All In: Calling His Bluff (Gambling With Love)

by Hart, Lane

  She let out a little moan as her head fell back, making my dick even harder.

  Picking her up I sat her on the edge of the bed to strip out of my clothes. Jules's green eyes were unfocused with lust as she watched my every move, her expression now more desire than apprehension, at least.

  I went ahead and grabbed a condom from my dresser to have ready, then climbed up on my high, king size bed. I waited for her to come to me when she was ready, instead of rushing her. Damn, Jules was probably going to need those wooden steps the furniture store tried to sell me to get on and off the bed. At six-four I told them that shit was just ridiculous, but she'd fall and break her neck getting down.

  What the hell was I thinking? It wasn't like she was going to be in and out of my bed for years. This would only last a few weeks, if I was lucky.

  Jules started crawling across the bed towards me, biting her lip and looking incredibly sexy. I reached for her, pulling her on top of me to taste her lips again. After a few seconds our mouths found an easy rhythm, and her body finally relaxed, lowering down until it was flush against mine. I couldn't hold back my groan at the feeling of her soft, warm skin rubbing against my own.

  I reached around to grab her ass with both hands, grinding her lower body into my hard cock, making her breath hitch. I was getting too eager, and distracted from my original plan. I rolled us over until I was on top of her, and started kissing my way down her body. Speaking of distracted, I had to put my mouth on her amazing tits.

  Jules's back arched and she made sounds of pleasure when I started devouring her heavy breasts with licks, nips and suction.

  Trailing a hand down between her legs while my mouth molested her nipples, I slipped underneath her panties. Working her magic spot, I had her coming in less than a minute. But I wasn't done with foreplay yet. I wanted her dripping wet and so fucking ready for my huge cock.

  I slid down the bed, taking her panties with me as I went. Then, lifting her hips up off the mattress with my hands cupping her ass, her heavy lidded eyes met mine before I licked her moist slit, making her writhe and moan. I worked urgently on her clit, needing to get inside of her before I died.

  Jules screamed my name to the heavens when she came, cradling my head to her body with both hands to keep me right where she needed me. Her body's response, her moans, and her taste made me crazy. Even as my balls threatened to explode, I couldn't quit pleasuring her with my mouth. I didn't, until she finally begged me to stop after she came the third time.

  I grabbed the condom and rolled it on while giving her a few seconds to recover from her last orgasm. Holding my weight up on my forearm, I lined my cock up to enter her. Her hips went wild just from my tip touching her overly sensitive flesh.

  "Let's try it this way first," I said through gasps. "And if it feels okay then I'll fuck you from behind." She nodded as her hands dug into my shoulder blades, urging me to push inside her.

  I stayed above her to watch her eyes, and make sure she was okay as I slowly eased into her.

  "Oh God," she said softly. Her eyes were closed, so I wasn't sure what that meant.

  "Good or bad oh God?" I asked, but I was pretty sure I knew which. Her pussy was still clenching around my cock from the aftershocks of her recent orgasm. It was too damn good, and I just knew I was going to embarrass myself by coming faster than a virgin.

  "It's good … Oh!" she cried out and grabbed onto my shoulders when I pushed in gently and hit her cervix, going as far as I could go. After her legs wrapped around me and she started raising her hips, I pulled back and thrust into her again, making her cry out.

  "Still good?" I had to ask again, and she nodded. I was dying from the brutal assault of pleasure starting at my cock and taking over my body, while trying to hold back to make sure I wasn't hurting her. "Okay, just say 'Ow' if something hurts, so I'll know the difference."

  "Don't stop," she said pulling my mouth down to hers. I started moving faster and harder when she didn't say otherwise. Surrounded by her tight heat, with her tongue plunging in and out of my mouth was making it damn difficult to hold off. Finally she started panting into my mouth and I knew she was getting close, right before she pulled away. I felt her pussy tightening around me, taking me right along with her, and making my body shudder in ecstasy.

  "Oh! Oh God, Dylan," she cried out as her back arched. Her nails dug into my arms while she bucked underneath me. With her eyes closed, pink lips parted in an 'O' while pushing her beautiful breasts towards me, she was absolutely gorgeous. I wanted to see her like this, coming underneath me, over and over again.

  I stayed inside her, feeling the incredible aftershocks until she finally came back down again. When her bright green eyes finally blinked open, she looked up and gave me a satisfied smile.

  "Better than Aaron?" I asked, hating that the prick took her virginity in such a shitty way years ago.

  She laughed. "Hell yes. So much better."

  "Goddamn right," I said, unable to help my own grin when I brushed my lips lightly against hers.

  "Now I know what all the fuss is about," she said, looking relaxed while rubbing her hands comfortingly through my hair. Being with her like this felt so damn easy and … right, like we'd done it a hundred times before. I'd worried it might be awkward, but it was anything but that.

  "Does that mean you're up for another round?" I asked, relieved it'd been good for her.

  "I'm ready to beg you to fuck me again," she responded, making me laugh.

  "That won't be necessary. Give me a minute to recover and then I'll gladly make you scream my name again."

  Her face went rosy red on top of our flush from arousal. "Don't be embarrassed," I told her, kissing each of her warm cheeks. "Men love to hear you scream their name. It's nice to know the woman you're fucking hasn't forgotten who's getting her off."

  "That ever happen to you before?" she asked with a smirk.

  "Hell no," I said unable to help my cocky grin. "A woman can't possibly forget when Big Dick Dylan's fucking her."

  "Ha! That's hilarious," she laughed, throwing her head back on the pillow. My mouth went down on her exposed neck, making her squirm when I licked and kissed her sweet, salty skin. "Damn, that tickles. Stop, stop!" she pleaded between giggles, pushing her palms against my unmoving chest.

  "Okay," I finally agreed, when my dick stood at attention again because of her squirming underneath me. "But only because I'm ready for round two. Now I want you face down and ass up, because that's the way I like to fuck," I quoted the song lyrics, as I climbed off the bed to grab another condom.

  "Are you serious?" she asked when I came back to bed. I was covered and ready to go again and she was still on her back.

  "Yes, I'm serious, woman, so get your ass up. Trust me. Did I let you down the first time?" I asked, with a smug smile. She shook her head, then rolled over, going to her hands and knees.

  "Goddamn," I said, as I palmed her ass once it was in the air. "I don't know which I like better, your perfect tits or your incredible ass. I think it's a tie for both making me hard as fuck." Kneeling behind her I lowered my hand between her legs, feeling her wet slit, and penetrating her with two fingers to make sure she was good and ready again.

  "Oh!" she moaned, and rocked back, already trying to fuck my hand.

  "Remember to say 'Ow' if something I do hurts, and any fucking thing you want when it feels good."

  "Oh God," she moaned, in response to my fingers moving in and out of her.

  "You ready?" I asked.

  "Yes. Oh! Oh God yes!" she cried out as she came on my fingers. I didn't let her finish. I grabbed her hips and plunged my cock into her.

  "Oh fuck!" she exclaimed, louder than anything I'd ever heard from her mouth.

  "This okay?" I asked, holding still until I knew she was alright.

  "Yes ... it's … really good. Please don’t stop."

  Thank God, I thought as I started moving in and out of her. I wanted to make her feel so damn good that no other m
an would ever come close to how I gave it to her. Wait. Where the hell had that possessive thought come from? That wasn't helpful for what we were doing here. I was supposed to make her feel sexy and more confident so she could fuck other men. I didn't want to dwell on how shitty that thought felt. Being in her was too damn good to worry about that now.

  "You know I've got a lot more cock, baby. You want it?" I asked her, doing my best to push aside the insane jealousy that had just tried to suffocate me.

  "Yes," she said, in almost a sob.

  "You want it harder and faster?" I asked, giving her a taste of both with the next deep thrust.

  "Yes! Fuck me harder, Dylan," she cried out, making me forgot everything else. Tightening my grip on her hips, I picked up the pace and fucked the ever-loving shit out of her.

  "Ohhh! Oh that feels good! Right there! Yes!" she screamed as she pushed her hips back against me. I could really get used to hearing her cries of pleasure.

  God it felt amazing pounding into her, taking her higher and higher until her insides clenched around my cock, knowing I was the only man who'd ever fucked her like this. Aaron may have taken her virginity, but I was the only one that had ever made her scream in ecstasy.

  "I'm almost … oh … please Dylan!" Jules was right on the edge and desperate to go over. Hell I was too, so I reached down and worked her detonation switch until she exploded around me.

  Her pussy squeezing my dick while she screamed my name in gratitude for getting her there felt incredible. So incredible I couldn't last any longer. With my own growling curse I thrust one last time into her before I collapsed on top of her back, my weight flattening her to her stomach.

  "Damn, Dylan," she said, between gasps. "You were right. That felt so fucking good."

  "Glad I could show you something new," I told her, kissing down her sweaty shoulder and back. I couldn't keep my hands or mouth off of her, even though my lungs begged for more oxygen. "And I'm glad you liked it. Does this mean you'll let me keep fucking you?" I was becoming addicted to being with this woman, and already wanted to take her again. I had no idea that sweet and shy Jules would be such a sexy little wildcat in bed.

  "Uh-huh. Is it always like that? Aaron just stuck it in then came instantly all three times."

  I laughed, even though my first few times were pretty much the same. Then I tried to think about how being with Jules compared to the hundred or so other women I'd been with, the majority of which had been back in high school. I couldn't pick out a single one, they'd all been so similar and unmemorable.

  "Was it … was it okay for you?" she asked hesitantly before I could respond, wrongly mistaking my silence as me being dissatisfied.

  "No, it's not usually like that. Being with you is fucking incredible, Jules. I can't get enough." Hell, who was I kidding? Sex with Jules was easily the best sex of my life.

  "Really?"

  "Hell yes. It was even better than all the times I've imagined fucking you, which has been more often than is appropriate for my best friend's little sister," I told her. "And I'm glad we finally got to finish what we started in Vegas."

  "Would you … do you think we would have … if Will hadn't interrupted?"

  During our weekend in Vegas, Will and I had left our hotel room to head to the lobby for Tyler and Jess's wedding when I realized I'd left my key card in the room, and might need it later. I grabbed Will's card and went back up to get my own, walking in right before Jules put her dress on. There she was, standing in nothing but a black strapless bra, thong and heels. I'd almost thrown her down and fucked her right then. Instead, I'd mumbled an apology, grabbed my key card and took one last quick glance before getting out of there for her sake.

  All through the wedding, and then later that night at the club with Will, I couldn't stop thinking about Jules. How fucking sexy she'd looked. How much I wanted her, and wondering if it was even remotely possible that she might want me too. So when Will went up to some girl's room later, I headed back to ours to see Jules. The second I walked into that dark room my cock compass pointed me right to the bed with her, and I couldn't help myself. I needed to know if I had a chance with her. Rather than just come out and ask her, I climbed under the covers and reached for her, hoping she wouldn't tell me to fuck off. When she told me she didn't want me to stop, I lost my shit. I'd tried to take things slow so I wouldn't scare her away, but I'd been about two seconds away from tearing all of our clothes off and fucking her when Will came back. My balls ached for a week afterward, despite how many times I jerked off.

  "God knows I wanted to in Vegas," I admitted. "Especially after I walked in on you changing. I couldn't stop thinking naughty thoughts about you after that."

  "Pervert," she said and I felt her laugh underneath me. "You weren't drunk that night, were you?"

  "No," I admitted. "I just felt like a shitty friend to your brother and wanted to try and shrug off my guilt. I don't know if you noticed that night, but I had to go take a cold shower to jerk off because I wanted you so bad. Now that I know how good it feels to fuck you, I really hate we got interrupted."

  "Me too."

  "Hell, I even laid there for hours considering waiting for Will to fall asleep to climb back in your bed. Although, now that I've heard your orgasms it would have been impossible to keep you from waking him up," I teased.

  "You could have covered my mouth with your mouth or hand to muffle my sounds," she said, surprising the shit out me.

  I pulled my semi-hard cock out of her to lay down on the mattress so I could see her face. "Are you telling me you would've let me fuck you with your brother sleeping just a few feet away?"

  She smiled and rolled to her side to face me. "Yes. Or you could have fucked me when he was in the shower the next morning, instead of lying and saying you'd been drunk the night before."

  "You naughty girl." I pulled her against my chest and kissed her. I wondered what else she might be up for during our little sexual education arrangement. "Would you let me fuck you in public where someone might come along and see us?" I pulled back and asked.

  She bit her bottom lip while she thought it over, before she answered. "Yes."

  "God yes. You're a sexy little exhibitionist." My dirty mind was already working overtime to come up with ideas of things we could do. "Would you let me fuck you with someone else watching?" I asked. I remembered my buddy Tyler talking about how hot it was to get it on with his girl in the back of a taxi.

  "Yes," she said softly, making me groan.

  "Want to try the public sex lesson tonight?" I asked hopefully.

  "I want to experience everything, and I trust you, so yeah. That sounds pretty hot."

  I couldn't help my grin as I kissed her again. All our talk of voyeurism had gotten me hot and bothered, so I pulled Jules's body against mine for her to feel that I was ready again, if she was. When she threw her leg over top of mine, my cock nestled perfectly right between her spread thighs. Since I still had a condom on I reached down and pushed myself inside her. Jules gasped and made that sweet, sexy, "Mm," sound of pleasure each time I rocked forward. With every thrust she became more frantic with her tongue in my mouth and hands in my hair.

  I'd never had sideways sex before, but hell if it wasn't amazing. Our limbs were all wrapped around each other like pretzels, our bodies pressed close without having to break our kiss. In this position the more than a foot height difference between us didn't cause any problems, and God she was so fucking tight.

  Thanks to my two previous orgasms I was able to keep this round going on and on like the Energizer bunny, even after her pussy put my cock in a vise with her orgasm. I was pretty sure I could give her at least one more.

  Grabbing her leg behind her knee, I pulled it higher up my side as I drilled into her harder and faster. I was getting close when I felt the first telltale signs of her walls tightening, signaling she was almost there again. "Give it to me, Jules. I want to feel your pussy squeezing the fuck out of my cock again."

  I rea
ched for her clit and as soon as my fingertip touched her she came. I stilled deep inside of her, letting her milk my release from me. "Oh yeah, just like that, baby. Fuck!"

  "Oh my God," Jules said between breaths, pressing her face against my neck. "Are you trying to … make me … OD on orgasms? What was that … like the seventh?"

  I laughed and kissed her forehead. "I can't help it. I'm trying to make up for lost time."

  A whole fucking year had gone by when we could've been doing this together. She wanted me, I wanted her. We could've been fucking like rabbits behind her brother's back. At the present moment, high on endorphins, being with Jules was so worth lying to my best friend.

  Jules yawned and then asked what time it was. I couldn't have cared less, but I looked around at the time on the DVR box for her.

  "Five-thirty."

  "Mind if I take a nap?" she asked softly, and I smiled knowing I'd worn her ass out.

  "Of course not," I told her, finally untangling myself from her to throw away the condoms in the bathroom. When I came back she'd already passed out where I'd left her. God she looked good lying naked in my bed. I didn't bring women here, just like I didn't show off my car, so Jules was the first woman I'd been with in my bed since I’d moved out on my own three years ago. Maybe I could talk her into coming back home with me tonight, too.

  I climbed up on the bed and gently pulled the covers out from under her limp body. I cuddled up to her ass, covered us both, and threw my arm over her waist to hold her against me. This is really fucking nice, I thought. A minute later, I was out too.

  Chapter Five

  Jules

  I woke up feeling like I'd been asleep for hours, but it was only seven. God, I'd been so knocked out from multiple orgasms that I'd even drooled, which was embarrassing. Turning my head to the side I saw that Dylan was still asleep behind me, so maybe he hadn't noticed my grossness. It was unfair how good he looked while he slept when I knew I had to be a mess. Ugh, I needed a toothbrush and a shower ASAP.