Bailey Ch. 02

I grabbed her by the love handles and proceeded to start fucking her, enjoying the fact that I was more in control now.

As I started fucking her harder, I reached down to wrap one hand around Bailey's cock. It was semi-hard and dripping with pre-cum, as I started stroking it nice and slow. I kept my free hand on her hip, as Bailey kept her face buried in the pillow.

Panting, grunting and sweating, I started to feel a very familiar build-up of pressure in my balls...I was getting close now, I could tell. I started jerking her cock faster, ramming her ass with everything that I had. Bailey was panting too, moaning and whimpering.

I was ready to go. I braced myself, biting my lip and grunting as my cock began to pulse, and I yelled out in pleasure. "F-Fuck!"

Bailey bucked her hips, pushing back against my cock as I began emptying my balls into her asshole. I came so hard, I lost track of how many seconds passed by before I started to feel a bit light-headed. I slumped forward on top of her for a moment, panting and sweating, my cock slowly beginning to deflate and eventually slipping free from her gaping hole.

As I slipped out, I pulled away from Bailey, who turned over onto her back and smiled faintly up at me. "I-I take it you enjoyed that?" She asked.

"Yes," I sighed, wiping the sweat from my forehead.

Enjoyed it, was an understatement; I had fucking loved it.

And I felt like a totally new person, no longer a virgin...I just got laid for the first fucking time, and it had been incredible. As the moment passed though, I took note of two things; one, Bailey was still incredibly hard, and I wasn't sure if she herself, had even managed to cum. On top of that, I noticed the not so satisfied look on her face, and it had me a bit concerned.

"Are you okay?" I asked.

"Me? Y-Yeah, I'm fine," she replied.

I didn't believe her, but Bailey moved over on top of me and laid her head on my chest. I just wrapped my arms around her and started rubbing her back, the two of us completely quiet.

After a few minutes of neither one of us speaking, I knew I had to ask; "Bailey...how was it for you?"

She lifted her head from my chest and smiled; it was a fake smile though, I could tell. "Me? It was great," she lied.

"Are you sure about that?"

"Sure, yes I'm sure," she scoffed.

I just stared at her and she sighed after a few seconds, pulling away from me and standing up from the couch...that was a good enough answer, I thought. I wanted to hear her say it though...she hadn't enjoyed herself nearly half as much as I had. "Tell me the truth," I said.

Bailey looked back at me for a second, hesitating.

"A-Are you sure?"

"Yes! I want to know...did you enjoy yourself?"

She sighed again, then shook her head...that's what I had thought. Bailey sat back down on the couch, and I sat back up beside her, looking down at my feet. "Why did you lie?"

"I didn't want to hurt your feelings," she shrugged.

"Hurt my feelings? Bailey, if you didn't like it, you didn't like it...that's all there is to it, right?"

She looked at me surprised, as though she had expected me to be hurt or offended by her lack of interest in what we had just done. Looking back on it, I should have picked up on it in the middle of the act. I knew she wasn't enjoying herself, I was just too caught up in my pleasure to care...realizing that almost made me feel like a complete asshole.

"You're not upset with me?" Bailey asked.

"No, of course not!"

She smiled and sighed in relief. "Sorry," she said.

"I guess, I just really don't like letting people down...I didn't see the harm in trying, since I'd never done it before, but, now that I have...I don't think I'm meant to be a bottom."

I nodded in understanding...that was fine. What was I going to say, right? If Bailey didn't want to be a bottom, then I couldn't force her to be a bottom. With that in mind though, it only seemed logical when Bailey asked the next big question.

"Would you want to try?"

I looked at her, confused at first; I didn't know what she meant.

"Try...try what?"

Bailey smiled, licking her lips. "You know," she said. She leaned back on the couch suddenly, wrapping her fingers around her cock and stroking it nice and slow; I got the point.

"Oh...Oh!"

Of course, that's what she meant! After all, Bailey preferred to be the top in the relationship, the dominant one...that meant, someone had to be the bottom, and obviously that someone would have to be me. "I'll be gentle, I promise," Bailey said, still stroking her big fat cock for me.

"I...Uh...w-well..."

Bailey could easily see that I was afraid of such a thing. She stopped stroking her cock and sat up on the couch, sliding behind me and wrapping her arms around my waist, holding me close. "I promise," she whispered, repeating herself.

I took a deep breath and exhaled, nodding my head.

I almost felt obligated, to at least give it a chance. After all, Bailey had given it a try, even though she knew before we even did anything that she wasn't going to enjoy it. Not to mention the fact that she hadn't gotten the chance to cum yet, herself.

"O-Okay," I said, anxiously.

Bailey quickly lifted her chin from its resting spot on my shoulder, as if surprised by my answer. "Really?"

"Yeah," I said, nervously. "I mean, you never know if you'll like something or not until you try it...right?"

Bailey kissed my neck, leaning back against the couch and pulling me closer to her now. As she did, I found myself sitting in her lap, and I could feel her hard cock pressing against my tight virgin asshole, as her hands slowly moved up and down over my chest in a soothing manner. "That's true," she whispered seductively. "I like a guy with an open mind."

I just sat there on her lap, as she continued to massage my chest and probe my ass with her monster of a cock for a few minutes. Finally, she shifted underneath of me and pushed me onto my hands and knees, grabbing the same bottle of lube she had used earlier. This time though, she was lubing her cock, and my asshole too.

"You're going to feel a little bit of pressure," she said, as she stroked her glistening cock and lined it up with my hole.

"Try not to freak out or anything...staying relaxed will make things go a lot more smoothly."

"Is it going to hurt?"

"A little," Bailey said. "But, if you stay calm, it won't hurt for too long."

I took a deep, shaky breath and exhaled as I tried to relax. I nodded my head, and Bailey pressed the tip of her cock to my anus. I felt her probing and poking around a little at first, teasing my hole...and then she threw her hips forward and slammed straight into me.

"FUCK!" I shouted, perhaps a bit too loudly, because Bailey's hand immediately moved to cover my mouth.

"Shhh," she shushed me. "I don't know if my mom's home yet."

Fuck, I thought.

My asshole was burning! Bailey had rammed all glorious ten inches of her cock, straight into me, without any mercy. Was this payback for how rough I had been with her, earlier? I stifled a cry, as she slowly pulled back and then drove herself right back into me again...harder this time, than the first.

"Fuck, you are so tight," she moaned softly.

Again, she pulled back just a little and then slammed forward, knocking the wind right out of my lungs. I swore I could feel her in my stomach with every thrust that she delivered. I could feel my hole stretching wider and wider, to accommodate her size. Her hands moved to my hips after a few minutes, and that's when she began to pick up the pace. Instead of pulling back slowly every few seconds, and ramming herself back into me as hard as she could, she was now giving me a nice, steady fuck, thrusting in and out of me, the couch shaking underneath of us.

Slowly, the pain began to subside. As it did, however, I became gradually aware of the fact that this was beginning to feel kind of...good.

Bailey kept her hand over my mouth, muffling my moans, as we suddenly heard footsteps walking around upstairs...her mother was home. "Stay quiet," Bailey whispered to me, trying to keep her noise down at the same time.

There was a knock at the basement door suddenly, that startled both of us.

"Bailey? Are you down there?"

"Y-Yeah mom, I'm here!"

"Did you eat dinner yet?"

"Yes! I'll be up in a little while, mom...promise!"

"Don't be to long honey, it's a school night," the woman called back, before walking away from the door. Bailey sighed in relief and giggled, smacking my ass, before she continued pounding me.

She pushed my face down into the couch cushion, grabbing me again by the hips and proceeded to get a lot more rough and aggressive. The room was filled with the sound of our bodies slapping together, and Bailey panting, as I was grunting and moaning into the couch cushions. Bailey grabbed a fistful of my hair and yanked my head back, and I gave a slight yelp as she did. "Tell me you love it," Bailey demanded.

"Tell me you love my cock in your ass!"

"Oh God...y-yes..."

"Yes what, Ryan?"

"Y-Yes, I...love your cock...in my ass!"

She let go of my hair and shoved my head back into the cushion again, giving me a smack on the ass and giggling. "Good boy," she said seductively. Then suddenly, she was flipping me over onto my back and spreading my legs wide apart. She pulled me forward some, lining up with my hole and pushing back into me, crushing my lips with her own as she began fucking me again.

"I wanna see your face when I cum inside of you," she said, as she broke the kiss. "Do you want my cum inside of you, Ryan?"

"Yes...please!"

I couldn't believe how much I was enjoying this. I had gone into it expecting to have the same result that Bailey had experienced when I fucked her; I didn't think I'd like it at all. Compared to how good it felt to fuck Bailey though, this almost felt even better. With every thrust she gave me, Bailey kept hitting something deep inside of me, that sent waves of pleasure rolling through my entire body.

My cock was hard as a rock again, leaking pre-cum...I didn't think I could achieve another orgasm, not after how hard I had came earlier.

Bailey started panting and groaning, as she seemed to slow down a little. Where she had just seconds ago been giving me a nice, long, hard fuck, she was now much more gentle and almost loving, as she gazed into my eyes. At that moment, I felt a chill run down my spine...I was falling in love with Bailey.

And I thought, maybe, she was falling for me as well.

"I'm gonna cum," she whispered, her voice shaking.

"I'm cumming!"

Then, without another word, Bailey buried herself balls deep in my ass and erupted. I felt her pulsing, I felt the hot ropes of cum, as they fired off one by one into my hole. At that same moment, I felt my entire body tense up and I cried out in pleasure with her. Bailey kissed me again, to keep me from getting too loud, her tongue sliding into my mouth and I wrapped my arms around her as we both shook together.

When it was finally over, Bailey broke the kiss and collapsed on top of me and sighed heavily. We stayed like that for a long time, until she finally lifted herself up and off of me, to reveal that I had made quite a mess, covering myself in my cum.

Bailey giggled, using one of her fingers to scoop my cum up and lick it, sucking on her finger for a moment. "Delicious," she smiled. "Turn over."

"W-What for?"

"I wanna see that creampie, I just made."

I laughed a little, rolling slowly onto my stomach, and Bailey gave my ass a nice hard smack. She spread my cheeks and examined her handy work, moaning, as she could see her cum leaking out of my bruised and gaping asshole.

"I filled you up," she said with a laugh. "Good thing you can't get pregnant, right?"

"Yeah," I scoffed, as I turned over and stood up now. "Good thing."

Bailey got up to, grabbing a towel from the bathroom and handing it to me so that I could clean myself up a little. Once I finished, we sat back on the couch together again and that's when she asked the same question I had asked her earlier.

"How did you like it?"

I looked over at her and I could tell by her facial expression, she already knew the answer...she just wanted me to say it.

"I loved it," I said truthfully.

"Really?"

"Seriously," I laughed. "I mean, I didn't think I would, but...wow...it felt really, really good...now I know why Brittany is so into you."

Bailey laughed at that, snuggling up to me and kissing me on the neck. We sat and talked for a few minutes before I noticed the time on the clock...it was nearly quarter after eight. I had to get home, and fast, or my dad would kill me for sure. Bailey's mother was expecting her upstairs too since it was a school night.

I walked home that night, with a bit of a limp, my asshole still quite sore from the pounding that I had taken. I was happy though. I'd lost my virginity...twice...and it was well worth it. When I got home, I half expected someone to say something about how late I was and also about why I was limping.

Fortunately, my father was downstairs in his "man cave" drinking with a few friends, and Mark was out on a date with his girlfriend, so I didn't have to worry about him either.

I went straight upstairs, got in the shower, and once I was cleaned up I went directly to bed; I was exhausted.

The next day at school, I found Bailey waiting right outside the front entrance, hiding in the smoker's corner with Nick and Tyler. As I walked up to the three of them, Nick looked up and smirked, waving his hand. "There's the man of the hour," he laughed. "How ya feeling there, buddy?"

What the hell was he talking about?

I looked at Bailey, who took a drag of her cigarette and looked away from me shyly...did she seriously tell them what we did?

"Uh...I'm good," I said, a bit nervously.

"Heard you and Bailey tried out some new things last night," Nick continued.

"Give him a break Nick," Tyler said, shoving his brother a little.

"Look, man, we're not making fun of you or nothing...Nick just likes to bust peoples balls a lot, that's all."

I nodded, still a bit embarrassed, as I rubbed the back of my head. Bailey stepped up to me then with a smile, wrapping her arms around my waist and pushing me up against the wall. She kissed me on the lips and I melted, letting go of that brief feeling of embarrassment and just enjoying the feel of her lips.

"I'm sorry," she said, as the kiss broke.

"Uh...huh?"

"I shouldn't have told them," Bailey said.

"I just couldn't help but brag about that sweet ass of yours."

She grabbed my ass, as she said that last bit, and gave it a nice firm squeeze. I jumped, and couldn't help but laugh, shaking my head at her. "Well, you're lucky that I like you," I replied.

"Should we leave you two alone now?" Tyler asked.

The bell rang at that exact moment, signaling the start of the day. Bailey let go of me, with a disappointed look and we started our way into the building, holding hands the whole way there.

My ass was still a bit sore from the night before. I wasn't limping quite as much as I had been, but I did find it a bit difficult to get comfortable while sitting down in each of my classes that day. By the time Gym class came around, I was actually relieved to have a class where I didn't have to sit...even if it was the one class, that I usually despised more than others.

Our gym teacher was absent that day...what a relief because the substitute teacher didn't have anything specific planned for us, which meant we could do whatever we wanted. So, I had taken up one corner of the gym room and was just standing there with my back against the wall, listening to my headphones. The sounds of Taking Back Sunday blasting through the speakers dulled out all the noise around me, and I was able to relax a little.

Would have been better if I could have sat down, but it wasn't worth the dull ache in my ass.

About halfway through the class, I decided to run to the bathroom. I walked into the locker room area and was heading towards the toilets, when someone grabbed me by the arm and yanked the headphones off my head, throwing them to the floor.

"H-Hey, what the-"

"Shut the fuck up!"

It was Billy...along with Tim, and their other friend, Shawn.

Before I knew it, Billy threw me against the side of one of the bathroom stalls. I hit the stall so hard, the door slammed against the inside, causing the entire thing to rattle. I dropped to the floor and Billy, along with his two friends, began kicking me everywhere.

It was a full-on assault.

My ribs, my face, my arms, my legs, they were stomping all over me without any mercy. Then it got worse when Billy got down on top of me and started straight up punching me in the face, over and over again, until Tim pulled him off of me and stopped him. I spat up a little bit of blood on the floor, rolling over onto my side and then back onto my back.

"W-What the fuck," I asked, my voice cracking as I spoke.

"What's the matter, cock sucker? Too much for you to handle?" Billy asked, with a sick grin.

"Fuck you," I groaned.

"You'd like that, wouldn't you?"

What the fuck was he talking about?

"That's right," Billy continued. "We know you been fucking around with Bailey...that little crossdressing freak...you like cock, huh? Figures a loser like you would be into that sort of thing."

That's what this was about?

"I-I don't know what you're talking about!"

"Of course you do! Come on, Ryan, you wait until everyone else leaves the locker room to take a shower...conveniently at the same time that Bailey takes one!"

Why did this even matter to them?

It didn't...I knew that...they were just fucking with me like they always did, and this was just one more thing to add to the list of reasons to give me shit. Billy knelt alongside me and leaned in close. "By the way," he said slowly. "Tell anyone we did this...and I'll break your fucking neck, next time."

And with that, Billy stood, laughing and walked out of the room with Tim and Shawn by his side. I heard the doors slam shut as they walked back out into the gym, leaving me on the dirty floor, bruised and bloodied.

It was Nick who found me there, probably about ten minutes after the whole incident occurred. I was humiliated and in so much pain, I just didn't feel like moving. He helped me up and carried me out to the substitute teacher, who of course, sent me straight to the nurse. And of course, the nurse called my father and before I knew it, he and Jamie were on their way to the school.

I would have preferred to keep the whole thing a secret, but the bruising on my face was way too obvious for that.

Now, I was sitting in the Principle's office, with my father and Jamie right alongside me...of course, they were trying to get me to talk.

"Mr. Daniels, we want to help your son...whoever did this should be punished, but unfortunately, Ryan isn't giving us any information on who exactly did do it to him."

I had shut down completely.

Billy warned me not to say anything, and that was a warning that I was taking very seriously. I hadn't even told Nick who had done this, because I knew that he and Tyler would take care of it, and that was the last thing I needed right now.

Chances were though, Tyler and Nick would figure it out on their own, even if I didn't tell them...they were smart enough.

"Ryan," my father spoke from beside me. I could tell by his voice, that he was irritated. Not with me...my dad was a hard ass, but he cared about his kids. He was more irritated with this whole situation and the fact that I was staying quiet.

"Tell us who did this...you don't need to be afraid."

"Oh, I don't do I?" I asked, sarcastically.

Maybe I shouldn't have responded that way...it seemed to pretty much give away to everyone in the room, that some sort of threat had probably been made, to keep me silent.