Journey to Girlhood Ch. 04

If you haven't read my previous stories in this series, please go back and do so. And thank you for all the comments - it really helps encourage me to write more!

So there I was, on Max's bedroom floor. Ass in the air, face on the ground sucking my own precum out of the carpet. My arms crossed behind my back and holding my skirt up, my caged clit soft, my thighs smeared with my own precum, my makeup ruined, tears running down my face, and the sound of Max jacking his thick cock behind me.

"How does it taste, Stacy?"

I groaned into the carpet and clenched my eyes shut tight, trying to hold back some of the tears.

"Too busy to reply eh? Oh well." I heard Max moving behind me, and then suddenly felt my panties being pulled to the side, and then Max's finger, covered in what I presumed was cold lubricant, pushed it's way inside my hole.

I gasped and raised my head from the carpet. "Don't! Please M- Please Sir, I don't want this please I'll-"

I had let go of the skirt and started to move my arms, but before the skirt had even begun to fall Max's other hand grabbed it and both wrists, pinning me where I was while he continued to probe my asshole.

"Stacy, you do want this. You begged for my cock earlier. You got so wet you made a mess. And this is how girls cum - getting fucked by a man."

With a pop, he pulled his finger out of my asshole.

"It's not like you have any other way to cum." As he said this, he moved the hand that had been in my ass down to fondle my cage, before giving it a rough flick with his finger. He chuckled at the gasp I gave when he did this.

"Have you finished rugmunching Stacy?"

"Sir?"

"Have you cleaned the floor faggot?"

I looked down at the carpet, now soaked in my drool. It was as good as it was going to get.

"Yes sir," I said. I left my mouth open after I said it and tried to spit, or drool, out the fluff in my mouth without Max noticing.

And then I yelled in pain, as everything went red and I felt Max's cock push inside me.

I felt his free hand move to my hip, and he used it to pull me even further onto his cock as he groaned. I cried, struggled to pull my wrists from his hold, and couldn't move. Writhing and gasping and just wanting something, anything to give relief, I turned my head and bit into my shoulder as I whimpered.

"Fuck your pussy is tight," Max growled behind me as he began to slowly thrust in an out of me. As the pain slowly subsided, I felt my cock pulse and strain against the cage in vain each time Max's full length entered me and pushed against my prostate. As Max started to pick up pace, my caged penis began to bounce against his heavy balls as he fucked me, and occasionally I felt a droplet of the precum continuously dribbling from my cage flick against my thighs.

My cheeks began to clap as Max picked up the pace even faster. As the pain subsided and Max began to fuck me, it began to feel pleasurable and I started to let out little gasps and moans every time his cock went to the hilt inside me. As I got used to his cock being inside me and loosened up, he started to hit just the right spot to send a wave of pleasure through me with every thrust.

I was so caught up in this pleasure, this numbness and brain deadness, and complete lack of control as he pinned me against the floor with my arms behind my back, that I didn't even realize Max was speaking to me until he let go of my wrists and smacked my ass.

"Too cockdrunk to listen slut?" said Max, slowing his pace but continuing to slide in and out of my asshole.

I wanted to say no, but instead I moaned and rolled my ass back onto his cock as he hit my prostate again. I sniffed. I could still feel my tears on my face. It had hurt at first - not just the fucking, but being pinned down and degraded. And I never thought I would want this. But now I had a cock inside me, I realized the thing I hated most about it was that it had slowed down. I was a cockdrunk slut.

"Please fuck me," I whispered.

Max slapped my ass hard, and slowed his thrusting down to a slow and teasing pace.

"Please sir - please fuck me," I said a little louder.

Max increased his pace a little bit, and I moaned again as his thick cock pushed against nerve centers I didn't even know I had.

"What do you want Stacy?"

"I want your cock. I want you to keep fucking me with your thick cock. Please sir please just - just keep going please!" I almost started to cry again, although this time for a completely different reason.

Max gripped both of my hips so tightly that I bit my lip at the pain, and then he began to fuck me. What he had been doing earlier was foreplay compared to this, his hips moving against my so fast and with such force that I fell forward and caught myself with my now free arms. I started to shake and moan as he used my ass, and was grateful that however rough he'd been with my throat he'd never been this rough. If he had done this to my throat I'm not sure I would have survived. But now, doing it to my virgin ass, it felt better than anything I'd ever felt.

One hand let go of my hips and moved up my back, before entangling his fingers in my hair. He pulled me up by my hair as he fucked me, and held my like that suspended above the floor as he continued to fuck me.

And then, with a guttural moan, I felt his hands clench up, his thick cock begin to pulse, and his warm seed begin to fill me. I moaned too and thrust my hips back to push his cock and cum even deeper into me, and felt another spurt of precum push out of the tip of my penis. My whole body was shaking, my legs quivering beneath me.

With what little strength I had I kept grinding my ass against Max's crotch, enjoying the feeling of his cock in my ass as much as I could before he pulled out. I imagined the last few drops of his cum being milked out of his cockhead as I did so, before he slowly began to go soft.

"Fuck Stacy, your pussy is even better than your mouth. And I think you enjoyed this even more than I did."

I nodded, which I knew was a strange thing today when I'd been forced into it against my will, the evidence in the tears and ruined makeup on my face, and the bruises on my wrists and ass.

"I did sir. I... I liked being fucked."

Max reached around and held my little balls and caged cock. His hand was huge compared to them, and I felt completely emasculated seeing the size difference, which had not been the same at all when I had been fondling his balls.

"You're so wet baby." As he said this, he used one finger to rub against the tip of penis, which was well lubed with my precum and just exposed in the piss-slit of the cage.

I moaned and my quivering legs finally collapsed beneath me, and I slid off of Max's soft cock and onto the floor.

"Pull those panties up, I don't want my cum dripping on the floor." I did as he said, and lay there in a quivering mess on the floor.

Max stood over me, playing with his soft cock as he did so.

"Overall you've been a good girl today Stacy. You're still learning, but I'm happy with your performance so far."

"Thank you sir," I whispered.

"Do you want to cum?"

I nodded. Max's cock had felt amazing, but I wasn't satisfied. But I was exhausted and my penis was still caged, so I wasn't sure I was able to even entertain the false hope of being able to cum.

Max went over to his desk, then came back with a tube of something and a key.

"I am open to rewarding my sluts. Occasionally. Would you like me to make you cum Stacy?"

I looked up at him and nodded, adding quietly, "yes sir".

Max threw the items in his hand onto his bed, and then effortlessly picked me up. Cradled in his arms I felt so small, and so feminine, compared to him. He lay me gently on the bed, and then knelt in front of me. Picking up the key, he inserted it into the cage on my cock and unlocked it, then gently removed the front part of the cage.

"Stacy, I don't normally touch girl's clits. But I can see how much you need this." He ran his fingers gently along my shaft, which was only semi-hard, and slick with my own precum. His skin was rougher than my own soft hands, but his fingers were surprisingly delicate with me given how much pain those same hands had caused me.

He pulled his hand away and picked up the tube, squirting some on my clit. He began to rub it in slowly. It didn't feel as good as the lube he had used earlier, and looked more like a white cream, but I knew there are different types of lube.

"I've been with cis girls that had bigger clits than you," said Max. Being masterbated by my bully while he made fun of my cli- my penis, after he had cum in my ass and brought me to tears wasn't how I had imagined my first handjob. But I was so pent up and horny and it still felt good.

Max teased me slowly, stroking me close but never quite to orgasm. I was still quivering, and whenever his thumb flicked my glans I whimpered, and feel my ass contract around his cum dripping out of me.

After a few minutes of Max slowly masterbating me it started to feel less pleasurable, and I looked down to see my clit had begun to go soft. I reached down to touch it, my fingers brushing against Max's as I did so.

"I- I'm sorry sir. I don't, I'm not sure why it's gone soft. I was so close to cumming."

Max chuckled and picked up the tube he had used as lube, and threw it onto my chest.

"It's lidocaine. It's a numbing agent. Sorry Stacy, but I didn't have all day. If you weren't going to cum before that started to take effect, you were going to take too long."

I stared at him with my mouth agape. I don't know what surprised me more, that he had done something so... so petty and cruel on top of everything else he had done, or that I had thought he would really jack me off without some kind of joke in it for him.

Max flicked my clit, hard, and I didn't react. I didn't feel a thing. He laughed, and then slid the front of the chastity cage back on, and I knew better than to protest when he locked my clit up once again.