Blackmail Diary Ch 02 1

Saturday 26th November

I woke early this morning with a moderate hangover and a raging hard-on. I needed her answer to my final question.

'Good morning' I texted.

Her reply was disappointing. It made it clear that she was less than comfortable with last night's events. 'This has got to stop! You need to leave me alone', it read.

'Are you forgetting something? You owe me' I responded.

'I'll give you money, anything. Just stop making me do things! Please!'

'I don't want your money.'

'Well that's all I can offer you. I can't do anymore of these things you've made me do. I won't.'

I made no reply. It was time for action. I spent the rest of the morning creating aliases on various social networking sites. I then posted the pictures she'd sent of her tits and pussy across a number of different groups and forums, one of which is directly related to our school. I included no description or explanation.

'I think you should look at these' I texted her, along with half a dozen links that led to intimate photographs.

'What the fuck are you doing!' she quickly came back.

'Do as I say and they will be removed before the end of the day. If you don't, I am going to start adding descriptions. This is your final warning.'

'Okay, I'll do anything just take them down.'

'First, I want an apology.'

'I'm sorry. I promise I won't argue again.'

'Good, but you still need to be punished.'

'What do you mean?'

'You are going to send me a video. And in this video you're going to slap yourself ten times. If the slaps aren't hard enough I'll make you do it again.'

'Slap myself where?'

'Your pussy.'

I was apprehensive. I knew that I had demanded a lot of her, and, if she didn't comply, I knew I would have a big decision to make.

The video was dark and grainy. The hand that held the camera was visibly shaking. But none of that mattered. I had the video, and I could see and hear everything I needed to. Truman was perched on the end of her bed, naked from the waist down. Her free hand left the shot and then returned quickly, planting itself on the perfectly bald pussy at the centre of the frame. The smack, was accompanied by a whimper and the faint mumble of 'fuck'. A couple of deep breaths followed, before her free hand settled a few inches in front of her cunt. After one final deep breath the hand began moving back and forth in rapid succession, smacking hard each time. After the tenth strike the screen went black.

'Good. If you ever argue with me again the punishment will be far worse. Understand?'

'Yes.'

Monday 28th November

I was sat in the library this morning trying to study. All I could think of was Truman. I knew that contacting her at this time of day was somewhat futile, she was more than likely taking a lesson, but I couldn't help myself. 'Reply as soon as you get this' I sent her.

By the time she did reply, a couple of hours later, I was in a physics lesson. That wasn't going to hold me back though. I put my phone under my desk and began tapping away.

'Where are you?' I asked.

'I'm in the staff room' she responded.

'I want you to take a marker pen and go to the toilet. Text me you're sat in the cubicle.'

'I'm there' she confirmed, after a short wait.

'Good. Now write 'I love sucking cock' on the wall.'

The next message I received was a picture, displaying red graffiti against the faded blue of the partition wall.

'Now take your top off' I ordered.

'Done' she replied, within seconds.

'Write 'slut' across your tits.'

Another photo arrived, her beautiful tits, marked as I had instructed.

'I'm done with you. Go back to the staff room.' I told her.

This evening, I decided it was time to revisit Friday night, and see if I could dig deeper into her warmer-than-expected reaction to the second bukkake clip I'd sent. To do this I simply sent it again.

'That's the same video from before' she sent in response.

'I'm aware of that. Did you enjoy it this time?' I replied.

'No, I didn't enjoy it last time either. It's disgusting.'

'I don't believe you.'

'Believe what you like. Do you want anything else from me? I want an early night.'

I was disappointed, I had convinced myself she had enjoyed it. Perhaps I was wrong.

Tuesday 29th November

Today was a bad day. First my parents were on my case, for various reasons I won't go into. Then I was in trouble at school, for various reasons I won't go into. Josie then started hassling me, and her friends soon decided to join in too. Yes, I behaved terribly; yes, I'm an arsehole, but it's over. That was your fucking choice, now leave me the fuck alone! Finally I had work, which was as it always is, very long and very boring.

It was 9 o'clock, I was in my bedroom drinking a beer, sulking. I didn't plan on contacting Truman. I couldn't be bothered with anything that required even the slightest effort. I was going to finish my drink, have one more maybe, go to bed and forget that the day had ever happened.

My phone beeped. A new message from 'T-man'.

'Why the fuck are those pictures still online?' it read.

I gritted my teeth in anger as I typed, 'Who the fuck do you think you are speaking to me like that?'

'I'm sorry but you need to take those photos down. Please!'

I went to my computer and thumped away at the keyboard. Via my alias, I logged onto a popular social networking site. The picture I'd posted of her tits in our school group now had a handful of comments - 'Nice', 'WTF!', 'Who's this? lol' - along with a fifteen thumbs-up.

I added to the comments, 'Believe it or not this is a teacher of yours...'

I knew this was a risky move that could, if seen by the wrong person, lead to an investigation into the authenticity of the statement. But, in that moment, I did not give a fuck.

'You should look at this' I texted, along with a fresh link to the picture.

My phone started ringing, 'T-man' flashed across its screen.

Good, I thought to myself, she's panicking.

I rejected the call and sent another message. 'I'm not going to speak to you, but I will punish you.'

'I'll do anything. Just take that comment off' she replied.

'I want pegs on each of your nipples for 30 seconds.'

A video arrived soon after, showing a close-up of her naked chest. A clothes peg was attached to each tit. She seemed to cope well with the pain, her breathing was controlled, and there was no whimpering to be heard. The video lasted a whole minute, with the pegs clamped to the nipples throughout. I was in no mood to offer her praise for having exceeded my expectations, in fact, I was looking for any fault I could find.

'Who said you could clean your chest?' I asked, referring to the instructions I'd given yesterday.

'Sorry' she replied.

Shortly after I was looking at a photo showing that she had not only re-annotated her tits, but she had also re-attached the pegs.

I was still reluctant to commend her, so instead I sent her instruction for tomorrow.

'In the morning you're going to dres in a skirt for school. No tights, no panties' I told her.

'Okay' she replied.

Wednesday 30th November

I had a lesson with her this morning. She wore a light pink blouse and importantly, she had on a skirt. There were definitely no tights underneath the skirt, but, naturally, it was difficult to determine whether or not she was pantyless. At every given opportunity I would stare intently at her arse, to see if there was any hint of a panty-line; there wasn't.

It was my intention to demand photographic evidence to confirm all my instructions had been completed, but unfortunately the day ran away from evening.

This evening too, lacked for any real interaction. I sent her a message around six o'clock, asking if she was home. She replied to say she was having dinner with her friend.

I then went on an unscheduled outing to the pub, and didn't give her much thought.

Thursday 1st December

This morning I woke up to a text message from Josie that read 'I'm not going to school today. I'm home alone. And very horny.'

I ended up spending the whole day with her. I fucked her every way I could imagine, all the while wishing she was Truman.

After I was done fucking her I was ready to leave, ready to walk out and prove I am the arsehole her friends keep telling her to stay away from. But she gave me those puppy dog eyes, and before I knew it we were sharing a starting platter at the local Chinese restaurant.

I got home late, and confused. I was in no mood to contact Truman.

Friday 2nd December

Today was another hectic Friday. Before I'd even left the house this morning I'd had one friend calling me about a game of football after school, and another trying to arrange this evening's drinking venues. I also had a string of texts from Josie, which were swiftly ignored.

With a full day at school, and a shift at work, on top of the plans I'd been making, I resigned myself to this being the third successive day that would see minimal contact between Truman and me.

I was very wrong. At about eleven o'clock this evening, I was sat in the local pub with my friends, and I felt a vibration in my pocket. I assumed it would be Josie, so ignored it. Half an hour or so passed and I headed to the toilet to take a piss. There were two new messages on my phone. The first a text from Truman that read 'The writing is beginning to disappear'. The second was a picture of her tits still bearing now faded letters of the word slut.

'You better re-write it' I texted, hurriedly. In less than a minute, another photo arrived.

'Are you at home' I asked.

'Yes' she replied.

'Are you alone?'

'Yes.'

I had now made my excuses and was walking home from the pub.

'Have you been drinking wine?' I quizzed.

'Yes I have' she answered.

'I want to see the empty bottle in your cunt.'

The next picture nearly brought on an eruption in my pants. It showed a dark red bottle with its entire neck buried in her hairless pussy.

'What now?' she asked, as I was still taking in the picture.

'Fuck yourself with it' I instructed.

I had to read to her next message a three or four times to convince myself I wasn't imagining it. 'Can I watch some porn while I fuck myself' it read.

I forwarded her a link to a favourite scene of mine. A man and woman in a toilet cubicle; he's rough with her, very rough. He slaps her face, spits in face, fucks her face, until she gags, and then pushes her head into to toilet bowl while he fucks her hard from behind.

I waited impatiently for her next reply. It came some fifteen minutes later, in the form of a video.

She was laying down on her bed, completely naked. Her knees were hitched up, the bottle was going in and out of her pussy. She moved the camera to show a laptop sitting on a bedside table; the clip I'd sent was playing. The camera returned to her, and the speed with which she fucked herself increased. 'Fuck,' she kept repeating, 'fuck, fuck, fuck.' She was going to cum. She began screaming in ecstasy and the screen went black.

'You came?' I enquired.

'Yes, I did' she confirmed.

'Did I say you could cum?'

'No, I'm sorry. I couldn't help myself.'

'You need to be punished.'

'Okay.'

I was so turned on that my hand was now shaking.

'Suck the bottle clean.' I ordered.

Minutes later I was watching her running her tongue along the bottle's neck. The visible marks that she had left earlier were disappearing as she circled the glass. She looked into the camera and smiled, then took the bottle neck into her mouth. She worked it back and forth, slowly at first, and then with more pace. I wished more than I'd ever wished for anything that I could be that bottle. Soon it was moving so fast that she started to gag. This didn't deter her though, she pushed the bottle further down her throat, and held it there. She went without a breath for at least half a minute before pulling the bottle free.With mascara running down her cheeks, she swallowed hard and took a deep breath of air. Finally, she turned to the camera, smiled again, and the video ended.

It was all too much for me; I now had a mess of my own mess to clean up.

Saturday 3rd December

I knew I had delicate situation to handle. Last night's excitement was almost undoubtedly fueled by her alcohol intake, and it was therefore highly likely that she would be regretting her actions.

I decided not to mention it, and instead set her a fairly simple task. I told her that, at some point over the weekend, I expect her to go a busy carpark and finger fuck herself.

She gave no reply, not even to confirm receipt, but I remain confident that during the course of tomorrow I will be watching her carry out my instruction.

Sunday 4th December

Around 1pm I was lazing on the sofa watching some crap on TV, when my phone beeped. I smiled, and retreated to my bedroom, knowing that I now had something far more interesting to be watching.

The car park was familiar, a retail park just the other side of town. She panned the camera around, showing that it was moderately active, with around a third of all the spaces occupied. The camera moved down, as she slid forward slightly in her seat and rolled up her skirt. She wore no underwear. Then came as very pleasant surprise, her free-hand left the shot and returned with a small pink dildo.

The toy headed straight for her pussy. As she began sliding it in and out, there were audible indications that she was aroused. She continued for a couple of minutes, the fuck-rate increasing, along with her moaning.

Suddenly she stopped. She moved the camera up and pointed it out the window, just a few yards away a woman was getting into her car. The video ended.

Monday 5th December

I had a lesson with Truman this morning. I couldn't help but stare at her for long periods, the whole time questioning if the weekend's events had been real. Had I really coaxed this beautiful, respectable woman into the performing of such debauch acts? Surely it was all just a figment of my imagination?

The longer I stared at her, the more I wanted her. Frustration was taking hold of me. I wanted to force her over her desk, to rip off her panties, to fuck her so hard that she'd scream and cry until her body couldn't take anymore. I wanted her mouth, her cunt, her breath. I wanted my cum on her and in her.

By the time I left the classroom my frustration was turning to anger.

'Where are you?' I asked her at lunchtime.

'I'm in the staff room,' she replied.

I was looking for any excuse to chastise her.

'Address me properly you fucking whore!' I insisted.

'Sorry Sir. I'm in the staff room Sir,' she corrected.

'Are you wearing panties today?'

'Yes Sir.'

'Did I say you could wear panties today?'

'No, sorry Sir.'

'Take them off.'

Within minutes I was looking at her black panties screwed up on the toilet floor.

'Have you ever been fucked up the arse?' I questioned.

'No Sir I haven't' came her reply.

'Why not?'

'I don't know Sir.'

'Have you ever fingered your arse?'

'No Sir.'

'Well what are you waiting for?'

The next photo showed her tight little arsehole engulfing the middle finger of her left hand.

'Does that feel good?' I asked.

'I'm not sure Sir' she replied.

This brief exchange had cooled my rage, but the frustration was still with me. After school I had a four-hour shift at work, during which I thought of little but Truman. More specifically, I thought of little but me fucking Truman. I walked through the logistics in my mind, and found nothing but obstacles. The crucial issue, I surmised, would be my loss of anonymity. Allowing her to discover my identity would be far too great a risk to take at this stage; it could end the game, or, worse, get me into some serious trouble. Accepting this, I questioned the feasibility of fucking her without revealing myself. A mask maybe? This seemed a little far fetched but I gave it some thought. I was actually on the verge of concluding it could work when I considered the legality. Yes, what I've been doing up to now is undoubtedly outside of the law, but fucking her, without full consent? That might be taking it a tad too far.

I left work defeated. On the drive home I reached for my phone and sent a text.

'I'm coming over to your house right now, and I am going to fuck you very hard' the message read.

Unfortunately, the recipient was Josie.

Tuesday 5th December

I woke up this morning, freezing cold, on the back seat of my car. Josie lay next to me, her head resting against. my shoulder.

We decided to take the day off school. Things were going great, it was if we'd never been apart. I started to remember how much she had meant to me, and regret having ever let her get away.

If something feels too good to be true it all too often is too good to be true. One of her friends phoned, asking why she wasn't in school. All her friends are shit-stirring little bitches - who think far too much of themselves - but the girl who rang, Emily, is the worst of them. By the time their conversation had finished, Josie was in floods of tears, and questioning if I could really commit to her this time around. I did my best to assure her I would, but it wasn't good enough. We were soon in the midst of a heated argument, centred on my past infidelities.

It was early evening when I arrived home. I was full of anger and resentment; I needed to let off some steam.

'Where are you?' I asked Truman.

'I'm home Sir,' she replied, instantly.

'Send me a picture.'

'Of what Sir?'

'Anything.'

I was soon looking at her naked tits, which still bore the word slut. It was a nice enough picture, but nothing exciting, nothing I hadn't seen before. I wanted something new, something different.

I decided to find out if she had a webcam. She confirmed there was one built into her laptop, but claimed she didn't know how to use it. I told her to set-up an account on a popular instant messaging service, and to download the corresponding application. I gave her the username for an alias I had created and a few minutes later I was accepting a new contact request from 'dfc7777'.

'Is that you?' I typed, my hands a little shakey.

'Yes, it is Sir' she replied.

I initiated a video call, safe in the knowledge that there was no camera attached to my own computer.

Truman sat on her bed, legs crossed looking down towards the camera. The room was dimly-lit. She wore what appeared to be pyjama bottoms and a hooded sweatshirt. Her hair was tied back.

She waved at the camera and then leaned forward to type.

'Do I not get to see you Sir?' she questioned.

'Of course not, you stupid slut,' I responded, 'I'm in a bad enough mood as it is without you asking me dumb questions.'

'Why are you in a bad mood Sir? Is it something I've done?'

'Take off your top' I ordered, ignoring her question.

She pulled the sweatshirt up over her head and threw it to one side, revealing a black bra underneath.

'Shall I take my bra off too Sir?' she asked.

'No,' I instructed, 'leave it on but take your tits out.'

She pulled both cups of the bra down and her tits fell free.

'Now smack one' I wrote.

Her left hand went up above her right tit and came back down with moderate force.

'Harder' I demanded.

Again the hand went up and down, impacting twice as hard as her first attempt had.

'Harder!' I repeated.

This time the hand went high above her head and crashed down with such force that the camera rocked.

I still wanted more. 'Hit it harder you fucking cunt!' I demanded.

Her hand went higher and crashed back down, and then she repeated it, not just once, not even twice, but three times, each strike more vicious than the last. When she was done her tit had a fiery glow, her breathing was rapid and tears ran down her flushed cheeks.