Dirty Naked Poker Pt. 02

Sam took his fingers, now lightly dusted in Kristen's marinade, and lubed up his penis. He put his other hand on Kristen's ass and then gradually moved himself into position. Then slightly slid forward.

"Oh!" Kristen broke out of her mumbling, "Hey Jay. Jason?"

I suddenly straightened.

"Come... come here for a sec," Kristen said. If Sam noticed, he didn't show it. At least he had the decency to not just... drive it home.

Kristen's eyes were wide as saucers and her mouth was even wider. Her tongue slightly lolled out. I looked at Emma. She just shrugged, holding her bestie's hand to her chest, protectively.

"That good?" I asked when I got close enough to whisper.

"Can't... can't tell," Kristen said.

"There's her hymen," I heard Ashley tell Sam.

"Jason," Kristen said, "JJ. Jay bird."

My sister's pet names for me. She'd been using them all night, I noticed. Spoken not in the mocking way that Kate or Ashley had used them, but like Emma herself did. With love, affection and even a little awe.

"I... Oh! Careful that... Just... just go slow Sam, OK?"

He grunted back.

Kristen motioned for me to come closer. Her lips brushed my ear. Sam was still plumbing her depths. I saw Kristen's free hand was knuckle-white on the table.

"Jason," Kristen whispered, "I just wanted you to know... I... I wish it was you."

And then Kristen's eyes rolled back into her head and she screamed in pain as Sam busted through her maidenhead.

A little tear ran down her cheek, but her face stayed still. When she had her breath back she continued,

"OK? I wish it was you that was doing... Yeah?"

I leaned in and kissed her lightly on the lips.

"Yeah. Yeah, me too."

I looked up at Emma to see if she'd heard and clearly, she had. She just smiled at me, a sad little wistful thing. Then suddenly, my anger drained away like Kristen and Emma had pulled the plug from me. I started filling back up again, but with sad.

"Just... just wait a sec..." Kristen called back, "Ssssssooooo... So full... I just, I just gotta get used to it."

"Yeah," Sam said, "Yeah of course. OK. Just let me know."

Sam wasn't a jerk, by any means but he wasn't exactly a gentle lover, either. I'm sure Kristen's comments about his size made him a little more willing to do things her way, though. Smart girl.

But the position Sam'd chosen said it all, really. was Kristen's first time and I don't think Sam really thought about it - how it should have been for Kristen. He was interested in fucking her for his own sake. That's not how a girl's first time ought to be, in my opinion.

Emma leaned in and whispered into Kristen's ear, though I could hear it all, easily.

"You think that's big," she said, "Maybe it's a good thing you chose the starter penis before getting on our big boy over there."

Emma nodded knowingly at my turgid cock. He popped a little in approval. Kristen kind of giggled. A pained little laugh.

"Yeah... probably..." Kristen told Emma.

"You OK down there?" Sam asked.

As I said earlier, Kristen - quiet, conservative Christian Kristen - transformed into someone very vocal and even a little rude once someone started at her. We knew the shock and pain had drained away, then, because she started talking. It was like getting the whole play-by-play on her first foray into fucking.

"That's... yeah... OK. I think I'm used to it a little. Just go ahead and..."

"You sure?"

"Yeah... yeah. Sure. Go for it."

"What's it...?" Emma started, then realized maybe now was not the best time for a Q&A.

"It's... he's inside me it's... strange. I feel so... so full. Like I never realized I was empty until something was in me and I... OH! He's working back and forth with me and it's like I can feel every ridge. Every bump. Every bit of him. AH, wait. Kinda hurts, too, though..."

I watched as Kristen slowly slid on the table, forced back and forth by Sam's furtive movements. I thought about how it would have been with me and realized I'd betrayed her. Like I'd done with my sister.

Damn.

I leaned into Kristen.

"I'm sorry," I said.

"F... for what?"

"I should've... I'm just sorry."

"Don't... oh that's nice... don't be sorry, OK?"

I stood up and watched, doing my best to keep my eyes on Kristen's reactions, rather than to what was causing them. She kept her eyes all scrunched up, made hot white nail marks in Emma's palms. Lay there and let Sam go as well as she could. The rollercoaster starts, you realize that you do not want to be on it, but at that point there's nothing to do but ride out your misery and hope for a quick end.

"That's... that's nice that's...ow, hang on just... your penis is like, it's jabbing me at a weird angle and it's like... oh wait, oh there it is. That's nice...OW... fuck, why am I so sore, it's just..."

"You want me to... you know?" Sam asked. He clearly did not want to... you know. His face was bright red and little bits of sweat ran down his face, his chest, his arms. He was bent over at the stomach like an old man on a walker, hands gripping Kristen's shapely buttocks. He didn't even pause as he asked if he should pause.

"No no... it's ok... keep... keep at it," Kristen said. Sam kept at it.

"It's...oh it's such a strange feeling, I've never... No wait, slow down... just slow down for a sec, OK?"

Everyone looked at Kristen, her blonde hair pasted to her forehead, her eyes no longer wide but small and not so much frightened as just... frustrated.

"It's feels like... kinda dry," she said, "Like I need to make more lubrication or just... I feel like I'm covered him in my stuff but it's like, kinda burning and OH!... Oh no, keep... keep going Sam, just... just keep... ffffffffuuuuuck."

Her head down now, Kristen stopped talking. The table gave little creaks... faster, faster then finally Sam threw his head back and...

"Ahhhhhhhhhhh," he shouted to the ceiling, arms thrown back.

"Oh!" Kristen said, she looked back.

Sam's head was down. His hands gripped her ample buttocks as he rocked back and forth, ever slower.

"Oh, Sam," Kristen asked, sort of aroused, sort of confused, "Sammy, did you cum?"

"Oh. Oh yeah," Sam said. He staggered back. Leaned against the wall and caught his breath.

"Kristen that was awesome. You're fucking awesome babe, you know that?"

"Thanks," Kristen said, kind of blushing.

"Did you... y'know?" Sam asked.

"It's OK baby. Maybe if you just..."

Sam answered by ripping off the condom. Then he threw it up against my wall where it stuck with a splat. There was a little streak of red blood running along the side. The last of Kristen's innocence, just tossed aside. He couldn't even use a fucking trashcan for it?

I put my hand on Kristen's shoulder and rubbed it, lightly. I just didn't know what to do. I'd always heard people say their first time was awful, but I'd never really understood how until that moment. I mean, I'm sure my first time was terrible but my girlfriend had been around a bit, and well, it's always good for the guy, no matter how bad he is so...

"First time's always bad, hon," Ashley said, "Don't worry, it gets better. Way better."

"Yeah, OK," Kristen said, still lying on her stomach. "It was nice, really, I got it. It just, I dunno it was weird, I just couldn't get wet enough and then the way Sam's penis was pushing into me and it just felt so big and my... I just felt sore, that's all. And a little dry... No it was really good. It was really fun. I'm really really glad I did it. Really."

"OK, well, you guys clean yourselves up, OK? We've still got a couple of hands to go," Ashley said.

Kristen groaned, then started to roll off the table. But Emma, still at the beautiful blonde's side, sort of gently pushed her back down. Then Emma bent over and rested her forehead on Kristen's. They shared a warm, weak little smile. Emma smiled wider and kissed her bestie right on the lips.

"Hang on," Emma said, "Hand's not over."

Everyone stopped. Ashley was already sitting back at the circle, shuffling the cards. Sam was walking out of the bathroom, his penis flaccid and fulfilled. I stood to the side, as confused as anyone.

"We didn't finish the bet," Emma said.

"It's cool," Sam said, "Jason you're off the hook. Though I'm sure it'd be a heck of time for both of us."

He winked, like we could ever share the same in-joke, now.

"That's fine," Emma said, "But not what I meant. Sam, Jason and Kristen, you were all in the hand when Jason raised to fuck. Everyone called and then showed their cards, right?"

I looked over at my sister and raised an eyebrow. Where was she going with this?

"Right," Sam said, "I had the Ace so both Jason and Kristen owed me a fuck. But I'm commuting Jason's sentence because... ew. Just no dude."

"Jason, what card did you have?" Emma asked.

"I had the jack of diamonds," I said, my old lucky card from fucking Kate. All hail the mighty jack of diamonds.

"And Kristen?"

"I had the 9, I think?" Kristen said from the table. It was weird the way she was just lying there, splayed. "No wait, I had the 10. Sorry, it was the 10 of hearts. Sorry."

"Don't be sorry," Emma said. She looked at me, her eyes asking: 'you see where I'm going with this now?' I looked back in a way that said 'no, no I do not.'

"Are we all good here?" Sam asked.

"Ugh. Really people?" Emma slapped her bare thigh with her palm, "You'd think that when you have the chance to... Whatever. Sam's Ace beat both Jason's and Kristen's cards. So Sam gets a fuck from Jason and Kristen. But Jay's jack beat Kristen's ten. So she still owes him a fuck."

Wait. Wait what? Holy fucking jack of diamonds! Lord of all cards, may the jack of diamonds forever be hallowed, holy fucking fuck!

"Emma I..." I started, but stalled.

"She's right, I guess," Ashley shrugged, "Does it matter?"

"Emmy I don't think I want to..." Kristen started. Emma shushed her, then turned and whispered,

"It'll be alright. Trust me."

""Kristen owes me a fuck I guess technically? But, ummm, I don't want to do anything that would... I mean she said she's pretty sore so..."

"It's OK," Emma said, "She's totally fine. Right Krissy? Tell him you're totally fine."

Kristen gave her bestie a look that said she was most certainly not fine. Emma knelt down and the two of them bickered back and forth for a moment. All I could really make out was Emma's end point.

"... and I was right, right? It was fucking awesome?"

"Yeah," Kristen said, almost dreamily.

"OK, so trust me now. OK?"

The ship tilted and groaned. A little "ooooooo" that seemed strangely dirty in the circumstances.

"OK," Kristen said.

"Good," Emma patted Kristen on the buttocks, like post-pep talk, and then turned to me.

"Go for it, JJ. You're good."

"Go for what?"

Emma gestured at her friend, lying on the table, head buried in her arms, like it was the most natural thing in the world. Throw a fuck into my friend, big guy!

"Emma I don't..."

"Jesus, do I have to... OK, come here."

Emma grabbed my elbow and pulled me to the back of the boat where no one could hear.

"Listen," Emma said, "You owe me big time, buster, so you're gonna do this for me, understood?"

"Emma, I... I don't think that's how this works. I hurt you badly and I solve that by... fucking your best friend? Not even porn is that ridiculous."

"Jason. Jay Bird. I... I'll admit I was really mad at you. Still mad. I'm still pissed at you for all your... bullshit. Look, Sam and I we... well we kind of cooked up this idea where... You know what, it doesn't matter. That's my best friend on the table there and she's hurting. It was her first time and it just totally sucked and I mean, soon it's gonna be my first time and I..."

"Wait, Emma, you're a virgin?"

"Yes. Shut up. Anyway, look, it should have been special for her. You heard what she said. I want you to make it special for her, OK?"

"Emma, I don't want to hurt Kristen. I've already done enough to fuck things up and I don't think fucking's gonna fix it."

"See? That's my point. You're not... you're not standing there just waiting to get your rocks off. I ask Sam for this, you know what he's saying? Hell yeah! And Kristen ends up in the same sucky spot, I promise you. You care about Kristen. You want her to feel good and I know KNOW that you'll make it happen for her. Just like I knew you'd get Kate last night and help Krissy out in our circle jerk this morning. I just... I know my big brother. He always sweeps in and saves the day. That's why I... You're gonna help Kristen. I just know you will."

"This is the weirdest weekend..."

"I dunno, remember Aunt Jack's cocaine wedding at the zoo in San Francisco?"

"Not funny."

"I wasn't joking..."

I groaned in surrender, then I walked over to Kristen's backside.

"So," I rested my hand on her exposed buttock, like it was a bedside table, "How do you want me to..."

Kristen rolled over slightly, searching me. I couldn't read her look. Fear? Desire? A little of both? Her eyes were suddenly like little microcosms of the summer sky. Bright blue with streaks of white. It was hard to tear myself away.

"You're really gonna do her?" Ashley asked, suddenly standing. Cards forgotten.

"Bet's a bet, right?" I looked at Emma. She nodded.

"I was thinking," I continued, "you might enjoy it more if you were on top, could control how we go. Or like, if it was missionary you might..."

"No," Emma said, "same thing. No changes."

"Just do her and be done with it, eh?" Ashley asked.

I looked over at Sam, standing in the corner, staring off into the distance. He hadn't said anything and I felt my stomach clench a little.

"Apples to apples?" I asked, "This isn't some... double-blind, placebo-controlled study we're doing here. I'm trying to do... I'm just trying to help Krissy. Like you said."

Emma crossed her arms and glared me down.

"OK, play that same song."

Gingerly, I helped Kristen roll back onto her stomach. She rested her head onto her folded hands. She shuffled her pudendum a little, putting it back into the starting position.

Her pussy, tight and pink before, now looked red and raw. Maybe a little angry. Already gaping and almost certainly ready. I reached over and ran my finger over Kristen's opening. She made little gasp that sounded like pleasure.

She was plenty wet, I'll tell you. Not Emma dripping, I'll grant, but there are waterfalls that look dry compared to that girl. If I was doing the weather report for Kristen's quim I'd say it was super humid with ongoing showers throughout the day and a 100% chance of penis by the afternoon commute.

Satisfied that Kristen was still in a condition where she might be satisfied I took a condom out of the box that Ashley had brought out and started to tear it open. I thought about asking her to slide it on for me like she'd done for Sam, but figured I was already getting more than anyone could ask for.

"Hang on," Emma said, "No condom."

"Em?" Kristen looked up, surprisingly small and scared.

"Not exactly the same then," Ashley said.

"I'm sorry, but what the fuck?" Sam shouted, "What's so special about him that's..."

"You're right Sam," Emma said, "I'm sorry. I just... I think based on what Kristen was saying about staying wet... That is, I'm hoping it might be better for her if there's no condom. Y'know? Like maybe she's allergic or something?"

"Oh what a load of crap," Sam said. He started pacing, swinging his arm like a boxer.

"She might be right," Ashley said, "Some people, the condom just makes it... I mean, it always feels better skin to skin but..."

"Emmy," Kristen said, "I guess that kinda makes sense but I don't want to..."

"Jason's totally clean, right JJ?"

"Umm, yeah, I guess, but I don't want to get Kristen, y'know..."

"I'm not on birth control. The pill," Krissy said, "I mean... it's against the church and I know that sounds kinda stupid now, but..."

Emma pressed on,

"But I'm sure you're in the safe part of your cycle, right? Rhythm method? All that?"

Kristen just shook her head, once, solemnly.

"I think, maybe... I think maybe that's why I've been so... y'know, ummm horny?" Kristen said the word like it was the dirtiest thing that could ever be said, "This whole weekend, my body is just begging for... y'know. Penis. Cock. And stuff..."

"Emma," I said. I'd been down this road, seen the end, turned around and walked back. I could draw the whole thing from memory.

"You'll pull out," Emma said, "Before... y'know?"

"We did the whole 'pull out' thing last time, remember? That did not go well. Well, I mean it did, but..."

"You'll pull out, Jason," Emma said, suddenly serious, staring me down. She crossed the room and then walked me back into the corner.

"You will," Emma said, "When you start to feel like you're gonna cum, you pull out. I don't know why that's so hard for you boys, but... You'll do it on her back or her tits. You'd like that right? Cum all over Krissy's gorgeous titties?"

Holy fuck it was hot to hear Emma talk about her bestie's breasties.

"OK to knock her up on her second time, I guess," Ashley said, chuckling.

"I'm serious, Jason," Emma said, "I don't care if you're glued into that girl. Even one of your potent brother-spermies goes in there, I'll take my fucking revenge. You hear me?"

"Fine," I said, "But then as long as we're making changes, I want Kristen to lie on her back, not her front."

"Fine," Emma said. Tough negotiations, these. You don't see the Camp David accords going into this level of detail. Of course, that's probably because you don't want to watch them, either.

Kristen rolled over on her back, languid and slow. She looked at me, legitimately nervous now. Her breasts shrank from impossibly immense to merely massive when she was on her back.

I know I've spent a lot of time on Krissy's titties but I'll tell you what. Her breasts were fine, but it was her hair - golden, poker straight, cool to the touch, long down to her bottom and thick enough to cover her front - that's what made her so astonishing. She was also pretty as all hell and in good shape from tennis, too. Maybe a little thick but like I said, I like that. Whatever. There was Kristen's fantastic hair and there was everything else. She made Rapunzel look like Captain Picard.

I reached over and gathered Kristen's hair, like pulling up dainty daisies. Then I lowered her locks over her chest, covering her little ears, her chest, her breasts. She smiled at me. I shrugged. A happy little shake.

"When you're ready," Emma said.

I looked down at the amazing woman lying in front of me. Her legs hung open, limply. Her pussy stared back, still gaping, as if to say, 'Well? what are you waitin' for?'

"You ready?" I asked her.

"Yeah," Kristen said, "Yeah, ok."

Just like with Sam. Same sort of half-permission. It would be different, I promised myself. I narrowed the whole world down to just Kristen and me. Her pussy and my cock. I ran my hands up and down her flanks, her butt, her thighs and ankles. Our eyes, already engaged.

As Kristen's lips let way to the head of my raging cock, I saw her pupils widen slightly. I ran my hands through her thick blonde pubes. Traced them from her tummy, down over her pussy to her cute little pucker and then back and around again.

Kristen rested on her elbows. looking down, trying to see our joining. Her mouth hung open slightly. She panted as I pushed in a little further. Made a soft, silent whine.

"That's, that's... Yeah I'm OK," Kristen said.

"Keep talking to me, babe, OK? Just keep... keep telling me what you need."

"I... OK... I need you to go a little deeper. It's... It's still pretty sore, but..."