Confessions From a Boarding School Pupil - Cover

Confessions From a Boarding School Pupil

Copyright© 2022 by Drax

Episode 18: The Last School Hump

Pedo Sex Story: Episode 18: The Last School Hump - 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  

I was in the clubhouse enjoying some peace and quiet and reading while sipping a cup of black coffee. Around midday, my peace and quiet was interrupted when Anna came into the clubhouse. She said she did not have a lot of time but if we hurried then we could have a ‘quickie’ before she had to be back in class. I stood up and said that we should get going and she agreed. She pulled her skirt up, panties down and I put my arms around her, pressed my lips tightly against hers, and pulled her tightly against me and squeezed her tight little ass. Despite being Ariadne’s boyfriend, I wasn’t going to turn down a quickie. I broke the kiss and told her to bend over the back of the armchair.

She obliged, turning around and bending over the back of the chair. I took a few seconds to admire her cute little ass. As I dropped my trousers and pants, I told her that I was going to fuck her from behind to which she told me that I could take her how ever I wanted. I fisted my prick-tip to her pussy from behind and nestled the head between her twat lips. I wiggled it slightly to moisten it with her cunt juice. She watched as I slowly drove it in, and Anna groaned as I entered her. I grabbed her waist with both hands, moving her back and forth, as my cock sawed her sweet pussy. I reached around and gently rubbed her flat belly before wrapping my arms around her slim waist and hugging her from behind as we fucked.

As I was still turned on from being with Ariadne, it did not take me long to start to feel the familiar tingling in my cock. This meant I was soon to cum. I stood up and held her waist as I increased the speed of my thrusts, which elicited increased and louder groans of pleasure from Anna. I gritted my teeth as I tried to hold off Cumming for as long as I could, but eventually I could not hold back any longer. I told her that I was going to cum and she told me she was going to do it first and a few seconds later, she cried out in pleasure as she came. As Anna was overcome with pleasure, I could not hold out any longer as my cock exploded and shot its load of hot cum up into Anna. I continued thrusting until every drop of my baby-juice was had left my cock.

I continued thrusting until every drop was inside the girl I’d just fucked. I remained inside Anna’s cunt for a few moments then I pulled out of her. I pulled up my trousers and pants. As Anna pulled up her panties, she told me that we need to spend more time together. I agreed and said we should try and spend some time alone here in the clubhouse. She then told me that the next time we fuck, she would let me get up inside her ass. After a quick kiss, Anna left and once again I was free to enjoy the silence of being the only on in the clubhouse. But my good luck would run out, you see somewhere within the 2 days following my tryst with Anna, I had caught a bad case of flu and was bedridden in the clubhouse.

Matthew checked on my three times a day so I was not lonely or going to mad. I actually enjoyed the peace and quiet from being sick but the vomiting not so much. I spent most of my time either asleep or puking in the bathroom so the time went by quicker than normal. I also managed to get in a little light reading when I was not asleep or blowing chunks in the bathroom. It was not until the Friday night when Matthew and Ms. Celeste came into the clubhouse that I learned the surprising future of the school. Ms. Celeste told me that when the school broke up for summer holidays in a week, that we would not be able to return once the holidays was over as the school would be closing down permanently.

This took me by surprise as I’d had to idea the school was in any kind of financial trouble. Ms. Celeste said the diocese that managed the school was not happy with the performance and would no longer fund it. I did not know what to say as I was still in shock, but there was sweet fuck all I could do about it. I asked her what do we do now, to which she told me that everything would be OK. I did not care about Li, Kara or Anna as the only girl or woman that I cared about was Ariadne. As it turns out things for the school would take a semi nosedive a day later. Some of the other parents found out about the forthcoming school closure and at first Mr. Grent denied it he soon had to change his tune and admit that the school was indeed going to close down.

Things for the school then went practically into free-fall. Some of the parents then said if the school was going to close down then they might as well take their kids out of the school before it closes down. Within 4 days, the school closure had been brought forward to the end of the week. Since the school was going to close down, we figured there was no point in doing any schoolwork so we all decided to just goof off until closing day. And on closing day, when I’d had a shower and breakfast, Mr. Grent told me that Matthew and Ms. Celeste had left early that morning within 10 minutes of each other, as had Anne-Marie. I was honestly heartbroken that I would not be able to see my girlfriend or best friend ever again, or so I thought at the time.

I was naturally bummed out by this news. I was then told by Mr. Grent that I had to wait in the waiting room at the front of the school as my transport home would soon be here. As I sat in the waiting room, I found myself thinking about Ariadne and how she was my girlfriend for just under a week. I realized just how much I actually missed her. I was shaken from my thoughts about her when Mr. Grent opened the door and said that Kara had to wait with me, I said that was fine but truthfully I could do nothing about it. He stepped aside and Kara entered the waiting room and sat on the couch opposite me. Mr. Grent told us to have fun while we waited, he then winked at me and left, closing the door behind him.

It then dawned on me that he had essentially given me permission to fuck Kara. And that is exactly what I did. I said to Kara that this would be our last chance to have sex and she agreed. She got up and came over to the couch I was sat on and we both laid down and began kissing passionately. We did this for a few minutes before Kara suggested that we get totally bare-ass naked which I agreed was a good idea. I went and closed the curtains in the waiting room and locked the door as to give us privacy. We practically ripped off our clothes and in no time we were both stood before each other totally naked; we then stepped up close to each other, wrapped our arms around each other, and kissed passionately.

It was not long before we fell onto the couch, still wrapped in each other’s arms and kissing madly. This would be the last time I got to fuck Kara so I was determined to make it one to remember. I broke the kiss and moved down to her legs, I then kissed her feet and licked her legs all the way up. I told her to turn over so I can kiss her bum-cheeks, which she did. I looked at her bum-cheeks and had one regret that I never got the chance to get my cock up it for a second time. “Would you blow me?” I asked. “Of course I will” she replied “Sit back and enjoy yourself”. She got off me and knelt in front of me, I sat up as she got in between my knees. “You’re nice and hard I see” Kara says as she spits on my cock.

“It’s easy to get hard when it’s you I’m looking at” I reply as she jerks me off. She does this for a few moments, all while making eye contact. She stopped after a few moments then pursed her lips, placed them at the tip of my rock hard cock, and gently pressed her head forward, slowly taking the entirety of my cock into her mouth. There is something relaxing about being sucked off, It is also so very calming about being given a blowjob by a girl at the same school as you; at least that is what I think about blowjobs. I reached forward and grabbed Kara’s tits and rubbed and squeezed them gently. Feeling her up somehow made my cock feel as if it got harder than it already was, I knew this was not possible.

But I swear to got that it still felt like it had gotten harder. Still keeping my cock in her mouth, Kara looked up at me and smiled. She winked at me before returning her attention to my cock. I looked down as Kara’s head bobbed up and down my engorged cock. I knew that this would be the last time that I ever did anything with her so I was determined to make the most of it. I held her head gently and guided it up and down my dick, I closed my eyes and sat back. The feeling of getting a blowjob from a girl I would never see again only made it even better. Kara used her tongue to rub the underside of my cock, causing me to groan in pleasure. “You like?” Kara asked, kissing the tip of my cock.

“Fuck yeah” I replied “You suck better than Li ever could”. What I had just told Kara was indeed the truth; she did suck cock much better than Li ever did. As she smiled and resumed the blowjob, I put my hands behind my head and sat back to enjoy her oral work. As she bobbed her head up and down, it dawned on me that I not only was I naked with another girl in the waiting room, I was breaking all sorts of school rules by doing with Kara what we were doing; but I did not care. School was closing down so there was nothing they could do to me if we got caught. I did not care what happened to Kara after school closed and why should I? She was just another fuck-buddy I had, with the other two being Li and Anna.

Admittedly Kara was a better fuck than Li and about on par with Anna, but that is it. There was nothing else I liked about Kara save for her fucking skills. Feeling the familiar tingling in my cock, I looked down at Kara and told her “I’m almost ready to cum”. Kara nodded and replied “That’s fine; remember to cum in my mouth”. I nodded and replied “OK”. She resumed the blowjob, bobbing her head up and down even faster than she had been. I gritted my teeth and did my best to hold off on cumming for as long as I possibly could. But Kara’s oral skills were to good and I could not hold back any longer. “Oh god, I’m cumming” I said to her “HERE I CUM” and a few moments later, I did indeed cum.

As my cock exploded and released its hot load of baby-juice into Kara’s willing mouth, I gritted my teeth and did my best not to groan in pleasure to loudly. Kara clamped her mouth around the base of my cock and took all of my cum into her mouth. She did her best not to let a single drop of my cum go to waste, though some did leak out of her mouth. “Well, that was a load and a half” Kara said, wiping some cum from her chin and licking it from her fingers “I almost didn’t take it all”. I smiled and replied “I’m glad you took as much as you did; you caused the hard-on that made the load”. For a moment, there was silence which was broken when Kara asked “Wanna fuck?” To which I replied “I’d love to, but might I suggest you wash your mouth out?”.

She nodded and asked with a smile “Why, do I have something in my teeth?”. I smiled and said “Your breath smells a bit like you’ve had cock in your mouth”. She then asked “Do you have any water?” To which I told her “There might be a coke or something in the fridge”. We both got up and I watched as Kara walked over to the fridge to get a coke. I watched as she bent over to get the coke and felt my cock start to get hard once again as I stared at her ass. “Enjoying the view?” She asked. “Very much so” I replied with a smile. She tossed me a coke and opened her own. She took mouthfuls of the coke and swilled her mouth out several times, clearing my cum from her mouth and spitting it into the sink.

“So, is there any chance I could get up your great-looking ass?” I asked as I sipped my coke. “Of course there is” Kara answered with a smile “But first I want your cock up my cunt”. I nodded and said “Of course”. She downed the last of her coke as I did mine. We then laid down on the couch with me on top. “I want to kiss your ass” I told her. “OK” Kara said as she rolled over. I licked and kissed each bum-cheek before giving them each a little bite. I grabbed her bum and squeezed and rubbed it gently. I was going to enjoy getting up inside her ass. “Turn back over please” I told her, which she did. I then licked and kissed her flat belly, this caused Kara to giggle. Licking her belly was something I’d wanted to do to her for a while now.

I spent a few seconds licking and kissing her belly before I licked my way up to her tits. I gently squeezed and rubbed them before I moved onto licking and kissing them. I had to admit to myself that Kara had decent looking tits. I gently bit her left tit and said she was glad I liked them. I gently bit her right tit then I kissed her passionately, sticking my tongue as far as I possibly into her mouth. There was no trace of my cum in her mouth as my tongue swirled around, I broke the kiss and fisted my cock to her cunt entrance. I then began to stroke my cock-head up and down her slit, just nudging my way in between her outer lips. Then I tickled the head of my cock through the light dusting of fuzz above her clit.

I gasped with the pleasure of that sensation. I would sure miss doing that to Kara when her transport came for her. My cock throbbed as my lust took over, unable to resist any longer, I pushed my cock-head back down to her slit. I nudged it around a bit, and pressed forward. “Oh god yes” She grunted as the head pushed its way into her well-used hole followed by the rest of my engorged fuck-stick. Once I was fully inside her, Kara said that “Roll over, I want to be on top”. I agreed and said “Sure thing”. We rolled over so Kara was now on top and looked down at me with a smile. She sat up and started bouncing up and down on my cock surprisingly fast and hard and I reached up and grabbed her jiggling titties.

As I rubbed and squeezed them, Kara told me that “I want you to fill me up with your cum until I’m overflowing with your baby-making juice”. I told said to her that “I would fill your every hole with my cum if you want me to”. Kara quickly replied with “If you can go for a second time, you can cum in my ass”. I nodded and answered “I’ll do my best to fill your bum as much as I did your cunt and mouth”. For the next few minutes, neither of us said anything as we enjoyed the fuck in silence save for the sound of our loins slapping against each other and the odd moan and groan of pleasure. As we fucked, I looked at Kara’s face and saw a look of total sexual pleasure on it and I was pleased with what I saw.

If she was having a good fuck then it stands to reason the guy she was fucking, which was me, would also have a good fuck. I only cared about Kara in regards to how much she was enjoying the fuck as if she enjoyed it then she would be more willing to honour her promise to let me fuck her ass. That is of course if we had enough time before her transport arrived. A few minutes later I felt the familiar tingling in my cock which indicated to me that I was soon to cum. Kara noticed this when I started groaning through gritted teeth. “Oh no, don’t cum yet I’m not ready” Kara told me as she slapped my across the face to try and forestall my ejaculation; and I can tell you it worked.

Years later, I would realize that Kara was trying something similar to a ‘Donkey Punch’ but instead of punching me in the back of the head or lower back she slapped me across the face. The shock of being slapped across the face had some effect and the urge to cum abated for a few minutes but it soon came back and I could no longer hold it back. Through gritted teeth, I told Kara “I cant hold back; I’M CUMMING”. And that is exactly what I did. I felt my cock explode and deposit my hot load of cum up inside Kara’s teenage twat. Kara groaned loudly as she came. She groaned in pleasure, and told me “Oh FUCK ME; my cunt is almost overflowing with your baby batter”. I loved hearing dirty talk like that when I’m fucking a woman or girl.

Even though she had cum and the last of my cum was up inside her, she kept bouncing on my cock for a few more seconds. With our bodies now covered with sweat, Kara got off my softening cock and collapsed on top of me. We laid there for a few moments as our slowly cooled with nothing but the sound of our breathing filling the room. A short time later, she got off me and we both got up off the couch and got dressed quickly. “Wow ... that hit the spot” Kara says “I’ll miss that when I’m at home”. I sighed and replied “Yeah, you were a great fuck Kara, absolutely top-notch”. Despite me lying to girls I was fucking by telling them that ‘I loved them’ what I had said to Kara was indeed the truth.

Kara was indeed a great fuck and I wished that I’d fucked her more often. “So, do you still want to fuck me up the ass?” Kara asked after a few more minutes of silence. “Oh hell yes I do” I replied “Only if you’re still up for it?”. Kara nodded and answered “Sure, lets do it”. Unfortunately, we did not have any time to fuck her ass as less than a minute later her transport arrived. Once we’d said a brief goodbye, I watched as she left then returned to the waiting room. Once I was sat in the waiting room alone once again, I knew that I would never see Kara again. And that did not bother me at all; I had only ever used Kara for sex and had no emotional attachments to her at all. Kara knew this and thankfully she felt the same way.

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