All In: Calling His Bluff (Gambling With Love)

by Hart, Lane

  Will: Good for you, sis. Glad to hear you're broadening your sexual horizons with my friend.

  Hell no.

  "Alright, I trust you. I just hate lying to him, you know?" he exhaled, rubbing his palms down his sheet covered thighs before he suddenly went wide-eyed. "Wait, you're not a virgin are you? Because if so, I can't-"

  "I'm not a virgin," I interrupted him. "But to be honest, I've only been with one guy like three times, missionary only, and that was back in high school."

  "Aaron Barnes?" he asked with narrowed eyes.

  "Yes. You remember him?" I was surprised Dylan recalled the name of the only person I ever really dated. Aaron and I had both been two years behind him and Will in school.

  "Of course I remember that douchebag."

  "Whatever," I said, rolling my eyes at his insult. Aaron was a nice, sweet guy. Dorky, but sweet. I'd never tell anyone that Aaron had three different occasions of premature ejaculation before we finally had sex for the first time. So goes the sad story of my sex life. "So how should we start?" I asked to get things moving along.

  "On your knees," he said quickly. "Oh, but get naked first."

  "What? Why do I need to be naked to suck your dick?" I asked, insecure about voluntarily getting naked in front of him so soon. Not much different from getting naked in front of Nick, thirty minutes after meeting him though. But Dylan seeing me that way was … weird. He'd known me forever and I didn't want to just stand naked and exposed in front of him.

  "Men want you naked when you go down on them. Come on, Jules. I've been dying to see what's hiding under that sheet of yours all fucking night."

  He wanted to see me naked? That's ... surprising, and he was going to be disappointed. But if we were going to do everything then he'd be seeing me good and naked on several occasions. More so than the two previous quick glimpses he'd had. I wouldn't mind seeing him completely naked either, and that was only fair.

  "If I have to get naked, then so do you," I countered.

  He gave me a cocky grin. "If you wanted to see me naked so bad, all you had to do was just ask."

  My face heated up. "That's not … I didn't mean …" I couldn't figure out how to respond to that.

  "I'm just fucking with you. I'll drop my toga as soon as you drop yours."

  Resigned to get it over with, I finally undid the halter top around my neck and let the sheet pool at my feet, then hooked my thumbs in the sides of my white thong to push them down my legs. Once again, it took all of my willpower not to cover my lady parts up.

  "Holy fuck, Jules. I'm gonna come before you even touch me," Dylan said, then cleared his throat and added, "You can, ah, leave the heels on."

  I couldn't take my eyes off of him as he stood up to lose his own toga and white boxer briefs, kicking them off with his flip flops. I didn't have time to appreciate his incredible body before I panicked. The man had not been bluffing about his size.

  "Jesus Christ!" I exclaimed when I saw his long, and I mean longggg, hard cock that reached up clearly past his bellybutton. "There's no way all that is going to fit in my mouth!"

  He laughed as he wrapped his big hand around his gigantic erection and stroked it. I swear the damn thing kept right on growing even larger right before my eyes. "Don't worry. It doesn't all have to go in."

  "Oh, okay. Good," I exhaled as I tried to get the courage to approach his intimidating one-eyed monster. Unlike Nick's, Dylan's cock was not only much, much longer, but straighter, and so thick I had a feeling it might even hurt squeezing in tight spaces. But I wasn't opposed to trying. Just a little … nervous.

  It was embarrassing how wet I was getting between my legs just standing here looking at his length. Where Nick's was rather unattractive and unappealing, I had to admit that Dylan's cock looked … pretty damn incredible. Just like the rest of him.

  "Before we go any further, there's something really important we have to do first," he said, his tone deadly serious. "Where's your ruler?"

  I laughed, just as he probably intended to try and put me more at ease. "I know you've already measured yourself."

  "Oh course I have, but no one believes me. I need an unbiased witness to confirm that I am in fact hung like a motherfucking horse."

  "Now you're just being ridickulous," I told him and he threw back his head back and laughed.

  "Fine, we can save the ruler for later, because I guarantee that when you put your mouth on me I'm going to get even bigger. But I need to know now if you want me to stop before I come or not," Dylan said, pulling my attention back up to his face.

  "You mean, am I going to ... swallow?" I asked and he nodded.

  "You don't have to. Some girls hate that shit, others don't mind. But you need to tell a man in advance so he won't piss you off."

  "Then no, not this time. If that's okay?" I asked. I needed to take baby steps with his big dick.

  "Hell yes, that's okay. It's no big deal," Dylan assured me. He looked around our room then finally grabbed some tissues from the box on our dresser before sitting back down on the edge of the bed.

  "Now what?" I asked. His deep green eyes looked up and down my naked body for several more seconds, making me feel even more self-conscious. At least he hadn't laughed or flinched in disgust yet. In fact, his gaze looked almost … hungry.

  "Come here," he said softly. I took a deep breath then went to stand between his long, spread legs. He was so tall we were almost eye-to-eye even though he was sitting down.

  Dylan's hands reached and grabbed my hips to tug me even closer to him. "Can I touch you?" he asked. I nodded, knowing he meant more intimately.

  Those big, warm hands of his slid up my sides until they cupped both breasts. His thumbs brushed across my tight nipples making me gasp. For the past year I'd been thinking about how it felt to have him touch me like this, and wanted to feel his hands on me again. The tingly sensation of his caress sent pulses of pleasure all through my body.

  "Damn, your tits are so fucking amazing, Jules. There's not a single man that'll be able to resist them. Well, no straight man," he added, his eyes finally leaving my breasts to look back up at me with a smile.

  "So I should flash men to make them want me?" I asked. A small moan slipped from my lips when his mouth suddenly moved forward and covered one of my nipples. I had to reach out and grab onto his broad, muscular shoulders when his tongue licked over the sensitive tip and my legs started to feel wobbly.

  "Hell no," he said quickly, before his mouth moved to the other breast, taking my nipple between his lips and giving it a gentle tug. "You better make them work for even a glimpse. Men like a challenge, and if you hold out long enough then they'll do anything you want just for a chance to see you naked."

  "After I lose some weight maybe, but ..."

  Dylan grabbed my small hand from his shoulder and covered his cock with it, stopping me mid-sentence. Well, he covered a portion of his cock with it. "I'm hard as fuck just looking at you, damn it. You don't need to lose weight. You're beautiful and sexy, Jules, and the only reason I agreed to this is because I'm a horny bastard."

  "Yeah, I know. You can't wait to come out of the closet and fuck some sluts, so let's get on with it," I told him, as I dropped to my knees between his legs. "So?" I asked.

  He groaned as he looked down at me then swallowed so hard I saw his Adam's apple bob. "All you've got to do is put your mouth on our dicks and we'll come. The wetter the better, and the head is the most sensitive, so you don't have to deep throat for it to feel good."

  "Deep throat?" I asked.

  "How much of a gag reflex do you have?" he asked running his hands through my hair and making me shiver from his gentle, affectionate touch. The gesture felt at odds from the large erection currently staring intimidatingly at my face.

  "I don't know," I admitted.

  "Then just start slow and only take as much as you're okay with."

  "Alright," I agreed, then with one hand holding him at the base, leaned down to wrap my lips around
the rim circling his tip.

  "God. Damn," he muttered under his breath, and closed his eyes.

  I ran my tongue over his dripping slit. It caused him to suck in a deep, shaky breath, so I kept it up. His hands moved away from my hair and both grabbed fistfuls of my comforter on either side of his thighs.

  I continued right on along with my exploration, moving my mouth around his smooth, hard cock, and licking the underside with my tongue as I went down and then moved back up.

  "Fuck yesss." His body shuddered and then he moaned, his voice deeper and huskier. "Please … please don't stop."

  I liked knowing I was responsible for making a big, sexy guy like Dylan feel good, and wanted to see what other reactions I could invoke.

  Here I was with the man I'd been crushing on my whole life, naked and on my knees with him in my mouth. I never thought anything like this would happen between us, even after the night in Vegas. The real life version was better than all my fantasies. Hell, I was surprised at how much I was enjoying having my mouth on him. I actually wanted to keep going for my own pleasure. I couldn't help but think about feeling him somewhere else, moving in and out of me. All big and swollen. Hard as a rock.

  Less insecure, I leaned forward to take more of him, blissfully closing my eyes as I guided his yummy, king-size cocksicle into my mouth. When I felt his tip hit the back of my throat, I sucked as I pulled away.

  "Oh hell yes, Jules," he groaned. "Do that again."

  When I opened my eyes he was watching me. Still looking up at him, I ran my tongue around the rim of his head again before I covered as much of him as I could take. Dylan gasped and moaned encouragement, then he reached down and filled both of his hands with my breasts. As he began kneading them in his large palms, warmth spread through me, making me grow even wetter between my thighs. I began sucking him faster and harder, using my hand to counter the movements of my mouth as I reveled in his touch, so freaking eager to please him. Too soon, he warned me he was close and pulled my head away.

  His hand covered mine on his length, guiding the strokes until he came with a curse, cum spilling down our fingers. He tightened both our grips, stroking furiously until his cock began to soften. After he cleaned us up with the tissue he fell backwards on the bed that seemed half his size.

  "Damn, Jules. That was sooo ... fucking … good," he said through gasps as his smooth naked chest rose and fell quickly. His arms were thrown limply on either side of him, one hanging off the bed. "Fuck. I'm gonna come again just thinking about … your mouth … so damn incredible. Jesus. I'd kill for a fucking condom right now."

  While he rambled ego inflating things, I wanted to keep exploring his amazing body with my mouth. Licking up his golden treasure trail to his flat stomach, and all around his belly button…but I thought that might freak him out.

  "That wasn't as bad as I thought it would be," I admitted. It was amazing how I felt more confident and sexy just after getting him off with my mouth. I'm pretty damn sure it wouldn't have been as enjoyable for me if I'd been sucking Nick off instead of Dylan. And if cock fighting was an Olympic sport, the man in front of me would hands down take home the gold every year.

  "Honestly, I really like sucking your cock. Can I practice again tomorrow and maybe try the whole swallowing thing?" I asked, as I stood up from the floor. Hell, why wait until tomorrow? Looking down at him he appeared ready to go again, and I wanted to taste him.

  While I was busy staring at his package, Dylan suddenly reached and grabbed me, pulling me down on the tiny bed with him, and making me squeal.

  "Now it's your turn," he said, flashing a devilish grin from above me.

  "My turn what?"

  "To come," he said, before sliding down the front of my body. I raised up on my elbows to watch as he went to his knees on the floor. In one swift movement he pulled me by my legs until my ass was almost hanging off the foot of the bed. Just as quickly, Dylan hooked his arms around my thighs to spread them wide before guiding them over the top of his muscular shoulders.

  "W-what are you doing?" I asked as I tried to squirm out of his firm grasp. "This is supposed to be about me learning ..."

  "I'm not a completely selfish asshole. If you give, you shall receive," he said, as he kissed my pelvis right above my waxed bikini area. No, he couldn't be going where I thought he was.

  "Wait, don't … Oh God!" I exclaimed. My head fell back and my pelvis jerked off the mattress when his tongue licked a path right up the crease of my lower lips.

  "You seriously don't want me to eat you out?" he asked. He looked up at me from between my legs with deep, hazy green eyes while pressing open-mouth kisses on my inner thigh. "Because I'd really," several more teasing kisses, "Really, like to taste you."

  "I-I don’t know."

  "What do you mean you don't know? No one's ever licked your pussy before?" he asked, and I gasped as his tongue did just that again.

  "No."

  "No? Jesus. Then let's see how loud I can make you scream your first time," he said. Swiping his tongue over my flesh again, he took my breath away when he simultaneously dipped two fingers into my entrance. "Mm. You are so fucking wet. Did sucking my cock really get you this turned on?"

  "Y-yes." I was barely able to respond with that one word answer, because my brain was short circuiting from pleasure overload. I'd never felt anything like it, and I was ready to beg for more.

  "You sucked me so fucking good. I can't believe my cock was the first one you've ever put in your mouth. Now it's only fair that I get to eat your pussy until you come all over my tongue."

  "Oh! Oh yes!" I moaned when his mouth covered my clit and sucked. Instead of trying to get away from his hold, my hips reversed course and began thrusting urgently toward his magical mouth and fingers.

  "Oh God, Dylan! I'm gonna … oh!"

  "You've had an orgasm before, right?" He may have asked something of the sort, but my pulse was thundering in my ears.

  "No!" I answered his question while whimpering because of his pause. "Don't stop! Please, Dylan," I begged. My body was wound up so tight it felt like I was going to snap. He laughed when I grabbed handfuls of his hair to grind my pussy against his mouth with utter abandonment.

  I don't really remember exactly what happened after that, other than Dylan's tongue moved in and out and all around my pussy until the world spun. My body became possessed and out of control, trying to levitate off the bed. Tremors racked through my limbs as I screamed and sobbed incoherently with the mind-blowing release of all that pent up pleasure.

  "Good God," I gasped out when I was able to speak the English language again instead of gibberish. "So that's what they call an orgasm? I had no idea they'd feel so freaking incredible."

  Dylan's laughter rumbled through me from where his mouth was moving up my stomach. I was too freaking relaxed from the ecstasy I'd just experienced to even care about him being near my flabby midsection.

  "So you liked that, huh?" he asked while his hands and mouth continued north, teasing my breasts. His tongue licked circles around one of my nipples before he sucked on it, making me squirm.

  "Nope. It didn't do a damn thing for me," I told him sarcastically. I'm sure there was a goofy-ass smile on my face when I finally gave in to my longing and combed my fingers through his hair.

  "I guess I'll have to try harder this next time," he laughed, then his mouth went back down to my sensitive flesh.

  "No, no, no. Oh … fuck ... yes!" I screamed as the pleasure hit me faster and even harder than before. I panted while my body tensed and bowed, riding out every single wonderful wave against his tongue.

  "Was that better?" he asked, kissing the insides of my still shaky thighs.

  "Wow."

  "Oh baby, it'd be even more wow if I could sink my cock into you and fuck you until you come again. Next time," he promised as he stood up from the bed. I liked how he'd called me "baby", and the idea of a next time already had arousal pooling low in my belly again.

  I wa
tched as Dylan unfortunately pulled his boxers on and then threw the sheet back over his tall, magnificent body. "I better head back or I'm gonna have to walk home. See you tomorrow?" he asked with a raised blonde eyebrow, while flashing me a knowing grin.

  "Yes," I nodded, sad to see him leave, especially since I knew he was going back to the girls he actually wanted to be with. Which reminded me of my side of our deal. "Wait a second," I told him, jumping up to grab my lipstick from the dresser. I noticed my body, especially my legs, wasn't really excited about me trying to make it work so soon after all the energy-zapping convulsions.

  Using the dresser mirror, I applied the red color thickly on my lips. When I turned around Dylan grabbed me by my waist and yanked me against the front of his body before his lips covered mine. It was only then that I realized we hadn't actually kissed during the mind-blowing orgasms.

  When his tongue darted into my mouth, like it had between my legs, tasting of my arousal, I couldn't hold back my moan, or stop my legs from going weak. The man knew how to kiss. Every-fucking-where.

  My arms wrapped around his neck so I could run my hands through his hair, unable to resist mussing it up a little more. I swiped my tongue over his and he groaned and gripped my hips tighter as our kiss deepened. Dylan's hard length pressed into my stomach, ready to go again, making me feel all needy.

  I somehow managed to pull back to kiss down his throat, leaving lipstick along the way. I didn't stop sucking on his neck until I gave him a very obvious hickey.

  "Damn, Jules," Dylan moaned, and then reached down to grab my ass as I kissed his Adam's apple. "You're making it really hard to leave."

  "There, now you look like you've been with a woman … or a transvestite," I laughed as I stepped back out of breath, looking over my handiwork.

  "Yeah, well it still might take a few PDAs to prove," he said as he ducked down to look at the marks in the mirror.

  "Sure, as long as Will's not around."

  "Fuck, we'll have to work around him," he said, then quickly grabbed something off the floor, too fast for me to see. "Lesson number two tomorrow?" he asked. I was already looking forward to it.