Sex stories

Short sex stories




The Boss

I awoke to a throbbing headache. Every heartbeat was an explosion of pain. It took all the strength I had just to sit up. My head spun for a second before I allowed my eyes to flutter open. Tears blurred my vision, making the world appear as a distorted mess. All I could see were colors and shapes.

I tried to speak, but only a faint squeal escaped. My throat was dry, keeping the words that difficultly formed within my brain from reaching the outside world. I tried a few more times before finally giving up.

I began to panic. Where was I? How had I gotten here? And why was my head throbbing?

It took a while for the confusion caused by my brutal return to reality to fade. By then, my vision had returned and I was finally able to study my surroundings.

I sat on the floor of a high-end office. A few pieces of furniture were present, but the room was for the most part empty. Whoever owned it had clearly just moved in. My gaze instinctively travelled to the black, hardwood desk, but the leather chair that stood behind it faced away from me. I couldn't tell if it was occupied or not.

I continued my inspection. I noticed a lamp standing in one of the corners. Its light only partly illuminated the room, keeping the rest of it bathed in darkness. A few file cabinets stood in another corner. The final two shapes stood on either side of the boor.

They looked human, but seemed frozen in place. They just stood there, motionless. Their bodies were bathed in darkness and all I could see were blurry shapes. I stared at them for a while before finally noticing their shoulders shifting ever so slightly as they inhaled and exhaled. They were alive.

I opened my mouth to beg for their help, but the words died in my throat when I realized they were probably responsible for my current confusion. The size of their frames told me any hope of escape was foolish. If they were indeed keeping me captive, freedom would remain but a hopeful dream.

I sensed their stares on me and felt a shiver run across my skin. This brought to light a fact I had up until now failed to notice.

I was naked.

Every inch of my young body was uncovered, making me feel even more vulnerable than I already did. I pulled my knees to my chin and hugged my legs. It helped warm me, but shivers still tickled my spine. I suspect they had something to do with the intense fear that filled me.

It took a moment before my dread faded enough for my brain to start functioning again. I took a second to revise my current situation. I had awoken to naked captivity in a dark and mysterious office. But how had I gotten here? And why?

"Don't be afraid." The voice emerged from the darkness, making me jump. My gaze instinctively travelled to the two human statues, but neither of them had moved. They seemed more like guards than conversationalists. Whoever had just spoken was somewhere else in the room.

I glanced around for a moment before a movement caught my eye. The desk chair was slowly spinning, gradually revealing the man sitting on it. He was old—probably in his mid to late forties. The coldness of his gaze sent another shiver dancing across my skin. There was something familiar about the man, but I was too terrified to piece the puzzle together.

"Here," said the man as he leaned forward and outstretched one of his arm. His hand clutched a glass of water. I stared at it, then at him. I could tell he was not the type of man to accept defiance, but the anger that had up until now been suppressed by my fear finally bubbled to the surface.

Forgetting about my lack of clothes, I leapt up and yelled something that was meant as an insult. But my throat was still dry and only a pathetic wheezing was heard.

I expected the man to smile, but he remained impassive.

"Take it," he insisted, nodding to the glass.

I eyed it suspiciously, but my thirst eventually won out. Rushing over to the desk, I snatched the glass from the man's hand and downed it in only a few gulps. A relieved sigh escaped me as I regained the ability to speak. The water had also helped diminish the intensity of my headache. Only two problems now remained: My lack of clothes and my mysterious captivity.

I focused on the man behind the desk. The sensation of déjà vu yet again gained me. I knew this man, yet my scattered brain refused to reveal his identity. I once more took in my surroundings, but that did little to help elucidate the mystery. Perhaps the answer lay somewhere in the past.

Ignoring the three men that stared at my naked body, I closed my eyes and focused on remembering every detail leading to my current situation.

I started with the basics. My name was Candice Swan. I was eighteen and still a virgin. And I had just been accepted into the college of my dreams. Aside from that, everything was a blur.

My eyes fluttered open and my gaze landed on the man behind the desk. The sight of his grim expression acted like an electroshock, igniting a flurry of memories that made my heart race with fear.

I knew who this man was. I had never met him, but I knew exactly who he was. His name was Frank Mazolla and he was the biggest crime boss this city had ever known. People spoke of him in hushed tones and fear gripped the citizens each time a particularly heinous crime was committed. The man had been arrested hundreds of times, yet not once had he set foot in a prison cell. He had connections, the type of connections that made him the most powerful and feared man in the city.

As terrifying as the man's reputation was, it was the memory of a particular newspaper article that made my heart skip a beat. According to law enforcement, dozens of young women—all of them eighteen years of age—had mysteriously gone missing around him. No one knew what happened to them, but they were never seen again.

The shock of my discovery made my fingers lose their stiffness. The glass slipped from my hand and crashed to the ground. I expected it to shatter, but it simply clattered to the floor and rolled under the desk.

The crime boss stared at me. I stared back. Silence filled the room. My hands started to tremble. Beads of sweat appeared on my forehead. Tears filled my eyes.

Finally, I couldn't take it anymore.

"What will you do to me?" I asked. I was surprised by the forcefulness of my voice.

The mobster didn't react. He just sat there, staring at me.

I didn't know what to do, so I simply stood there and waited. I wanted to cover myself up, but I knew it would be interpreted as a sign of weakness. I couldn't afford to look weak.

"I won't hurt you," finally said the man. Relief washed through me. "Unless you're a bad girl. Bad girls get punished."

The sigh of relief forming within me died in my throat. Fear shot through me again, now more intense than ever. I was so terrified I barely even noticed the man open one of the desk drawers. It wasn't until he handed me the item he retrieved from it that I realized what was about to happen.

"Put it on." His voice was firm, but polite. My eyes landed on the item he kept balanced on his open palm. It was a black leather collar. Attached to it was a long leash. Its purpose was obvious.

I couldn't speak. I could barely breathe. I just stood there, staring in the collar in disbelief. Its presence, combined with my lack of clothes and my virginity left no doubt in my mind as to the nature of the events about to unfold. I was the latest in a long line of beautiful young women to vanish under mysteriously circumstances. No one knew what had happened to my predecessors, but I feared it involved a lot of pain. All I could do was play along. Either I would satisfy the boss so thoroughly he chose to let me go or I would die in the most pain-free manner possible. It was a grim through, but it was the only one that filled me with a meager sense of hope.

My hand trembled as I reached for the collar. The boss's gaze remained fixed on me. His face was impassive and his hand remained perfectly still. He had done this countless times before and, unlike me, he knew exactly what was coming. All I could do was play along and hope for the best.

I took the collar and brought it up to my neck. The leash unrolled. One end was attached to the collar, the other remained in possession of my captor. He watched with a complete lack of emotion as I slipped the collar around my neck and slipped the prong into the middle hole.

"Tighter," said the boss. His voice was void of emotion.

I pulled the collar tighter and once again slipped the prong into a hole.

"Tighter."

I gave the man a pleading glance, but he ignored it. I slipped the prong into the only remaining hole. It was now so tight I felt a constant strain against my neck. I could still breathe freely, but the leather against my skin was a constant reminder of my total and utter lack of power. My captor had complete control over me and he wanted me to know it.

He tugged on the leash. I followed, almost stumbling forward in the process. I quickly regained my balance and let the boss reel me in. He kept pulling until only a foot of leash remained.

"Get on all fours." He said it as if it were the most normal thing in the world. The thought of debasing myself to such an extent repulsed me, but my dignity had already been shattered when I had agreed to wear the collar. I grit my teeth and did as told.

My captor said nothing for the longest time. He just held the leash tight and stared straight ahead like we was observing something of indescribable beauty. Only there was nothing there.

I stood there, wondering how long I would be asked to remain on all fours. Within minutes, my knees had begun to throb. The floor was made of hardwood and the blood was pooling in my legs, making them go numb. My elbows soon began to shake, though I could not tell if it was from exhaustion or fear. All I knew for sure was that I could not hold this position for much longer. Just when I was about to crumble to the floor, the boss finally gave me permission to stand.

"Sit," was all he said. His chair swiveled toward me and he gently patted his lap. My heart began to race at the thought of sitting in the lap of the most feared man in the city, but I knew refusing to do so would be far more dangerous.

As soon as I was seated on the man's thighs, he began petting me. Only he didn't pet my hair. He pet my back, as it I were some sort of an animal. Given the collar I was wearing, the man's demands were beginning to make sense. He wanted me to pretend to be an animal. His skin was ice cold and made my hair stand on end, but I resisted the urge to shy away from his touch. The safest thing to do was play along and hope he allowed me to live.

He pet me for a while, his gaze focused on nothing in particular. It was an odd feeling to be treated like a pet, but I preferred it to the pain that would undoubtedly have followed a refusal to play along.

"Get off," he finally said. I instantly hopped off, all too happy to put an end to the weird animal roleplaying.

My relief was short-lived.

"Sit on the desk."

The massive hardwood desk stood behind me, so all I had to do was lean back, place my hands atop it and lift myself onto it. A shiver ran through me as the cold surface made contact with my body. The boss and I now stood across from each other.

"Spread your legs."

My heart skipped a beat. There could only be one reason why he would ask me to do this. Unfortunately, there was nothing I could do to stop it. I slowly spread my legs, revealing the tight, clean-shaven pussy that stood between them. My captor eyed it with great interest, a barely noticeable smile curling his lips as he did.

"Play with yourself."

Part of me was relieved that was all I was being asked to do. Another part suddenly felt self-conscious. I glanced over my shoulder at the two guards. They still stood there, perfectly still.

"Don't worry about them," said the man. My nervousness had clearly not gone unnoticed. "They will do whatever I tell them to." To prove his point, he gestured for the two men to step forward. They did, emerging from the shadows for the very first time.

I almost gasped at the sight of them. Now that their faces were revealed, I realized they were more than similar in shape and size. They were identical. They were twins. Even their clothes—black suits that could barely contain their bulging muscles—were identical. Their heads were completely shaved and their jaws square. Their eyes were emotionless, but behind that emotionlessness stood cruelty.

"Tom," said the boss. "Punch your brother in the face." Tom—the left twin—didn't even hesitate before clocking his sibling in the face. The brother didn't flinch, not even when blood began pouring from his nose. He just stood there, emotionless as ever, until he and his brother were given permission to return to their posts. Moments later, the darkness swallowed them once more.

I could hardly believe what I had just witnessed. My captor's demonstration did more than simply prove how tough and uncaring the twins were. It also showed me how powerful they were. If I did anything to displease the boss, the guards would not hesitate to bring their wrath down upon me. Unlike the wounded twin, I knew I could never survive such a blow. I was now more determined than ever to obey the boss's every command.

I did not wait for him to repeat the order. I lowered my hand to my pussy and began slowly teasing my clit. My heart was racing madly, though it had nothing to do with the sexuality of the situation. I continued teasing my slit, massaging the labia one second and flicking the clit the next. A little arousal snuck into my body, but the fear that filled me kept me from enjoying the feel of my fingertips brushing against my opening. Thankfully, my captor seemed to be enjoying himself.

"Insert a finger."

My heart skipped a beat, but I did as told as if nothing had happened. I slid it deeper and deeper until every last inch had been swallowed up. I couldn't believe how wet I was. Perhaps the fear was acting as a boosting agent, making my arousal more potent. All I knew was that I had only been asked to insert the finger. I kept it buried within my wet slit until I was asked to do otherwise.

"Pull it out and lick it."

I had pleasured myself countless times, yet I had never once tasted myself. I guess there's a first time for everything. I gently retracted my finger and brought it up to my lips. I slowly slipped it into my mouth and closed my lips around it. I used my tongue to lick the pre-cum from the appendage. I almost moaned when I realized how sweet it was. Part of me regretted having waited this long to try it while another was simply relieved something good was coming out of all of this.

The boss waited until I was done before giving his next command. "Finger yourself. With two fingers." I lowered my hand to my pussy and slipped two fingers into it. I almost moaned when the digits began gliding in and out of me. Not because I was turned on, but simply out of habit. Thankfully, it was one I quickly learned to suppress. It was in silence that I fingered myself, slowly increasing the speed with each new penetration.

I expected my captor to begin stroking his cock through the fabric of his tailor-made pants, but he just sat there and stared at me, emotionless as ever. I had no idea how a man could be this cold and unfeeling, but I preferred this to an overzealous man who couldn't keep his hands to himself.

I kept going until something unexpected happened. I started to enjoy myself. It was such a familiar feeling I almost didn't realize what was going on. By the time I did, it was too late. I was turned on and nothing short of a miracle would keep me from climaxing. Part of me was repulsed by my behavior, yet another was relieved the fear that had inhabited me ever since my brutal return to reality was finally gone. The arousal coursing through my veins was all I could now feel.

At first I tried to resist it, but it quickly became evident that would be impossible. I'm not quite sure when it happened, but I eventually gave in to it. Moments later, I was moaning blissfully. My eyes rolled back in my head and my head was thrust back. My breasts rose and feel to the rhythm of my rapid breaths. An orgasm began to sneak up on me. It was only a matter of time before it took hold of me and brought me to climax.

It was not meant to be. Moments before reaching the point of no return, the boss's voice filled my ears. "Stop," it said. I tried to obey, knowing what would happen if I didn't, but my body refused to response. My fingers continued darting in and out of me, luring my orgasm ever closer. I struggled to regain control of my body, but it was useless.

I continued to fight, but it was becoming increasingly obvious I would not regain control in time. But then something made contact with my face. It was cold and felt oddly familiar. It was a hand. Pain shot through me and put an immediate end to my lack of control. Instantly, I yanked my fingers from my slit.

"I'm sorry," I apologized as soon as my eyes flew open. They were filled with fear. So was the rest of my body. My captor didn't respond. He just stared at me, unblinking. I instinctively lowered my gaze, hoping such a sign of submission would be enough to convince him to spare me.

It was.

Acting like nothing had happened, the man gave his next command. "Approach." I didn't understand its meaning until I realized it was meant for the two bodyguards. I turned to them just as they emerged from the darkness. The one who I knew not the name had stopped bleeding. The blood had been wiped away, leaving only a slight swelling as proof of his injury.

"Remove your pants," instructed the boss. Fear shot though me as my mind began to race in search of a non-sexual explanation for such a request. None were revealed. I watched in horror as the twins untied their shoes and removed their socks, before slipping out of their respective pants. The final pieces of clothing to leave their muscular bodies were their boxers. Another lightning bolt of terror shot through me at the sight of their cocks. They were large, though far less impressive than their physiques indicated. Still, I doubted a young little thing like me could handle either one of those members, let alone both.

I didn't realize I was holding my breath until I started to run out of air. Inhaling deeply, I did my best not to stare at the guards' shafts. I only now noticed they were half erect, proof that they had enjoyed watching me pleasure myself. Realizing this chased away the last few shreds of arousal from my body. Only fear and repulsion remained.

"I assume you know what to do." It was my captor who had spoken.

I honestly had no idea what he expected of me, but I was afraid to admit it. I simply nodded and slipped off the desk. I slowly made my way around it. Since the boss did nothing to stop me, I assumed I was doing the right thing and kneeled before the twins. My face was now less than a foot from their cocks. They twitched in anticipation.

I feared I knew what was expected of me, but I wanted to give the boss one final chance to change his mind before it was too late. I peered back at him over my shoulder. I expected him to just sit there and stare at me with that emotionless expression of his. Instead, he nodded. It was only a slight nod, but it was enough to crush the last shreds of hope I had left. I now knew for sure what was expected of me.

I turned back around and focused on the cocks that stood before me. They looked even larger than before. More out of desperation than curiosity, I glanced up at the twins. They just stood there, staring down at me emotionlessly. With that, I knew my fate was sealed. Either I sucked their cocks or their boss would allow them to pummel me to death. For a split second, I considered letting them end my life, but then my survival instinct kicked in and, suddenly, all that mattered was living to see another day. Taking advantage of this to overcome the fear that gripped me, I reached out with both hands and wrapped five fingers around each member.
I was still a virgin, which meant I had never before touched a cock—let alone two. I was surprised by how hot they were. I also felt the blood course the veins that riddled them as I wrapped my fingers around them. I chose to believe the best way to proceed was to get through this as quickly as possible. Hopefully it would be over before my repulsion outweighed my fear. If that happened, this would be my first and last sexual encounter.

I began moving my hands up and down the length of the shafts. Each stroke lured more blood to the members, making them grow in both length and rigidity. It took only a few seconds before they were both fully erect. As soon as I was confident they wouldn't go soft on me, I picked one at random and let go of it. Acting before my body could realize what I was up to, I leaned forward and wrapped my lips around the tip of the shaft.

The cock shuddered as I forced it deeper and deeper into my mouth. I kept going until it reached my uvula. Once that happened, I pulled back and began swaying back and forth. The shaft felt even hotter in my mouth, but my saliva helped cool it down. It was the perfect temperature. In a matter of seconds, I had grown accustomed to the sway of my body and the slight saltiness of my sexual partner's member. Giving a blowjob had now become second nature. I couldn't believe how quickly it had happened, but I was thankful it had. Had I been forced to battle my repulsion the entire time, I never would have survived my first sexual encounter.

I worked the first twin's spear with my mouth while using one of my free hands to keep the second one busy. My hand was wrapped tightly around his shaft. My arm muscles worked hard, forcing my hand to travel up and down the entire length of the man's member. It still felt as hot, but most of my attention remained focused on his brother, keeping me from noticing such a detail.

After a while, I switched cocks. Moments after my lips encircled the second twin's pole, a voice filled my ears. It was the boss.

"Deeper." That was all he said. It was enough.

I pushed forward, forcing the man's cock farther into my mouth. It quickly reached my uvula, but I kept on pushing, terrified of what would happen if I failed to obey my captor's request. I pushed and pushed, the rigid member was too massive to proceed any my further. I kept pushing, praying for it to slide into my throat. My eyes started to water and I felt my gag reflex being activated, but still I pushed. I began to choke, but still I refused to give up.

"Deeper." This time, the voice was more forceful. He was getting annoyed.

I kept trying, but no matter how hard I pushed, the cock refused to enter my throat. I finally gave up and, momentarily pulling away from both members, turned to the boss.

"I-I can't," I croaked.

I saw a movement, but my tear-filled eyes blurred my vision, keeping me from seeing what my captor was up to. It was only when I felt a hot tongue lash as my skin that I figured it out. The pain that followed left no doubt in my mind. I had just been whipped.

"Try again!" growled the boss. All I saw of him was a blurry shape, but I could still see clearly enough to notice his raised arm. I couldn't see the whip, but I knew it as there and the last thing I wanted was to hear it crack again. I turned back to the twins and once more tried deep-throating one of the members.

I tried relentlessly, but to no avail. The cocks were just too big to fit in my throat. The boss whipped me a total of three times before finally accepting my claims that further penetration was impossible. He simply instructed me to make the twins come and sat there, watching as I got to work.

I sucked and jerked, alternating between the twins half a dozen times before the cocks finally came to life. I had been so focused on getting the brothers to climax that I had failed to plan ahead. What was I supposed to do now? I was struggling with that very question when my captor's voice entered my auditory canals.

"Let them come in your mouth."

I ignored the wave of repulsion that washed over me and focused on the few drops of arousal that snuck their way into my body. I pulled back and opened my mouth wide. Once I was certain both cocks were aimed right at it, I closed my eyes and doubled the intensity of my hand thrusts. It took less than a second for the brothers to climax.

They came at the exact same time. Squirt after squirt shot past my lips and splashed across my tongue. It took a second for my taste buds to identify the flavor that accompanied the semen, but when it finally did, I began to gag. The cum was far saltier than I had anticipated. There was also a slight bitterness to it. My first reaction was to spit out the foul-tasting liquid, but the boss spoke before I could.

"Don't you dare spit," he warned. There was no anger in his voice, but I knew better than to disobey such an explicit command. I fought my repulsion and kept my mouth open.

I continued jerking off the twins until their final squirts landed in my mouth and their cocks went limp in my hands. I released them and let my eyes flutter open. I was surprised that every last squirt had found its way into my mouth, but truly astonished by how much cum there was. I had to seal my lips to keep the hot liquid trapped within my mouth. I turned to the man in charge and waited for his instructions.

"Swallow." That was all he said. I expected to be repulsed at the thought of ingesting all that semen, but I felt only relief. I knew the foul taste would vanish shortly after the cum was gone. I swallowed. A moan of relief escaped me. I prayed the boss hadn't interpreted is as a moan of delight.

By the time the saltiness of the semen had faded, the twins were back at their posts, pants once more hanging from their waists. It was only then that I realized they had seemed impervious to my hand and tongue strokes. They may have come, neither of them so much as grunted when I made them climax. I guess they knew their boss did not stand for anything short of total and complete professionalism.

"Stand up," instructed my captor, drawing my focus back to him. I did as told. He spoke again. "Lie down." He was pointing to the desk. Without a moment of hesitation, I hopped on and pressed my back to the hardwood surface. A shiver ran through me at the touch of the cold surface.

The boss stood up for the first time. He still wore his black, hand-tailored suit, only now the pant zipper was down. His cock protruded from the orifice. It was fully erect and far larger than I ever could have imagined. The boss was not a tall man, yet his member was larger even than the twins'. In fact, it seemed better suited for one of the gargantuan body guards than a man of the boss's stature. Yet there it stood, hard as rock and riddled with veins.

My heart started to race as I eyed the member fearfully. Fear soon washed over me as the man took a step. The cock barely even moved as he approached. My palms grew sweaty and every cell in my body cried for me to flee. But I knew that was not an option.

"Please don't do this," I begged, terrified at the thought of losing my virginity to such a well-endowed man.

He didn't answer. He just kept walking, his cock growing ever closer to my virgin body. In a few steps, he reached the desk. Reaching out, he grabbed my waist and, with surprising strength, pulled me toward him. My legs fell over the edge of the desk. The boss pried them apart slowly, revealing the clean-shaven pussy that lay between. Terror deformed my traits as I watched the man bring the tip of his cock to the mouth of my slit. I thought of making a run for it, but I knew the twins would grab me before I could take two steps. The only way out of this was to let this repulsive man take my virginity and hope he showed me mercy for being such an obedient captive.

A shiver ran through me as the tip of the boss's cock made contact with my lower lips. His hands grabbed my waist in a firm grip. His eyes traveled up my body until they reached my eyes. His gaze was void of emotion, but a faint smile curled his lips. He clearly enjoyed having total control over me. I had no doubt this was the only way he could get off. He was so pathetic.

He jerked forward. His cock shot into me. I cried out in surprise. The initial shock quickly faded, leaving place to pain. Waves of it washed over me, bringing tears to my eyes. But I could still see the boss, grunting as he forced himself deeper and deeper into me. It felt like I was being ripped apart from the inside. Pain tore at my insides as my virgin pussy was stretched past its limits. A distressed shriek formed in my throat, but I refused to let it out. I would not give him the satisfaction.

My captor kept pushing until every last inch of his cock was inside me. I had trouble believing such a thing was possible, yet there was no denying it. The pain that filled me was proof of it. The boss remained inside me for a few seconds, clearly enjoying the pain he was bringing me. Then he started rocking back and forth. I expected the pain to fade, but it doubled in intensity. Each new penetration brought fresh waves of it.

My sexual tormentor began pounding me. He drilled me mercilessly, clearly thrilled with the pain he brought me. Grunts began flowing past his lips as he forced himself into me with unyielding intensity. I retreat into myself. I tried pretending I was somewhere else, but the pain kept dragging me back. I tried to picture myself with someone less repulsive, someone younger. It didn't work. Nothing did.

I was trapped within my own body, unable to escape the hell that had become my life. Pain gripped me, keeping me from fighting back. What little sanity I had left told me to remain calm and pray the boss was a premature ejaculator.

He wasn't.

He rode me mercilessly, each thrust more powerful than the last. It took a while, but the pain finally started to fade. It happened so gradually I didn't notice until it was too late. With each drop of pain that left my body, one of arousal took its place. I tried to fight it, but I was too exhausted to deny my body the relief it so clearly craved. As wrong as it was for me to enjoy feel of my captor's cock drilling my virgin body, it was a welcome change of pace from the fear and pain that had accompanied most of my imprisonment. As repulsed as I was with myself, I knew the only thing I could do was give in to the arousal. Not only would it help me get through my first real sexual encounter, but accepting my fate would mean I was no longer being raped. It was the only safe way for me to strike back at my tormentor.

I started to moan. The boss was so surprised he froze mid-thrust. The tears having finally left my eyes, I was able to see the man's reaction in all its glory. Disbelief deformed his traits, giving him an almost comical appearance. Encouraged by this, I started moaning louder.

The man remained frozen in shock for a while longer before the disbelief dropped from his face, resolve quickly taking its place. He began fucking me again. He rode me with all his might, obviously desperate to put an end to my defiance. But each time he forced himself into me, I moaned, letting the arousal that filled me take over. At first I faked it, but as the pounding intensified, my feelings grew genuine. The man between my legs still repulsed me, but I had grown addicted to the feel of his cock within me. I continued to moan as my impending loss of virginity grew closer and closer. I no longer cared that this entire ordeal had been forced upon me. I was about to lose my virginity and that was all that mattered. In a final act of defiance, I told my captor exactly what I was about to do.

"I'm gonna come!" I screamed. My back was now arched. My head was thrust back. My eyes had rolled back into my head. My entire body was trembling with excitement. It was only a matter of seconds before I climaxed. Once that happened, the boss would lose that little power he still had over me.

There was one thing I had failed to take into account. That very thing turned out to me my undoing. The boss suddenly stopped pounding me and pulled out, cutting me off moments before climax. I was so surprised I didn't know how to react. I just lay there, frozen in disbelief. By the time I recovered, my captor had flipped me over and was now pressing the tip of his cock to my anus. I froze.

Time seemed to slow down. A series of thoughts flashed through my mind. Losing my virginity to save my life was one thing, but letting my captor sodomize me was quite another. How far was I willing to go to optimize my odds of survival? Could I even live with myself if I debased myself to such an extent? What about me family? What if I survived this ordeal, only to have them find out what I had done? Could I survive such humiliation?

As soon as the answer was revealed, time seemed to speed up again. The tip of my captor's cock dipping past my anus was the last straw. I lost it, I went completely insane. I started to fight, wiggling out from under the boss. I kicked and punched. A few of the blows landed, but most hit nothing but air. I began to scream, hoping my high-pitched shrieks could destabilize my captors long enough for me to make a run for it. I somehow made it to my feet and bolted for the door. Hope began to swell within me as I realized there was a slim chance I could actually escape. Then I laid eyes on the twins and all hope was lost. Unlike their boss, the massive bodyguards seemed unimpressed by my outburst. They just stood there, waiting for me to make a move for the door. I knew it was hopeless, but I was desperate. I lunged for the door.

I never made it. The twins grabbed me before I even got within a foot. Lifting me into the air with their powerful arms, they carried me back to the desk and slammed me down upon it. The air was knocked from my lungs. The twins took advantage of this to bend me over the edge of the desk. By the time I started breathing again, I was pinned in place, unable to move a muscle.

"Hold her down!" ordered the boss. I couldn't help and smile when I heard the anger in his voice. But my smile quickly faded when I saw the man reach for the whip that was slung over the black leather chair. I followed him with my eyes until he vanished behind me. Gritting my teeth, I waited for the pain to arrive.

He whipped me three times on each cheek. My ass felt like it was on fire, but I refused to cry. I didn't even squeal. Not until the man dropped the whip and stepped up to me. His hands spread my cheeks apart. As soon as my asshole was revealed, he pressed the tip of his still erect cock to it. I held my breath, waiting for him to make his move. I didn't have to wait long.

He jerked forward with all his might, forcing every last inch of his member into my tight hole. I expected to feel a crippling pain take hold of me, but it didn't. The boss began pounding me, but still there was no pain. I waited, knowing the pain would come. But it never did.

My captor fucked me like there was no tomorrow. The entire length of his spear repeatedly shot into me, yet not a drop of pain appeared. It made no sense, none whatsoever. Such a mystery kept me occupied for quite a while. By the time I realized what was happening, it was too late to stop it. Arousal had returned to my body, now more potent than ever. It flowed from my heart with each beat. It spread through me through my veins. It inhabited my every cell. The feel of my captor's cock drilling my ass was all I could think about.

I hated myself for it, but there was no denying how much I enjoyed my first anal drilling. Perhaps it was the knowledge that in doing so I was defying my tormentor. Perhaps it was because I was so desperate to lose my virginity that I was willing to let a man more than twice my age live forever in my memory as my first lover. Or perhaps it was simply that I enjoyed anal. All I know for sure is that I was rapidly nearing climax and nothing could stop it. To my utter surprise, I was actually looking forward to losing my virginity.

I waited until the last second to say it. By the time the words "I'm gonna come!" left my lips, it was too late for the boss to stop it. Clearly aware of this, he continued pounding me, pushing me past the point of no return. Moans shot past my lips as my entire body came to life. My eyes rolled back in my skull. My head shot back. My back arched. The cold wood of the desk felt great against my erect nipple. My sweat-covered body began to tremble. The shuddering intensified until only my pussy was shivering. It shook uncontrollably for a second, then grew still. A second later, I started to squirt.

The cum shot out of me. It splashed onto my thighs and ran down my legs. It felt so hot against my skin. As did the semen currently being pumped into my asshole. Squirt after squirt of it flowed into me, lubricating my rectum and making my captor's penetrations even easier.

I don't know how long my orgasm lasted. It could have been a few seconds like it could have been an hour. All I know for sure is that I had never felt this satisfied in my entire life. When the man's cock finally went limp and slipped out of me for the final time, I crashed down onto the desk. Moments later, the twins released me and I fell to the floor. That was where I remained for the next few minutes, gasping for air.

As my strength gradually returned, I was able to take a moment to gather my thoughts. I was no longer a virgin. Nor was I an anal virgin. Worse even, I had lost them both to the most dangerous man in the city. But the worst part of all was that I had fought back. Any hope I may have had of surviving this ordeal was gone. It was only a matter of time before my life came to an end. All I could do was hope my death would be quick and painless.

I thought of going down fighting, but I was too exhausted to open my eyes, let alone fight for my life. I simply lay there, waiting for a blade to slice my throat or a bullet to penetrate my skull. But neither of those things came to pass. In fact, nothing at all happened.

When I could no longer stand it, I opened my eyes. All I saw was the dark ceiling. I sat up and glanced around. I was alone. I stood up and studied my surroundings a second time, but there was no sign of my captors. I was completely alone.

It made no sense. Why had they chosen to leave? I had seen their faces, taking them down would be as easy as going to the cops. Perhaps the boss knew he had nothing to fear because of his reputation. No cop in his right mind would dare go up against him, especially not for something as trivial as a rape claim. Or perhaps he had suddenly grown a conscience. Either way, I was now free, and that was all that counted.

The first thing I did was remove my collar. I chucked it into a corner of the room and glanced around in search of my clothes. When I found nothing, I decided to search the desk. But I quickly forgot about that when I noticed something on the bare surface of the desk. It was a small sheet of paper with a few paragraphs scribbled upon it.

My hand trembled as I reached for it. Scooping it up, I brought it up to my face.

Dear Miss Swan,

I know you believe me to be a monster, but a man in my position cannot afford to look weak. That is why no one has ever known the true source of my motivation. I do not do the things I do out of malice, but self-preservation. No one but me—and now you—knows this, but I suffer from a disorder that prevents me from having an orgasm. That is why I have kidnapped and forced myself upon so many young women. My hope was that the tightness of their youth would allow me to climax, but to no vail.

Then I met you and everything changed. I do not know what it is about you, but you have given me something I have dreamed of my entire life. To show my appreciation, I have chosen to let you go. I hope you can forgive me for what I have done. I will never forget you or what you have done for me.
Frank Mazolla

I couldn't believe it. What was so special about me? How had I accomplished something so many others had failed to do? And what about my own loss of virginity? Would the memory of my captor's cock inside me haunt my every waking moment or could I grow to accept the manner in which I had lost my innocence? Many more questions bounced around my mind, yet not a single answer was provided. All I knew for sure was that I was proud of my accomplishment. Not many people could claim to have survived an encounter with the feared Frank Mazolla. But I could.

boss   the  

Feb 7, 2018 in romance

Tags

Search