Confessions From a Boarding School Pupil - Cover

Confessions From a Boarding School Pupil

Copyright© 2022 by Drax

Episode 9: A moment with Anna

Pedo Sex Story: Episode 9: A moment with Anna - 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 few days, life at school was rather quiet. The clubhouse was used infrequently and on Tuesday morning, that all changed as I was summoned to Mr. Grent’s office along with Matthew, Anna and Ms. Celeste. “What’s the problem sir?” I asked as the four of us entered his office. “There has been a complaint about the clubhouse and how it is run” Mr. Grent told us as we all sat down “Which is why I’ve called you all here”. He sits back and says, “It has been brought to my attention that the Clubhouse is seen as an ‘elitist members only’ club...”. I thought it was just the elitist members only club, which was part of its appeal. “Who complained?” Anna asked “And why?”. We all wanted to know had complained about our clubhouse.

Mr. Grent replied with “I can’t say, but this person has lodged an official complaint about it; they are demanding changes are made to the clubhouse”. None of us wanted the delicate balance of the clubhouse to be changed. “Have no fear; I will not be making any changes to the clubhouse” he tells us “But for the sake of keeping the complainant satisfied, I’ve taken control of it”. Ms. Celeste frowned and asked, “I thought I was in charge of the clubhouse?”. Mr Grent replied with “Have no fear, you are still in charge of the clubhouse; but for all intents and purposes I am”. We all breathed a collective sigh of relief as the clubhouse was still ours. “That’s all I needed to tell you, you can go” Mr. Grent said to us.

As we rose to leave the room, Mr Grent called out “Jay, can you hang back for a moment”. I waited until the others had gone then I sat back down and asked “What’s up?”. Mr. Grent smiled and asked “You understand why the clubhouse is under my ‘control’, yes?”. I nodded and replied “Yes sir; some interfering old fool complained so you put it under your control to pacify said complaining old fool”. He nodded and asked “Very good; and?”. I frowned, not knowing what other reason there could be. Mr. Grent saw this look of confusion on my face and asked “While the identity of the complainant is off limits, do you want to know just what EXACTLY they complained about?”. I nodded and said “Indeed I do”. I was curious as to what the complainant had actually complained about.

“The complainant said they saw Kara creeping into the clubhouse” Mr. Grent said “They thought she might be up to no good; as in having a spot of tiffin’”. It then all made perfect sense as to why they had complained; they thought Kara was fucking someone. She had been fucking someone, me in fact. “She wasn’t up to anything bad” I replied “Whoever complained is an interfering old goat”. He smiled and said “I thought as much”. As I got up to leave, he called out “Next time you want tiffin, make sure it is not observed”. I took the hint behind his statement and replied “I understand sir; thank you”. He nodded and replied “You’re welcome; and this conversation never happened”. As I left the office, I was pleased that he’d tipped me off to be more careful.

I was also pissed off with whoever had complained had almost cost us the clubhouse. I also reserved a small part of my anger for Kara as it was her sloppiness in sneaking up that had caused the complaint to be lodged. The rest of the morning was quiet and uneventful, and come lunchtime it was just as uneventful. After lunch, we went to the clubhouse to relax until afternoon classes began. I wanted to tell the others what Mr. Grent had told me about tiffin but I had promised to keep it secret. “So, who do you think complained?” Anna asked. “I’ll bet it was Mrs Eardirt the batty old broad” Matthew replied “Who else could it be?”. We all knew that it had to be her, who else would complain specifically about the clubhouse.

“She’s had it out for you and me since we refused to join the Duke of Edinburgh bullshit” I replied. She had indeed been royally pissed off that we’d not wanted to join the D of E after that one camping trip we’d been on. In the weeks since said camping trip, she had repeatedly tried to get Matthew and myself to join her D of E group with a 100 percent failure rate. This only served to anger the old fool even further. But as it was voluntary she could not forces us to take part. When afternoon classes began, I had a free lesson wherein I could do what I wanted so long as it was educational. We all knew that when we had a free period, we’d just spend it hanging out in the clubhouse and doing nothing educational at all.

I decided to do just the same thing and just lay about reading and drinking copious amounts of coffee. I was not expecting to have a booty-call with Kara after what happened last time, but I was more than surprised when Anna came back into the clubhouse. “What’s up?” I asked “Didn’t know you had a free lesson today?”. She smiled and replied “I took n free lesson swap with Kara, she got mine yesterday and I got hers today”. I smiled, knowing that as we both had a free lesson, then we could maybe fool around; a fact that I pointed out to Anna. “We’re alone” I say to her with a smile “We could have some fun and no-one would catch us”. She looks at me, smiles and then says “Then let’s get naked shall we?”. And before I can say anything, she quickly strips out of her clothes.

And in just a few seconds, the Ukrainian Teenager is stood before me totally naked. “You like?” Anna asks, to which I reply “Oh good god I LOVE it”. She smiles and tells me “Now you...”. I understand what she has said and in just a few seconds I was soon as bare-butt naked as Anna was. “So, what do you want to do and where?” I asked, to which she replied “For the moment, lets just kiss”. I step up to her, we wrap our arms around each other and kiss passionately. As I put my hands on her firm Ukrainian ass, I felt my cock poking her in her flat belly. I knew that eventually I would get to put my cock up inside her, but for now I was enjoying the naked kissing with the Ukrainian teenager. We each let out a gentle but pleasured groan.

Our lips locked and parted slightly as our tongues slipped out to explore each other with tender touches. As we kissed, I could not help but think that we might get caught just as I’d got caught with Kara a few days previously. Even if we did get caught by Ariadne, it would not be as bad as this time we were only kissing and not fucking like I had been doing with Kara. I was shaken out of my thoughts about getting caught in the act when Anna jumped up and wrapped her legs around my waist, locking her heels behind my back. I was now stood in the middle of the clubhouse living room holding the naked Ukrainian teenager as we kissed. “Oh god Jay” Anna moaned, breaking the kiss “I love you so much”. Now I have to admit that this caught me off guard.

Anna had never said this to me before nor did I have any inkling that she felt that way about me. “I love you to Anna” I replied right away “I love you more than I could ever love Li”. What I had just told Anna was indeed the truth; I did love her more than I loved Li. Looking back on this now, with the power of hindsight I did not love Anna but rather I was in LUST with her; which was way more than I ever felt for Li. “You’d be my boyfriend?” she asked “You’d leave Li for me?”. I nodded and replied “Indeed I would; in fact of I could dump her, you could consider her dumped as of right now”. Anna looked at me, smiled lovingly and kisses me gently. She breaks the kiss and says “Then my dear boyfriend, I suggest we lay down and get comfy”.

I smile and reply “I wholeheartedly agree”. I carry her over to the couch and we lay down; we then resume the kissing. As we roll around on the couch, I keep my hands on Anna’s firm teenage ass. As our tongues explored each others mouths, my cock ached to get up inside Anna. We were rolling around on the couch so much that we almost fell off. “That was close” Anna says as we sit up. “Indeed it was” I reply as I slip my arm around her shoulder and squeeze her tits gently. For the next few minutes, that is all we did, not that I was complaining mind you. Anna’s tits with just the right size for groping when you’re kissing, fucking or just fancy a grope. “Want me to blow you?” Anna asked, breaking the silence. “Now that would be just lovely” I replied with a smile.

With a smile, she got off the couch and knelt in front of my splayed knees and reached for my prick; she then parted her lips as she raised the head of my now-fully-erect cock to her mouth. With a wink, the naked Ukrainian teenager pursed her lips into a bow and slipped the tight fleshy ‘O’ around the tip of my cock. Smoothly, she continued to slide down the shaft, taking the prong deeper into her wet maw to the accompaniment of my pleasured hiss. “Oh wow that’s good” I groan in pleasure “Oh yes this is so good”. As her head bobbed up and down my cock, I sat back and closed my eyes to enjoy her oral workings. I had to admit that Anna give really good fucking head, she was second only to Ariadne in terms of how good her oral skills were.

If I were standing up, my knees would have buckled as soon as she started sucking me. Over the next few minutes, I gently held her head as she continued blowing me. She used her tongue to massage the shaft which almost made me cum right then and there. I sat back and held her head gently. I opened my eyes and watched as she continued the blowjob, still using her tongue to massage the shaft. “Oh god, I think I might cum soon” I groaned in pleasure “Oh god I’m, going to cum soon”. What I told her was indeed the truth, I was so close to cumming I had to tell her as I did not want to cum in her mouth without letting her know first. Although the idea of cumming in her mouth without warning and choking her did sound like it could be fun.

As I held her head gently, I sped her up, I slowed her down, while she continued to do her best to suck, slurp, and lap at the slab driving in and out of her face. I knew that I would cum soon so I did my best to hold back as best as I could. After a few more minutes, I let go of her head and leaned back as Anna took the entirety of my rock-hard cock into her teenage mouth with ease. Thanks to her fantastic oral skills, I told Anna, “I’m going to cum real soon” And a few seconds later, that is exactly what I did. My cock shot its roping ejaculate directly into her oesophagus, towards its objective in her fourteen-year-old tummy. She clamped her mouth around the base of my cock and kept it there. She kept it clamped around the base of my cock.

She kept it there until the last of my cum left my cock and was deposited in her mouth. “Oh wow, that felt so good” I say, panting in pleasure “That was just fucking spot-on”. Anna got up and went to the sink and downed two glasses of water. She used the third glass to swill the last of the cum from her mouth. Once she’d rinsed the cum out of her mouth, she smiled at me and said “You certainly gave me a full load”. I nod and reply “It was your fantastic oral workings that got me worked up enough to provide you with the full load”. Anna got another glass of water and swilled her mouth out one final time before she moved back to the couch and sat down next to me. “Let me know if and when you want to go again” Anna says, resting her head on my shoulder.

“I will want to go again” I reply “But not for a while”. Anna looked down at my cock, which was semi-flaccid and it was slowly getting hard again. “Looks like you’re going to be ready sooner than you thought” she says, indicating my slowly hardening cock. I smile and reply, “It’s because you’re so unbelievably hot that it’s getting hard again”. I looked down at my cock and could tell that it would soon be as hard as it was before. “It may get hard again soon” I say “But I will need a few minutes to rest before I’ve got the energy”. Anna nodded and replied “I understand; I’ll be right here waiting to go whenever you are”. For the next few moments, we just sit there in naked silence until Anna breaks the silence and asks “Would you like to go to bed?”.

I smile and answer “Now that would be a good idea; your room or mine?”. Anna smiles and says “I want to take my boyfriend to my bed; so my room”. We stand up and Anna leads me into her room where we get straight into bed. We cuddle for a few moments before we wrap our arms around each other and begin kissing passionately. We rolled around the bed as our hands roamed over each other’s bodies and our tongues explored the inside of each other’s mouths. Honestly at this point, I would have been more than happy to settle for the naked kissing; but thankfully that was not to be. “Let’s fuck” Anna said, breaking the kiss, to which I reply “Well, if you absolutely insist”. I looked down as I fisted my cock to Anna’s cunt.

With a smile, I pushed my cock slowly forward, within a few seconds, all of my rock-hard fuck tool was inside the naked teenager. “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 anyone’s attention and run the risk of getting caught”. This made sense as after Kara and myself had been caught by Ariadne, I wanted to avoid getting caught in the act for a second time. “Oh god this feels so good” Anna says with a pleasured groan “The first fuck as boyfriend girlfriend”. I leaned down, kissed her, and replied “The first of many fucks as boyfriend girlfriend”. She wrapped her legs around my waist and held me tightly as we began fucking.

It felt good to be able to have a normal sexual encounter with Anna, though that is not to say that getting blown off by her in the swimming pool bathroom was not fun to, which it was. As well as taking the bath with her which was just as fucking good. As I thrust in and out of Anna’s cunt, I could not help but think about this is roughly at the point where Kara and myself got caught fucking and that if we were going to get caught then now would be the most awkward time for that to happen. I listened for the sound of Ariadne coming into the clubhouse, and when I heard nothing, I breathed a sigh of relief. I kissed her gently and said “You are so much better than Li ever could have been”. “Oh god thank you so much” Anna says “This is just what I want from a boyfriend”.

I leaned down and kissed Anna passionately; kissing while you’re up inside a girl is just spot on. We rolled around for a few moments until Anna ended up on top. “I’m going to take my time” Anna told me as she slowly started bouncing up and down my cock “I want this to last as long as it can”. I reach up and gently hold her titties and say “Take as long as you want; we have all the time we need”. As she settles into a slow and steady bouncing motion, at that moment I would not have cared if we’d got caught. Fucking Anna was so much better than fucking Li or Kara. But as good as she was, she was no-where near as good as Ariadne. I pulled Anna down into a gentle kiss where we rolled around for a few moments and ended up with me on top once again.

As I looked down at Anna, and I wished I’d met her before I met Li. If I had met Anna before I met Li then I’d not have cheated on her with Kara as Anna is just so much more hotter than that silly chink bitch. Although I probably would still have had the occasional quickie with Kara if she wanted it. I looked down at the naked Ukrainian girl i was stabbing with my cock and saw on her face a look of pure pleasure and enjoyment. We rolled over and she ended up on top, I looked up at her and she had the same look of pure pleasure on her face that she had when I was on top. I reached up and gently held her slim waist while watching her titties as they jiggled. I reached up and gently cupped her tits in my hands, gently holding them before moving my hands back to her waist.

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