Worst Date Ever

by J. S. Cooper

  “So …?” he whispered.

  “So,” I breathed, wondering what he was going to do next. I didn’t have to wait long because then I felt him moving his hand toward the front, slipping it down between my legs and touching my wetness. His fingers gently rubbed my clit and he groaned as he felt how wet I was already.

  “Oh, shit. You want me so badly, don’t you?”

  “Maybe, maybe not.”

  “Maybe not nothing,” he groaned and kissed me hard. I moaned against his lips as his fingers teased me. This was fucking hot. I’d never made out in an elevator before, and I’d certainly never had someone play with me in an elevator, but there was a first time for everything, and I liked it.

  He lifted me up, and instinctively, I wrapped my legs around his waist. He leaned back into the back wall of the elevator, grunting as I wrapped my hands around his neck, and pulled his face into mine so that I could kiss him harder. “Oh, fuck. I would fuck you right now if I could,” he said.

  “Oh, yeah?” I mumbled against his lips, wishing that he would. I groaned when I heard the ding of the elevator, and he let me slip back to the floor.

  “We’re nearly at my apartment. I guess we’ll have to do it next time.”

  “Yeah, next time,” I said, even though we both knew there was not going to be a next time.

  He grabbed my hand and pulled me out of the elevator. I gasped as we walked into a huge apartment with wall-to-ceiling windows. I stared all around me. I could see the New York skyline from a distance. “Oh my gosh, is that the Chrysler building?” I walked over to the window. He laughed as he came up behind me.

  “Yep.”

  “Wow, this view … I don’t know what to say.”

  “Surprise.”

  “Is this the penthouse?”

  “Yep,” he nodded.

  “But anyone can get here. They just have to press the button. There’s not even a—”

  “No one else can get here.” He shook his head. “That’s my private elevator.”

  “But it goes to all floors.”

  “Because I have access to every floor,” he explained. “No one has access to this floor except for me.”

  “Oh, wow.” I stared at him through narrowed eyes. So he was rich. Really rich. “And you let me pay for dinner?” I poked him in the arm. “Really?”

  “What? You offered.”

  “But you’re rich, I’m not.”

  “So why did you offer if you didn’t want to pay?”

  “Because you were calling me a gold digger!”

  “Does it make a difference that I make more money than you?” He looked into my eyes. “Are you saying that you are a gold digger?”

  “No, but you could at least have offered to pay the tip.”

  “I could have.” He grinned. “But I didn’t.”

  “You’re an asshole, you know that, right?”

  “I think we already figured that one out,” he said, “or at least you did.”

  “Whatever.” I shook my head.

  “Why? What do you want to do to me? Am I a bad boy?”

  “You’re a really bad boy.”

  “Are you going to cook me some dessert now?”

  “What? What are you talking about?”

  “The kitchen is that way.” He grabbed my hand and pulled me to the side of the apartment where we came to a large, open-plan kitchen with a huge white island in the middle.

  “Wow. This is beautiful.”

  “Everything you need is in the cupboards,” he said, “You can find it.”

  I blinked at him. “Find what?”

  “Aren’t you going to make me a dessert?”

  “Uh, why would I be making you dessert?”

  “Isn’t that what you wanted?” He looked at me through narrowed eyes.

  “What are you talking about?”

  “I thought you said you love to come back to a guy’s place and make them dessert before the real dessert.”

  “Um, okay …”

  Obviously, this was some bullshit that Abby had come up with. Maybe I’d take the death penalty twice because she had really talked a lot of nonsense.

  Jack and I stared at each other for a moment. “So … I guess you’re not going to make me dessert,” he observed.

  “I’m not enough?” I said softly as I walked over to him.

  He gazed at me through narrowed eyes. “Maybe. Why? What have you got to show me?”

  “Oh, I have everything to show you, big boy.” And then I did a move that I’d only seen in movies. I pulled up my dress and let it drop on the floor so that I was just standing there in my bra, panties, and heels. His jaw dropped and he whistled as he looked over my body.

  “Okay. I have to admit, I didn’t see that one coming.” He swallowed hard. “You are so fucking hot, but I guess you already knew that.”

  I smiled. “Now it’s your turn.”

  “My turn?” He grinned. “What do you want me to take off first?”

  “Hmm, let me think,” I said, as I walked over to him and press my finger on his lips. I grabbed him by the collar of his shirt and pull him down to kiss me. I kissed him hard and then reached down and squeezed his cock. He groaned as my fingers left it. “Come with me.”

  I led him to his massive living room and pushed him down on the couch. “You know something I’ve always wanted to do?”

  “No.” He shook his head. “What?”

  “Do you have any music?”

  “Music?” He looked confused.

  “Like a stereo, an iPad, Spotify. Something I can play some music on?”

  “Yeah. Why?”

  “You’ll see,” I said. “Where do I access it?”

  “Hey, Google,” he said, and I laughed.

  “Fine. Okay. And do you have any mood lighting in this fancy penthouse of yours?”

  “Of course,” he said. He pressed something on the wall and all the lights in the apartment went out. It wasn’t dark, though. Because of the city lights, we were surrounded by lights from every other building in New York City.

  “This is good.”

  “What are you going to do?”

  “You’ll see,” I laughed. And then I thought for a minute. “Hey, Google, play Drake.”

  “Playing Drake,” Google responded.

  Before I could count to ten, Drake’s latest hit was playing. I started swaying my body back and forth to the beat of the music, almost but not quite touching Jack. He reached up to grab my waist and I pushed his hands away. “No, no touching. They don’t allow touching here.”

  “They don’t allow touching, where?” He looked confused and looked around. “This is my apartment.”

  “Shh,” I said, putting my finger against his mouth. “No talking. Izzy doesn’t like it when you talk.” I leaned closer and brushed my breasts back and forth against his nose and lips.

  “Izzy, huh?” He grinned. “Well, where are we, Izzy?”

  “We’re at the strip club. The most exclusive strip club on the Upper West Side. No,” I changed my mind, “actually, the Upper East Side.”

  “Oh, I see. And you’re a stripper?”

  “I’m an exotic dancer. The best you’ve ever seen.”

  “Well, you’re the best something I’ve ever seen.” He nodded, his eyes lighting up, and I laughed. He was an asshole, but I was glad he was going along with it.

  This was actually a fantasy of mine. I don’t know why, but I’d always wanted to be a stripper for one night at an exclusive strip club and seduce the hottest man there and have him begging for more. And this was real life. I was never going to go to a strip club to be a private dancer. And I certainly wasn’t going to fuck some stranger in a strip club, but hey, I could live out my fantasy here and no one would judge.

  Jack wouldn’t judge me. He didn’t know me. And even if he did, I didn’t care because tonight was just about me and him fucking our brains out and having the time of our lives and living out my fantasy. I’ve known as soon as
we’d walked in and I’d seen his amazing penthouse. This felt like something out of a fucking amazing movie. More amazing than a movie, but I wasn’t going to think about it too hard.

  “So, Izzy, can I—?”

  “Shh,” I ordered. I put on a Russian accent. “Izzy doesn’t like it when you interrupt.” He laughed. I think he realized that I didn’t really know what I was doing, I was just having fun.

  “Well, Izzy,” he said, with a French accent, “please let me know how much the dance will cost.”

  “You’ll see afterwards. It will be worth all the money you’ve got.”

  “All the money I’ve got, huh? Well, then, that’s going to be one really good dance.”

  “It’s going to be the best dance of your life.” And then I straddled him. I moved my hips back and forth and closed my eyes as I sang along to the music. I could feel him growing harder and harder beneath me. And I loved it. I started flicking my hair back and forth and running it across his face.

  I felt his hands on my waist and opened my eyes. “Naughty boy. Customers cannot touch.”

  “What if I throw in another hundred?” he said, his eyes veiled.

  “Hmm, I don’t know.”

  “Fuck, Izzy. You’re fucking sexy as hell.”

  “Am I?” I stood up and turned around, moving my hips back and forth so that my butt was in his face, gyrating, but not touching anything. He groaned and I laughed as I turned my head around to look at him.

  And then he slapped me on the ass. I should’ve stopped him, but it felt dirty. It felt sexy. And then he slapped me again, not hard, just teasing. I groaned as I felt his fingers slip between my legs and he rubbed me through my panties. “Naughty boy,” I turned around and dropped onto my knees, looking up at him between his legs.

  “I am a naughty boy, aren’t I, Izzy? Are you going to punish me?” he said, looking down at me.

  I nodded my head without speaking. And I reached up and I grabbed his belt and pulled it out of his pants. I quickly unbuckled his pants and unzipped him and started pulling them down. I groaned out loud as I saw his hard cock through his tight black boxers. I licked my lips and he grinned.

  He started undoing his shirt and I let him. If he wanted to help me, who was I to say no? He threw his shirt onto the ground and then I quickly undid his shoes. He slipped them off and then I pulled his pants off.

  Now he was sitting in only his boxers. His chest was magnificent. He was strong and muscular and tan. I leaned forward and kissed him in the navel and then licked my tongue across his washboard abs. I felt his hands in my hair and moaned as he tugged. I pushed him back and then kissed my way down his stomach towards his cock. I placed my mouth on his cock through the material and he groaned as I sucked the tip. I then pulled his boxers off and his cock sprang free. He was ginormous, probably the biggest guy I’d ever seen in person. I licked my lips again and he laughed.

  “Like what you see?”

  “Maybe.” I loved what I saw. I got up, straddled him again, allowing the length of his cock to sit between my legs so that as I rubbed back and forth, I could feel the tip of him rubbing against my clit.

  “Oh, shit,” he said, grabbing my hips.

  “Oh, yeah.”

  He undid my bra. I let him unclasp it and it fell to the ground. He moaned as I reached and grabbed his head and pulled it down into my breasts and rubbed my nipples across his face then took one in his mouth. I moaned as he tugged and teased me. This was so fucking hot. I could feel my panties were drenched as I felt his hardness between my legs. His fingers ran down my back up and down, up and down lightly tracing the curve of my spine as I increased my tempo on top of him.

  Without warning, I jumped up and turned around so that I was straddling him with my back against his chest. I grabbed his hands and placed them on my breasts so that his fingers were teasing both of my nipples. I moaned as he pulled and tugged on them and kissed my neck. I wasn’t going to last much longer, and I didn’t think he would last much longer, either. I stood up and pulled my panties off, loving the look in his eyes as I stood there naked in front of him. And then I sat down on his lap and I pulled my legs up so that my calves were hanging over his shoulders on either side.

  And then I started dancing. Moving my hips back and forth so that my pussy was mere inches from his lips, knowing that he could smell my wetness. He groaned for a few seconds. And then before I knew what was happening, his tongue was licking my clit and he was holding me on his lap. His mouth was buried into my pussy and I started moaning as he sucked on my clit and his tongue entered me. This wasn’t exactly how I planned it to go, but I wasn’t going to complain. The feel of his warm tongue licking and teasing me was pure joy. It was fucking amazing. So amazing that I was on the verge of an orgasm within a minute. He obviously knew what was happening because he then pulled away and shook his head laughing.

  “Sorry, I forgot. I’m not meant to touch, Ms. Izzy.”

  I moaned as I moved my leg and sat back down on top of him, placing his cock between my legs. And I started rubbing back and forth on him, my breasts bouncing against his chest as he held my hips. I leaned forward and I kissed him. I could feel the tip of him close to my entrance. It was too fast, too soon, but I had no desire to stop it.

  “Fuck.” Jack pulled me off him and jumped up. “Come.” He grabbed my hand and he pulled me towards his bedroom. “I don’t have any protection out here.”

  I followed him to his bedroom. He had a king-size bed and a view that was unlike anything I’d ever seen before. He grinned as he came up behind me and ran his fingers down my spine and down the crack of my ass.

  “I take back what I said,” he said softly in my ear.

  “Oh, what was that?” My entire body was ready to be taken by this gorgeous hunk of a man.

  “This isn’t the worst date ever,” he growled as he pulled me towards him. “This is the best fucking date I’ve ever been on in my life.”

  And then he pulled me down onto the bed with him.

  For once, I agreed with him. This was the best fucking date ever.

  Chapter Ten

  Jack kissed me on the lips and ran his fingers down the side of my body. I trembled as he stared down at me.

  “You’re nothing like I thought you would be, you know?” he said, as he kissed me once more.

  “Oh, yeah?” I said, running my hands down the side of his muscular body, shivering at the warmth. How was it that he was so perfect? How was it that he had a body that looked like it was sculpted by one of the great sculptors? He was even better than Michaelangelo’s David.

  “You’re fucking sexier than I ever thought you would be.” He kissed the side of my neck. “I want you to touch yourself,” he whispered softly in my ear.

  My eyes flew to his. “What?”

  “Touch yourself for me. We played out your fantasy. Now play out mine.”

  He took my hand and placed it between my legs. That obviously wasn’t an unfamiliar place to me, but it was an unfamiliar feeling touching myself in front of someone. I’ve never done that before, but I had fantasized about what it would be like. I closed my eyes. I was horny, and I could feel myself becoming hornier as I played with myself. I didn’t feel ashamed or nervous, and when I heard him gasping, my eyes flew open. He reached down and grabbed my hand, moving my fingers up and down on my own clit.

  “Where the fuck is your condom?” I said, all thoughts of leaving him with blue balls gone. I needed to get fucked by this man. I needed to feel him inside of me. Nothing would feel better.

  “Someone’s a little anxious, aren’t they?” he chuckled as he reached over to his side table and opened the drawer. He pulled out a bunch of condoms, ripped one open, and slid it down on his hard cock. “So, Izzy, what position would you like to start with?”

  “Shut up.” I pulled him down on top of me, wrapping my legs around his waist. He kissed my lips, and I ran my fingers through his hair, pulling hard and moaning as his tongue entered my mouth.<
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  We kissed and rolled around on the bed, and then I felt the tip of his cock at my entrance. I moaned as he slid into me slowly. It hurt slightly, and I gasped. He paused and pulled out, shock in his eyes.

  “Are you a virgin?” he asked.

  “No,” I laughed, shaking my head. “I told you it’s been a while.”

  He stared at me for a few seconds, and I could tell he was trying to figure out whether or not I was telling him the truth.

  “Look, it’s been over a year. I guess I’m a born-again virgin. And it’s not going to hurt for long. Please.” I reached up and pulled him down, and he groaned as I bit his lip and ran my fingers down the back of his ass. I felt the tip of his cock at my opening again, and he reached down and rubbed my clit. He could feel how wet I was. I moaned as I spread my legs for him, and he grunted as he pushed inside me a little bit at a time, until he was fully inside of me, stretching me out, and it felt like heaven.

  “Oh, my God, you feel so good,” I gasped. Then he started thrusting, and my breasts bounced against his chest as he hit all the right spots.

  “Oh, yes. Please, please, please! Jack, fuck me harder. Fuck me harder!” I screamed. That seemed to turn him on even more. Pulling my legs over his shoulders, he fucked me deep and hard, like I’d never been fucked before in my life. His eyes stared down into mine, and when I went to close them, he shook his head.

  “I want to see your face. I want to see your eyes as I make you come,” he whispered then leaned down and sucked on my nipple. Then he reached down and started playing with my clit as he fucked me, and that was all it took. I screamed as he pounded into me, his balls slapping against my underside, and then I came fast and hard, my body shimmying and shaking underneath him. He stilled for a few seconds and then slammed into me one, two, three times, and I felt his body shuddering as he came as well.

  He collapsed on top of me, kissing me on the side of my face before slipping out of me.

  He pulled the condom off of his still hard cock and placed it on the side of the bed. I laughed, reaching over to stroke the side of his face. I’d never expected to be here naked, fucking some strange guy on a first date, but it felt good. It felt amazing.