Headmaster free porn video

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100% fiction!

The PE teacher had buzzed ahead telling me to expect you. She had not however, prepared me for exactly what I was to be punishing you.

I could easily have lost my job for the punishment I chose for you. Christ, I really should lose my job for the punishment I chose for you.

There was a knock at the door…

“Come!” I shouted.

You stepped inside. You were still wearing your gym clothes…a tight, powder blue top, showing-off those incredible, juicy tits to perfection. Below…you were wearing a tiny gymslip, displaying far too much of your smooth, naked thighs and on your feet, a simple pair of white training shoes.

God you looked good! You looked simply too good.

It could be incredibly difficult being the head of the school at times, particularly when I had to punish naughty sixth form girls. Particularly when I had to punish naughty sixth form girls…like you. Yes you were 18. Yes you were a woman now, but I was your headmaster and, from the moment the thought entered my mind, I truly knew I was in the wrong.

I could feel my cock twitching hard as I looked up at you standing still before me.

I always had a philosophy of punishing my students in a way somehow related to the crime that they had committed, but perhaps in this case I should have forgotten about that, but, as you well know, for right or wrong, I did not.

“So young lady! What have you been up to this time?” I asked.

You stared down at your feet, your cheeks flushing scarlet.

“Well come on girl, I don’t have all day!”

You looked up at me briefly, mumbling something quite inaudible.

“For goodness’ sake girl, speak up! I doubt anything you have done now can be any more shocking than the things you have got up to in the past now can it?”

How wrong could I be?

Finally, you looked up, your eyes piercing my own and said in a full, clear voice…

“I was caught touching myself in the changing room Sir.”

It was my turn to blush now. I stared down at my desk, pointlessly shuffling papers from one place to another and swallowing hard, but there was another more powerful emotion than embarrassment making itself known. My cock was hard and pulsing. I wanted you and as I took a deep, calming breath I decided…I might just have to take you.

I looked up, a little more composed now.

“I see. Well…a young lady of your age should not know about such things, let alone be performing them during school hours. You do realise I will have to punish you don’t you?”

You nodded your head, more than a little nervously.

“As you know…I like to relate your punishment to the deed you have performed. Remember that time you were caught littering and I made you clean the entire school yard?”

Again, a wordless nod.

“Well…I am going to start by humiliating you. If you enjoy touching yourself so much you can show me…”

“But sir…” you protested and really I should have backed down.

“No buts young lady. My mind is quite made up. Now…pull over that chair, remove your underwear and sit down. I want to see what you find so stimulating about that body of yours.”

I watched you, secretly enjoying your discomfort, as you remained standing still in the centre of the office, staring at the floor, your cheeks burning red.

“Good God child! Must I do everything for you?”

I stood up, my erection sore and obvious beneath my trousers and came around to the front of the desk. I dragged over a low armchair and placed it next to you.

“Lift up your skirt,” I shouted and with shaking hands you did as you were told, exposing white cotton panties, your little slit tracing a thin line across the tight cloth.

I slipped my fingers beneath the elastic waistband and drew them down quickly, exposing your beautiful smooth pussy.

“What’s this?” I questioned. “Have you been shaving your pus…your vagina?”

“Waxing sir,” you replied, your voice barely more than a whisper.

“Well…I am starting to learn what a truly naughty girl you are and that making you recreate your deviant act may not be nearly enough of a punishment.”

I couldn’t could I? I wanted nothing more than to take out my big, swollen cock and force you over my desk…press it inside of your tight little cunt, but surely I would lose my job?

I swallowed hard, my dick pleading to be removed and stepped back behind the desk, taking my seat once more.

“Alright young lady…go ahead. Show me exactly what you were doing.”

I watched as you slipped out of your panties entirely and sat yourself down on the edge of the chair. I reveled in your discomfort, your eyes glossy on the brink of tears, your cheeks burning, as you leant backwards.

“Well come along girl open your legs!” and you did so.

Your sweet little pussy was spread wide, but not quite wide enough for my liking.

“Oh come now child, wider! Hook your legs over the arms of the chair!” I instructed and it was an amazing sight to behold as you finally obeyed, slowly opening your legs as wide as possible over the arms, slipping your bottom to the very edge of the chair, your pink, swollen pussy lips parting at the last moment and displaying a thin, silvery line of moisture.

It was no good, I could not watch your show without giving myself a little pleasure too, but this would really be all I would do, I lied to myself. I unzipped my fly and pulled out my raging hard-on, hiding it from you behind the desk and slowly, I began to pump.


“Ok that’s better, now touch yourself exactly as you were caught doing.”

Tentatively, you reached your right hand between your legs and, taking two fingers, you began to slowly and awkwardly play with yourself. Your eyes were tight shut, through embarrassment or pleasure I could not tell, but I really didn’t care. The sight of you playing with your perfect little pussy was something special and I began to slide my fist up and down my cock harder still.

“Come now, do it properly for goodness sake! I know exactly how naughty little girls touch themselves you know. You will thank me for this punishment one day.”

My last instruction seemed to have switched something in your mind and I watched as you relaxed a little further back into the chair and, biting against your lower lip, you began to caress yourself so beautifully.

Your fingers slid up and down your shiny, wet slit, lubricating them with creamy juice before they slipped under the tiny fold of skin and sought out your swollen clit. You circled round and around, up and down and side to side, sometimes fast sometimes slow. I could see your body jerk as spasms fired through you.

As I fucked my fist hard behind the desk, I realised that you might actually cum for me. I could have cum too, but I knew I shouldn’t let that happen…should I?

You were moaning now, your hips oscillating and giving themselves to the tease of your fingers. Without any prompting from me your other hand slipped between your legs too and I felt a monumental shudder fire from the base of my spine to the tip of my cock as I watched you slip two fingers inside of your cunt, fucking yourself slowly, but deeply as you played with your clit.

This had gone too far already. I knew that with one word from you, I would be in trouble beyond my wildest dreams so, I decided there and then that if my career was over because of one dirty, little schoolgirl, I would make sure it was all worthwhile, make sure she got exactly what she deserved.

“Stop!” I called through parched throat and your eyes sprang open, your fingertips still inside of your pussy. You looked up at me with a nervous expression, worried that you had done something wrong. How could you have? You masturbating for me was just about the prettiest thing I have ever witnessed, but I could not possibly tell you so.

“Stop it girl! You seem to be enjoying yourself far too much. I think you are a bit of a slut aren’t you? I think you give yourself to all the boys don’t you?”

You shook your head quickly, removing your hands and closing your legs.

“I don’t believe you. Do you know what fellatio is? Have you ever put a penis inside of your mouth? Have you ever sucked on a nice, hard cock?”

Again you looked to the floor, but this time rather than shaking your head you nodded…gently and shyly.

“Speak up child, for goodness sake!”

“Yes sir” you muttered.

“I thought as much. Well…as part of your punishment, I think you should suck my cock. Is that understood?”

“Yes bu…”

“Yes what young lady?”

“Yes Sir bu…”

“No buts girl, now sit up straight.” I instructed.

I slipped my dick back into my trousers, even pulling the zip up again before standing and stepping round in front of you. I looked down and saw that your pretty little face was at exactly the right height for my cock.

“Alright then! If you enjoy sex so much you are going to show me exactly what that cute little mouth of yours can do. It may feel a little strange, sucking your headmaster’s dick, but it will be a useful lesson for you to learn. Trust me, it will be strange for me too, but I am willing to make the sacrifice for the good of one of my pupils.”

What a lying bastard I was. This had gone far beyond anything I could have dreamt of, but here you were, a beautiful young woman, completely at my mercy. I was abusing my position, I was abusing you and it felt so fucking good.

I unfastened the buckle of my belt, released two trouser buttons, drew down the zipper and dropped them to the floor. I quickly slipped my hands inside the waistband of my shorts and pulled the elastic wide over my erection and dropped them too.

I had to stifle a grin as I watched you staring at my cock, wide-eyed and nervous.

“Suck it,” I ordered and you looked up at me…your eyes dark and moist.

“Don’t worry I will help you,” I said, a little softer now and I ran my fingers into your hair, pulling your head down towards my stiff prick.

I shuddered as I felt my dick press tight against your hot, soft cheek, but I really wanted to see what your delicious, young mouth could do.

I gripped your hair more tightly now, pulling my hips back and directing myself towards your lips. You parted them anxiously as I slowly thrust forwards. Your mouth wasn’t wide enough to avoid my cock as I entered you and I exhaled a deep, shuddering breath through my nostrils as I felt your lips brush against me. When I was as deep as I dared to go - I didn’t want you to gag, not yet anyway - I relaxed a little.

“Ok child, you have been a very naughty girl indeed. We know that and this is the logical next stage of your punishment. Suck my cock just like you would one of those awful boyfriends of yours and we will forget this matter ever occurred. Alright?”

Again, I had to hold back a moan as I felt you nod against my erection, causing your hot, wet tongue to press against it.

“good girl. Now…fuck me with your mouth.”

It was pure bliss to feel your lips close against me so tightly, to feel you sucking hard against my cock, drawing saliva into your mouth so that you could give me the slippery, wet blow job you had no doubt given to so many boys before. Slowly you began to draw your head back and forth, my hands still woven into your hair, sucking me so sweetly. Once or twice you pulled a little too far out and the seal was broken, creating an impossibly delicious slurp that caused my muscles to tense and my prick to twitch against the roof of your mouth. It was hell trying to stifle my pleasure. I would be unable to soon enough, but I still had to maintain the pretence that I was forcing you to do this as part of an important lesson you needed to learn. Of course, I was doing it because the sensation of a beautiful young woman sucking my cock was just about as good as it got.

As time went on and you began bobbing your head against me faster and faster, you appeared to relax a little, you seemed to be sucking me with the intention of pleasuring me and not just because I was forcing you. I felt your tongue press against the back of my cock, applying wonderful pressure with every withdrawal. You felt too fucking good and I began to release groans of pleasure with every ass-clenching thrill that shot through my dick. I started to fuck your mouth as you sucked me, thrusting my hips into you, pulling your head onto me, all gently at first, but then harder and faster with greater abandon. A few times I heard you gag as my cock inadvertently pressed against the back of your throat, but you were a good girl, you regained your composure immediately and continued to let me use your mouth for my own selfish gratification.

My prick was so unbelievably tense now, bolts like lightning shot through me with every thrust of my hips, every deep pulsing suck from your lips. You really did know what you were doing. You would occasionally force your head back, letting my cock slip from your mouth and licking at it ravenously as though it were an ice-lolly, but always, you would return it to your hot, wet mouth and always to my thrusts.

I could feel myself drawing nearer and nearer to that inevitable moment. Pulse after shuddering pulse fired through my shaft, causing me to cry out far too loudly. I thought about cumming in your mouth, about withdrawing and shooting across your pretty little face and the image alone caused another massive shudder to erupt through me, but no…it would have been wrong of me. A headmaster should not cum down the throat of one of his pupils and besides…I wanted to fuck that tight little cunt of yours.

I grabbed your head tight, holding you in place and stopping you from sliding your lips any further. I threw my head back and drew quick relaxing breaths before looking down at you. Again, your eyes stared up at me, questioning me, wondering if your punishment could possibly be over, but as I watched you, my cock still held within your mouth, I smiled…

“Well now young lady! I can see you know exactly what you are doing which is a great disappointment to me. It just goes to show what a bad little thing you really are and I am afraid your punishment cannot end quite yet.”

I felt a little moan of yours pulse through my cock. Was it fear or pleasure? I wasn’t sure, but it didn’t matter to me either way.

I drew my cock from your mouth, one of the saddest things I have ever had to do, but quite necessary in order to move on to the next stage of your punishment.

I pulled my shorts and trousers up, fastening them loosely around my swollen cock - I hadn’t quite finished using it on you just yet - and held out my hands.

You reached up and I guided you to a standing position. You looked up at me through large, glassy eyes and I, in turn, smiled gently down at you.

“Alright now, you are receiving your punishment very well so far, but it is not over just yet. You still need to know what a naughty little slut you are. I know that disciplining you in this manner is perhaps a little childish for someone of your age, but I have a feeling it might prove effective. Now place your hands on the desk like this…”

I positioned your palms, a little more than shoulder width apart, against the edge of my desk. My hands slipped between the inside of your upper thighs as I guided your legs apart and backwards. I couldn’t resist sliding one hand upwards and stroking it across your waxed smooth pussy as I stepped away.

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Ever since I was sixteen, I found myself attracted to girls. I would sit in class and fantasize about being intimate with them. I would sometimes go to the restroom during study hall, go into a stall and quietly masturbate. After school at home, I would masturbate to the fantasies I had about some of the girls in my classes and even a few of my female teachers.This went on for two years, I was too afraid to act on my desire of being with another girl or woman. The thought of coming out...

Taboo
2 years ago
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Wake Up Sleepy Head

Even as I slept, I knew that what was going on inside my head was nothing but a dream, albeit a wonderful dream. It was my wedding day, according to my dream. Somehow I knew that the love of my life, my handsome and sexy (read, virile) Larry, laying naked against me, was to be my groom, forever, to love and to cherish, and to fuck, till death do us part. We would have children, as the Bible commanded. I envisioned the traditional girl for me and a boy for him, in no specific order. My nose...

4 years ago
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An afternoon stroll

We were walking in the middle of the woods. It was a clear, sunny afternoon. "There." You said, pointing to a tall oak tree. We were in the thick of the woods, about a mile or two from civilization. You started to kiss me, slow and tender at first, then more urgently as you started taking my clothes off. In less than one minute, I was standing in front of you--completely naked. You looked me over and smiled intently. You were disrobing as well. My eyes were glued on you. My eyes drifted to your...

3 years ago
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Secrets of Liberty Mountain Yesterdays TomorrowChapter 28

Consciousness came slowly, on the installment plan, one sensation at a time. I groaned and opened my eyes to a room full of sunshine. Dancing clusters of sparkles and glowing dust motes drifted in the sunbeams filling my field of vision as I attempted to focus and give the optical center of my brain a chance to sort out the dazzling array of visual information. For several moments I stared at the ceiling and tried to remember where I was. Naked, sirene, and warm in bed with my partner next...

2 years ago
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My first time

It was end of my semester at college. I was using Tinder to get a bit familiar with girls and with one of them I actually did. We talked a lot as I was already past my exams and one day, since we lived in same city, we decided to meet.Day of our meeting was nice, like almost every other of ending summer. She was living quite far from me, at the other side of town but I decided to take a walk and enjoy this afternoon as much as possible. Good thing that we exchanged phone numbers as I got few...

2 years ago
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Dear Cho

An old friend John wrote this for me, it's his letter.I want to hold you down and enjoy you. Normally I would tie you up so I could take my time with you, but this time I want to feel you struggling against me, trying to resist me - trying to fight your way off your bed, or your couch, or wherever you are when I decide I want to have you. I'd grab your wrists, pull them behind you and slide a hand up under your shirt so I could play with your breasts. Pretty soon that wouldn't be enough though...

4 years ago
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Amma Nanna Dengulata

Na peru sai arun. Memu oka double bed room flat lo untam. Naku age 18. Naku late ga chelli puttindhi.Tanaki ippudu 5 months.Ma nanna peru somesh. Ma amma peru supriya.Tana age 43. Tanu chala sexy ga untadi.Oka roju nenu intlo unnanu.Eveng 4 ayyindhi. Aadukovadaniki bayataku vellanu.Aa time lo nanna amma intlo ne unnaru.Ne bat marchipoya. Adi teeskuni ravadaniki intiki vella.Bayatanunchi Chooste amma ni nanna venaka la nunchi pattukuni unnadu.Amma enti andi em kavali ani adigindhi.Daniki nanna...

2 years ago
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Suhara of Curses Chapter 10 Returning Favor

The ebony staff was exactly as Jaux remembered it from Theema's artifact room. The entire length of the stave looked like a very thin cone of rough black ice, or as if someone had broken off a black stalactite. An abstract dome cage of black stone formed at the top, perfectly trapping a fist-sized purple sphere. The other end of the staff was much thinner, but still rounded out enough that it wasn't quite a sharp spear point. "Oh, that's cool," said Frey when she saw the staff lying on...

3 years ago
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Im Glad I Snuck In

I take a deep breath as I flick the headlights to my grey pickup truck off and downshift into first gear. I turn into your drive way and turn off my truck. I stick it into neutral and coast silently closer to your house. I hit the brakes and put it back in gear and pull on my e break as you carefully open your door and wait for me to climb out. I slip out of the truck quietly shutting the door and move as fast as I silently can to you. We sneak through the house and into your room. I smile as...

2 years ago
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cuckold to the gardener

Mum an Dad had split up and dad left he told it was because mum was fucking someone , but on the up side i got a lot of money as dad was very rich an he told me to get my own place an have some fun for a few years (as i was only 19) an then call him for a job if i wanted one . so that's what i did a nice house with a garden an a pool , a nice car an a sexy little blond teenage girl called Lisa .Lisa was 17 an just out of school, about 5ft 2" tall she was slim but had a nice full bubble butt an...

1 year ago
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What a ride

Nikki stopped and wiped the sweat from her brow. She looked up at the blazing Florida sun and groaned. It was only 12 o'clock noon and the temperature was already in the hundreds. She had been lost for nearly an hour now, looking for her friend's apartment, and her black t-shirt was sticking to her. She decided that if she couldn't find any familiar roads or landmarks soon, she might have to hitchhike. The decision was made for her. A dark blue mini-bus pulled up next to her and stopped. Nikki...

First Time
1 year ago
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Sex make a happy family2

Dear Friend Sanjay here again to tell you my life story. The day was 5 years back. My father left for office at 8.30 Am and sis at 9am. At 9.30 mom left for office our maid servant went to her native home. My college was close. So I programmed to watch Blue Films all the day. As soon as mom left I started the film that was incest movie. Daughter was lying on bed father entered and kissed on toe of daughter within few minute they opened their dresses and started sex after few minute brother...

Incest
3 years ago
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SpaceChapter 46

I looked at this since I was cast into the highlands. This was a great defensive weapon but I could not see how to use it. There were a lot of unknowns in this situation but the computer entities did not mind. It gave them something to do. One fact was made very evident, the mental powers had to be explored even more. This meant that sixth dimension and possibly others were behind all of these phenomena. Erica was usually near to me and said verbally, "There are still some Wikki that would...

4 years ago
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Neighborhood Boi Slut Ch 8 P2 Julies first

As we turned the corner on to our street from walking home from our shopping excursion, I saw Paul's parents car in their driveway. "Hey Julie, have you ever met Paul? I have been hanging out at his house a lot. That's where I get the pot from.""No, I knew some people had moved in but I havent talked to them.""let's go see if he has any. I want to get high"I had forgotten about being made up and wearing Julie's old clothes, it just seemed like natural. I walked up to the door and knocked....

2 years ago
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Bitter LoveChapter 9

In August 1916, the second anniversary of the beginning of the war to end of all wars, Major Frank Maloue found General John French was a pompous ass. The man was so arrogant his whole staff had a strong dislike for him. The man was fighting a nineteenth century war in the twentieth century. The artillary was accurate than before. Rifles were easier to load and fire. Machine guns were plentiful with the ability that only one could cut down hundreds within minutes. Then there were poison...

3 years ago
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Tenant Marie and Daughter Part 2

They had given John another pain killer and put him to bed. It was early so the girls went out to get clothes for morning. Marie stayed to watch John. She went into the bedroom and looked at the man that had probably saved her life and was hurt because of it. She went over and bent down and kissed him softly. She whispered “Thank you John Johnson for everything”. She pulled up a chair and sat there looking at him. Then she remembered the looks on her daughter faces and some of the...

4 years ago
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Discipline on The Croft Part 2

The MacDonald croft was on the edge of the village in a spectacular elevated spot, set back from the road and looking out to sea. I had just started walking up the long track leading up to the croft as a Land Rover appeared from one of the fields and turned towards me. Iain MacDonald leant on the door and smiled a greeting to me. “Young Angus! Fine day it is! You’re up and about early for being on your holidays, are you not? I thought young lads didn’t see much before early afternoon surely?” I...

3 years ago
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Hunter Ch 0102

Beepbeepbeep…beepbeepbeep. Hunter opened his eyes from his doze and carefully reached up to retrieve his watch from his forehead. His heart started accelerating in anticipation. Pressing the light button on the watch, he checked the time, he had 4 minutes, forty seconds to go. The altimeter gave the altitude at 34,000 feet. Putting on the watch and slipping the GPS from its strap, Hunter verified that they were still on track. Replacing the GPS, he quickly reached in an inside pocket and...

4 years ago
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Impregnated by My Nephew Pt 1

Sometimes nature has its own plans to set up situations which many times go out of control. Though many leave us with a sour impression, many a times though unwanted, they throw up surprises that even leave you spell bound. This is my experience, which I had experienced in my weak moment, but had now turned out beautifully. You may call it i****t or a swap; but who are we to challenge nature and the lust it erupts in us?I am Seema, married to Ashok, who is 34 years. I am not voluptuous, nor one...

3 years ago
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Desire Chapter 2

STANDARD LEGAL STUFF: *This is completely fictional, except as already noted persons, places, and events referred to in this story are completely fictional. *If it is illegal for you to be reading this, either because of age or some other factor, STOP READING NOW! *Lastly, if stories involving Transgender issues, young teens, sexuality, nudity, etc. are a turn off for you, STOP READING NOW! If none of this applies, sit back and enjoy. Feedback appreciated; send to...

2 years ago
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Voyeurism from an early age

As I mentioned in a previous story, I came from a village where a lot of the population knew each other / were related / friends of friends etc. Well trying to find out about sex was a hit and miss affair. Way back when I was a young teen I was a randy little bugger always trying to get a look up a skirt or down a loose top anything that could trigger a wanking fantasy.The local den for ilicit youthful smoking was a disused male/female toilet block which was gutted to leave just a shell. It was...

3 years ago
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Halloween party

Back when I was younger a friend asked me if I wanted to go to a Halloween party. I asked do I need to dress up. Of course he said. Wondering what I should dress up as, my sister came in carrying her costume. Having a kinky side I asked her it I could wear some of her clothes. She just stared at me for a minute, then said are you for real. Yes I said. Steve invited me to a party and I wanted to surprise him. She said I have to think about it. Little did I know she ran to her room and called a...

4 years ago
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A MasqueradeChapter 2

The next month was slow torture. I spent my days laying around my motel room, or sitting by myself on the bus as we rolled down the road to the next set of shows. I called her from the green rooms or from the motel every night. The sound of her voice inevitably turned me on, and I'd be like a rock at the end of our conversations. I normally shower in the morning, but I started taking them right after getting off the phone with Em so I could jack off without making a mess. She would ask me...

2 years ago
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Exclusive First Time Interview0

John Malone a self made Billionaire. CEO of Multinational Malone Industries. Texas Political Power Broker, Phililanthropist, Divorced five times, Currently married to a beautiful chiniese model, singer, Director of an International Charity, and Philianthropist. A Womanizer, Real Estate Mogul, and Defense Lawyer. This will be the lead story on our news casts and will bring national attention to you as the reporter that got the only interview. Catherine called me to arrange an...

2 years ago
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A New Old Watch 9th in the STOPWATCH SeriesChapter 63

Aboard the Pretty Penny, the crew watched in horror as the explosion jellied the four men in the water. Wikipedia says: The effects of an underwater explosion depend on several things, including distance from the explosion, the energy of the explosion, the depth of the explosion, and the depth of the water. Underwater explosions are categorized by the depth of the explosion. Shallow underwater explosions are those where a crater formed at the water's surface is large in comparison with...

2 years ago
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Monster Hunter Whore

You raise your hand to shield your eyes from the sun, not accustomed to the tropical climate. Your snow-pale skin and waistlong blonde hair stand as testament to that fact. Still, you have no doubt that your skin will stand impervious to the sun’s rays, refusing to tan or burn just as it has your whole life. Your impossibly light skin tone has gotten you quite a lot of unwanted attention, and it’s unlikely that this sunny tropical land will be any different. You stand clad in a tanned leather...

1 year ago
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Vennoa the Halfelf SorcererChapter 7

Vennoa and Tempest traveled towards Tensia in a caravan, and their trip was mostly uneventful. The caravan encountered some bandits along the way, but before Vennoa and Tempest could get off the caravan to help fend off the bandits, some armored riders had arrived, and the bandits scrambled off as quickly as they could. From the rags that the bandits had been wearing, Vennoa figured that they were likely poor and hungry. She almost felt sorry for them. The armored people had identified...

4 years ago
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Shortest actual datewith sex

I met Kimberly through an online dating site in my final year of college. Like most online dating, we emailed for a couple days and agreed to meet. Surprisingly, she didn't mind having me pick her up at her apartment. So I showed up at her door just after 5pm on a Saturday night. She opened the door and motioned me inside...since she was on the phone with someone. I stood there awkwardly for several minutes as she walked around her small apartment just talking loudly and laughing. I got the...

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