Confessions From a Boarding School Pupil - Cover

Confessions From a Boarding School Pupil

Copyright© 2022 by Drax

Episode 24: The Retard, The Quickie & My Boss' Friend

Pedo Sex Story: Episode 24: The Retard, The Quickie & My Boss' Friend - 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  

When I got home, I still felt like a giant pile of crap so I hurried the fifty feet or so from the bus strop around the corner. As I approached my front gate, I could not help but notice that we had new neighbors moving in one door down from us. “New neighbors?” I asked Matt. “I think so” he replied “If they are, I’ve not seen them before today”. As I walked down the path, I noticed a young girl helping to unload stuff from the boot of a car parked on the driveway. “Vanessa, bring the kettle in next” I heard a woman, who I rightly guessed was her mother, call from the house. Vanessa was a very beautiful if not a totally fucking stupid girl as I would find out later. For a 14-year-old, she had a stunning body.

She was very slim, but fully-shaped. Her long brown hair matched her beautiful brown eyes, and her breasts were developing beautifully. They weren’t very big, about A-size, but they were very firm. Because she was half Filipino/half English, she had nice tanned skin and could often be mistaken for half-black. As i would find out later on, she often didn’t wear a bra, yet still her breasts didn’t suffer from gravity and despite being contained beneath a t-shirt, they stood proudly forward. I went inside and asked my mother “New neighbors?”. She nodded and told me “They just moved in; haven’t met them yet so have no idea what they are like”. I grabbed a soda from the fridge and told my mother “I don’t feel to good so is it OK if I just go lay down?”.

While I was not actually unwell as in feeling like I wanted to blow chunks, the Whiskey I’d had at Leanne’s was still making me feel a little sour. “Of course you can” mother told me “If you need anything just let me know”. I nodded and replied “I will”. I then took my soda and went up to my bedroom. I would have normally laid down on my bed in the buff, but since my mother was home, I put on my pajamas. I soon found myself falling fast asleep. I slept the rest of the day and did not wake up until the following morning. I spent most of the next morning up in my room as I still did not feel very well. Thankfully my mother had left me alone for the most part. Apart from checking on me every now and then, I was left alone in peace and quiet.

But as you can already guess, this would not last. “JAY, I NEED YOU DOWN HERE” my mother called from the bottom of the stairs. I checked my alarm clock and was annoyed to find that it was only 11:30am. “HOLD ON” I replied as I got out of bed and stretched. I was tempted to just go back to bed but mother would just keep calling me until I came down. I then headed downstairs where I saw Vanessa sat at the kitchen table. As I have already mentioned, despite her good looks Vanessa was as dumb as a bag of doorknobs. This may sound harsh but it is the truth, and it was something that would work in my favor as you will soon find out. “Hi...” she said with a cherry smile. “Hello” I replied, I then turned to my mother and asked “And what did you need me for?”.

Mother indicated Vanessa and told me “Ms. Hewlett needs someone to keep an eye on Vanessa”. Knowing what my mother was going to suggest, I decided to have a joke at her expense. “And she wants you to look after her” I said “That’s good of you”. Vanessa giggled and said to my mother “He’s funny”. My mother put her coat on and told me “You’ll be looking after Vanessa; I’ve got work”. Before I could reply, my mother had got her keys and said “I’ll call you both at lunchtime; bye” she then left the house, closing the back door behind her. “So what do we do now?” Vanessa asked. “I have no idea” I answered her “I want to go back to bed as I don’t feel well”. She smiled at me, stood up and said “OK, you can go”. I frowned and told her “I can’t go as I have to keep an eye on you”.

Despite her total dumb-ass intelligence, Vanessa understood and said to me that “You go to bed, I’ll bring you a drink”. I shook my head and replied “I can’t go back to bed, I’ve got to keep an eye on you”. Now despite her previously mentioned total lack of intelligence, she did occasionally hit upon a good idea, and what she said next was not only one of these billion in one ideas, it also worked in my favor. “Why don’t we both go to bed?” she suggested “That way you can rest and keep an eye on me at the same time”. Now I must admit to being tempted to agree and take her back to bed with me, but as she was a total fucking idiot, I had to hold myself back. Taking an empty headed simpleton girl to bed felt like I would be taking advantage of her.

“I don’t want you to get sick to” I said, lying through my back teeth “Besides, you’re only 14”. I know she was the same age as me, but as she was a total dimwit of the highest order, I had to turn her down; that and the fact I genuinely did not feel well; which as you already know was the hangover. “OK” she said with a cheery smile “You go lay down and feel better; I’ll bring you a drink later”. Given the fact that the hangover still had a grip on me, I agreed with her. “OK” I told her “Thank-you and make the drink a coke, yes?”. Vanessa nodded and replied in her usual cheery tone “OK, I’ll bring you a Coke later”. I smiled then went back upstairs and back into bed. I felt slightly guilty about leaving Vanessa downstairs on her own.

But the hangover determined my actions and those actions were that I go back to bed. A few moments after I went back to bed, I fell fast asleep. I awoke sometime later and felt slightly better, so I decided to get up and go downstairs to keep an eye on Vanessa. As I rolled over, I was momentarily confused at what I saw; Vanessa stood at my bedside totally stark bollock naked. Presuming I was still asleep, I thought that what I was seeing was nothing more than a dream. But I soon realized that it was not a dream when Vanessa leaned down and kissed me on my forehead. “What...” I stammered “What’s going on ... why are you naked?”. Vanessa smiled and said “Why not?”. Despite her being stupid, I could not fault her answer.

“But why are you naked in MY room?” I asked as I sat up. “It’s lonely downstairs on my own” she told me “So I thought I’d come up and keep you company”. I yawned and asked “That explains why you’re up here, but why are you naked?”. She shrugged and replied “Why not?” she then added “Besides, you can’t be in bed and be wearing clothes”. As I was about to say something about wearing pyjamas, she smiled at me and asked “You like me without clothes?”. Before I could do or say anything else, Vanessa got in bed next to me and pulled the duvet up around us. “I knew you like me without clothes” Vanessa said as she cuddled up to me. I was momentarily caught off guard as she slid her arm around my waist. For a moment, we just said nothing until Vanessa broke the silence.

She looked at me asked “Do you want to be naked to?”. I was to unwell to put up any kind of resistance, not that I would have done if I was not unwell. “Do you like me naked?” Vanessa asked “Do you?”. I hesitated before replying. But before I could reply, Vanessa asked again “Do you like me naked?”. She pulled the duvet covers back, revealing her naked form yet again. I could not help but stare at it as Vanessa asked “You like me naked, don’t you?”. From the tone of her voice, I could tell that she genuinely wanted an answer. But before I could give her an answer, she took my hand and placed it on her left tit and held it there. “Vanessa, I don’t think I should be touching you like this” I said “I’m supposed to be babysitting you, not touching you”.

That was not what Vanessa wanted me to say, tears formed in her eyes and she pushed me in the chest. “You don’t like me...” she said, crying as she got out of bed “You don’t like me ... your just like the boys at school...”. She then ran out of my room crying. With a sigh, I got out of bed and went after her and found her in the kitchen trying to open the back door, which was on a deadlock. “Are you OK?” I asked Vanessa, reaching out to put a hand on her shoulder. “YOU DON’T LIKE ME” Vanessa yells as she pulls away “YOU’RE JUST LIKE THE BOYS AT SCHOOL”. She tried to push past me to get to the back door, but I stopped her and asked “Will you calm down, please?”. “And what are you talking about?” I asked “What about the boys at school?”.

Vanessa pulled away from me and said “THE BOYS AT SCHOOL DON’T LIKE ME; YOU DON’T LIKE ME”. I frowned and asked “What have the boys at your school got to do with this?”. Vanessa tried to push past me to get to the back door but I stood fast. “THE BOYS AT MY SCHOOL” Vanessa said, tears now forming in her eyes “NONE OF THEM WILL LIKE ME JUST LIKE YOU”. It then dawned on me that my rejection of her caused this display, and it might surprise you to know that I actually felt guilt about it. “I never said I didn’t like you” I told her “I just said...”. She interrupted me and yelled “YES YOU DID, YOU DIDN’T WANT ME”. I knew that this would not be cleared up in a few seconds. This would be a lot harder to resolve and would invariably involve a lot more shouting.

“I NEVER said I didn’t like you” I told Vanessa “I only said it was not right for you to be NAKED in bed with me”. She looked at me, the tears still streaming down her face as she asked “You like me?”. I was thankful that not only had she stopped shouting but that she had stopped trying to get out the back door as she was still stark bollock naked. “Yes, I like you” I told her “I just think it was not right for you to be naked in bed with me”. I then quickly added “I’m not well and don’t want you to catch what I’ve got”. Obviously she could not catch a hangover, I just wanted some peace and quiet until I got over the fucking whiskey-induced hangover. That and I was feeling unwell from the cold I was developing from fucking outside with Leanne.

“So can we go to bed?” Vanessa asked me. “OK” I replied. She took me by the hand and the two of us went back upstairs to my bedroom. “OK, now you have to get no clothes” She says to me “We sleep the same”. Seeing as I was still tired and feeling unwell, I did not argue and stripped out of my pyjamas and got in bed. After spending the night with Leanne, I was not looking to get laid again so quickly, but Vanessa did look so good naked I could not help but want to fuck her. “I still feel unwell” I told her as she got into bed next to me “So can we just cuddle?”. Vanessa nodded quickly and replied “Yes, yes we can”. She cuddled up next to me and put my arm around her waist. She looked under the covers and looked at my rock-hard cock and smiled.

“I did that” she said “I made you get hard”. I nodded and replied “Yes you did”. She rested her head on my shoulder and reached down and gently squeezed my cock. “This feels nice” Vanessa said to me “It feels hard and warm”. She looked at me and asked “Do you really like me?” to which I replied “Yes, I just did not want you to catch what is making me feel unwell”, She smiles and replies “That’s nice; you being nice to me is nice”. For the next few minutes, we just cuddled and it was not long before Vanessa fell fast asleep. I looked at the sleeping retard next to me and still found it hard to believe that a mentally retarded girl like Vanessa could have such a hot body. Despite having an aversion to laying with retards and cripples, Vanessa’s body managed to get me turned on.

And as I gently rubbed her flat belly, I could not help but be disgusted and turned on at the same time. I was turned on by how hot she was, by the firmness of her bum, her flat belly and her perky titties. But I was also disgusted by the fact that she was a retard, a mentally disabled freak, an idiot. But there was no denying that Vanessa was hot, so long as she kept her mouth shut. Not long after she was asleep, I also drifted off. When I got up the next morning, I was relieved to see that Vanessa was not in bed next to me. It was not because I did not want to sleep with her, I did want to sleep with her. I just did not want to have to explain to her mother and mine about why I took a ‘mentally retarded’ girl to bed.

I was also surprised that Id sleet all of the previous day but was glad the hangover was gone, all I had now was the oncoming cold. After I got dressed I went downstairs and was surprised to see Vanessa’s mother sat at the kitchen table. “You must be Jay” she says politely “I’m Ms. Hewlett...”. For a moment, I thought that it was all over and that she knew what Id done with Vanessa, but much to my relief that was not entirely the case as you will soon find out. “Yes, I’m Jay” I replied, hoping I did sound as nervous as I was “Its a pleasure to meet you, Vanessa told me nothing about you”. Ms. Hewlett smiled and replied “She can be a little forgetful at times”. I moved to the fridge and got myself a glass of milk.

I then turned back to Ms. Hewlett and asked “Speaking of mothers, where’s mine do you know?”. She sipped her coffee and replied “Had an early call for work, which gives us time to talk”. I was nervous as I sat down, Ms. Hewlett looked at me and said “I know you slept with Vanessa”. As a panicked look crossed my face, Mrs. Hewlett smiled and said that “Relax, you’re not in any kind of trouble”. When I frowned and she told me “Vanessa was happier than I’ve ever seen her”. She sipped her coffee and said “Also when I came to get her, she said you’d had sleepy time with her”. I again thought I was going to get in shit with Vanessa’s mother for sleeping with her and yet again I was wrong as you will find out below, though I was still nervous.

“There is no need to look so scared” Mrs. Hewlett told me “Vanessa said you just slept naked together and didn’t do anything else”. I was still slightly uneasy but Mrs. Hewlett told me “Will you relax, you are in no kind of trouble”. She got up from the table and went to pour herself another coffee, which afforded me the chance to check her out. Mrs. Hewlett was Caucasian and was about 5’6, had long brown hair tied back in a simple ponytail. She wore a knee length black skirt that while it showed off the curve of her bum, did not show just how good it looked. Even though she was wearing a white blouse and a green sweatshirt, I could tell that she had an impressive set of tits on her. “You look confused” She said to me, to which I answered “I am...”.

With her coffee refill in hand, she sat back down at the table and said “I’m a teacher did you know”. Seeing me frown in confusion, Ms. Hewlett told me “As a teacher, I’m not supposed to do certain things with my students”. For a second, I did not know what she was hinting at. “I’m not one of your students” I told her “I don’t start at my new school until the winter term”. It then dawned on me what she was talking about when she was talking about. “Now you get what I meant, yes?” she asked me, to which I replied “Yes...”. As she got up from her chair, I said “I’m seeing your daughter...”. Ms. Hewlett shrugged and said “That’s your problem”. She walked up to me and stood in front of me and said “I want to see just what my daughter sees in you”.

I tried to reply but all I could do was stammer. She grabbed me by the collar and led me into the living room. “I’m seeing your daughter” I told her “I don’t want to hurt her”. Ms. Hewlett replied “Then don’t tell her” and what she did next took me by total surprise; she stuck her hand down my trousers and grabbed my cock. She squeezed it gently and said “No wonder Vanessa likes you”. I managed to stammer a reply of “Thank you ... yes ... wow”. Ms. Hewlett pulled my trousers forward and looked down at my cock and smiled. “Very nice” she said “Very nice indeed”. She took her hand out of my trousers and said “I’ve seen yours, now you can see mine”. As she began to undress, I felt like my cock was going to explode.

When she was down to just her bra and panties, she told me “Your clothes, loose ‘em”. I wasted no more time and pulled my clothes off as quickly as I could and was soon naked with my cock standing straight out in front of me. Ms. Hewlett removed her bra and panties and stood before me as naked as I was. Ms. Hewlett grabbed hold of my cock and guided me to the arm chair and pushed me down into it. “Good boy” she said as she climbed onto the chair and knelt over my cock “Now lets see just how good you are”. She fisted my cock to her cunt-hole and sank down, quickly taking it all in. She put her hands on my shoulders and told me to “Hold my waist”, which I did. “This is just right” Ms. Hewlett says to me “This is just what I need”.

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