All In: Calling His Bluff (Gambling With Love)

by Hart, Lane

  Of course with other women I'd never trusted their word on the birth control issue. I wouldn't risk the possibility that they'd try and get knocked up to take as much money as possible. I didn't want to reproduce with a leech. I trusted Jules, and knew that even if she was to accidentally get pregnant while we were together, it wouldn't be a tragedy.

  "Okay, then forget the condoms."

  "Seriously?" I asked with a grin.

  "Yeah. Unless the gold diggers gave you herpes or some shit."

  I laughed. "No, I promise you I don't have herpes or anything else. I've never not used a condom, because like you said, that'd be a helluva way for a gold digger to fuck me over. I can give you proof if you want it. I get checked out all the time just because I like flashing my huge cock at people." It was the long ass cotton swab I hated.

  She laughed. "I trust you. And you know I was only with Aaron, and he was a virgin. Even so, we used condoms and I was on the pill back then."

  "God I hate hearing that prick's name," I told her. "I should've threatened to cut his dick off so he wouldn't have screwed you."

  "Who was your first?" she asked.

  "Amy Sanders."

  "I don't remember her."

  "Yeah, you probably wouldn't since she was two years older than me and Will. She was a junior our freshman year."

  "And?" she asked. "What happened with her?"

  "It happened during one of the first big parties in the basement of our new house. You know my bedroom’s down there, too. She asked me if I wanted her, and as a horny virgin of course the only answer was yes. She took control, probably figuring it was my first time. Hell, she even put the condom on me, then she climbed up and fucked me. It was a wet dream come true, even though I only lasted a minute. Then, no shit, she asked me to take her shopping before the cum dried. At the time, I didn't give a fuck. I would have done anything she wanted to get her to fuck me again. So she sucked my dick or fucked me every day for a few weeks. After her was Shannon Stevens, then Rachel Anderson and so on until I graduated. Pretty much the same pattern, only varying in material requests. I had no idea girls could be whores that young, but they definitely can."

  "I'm sorry," she said softly.

  "I didn't see it then, and I was getting off so I can't really complain. Mixed in with the gold diggers were the girls who didn't necessarily care that I was rich, they'd just heard I was hung and wanted to find out for themselves. That was pretty awesome, and regardless of what they say, women want to be fucked with big cocks. Or at least my big cock."

  "I have to admit that I do like being fucked by your big cock." Her words instantly inflated my ego and the cock in question.

  "From now on, every other man will just be a disappointment, you know." I was an asshole for wanting other men she was with to be a letdown, but I couldn't help it. I'd become more than protective as her older brother's best friend. I wanted Jules all to myself. The thought of another man's hands on her, and God forbid, his dick, made me want to kill someone.

  "I know," she conceded with a sigh, before she changed the subject. "So when you started school at Madison you decided to hide the money?"

  "Yep. No money, no reputation, just me. It was intimidating to not have it so easy and have to actually work for women to want me. It was a hit to my confidence when just “me” wasn't enough. I was so bad at it that they didn't even think I was straight."

  "I think I understand why the Sigs thought you were gay," Jules said with a giggle.

  "Oh, really?" I asked, unsure I really wanted to hear the explanation.

  "Yeah. You look too good to be straight, and when you dress nice you look like you're either rich or gay. Since you hide the money … well, that only left gay."

  I let out the breath I'd been holding. That wasn't so bad. In fact, it was even a compliment.

  "Well damn. Maybe you're right. But agreeing to go see Magic Mike with them probably didn't help my case either," I told her, making her laugh. A full out, belly busting, complete with cute snorts, laugh.

  "You didn't!" she sobbed between giggles. "Oh my God!" She wiped tears from her eyes as she caught her breath. "That's the funniest thing I've ever heard. I can see you sitting there in a theater full of women … it's too funny," she said, and then laughed a few more minutes, making me smile the whole time.

  "Hey, it wasn't all bad. I mean, it starts out with girl on girl action and several titty shots," I said in my defense.

  "Ugh. I forgot about that," she said, and shook her head while a smile still brightened her face.

  "Well, at least you've helped me clear it all up," I told her.

  "Yeah. And now they know you're straight and loaded. They're probably plotting their seduction of you as we speak," she said. When I glanced over she'd turned her head away to look out the window.

  "They can plot all they want-" I started, but was interrupted by the ringing phone. It was mine, and I had a feeling I knew who it was. Will. "It's your brother," I told Jules after reading the screen.

  "Hey, Will."

  "Hey, where are you? I just stopped by your apartment and saw the Porsche was gone," he said.

  "Ah, yeah. I'm in it right now heading to the Parkway."

  He laughed. "You're on the Parkway in your Porsche? Are you feeling okay? Same girl from last weekend?"

  "Yeah."

  "And you're letting her see your ride already? You must have lost your mind bringing out the big guns just to get some ass."

  "It's not like that," I said, maybe a tad too defensively.

  "Whoa. You really like her and you actually trust her." He said it as a statement, not a question.

  "Yeah, I do."

  "Well damn. And you're sure she's not an undercover gold digger?"

  "I'm absolutely certain she's not."

  "Okay. So then why are you hiding her?"

  "I'm not hiding her. I just … like being alone with her. I don't want you scaring her off."

  "Uh-huh. I've known you for thirteen years and this is the first time you've ever blown me off for almost an entire week for a girl."

  "I'm sorry. Look, I'll see you tomorrow night, okay?" I asked, trying to get him off the phone. I hated lying to him, but I hated thinking about what his reaction would be if he found out why I was lying.

  "Alright. Have fun," he laughed, then hung up.

  "Tomorrow night?" Jules asked after I put my phone away.

  "Yeah, I can't keep blowing him off, so I invited him to the Sig party."

  "Oh," she said quietly.

  "Should we just tell him?" I asked her, and she laughed.

  "You want to tell him that you've been fucking me so you could come out and fuck Sigs, in exchange for you agreeing to fuck me every which way so I can fuck other men?"

  "Well, I wouldn't exactly put it like that," I told her. Thinking it over though, I couldn't figure out what I'd say that wouldn't piss him off. "We wouldn't have to tell him how it started out between us."

  "Yeah, I'm sure just the 'we've been fucking each other' part would go over real well. I don't want him to be pissed at you because you agreed to do this for me, and you know he will be, regardless of what you say."

  Will was my best friend, and I didn't want to give him a reason to hate me. "Fine. I guess it's best if we just keep things how they are."

  "You think?" she laughed again, and then turned the radio up, ending the discussion.

  Two hours later I couldn't wait any longer to take her, even though it was still daylight. I found a pull-off on the parkway and prayed no one would come along for a few minutes.

  "You ready?" I asked. She nodded, then climbed out of the car and met me in front of the hood.

  "Wow, the view up here is beautiful," she said, as she looked out over the mountains. The sun was just starting to set. The leaves on all the trees were changing to fall colors, and they seemed to glow under the dimming sunlight. The rolling mountains looked almost purple in the shadow of the coming darkness.

  "The
view is about to get even better," I told her, pulling her to me.

  I kissed her for all I was worth, while undoing her jeans. She didn't even protest when I started lowering them and her panties down her legs. I sat her on the hood to remove her shoes, so I could get her undressed. Kneeling down on the ground in front of her I parted her thighs and raised her hips to lick her pussy, making her cry out and squirm until she came.

  Getting back to my feet I made quick work of my zipper, then pulled her to me, wrapping her legs around my waist as I entered her. Nothing had ever felt so fucking good. I became a man possessed, feeling her tight wetness without the barrier of a condom. I pushed her shirt up to expose her bra covered titties as I pumped in and out of her, refusing to finish until I felt her pussy clench around my cock when she came again.

  "Come for me Jules," I ordered as I rubbed her clit, until her hips rocked frantically with her orgasm.

  "Oh God, Dylan!" she moaned as her back arched off the hood. "You feel … so … good!"

  I knew I'd never forget how amazing she felt, or how gorgeous she looked, laid out half naked writhing in pleasure on my ridiculously expensive sports car while I came in her for the very first time.

  After she relaxed, her limbs were all sprawled limply on the hood.

  "That was even better than I imagined," I told her as I leaned down over her, pressing my chest against hers to kiss her.

  "You're gonna dent your car."

  "I don’t give a fuck. I told you, it'll be worth it."

  "I better get dressed before someone comes along," she said quickly. I hoped her state of undress was the only reason she was in such a rush.

  "Alright. And I guess we can head back. But when we get home, you're going to put on that lingerie so I can take it off of you again."

  "That works for me," she agreed with a smile.

  I helped her dress again, then we sat back down inside the car to leave.

  "You know, I like this car a helluva lot more now," I told her. "And I won't be able to look at it again without thinking about you. How unbelievably beautiful you were, laid out on the hood while I was inside of you."

  When she turned and looked away I reached over and grabbed her chin, to turn her face back towards me. Her eyes shimmered with unshed tears when they met mine.

  "What's wrong?" I asked. She shook her head, and turned away again. "In case I haven't made it clear, I don't want anyone else, Jules. However we started, after Friday night I can't even think about anyone but you. Hell, after that night in Vegas I couldn't think about anyone but you."

  Chapter Thirteen

  Jules

  Dylan's words were still bouncing around my head as we drove down the highway back to Greensboro. Of course he was saying he didn't want anyone else, because Megan wasn't all over him yet. And maybe she never would be. But I had a feeling now that she knew how rich he was, she was going to throw herself at him, and he'd give in to her regardless of her ulterior motives.

  "So Jules, what do you want to do when you graduate in a few years?"

  I laughed as I thought of my future goals. "You know going to school at an expensive private university like Madison to be a social worker is almost as ridiculous as driving through McDonald's in this car."

  "What? No, it's not. Well, maybe if you were paying tuition and that's what you were going to do. It'd take twenty years to pay it all back on a social worker's salary," he said, which was true.

  "I know, but I'm not paying for it, and that's what I want to do."

  "Why'd you decide on social work over psychology?" he asked.

  "After all that happened to Jess and her brother last year, I decided I'd rather work in a place for runaways. You know, somewhere kids can be safe away from their own abusive families. A place where they can finish school and get jobs to thrive on their own, even without their parents. Can you believe there's not a single place for runaways within a two hundred mile radius of Greensboro?" I asked in disbelief before continuing on. "And psychology, well, I just saw it as listening to a bunch of rich kids talking about their rich kid problems."

  "That's a good plan. I can’t even imagine what Jess and Jon went through at home, or how they must have struggled when they first left."

  "Me either. I know social work won't pay well or whatever, but I'd rather do something I'm happy with and that will really help kids who need it than something that will earn more money. What would you do if you weren't going to work for your dad?" I asked, wondering if he'd ever wanted to do something else.

  "Shit, working for a beer company is pretty much my dream job. The fact that it's my dad's makes it even more awesome. What he did with it, going from being a microbrewery to the number three brewery in the country, and moving up in the ranks internationally is pretty amazing. I want to make sure it keeps going strong."

  "Making tons of money doesn’t suck either, right?" I asked him with a smile.

  "Hell no it doesn't," he laughed.

  ...

  A few hours later when we got back to Dylan's apartment, he insisted I put on one of the outfits he'd bought at the sex store. Since he was so excited about the garters and hose I decided on that one after a quick shower. Those, along with the black lace halter top bra, looked pretty good on me … other than exposing my stomach, which I'd rather have covered.

  I stepped out of the master bathroom, expecting Dylan to be waiting for me in bed … but nope, it was empty. Huh. I headed down the hall, and finally found him stretched out on his leather couch watching Harry Potter on his big ass TV. This was just like any other Friday night for me, except I wasn't alone in my dorm, and I wasn't wearing my girly comfy pajamas. Instead I was wearing a slutty black lace outfit that barely covered any skin. Oh, and there were no Reese's, which was a good thing for my fat ass.

  Wearing my roommate's red fuck me heels, that matched my bright red slutty lipstick, I ran my finger through my hair and strutted as best I was capable in front of the TV before climbing on top of Dylan.

  "Fuck, Jules," he said with a big grin, rubbing his hand over my bare ass, then down the garter straps. "You are the sexiest woman I've ever seen."

  "You don't have to try and woo me with B.S. flattery. I'm a sure thing," I said, partially quoting one of my favorite movies. A movie about a hot, obscenely rich man that screws a poor, lowly prostitute. The similarities were unnerving actually.

  "It's not B.S., and if you're a sure thing then what are you waiting for?" he asked with a smile.

  I kissed him and then climbed back off of him, making him quickly scramble up. "Where the hell are you going? Get that fine ass of yours back here and fuck me senseless."

  I headed for the pool table, and grabbed one of the sticks hanging on the wall rack behind it. "You're not up for a game of pool?" I asked, then stretched across the table to reach a few of the balls to rack them, flashing him my ass. There were a few things left on his erotic wish list that we needed to check off. Pool table sex was one, sixty-nine was the other.

  When I looked over my shoulder Dylan was standing there holding his phone out in front of him.

  "Please tell me you didn't just take a picture," I said, straightening from the table.

  "Goddamn right I did. I didn't get one of you on my car, which really sucks. But this one, um, this one is going to be blown up on a canvas so it can hang over my bed," he said as he looked down at the screen.

  My face heated instantly. "No! Delete it and delete it now, Dylan!"

  "No way. You and that outfit ..." he groaned and grabbed the bulge in the front of his jeans. "You're pin-up gorgeous, Jules."

  "If I see that picture on the internet or on your wall I'm going to kick your ass."

  "It won't go on the internet."

  "Dylan, you can't put a picture like that up on the wall. Your parents will see it! My brother will see it!"

  "Don't forget my housekeeper too," he added unhelpfully. "And my dad's already seen you naked in the hot tub."

  "That was dif
ferent, all he could see was my shoulders."

  "Alright, that's enough talking, because it's an argument you won't win. And now you know I'm gonna have to bend you over and fuck you right here," he said, running his hand over the green felt as he stalked toward me. His eyes were on mine and scorching hot when he reached down to undo his jeans, then pulled out his hard cock.

  "Well, I'm not sure I'm in the mood anymore," I countered with my hands on my hips.

  "Oh baby, that's a lie if I've ever heard one," he said, wedging his long leg between my thighs and pressing his massive body against mine. "Your hard nipples, and," his fingers glided over my slit, then pushed into my opening, "Oh yeah, very wet pussy, say otherwise."

  "Umm," I moaned as I held onto his shoulders, unable to argue anymore as my eyes closed with the building pleasure.

  "Now," he said, nipping at my ear before kissing down my neck, while his fingers kept moving in and out of me. "Face down. Ass up. Because you know that's how you like to fuck."

  My orgasm was barreling down on me, making me grab tightly onto Dylan's upper arms to hold myself up, but he pulled his hand away making me groan in aching need.

  "Please," I begged when he turned my body around. I barely had time to brace my palms on the table when he thrust into me hard. My release came immediately, and I cried out as he fucked me harder and harder. There was nothing sweet or nice about this time with him. Just dirty, intense fucking, and I couldn't get enough as I came again, still begging him for more.

  By the time Dylan stopped moving and collapsed on top of my back I may have come three times. It was hard to keep track with pleasure continuously rolling through my body.

  "Was that as good for you as it was for me?" Dylan asked, pressed against me and still breathing heavy.

  "Oh yeah. Multi-orgasmic. So damn amazing."

  "Not using condoms is awesome."

  "Oh shit! I forgot my pill again today," I exclaimed, and he jumped up off of me. "Just kidding. I'm on the shot."

  "Damn, Jules. I think you just scared my dick away for the rest of the night. Hell, maybe the week."