Trapped! Pt. 01

Trapped

Part 1: A Trap Is Sprung

As a teacher, I shouldn't admit this. But sometimes you have students you just hate. And for almost a year I had hated Jessica Dane.

I was only 25, fresh out of university, straight into a job teaching English. For all my life I was poor, short, thin, and pale. My only saving grace appearance wise was my long, rocker hair (although I was tragically ginger). Comparisons to hobbits were made while I was in university. But before that I was just a pathetic nerd. Fodder for football jocks who kicked my ass at every opportunity. And perfectly ignorable by cheerleaders who seemed to put out for everyone but me. But why did I hate Jessica Dane?

She was the embodiment of everything I had hated about popular girls when I was at school. She was a cheerleader, she was popular, had rich parent who seemed never to be actually at home taking care of her, and she was very good looking. Long blonde hair surrounded her head like a halo, framing her high cheek bones and piercing blue eyes. Her body was already perfect despite only just having turned eighteen. The girl seemed to love flaunting her toned abs and shapely legs, wearing shorts tops and even shorter skirts to all her classes. Including mine. And I couldn't help but look.

And to add insult to injury. She was one of the smartest students in the school. Despite never ever paying attention to me or any other teacher she never failed to do well in every test. Some would claim it was due to studying outside of school, but I had my doubts.

Of course every other teacher loved her. 'She's going places' I was told, every day. By colleagues who were unaware of my deep hatred of her. And unaware of the fact that I couldn't help but fantasise about her in a cheerleader outfit, on her knees, giving a long suffering nerd what he deserved.

I wanted, I needed to catch her out somehow. I needed to punish her for her perfection. And I got my chance.

--8--

I looked over the test I had prepared on the works of Rudyard Kipling. Just twenty questions, but they were all very difficult (the rest of my students were suffering in my attempts to stump Jessica), and I was very pleased with myself for having come up with them.

It was my last class of the day, the heat had forced me to open all the windows and doors just to cool the place down, and the bustle of the corridors dissipated as students found their classrooms. For a few moments everything was quiet apart from the soft murmur of my students as they lined up outside my door.

"Oh god Jen." Said a soft voice. Jessica's soft voice. "I'm so nervous. This plan had better work."

I got up silently. Confused. She was talking to her best friend and fellow cheerleader Jenny. But what were they talking about?

"It will Jess, I'm sure." Answered Jenny.

"I should have just studied." Sighed Jessica.

This was about the test. I felt strangely triumphant. I knew I shouldn't have felt proud to have a student about to fail a test.

"But then you wouldn't have been able to go out with Danny." Said Jenny, matter-of-factly. "Don't worry. Just trust me about this."

I stepped out into the corridor looking at Jessica and Jenny. Both of whom looked like they were hiding something. I frowned at them. They just smiled back.

"Right gang." I told my class. "Time for a test."

They all groaned.

For those who don't know. Presiding (invigilating technically) over a test is incredibly boring. And not even my suspicions about Jessica could make me want to look at a bunch of students writing in silence for an hour. So I read a book, occasionally getting up and walking a quick circuit of the room to remind them all I was still there.

And it was on one of these small constitutionals that I spotted a phone in Jessica's hand. She had hidden it well. If I was closer to her, or even at a slightly different angle I wouldn't have seen it, but there it was. I could see she was looking over a text conversation of some kind. Every so often she would look up at her text paper and scribble something down. It took a lot of my willpower not to leap for joy. It took all my willpower not to jump over and scream GOT YOU! Right in her face.

As it happens another, darker part of my brain spawned a horrible idea.

When the test was over I collected the papers from my students desks, dismissing them one by one till only Jessica was left. I looked down at her, putting on a disappointed look.

"Jessica. Can I have your phone please."

Her shoulders slumped in defeat and tears pricked at her eyes. She reached into her pocket and produced her phone, which I took gently.

"Come with me." I told her.

She slowly rose and followed.

--8--

My office in the school was on the top floor (the forth), with a solid wooden door, and solid walls. The only window to the outside being so small it let in almost no light. And it had no security cameras. I didn't need them, my personal computer was a laptop I took with me everywhere. And no one was going to rob an English teachers office for anything else. It was perfect for what I had planned.

I was going to humiliate Jessica. I was finally going to fuck a cheerleader. And I didn't care that it was going to be very illegal. I was going to put her on her knees and put my cock between her perfect lips.

Whilst on the way I had scrolled through Jessica's phone and found the texts she had been receiving. Not the complete answers to my test, but big hints and helping hands. As I sat down behind my desk I showed her the evidence. Jessica didn't say a word, she just stared at the floor.

"You know Jessica. I never had you pegged as a cheater." I lied. I had always suspected. "I am very disappointed." Another lie. I was giddy as a school boy who was, well, about to fuck a cheerleader.

"I'm sorry sir." She said looking up at me for the first time. Her eyes were damp, but she hadn't started to cry yet.

I sighed dramatically. "I should take this straight to the principal." Jessica breathed in sharply. "But I think you deserve a second chance." I raised an eyebrow at her.

Jessica licked her lips. Had she guessed what I wanted already? "What kind of chance sir?" She asked, almost huskily.

Deciding to just get it all over with, I stood up and stepped around my desk. I unbuckled my belt and dropped my slacks to the ground. My semi-erect cock springing free. Jessica gasped and I stepped forward, stepping out of my crumpled pants. Getting between her and the door. "I think you know what I want." I breathed.

Jessica hung her head in shame. Reaching down, she pulled her skirt and panties down and let them fall to the floor. Revealing a completely shaved pussy. I growled in desire as she turned to sit on my desk, spreading her legs and kicking off her shoes. And I finally noticed the thigh length stockings she was wearing.

"Just get it over with." She sobbed.

I tried to be casual as I stepped over to her. My cock was now fully erect. I couldn't take my eyes off her perfect cunt as I did so.

Which is why I didn't see her grab her phone from my desk. But I did notice the flash as she took a picture of me.

I was in shock. She had taken a picture of me. A full body photo, my face clearly visible. My look of lust clearly visible. And Jessica was laughing as she showed me the picture that would get me sent straight to prison.

"It's already been uploaded to my cloud." She explained as I scrabbled to pull my trousers back on. "But I wonder who should get the first copy. The principal, or the police."

I fell to my knees. My pants still around my ankles. "Please no!" I begged her. "Please Jessica. I'll do anything."

"I seem to remember you wanted me to do anything just a few moments ago." She laughed again. "Perhaps I can think of something I want you to do for me."

Jessica was still sitting on my desk and she spread her legs again. I couldn't help but look.

Jessica giggled. "You're such a stupid pervert." She looked me over appraisingly. "With a small dick too. But that won't matter so much."

I looked down at my member. I'd never given much thought to how big it was compared to other men. It was about four inches long, with not much girth. I'd never received any complaints from the two women I'd managed to bed in my lifetime (but they had both been drunk so maybe they weren't the best sources).

Jessica sat back further on my desk. Spreading her legs even more, slightly parting the dark lips of her shaven pussy. I couldn't help but stare, And get rock hard all over again.

"You love my cheerleader pussy don't you." She giggled. "I bet you wanted to bend me over and fuck me while I cried like a bitch."

I didn't answer. I just lowered my head, trying but failing to tear my eyes from her perfect body. Jessica shifted forward, putting her stocking clad foot onto my cock. I gasped at the sensation. The warmth of her flesh, and the gentleness of the silk felt amazing. I gasped again as she began stroking me with her foot.

"I know you've wanted to destroy me for ages." Jessica said seriously, but she continued to stroke me. "I could also see that you've wanted to rape me for ages." The word 'rape' send needles through my brain. But of course she was right, I had just tried to rape her. "So me and Jenny cooked up a little plan. To have a little fun with you."

All of a sudden I could see the trap I'd fallen into. And I finally looked up into Jessica's face. "So this means you never really cheated?" I asked quietly, in defeat.

"No." She laughed. "I never needed to cheat before today. I'm just that smart dickhead."

"What do you want me to do?" I asked. Knowing the only way to stay out of prison was to do exactly what I was told.

Jessica added her other foot to my swollen cock, and began stroke my whole (short) length with her feet. I almost cried out at the sensations, she knew what she was doing and I was now fast approaching climax.

"I want you to go to the motel on the north side of town at 5 PM sharp."

I knew the place she was talking about. Everyone knew that the motel on the north side of town was for incredibly seedy meetings, hence it being surrounded by prostitutes morning, noon and night.

"Room 1-20. Don't be late." She warned me.

I made sure to commit it to memory. Which was very difficult considering she was now fully wanking me off with her feet. It was obvious I was close from the way I was breathing, my gaze had also returned to her now visibly damp pussy. A part of me realised she was getting off on blackmailing me.

But just as I was about to cum on my office floor. She stopped, and stood up.

"Please." I whispered. Looking into her eyes.

She glowered down at me. "You don't get to cum with my help yet you fucking ass-hole." I could see she had tears in her eyes. "Just don't be late you cunt."

Jessica began to angrily collect her clothes and put them back on. I couldn't move, all I felt was on overpowering feeling of guilt, and shame.

--8--

On the way to the motel (called The Parade Motel if you're interested) I was sick with nerves. I could barely control my car, my feet and hands were shaking so much.

I parked up on the far edge of the main lot, I really didn't want to be seen here by anyone. As a bachelor people would only draw one conclusion. And that conclusion would involve one the practically naked women standing around the motel office.

I pulled up my hoodie and exited my car, trying to make myself as small as possible.

A few moments later I was at the office. I had tried to identify where room one-twenty was, but I just couldn't see it. So now I was having to brave the cordon of hookers and risk asking the staff who worked here. And if Jessica had booked the room in person, it could create a problem.

I ignored the questions of whether I 'wanted a good time' and stepped into the surprisingly clean and well lit motel office. The only thing that made me balk was the way the (rather fat) guy sitting at reception was resting two legs but only one foot on his desk, his left leg having been amputated at the knee.

"Well hello there." He greeted cheerily. "I take it you're actually here for the night, by the way you haven't got a hooker hanging off your arm." I blushed at his forthrightness. He laughed and continued, "Or maybe you are here for a quick fuck, you just haven't chosen a girl yet." He pointed to a tall dark woman through the window. "I recommend Aisha. She could suck the chrome off a trailer hitch."

My mouth fell open in shock. The guy just smiled, holding back a laugh. For a few moments neither of us said a thing.

"I'm trying to find room 1-20." I told him.

His grin became a small, knowing smile. "I'm Jimmy." He told me, holding out his hand for me to shake. "We'll be seeing a lot of each other I imagine." I didn't take his hand. I just looked at him in confusion.

"It's on the second floor. The last door on the left side. It doesn't have the number on it, that's why you couldn't find it." He explained.

I walked out of the office even more confused than I entered it. But I did spare a glance at Aisha. She was tall, very dark skinned, and wearing very little. A leather skirt that was an insult to most belts, a pair of long PVC boots, and a small denim jacket that didn't even conceal her enormous breasts, which were held in check by a cherry red bra.

"100 bucks for a half hour honey." She told me huskily, and I realised my glance had become a stare. "Call Jimmy and he'll send me up if I'm here."

I turned my attention away from her and down to my feet.

Part 2: A Man Brought Low

I soon found room one-twenty. It took me a few calming breaths to even raise my hand to knock, I was dreading what was to come. What was Jessica going to do to me? How was she going to punish me?

Suddenly the door opened without me knocking. I saw a flash of Jessica's arm as she reached out and pulled me into the dark of the room. I was able to take in the fairly standard décor of the room, with a pair of single beds, before I got distracted by what Jessica was wearing. Which was very little. Just a red push up bra, red crotchless panties, and red thigh high stockings with a matching garter belt.

"You're late." She told me franticly. "He likes people to be punctual."

I suddenly became aware of the sounds coming from the en-suite. The sound of someone showering.

My mouth went dry. So this is what she wanted me to do. "You want me to have sex with a man don't you."

She grinned. "A cookie for the smart man. But don't worry teach, that won't happen right away." She looked me up and down. "But you do need to be naked."

I nodded, getting the hint. I began to strip slowly, revealing my scrawny body to a giggling Jessica.

By the time I was done the showing had stopped and the door to the bathroom had opened revealing it's occupant.

The first thing I noticed was his height. He was damn tall, at least six-five. The next thing was his long blonde hair. It cascaded around his shoulders, down his back to well past his shoulders. Finally was his muscles. He wasn't big like a weight lifter. He was thin, but toned to perfection. If a statue of a Greek god came to life, it would have looked like this man. I couldn't help but follow his abs down his body with my eyes, water from his shower glistened on his lightly tanned skin. My ogling only stopped when my eyes came to the towel wrapped around his waist.

"Don't worry. You'll get to see it soon." He told me. His voice held a deep, rich tone. And it was only improved by a crisp English accent. His words made me realise I had essentially checked this guy out. "Stand in the middle of the room." He ordered. And I obeyed.

He walked around me slowly, looking at me from all directions. Inspecting me. Sizing me up.

But as he continued his circuits around he began to touch me. He ran his long fingers down my arm, then up my back. I shivered. He put a finger under my chin, lifting my head, revealing my lack of any kind of beard (it was a point of personal shame that I'd never been able to grow a beard). The finger trailed down my neck over my shoulder. I shivered again. But not from the cold. The room wasn't cold at all.

Then he slapped me on the ass. I leaped forward with a whimper. He grabbed my shoulder and pulled me into him. My back was pressed against his muscled chest. One arm wrapped itself around me, holding me close. And the other snaked around my belly and down to my cock, which I noticed (with some embarrassment) was as hard as it had ever been.

I released a breath as he took me into his hand and began to manipulate my cock. And he whispered into my ear

"So I heard you tried to blackmail my Jessica here."

Jessica had since sat on the bed in front of me, and spread her legs to show me her glistening cunt. I could only nod.

"I don't like that." He told me. "No one fucks my slut without my permission."

I gave a small sigh of pleasure. "I'm sorry." I muttered.

He laughed, pushing me forward. I fell to the floor with a crash, where I landed right between Jessica's legs. I was only a foot away from her pussy. I could smell it's sweetness. I licked my lips.

"Don't even think about it." She snapped at me.

The man stepped over me, to Jessica's side. "He clearly needs training."

Jessica nodded, and I became more confused and somehow even more worried.

"I'll train him. He'll be amazing for you after I'm done with him." She said. "But otherwise?"

"He clearly has potential. I think he can learn a quick lesson right now."

He looked down at me, finally meeting my gaze for the first time. I felt myself wither and shrink under his granite eyed stare. "Suck my dick." He said forcefully.

I almost fell backwards in shock. But I soon leaned the order wasn't for me as Jessica pulled down his towel, revealing his cock.

It was huge. Circumcised, almost eight inches long and with a thickness to match. And Jessica took the whole thing in her mouth with ease, moaning like a porn star as she did so.

"You've never sucked a dick before have you." He said, and this time I could tell it was aimed at me. I shook my head.

"You're going to love it." He told me as Jessica moaned again. Now I could see she was furiously fingering herself as she expertly worked the guy's huge member.

I shook my head again. and he just laughed. "You are going to love it, or Jessica here is going to send that picture of you straight to the police."

I felt tears prick my eyes. This was where my life ended. I was going to be beholden to these two sickoes for the rest of my life.

"I bet you want to taste my cock." He continued. "I know you want to taste my cum." Jessica moaned again, louder than ever.

"I know you want to taste my cum, because If you do. I'll let you fuck my slut Jessica here." This time I did fall back in shock. I looked up at his face. He meant it.

"I'll let you use her, abuse her. For however long you can last. You can call her whatever you want. Put her in whatever position you want. Slap her, pull her hair, cum in her mouth, on her tits. Even in her ass, I promise she'll even love it. She'll let you use her worse than the whores out front."

Jessica suddenly pulled the cock from her mouth and looked at me. "Please, taste his cum. I want to be used." She moaned.

I heard my mouth speak before my brain had even decided. "Ok."

"Alright then." He said happily. "You can fuck Jessica once. Then you taste my cum. Deal."

I hesitated for a brief moment. "I'm not sucking your cock." I told him. I sounded braver than I actually was, and I sounded as quiet as a church mouse.

He nodded. "Ok." Surprising me. And a part of me wondered how he was going to get me to taste his cum. But that thought was buried beneath a wave of giddiness as I saw Jessica lay back on the bed, spreading her legs.