Tuesday 22nd November
Miss Tan was not in college today. I was a little concerned. What if she turns herself in? What then for me?
I shook off my worries, she would be a fool to confess to everything at this stage.
‘Why aren’t you at college?’ I asked her at lunchtime.
‘I didn’t feel up to it. I’ve got a lot on my mind. Mainly because of you!’
‘Because of me?’ I replied, in disbelief.
‘Yes, you’re scaring me.’
‘You have nothing to worry about. Do as I say and no one will ever find out about what you did.’
I had to work tonight. It was nearly midnight by the time I arrived home.
‘Are you still awake?’ I texted.
‘Yes’ she responded.
‘Are you going to be in college tomorrow?’
‘Yes.’
‘Good. I’m going to ask you some questions now. Okay?’
‘What sort of questions?’
‘The sort you won’t want to answer. But you’re going to. Understand?’
‘Yes.’
‘How many men have you been with?’
I waited over an hour for a reply. Just as I had given up hope of one coming my phone beeped.
‘Five’ the message read.
‘And how many woman?’ I replied, hopefully.
‘None’ came her expected, but still disappointing, response.
‘Do you like sucking cock?’
‘No’.
‘Do you like having your pussy licked?’
‘Sometimes’.
I am delighted with myself. She may not have appreciated it at the time, but she has now given me an extra layer of collateral. It would have been difficult for me to come forward about the accident at this stage. Had I done so, I would have had a lot of questions to answer myself. I withheld information from the police; not to mention the fact that I have been blackmailing a school teacher. Now though I have a far more feasible weapon at my disposal. Two text messages, sent within minutes of each other. The first from my phone asking if she enjoyed cunnilingus; the second from hers with a tentative reply. I could, in theory, take these messages to a number of sources, my parents, my older sister, another teacher, and tell them that I am uncomfortable with the relationship I’m having with this teacher. If I did this, what could she possibly do? She couldn’t tell anyone I was blackmailing her, they would ask how and what with. Her only feasible option would be to resign, in the full knowledge she would never be allowed to teach again.
My final message of the evening detailed the above theory. Miss Tan made no reply.
Wednesday 23rd November
I had no lesson with Miss Tan today, but I did see her on a few occasions. She didn’t look too good. She was very pale and wore no make-up.
‘You look ill’ I texted her, as I climbed into my car at the end of the school day.
‘I didn’t get much sleep’ she replied.
It was time, I decided on the drive home, to set her a little assignment. Nothing too challenging, just something to ease her into the game.
‘Do you ever watch porn?’ I asked.
‘No’ came her predicted response.
‘Later tonight I’m going to send you a link to a porn clip. You’re going to watch it. All of it. Understand?’
‘Yes.’
Later in the evening I sent a link to what is a fairly typical porn clip. It features a well known female pornstar with two men.
‘Have you watched it yet?’ I asked, shortly after having sent it.
‘I’m not at home at the moment.’
‘Where are you?’
‘At a friend’s house.’
‘Let me know when you’re back.’
I waited a couple of hours, and then started to grow inpatient.
‘Are you home yet?’ I asked.
‘Yes’ she replied.
‘I told you to let me know when you were back!’
‘Sorry, I’ve only just got in.’
‘Have you looked at the link I sent you?’
‘Yes’
‘Tell me what happens in it then.’
‘A dark haired woman has sex with two men.’
‘How does it end?’
‘They ejaculate on her breasts.’
‘Did you enjoy it?’
‘No.’
‘Oh well, I’ll have to send you something a bit more interesting next time then.’
Thursday 24th November
I think I’m getting a bit obsessed by this situation. All day long I’ve been thinking about her, last night I dreamt about her. This afternoon Josie, my ex, sent me a text message saying that she was missing me, and having second thoughts about the breakup. A couple of weeks ago I would have done anything imaginable to get this girl back in my life; today, it just seemed irrelevant. I didn’t even reply to her message.
‘Where are you?’ I texted Miss Tan, at half six this evening.
‘At home’ she replied.
‘I want a picture’ I told her.
‘A picture of what?’
‘You. Your face.’
‘Why? You know what I look like.’
‘Just do it. Now!’
A picture arrived shortly after. Her miserable expression, coupled with the fact she wore no make-up, made her look almost unattractive.
‘Why do you look so unhappy? And why aren’t you wearing any make-up?’ I questioned.
‘Because I’m not happy, because you won’t leave me alone.’
‘Send me another picture. With make-up and a smile this time.’
She did as instructed, I was soon looking at the second picture, in which she now wore lipstick, a little eyeliner and an uncomfortable smile.
‘Much better. You look pretty again now’ I informed her, before asking if she was ready for some more porn.
She didn’t reply but I forwarded a link. The video I directed her to features one of my favourite pornographic niches, bukkake. The word alone makes me hard.
‘I’ve watched it’ she replied, a short while later.
‘Tell me what happens in it.’
‘A lot of men, ejaculate over a girl.’
‘I don’t like the word ’ejaculate’. It’s too formal. Tell me again what happens.’
‘What word do you want me to use in its place?’
‘Use your imagination.’
‘A lot of men cum all over a girl.’
‘Did you enjoy?’
‘No I didn’t.’
‘How does it end?’
‘The girl swallows it all.’
‘Do you swallow?’
‘No. Can I go to bed now please?’
I made no reply.
Friday 25th November
Today was very busy. I had a full timetable at school, five very long lessons - none of which were taken by my favourite teacher - followed by an incredibly boring three-hour shift at work. Once that was done, I went home, had a quick shower and headed out for a few beers. It turned out to be a very good night.
I arrived home quite drunk but by no means paralytic, some time around 1am. I wasn’t planning on contacting Miss Tan, but as I climbed into my bed thought, why not give it a shot?
‘Are you up?’ I texted.
‘Yes’ she replied, almost instantly, to my surprise.
‘What you doing?’
‘Not much, just got back from my friend’s house.’
‘Is this friend male or female?’
‘She’s female.’
‘What did you get up to?’
‘Watched a film, drank some wine.’
‘I want a picture.’
‘Of?’
‘Your tits.’
I was waiting for a hostile response, and, when my phone beeped its little beep a few minutes later, I assumed I would be reading one. But I wasn’t. Instead I was looking at her beautiful naked tits.
‘Nice’ I responded, not wanting to fully convey how surprised I was at the ease of her compliance. ‘Now send me one of your pussy’ I followed.
Surely a protest is coming this time, I thought to myself. Again though, I was wrong. Her naked pussy was soon on full display on the screen of my mobile phone. Above it lay a patch of neatly trimmed dark hair.
‘I don’t like the hair. Get rid of it’ I demanded.
‘All of it?’ she questioned.
‘Yes.’
‘Now?’
‘Yes.’
After a relatively short wait, I was looking at an almost identical picture to the one I’d received previously, the only difference being my requested amendment.
‘Very nice’ I told her.
‘Thank you’ she replied.
She was thanking me now? This was all too much. I knew I needed to capitalise on her unexpected williness to follow my instructions, but the alcohol was stifling my imagination.
‘I’m going to send you some more porn’ I informed her.
‘Okay’ she replied.
The clip I sent her the link to this time again centres on the art of bukkake. It stars two girls, one who catches the cum directly from its source and the other who has it spat at her via the mouth of the other.
‘I’ve watched it’ Miss Tan confirmed, about ten minutes later.
‘Did you enjoy?’ I asked.
‘It was okay’ she replied, to my astonishment.
‘Really? What did you like?’ I probed further.
I was eagerly anticipating her next response. She liked it, I kept thinking to myself. She may have only said it was okay, but that was a giant leap from what I had expected. My excitement soon turned to frustration, as my phone remained painfully silent. I chased once, twice and even a third time, but there was nothing. I do not know if she fell asleep, or if she came to her senses.
As the clock ticked over to 3am, I decided to let go of my frustration and drifted off to sleep.
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. Miss Tan 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 Miss Tan. 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 college, 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 Miss Tan. 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 ‘Miss Tan’.
‘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 college 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, ‘Miss Tan’ 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 college. 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 college 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 Miss Tan.
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 nearby Chinese restaurant.
I got home late, and confused. I was in no mood to contact Miss Tan.
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 college, 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 college, 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 Miss Tan 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 Miss Tan 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 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 college. 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. Miss Tan 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 Miss Tan. 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 Miss Tan. 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 ‘TAN’.
‘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, ‘TAN’ 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 college. 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 college 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 Miss Tan.
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 Miss Tan.
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 college, 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 Miss Tan 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 Miss Tan 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 Miss Tan 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 college I had a four-hour shift at work, during which I thought of little but Miss Ta. More specifically, I thought of little but me fucking Miss Tan. 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 Miss Tan.
‘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.
Miss Tan 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.
‘Go and get your dildo’ I ordered, consciously making no attempt to acknowledge her efforts.
She disappeared from the screen, and returned within seconds, dildo in hand.
‘Suck it’ I instructed.
With the base gripped tightly in her right hand she began moving it in and out of her mouth.
‘Guess what you’re going to do next’ I typed.
‘Fuck myself Sir?’ she replied, breaking off her plastic fellatio.
‘Yes. But not your pussy.’
‘My arse Sir?’
‘Yes.’
‘Now Sir?’
‘Yes.’
She nervously bit her lip, shuffled away from the camera and began sliding her pyjama bottoms down her legs; she wore no panties.
‘What are you?’ I asked.
She leaned forward again, to answer my question via her keyboard.
‘No!’ I stopped her, ‘don’t type it, say it!’
‘I…I’m’ she stuttered, quietly, ‘I am a slut.’
‘Louder!’ I typed.
‘I’m a slut’ she repeated, still not loud enough.
‘Louder!’
‘I am a fucking slut.’
‘Louder! Tell your neighbours, you fucking whore!’
‘I am slut,’ she shouted, ‘I’m a dirty fucking slut!’
‘Good, now put that plastic cock in your fucking arsehole!’
She threw herself down on to the bed, lifted her bum and planted the toy in its target.
I sat back, cock in hand, to enjoy the show. It had an uncomfortable beginning. There were a chorus of distressed moans, accompanied by numerous profanities, as she cautiously moved the dildo in and out.
Within a couple of minutes she began to relax. The moans continued, but not all were quite so pained. The repeated outburst of ‘fuck’ seemed to have evolved from ‘fuck, that hurts’ to ‘fuck, that actually feels okay.’ Soon, it was more akin to ‘fuck, that does feel good’ and then ‘fuck, that feels really good.’ Her free hand was lightly caressing the inside of her thigh. She wanted to touch herself.
I was now pulling on my cock so hard I knew I had only seconds before there would be an explosion. I reached for a box of tissues, but then stopped. Why waste a perfectly good load of cum? I asked myself.
‘Stop!’ I wrote. She looked up at the screen as my message sounded its beep. ‘That’s enough for tonight,’ I continued, ‘I’m going to bed.’
That was a of course a brazen lie, there was no possibility of me sleeping in my current state. I jumped in a cold shower, and thought through my plan for tomorrow.
Wednesday 7th December
7.30am, as usual, I was woken by my alarm. Today instead of reaching for the snooze button I found my phone and began tapping away, to put my plan into action. ‘You can wear your panties to school today’ I texted.
9.05am, sat in a maths lesson I initiated stage two of the plan. I sent her a message telling her that she was to go to a specific cubicle in the boy’s toilets, where she would remove and hide the panties I had so graciously allowed her to wear.
10.28am, I was studying in the library, when I received confirmation from Miss Tan. ‘They are under the toilet brush holder Sir’ her message read.
12.29pm, I took a lunchtime trip to the toilet, heading to a very specific cubicle. The panties were a dark blue cotton. I wrapped them around my cock, and began pumping away. I came quickly, my fat load soiling a large portion of the knickers. I then began wrapping them using toilet paper and a roll of sticky tape I had stashed in my bag. Once the parcel was back under the toilet brush where I had found it, and I was far away from the scene of the crime, I sent another message, telling Miss Tan to retrieve it. She was given strict instructions not to unwrap the paper.
8pm, I arrived home from work, wolfed down some dinner and darted up the stairs to my bedroom, locking the door firmly behind me.
‘Are you home?’ I texted.
‘Yes I am Sir.’ she replied.
‘Did you pickup the package?’
‘Yes Sir I did.’
‘Go to your webcam.’
Finally the real fun could begin. The scene was much the same as it had been yesterday evening , she sat on her bed, looking down on the camera. Tonight she wore a white t-shirt. By her side lay the crudely wrapped panty package, and her pink fuck-toy.
‘Have you any idea what I’m about to make you do?’ I asked, via the instant messenger.
‘No Sir,’ she typed in response, ‘I don’t.’
‘Does that scare you?’
‘A little Sir.’
‘Does it excite you?’
‘It does Sir.’
I took a deep breath to compose myself. ‘Open your present’ I instructed.
She picked up the parcel, her hands trembling, and began tearing away the tissue. Slowly, she pulled the panties free.
‘Can you see what I’ve done to them?’ I questioned.
‘Yes Sir, you have cum on them.’ Her breathing deepened, and her face flushed red.
‘Take off your clothes,’ I demanded.
She edged away from the camera and began to undress.
‘Are you wet?’ I asked as she threw her bra to the side of the bed. In reply she entered two fingers into her naked pussy and produced a substantial squelch.
‘Pick up your toy,’ I ordered next. ‘Do you want to fuck yourself?’ I followed.
‘Yes,’ she said outloud, ‘I really want to.’
‘You really want to what?’
‘I really want to fuck myself, Sir.’
‘You have my permission.’
She leaned back and planted her toy into her cunt. I watched for 3 or 4 minutes as the dildo brought her close to climax.
‘Do you want to taste my cum?’ I asked.
She continued fucking herself, and nodded her head. I wasn’t able to finish typing my next instruction. It would have told her to stop what she was doing, to pick up the panties and to lightly run her tongue across the gusset. But before my fingers could even reach the keyboard, she had taken the panties and stuffed them in their entirety into her mouth. The speed with which she fucked herself increased. I could hear her sucking on the cum-stained underwear.
My hand found my cock, knowing that I didn’t have long before she would be cumming, and the show would be over. Muffled screams soon escaped her panty-filled mouth, and she fell back onto the bed. My balls erupted.
As I watched her laying there, trying to regain her composure, with deep uncontrolled breaths, I made a big decision. Regardless of the obstacles and risk that may lay in my path, I will, in the near future be fucking this slut.
Thursday 8th December
I woke up this morning tingling with excitement. Over night I had thought through numerous plans that I truly believed would end with me fucking Miss Tan. They were risky and none of them were perfect, but I genuinely believed that more than one of could work.
Tonight I go bed heartbroken. A silly mistake has ended my hopes and ended the game.
I was sat in a lesson of hers today. The class was working quietly, when my phone started to ring aloud in my pocket. I always turn it off before a lesson, always. I reached quickly to reject the call. As I lifted it out my heart sank and my stomach turned.
The word ‘slut’ flashed across the screen.
Thursday 22nd December
It’s been two weeks since my last diary entry.
After leaving the classroom that day I drove straight home, and hid in my bedroom. I barely left it for a whole week. I didn’t go to school, I didn’t go to work, I didn’t see my friends. I told my parents I was ill and, thankfully, they asked few questions.
When I did return to college a week later I went straight to my head of year and pleaded for permission to drop English. I was flatly refused.
When attending her lessons I now don’t say a word, and I avoid eye-contact at all costs.
I’ve made no attempt to contact her, and have had no intention to. I’ve deleted her phone number, and, reluctantly, I also deleted all the pictures and videos she had sent me.
Today was the last day of the college term before the Christmas holidays. Most my friends were heading out for some drinks this evening, but I wasn’t in the mood. Instead I went home and watched a couple of films.
Just after midnight, as I lay spread out across the sofa, my phone beeped.
The message was from an unknown number.
‘Are you missing me?’ it read.
‘Who is this?’ I replied quickly, not daring to hope.
‘Have you forgotten me already?’ came the next reply.
I sat up. My stomach fluttered.
‘Is this Miss Tan?’ I sent nervously.
‘Yes Sam, this is Miss Tan.’
I took a deep breath.
‘Have you missed me?’ she asked again.
‘Yes!’ I replied.
‘Well don’t be a stranger. Speak to you soon x’
Friday 23rd December
I lay awake for hours last night wondering if I should continue the conversation. Her last message had been very final; she wanted to speak ‘soon’, not now. There were dozens of questions I wanted to ask, but I convinced myself that I shouldn’t ask them. Not yet anyway.
Today I woke up with a plan: let her come to me.
That plan died a death at around 4pm.
‘Why did you text me last night?’ I asked.
‘I don’t know. I shouldn’t have,’ she replied.
I wanted to punch the wall.
‘You must know!’ I demanded.
A couple of hours past, in the absence her reply, I lost all discipline and bombarded her with messages.
‘Don’t fucking ignore me!’
‘Send me a picture now!’
‘I’m going to the police!’
The messages continued, on reflection, each one reads more pathetic and desperate than its predecessor.
Tuesday 3rd January
The Christmas break has been and gone, today was my first day back at college. And what a day it was.
I arrived around 9 o’clock. I had a maths lesson first thing, followed by English with Miss Tan - something I’d been dreading the entire holiday. Before my maths lesson I went to my locker to get some books. Waiting for me there was a present far greater than anything I had received over Christmas.
A large white envelope sat on top of my text books. In block capitals it was addressed to SIR. I threw it into my bag and made a beeline for the nearest toilet.
Inside there was a black thong, and a hand-written note.
‘Dear Sir,
I am deeply sorry for the way I’ve behaved.
I will do anything to be your slut again. I know I must be punished.
Please take me back.
Your Slut’
My cock was so hard it hurt; my hand was shaking uncontrollably as shoved the panties into my pocket.
The maths lesson was a write-off. I didn’t hear a word of what I was being taught.
Walking over to my English class I was excited, nervous and more than a little nauseous. I was confused when I entered the room, as were my classmates. All the tables had be rearranged, and were pushed to the wall. A single desk remained in the clearing.
‘What’s going on?’ one of the girls asked Miss Tan.
‘We’re doing a practice exam today’ she explained, her cheeks bright red, ‘all the desks have name tags. Can you find your seats as quickly as possible please?’
There were numerous protests from the other members of class. Some claiming it was unjust for us to have an exam sprung upon us without prior knowledge. Others questioned why the exam required the seating alterations. She fended off the revolt and everyone started to take their seats. I looked for mine.
‘I can’t find my seat Miss,’ I explained.
‘I must have forgotten you,’ she said, casually looking round the room, ‘just sit there’.
She pointed to the desk in front of hers. The one desk that could see hers during today’s lesson.
I sat down and tried to make eye contact, but she was very deliberately avoiding it.
Ten minutes passed. My eyes hadn’t left her, but she remained focused on the paperwork in front of her. When she did look up she still resisted my gaze. I was beginning to grow frustrated, when her hand moved to her chest. My initial assumption was that she was relieving an itch. A button on her blouse popped open. And then another. And another.
I could now see a black bra beneath the blouse. Peeking up from below it were three lines drawn in red marker pen, which I knew formed part of the word ‘slut’.
My eyes were drawn to movement under her desk. She slowly began to spread her legs. I shook my head in disbelief, as her bald cunt came into view.
I looked back up and finally made eye contact. She smiled, bit her lip and pulled her phone out from under some books on her desk. I returned the smile, and reached quickly for my phone.
‘You filthy whore,’ I texted.
‘Are you hard?’ she replied.
I looked up and nodded.
‘Are you wet?’ I asked. She echoed my nod.
An idea sprang into my head from no where.
‘I want you to pick a girl in this room,’ I instructed.
‘Any girl?’ she wrote back with a confused frown.
‘The one you think is the prettiest.’
