we were alone at last, Master and submissive.

  “Did you have fun?” Damien asked, leading me by my leash into the bedroom.

  “I did.” I nodded. Though I was extremely exhausted, I could hardly wait for what was coming next.

  By the time we got to the bedroom, there was already a tint in his pants. Damien turned on me, gripping my hair and pressing me up against the wall as he attacked my mouth with an onslaught of kisses. He grabbed my leg, pulling it up over his hip, and I could feel the hard bulge of his manhood pressing between my pussy lips, the material of his pants rubbing out the first ounces of pleasurable sensation between my legs.