Confessions From a Boarding School Pupil
Copyright© 2022 by Drax
Episode 33: Caught in the Act
Pedo Sex Story: Episode 33: Caught in the Act - 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
After Nurse Shaik had gone, I spent the rest of the morning reflecting on what had just happened with Nurse Shaik. Having her blow me off and spending the night with her was the best thing that had happened to me since I had met Ariadne back at school. As I had often done since I first fucked Ariadne, I tried to figure out just why women and girls liked me enough to fuck me and take me to bed in some cases. As far as I was concerned, I was just an ordinary 14 year old boy, indistinguishable from any other boy my age. I could dismiss Kara, Li, Anna and Vanessa as they were girls my own age and dating girls the same age as you is nothing new. Ariadne, Leanne, Jennifer, Eliza and Shania were a different matter altogether.
They were older than me and in my opinion they could have had any other man they wanted, but they chose me. Now I am not complaining about this, I just could not understand why they and subsequent women and girl liked me as much as they did. I was not going to do anything to change the situation, I just could not figure out my success with the opposite sex. Out of all of the women and girls I’d been with at that point in my life, there were only two that I actually cared about; Ariadne and Shania. I was genuinely in love with Ariadne and had wanted to spend the rest of my life with her before she’d been taken away thanks to that mega-bitch Leanne. And as for Shania, the feelings I had for her were getting stronger each time I was with her.
They would soon be the same as I had for Ariadne, maybe a degree or two stronger. The rest of them were just good looking girls and women that I enjoyed fucking but did not have strong feelings for, and that suited me just fine. After lunch which consisted of Tomato soup and fried potato cubes and ice-cream, I decided to go for a walk. Aside from stretching my legs, it would allow me to check out any good looking women or girls. I made my way to the shop where I got myself a coffee and a Twix. And on my way back to the ward, I stopped at the second floor Observation Area. I only sat here because I didn’t want to risk spilling the coffee which seemed a little hotter than it normally was.
I knew that it would not be pleasant for Shania when I got rid of her, but at that point I did not care. I did not like how clingy she had become and her declarations of love were starting to get more than annoying. As I have said previously, having a purely sexual relationship with Shania would have worked out perfectly if only she hadn’t said that she ‘loved me’ and that ‘We were now boyfriend and girlfriend’. If I am being honest, I never actually loved Shania rather it was better described as being ‘in pure lust’ with her. I could have easily settled into a purely physical relationship with her, but as she’d said what she said that plan was now dead and buried.
Once I’d finished my Twix and coffee, I decided to go back to the ward and headed for the lift. As I waited for the lift to arrive, I checked out some of the girls and women that were in and around the visitors’ and walking wounded entrance. Before you all start on at me, I know that is not the proper name for it. But you see, at the time of writing this, I could not remember its proper name. There were indeed some good looking girls and women, more than on of them I would have loved to get up inside, there was one black girl who looked so cute, but my ‘girl watching’ was interrupted by the arrival of the lift. As I stepped into the lift, a familiar voice called out “Hold the lift”.
I turned around and saw Dr. Hellruy rushing for the lift. I held the door for her and she smiled and said “Thanks cutie”. The lift ride was only a few seconds so we could not strike up a conversation. I did spend the few seconds of the lift journey it trying to discretely look at her ass. “Enjoy the view did you?” Dr. Hellruy asked as the lift doors opened. “Yes, I did” I replied with a smile. “I will have to come and administer another dose of medication to you” Dr. Hellruy says as we exit the lift “It looks like you might need a larger dose”. I smile and replied “I look forward to it”. She winked at me as she left, I exited the lift and went back to the private room. When I got back to the private room, I noticed a really cute girl.
She went into another one of the private rooms and I have to admit that she looked good. I never imagined that at that point that I would end up in bed with her, but if I got the chance then I would not object. She looked to be in her late teens, possibly her early twenties and was of Asian decent. She had long black hair tied back in a ponytail and was wearing hospital pajamas and a green T-shirt; and as she did not see me I went into my room. As I opened my coke, I barely had enough time to take a sip when Dr. Hellruy entered the room. “Is it time for my meditation already?” I asked with a smile. “Not exactly Mr. Wilson” she says “We have a problem and we think you might be able to help with it”.
Now this was something I’d not heard before that someone in a position of respect had a problem that they needed my help with. “What could you need my help with?” I asked with a frown. “We’ve got an emergency coming in and we’re short on space” Dr. Hellruy explained “Which is why I’m here”. She paused, then said “Just for tonight, we’d like you to share this room”. I looked around the room then asked “Can two beds fit in this room?” To which Dr. Hellruy replied “It will be a squeeze, but yes two beds can fit in here”. Just as I was thinking that sharing the room was going to be interesting, Nurse Shaik enters the room and whispers in Dr. Hellruy’s ear then leaves the room. “Trouble?” I asked.
Dr. Hellruy replied “It would appear to be good news; the emergency I mentioned has been taken to another hospital so you don’t have to share this room”. I was relieved that I would not have to share the room with anyone as if I had shared, then I would not have been able to spend the night with Nurse Shaik or Dr. Hellruy. “So, I have the room to myself?” I asked, Dr. Hellruy replied “That’s right, so I can come and administer the medication later without being disturbed”. I then asked, “Why not stay the night? I might need medication during the night”. Dr. Hellruy smiled and replied, “Now that is a good idea Mr. Wilson and one that I will have to take you up on, but not tonight”. I then asked “Work?”.
To which she answered “That and family commitments otherwise I would have”. I was under no illusion that a total hot nut-buster like Dr. Hellruy was single, I would have found it unbelievable if she was single. “I’ll save you a spot and keep it warm for you” I told her, patting the bed “Just let me know when you’ll want it and I’ll have it ready for you”. I did not think that Dr. Hellruy would actually be able to spend the night with me, but I felt that I had to at least offer her the chance. “Next time I’m free, I’ll take you up on that” she replied with a smile. She leaned over and kissed me then told me that “I have to go, but remember to keep that spot warm for me”. She winked at me then left.
I smiled knowing that I would be able to sleep with Dr. Hellruy besides just fucking her. I finished my coke and sandwich and lay on the bed for a few moments. I could not stop smiling at the thought of spending the night with Dr. Hellruy and being able to have my hands on her and be inside her all night. While this was something I was looking forward to, I knew that cuddling up to her would be good but not as good as it was with Nurse Shaik. I must have dozed off as I was woken by housekeeping who were bringing a hot drink around, of which I had tea. Once I had finished my tea, I spent the rest of the afternoon playing on my iPad and watching the world go by outside my window.
As I settled into playing a game, I got an email from Leanne which caught me off-guard as I did not know she had my email address. I was not in the mood to tell her to ‘Go to hell’ so I ignored the email. And as she did last time she tried to contact me via Facebook, she did not give up so easily. I got 7 more emails from her which prevented me from playing the game as they beeped until they were read. I was more than a little annoyed with her, and seeing as I did not want any more of her begging emails to interrupt me, I opened them. Each email from my former boss and mega-bitch seemingly got more desperate as it came in. The first one read:
“I love you; please forgive me Jay. We can work things out and still be together”.
I grunted in derision and clicked reply:
“You got rid of Ariadne; go to hell you backstabbing bitch”.
After I sent the reply, I clicked on the second message:
“Please do not allow one mistake to ruin what we have. We had something special and we cant let it go because of one mistake”.
I did not reply to that message rather I clicked on the third message:
“I love you Jay. I know you love me to. We have to work things out”.
Instead of replying individually, I clicked on all four messages and sent a group reply:
“You got rid of Ariadne, the woman that I loved. I do not love you, never message me again, go to fucking hell”.
I sent the reply and set her emails to ‘Spam’ so that they would be sent to the ‘Spam Messages’ folder. Once I’d dealt with Leanne’s emails, I was able to enjoy playing my game. After belting out a few levels on the game, I decided I’d had enough of gaming for a while. As I clicked off the game, I noticed one last email from Leanne that had come through just as I’d set her emails to spam. Seeing as this one had a large attachment, I grew curious and opened the email:
“Jay, I know you do not want to hear from me again but I beg you to listen to me please. You have to understand that what I did, I did out of love; pure unending love. I knew you would not love me the way I love you while your former teacher was still on the scene. So yes, I turned her in to the council and got her arrested, but I did it for the purest reason anyone could do anything; love. From the first moment you walked into the shop to ask about the job vacancy, to the first time you put your arm around me, to the night we spent together right up until now I still love you. I know you still love me otherwise you would not have replied to the emails telling me you don’t love me. I am begging you Jay, my love, please do not give up on what we had. I love you”
I did not believe a single word that she said after she’d got rid of Ariadne and I was tempted to delete the message right then and there. But my curiosity got the better of me and I opened the attachment. It was a slideshow of photos of the two of us from my first time and the video store right up until the night I spent with Leanne. As I watched the slideshow I would be lying if I said that I no longer found Leanne to be attractive; which she was. But it was not her beauty that was in question rather it was the fact she’d got rid of Ariadne to have me to herself. Some guys might find that flattering, and deep down I suppose I did a little, but that was not the problem here.
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