The Diary Ch. 01

Day 1 - Sunday

About a month ago I stumbled across some pictures of my teacher online. By today's standards they aren't anything particularly outrageous - apart from a couple where she is completely naked, most just show her topless. They were posted on an amateur porn site under the title of "Naughty School Teacher" some five years ago.

Before seeing those images I'd never really been overly interested in Mrs Jones. She was attractive, but there have been many teachers I have lusted after during my years at the school and she wasn't one of them. After I had seen those pictures, however, I became obsessed with her. I have spent hours trying to find more, crawling through dozens of different websites and forums. Alas, all I was able to dig up were a couple of very tame social media profiles, which contain not so much as bikini shot between them.

Last night I was celebrating my friend's eighteenth birthday. He was the last one amongst our friendship group to reach this milestone, so it was quite a heavy night. When I arrived home - extremely intoxicated - I did something incredibly risky. I created a fake user profile on one of the social media platforms I'd found her on, and sent her a message.

"I love these pictures." I wrote, attaching the links I'd found, "I would love to see more."

I woke up this morning with a heavy hangover, that was dwarfed by the feeling of regret and shame swelling up from the pit of my stomach. How could I have been so stupid? I asked myself.

I quickly logged on hoping I could delete the message before she saw it, but discovered I was too late. Though she had not replied, I could see that the message had been read.

"Fuck," I grunted to myself.

My self loathing didn't last long, however. Yes, my actions may have been foolish, but they'd done nothing to quell my absolute obsession with this women. Soon enough those feelings of shame and regret had been almost wholly replaced with an overwhelming sense of rage. How dare she just ignore me? I thought. A very large part of me knew I was being petulant, but a louder voice was screaming at me to up the ante.

If I wanted to get anything from her I was going to need to threaten her with exposure. I knew how dangerous this was going to be, but it was a risk I just had to take.

I started to formulate a two-stage blackmail plan.

Stage one, was simple enough. I sent another message, this time telling her that if she didn't send me more pictures I would start showing the ones I'd found online to people at school.

"Who is this?" she replied, almost instantly.

"A pupil of yours." I answered.

"A current pupil?"

"Yes."

My heart was racing and my hands shaking. I couldn't quite believe what I was doing.

"You realise how much trouble you'll get in for this?" she followed.

"It doesn't need to come to that..." I answered.

"If you send me anymore messages I'll be contacting the police."

With that, stage one was complete, precisely as planned. I had gone to her with a deliberately unrealistic proposal. Whilst I was sure the threat would have scared her, she would have no doubt realised how difficult and risky its execution would be for me. I wanted her to have this false sense of security before delivering my second, more realistic ultimatum.

From looking through her social media I know that she has been married a long time - her oldest daughter is around the same age as me, so it's reasonable to assume it's been close to some twenty years. In the pictures, however, which were posted only five years ago, she isn't wearing a wedding ring. Now, that might not have meant anything, but, coupled with the very fact such images exist and that they have been posted online presumably without her knowledge, I couldn't help but wonder if, perhaps, they weren't taken by her husband.

If I was wrong about this my plan would be scuppered, but I pressed on with a good degree of confidence.

"How about I send the links to your husband?" I wrote.

I waited anxiously as "Kate is typing..." flashed across the top of my screen.

"What exactly do you want?" she asked, to my delight.

I pumped my fist in celebration.

"Hmmm." I replied, "I think for now I just want to see your tits."

"Then what?" she quizzed, "You'll leave me alone?"

"Probably not. I guess you'll just have to wait and see."

I was expecting more back and forth. A little more fight and negotiation, but instead, to my utter delight, she sent a picture.

It wasn't a particularly good picture, it was a bit dark and blurry, her top had been yanked up and her bra yanked down. It also didn't show her face.

None of these shortcomings matter though. The important thing is that she complied.

Day 2 - Monday

I saw her a few times at school today. She seemed normal, there was certainly no obvious signs of distress.

I decided to wait until around 6pm this evening before contacting her.

"I would like some more pictures." I wrote.

About an hour later she sent an image almost identical to yesterday's.

"You can do better than that!" I replied, "At least include your face."

"I'd really rather not." she responded.

I knew I needed to be very strict with my next message. She had to believe I was absolutely serious about exposing her, and that rejecting my demands was not acceptable.

"I don't give a flying fuck about what you'd rather not do!" I began, "Send me another picture right now. I'm not pissing about here - I will send your husband those links!"

I clenched my fist as I was awaited her response, and then cheered "Yes!", as it flashed up on my screen.

She had sent another picture. This time she was standing in front of the bathroom mirror, her face was flushed pink and her beautiful tits were on full display.

I was very tempted to ask for more, but managed to keep my discipline. This is a marathon after all, not a sprint.

Day 3 - Tuesday

I had a lesson with her this morning. Again, her behaviour and demeanour seemed pretty normal. She is doing a good job of hiding the anxiety she must be feeling.

A short while after the lesson had finished I messaged her.

"I want to see your pussy." I wrote, "Go to the toilet at lunchtime and take a picture."

She did this without argument. Just like in the ones I had found online, the picture she sent showcased a sizeable bush. I have no problem with this - I actually find it quite a turn on - but, as a shear power play, I wanted her to think otherwise.

"That hair has to go." I sent, "You've got until 8 o'clock tonight to send me a picture of your perfectly bald cunt. Understand?"

She didn't reply, but a little after 6pm, some two hours before her deadline I received exactly what I had asked for.

"Much better." I replied.

Day 4 - Wednesday

This morning was a bit of a rollercoaster. I woke up with a raging hard-on, and reached straight across for my phone.

"Where are you?" I asked her.

"At home." she quickly replied.

"What are you doing?"

"Getting ready for work?"

"Let me see."

A couple of minutes later she sent a picture of herself standing in front of a full length mirror. Her hair was wet and she had a towel wrapped around her body.

"Are you alone?" I asked.

"No." she replied, "My kids are downstairs."

"What about your husband?"

"He's left for work."

"Did he like your pussy?"

"He didn't notice it."

I was happy with the way the conversation was flowing. Not only was she answering my questions, but she was doing so nice and quickly. That was about to change.

"How often do you have sex with him?" I asked.

"Please don't ask me things like that." she replied, "I'll send you pictures, but I'm not going to talk to you about my sex life."

"Cunt!" a grunted through gritted teeth, as I read this.

"You will answer any fucking question I ask!" I typed furiously.

"I don't want to talk about my sex life." she reaffirmed.

I took a deep breath and tried to calm myself down.

"I promise you that if you don't start doing exactly as you're told I'm going to show him everything." I wrote, a few minutes later, "This isn't a game."

What followed was unexpected. Instead of acknowledging my demand she sent another picture. It showed her back in front of the mirror, this time with no towel. It was a great shot, there was no denying that, but it wasn't what I had asked for.

"Absolute last chance." I typed, "If you don't answer my question immediately this is over."

I prepared myself for what that meant, knowing that I would have to follow through with the threat if she didn't comply.

"Not often." she answered, this time, to my relief, "About once a month."

There were tons more questions I wanted to ask, but her earlier resistance had rattled me. I decided to leave her be.

Day 5 - Thursday

Something unexpected happened today.

I walked by her in corridor at around 10am, and almost did a double take. In all my years at the school I'd never seen her looking so made up. Her hair was neatly tied back, her makeup meticulous, and - instead of one of her usual mundane skirt and blouse combinations - she wore a long floral patterned dress that buttoned up at the front.

As soon as it was safe to do so, I messaged her to tell her how good she was looking. Somewhat frustratingly, she didn't respond, and I had to follow up at lunchtime.

"Why are you so dolled up?" I asked.

"No reason." she replied.

No reason? I thought to myself. It's surely not just a coincidence that a few days after I started all this she's coming to school looking so damn hot?

"Let me see what you're wearing under that dress." I demanded.

A couple of minutes later I was staring down at a picture of her in a toilet cubicle. The buttons of her dress had all been undone to reveal a black bra with matching panties.

"Fuck," I whispered to myself.

I hadn't planned on making my next demand quite so soon, but I couldn't resist.

"Let me see you see finger yourself." I wrote.

"Are you being careful where you're looking at this?" she asked.

"Yes." I replied, "Very careful."

I waited anxiously for her next message. A few minutes later the thumbnail of a video appeared on my screen. I took a deep breath and pressed play.

It was only a short clip, some twenty-five seconds in length. It showed her sitting on the toilet, her free hand resting lightly on her stomach. Her breathing was heavy. She slowly ran the hand down and slid it into her panties.

A soft moan was audible as the hand began to rock gently back and forth.

"Fuck," I again whispered.

I must have watched the video about a hundred times.

By the time I got home school I was so horny I could barely think straight.

"I want another video ASAP." I messaged, almost as soon as I walked through the front door.

"What sort of video?" she asked.

"Same as earlier, but no panties this time."

She carried out the instruction very quickly. Just five minutes later the video arrived. This time she was sitting on a chair. The bottom six or seven buttons of the dress had been undone, and her panties were no where to be seen. Two fingers immediately slipped into her pussy.

"Shit," she whispered softly.

I was lying down on my bed as I watched - rock hard cock in hand, when I suddenly realised where she had filmed this. It was her classroom! She filmed this after school in her fucking classroom!

It was more than I could take. My cock exploded.

Day 6 - Friday

I was a little nervous when I woke up this morning. Yesterday had gone so well that I was fearful I might do something to detriment my progress.

Then, as I was making my way into school, I gave myself a bit of a reality check. I had on my phone a video of Mrs Jones fingering herself in her classroom. A video that she had sent to me - a student of hers.

I had her marriage, her career and entire social standing all firmly in the palm of my hand. At any time of my choosing I could destroy any or all of these things, within a matter of minutes. There was almost no request I could make that she could sensibly refuse.

"Tell me about those pictures I found online." I demanded, as I arrived at school.

"What do you want to know exactly?" she asked in reply.

"Who took them?"

"Someone I was having an affair with."

"Who?" I probed further.

"Just some guy I met in a bar." she explained, "I should never have let him take them."

"Do you cheat on you husband a lot?"

"No. Not often."

"But you have more than that once?"

"Yes."

"How many times?"

"3. No one since the guy who took the pictures."

I was delighted with her candid responses. It occurred to me that she too probably realised the things she had sent me over the last week had strengthened my hold on her, and resistance really was now completely futile.

"I think you should suck my cock today." I wrote next, almost surprising myself at my sudden and extreme escalation.

"You really want me to know who you are?" she replied.

"I've considered that. What difference does it make? My anonymity doesn't really matter. If you try to get me in trouble you're majorly fucked. End of story."

At the moment the bell rang to indicate the start of the first period. I slipped my phone into my pocket and tried to forget about our ongoing conversation.

Her next reply didn't arrive until lunchtime.

"So when exactly?" she asked.

I took a deep breath and then puffed out my cheeks. Was I really going to do this?

"Straight after school." I replied, still not really sure I was being serious.

"Where?" she questioned, "I'd rather not do it here. Can we meet somewhere else?"

I took a few minutes to consider a suitable location. There was an abandoned industrial estate about fifteen minutes from school that I thought would be ideal.

I tortured myself for next couple of hours. There were two conflicting voices fighting in my head. The first told me, that this was too much too soon. The second kept asking what could possibly go wrong - I had everything under control - she was mine for the taking.

There was really little debate.

I left school a bit early so I could arrive at the industrial estate comfortably before she did. This was a decision I regretted almost instantly. The longest hour of my life followed.

Soon enough I saw her car driving down the long decrepit road that lead to the car park where I had been waiting.

I can't remember having ever been so nervous in my whole life. I gritted my teeth and told myself to hold my shit together.

She climbed out of her car and walked over to mine.

"So it's you?" she said, as I wound down the window.

"It is," I replied, confidently.

An awkward few seconds of silence passed, as she starred down at the ground.

"You getting in then?" I asked.

She nodded, then walked around to the passenger side door.

"What exactly do you want me to do?" she questioned, as she climbed in.

"Exactly what I said earlier," I replied, cooly, "I want you to suck my cock."

"I really don't think we should do this," she sighed, "We're both going to get in so much trouble."

I shook my head.

"No we're not," I assured her, "No one's ever going to find out, unless you do something stupid."

"I hope you're right," she shrugged.

I wasn't going to waste anymore time. I unzipped my jeans and pulled out my cock. It started to swell immediately.

"We're really doing this then?" she said, looking down at it my cock.

I nodded.

She turned slightly to face me, swept her hair over her right shoulder and then leaned down, engulfing my cock in her mouth.

"Fuck," I couldn't help but moan, as her lips tightened around my shaft.

I've been the lucky recipient of many a blowjob over the last few years, but none compared to what I was experiencing at that moment. Whilst her technique was solid, it was the reality of the situation that was driving me quickly to the edge. I couldn't quite believe that this hot-as-fuck-married-mother-of-two - who just so happened to be a teacher of mine - had my cock in her mouth.

I gritted my teeth and tried with all my might to not allow my balls to erupt. I was doing well until she suddenly pushed her head down and took my cock into her throat. Her subsequent gagging was more than I take.

"Shit," I grunted, "I'm gonna cum."

A heavy jet of jizz shot from my cock and filled her mouth. She paused for a moment, it seemed like a hesitation, and then with a single large gulp she dutifully swallowed everything I'd given her.

I looked towards her as she sat back up. Her cheeks were a bright pink and her eyes streaming. She had never looked sexier.

I considered taking her out the car, bending her over the bonnet and fucking her senseless.

"You can go now," I told her, instead.

"Ok," she whispered softly in reply.