Confessions From a Boarding School Pupil - Cover

Confessions From a Boarding School Pupil

Copyright© 2022 by Drax

Episode 21: The Morning After the Night With the Babysitter

Pedo Sex Story: Episode 21: The Morning After the Night With the Babysitter - 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  

During the night, I had to get up and go for a piss; when I’d done in the bathroom I flushed the toilet and went back to my bedroom. When I entered my room, I stopped in the doorway and sighed in pleasure at what I saw. Brook had turned over and the duvet had fallen away from her tits and one leg was hanging out of the bed. She looked so fucking hot I wanted nothing more than to walk over to her and fuck her brains out as hard as I could. But I did not want to wake her, I was more than content to simply stare at her naked form. As I reached down and gently stroked my cock, Brook must have sensed I was not in bed. “Jay...” she says during a yawn “Come back to bed”. She sits up and the duvet falls away from her.

She notices my erect cock and says “Come back to bed, I’ll keep that warm for you”. I smiled and got back in bed with Brook, she cuddled up next to me and began stroking my cock as I gripped her bum gently. She did this for a few minutes, then kissed my cheek and said “There you go; all nice and warm now”. I squeezed her bum tightly and replied “Indeed it is...”. She yawned and said “If you want to put it up me, go ahead”. She yawns and turns her back to me and adds “Just don’t get it in my hair...”. I frowned and asked “Are you sure?”. She yawned and replied “Sure...”. After a few moments, I realized she had fallen asleep. I looked at her and was so very tempted to put my cock up her while she was as asleep; but I decided against it as it didn’t feel right.

Instead I just wrapped my arm around her and cuddled up with her. Though I didn’t fuck her while she was asleep, I did take this time to grope her naked form. Brook was a hot piece of ass and I was naked in bed with her, and I wanted to enjoy feeling her body for a while longer. As I rubbed her flat belly, I also rubbed and squeezed her tits gently. Brook had a fucking hot body and I wanted to make sure that I got my hands on as much of it as I could. I reached down and rubbed the top of her legs then put both hands on her firm ass. I liked her ass and wanted to fuck it, a fact of which I made a mental note to ask Brook about doing it in the morning. And a few moments later, I to was taken by the loving grip of sleep.

I yawned as I turned over wherein my gaze at once fell on the sleeping form of the babysitter Brook. I could have just stared at her sleeping form for hours, but it was interrupted by Brook herself. “Hey there” she said, kissing me gently. “Good morning beautiful” I replied, returning the kiss. We just laid there in each others arms for a few moments, not wanting to get out of bed. “Did you sleep well?” I asked her. “I had the best nights sleep I’ve had in my entire life” Brook said as she cuddled up to me “How about you?”. I smile and reply “Best nights sleep ever”. She kissed my cheek and replied “I could not have said it better myself my love”. I had indeed slept well sleeping next to such a hot girl that I’d fucked.

“So, what were your other girlfriends like” Brook asked “Were they better looking that me?”. I looked at Brook, frowned and asked “What do you mean?”. I knew exactly what she meant, but I wanted her to say it first. “What were your other girlfriends like?” Brook asked with a smile “I’ll bet they weren’t as good looking as me”. I answered with “I’ve only had three girlfriends before you; you’re the best looking one ever”. Brook smiled, kissed me gently and said “That’s why I love you; you’re always honest, plus you’re hot as fuck”. I smile and reply “And I love you to Brook”. What I had said to Brook was the truth and a lie at the same time. I did not love Brook and while she was a hot fuck, I still had feelings for Ariadne.

But out of all the ‘Official’ girlfriends I’d had, meaning Ariadne and Karruche, then Brook was indeed the hottest, at least that is what I told her. “We should get out of bed at some point” I say, to which she tells me “That we should, but lets lay here for a while longer”. As we laid there in each others arms, I had to admit that I was more than a little annoyed that I could not openly sleep with Brook; like I had been doing with Ariadne. But I realized that this would not happen as Ariadne and myself had genuinely been in love while as far as Brook was concerned I was just is total and utter lust with the hot teenage blond babysitter. “Did you really mean it?” Brook asked “I’m the best looking of your girlfriends?”.

I looked at her, smiled gently and told her “Li and Kara were nothing compared to you. You are blond babysitting perfection while the rest are total dirt”. Brook leaned in and kissed me passionately. “My ex-boyfriend never said such kind and loving things about me” she said, breaking the kiss and hugging me “That’s why you are so the perfect boyfriend; you treat me perfectly and you’re hot as fuck and fucking great in bed”. It was always nice to get compliments from the girls I was fucking as it showed they liked me. “I don’t want to get out of bed” I tell her “I want to stay here with you”. To emphasize my point, I rubbed her bum gently and gave it a gentle squeeze. Her bum felt just as god first thing in the morning as it did the previous night.

“As I said before, we’ll have to get out of bed eventually” Brook told me “But not before we’ve had a few more minutes in bed together”. As we lay there in bed, I moved my hand from Brook’s ass and slid it around her slim waist while using my other hand to grope and feel her tits. We then wrapped our arms around each other and started kissing madly. As our tongues explored the inside of each other’s mouths, we started rolling around under the duvet. Brook reached down and gave my cock a gentle squeeze and began to gently toss me off. I laid on my back as Brook continued tossing me off and I said to her “This is SO good; you’re really good at this”. Brook smiles and says “I’m glad that you like it”. Brook stops tossing me off and asks “Would you like me to get on you?”.

I smile and reply, “I’d love that; but do we have the time?”. Brook straddled my waist and replied “We can make the time”. She reached down She reached down and gently took hold of my fully erect cock and fisted it to her cunt-hole. We just looked each other in the eyes for a few moments, neither of us saying anything. “Oh wow that’s the stuff...” was all I said as she slid down my cock, taking it all the way inside her in one swift motion. When it was all the way inside her, she looked down at me as she took my hands and placed them on her slim waist. Brook moved up and down my cock not fast, but in a slow motion. Brooke looked down at me and smiled a smile of love. “oh God” she groaned in pleasure “This is the only way to wake up in the morning; a good fuck with your boyfriend”.

I looked up at Brook and replied “And what better way to wake up than your hot girlfriend riding you”. Now as I have mentioned in the past and that I will go on to mention again, I did not love Brook even in the slightest; it was nothing more than pure unadulterated lust. With a look of total love on her face Brook said “I love you Jay, even though you’re only 14 I really, really do love you”. In response to what Brook had just said, I found myself replying rather swiftly that “I love you to”. Even though I uttered the words, I found it hard to believe that I told Brook that I loved her. I suppose I told Brook that I loved her because I was up inside her. As I have just said I did not love Brook, but when you’re up inside a girl you tend to say whatever comes to mind.

You say what ever comes to mind to keep her happy; or at least that’s what I do. The only other person I said I loved was Ariadne, but wherein I truly meant it when I said it to her, to Brook I certainly did NOT mean it. I was shaken out of my reverie by the sound neither of us expected to hear; the front gate slamming shut. Brook got off me and we sat up in bed, expecting the front door to open and for mother to come home and for Brook and myself to be caught in bed. We both breathed a sigh of relief when we heard the wheelie bin being put back inside the front gate. “It was only the fucking bin man” Brook says as we both lay back down. “We can’t resume the fuck” Brook tells me “We need peace and quiet for that”.

I nodded and replied “Fair enough”. For the next few moments, we were both silent until Brook said that “At some point, we should consider getting out of bed”. I replied with “Do we have to? I just want to stay in bed with you”. We just cuddled for a few moments before Brook said to me “We should get up and out of bed before your mother comes home”. I sigh and say “I suppose you are right”. We both get out of bed and begin to get dressed; which did not take us long. “Last night was amazing” Brook said to me “There is no one else I want in my life and in me than you”. I slipped my arm around her waist and told her a lie that she fell for hook, line and sinker. “And there is no one else for me” I told her “To get inside anyone else now would be absolutely crap”.

She hugged me gently and said “That’s just the thing I need to hear to help me get up and out of bed; now let’s go get some breakfast. Despite the fact that I was not hungry, I went downstairs into the kitchen with Brook where she proceed to put on a pot of black coffee. “You want anything for breakfast?” Brook asked. “I’d love a hot slice of this” I reply, putting my hand on her bum and squeezing it gently. “You can have some later” Brook says with a smile “For now, its just coffee”. Until the coffee was ready, the two of us just sat in silence on either side of the breakfast bar. As we waited for the coffee to brew, I could not help but to think just what life would be like if a full-blown relationship with Brook was possible.

If we could have a full relationship, it would be one of mild scandal as she is my 18-year old boss and I’m just her 14-year old charge. But putting any scandal aside, any potential relationship would be fantastic for just the sex alone. As Brook was not much older than myself, there would be some scandal if we did have a relationship that was known to the public but not as much scandal there would be if she were the same age as my boss. “You are really hot” I tell Brook “Are you SURE you want to be my girlfriend?”. She turns to face me and replies “Of course I want to be your girlfriend; you need to have more confidence in yourself”. I felt the need to ask Brook that as she was so fucking hot. I was so pleased with her reply as it meant she genuinely wanted to be with me.

“I take it the moratorium on condoms is still in effect?” I asked. “Yes indeed it is” Brook replies “I want to feel my boyfriend inside me and not some piece of rubber”. Even though I already knew she didn’t want to use condoms, I thought it would sound good if I asked her again. As Brook turned back to make the coffee, I let my gaze fall upon Brook’s ass and felt my cock getting hard once again. She had a really nice looking bum that I just wanted to get up inside and have my hands on it. “What we did last night was so good” Brook says “But we have to keep it on the down low for a while at least, yes?”. I nodded and replied “Exactly; I don’t want anyone to know we slept together”. This was just what I’d been thinking about, but I did not tell her that.

“We’ll have to keep it secret until you come over to babysit me” I tell Brook “That seems to be the only way we can be together”. What I had just told her was indeed the truth; restricting our relationship to when she babysat for me was indeed the only way we could see each other. “I agree” Brook replied “It will be hard but its the only way to go”. I stand behind her and press up against her and say “That’s not the only thing that’s hard”. She smiles and asks “You don’t want to be doing me when your mother gets home, do you?”. She had a point so I moved back to the table and sat back down, but not before I gave her ass a gentle slap. “Let’s go into the living room” Brook told me “The couch will be more comfortable”.

I got up and followed her into the living room wherein we both sat on the couch. “So, I have to ask you this” Brook says “Are you really OK with being my secret boyfriend?”. I looked at her and could tell that this was a serious question. “Yes, I am ok with it” I replied “It will have to be this way until I’m legal”. Now as you are all aware, I was a little nervous about Brook calling me her ‘boyfriend’ or ‘Her secret boyfriend’ but I had to put up with it to ensure she still slept with me. “Can you wait two years until I’m legal?” I asked, to which she replied “Of course I will; when you’re in love the time will fly by”. I had to play along with Brook and pretend that I loved her when I really did not. I would say that I was in lust with Brook, not love which suited me just fine.

“I would like to be able to spend the night with my girlfriend and not have to rush in the morning” I told Brook “Maybe we can spend the night at your place when you next look after me?”. Suggesting that she could look after me at her place was one of my better ideas. “Now that is an excellent idea” Brook said, slipping her arm around my shoulder “We would be able to take our time and act like the couple we secretly are”. I put my arm around Brook’s waist and rested my head on her shoulder. Right then and there, and that very moment, I did not feel nervous about being her secret boyfriend. and if I was being totally honest with myself, sat there on the couch with the babysitter felt just right despite me not wanting to be in a relationship with her...

After a few moments of cuddling, 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; and it looked good. “Enjoying the view?” Brook asked with a naughty smile. I replied to her question with “Very much so; so much so that I’m going to do this...”. I slid my hand down her shirt and squeezed her tits gently. “If you’re going to do that, lets do it properly” Brook says “But first you need to let go”. I took my hand off her tit and she took off her shirt and bra and sat on the couch topless. “Now if you want to play with them, you can now do so properly” Brook tells me as she lays down on the couch. “Are you sure?” I ask, to which she replies with “Of course, I am sure; now enough talk, get to work”.

I smile and reply “Never argue with a lady”. I lay on top of Brook with my head on her boobies, which as well as feeling really fucking amazing, allowed me to feel and kiss her fucking amazing tits. We did this for a few moments, before I sat up. “Is there a problem?” Brook asked as she sat up. “No, there’s no problem” I replied “I just wanted to change position and have you on top”. Brook smiled and said “Then lets get on with it shall we?”. We changed positions and I lay down while she laid on top of me. She moved up so her boobs were above my face, she then told me “Have fun”. I leaned up and began licking and kissing her breasts, which elicited a groan of pleasure from Brook. We did this for a few minutes before Brook laid on top of me.

“That was fun” Brook told me, to which I replied “Yeah it was”. Brook then asked “So, I take it you like my boobs?”. I nodded and replied quickly with “Indeed I do, they are the best boobs I’ve ever seen”. What I had just said was indeed the truth. At that point in my life, Brook’s tits were indeed the best that I’d ever seen. “When I look after you next, do you want it to be at my place?” Brook asked “That way we can sleep together and take our time”. What she had just said made perfect sense. “Now that is a good...” I begin to reply. I was interrupted by the sound of someone knocking on the front door. We both froze for a few moments as the person knocked again. “Who is it?” Brook asked in a whispered voice. “I have no idea” I replied “Let’s just stay quiet, they might fuck off”.

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