Downfall of the Teacher Ch. 05

Story Info
Miss Stephenson embraces the blowjob challenge.
6.5k words
4.57
11.4k
12

Part 5 of the 5 part series

Updated 06/11/2023
Created 04/19/2022
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I'm guessing by now you're getting a little tired of me complaining about how hard it was to teach a class with everything that was going on in my head? Well at that point if all I had to contend with was the memory of Jake bending me over and screwing me over my desk it would be bad enough, but my mind wanted to work out how I was going to find five dicks to suck over the next week and not teach the intricacies of comprehension to a bunch of uninterested fourteen year olds.

Phycologists would probably have a field day analysing my thoughts that afternoon. Had Jake knowingly tapped into my love of a challenge? Was the thought of servicing so many men a form of self-validation? Was my inner slut thrilled that it was about to be let loose? Or was I already looking forward to how good Jake's dick would feel knowing what I'd done to earn it?

I fantasized about how I'd go about the task... I imagined setting up a fake Tinder profile and going on a series of dates where I'd suck cock in return for them buying me drinks. After my fun on Sunday I could keep on visiting the gym and providing car park blowjobs until I'd hit my target - with the added bonus that after all those exercise sessions I'd be in amazing shape! Or maybe I'd just go out clubbing, let myself into the men's bathroom and blow whatever lucky guys came in. Why was the thought of having men queuing up to use my mouth turn me on so much? Would I be picky with who I chose? Would I go after hot, young, muscular studs, lustfully sucking their great big dicks until they blessed my mouth with their cum? Or would I be less discerning, seducing less attractive men knowing they would savour each and every second their cock was between my lips?

Needless to say, despite the relief Jake had provided me earlier in the day, by the time the school bell rang I was one great big horny mess. How had Jake turned giving out blowjobs to strangers the sexiest thing I'd ever imagined? I checked my watch - Tony wouldn't be home till half five, so factoring in travelling somewhere I'd have roughly an hour to find a target, persuade him to let me give him a blowjob and then perform the deed. I could feel the adrenaline pumping through my veins as I gathered up my possessions when behind me I heard a knock followed by the classroom door opening.

"Good afternoon Hannah, how has your day been?" came the voice of Colin the school janitor, snapping me out of my blowjob daydreams. Despite not being on the teaching staff he'd been one of the most welcoming of my co-workers, providing plenty of advice on how to handle students. With his retirement on the horizon I knew I would miss his help and support.

"You know what, it's been pretty good," I replied, smiling in a way I hoped wouldn't give away that the highlight had been being bent over my desk and screwed by one of my students.

"Yes, that's what I came to talk about... I came to see you earlier, but there were some shall we say, interesting, noises coming from your classroom." He paused, allowing the significance of what he'd witnessed to sink in. My career, my relationship, my life could all be over depending on what he decided to do. "I've worked at this school for a long, long time you know. You're not the first teacher to give into temptation in the classroom, not the first by a very long way. We're all human after all, but I need to make sure that this was just a one off that won't be happening again."

"It was just one moment of weakness... things have been difficult at home and I needed to get things out of my system. It won't happen again." I lied, knowing fine that my body was Jake's to do with however and whenever he pleased.

"That's all I needed to know."

"Thank you," I said, relieved that things wouldn't be going any further. "Is there anything I can do to show my gratitude?"

He paused for a second before answering. "Actually yes... ever since you started working here I've been absolutely mesmerised imagining what you keep in your blouse. Would you make me a happy old man and give me a quick glimpse?"

It took me a minute to process what he'd asked, was the only reason Colin had befriended me because he was hoping one day to exploit a situation to see me topless? My mouth went dry... was he really expecting me to flash my breasts at him? He'd phrased it as a favour, but whilst he'd promised not to tell anyone about me and Jake I knew that if I didn't comply with his request my life could end up in ruins.

I didn't want to believe that Colin would get me into trouble, but I couldn't risk not doing as he'd asked. As I slowly unbuttoned my blouse I started to feel a thrill at flashing my breasts at an older man. As I let my top fall to the ground his eyes were fixed on my cleavage. I reached behind my back and undid my bra which too fell to the floor.

Colin inhaled sharply at the sight of my exposed breasts. "You might not think it looking at me now, but in my younger days I was a bit of a lady's man," he told me. "I had more than my fair share of women, but none of them had tits as fine as yours."

"Thank you," I replied.

"Would you make an old man very happy and let an old man have a quick feel?" he asked.

I knew I should put a stop to this, to draw a line as to how far this was going to go, but at the same time he still held all the cards. Meekly I nodded in agreement. With his proposal accepted Colin stepped forward and placed his hands on my tits and slowly explored them with his fingers, before he lowered his head and began to lick my nipple. Any disgruntlement I had that this was more than I had expected vanished as I sighed in pleasure at what his tongue was doing to me.

The problem with having large tits is that guys think they can do anything to them and it'll be turn on for me. The majority of men I've been with thought that roughly grabbing and pulling and biting my breasts was a sure fire way to get me going. But not Colin. Colin's tongue, lips and fingers worked with surgical precision, leaving me gasping with pleasure as my nipples were teased as they'd never been before.

But then a dangerous thought entered my brain, if his tongue felt this good on my nipples, how good would it feel on my clit? And once that thought took root there was no ignoring it. A look of disappointment passed onto Colin's face as I pushed him away from, until he noticed I was undressing myself further. For the second time that day my skirt and knickers fell to my classroom floor. I climbed onto my desk and spread my legs, inviting Colin to bury his head between them, an offer he didn't hesitate to take up. Having spent the afternoon fantasising about sucking dick my body was already in a state of high arousal, and as Colin's tongue expertly worked my clit I could only lie back and gasp in pleasure. It didn't take long till for the second time that day my classroom was filled with the sound of me screaming as I came.

Colin stood up and watched my naked body until the orgasm stopped rippling through it. "Well Hannah thank you for your time," he said to me as if all that we had done was share a cup of coffee "but I need to finish off my rounds."

"Thank you, thank you so much," I panted in gratitude.

"No, the pleasure was all mine," he replied as he walked out of the classroom, a visible twinkle in his eye.

As I dressed myself I reflected on my day. Without leaving my classroom I'd had two men make me cum - one a teenage student and one the sixty something school janitor. And I didn't regret a thing.

So where does a girl go after a day at work like that? Fucked and then fingered till I came by one of my students then licked out by the school janitor. I knew how close I'd come to having my whole life crumble in front of me, but I guess that was a part of the thrill of my new life which I was now living. That and the mind blowing orgasms.

As I pulled into my driveway Tony text to say he wouldn't be home till late as he had some important business he needed to sort out. Normally putting his work ahead of spending time with me would put me in a shit mood, but at that point Tony was already part of old Samantha's world and had no role in my new one.

Not being in the mood to cook I sent in an order for pizza - don't judge me, orgasming that much leaves a girl hungry! With food on its way my mind wandered back to Jake's challenge. Giving five blowjobs to different guys within a week didn't sound difficult, but I was in danger of my first night of my quest passing without making any progress. And then a thought passed in to mind... I remembered all those terrible porn scenes where the bored housewife can't find her purse so has to pay for her delivery using her mouth. And the more I thought about the more convinced I was that it was a good idea, until I found myself running up my stairs to put on something more seductive.

I quickly stripped before pulling on a pair of white panties and matching corset top, which not only failed to fully cover my tits but also left my nipples visible for the world to see. As I glanced at myself in my mirror a sense of unstoppable power from how I look. No man would be able to say no to me to dressed like this, not until they'd given me the mouthful of cum that I wanted.

I sat down by the upstairs window hoping to be able to make a judgement call on the delivery boy before we came face to face, dressing gown to hand in case I decided to back out. But the longer I waited for him the hornier and sluttier I felt, before I realised that no matter who turned up at my front door with pizza was going to get their dick sucked. I've always been an impatient, so it was a relief that it didn't take long for the pizza to arrive. As I watched the delivery guy walk up my driveway I was relieved that he was at least passably attractive. I rushed downstairs ready to greet him my heart racing at the thought of what I was about to do.

I can't deny that I felt a thrill answering my front door to a complete stranger whilst wearing next to nothing. Actually it was much more than a thrill, I felt like a super confident seductress. A couple of weeks ago I couldn't have imagined doing anything like this, but now it just felt like another stage of an exciting adventure.

"Hi I'm Darren, did you order a large Hawaiian?" he asked, his eyes darting around not knowing where to focus but regularly falling back to my tits.

"That's mine, bring it inside," I replied, closing the door after he entered before taking the pizza off him and placing it on the sidetable.

"Uhhh.... what's going on?" he asked, suddenly realising that this wasn't going to be a standard delivery.

"I just wanted to say a special thank you for such a quick delivery," I told him whilst deliberately sticking out my chest and putting on my best slutty grin.

"Ummm... I've kinda got a girlfriend," he protested, not realising he had no say in what was about to happen.

"Don't worry I won't tell her. And I promise you I suck dick far better than she does," I informed him, but he didn't seem convinced. I turned to plan B, reaching behind my back down before whipping my bra off.

He stood open mouthed, his stare fixed at my exposed breasts. He didn't speak, but the newly appeared bulge in his trousers showed me my persuasion skills had worked. I stepped closer to him and placed my hand on his chest before allowing it to slowly glide down to his erection.

A friend of mine once had a phase of sleeping with happily married men. When I asked her why she did it she said she got off on the thrill of watching their will power crumble, of seeing their loyalty to their wives evaporate as their desire for her crushed all logical impulses. And as I stroked Darren's cock through his trousers I realised exactly what she'd meant.

But I wasn't here to tease him, well not for long, I had a task to complete... plus the longer this took the colder my dinner was getting. I lowered myself to my knees in front of him and quickly undid his trousers, pulling them down to reveal his hard six inch penis. I found myself salivating at the sight of it as I wrapped my hand around it and gave it a quick tug, before the desire to have it in my mouth became too strong.

As soon as his dick slipped between my lips Darren began groaning loudly. As my tongue massaged his cockhead I could tell that whatever he got from his girlfriend good head wasn't one of those things. Already I could tell two things - he wasn't going to last long, and that he was going to give me a good load when he came. My mouth went into overdrive, sliding up and down his shaft before he exploded inside my mouth.

Having swallowed his cum I stared up at him grinning, watching the realisation of what had just happened and the guilt of cheating on his girlfriend overpower the fading sensation of having his dick sucked.

"I... I need to go," he stuttered as he pulled up his trousers before making a hasty departure from my home.

With Darren gone I had one final task before I could start on my well deserved pizza. I grabbed my phone and typed "One" before sending it to Jake. Seconds later he replied "Well done, you're becoming a proper little slut Mrs Stephenson. Four more to go for your reward". I smiled in anticipation, both for the four blowjobs I would be giving and for what Jake would do to me afterwards.

Is there a better post blowjob food than pizza? Not that I've come across. Still, one carb overdose later on top of all the excitement for the day and it was early to bed. When you're a wild seductress like I was rapidly becoming you've got to be looking your best after all!

Around midnight I was woken by Tony drunkenly pawing at my breasts. Not so long ago I would have played the diligent girlfriend and give him what he wanted, let him have his five minutes of fun, but the rapidly evolving new me wasn't interested in an unsatisfying fumble. Somehow I persuaded him I wasn't in the mood and that I'd make things up to him later in the week.

I spent the morning at school jumping every time my classroom door opened - an enticing mixture of excitement and fear that Jake could turn up at any time. As much as I wanted to see him, be thrilled by him, the sensible part of me was still whispering that at any moment I could be caught out and my whole life come tumbling down. But even in the school corridors Jake was strangely absent. It was only when I returned to my classroom after lunch that he made his move. On the middle of my desk was a box and label that hadn't been there when I'd left I picked up the label and read it: "For my favourite teacher, Well done on completing the first of your tasks. Here's a little something to help you reward yourself after you finish the next ones x"

Intrigued I opened the box and stared at the wand vibrator inside. Normally teachers are supposed to declare any gifts they receive from their students, but I figured this one would be kind of difficult to explain. Deep down I knew what Jake was doing... by getting me to masturbate after giving head he wanted to condition me to connect sucking dick with my own pleasure, to correlate having a mouthful of cum with my own orgasm. If only he realised how little encouragement I was needing to blow complete strangers, how just the thought of a stranger's cock was causing my pussy to tingle wildly.

Without thinking my fingers switched the vibrator on, causing it to hum hypnotically. If not for the school bell ringing to sound the beginning of afternoon sessions I would have used it there and then, hell, it wasn't like I was a stranger to having orgasms in my classroom was it? All I knew was that I couldn't wait till work finished so I could get out, suck some dick and then try out my new toy. After setting my class a comprehension exercise I checked my calendar and remembered I had promised one of my former pupils I'd go and watch the new show he was involved with.

Arrogantly I like to believe that so many of my former students had stayed in touch with me after they'd left school because I'd been an inspiring and brilliant teacher, although deep down I realised that having spent their teenage years staring at my tits as I tried to teach them they thought once they'd reached adulthood they had a chance with me. Lee had been one such student who'd stayed in touch. He'd always been a lovesick little puppy in my classroom, always offering to help teacher, with his devotion extending to going to film school after graduating presumably in the hope that as a successful actor he'd be able to sweep me off my feet and get into my pants. So when he had messaged to say the performance group he was in were coming to town to put on their new show I felt compelled to accept his invitation.

So that's how I ended up sat in the front row of my local theatre watching "Crackpipes and Tinder Hook Ups", a self described wild and extreme look at drugs and dating in the 21st century - needless to say "prepare to be shocked!" concluded the preview of the piece. It goes without saying then that the only thing shocking was the atrocious dialogue based around the shallow observations only a group of nineteen year olds could consider to be earth shattering. If not for the fact I had a personal connection and had promised to meet Lee for a drink after the show I would have left during the interval.

Things though took a turn for the better as the second half of the performance began. As the curtains pulled away Lee stood there, completely naked. His body was better than I thought, more toned and muscular than I expected of someone who'd always struggled with nerves and confidence. But that wasn't where my focus was drawn to.

What does a perfect penis look like? Length, girth, and a nice big throbbing cockhead would probably be top of my list, and whilst it might not quite have matched Jake's dick for size the one on show was quite simply the most beautiful manhood I'd ever set eyes on. I sat open mouthed, barely taking in a word of his monologue, as I stared at that immaculate dick. My cunt ran wet as I imagined all the ways I'd pleasure that cock, slowly teasing it until it could take no more, and how in return it would give my body what I needed. As soon as I saw it I knew I was going to have some fun with that dick, now I just had to engineer a situation for it to happen.

Much to my disappointment Lee left the stage and when he came back his clothes were sadly back on. If I'd thought the first half of the show had dragged it was nothing compared to the second as my body quivered with excitement at the unexpected treat that was hopefully in store for it. Jake had been exciting to be with, his cock unbelievable wherever he put it, but there was something thrilling about the thought of seducing sweet, quiet Lee and devouring his giant dick.

When the curtain eventually fell for the final time I forced myself to be patient, waiting for all the other attendees before I snuck backstage. Years of being part of the local amateur dramatic society meant I knew how the changing room set up worked and most importantly where to check who had been allocated which one. My heart fluttered as I read Lee's name next to room 16 before setting off down the corridor to find him.

Excitedly I knocked on the door... My heart thudded in my chest as I waited for the for him to answer. Would Lee be receptive of my approach or was I full of myself assuming that my students secretly wanted me? Was I about to make an utter fool of myself throwing myself at a man a decade younger than myself? Would I open that door to find someone else had beaten me to and Lee was already pounding away a lucky groupie? After what felt like a life time the door opened and Lee stood in front of me. His skin looked wet, as if he hadn't had time to dry himself properly after a shower, and all he wore was a towel around his waist under which the bulge of his dick could be clearly seen.

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