Bailey Ch. 02

All characters in this story are 18 years old or older.

Sorry for the wait. Still wrestling with this whole writers block thing. I got a lot of good feedback on Chapter 1 and I'm very thankful for everyone's comments. So, here's chapter 2. Hope you all enjoy as much as the first one. There's some slight violence and a bit of drama in this one, so if you're not into that sort of thing, you might want to skip this one.

Whiskey

*****

It was a Monday afternoon. The lunchroom was packed, like usual, as I walked through the double doors and spotted Bailey sitting with the usual crowd. Nick and Tyler were talking about one of their favorite bands coming to town when I walked up behind them and yanked Bailey's hood over her head from behind.

She jumped, startled and spun around on her stool to face me. "You jerk," she sighed, pulling her hood back again.

"Did I scare ya?" I asked, with a grin.

"No, of course not!"

"Don't let her fool you," Nick chimed in. "She was terrified."

"Shut up," Bailey sighed, before punching Nick in the arm.

I sat down between Bailey and Tyler and cracked open a can of soda that I had bought from the vending machine. For a few minutes, me and Bailey just sat in silence, while Nick and Tyler babbled on and on about getting tickets to see Rancid, and Michelle was busy talking to her friend Nicole about something.

I was thinking about my conversation with Mark a few days earlier, and I wanted to talk about it with Bailey...after everything we had done together on Saturday, I felt it was necessary to establish exactly what would happen next...but, I felt weird bringing it up in front of everyone else.

"Hey," I said, giving Bailey a nudge. "Can we talk?"

She blinked, looking as nervous about it as I was.

"Sure," she said, standing up and taking my hand.

Bailey then proceeded to lead me through the lunchroom and outside, onto the patio where students were allowed during the lunch period. She pulled me all the way over to a corner where none of the staff could see; the smokers corner, as it was called. Bailey proceeded to light up a cigarette and smiled at me. "So, what's up?"

Now that we were alone, I didn't think I could bring myself to say what I had intended to say.

Why was I so nervous about it, anyway?

We had hooked up on Saturday, so why did the idea of asking whether we were boyfriend and girlfriend or not scare me so much? After hesitating for way longer than I had intended, I sighed and shook my head. "Nothing," I said, smiling at her.

"Guess I just wanted you to myself..."

"Oh yeah?" Bailey giggled.

She flicked the ash from the tip of her cigarette, before pulling me further into the corner and pressing her lips to mine. I kissed her back, the taste of cigarettes heavy on her breath...I didn't mind. "So," she said, as she broke the kiss.

"Did you enjoy what we did on Saturday?"

"Uh...y-yeah, it was...great," I laughed.

"Great?"

She was looking at me now, as though she didn't believe me like she might have thought that I could be lying to her or something. "Just great?"

"Okay," I said, with a grin. "It was incredible."

"Now that's more like it," Bailey said, before kissing me again.

"Whoa!"

We both jumped and looked up to find Michelle and Tyler standing there, staring at us in shock. It was Michelle who had reacted first, and was now on the verge of laughter, as she stepped forward and hugged me and Bailey both together.

"Oh my God," she said, as she hugged us tightly.

"You two are together now? You're such a cute couple-"

"No, we're not," Bailey interrupted, laughing as she pushed her friend away and gaining my attention. "I mean...we sort of are but, not really."

"So, you're like...friends with benefits?" Tyler asked.

"Yeah," Bailey replied, looking over at me. "Friends with benefits...right, Ryan?"

Well, there was my answer and I hadn't even had to ask the question...Tyler and Michelle had done that for me.

"Right," I nodded in agreement.

The bell for next period rang and Bailey groaned in frustration, stomping out her cigarette and turning towards me; off to the gym, we went.

Gym class went the way it typically always did.

Other students harassing me, and tossing basketballs at me, laughing hysterically when the ball would hit me right upside the head. Sure, I'd had a brief break from all of this garbage, after Tyler and Nick had found out last week. Most of them stayed away from me after that but not everyone had gotten the memo.

When gym class was over, I hid in the bathroom like I always did...God, I was so fucking pathetic, I hated myself sometimes. As soon as I was certain that the locker room and shower room had cleared, I stepped out of the bathroom and started undressing. I grabbed my towel and made my way to the showers but I paused, as I heard the shower running already.

Bailey.

I had completely forgotten that she would be in there. Not that I minded at this point, and for obvious reasons, I was pretty sure she wouldn't give a damn either. I smiled, stepping into the shower room and sure enough, there she was with her back turned towards me.

My eyes took in the sight of that gorgeous bubble butt of hers, as I slowly walked up behind her, hoping to catch her by surprise like I had done earlier in the lunchroom. This time though, Bailey turned around and caught me, before I could scare her.

"I was wondering what was taking you so long," she said, with a seductive grin.

"Sorry," I said, blushing. "I usually take cover in the bathrooms...you know...until everyone else is gone."

Bailey frowned, taking me by the hand and pulling me under the stream of hot water. "They gave you a hard time today," she said, referring to the usual crowd of bullies.

"It's nothing," I replied, as she rubbed my head where I'd been struck with at least two or three basketballs.

"It's not nothing," she said, defensively.

"Ryan, you should seriously stand up for yourself one of these days...you can't let them keep getting over on you like that."

She was right, I knew but, just the mere thought of getting into a fight caused me some pretty intense anxiety. Bailey wasn't going to push the matter though...she could see the frustration in my eyes and she smiled, leaning in to kiss me on the mouth. My cock was instantly hard as a rock, and I felt it pressing against her much bigger one, which was equally hard.

"Maybe we shouldn't in here," I suggested, not knowing if it was the best idea to get it on in the boys shower...we could easily get caught by a staff member or another student.

"Relax," Bailey said softly. "We got time for a quickie..."

With that, Bailey was pushing me down onto my knees in front of her, until I was eye level with her raging hard-on.

I put aside my uneasy feelings and wrapped my lips around the head of her cock, quickly engulfing the whole thing and started trying to deep throat. Bailey moaned, running her fingers through my hair and looking down at me with lust.

"Take your time," she whispered.

"Don't push yourself...you're doing just fine..."

I was still getting used to the whole deep throat thing. I had done a pretty decent job last time but, I still had a little trouble suppressing my gag reflex enough so that I wouldn't choke from time to time.

As Bailey held my head with both hands now, she began thrusting her hips forward, fucking my mouth with more and more speed and force. Her heavy wet balls kept slapping against my chin, water from the shower splashing against my chest. I pulled back just a little for a moment and looked up at her, to see her biting her lip and staring back down at me. "Fuck, Ryan...I'm gonna cum soon," she warned, as she thrust her cock back down my throat again.

That's exactly what I wanted to hear.

I started bobbing my head faster again, reaching up to play with her small but, firm breasts, as I pushed her closer and closer to her climax. Finally, her legs began to shake and she forced my head all the way down, holding it in place, as she started grunting. "I-I'm cumming," she gasped.

"I'm cumming..."

Leaning her head back against the shower wall, Bailey reached up with both hands and quickly covered her mouth, to try and stifle her cries as she erupted like a volcano in my mouth. Her cock pulsed and throbbed, rope after rope of cum splashing across my tongue and shooting straight down my throat. Just like I had done the day before, I swallowed every single drop, loving her sweet, sweet taste.

Bailey finally finished cumming, still a bit shaky, as I continued sucking on her sensitive and now softening cock until it went completely flaccid.

"Great job, Ryan," she giggled, as she reached down to pat my cheek. "Now, we should probably hurry up and get out of here."

I stood up and we shared a quick kiss, before shutting off the showers and rushing out to the locker area to get dried off and dressed.

"Meet me outside, after last period," Bailey said, as we went our separate ways.

"I'll be there," I promised, before darting down the hallway.

I just barely made it to class, before the bell rang...thank God for that. I would have hated to get detention, on just my second week at this place.

After the last class of the day had ended, I made my way outside to meet with Bailey; she wasn't out there yet though, so I wound up standing around and waiting. As I was waiting, I looked up and panicked, when I noticed two of the students from gym class that loved throwing balls at me...Tim and Billy.

Of course, they just had to notice me standing there too and instantly started walking right in my direction; great, I thought. Here we go.

"What's up, loser," Billy said, shoving me hard. I stumbled backward and fell onto my ass, and Billy and Tim both started laughing hysterically.

"Fuck off," I said, angrily.

"What did you say?" Billy asked, kneeling in front of me and getting right up in my face. "You got a big mouth, for such a little shit."

"I said, fuck off," I spat, becoming angrier now.

My reaction didn't seem to help me though, as Billy suddenly straight up slapped me across the face. "Don't talk to me like that," he said through gritted teeth.

"Hey!"

We all turned around, to find Bailey standing a few feet away from us, glaring at both Billy and Tim. "He said, fuck off..."

Billy and Tim glanced at each other, then back to Bailey, before Tim scoffed and shook his head. "Whatever," he said, and proceeded to walk away first.

Billy watched his friend walk off, then glared back at Bailey, before flipping her the middle finger and following after Tim...I was saved from more torment.

And it had been Bailey, who had saved me.

"Thanks," I said, as she walked closer to me.

"I owe you for that."

"It's no big deal," Bailey shrugged. "I figured you go through enough of their bull shit during gym, why should you have to put up with more of it, after school lets out?"

"You're not wrong there," I laughed.

"Let's head back to my place," Bailey smiled, as she hooked her arm under mine and led me down the street. I loved how she seemed to take control of the moment...it was actually kind of a turn on.

When we got back to Bailey's house, she led me straight downstairs to the basement and locked the door on the way. Her mother was still at work, but she wasn't taking any chance of anyone walking in on us together. Bailey shoved me onto the couch and climbed on top of me, crushing my lips with her own and shoving her tongue down my throat. I groaned, wrapping my arms around her and deepening the kiss, as she started panting and dry humping.

My hand moved up her side and under the front of her shirt, feeling her small breasts, playing with her nipples. She broke the kiss and smiled.

"Wanna watch some porn together?"

"W-What?"

The question was so random, Bailey took me by surprise. She wasn't waiting for a response though it seemed, as Bailey climbed off of me and grabbed her laptop, sitting down and turning it on. "What are you in the mood for...gay, straight, in between?"

"I-I don't know...you pick?"

Bailey shrugged, as she pulled up her web browser and went directly to a website full of transsexual porn...or...shemale, as it said on most of the videos that she pulled up to watch.

One of the first videos she played was of a tall blonde, with broad shoulders and huge tits. Her arms and legs were well-toned and she had the prettiest green eyes, to compliment her oval-shaped face. Between her legs though, was an enormous cock, about ten long inches and very thick. On his knees in front of her was a man, quite built himself, eagerly sucking at her cock.

I watched, as he bobbed his head and made all kinds of loud sucking and slurping sounds, while the shemale leaned her head back and moaned in pleasure. She kept her hand on his head, fingers running through his curly hair, forcing her cock deeper down his throat with every thrust. My own cock began to stir, and I looked over to see that Bailey had slipped out of her pants, and was now stroking her huge cock to the video.

The video carried on for a few minutes, with this guy sucking his partner's cock before the scene switched and showed the blonde leaning over the side of the couch. The guy got behind her and proceeded to start pounding her ass, slamming his cock in and out of her hole without mercy...it was so hot. I slid out of my pants now, and started jerking, just like Bailey.

As I was starting to get really into it, Bailey reached over and pushed my hand away from my cock, replacing it with her hand. "Why don't we help each other out?"

I smiled back at her and nodded, before reaching over and wrapping my

fingers around her cock. We proceeded to stroke each other while continuing to watch the guy fucking his shemale partners ass. After a while, the scene changed again. This time, it showed the guy laying on his back, while the blonde moved over him and spread his legs apart.

I watched, as she lined her monster cock up with his ass and proceeded to push into him. He moaned loudly, as she began to slowly thrust in and out of him, making it easier on him then he had on her...at first.

Gradually, she began to pick up the pace, until she was fucking him just as hard as he had fucked her. Bailey moaned beside me, her hand pumping my cock faster and faster. I looked over and she was biting her lip, panting now and sweating a little.

She was getting close...and I was too.

As the video carried on, Bailey and I started panting harder and moaning more and more. Bailey lifted her ass off the couch, with a gasp and whimpering, her cock began to pulse. I watched, as she shot off several thick, long ropes of cum into the air. At just about the same moment, my cock erupted, firing off a good couple of shots of my own, before I sunk back against the couch.

We were both out of breath, glistening with sweat, as the video continued playing on the laptop...we weren't watching anymore though.

Bailey sat forward, pausing the video and getting up to grab a towel for the both of us to clean ourselves with.

As Bailey handed me the towel and I wiped the cum from my stomach, she flopped back down on the couch beside me and smiled. "So, that was fun, right?"

"Yeah," I chuckled. "It definitely was."

"Do you...wanna try anything you saw on the video?"

I hesitated, biting my lip, wondering which part exactly she meant to try. "Uh...l-like what?"

"Like...maybe we could...go all the way?"

Was that a real question?

"Yeah, I'd love to! I-I mean...if you want to, that is."

"I-I do," Bailey smiled eagerly.

We were both on the same page, it seemed.

My stomach was in knots. We'd fooled around Saturday and again just now, but that was just foreplay...we were talking about the real thing now. I was about to lose my virginity. That's when I realized, we had one small issue to work out before we could make that happen...I was a little nervous about the answer that Bailey might give me though.

"So, um...h-how do we do it?"

"Have sex?" Bailey asked amused. "I mean, it's pretty simple."

"No, I know, I mean...like..."

I trailed off, too nervous to straight-up say what I was thinking. Bailey seemed to put two and two together though, and I was surprised to see her blushing a little. "You mean...which one of us is the top, and which one is the bottom?"

"Yeah," I nodded, glad that she'd figured it out on her own.

"To be honest...I'm not sure," Bailey admitted.

That was a bit shocking to me.

Bailey seemed like the type who always knew what she wanted, but oddly enough, she seemed almost as nervous about this whole thing as I was. "I've never actually had sex with a guy before," Bailey said, after a few moments of silence.

"W-What? Really?"

"Really," she laughed nervously, as she blushed harder.

"I mean, girls sure but...boys? I've never been with one before you, so I don't know which one I'd prefer."

"So then...I guess this is a first for both of us?"

Bailey smiled and nodded. "I guess so..."

I had no idea how this would work out, and clearly, Bailey was in the same boat. It was all about figuring out what we both liked since neither of us had done it before. We sat in silence for a few minutes, each of us trying to figure out what to do.

Finally, Bailey spoke up, a bit nervously. "I guess...you could be on top if you want."

"A-Are you sure?" I asked.

Bailey smiled, reaching under the couch cushion and pulling out a bottle of lube. I laid back and Bailey climbed on top of me, popping open the bottle of lube. She squirted some into the palm of her hand and started stroking my dick until it was fully hard and nice and slick with lube.

Then, she reached back and applied some to her asshole, before positioning herself over my cock. We made eye contact for a moment, and I could see that she was just as nervous as I was. Biting her lip, Bailey slowly lowered herself down, the tip of my cock pressing against her puckered hole and slowly it popped into her. We both gasped loudly, as the head slipped into her asshole.

Bailey bit her lip even harder, squeezing her eyes shut in discomfort and pain, while I groaned in pleasure.

"Holy fuck," I moaned.

She was so damn tight, it felt like her asshole was gripping the hell out of my cock, squeezing it tightly. It took me a few moments to notice the pained look on her face, and when I did, I reached up to grab one of her hands. "Are you okay?"

"Y-Yeah," she stammered, her voice shaking. "I'm fine."

"Are you sure?"

"Just...give me a second..."

My hands moved to her sides, sliding up and down over her hips in an attempt to try and comfort her. After a few moments, Bailey took a deep breath and exhaled, before sliding further down onto my cock. The more she took, the more it started to feel good, at least, for me.

Finally, she bottomed out, taking my entire cock balls deep in her ass. My hands moved to her hips and held on to her tightly, as she looked down at me, and I heard her grunt.

"You are so...fucking tight," I moaned.

Bailey didn't say a word though.

She waited a few seconds before she started slowly moving up and down on my cock, riding me gently. Gradually, she began to pick up the pace. That pained expression never seemed to fade though, and after a while, as much as I was enjoying myself...I had to call her out on it. "You're not enjoying this, are you?" I asked as Bailey sighed heavily.

"It's fine," she insisted. "Maybe...let's try another position."

I could tell she did not want to give up so easily. I nodded, and Bailey slowly lifted herself off of my cock and rolled onto her hands and knees. I got behind her, spreading her ass cheeks and pressing the tip of my cock back to her entrance. With a hard thrust, I pushed straight back into her. Bailey slumped forward on the couch, burying her face in the pillow and gasping.