Confessions From a Boarding School Pupil - Cover

Confessions From a Boarding School Pupil

Copyright© 2022 by Drax

Episode 6: The Clubhouse Cum

Pedo Sex Story: Episode 6: The Clubhouse Cum - 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  

Over the next week, I was able to enjoy some peace and quiet plus I was able to sort out the next place I fucked Kara, Li or Anna. As it turns out, there was an old flat on the floor above St. Pats living room. It had gone unused since the late 70s and was a musty-smelling shit-hole, but all it needed was a clean-up and it was as good as new. And before you ask, Matthew and myself managed to get out of cleaning duties by telling Mr. Grent we needed to talk to him, he knew it was a bullshit excuse but he let it slide. When the flat was cleaned out, there was much discussion as to what should be done with it. The prevailing opinion was that it be used as a sort-of clubhouse for the best behaved kids.

This is exactly what Mr. Grent said it was to be used for. Mr. Grent said to avoid any kind of favouritism or accusations of being unfair that he would decide who used the clubhouse, which is why Matthew and myself knew that we’d get in for sure. We’d always made sure our grades were the best we could do, that and we knew how to kiss ass at an expert level. So naturally we were the two first in the clubhouse, and the teacher that was assigned to be the chaperon of those in aforementioned clubhouse was the sports teacher, Ms. Celeste. The other person to be in the clubhouse with us was by a genius stroke of luck was Anna; Mr. Grent said that having two boys and two girls in the clubhouse would even things out.

The first time we got to spend in the clubhouse was the following day. Mr. Grent gave the four of us our own key and told us that we would be reviewed on our status in the club every to weeks, which we all said was fair. For me, this was half good and half bad; half good because I was in with Anna and half bad because there was a teacher keeping an eye on us. But little did I realize just much fun I would get out of having a teacher with us. Our first time in the clubhouse came after school had finished and evening meal was over and done with. Ms. Celeste told us that while we were in class, a little bit extra redecorating had been done for us. When we went up to the clubhouse, we saw exactly what Ms. Celeste was talking about.

Two of the three bedrooms had been fitted with new beds and had our names on the doors. She told us that those in the clubhouse, meaning Anna, Matthew and myself, would be sleeping up here instead of downstairs in our regular bedrooms. She said that the third bedroom was to be her bedroom as she’d been told by Mr. Grent that she’d have to sleep in the clubhouse as the chaperon. I did not know at the time but learned some years later that she was close to turning down the job of clubhouse chaperon until she heard that I would be there. She pointed out that her room was between mine and Matthew’s room and Anna’s room so she could put a stop to any kind of night-time sexual shenanigans.

Once the three of us had moved our personal belongings into our rooms, we settled down for a quiet cup of tea, during which Ms. Celeste told us we could call her by her first name; Ariadne. During our first few hours in the clubhouse, Ariadne told us that we could stay up later than the rest of the kids so long as we behaved and did as we were told. Anna then joked that she’s not sharing me with Ariadne, no matter what she tells us to do. Even though we joked about it, I saw Ariadne steal a glance at me, and not for the first time since we were in the clubhouse. Once we’d finished our tea, we all decided it would be best if we called it an early night as not to push our luck.

As we headed to our rooms, Ariadne managed to get in a quick grope of my ass without Anna or Matthew noticing. I know that you might think that we got down to fucking right away, and as much as I’d like that to be true, it wasn’t. The first sexual hook-up in the clubhouse did not occur until midway through our second week. On the day in question, I had been selected as the cleaner for the clubhouse, which means exactly what it sounds like. I had spoken to Mr. Grent and said that I would need to take time off from school for the day to get the clubhouse cleaned up properly. He agreed and said he’d clear it with the teaching staff so I would not get accused of skipping school, which I kind of was in a way.

Seeing as the Clubhouse was rather warm that morning due to the rather inclement weather and the fact that I would be in the clubhouse on my own, I decided to do the cleaning in just my boxer-shorts and a T-shirt. It was around the 45 minute mark when I heard the door to the clubhouse open. I figured it was Matthew or Anna but I would turn out to be wrong. I heard the voice of Ariadne calling out and asking if anyone was in, to which I called out that it was me and I was doing the cleaning. She came into the living room and saw me in my boxer shorts and T-shirt and just sighed. I asked if she was OK to which she replied, while still staring at me, that she was just fine.

I asked her again if she was OK as she just stared at me and said that I was fine. It was then that it dawned on me that she wanted me, which made the butt slap make sense and it also suited me just fine. She walked up to me and stroked my face and asked if I was alone in the clubhouse. I said apart from the two of us we were alone. She took a step back and looked down at my boxer shorts, which by now were sporting a massive tent due to my erect cock. She smiled and said that she could tell I was pleased to see her and what she did next I wanted her to do but did not expect that she would. She stepped back up to me and stuck her hand inside my boxer shorts and grabbed hold of my cock.

I stammered that it felt nice having her hand on my cock, she replied by gently squeezing it. She then says that she knows about me and Anna, having seen me climbing out of the swimming pool window. She then says that she does not care about Anna, my so-called girlfriend Li or any other girl I might be dicking about with. She said that only one thing mattered, and that was me and her. I asked what she meant, and she told me that if the chance for us to spend the night in bed together, then we would take it to which I replied that sounded really good. She then said again she did not care about Anna, my so-called girlfriend Li or any other girl I might be dicking about with so long as I came back to her at night.

I agreed and told her that I would not sleep with any other girl, she replied that I was still allowed to be with any other girl I might be dicking about with so long as precautions were taken to which I said that was par for the course. It wasn’t as I’d never used a condom before at that point but if it meant keeping in Ariadne’s good books then I would start to use them, even if I had no way of actually getting hold of them. She then leaned forward and gave me a big kiss, slipping me some tongue as well. She broke the kiss and told me that she did not mean protection as in condoms, she meant protection as not dicking about with every girl and pulling out before I cum so I don’t knock any of them up.

I agreed and she smiled, removing her hand from my boxer shorts. Then taking me by the hand, she led me into her bedroom telling me that we can’t ‘make love’ in the living room. ‘Make love’ was an interesting choice of words as with Li, Kara and Anna it had always been ‘fucking’, Ariadne using the term ‘Make love’ was something that I’d never heard before at that point in my life. And I would soon learn just why she had used that phrase instead of ‘Fucking’ or some other term for a quick bang. Once we were in her room, she told me to lose my clothes, so I did as she said and removed my t-shirt and boxer-shorts, and stood before her totally naked with my hands covering my cock and balls.

She then made my cock start to get as hard as it could by starting to remove her own clothes. I watched as she stripped down to just her black lace bra and panties, my cock was now as hard as it could get, I was also more than a little nervous. Ariadne must have known I was nervous as she smiled at me and said that there was no need for me to be nervous, to which I said there was. I said I’ve never been with a full-grown woman who is a teacher which is why I was nervous. Ariadne smiled and told me that when we’re done, I’d never want to be with anyone else. She said I’d never want any of the ‘Silly little school bitches’ ever again, as she so eloquently put it. And I tended to agree with her.

She tells me to lay on her bed which I do, she gets on the bed in between my legs and she swallows my cock. I was in haven as I just lay back on the bed and let her suck me, this blowjob was only a few seconds old and was already better than any blowjob that I’d received at that point in my life. She works my cock, sucking it deep, then coming up for air and licking the head while jacking the shaft with her soft hands. After a few minutes she stops the blowjob and sits up, telling me she is going to match my dress sense which meant only one thing; she was going to strip off. I asked if she was going to strip, and she replied by getting off the bed and slowly sliding her panties down her smooth legs and kicking them aside.

She then she removed her bra and tossed it aside to her panties. She put her hands on her hips and asked if I liked what I saw, to which I replied that she looked like perfection. She turned her back to me and glanced over her shoulder at me and asked me ‘Does my bum look big?’. I sighed happily and said that her bum looked perfect just like the rest of her. She turned back around and walked over to the bed and said that we should get under the covers, which we did. The feeling of her cuddled up to me as we were both naked felt just so relaxing. For the next few moments we just lay there in each other’s arms, enjoying the peace and quiet. After a few minutes of naked cuddling, Ariadne looked at me.

She asked if I was ready, to which I told her I was ready from the first moment I saw her. We kissed passionately for a few moments before she broke the kiss and straddled my waist, positioning herself over my cock. She looked down at me and smiled as she fisted my cock to her cunt hole; making sure that just the tip was inside; she asked me to hold her hands, which I did; she then smiled at me lovingly as she slowly sank down my rock-hard cock. For a few moments, she remained still as she allowed me to get used to my cock being inside her and for her to get used to the feeling too. Using her leg muscles she raised herself up then sank back down slowly, setting the pace for the fuck.

As you already know from what you have previously read, I was not one for slow fucks as I was more used to quick ones that were over relatively quickly. But this slow fuck felt absolutely amazing and was already better than Li, Kara and Anna all merged into one. Ariadne looked down at me and said that this was the best fuck she’d ever had, to which I asked if she was telling the truth. She told me that she was indeed telling the truth, and when I said I find that hard to believe, she stopped the fuck. She told me that I needed to have more confidence in myself and have the belief when a woman tells me that this is the best fuck she’s ever had, that she could be telling the truth; which she was.

I honestly did not know what to say, I’d never been given such a kind compliment by a woman before in my entire life. She resumed the fuck and told me that when she said that this was the best fuck she’d ever had. She told me that she was not lying to me and that she would never do that. I told her that after being in bed with her any other girl would not be even remotely close to being as beautiful as she is; I then said four words which would change my life: ‘I love you Ariadne’. With tears of joy in her eyes, she replied that she loved me to, and before I could say anything else she let go of my hands, leaned down and kissed me passionately. And boy oh boy did she kiss better than Li, Kara or Anna.

And as our tongues swirled about in each other’s mouths, it dawned on me just what I had said when I told Ariadne that I loved her. Now I must admit that I felt a modicum of panic when it dawned on me that I had told my gym teacher, who I was fucking, that I was in love with her. I’d never said ‘I love you’ to Li, Kara or Anna nor had I ever had any inclination to ever do so; but at that very moment, I just could not figure out why I had said what I said. Her lips deeply kiss mine and she wraps her arms around me. I feel the warmth of her love flood through my body as Ariadne broke the kiss, it then dawned on me why I had told her that I loved her, and it was a realization that I had never felt before.

The reason I had told Ariadne that I loved her was because I was genuinely in love with her. She slowly sat back up and told me that if she could she would live with me right then and there and I replied that I wanted that to. She once again asked me to hold her hands, which I did instantly and for the rest of the fuck neither of us said a word. It was not much longer until she started bouncing up and down on my cock faster and faster, telling me that she was soon going to cum. A few seconds later she told me that she was going to cum, which she did a few moments later. and when I felt her cum and accompanying groans of pleasure, that was it I could no longer hold back.

I groaned out in pleasure and said that I was cumming, Ariadne’s cunt muscles clasped my rock-hard cock tightly as the jets of cum squirted deep into her middle-aged belly. Once the last drop of my cum was inside Ms. Celeste’s flat belly and when we’d both come down from the pleasure of the orgasm, she climbed off me and collapsed on the bed next to me. We just laid there in naked silence for a few minutes, gently holding hands. She sighed and said to me that she wanted to stay in bed with her boyfriend all day if she could to which I said that I’d better get going before he arrived. Ariadne said that it was lucky I was her boyfriend as with jokes like that I’d make a lousy comedian.

As we were about to kiss, Ariadne’s wristwatch alarm beeped, she looked at it and did not like what she saw. She got out of bed and hurriedly began to get dressed, and as I got out of bed and also began to get dressed, she said she was going to be late. I frowned and asked what she meant to which she said she had a gym-class in 10 minutes and that she was going to be late if she did not get going. Once we were both dressed, Ariadne said that she would be back later-on that day as usual. We then shared a quick kiss then she left the clubhouse. Once I was alone, I went into the kitchen and got a cold glass of water then went into the living room and sat in one of the armchairs and took stock of how my life had changed.

It had changed so rapidly in recent days. From the moment the clubhouse had opened, my life changed when I met Ms. Celeste, who was now my “secret girlfriend”. I could not believe my luck that I, a 14 year old schoolboy now had a middle-aged woman as my girlfriend, but not just any middle-aged woman. Ms. Ariadne Celeste was my gym teacher and was in the best physical shape I had ever seen and would ever see for many years to come. I still found it very hard to believe that she actually wanted me as her boyfriend. But I was not going to ‘look a gift horse in the mouth’ as the saying goes. I finished my glass of water, then went into Ariadne’s room and made the bed; which did not take me long.

I then decided to skip the rest of the school-day and spent the rest of the day either tidying up the clubhouse or just sitting in an armchair reading. I also used the peace and quiet to reflect on what I had done with Ariadne and just how I really felt about her. I was never one of these guys who seemingly fall in love at the drop of a hat. In fact I used to say that I was incapable of falling in love, I’m glad to say that I was wrong and that is what I found myself surprisingly worried about. I did not want to admit it to myself that there was the possibility that I was actually in love with Ariadne. At that moment, I honestly could not tell why I was worried about being in love with Ariadne.

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