Confessions From a Boarding School Pupil - Cover

Confessions From a Boarding School Pupil

Copyright© 2022 by Drax

Episode 52: Porking a Pornstar: Chelsea Hope

Pedo Sex Story: Episode 52: Porking a Pornstar: Chelsea Hope - 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  

The morning after my fuck with Jennifer, I yawned as I sat up in bed and yawned. I had woke up just in time for breakfast which was bran flakes, toast, coffee and orange juice. Once I’d finished breakfast, I decided to check the website and see if there was anyone that struck my fancy. I logged onto the website and checked out the women listed there. There were a few new women listed and as I was about to book a meeting with one, I received a message from Dr. Hellruy:

Hello my teenage sex-toy, I need a favour. I have a 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.

Knowing that whoever it would be would be hot, I clicked on the link and could hardly believe who it was; it was porn star Chelsea Hope, whose real name was Gemma Tomkinson. After fucking Rio West, I knew that this was not a prank. I sent a reply to Dr. Hellruy:

Another porn star wants a NSA hook-up; How do you know them?

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

She was a patient a few years ago and we kept in touch. You like her, and I know that you want to meet her

I had to admit than Eliza was right, I did find Gemma to be a lot better looking than Rio West. I sent a reply to Eliza:

Only if its OK with you

Her reply came swiftly:

She’ll be in the office in 10 minutes; have fun

I sent a reply:

I will indeed have fun

I sent the reply and then got up, got my lanyard and sandals on. Not knowing if she’d want me to wear them, I took the condoms with me just in case. I left my room and headed down to the shop to grab a couple of sodas, and when I noticed that I was 10 minutes early, I did not know what to do, so I sat down on a bench and decided to wait until Gemma got here. I opened one of the sodas and took a sip, watching the people as they came and went. As I watched people coming and going, I wondered out of all of the women and girls I would be fucking next. I always found it interesting to watch the people as they came and went as I never seemed to see the same people twice; unless they were here visiting someone.

As I took another sip of my Soda, I oddly found myself to be nervous. It was the same nervousness that I felt before I fucked Rio. I was nervous about having sex with a porn star whose very job is to have sex on camera, that and the fact they’d been with guys who were bigger than I was. After a few more minutes of watching people come and go, I headed to the office where I found that Gemma was already waiting for me. She was 5ft 9in tall, had green eyes, brown hair and impressive 34E boobs. “You must be Jay” she says, shaking my outstretched hand “Eliza has told me all about you; I’m Gemma”. I smiled and replied “It’s a pleasure to meet you to Gemma”. I could not help but stare as she was wearing a red and white striped bikini.

“So, I hear you want an NSA hook-up?” I asked, tearing my gaze away from her tits, to which she replied “Indeed I do; Eliza and Rio both said you were fantastic”. It was nice to hear that both Eliza and Rio both had said good things about me. “So, what do you want to do first?” I asked “And I have these if we need them”. I took out the box of condoms from my pocket, Gemma took them from me and tossed them in the trash. “We wont need them” she tells me “I want to feel your cock inside me and not some piece of lubricated rubber”. Gemma grabs me and pulls me into a passionate kiss, wrapping her arms around me and holding me tightly. I wrapped my arms around her and returned the kiss.

I put my hands on her bum and squeeze it gently, even through the fabric of her bikini bottoms it felt fantastic. We kissed for a few moments before Gemma broke the kiss and said “Eliza and Katie said you were a good kisser but not that you were this fucking good”. “I’m glad you liked it” I reply “And I hope you enjoy the rest of what we do just as much”. She slipped her hand into my pyjama bottoms and grabbed my cock and said “Oh I’m in no doubt that I’ll like what else we do; Eliza and Rio both told me all about you”. While keeping her hand on my cock, Gemma pulled me close and resumed kissing me. As I put my hands back on her bum, her cock squeezing felt absolutely fucking amazing.

“Put your hands inside my bikini and grab my ass” Gemma says, breaking the kiss. “OK” I reply with a smile as I do as she says. As I slide my hands inside her bikini bottoms and onto her ass, she resumes the kiss while keeping a firm but gentle grip on my cock. As we resumed kissing, I was already enjoying myself much more with Gemma than I had been with Rio; but that was because Gemma was way hotter than Rio. As I squeezed her ass, I could tell that Gemma felt my cock get as hard as it could. She took her hand out of my pyjama bottoms and wrapped her arms around me. We kissed passionately for a few minutes before we had to break the kiss as we were both out of breath.

After a few wordless moments, we resumed the kissing. As our tongues swirled around each others’ mouths, I could not help but hope that we could continue kissing for a few minutes as Gemma was a great kisser. “So, where shall we do it first?” I asked Gemma as she then broke the kiss and stuck her hand back down my pyjama bottoms and squeezed my erect cock firmly. “I have an idea” Gemma says as she takes her hands out of my pants. She took a step back and began to stripped off. If it were possible for it to do so then my cock would have gotten even harder as she stripped out of the bikini and stood before me totally naked. “Now that we’re naked, we can do a lot of this...”

She says before she steps up to me and pulls me into a passionate kiss. As she wraps her arms around me, I put my hands on her ass and squeeze it gently. As we kiss, I smile inwardly at what is happening. I’m kissing a naked porn star and will soon be fucking her; my life was fucking awesome. “Get naked” Gemma tells me, breaking the kiss. I do as she says and am soon stood before her as naked as she is. “Very nice” Gemma says, looking me up and down “Rio said you were hot but not as hot as you really are”. I smile and reply “I’m glad you like me; and Eliza never said you were as hot as you are”. She looked me up and down then asked “Would you mind if we just cuddle for a while?”.

I answered with “Whatever you want to do is what we’ll do”. She took me by the hand and led me over to the bed, we got on and cuddled up to each other. “This is nice” Gemma says resting her had on my shoulder and draping her left leg over mine “When you’re fucking all day at work, sometimes all you want to do is cuddle with a nice guy like you”. I put my hand on her tits, gently rub them and reply “I like naked cuddling to”. Now as you will all be aware; I do so enjoy naked cuddling and today was no exception. So, for the next few minutes, we just lay there in silence. Although she was a porn star like Rio, I found Gemma to be far hotter than Rio. “Do you have a girlfriend?” Gemma asked, breaking the silence.

“No” I replied “I can’t find one who accepts my job here at the hospital”. Now that was a lie as there had been two people, Shania, Christi and Katy, who had wanted me as their boyfriend and accepted my job in the hospital. I’d got rid of them when they started getting clingy and wanting me to father their kids. “Same goes for me and a boyfriend” Gemma says “Which is why this arrangement with you is just perfect”. There were a few more moments of silence, before Gemma asked “Would you be willing to see a few of my friends?”. I frowned and asked “What do you mean?”. I knew exactly what she meant. I just wanted her to actually say it. “What I mean is would you be willing to do for them what you’re doing for me” Gemma tells me.

“I would of course clear this with Eliza first” she adds. The thought of fucking other porn stars was a very exciting idea, especially if they were as hot as or even hotter than Gemma. “That would be a good idea” I replied, kissing her neck “I look forward to working with your friends as closely as we are doing”. If Gemma’s friends were half as hot as she was then this would be so much fun. I was then caught off guard when Gemma asked me “Would you be interested in an off the books project?”. I frowned and asked “What do you mean?”. She looked at me, and as she gently stroked my cock she said “Some of my friends want to retire from the porn game and start having a family”.

Now I had to admit that when I heard that, I began to panic as I did not want top start a family with any of them; but thankfully that is not what she was going to say. “Those that want to leave and start a family are having trouble getting in the family way” she continued “Would you be willing to help them get in the family way, if you know what I mean?”. I did indeed knew what she meant, and I tried to hide my eagerness to do it as I asked “And you want to keep this from Eliza?”. She nodded and replied “It would be best if we did, at least for the first few. We don’t know how Eliza will react to this”. I had to admit that her reasoning made sense; but I could not just do something like this behind Eliza’s back.

“I’d prefer it if we just told Eliza” I tell Gemma “She’d be open to it so long as it does not effect my job here”. She smiled and asked “You really like her, don’t you?”. I replied with “She’s been really nice and good to me, so going behind her back is something I’d not want to do”. Gemma kissed me gently and said “This is one of the reasons you’re so popular; your loyalty”. It was nice when they said nice things about me. So for the next few minutes, we just silently laid there in each others arms, until Gemma broke the silence and said “Lay down on the desk; I want tub rub you down”. This would not be the first time a woman rubbed me down as Daisy had been the first.

“This is going to be nice” I say with a smile as I lay down on the desk “Getting rubbed down by a porn star”. I laid face down and rested my head on my arms; Gemma got off the bed and stood next to the table. “Ok, I’ll start with your shoulders” Gemma says as she rubs my shoulders, she then moves to the head of the desk and as she rubbed my shoulders and neck, I could feel her tits pressing against the back of my head when she rubbed further down my back. “Having fun?” Gemma asked me, to which I reply “Indeed I am”. She rubbed my shoulders for a few minutes before she stopped and asked me “You ready to get up me?”, to which I replied “Ready, willing and very able”.

I sat up and as I got off the desk, her gaze immediately fell onto my erect cock. “You like?” From her gaze, I already knew the answer, but I still asked, she stepped forward grabbed my cock and replied “Oh I like it very much”. She led me to the bed and we got on and she asked “Do you want me to blow you first?”. I wanted her to blow me so fucking bad, but this was not about what I wanted so I replied with “If its what you want to do then that is what we’ll do”. Gemma leaned down, kissed me gently and replied “You are so thoughtful and kind; its one of the reasons women like you so much”. I smiled and replied “It’s not all about my enjoyment, yours matters just as much”. What I had just said to Gemma was the truth.

The pleasure of the woman or girl I was with also mattered, as they had booked me what they wanted was just as important. “Let me ride you first” Gemma says as she positions herself above my cock “I’ll blow you later”. She reached down and grabbed my cock, fisting it to her cunt hole and placing just the tip inside. “Oh wow...” she sighs as she slowly sinks down my cock “This is fucking amazing”. When she had sank down all of my cock, she just stayed there for a few moments before she placed my hands on her slip waist and slowly started bouncing up and down. It looked like this was going to be a slow fuck, which I did not mind at all. As I have mentioned a few times before, occasionally taking things slowly was good.

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