Confessions From a Boarding School Pupil - Cover

Confessions From a Boarding School Pupil

Copyright© 2022 by Drax

Episode 66: Sleeping With Sara

Pedo Sex Story: Episode 66: Sleeping With Sara - Welcome to the “Confessions From Boarding School” series. The stories contained here-in will be detailing the sexual adventures and shenanigans I got up to and involved with while I was at and after I left boarding school.

Caution: This Pedo Sex Story contains strong sexual content, including Ma/ft   mt/Fa   Teenagers   Blackmail   Coercion   Consensual   Drunk/Drugged   NonConsensual   Pedophilia   Rape   Reluctant   Romantic   Teen Siren   TransGender   School   Cheating   Incest   Daughter   Uncle   Niece   Nephew   Grand Parent   Rough   Spanking   Harem   Interracial   Black Female   White Male   White Female   Oriental Female   Hispanic Female   Indian Female   Anal Sex   Massage   Oral Sex   Tit-Fucking   Voyeurism   Babysitter   Public Sex   Small Breasts   Teacher/Student   Prostitution  

My next sexual encounter came two days after I’d used and abused Christina. I had called in the favour Eliza owed me and had taken the next day off wherein I’d just laid on my bed stark bollock naked, enjoying a few cold sodas and surfing the net on my iPad. The day after my day off was when I had my next sexual adventure. It was just after breakfast and I was enjoying a decent cup of hospital coffee when Dr. Hellruy came in to see me. “And how is my favourite patient this morning?” she asked with a smile, to which I replied “I’m rested and ready to get back to work my sex doctor”. She smiled and replied “Well, that is very good news to hear as I have a special one for you”.

Now when she said things like or similar to this to me in the past, it always meant that she had a specific woman she wanted me to see, not that I minded. When she asked me this, the women were always so very hot or they were for me to smack around and generally use and abuse. “So, what’s her name?” I ask “And what does she want me for?”. Eliza smiled as she sat on the end of the bed and told me “This one is different as you will soon see”. She gets my iPad and logs onto the email; she loads an email from the day before and shows me the picture. “Her name is Sara Anderson and she was admitted two days ago” she tells me “She’s 14 and like you, she is very sexually active”.

The girl in the picture is skinny and has a light tan she is laid on a sun lounger and is wearing a blue and white bikini. She has an impressive chest for a girl her age which my gaze repeatedly fell upon. “So she wants to use me?” I ask, wondering why a hot 14 year old girl would need to see me. “She needs to be with someone her own age” Eliza tells me “So would you mind seeing her?”. I looked at the picture once again and replied “Only because you asked me so nicely”. She reached under the covers and gave my erect cock a squeeze and said “She’s already in the office waiting for you”. She got up off the bed and headed for the door, telling me “This will be new for you, seeing someone your own age”.

I got out of bed and replied “New but oh so enjoyable”. As she left the room, I grabbed my lanyard and got my sandals on. I put the iPad in the drawer and left my room. As I left the ward, I was pleased to see that the nurses were back at the station and were once again checking out my ass as I left. As I headed down to the office, I actually found myself feeling a little nervous. Sara would be the first girl my own age I’d fucked since I did that retard Vanessa, not that I was complaining about Sara’s age. I was enjoying my job as ‘Hospital Fuckboy’ and enjoyed meeting and fucking the women and girls that came to see me. But I had to admit that it was going to be nice doing someone my own age.

After going to the pharmacy to buy condoms just in case she wanted me to use them, I reached the office. I knocked on the door and a voice from inside replied “It’s open Jay”. I opened the door and stepped in and almost choked when I saw Sara. She was sat in the armchair wearing the same bikini from the photo. “Wow ... you look even better in person” I say as I close the door “Your picture does not do you justice”. She smiles and replies “I could and will say the same about you”. As I shake her outstretched hand, I can’t help but stare at her slim and hot body. “Enjoying the view?” Sara asked with a smile as she posed with her hands on her hips. “Yes indeed I am” I reply “And I did not mean to stare”.

“Stare all you want” Sara says with a smile “So long as you extend me the same courtesy”. I nod and say “You can stare all you like”. So for a few moments we just stare at each other. “If you’ll excuse me, I just need to go to the bathroom” I tell her, to which Sara replies “I’ll be here waiting...”. As I turn to head into the bathroom, she sees the condom packet in my pocket and says “You won’t need them, I want you inside me not some piece of rubber”. I take them out of my pocket and put them in the drawer before I head into the bathroom. I move to the sink and swill my mouth put with a glass of water, my throat had become dry due to my slight case of nerves.

I swallow the water and down two more glasses. There’s a prize out on the couch waiting for me, a hot 14 year old girl waiting with wide-open legs. I leave the bathroom and find that Sara is now laid on the bed waiting for me. “So, what do you want to do first?” I asked, to which she replied “Let’s just have a kiss and a grope; after the past few weeks I’ve had that will be just what I need”. I nod and reply “If that is what you want to do then that is what we’ll do”. I get on the bed next to her, we wrap our arms around each other and we begin kissing and groping each other. As I’ve mentioned previously, Sara was the first girl that was my own age I’d been with since Jennifer brought her retard daughter in.

As you all know, she brought her in for me to fuck not long after I was admitted to hospital. Kissing and feeling up a girl my own age for once felt so fucking good. “Oh god this is SO much better than my dad” Sara says, breaking the kiss. “Your dad?” I ask, trying to hide how turned on I was by what she’d just said. “Yeah, I lost my virginity to my father” Sara replied “I was drunk so didn’t remember much of it until recently”. I frown and ask “What happened recently?”. She hesitated, then said “My asshole father set me up to be raped by one of his friends; that’s why I was admitted to hospital”. Hearing that she’d been fucked by her father and then raped by one of his friends turned me on.

But as I did not know how she felt about it, I did not react. “You father is an asshole” I say, stroking he face gently “Doubly so for setting you up to be raped”. What I had just told her was indeed the truth; her father was an asshole for fucking his own daughter and an asshole for setting her up to be raped. I was so turned on by the thought of two old men having their way with the hot young teenager. “That’s so nice of you to say” Sara said warmly “It’s nice to hear that from a guy my own age”. We then resume kissing and groping each other. As you know, I’ve had sex with women who are way older than me which I’ve enjoyed so fucking much, but the thought of older men having their way with Sara.

Be it done to her willingly or unwillingly, turned me on so much. As we kissed, I slipped my hand into her bikini bottoms and gently rubbed and squeezed her firm teen ass. I moved my hand from her bikini bottoms and onto her flat teen belly which I rubbed gently. I then slid my hand up her front and into her bikini top, gently rubbing and squeezing her tits. “Oh god Jay, I want you” Sara tells me, breaking the kiss “I fucking want you inside me right now”. I smile and reply “Never argue with a beautiful girl”. We get off the bed and get out of our clothes then get back on the bed, and let me say that she looked absolutely fantastic naked. I could see why her father and his friend had both had to fuck her.

“Fuck me Jay” Sara says as she lays back and opens her slim legs “Fuck me and cum in me”. I positioned myself between her legs and placed my cock at her cunt with just the tip inside. She wraps her legs around me as I plunge my cock into her. After fucking so many women and girls who were always so much older than me, fucking a girl who was the same age as me felt fantastic. Her cunt was nice and tight, and I smiled and began to slowly move my hips in rhythmic thrusts. As we fucked, she moaned gently and said “You feel so much better than my dad”. She lets out a tiny whimper of pleasure from her throat as I enter her. “Oh GOD thus feels so good to have someone inside me who isn’t my dad” She says.

I kiss her neck and say to her “You are so beautiful Sara, you should be treated better than how your dad treated you”. Truth be told, I was jealous of her dad taking her virginity but there was nothing I could do about that. For the next few minutes, we fucked in silence with only the sounds of our mutual grunting and groaning in pleasure. We broke the silence occasionally as we kissed madly, seeing how far we could get our tongues down each other’s throats. “You feel SO tight” I say, breaking the kiss whispering in her ear “I’m not going to last long inside you”. Sara replied with “Keep going as long as you can”. I was determined to last as long as I could inside Sara, if she had been any other woman I would have cum by now.

As I thrust in and out of Sara, the tightness of her cunt in comparison to the other women I’ve fucked was not lost on me. Now don’t get me wrong, I love fucking other women as part of my “Hospital Fuckboy” duties, but after fucking so many women who were older than me it felt absolutely fantastic to fuck a girl who was the same age as me. If her cunt was this nice and tight, I wondered if her bum hole would be just as tight. I shut my eyes and began to thrust into her with increased pace, knowing I would not last much longer. After a few more seconds, I grunted and called out “Oh god, I’m going to cum”; Sara replied immediately with “Cum in me Jay, please cum in me...”. And just a second later, that is what I did.

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