The Baseball Trip Pt. 04

We both sort of smiled at each other. A bit of a pained look, the shared misery that's best expressed with sullen happiness. We both felt betrayed. Let down.

"OK," Kelsey said, "We're gonna fix this." She pulled out her phone and started texting. I tried to look over her shoulder, but she turned away. Gave me the 'just a sec' sign. A moment later she finished typing and put her phone back down on the bed.

Then she leaned in and kissed me. Our lips had been all over each other's bodies, but somehow this was our first kiss. I tasted at her thin, pink lips and the world felt suddenly all the sweeter. Then Kelsey pulled back, only slightly. Our noses almost touching.

"OK, she said, "here's the deal."

Another light kiss, again on the lips. Smack.

"Julia and Sarah have our tickets. They're going to go get dinner and see the show. They'll be out for hours."

Smack.

"I'm going to stay here. And 'comfort' you. In your time of need. If that's OK with you?"

Smack

I just nodded dumbly. Tried to put our lips back together, but Kelsey held her distance.

"I know I'm not Sarah," she said.

"You don't have to be. You're you - Kelsey. Wonderful, beautiful, amazing Kelsey."

She smiled at me and kissed me again. Then broke apart.

"I'm not upset. Like I said, this is just fun. Nothing serious. No feelings or jealousy or any of that." She snaked her tongue into my mouth. I slid back against her. Gripped at her shoulders and she squeezed back. Both of us holding on. Kelsey stopped us again, then grinned. Cat with canary.

"And with that in mind, you and I are going to spend the evening taking revenge on my older brother. Doing his little sister ought to do nicely, don't you think?" she said.

The grin spread across my face, threatened to swallow my ears, my eyes, all of it. Kelsey was smiling, too. Shyly. Shining. She stood up from the bed, leaving me still sitting there. I noticed Kelsey was panting a little. Shivering. The little blonde hairs on her arms stood up straight.

"Kelsey, I know you're a... I mean, are you sure you want to do this?"

The beautiful teenager responded by reaching down and ripping her shirt right over her head. Bra and all. Gone in one smooth, sweet motion. Her breasts, surprisingly sizable on her small frame, hung high on her chest. Pink nipples stood out sharply.

I ran my eyes over her. Ravenous. Then I looked back up at her face. Seductress, yet also a little scared. Like she knew, in that moment, exactly how much she wanted this and what that meant for her. So flawless and exposed.

She leaned forward and kissed me, almost tentative this time.

"Kelsey, honey, your first time... I mean, my first time with Anna it was terrible. I mean really, really bad. It hurt her and that hurt me and it... You should do it with someone special."

"I am doing it with someone special," she whispered, then kissed me again. Much harder with tongue and teeth. I felt her breasts dangling over my hands. "I'm doing it with you."

Kelsey let me go, then slowly slid down her pants and panties, shimmying them down her legs. Her bare pussy was right at eye level, almost smiling at me, I swear.

"Fffffuck Kelsey." I was definitely going to have to work on other things to say when faced with an amazing, naked woman.

The beautiful teenage blonde stepped forward. Lifted me up so I stood in front of her. Pulled my shirt over my head. Then reached down and undid my belt. My pants pooled at my feet. My boxers joined them. We were both naked, our eyes tracing the shape of each other.

Then we pressed our lips together once again. I grabbed her skinny shoulders. Squeezed. Then turned and pushed her back onto the bed. She crumpled beneath me, held her lips pressed to mine.

"You're amazing," I told her.

"You are too."

"I'm just a guy. A stupid, lucky guy."

We were still kissing. Rolling. I held her arms, her sides, her hips. Tried to keep myself from just diving at her most sensitive parts. Not yet.

"You're THE guy. My guy," Kelsey said.

"So wait. The brother thing from before?"

She giggled a little. "I mean... I'm not going to lie to you and say it isn't a turn on. You know, as an idea. But it wasn't exactly my big brother I was getting off on when I was younger. More like my big brother's best friend."

I rolled her onto her back and started kissing down her jaw to her neck. She sighed and stretched.

"So you've had a crush on me this whole time?"

"Not... God you make me sound like such a weenie."

"You're not a weenie. I'm... You're so fucking fantastic Kelsey and I know you can't just see it yet but just wait. You're gonna blow boy's minds. Especially if you blow their other parts, too."

"Oh brother," Kelsey said and rolled her eyes.

"Oh... sister..." I kept kissing her. Kelsey grabbed my face. Held my attention.

"That would be fun," she said, "But... don't. Not tonight. I want it to just be me and you. OK?"

I smiled, went back down to kissing at her neck. Slowly working down to her collarbone.

"Besides, with awful jokes like that one, I don't know if I'm really ready for this after all."

I moved up and kissed her lips.

"You love my awful jokes," I told her.

"I just hope you get to sucking on my pussy soon so I don't have to hear them anymore."

"Clever girl," I smiled, then moved back down to her chest. I dragged my tongue around the outside of her areola, teasing at her tits without touching their most sensitive spots. Kelsey kept trying to shift herself, trick me into licking at her erect nipples, but I deftly dodged. Finally she just grabbed at the back of my head and shoved me down.

I took the little nubbin into my mouth and held it there, lightly bit at her while she moaned. Gasped.

"Now start licking a little lower, would you?" Kelsey said. I'd forgotten how directive she could be.

"What, like here?" I kissed her stomach. She groaned, then shifted herself upward, making sure my lips would meet their mark.

I stared down at her perfect pussy. Pink lips pouting. Then paused and looked up at Kelsey. The blonde teenager just raised an eyebrow at me. I smiled, then dove into her glistening mound. I started at the bottom, just lapping up her juices, then worked up to her clit. Again, teasing at her.

Kelsey's legs slowly wrapped around my shoulders as I licked from bottom to top, again and again. Then finally I slid a finger inside of her and focused my oral attentions on her magic button.

"Oh... fffffuck that's nice," I heard her sigh muffled through her thin legs. Perhaps for the last time, my finger touched the thick ring of flesh that marked her virginity. I stopped and looked up.

"Do you want me to...? I could do it now and maybe it might not hurt so much when we..."

"No! No. I want it on a cock. Your cock. Please." The sexy teenager strained. I pulled my finger back and found the little bit of roughness on the roof of her snatch. Started petting it lightly while I went back to her clit.

No more playing around, I pressed my tongue hard onto her clitoris and worked it for all I was worth.

"Oh... OH! Close... getting... OH!" Kesley's body went straight. The walls of her pussy squeezed down on my digit. I let it force me out, little bits of white froth on her legs, my hand, the bed. Liquid Kelsey all over. She giggled a little. I slid up to kiss her, then stopped. Some girls didn't like to taste their own...

Kelsey grabbed my face and pulled me down, squeezing my skull so hard it hurt. Well she certainly wasn't shy about putting my head where she wanted it.

"You're a quick cummer," I said.

"Maybe you're just really good at getting me going."

"I hope so. You're so incredible, Kelsey. I just want to make you feel incredible."

"You do. I do. Now, there seems to be something else we wanted to do." She reached down and grabbed my cock. "Oh yes. There he is."

She smiled and jerked me a few times. I was so hard it hurt, and my balls just ached even more badly. Oh crap.

"Kelsey, I don't have a condom. Are you...?"

"I don't have one either," she said, thinking. "It's OK."

"Are you sure? I mean, I'm clean and everything and I know you are, too, but I don't want to like..."

"I want my first time to be bare, anyway. It should be skin on skin. But, like, don't like... cum. Inside me, I mean. It's OK to cum just..."

"Just not in you."

"Yeah. Tits, face, ass, wherever. Is that OK?"

"Kelsey, whatever you want is fine. I just want to make sure I'm doing right by you."

"Good, then what I want is this," she squeezed my cock pointedly, "In this." She pointed at her waiting pussy. It had gone from pink to purple. The lips hung open, obscene. I could see the moisture dripping down and, obviously, I could smell her essence as well.

I tried to slide my mouth back over her but she pushed me away and wagged her free finger. First pointed at my cock, then at her hungry hole.

I'll admit it, at that moment, I got nervous. Kelsey and I weren't dating. We weren't anything. But I didn't want to hurt her or disappoint her in any way and, like I said, I knew what a first time was like for a girl and most of what I knew was that it s-u-c-k sucked. And sure, I'd gotten her worked up with my mouth and she seemed wet and wild but...

Kelsey pulled me forward with my cock. Spread her legs and brought me to her center. I reached up and stroked her hair. Kissed at her cheeks and mouth. She rested the tip of my cock at her entrance. I felt her little nether lips tug at it. Urge me forward. Every instinct demanded I slam home. I held there.

I caught her eyes. Now Kelsey was the one who looked nervous. I smiled.

"Maybe I should suck your... penis."

"My cock?"

"Yeah, like, would you want that?"

"It might help with lubrication," I said.

"In porn they always... Like the girls always go down on the guy before they..."

"How much porn are you watching?"

"Shut up."

"It's not... There's no ritual here. I went down on you because I thought it would get you wet and that cumming would help loosen you up a little. I'll do it again if you'd like, but I don't think that's what you want."

"It's just... You have a really big cock. I haven't..."

"You just told me you watch porn!"

"That's what I mean! It feels really big and I don't want it to hurt."

"Do you want me to stop?"

"No, I want you to..."

"I'll take care of you. I promise. If it hurts, we'll stop. If it really hurts we'll, I don't know, go watch porn and do something else, OK? Incest porn."

"I never should have admitted to that." Kelsey sighed and rolled her eyes.

"It's OK. You shouldn't... I'm going to stop."

I started to pull back, but Kelsey's hand shot down and grabbed my shaft. Held me in place.

"No!" she said, "Don't you dare."

I stroked her hair and kissed her again.

"Just... just go slow," she said.

"And no cumming in you," I said.

"Preferably no."

"And remember why we're doing this," I told her

Kelsey tilted her head slightly.

"To take revenge on your brother."

She laughed and as she did, I slid myself forward. Her laugh sort of morphed into a low groan. Not in pleasure, but not exactly pain either.

"Oh, you're cruel."

"Not nearly as cruel as I will be in a moment," I said.

"Is it... How much? Feels like a lot."

"Just the head. The head of the head, really," I said. My hips were absolutely straining but I held them back. Moved forward a little more. Sheathed in her snatch, it was like my whole existence - every nerve, every part of me - was snaking into that pussy.

There was a whole world of sensations surrounding us - the bed, the sunlight, the beautiful woman beneath me - but I only felt two things: wet and tight. Kelsey was dripping. I could already feel her liquid sliding down my shaft and over my balls. A tremendous little tickle. And yet, at the same time, sliding forward felt like this incredible effort as her pussy walls slowly adjusted to my shaft.

Actually, I felt a third thing. An imperative, a need, to just pound my cock into poor little Kelsey's pussy, pain be damned. And every second I was fighting it, a wrestling match in my head to mirror the one that Kelsey and I were undergoing on the hotel bed.

I looked down at her and saw she was staring forward. Sweating. Panting. Looking little and afraid but also wanting. I smiled and she smiled back. I kissed her lightly on the lips.

"Little more?"

"Yeah."

I let myself lean forward more. I felt it at my tip. The barrier. I knew I could push forward and just...

"Big push coming," I told her.

She nodded, gamely, but I could tell this wasn't going well. She seemed to be mumbling to herself.

"Too much... too much..."

I started to pull back but she grabbed my ass and stopped me.

"I don't want to hurt you, Kelsey."

"Someone will. Eventually someone's going to have to do this and I want it to be you, OK?"

At the same time, she pushed me forward, her hands on my ass.

"What if you sat on me and then you could control it?" I asked.

"No. Want you... Want you to do it. Be my first. Don't... don't you want it? Want me?"

"I do."

"Oh, Ben, you're gonna break my little pussy. Don't you want my... my juice all over your big, hard cock? Yours only. I could be a hundred and there'll always be a little part of me that's yours. I want that. I want you to give that to me"

I went forward a little more.

"That's... that's it. Fill me. Stuff me full. Pound me with that cock. I want to... I want to see it. My blood on your cock. Come on. Show me. Give it to me. I want it so bad.

"This is it," I told her, rearing back for the big plunge. Kelsey nodded, brave face.

I pushed forward, felt my cock freeze in place, then burst forward.

"OH! ooooooooo," Kelsey mewled and I saw a tear pool at the corner of her eye.

"Is that... that it? You whole cock? I got it all?"

I looked down.

"Little more."

"Goddammit, Ben, are you sure you're just average?"

"Are you OK?"

Kelsey tried to shift around and winced.

"Not really, but let's... let's get this over with."

"There's the romance I'm looking for."

Kelsey's face shifted into a little girl pout.

"Oh come ooonnn Ben. I want alllll of it. Haven't I been good enough to earn it?"

I shook my head, readjusted then did my best to slide in to the hilt. My balls lightly scraped against Kelsey's bottom. I leaned forward and wrapped her close.

She sighed, more from relief than contentment. After a minute she seemed to get restless.

"Still hurts?"

"Yeah. A lot. Like, so much. What the hell, you bastard?"

"You told me to."

"And if I told you to jump off a bridge would you do that?"

"If I could land in your perfect pussy? Probably."

Kelsey laughed and I felt it everywhere. In her shoulders as I held them tight. On my cock as her pussy rumbled along with the rest of her body.

"Can I see?" she asked, suddenly.

"You mean, like..."

"Yeah. I want to see it all inside me."

I shifted (Kelsey moaned as I slid back and not in a good way) and let her lean forward to look at where we were joined. There really was some blood on the part of my shaft that was now exposed. The rest was good and buried. Like a weird, dirty magic trick, my cock just seemed to disappear inside the tiny teenager's twat.

"Wow," Kelsey said, "That's so cool."

I saw her eyeing the blood on my cock.

"I really hope the hotel washes these sheets," she said. "Thoroughly."

Sitting slightly up made Kelsey's breasts dangle alluringly, so I leaned forward and took one into my mouth. Just suckling lightly.

"Mmmmmm..." Kelsey said and then slowly let herself lean back, pulling her tit out of my mouth. My cock slid forward with her, re-burying himself in her velvet underground. She kind of hissed in pain as he did so.

"So that's it?" she asked.

"Well, usually we'd move back and forth for a bit until, ideally, we reach some sort of a climax."

"You make it sound so romantic."

Like I said, Kelsey was a smart girl well before she'd grown into a beautiful woman and I could see her logicking her way through this. "Well, let's try that," she said. I smiled and kissed her. Started to withdraw and then slid forward, a micro-thrust, really.

"Ow," Kelsey said, "Ow. ow. ow."

"Sorry."

"Keep going."

I pulled back again - God, this was hard, I wanted to just fuck her so bad, her pussy was so wet and tight and I... I couldn't. I wouldn't. I would make it good for her. I'd find a way.

"Ah! Dammit. Why does this hurt so bad?"

"You get used to it," I said, "Not the pain, I mean, the..."

"The penetration?"

"Yeah. And then it starts to feel good. And then really good. At least, that's what I've been told."

I started sliding back again.

"I don't think I can do this..." Kelsey said suddenly, her voice small.

"It's OK," I said.

"Are you sure? I mean, we could start again in a little bit or maybe I'll just suck you off. Oh my slutty little mouth would love to take your..."

I held my hand up. Looked her straight in the eyes.

"It's OK," I said.

Kelsey nodded meekly. I withdrew. My cock was garish - striped with Kelsey's virginal blood and white streaks of pussy juice. Purple and aching. She looked at me, then slid her eyes down.

"It's fine," I said, pointed, "I'm gonna have to go take care of this. Red cock. Blue balls."

Kelsey giggled and I remembered what it felt like when I was inside her and she was laughing. She curled her legs up to her and wrapped her arms around her knees. She looked young and scared and I went over to comfort her.

"It's OK, just... disappointed," Kelsey said.

"I'm sorry."

"Not you, Me. I'm so mad at me."

"We can try again, you know. Any time."

I heard some bleeping bloops. My phone, rumbling through my pants' pocket at the end of the bed.

"You should get that," Kelsey said, "It might be the girls."

I reached down to my jeans and pulled my phone out of my pocket.

"Ugh. No." I showed her the screen: Jim.

"No, thank you," I said, starting to toss my phone away.

Kelsey raised an eyebrow at me, then leapt forward. I looked down at the naked beauty, all pink and perfect. Her little bum shook slightly as she reached for the phone. Below it, her pleasure center still dark and dripping.

Kelsey slid her thumb across the screen and answered. She lay on her stomach, blonde head propped on her arm. Legs up, feet dangling. Like a high school girl taking a call from one of her girlfriends. Only completely naked. I saw her switch it over to speaker. I sat back against the pillows and listened. Our legs sort of tapped at each other.

"Ben? Hey man, listen. I'm so glad you picked up. What I said before... Look, I don't like how we left things and I was hoping we could... Am I on speaker?"

"Hi Jim," Kelsey said, flatly.

"Uh... who is this? Do I have the wrong number?"

"It's Kelsey. Y'know, your sister?"

"Uhhh.. Hey Kels. Um, why do you have Ben's phone? I really want to talk to him and I..."

"Ben's busy right now," Kelsey said. She put the phone down on the bedspread. Then, pointedly, she rose up on all fours. Almost like we were about to fuck doggystyle. Though that was obviously not what the still-somewhat innocent teenager could possibly have in mind.

"Well, I mean," the phone continued, "Could you go get him? It's kind of important."

Kelsey wagged her head toward her ass, then looked over at me.

Holy... We were about to fuck doggystyle. Holy holy holy holy fuck! Kelsey must have seen my eyes widen in shock because she just smiled and wagged her head at me again.

"He's in the room, Jim," Kelsey said, "He's just busy right now. Too busy to talk to you, anyway."