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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John and I had just started our senior year when the following took place. Everyone that took part in this event was over 18. John and I both turned 18 when we were still in the 11th grade. John had a good job working in his father’s company back in high school. He was always buying me new outfits and makeup that he liked me to wear. These events took place in the mid-80’s. We both loved singers like Cindy Lauper and Madonna. Most of the stuff he got me matched Cindy Lauper’s style. I went from...

2 years ago
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Classroom Ass Tease

Jessica chewed the end of her biro. She was trying to act coquettishly but felt nervous. Jessica was not the type to become infatuated but here she was sitting at the front of a crowded lecture feature making eyes at her college tutor. She crossed her legs for the fourth time and undid a button on her blouse. She glanced at his crotch for any sign of a reaction there but saw none.Disappointment and frustration had led her to this out of character course of action. Jessica's flat mate Casey had...

1 year ago
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A Bad Day At The Office

Emma really couldn’t understand how she ended up in this embarrassing position. Here she was a full grown women standing in her bosses office with her nose pressed against the wall, her hands on her head and her well spanked bottom on full view for anyone who entered the office to witness. Standing at just shy over 5’ 2’’ she was perfectly proportioned. She had a nice firm backside, tanned slender legs and pert breasts. Her shoulder length brunette hair and her stylish dress sense gave her a...

Spanking
3 years ago
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Confessions of a chronic Masturbator

Ever since I was a k**, i heard stories from the other girls in school about the penis. To me the penis became somewhat of a mystery that I wanted to be a part of but never had the courage to be a slut like the others. Mostly because I was overweight and did not have a great clothing sense.I went online almost everyday and checked out pictures of guys showing off their "dicks", It was amazing how everyone seemed to have a different kind. Some thin and long, some short and thick, some bent like...

2 years ago
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A Fresh StartChapter 86 Fall 1984

I came home from the office on Friday a week later and was greeted at the door by my son. “Hi, buddy, what’s up?” “Mommy’s crying,” he told me. “Mommy’s crying? What’s wrong?” “I don’t know.” “Did you do something?” I asked. “I don’t know,” he repeated. “Did I do something?” “I don’t know.” I just nodded down at him. “Okay, I’ll go talk to Mommy. I’m sure we did something.” He headed back to the living room, and I followed him. I dropped my briefcase in the living room, and then went...

2 years ago
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SandcastlesChapter 5

" ... But I get to make one condition to be specified only after you agree. Take it or leave it," I said in a last ditch effort to keep my position of superiority, even if it was imaginary. I was praying she would leave it. There was no fucking way I could last that long in that moist steaming cauldron of her sexy mouth, so hot and moist, tight ... Stop it, you idiot! You'll lose before you start! "OK. When do you want to lose?" she asked simply Oh, shit I'm a goner. Maybe if I go...

2 years ago
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Shipwrecked 5

As I was getting up, JoanI and Jessica walked into the hut and announced that they wanted to go fishing. I looked at the two of them, blinked, and shrugged my shoulders. They picked up the tackle gear and poles and headed out to the south beach where we had found good fishing before. I walked out to the beach for a quick rinse and then made a little breakfast. I had found some coffee bushes during a walkabout and picked enough beans to keep me in coffee for a bit. I put some on the fire and...

3 years ago
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Consensual Sex

“Mr. Chandler!!!!” Todd turned at hearing his name called. A sixteen year old beauty was facing him. Wholesome good looks, perky breasts, and a tiny waist perched atop a delightful bubble butt, tapering down to a pair of gorgeous gams, aptly displayed by her Daisy Dukes. Her low slung shorts exposed her hip bones, and her belly shirt showed off her tight stomach. Her belly button peeked out of the bottom of her shirt. She showed off a deep summer tan. But not that he would notice that sort of...

2 years ago
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Disparate HousewivesChapter 31 Car Problems

Georgia frowned as she approached her car. When she parked it, her SL500 had been the only car in the aisle of the mall, and she had been able to park nose-in in the first non-handicapped spot near the entrance. Now she was boxed in on three sides. In front of her were three cars, on her passenger’s side was a gigantic oversized black SUV with tinted windows, and on the driver’s side was a monstrous and dilapidated white van belonging to a local plumbing contractor. Georgia slid between the...

2 years ago
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Nice surprise when you get home from work part 4

Giggling as you kissed me, I tried to wrap my arms around your neck. You stopped me. “No.” You said shaking a finger in front of my face. I gave you a confused look. You had got off of the bed and moved to the dresser. “What are you doing? I asked you, trying to see what was in your hands. “You are gonna with you were nicer to me.” You turned to face me with a grin on your face. You held in your hands a few neck ties. You walked over to the bed, climbed on me and started to tie me up; one...

Straight Sex
2 years ago
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My Second Encounter with Kat Kat Makes Dessert

It’s late Tuesday morning and I am lying in bed recounting the events of Monday afternoon and I still can’t believe what I had gotten myself into with Kat. All those fantasies I had about her were nothing compared to the real thing. Just then my cell chirped with a text message from Kat. “Just wanted you to know that I’m thinking of you” was all it said. A few seconds later my phone chirped again and to my surprise there was picture of Kat’s sweet pussy all wet with a finger rubbing her clit in...

3 years ago
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Sex under Duress

It had been a very wet July back in 1993. It rained almost every day during that month. So when there was an afternoon that was sunny, I decided to take advantage of it. I went golfing! I skipped my summer class (so did my professor) and drove out of town to a small nine hole course. It was one of those small community golf courses that was very cheap to play. So I wasn't surprised that only one car was in the gravel parking lot as I pulled in. I walked in and a familiar face greeted me through...

3 years ago
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The Santa

An Edgar Allen Poe-m for Christmas Copyright© 2005 Russell Hoisington (With deepest apologies to the author of the original.) Once upon a midnight, dearie, while I sat with eyes so bleary, Viewing many a strange and curious website of forbidden lore, While I nodded, lightly napping, from the fireplace came a tapping, As of someone gently rapping, rapping at the damper door. " 'Tis some rodent pest," I muttered, "tapping at my damper door; Only this, and nothing more." Ah,...

1 year ago
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BlacksOnCougars Mckenzie Lee 10212022

Mrs. Lee really likes the young man who is dating her daughter. Now if only he would fuck her in the ass. You see Mrs. Lee knows a young girl will stray if you are not properly laying that pipe. Especially when it comes to the poop chute. That’s one way to make sure she does not go off straying for some strange. You show a girl you can properly ass fuck her and she never leaves you. Being the good mom she is McKenzie lets Lawson know in no uncertain terms she is going to train him on how...

xmoviesforyou
2 years ago
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Moments in a LifeChapter 17 Zo

Things in general were going well for Bob Lacy. He didn't have any complaints. Well maybe there was something that was bothering him and that was the relationships he was having with women. He was having dates and having sex with women but in thinking about it that's only what is was, sex. It was pure physical attraction to a member of the opposite sex. The women he had been with he assumed had this same physical attraction to him as well. Some had hinted they wanted more in a relationship...

4 years ago
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Twins n best buds IX

Since a lot of people wrote and told us we should keep the stories shorter thats what we are going to try and do. Let us know what you think. The next morning we were awakened around 10:30 when the phone rang. I answered it. Since it was Gavin’s dad I threw the phone at him and he woke up when it hit him. As soon as he finished talking he threw the phone back at me and said he had to get going because his parents were ready for breakfast and then they were all going out to see some...

4 years ago
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A Flash of Moms FleshChapter 3

For a moment Sarah couldn’t move. Finally, she closed her legs, tugging her dress down and sitting up, her face flushed with the glow of her orgasm, but also with the embarrassment being caught. Karen, too, had gone stiff. She had been in the process of smoothing her tight skirt over her curvy hips and legs and when Jimmy came in unexpectedly, she had whirled to face him, her skirt still about her hips. As his mother tugged her skirt down, Jimmy’s eyes swung to his aunt and he saw her...

1 year ago
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The girls at Baker House

The girls at Baker House are at it again, they just love to distroy young guys gonads !(Ref. see “New Collage Wrestling”) More Crazy Frat Parties The wrestling parties had all but died out, the local police and the collage administrators really started to crack down on them. They were getting pressure from the parents of some of the boy’s coming home for the...

2 years ago
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I fucked my Sexy Sister8230

Hi I am Vinaya from GAO and my sister Amrita she is very bold, beautiful and sexy girl she model and burning actress whom I fuck and I got really taste of her. I am 18 and she is 22 so I got taste of really sexy girl. After I fuck her I know how hot she is and why guy are behind her. I got the true pleasure of life One day I was sleeping in the bed in noon and she also come before she came I had been already slept and she came and slept in the same bed but difference is half feet. I don’t why...

Incest
3 years ago
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Life in the NeighborhoodChapter 12 Gregs New Job

About mid January Tracy announced to me that she could not continue coaching the cheerleaders and was taking maternity leave. It was time for me to take over for her. It was a good idea she had, earlier, for me to phase in my involvement with the squad so my taking over would be smoother. By that time I knew every one of the girls by name and their capabilities. I did not plan any changes in organization so all the girls knew exactly where they stood. The flirting and mischief by the...

4 years ago
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What I cant give my wife

I turn the Tv off and go into the bedroom ,its very late and I am so tired I lay down and look over at her pillow and smell her lingering body lotion scent and smile and wonder what she is doing ,my cock stirs but Its too sore to jerk off again so I push the thought from my mind and drift off to a deep sleep.Something wakes me and I see a soft light when I first wake up after I clear the cobwebs I realize Lori is home and shes in the bathroom ..I hear running water and in a few minutes she...

2 years ago
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Little sis and I part 4

Billy and his sister continued making out when all of a sudden they heard a car pull up in the driveway. “Shit!” Billy said, “It’s been two hours already? Phoebe, go take a shower and I’ll clean up here.” Phoebe ran across the hall to the bathroom and started the shower. The warm water felt good on her slim frame. She used the shower hose to massage her burning asshole. It helped a little. When she was done she got out and noticed “no towels!” Someone had put them all in the laundry and not...

4 years ago
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Blacksmith And A Lady

It was a cool spring night and the trees whispered to each other in the wind. James listened as the fowl of the woods sang their beautiful song to the night. He loved going out into the woods at night and taking his bath in the stream while listening to the birds sing.  Stripping off his blacksmithy’s clothing, he lowered his naked, muscled body into the water. It had been a long day at the shop, with five horses needing to be shod and he had needed to finish off the ten sets of armour complete...

2 years ago
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Taking The Thompson Women 2 by loyalsock

She tried to regain her footing. "So... What's that?" She asked; pointing to a bag I brought with me."A surprise." I replied."For me?" she asked hopefully.I nodded, and walked up to her bedroom. There was no talk of studying. I sat down on the bed, and handed her the bag. Curious, she opened it, and inside, she found a light blue swimsuit. "This is beautiful!" She gasped."Its for you." I said, smiling."Thank you!" she said, and she gave me a hug and a kiss, she was already u*********sly...

1 year ago
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Noras Tale 5 Dawn Breaks and So Does Lauren

As it turned out, Levi didn’t get his hands on me for awhile, not that either of us was happy about it. I couldn’t allow my weekend experience to bleed into my school week. Those two days had been a blast – a taste of what my summer might be like after graduation, but I had too many responsibilities to be fooling around during the week. After the craziness of it all, my Monday was completely mundane. I hadn’t even had the time to flaunt myself for Levi in the morning, as I had swim practice...

Bisexual
2 years ago
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Magical Hearts chapter 5

I held Isabels hand as I heard the beginnings of Justins magic, I had time to grown but not much more than that before I am awaken in the morning. The Wedding Day: Chapter 5. Isabel is kissing my hand. She says to the curtain, That was the longest night of my life, even with Justin putting us to sleep. I chuckle and say, I was thinking that just before Justin begin his sleep spell. That was odd I remember dreaming one normally does not dream under a sleep spell. Isabel asked, What did you...

1 year ago
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InterracialPickups Coco Lovelock 12082022

Ray loves going to resorts in Mexico and finding girls to film on his phone. Take today for example. He finds a wayward lamb away from the flock lounging out by the pools at the hotel. He walks up with his phone filming her as he finds it to be a quick way to break the ice. After all – every gen z loves being filmed. We are in a world of narcissism and self celebrity – just a million clicks away from going viral. Is anybody under 30 not a podcaster or influencer? Now when Ray starts...

xmoviesforyou
2 years ago
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  • 17
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Schoolgirl Slut

Introduction: Emily lived in a suburban neighborhood where she was very well known by all the men. She lived with her father Rick, her mother Caren, and her two older brothers Mike and Tim. Rick, her father was quite the popular guy on the block. He held weekly poker games, block party barbaques, and football parties regularly. All the men were very fond of Ricks little girl who was shaping into quite a beautiful women. It was summer time and Emily was going to be a freshmen in highschool. She...

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