Confessions From a Boarding School Pupil - Cover

Confessions From a Boarding School Pupil

Copyright© 2022 by Drax

Episode 22: Head on the Road

Pedo Sex Story: Episode 22: Head on the Road - 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   Oriental Female   Hispanic Female   Indian Female   Anal Sex   Massage   Oral Sex   Tit-Fucking   Voyeurism   Public Sex   Teacher/Student   Prostitution  

As I sat in my room hurling abuse at a video-game, I could not help but think about Ariadne and how I would not see her again. I had just got used to having a girlfriend only to have her taken away from me so soon. Despite not wanting a girlfriend at first, I had come around to the idea of having my hot-as-fuck former gym teacher as my girlfriend. This would explain the feelings of guilt I’d had when I first stared at Brook’s ass and when we’d fucked both times. I now felt no guilt at having fucked Brook since Ariadne was no longer in the picture. I now had a new girlfriend in the form of my blond babysitter. That said, I would drop Brook like a hot stone if Ariadne ever came back.

That is no disrespect towards Brook, but Ariadne was just so much more hotter than my babysitter ever could hope to be. That said Brook was a good fuck and I hoped that I would get the chance to get up inside her once again. I did find it interesting how I ended up in bed with Brook; it started off by me giving her a compliment on her bikini, her crying then us kissing and ending up fucking in bed. I had figured out that her boyfriend was not to supportive of her and said some unpleasant things to her, which is why she cried when I complimented her. Despite how I ended up in bed with her, as I said just a few lines ago, Brook was a good fuck. Plus she was a hot and skinny blond which helped.

For obvious reasons, I hoped that Brook would come back to babysit me in the very near future, hopefully wearing her cute red bikini. I knew that there was an easy way into her pants and that was to compliment her and say that her ex-boyfriend was a total prick. After briefly getting my cock up inside Kara’s ass, I wondered if Brook would be up for me fucking her up her bum. I made a mental note to ask her if she’d be up for letting me fuck her sweet ass. And on the subject of Kara, I also made a mental note to ask Brook if she’d be up for taking a hot bubble bath with me. Remembering how good it was to bathe with Kara, then taking a hot bubble bath with Brook should be so many fucking times better.

I also began to think what it would be like to bathe with Mia and found myself wanting to take a hot bubble bath with her. I toyed with the idea of going to see if I could get a booty-call with my middle-eastern beauty, but I could not think of a good enough reason to sneak out and see her. I silently cursed the fact that we did not need any groceries so I could not use that as an excuse. I also cursed the fact that I was not home alone as I’m sure that Mia would have come over to ‘Babysit’ me. I’d only had one encounter withy Mia so far and wanted more. I did not how or when Mia and myself would get naked again but one thing I did know was that we would end up naked again and that was for certain.

Just as I was about to get up and change games, I was interrupted by the phone ringing. Now I have to admit that I was tempted to just let the phone ring off, but that choice was taken out of my hands as my mother answered it. “JAY, ITS FOR YOU” my mother called out. I got up and picked up the phone and said “GOT IT”. When I heard her put the phone down, I asked “Hello?”. I was surprised when I heard Mia’s voice on the other end. “Hello my teenage fuck-toy” she says “How are you feeling?”. I smile and reply “I’m doing well, thank-you. How about you?”. She replied with “I’m fine; I just called to say we can meet up in a few days; if you’re interested”. I smiled and replied “Good; I’ll let you know what day; bye”.

After she’d hung up, I put the phone back down and returned to my bed and video game. I smiled at having spoken to Mia and knowing that we could meet in a few days. “I wonder where we’ll do it this time?” I asked myself with a smile “I hope we get to go to bed”. While I had enjoyed fucking Mia in the armchair in her living room, I really wanted to get her into bed. As I swore away at the video game, I could not help but think about the fact that she had ‘groomed’ me by flirting with me and saying she wanted to fuck me and always telling me how hot I looked and saying she’d like to see me naked. None of this really bothered me as it all boiled down to me having sex with a hot girl in her mid twenties.

Now as you might have already guesses from what you have read in previous episodes, I do so very much enjoy having sex. And while some of you may consider me a victim of sexual abuse, and the law might very well agree with you on that, but here’s the kicker; I do not agree with you OR the law. I am in no way a victim of any kind or form of sexual abuse. Every sexual things that has been done to me or by me I have done willingly and with enthusiasm. I do not understand why, if anyone were to find out the sex I’d been having and with who, would say that I was a victim of abuse and my sexual partners were not that but my abusers. As you can see, they would be talking total fucking bollocks.

I paused the game to go to the bathroom, and once I’d finished the piss and flushed the toilet I cast my glance downwards to my semi-erect cock. I found it odd that so many girls at Brentford Court and here at home were so enamoured with it. If it gave them pleasure then I was not going to deny them it as I got as much fun out of it as they did. As I was feeling a bit horny, I briefly considered jacking off into the toilet, but as I felt that was to seedy I decided not to do it. I headed back into my bedroom but now I was sporting a rather impressive hard-on and had no way to abate it short of tossing myself off. As odd as this may sound, I decided not to toss myself off until I finished the game I was playing.

After loosing at the game I was swearing at, I decided to give up on the game. I’d had enough of the game for a while and put on a DVD. I never got anywhere near anything like that as my thoughts were interrupted by the ear-piercing sound of the doorbell. Cursing the wretched piece of crap, I ignored it and tried to carry on with selecting a DVD. But my gaming was interrupted by my mother. She yelled up from the bottom of the stairs “JAY, YOU HAVE A GUEST”. I got up off my bed and went downstairs to see who it was. And when I got to the back door, I was surprised to find it was my boss Leanne. “Leanne, I’m not late for work am I?” I asked, thinking I was, not that I’d ever been late before.

“No, you’re not late for work” Leanne replied with a smile “But I do need to ask you a huge favour”. I stepped aside and said “Please, come in”. As she stepped in, I could not help but snatch a quick glance at her bum. I stepped into the kitchen with her and she said to my mother “I need Jay’s help with a serious problem”. Ever one to have a joke, I smiled and said “I told you not to open the crack den at the shop”. She turned to me and said “It’s not the crack den, its the porn studio”. My boss could make me laugh, which is one of the reasons I liked her so much. “The problem I need Jay’s help with is at home” Leanne told my mother “My security alarm is screwed up and I don’t feel safe without it”

“Given the fact that there were to break-ins on my street these past three weeks” Leanne added. For a second, I was confused as to why Leanne was at our house talking about an alarm, then what she said next made it all clear. “As my alarm is not working, could I ask Jay a favour?” Leanne says “Could he stay at my place until the alarm is repaired?”. Knowing why she wanted me to stay at her place, I still had to act confused. “Why me?” I asked “I mean why not ask a family member?”. I knew why she was asking me, I just had to make out as if I didn’t know. Leanne turned to me and “My nearest family member is in Manchester and as for why I asked you, that is simple; I trust you”.

This was all an act on her part as she was just saying this so she could take me home and get me into bed, which I did not mind one bit. I turned to my mother, who said “Its not up to me, its up to Jay and if its OK with him then its OK with me”. Leanne turned to me and asked “So, will you help me or leave me all on my own?”. I smiled and asked “So if you’re on your own, I can just swipe your car?”. Seeing my humour for what it was, a way to deflect attention away from her true intent, Leanne smiled and replied “You can’t drive, so why would you steal my car?”. I chuckled and Leanne asked again “So, will you help me?”. I waited for a second before I replied “As long as there is coffee, I’ll do it”.

My mom smiled at me and told me that “I’m proud of you for helping your boss like this”. I chuckled and replied “If there’s free coffee them I’m there”. As I have previously mentioned, I was using humour to deflect my true feelings about what had just happened. I was in fact overjoyed that I was going to be able to spend time in bed with my boss. “So, when do you need me?” I asked, to which Leanne replied “As soon as possible; I have a few errands to run and I need my house looking after”. I turned to my mother and said “I might have to leave a little early”. My mother nodded and replied “No problems, you are a good person for helping your boss in her time of need”.

I was thankful that my mother did not know the real reason I was helping Leanne or she never would have let me go. “So, let’s get going” Leanne says “I don’t like leaving my house unprotected”. I got my jacket and trainers on, and as I headed for the door, my mother once again said to me that “You are a good man for helping your boss”. I smiled and said “Coffee me like, go where it is free”. I followed Leanne out of the door and down the footpath. As I closed the front gate behind me, I turned back and waved to my mother, who waved back. I got into Leanne’s car and we drove away. During the drive to Leanne’s house neither of us said very much, not because we had nothing to say.

I have to admit to feeling somewhat nervous about what we were on the way to do; even though I knew there was no reason to be nervous. I would soon be doing something that I’d wanted to do for so long. I suppose finally getting to do something that I’d wanted to do for so long was reason enough to be nervous. I was also reluctant to admit this but I was nervous about being able to perform well enough to satisfy Leanne. Sure I’d fuck other girls and women before, but this time it was different. This time it was someone who had genuine feelings for me, and so I wanted to be able to sexually please her. I suppose it was my secret worrying about not being able to please Leanne that made me the most nervous.

We did not say much because we both knew what we were going to soon be doing so there was no reason to talk about it. Unexpectedly, half way to her house, Leanne pulled over into a lay-by and asked me “Would you like a warm-up before we get to the main event?”. Knowing exactly what she was talking about, I replied with “I’d love a warm-up, thank-you”. Knowing what to do next, I undid my seat belt and unzipped my trousers and got my cock out. “Get ‘em down” Leanne said. “No problem”, I replied with a smile. I pulled down my trousers and pants and slid them down to my ankles as Leanne undid her seat belt. “This will get you in the mood for the fun later” she told me as she leaned over.

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