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   White Female   Oriental Female   Hispanic Female   Indian Female   Anal Sex   Massage   Oral Sex   Tit-Fucking   Voyeurism   Babysitter   Public Sex   Small Breasts   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 skinny hot blond babysitter. That said, I would drop Brook like a hot stone if Ariadne ever came back to me.

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 simple and genuine 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 a lot.

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 than it ever was with Kara.

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 with 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; and was something to look forward to.

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 babe”.

After she’d hung up, I put the phone down and went back 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 middle-eastern 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.

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 enamored 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. As I sorted through my library of DVDs, I glanced down at my cock which was tenting in my trousers and once again contemplated tossing myself off, but as before I decided against it. I then had the idea of calling Mia and seeing if she was up for some super sexy fun time but I had to nix that as I wasn’t free at the moment. It was at times like this that I wished Brentford Court was still open as I had a few fuck buddies I could choose from whenever I wanted to get laid. 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 selection of a DVD 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 favor”. I stepped aside and said “Please, come in”. As she stepped in, I could not help but snatch a quick glance at her bum, and could feel my cock aching to get up her. 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 my home” Leanne told my mother “My security alarm is screwed up and I don’t feel safe without it”. It looked as if my mom was buying what Leanne was saying. “Given the fact that there were two break-ins on my street these past three weeks; one only last night” 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 favor?” 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 as you all can imagine 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 humor 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 or three them I’m there yesterday”. As I have previously mentioned, I was using humor 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 sat down and got my jacket and trainers on. And as I got up and 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. Then with a wink, she pursed her lips into a bow and slipped the tight fleshy ‘O’ around the tip of my cock. Smoothly, she continued to sink down the shaft, taking the prong deeper into her wet maw to the accompaniment of my pleasured hiss. I placed one hand on her head and then closed my eyes as I enjoyed the blowjob. This was the result of the sexual tensions that had been building between Leanne and myself for many months. We had shared the odd glance and maybe an extended hug or a quick grope, but this was the first time it had gone beyond that.

I knew that what were doing was even more illegal than what I’d done with Brook but at that very moment I just did not care. When you are with the right woman or girl, getting a blowjob from them can really calm you down, or at least I find that it calms me down. I looked down at Leanne, who looked up and winked at me as her head bobbed up and down on my dick. While this was not my first blowjob, it was the first time I would be blown off in a car. I looked out of the window and for a second it felt as if my heart had stopped and my blood had run ice cold. I thought that we were going to get caught as a car looked as if it was approaching us. Thankfully the car drove past us and pulled in at the far and of the lay-by.

I breathed a sigh of relief and said “For a moment I thought we were going to get caught”. Leanne looked up and briefly stopped the blowjob and told me “I picked this spot so we would not be seen”. She indicated the trees to the right of the car and said “Those trees will provide us with all of the cover we need”. I had to agree with her, the way the trees were hanging over, no one would see us unless they were stood outside the car and were looking in. “I made sure this was a secluded place before I picked you up” Leanne told me “No one will see us or catch us”. Leanne leaned up and kissed me passionately while keeping a gentle grip on my cock. As I breathed a sigh of relief, Leanne kissed the tip of my cock and resumed the blowjob.

For the next few moments, I just sat back and enjoyed the blowjob. I watched as Leanne’s head bobbed up and down my rock-hard cock I sighed in pleasure. If this was how good car blowjobs were then I made a mental note to ask Leanne if we could do this again. She stopped sucking me off and looked at me, then without saying another word she kissed me and stuck her tongue into my mouth while gently stroking my cock. She kissed me madly like that for a few seconds, and when she broke the kiss I was out of breath. “Wow ... that was intense” I say as I try to catch my breath. “Glad you liked it” Leanne says with a smile and she kisses me gently “But now it’s back to the main show”. With a wink she took my cock back into her mouth and resumed sucking it.

I closed my eyes, sat back and enjoyed the feeling of my middle-aged boss sucking on my teenage cock once again. As this blowjob was taking place almost right out in full view of the public, I made a mental note to see if Leanne would be up for sucking or even fucking outside when we got back to her home. The idea of being out in the open and engaged in sexual activity really turned me on. As she sucked me, I put my hand on her jeans-covered bum and squeezed it gently. Even though I was feeling her bum through her jeans, it still felt fantastic and knowing I would soon get to touch it proper was all the more fun. I looked down at the middle-aged woman going to town on my cock with her mouth and smiled.

I was only 14 years-old and already in that point in my short life I’d had more sex than anyone else I know; be they sexually active teenagers or sex-addicted adults. She looked up at me, well aware that this pleased me and sensing that I wanted to hold off on cumming for as long as I could. Being sucked off in my bosses car was one of those fantasies that I’d had about Leanne, which was now coming oh so very true. I looked down at her as her head bobbed up and down my cock and smiled; my boss gave great fucking head and I would soon find out just how good in bed she was. I could have just sat there and let her suck me off all night. But that was not to be, as after a few more minutes, the tingling feeling in my cock grew stronger which meant I was not going to last much longer.

She worked along the length of my cock; from the tip of the head right down to her nose being buried in my emerging pubic hair. she stayed like that for a few seconds then rose back up then back down again. After a few more moments, I could not hold back any longer. “Ooh ... good god ... here it comes” I groaned “Get ready OH GOD I’M CUMMING”. Leanne clamped her mouth around the base of my fuck-tool as I felt the first gob of cum worked its way up the shaft of my cock and into her mouth. As my cock exploded the rest of my cum into Leanne’s mouth, she clamped her mouth around the base of my cock. My boss did her best to not waste any of it and take all of my cum into her mouth. Her mouth clamped around my cock made sure that non of it was wasted.

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