"Thank you so much for helping us, Anon." Lyra says while you pack up your books.

"Anytime." You reply. "Always glad to help."

"What do we owe you?"

"You should know by now that my services are always free."

"Oh yeah. I keep forgetting that." The mint colored girl replies before giggling. "I'm glad that you're always around to help me and my friend here with our homework."

"Yeah." Bon Bon adds. "You're really helping us out here. Big time!"

"No problem at all. Well, I'll see ya'll later." You say before exiting Canterlot High's library. Letting out a sigh of relief, you begin walking towards your locker, eager to head home for the night. Being a tutor for CHS is hard work, but the fact that most of your clients are rather attractive girls balances the scales in terms of it being worth all of those late nights cramming in all the knowledge you could. Your client list ranges from Lyra & Bon Bon, always together, to "The Great and Powerful" Trixie, leading up to Vinyl Scratch, who you always wonder if she can even hear you over her music. The reputation you've garnered as one of Canterlot High's top tutors, let alone the only one who does it for free, makes your schedule very hectic.

Walking towards your locker, you feel your phone buzzing in your pocket. "Might have to let this one slide." You think as you pull the phone out of your pocket to see who it is, only to see it is a text message from an unknown number. "Guess not. Don't want to look bad for someone who is asking for the first time." Shrugging your shoulders, you press the button that opens the message.

"Hello Anon...

I was hoping that you could give me some help studying for a rather important test that is coming up soon.

Normally, my friends would help me, but this time, I feel a personal one-on-one study method would be better.

And I hear you're one of the best tutors out there.

Please respond as soon as you read this. It would make me ever so happy if you help me out.

Signed,

Rarity"

"Rarity?!" You scream internally as your eyes widen while looking at the name on the screen. Rarity is one of the hottest, sexiest, and most popular girls in the entire school. Plus, it doesn't really help that you've had a bit of a crush on her. Ever since you first met her, you've had this feeling. Kind of like this movie that you've seen involving a man, a woman, and a ship. The fact that she is asking for your help comes at such a shock that you lean back against your locker door as you feel your body lose it's balance for a moment. Giving another look at your phone to make sure you read it correctly, you begin typing a response.

"Hey Rarity,

I'd be glad to help you in any way I can. What exactly do you need help with? I ask this so I can bring the proper textbook.

Also, where and when would you like to meet up?"

It isn't long before you get a reply from her.

"Well...

I need help with some algebra homework that needs to be done by tomorrow.

Also, I'm at my clothing shop so perhaps you could stop by in a bit?"

"Algebra?" You say while letting out a little sigh. "Not exactly my strongest subject." You then give another look at the text. "But this could be my best chance to actually be with Rarity!"

"Sure. I can help you out with that. Just give me a few minutes to get my things and I'll be over."

Not even a minute passes before she texts back.

"Thank you ever so much, darling. See you soon! ;)"

"A wink? Must've been a typo or something." Not giving it much extra thought, you grab your algebra textbook and a spare notebook from your locker. Once you get it all into your backpack, you race down the hallway and out the front doors of the school, sliding down the railing of the stairs before rushing off towards your car. Not long after, you're driving out of the parking lot and out onto the highway towards Rarity's shop. The trip itself doesn't last very long as her shop isn't far from the school. Your hands are shaking in nervousness as this will be the first time that you'll be having a tutoring session with Rarity and you don't want to mess it up. Parking near the entrance of the store, you turn the car off and look towards the building. "Okay... you can do this." You think, moving your hand towards the door handle. "It's just like any other session. Even though this time, you're helping the girl you have a crush on." Taking in a few deep breaths, you open the door and step out of your car.

Walking towards the door of the shop, you feel your stomach grow uneasier with each step closer. "Get a hold of yourself!" You yell internally, stopping just outside the door. "Just pretend it's just another session. Nothing special." With that thought running across your mind, you slowly push against the door and walk inside. A little bell mounted above the door rings, making you jump slightly before you hear her beautiful voice.

"Come in!" Rarity's voice echoes from a room behind the counter.

"Rarity? It's Anon." You yell. "You asked me for help with some algebra?"

"Yes I did, darling." She replies, but not yet emerging. "Could you give me one moment though?"

"Of course." You reply, setting your backpack down on the counter. "So how are you doing today?"

"Oh I'm doing fine." She replies as you hear her slowly moving towards the doorway. "I do apologize if I interrupted anything that you were doing."

"Actually, I wasn't really doing anything when you texted me."

"That's good." She says before stepping through the door. Your eyes widen in her sheer beauty as she approaches the counter. "So..." She begins while leaning forward, letting her arms rest on the counter, giving a full view of her upper body, particularly her breasts in their cloth prison. "Could I ask you of something? Sorry if it would seem a bit odd of me to ask."

"Anything."

"Could we move somewhere more eh... private? I have a small bedroom upstairs in case I end up spending the night here while making dresses."

You gulp a little before replying. "Oh uh... sure. That's fine. Lead the way."

"Splendid." She replies. "But first, I need to take care of one thing." She walks out from behind the counter and goes over to the door. She then flips a sign around saying "Closed" on it before locking the door. "There we go. Can't have any unexpected guests during our study time now, can we?"

"I suppose so." You reply. You can feel your heart beat a bit faster knowing that you're now locked in the same room with a stunningly gorgeous woman. Picking your backpack up off of the counter, you watch as she begins walking towards you. In an unexpected move, she takes you by the hand and starts leading you towards a stairway leading up to the small residential area above the shop. The feeling of her smooth fingers interlocked with your's makes your breathing start to quicken as she leads you up the stairs, through a door, and into a small, yet nicely decorated room with a full sized bed, desk, mirror, dresser, another door, and a little tv.

"Do make yourself at home." She says while turning on the lights. "I must say that it is rare that I would be asking for help from someone other than my friends, but they insisted that I give you a try."

"That's odd." You reply. "I've never had a study session with any of your friends before."

"Well, they heard you were one of the best. And the only one that doesn't charge for helping."

You chuckle at what she says. "Well... I'm just trying to be a nice guy and help others when needed."

"Such generosity." She replies. "I've never known a guy like you before." You open your mouth to reply, but stop when you see that she is gazing at you with those cute sapphire colored eyes of hers. "What's the matter, darling? Opal got your tongue?"

"Opal?" You reply before hearing a small meow beneath you. Looking down, you see a small cat with a purple bow in her fur rubbing up against your pant leg. "Ohhh!" You say, letting out a small laugh. "That's a good one."

"You think so?"

"I do." You then see a slight shade of red appear on her cheeks after you say that.

"No one besides my friends think my jokes are funny."

"Seriously?" You ask in a surprised tone. "Wow. That's crazy."

"Quite so." She replies before sitting down on the bed. She pats the spot next to her, motioning for you to sit down next to her. You are hesitant at moving from your spot. "You gonna tutor me from over there?" She asks, giggling slightly. "It would be much better if you were sitting here. Come on, don't be shy. I promise I won't bite." She lets out a small giggle again. "Well, not hard at least."

"Be gentle." You reply before both of you begin chuckling. You then proceed to slowly walk over to the bed and sit down next to her. "So... what exactly do you need help with for algebra?"

"Oh!" She replies. "My sheet is in my bag over there. Give me one moment." With that said, she stands up and walks over to her bag sitting on the other side of the small room. But once she gets to the bag, she doesn't crouch down to get the paper that is within. Instead, she bends over, giving you a complete view of her skirt covered derriere. Looking towards her momentarily, you turn your head, looking away as you feel your cheeks get warm. A minute or so of her being bent over passes before she straightens herself up. She then turns around and walks back over to the bed. "I need help with all of these problems. I do hope that you'll be able to help me with them."

"Alright." You reply, pulling out your textbook. "Let's get started."

Once you begin, Rarity decides to lean closer towards you so she can "see the book better" as she put it. As the minutes pass by, the space between your body and her's slowly closes until you feel her side pressed up against your's. The soft touch of the skin on her arm pressing against your's slowly makes your crotch begin to heat up. Every breath you take through your nose has a lingering smell of her perfume. Sensing your member begin to grow, you place the book down on top of it to keep it hidden. "So...." You begin to ask. "Think you got it now?"

"I think I might." She replies, gently resting her head on your shoulder for a moment.

"Alright then." You say in response. "So... what is the formula for finding the area of a sphere?"

"Take four times pi times the radius squared."

"Correct." You reply. "And the volume?"

"Four thirds pi times the radius cubed."

"Correct again. Final question. Volume of a cone?"

"One third pi times... the radius squared times the... height?" A few seconds pass before you give a response. "Well? Spit it out, darling!" She says. "Am I right?"

"100% correct."

"I can't believe it!" She says in excitement. "I finally know how this works!" In her excitement, she grabs you and pulls you in for a massive hug. "Oh thank you! Thank you so much, Anon!" This sudden move leaves you speechless as she lets go. "Without your help, I probably would have flunked that test for sure."

"Glad to see you're a good learner." You reply. "Maybe you just needed a different scenery to get it down."

"Or maybe I just needed a different person to teach me this stuff." She says. "One that is more friendly to be around than a teacher."

"That too... I suppose." You reply while getting up. "Hey uh... you have a bathroom up here I can use?"

"Yes. It's just behind that door." She says, pointing to the other door in the room.

"Thank you." You reply. "If you want, you can look through this notebook for more formulas." You gently toss her your notebook from your bag

"Splendid." She says before catching it.

"Be right back." With that said, you disappear into the smaller room and shut the door behind you. "Well, this is going better than I thought it would." You think as you stare at yourself in the mirror. You continue to stare at yourself until you feel the burning in your crotch fade. "Much better." You then step out of the room only to find Rarity now staring at you with lidded eyes.

"Why Anon... I didn't realize that you were a poet."

"Poet?" You ask before you see the cover of the notebook you tossed over. The one that you have all of your math formulas written has a red cover. The one in Rarity's hands has an orange cover, the one that has a certain poem about a certain purple haired girl. "Shit! I grabbed the wrong notebook!"

"Yes." She replies. "I even found this lovely little poem that you've written about... me."

"Oh fuck!"

"Such purple hair, I can't compare,

With skin as white as snow,

Is there any girl out there more perfect?

The answer, I do not know.

Her eyes are as blue as sapphire,

She has a voice that can soothe a beast,

To say that no one can match her in elegance,

Is in fact saying the very least.

There is only one with so much beauty,

Because my eyes need no more clarity,

For the one girl who has it all...

That girl's name is... Rarity."

As she reads the poem, your cheeks begin to turn a deep shade of red. "Oh my!" She says, her cheeks turning a deep shade of red too. "No one has ever written a poem about me before." She turns her gaze back towards you. "Do you really feel this way about me?"

"Well... umm...." You say before sighing. "Yes. All of it is exactly how I feel."

"Oh... my!" Her hand covers her mouth for a moment before she lets it fall to her side. "I've never had a guy feel this way about me before." She slowly gets up and begins walking towards you, her eyes still lidded and she is now giving a little extra swing to her hips as she gets closer.

"Uhh... Rarity?" You ask, slowly starting to back away. "What are you doing?"

"I just think it is time that you receive your payment for helping me."

"Oh but umm..." You say while gulping slightly. "I don't really charge for my services. You know that."

"I'm sorry darling." She says. "But after all you've helped me with and now that I know of these feelings you have for me, I simply can not let you leave here without a proper thank you."

"No really. It's quite alright." You reply before your back hits the wall. Soon after, she stops in front of you and places an arm on both of your shoulders.

"I insist." She says in a soft tone. She then slowly leans in, her head moving closer towards you as the scent of her perfume fills your nostrils once again. You close your eyes, not knowing what to expect. Not even a second passes before you feel her lips make contact with yours. You hear a slight moan as she presses them against yours more until you feel her tongue try to make it's way into your mouth.

"Holy fuck!" You think as she continues with the kiss. Her tongue now forces it's way inside your mouth and begins to play with yours. Her soft moaning instantly makes your crotch heat up again as she presses her body against yours, forcing you up against the wall. A minute of this passes before she breaks the kiss, both of you breathing heavily as she does.

"Mmmmmmmm..." She moans while keeping her body pressed against you. "I have a feeling we're both going to enjoy this." After saying that, she pulls her body away from you, grabbing your hand in the process and leads you back over to the bed. "I'm going to make sure that you are rewarded for this."

"Rewarded for having a crush on you?"

"Yes and also for being the first guy that has shown me that he has genuine feelings for me, whether you meant to or not." She replies as you both reach the side of her bed. "I just have one question. You do have protection, right?"

"I actually do keep one on me in my wallet just in case the moment arises. Never really used it before though."

"So this will be your first time then?"

"Yes." You reply before processing what she just asked. "Wait... what?"

"Anon... I'm not going to lie. I've kind of had a bit of a crush on you myself."

"You're joking."

"Nope. I've admired the way you've been helping others without asking for anything in return. It reminded me of well.... me. Plus, you are rather cute for a tutor." Before you have a chance to respond, she throws herself at you again, pressing her lips against yours in a flurry of short, yet passionate kisses. Soon, they're pressed firmly against eachother as her tongue once again invades your mouth. While both of you are kissing, she leans forward, pushing you onto the bed with her landing on top of you.

"Holy shit!" You think while her tongue wraps around yours. "I wasn't expecting to lose my virginity tonight!" As you think this, she sits up on top of you and moves her arms down to her shirt.

"Are you ready for this, darling?" She asks, her hands clenching the bottom of her shirt.

"Yes!"

"Splendid." She says before slowly removing her shirt, revealing a purple bra underneath. She gives her breasts a playful swing as you gasp in awe of the beauty in front of you. Giggling at your reaction, she moves her hands behind her back, leading to the purple bra falling onto your chest. Your eyes widen as you see the girl who you've been crushing on for months is now sitting on top of you, topless.

"I'm not worthy of such beauty." You say as she motions for you to take your shirt off.

"Nonsense." She replies while you do as she asks. "Take pride in knowing that you're going to be the one who takes my virginity away." After that, she lays back down upon your body, pressing her now naked breasts against you. Your lips meet once again while your hands now run along her back, making her moan as they go down her spine towards her skirt, stopping just before you reach her soft cheeks. She breaks the kiss and moves over to your ear. "Don't be afraid." She purrs softly before giving your ear a little nibble. After you hear that, your hands slowly venture down her skirt until they slip beneath, making her moan slightly once you touch her panties. Wanting to increase her pleasure, you give her ass a little squeeze before running a finger between her thighs until you find a rather damp spot. She moans in delightful pleasure as you press against the dampness.

"I can't believe this is actually happening!" You scream internally as Rarity moves her hands down your body before you feel her hands undo the button of your pants. She slips a hand inside, gently squeezing your now erect member, making you let out a soft moan.

"Mmmmmmm.... you like that, darling?" She asks in a seductive tone.

"Yes." You reply. "Yes. I love it!"

"Well then...." She says before slowly beginning to slide down your body. "You're going to really love what I'm about to do." Her hands grab the edge of your pants before she pulls them down to your ankles, revealing your boxers and your fully hardened member. Letting her hand venture inside, you feel your shaft get squeezed again before she pulls your boxers down. "Well now.... looks like someone is enjoying this." She says as she gazes at your cock. Her soft fingers gently run up and down your length, making you moan slightly before you feel her lips kiss the tip.

"Fuck!" You think as she continues kissing the tip of your shaft. She then lets her tongue run up and down the side, gently covering your member with her saliva. A minute passes before you feel her lips kiss the tip once again.

"Do you want more?" She asks while playfully running a finger up the length of your cock.

"I have a feeling you know the answer." You reply, making her giggle. She then opens her mouth, letting your cock feel her warm breath before she slowly begins taking it inside. Your moaning grows louder as she gently begins bobbing her head up and down, taking more and more of you in her mouth with each descent. Her tongue gently wraps around your cock, making both of you moan in pleasure. As she moans, her throat begins to vibrate around the tip whenever she tries deep throating your cock, making your moaning grow even louder. "Ohhhh fuck! This feels so amazing Rarity!" You groan as she continues until letting your dick out of her mouth with a loud popping sound.

"I'm glad you're enjoying yourself hun." She replies.

"Nicknames now?" You think as she goes back to sucking on your cock. As her tongue swirls around your entire length, you can feel yourself inching closer to your inevitable orgasm. Rarity seems to sense it too and slowly takes your cock out of her mouth.

"Wouldn't want to spoil the fun now, would we?" She asks in a playful tone. All you can do in response is shake your head since her amazing blowjob has left you speechless. She giggles at your actions and stands up. "Besides. I do believe it is my turn to get some pleasure."

"The pleasure... would be all mine." You reply, getting up so she can lay down on the bed. Turning around, you lean forward and begin to pull her purple skirt off. She giggles as you find her purple panties are extremely damp. "Looks like someone else was enjoying that blowjob just as much as I was." You say in a playful manner.

"Guilty as charged." She replies. "I simply couldn't help it." You chuckle in response while slowly removing her panties.

"This is the moment I've been dreaming of!" You think once you get a glimpse of her soaking wet, snow white pussy. "It's so beautiful!" You get down on your knees and she proceeds to spread her legs wide open.

"Mmmmmmm.... eat me Anon." She commands in her seductive voice. "I want you to go where no man has gone before." You gladly oblige to her request as you slowly lean in, smelling her ecstasy as it surrounds you. You slowly stick your tongue out and give her slit a slow lick, making her hips move as she moans. "Ohhhh yes Anon. Keep doing that!" You do it again only this time, you slide your tongue between her lips, getting a taste of her sweet, succulent juices. With each of her moans encouraging you to do more, you slide your tongue deep inside her pussy, going in as far as possible. "OHHHHhhhhh!" She cries out in response to your sudden move. "That feels soooo good Anon." You continue sliding your tongue in and out of her pussy while her legs wrap themselves around the back of your head, keeping it still as her moans grow increasingly louder.

"Keep going Anon!" She moans in pleasure. "I'm about to cum!" You'd reply, but her legs keep your lips firmly pressed against her sex. So you decide to let your actions speak for you. Without warning, you begin licking her clit while sliding a finger inside her. "OHHHHHHHhhhhh FUCK!" She cries out.

"Must have hit her sweet spot." You think as you continue fingering her ever increasingly wet pussy. Soon, you feel her inner walls begin to tighten around your fingers as her thighs press against the sides of your head.

"OHHHH FUCK!" She cries out before you feel your finger become drenched in her cum. You pull your finger out of her pussy before sliding your tongue across her slit one last time, tasting her cum. It was rather sweet when you began swallowing some of it. "Ohhh Anon. That was simply divine!" She says while you get up. "Now there is something that I think both of us want to do."

"Turn in... our V-cards?" You ask, wiping a bit of her cum off of your lips.

"Bingo." She replies while gently caressing her breasts. "The time has come. Give me that condom you said you had."

"Alright." You reply, bending down to get your wallet out of your pants, which are still around your ankles. Opening the wallet, you pull out the condom and hand it to Rarity. She proceeds to rip the packaging and pull out the latex cover.

"No going back now." She says while placing the condom on your still erect member.

"Why would we want to go back?"

"Good point." She replies. She then spreads her legs wide open once again. "Please be gentle, Anon."

"Don't worry, Rarity." You reply. "I'll be as gentle as I can be." With that said, you slowly place the tip of your newly covered shaft at the entrance of her moist pussy. "You ready?"

"I believe you already know my answer, dear." She replies.

"Very well then." Seconds later, you slowly begin to penetrate her pussy with your cock. Roughly halfway in, you feel a slight resistance before Rarity lets out a gasp of pain.

"Fuck!" She cries out, making you halt your momentum.

"Are you alright? Did I do something wrong?" You ask in a panicked tone.

"You just popped my cherry, darling." She replies. "Don't worry, I'm fine. Please, go on. Just be gentle."

"Alright." You say, continuing to slowly slide your shaft inside. Once it disappears inside her, you begin to pull out as gently as possible. Once halfway out, you push it back in and slowly start repeating the process. Rarity begins to moan again as she begins squeezing her breasts together. "I can't believe it!" You think as you continue going in and out. "I just gave my V-card to Rarity! The girl that I've been crushing on for months! This is the greatest night of my life!"

"Could you go a bit faster, darling?" She asks, snapping you out of your inner celebration. You nod your head before adding a bit of speed to your thrusts. Rarity's moans grow louder with each inward movement. She sits up slightly and wraps her arms around you, gently kissing your lips as you continue to go a bit faster. "Yes Anon!" She moans after breaking the kiss. "This feels so amazing!"

"Yes! Yes it does!" You reply before gently squeezing her breasts with one of your hands.

"Ohhhhh!" She groans at the feeling of it. "Mmmmmmm.... that feels so lovely." As you're squeezing her breasts, you get the feeling of your orgasm beginning to develop.

"Ohhh Rarity!" You say as she begins moving her hips to synchronize your movements. "I feel like I'm about to cum!"

"Do it Anon!" She replies. "Cum inside me!" It isn't long before you fulfill her request.

"Fuck!" You cry out. "I'm c-c-cumming! Oh fuck! Yes! Yes! Yes! SHIT!!!!!" You try to hold it back as long as you can, but the pressure becomes too great and your orgasm explodes inside the condom while you are completely inside her. You give a few final thrusts before slowly taking your cock out of her pussy. You both breathe heavily as she watches you peel the condom off. You decide to check for any rips or tears to see if there was any leakage. "Phew." You think upon finding the condom completely intact.

"That felt simply wonderful." Rarity says as she lays on the bed, breathing heavily.

"I feel the same way." You reply. "Hey umm... I know we just had sex and all, but I was hoping if..."

"Yes?"

"Would you perhaps like to uh... go out with me sometime?"

"I'd love to." She replies before gently kissing you on the lips. "Umm... I have a question for you."

"Yes?"

"Would you like to spend the night here with me?" She asks. "I could order some pizza and we could just cuddle on the bed while watching tv."

"I'd like that very much." You reply, giving her a gentle hug while your hands venture down to her cute ass, giving her cheeks a gentle squeeze. She lets out a soft moan.

"Ohhh. You're a naughty one." She says in her seductive tone. "Just the way I like it."

Author's Notes:

Thank you all so much for enjoying this first entry. It makes me glad to see that this idea for a series is turning out to be a very good one. Also, that poem about Rarity is indeed an original, not copied poem. Something I've never done for a story before.