Confessions From a Boarding School Pupil - Cover

Confessions From a Boarding School Pupil

Copyright© 2022 by Drax

Episode 50: Erica’s First Time

Pedo Sex Story: Episode 50: Erica’s First Time - 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 next sexual escapade came 2 days after my interrupted fuck with Naomi; and it all started just after I’d finished breakfast. “Hello my teenage lover” Eliza said as she came into the room, to which I replied “Hello Doctor hot-stuff”. She sat on the edge of the bed and said “The website will be off-line for a day or two as I get the updates online”. I knew that the updates she was talking about were the ones Rio had wanted. “I understand” I said as I reached out and put my hand on her leg “It will give me a few day’s rest”. Eliza smiled as I slid my hand up her skirt and rubbed her thigh. “Indeed you can rest” Eliza says “You might rest better without your hand up on my leg”.

I smile and reply, “I could, but then I’d not be feeling you up; you can see the bind I’m in”. She smiles as I rub her leg gently. “So, for the next day or two you can just lay back and relax” She tells me “Though I might have to check up on you thoroughly”. I smile, remove my hand from her leg and reply “Then I look forward to that”. As she gets up and heads for the door, she turns to me and says “Though the website may be down, you might have an appointment of sorts later”. I frown and ask “How?”. She replies with “A friend has a daughter that wants to get laid; I’ll bring you all of the details when she sends them to me”. She blows me a kiss then leaves the room; my gaze on her ass.

Once I was alone again, I laid back and smiled; even with the website off-line, I would still be getting laid. I then realised that until Eliza came back with the details on her friend’s daughter, I had time to myself. I decided to mess about on my iPad for a while, and I found myself looking at the picture Kara had sent me a few days ago. Despite her being the school whore, I still found her to be attractive and wouldn’t mind getting up inside her again. I typed out a message to Kara:

Hey there; not heard from you in a few days so I thought I’d drop you a line to see how you’re doing

I sent it and returned to looking at the picture she’d sent me. She looked so good in the underwear, but my train of thoughts was interrupted by the iPad beeping, telling me I had a new message, so I clicked on it:

Hello Jay, this is Shannon and I’m Kara’s sister. I’m sorry to have to tell you this but Kara died two days in a car accident. I have been meaning to call you about this but did not know if you were still in hospital or not. If you need to talk, just drop me a line

Now I have to admit that I was shocked by what I’d just read; Kara had died. Back then, I did not know why this bugged me as much as it did. But looking back on it, it bugged me as much as it did because I genuinely liked Kara. This news put a downer on my mood and I did not feel like doing anything for a while. I looked at the picture that kara had sent me and sighed, it was sad knowing that I would no longer be able to get up inside Kara or spend any time at all with her. I was shaken from my thoughts about Kara when I received another message from Shannon:

Hey there Jay, I couldn’t send this message before as my friend was around. Kara told me all about what the two of you got up to at school. She said that the two of you used to get up to all sorts of sexual shenanigans and hijinks. If you want to do that with me, and I hope to god you do, drop me a note and I’ll get to you ASAP. Please find attached a picture to help you make your mind up.

I looked at the attached picture, it was of Shannon leaning against some rocks on a beach wearing a red and white bikini. As soon as I saw this picture, I knew that I had to meet and get into bed with her. I sent her a reply:

Hey there Shannon, I must say that I enjoyed your picture very much and I would very much like to do that with you. Drop me a line when you can come down to the hospital and see me.

I sent the message and did not have long to wait for a reply:

Hey Jay, I knew you’d want to meet with me. I’m currently at work and won’t get time off for just over a week. I’ll let you know when I’m free.

I smiled, knowing that I would soon be able to get up inside Kara’s hot younger sister Shannon. Judging from the picture she sent me, Shannon looked to be just as hot as her late older sister was. I was looking forward to getting up inside Shannon so I could compare her to Kara. I smiled then laid back, I was pleased beyond belief that I was going to be able to get laid with Kara’s sister. With being in such a good mood, I did not know what to do with myself. I decided to get up and go for a walk to the shop and get a sandwich and a coke, but no sooner had I got up then I got a visit from Dr. Hellruy. “Hey there gorgeous” I said with a smile “Is it time for my examination already?”

She kisses me gently and says “If it were, we’d both be naked and in bed by now”. We sit on the bed and she says “Remember earlier when I mentioned my friend and her daughter?”. I nodded and she continued with “Well, she’s been in contact, and wants to go ahead”. I frowned and asked “Wants to go ahead with what?”. Eliza tells me that “My friend has a daughter called Erica, who wants to lose her virginity to her boyfriend, but Erica’s mother does not like her boyfriend”. I nodded, and asked “And she wants me to do the deed?”. Eliza nodded and replied “She does; I showed her a picture of you and she thinks you’re a better person to take her daughter’s virginity than the daughter’s boyfriend”.

It was a nice compliment that I had been chosen to take the virginity of a girl. “But what does Erica think of this?” I asked “I don’t want to do this if she isn’t willing”. I did not want to rape Erica, if I was going to take her virginity I wanted her to be a willing participant. “I’ll find out” Eliza tells me “I think it has been sorted out with Erica”. Eliza pulled out her cell-phone and taps out a text message then sends it. “Now all we have to do is wait” she says, she looks at me and asks “While we wait, want me to toss you off?”. I smile and reply “Now that would be...”. I was interrupted by Eliza’s phone buzzing, letting her know she had a text message. She read the message and smiles.

“It’s all been sorted with Erica, who has agreed to this willingly” she tells me “She’s been shown a picture of you and wants to meet you for this”. I frowned and asked “How has she seen a picture of me?”. Eliza told me that “I took a sneaky picture of you and showed it to her”. Seeing a frown forming on my brow, she then said “She thinks you’re cute and wants to go ahead with this, it will take place here when she gets here”. I was relieved that she’d anticipated the questions I had, but there was one more I needed asking; “What does Erica look like?”. Eliza calls up a picture on her phone then taps a few keys, hands the iPad back to me and tells me “I’ve just sent it to your iPad”.

She gets up off the bed and says “I’ll let you know when she arrives”. She winks at me then leaves the room, closing the door behind her. Once I was alone, I pick up my iPad and check the messages and just as she said, she had sent the photo to me. It showed Erica sat on a wooden dock, wearing a red bikini top and black bikini bottom; she was incredibly fucking nut-busting hot and I could not keep my eyes off the picture of her. I could not wait until I met Erica and could get up inside this hot teenage piece of ass. I decided to make a quick run to the shop as I’d mistakenly thrown out the box of condoms I’d bought. I got my sandals on, grabbed my lanyard and headed out.

And as usual I felt the welcome gaze on my bum of the nurses at the nurses station. I got to the shop and bought a pack of condoms as well as a Cherry Coke then made my way back to the ward and my room. Once I was back in my room, I found myself unable to relax as I was more than a little nervous about what I was going to be doing. I was going to be the first person to have sex with a nut-bustlingly hot girl; but this would not be the first time that I’ve done this. I had been the first person to have sex with Christina which had been just fantastic and I was looking forward to getting up inside the Ukrainian teenage beauty as soon as she had some available time.

But for now, my main focus was Erica and the fun that was to be had with her. I laid on my bed and did not know what to do until Erica arrived; thankfully the decision was taken out of my hands as I found myself falling fast asleep. I was awoken a few hours later by Dr. Hellruy. “Hey there sleepy-head” she says with a smile “You have a visitor”. I sit up and ask “Erica?”. She nods and says “She’s waiting outside”. I get off the bed and made sure that my clothes were straight and that my hair was neat. “OK, send her in” I say. Dr. Hellruy gives me a quick kiss then exits the room, and a moment later Erica steps into the room, closing the door behind her. “Hi” she says a little nervously “I’m Erica and you must be Jay”.

I shake her hand and reply “Indeed I am; its a pleasure to meet you Erica”. She looked just as good in person as she did in the photo. “So, did Dr. Hellruy explain everything?” Erica asked, to which I reply “Yes; you want to loose your virginity but your mom was not keen on your boyfriend”. We sit down at the coffee table and Erica told me “That’s exactly it; mom was not to fond of my boyfriend at the time so when she saw you, she liked you and so do I”. I smile and reply “And I like you to”. There is an awkward pause, then I ask “So, what do you want to do first?”. She taps her shoulder bag and says “I need to get changed into something more comfortable”. I nod and say “OK, I’ll do the same”.

We both get up and I watch as she disappears into the bathroom and closes the door. I move back to the bed and strip down to my boxershorts, taking a few moments to make sure my cock was at its maximum hardness which it was. I sprayed on some aftershave to make sure that smelled good. I then just stood at the foot of the bed and waited for Erica to come out of the bathroom. I checked my cock yet again to make sure that it was still rock hard, which it was. This was the most nervous part, waiting for Erica to come out of the bathroom, but after a few moments I did not have to wait any longer. “I’m ready” Erica says as she exits the bathroom. And she was wearing the same bikini she’d been wearing in the picture.

When I saw her bikini-clad form I nearly blew my load. “Wow...” I say “Just wow...”. Erica smiles, puts her hands on her hips and asks “So, I take it you like me?”. I nod and reply “I like you as much as you do me”. She steps up to me and looks me up and down. “Wow...” She says with a smile “You’re so much hotter than my ex”. As I smile at the compliment, we wrap our arms around each other and kiss passionately. I reach around and gently grab Erica’s bum through her bikini bottom, and let me just say that it felt just as good as it looked. We kiss like this for a few moments before Erica jumps slightly, wrapping her legs around my waist with my hands holding her firm teen ass.

We stumble back to the bed where Erica gets down and says “Lets get in bed”. We get in bed and cuddle up witch each other before we resume kissing. Our tongues explored the inside of each others mouths while our hands roamed over each others bodies. We continue kissing passionately for a few moments before we stop. “Wow...” Erica says panting “That was a great fucking kiss”. I nod and reply “You are a great kisser; your boyfriend is a lucky guy”. Erica looked at me and said “I have to be honest with you; I don’t have a boyfriend anymore”. I frown and ask “Why not? Did he dump you the blind fool?”. If he had dumped Erica, then he was not only a blind idiot, but a dumb prick to boot.

“He didn’t dump me” Erica told me “Rather I dumped him”. She cuddled up to me tightly and then said to me that “I dumped him when I saw the picture of you; I’d rather be with you than be with him”. I looked Erica in the eyes and asked “Did you really dump your boyfriend to be with me?”. She kissed me gently then answered “Yes...”. It felt good that she’d dumped her boyfriend for me, as this meant that she was really into me and genuinely had feelings for me. Now before you all go and start moaning at me that I’ve said in the past that I don’t want a girlfriend, I still don’t. It’s just with Erica I could pass her off as my girlfriend easier that any of the other women who’ve wanted it so far.

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