You meet Jessica the next day

You show up to school early. Your little sister had to make it to her school early for her volleyball practice at her school anyways. You talked a while with her, she was excited to be going on a similar retreat for her team. She noticed a happy apprehension, a glow about you but couldn't get you to spill the beans. You lied to her and told her you were working on something with a classmate and it was a fun project. She knew that you and your friends had a habit of making the boring school projects as funny or ridiculous as possible while still following them to the letter of their instructions.

"Nerds." She giggled as she got off at her middle school.

After she was out of the car and your mother was the only one left with you the drive was initially silent. Then when she got to the nearest stop light.

"So, who's the lucky girl?"

"What?!" You gasped, chocking on your own spit. Your mom giggled at your embarrassment.

"The smell of the girl on your clothes wasn't exactly subtle." She gave a wry smile.

"Jessica." You admit, heat steaming off your ears.

"Wow, she has gotten your attention."

"Mom..." You trail off, too embarrassed to complete the thought.

"Does she have a big dick?" She teased.

You just wrap your seat belt around the side of your face staring out the car and avoiding the gaze of your mom with the seat belt.

"Oh my God. I was just kidding." Your mom holds her mouth agape. "Is she pretty?"

"She's... a cheerleader."

"Very pretty then." She giggled. "But, how is she? Not too rough with you, is she?" Her motherly concern shone out.

"No... at least not yet." You admitted. With her reputation it seems you have lucked out.

"I want you to be careful." Lisa adopts a commanding tone. "You're a boy, you can't be as carefree and easy as a girl can. That's why you have a shorter curfew than your sisters."

"I know mom."

"I'm just concerned for your well-being." She squeezes your arm with her large hand. Even with her soft gesture you can tell that she is stronger than you'll ever be. "And we'll have to go shopping for toys later."

"Toys?" You find yourself confused at the turn in conversation.

"Butt plugs, dildos and such...."

"What?!"

"You have to practice to be able to take her." She said matter-of-factly.

"Mom!" I was horrified with shock.

"I remember when your father and I started. He seemed to think that it was something a little lube could easily-"

"MOM!" I yelled. This was simply too much for me.

"Well, you should prepare yourself."

"Thanks mom." I was thoroughly done with the conversation.

"I love you."

"I love you too."

Lisa, your mother, dropped you off at your high school shortly afterwards. Just as she promised, Jessica was waiting there for you sitting under a tree on the front lawn. She had her phone out and was watching something while texting.

"Hey!" She waved you over.

"Hi!" You lightly run over to her.

"Sit." She pats the patch of grass right next to her. You mused about sitting on her lap instead but then remind yourself that she can easily get a hard on where everyone can see. You notice your mother winking and blowing at kiss at you as she waits for the line of cars to leave the drop off in front of the school.

"So...-" You begin.

"Your mom's hot." She cuts you off and makes you freeze. "So that's where your good looks come from."

"Thanks?" You wonder aloud to yourself.

She grew an amused expression and pulled your head in and kissed your forehead. She was far too sexy while she did it. An expert tease. You can still feel your mom's eyes staring straight at the two of you. Jessica notices your hesitation and rolls her eyes.

"Come on." She smiled as she hopped up and held out her hand to help you pull yourself up.

You follow her towards a class room in one of the older buildings that were hardly ever used. Once again, she had the key for it and locked the door to hit. The blinds on the windows long since locked closed. You move your way towards the center of the room while she locks the door behind you.

"Is your dad as cute as you?" She big her lip as she sauntered over to you.

"He passed away when I was really young."

"Oh." Her face grew sad. "I ruined the mood, didn't I?"

You don't know what to say so you simply nod your head.

She corners you over an old-style wooden desk. She leans down, her arms around you, her hands slamming down on the wooden surface. Her face is level with yours as she leans down, her eyes still filled with carnal want. Her hot breath was almost distracting as her large breasts heaving to just within millimeters of your own chest. Each time she breathed your eyes were drawn to them, yearning for their soft touch. She grew a wicked grin, she knew how flustered boys got when she did this. And you were cute.

"That better?" She leaned back. Your heartbeat was throbbing behind your ears as your penis was tenting your jeans. "There's my little slut."

Her finger runs down your upper lip and forces its way into your mouth. Her other hand unbuckles your pants and pulls them down to fall around your ankles.

"Suck it." She commands.

You do. You suck and tenderly play with the finger in your mouth. Your tongue dances over it as you rub it into your cheeks and lightly caress it with your teeth. You never take your eyes off of hers. Her penis begins to harden, and you watch as she adjusts her panties to pull her dick out before it's too late. It hardens before you, springing to hit the underside of the desk you were leaning on. You further your attention to her finger, taking it out and licking up and down as if it were her dick.

"Have you done this before?" Jessica's breath was becoming ragged.

In response you slowly took her finger into your mouth seductively. You bring your legs together, squeezing her fat cock between your thighs. She quickly takes the hint and starts to hump your legs as you continue with her finger. You worship it as if it were really her penis. Her humping becomes quick and erratic. She was close. Her eyes were fixed on your eyes and lips earlier, now they were shut as she was trying to keep herself going without loosing her balls below. Finally, you wring it out of her by taking her finger out and kissing it softly.

That unexpected action sent her over the edge. Her pelvis slammed into your own, your own boner was pinned against her stomach. Her blushing face and panting were too cute to pass up. You pull her into a hug and kiss her on the lips. She freezes her dick spewing wildly. Soon she melts into your arms and then holds you back. Her larger arms hold you to her. Neither of your lips part, you both act as if it's your first kiss. For you that's certainly true. (You had a friend in middle school and you aren't counting that one) Jessica breaks the contact between your lips. Her forehead resting on yours as you both breath heavily. Your eyes lock and smile at each other.

"I can't believe how good that felt."

"Well, you were too hot and ready for anything else." I smirked at her.

"It's too late to go any further. We'll both need to move across campus to get to our first classes." She bit her lower lip. She leaned down and kissed you on the lips again. She was very hesitant about it.

"Can't skip a class? This is the last time you'll see me for days."

"Tempting. But I've already missed too many this year thanks to my previous toy." She played with your lips with the same finger you sucked on. Your own saliva coated it and shone with light coming through the window.

"Trevor?"

"Oh? You've heard of him?" She looked away, her eyes darting to the windows and then back to your gaze, which remained fixed and serious.

"I heard he had to undergo therapy thanks to you."

"Like I said, we're going at your own pace, my little slut." She cut you off. "Partly so that doesn't happen... again."

"I'm the slut?" I mock sneered. "I'm not the one who's already kissed my 'slut' without even going on a date once."

Jessica's face grew redder than you had even imagined.

"D-Don't tell anyone we did that alright?"

"Oh?" I said unconvincingly.

"Please. The girls on the team..." She grabbed your arms firmly. You couldn't shake her off if you wanted to. "They wouldn't understand. I have a reputation as a gentleman killer."

"I know." I surprised her.

"And you still came after me?"

"I think you're really pretty." I began, her blush deepens. "Besides, I actually really liked it when you were rough with me."

"Now that's unfair. All I got was your thighs this time." She unlocked the door after putting her panties back on. "I'll be sure to be rough next time. Prepare yourself." She gave a wink and a smile before heading out int a different direction.