The Headmistress's Daughter free porn video

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I was excited. I had moved with my family to a new town, which meant a new school, new friends, and new girls. At seventeen, I had all the bravado I needed to get the girls I wanted. Being quite a pretty boy and having been blessed with a larger than most package helped.

The first day of school came and I had a meeting with the headmistress. She was a beautiful woman in her forties and I found myself getting hard as we spoke. She had all my papers and evaluations from my last school, so I wasn’t worried. I wasn’t a straight A student, but I was higher than the average.

There was a knock on the door and a beautiful girl walked in, she was amazing.

“Hey mom, I'm about to head into class.”

The young girl gave the headmistress a peck on the lips and walked back out the door.

“That’s my daughter, I believe she is in the same class as you. She’s a good girl, you’d do worse than become friends with her.”

She gave me a gleaming smile and then sent me on my way.

I found my way to class and got comfortable. I happened to be sitting next to the headmistress’s daughter and she gave me a wide smile. I somehow knew she was going to be a good friend and could tell that her mother, our headmistress wouldn’t be opposed to it.

-----

The day went by slowly and soon it was time for PE. It was interesting, unlike the other schools I had been to, where there were separate changing rooms for the girls and the boys, the showers seemed to be open plan. There was a sort of partition between the boy and the girl’s showers, but you could easily walk into the other showers.

And so once everyone had finished PE and had their shower, I found myself alone. I loved showers and was alone in my own world for a minute. Then I heard moaning, I looked about and saw the small partition between the showers. There she was, Jane, the headmistress’s daughter, sitting on the floor of the girl shower, naked and masturbating.

She saw me right away and smiled. She didn’t bother stopping. She just stared at me as she carried on probing her wet pussy with her fingers. I could not help but get hard. I decided I would join her in masturbating. I pulled down my shorts that I was wearing and started to stroke my already rock-hard cock.

She smiled up at me and motioned that I should come and join her. I sat on the floor next to her and started to jerk off. She seemed to love it and finger fucked herself as she watched me.

I watched as her orgasm washed over her like a tidal wave, making her whole body shake. As she calmed down, she looked at me and smiled.

“Wanna fuck?”

I smiled and nodded.

“Cool, but you have to be rough with me. I like to be treated like the slut I am.”

I smiled and stood up. She got to her knees in front of me and grabbed hold of my crotch. I felt her lips wrap around my cock and it was one of the best feelings ever. She was a great cock sucker and knew what she was doing. I grabbed the back of her head and started to fuck her mouth. At first I was gentle, but with some encouragement from Jane, I started to fuck her mouth hard, forcing my cock down her throat and making her gag.

Her hands gripped my ass as she looked up at me with a mouth full of cock. Gone was the innocent looks, replaced by the look of sheer lust. I pulled my cock from her mouth and helped her to her feet. I gently pushed her up against the wall of the showers. Pushing my cock into her waiting hole, I gently grabbed hold of her neck and started to pound her pussy as hard as I could, watching her eyes roll back in her head.

Me holding her by her neck seemed to turn her on more than the actual fucking, so I squeezed gently on her neck, making her get short of breath. I kissed her on the lips and gently slapped her face, which too seemed to excite her.

As I fucked her, pinning her to the wall, I grabbed and caressed her body as I slapped her gently on her face and breasts. She seemed to really enjoy it and kissed me back while begging to be treated roughly.

I pulled my cock from her pussy and turned her around. I wasn’t thinking about her ass, but she right away spread her butt wide open for me. It looked so good that I couldn’t deny her. I pushed my cock up her ass and felt her push back against me, so my cock was all the way inside her ass. I pulled her back against me by her throat. And started to kiss her neck. I kissed her neck as my hand was firmly on her throat and my spare hand roughly caressed her breasts.

I could see the red marks on her breasts and neck as I started to fuck her for all I was worth. Her groans and whimpers echoed around the shower room and I couldn’t help but kiss her neck harder, making my mark on her neck.

Jane pulled away from me. Getting to her knees and taking my cock into her mouth. She seemed to savour the taste of her ass on my cock, told me how good her ass tastes. She stood back up and once more she spread her ass. It looked so good that I couldn’t just fuck her ass, I had to play with it.

I pushed two fingers in her ass, making her groan. I started to finger her butt, mesmerized how easily it took my fingers. I gently pushed another finger in, fingering her harder. She seemed to enjoy it too, pushing back against my fingers. I decided to see how far I could go and pushed the rest of my fingers into her ass. I could feel her body shake and her ass seemed to grip at my fingers. She really got off on being anally fingered and I could feel her body shake as she had another orgasm.

“Enough playing with my ass. Fuck me hard.”

I pulled all my fingers from her ass and replaced them with my cock once more. I held her around the waist as I started to slam her ass with my cock. She groaned and let me have my own way with her, fucking her for all I was worth.

She pulled away from me and once more licked my cock clean.

“Okay, I want you to finish up in my pussy. Fuck me hard and cum inside me.”

I smiled and pulled her close. I slipped my cock inside her pussy and lifted her by her ass. I pushed her up against the wall and started to go to town on her pussy. She started to groan and whimper as I fucked her as hard as I could. Her body seemed to shake, and I knew if she had another orgasm while I was inside her I wouldn’t last.

We kissed roughly, her biting at my bottom lip. I could feel myself getting close and grunted as I could not hold back any longer. I shot my load deep inside her tight hole which made her cum once more. We held each other close as we both came down from our sexual high. She kissed me passionately pulling me close as we both slid to the floor.

I pulled away slowly, my cock slipping out of her pussy. We both just sat there looking at each other. I laughed, she looked a mess. She had red marks all over and her hair was dishevelled. She stood up and to my surprise spread her pussy lips and started to pee. It was a long stream of golden liquid and I could feel my own piss rising in my crotch. As I started to pee, Jane grabbed the base of my cock, making me pee on her. She seemed to really enjoy my hot piss on her face.

After we finished relieving ourselves, Jane turned on the water to the shower and we both washed each other thoroughly. She took care in washing my cock and balls, as I made sure her pussy and ass were squeaky clean.

As we separated to go to our respective changing rooms she turned to me.

“Jason, wanna come home with me after school? Mom always stays a bit later, so we’ll have plenty of time to fuck again.”

I nodded and smiled.

-----

After school, we went back to her house where we had sex in her bedroom. We went back downstairs in our underwear just as her mother walked in the door. My headmistress gave me a huge grin.

“I told you she’d be good for you.”

What a great first day of school.

 

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When we entered the dining salon, all conversation stopped. I had changed from my travel clothes earlier, but was still in black. Esther was in a peach colored evening gown. As I said before, she was ravishing. Martha and Hatty walked behind us in their evening gowns. It was plain that everyone wondered who this girl was with the Royal Executioner and the Guild Master for companions. Certainly most of the apprentices and the other Guild members had not met, or been introduced to Esther. None...

2 years ago
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EstherChapter 2

“Are the statements, that the Lord Executioner made, true?” the Village Chief demanded sternly. “Yes, Un ... Uncle,” the young man finally answered very quietly. “A week in the stocks,” the Village Chief pronounced, “and the same for those two friends of yours.” The Village Chief then turned to me to apologize. “I am sorry I doubted you, Lord Executioner. It would appear that I need to pay closer attention to what is going on with the workers in the fields.” “An excellent idea,” I replied,...

1 year ago
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Theresas Deportment

"Language Theresa!" "But Mrs. Bradshaw, I only said..." "Hush Theresa, I will not have such rude vernacular spoken in my boarding house! Also, kindly remove your elbows from the tabletop. More over, the fork was placed on the left side of your plate for a specific reason." Theresa blushed as she looked around at the other five girls, some of them putting on airs. "I never ate before with my left hand Mrs. Bradshaw." "You are a student now in the most prestigious Ladies College in...

2 years ago
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Esther III

Esther III ? by: TamarainRubber Even though we knew we were going to be late for Lisa's party, we couldn't keep our hands off each other. For the next hour or so we grabbed each other like wild cats in heat. Her breasts heaving and her lungs gasping for oxygen, Esther still found the energy to warn me not to cum. At some point she did pull my cock out from behind my rubber bloomers and shoved every inch into her mouth. The clothes she had dressed me in only made me harder and,...

4 years ago
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Katherines Style Part Two

The next day I was in full Katherine mode from the moment I unlocked her door. I greeted Sunshine just like Katherine did, using the same tone of voice and gestures. Of course Sunshine reacted just she would with her female owner. As soon as I took her for a short walk and fed her, I went straight to my bedroom, well after the prior day I felt so much more comfortable there, I wanted it to be my bedroom. I took a shower and shaved everything again. I didn't know how I was going to...

2 years ago
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Esther IV

Hope you like Esther's latest installment! ESTHER FOUR By TamarainRubber I obediently followed Esther down the long narrow hallway that led into an enormous room filled with the sounds of clinking glasses, soft whispers and a bevy of leather-clad women and men dolled up as maids, rubber babies, and crossdressing sluts like me. Strangely enough (and very much to my pleasure), there was little if any evidence of the S&M parties I had only read about, but never...

3 years ago
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Katherines Style Part 3

The front door opened and again Frank came in, a little less dramatically than the day before but no less intimidating to me as I felt timid and weak dressed in my mother-in-laws things. Frank was half expecting me to be dressed as my normal slouchy male self, ready to put a stop to all this, but he was happy when he saw I didn't have the fortitude to do that. He actually smiled at me, "There's my little wife. That dress looks nice on you." I smiled back not knowing what to do, it...

4 years ago
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Absinthe makes the heart grow fonder

Caroline dumped her books so loudly on the table that it caused Mike to look up momentarily from his laptop.“Hi, Caroline, I take it the tutorial didn’t go so well?”Caroline slumped onto the chair opposite him.“The pompous bitch basically told me to start again.”“Look I know nothing about art, I don’t even know what I like, but I do know that you know your stuff. Why don’t I get you a drink and we can talk about something else.”As Mike placed the two pints of beer down on the table, Caroline...

Fantasy & Sci-Fi
3 years ago
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Mother and daughter

Recently while I was on a business trip for a few days I had what was a rather unexpected but delightful experience. I was staying in one of the new suite hotels and was traveling alone planning on spending my time at company meetings and watching tv in my room. I went down to the lobby to get a drink as the hotel offered free cocktails between 5:00 and 7:00 . As I had little to do and knew not a soul I began to wander around the lobby watching the people as they milled around and socialized....

3 years ago
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Esther stone

Esther sat on the side of the road, freezing, she feared that if she didn't find a place to stay soon, she probably freeze to death.Lately life had been pretty fucked up for Esther, both her parents had die before she could barley talk, and this year she had run away, because her foster parents were abusive.She had no one now, and was stranded on the side of the road. Esther picked herself off of the ground and started walking again, until a huge house came in sight. "Warmth." She said, she was...

2 years ago
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Mother and Daughter

Mother and daughter were roughly dragged from the back of the white van. Both had their hands bound behind them with strap ties and duct tape was plastered over their mouths. Their eyes quickly took in the surroundings. It looked like a large abandoned warehouse, dark, dirty and cool. Jill, the seventeen-year-old daughter, was dragged over to an area where two men were busy untangling numerous ropes. Ruby, the forty-two-year-old mother was herded over to an area about ten feet in front of Jill....

2 years ago
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Esther Stone part 2

When Esther had woken up the next morning laying next to Romeo, she almost freaked out, but the all of the memories from the night before flooded into her brain."Oh god." She sat up and looked at Romeo's sleeping figure next to her, his teal hair was tossed about the pillow, and he chest heaved up and down, Damn he is so hot, she thought, I acted kind of crazy last night, her face burned, ugh, what the fuck was wrong with her these days? She felt Romeo's body shift a little and her heart sped...

4 years ago
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Esther II

Esther II By TamarainRubber I had found the woman I had been dreaming about, hoping she would be my lover for years to come. Esther was the first real lady I had encountered who actually seemed to be honest about wanting to share my passions. I prayed that I would not be disappointed. From how she reacted, I didn't think I would be, but I was the planet's biggest skeptic. For the past four hours, Esther made me try on an incredibly sexy collection of female fetish wear that...

4 years ago
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Athena Goddess of Wisdom

Chapter 1 – The Birth of a Goddess Zeke cracked his knuckles and spread out his fingers. They touched the black glass in front of him and the desk lit up. A white keyboard appeared and he started to type on the touchscreen desktop. His fingers bounced around the screen, typing across the keyboard of light. You see, Zeke was a genius beyond his years. He was currently eighteen and in his second year of college. His masterful mind crossed with a youth of video games made him into one of the...

2 years ago
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Mothers Little Helper Her Mothers DaughterChapter 8 Her Mothers Daughter

Her Mother's Daughter Chapter One "Mom's not back," I said and it wasn't a question. My dad just frowned at me and he looked like he hadn't slept all night. The last two nights, I should say, since Mom had left Saturday afternoon and it was Monday morning now. He'd called everyone, but the only one who had seen her was Stacy and that had been at a dance club downtown, sometime before midnight. Stacy had Mom's purse though and she was going to bring it by on her way to...

2 years ago
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Father daughter

You decide the age if you want to know the age range just in box me Whatcha building?”I had not heard or seen her enter the garage, but when I heard the question and looked up from the board I was sawing, I recognized her immediately. I did not know her name, but I knew she had moved in across the street a few days prior. When I’d first noticed her playing in her front yard, I was struck by her youthful beauty. Just a few hours before she showed up there in my garage, I had watched her playing...

1 year ago
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Theresas Deportment

"Language Theresa!" "But Mrs. Bradshaw, I only said. ..." "Hush Theresa, I will not have such rude vernacular spoken in my boarding house! Also, kindly remove your elbows from the tabletop. More over, the fork was placed on the left side of your plate for a specific reason." Theresa blushed as she looked around at the other five girls, some of them putting on airs. "I never ate before with my left hand Mrs. Bradshaw." "You are a student now in the most prestigious Ladies College in this country...

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