Crossing the Line

Story Info
Exploring some taboos.
4.5k words
4.36
97.5k
29
3
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I've written this story at the request of a fan. It is purely fiction. I want to give a prologue that quickly explains my attitude to the issues it raises. Certain things happen in this story that I would not want to happen in real life. In real life I believe in equality and consent. I have moral values. However, my mind is a safe playground for any fantasy I choose. If fantasies remain fantasies and do not become obsessions, they are safe. They are also exciting. Enough of that, you're here for my story.

The internet became part of my life from the moment my parents first taught me to use it. It opened up a world that was so much wider and more exciting than the real world that I spent my childhood living in. By the time that I was eighteen I had surfed and chatted for years. At eighteen, though, I was ready to take things further. In the long summer before I went away to university, my parents bought me my own computer. It was put in my room. I think it was their way of letting me know they trusted me. Before I had always had to use the family computer. I had known all the time that dad could check up on my browsing if he wanted to. Not that my parents are like that, they respect my privacy. It still held me back, though, knowing that if I had looked at something naughty there was a chance my dad might have found out. My parents would never have shouted at me about it, they would just have talked it through with me. They're reasonable and liberal people. Trouble is, I didn't want to have that discussion with them.

The computer in my room opened some doors that I had only been able to walk by in the past. Naturally I had, well, peeped through the keyholes of those doors in the past but I had never properly explored the rooms beyond. I'm not ashamed to say that those summer nights with my new computer were spent exploring every adult site I could find. I watched endless clips, flicked through image after image, chatted to people with fantasies and fetishes I had never imagined. I always remained safe and never revealed too much about myself. Most of the time I wouldn't dare to play when my parents were home but, luckily for me, they are bopth busy people, always travelling for work. My mum is heavily involved in social work and travels in this country and abroad. Dad is a financial consultant, disappearing all over the world whenever a company needs him. That leaves little me, the spoilt brat, home alone with my toys. Those hot summer evenings alone in the house were a time of intense pleasure and self-discovery.

Then came Libertine.

I met him in a chat room where I was constantly bombarded with requests for private chats from men with names like "roughdaddy" and "eightinchesoncam". Why did Libertine appeal to me? Mainly because he was so articulate and witty. He amused me. He was also incredibly frank. He never tried to pretend that he didn't want to talk about sex. From our first conversation we were discussing our desires and fantasies. The night we met we enjoyed a session of roleplay that was kinky enough to make me feel guilty the next morning. He liked to dominate and I liked to explore my submissive side. While he played our game he told me what to do in real life and I happily obeyed his instructions. I rub my clitoris, pushed fingers into myself and, eventually, used the handle of a hairbrush to fuck my arse. I had played with my anus in the past but it was Libertine who got me to go further than just play. I'll never forget rolling a condom down the unyielding plastic of that handle. Looking at it before I positioned it behind me and started to push against my already wet anus.

Within a week he had convinced me to share my MSN with him. I took very little prompting to buy a webcam. I remember feeling a thrill of guilt and pleasure as I brought it home and hid it in my desk draw. It wasn't until the house was empty that I dared to try it.

I saved it for Libertine. He was the only person I wanted to try it for. When he eventually came online, my throat constricted and my heart began to pound. He wasn't pushy. He didn't even ask about the cam. When I mentioned it, he seemed pleased but he didn't start begging me to turn it on. His coolness was what won my admiration. Other men were always begging for more and more. One picture was never enough. They always wanted more pictures, phone sex, my address, my body, a meeting. Libertine just wanted me to enjoy myself.

I had already seen his cock and his body on cam. He was far older than me. He said that he was fifty but he was in great shape for his age. Although I found it hard to judge things on the cam, his cock appeared huge. In my mind it was even larger, something to fear and desire at the same moment. He never showed his face. He said that it was more exciting to remain slightly anonymous. I agreed. In my mind he could be whoever I wanted him to be. All I needed was his body, his cock and his words on the screen.

As he guided me through installing my camera, I felt like I was a virgin again. I was about to enter a world that I didn't really understand. I thought I knew what I wanted but part of me wanted to switch of my computer and run downstairs. Needless to say, I didn't do that.

When the image first flicked into life, I felt more exposed that I had ever been. I was fully clothed but I felt naked. I hurriedly adjusted the cam so he could see as little of my room as possible. I kept the camera's eye on my breasts and body. I had lost weight recently and was proud of my new look. My tight t-shirt look good over my small, pert tits.

He told me that I looked great. We chatted about how it felt to be on cam. He didn't ask me to undress or make any innuendoes. He just chatted. The more we typed the more I was longing to show more of myself. I rubbed my hand across my breasts to see if he noticed. He did, of course. He said he wished he could do that. I asked if it turned him on. I asked if I should do it again. He said he would love that.

Within five minutes I was shirtless and braless. I played with my breasts, feeling like a porn star. He showed me his swelling erection and then took it out of his jeans. I watched in fascination as he stroked himself, knowing that I was the cause of his desire. My insides were hot with arousal and shame. I could feel how wet I was getting and I knew that this would go much further before the end.

I won't go into all the details, it would take too long. Anyway, that isn't the point of this story. You all know what happened in this part. Yes, of course my jeans and underwear came off. Of course I rubbed myself for him. I spread my lips, pushed two fingers deep into me. I gave him every view, every angle he asked for. Our conversation got filthier. At first I called him Master. By the end I was calling him Daddy. The fantasy got kinkier, more taboo. When he came, I was balancing precariously on my hairbrush handle, taking it deep into my arse. The mixture of pleasure and pain was so powerful that I managed to orgasm simultaneously with him.

He never asked to see my face.

When we had both recovered a little, he talked to me about our fantasy. He checked that it had not gone too far. I explained that the elements of rape and incest were taboos but that is partly what had turned me on. He told me that he wished he could come to me for real, sneaking into my house in the night. It was the first time he had ever crossed the line and mentioned meeting in real life. I politely told him that online was more than enough. He just said that it was enough for now. He told me that he wondered if we would want more in the future. I told him that nobody could know the future.

After some affectionate small talk, we both went offline. I had dreams that were vivid, erotic and bizarre. I had begun swimming in an ocean of desires that I had only ever watched from the shore.

Imagine my disappointment when Libertine ceased to be online. I went for four nights without his company before I emailed. We had never exchanged phone numbers, so I had no other way to contact him. He didn't reply to my mail the next day. I hated myself for missing him so much but I could not hold back from sending another message. I let him know that I wanted him. I was explicitly sexual about how much I had pleasured myself in his absence. I thought that I could get him out of hiding if I aroused him enough. I wrote that I lay in bed at night longing for him to open my bedroom door and take me by force. I went into detail about how he would abuse me and the pleasures we would both feel. My language veered from vulgar to almost poetic in my desperation to make him interested in my again.

I tried to find the same joy online that he had given me but nobody else knew my mind like Libertine. One night in late August, alone in the house, feeling hugely disappointed with my online games, I went to bed to sulk and sleep.

When I woke up, he was already on top of me, holding me down. One hand was over my mouth. I tried to scream but he muffled it. My eyes were wide but in the semi-darkness and confusion, I could see very little. He was wearing a black balaclava. I knew it was Libertine. We had discussed this scenario. He had taken my email as an invitation. How had he found me? That was not important. What was he going to do? That was inevitable.

I didn't want this. Online I was always in control, always one flick of a switch away from safety. This made me too vulnerable. For a second I managed to writhe my face free of his hand and I screamed. He slapped me. I gasped at the pain. He had not hit me hard but the strength of the blow told me he could hit me a lot harder if he chose to.

He stood up and dragged me from the bed. By this time I was so afraid that my will to resist had gone. I thought that my only tactic could be compliance. I knew what he wanted. Perhaps if I gave it to him, I would be safe.

He dragged me to the wall and, to my surprise, he switched on the light. He had positioned himself behind me and was holding me around the waist with one arm. I could feel the hard bulge of his cock against my back. With the other hand he was reaching for something in his pocket. I shut my eyes, terrified of what tool he might be searching for.

I heard the crumple of paper. I opened my eyes to see what he was holding in front of me. It was a copy of the email I had sent him. He had highlighted certain sections. Feeling a cold dread fill my chest, I read my own words, words that had condemned me.

"...I want you to come to my room in the night..."

"...take me as roughly as you like, use me like a slut..."

"... I'll take your massive cock in my pretty, little mouth..."

"...and when you're entering my tight, shaved pussy, I'll call you Daddy..."

"...when I suck my own juices from your shaft, I want you to cum in my mouth and all over my face, just like I'm a slut in one of the clips we watched..."

There was no point in arguing now. I could try to explain that all I had wanted was his attention again. My words defied me. He was here and he would take what he wanted. I had invited him to do it. Feeling humiliated, I started to cry. "Please!" I moaned, my voice cracking with fear. "Please don't!"

In answer, he thrust his hand down between my legs. I was only wearing a long t-shirt, nothing else. His fingers rubbed my lips and clit. They were still wet from my time on the internet earlier on. I knew how he would interpret it. I wanted him. The feeling of his fingers was, no matter how afraid I felt, powerfully arousing. He was full of lust but it hadn't taken away his skill. I almost collapsed against him as he molested me. He was panting in my ear and I felt my legs buckle. It was all that he needed to push his finger inside me. I shouted as it entered me but my yell would not have sounded like distress, not to him. He grunted in satisfaction, lifting me from the floor so his probing finger could get deeper inside me. He rubbed it around as though he wanted to explore every inch of my pussy, claiming his territory. Then, swiftly, he pulled the dripping finger from me and thrust it against my lips. I considered biting him but I didn't want him to hit me again. I had to submit. I would be safe if I pleased him. I sucked his finger, tasting my own wetness.

He lowered me to the ground and my knees gave way. I half knelt, half sat at his feet. He stepped in front of me, putting a hand over my eyes. Even though he was masked he didn't want me to look in his eyes. Perhaps he was afraid he would stop if we looked at each other. He needed the anonymity to do these things. I considered fighting back and pulling off his mask but I knew he was too strong. He was also insane enough to break into my house and do this to me. I didn't want to find out what else he might be capable of.

He reached down, took my hands and brought them up to the bulge in his jeans. I knew what he wanted. If I stalled the same things would still happen to me, they would just be more difficult. Biting my bottom lip, I began to rub his crotch. His breathing quickened and he used his free hand to unbutton his jeans. Humiliated by my own obedience, I reach into his jeans and, with some difficulty, managed to free his cock. It was huge and hard, difficult to manoeuvre out of the tight fabric. Eventually, though, the thing that I had desired was in my hands. It was just as big as I had thought. I could hold both of my hands on the shaft and still the head protruded. I was still crying as I began to suck the hot shaft.

He couldn't suppress his moan of pleasure. I hoped that he remembered I was uncomfortable with deep-throat because a cock this size could suffocate me. I whimpered as he grasped my head but, fortunately for me, he never plunged too deeply. He was rough, though, and so fast that all I could do was keep my lips wrapped around him as he used my face.

I could feel the pleasure building in his throbbing shaft. I wondered if I could escape some of his lust by making him cum quickly. I whined pathetically as he fucked my mouth, hoping that the sounds of my vulnerability would arouse him more. His movements did get fiercer for a moment but, as if he knew my ploy, he suddenly pulled out, leaving me gasping and wet-lipped.

He manhandled me to the bed, pulling my t-shirt over my head as he did so. Without speaking, he push me onto all fours. He had always told me how he liked to enter a woman like this the first time. He said it was more animal, more pure. I didn't move as I felt him clamber onto the bed behind me. There was no point. Nobody would be able to come and save me in time, even if I did succeed in getting out of his grasp. I hung my head and waited for the inevitable. He positioned himself behind me and began to rub the tip of his cock up and down my slick pussy lips. He didn't enter me straight away, instead, he pulled out my email again. He began to wave it in front of me, stabbing at it with a pointing finger. The word was, "Daddy."

Could he force me to say it? Could I break that taboo just to please him? I had typed it a hundred times on the net. Could I say it aloud? What would happen if I didn't?

He grabbed a handful of my hair and yank my head back, throwing the paper to the bed. Then he began to spank me with his other hand. It was not the playful spanking that I had occasionally enjoyed with my boyfriends. It was punishment. I had not realized how much a spanking could hurt. My parents had never hit me when I was a child and I didn't know the pain that could be inflicted. He hit me fewer than ten times before I burst out with the words, "Sorry Daddy! Please fuck me!"

A cock would be better than a beating. He wasn't going to use protection, that was obvious. I was on the pill so I had no fear of getting pregnant. I had told him that online. I just prayed he had no diseases. I thought about telling him to fetch a condom from my bedside cabinet but I knew he would just laugh at me.

Slowly, so I could feel every inch of his intrusion, he pushed his massive cock into my small pussy. I gasped and moaned, bunching my hands into fists. I had never experienced anything of that size inside me. He was slow but relentless, pushing until I could physically take no more. He could have given more but I would stretch no further. He was pushing into my depths, stretching me more than I had ever felt. Then he slowly drew back, only to plunge in again. Then again. Then again.

He began to increase his rhythm until my pussy obediently stretched and lubricated for him. As it became easier to fuck me, he increased his speed and violence. He yanked at my hair, pulling my head so far back I wanted to scream but each of my little yelps of pain just made him harder. His other hand reached underneath me to rub firmly at my clit. He was rougher than any man I had been with but I couldn't stop myself from loving his touch. I decided to give in to my body. It was the only way to survive.

How long did it take him to make me cum? I couldn't say. I felt like he was fucking me for hours. Every time that I thought I would cum, I reached a higher level of pain and pleasure. I had not known that my body could feel so electrified. Every nerve was on fire with ecstasy or pain. He groped, squeezed, pinched and slapped. He even throttled me, bringing me so close to blacking out that I thought I would die before he had fully enjoyed himself. When I breathed again, my head flooded with light and suddenly an orgasm was controlling my body. I screamed, knowing that nobody would hear but him and he would be delighted. My body didn't seem to be my own. I was just an organ of his pleasure.

Before my orgasm had finished, he had pulled out of me and thrown me onto my back. I knew what he wanted. My mouth and my face. He was dangerously close to orgasm and he didn't want to miss the spectacle of his semen covering me. Without any protest, I shut my eyes and opened my mouth. I lay back, propped against pillows, my face at the perfect angle for him to defile it.

He covered my eyes. I was surprised. They were already shut. He obviously didn't want me to look at him. After a short pause where he seemed to fumble with his clothing, he began to masturbate with his other hand. I could smell myself all over the hot cock that brushed against my face. His hand beat furiously, sometimes hitting me. He made no apology. I kept my jaw slack, ready to receive his cum. I wondered if it would be over when he had satisfied himself.

He was grunting with exertion, seconds away. Suddenly, he pulled his hand from my eyes and shouted, "Look at me!" I blinked, not understanding what I was seeing. He had taken off his mask.

I was looking into the face of my father.

"Daddy?!" I gasped, my whole world dissolving.

Then he came, his cock pumping jet after jet of hot cum into my mouth and over my lips. He watched my horrified face as he coated me with his seed. He looked astonished, appalled and furious.

When he finally finished cumming, he collapsed next to me on the bed and pulled me close to him. I didn't resist. I couldn't. I no longer knew what was happening. He cuddled me too him and whispered gently to me about how good I had been. I turned away from him but he pulled me back, my buttocks against his throbbing penis. I can't repeat all of the words he said. I can't remember most of that time. My body was present but my mind had left it. All I know is that he told me that it hadn't been "us" that had done it. Not the real "us". He told me that it was only our internet selves, our fantasy selves. He explained how he had been monitoring me ever since I had been given the new computer. He had spied on me through our network. Eventually he couldn't just watch any longer. He had invented Libertine so that he could learn about me. He had gone so far into his fantasy that it had frightened him and he had tried to resist. Then my emails had come. I had worn away his resistance. I had tempted him.

12