Confessions From a Boarding School Pupil - Cover

Confessions From a Boarding School Pupil

Copyright© 2022 by Drax

Episode 58: A Deuce of Pornstars

Pedo Sex Story: Episode 58: A Deuce of Pornstars - 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  

For the next 2 days after my usage of Perlita, I had some peace and quiet as I’d not been feeling to well. It was not as bad as previous times I was unwell and I did not pass out or was delirious. I had 2 days of peace and quiet, which was sporadically interrupted by Dr. Hellruy who came to check on me. It was on the third day when I started to feel better that things started to get back to normal. I’d just finished breakfast when Eliza came in to check on me. “And how is my favourite patient feeling today?” She asked as she came into the room “I hope you’re feeling well?”. I smiled at her and replied “I always feel better when I see you my love doctor”. She steps up to my bed, leans down and kisses me gently.

“I can tell you’re feeling better” she says, breaking the kiss “But seriously, are you feeling better?”. I nod and reply “I feel as fit as a fiddle”. I pause, then ask her “Was my illness caused by you trying to figure out how to keep me here?”. Eliza nodded and replied “Indeed it was; I was trying a new method; how did it make you feel?”. I replied with “Not as sick as I did before and there was no buzz of a headrush”. I reach up and squeeze her bum as she replies “The new method works then; but it will need some refining”. She looked at my hand on her bum and asked with a smile “Enjoying yourself?”. I nod and reply “Oh yes, but I would be even better if you got in bed with me”.

“If I could Jay I would” she replies “But I only came in to see how you’re doing as I have rounds shortly”. I take my hand off her bum and reply “When can I see you again?”. Eliza smiles, kisses me gently then says “As soon as I have the time, I’ll come back here and fuck your cock right off”. She heads for the door, opens it then turns to me and says “In the meantime, might I suggest you checkout the website for someone to keep you occupied until I can join you”. She winked at me then left the room, closing the door behind her. I took her advice and decided to check put the website and see if I could find a fuck buddy. I got my iPad out of the drawer and logged onto the website.

Not long after I logged on, I found several women who had only been recently added. But before I could message any of the women on it, I received a DM from Dr. Hellruy:

Hello my teenage sex-toy, I have another friend who could do with a NSA hook-up. Check out the link below to see what she looks like then get back to me.

I clicked on the link and was not as surprised as I thought I was going to be when I saw who exactly it was. It was another adult film star, this time Rylee Reed, whose real name was Gemma Stone. I sent Dr. Hellruy a quick message:

I’ve checked her out.

I sent the message and did not have long to wait for her reply.

Do you want to meet her?

I replied quickly with:

Only if its OK with you

Her reply came swiftly:

She’ll be in the office in an hour; have fun

I sent a reply:

I will indeed have fun, but not as much as I would have if I were with you

I sent the reply and then got up and put the iPad in the drawer. I decided to grab a quick shower before I met with Rylee; I grabbed a towel, stripped off and went into the bathroom and took a nice hot shower. As the hot water cascaded down over my naked form, I made a mental note to ask Eliza just how she knew so many porn stars, not that I was complaining. I then made another mental note to suggest a new section for the website; ‘Adult Entertainers’. I did not mind at all when Eliza asked me to meet her porn star friends, I just thought that a dedicated section on the website would be easier. After I’d washed my hair, I got out of the shower and dried myself off, and as I left the bathroom, I noticed the time: 9:45am.

Rylee would be at the office in 15 minutes. I got a clen set of underwear and pyjama bottoms on and put my t-shirt back on. I grabbed my lanyard, slipped into my sandals, got my iPad from the drawer and left the room. And as usual when I left the ward, I could feel the nurses staring at my bum as I left; that always made me smile. I made my way to the elevator and down to the office. As I passed the main entrance, I saw the time was now 9:50am; Rylee would be at the office in 10 minutes. Not wanting to be late, I hurriedly made my way to the office. As I went in and closed the door behind me, I sat down at the desk and decided to send Eliza a quick message:

Hey there Doctor Sex, I just thought I’d message you and ask a favour for the office?

I sent the message but did not have to wait long for her reply:

Sure; what is it?

I quickly typed the response:

A mini-fridge with sodas and condoms, just in case?

As before, once I sent the message I did not have to wait long for her answer:

I’ll get on it and let you know

I smiled and before I could reply, there was a knock at the office door. I put the iPad down and called out “It’s open”. A second later the door opened and Rylee stepped it. “You must be Jay” Rylee said with a smile. I shook her outstretched hand and replied “Indeed I am; it’s nice to meet you Rylee”. She took off her coat and hung it on the coatrack and put her purse in one of its pockets. “So, what do you want to do first?” I asked “And where do you want to do it?”. She looked me up and down, then asked “For a while, can we just cuddle?”. I nodded and replied “Of course; couch, bed, armchair or office chair?”. Rylee indicated the couch and said “Couch and sans clothing”.

Needing no further instructions on what to do, I began to undress as did Rylee. “Wow ... for a kid you’re sure as hell look fucking hot” Rylee says as we both finish undressing. “I’m glad you like what you see” I reply “And you’re fucking hot to”. We moved to the couch and Rylee said “You lay down then I’ll lay on top of you”. I laid down and Rylee got on top of me, and we wrapped our arms around each other. “This is nice” Rylee says with a gentle smile “Just hugging with a hot guy instead of getting railed”. I hold her slim waist gently and reply “Naked cuddling on the couch can be very relaxing”. I always enjoy naked cuddling no matter which woman or girl it is with.

“In my job, I very rarely get to just cuddle with a guy” Rylee tells me “So laying here with you like this is so relaxing”. I slid my hands from her waist and onto her bum which I held gently. “I enjoy naked cuddling” I tell her “We can do this for as long as you want”. As we laid on the couch, I began to wonder what happened to Gemma Tomkinson. She’d wanted to make kiddie-porn films with me and other porn stars that she knew. I had asked Eliza about this and she had told me it was nothing to do with her and that she would sort it out. From then on, I’d not heard from Gemma and presumed that Eliza had dealt with her. I would never go behind Eliza’s back for anything related to sex.

I have to admit that it would have been interesting to make the films with Gemma and whoever else she got. “Fancy a game of tonsil hockey?” Rylee asked, to which I replied “I would love a game of tonsil hockey with you Rylee”. She looked at me with a smile on her face and kissed me passionately; I returned the kiss as I squeezed her bum gently. As we laid on the couch kissing, I could not help but be reminded of my last day at Brentford Court where I had fun on the couch in the waiting room. They were some good fucks that I’d had on that couch, but my pleasant memories of my last day at Brentford Court did not last long. I remembered the news I was given on the day that school closed; Karruche was pregnant with my child.

I wondered just how many of the girls and women that I’d fucked were now with my child. It unnerved me that one of the women I’d fucked was now up the duff with my child. As I was still only a child myself I did not want to have kids. And if I am being totally honest, with Ariadne out of my life I now never wanted to have kids. I was shaken from my thoughts about Karruche and her kid when after kissing for a few minutes, Rylee broke the kiss and asked “Do you have a girlfriend?”. I smiled and replied “No; I can’t find one who accepts what I do at the hospital”. Rylee nods and adds “It’s the same with me and my porn career”. She was silent for a moment then said “It’s a shame there is not something that benefits both of us”.

I smile and reply “If there was, we’d have to act upon it”. We then wrapped our arms around each other and once again began kissing passionately. As our tongues swirled around in each others mouths, I put my hands on her bum and squeezed it gently. If my cock could have gotten any harder then it would have done. We break the kiss and Rylee cuddled up next to me and draped her right leg over mine as she gently stroked my dick. “I never thought that I could have so much fun just hugging and kissing a guy” Rylee says, to which I reply “I’m glad you are enjoying me as much as I’m enjoying you”. We smile at each other then resume just laying there on the couch; I really enjoyed naked cuddling with Rylee.

I was enjoying it so much that if this is all she wanted to do then that would be fine with me. We cuddled in silence for a few minutes, with the only sounds coming from our breathing. We just laid there in silence for a few more minutes before Rylee asked “Want me to get on you?”. I smiled and replied “That would be nice, yes”. We kissed passionately for a few seconds before Rylee broke the kiss and straddled my waist. “Do you want me to wear protection?” I asked her, to which she replied “No, the guys I deal with at work have to wear them; I want to feel YOU inside me, not some piece of rubber”. She reached down and gently took hold of my fully erect cock and fisted it to her cunt-hole.

“Oh yes...” was all I said as she slid down my cock, taking it all all the way inside her in one swift motion. When it was all the way inside her, she looks down at me and says “I’m going to fuck you nice and slowly; I want this to be a loving fuck”. I put my hands on her slim waist and reply “Nice and slow is just fine with me”. She groaned in pleasure as she used her leg muscles to raise herself up my cock before lowering herself down again. She waited a few moments before raising up then lowering down again; I was going to enjoy slow fucking with Rylee. As I’ve mentioned before, I do actually enjoy slow fucking just as much as I enjoy a quickie. Slow fucking Rylee was different to my last fuck.

The last to me I ass fucked a girl was when I used and abused that Filipino girl Perlita. Slow fucking with Rylee felt like slow fucking with my backstabbing bitch of an ex-boss Leanne, but Rylee was significantly much better looking that Leanne ever was. “Hold me Jay” Rylee said gently “Hold onto me”. I sat up and Rylee wrapped her legs around my waist and we hugged each other tightly. “This is just what I need” Rylee said, groaning in pleasure “You are just what I need after a day fucking dumb guys you are just right”. I smiled and replied “I’m glad you like me”. For the next few minutes, we just fuck in silence while holding each other. As we hugged, it suddenly dawned on me that Rylee might actually like me.

She liked me as in really like me as in she might want me to be her boyfriend. I hoped it was not that as she was hot and I wanted to continue fucking her. “After today, I defiantly want to fuck you again” Rylee says, to which I reply “A regular hook-up?”. Rylee sighs in pleasure and replies “Oh yes, I need a regular hook-up with a decent normal guy like you”. She then kissed me passionately. And as our tongues swirled about in each others mouths, she kept sliding up and down my cock. Rylee broke the kiss and we returned to hugging as we fucked. For the rest of the fuck neither of us said a word, which was just fine with me. The silence inadvertently allowed my mind to wander.

And oddly enough I found myself thinking about getting caught. Thanks to Eliza, I now had a safe place to fuck the women from the website; as well as any other women or girls that I ended up with; though certain girls and women I did fuck in my room. I was shaken from my thoughts by Rylee when she started bouncing up and down on my cock faster and faster, telling me that “I’m almost there”. And a few seconds later she told me “I’m going to cum” which she did a few moments later. “I’M CUMMING” Rylee cries out “I’M FUCKING CUMMING”. Using her cunt muscles, Rylee griped my cock as it unloaded its full load of cum into her flat belly as I cried out “HERE I CUM, HERE I CUM”.

I thrust upwards to meet her bounce as the last drop of my cum was deposited in the porn star’s pussy. We stayed like that for a few moments to make sure the last drop of my cum was deposited up inside Rylee’s belly. Once when we’d both come down from the pleasure of the orgasm, she climbed off me and collapsed on the couch on top of me. We hugged each other in silence for a few moments until Rylee asked “You were fantastic; did you enjoy yourself as much as I did?”. I squeezed her bum gently and replied “You were simply spot on”. What I had just told Rylee was indeed the truth, she was indeed a great fuck and had been just spot on for one of Eliza’s porn star friends.

“I should have turned the fucking thing off” Rylee curses as her cell phone starts ringing “Sorry, it might be about work”. As she gets off me, I nod and reply “I understand”. She grabs her cell phone and answers it “I’m busy; what is it?”. I sit up and watch as she paces up and down, listening to the call. “That won’t be a problem as I can be there in half an hour” she says “I’ll see you then”. She hangs up the call and turns to me and says “That was about work; I’m needed for a few reshoots”. As I get up off the couch, I nod and reply “Work is work, I understand”. I step up to her, grab her bum and squeeze it gently and say “As long as you had fun, that’s all that matters”.

We kiss for a few moments before the breaks the kiss and I stand back and watch as Rylee gets dressed. “I wish I could stay longer” Rylee says as she puts her underwear back on, to which I reply “I wish you could stay longer to”. What I had just told Rylee was the truth; I did wish she could stay longer as she was not that bad looking and we could have done so much more. As she got dressed, I checked out Rylee’s slim form and could see just why she was so good as a porn star. I took in an extended look at Rylee’s ass and understood why she was a popular choice for bum fucks. “You were really nice” Rylee says as she finishes getting dressed “As soon as I can, I will want to see you again”.

I smile an reply “As soon as you can, I will be waiting right here for you”. We kiss passionately for a few moments before she breaks the kiss and says “I’ll see you next time”. I nod and reply “I look forward to it”. She opens the door and steps out, she looks back at me and winks before she closes the door. Once Rylee had left the office, I made sure that it was neat and tidy, which it was. I took a few moments to just sit in the armchair and rest, I hadn’t realized that fucking Rylee had been as energetic as it had been. Out of the 3 porn star friends of Eliza’s that I’d fucked so far, including Rylee, the latter seemed to be the most normal-looking one of all.

She did not have the large tits that Rio or Hope had; she just looked like a normal girl. I will point out that she did have a nicer bum than the other two and a cute smile too. I looked at my clothes on the floor and wondered if I should get dressed; but as I was in the office on my own, I decided against it for a while. The aircon was on and the cool air felt good on my naked form. As I sat in the armchair, I found that the peace and quiet that I now had allowed my mind to wander, and for some explicable reason I found myself thinking about Karruche. “Why would I think about her?” I asked myself “I have NO desire at all to have kids with anyone; let alone with her”.

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