To My Brother's Cocky Best Friend

by J. S. Cooper

  "Oh, yeah? What'd you want to do?" I pulled her close to me so that her breasts were crushed up against my chest then bit gently on her lower lip.

  "I'll show you," she said. With a sexy, mischievous smile on her face, she slid to her knees and slowly undid my zipper. She reached in and pulled out my big, hard cock, giving a little gasp when she saw it.

  "Yeah, I thought you'd like my big C," I tried to joke but I was so turned on I could barely think straight.

  She just shook her head. "Shh," she said. And before I knew what was happening, her lips were around my cock, and she was sucking. She was sucking as if it was a lollipop that she'd been after for months and months and months. I leaned back into the wall and groaned as I felt her warm lips moving up and down on me. It had never felt like this before. I had received many blowjobs in the past, but not one woman had done what Olivia was doing to me right now.

  "Oh, fuck, Olivia. Don't stop." I gasped as she deep throated me. She seemed to be fitting more and more of me into her mouth. I grabbed the top of her hair. "Oh, Olivia, don't stop." I was grunting now, and I didn't care. This was the sexiest thing I'd done in a really long time, and part of the thrill was knowing we could be caught at any time. I was shocked that Olivia was doing this and after I finished, she stood up and looked at me with a sweet, yet slightly embarrassed expression. “That was amazing.” I kissed her passionately wishing I could return the favor right then and there.

  We made our way back into Olivia's apartment about twenty minutes later. She’d brought me to the most explosive orgasm I’d ever had and had swallowed my juices as if they were the finest champagne. My entire body was buzzing with electricity and I knew she could feel it.

  We hurried into her apartment, barely able to keep our hands off of each other. When she pulled away from me to turn the light on, it felt like too long. I followed her into the room and closed the door behind me. I stared at her for a few seconds, relishing her shining eyes and glowing skin, before pulling her into my arms and kissing her softly on the lips. She melted against me, her eyes bright as they stared into mine.

  I pulled away slightly. "Are you sure you want to do this, Olivia? Because if we do this, there's no turning back."

  "I know," she said softly as she kissed me back and then sucked on my lower lip and tongue. "I know."

  "Good, because I'm going to have my wicked way with you. And I'm going to make sure that you never forget who I am."

  "Oh, Tyler," she laughed. "I've never forgotten you yet. How could I?"

  I grinned. "Do you remember that time when you walked in on me in the shower?"

  "Yes, it's burned into my brain," she smiled.

  "What's burned into your brain?"

  She giggled. "You know."

  "No, I don't know. Tell me."

  "Tyler," she bent her head against my chest, avoiding my gaze, "I'm not going to tell you."

  "Hmm, if you tell me, I'll give you a treat."

  "What's the treat?" She demanded.

  "You’ll have to wait to see."

  "Fine. When I walked in on you in the shower that day, I saw your penis and it was huge. And I always thought to myself, 'Wow. I never knew that Tyler would be so well hung.'"

  "Ah, so you think I'm well hung, huh?"

  "I'm not saying anything else about that. What's my treat, Tyler?"

  "Come with me." I grabbed her hand and then I led her towards the bedroom. "Take off your dress for me, please, dear."

  "You want me to take off my dress myself?" She pouted slightly. "I thought you were going to take it off for me."

  "Would you rather I take it off for you? Because I'm very excited right now and I don't know if that dress is coming off in one piece."

  "What do you mean?"

  "I mean, I’m afraid I’ll tear it off you literally. With my teeth."

  "Oh, yeah? I don't think your teeth are strong enough."

  "You want to bet?"

  "No, no!" she said quickly. "Just in case." She undid the zip and slipped the dress off. It fell to the ground and I stared at her beautiful body. She was wearing a black lacey bra and a black thong. I sucked in my breath.

  "Absolutely beautiful. You are gorgeous, Olivia. Absolutely gorgeous." I ran my fingers across her bare stomach toward her panties.

  She gasped. "What are you doing, Tyler?"

  "What do you think I'm doing?" And then I paused as suddenly I stopped. "You're not a virgin still, are you?"

  "What? No!" She shook her head, "Are you crazy? I'm 27 years old."

  "Well, I don't know. I didn’t know if you were waiting for me." She paused and looked down on the ground. "What? What is it, Olivia?" I asked her gently, curious as to why her expression had changed and she looked embarrassed.

  "You want to know something, Tyler?"

  "Yeah, I always want to know something."

  "Well, when I was younger, I was saving myself for you."

  "You were?" My jaw dropped. "What? How did I not know this?"

  "Well, you didn't know because I didn't tell you, obviously. But I had it in my mind that you would be my first, you know? And then you never even flirted with me, so when I got to college and I got my boyfriend, I figured what's the point of waiting?"

  "You were waiting for me? Seriously?" I looked at her in surprise, my heart racing. "I never knew that. I mean, I kind of figured you had a little crush on me when we were younger, but I never thought you had a real crush. I never thought you liked me like that."

  "Well, you know, I kind of did, but then I got over it because you're such a cocky, arrogant asshole."

  "You still think I'm a cocky, arrogant asshole?"

  "Well, maybe not arrogant and maybe not an asshole. But yeah, you're still cocky."

  "I don't think I'm cocky. I'm self-assured."

  "Self-assured? You just think you're the bee's knees."

  "But do you think I'm the bee's knees?"

  "I'm not going to answer that."

  I chuckled. "Okay, then. Take your bra off for me now, Olivia."

  "No, I don't think so."

  "What do you mean, 'no, you don't think so'?"

  "I'm not going to take off my bra and be practically naked when you still have on your clothes."

  "Well, why don't you help me get rid of some of these clothes?"

  "You want me to help you, but you didn't want to help me?"

  "Well, I don't think you're going to rip my shirt, are you?"

  In response, she grabbed the top of my shirt and pulled. A couple of buttons flew off and fell to the ground and my jaw dropped.

  "Wow, you really want me, don't you?" I laughed.

  "Yes, I do, Tyler. Yes, I do want you right now." Before I knew what was happening the rest of my shirt was off and her hands were on my belt buckle. She undid my belt and then unzipped my pants and slipped them down. I stepped out of my pants so that I was standing there in just my boxer shorts, staring at her in just her bra and panties.

  "Oh my God, I want you so badly," I breathed.

  "I want you, too," she whispered and then kissed me.

  "Do you know how long I've waited for this moment, Olivia?"

  "Yes," she said. "Almost as long as me."

  And then we fell back onto the bed. I didn't know where her limbs began and mine ended; all I knew is that I had to touch her. My hand went down her stomach, then stroked down her hips. She gasped as I sucked on her tongue and then my hand went behind her back and undid the clasp of her bra. It fell off easily and my hands quickly took her breasts into them. I pinched her nipples and she whimpered. I loved to hear the sound of her whimper, so I pinched a little harder.

  "Ouch, that hurt, Tyler!"

  "Did it? Let me kiss it better." I leaned down and took one of her nipples in my mouth and sucked on it lightly, gently, and then hard. I sucked on it until she cried out.

  "Oh, Tyler! Oh, Tyler!" I was growing harder and harder. And she reached down and rubbed against my cock in my briefs. "Take your b
riefs off," she said. "Please?"

  "Only if you take your panties off."

  She looked at me with veiled eyes and said, "I think that's for you to do, Tyler." I didn't need her to say anything else. I reached down and pulled her panties off and threw them to the ground before standing up and quickly pulling off my briefs. My cock sprang free and she stared at it with awe in her eyes. I winked at her and stood tall, loving the fact that she was so impressed by my size. I got back down on the bed and spread her legs open wide so that I could view all of her. She looked up at me innocently, and I knew that this was a lot for her, just as it was a lot for me.

  "You can trust me, Olivia. I'm not going to hurt you, okay?"

  "I know. Hurry up and touch me," she said. "I want to feel you, I want to feel all of you. I want you to fuck me."

  "Did I just hear you correctly?" I chuckled. "Did you just say you want me to fuck you?"

  "Shut up and do me good." She grinned at me. "I'm not going to say it again."

  "Your wish is my command, baby."

  I kissed down the valley between her breasts, down to her stomach, and then lower until my mouth came in contact with her clit. I licked it, relishing the gasping sound she made. She tasted so sweet, like strawberries and champagne, and I never wanted to stop licking her up. Her wetness covered my mouth. My tongue licked her opening and she closed her legs and tightened them around my head. She cried out, pulling on my hair as I fucked her with my tongue. I wanted to make her come as hard as she had made me in the alleyway. I paused for a few seconds, wondering if any more of my hair was going to fall out, but soon relaxed again as she whimpered my name and begged me to fuck her.

  My tongue slid in and out of her until her thighs were trembling and then I felt her coming hard and fast on my face, panting and crying out as she orgasmed. I grinned as I licked up her juices and then reached down to grab my wallet from my pants so I could pull a condom out. I ripped open the packet, my fingers trembling with eagerness, and threw the wrapper onto the ground before slipping the rubber onto my rock-hard cock. I stared down into her eyes and kissed her hard, caressing the side of her face as I positioned myself over her.

  I wiggled my eyebrows at her. “Are you ready for some Tyler Redwood loving?”

  She giggled. “Give me some of that BC, Tyler.”

  I growled into her mouth as I thrust my cock inside of her. She cried out as I filled her up, her pussy walls closing in on my cock nice and tight.

  “Fuck, you feel so good,” I mumbled against her lips as I slammed into her. Her breasts bounced against my chest and I leaned down and pinched her nipples. Her back arched and her thigh muscles tightened around me. I groaned as I felt her fingernails digging into my back.

  “Go harder, Tyler, harder and faster.” Her voice was uneven and I loved the frenzy of it all. I grabbed her legs and flung them over my shoulder and increased my pace so that I was slamming into her pussy with gusto. Everything turned me on—the sound of my skin smacking hers, the sight of her lips parted with pleasure, the little moaning noises she made. It didn’t take long for me to build up to an orgasm and I reached down to rub her clit. We climaxed at the same time, gasping and trembling against each other.

  I collapsed on top of her and kissed the side of her face. I let my cock remain in her as long as possible as I loved the warm protection it provided.

  My phone beeped, breaking the spell.

  I groaned. “I should check that.”

  I kissed her on the lips and she smiled lazily in return. I rolled over and pulled my limp cock out of her wet pussy. I grabbed for my phone with one hand and pulled the condom off with the other. As soon as my hand touched the condom, I froze. It felt sticky and wet, and as I slid it off, I realized it had broken.

  “Fuck.” I muttered under my breath and then I looked at the text message on my screen.

  Derrick had sent a message. Bro, good news, I’m engaged.

  “Fuck,” I said again and this time Olivia sat up and stared at me.

  “What’s wrong, Tyler?”

  “Do you want the bad news or the bad news?” I asked her, trying to joke, but instead, my voice cracked.

  “Oh shit, what is it?” She looked nervous and I could feel the blood draining from my face. She was going to absolutely kill me when she found out what I had to say.

  “Well, it looks like the condom may have broken, and uhm, congratulations are in order, Derrick just got engaged.”

  She gasped and I attempted another joke.

  “It’s not so bad, right?”

  Chapter 15

  Olivia

  * * *

  “It's not so bad, right?”

  Tyler's words reverberated in my head. Was he joking? It's not so bad. These were the worst two things that I had ever heard in my life! One, how did a condom break? How long had he had this condom? Years and years and years? And why of all nights did he have to choose to use this condom with me? And why did it break? Oh my God. If I found out I was pregnant, I would be absolutely dead. My parents would kill me, and Derrick would kill me, but I didn't care about Derrick right now because what the fuck? Derrick was engaged to Tiffany? Was he out of his ever-loving mind?

  I couldn't believe it. My brother, who said he'd never get married. My brother, who never dated one woman for more than two months, was now engaged to a woman he had known for two days? Oh, my gosh. It didn't even make sense to me.

  “What do you mean he's engaged to Tiffany?” I said to Tyler as he stared at me with worried eyes.

  “Um, is that what you want to talk about first?”

  “Yeah. That's what I want to talk about first. He just told you he's engaged? Read the text message to me.”

  Tyler opened up his phone again and cleared his throat while he said, “‘Hey, bro, good news. I'm engaged.’ That's it.”

  “That's it? Are you sure he's not joking?”

  “I don't know why he'd joke about something like that.” Tyler cleared his throat. “Um, but yeah. Shall I text him and ask him if he's joking?”

  “Yeah, please do. I want to know what’s going on. And Tyler, how did your condom split or break or whatever?” I tried to keep a reasonable tone because I didn't want to get angry, but I was really angry. How could this have happened? Yes, we just had the best sex of my life, and yes, I wanted to do it again, but whoa, I was totally, totally out of my mind right now.

  “Um, I don't know what to say, Olivia. It's not like I planned this.”

  “I know it's not like you planned this, but how did it break?”

  “Olivia, I don't know. These things happen every once in a while.”

  “What'd you mean these things happen every once in a while? I've never heard of it happening before.”

  “Um, go on to Google and search. You'll see it's happened plenty of times.”

  “I don't I want to go onto Google right now, Tyler. How long have you had that condom in your wallet?”

  “I told you I haven't had sex in a long time. So … it's been a while.” He sighed. “Look, I'm sorry. Obviously, I didn't plan for this to happen. I mean, if I would have known it was going to split, I wouldn't have used one.”

  “What do you mean, you wouldn't have used one?”

  “I'm joking. I'm joking.” He held his hands up.

  “Of course you would joke at a time like this.”

  “I would have used one, Olivia. We don't want you to get pregnant.”

  “No, I don't want to get pregnant.” I sighed. “Oh my gosh. I just don't know what to do.”

  “Well, you could always get the … What is it? The morning-after pill?”

  “Yeah, I guess I'll have to do that.”

  He paused and said, “Unless you don't want to.”

  “Unless I don't want to what?”

  “Unless you don't want to get the morning-after pill.”

  “Why wouldn't I want to get the morning-after pill?”

  “I don't know. In case you want to have a baby.”


  “Tyler,” I looked at him and narrowed my eyes. “What do you mean in case I want to have a baby?”

  “I'm just saying, if you want to have a baby and this happened and we ended up getting pregnant then, hey.”

  “Tyler, this is the first time we've had sex. We're not even in a relationship. Do you hear me? We cannot have a baby together right now.”

  “I mean, I don't mind. I'd love to have kids with you.”

  “Tyler …” I stared at him in shock, not sure what to say. “I mean, you know I like you, and that was amazing, but we aren't even dating.”

  “Well, maybe we should be dating.”

  I was starting to feel confused and flustered and angry and Tyler was making it worse. “Tyler, I think you need to leave.”

  “What do you mean? It's the middle of the night.”

  “I mean, I think I need to be alone right now. I need to call my friends and I need to talk to them because this is just a lot.”

  “You don't want to talk to me?”

  “Tyler, no, I don't want to talk to you because I need to talk about you. This is crazy.”

  “Just about the condoms thing or the great sex as well?” He had a cocky grin on his face.

  “Tyler, really?”

  “I'm just curious. I mean, I know you're mad. It's not like I planned this, you know.”

  “I know you didn't plan it, but it's just a lot, okay? I'm feeling overwhelmed and I just can't have you here right now. I need to talk to my friends.”

  “Okay. Are you going to tell them the sex was good or bad, though?”

  “Really, Tyler?”

  “I'm just curious what you thought so I know for next time. Do I do it the same way, do it differently?”

  “The next time? That's a big assumption, isn't it?”

  “Olivia, the way you were screaming my name, I'm pretty confident there will be a next time.”

  “Ha ha, Tyler. Ha ha.” I couldn’t believe that this was what he was focusing on right now. Was he trying to make me crazy?

  “Ha ha indeed, Olivia. But if you really don't want me again, then okay.” He had a pitiful look on his face now.