ASSaulted

I turned my head away. "Not now...", I muttered, defeated.

"Okay, then I'll just fuck your ass now, and you'll have two weeks to find a dude you can deal with. Then I'll get my turn. Remember though, if you don't find a guy, I'm still fucking you in two weeks. Or you can flush your college career down the drain. Oh, and when you get fucked, I want pictures. Full body nude. Sperm dripping from you. At least a dozen."

"Bastard...." I breathed.

"Call me what you want, at least I'm not a brainless, cheating bitch like you. Ready to get your ass fucked?"

"Please be gentle, I've never put anything other than my finger in... in my ass", I begged again, "Don't hurt me."

In response, a second finger soaked with pussy juice went into my ass.

"Fucking damn it!" I cursed, "what did I just say?"

My blackmailer just laughed, "This is me being nice. Getting you nice and stretched before putting this in." And with that, he slapped his dick up on my pelvis.

It took me a second to realize what was sitting inches from my vagina and ass, while he continued fingering my ass. But my nipples hardened and within a few seconds my vagina started dripping even more as they moved around and in and out of my ass. I gasped, "It won't fit. You're gonna rip my ass apart!"

"Might feel that way for a bit, but I doubt you'll rip and that's gonna feel so good", he told me, "Heck, if you're lucky you might even get your first orgasm."

Try as I might to deny what my body was feeling, I was breathing hard when I said, "I doubt that."

My blackmailer briefly moved away from the bed. A moment later I heard a squirting sound, the next he was back between my outstretched legs and suddenly started rubbing a cold, slimy substance all over my asshole. The unexpected sensation made my legs instinctively flail, but the handcuffs were doing their job, keeping my limbs bounded.

"Calm down, it's just lube", he said as his fingers worked their way deeper and deeper into my ass, "It will help to lessen the pain for the both of us, trust me." The truth was, I couldn't care less what was its purpose, the only thing on my mind at the moment was his fingers pumping in and out of my tight asshole at increasing speed.

As much as I didn't want to show any enjoyment, my own body was betraying me. My breathing was getting more and more ragged and fast. My blackmailer must have felt it too, as his other hand latched onto my clit and rubbed frenetically, pushing me over the edge. Without missing a beat, while my whole body was still twitching from the mind-blowing orgasm, he pulled his fingers out of my tender asshole, pressed his dick's head against the sweet pucker of my ass and pushed.

Despite the combination of lube and my own arousal helping vastly, I grit my teeth as I felt him begin to push inside my ass. My ass tightened and I whimpered, overcome with pain. It hurt so badly. But he continued to inch his way in, making me scream and buck. It was excruciating.

"Relax, Olivia. It will make this easier for you."

"Easy for you to say, you heartless bastard", I shot back. However I did take his advice and tried to relax my ass. A moment or two later I could feel his balls against my ass and knew he was completely inside of me. My blackmailer slowly slid his cock out of my ass and then back in again. I continued to writhe in pain. I couldn't get used to the feeling. I wanted him out of me.

Again I felt him slide out of me. This time I didn't feel him right away, and sighed with relief. But suddenly I felt him ram his cock inside of me. This amplified the pain, ripping a scream from my throat. He continued to thrust brutally inside of me, eventually lacing the pain with a bit of pleasure.

I sucked in air, attempting to get my mind off the horrible pain. I heard him groan, as he increased his pace. At this point I could feel my stomach muscles tighten. I recognized this sensation from earlier and knew an orgasm was stirring. My pussy walls began tightening and twitching. I tried to fight off the orgasm; I didn't want to enjoy what he was doing.

My blackmailer continued to increase his speed, breathing heavy. His hands had found my tits, squeezing them roughly. He must have been pistoning in and out of my asshole for a minute or two max, when my own orgasm hit me. I arched and strained against the bonds as tingling pleasure radiated through my body, making my clit twitch madly with pleasure. I moaned loudly and shuddered, consumed with satisfaction.

During my second body rocking orgasm, I vaguely heard him moan as he reached his peak. He thrust hard into me a couple more times before entering into his own orgasm. When I felt his last few thrusts and his seed pour into me, I was plunged into another intense orgasm that was almost painful. As the pleasure stopped surging through my exhausted body, I struggled to catch my breath.

He gave my tits one last squeeze, and without a word, he pulled his dick out, walking away from the bed. I heard him unlocking his phone and snapping a few photos just as the first glob of his semen started drooling out of my ass. I imagined him smiling proudly at the scene, which filled me with anger once more.

"You gonna let me out now? I need to pee." I demanded.

No answer. He wasn't planning to leave me all tied up like that, was he? "FREE ME, YOU SICK PRICK", I shouted in desperation. "I did everything you asked, let me out now...", I whined as tears filled my eyes again.

Suddenly, I felt him place a thread in my hand, tying it to one of my fingers. "I could let you pee yourself right here and leave you like that, but even I am not that sadistic. However I can't just uncuff you either and run the risk of you seeing me. On the other end of this string is one of the keys to your handcuffs. Pulling the strings will give me time to get out of your house where you won't be able to find me, then you'll be able to unlock yourself."

"Fuck you." I snapped while immediately starting to work on the thread.

"You will", he replied. "With your pussy in two weeks, maybe again with your ass in the meantime. That was great."

"Like hell I will. I'll make sure to find your identity beforehand, and end this fucking little game of yours!" My plan was clear: get the key as fast as possible to free myself, and keep my blackmailer around long enough so that I could at least catch a glimpse of him.

"I won't bet on that", he said cockily, giving my ass a good slap.

"Fuck you, fuck you, FUCK YOU", I shouted repeatedly, but he was already gone.

It took me longer than I expected to free myself. Even with the key in hand, trying to find the hole while blindfolded was harder than I imagined. As soon as I got rid of the handcuffs, I bolted to the toilet. I really needed to pee, I wasn't bluffing.

I returned to my room after and looked into the mirror at the damage the bastard had done to my asshole. Although it was still hurting like crazy, there was no visible mess at least. I couldn't say the same for my pink bed sheets, as I looked in frustration at the smears on my bed. They were completely ruined.

Then I noticed the video call was still going and promptly ended it. I sat back on my bed gingerly and sighed. There were so many things on my mind. It was so painful, yet why did my body enjoy it so much? Also, how was I supposed to find a suitable guy in two weeks and convince him to take my virginity? I decided to postpone for now my search for answers. I wanted only one thing: a long, hot bath to get rid of the filthy feeling that clinged to my skin.