Confessions From a Boarding School Pupil - Cover

Confessions From a Boarding School Pupil

Copyright© 2022 by Drax

Episode 36: Sleep With One Doctor and Call Me in the Morning

Pedo Sex Story: Episode 36: Sleep With One Doctor and Call Me in the Morning - 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  

Once I was alone in my room, I laid back and could not help but to smile yet again. I could not believe the position that I was in; I was now the ‘Hospital fuckboy’ and would be getting laid with hot women on a regular basis. Plus with Dr. Hellruy being able to make my condition worse on command, I would be able to stay in the hospital for the foreseeable future. My cock throbbed in anticipation of all the pussy I would soon be getting. I knew that this made me a child prostitute and I did not give a flying fuck about that. I was getting laid with good looking at hot fucking bitches and I could not be happier. I was so unbelievably stoked at my new job that I could not sleep, which is what I really wanted to do.

I wanted to get some sleep so I could be ready for my spending the night with Dr. Hellruy. I decided to read or play games on my iPad in the hopes it would tire me out. After a few hours of playing a gamer and reading a few chapters of a Star Wars novel, I was fucking ecstatic when I finally was visited by the gods of sleep. I put my iPad away and got settled down. A few moments later, I was taken by the gods of sleep. Sometime later, I was awoken by the feeling of the bedcovers being pulled back. I could not be happier when I saw that it was Dr. Hellruy. “Did I wake you?” She asked with a smile. “It’s OK being woken by you” I replied. I sat up and she leaned down and we shared a quick but passionate kiss.

We broke the kiss after a few seconds and Dr. Hellruy began to undress. “Do not call me Doctor” she told me “We’re an item so call me Liz, OK?”. I nodded and replied “OK Liz”. I then began to undress, but as I was only wearing hospital pajamas, I was bare-butt naked again in no time. “You look so fucking good” Liz told me as she grabbed my cock and stroked it gently “I can tell you like me...”. To emphasize her words, she squeezed my cock firmly, now I had to admit feeling better than I thought it would. She stood before me now clad only in her matching lace bra and panties, and as I stared at her tits and belly, I could feel my cock getting as hard as it possibly could. “Before we fuck, can we just kiss and cuddle?” Liz asked.

I immediately replied “Or course it is; whatever you want to do is what we’ll do”. She smiled, then pulled me into a passionate kiss, letting go of my cock and wrapping her arms around me. I wrapped my arms around Liz and for the next few moments, we just stood there kissing passionately. After a few minutes of kissing, Liz broke the kiss and told me to “Get in bed”. I got back into bed and watched as Liz moved to the door and locked it and made sure the blind was drawn. “So we’re not disturbed” Liz told me as she swiftly removed her bra and panties and stood before me totally fucking naked. “Wow, you look so perfect” I said to her “We should have done this sooner”. She nodded and replied “If I could have done then I would have”.

She got into bed next to me and it felt so good that I felt as if I was going to blow my load right then and there. “All that matters is we’re doing it now” Liz said “So let’s just lay back and enjoy it”. For the next few minutes, we just laid together in bed, cuddling up to each other. And if this is all I would get to do with Liz tonight, then it would not be time wasted. With one hand on her flat belly and the other on the small of her back, I felt as if I could have stayed laid there like that with her for the rest of the night. After a few more moments of naked cuddling, Liz gently slid her hand down my body and gently took my cock in her hand and slowly started to jerk me off. I looked into her eyes and she leaned in and we kissed gently.

As our tongues began exploring each other’s mouths gently, I once again could not help but internally scream in joy at the fact I was in bed with an incredibly sexy doctor and soon we would be fucking. This was no ordinary doctor I was in bed with, I was in bed the Doctor that was essentially my pimp and I did not care about that latter part. Yes you did indeed read that right, I did not care that I was in bed with the doctor who was my pimp. After a few moments, she broke off the kiss to focus all her attention on the cock in her hand. She stared at me intently, pumping in long, slow strokes, from the base to the tip; all while maintaining eye contact. She stopped jerking me off and said “I want to go on top”.

I nodded and answered with a smile “Never argue with a lady”. She climbed on top of me and gently fisted my cock to her cunt-hole. She slowly sank down my engorged fuck-tool until she bottomed out. She just stayed there for a moment, grabbing my hands and placing them on her waist. “I’ve been looking forward to this since you first came in” Liz said as she slowly started bouncing on my cock “Now I’m actually fucking you, I’m going to enjoy this...”. I sighed in pleasure and replied “I’m already enjoying it Liz”. She smiled at me as we began to fuck. For the next few minutes, neither of us said anything, preferring fucking in silence. It was at times like this that I wished that I had four hands.

With four hands I could keep two on her slim waist and two on her impressive cleavage. I slid my hands up her sides and then onto her chest, lovingly kneading and squeezing her tits gently. As we fucked, I could not help but reflect on just how fucking good my life was. I was now in a position where I would get more sex in my life than most people would ever get in their lifetimes. Despite the fact that I was essentially now a child prostitute, I could not have been happier with my life. And despite the fact that I would be having sex with many different women and girls, there were indeed more than one that I genuinely cared about; Shania and Liz being the main ones at that current moment in time.

A few moments later, I was shaken out of my thoughts by Liz when she pinched my nipples and said “Come back to me Jay; don’t zone out on me”. I smiled and replied “Sorry, I was distracted by how fucking hot you are”. I leaned up and kissed her tits gently, Liz sighed and said “That feels so good”. I laid back down and said “I’m glad that you like it”. She looked down at me, smiled and replied “I like EVERYTHING about you Jay”. She then leaned down and kissed me passionately while still riding my cock. As she sat back up, I felt her clench her cunt muscles around my cock, and because of that it did not take too long for the familiar tingling feeling in my cock to make its pleasurable presence felt, which meant only one thing.

“Oh god, I’m almost ready” I grunted through gritted teeth “I’m almost ready to cum...”. Upon hearing this, Liz began bouncing up and down on my cock faster and told me “Not yet baby-boy; I’m closer to cumming than you...”. A few bounces later, she did just that; “Here I come baby boy” Liz grunted “Oh god here I cum...”. A few grunts later Liz did indeed cum, as she moaned in pleasure, I grunted and gritted my teeth as I tried to hold off on cumming for as long as I could. I lasted as long as I could but I did not last very much longer. A few seconds later, my cock exploded and released it’s load of hot cum up inside the gorgeous doctor that I’d just fucked. Liz bounced up and down on my cock a few more times until all of my cum was up inside her.

She then stayed on-top of me for a few moments as she caught her breath. For a few moments, we just laid there in silence with the only sound being the sound of our breathing. “I fucking love you” Liz said, looking me directly in the eyes “This is not some post-sex; I really do fucking love you”. Before I could reply, she kissed me. “I can see why Nurse Shaik likes you so much,” she said, slowly breaking the kiss “I can’t believe I have a 14 year old boyfriend”. She rolled off me then cuddled up to me as I said “I can’t believe that I have a nurse girlfriend”. As we lay on the bed, our naked bodies slowly cooling, I found it hard to believe that I had yet another adult woman who said she loved me after we’d fucked.

“I take it we have to keep this on the down-low?” I asked, already knowing the answer. “Alas we do, yes” Liz replied “For the sake of your job and not getting a whole lot of people arrested; the two of us included”. I already understood the reasons why we had to keep it quiet, it just felt like the right question to ask. “Can you spend the night?” I asked, to which she replied “Of course I can, though I’ll have to be up early tomorrow to avoid getting caught”. Liz having to get up early was not a problem for me as I understood why she had to be out early. “As long as I can get to say ‘good morning’ and ‘goodbye’ before you leave, I guess that getting up early won’t be a problem”.

She kissed me on the forehead and replied with a slight smile “I think that can be arranged”. I was usually up early when I slept alone so being up when Liz had to go would not be a problem. Liz draped her right leg over mine as she gently stroked my dick and said “What we did was just right, just what I ... just when WE needed”. I nodded and replied “Indeed it was; I will definitely sleep soundly with you at my side tonight”. What I’d just said to Liz was indeed the truth; I did sleep better when I slept next to a woman/girl. Unlike when I had laid with Leanne where I was internally screaming at her calling me her boyfriend, this time it was and did indeed feel different.

I enjoyed laying with her and fucking her, but unlike with Leanne, the idea of Liz calling me her boyfriend did not make me feel nervous. I would not say that I was in love with Dr. Hellruy, but I did care about her more than most of the girls/women that I fucked. “What do you think of your job?” She asked “I mean, what do you really think of the title and such?”. I was silent for a few moments as I had not expected that question. “I do so very much love my job” I replied “The title is spot on and the website is just perfect”. Giving my cock a squeeze, she then asked “I’m glad you like it; do you have anything you don’t like about it?”. Honestly, I could not think of anything about my job that I did not like.

“There is one thing that I can think of” I replied “It’s not a dislike rather its a suggested improvement?”. Liz smiled and asked “And that is?”. I answered with “On the website, maybe there could be something that indicates which women I’ve met and how many times?”. Liz nodded, smiled and told me “Now that is a really good idea”. She kissed me passionately while she gently fondled my cock and balls. She did this for a few moments before stopping and cuddling up to me once again. For the next few minutes, we did nothing but lay there totally naked and wrapped in each other’s arms. After a few more minutes, I realized that Liz had not asked any more questions or said anything else as she had fallen fast asleep.

With Liz now fast asleep, I was able to slide my hand down her back and squeeze her bum and feel her tits as I waited for the gods of sleep to come and visit me. A few moments later, they did come and visit me and I fell fast asleep. I awoke a few hours later when I wanted a glass of water. I smiled and looked at the sleeping Liz as I looked under the bedcovers and as I gazed at her naked form, I knew that I wanted to fuck her yet again, but I did not want to wake her. I slowly got out of bed and went to the bathroom for the aforementioned glass of water, when I went back into the room, I approached the bed and got back in, and then watched as Liz turned over and now had her back to me.

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