The Virgin Dating Game

by Sky Corgan

  He was silent for a moment, thinking. “It would be a really big deal for me to give up control.”

  “And that's why it's so important to me. I know you've never done it before. At least, she made it sound like you've never done it before. That's why it would be such a great gift.”

  Damien sighed again, “You do realize that if I do this, I'm so asking you for anal for my birthday.”

  I giggled, “Sure, I'll give it to you up the butt for your birthday.”

  “Cheyenne, I'm serious. You're asking me to do something that's going to make me very uncomfortable.”

  “Why would it make you uncomfortable? You trust me, don't you?”

  He hesitated, making me feel absolutely horrible.

  “You don't trust me,” I said.

  “It's not that. It's not you,” he stumbled over his words. “I just don't trust anyone to that degree.”

  “I promise I won't shove anything up your butt.”

  “Then what would you do to me?”

  “I don't know. I haven't thought that far in advance yet.”

  “You're lying.” He furrowed his brow.

  “No. Really. I mean, flogging you might be nice, but I really don't know. I haven't thought much past the point of actually having you tied up.”

  “Well, that doesn't make any sense.”

  “It doesn't matter. It's what I want.”

  I felt like we were at a stalemate. He wasn't going to budge, and I truly didn't want anything else from him. The best I could hope for was to salvage the rest of the evening.

  “My father is coming home tomorrow. I want you to meet him,” I changed the subject.

  “Another request I'm not very comfortable with.”

  “Comfortable with it or not, you agreed to it. You'll come over for an early dinner on Friday, around six o'clock. Afterward, I'm taking you to meet my mother.”

  “Both parents in one night. Double whammy,” he sounded genuinely unhappy.

  “I'm celebrating my birthday with them on Friday, and I want you to be there. We've been together for a while now, and they still haven't met you.”

  “Don't you think they'll have issues with me being older?”

  “My mother doesn't care. My father doesn't know, and if I don't tell him, I doubt he'll figure it out. You don't look your age.”

  “But I look older than you.”

  “By a few years. It's normal for a girl to date a guy who is a few years older than her.”

  “Fine. I'll meet your parents,” he relented.

  “I told them you're my boyfriend, so I'll expect you to play the part.”

  “So demanding. Are you sure Danica didn't get in your head?” he teased, pinching my side.

  I swatted his hand away. “I think it's good that I'm being more open and honest with you about what I want.”

  “I suppose.”

  “What? Would you have me silent, barefoot, and pregnant in the kitchen?”

  He arched an eyebrow, and I couldn't tell if the look was sarcastic or disturbed. “I'd rather you be bound and gagged in the bedroom.”

  “Friday. My house. Six o'clock. Wear something nice. I want you to make a good impression,” I said before leaning forward to give him a sloppy kiss on the lips.

  “Yes, ma'am.”

  On Thursday, my father arrived home from another long run on the road. He greeted me with tempered enthusiasm, probably still weary from the road. By Friday, he was in a much better mood, though that could have been entirely because it was my birthday. Whatever the case, he seemed a lot happier.

  When I got home that afternoon, I took a quick shower and then went to work cooking dinner. My father had offered to take me out to eat for my birthday, but I really wanted to make dinner for the two most important men in my life. Perhaps it seemed a bit strange, but it meant a lot to me, watching them both enjoy a meal I prepared with my own hands. Hopefully, they'd get along, and the evening would be perfect.

  The doorbell rang at promptly six o'clock. Damien was punctual as ever. He was dressed to impress in a pair of black skinny jeans and a beige sweater with black loafers. His hair was neatly spiked, but he still had his five o'clock shadow. Apparently, shaving hadn't been part of cleaning up. Regardless, he looked more put together than normal.

  When I opened the door, he smiled warmly at me, though I could see the discomfort behind his eyes. No matter how hard he tried to hide it, I could tell he was nervous about meeting my father. I couldn't help but wonder when was the last time he'd been introduced to a girl's parents.

  “Mister Grear,” Damien greeted my father in the living room. He had been sitting on the sofa watching television and promptly stood when Damien and I entered the room. They shook hands, locking eyes in a very awkward manner.

  “Mister Reed, it's a pleasure to finally meet you,” my father replied before releasing Damien and taking his seat on the sofa. Damien sat in the armchair.

  “The pleasure is mine. Cheyenne tells me you're an over the road truck driver. It sounds like hard work.”

  “Not so much hard as it is long.”

  Phew. They're talking and getting along. Good deal.

  “I'm going to leave you boys alone for a bit while I finish setting the table,” I said before leaning down to give Damien a kiss on the cheek and then retreating to the kitchen.

  When the table was set, I called them into the dining room for dinner. We started with a simple garden salad, though my father barely touched his. The main course was roast beef with mashed potatoes, and dessert was yellow birthday cake with chocolate icing that my father had bought earlier in the day when he had gone out to get groceries for the dinner. Most of the meal was spent in silence. While the ambiance was pleasant, I could tell that both men were a bit uncomfortable in each other's presence.

  When dinner was over, my father gave me a birthday card with fifty dollars in it. That had been his customary gift ever since I turned sixteen. I wasn't sure if it was because he felt he had lost touch with me, or because he just thought that money was the best gift for a woman grown. Whatever the case, I took it graciously and thanked him, giving him a big hug and kiss upon the cheek.

  Before we left, Damien and my father exchanged goodbyes. Things couldn't have gone more smoothly. While I couldn't tell if my father truly liked Damien or not, he hadn't scowled at him or said anything demeaning or degrading, so I took that as a good sign.

  My mother received Damien with far more vigor. As soon as she laid eyes on him, the first thing she said was, “Oh my. You're even more handsome in person.” To which Damien gave me a funny look, and I was forced to explain, with some embarrassment, that I had shown her shirtless pictures of him.

  To make matters worse, my mother took the liberty of lifting up his sweater to see if his abs were real. He took all of her poking and rubbing with grace, absorbing her flattery as if it was normal conversation. I, on the other hand, was beet red when she was done with him.

  Once the introductions and my embarrassment were over, we settled down in my mom's living room to open presents. If there was one thing that my mom loved to do, it was shop for me whenever there was a gift giving holiday. She got me three shirts, a pair of pajama pants, a pair of shorts, some body wash and a loofah, and a toothbrush. Much like my dad's fifty dollar card, I could always count on getting a toothbrush as a gift. Apparently, my mom worried that I didn't change mine out enough.

  Damien and my mother got along surprisingly well, which I was pleased with. She was even able to make him smile and laugh a few times. By the end of the night, she was hugging him like he was her son and I was the stranger. Traitor!

  We ate another round of birthday cake, this time chocolate with chocolate frosting, Damien loaded up his Corvette with my birthday presents, we said our goodbyes, and then my mother ran outside and humped Damien's car before we left. My eye twitched as I watched her, my mouth falling open into a horrified gap.

  “Marry this one,” she blurted out. “He has
money.”

  Damien laughed lightheartedly, but I was absolutely mortified. In all honesty, I was never happier to get him away from her. While I loved her dearly, I wasn't sure how much more humiliation I could stomach. It would be a long time before I brought the two of them together again, or at least not until I had a talk with my mom about what she could and couldn't do around him. Weirdo.

  “Your mom is funny,” Damien told me as he started the engine.

  “My mom is embarrassing,” I grumbled.

  “I think she likes me.”

  “A bit too much.”

  “I think she likes my car more.”

  “You should wash it tomorrow.”

  We drove back to my father's house in silence. Well, not so much silence. Damien had the radio on, but we weren't talking. I was too busy wondering what my dad thought about him. Who knows what Damien was thinking about?

  When we arrived, Damien killed the engine to spend a few more minutes with me before he had to send me back inside.

  “You should come in,” I suggested with a devious grin.

  “I'm not having sex with you while your father is home.”

  “Why not?” I pouted.

  “Because you're too loud.” He smirked.

  “That's your fault. Maybe if you weren't so rough, I wouldn't be so loud.”

  “You like it rough.”

  “Yes, I do,” I admitted, feeling my clit pulse in agreement.

  “I like your parents,” he changed the subject.

  “I'm glad. I still want you to come inside.”

  “We'll have all day tomorrow together.”

  “Tomorrow isn't my birthday though. Tonight is my birthday. And I want birthday fuckles.”

  “You'll get birthday fuckles tomorrow.” He gave me a warning look.

  “We could do it in the car.” I slid my hand onto his thigh, sneaking it up to his cock.

  “Chey, I'm not fucking in this car. Do you have any idea how uncomfortable that would be? We'd probably break something.”

  “You're no fun.” I pulled my hand away, frowning.

  “Tomorrow. I promise. I have lots of things planned for you that you're really going to enjoy. Good things come to those who wait.”

  “What kind of things?” I wiggled in my seat with a grin.

  “You'll find out tomorrow. Now, you better get back inside. I'm supposed to be making a good impression, remember? I wouldn't want your father to think I'm defiling you out here.”

  “I wish you were defiling me out here,” I huffed. “Can I at least masturbate tonight? It is my birthday, after all.”

  He sighed, “Fine. I'll allow it. Just tonight though.”

  “Yay!” I jumped up and down in my seat like a small child. “I shall fap to thoughts of being with you tomorrow.”

  “Good girl. Now, go inside and spend time with your father.”

  “Yes, Sir.” I leaned over to give him a final kiss before exiting the vehicle and popping the trunk to get my presents and take them inside.

  With a content smile on my lips, I watched Damien's car until it disappeared around the corner. Tonight couldn't have gone any better. I just hoped that the following day would be equally awesome.

  By the time I got inside, my father had already headed to bed. It wasn't until the next morning that I was able to ask him what he thought of Damien. He didn't seem too opinionated. All he said was that Damien seemed like a good guy, and as long as he made me happy, that was all that mattered. It was the best I could hope for since they had only met once. My father had never been very invested in my love life, but it made me happy to know he approved of Damien.

  I arrived at Damien's house a little after noon only to transfer vehicles and head back out on the road. He took me to eat at a Brazilian steakhouse. The atmosphere was a bit stuffy for my taste, but the food was excellent. There were cuts of beef and lamb and pork, along with sausage links, and chicken legs, and bacon wrapped chicken breast. Most of the meat was served rare, which wasn't to my liking, so I mainly dined on chicken and pork. Afterward, Damien asked if I'd like dessert, but there was only one kind of dessert on my mind.

  When we got back to his house, I was feeling less than sexy from having such a full stomach, but that wasn't going to stop me. We sat on the sofa for a few minutes to let our food digest, and when I had had enough of lazying around, I began pawing at Damien's jeans.

  “What?” he asked, looking down at me with hooded eyes as if he was about to fall into a meat coma.

  “Birthday fuckles. You promised.”

  “Can we take a nap first? I'm not exactly at the top of my game.”

  “Fine,” I sighed, standing and grabbing him by the hand to pull him towards the bedroom.

  “What are you doing?”

  “Putting you to bed. The sooner you sleep, the sooner we fuck.”

  “You're so impatient,” he laughed. “Didn't I tell you that good things come to those who wait?”

  “I never claimed to be patient.”

  We curled up together on Damien's bed, and within half a heartbeat, he was snoring loudly by my side. I smirked at him, watching him sleep. While the sound coming from him was less than attractive, he still looked gorgeous, and oh so rapeable. What would he do if I took his cock out and started sucking on it? Probably get mad. I scowled at the thought, settling down beside him and closing my eyes to sleep.

  The day passed by unnoticed, thanks to being asleep for most of it. When I finally awoke, Damien was nowhere to be seen. I yawned and rubbed my eyes, then rolled off the bed to go search for him. Not surprisingly, I found him in the living room, curled up on the sofa with a book. The man loved to read.

  “What time is it?” I asked, yawning again.

  He looked at his watch. “Almost four.”

  “What time did you get up?”

  “About thirty minutes ago.”

  “We slept for a long time.” I leaned on the side of the couch, looking over at him.

  “We did.” He set the book down, returning my gaze. “Are you ready for part two of your birthday present?”

  “Part two?” I gave him a curious smile. “There are parts to my birthday present? I thought it was just going to be dinner and sex.”

  “Well, dinner was part one. There are three more parts though.”

  “And what are the other three?”

  “Would you like to find out?”

  “Mhm.” I nodded.

  Damien stood, rounding the sofa and taking me by the hand to lead me out of the room. We turned the corner to the classroom, and I could only imagine he had a special session planned. My heart drummed softly in anticipation, my body quickly warming up from thoughts of kinky sex. Out of habit, I took a seat on the bed, assuming the Teach position, wondering if I should be undressing instead. I would wait for Damien's order. When we were inside this room, my submissive nature was stronger than ever, perhaps because this was where most of my training took place, and most of my punishment as well.

  Damien went to the chest of drawers and opened up the top drawer, looking at the contents with a sigh before he turned around to face me. “This is part two,” he said.

  I sat there for a moment, confused. “What is, Sir?”

  “Come find out.”

  Apprehensively, I stood, wondering if this was some kind of trick or riddle. When I looked in the drawer, I found a restraint system, a flogger, a ball gag, a blindfold, a thick leather collar, nipple clamps, and some rope. I was no less confused than before. Did he mean to have another scene with me?

  “Should I get undressed, Sir?” I asked.

  “If that's what you want.” He looked down on me, but his eyes lacked the intensity I was used to seeing.

  Nervously, I began shedding my clothing, folding each garment as it came off and placing them on the chest of drawers. Damien stayed by my side, as still as a statue, watching me. His gaze made me uncomfortable, but I continued until I was naked, presenting myself before him.
r />   “What now, Sir?”

  “Whatever you want. This is your gift.”

  I peered down into the drawer, trying to compose my own fantasy. Nipple clamps weren't my favorite thing, so I'd take a pass on those. We'd never used a ball gag before, but I didn't like the idea of not being able to vocalize my safety words. The flogger was familiar, definitely something I wouldn't mind experiencing again. Everything else in the drawer was Chey approved.

  “I want birthday spankings,” I said, thinking that was the only thing missing.

  “Alright. If that's what you want.”

  Damien sat on the edge of the chair, leaving enough room, so I could lay over his lap. I did so as daintily as possible, my cunt already pulsing from the desire to feel his large hand warming my backside with sharp slaps.

  “Nineteen,” Damien said. “Count them off and thank me after each one.”

  “Yes, Sir,” I replied enthusiastically, trying not to wiggle.

  The first blow sent delicious heat raging through my butt.

  “One. Thank you, Sir,” I responded.

  Each strike added to the fire, landing on alternating ass cheeks. My mouth twisted into a lusty grin, my loins moistening at the pleasurable pain. By the time Damien got to nineteen, I was worried my juices might start running down my legs. I made a soft satisfied moan as I pulled myself off of his lap, standing in front of him.

  “Did you enjoy that?” Damien asked.

  “Yes, Sir.”

  “What else would you like for me to do?”

  “I suppose I would like to be restrained, blindfolded, and flogged, Sir.”

  He gave me a half-quirked smile. “This isn't what I expected at all. Or perhaps you mistake my intent.”

  “What?” I looked up at him, breaking away from my submissive stance.

  “The stuff in the drawer isn't for me to use on you. It's for you to use on me,” he paused. “Unless, of course, that's not what you want. I would gladly use it on you instead.”

  My mouth fell open in disbelief. Was he actually going to let me dominate him? After all of that arguing about it.

  “I did misunderstand,” I replied quickly, feeling a bit embarrassed about it.