Black Mailed into a Relationship?

by Shadowheart016

Rating: mature
Tags: Human, Romance
Length: 2245

Miss Cheerilee wants Scootaloo.. She has for a while and now.. Now she has him.

Miss Cheerilee wanted Scootaloo for a while now. And now she has a way to make him hers. And he can't say no. All he can do is hope no one finds out.

Published 1970-01-01 00:00:00 UTC
Last updated 2015-11-06 15:39:33 UTC

Detention

Scootaloo sits in the back of the class in between Sweetie Bell and Apple Bloom, drawing a picture of Diamond Tiara naked, her arms covering her breasts as her free hand covers her vagina. He is finishing up shading her thighs when a black skirt, which hid thick thighs and a huge ass, comes into his field of view.

Freezing up Scootaloo slowly looks up meeting he disappointed gaze of his teacher since he was just a young colt, Miss Cheerilee. She shakes her head slowly.

“Scootaloo, you will see me after class has ended,” Scootaloo’s face became visibly red as she spoke, “is that clear?” At the slow nod of his head she looks at his ‘artwork’ before continuing, “And bring this with you”

As Miss Cheerilee turned to walk away Scootaloo quickly tucked his masterpiece away. The rest of the class was filled with questioning looks from Sweetie Bell and Apple Bloom along with the rest of his classmates.

At the end of class and everyone had fled the  building to enjoy the evening and their weekend Scootaloo slowly walked to the front of the class where Miss Cheerilee awaited, her legs crossed with her hands in her lap as she sat on her desk a distasteful look on her face.

Scootaloo slowly pulled the ‘artwork’ out, holding it close to his chest, “Y-you wanted to see me..” he said nervously.

Cheerilee nodded slowly before holding her hand out, clearly wanting Scootaloo to hand her the picture he had drew earlier. Lowering the picture to just in front of her Cheerilee takes it looking at it for a moment before a smile barely noticeable smile touches her lips, “Well, we have two options, one, you can spend tomorrow in detention or you could spend two days next week in detention.”

Scootaloo shifts from foot to foot, “But.. Tomorrow is Saturday... “ Miss Cheerly nods as if to say, yes and “We don’t have school tomorrow… How can i have detention?”

Miss Cheerilee sighs as she uncrosses her left leg from her right, then she lays her right over her left leg. Sitting up straight her legs once again crossed she smiles, “It would be saturday school though you would be doing that same as if you were in detention.” Glancing down at the drawing she looks up at Scootaloo, “How would you know what she looked like undressed?”

Scootaloo’s face turns bright red as he tries to find a way around the truth. Right as he is about to speak Miss Cheerilee raises her hand stopping him, “Never mind, we can discuss this at detention… Tomorrow?”Cheerilee asks with a raised eyebrow. When Scootaloo nods Miss Cheerilee dismisses him to go home.

The next day, Scootaloo walks into the classroom to find Miss Cheerilee bent over her desk looking at something, giving Scootaloo a clear view of her plump ass which is partly covered by her dark purple panties.

Miss Cheerilee stands up turning around to find Scootaloo standing there with bright red cheeks. “Oh, good you’re here. You can take a seat.. On the front row.” Scootaloo nods and quickly takes a seat careful not to make eye contact.

After a moment Scootaloo looks up to see Miss Cheerilee looking at the drawing of Diamond Tiara. She walks up to his desks, shaking her hips a lot more than she normally does. In doing this Scootaloo couldn’t help but notice how tightly fitting her clothes were, which showed off all of her curbs including a bit of cleavage from her shirt which wasn’t quite buttoned all the way up.

Placing the drawing on the desk Cheerilee pulls up a chair sitting in front of the desk that held Scootaloo, crossing her legs. Pointing at the drawing she smirks, “Now, how about you tell me how you know what she looks like naked? Hmm?”

Scootaloo stares at the picture he had drew the day before, “I um… you see.”

Miss Cheerilee cut him off with a raise of her hand, “I’ll tell you what I think.. I think that either you have been spying on her or you have done things with her..”

“I-I didn’t do anything with her!” Scootaloo stammered not realizing his mistake.

“Oh?” Miss Cheerilee’s eyebrow raises a bit, “So you were spying on her?” At her words Scootaloo’s face lights up bright red.

“N-no ma’am!” He manages to spit out half scared Miss Cheerilee will tell Diamond that he had spied on her.

Cheerilee laughs lightly. “Someone's flustered.” As she spoke she raised a hand to his cheek brushing him lightly with her fingers tips, “How old are you now?”

Scootaloo pulls away confused, “18?”

Miss Cheerilee grins standing she leans over the desk revealing more cleavage, Scootaloo’s eyes instantly focused on them causing his stallionhood to harden. “Oh? Is it a nice view? Would you like for me to show you more?”

Scootaloo looks up quickly, locking eyes with her. She unbuttoned a couple of buttons on her shirt revealing her dark purple laced bra. See this caused Scootaloo’s erection to twitch with excitement, but he looked away.

Cupping his cheeks, Cheerilee made him turn his head and look back at her. “Now don’t be that way.. You will look at a girl without her permission but if a woman wants you to you won't?” Scootaloo bites his lip trying hard to not look down at her huge bouncy beautiful breasts.

Releasing him, she walks over to a stack of drawing paper grabbing a few sheets and a couple pencils she walks back to Scootaloo, who is watching her every movement, laying the drawing supplies down in front of him, she grins seductively, “how about draw me naked?”

Scootaloo looks at the paper, “But you're my teacher… It would feel wrong.”

Miss Cheerilee sits on the edge of his desk cupping his chin causing him to look up at her, “You can draw me or I could give Diamond Tiara a call if you’d like?”

Scootaloo’s bottom jaw drops leaving her jaw hanging open, not sure how to respond. After gathering his wits he looks up at her, “Are… Are you blackmailing me?” The only response he got was a sly grin. Biting his lip he looks at her, “well, I guess I could draw what I Imagine you look like naked..”

Miss Cheerilee stopped him, “Or I could strip and you could draw what I really look like naked.” It wasn’t a suggestion. She wanted him to do it. Or else.

After a slow nod from her student she pushed her chair out of the way and stood in front of Scootaloo, “Oh, and I better not catch you looking away while I strip. I am doing this for you too…”

At the bite of Scootaloo’s lip Cheerilee begins to unbutton her top the rest of the way, exposing the skin underneath. Pulling her shirt off she drops it on the floor, lust filling her eyes. Cheerilee then reaches behind her back unclasping her bra she lets it slide down her arms and fall on the floor as her huge breasts jiggle a bit.

As she unzips the zipper at the left side of her skirt, she bites her lower lip as she takes notice of Scootaloo shifting from side to side pushing lightly on the top of her skirt it slips down her legs and she stepped out of it then standing just in her panties she giggles as Scootaloo’s blushing face.

“Would you do me a favor sweaty?” Miss Cheerilee asks him biting her lip seductively.

Scootaloo nods his head slowly not liking where this is going.

“Will you come help me get these panties off?” Cheerilee asks before she runs a hand up her thigh over her panties to her breasts caressing herself slowly.

Scootaloo’s eyes widen, “I-I thought you were going to strip for me. Not Have me strip you…” Scootaloo starts to look away but turns back to her fearing the punishment she might have in store.

Cheerilee pouts slightly, “Awe… fine. But since  you won't, after you finish drawing me I have another activity for us!” She finishes what she says with a smile before she pushes her panties down. Picking them up she dangles them in front of Scootaloo. “hold on to these for me. they are my favorite panties.”

After a pause Scootaloo reaches up grabbing the panties Scootaloo reaches up grabbing the panties Scootaloo sets them on the desk next to the drawing materials.

Cheerilee walks over to her desk and sits on the edge her legs spread slightly biting her lower lip. “Now, draw me just as good as you did her… Okay?”

As Scootaloo nods and picks up the pencil to start drawing he notices Cheerilee rubbing her vagina and staring intently at him.  Blushing, he starts to draw making quick light strokes trying to get done with this as quick as possible. It wasn’t that he didn’t think his teacher was beautiful, because she is. Its that she likes him and it felt wrong… In a good way.

A short time later he finishes drawing his teacher. When he is done he places his pencil on his desk and looks up at his teach, whom is still rubbing herself. “I’m done.” When he says this she starts to rub herself faster panting, then her body tenses as she moans as she orgasms.

Blushing Scootaloo watches as she recovers. When she does she walks over to him looking at his drawing of her. He glances down looking at her soaked vagiana.

“Close your eyes,” Cheerilee, who is standing next to him, her breasts at his eye level says. Scootaloo does what she says. Opening his mouth to speak Cheerilee slips two of her cum soaked fingers into his mouth, “Mmm, now suck on them Scootaloo.” His eyes fly open. Cheerilee’s eyes are closed and she has two fingers on her other hand inside of herself moving in and out. Scootaloo closes his eyes and starts to suck gently on her finger. After a moment Cheerilee whispers, “Tongue…”

Guessing as to what she wanted he runs his tongue along the underside of her fingers and is rewarded by a moan from his teacher. Cheerilee pulls her fingers out of his mouth with a wet pop. Opening his eyes, Scootaloo took note that she had stopped fingering herself. Blushing he looks up at her, “Was that the activity you mentioned before?” Scootaloo fidgets a bit his Stallionhood throbbing with excitement.

Cheerilee shook her head as she licked her fingers clean. “no… That, my new toy, was a preview.”

Scootaloo nods slowly before giving a confused look, “Your new toy?” He asks not understanding, “I thought this was just for today… It is just for today… Right?” He asks a worried tone in his voice.

Cheerilee giggles, “Oh no… You're mine now… That is unless you want Diamond to know?” She giggles again. “Now. help me get dressed we will finish detention at my house.” Sighing Scootaloo stood up holding out her panties for  her to take.

Biting her lip she smiles, “No… You’ll be dressing me.” Scootaloo’s jaw dropped before he sighs knowing she would hold this over his head. Getting on his knees he holds her panties out so that she can step into them. Once she has stepped into them, he runs her panties up her legs, when they reach her thighs his fingers begin to brush against her huge thighs, which are  way to big for her panties. After getting them on her he fixes them in the back and grabs a handfull of her ass.

With a gasp Cheerilee jumps slightly before biting her lip and leaning back against Scootaloo, “Mmm… And why did you do that?”

Scootaloo grins, “Well, if I am going to have to do this, I am going to have fun with it..” Standing in front of her, he reaches over to her desk grabbing her bra, slipping it up her arms and fixing it on her breasts, he steps behind her slipping her clasps together. He kisses her neck reaching around her cupping her breasts caressing them roughly and is rewarded with a moan from Miss Cheerilee. Running a hand down her body slipping it under her panties he begins to reb her causing her to moan more.

After a few moments of teasing he slips a finger inside of her, as he slowly fingers he he kisses her neck lightly. After a few seconds he stops abruptly and walks around her grabbing her skirt and kneeling in front of her he holds it out for her. Cheerilee glares down at him, “Why did you stop?!” Her cheeks are bright reed and her panties are soaked.

“Because, I wanted to tease you a bit.” Scootaloo replies, “Now I would like to finish up getting you dressed.” With a sigh, Cheerilee steps into the skirt. After pulling it  up Scootaloo zips it and grabs her shirt and puts it on her then begins to button it from the bottom up. When he buttons the second to top button Cheerilee leans forward kissing his lips. Her tongue quickly finds its way into his mouth and becomes entangled with his tongue as she kisses him and he kisses back. Pulling away with a gasp, Miss Cheerilee grins at Scootaloo pulling him by the hand to the door. “Hurry up.. I can’t wait to show you my bedroom...”