To love an older woman
Rejection
Load Full StoryNext Chapter"I'll catch up with you guys later. I gotta return this."
Your friends look to see the book you're holding up and scoff.
"Anon, why do you even waste your time reading?"
"Its not a waste of time you uneducated Fuck. You should try it some time."
He shrugs. "Whatever, Anon."
Your friends walk off as you head to the library.
You're excited. REAL excited. You stop by the library often these days. You enjoy reading. You really do, but Ms. Cheerilee tutors in the library after school on Fridays.
You're Fucking ecstatic. Maybe you should start taking tutoring with her.Fucking brilliant.
You've always had a thing for older women. Her overall friendliness and happiness is just contagious to you.
You look down at your book and flip through it nervously as you make your way to the library. Heading up the stairs, you look to your right down the hallway.
Library
‘Alright, here goes nothing.’ You make your turn and approach the large library doors.
Pushing them open, you're immediately hit with the familiar, musky scent of books. Fresh.You glance left. Then right.
"Afternoon, Anon." You glance over at the reception desk.
“Afternoon." you say, walking up to the librarian.
“Say, have you seen Cheerilee around?"
She shakes her head. "She cancelled for today."
‘Fuck.’ “Ah, well...okay. Thanks for the info."
"Is there anything I can help you with?"
You nod. "Yeah, I need to return this...and I'm going to see if I can find something worth checking out."
She takes your old book and you begin sifting through the shelves. You're drawn to science fiction novels, but you're looking to expand today...maybe fantasy or something.
You drag your index finger across potential titles. “No....No...No...." you mumble to yourself. Nothing is really sounding interesting to you.
"You just grazed over a couple of really good ones."
You glance over.
Twilight Sparkle. You've seen her here in the library a couple times, but never spoken to her. “Yeah? Like what?"
She leans over next to you and starts poking through what you've already looked at. "Liiike...This one." She pulls a book from the shelf and holds it up to you.
“When Two Become One?"
"Yup! Its about a guy who gets transported to another world and falls in love with someone from there."
Romance? “Pffft" You scoff.
She glances at you. "Romance can be a very interesting read!" she retorts.
You shrug. ”Nah, not my thing. Not one of those lovey types of people."
"What kind of stories do you like?"
You think over her question for a moment, not really realizing you're having a conversation with a total stranger. “Oh, well...Action, Adventure, Science-ficition..."
“Ooh! Good taste! But, maybe you should go outside your comfort level."
She offers the book to you.
“I dunno..."
"Whats your name?" she asks.
Oh. My names Anon. Nice to meet ya."
"A pleasure. I'm Twilight Sp-"
“Sparkle."
"You've heard of me?"
“Well, yeah, you're in the Rainbooms."
"A fan?"
“Oh yeah! You and Rainbow Dash have amazing voices. And her guitar work is fantastic."
"Whats your favorite song?"
“Music In My Soul...easy."
"Wow. Didn't know we had any actual dedicated fans...."
You take the book that she previously offered to you. "Yeah, I've been listening for awhile now." You glance down at the cover.
"I...guess I'll give this a read. Thanks for the suggestion."
"No problem, Anon. Did you want to hang with the band sometime?"
"What, like actually get to meet everyone?"
She nods.
"That would be Fucking fantastic!"
She's taken aback by your foul language, but she nods in agreement.
"Sounds like a plan. I'll talk with them about it...you can find me in the library after school most days. Meet me on Monday."
"Okay, sounds good."
"Nice meeting you, Anon."
"Feelings mutual."
She walks off with a wave and goes back to her table where she's reading some weird looking book. She's pretty cute. You guys hit it off pretty well. Your thoughts still focus on Cheerilee, though. Ah well. You've got a whole weekend to relax, what are you worried about?
Taking the book back to the front, you hand it to the librarian. "Anon, I had no idea you were that type of guy."
"What do you mean?" You glance down at the book.
"O-Oh, It was just a suggestion from Twilight, not my usual re-" She laughs at your sudden stuttering. "Just kidding..." She swipes it with the laser scanning doohickey and hands it to you.
"Its due in one week."
"Oh, and Anon?" You take your book bag off.
"Yeah?" Putting your new book into the backpack she says, "I have a surprise for you."
You turn and look at her. "Eh?"
She smirks and points to the library entrance. There are two windows on each side of the library doors...through on of them you can see Ms. Cheerilee. Heart skip.
The librarian laughs at your reaction. "Anon, your face is all red."
You glare at her. "What are you talking about?"
"Anon, you don't even take tutoring sessions with Cheerilee, yet you come in to see her everyday...and girls can tell these kinds of things. You like Ms. Cheerilee."
You roll your eyes and sling your backpack back on. "Yeah, I guess I do." you say, accepting your defeat.
"Don't you think she's a bit..."
"Too old?"
She nods. “Yeah, she must be in her mid 30's...and you're...well, in High School. You got to think of it realistically, Anon. Women her age want a man. Not a boy."
"You calling me a boy?"
She shakes her head. "No, but you have to understand that she is probably going to see you that way."
You give a discouraged look.
"I'm not telling you to give up or anythi-"
The library doors open. Cheerilee enters, walking up to the reception desk.
"Did any of my students come by?"
The librarian turns to her. "Yes, but they've left already...I thought you cancelled...?"
"I did, but my after school plans ran into some...complications."
"Sorry to hear that....though." The librarian looks over to you. "Anon was looking for you though!"
Cheerilee glances over at you. "Oh! Hi, Anon!"
"Hi..."
"What can I help you with?"
The librarian blurts out, "He needs help with his math!"
You glance at the librarian. Then back at Cheerilee. The librarian gives you a GO! signal
With a sigh you say, "Yeah. Math."
"Okay, well have a seat at one of the tables and I'll see what I can help you with."
The librarian gives you a thumbs up. Well at least she tried hooking you up. You walk over to the table, nervous as fuck. Just play it cool and everything will be fine, Anon.
You pull out her chair for her.
She giggles, "Why thank you, Anon! Such a gentleman!"
"Yeah. No problem." She sits down and you push her chair in for her. Okay, could NOT be going better so far. Sitting across from her at the table, you pull off your backpack and remember that you don't have math this semester. Shit.
She waits patiently as you pretend to dig through your backpack.
"Uhh, Cheerilee?"
"Hmm? Yes, Anon?"
"I uhh...I don't actually have math."
She gives you a confused look. "Then...what did you want to see me for?"
You rub the back of your head. "Well I was wondering if I could talk to you about something kind of personal."
You talk to her on a regular basis, so something like this isn't entirely out of left field.
"Okay, Anon...well, what did you want to talk about? I must say this is kind of out of left field."
"Well, theres something I need to tell you."
"Well, you can tell me anything, Anon. I may not be your teacher, but I'd certainly like to help."
You breathe in slowly. You breathe out slowly. "Well, Cheerilee, I was wondering if you want to like" You fiddle with your fingers, staring down at them. "Maybe...spend some time together after school..."
She blushes."Wh-What? What do you mean?"
"I don't know, like...going out and getting a drink or something."
She starts shifting in her seat, looking kind of uncomfortable. "Gosh, Anon...I don't know what to say..."
"Will you at least consider it?"
"Anon...you're a great student, and a very handsome man, but...I feel as if you're too youn-"
"Too young? Come on, age is just a number."
She blushes again. "Anon, I just think that you would be better matched with someone your age."
"Women my age don't really know what they want. They're still experimenting with what they want. I'm past that stage."
She giggles. "Anon, you're still young too. You have a lot of things left to figure out."
She stands up."I'm really flattered, Anon...but I think we should stay friends."
Ouch. That almost physically hurt. Disheartened, you nod slowly. Trying not to show disappointment, you smile.
"Right. Friends. Thanks for at least listening to what I had to say, Cheerilee."
She waves her hand dismissively. "No problem, Anon...I should really get going though."
"Right..."
"Goodbye, Anon." With that, she walks towards the exit.
You lean back and sigh.
Author's Note
A work in progress i've used on 4chan and edited for this format. I've been working on this for quite some time. Hopefully better than my other stories.
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