Well I'm back to doing a new fanfiction, after the 'taking a bit of time to finish the story' By Her Side, but since there's a lack of Lessie Lemon, I'll have to do a new oneshot, inspired by a porn clip I found somewhere. In this one, Luke imagines Jessie as a prep schoolgirl. Enjoy!

I don't own Jessie, but if I do, Lessie would be happening =)

Jessie was taking a bath, and was rinsing her entire body after she soaped it. She can feel the water dripping in every part of her as she feels herself while cleaning everything- she feels her nipples harden with the water, and her eyes was closed as she imagines someone- or somebody- giving her pleasure.

She then proceeds to get the showerhead and set it to a bit hot and places it between her thighs, and she moaned from the sensation coming from her clit. She then rubs and mashes her cup D breasts and her moaning intensified.

Ever since the Rosses allowed her to go study in Manhattan prep, she decides to live in the school's boarding home so she can spend time to study more to expand her skills. However, what did didn't know that someone in the family was chosen to be its headmaster…

As the pressure builds up, Jessie can't take it anymore and ends up shutting down the showerhead and she collapses, but she cummed hard as she gushes a big amount of cum, which makes her moan louder in an ear-splitting one. She then tried to catch her breath as her breasts rise up and down. She then reaches for the showerhead and turns it back on so she can clean up a bit more and get relieved before she gets out of the shower.

Minutes later, she was now dressing up to get ready to go to the classroom. Luckily she was the only one there (as well as during the time she was taking a shower) so she was relived no one heard her moans. She started picking out a white and pink panty and slipped it in, accentuating her butt. She then wore a front hooked pink and white lacy bra which really supported her cup size. She then proceeds to put in her buttoned school top and then her school skirt and tie. She finally puts on the school's blazer to complete the attire.

Jessie then looked at the clock, and noticed she was extremely late. Before she can get out of the room, the door opened and someone came in.

"Miss Prescott, why aren't you downstairs for the morning school gathering?"

"Luke? When did you become the headmaster in the school?"

"Dunno, but why the heck you're late every single time?"

"I'm really sorry, it just takes me a lot of time to prepare for school and get ready. I'm really sorry that I am late recently."

"OK, I'll let it go, however, since you've been recently late in the morning, You'll have to spend time with me… right now."

"Um, what?"

"You heard me Miss Prescott. This is your punishment. And think of it, it isn't bad."

"I don't understand…"

"Follow me to my office, we'll see."

She then followed the young 12-year old headmaster to his office. And then they got there, she locked the door because this was between the student and the headmaster.

Before she can sit, he then said, "No, don't sit, stay standing. I'll be with you in a few seconds."

As he finally got near the girl, he finally resumed talking. "Ah. Miss Jessie Prescott. I remember that cuteness, the hotness. All of it. I remember the last time you were with us, you were my nanny with the other siblings I have. Now, I got it where I want you to be, under my skin."

"Luke… I don't get it…"

His hands then traveled all around the 18-year old's hot, curvy body. "I didn't know you were so hot. And not to mention you're not squirming a bit. Getting turned on Miss Prescott?"

Jessie got a bit blushed that he knew that he was turning her on. She then said, "I am…"

"Good. Now, open up the buttons."

She obeyed the young headmaster and slowly unbuttoned her blazer but before she can take it off, Luke then grabbed the hem of the blazer, stopped her and said, "No, you're not taking it off. They'll have to stay…"

She was only allowed to take off the necktie, and Luke saw her school top and said, "You only buttoned 2 of them? How naughty."

She then revealed she was wearing the lacy pink and white bra, and that only made Luke drool. He then came near to her and caressed the restricted tits with his fingers.

"Do you love what you see, Luke?"

"I'm loving it… and so is your sexy voice."

Luke kept having his fingers do the magical touch on Jessie's cup D tits, as Jessie closed her eyes and mumble like she was being pleasured.

"Now, unhook the bra."

Jessie slowly unhooked it, still following the headmaster's precaution not to remove a single piece of clothing unless he said so. He saw her nipples were already erect and he said, "I love with when it's hard to the touch. Let me rub it more so you can moan."

Using the bra's lacy parts, he used them and rubbed it on her nipples. Jessie, feeling the bit of pain from the nipple rubbing, finally moaned the sweet moan Luke was dying to hear. "Yes, Jessie. Moan your heart out, I want you."

"Umm, Luke, don't stop, don't stop rubbing them… ahh"

Luke was enjoying this that she can't handle the buildup so much that Jessie finally moaned, "Luke… The pressure… it's building up… I… can't… take it… anymore…!"

"What pressure?"

As she moaned, Luke was squirted with breast milk from Jessie. He was surprised to see her lactate too early despite not being a mother, and she fell down the floor because her legs can't take the pressure from it. As he saw Jessie's hot body having milk in parts of her upper body, the lactated schoolgirl looked even hot for him to handle and he already had an erection in his pants. She was panting from the buildup that happened as if she was all out of energy.

"Wow, you really had to lactate early in life. You're not even a mother yet, yet it happened? How slutty. I like where this is going."

Luke crawled close to Jessie and licked her body where the milk spread throughout. He lapped it up, making sure no milk was left.

"Lap it up, Oh Luke, or momma's gonna be upset"

As he was finished, he then squeezed Jessie's tits and more milk came out like a fountain. Luke then lapped it all up, and then fondled with her tits and even bit her nipples, making Jessie moan.

Luke however, can't take the pain anymore, so he then asked, "I bet you had a fantasy of sucking cock, didn't you?"

"I do headmaster… I wanted to try it."

"Very well then, you got it!"

He then removed his pants and after removing his boxers, Jessie was quite in awe at what she sees- it was a 7-inch cock! Luke was relieved he finally got his pants out of the way, and then Jessie got up and crawled to where Luke is and began sucking his cock. Luke was tickled at 1st, and then he finally emitted moans too.

"Oh Jessie, don't stop, keep going!"

She was too busy sucking the young one's cock she didn't care what Luke thinks. Luke, getting really twitchy, ends up slapping her left boob and she didn't budge. Instead, milk dripped again, and Luke's hand was wet. Luke then got twitchier and he feels like finally blowing the load on her.

"Jessie, I'm going to-"

However, it was too late, his cum blasted at Jessie's face and he was disappointed that he cummed earlier than expected. "Oh boo… this isn't what I was expecting…"

Jessie however smiled that she had cum on her face, and some of it fell on her mouth and said, "Mmm, I like what I'm tasting right now… You're really good."

"I'm glad you said so. Now, can I…"

"You can shove that dick in my hole, Luke!"

He was startled with the schoolgirl's words he did just that. He removed her panties but he found out she already soaked them while it was all happening a while ago. "Ah, you're already wet before I can get there… you're really horny now. Let me lap it up for you."

"Luke, I meant put it in my- OHH! LUKE!"

Luke started to bring his tongue in her opening and she loved it as his tongue lapped up her pussy, and later it entered inside. Jessie was feeling like she was drilled from the inside, as Luke continued to eat her pussy until she can't hold it no more.

Luke was finally done and proceeded to bring his dick into her pussy. As he slowly brought it in, both of them were hurting because Jessie was tight. "Ooh, Jessie, you're so tight!"

"Please Luke, Punish me, punish me for being a late girl! Push that cock inside of me!"

"I AM punishing you! Now, let's get down to business."

Luke sped up and humped faster, and he can hear Jessie's moans becoming more and more louder. He felt like he's nearing to cum, while Jessie felt like she had to pee, since his cock has already reached the spot where she feels like peeing on him right now.

Finally, both of them moaned in unison: "I'M GONNA CUM NOW! AHHH!"

Fearing he would impregnate Jessie, he pulled out and Jessie cummed on Luke hard that she fell down and started moaning like it hurts while writhing in the aftermath of her cum. Luke ended up cumming on Jessie's breasts. "Ohhh Luke… I'm… I'm… Ahh"

Luke then rubbed her pussy to relive the pain of cumming. "There there… It's ok. It's over now."

"Come here, Luke…"

She kisses Luke and they share another round of passion between student and headmaster, all while fondling Jessie's tits.


Luke got up in the middle of the night, and sighed.

"Oh man… that was all a dream! And I thought it was real…"

Then he noticed that he had a wet dream all along. He ends up going to the bathroom and changing to a new set of pajamas, and went back to bed with a smile on his face.

"Someday Jessie… I will taste those tits of yours. Just you wait."

Well this is it, I'm finished doing this story, took me days before I finished doing this story. Hope you guys like it, and hope someone else makes a Lessie Lemon!

Leave reviews!