Confessions From a Boarding School Pupil - Cover

Confessions From a Boarding School Pupil

Copyright© 2022 by Drax

Episode 5: Fucking A Fatty

Pedo Sex Story: Episode 5: Fucking A Fatty - 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  

Despite all of my luck with Li, Kara and Anna, there was one pupil I did not speak to at Brentford Court. And that was a girl called Olivia Benton, she was a total loser who was also the school’s token fat-girl, or plump-girl given who you asked. I always avoided her because I had zero in common with her, but as you will read below, I would end up in bed with her. It all started the morning after my oral encounter with Kara and Li in the swimming pool. I was on my way down to class when the head teacher Mr. Grent called me over for a moment and said he needed to ask me for a massive favour. “So Sir, what’s this favour then?” I asked. “I need you to shlep some crap out of the old self-care flat” he tells me.

“It’s not too much, just two boxes of junk” he added. I figured that this was better than going to class so I replied “Sure Sir why not; it will Get Me Out of class for an hour or so”. He then told me that “you will not be doing this alone of course; I’ve arranged for Olivia Benton to give you a hand”. I tried not to show my annoyance at having to work with the school loser and fatty. “Fair enough” I replied “Two people will make this go quicker than just me on my own”. Mr. Grent smiled and said “Thanks Jay, I owe you one”. I nodded and replied “I’ll chalk it up with the others”. I nodded To him then left his office. I really was not pleased at all at having to spend any time with Olivia Benton.

But I was doing the head teacher a favour so I had to suck it up and put on a brave face as it were. Before I went to the self-care flat I made a quick pitstop in my room where I grabbed a 6-pack of cherry coke out of the mini fridge hidden in my locker. This was not shared with Olivia, rather it was for myself as I figured if I was going to spend more than a few seconds with the fatty loser then I needed to have plenty of caffeine at hand and within me. I grabbed a cherry coke from another six-pack and downed it in one go. I then made my way to the self-care flat, which was at the end of the hallway and up a flight of dusty stairs. Olivia was already there when I got there, and as soon as she saw me she smiled.

“Hey Jay, so you’re the one who’s helping me?”. She said cheerily. I put the six pack on the window ledge and replied “It would appear that I am yes”. She smiled at me, pointed at two boxes and told me “All we have to do is take them down to the dump and we’re finished”. I looked around the dusty and empty flat, all that remained in what was supposed to be the living room was a tatty couch whose best days were decades behind it. “I was counting on this taking more in 10 minutes” I told Olivia “This is going to be done in less than that”. She nodded and replied “That it will; unless you want to arse about here for a while and kill some time?”. Now I have to admit I had not expected her to say that.

And in all honesty, I would rather sit and talk to the school fat-girl loser then be done in less than 10 minutes. “OK Let’s do that” I replied “So, what exactly do you want to do too arse about?”. I got the six-pack and As I was trying to be polite, I offered Olivia a can of cherry coke. “Thank-you” she said with a smile “And to answer your question, we can always sit and talk for a while”. As I could not think of anything better to do, I replied with “OK, let’s sit and talk”. I was not really looking forward to having to sit and talk to Olivia for any length of time, but talking to the school fatty loser was better than doing the job and being done in less than 10 minutes.

“So, what shall we talk about?” I asked as I opened my coke. “We can always talk about why you volunteered to help me with this?” Olivia asked “We can talk about how you’re the only person to volunteer to help the ‘school fatty’ as I know I’m called by some kids here”. Now that was a question I had not expected her to ask and I was caught off guard by it. For some reason I did not have the heart to tell her that I had not volunteered to do this, that I had been asked to do it by the head teacher. “Why shouldn’t I help?” I asked. “Because I’m the school fatty” she replied “I notice that very few people want to talk to me or even be near me”. I could tell that she was depressed.

As I figured it would be bad to depress her even further, so I did my best to be friendly. “I’m here” I told her with a smile which I hoped did not look as forced as it was “And I wouldn’t listen to what the other little shits in this school say; I don’t listen to what they say about me”. She looked at me with a frown and asked “What things could they say about YOU?”. I sipped my coke and replied “They say I’ve got yellow fever, that I’m a Chink toy; they also say I’m a skinny looser”. She looked at me, sipped her coke and asked “I take it they call you those first things because of Li?”. I nodded and replied “Yes they do, and as for the “skinny loser” insult, I think they’re just jealous”.

What I had just told Olivia was of course total and utter bollocks; no one at school had ever said any of those things to me, I just said them to Olivia in an attempt to make it seem as if I had been gossiped about and insulted by the others kids. “I didn’t know people had said things like that to you” Olivia says “I’m so sorry”. What she just said sounded like it was genuine. “It’s OK” I reply “I don’t let it bother me”. Olivia sipped her Coke and sighed. “I wish I could” she says “But when you get it almost all the time it’s hard to ignore”. I could tell by the tone of her voice that she was unhappy talking about the bullying that she had received. And at that moment, for some unknown reason, I felt sorry for her.

“I get bullied almost every day” She tells me, her voice almost breaking “I just want one friend; just one person to say one nice thing to me”. She looked really depressed and there were tears in her eyes. And once again, I felt sorry for her, so I got up and sat next to her. “I’m here with you” I said to her, hoping I sounded as genuine as I hoped it would. “You have a cheery demeanour” I tell her “Which makes me look like a miserable git”. I know what I just said was not exactly top-notch stuff, but it was the best that I could come up with at short notice. “Really?” She asked, “You think I’m cheery?”. I nodded and replied “Yes indeed, given what you’ve told me how you are treated it’s a miracle you keep so cheery”.

She looked at me as she wiped the tears from her eyes, and what happened next was something that I genuinely did not expect to happen; she leaned forward and kissed me gently. I was caught off guard by the kiss, even more so when she put her hand on my face and held me gently. “You are the only person to treat me with any kindness” Olivia says, breaking the kiss. “Why shouldn’t I treat you with kindness?” I asked “I don’t see any need to be unpleasant...”. She interrupted me by kissing me again, this time I found myself gently holding her hand. After a few moments, we break the kiss and for just a few short seconds, we just stared at each other until Olivia breaks the silence.

“Why don’t we go lay down, it will be more comfortable for us” she said to me. I nodded and replied “Only if it’s what you want to do”. She looked at me with what I now know was a look of total love and said, “It is what I want...”. We got up off the couch and were still holding hands, we went into one of the bedrooms. While it was sparse and had almost nothing in it, it did have a bed and a few pillows. “You’re the first guy I’ve undressed in front of,” Olivia said as we began to undress. For a moment, I just watch as she takes off her shirt and bra. Now standing before me topless, I just stared at Olivia as I genuinely could not believe that I found her attractive in any way.

“Wow...” I said, staring at her as she slid her jeans down her legs “You look so good”. Olivia smiled at me as she removed her panties and replied “I’m so glad you like me”. Now standing before me totally naked, I had to admit that she looked good. “OK, now you” Olivia says with a smile. Realizing that she is talking about me getting undressed, I quickly strip off and I am soon standing before her as naked as she is before me. “Wow, you look nice” she says with a smile while staring at my erect cock. She stepped up to me and reached out and gently began stroking my cock, and as she did I reached around and took hold of her bum and squeezed it gently. “You feel nice” Olivia says with a smile.

I smile and reply “And so do you”. We just stare at each other for a few moments then lean in close and begin kissing one again. She lets go of my cock and wraps her arms around me. As we stand at the foot of the bed kissing, I still find it somewhat hard to believe that I was in the position that I was in; kissing naked with the school fat loser and what’s more I was enjoying it. I could not tell you why I was enjoying naked kissing with the school’s fat loser. She was nowhere near the type of girl that I normally liked, so why I liked her evaded me. After a few minutes of kissing and groping, Olivia broke the kiss and said “Let’s lay on the bed; it will be more comfortable for us”.

I smiled and replied “A good idea”. We went to the bed and got on and immediately started kissing and groping again. We carried on like that for a good 10 minutes, just kissing and groping each other. And as we kissed and groped, I still could hardly believe that I actually found Olivia attractive. She was not the type of girl I normally went for yet here I was, naked and in bed with her as we kissed and groped. “Wow” Olivia said with a smile as she broke the kiss “That was spot on”. I smile and reply “Yeah, that was really fine”. She smiled at me and asked “Want me to get on you?”. I nodded and replied, “Only if it’s what you want”. Olivia smiled at me and said “There is nothing I want more than to have sex with you”.

With a wink, she kissed the tip of my cock then kissed her way up my body, kissing my stomach and chest until she was on-top of me. “Are you ready?” She asked, to which I replied “Most assuredly”. She reached down and took hold of my cock, which she placed the tip just inside her cunt. “I’ve never had a cock inside me before” She tells me “Yours will be the first”. She looks at me as she lowers herself down my cock. I looked up at Olivia and on her face I saw a look of pure love. “Oh god Jay, I love you” Olivia said as she began slowly riding my cock “Oh god I fucking love you”. I reached up and put my hands on her tits and replied “Oh wow, I love you to ... you’re so good Olivia; so FUCKING GOOD”.

I did not actually love Olivia, but when you’re up inside a girl you can say things that you don’t mean. As she moved up and down my cock, I had to admit that Olivia was a way better fuck than I’d ever imagined. I slid my hands down from her boobs and held onto her waist; I also had to admit that Olivia was more attractive than I ever gave her credit for. She leaned down and kissed me passionately, we wrapped our arms around each other as we kissed. We broke the kiss as we rolled over until I was on top of her. “Do me Jay, rock your cock in my cunt” Olivia tells me as she wraps her legs around me “Shoot your spunk in my twat when you’re done”. I smiled and replied “Always do as the lady orders”.

As I settled into a gentle but firm thrusting motion, it occurred to me that we could get caught in bed. “What if ... we get caught” I asked as I leaned down and kissed her neck. “Who gives a fuck” Olivia replied “If we get ... caught then we ... get caught; we’re only ... making love”. Now I’ll admit that I never looked at it as ‘making love’ I’d always viewed what I’d done with Li, Kara and Anna as just sex, nothing more nothing less. As I thrust in and out of her cunt, I wondered just what it would be like to be in a sexual relationship with Olivia like I was with Kara and Anna. I was shaken out of those thoughts by Olivia, who kissed me and said “Let me know when you’re ready”.

I nodded and asked “So I can pull out?”. She shook her head and answered “So I kiss you so we don’t scream in pleasure and get caught”. What Olivia had just said made perfect sense, if we wanted to continue fucking then we needed to remain quiet when we both climaxed, which was not a problem. Not waiting until I was ready to cum, Olivia pulled me down into a passionate kiss. We rolled around as we kissed and so we ended up back with Olivia on top which was fine with me. She broke the kiss but stayed on-top of me and whispered in my ear “I’m almost there”. As she sat back up, I put my hands on her waist and held her tightly as she increased the speed of her bouncing on my cock.

“Keep this up and I’ll be there soon too” I told her. What I had just told her was not far off from the truth. I had felt the tingling in my cock but had held off on saying anything as I wanted the fuck to last as long as it could. A few moments later, Olivia told me that “Oh god I’m almost there”. She began bouncing on my cock faster with each second which made me want to cum even sooner. And a few moments later, that is what I told her when I said, “I’M CUMMING”. No sooner had I said that then Olivia leaned down and kissed me passionately. As her tongue entered my mouth, I felt my cock explode and release its massive load of cum inside Olivia’s teenage cunt. The kissing worked as it also muffled both our groans of pleasure.

As I felt Olivia cumming on my cock, I gripped her ass as hard as I could. After we’d both cum, Olivia just laid still on-top of me, and I hugged her gently. “Wow ... that was just ... wow” Olivia said as she caught her breath. “Yeah, it was, wasn’t it?” I replied. For a few more moments, we just laid there before Olivia told me “We should get dressed before anyone comes up here”. I nodded and replied “Yeah, I suppose that we should”. She got off me and we both got off the bed and began to get dressed. “Wait a second” I said “Do we HAVE to get changed?”. Wearing just her panties, Olivia turned back to face me and asked “What do you mean? We can’t sit around naked”.

I smiled and replied “Actually, we can if we don’t get out of bed or if we lay on the couch”. Oliva then asked, “You want to cuddle naked with me?”. I nodded and answered “Of course I do; it would be the perfect way to relax after making out”. She smiled and removed her panties. Standing before me naked, she smiled said “Then what are we waiting for; lets go”. I took her by the hand and we went into the living room. We laid on the couch and cuddled up to each other. As we laid on the couch, I found myself enjoying being cuddled up next to Olivia which I found strange if I was honest. Olivia was not the type of girl I would normally want anything to do with. But here I was, cuddling naked with her on the couch after fucking her. I do not know what OI was thinking when I fucked her, but I found it to be very enjoyable as was the naked cuddling. “A shame we can’t do this all day” Olivia says “If we could, we’d both never get out of bed, but then again why would we want to”.

I kiss her gently on the cheek and reply “Now that is a way I’d like to spend my day; cuddled up in bed with you”. For the next few minutes, we cuddled in silence and I kept one hand on her chest which I rubbed and squeezed gently. I guess we both must have fallen asleep as the next thing I know the clock on the living room wall reads 1:45; meaning we’d been asleep for more than an hour. “We should probably get dressed” I say, to which Olivia replies “Yes, but not before this...”. She kisses me passionately for a few seconds, putting her tongue in my mouth. After a few minutes, she breaks the kiss. We both get up off the couch as we head back into the bedroom.

And as we do, I can not help but steal more than one glance at her bum. As we are about to get dressed, I looked over at Olivia and had to admit that she was a better looking girl than I’d ever given her credit for. “Has anyone ever told you that you have a nice bum?” I asked, stepping up to her and rubbing her bum gently. “Only you” she replied with a small smile as she stood up. I stand behind her and rub her bum gently while slipping one arm around her waist. “This feels nice” she says as I wrap both arms around her waist and hug her gently “The hug and your dick poking me in the bum”. I hold her gently as I reply “I can’t help the dick, its your fault its like this”. I hug her then slid my hands up her body and squeeze her tits.

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