The Hottest Hearts and Hooves Day Ever

by StormLuna

Rating: mature
Tags: Sex, Twilight Sparkle, Anthro, Cheerilee, My Little Pony: Friendship is Magic, Porn
Length: 6692

Another Hearts and Hooves Day has arrived and like she always has been, Miss Cheerilee is alone. For many years she was fine with it but just once, she wishes she had somepony to be with, even if it is just somepony to have some fun with.

Another Hearts and Hooves Day has arrived and like she always has been, Miss Cheerilee is alone. For many years she was fine with it but just once, she wishes she had somepony to be with, even if it is just somepony to have some fun with. While they are plenty of single mares to choose from, she has her eyes set on a lavender hottie.

Fetish tags: Watersports, anal fingering, oral and horn sex.

Published 2018-07-06 01:50:06 UTC
Last updated 2018-07-06 01:50:06 UTC

Afternoon Preparations

Hearts and Hooves day had arrived again and like it was every year, Miss Cheerilee, the local school teacher was without a special somepony. Not having a special somepony never really bothered her as she had seen too many ponies go through heartbreak but that didn't mean she didn't want at least a little something for the holiday. While romance wasn't exactly on her want list, having some fun was and she began to think about who she could approach over it.

Afternoon had arrived and after school was over, she headed home and plopped down on her couch. She sighed, "Ugh, another Hearts and Hooves Day alone, all alone!"

She sat there in disgust until something popped into her mind. She said to herself, "You know, its going to be a whole lot easier if all you want is some fun! Romance is overrated but unwinding is exactly what I need."

Cheerilee had one problem though, simply going and hitting on random mares or asking them if they'd be up for a hot night would not make her look good, especially given she was the local teacher. She thought to herself, "Hmmm....who could I approach that would be single and wouldn't tell anypony I asked them about it?"

As she sat there, a list of the hottest mares she knew were single began to cross her mind. She first thought that the local florists might want a fourth but realized that they may go spilling the beans if she approached them. She then thought about Fluttershy until she knew that wouldn't work, "Seriously Cheerilee? That is the last thing Fluttershy would want, asking her would terrify her!"

She continued to think until a certain pony, a certain lavender unicorn that she had had a crush on for ages crossed her mind. She said to herself, "That's it! I could go visit Twilight because I know she's single! Perhaps if I dress sexy enough, I could see if she'd be interested in us studying together maybe something would happen!"

Once she thought of that, she knew who she wanted. She had decided that she was going to go after Twilight and try to seduce her. She knew that she would have to dress to impress so she headed to her closet and began to dig through her clothes. With the exception of what she wore when she was in college, she had next to nothing in the way of apparel that had any sex appeal.

It took her a while but after fifteen minutes of digging, she found her clothes that she had planned on throwing out a long time ago. As she picked them up she couldn't help but remember the days when she and her girlfriend would go out clubbing and seducing as many mares as they could. She smiled and said, "I just hope that if I can do this, I'm just as good now as I was then." She then examined her clothes more closely and added, "And I hope I can still fit into these!"

After several minutes of reminiscing about her more exciting past, she slipped her clothes on and surprisingly to her, they still fit as good as they did the last time she wore them. Once she was dressed, she stepped in front of the mirror and couldn't help but admire herself until she noticed something different, her breasts. She grabbed them, pushed them up like they were back in the day and cheered, "That's more like it Cheer, now let's go get Twilight!"

As she headed for the exit, she couldn't help but feel a sense of confidence and more importantly, she felt young again. She began to realize that for so long, ever since becoming a teacher, that she had lived a mundane and boring life. She felt like she had missed out on so much, she felt like too much of her life had been wasted being rigid like a teacher should be and she knew that while she still had sex appeal that she may as well take full advantage of it.

Twilight's Unexpected Visitor

After deciding to pay Twilight a visit and dressing in a way she had not in ages, Cheerilee headed towards the library hoping she could accomplish her objective. Many ponies could help but stare in shock as they saw her heading down the street, dressed the way she was. Before she could even get there two of her students stopped her and gasped, "Miss Cheerilee, is that you?"

It was Diamond Tiara and Silver Spoon. Cheerilee knew that this likely would not bode well if the two saw her like this but began to try to think of a lie to tell her. She replied, "Yes Diamond Tiara, it's me."

She continued to stare at her teacher and asked, "Why are you dressed that way?"

Silver added, "I never thought you'd, like, dress like that."

Cheerilee began to become more nervous and she finally came up with a lie, "Well I'm going to see Twilight because she has invited me to join her friends for a costume party tonight and I decided to go as an 80s club girl."

The two couldn't help but snicker a little Diamond Tiara snickered, "Wow Miss Cheerilee, I never knew you'd allow yourself to be seen like this!" She gave her a smile and continued, "I guess you're not so lame after all!"

Silver giggled, "Now don't have too much fun with Twilight and her friends!"

Cheerilee gave her a nervous smile before finishing, "Well it was nice talking to you two but Twilight is expecting me and I can't be late."

Once they parted ways, she could hear the girls speculating about what was going to happen, about how they thought that Cheerilee wasn't so rigid and how her and Twilight were likely going to have lots of fun. When she finally got to the library she knocked on the door, hoping that Twilight would answer sooner rather than later.

When the door was finally answered, it was Twilight. She took a good look at her and gasped, "Miss Cheerilee, is that you?"

Cheerilee replied, "Yes Twilight, it's me." She then looked in and asked, "May I come in?"

Twilight wasn't sure what to think about the whole situation but figured that maybe there was a reason for her dressing the way she was. She pointed in and replied, "Of course, go on in."

Once Cheerilee got in she plopped down on the couch and asked, "So, where is Spike?"

Twilight replied, "Oh he got called up to Canterlot on royal business so I'm all alone this weekend." She took a closer look at Cheerilee and asked, "So Cheerilee, why are you dressed like a hooker? Is there a costume party somewhere?"

Cheerilee gasped, "I'm not dressed like a hooker but I did dress this way for a reason." She then thought of a good lie, "Well as you know its Hearts and Hooves Day and given that I'm single, I just wanted to feel young again."

Twilight gave her a curious look and asked, "Ok, you're single but why would dressing like that and coming to visit me have anything to do with what day it is and feeling young again?"

Cheerilee realized that perhaps this was not going to work out and thought she better cut her losses before she made herself look worse in Twilight's eyes than she already had. She turned towards the door and replied, "Never mind Twilight, I guess I'll see you later."

As Cheerilee turned around, something began to cross Twilight's mind. She had always found Cheerilee attractive and given that Spike was gone, she thought that maybe this was fate trying to tell her something. She rushed to Cheerilee, grabbed her and said, "Wait!"

Cheerilee turned around and nervously asked, "Twilight, you're not going to......"

Before she could finish her question, Twilight had grabbed her breasts and was giving her a smile, "I think I know what this is about!"

When Cheerilee her smile she began to think that perhaps things might turn out alright after all and knew for sure when Twilight reached around and planted her hand on her flank. Twilight gave her a smile and continued, "You're all alone and you think I'm hot, don't you?"

Cheerilee turned beet red and replied, "Uh maybe!"

Twilight grabbed her by the hand and ordered, "Well now that I know that, how about we have a bit to eat" she then began to giggle, "and you can see just how hot I am!"

This was not what Cheerilee had expected to hear from Twilight. She gave her a smile and said, "Oh you're on Twilight, you're on!"

Twilight swatted her butt and giggled, "Just call me Twily, no need for formalities now."

Cheerilee replied, "Well then, you can just call me Cheer!"

The two gave one another seductive grins and laughed again. Twilight knew that behaving like this was wrong and would probably enrage Celestia but something about it felt so right. Something about it made her feel free, free from Celestia's control and she liked it, a lot.

Cheerilee's History

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.

Twilight's First Time

Once the two got up to Twilight's bedroom, the very first thing Cheerilee did was grab Twilight and remove her undergarments, revealing Twilight's breasts in all their glory. She grabbed them with a smile and began to suck on them, bringing out a moan of delight for Twilight. She stood up tall, removed her own and giggled, "You know, you can taste mine if you want."

Twilight gave her a smile, leaned forward and began to suck on Cheerilee's. As she did this, Cheerilee began to moan gently and run her fingers through Twilight's mane. It would not be long until Cheerilee pulled her up and ordered, "Your bed, now."

Cheerilee had a very demanding tone of voice in her order and Twilight found that very attractive. She laid down and giggled, "My my, so demanding" She spread her legs wide and continued, "Well Cheer, come and get me!"

Cheerilee licked her lips, "Oh my, all of you looks so tasty!" She began to eyeball Twilight's vagina and giggled, "And your prize looks so needy!"

Twilight nodded and gave her a smile. Cheerilee knew that was Twilight's way of telling her to get started. Cheerilee had always been the type that liked to take her time with her partners so she first began to suck on Twilight's toes which made her giggle a little. Cheerilee stopped momentarily and asked, "Ticklish are you?"

Twilight giggled, "Yes, now get back to work!"

Cheerilee smiled and got back to work on Twilight. At first it was just the toes but then she began to move up her leg. Cheerilee moved so slow that it took her half an hour to reach Twilight's inner thigh, the area that really excited her because of what she would do there.

She began smelling something, something sweet. She held her head up and giggled, "My, my, somepony's ready isn't she?"

Twilight moaned, "Mhmm!"

Cheerilee couldn't help but giggle a bit. That was one thing that she absolutely loved, getting her partners to give simple, cute responses like that. As she slowly moved closer and closer to what she wanted, she could feel Twilight's wet folds up against the side of her face and realized that if she didn't hurry up, that Twilight may cum before she even had a chance to taste her.

When Cheerilee finally reached her target, Twilight let out a gasp, "Cheer!"

Cheerilee stopped for a moment and asked, "You like?"

Twilight gave her a smile, "Mhmm!"

Cheerilee gave her a smile and got back to sucking. Given how close she was to climaxing, Cheerilee knew she had to do something. After another minute of sucking, she remembered something from her college days. She remembered that if she massaged a mare's cutie marks just right, that she could drag out her orgasm for quite some time while bringing her massive amounts of pleasure.

Once she began to massage Twilight, she immediately began to breathe heavier and began calling out her name, "Cheer, Cheer oh Cheer! Yes baby yes, probe me baby, probe me!"

Cheerilee buried her face deep into Twilight's marehood and began to probe her. Soon she found her head locked into place by Twilight's legs. Cheerilee continued to suck harder, probe her as deep as she could and massage Twilight as firmly as she could. Twilight's breathing became more intense and she began to sweat which is something that Cheerilee always loved, when her partners would begin to sweat.

An hour had passed and Twilight's breathing had become so heavy and her heart was beating so fast that she had begun to shake. Cheerilee knew the time was approaching, especially when she heard, "Oh Cheer, oh Cheer, oh Cheer, I gotta, I gotta, I gotta, I gotta cummmmmm!"

Immediately Cheerilee's mouth was filled with Twilight's nectar, nectar that was sweeter than anything else she had ever tasted. Once she had swallowed it, she noticed that her lips were coated in it and made her plans for what she would do. She crawled up on top of Twilight and ordered, "Lick them clean."

Twilight did as ordered and then pulled Cheerilee down into a passionate kiss. They wrapped their bodies tightly around one another and immediately, Twilight pulled Cheerilee to where she was on her back and began to grind her. This brought back so many wonderful memories for her, those rare moments when she would be the sub. Twilight continued to grind her harder and harder until she, like her, was covered in sweat and this turned Twilight on.

She stopped for a moment and giggled, "You know, you feel really good all sweaty."

Cheerilee was in such a state of pleasure that all she could do was moan, "Mhmm!"

For the first time in her life, the almost always assertive Cheerilee had been brought to giving such responses and it only turned Twilight on further. She resumed her grinding and wrapped herself entirely around Cheerilee, massaging her, kissing her and yanking on her mane. Cheerilee's moaning became louder and louder the more Twilight worked on her and by the time Cheerilee climaxed, both mares were so sweaty that even their manes were wet and their bodies were hot and sticky.

Twilight gave Cheerilee a smile, "You know, you feel so good when you're hot and sticky like this."

Cheerilee was still in so much of a daze she replied, "Mhmm!"

Twilight giggled, "My my Cheer, I really rocked you didn't !?"

Cheerilee had finally began to come out of her daze, "Wow Twily, are you sure you've never done this before? Nopony has ever brought me down like that!"

Twilight couldn't help but laugh, "Well maybe those past lovers of yours simply didn't try hard enough." Her laugh became louder as she continued, "Perhaps they simply didn't have the Sparkle it took to bring you down." She got up off the bed and continued, "And now, it is my turn!"

Cheerilee couldn't help but wonder what Twilight had planned but wondered why she would stand up to do it. Things then began to cross her mind that perhaps Twilight had plans for her that none of her previous lovers ever did, things that she had never experienced before.

Turning the Tables

Twilight Sparkle had just received her first experience from Miss Cheerilee but receiving is only part of the experience. Once both mares were completely coherent, Twilight had got up and ordered Cheerilee to stand up. This was something that had only happened with Cheerilee on one other occasion, a lover wanting to please her while she was standing up.

Twilight got down on her knees, smiled up at Cheerilee and asked, "You ready Cheer?"

Cheerilee replied, "You know Twily, this is only the second time anypony has ever done anything with me standing up."

Twilight couldn't help but laugh, "Oh and here you claim to have been so wild in college, to be so experienced yet this is only the second time you've done anything this way?"

Cheerilee gave her a nervous laugh. At that moment, Twilight had a feeling that she may be able to do something nopony had ever done before but wanted to wait until just the right moment. She gave her a smile and continued, "Very well, let's get started!"

Twilight crawled towards Cheerilee, planted her hands on her flank and began to suck on her. Immediately Cheerilee began to moan gently and pressed her legs tightly around Twilight's head. With her head locked securely in place, Twilight began her plan to see if there were things that maybe Cheerilee was exaggerating about. She began to move her hands towards Cheerilee's crack and she could hear gasps of pleasure coming from her lover but merely moving them there was not even close to what she wanted to do.

As she moved her hands closer and closer to her hole, Twilight could tell that there was beginning to be a bit of nervousness coming from her. She continued to move her hands slowly until she finally reached her opening and when she inserted a couple of her fingers, she heard a gasp, "Twily!"

Cheerilee's legs loosened their grasp on Twilight's head allowing her to pull her head out. Twilight giggled, "What's wrong Cheer, never done this before?"

Cheerilee gasped, "Just once and it hurt."

Twilight replied, "Don't worry Cheer, I'll be gentle with you, ok?"

Twilight immediately buried her face back in Cheerilee and slowly moved her fingers further and further into her behind. The further Twilight pushed her fingers, the more nervous Cheerilee became. Just as Twilight got her fingers pushed all the way in, Cheerilee gasped, "Twilight!"

Twilight pulled her fingers out and asked, "Cheerilee, are you ok? Did I hurt you?"

Cheerilee replied, "No, it has just been so long."

Twilight gave her a smile, "I see." She shoved her fingers back in her, resumed her sucking and began to thrust her gently. Given that Cheerilee had brought up pain in the past, Twilight was careful not to get too rough with her.

Eventually Cheerilee grew enjoy it and began to call out Twilight's name, "Oh Twily, oh Twily! Harder, faster, deeper!"

Twilight stopped sucking momentarily and asked, "Are you sure about that? I don't want to hurt you."

Cheerilee replied, "You won't!"

Twilight gave her a smile and got back to work on her. As she began to shove her fingers further back with greater force, Cheerilee's breathing became much heavier and much quicker. As Twilight continued to thrust her fingers in deeper and harder, Cheerilee began to scream, "Oh Twily, Oh Twily! Yes baby yes, yes baby yes!"

Twilight took that as approval to get rougher with her and was soon thrusting her as hard and as fast as she could. Soon Cheerilee was getting ready to climax, "Oh Twily, Oh Twily, Oh Twilyyyyyyyy!"

As her nectar flooded out of her marehood, Twilight got a taste but then began to rub her face all over her, making sure to get soaked in the warm liquid. When Twilight pulled out and Cheerilee noticed what she had done, she asked, "Why Twily? Do you not like the taste of me?"

Twilight replied, "Oh I like your taste just fine but I thought it would be really hot to be covered in it."

This was something that none of her prior lovers had ever done and this again caused Cheerilee to wonder. She asked, "Twilight, do you simply have very strange and erotic fantasies or have you been lying and have you done this before?"

Twilight giggled, "Come on Cheer, I went to Celestia's school and nopony ever engaged in these kind of activities." She looked up at her marehood and continued, "There is one more thing I want to do though, something I think you'll find hot, very hot!"

Cheerilee gave her a smile, "Something I'll find hot huh?"

Twilight giggled and began to move her horn towards Cheerilee's marehood, which caused her to shy back. She gasped, "Horn sex, you want to give me horn sex?"

Twilight again giggled, "You've never been with a unicorn, have you?"

Cheerilee gave her a nervous reply, "Well I danced with one once and she took me home with her but I was afraid of the idea of horn sex so she let me out of it."

Twilight couldn't help but snicker, "Seriously, the wild child has never had horn sex?" She gave her a seductive smile and added, "Well then, how about you let me be your first?"

Cheerilee gasped, "Are you sure this is your first time? Are you sure you haven't done this before?"

Twilight snickered, "Trust me, this is my first. Like I said, I went to Celestia's school and she never allowed her students to do things like this."

Cheerilee replied, "Very well but please don't be rough, please don't hurt me."

Twilight began to move her horn towards her folds and said, "Don't worry, I won't."

Twilight raised her head and began to insert her horn into Cheerilee bringing a gasp from her, "Twilight!"

Twilight replied, "Don't worry Cheerilee, I'll be gentle!"

All Cheerilee could do was hope she would but Twilight was hoping that she could get out of denying herself so much pleasure so she decided to cast a spell, a spell that would turn any pain into pleasure. She lit her horn and pushed it further up inside her. She grabbed Cheerilee's flank and began to thrust her. Cheerilee began to moan in pleasure as Twilight worked on her, "Oh Twily, Oh Twily, Oh Twily!"

Unicorn horns are very sensitive and feel of Cheerilee's hot, wet, sticky walls pressing up against her caused her to squeal in ecstasy. She began to release more energy into Cheerilee to not only give her more pleasure, but to cause her vaginal muscles to continue to contract tighter and tighter against her horn. While Twilight was thrusting her, she looked down and noticed that Twilight had her whole horn in her and also saw a glowing coming from the base of her horn. She gasped, "Twi......."

Twilight again released more energy into her and continued to thrust harder and harder and eventually she heard a loud squeal of pleasure come from Cheerilee when she finally fully penetrated her. Twilight could feel that her partner was about to climax again but for her, this was something she was not about to let happen. She released more energy into her to delay the orgasm for as long as she wanted. Twilight continued to thrust harder and as deep as she could to give not just Cheerilee, but herself the maximum amount of pleasure.

After two hours of thrusting, she heard Cheerilee call out, "Twilight, stop! I've gotta pee!"

Twilight simple gave her a giggle and continued to work on her. Twilight had many fantasies and being peed on was one of them. Eventually Cheerilee couldn't hold it anymore and a flood of hot liquid poured out of her onto Twilight's head and into her mane, "Oh yes Cheer, yes, yes, yes!"

Despite being soaked, Twilight would not stop until she got another orgasm out of her. Finally she stopped with the delay spell and her partner finally climaxed and Twilight pulled out and leaned forward, allowing her mane to get soaked with her cum. This felt really good to Twilight and she finally decided that the time was nearing to tell Cheerilee the truth.

When Twilight finally stood up, she leaned her head forward and demanded, "My horn, lick it clean now!"

Cheerilee complied and began to lick the horn clean, bringing out moans of pleasure from Twilight, "Oh Cheer, yes, yes yes! Suck it baby, suck it baby!"

Cheerilee went from licking it to sucking on it, causing Twilight to call out, "Suck harder baby, suck harder, suck harder!"

Again Cheerilee complied until she could tell she had sucked every last drop of her nectar from the horn. Twilight stood up and gave Cheerilee a huge smile and giggled, "Gotcha!"

Cheerilee asked, "What do you mean gotcha?"

Twilight continued, "This wasn't my first time hot stuff." Cheerilee gasped in shock causing Twilight to continue, "When you have a bunch of fillies suddenly growing into mares, things are going to happen. Once we came of age, my friends and I did this fairly often."

Cheerilee asked, "Seriously, so you're not so innocent after all?"

Twilight replied, "Nope, I'm not. How do you think I knew all those spells? How do you think I knew the spell to delay your orgasm? How do you think I knew the spell to cause your walls to contract?"

After Twilight had begun working on Cheerilee, she couldn't help but wonder if Twilight actually had experience but after this admission, she was shocked that she had that much experience. She asked, "Ok, so you and the other mares did stuff like this all the time but have you ever been with a non-unicorn before?"

Twilight replied, "Actually no, I haven't." The fluids Cheerilee had soaked Twilight with were beginning to dry and that was one thing that she was not a fan of. She grabbed Cheerilee's hand and continued, "How about we get washed off and then we can have some supper and talk about this more? It isn't a good idea to let bodily fluids dry on the body."

Cheerilee replied, "That sounds good but I won't have any clean clothes to wear home!"

Twilight said, "You may just have to wear the undergarments you came in but you can borrow some of my clothes to wear home. I doubt you want to be seen in your clubbing clothes by everypony eating outside at the cafe."

Cheerilee nodded and followed Twilight into the bathroom so she could shower with Twilight. She couldn't help but admit to herself that what the two had done felt good and was a bit afraid to bring it up to Twilight that she wanted more, much more.

An Odd Suppertime Discussion

After the two had showered and got dressed, they headed down to the dining hall to not only have supper, but also discuss more about the day and so Twilight could discuss her past. Once they got down there Twilight asked, "Hayburgers ok?"

Cheerilee replied, "Yeah that sounds good."

Twilight normally had a chef to cook such things but that day he was gone so it was up to her to cook the meal. As she cooked their meal, she couldn't help but wonder how Cheerilee would react to everything that she was going to tell her, how she would react when she just told her everything that she and her Canterlot friends used to do.

Thirty minutes after getting supper cooked, Twilight carried it back and set their plates down. Cheerilee licked her chops and asked, "You cooked this yourself?"

Twilight replied, "Of course, it's not like Spike is around or there is anypony else here to cook it. Now let's talk about more important things" Twilight got a huge smile on her face as she continued, "such as my past."

Cheerilee gave her a smile, "Oh? I take it your past is anything but boring like you claimed at first?"

Twilight began, "Yes. When I was in Celestia's School for Gifted Unicorns, I did most of my studying with five other unicorns, all roughly the same age as me. While I have referred to them as friends, I'd say we were more acquaintances that had to study together."

Cheerilee asked, "So you weren't as close to them as you made it sound?"

Twilight continued, "Correct. I didn't care to spend much time around them when we were fillies but once we began to mature, things began to change. While I never became real close to them emotionally, all of us did become very close physically."

Cheerilee's eyes grew wide as she asked, "So you were all lesbians?"

Twilight was shocked that Cheerilee would give such a reaction considering that she likes mares too. She replied, "Of course and naturally at that age we wanted to experiment and given how much time we spent together, all of our experimenting happened together." She gave her a smile and continued, "And most of it happened in my study tower, out of Celestia's watch."

Cheerilee knew a bit about how Twilight was and how she always wanted to look good in the eyes of Celestia and was shocked. She asked, "Weren't you afraid of Celestia catching you?"

Twilight couldn't help but giggle, "No, none of us were. She very rarely interrupted me when I was in my study tower and when I had them over studying, she just left us all alone because she thought that maybe, just maybe I was growing close with them." Her giggle turned into a full blown laugh, "Oh I was growing close with them alright, but not in the ways she intended!"

Cheerilee became more curious, "So what sorts of things did you do?"

Twilight developed a deep blush, "Lots of watersports, lots of bodily fluid consumption, bondage, role playing, dom/sub activities, lots and lots of horn sex, lots of horn sucking, biting, licking and sucking."

Cheerilee was shocked at how experienced Twilight was when it came to bedroom activities. She gasped, "Seriously, you've done that much? That is a whole lot more than me."

Twilight replied, "Yes but outside of those six and now you, I haven't been with anypony else" her face turned red as she continued, "and I certainly haven't done any clubbing and having fun with mares I've just barely met."

Twilight gave her a wink and a smile causing Cheerilee to wonder something, "Wait a minute, are you telling me you'd want to go clubbing sometime and do what I did?"

Twilight replied, "Yes but it would have to be someplace back east, far away from the eyes of Celestia." She got a huge smile on her face and continued, "The idea of hooking up with a random mare does sound incredibly hot!" Her smile got bigger as she asked, "And I'm betting that there is a lot I could teach those mares, especially those non-unicorns, the ones that could use a little Sparkle in their lives."

Going clubbing, something that Cheerilee had not done in so long she could barely remember what it was like. For years the thoughts of engaging in such an activity would be uncouth given that she was a teacher but here was Princess Celestia's protege wanting to do it. She began to think that maybe, just maybe she should really let her mane down, a whole lot more than she did just having fun with Twilight. She gave her a smile and asked, "I take it you want us to go sometime?"

Twilight approached her, grabbed her breasts and replied, "You pick up on hints quite well don't you sexy girl?"

Again Twilight referred to her by something other than her name. Cheerliee liked it and said, "Yes, I do." She groped Twilight and continued, "Spring break is in a month and I'll have a full week away from school so maybe we could go on a little trip to Marentreal. I know of a club for lesbians that you'd love."

Twilight asked, "Oh really, I take it that is where you used to go?"

Cheerilee replied, "Yes and I'll be honest, if it is still like it was, a lot of unicorns go there and they tend to like to dominate their partners."

Twilight laughed, "Them dominate me, I think not! With as experienced as I am and that outside of Minuette, I dominated the other girls up in school I think I can handle it on my own."

Cheerilee gasped, "Wait a minute, do you mean Minuette the dentist. The rigid, business first dentist here?"

Twilight replied, "Yes her." She then began to giggle, "You know, I bet if we could get her to let her mane down for a change, we could do a three way and you could see how dominant she used to be." Her giggle became louder as she continued, "She was a bit of a sadist though. You know how I cast that spell to turn your pain into pleasure? She would never do that, she would enjoy hearing cries of pain and only thrust harder the more you cried."

Cheerilee's eyes grew wide, "Well on second thought, I think I'll pass on her."

Twilight snickered, "Probably for the best because she even hurt me." Her voice became more calm as she continued, "Besides, I doubt she'd be interested in any fun and I know she certainly wouldn't take time away to go clubbing, even if it meant she could 'punish' random ponies, I doubt she would shut down shop." She became a bit frustrated and finished, "Money is too damn important to her. Once she got into dentistry, her wild side died and her desire for money became insatiable."

Cheerilee sighed, "That is true and I doubt other ponies would be interested in getting it on with a sadist like her anyway."

By this point the two had finished their supper and Cheerilee felt as though she had accomplished what she wanted to that day, that perhaps it was time to go home and Twilight noticed her gazes towards the exit. She asked, "So Cheer, why are you looking towards the exit?"

Cheerilee saw a slight glare coming from Twilight and replied, "Well I was thinking of maybe going......."

She suddenly found herself grasped in Twilight's aura as Twilight asked, "Certainly you don't want to go home this soon?" She got a sadistic smile on her face as she continued, "I would have thought you'd want to stay longer, longer as in all night!" She picked Cheerilee up with her aura and began to pull her towards her bedroom and giggled, "Sorry Cheer but you're staying all night and since you thought about leaving, I'm dominating you all night long."

Cheerilee did like to be dominated once in a while but she was no fan of being dominated all night. She replied, "Seriously, all night?"

Twilight got a smirk on her face and replied, "Yes all night. Now unless you want me to take you over to Minuette's, bribe her and have her punish you severely all night long, you'll let me do this."

Cheerilee remembered how it was not that long ago that Twilight had brought up that Minuette would be far too rigid to engage in any activities and asked, "But I thought you said that she would never engage in these kinds of things?"

Twilight replied, "Oh I can just bribe her with what she loves most, money. If I give her enough she'd gladly punish you." She gave Cheerilee a sadistic smile and continued, "So Cheer, which will it be, me or Minuette tonight?"

Cheerilee sighed, "You Twily, I know you're not a sadist who delights in the pain of others."

Twilight gave her a smile and began to lead her back up to the bedroom. While she was leading her up there, Twilight had a smile on her face as she couldn't help but wonder how Minuette really would be with her and began to wonder if she should talk to her old "friend" about this. She thought to herself, "Cheer liked it earlier, maybe she'll like two horns in her at once more!"