Confessions From a Boarding School Pupil - Cover

Confessions From a Boarding School Pupil

Copyright© 2022 by Drax

Episode 12: A moment with Anna II

Pedo Sex Story: Episode 12: A moment with Anna II - 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 escapade happened just a few days after my bunk-up with Anne-Marie. It happened on a Friday morning; I was in the clubhouse as I was not feeling very well, now that right there was a dirty lie. You see, there was a school trip I did not want to go on so I feigned being sick. I did not want to spend hours on a coach with Ms Tran. So Mr. Grent told me to stay in the clubhouse; I think he knew that I was feigning being sick but thankfully he didn’t say anything. It was a few minutes after everyone else had gone on the school trip when my peace and quiet was interrupted by Mr. Grent as he came into the clubhouse. “Hello sir” I said, feigning a sore throat “How’s it hanging?”. As he came into the living room, I noticed that Anna was with him.

“Jay, I need a favour” he says, to which I replied with a weak smile “OK sir, you can stop asking; I’ll sleep with your wife”. Mr. Grent shot me a look then said “Seriously Jay, I’ve got a favour to ask”. I smile and say “As long as this favour has nothing to do with Ms Tran, then how can I help?”. Mr. Grent smiled at the joke. Ms Karrueche Tran was the English teacher at Brentford Court. She was strict and came across as humourless robot so the kids at school had taken to calling her “Robo-bitch”, behind her back of course. “No, it’s got nothing to do with Ms. Tran” Mr Grent tells me. I nodded and asked “What is it?”. He indicated Anna and said “Like you, Anna is not feeling to well, so she’s staying up here, OK?”.

I frowned and asked “She’s already a member of the clubhouse sir, you don’t have to ask”. He replied quickly with “I know; but you are supposed to be here on your own as you’re not well”. He was right when he said that as I WAS supposed to be on my own. “Since the two of you are not well, I figured it would make sense to have you both here” He added “Plus you’ll have the entire day to yourself”. Now that was something I was looking forward to; having some peace and quiet. “Now that is a good idea” I say, I turn to face Anna and tell her “You know where everything is; knock yourself out”. As she moves into the kitchen, she winks at me. “Well, now that you two are settled, I’ll get out of your hair” Mr. Grent says.

And as he heads for the door, He indicates that I should follow him, so I do. “I’ll see you to the door sir” I say, just loud enough for Anna to hear. Once we’re at the door, Mr. Grent turns to me and says “Since you two will be alone, whatever you do, just be safe...”. I nodded and replied “Yes sir...”. I watched as he left, and when I closed the door behind him, I went back into the living room where I was momentarily shocked when I saw Anna sat in the armchair totally naked. “Wow...” I say as I sit on the couch “I must say how much I like how you’re dressed”. As I looked at Anna and made a piss-poor attempt not to stare at her naked form, she asked “Can we sleep together?”. I frowned and asked “Do you mean overnight or just for a while?”.

Anna smiled as she got up, taking my hand in hers she leads me into my room and says “What perhaps I should have said was ‘Lets go to bed’...”. I nod and reply “Just give me a moment to get changed”. She smiles as I hurriedly get out of my clothes and stand before her as naked as she was. “Now that’s much better” Anna says as she steps up to me, we wrap our arms around each other and kiss passionately. I slid my hands down and gently grabbed her bum and squeezed it gently. Doing this had the effect of making my cock get as hard as it possibly could. Anna had a really nice We kissed like that for a few moments before Anna broke the kiss and said “Let’s get in bed; we’ll be warm and more comfortable”. I smiled and answered “Now that is a great idea”.

We both got in bed where we cuddle up to each other and resumed kissing, which felt even better once we were in bed. Knowing that we had the entire day to ourselves allowed us to take our time, allowing us to kiss passionately and slowly. This was different kissing to what I did with Kara, Li and Anne-Marie, it was more akin to the type of kissing I did with Ariadne. I was by no means in love with Anna, it just made a welcome change to kiss passionately with one of my side-chicks. After 7 minutes of kissing and gentle groping, we stopped and Anna said to me “It’s nice to have some time to ourselves”. I nod and reply “Indeed it is; we don’t have to rush for fear of getting caught; we can take our time and have more fun”.

For the next few minutes, we just lay there in each others arms, enjoying the peace and quiet. I looked at Anna and realised just how fucking hot she actually was and smiled. I was going to enjoy spending the day with and in her; I would also have been fine just laying there in bed with her she was that good looking. “So, what do you want to do now?” I asked, to which Anna replied with “Now that is a very good question; I thought we could start with some more of this...”. She leans in and we resume kissing. We were able to take things slowly, safe in the knowledge that we would not get caught. I placed my hands on her slim waist and held her gently as we put our tongues as far into each other’s mouths as we possibly could.

We then began rolling around the bed as we kissed, and after a few moments, we fell out of the bed. “Well, that’s a first” I say with a smile, to which Anna replies “Me too; it may be the first time I fall out of bed with my secret boyfriend but it won’t be the last”. We get up and as I gaze at Anna’s naked form, she says “Let’s go into the living room and fuck on the couch”. I nod and reply “Good idea; lets go...”. She takes me by the hand and we walk out of the bedroom and back into the living room. “Lay down” Anna tells me “I want to be on top”. I got on the couch and laid down, Anna climbed on top of me and smiled as she fisted my cock to her cunt hole, making sure that just the tip was inside. I held her hips gently as she smiled at me.

She looked me right in the eyes 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. She sighed happily as she set the pace for the fuck. As we settled into the fuck, it came as no shock to me that I liked Anna more than I liked Li. And it goes without saying that I like Anna more than Kara. As I looked up at Anna, it became clear that she was doing her best to make the fuck last, and that was just fine with me. I enjoyed slow fucks from time to time if they were with the right girl, such as those I have with Ariadne or with Anna.

I slid my hands up her body and gently took hold of her titties and squeezed them gently and told her “Your boobs are perfect”. She smiled and replied “They’re only for you; all of my body is just for you”. As I squeezed them gently, Anna leaned down and kissed me gently then sat back up. Slow-fucking with Anna was fantastic, she rode me slowly but firmly as I rubbed and squeezed her teenage tits. As I looked up at the Ukrainian teenager as she rode me, I knew that I would not last much longer. I suspect that Anna was also close to cumming as she began to grind on me harder and faster than she had been before. “Are you close to cumming?” She asked, to which I replied “Yeah, I’m close”. She looked down at me and told me “Hold on as long as you can; I’m almost there”.

A few seconds later, Anna came, and as I felt Anna cumming on my cock, I grunted through gritted teeth. I was doing the best that I could to try and hold off of cumming for as long as I can; I wanted the fuck with the Ukrainian teenager to last as long as it possibly could. But holding back was difficult when Anna cried out “FILL ME WITH YOUR CUM YOU NAKED BOY”. And when she said that, I could not hold back any longer. “Oh god I’m cumming” I groaned “I’M FUCKING CUMMING IN YOU”. I cried out in pleasure as my cock exploded its load of hot cum up inside her tight, flat belly. I looked as her teenage titties I watched they bounced, I slid my hands onto them and held them gently. I thrust upwards to meet her bounce as the last drop of my cum was deposited in Anna’s pussy.

With one last thrust, I felt the last of my cum leave my cock and deposit inside the teenage girl. “Oh wow...” I say “That was epic”, Anna smiles and replies “Yeah it was”. She collapses onto me out of breath, and we just lay there for a few moments as we catch our breath. I gently hold Anna’s slim hips as we lay there in silence. I would have been perfectly content to just lay there with Anna for the rest of the day. “We should probably get up and out of bed” Anna says as she rolls off me, to which I ask “Why? we have the whole day to be together”. She turns to me and says “We should go into the living room and cuddle on the couch”. I smile and get off the bed, Anna takes me by the hand and we head back into the living room.

We move to the couch and I sit down and Anna sits next to me and wraps her arms around me. “So, what do you want to do now?” I ask as I wrap my arms around her, to which she replies “For the moment, lets just sit here and cuddle”. And that is exactly what we did; we sat on the couch and cuddled. Naked cuddling is something that I enjoy doing with Ariadne and it was obviously something I now enjoyed doing with Anna. “Let’s lay down” Anna says, breaking the silence, to which I reply “Sure...”. We lay down and Anna lays with her back to me as I slip my arm over her slim midriff. For the next few moments, we were just laid in silence, cuddled up on the couch and enjoying the peace and quiet of being alone in the clubhouse.

As I gently rubbed Anna’s flat belly, she asked me “Who do you like most, Li, Kara or me?”. I replied quickly and told her “It should be obvious that i really like you more than those other bitches”. She turned to face me and asked “Do you really mean that?”. I nodded and replied “of course I mean it; you are a statuesque goddess compared to those two hags”. Upon hearing those words, Anna smiled at me lovingly and kissed me gently. “I want no other guy inside me other than you” She tells me, to which I reply “If I could dump Li and Kara for you, then I would do so”. What I had just told Anna was the truth. If I could ditch Li and Kara for her then I would do so. Not because I loved Anna but because she was a much nicer person than either Li or Kara.

“This is nice” she says “Just being able to spend time with you and not having to rush about or have to worry about getting caught”. I kiss her gently and reply “I wish we could spend the night together”. Now that was indeed the truth; I really did wish I could spend the night sleeping totally naked with Anna. “It is such a shame the school outing can’t get lost along the way home” Anna says with a giggle “Then we could finally spend the night naked together”. It would be an interesting and very enjoyable night if Anna and myself could spend it together. “We can only hope that the outing gets lost” I say “Spending the night with you would be perfect”. While I meant the latter, I did not actually want the school trip to get lost.

And that was for the simple fact that Ariadne was one of the chaperones. An illicit thought entered my mind; what if I had been left with Ariadne instead of Anna. While it was an entertaining thought, I doubted that it would have been any different to what Anna and myself were doing now I then began to think about what else Anna and myself could get up to with our time together and it was all so much sexy fun I almost came right then and there. As I laid with Anna, a surprising thought entered my head; I wish she’d been my girlfriend instead of Li. If she had been, then I would not have felt the need to have an affair with Kara as I would be getting sex on a regular basis. That said I probably would still have fucked Kara because she was a total whore.

She was nothing more to me than an easy source of sex whenever I wanted a quick hummer or a quickie. I have mentioned it before but if Li had put out more, then I doubt I would have jumped into bed with Kara so quickly. “So, what do you want to do and where do you want to do it now?” Anna asked, to which I replied “How about a blowjob in the armchair?”. Anna smiled and said “Then please take your seat as the fun is about to begin”. We got up on the couch and moved to the armchair, I sat down and she knelt down in front of me. “You just sit back and enjoy yourself” Anna told me as she got in between my knees and kissed the tip of my cock “Here we go...”. I watched as she took my whole cock into her mouth and clamped her lips around the base.

And as she started bobbing her head up and down, I sighed in pleasure and closed my eyes. I leaned back and enjoyed the blowjob. As I have mentioned before, Anna was fantastic and sucking my cock and I was thankful that I had this alone time with her to enjoy her oral skills. The best blowjob I’d received from Anna so far had been the one in the swimming pool toilet cubicle, but this one was giving that one a run for its money. “This feels so good” I say “Your mouth is so fucking good”. As she had my cock in her mouth, she did not respond save for using her tongue to lick the tip of my cock. I looked down at Anna as she concentrated on my cock, I still found it hard to believe that we had this time together but here we were; in the clubhouse and she was sucking my cock.

I wished there were more school outings that I could miss out on so I could spend time alone with one of my “side-bitches” as Ariadne called them or even with Ariadne herself. But I was glad that I had this time with Anna and I was determined to enjoy every second that we had together. Anna was so good at sucking my cock that I soon felt the familiar tingle in my cock that meant I was going to cum soon. And while I didn’t tell her she somehow knew and increased the pace of her oral workings. “Oh god, I’m going to cum” I grunt through gritted teeth “I’M GONNA FUCKING CUM”. And a few moments later, my cock spasms and releases its hot load of cum directly into Anna’s warm, wet mouth. And this blowjob felt better than the one I got from her in the swimming pool toilets.

She clamps her mouth around the base of my erect fuck tool and makes sure that all of my cum goes into her throat. I watch her and can see that none of my cum leaks out; she’s taken all of it into her mouth. I sigh in pleasure as the last of my cum is deposited in Anna’s teenage mouth. “Oh my fucking GOD that was fantastic” I say as Anna sits back “You are fantastic at this”. She gets up and goes into the kitchen and gets a glass of water; she gargles with it then swallows; she does this a few times to ensure that all of my cum was washed down. “There, that’s better” she says with a smile “All of your cum has been washed down”. She checks her mouth in the mirror by the sink and gets another two glasses of water and washes her mouth out.

She does this to ensure there is no trace of cum in her mouth or throat. “You certainly can give a full load” Anna says as she lays down on the couch, to which I replied “You caused me to give such a generous load”. For the next few moments, neither of us says anything as we just sit there in silence. As I sit in the armchair, I look over at Anna and get up off the chair and mover to the couch, I get on it and lay down next to the naked teenager and we cuddle up. For a few moments we just cuddle on the couch in silence, enjoying the peace and quiet afforded to us for being the only ones in the clubhouse. “I could do this all day” Anna says “Just cuddle up naked with you”. I kissed her cheek and replied “Instead of going to class we could spend all day with each other”.

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