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The Headmistress's Daughter

"starting a new school year could be fun."

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Competition Entry: Back to School

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.

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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.

 

Published 
Written by Sholbin83
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