The Hottest Hearts and Hooves Day Ever

by StormLuna

Cheerilee's History

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After having a bite to eat, Cheerilee and Twilight headed back into the library and plopped down on the couch. Twilight looked at herself and then at Cheerilee and said, "You know, I feel so plain right now." She tugged on her shirt and sweatpants and continued, "So lame."

Cheerilee removed her halter top and said, "You know, since it is just us, why don't you remove these clothes? You'll feel a lot better if you do."

Given that Cheerilee had removed her clothes, Twilight figured that she could do the same. When she did, she revealed something that nopony knew she had, huge breasts. The moment she saw them, Cheerilee licked her lips, "Oh so this is why you wear larger shirts?"

Twilight blushed, "Maybe!" She noticed how Cheerilee's were pretty much the same size as hers and added, "And this is why you dress so conservatively isn't it?"

Cheerilee replied, "Yes. I really don't want my students being distracted by them." She then tugged on Twilight's pants and suggested, "How about you remove these things and then we talk some more?"

Twilight nodded and once the two had stripped down to nothing but their undergarments, Cheerilee draped herself around Twilight, stroked her leg and asked, "So Twilight, have you ever been with anypony like this before?"

Twilight's face turned red, "Um, no! I've never been like this!" She then groped Cheerilee's breasts and continued, "I take it you have?"

Cheerilee couldn't help but giggle, "Oh yeah, back in college I was the envy of all my marefriends!"

Twilight asked, "ALL of them? You had multiple marefriends?"

Cheerilee knew that Twilight likely thought she meant marefriends as in ponies she was in a committed relationship and figured that she needed to be more specific. She replied, "When I say marefriends I just mean my friends. That is what we called one another and I tell you, we had some really wild times."

Twilight asked, "Really? What sorts of things did you do?"

Cheerilee began to run her hand up Twilight's leg and replied, "Oh we'd go clubbing every Friday and Saturday night and we'd all get pretty kinky on the dance floor."

Twilight had a look of confusion on her face and Cheerilee found it downright adorable. She figured that a lot of things she has done in the past that Twilight would be incredibly naive about it. She wrapped herself around Twilight and giggled, "You have no clue what I'm talking about do you?"

Twilight replied, "Uh no, that is something that Celestia never taught her students about."

Cheerilee giggled, "Oh Twily, we're going to have to get you out to Marentreal sometime and get you some experience!" She saw Twilight blush a bit and continued, "Ok, about the kinkiness, we'd all go to the club, mingle with random mares and if we got along and found one another hot, we'd grind, grope and kiss passionately out on the dance floor."

Twilight asked, "You'd do that with random mares, you mean mares you just barely met?"

Cheerilee had a feeling that this may cause Twilight to suddenly want out of this situation but also really wanted to tell her about this. She got up into Twilight's face, gave her a passionate kiss and continued, "Yes. One time me and this pegasus got so hot and heavy that we stripped naked right there on the dance floor."

Twilight gasped, "You did what? Didn't you get thrown out?"

Cheerilee laughed, "Yeah we did but hey, she still went home with me and I got what I wanted so it was all good." She could sense further discomfort coming from Twilight and this was something that she did not want. She grabbed Twilight by the hand, pulled her up and suggested, "Enough about that. How about we go up to your room for some fun?"

Twilight gave her a nervous smile, "That sounds good to me."

As Twilight was being led up to her bedroom, she was still trying to fathom everything Cheerilee had told her. She couldn't help but wonder if Cheerilee was simply exaggerating to make herself sound more experienced than she was or if she was indeed telling the truth and truly was that wild when she was in college. One thing Twilight did know though was that she wanted fun times with Cheerilee but going clubbing like that was something that she definitely wouldn't do.

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