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The Bucket List - Riley

Joe crosses off the first item on his bucket list
Joe loosens his collar a bit as he leans back in his chair. It has been a long day for him. The students in the earlier classes are not exactly keen on listening to his orders, making him do more than what his job description requires. Finally approaching the last block of the day, he can let out a long breath. This is his favorite class by far.

Because this is a senior class, the students are all over the age of 18. Most of them are mature enough to not blow a spitball on someone else’s back. Most importantly, he can enjoy fantasizing about the cute female students in the class without feeling any bit of guilt. In fact, he has been making a list of all the girl he would like to get a “taste” of before they graduate.

The bell rings and groups of students start pouring in. As he is about to close the door a tiny body squeeze through the crack in desperation. “Sorry I’m late Mr. Eriksson, I lost track of time in the library.” A tiny voice comes through the girl’s open lips.

“That’s quite alright Riley, I know you wouldn’t be late on purpose”

He closes the door after him as the class begins; catching a glimpse of Riley’s back just before she sits down. Riley has been on his radar for awhile now. He often catches himself fantasizing about her tiny body, standing no taller than 5’3"; his hands around her narrow waist, holding her up while he drives himself into her. He imagines himself shooting his load all over her pretty little face as he strokes himself over the limit, ejaculating all over the shower floor.

Today is a review class before a test, so Joe doesn’t have much to say, allowing the class to work until the end of the school day. He sits back down in his seat, pulling open his laptop cover to surf the web. Riley sits right across from the teacher’s desk and it is hard for Joe to not catch her in his peripheral vision, drawing his attention away from the computer screen. Today she is wearing a grey sweater with a pink scarf. Her silky brown hair in a bun, with a cute little flower complementing it. He catches himself wanting to see more of her as he looks down below her desk. The first thing he sees is a pair of leather boots. As he moves his eyes higher, a pair of long socks peers over the edge of the boots, wrapping around skin-tight leggings that hugs her skinny legs.

He snaps back to reality as another student taps him on the shoulder, needing to ask a question. After he explains the question to the student, he turns his focus back to Riley. She stares down at her paper, trying to figure a problem out. Her red lips wrapping around the end of her pencil. He feels his pants bulging watching her, almost falling into another fantasy. Forcing his attention back to the computer screen, Joe tries to eliminate any thoughts of Riley. On his computer, he pulls up the list he has been making of all the girls he wants. Riley is on the top of that list. With only a week of school left, he has to act fast. Finally, he decides that he is going to start on that list today. He has the perfect target to begin with. He thinks to himself as he shifts his eyes to Riley, who is completely oblivious to what is going on in her teacher’s mind.

Time passes agonizingly slow for Joe as he constantly checks the time, wishing the hands would tick faster. With a couple of minutes left before the end of school, he stands up to address the class, “as you all know, next day is your big exam. So go home and study hard. You may pack up now and leave when the bell rings”

The bell rings and all the students rush out of the room, suddenly full of energy with the school day coming to an end. As Joe expects, Riley has just stood up and started to pack. She is a quiet girl who doesn’t have a lot of friends, often spending her time studying or reading. He walks up to her, “Riley, I know you don’t come to class late on purpose, but this is becoming a problem.” Looking down at her, he just realizes how much she is shorter than him.

“Sorry Mr. Eriksson, I just get so carried away reading and keep forgetting to check the time. When the bell rings I just never have enough time to pack up.”

“I understand, but if you are late for next day’s test you will be locked out and receive no marks on your test. I know you studied hard and I don’t want to see that happen.”

“I will make sure I come on time next time. Speaking of the test I have a few questions to ask you," she says as she pulls out her assignment from today’s class. “I find this really difficult, but I want to get a high mark on this test. Can you give me some tips?”

Joe quickly formulates a plan in his head. He pretends to read her assignment. “This doesn’t look too good Riley, you are really struggling with this topic.”

Her expression quickly changes to a worried look. “I thought I was just struggling a bit, but it looks like I’m not going to do well on this test.”

“It’s ok Riley. You did well on all the other tests. This test shouldn’t drop your marks by too much; however, if you want a really good mark, there is one other way...” He puts his hand on her shoulder.

Riley stares back for a few moments, stunned. She gathers her thoughts, searching for the appropriate words. “I...I don’t understand what you mean.”

“Oh I think you understand exactly what I mean.” He shifts his hand from her shoulder down to her arm, feeling the roughness of the wool sweater as he strokes it up and down. “You’re a smart girl aren’t you?”

Tiny drops of sweat begins to form on Riley’s forehead as she considers her options. Finally, she responds reluctantly. “O....Ok, I will do what you asked as long as I get a good mark on that test.”

A smile forms across Joe’s face. “Of course I will give a good mark to a smart little girl like you.” He snakes his arm around Riley’s back, pulling her body close to his. Eagerly, he lands his lips on her rosy cheek. She jumps back a bit but does not resist. He continues, this time landing a kiss on her glossy red lips. Riley just stands there, letting this 50-year-old man have his way with her. Little does she know the kissing should be the least of her worries.

“I want you to kiss back.” Joe instructs. Riley complies by pecking him back on the lips. He then parts his lips, making Riley mirror what he is doing; he enters her mouth with his tongue, entangling it with hers. Meanwhile, his hand moves from the arch of her back slowly down to her tiny swell of an ass. His fingers squeeze her small cheeks. Riley doesn’t have much of a curve, but years of dancing has toned parts of her body, such as her ass, well. Wanting to feel more flesh, he finds the waistband of her leggings. Reaching his hand inside, he grabs her firm ass once again.

Feeling he should move on, Joe parts their kiss and pulls his hand out of her leggings. “I know you are still a virgin and never had any boys in your life so I will talk you through this. You’re a smart girl, you’ll learn fast," he says, motioning her to get on her knees as he leans back against a desk. “Sucking a cock is really easy, soon you’ll find yourself on your knees in the bathroom giving boys the time of their lives.”

Riley kneels down in front of him, unzipping his zipper with her delicate little hands. Then she pulls out his semi-erect penis.

“Lift my cock up while stroking it, then use your tongue to lick my balls.” She does exactly what he asks, stroking as she lifts his cock. With just a few strokes using her warm little hand, he is already fully erect. Parting her lips, she puts her tongue on his scrotum, licking the rough skin with small flicks.

“Yes! That’s it!” he exclaims at his new found pleasure. “Now put my cock in your mouth and think of your own ways to pleasure me.”

Without saying anything, she wraps her lips around his warm rod. She bobs her head up and down at the length of his penis. Her tongue flicks the glans, where all the nerve endings are.

“I..I knew you’d figure it out by yourself.” Bathing in pleasure, Joe has trouble speaking. He grabs the back of her head and forces himself deeper down her throat. Listening to Riley gag almost sends him shooting his load. He holds it in quickly; he has not even started with this little body yet.

“Look at me.”

Riley looks up with her bright blue eyes.

While she expertly work on his cock, he leans forward. Joe unties her hair tie. He allows her hair to fall down to her shoulders. He grabs the flower in her hair just before it could fall. Leaning back, taking in the fragrance of the lily. Joe wonders if it’s from the flower itself or Riley’s hair.

Satisfied with her sucking, he grabs her under her arms and pulls her up to her feet. She looks down and quickly brushes white dirt off her dark leggings where her knees touched the ground.


Riley nods shyly, looking down at the ground. Joe lifts a finger under her chin and tips her head up to look at him. Then he wraps his fingers around her hand and pulls her to his desk. He bends her face first down onto the desk with her ass in the air. Joe takes place behind her. She looks back at him, a worried look on her face.

“Don’t worry Riley, I’m not gonna penetrate you yet.”

Joe plants his feet outside of hers and squeezes her legs close with his knees. He then proceeds to pull her thighs open a bit and sticks his now rock solid cock between them before he shuts them around his rod. He begins to thrust with his hips. The soft fabric of her leggings rubs against his bare skin. He gathers her hair in one hand, tugs it, and pulls her upper body off the table; all the while spanking her tight little ass.

Remembering telling himself earlier to not to get too rough at first so he doesn’t scare her off, Joe gently loosens his grip on her hair, letting her body fall back onto the table. He then places that hand on her chest and feels her tiny breasts through her sweater. The hand he used to spank her is now in her crotch, poking at her vagina through the fabric. Then he reaches in past the waistband. He pushes her panties to the side. He finds her clitoris and circles his finger around it.

With the increase of the force he thrusts between her thighs, he also begins to circle her clitoris faster and faster.

Riley is letting out moans now: quiet little yelps, but distinctly. Feeling daring, he moves his finger to her opening. Joe feels resistance as he tries to poke his fingers in. He uses a little more pressure, forces it in. Her head comes off the table in shock before it falls back down again. Her arms are outstretched. Her fingers wrap tightly around the edges of the table.

“Wow, I barely poked my finger into her pussy. How tight would it feel when I try to poke my cock in there?” Joe thinks to himself.

As time goes on, Joe starts to thrust furiously. His body pushes into hers and she in turn pushes against the table. The two body masses make the whole table squeak with movement. His finger moves tirelessly in and out of her tiny opening as she lies flat on the table. Her eyes close in pleasure.

Joe looks through the window on his door to see the hallways empty. He checks the time. It has been over an hour since school ended. Everyone has already left the school. He parts his knees and allows her legs to part. He pulls out his cock, but keeps the hand in her leggings in. He pulls Riley up with his other arm.

“Let’s go for a walk in the hallway.”

Holding her by her pussy and under the arms, Joe pulls Riley’s tiny body off the ground and carries her straight up out into the hallway.

“Where are you taking me?” Riley asks with a shaky voice. She sounds scared that someone might catch them.

“Don’t worry baby, daddy won’t let you get hurt... A lot.”

Joe stops next to a row of lockers as he drops her to the ground before shoving her face first into the lockers. The hand in her leggings begins to explore her insides again. The other moves to her smooth little ass. He grabs it with force.

“What a tight little ass...” Joe exclaims.

He moves that hand to her waistband, his fingers grip the edge. Then he pulls it down slowly. The fabric turns inside out until it reaches down to her knees. He grabs the exposed flesh once again and sinks his fingers into her creamy flesh.

Joe lets go of her. He tells her to lie down on the ground facing up with her mouth open. He then gets on one knee over her head and aims his cock into her mouth. He wraps his arms around her back and pulls her off the ground upside down. She lets go of his cock for a second, shocked. Then she quickly regains her composure as she is often upside down during dance. She grabs his cock again and puts it in her mouth.

Joe’s head is now between Riley’s bare legs. Her feet dangle over his shoulders. Her leggings stretch tightly behind his head. He feels Riley working hard on his cock, so he decides to return the favor. He moves her panties to the side once again, this time with his tongue. Then he licks her now humid pussy from the clitoris all the way to the end of the opening. He feels her body shaking, reacting to the lick, before burying his tongue into her opening.

Riley drops Joe’s cock in pleasure and lets out a gasp. Her eyes watery, as he works his experienced tongue down her virgin pussy. She works her lips back around his cock through all the pleasure. She sucks even harder now to please her teacher.

Soon, Riley has built enough pleasure that it is almost impossible to ignore. He throws his head back in pleasure. Pinning her to the locker with his torso, Joe grabs her ankle and throws them over his shoulder. His hand grips onto the leather of her boots. He holds her by her ankles against the lockers. He now thrusts his cock into her mouth. The back of her head banging against the lockers. The sound echoes down the empty hallway.

Close to orgasm once again, he stops and drops Riley safely down to the ground and helps her to her feet.

“Did you enjoy that?”

Riley looks down again, this time nodding with a smile. Cute little dimples appear on her cheeks.

Joe wraps his arm around her waist and walks her to the front glass door. He pulls up her sweater, over her arms along with the T-shirt inside. He throws them onto the nearby bench. She doesn’t wear a bra because her breasts are small. Joe pushes Riley against the glass door. Her tiny breasts lean flat against the coldness. If anyone walks past right now, they can see her clearly. Joe grips Riley by the back of her neck. His hand takes a hold of his cock as he aims at her pink slit.

“This might hurt a little.”

He tests her limits by pushing just the head in. She squirms with pain. Slowly, he enters inch by inch. Before she knows it, he has buried all his seven inches into her. He then slowly pulls his cock out before pushing it back in, until the motion meets no resistance from her pussy. Soon enough, he is ramming his length in and out of her. She screams out in this new found pleasure.

“Yes Mr. Eriksson! YES!”

With one last hard thrust Joe rams Riley off the ground. Riley, still impaled on his cock, collapses against the window. She gasps for air. Joe holds his cock in deep for a few seconds before relaxing and pulling out gently.

“Now that you are use to this, let’s try some other positions so you get the hang of it.”

He pulls her over to the bench and lays her on top of her sweater.

“I can’t believe I haven’t pull this down yet.” He chuckles before he grips the strings of her panties and pulls it down to her knees where her leggings are. Then he pulls both of her legs up on his shoulder. He moves forward and impales her again. He looks at Riley in the eye and she looks back with her innocent glare. This makes him want to push himself in deeper as he turns up his ramming; one hand holding her legs while the other cups her breasts.

“Let’s get this out of the way too.” He pulls out and drops her legs. He peels her boots off, and then he grabs her long socks and pulls them off too. Lastly, he pulls her leggings and panties off. He moves forward to stuff her panties into her mouth. She hesitates but lets him put it in eventually. He pulls her off the bench and makes her kneel before it. Her elbows are on the bench to support herself. He wraps her leggings around her neck before he straddles her ass. He enters her pussy from behind. while he pulls on the leggings, he rams her again and again as he turns her inside out.

As Joe is taking away this young 18-year-old’s innocence he jokes, “Guess you’re not a virgin anymore are you?”

Joe looks outside and sees it’s getting dark outside. He decides he needs to finish soon; but he needs to do a couple of things first. Laying Riley down on the bench once again, he grabs her by the ankles. He wraps the bottom of her feet around his cock and pushes through the little arch of her feet.

Joe feels like he will explode as he grinds her soft feet. He quickly moves forward and throws each of her legs on his shoulders. He enters her newly abused pussy one last time and gets only a couple of strokes in before he unloads his cum inside her. Riley is in too much pleasure to worry about getting pregnant.

Joe pulls out after he releases all his seeds inside her. White liquid drips out of her. Riley lies on the bench with her eyes closed, lost in her own little paradise. Joe pulls out his phone and takes a photo of the girl he has just ruined, with cum still leaking out of her. He calmly grabs her leggings and wipes all the juices, hers and his, off his descending cock.

“Wow Mr. Eriksson! I never knew I could have so much pleasure!” Riley says as Joe pulls up her stained leggings for her.

“If you want, Riley, we can always do this again soon.”

“That’d be great!” Riley says as she steps back into her boots.

“It’s getting late now, be careful walking home ok?”

“I will! Bye Mr. Eriksson!”

Joe smacks the young girl’s ass one last time before he helps her out the door. Then he walks back to his desk. He opens his drawer and throws her panties and the picture he took in there. He locks it shut. Smiling to himself as he pulls out a bucket list and crosses off the name Riley.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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