Confessions From a Boarding School Pupil - Cover

Confessions From a Boarding School Pupil

Copyright© 2022 by Drax

Episode 1: Cumming In Kara

Pedo Sex Story: Episode 1: Cumming In Kara - 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 name is Jay Wilson, I am currently 25 years old and what you are about to read is a record of my sex life from the first time at boarding school right up until the present day. But before we get started, there are a few things that I need to get out of the way first. I have never used any kind of drugs and with the exception of at the specific request of a girl, I’ve never got a girl drunk to fuck her. The oldest girl/woman I’ve been with is 56 and as for the youngest was two days after turning 14. I’ve forced a few girls to have sex with me against their will, though one was coerced into doing so by her parent. There have been times where I’ve almost been caught in the act with a girl/woman and there have been times I’ve actually been caught.

There have been times where I’ve not wanted to fuck where the girl/woman wanted to because of a fear of getting caught. This is also the record of how I went from a normal 14 year old schoolboy to my current status as the ‘fuck-boy’ of my local hospital. The things you will read may seem unlikely but I assure you that what you will read within is entirely true and 100% accurate. In the name of privacy, names have been changed in order to protect the identities of certain people. Everything you will read within is written as best as I can recall it, and any mistakes are entirely my own. Certain situations depicted within I have used the correct terminology when describing them as I’m writing this.

But sometimes when they actually happened, I did not know all the correct terms. You will also read within certain terms and words which some of you might find offensive; these have been included to keep everything accurate. Now that has been explained, lets get started shall we. I started at Bretford Court School just a few short weeks after my 12th birthday. The school was located in the middle of the countryside and had farms within spitting distance at all points of the compass. Which as you can imagine was not a pleasant smelling place every muck-spreading. At first I did not like the school, but that all changed two years later and just a few days after my 14th birthday when I met Li-yang.

She was the 14 year old girl who would become my ‘Girlfriend’. Calling Li my girlfriend was a way over exaggeration of what the relationship actually was. While Li considered me her loving boyfriend, I viewed her very differently. To me she was nothing more than an easy source of sex, a quick chink fuck-toy. She was nothing more to me than something to bang when I was in the mood for coitus. This is why I cheated on Li every single chance that I got, I honestly did not love her, I just loved banging her. And there-in was probably 90% percent of why I cheated on Li. Whenever I wanted to get up inside Li, wanted some oral relieve or just generally wanted some action, 99% of the time Li would say words to the effect of “I want to wait”.

She also said “We have to wait until we can be a proper couple”. I would tell her that we can’t be a proper couple until we leave school at 16 or we move in together, which I told her was not possible with the two of us being only 14. At least I did get some from her occasionally, but it tended to be nothing more than a blowjob. The first time I cheated on Li was during the ‘Special Weekend’ of the winter of 1997. Before we go any further, I feel I should explain what the ‘Special Weekend’ was to avoid any confusion. The ‘Special Weekend’ was a school-originated holiday where those that could go home for the weekend did so, particularly those who lived in Bristol or Birmingham or the surrounding areas.

With a majority of the kids gone, the weekend was made a bit ‘extra-special’ for those of us that lived to far away to go home for the weekend. On that Friday morning, I found out that Li would be going home for the weekend to attend a family funeral, so my weekend started with me saying goodbye to Li and telling her that I would see her after the weekend. After I gave her a quick kiss goodbye, I watched her get in the car and drive away. Now I will fully admit that I was a little annoyed to see her go home for the weekend, but I fully understand why she had to go home. I was also relived that she would be gone for the weekend as she had slowly started to become increasingly clingy of late.

The rest of the day at school was average at best; my best friend Matthew and I did as little work as we possibly could on Friday afternoon. We spent the rest of the school day just clowning around and throwing pencils erasers around the class at each other. Unfortunately, my high-spirits were dampened by Creosote; the gardener had used it to wipe out some particularly nasty and persistent clumps of weeds near our class. The stench of the creosote made me feel like I wanted to blow chunks, which I came close to doing more than once. And finally, the school day ended we could not wait to get back to my room get out of our stinky school uniforms which were sodden with sweat and wreaked of creosote, and into more relaxing clothes.

At tea, which was our evening meal, we found out who would be at school over the weekend, and there were not many people left over the weekend. Including Matthew and myself, there were seven of us left in school for the Special Weekend. One of those people that would be left in school for the special weekend was 15 year old Kara, who through the power of hindsight, I can now see that she was a total and utter bitch of the highest degree. She was the type of girl who if she liked a boy would go after him whether he had a girlfriend or not. And as my luck would have it, I was to be seated next to her for tea. The evening meal went despite me feeling unwell and wanting to blow chunks more than once.

During tea, Kara told me that since I was feeling unwell if I needed anything that all I had to do was ask and she’d do it. Now as I was feeling unwell, I was not in the mood for Kara’s flirting and sexually suggestive actions. I wanted to tell Kara to “Get stuffed” in stronger terms but alas I could not as I was at the tea-table and there was staff around. I told her I didn’t need any help and that all I needed was peace and quiet and maybe to lie down in my room for a while after tea was done. When the evening meal was over, Matthew and I volunteered to clear the dishes away and set the table for breakfast. Now I can assure you that we did not volunteer to do this because we wanted to be helpful.

We did this so we could wax lyrical about our favorite topics; Dr. Who, Star Wars, and Power Rangers. It also gave me some peace and quiet away from Kara, who Matthew pointed out to me after the fact, that she was flirting with me. I told him I knew she was flirting but that as I did not feel well, I wasn’t really interested. Knowing that I hardly got any from Li, Matthew suggested that I take advantage of Kara’s advances to get me “Some sweet sex with a future whore”. I agreed and said that I’d do just that once I felt better. A half-hour later, we had done the dishes and set the table for breakfast so we headed back to our group’s living room, and as I was still feeling rather unwell, to my annoyance I saw Kara.

It turns out that as there were only seven of us left in school for the weekend, it had been decided that St. Pat’s living room would be used for those of us left. Despite what I’d said to Matthew, I was still feeling unwell and had hoped I would not have to see Kara until the following morning but I was annoyingly disappointed; I was in no mood to argue or complain about it. Opting to sit at the back of the living room so I could play checkers with Matthew in peace and quiet, I had hoped that Kara would leave us alone; I was wrong. No sooner had we started our game, she sidled over to us and sat at the corner of the table under the pretence of watching us play checkers, but both Matthew and myself why she was really there; to flirt with me.

Deciding this was as good a time as any, I decided to allow Kara to flirt with me and even flirted back a little. Kara told me that she knew I couldn’t resist her advances and that Li would never have to know. I asked what she meant and she replied by putting her hand under the table and squeezing my crotch. She kept her hand there for the next few minutes as Matthew and myself played checkers. I have to admit that Cara squeezing my crotch felt good. After about 10 minutes, Mr. Grimms had entered the living room. I got up and told him that I still did not feel very well and that I was going to go lie down in my room for a while. He said he’d come to check on me later and would wake me up when supper was ready.

But before I went to my room to lay down, Mr. Grimms had the school nurse come to the living room and give me some medication. Nurse Shelly Anderson arrived quickly to give me some medication, she told me that the medication would help me sleep, though she did whisper that she could help me sleep better than the meds. I replied that I would prefer that to the meds but since we couldn’t, I took the medication. thanked Mr. Grimms and Nurse for their help, then I went to my room where I enjoyed a couple of hours of blissful peace, quiet, and sleep. True to his word, Mr. Grimms woke me up when supper was ready, and much to my surprise, I felt a whole lot better than when I went to sleep. He also told me that he checked up on me a few times while I was asleep.

He told me that aside from a few mumbled curse-words I was fast asleep. When I got back to the living room, and seeing as I was feeling better, I felt as if I could hold down more than the single cup of tea and slice of toast that I’d had for the evening meal. Sitting at the back of the living room with Matthew, I had hoped I’d have been able to eat my flapjack and drink my coffee in peace and quiet with my best friend but as you can probably guess I did not get that. Kara soon sidled over to us and sat at the corner of the table next to me. Matthew tried not to let it show that he was doing his best to not laugh, but as he was my best friend I did not slap him with a flapjack. Kara sat as close to me as she possibly could without sitting on my lap.

She made small-talk with Matthew and flirted with me as much as she could without making it too obvious to anyone else in the room. Now up to this point, the maximum edge of Kara’s flirting had gone no further than sitting close to me, resting her head on my shoulder and putting her arm around my shoulder; but during supper, she went one step further. When Mr. Grimms turned his attention to fixing the TV volume, Kara put her hand under the table and onto my leg and rubbed it. Now I will admit that this caught me off-guard, but before I could tell her to stop as she could get caught, she quickly moved her hand onto my crotch and squeezed it again. She told me that she could tell I liked it, giving my rock hard cock another squeeze.

She did this as if to illustrate her point. I looked at her and she simply smiled before getting up from the table and sitting in front of the TV. I asked Matthew if he saw what she did and said that indeed he did and asked what I was going to do about it. I told him that given the fact Li had not yet allowed me to get up inside her, I was going to see how far I could go with Kara. He said that I was definitely going to get inside Kara sooner than I would ever get inside Li. I sat on the couch and a few moments later, Kara came back into the living room and sat next to me. Given how the couch was placed in the living room, Kara could and did put her hand on my leg without being seen.

I must have dozed off because when I woke up, Kara was cuddled up next to me on the couch. I looked at my watch and saw that it was 9:30 pm and I’d been asleep for at least an hour. Matthew of course did nothing to wake me up as he thought it was funny. As I tried to get up from the couch without waking Kara, I noticed that the top button of her shirt was undone which at the angle I was sat at allowed me to get a quick glimpse of her cleavage. I moved my gaze away from Kara and managed to get up from the couch without waking her. It was then that I realized that the button on her shirt could not in any way whatsoever have come undone on its own; meaning that she had to have undone it herself. Now as I mentioned previously, the problem with Kara was that she was a bitch.

She was the type of girl who if she liked a boy would go after him whether he had a girlfriend or not. And much to my embarrassment I only realized then that it became clear she was flirting with me as she obviously liked me. Before the Special Weekend, Kara had never shown any interest in me, and the reason she was trying it on with me because Li was not at school over the weekend. I was most assuredly going to use this to my advantage and see if I could fuck Kara. I stayed on the couch with Kara until 9:30 pm when we all had to go to bed so I quickly went to my room. When Matthew came in a few moments later, he told me that Kara wanted to know where I had gone; wherein I jokingly told him that if he told her where I was, I’d slap him.

I also said that after slapping him, I’d him sleep in the hallway so I could fuck Kara. He said that he said I’d gone to bed early as I was still feeling a bit off; which was the truth. I got changed into my pyjamas and went to the bathroom to fill my juice bottle since the sink in our room was not working. As I was about to enter the bathroom, Kara called out to me as she had been waiting just inside the doorway to the bathroom; wearing her pyjamas and dressing gown. Kara said that she wanted to talk to me without the fear of being overheard as we’d not had any privacy for the rest of the day. I told Kara that I was still not feeling well and was not really in the mood for her flirting which is when she made her move; she kissed me.

It was easy to say that I was caught off guard by this, if I’d not been feeling unwell then I would have seen this coming. But since I wasn’t feeling well I didn’t. For a few moments, I did not stop the kiss as this was what I had wanted from the moment she started flirting with me. After a few moments, I broke the kiss and told her that I had a girlfriend in Li and that I would not cheat on her. She said to me that since Li was not at school for the weekend, we could have some fun without her ever having to find out. She also told me that there was no harm in two people enjoying the company of each other as we would be causing no harm or problems. Once again I pointed out to her that I had a girlfriend.

Kara replied to this by saying that if Li would not put out for me then she would. Kara then asked me what harm it would do? Li would never find out if neither of us told her. She also said what we did would only be known by the two of us. Kara also pointed out to me once again that what would be the harm in two people who like each other having some fun without Li ever having to find out. Kara noticed that I’d been staring at her cleavage and said that if I was not attracted to her then I would not be staring at her chest. I was embarrassed that she had caught me staring at her chest and there was no way I could deny it. She then did something else that I did not expect her to; she undid her dressing gown and took it off.

It was at this point I almost had a fucking heart attack. Her chest was small but nice and I had to make sure I didn’t drool. She asked me if I liked what I saw and I remembered just stammering and stuttering in reply. I stuttered and stammered at the sight of the half-naked girl that was stood before me. Kara smiled and pointed to my pyjama bottoms, where if I was lying down, I would be “pitching a tent”; she said I obviously liked what I saw. My cock was indeed at full hardness and had been since we kissed. I tried telling her that a half-naked girl would get any straight man aroused but she seemed to know I was trying to cover myself, which is more than can be said for her. I had to admit that Kara did indeed look good which she seemed to know.

The source of this story is Storiesonline

To read the complete story you need to be logged in:
Log In or
Register for a Free account (Why register?)

Get No-Registration Temporary Access*

* Allows you 3 stories to read in 24 hours.

 

WARNING! ADULT CONTENT...

Storiesonline is for adult entertainment only. By accessing this site you declare that you are of legal age and that you agree with our Terms of Service and Privacy Policy.


Log In