Breaking Jake

Final chapter with Jake and Stu. Let me know in the comment whether or not you want to see either pop up in another story!

"Please, don't answer the door! No one can find me like this." Stu glared at me and pulled his underwear on and answered the door. I was nervous. I could scream for help and hope that someone heard me and didn't assume that I was compliant in this impromptu BDSM venture and they'd be able to help. However, this was at the risk of pissing Stu off further, and having everyone know the truth. I decided on the first option. "HELP," I screamed so loudly that I was surprised the neighbors did not hear. "HE FUCKING RAPED ME!" Soon several men spilled inside the room. Out of the five all of them looked like they belonged on the cover of men's health with bulging muscles and shirts that were too tight. The more concerned of the two sat down on the bed next to my head. "What the hell Stu!" Stu sat silently in the throng of assorted men. They all resembled him in height, yet varied in skin tone and size. Two were muscular, white men one with a beard, and one without. The other was relatively bigger, yet still tall in stature. The last man who was by my head looked like a Caucasian version of Stu except with a stubbly black goatee. The rest of his body was massive. The man untied my hands while the other two unbound my ankles.

"He raped me!" I sat up trembling.

The man petted my head as if to comfort me while I noticed his hands sliding down my chest area. "What," I muttered.

"You were supposed to wait for us to here man!" The man said while staring at me with a strange look.

"Sexy ain't he Derek?" Stu smiled and I finally saw what was about to go down.

"Please man. I'm not a whore. You can't turn me out to other guys that's sick." I spat nearly in tears, and scrambled to get off the bed.

Suddenly, Derek became violent and wrenched me back on the bed by my ankle. "Hold him guys." He said to the rest of the men. With that they all proceeded to grab me by arms and ankles while Derek gathered me in a headlock. I tried scratching at his arms to get free. I couldn't breathe properly and my attempts at kicking the other two large men were made in vain. "Open your mouth," The man whispered harshly into my ear. "You're going to make good on your promise, and when that's done all will be over, and you'll be rid of us. You have my word. Now you can go down kicking and screaming or you can let me make this easy, hell even more enjoyable for you. You decide."

I chose the latter. I screamed more loudly for help when a sudden jab to my stomach caused me to see stars. I opened my mouth in surprise when two pills were jammed down my throat. "SWALLOW!" Derek commanded. "I swear to God if you don't swallow. I'll make your life a living hell."

His tone let me know he was serious. I swallowed hesitantly. Immediately, I started to feel the effects of whatever drugs I had taken. I was acutely aware of everything that was going on yet my muscles felt like they had been halted. I couldn't move anything nor could I stop what was about to happen.

"The muscle relaxer should be strong enough to keep him still until we finish." Derek said to Stu unbuttoning his own shirt.

"Good," said Stu stepping out of his boxers once more. He grabbed me by the ankles and swung my body to the side of the bed. "Who's first?" Stu said smiling. A fear of dread spread through my entire body. They were each going to take turns fucking me like some kind of sex toy, and there's nothing that I could do about it. Derek seemed to be the first volunteer. I squeezed my eyes tight so as not to see the initial plunge. I felt a hand take out the dildo, and for a moment my ass felt safe. The man must have made a move as to try and fuck me because Stu said stop in a way that haulted all activity.

"The best way to inspire a good fucking is through marking the ass as ours." He smiled coyly and produced a bright red paddle from his bag of hell. "Derek you may do the honors while I go fetch condoms. The store across the street has them. Wouldn't wanna catch anything." He winked at me and told the boys to have fun while he dressed and left.

After having seen Stu leave, Derek the rowdiest of the group took it upon himself to "mark" my ass. "Let's get that ass bright and red for you babe," he said sadistically.

Suddenly, the wooden paddle felt my flesh. The pain made me instantly tear up, and I felt my ass grow red. I whimpered in pain trying my best to not give them the satisfaction that they so desired. Each whimper brought an excited buzz among the men. Some were slowly undressing. Two of the larger men were rubbing each other's growing hardons through their workout shorts all while I yelped in pain.

"Please stop!" I begged. My ass more than likely resembled a tomato at this point and the skin from my ass felt like it'd peel off with one more whip of the paddle.

"Now say you're sorry and that you'll be a good boy." Derek made no efforts to conceal his large boner in fact most of the men were in the corner in various states of undress. Making out, moaning, and feeling one another. "We bring out the paddle again if you act up. Now say yes sir!"

I croaked out a compliant, "Yes sir" to which I heard the door swing open. Another round of poppers was applied to my nose by someone I didn't know as Stu walked over to me. He sound irritated and he shoved Derek up against a wall. He slapped him roughly and jabbed his finger against his chest. "Pull that shit again and I'll tell everyone about Mexico."

"No need to make threats man! Just having a little fun." Derek said nonchalantly. "Didn't mean to fuck over your boyfriend!"

Derek giggled and took one of the waiting condoms from the brown bag Stu was carrying. "Now to bust this ripe ass open." He rolled on the condom and shed his shirt revealing a body that outshined all the others. My ass stung further as I heard the sound of Derek spitting on my hole as a form of extra lube. Mistakenly I opened up my eyes just in time to see and feel his hard dick pressed against my hole. I desperately wanted to shut my eyes again, aware of how huge the man's dick was simply from feeling the girth alone, yet I was oddly intrigued. I had only ever been fucked by Stu. This new man piqued my curiosity and once again I'm ashamed to say that my penis became enlarged once again. I moaned in shock as he entered me. This was a new type of pain. Whereas I had experienced dicks that were long in size I had never experienced a dick with such girth. Could I have screamed without evoking further rage I would have done so, yet all I could do was look away and lay breathlessly as the man pushed in further and further. My asshole was being stretched to extraordinary lengths and Derek wasn't being gentle at all forcing himself into me inch by inch with no heed to the amount of pain that was being caused. My body and mind fell into shock again and I screamed inwardly.

"Stop! Dammit you're hurting him." I hazily made out the words that were coming out of Stu's mouth. "This is supposed to be sensual and pleasurable not some giant prison shank." Stu had shed his clothing long ago as well and was jacking one of the other more muscular men when he stopped and glared disapprovingly. Derek smiled. "Sorry man. Didn't realize you hadn't broken him in properly." With that Derek proceeded to make an attempt at going easy on my poor asshole. However, I was still in immense pain for several minutes as he pounded away with my legs on his shoulder. Another man with brown skin and brilliantly white teeth approached where my mouth was and stuck his dick inside wordlessly. The uncut cock slid down my throat easily and I made no effort to bite, afraid of his adverse reaction. "Siith" I said with a mouthful of cock. Derek had taken his dick out of my ass, and a new one had replaced it. From the corner of my eye I could make out the larger man. His dick felt fat as it entered me. He knew how to work it well. I soon began to feel a pleasure in my ass that turned my dick harder. I soon felt another dick in my mouth that felt as if it belonged to Derek. It was thick and he shoved it so far down my throat that I gasped for air. He pulled it out due to Stu's reprimanding him.

I'd never heard concern in Stu's voice just lust and possessing ever sense the first time we fucked. He seemed...caring and worried about me. Soon everyone started to focus primarily on me as opposed to before when they were 69'ing one another and kissing passionately in various corners of the room. I felt hands touch my abs and run through my hair. A mouth soon encased my own dick as another entered my ass and mouth. They were taking turns pleasuring themselves, yet pleasuring me primarily. There was no longer pain in my ass and each dick that entered my mouth I sucked desperately and with hunger. I was even surprised at my enthusiasm. Oddly, enough no one came. I tasted the precum of all of the men, yet not one came into my mouth, that is until it was time for Stu's turn.

A man tenderly stuck the tip of his dick in my mouth. Surprisingly, I remembered the feel. The shape and girth were so familiar to me that I sucked almost instinctively. By now I knew that it belonged to that of Stu, the deep, chocolate color of it becoming clearer in my sight. My head sat between the two muscular thighs, as he stuck himself inside my mouth deeper. As he started to moan in pleasure a peculiar thing happened. Although the drugs had made me weak I used what remaining muscles in my tongue to flick the slit of the dick. I was actually starting to enjoy servicing him! He held my held up so as not to choke me. This was unlike the other men who had entered the room horny and willing to fuck a corpse if need be it was sensual, yet carnal, and painful yet gratifying all at the same time. Being with Stu was an assortment of emotions that I couldn't figure out. All I knew was that his moans were encouragement and each guttural one made my already hard dick twitch harder.

One of the other guys named Joey withdrew from my ass and said, "Can we please cum? This hot piece of ass is ready for it. He slapped my raw and reddened ass, and I flinched in pain."

"That's my ass you're talking about," Stu said somberly. "And I will be the one finishing." He took the dick out of my mouth and another one was unceremoniously tossed in. Soon I felt my tender ass lift into the air, and my legs hoist onto his shoulders as Stu took the job of fucking me last. A tongue flicked in and out of me, and I moaned in ecstasy. To some extent I was actually enjoying myself and it shamed me. After rimming me for a couple of minutes Stu gently plunged his dick into my ass. This time it felt different somehow. He took his time with my stretched orifice first inserting the head then slowly gaining traction as he'd done so many times before. I couldn't quite make out how it was different but as I felt him slide into me over and over again I couldn't help but to feel an overwhelming sense of pleasure unlike any I'd experienced before. He licked my foot seductively and I felt another pair of men fuck loudly next to us. Soon Stu relinquished my foot and kissed my neck. "I'm going to cum he whispered." As I felt Stu start to cum another man had taken to jacking my dick while Stu pistoned. As soon as Stu's seed coated my ass an unbelievable orgasm sputtered from my cock as well covering my abs. Stu groaned a content groan. The other men ceased fucking next to me and made a circle around me while jacking. One by one cum flew everywhere. By the time each man was done my hair, body, mouth, and ass was covered in it. Derek even held me roughly by the hair as he forced me to swallow his bitter semen. After everyone was finished Stu loudly commanded them leave.

As everyone spilled out of the room with clothes, and dicks in hand Stu wordlessly went and closed the door behind them. I sat unable to process my feelings. It had all felt so wrong when it was happening like a prison yard rape. Yet, I missed the sensations. I had been given such amazing pleasure in those two hours more so then I'd ever gotten with anyone. Stu came back and removed the nipple clamps, and picked me up like a rag doll still not saying a thing. The dried cum still entrenched in my hair, I felt like a dirty whore, and it took all of my energy not to cry in his chocolate, sensual arms right then. I buried my head in his chest as we headed for the bathroom. He set me down in the tub and turned warm water on. I pondered what would happen next as the tub filled with soothing waters that rushed over my entire body. Stu left and came back with a washcloth and sat behind me in the tub, legs and body pressed up against mine. His heart beat fast against my chest, and I grew a boner once again without even thinking about it. Every part of this was sensual, and amazing. Stu ran the washcloth over my abs cleaning the dried cum from my worn and over-sensationed body. He turned the shower on and the cum disappeared from my hair cleansing me from any hate or guilt I had felt from Stu's hands. Suddenly, I felt his hardening dick press against my ass. As he groped it he kissed all down my spine, and over my face. Without saying a word he pressed himself into me, and I gave over to his passion. I kissed him back just as deeply and ground my hips into him under the warm, encompassing water. He grabbed my body and played with my hair while kissing my neck.

"You will always be mine," He said matter-of-factly, yet strongly as if I had no other option. I kissed him back and continued to ride him, and in that moment I knew it was true. I wanted Stu more than anything in this world, and no matter how much I wished I could hate him I couldn't. He had opened me up both literally and physically speaking and we would be my largest regret and yet my hugest accomplishment, yet I didn't care. "Just fuck me." I whispered softly. And with that we melted into one another.