Hard on the Trail

I had been waiting days for Daddy to show up again. I had waited long enough I had started to wonder about his life outside of my ass. We had agreed in the beginning that I was to not know his name nor anything about his life. But I started to wonder if he lead a double life. A wife? Kids? Maybe that is why he was obsessed with the idea of me calling him daddy? Maybe he never had kids? Or maybe it went into a dark place. Had he been abused? Had he been the abuser? I didn't want to think about that. It made it dirty and what we had was too amazing for me to think about how wrong it was.

Didn't matter if he had a wife, some day I'd have a girlfriend again and this would have to end. Would he allow it? He would have no choice.

I'd been wearing the pj's to bed every night. I had gotten a few action figures and spilled them out around my bedroom floor. I figured it'd give Daddy something to step on when he showed up. Get him all fired up and mad before I even woke. Something to motivate him to teach me a lesson. What a naughty boy I'd been, leaving my room a mess!

Finally, one night, I woke to hear a growl, "DAMN IT!" it worked, he was here, he'd stepped on one of my toys! I didn't move, how would he wake me? He stumbled around my bed and stood over me for a while. Through my eyes only open a crack I could see him standing there. He looked like he was stroking his cock. He'd already taken off his clothes. All but a pair of boxers. The moon outlined him well and his cock was definitely hard. Mine flexed and I wanted to stroke it, but I'd give myself away.

He crawled into bed behind me, tucking himself in and putting his arms around me. This was oddly gentle, not at all what I expected. Maybe my acting was too good. I felt his rigid cock pressing against my ass. My dick flexed again, oh how I wanted him inside me. His hand reached around my stomach and slid down to find my fully erect masterpiece. He moaned as he began to rub my dick through my spiderman pjs. I moaned. He leaned forward and whispered, "keep quiet!" as he reached behind me and unbuttoned my butt flap on the pjs. I pushed my ass out towards him. Trying to tempt him with my opened butt flap. He slid his right arm under my side so his hand was on my stomach, his left hand slid into my open butt flap and he began to massage my ass cheeks. I moaned again as his fingers traced around the crack, teasing me. "Boy, you better keep your mouth shut about this or I'll just have to come in with tape and a gag next time. You got it?!" I nodded and with that he used his right arm on my stomach to flip me onto my knees.

I heard him spit, wow spit? We hadn't used that in a while. I wondered why he wouldn't go with lube. Maybe he wanted to act like this was a spur of the moment event. Whatever the reason, his spit covered fingers began poking my ass hole as he bent over me and whispered in my ear again. "your mother won't let me fuck her tight ass!" oh...he really was going to play this role tonight...was she supposed to be in the next room? "So I'll just have to fuck yours instead! And if you say one word about this, I'll show you such an ass pounding you won't sit down for weeks! Understand?!" I remembered the last time he had been here and I knew he could deliver such an ass pounding. I would behave...mostly.

I moaned again as his fingers slid into my ass and immediately found my button. I started to push back into his fingers. With every pump my pjs would tighten around my thighs, a constant reminder that I was dressed as the young boy being corrupt. Oh how fucking kinky this all was. I moaned, "oh daddy! Touch me!" he moaned and slid his fingers out. I heard a jar opening, so he had brought lube.

"What I'm about to do, it might hurt, but it'll be worth it. I brought plenty of lube so if it gets too dry just bite down on the pillow and I'll know to get more.

What was he about to do? Why did he need so much lube. I felt the first bits of gob hit my ass. This wasn't the normal runny lube we used, it was more like a paste. Like he was coating me with crisco. Had he raided my kitchen? Before I could think much about it I felt the hardest prodding I'd ever felt. It wasn't his dick, what in the fuck was he shoving in my ass. It was this incredible mixture of pleasure in pain, I looked over my shoulder and saw it was his hand. How many fingers was he using. I felt myself stretching more and more I began to moan out hard. Almost a growl, with his free hand he clumped more goo on and whispered, "almost there...just a little bit more." I still didn't understand, all I understood was pain. Maybe if I cried out to him he'd make it stop. Get in character...get into character.

"Daddy, ow, please stop, daddy. It hurts!"

"Just a little more. You can take it" his free hand rested on my lower back. Whether it was to comfort me or to hold me in place I wasn't sure. But I knew I couldn't take this. Damn it, why didn't we have a safe word?

"Daddy no, please, please stop! I'm too small. I'll wake mommy."

That made him flinch. Had I hit a nerve? He said, "Then I'll have to do this fast. It'll hurt, but only for a second and then it'll feel amazing. You'll see, let daddy show you."

I was going to ask what but before I could I finally understood what he was doing. With one quick ass ripping thrust he had his entire hand inside my ass. "MOTHERFUCKER!" I screamed out!

He grabbed my hair and shoved my face into the pillow. Growling into my ear, "You shut your fucking mouth! You think my foot didn't hurt when I came in here to tuck you in and found your toys all over the fucking floor?! You think that was funny? Fucking dip shit! Well, now we're fucking even!" He started moving his hand around inside me. It felt so large, foreign and odd. Now that he was in to his wrist the burning tearing pain had stopped. It was just an exceptionally full feeling. "Now you keep your mouth shut, you got it?"

I moaned that I understood and he released my head. Putting his hand back on my ass cheeks, separating them as if to examine his work. He started to pull back a little, I whined at the pain of his hand starting to exit my ass, but before it would he shoved it back in. I had tears in my eyes as I asked, "Why are you doing this daddy?"

"Because, daddy is going to fuck your ass tonight boy, and I need to make sure you have room for daddy's big dick." Ah, so we were pretending this was the first time again were we? He really liked taking cherries. I hadn't thought of that, how many other men did he have one the side? how many cherries was he popping on the trail? Maybe he didn't have a wife, maybe he had many other boys out there calling him daddy and letting him fuck their ass. The idea made me mad and oddly competitive. I wanted to be his only one.

"Oh daddy, don't. Not my ass! I'll clean up my room I promise."

"Too late now, you're tight little ass has me all worked up. You feel this?" He shoved his dick against the pj's on my inner thigh, "that's what your ass does to daddy. Your mom can't get me that hard. But you can." He started to pump his fist. It hurt...so I let him know. I cried and whined in pain. "Yeah, you'll learn to like it. You're going to be daddy's little bitch. Mmmm stretch that ass out for daddy's big cock!" He started to pull his fist out further each time than the last. It still hurt but the pain slowly subsided enough for me to enjoy it. My flaccid cock begin to stand up to attention again. "Mmmm fuck, I can't wait any longer."

"FUCK" I moaned aloud as I felt him yank his fist out of my ass with a loud slurping pop noise.

"SHUT UP BOY!" he growled as he raised himself up over me and rammed his dick into me. "I haven't cum for days and I have a big load I need to get out. You're just what I need and you're going to take every drop. You spill any and I'll make you lick it up."

"Fuck. okay daddy. I'll be good."

"SHUT UP! Not another word. do you understand me?"

So that was how this was going to be. Just me moaning into a pillow while he degraded me. I could do that. The stretching he had done made his dick ease into my ass like nothing. I could feel the gape. Guess he'd liked treating me like a cup last time. I was daddy's little cum bucket. I reached underneath my stomach to the flap of my pjs and pulled out my hard dick. I started stroking it with every thrust from Daddy.

As he thrust into me he continued to grunt and degrade me, "Yeah, oh yeah you fucking slut! I knew you'd take daddy's dick like a man! Too bad your mom didn't know how to fuck. You're tight little ass feels so good on daddy's dick! OH fuck yeah. You take it you little bitch. Yeah...that hurt, huh? Too bad boy! You keep your mouth shut. Yeah, fucking right." his thrusts began to pick up pace. "You fucking liking that, you dirty little prick? You rubbing your dick? Daddy going to make you cum?" I moaned, "yeah, you like daddy's dick don't you! Deep inside your ass, going to fill your ass! Don't spill a drop, you remember?"

All I could do was moan and then, just like last time, he started to pound me harder, deeper. This was still new to me. Made me feel like he really was popping my anal cherry. But the harder he pumped, the dirtier and rougher he got and the closer it made me. I cried out in pain and pleasure as I felt my dick squirt all over my bed sheets and a little on my pjs.

"OH YEAH! You fucking cum boy? Yeah."

I whimpered and moaned. Just like last time, once I came it started to only hurt. I braced myself for the pain that remained while Daddy finished off. Burying my face into the pillow I whimpered and groaned in pain.

"Yeah, you fucking little bitch. You take it. That hurt? Huh? Yeah? right in your ass? Deep in your ass. You little pussy, I'll show you what it takes to be a big man!" His words turned into grunts and I felt him begin to stand up, he was about to finish. Thank god! I couldn't take much more, there were actual tears in my eyes. I needed to learn to last longer, or fake an orgasm just before he came. As long as I was hot the pain was hot. I stood my ass up and felt his feet insanely close to my face. I saw his toes twitching on my bed as he thrust downwards into my ass.

"Here it comes boy! Get your ass ready and don't even think of fucking moving. I don't want a mess you get me!" I nodded "Fuck yeah, I'm going to fill you, just like the bitch you are! ARRUUGGGG" and with that I felt the spurts of hot cum start filling my ass. Just like last time I could feel it settle at first, but with every jiggle he caused when he thrust once more it'd go further down into my bowels. He just kept going, it seemed the longer he was away the bigger his load was. I reached up between my legs and grabbed his balls. Squeezing and playing with them as he came. He must have liked it because he moaned louder and made one final thrust deep into my ass. Hurt like anything else but it meant less load being spilled in just my anal cavity. After a few seconds he pulled his dick out of my ruined ass hole. He just stood there holding my ass cheeks for a bit. What was he doing? Then I felt his thumbs on either end of my opening pulling me wide open while his palms circled and massaged my cheeks, as he did this I felt a cold fluid dribbling down into my bowels. He was massaging his cum deep into me. Fucking hot!

Once he was content he slapped my ass cheek and flopped down beside me on his back. I slowly eased onto my back, careful not to squish my swollen stomach. I was beginning to like this feeling of having my gut inflated with cum. Even if it meant waiting a long time between his ass poundings.

He must have worn himself out because when I looked over he was sleeping. He never had slept in front of me before. My heart jumped. I curled up into him and tried to get some sleep myself.

I woke a few hours later with Daddy climbing out of bed and hurriedly putting his clothes on. Shit, if he did have a wife she'd have wondered where he was. Maybe I should ask him. I cleared my throat to get his attention, "Daddy?"

"Mmmm?"

"What takes you so long?"

"What?"

"You know...sometimes you're gone for a long time? Do I bore you? Or are there others?"

He smirked, "boy, there is no one like you out there." He pulled his socks on.

"then why do you take so long?"

He stopped, he seemed to think about this for a while. "do you get impatient waiting for daddy?"

I nodded, "A little. Some nights I'm up all night with a hard on. But I don't want to jack off in case that's a night you let me punish you. Cause I don't get to fuck your...Daddy's ass as much as you get to fuck mine." He turned his mouth down in a sad thoughtful look. "it's alright, I don't mind...you give me the best orgasms. Don't get me wrong. I just ... I just wondered. I want to keep you around. At least for now. I mean, we both know I'm not gay."

He laughed, "yeah....you're not gay" he grinned, "listen...maybe it's time...." he stopped and seemed lost in thought.

I sat up a little in bed, "time for what?"

He lay down in the bed beside me, propped up on his elbow, he traced his fingers down my chest. Did he mean it was time for me to fuck him again? "Get dressed." he commanded, "It's time we find you a cum slut."

My eyes went wide, "A what?!"

He laughed as he stood up and reached for his other sock, "A cum slut. Did you think I didn't have a daddy too?"

If my eyes hadn't already been as wide as possible that would have done it. So he had a daddy?! That's why he took so long? He had someone else that came and fucked him when they wanted to? He wanted to get me one? I was going to be someone else's daddy? Oh fuck! The idea was getting me so hard. He looked down at my cock and laughed again, "Save it" he said, "We're hitting the trails, I've got just the right one picked out for you. I think you'll get along just fine!"

And with that he tossed a t-shirt at me and started down the stairs.

(to be cont.)