Blackmail Diary Ch. 01

'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 dress 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.