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Chapter 17
by
astronym
Who shall we watch?
Jacob tearing Max open.
Perspective: Max
Oh fuck, oh fuck, oh fuck, it's happening. As Jacob led me by the hand away from the living room (leaving Aaron and Thomas alone to do God-knows-what), that thought kept running through my head. Oh fuck. This is happening.
It had only been about an hour since I had told Thomas my kink, and Jacob had known for even less time. But here we were, about to live out one of my kinkiest fantasies in real life for the first time. He took me to my bedroom, and closed the door behind us. For some reason, this made me giggle - we were hardly about to do anything private - but I liked the thought. I turned around and pressed myself against Jacob, meeting his soft lips with a kiss, and another tug on his spit-covered dick. It was still big, but had softened a little from the short walk. That was probably for the best - it wasn't his cock I wanted right now.
"On the bed," he ordered. He had slipped into the dominant role very quickly. I didn't hesitate, and hopped up on all fours. He placed a hand on my back and pushed - I immediately lost my balance and my arms fell away, my head toppling onto the pillows. Now my ass was pointed into the air. I gave it a little wiggle, and he grinned before a hunger took over his eyes. "Toys?" he said. I pointed at the bottom drawer on my bedside table, not wanting to speak, to ruin this moment.
He bent down and pulled open the drawer, and his eyes lit up. There were eight dildos in there of different sizes, some decently large anal beads, and four butt plugs too. I could tell from his face he didn't know where to start, but I needed him to make a decision - I needed to be filled.
"Got a favourite?" he muttered.
"Silver," I gasped. I started to touch my cock, but he casually swatted my hand away. The sting felt so good against my dick.
"No touching," he said. "You're a hole, remember?"
"Yes Sir." I didn't mean to moan, but I did.
"Good. Good little bitch." Jacob brought the silver dildo out. It was ridged and absolutely huge - the largest I could reliably take. I had two others that were thicker, but even with Aaron's reassurance in the living I really didn't want to wimp out on my first attempt. He also pulled the lube from the drawer and carefully squeezed a dollop on the very end of the dildo. I watched as he went to drop the lube bottle back into the drawer.
"Leave it out," I said. "We'll need a lot more."
He nodded and set it on the table. "You can _take _this?" he asked, obviously admiring. I nodded and began to explain that I had been practicing for months when he ran a cold lubricated finger across my ass-crack, and my words evaporated against the moans.
"Please, Sir," I breathed.
"Please, Sir... what?" he said, gently teasing the edge of my ass.
"Please, Sir, fill me up."
One finger, then another. A satisfied little exhalation from Jacob. "More?" he asked.
"Hnnnngg," I said. He took this as the affirmative I intended, and squeezed a little more lube on his fingers. A third finger pushed past my sphincter. He was being rough, but I loved it - I felt perfectly used, a hole for him to explore.
"Fuck, Max. You feel so good, bitch." He pushed in deeper, still three fingers but now deep enough to curl them inward. He stroked my prostate and I almost leapt a foot into the air.
"FUCK!" I yelled, and his fingers slipped out as I writhed.
"Oh, oh, are you okay?" he said, the deep growl in his voice immediately replaced with real concern.
"Putthembackinpleasefuckpleaseputyourfingersinme." I said, pushing my ass up towards him. Part of me was ashamed to be so **** to feel that pleasure again, and I think I'd have done anything for him right then. Part of me got off to that shame, of course. Luckily, that was all the begging I needed to do, as Jacob didn't hesitate to slip his fingers inside me.
"Mmf, that fucking pussy," he said, as he began to thrust. His fingers pushed in, out, in out, and I felt every part of me come alive. I melted into the bed, no longer even perceiving my physical surroundings, only feeling every jolt and thrust Jacob gifted me. I began to whine, a repetitive "uh, uh, uh" that Jacob seemed to love, as he growled low and deep, his mouth now right next to my ear, "Ready to take this thing?"
I nodded. He released his grip on my insides and I had a moment to breathe. "Wait," I said, still gasping for air. I flipped myself around so I was lying on my back, and raised my legs into the air to expose my wet and trained hole. Jacob grabbed the silver dildo and got between my legs, using his own legs to push mine apart even further. He positioned the false cock at my entrance, his own impressive dick still rock-hard at the sight, and gently began to push.
It's remarkable how much willpower can do for your bodily function. I took just one deep breath and relaxed myself and the enormous dildo slid about a third of the way in without meeting any resistance. "Jesus Christ, Max," Jacob said. "I mean... I mean, Jesus Christ!"
I grinned and gritted my teeth. "Deeper," I said, remembering to add "please."
He pressed the base of the dildo against his stomach and pushed closer. "Yeah," he muttered, "take it, take it." I did as I was told, feeling it fill me up and up. He gave the back half of the dildo another coating of lube, and kept pushing. He seemed to have learned I liked it rough, and I showed my appreciation by pushing back. Soon it was almost entirely inside me.
Then, just as suddenly, it was gone. I whined a soft whine of ecstacy and felt my heartbeat start to pound as I saw what Jacob was doing. He had propped the dildo on the table and was instead coating his fingers in lube. All five of them.
"No such thing as too much lube, right?" he grinned. "Ready to take my fist, faggot?"
"Sir... please fist my pussy."
I was loose enough by this point to take three fingers, and barely felt them slip in. The fourth gave a slight tingle as it stretched me back out again, and Jacob seized his moment, pushing his thumb beyond the boundary. Yet another coating of lube and I had his knuckles. He whispered a soft "Fuck..." that, to me, read as genuine appreciation. I felt a moment of pride in my talent, and then he pushed.
I lost all words once again. A low visceral groan escaped my throat as Jacob pushed his fist deeper and deeper inside me. This was nothing like the dildo - it was warm, and I could feel every tiny movement he made against my nerve endings, magnified a thousand-fold. He began to work it in, carefully rotating as he thrust in and out, shifting his angle, stretching me wider and wider with every push. I clutched the edge of the bed and began to cry tears of pleasure. "Don't stop, don't stop" I somehow managed to spurt out, and he met my eyes and grinned.
"I say when we stop, bitch," he said as he took one last push. I had been in such a trance that I didn't realise until now - he had done it. His whole fist was inside me. From my angle on the pillow I could just see his wrist disappear into my asshole. I clenched and he smiled. "Good boy," he said. "Now touch yourself for me."
I reached down and stroked my cock on his command as he began to pound my pussy harder and harder. He was practically punching my insides and it was unbelievably intense. It was pain and pleasure blended into one and I could no longer differentiate. With my hand on my dick I felt connected to his hand inside me, and I could tell that he wasn't holding back. I was soaked in sweat, and I realised Jacob was breathing heavily too, loving his control over me. Suddenly, I felt a pressure inside me, and I clenched. He must have felt it, because he immediately said "Beg for it, fag. Beg to cum."
"Please, Sir!" I immediately launched into a whimpering entreaty. "Please let this faggot hole cum from its pathetic little cock while you wreck its insides. Please, I need it, I need it...!"
He locked eyes with me and leant down, the shift in angle pressing against my prostate. His nose was inches from mine. "Cum for me."
I exploded outward. Both of us immediately became soaked in strand after strand of cum, and it just kept coming, for what felt like minutes. (Okay, it likely wasn't, but let a boy dream!) Slowly, Jacob extracted his fist, and collapsed next to me. "Towel," I murmured. My legs were shaking, and I didn't know how to say anything else. Luckily, Jacob got the message, and grabbed the blue towel from the same drawer - the designated cum towel - and started to clean me up. I tried to take it from him, but he easily swatted my hands away.
"It's okay," he said, noticing that my legs still hadn't stopped. "I'll take care of you."
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Second Year
The gayest houseshare in Britain
Jacob, Thomas, Max, and Aaron. Though they don't know it yet, they're about to have the hottest, cutest, most awkward and most adorable year of their lives. Your likes and comments are always appreciated. I've been thrilled with the reception of this story so far!
Updated on Jun 19, 2024
by astronym
Created on Jul 19, 2018
by astronym
- 91 Likes
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- 26 Chapters
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