Chapters Twilight stared into her closet and frowned closing the door and crossing her arms. “Spike! Spike, did you pick up my yellow dress from the dry cleaners?”
Spike poked his head into Twilight’s room and quickly covered his eyes seeing that Twilight was standing there in just her underwear, her tail flicking back and forth. “Yeah! Of course I did Twilight. It’s on the right side of your closet… Also would you please put a shirt on or something? I mean, nopony or dragon needs to see that!”
“Don’t worry Spike when you grow up i’m sure there will be some pony you’ll want to see in just their underwear.” Twilight smirked as she reopened her closet shoving all of her clothes to the left side, revealing the simple yellow dress Rarity had made for her last year on her birthday.
Spike rolled his eyes under his palms with a grunt. “Yeah, but it’ll never be you that i’ll want to see! It’s just gross!”
Twilight laughed as she heard his footsteps go down the staircase and shook her head. “Boys. Sometimes I don’t think they ever really grow up.” She looked over at the time and groaned. She had lost track of time again! “I’m going to be late if I don’t hurry up.”
Luckily it never took Twilight very long to get ready. A bit of eye shadow, some mascara, a touch of lipgloss and a brush of her mane was all she needed. Her magic pulled her zipper up as she dug around for the yellow pumps that went with the dress and her purse. “The Princess would have my head if she saw how disorganized I am right now!” Twilight closed her eyes before bringing her arm to to her chest and breathing in and out a few times. The technique her sister in law had taught her was a life saver.
Spike glanced up from dusting as she walked down the stairs and whistled. “Wow, Twilight, you clean up pretty nice!” He grinned as he saw the blush color her cheeks. “So what’s this date celebrating again?”
“Oh! Well I wasn’t thinking of it like that but, you are right. This makes it five months that Cheerilee and I have been marefriends. It doesn’t feel that long.” Twilight smiled at how nervous she had been that day when Cheerilee had asked her to come by the school after class. She coughed delicately “Anyways I made a reservation at the Sundrop Cafe for five PM, so I really need to get going.”
“Should I wait up for you? Or are you planning on staying the night at her place?” Spike grinned returning to his dusting missing the expression of agony on Twilight’s face as she shook her head.
“No, I’ll be home before ten tonight. Don’t worry… Anyway see you later!” Twilight shut the door lightly behind her and leaned against it eyes closed for a moment before smiling. “Oh well, we aren’t to that stage of dating anyways, so relax Twilight. All that is going to happen tonight is a nice dinner with the pony you love…” She shook her head and with a small smiled headed towards the cafe.
Cheerilee glanced over at the clock with a small shake of her head. Twilight wasn’t late, not yet anyway, but it was getting close.
“Cheerilee! Cheerilee, I’m sorry I’m late!” Twilight walked over as quickly as she was able to in her heels. She stopped in front of her, chest heaving.
“Not much of an athlete, are you Twilight?” Cheerilee smiled, waiting for Twilight to catch her breath before touching her lips to Twilight’s cheek.
“I’m really not. I’m not not sure how I was able to take fifth place last fall! I guess it helped that Applejack and Rainbow Dash kept slowing down the other runners with their antics.” Twilight shrugged before leading Cheerilee into the cafe and smiling at the earth pony mare who was their hostess. “Two for five pm under the name Twilight?”
“Ah yes, please, follow me.” The mare grabbed up two menus and led them to the back of the darkened cafe to where a two top was set with a lit candle. Twilight smiled before pulling out Cheerilee’s chair for her.
“Well aren’t you the gentle colt.” The hostess smiled, not noticing how Twilight swallowed hard before sitting down across from Cheerilee. She took the menu offered to her with a gentle nod.
“Your waitress will be here shortly, but if you’d like, I can take your drink order.” The hostess took out a small notebook, still smiling as Twilight nodded.
“A bottle of Cherry wine and two glasses please.”
“Of course. I’ll be right back with that for you.” She turned and walked away as Cheerilee smiled, taking Twilight’s hand and running her thumb over her knuckles.
“Wine? I didn’t think you really drank.”
“Oh? Well, I don’t normally… sometimes a glass with the girls, but uh…” Twilight trailed off before shrugging. “I guess I just don’t like to be drunk is all.”
“I can understand that, but tonight is a special night, isn’t it? Five months together hmm?” Cheerilee smiled, enjoying the blush that slowly covered Twilight’s cheeks.
“Y-yes, five months since you asked me out.” Twilight took a sip of her water glancing down at the table.
Cheerilee laughed while rolling her eyes. “Well by that time, I had to ask you since you hadn’t caught the fact I wanted you to ask me. Tell me Twilight, did you ever date anypony before me?”
Twilight took her hands back and swallowed, placing her hands in her lap. “Cheerilee, before we started dating, I had never even kissed a pony outside of my family. I guess I just wasn’t interested.”
“And now?” Cheerilee leaned forward, giving Twilight a eyeful of her cleavage.
Twilight licked her lips, struggling to keep her pulse normal as she took a sip of water. “N-now? Now I’m happy to be dating you.”
At that moment the hostess walked up with the bottle of cherry wine, as well as an ice bucket. She set the bucket on the table, along with two glasses, before holding the bottle out to Twilight to allow her to peruse the label and either accept or reject it. After a moment, Twilight nodded her head and the hostess opened the bottle before placing it into the ice bucket. “Your waitress will be along in a few minutes ladies.”
Twilight nodded, lifting up her menu and perusing it eagerly. She herself had never been here, but had asked Rarity where the best date places in or near Ponyville might be. After several moments of Rarity happily shrieking and holding Twilight close, the young mare had started taking notes on everything Rarity said. The Sundrop Cafe had been right at the top of Rarity’s list, both for the food and atmosphere of the small restaurant. From what Twilight had seen so, far Rarity was spot on in her analysis.
“So, Twilight, what are you planning to get?” Cheerilee looked up at Twilight over her menu, trying to figure out what Twilight might have in mind. What are you thinking Twilight? What is it that is on your mind?
“Oh! Well, this roasted mushroom lasagna looks delectable. So I think I’ll get that. What about you, Cheerilee?” Twilight smiled, setting down her menu, not noticing how Cheerilee’s eyes had begun drifting over Twilight’s body.
“I’m thinking about something purple and delectable…” Cheerilee licked her lips, hopefully Twilight would catch her meaning.
“Oh well they have a fantastic eggplant parmesan!” Twilight beamed, pointing it out on the menu, not noticing Cheerilee sigh.
Swing and a miss… For somepony so smart, she is quite dense…
“That does sound good. Yes, I think I'll have that.” Cheerilee closed her menu and smiled as Twilight poured some of the now chilled wine into her glass. “Ah, thank you Twi…”
“Of course.” Twilight poured herself half a glass and took a sip with her eyes closed. “Cool, but not cold… it’s perfect.”
“It’s not the only thing that is perfect…” Cheerilee smiled as Twilight’s cheeks flushed red. Oh it’s so much fun to make her blush.
As Twilight swallowed several gulps of her wine, their waitress walked over with a large smile. She was a unicorn with blue fur and a white mane who was definitely not lacking in “talent”. “Good evening ladies. Can I interest you in any appetizers, or are you ready to order?” She pulled out her notepad as Twilight swallowed her last gulp of wine, before pouring herself a bit more. “Or do you need a few more minutes?”
Twilight shook her head, glancing over at Cheerilee before her eyes darted back down to her menu. “N-no we’re ready. I’d like the roasted mushroom lasagne.”
“Garden salad or soup?” The waitress asked, jotting down Twilight’s order with a smile.
“Garden salad with ranch please.” Twilight closed her menu and handed it over to the waitress as she focused her attention towards Cheerilee.
“And you Miss?”
“Ah yes. I’d love your delectable, purple eggplant parmesan.” Cheerilee licked her lips. “With a garden salad, and the italian dressing on the side, if you could?”
“Of course, and I’ll be back with your salads in just a few moments.” The waitress took the menu offered by Cheerilee, and walked away her heels clicking on the floor.
“She was quite nice looking, wasn’t she?” Cheerilee smiled, glancing over to see Twilight pouring herself a bit more wine. “Hey, save some of that for me, hmm?”
Twilight jerked up to see Cheerilee smiling gently while holding out her now empty glass. “Ah yes, of course!” Twilight filled her glass half way up as the waitress returned with their salads. Twilight quickly began munching at her salad, if only to have something in her mouth so she couldn’t say anything stupid.
Cheerilee slowly poured her dressing over her salad before taking a small bite. She then licked the dressing from her lips, causing Twilight to shiver and shift in her chair. “They make a fairly good salad. I’m eager to see how our main dishes turn out, hmmm?”
Twilight nodded while stuffing more salad in her mouth and crossing her legs. She tried to listen as Cheerilee talked about how her day had gone, but found her attention traveling from Cheerilee’s plush lips down to where the smallest amount of cleavage was visible. She took a deep shaky breath and swallowed hard. “Cheerilee, I…”
At that moment the waitress returned, setting down their dinners. “Enjoy!” With that, she quickly walked away, not wanting to interrupt the young couple.
Twilight watched as Cheerilee took a bite and licked her lips again. “Mmmm, you were right Twilight, this is wonderful…” She cocked her head as she saw Twilight shift again. “Twilight, is something the matter?”
“T-the matter? Of course not e-everything is fine!” Twilight grinned as she once again shifted, before taking a large bite of her still hot pasta. “Ouch!”
“Twilight?” Cheerilee frowned as she paused over her water. “Please talk to me? Did I do something? I was just trying to tease you a bit that’s all.”
Twilight took a gulp of water swigging it around in her mouth, before swallowing with a relieved sigh and looking down at her plate, before squeezing her eyes shut Am I really considering this? I am… Celestia help me… Twilight took a deep breath and looked back up to see Cheerilee no longer smiling.
“T-there is something wrong, but this really isn’t the place to talk about it… I… it could change everything about how you feel about me… but if you really want to further our r-relationship?” Twilight saw Cheerilee give the barest of nods before she took another deep breath. “Come by the library tomorrow early. Say around eight. I’ll tell you everything you might want to know.” And possibly a lot you never had any desire to know.
“Alright Twilight. I’m guessing our date is over for tonight then,” Cheerilee asked gently. She knew dating Twilight Sparkle wasn’t easy, and that this was just par for the course. Though, she was curious what it was that had Twilight so worked up.
“I’m sorry. I’ll make it up to you if you still want me to after tomorrow.” Twilight lifted her napkin to her lips and wiped her lips before lifting a hand to summon their waitress back. “I’m sorry, but something has come up. Could we get some to go boxes?”
The waitress nodded. “Of course. I hope everything is alright. I’ll be right back with your check and the boxes.”
Twilight opened her purse to pay for the meal, but paused as she felt Cheerilee’s warm hand cover her own.
“I got it this time. You can pay next time, I promise. I’ll see you tomorrow, eight AM, I promise.” Cheerilee smiled taking the check from their waitress as Twilight carefully placed her pasta in her to go box and hesitated before brushing against Cheerilee’s cheek with her lips.
“Eight AM, I promise…” With that, she left the restaurant and headed home, her shoulders slumped. Luckily the lights in the library were still on. She’d need someone to talk to about this. First she needed to put her food away, and then maybe take a shower though. She shivered again, squeezing her eyes shut before walking inside.
A long cold shower.
Author's Note
Hope you guys enjoy this commission. It will be three chapters long. I hope to have it done by October. But, we'll see! Leave a comment and a thumbs up if you enjoyed!
If you have an idea you want to commission PM me and wre'll work something out!
Twilight paced back and forth, her hands behind her back. It was almost eight in the morning, which meant Cheerilee would be there any moment. She bit her lip and laid down on her bed, placing her head in her hands and gripping her mane tightly. “H-how is this happening? I never wanted anypony to find out about this…”
Downstairs, Spike was cleaning up after breakfast when he heard a very familiar knock. One knock, then two quick ones. He dried his hands off on his jeans and hurried towards the door, pulling it open to reveal Cheerilee, her mane pulled back into a ponytail, wearing a pair of jeans and a purple blouse.
“Good morning, Spike. Twilight asked me to be here at eight, so... here I am. Is she here, or did she leave?” Cheerilee smiled gently as Spike shook his head.
“Nah. She considered it—I won’t lie—but I talked her down. She’s waiting for you upstairs, but, um…” Spike stepped aside so Cheerilee could walk in, then closed the door. “Look, before we head up, you have to understand that this is a big secret for her. Very few ponies know about it. I mean, the last pony to find out was Princess Celestia , of all ponies.”
Cheerilee nodded, and then wrapped her arms around Spike. “I know how scared she is, Spike. I promise I will listen to her. I love her, and I want to be with her. And being together means taking care of each other and accepting the good with the bad. Okay?”
Spike nodded, his face buried in her chest. “A-And if you don’t stay together?”
“I swear to you Spike, I would never use anything this important against Twilight! If we ever part, I will keep it to my death.” Cheerilee stroked the dragon’s green mane. “I promise.”
Spike nodded before pulling back. “Alright. You should probably go on up before she works herself up even more than she already has.”
With a confidant wink, Cheerilee headed up the stairs, her ears flicking, listening for any sounds coming from Twilight’s room. Silence. She bit her lip before knocking on the door. “Twilight? It’s me. May I come in?”
After a few moments, the door opened with a burst of lavender magic. Cheerilee peered into the room to see Twilight sitting on her bed, still in her nightgown, her face buried in her hands. Cheerilee’s eyes widened as she rushed over to her.
“Twilight, sweetheart? Are you alright? Talk to me!” She brought her hand up to touch Twilight’s shoulder and froze as the younger woman threw herself into Cheerilee’s chest, Twilight’s own heaving from quiet sobs. Cheerilee simply brought her arms around her younger love and held her tight as she cried. Whatever this is, Twilight must be so scared... After several moments, Twilight pulled back, wiping her red eyes.
“B-before I say anything, I need your word that you won’t tell anypony,” she whispered. “Please… no matter what happens between us…” Twilight’s soft voice trailed off as Cheerilee took hold of her chin and brought her into a tender kiss.
Cheerilee pulled back with a soft smile. “Never. I will never break your trust, no matter what. I love you, Twilight. You can trust me.”
Twilight nodded and took a deep breath. “Alright, I’ll tell you. Just… please, don’t rush me. It’s a hard story to tell.”
Cheerilee nodded, and got comfortable as Twilight got up off the bed and began to pace back and forth.
“I wasn’t a normal foal,” she began hesitantly. “I was never interested in friends or playing, really. I kept to myself and spent most of my childhood reading. For a long time, I felt as if something was missing in my life. Then I got my cutie mark. Everything was finally making sense… except one thing.” Twilight paused, and put her hands behind her back.
“Cheerilee, didn’t you ever wonder why nopony knew that Twilight Sparkle was Princess Celestia’s student?” she asked quietly. “I mean, normally you couldn’t have kept that out of the news, right?”
Cheerilee considered that for a moment, and realized that she had never thought about it. But it was true Twilight’s name and picture should have been all over Equestria.
Twilight shook her head with a smile. “It was part of an agreement between my parents and the Princess. A condition of her taking me as her student.” Twilight swallowed hard. “Due to my… medical condition.”
“Twilight, a-are you sick? Is it serious?” Cheerilee asked in a sudden panic. It had never crossed her mind that the secret would be a medical condition…
Twilight licked her lips nervously. “It… it’s a matter of opinion whether it’s a serious condition or not, I suppose. Cheerilee, when I was born, I… I-I was a colt.”
Cheerilee’s mouth opened as she blinked a few times in complete shock. “A… you were born a colt?”
Twilight winced at the unencouraging reaction, but nodded. “Yes. My name was Dusk Shine. I never felt like a normal colt. I had no interest in anything the other colts did. All I wanted to do was study. And, well…sometimes, I would watch the fillies in the neighborhood play. I wanted to be like them. In fact, I…I took a neighbor’s dress from their drying line. She was a few years older than me…”
Twilight closed her eyes, a small smile tugging at her lips. “I had never felt more comfortable in my own skin than the first time I put on that dress. I played in it for a few hours, trying to keep myself hidden, until my Mother came upstairs, surprising me. I panicked, but Mom… Mom wrapped her arms around me and held me tight. She told me that she didn’t understand, but that she would learn. No biting questions. No yelling. She just held me as I cried. The next day she came home from work with a bag from a filly clothing store. She came over to me and handed it over with a smile. I opened the bag to find a pretty yellow dress with a white peasant collar. It was perfect, and in my size. I just looked up at her with big eyes and couldn’t stop smiling. Mom understood… she still loved me.”
Twilight wrapped her arms around herself as she remembered that day. “Mom had talked to Daddy while they were in bed the night before. Neither of them understood why their youngest son wanted to be their daughter, but they both supported me. They loved me. After that it was a whirlwind of counseling and doctor’s appointments. I was diagnosed with gender identity disorder, and it was decided when I reached puberty I would be given infusions of estrogen so I would grow into a mare.” She cupped one of her breasts. “Which is why I have these. My big brother had a bit of a harder time accepting than my Mom and Daddy, but he came to adore having a little sister. In fact he was the one to choose my name. Twilight Sparkle.”
“So… You are a transmare, Twilight?” Cheerilee asked after a moment.
Twilight nodded, looking down at the floor. “I understand if you want to leave now. I know—” Twilight stopped talking as Cheerilee kissed her softly.
“Twilight Sparkle, I need you to listen to me. I love you, you silly mare. I love everything about you, and I don’t plan on going anywhere. Do you understand me?” Cheerilee kissed each of Twilight’s eyelids, her lips brushing against salty tears.
“I… I love you too,” Twilight confessed, her voice breaking in relief. “I love you so much that I was so scared! Shining, he, h-he was always worried what ponies would d-do to me. H-He even told Cadance that if she told he would break up with her, and they’re meant to be!”
Cheerilee laughed softly. “And we aren’t?”
“I-I never said that! I just… you… you want to have sex at some point, right?” Twilight’s cheeks gained a rosy hue as she thought about it.
“No, Twilight, I don’t want to just ‘have sex’. When you are ready I want us to make love . Why do you ask?” Cheerilee cocked her head as Twilight reached for the buttons on her nightgown, slowly undoing them, revealing her perfect large breasts and toned tummy. For working as a librarian, Twilight was in fantastic shape. Finally, she stood in just her panties, her tail waving back and forth nervously.
“Well… magic and hormones can do a lot, but they can’t change everything. I had the option of having a bottom surgery, and after seeing pictures of the results I decided that it wasn’t something I wanted. W-What I mean to say is that I still have a colt’s… you know.” Twilight’s fingertips slid under the top of her panties.
“A-A colt, not a stallion?” Cheerilee winced, realizing how her query sounded, but Twilight smiled.
“Well, my shaft and testacles ceased maturation once I was taking estrogen on a regular basis. Remember, I was still a colt when this occurred.” Twilight shrugged. “I… I could show you if you wanted?”
Cheerilee licked her lips as she considered how best to respond before smiling. “Well, I was going to see anyways, wasn’t I?”
Twilight blushed, her eyes focused on the floor as she nodded. The tips of her fingers pulled at her panties and slowly slid them down her legs.
Cheerilee swallowed as Twilight’s hidden genitalia was revealed. The first thing she could see was the curly dark blue hair poking out of the top of her panties. Cheerilee snickered internally. It looked as if Twilight had never seen a razor in her life. I’ll make sure to fix that. She watched as Twilight paused, glancing up at Cheerilee, who gave a simple nod. Twilight pulled her panties all the way down, revealing a small black shaft speckled with purple splotches. It wasn’t that big at all, maybe an inch, an inch and a half. Nestled between Twilight’s legs were two small testicles, each of them about the width of a bit.
“So, yes, as you can see, I… I’m not exactly anything to write home about.” Twilight blushed, her hand subconsciously covering her small penis.
“No, no, don’t say that.” Cheerilee stood up and kissed Twilight’s lips. “I told you that you are beautiful, no matter what. Though I do have a few questions.”
Twilight nodded enthusiastically. “Yes! Questions I can do. What are you wondering?”
Cheerilee tugged Twilight’s hand away from her crotch and kissed each of her fingers. “Good. Now, relax. First, how sensitive are you?”
Twilight smiled, practically cooing from the attention she's being given. “I really don’t have a good understanding of how sensitive it should be. But, I feel it’s enough for me.”
Cheerilee nodded, and, while still cradling Twilight’s right hand against her cheek, she slowly ran a single finger tip down Twilight’s shaft, pulling back once she reached the tip of its head.
Twilight shivered as her shaft grew erect from the gentle touch, doubling in length and width, much to Cheerilee’s delight.
“Well, that answers the second question I had.” Cheerilee got to her knees and ran her thumbs along Twilight's small ball sack, before cupping it in her hand. She glanced up to see Twilight with her head lolled back, and her eyes closed. “Well, it’s obvious to see that you and I can be together. So, what about our future?”
“F-future?” Twilight moaned out, having a bit of trouble concentrating. Her legs shook as Cheerilee continued to run the tip of her thumb over her testicles.
“Of course. I’m not planning on going anywhere, and I don’t think you are either.” Cheerilee looked up to see Twilight shake her head. Her mouth opened, and quiet moans escaped through. “Well… At some point I’d like to be a mother.”
“... N-not a possibility without a lot of magical assistance. I don’t make sperm.” Twilight closed her eyes, worried that her answer would cause Cheerilee to leave.
Cheerilee paused in her stroking before kissing the head of Twilight’s shaft, causing her to shudder. “Mmm, guess that means we’ll never have to worry about condoms then.”
Twilight jerked back from the touch of Cheerilee's lips “Y-you mean you aren’t leaving?”
“Oh Twilight, my little love, I’m not going anywhere. I want to talk to you, love.” Cheerilee stood up and kissed Twilight lightly before pulling away and smiling. “I think you should tell your friends.”
“W-what? Tell my friends… a-about my secret ?! I can’t! They’ll leave me and, a-and I’ll be all alone again!” Twilight wrapped her arms around herself. Her erection faded as she trembled, tears running down her cheeks.
Cheerilee wrapped Twilight into a gentle hug, and cooed softly into her ear. “Twilight, my love, I know they will never leave you. You and your friends are so close. Closer than any friends I’ve ever seen.”
Twilight glanced up with glazed eyes as Cheerilee stroked her hair.
“I’m sure even Princess Celestia would tell you the same.” Cheerilee smiled gently.
“The Princess…” Twilight laid her head against Cheerilee’s chest. “Cheerilee, would you be here with me if I asked the girls over to… to talk with them?”
Cheerilee lifted Twilight’s chin to look into her glimmering eyes. “I will be here whenever you need me, even if you may not want me there.”
Twilight giggled a bit, and then touched her lips to Cheerilee’s. “Thank you. I love you.”
“And I love you my little love. Now, before we invite your friends over, I think you should get dressed, hmm?” Cheerilee smiled, and gave Twilight a quick squeeze before letting her go. “I’ll go downstairs and wait alright?”
Twilight nodded, quickly pulling her panties back on before running to her closet to search for something to put on.
Cheerilee smiled and headed downstairs, only to stop dead in her tracks at the bottom of the stairs at the sight of Princess Celestia sitting on the couch, nursing a cup of tea. She glanced up and set her tea down.
“Hello. You must be Cheerilee?”
Cheerilee nodded meekly before bowing deeply. “Yes I am, Your Highness.”
“Now now, my little pony, If you are dating my precious student, you have no need to bow to me. Come, sit next to me.” Celestia patted the cushion beside her.
Cheerilee nervously walked over and sat down as Celestia lifted her cup and took another sip of tea.
“Mmm, Spike does make a good earl grey tea. Would you like me to ask him to make you a cup?” Celestia smiled gently.
“Ah, no. No thank you, Princess. I, um… I didn't see you when I got here.” Cheerilee intertwined her fingers in her lap, internally reaching for all the experience she had accumulated from years of parent-teacher conferences.
“I only got here about five minutes ago. Spike sent me a letter, no doubt worried that Twilight might need me. I’m very relieved to see he was incorrect. Now, seeing as you are still here and I do not hear my Twilight in tears, am I right in saying that she told you her secret?”
“Yes she did, Princess.” Cheerilee smiled with a slight nod.
“I’m very glad to hear that. Well, now that she has told you, are you planning to stay with her?” Celestia set the cup down with a quiet clink.
“I am. I love Twilight Sparkle very much. I don’t plan on ever leaving her.” Cheerilee smiled brightly.
“I’m glad to hear that. You seem like a very kind mare, and I’d hate to send you to the Sun.” Celestia beamed with a wink as she stood up. “Well then, I have to get back to Canterlot; I left a few nobles mid-decree.”
“Of course, Your Highness. May I assume that we’ll be talking again soon?” Cheerilee stood up a few moments after Celestia.
“I would count on it. Until then, Cheerilee.” She bowed her head and vanished in a flash of light as Twilight came downstairs wearing a denim skirt and white blouse.
“You look beautiful, Twilight.” Cheerilee smiled, taking Twilight’s hand and kissing it.
“Thank you. I was just about to head over to Sugarcube Corner. If I tell Pinkie that I’d like to talk to all of the girls this afternoon, I’m sure she’ll make sure that they all get here.” Twilight smiled, entwining her fingers with Cheerilee’s. “Would you come with me?”
“Of course I would.” Cheerilee smiled and gently tugged Twilight to the door. “Let’s go now, before you can lose your nerve.”
Twilight nodded and opened the front door. Cheerilee stepped back in shock to see Pinkie Pie standing right outside, grinning ear to ear.
“Hi Twilight! Hi Cheerilee! I just wanted to let you know that everyone will be here in a few minutes! Can I come in?” Pinkie bounced excitedly in place.
Twilight blinked and nodded wordlessly, stepping to the side as Pinkie bounced in. Cheerilee squeezed Twilight’s hand.
“I know this is sooner than you had hoped, my little love, but I will continue to stand by your side.” Cheerilee smiled. “And at least this means you shouldn’t be able to lose your nerve.”
Twilight simply nodded and lay her head on Cheerilee’s shoulder. The older mare led her to the couch and wrapped an arm around her, as one by one Twilight’s best friends came in. Finally Rainbow Dash wandered in stretching her arms above her head.
“What’s up? One minute I’m enjoying the greatest nap ever, the next minute Pinkie was yanking on my tail saying Twilight needed to tell us all something super important, so here I am. What's the super important thing, Egghead?”
Twilight stared down at her lap, her hands trembling.
“Twi? What is it, girl? Ya know we’re all here for ya.” Applejack kneeled in front of Twilight and took hold of one of her hands.
“She’s right Twilight,” Fluttershy chimed in. “N-no matter what, we’re your friends.” She smiled nervously, her mane falling into her face, covering her right eye.
“But of course, darling!” Rarity agreed. “Why would you ever feel unable to tell us something!” She firmly shook her head.
“Yeah, Twilight! No matter what, we’re going to be bestest friends forever! I mean, how couldn’t we? We’re the Elements of Harmony!” Pinkie beamed, wrapping her arms tightly around Twilight.
After a few more moments Twilight looked up tears rolling down her cheeks. “Everyone… my friends… I… a-alright.” Twilight took a deep breath and told them everything. About her past, and especially about Dusk Shine. The entire time she spoke she stared down at her hands and her friends stayed silent.
“Oh, Twilight… did you really think that this would make us hate you? Or think of you as less of a mare?” Rarity gently lifted Twilight’s chin while using her magic to wipe away her tears. “Oh my darling, Twilight, do not cry. You’ll ruin your mascara. After all, we mares have to take care of ourselves!”
Twilight blinked and sniffled. “Rarity… Rarity, do you really mean it?”
Rarity huffed. “Of course! Do you consider me a liar, Twilight Sparkle?”
“Never, I promise. W-What about the rest of you girls?” Twilight glanced at the rest of her friends.
Applejack took her hat off and sighed. “Twi, Ah can’t say Ah understand all of this. Don’t rightly know how Ah’d feel if any other mare told me they felt this way but… shoot, Twi! We’ve been through everything this here world could throw at us. And if Ah didn’t leave ya during any of those times, Ah ain’t going anywhere now. Face it, Miss Twilight Sparkle - yer stuck with me.” Applejack smiled, placing her Stetson on Twilight’s head and firmly grasping her shoulder.
“Eh,” Rainbow Dash shrugged, extending her wings. “From the sound of your story, you haven’t changed much since you were a kid. Colt or filly, you’re still an egghead!” She smiled before ruffling Twilight’s mane. “But you’re our egghead, and we wouldn’t change you for anything.”
“She’s right, Twilight. Nothing you say or do is going to make us leave you. We love you, Twilight.” Fluttershy smiled, taking Twilight’s hand in both of her own.
“Yeah! How could this change anything!? I mean, you still love books and vanilla cake!” Pinkie grinned, wrapping Twilight in a tight hug before glancing over at Cheerilee and winking. “But, we can have a ‘Twilight Told Us Her Biggest Secret and None of Us Cared Party’ later, cuz I think these two want to be alone!” She forcefully rounded up the others before escorting them out, stopping to poke her head back in. “Let me know beforehand when you plan on getting married! It’s gonna be even betterer than Cadance and Shining Armor’s!” With a cloud of pink, she disappeared and closed the door shut behind her.
Twilight fingered the Stetson still on her head and began to laugh until tears were once more running down her cheeks, and she looked into Cheerilee’s eyes with a giant grin. “I-I did it, I told them… a-and they still love me!”
Cheerilee captured Twilight’s lips in a short kiss, nipping her bottom lip. “They aren’t the only ones who love you, my silly mare.” She raised her voice a bit, so as to be better heard. “Spike! Twilight and I are going to be studying for the rest of the day! Would you mind going over to Rarity’s?”
“Sure! Not a problem. Should I grab dinner on the way home?” Spike asked, grabbing his jacket from the closet.
“Some hayburgers and fries would be wonderful. I’ll even pay you back!” Cheerilee called, hearing the sound of Spike’s grunt of agreement, followed by the recognisable sounds of him shutting and locking of the front door.
Twilight looked up at Cheerilee, her head cocked to the side. “Studying? What type of studying will we be doing?”
Cheerilee pulled Applejack’s stetson off of Twilight’s head before setting it someplace safe. “My favorite subject, little love. Biology. ”
Biology *Clop*
Twilight’s eyes widened before she looked down at her hands “B-biology… do you mean?”
Cheerilee smiled, lightly gripping Twilight’s chin, lifting it so she could better look into her eyes. “Of course, my Twily. I’ve been aching to study biology with you and nothing is going to stop me.” She pressed her lips against Twilight’s, lightly lapping at them, asking to be let in. After a brief moment of waiting, Twilight’s lips opened just enough to allow Cheerilee’s tongue to slip through. Cheerilee’s hand gripped the back of Twilight’s head, holding her in place with a light moan.
Twilight’s eyelids closed as she pressed her tongue against Cheerilee’s, following it in a new dance that she had been shyly, yet eager, to learn. After a moment she pulled back, a line of saliva connecting them for a brief moment “Wow… I’ve never kissed like that…”
Cheerilee nodded, placing both hands on Twilight’s waist, slipping her thumbs into the top of her skirt. “A precursor to our lesson, though. I’m afraid we are both over dressed for this. Now as you already took your clothes off earlier, it just is not fair to ask you to do so again. Instead I will ask you to undress me in any manner you wish and then I shall do the same with you. What do you say my little love?”
Twilight stared for a moment a red flush covering her cheeks before she slowly smiled. “Yes… yes I think I’d like that.” She stood up, causing Cheerilee to lose her grip as she gave her a once over. “Stand up and stand in front of me, please?”
After a brief moment Cheerilee stood in front of Twilight, her arms hung limply at her sides. “Well my sweet love, I’m ready.”
Twilight’s hands reached out to the buttons on Cheerilee’s blouse, her fingertips trembling as she slowly undid the first button. She licked her lips and looked up at Cheerilee to see her smiling lovingly. Feeling spurred on, Twilight quickly undid the rest of the buttons, leaving the blouse open and revealing a glimpse of Cheerilee’s white bra.
“If I had known today would be the day, I’d have put on something a bit more… enticing.” Cheerilee took Twilight’s hand and placed it on her right breast.
“I-I think you are enticing even without attractive clothing… I mean…” Twilight blushed as she stroked Cheerilee’s breast through her blouse. “You take my breath away…” After a brief moment she reached for Cheerilee's open blouse and tugged it off in one quick yank, letting it fall unceremoniously to the floor.
“So what do you think? Do I look alright for an old mare?” Cheerilee grinned as Twilight seemed to be staring at her topless form. “Oh come now Twilight don’t lose it before you even get my bra off.”
“Right. The bra… I just…” Twilight paused, gazing at Cheerilee’s bra as if it was a new equation she wasn’t quite able to work out. “I need to undo the clasp… but you don’t seem to have one like I do…” She chewed her lip before giggling “Oh right. Yours would be on the back then wouldn’t it?”
Cheerilee lifted an eyebrow “Mmmhmm. I’m starting to wonder just how much of your blood goes to that cock of yours when you are aroused, my little love.”
Twilight squeaked in response as she went behind Cheerilee and began tugging at the clasps on her bra, her tongue poking out between her lips until, “Got it. I can’t believe how much easier it is to put a bra on then to take it off. I wonder if that may be part of the design.” While she spoke she traced her right index fingertip down Cheerilee’s spine, marveling at how soft the fur on her back was.
“That felt nice… Again?” Cheerilee mumbled while allowing her head to fall to the side.
“Of course, you are so soft…” Twilight ran her fingertip down Cheerilee’s spine again and again as she heard Cheerilee humming in the back of her throat. “Careful or I might think you are part cat.” Twilight lifted her left hand and slowly pulled the bra strap off of Cheerilee’s shoulder before doing the same with her right hand. A soft thump on the floor was all the evidence Twilight had that the bra was no longer covering her lover’s breasts. She closed her eyes tightly for a moment before reaching from behind Cheerilee and cupping a boob in each hand “Oh… you are so very soft…”
Cheerilee opened her mouth to answer, before stopping as Twilight’s fingertips brushed against her nipples, causing a moan to escape her lips.
“Did I do that right?” Twilight questioned, biting into her bottom lip as Cheerilee brought up her hands and laid them over Twilight’s in answer.
“Come out from behind, my love. I want to be able to see you, not just feel your hands.” Cheerilee’s voice was husky as she felt Twilight pull back and smiled as she reappeared in her sight. It was obvious from the slight bulge that was visible through Twilight’s skirt that she was enjoying this as much, or more, than Cheerilee was. “There we go now… I want you to take one of my nipples in your mouth. Suckle lightly and please don’t bite down no matter how nice I may taste.”
Twilight’s ears pinned back as she licked her lips and nodded. Slowly she took Cheerilee’s left breast in her hands and brought her lips to Cheerilee’s nipple. She gave it a soft kiss before opening her mouth and touching the tip with her tongue, shivering at the taste and touch. She felt it harden against her tongue and slowly wrapped her lips around the nipple, suckling gently. Her eyes closed as above her Cheerilee’s mouth had opened in a silent moan as Twilight grasped her right breast with her hand, pinching her nipple with her fingertips, enjoying the soft squeaks that were now escaping her love’s mouth.
After a few moments Twilight pulled back. A bit of saliva remaining on Cheerilee’s nipple caught the light before Twilight kissed it, then slowly trailed kisses from her nipple down to her belly button. Twilight paused a split second before giving it a slow lick and turning her attention to the jeans Cheerilee was wearing. Down on her knees Twilight took hold of her waistband with both hands and hummed. “If you had a spare outfit here I’d use my magic and burn them off of you.”
“Mmm I’ll keep that in mind for next time.” Cheerilee allowed her head to loll back, her eyes closed as she felt Twilight’s fingertips under her waistband. Slowly her jeans were tugged down her hips. Cheerilee lifted her feet one at a time, allowing Twilight to fully remove her pants.
“...” Twilight looked up, biting her lip before looking back at Cheerilee’s panties. The only remaining barrier between her and Cheerilee’s pussy. She took a deep breath before grabbing hold of the waist band with her teeth. Nervously gripping hard as she could she yanked her head down and yiped falling back onto her tail, Cheerilee’s ripped panties in her mouth.
Cheerilee covered her mouth to keep from both crying out from the snap and laughing at the sight of Twilight flat on her back her torn panties hanging over her face. “Oh Twilight…”
“Sorry! Sorry! I was I just thought…” Twilight sat back up, a blush covering her cheeks “I saw it on an old porno Shiny didn’t know I was watching… I thought it looked sexy.”
“Mmm, maybe next time we try that I’ll wear edible panties hmm?” Cheerilee smiled as Twilight’s blush increased. She stretched her arms over her head and looked down at Twilight. “My turn…”
Twilight stood up trembling. At any other time she would be terrified at what might be coming. Now though? She was trembling in anticipation. She felt Cheerilee’s eyes roam over her body before pausing at her horn.
Cheerilee licked her lips as she took Twilight’s horn in her hand, causing the unicorn to shiver. “Oh… Is Twitwi’s horn sensitive?”
“Uh… uhhuh…” Twilight’s eyes rolled back in her head and her tongue poked out of her mouth.
“Mmm how about that… I wonder.” Cheerilee slowly ran the tip of her tongue from the base to the very tip. A smile spread across her lips as she heard a small gurgle escape Twilight's throat. Taking that as a good sign, she wrapped her lips around Twilight’s horn and began suckling on the rounded tip.
Twilight wasn’t sure what was going on, all she knew for certain was that it felt amazing. Her knees began to shake before she almost collapsed to the ground. Cheerilee barely caught her as she continued to suckle on the tip of Twilight’s horn.
After making certain Twilight was not hurt from her sudden collapse, Cheerilee took more of Twilight’s horn into her mouth. She bobbed her head up and down its length, enjoying not just the feel of her new found toy but also the effect it seemed to have on her normally shy love. As Twilight’s breathing increased and tiny pants escaped her lips, Cheerilee took more of Twilight's horn in her mouth until she was almost gagging. She paused a moment and pulled back to see Twilight trembling and her eyes glazed over. The pants escaping her mouth caused Cheerilee to return to her suckling and after a moment she swallowed the entirety of Twilight’s horn down her throat barely getting past her own gag reflex. It was worth it.
Twilight groaned as she subconsciously began thrusting her head back and forth. Feels… so nice…
Cheerilee’s eyes widened as the felt the horn being thrust back and forth in her throat. Though unusual, she quickly grew to like and possibly even love the feeling. She wrapped her lips as tight as possible around the base of Twilight’s horn and suckled. After a few moments she pulled back as Twilight’s horn was growing hot. She backed away to see Twilight’s eyes closed and her horn glowing like she was casting a spell.
“Pl-please don’t stop… feels good, want, need!” Twilight opened her eyes which were still glazed over.
Cheerilee bit her lip before reaching for Twilight’s horn with her hand and wrapping her fingers firmly around it before moving her fist up and down. Slowly she went at first, feeling the spirals growing warmer to the touch, then faster as small sparks came from the tip. Twilight was now moaning. She thrust her head back and forth so to move her horn faster through Cheerilee’s grasp until she cried out and a purple liquid came squirting from her horn, which landed on Cheerilee’s chest and face.
Cheerilee closed her eyes just in time not to get the purple liquid in her eyes, but poked her tongue out to curiously lick the goo off of her top lip. It had a very familiar constituency that she readily recognized. Afterall though Twilight may have been a virgin Cheerilee had been around a few times. She lapped up all that was within reach of her tongue. It had an interesting yet enticing taste. It was salty like most ejactulate was, but, there was something more. A sweetness maybe? She’d have to do many more taste tests to figure it out exactly. Not now though…
“Twilight? Wh-what was all that?” Cheerilee grabbed her torn panties and cleaned the dribbling mess off of Twilight’s horn as the mare blushed.
“I, I have never personally experienced it before now, but, A unicorn’s horn is one of the most sensitive parts of our bodies. It’s full of receptors of all types, including pleasure. B-basically you made me feel so good that my magic kind of exploded.” Twilight glanced away from Cheerilee, gazing down and admiring her own feet.
“So, unicorn stallions have two cocks?” Cheerilee asked after a moment of thought, causing Twilight to nervously giggle.
“I guess if you wanted to look at it like that?”
“How very… interesting.” Cheerilee licked her lips. Oh yes she planned on examining this a lot more in the future. She lifted Twilight’s chin and kissed her forehead right under her horn. “What other surprises do you have in store for me, my little unicorn?”
Twilight opened her mouth, probably ready to tell Cheerilee all the differences between earth ponies and unicorns before closing it and smiling.
“Oh. I see. I’ll have to find out for myself hmm?” Cheerilee kissed each of Twilight’s eyelids, peppering kisses down Twilight’s face, stopping briefly on her lips and nibbling her bottom lip.
“Mmmhmm, after all we are both scholars so where would the fun be in my just telling you?” Twilight kissed back, sliding her tongue in between Cheerilee’s lips. She whined as Cheerilee pulled away after a few seconds.
“Now, now, Twilight it’s my turn. You got to have your fun and undress me.” Cheerilee touched the tip of Twilight’s nose with her tongue.
Twilight’s eyes crossed as her nose was licked before giggling. “...Fair is fair right… bu-but will you hurry? Please?”
Cheerilee took a step back and shook her head “No..” She breathed in before taking a good long look at Twilight, including what she was wearing. She smiled before running her fingertip from the bottom of Twilight’s throat, tracing down to just touching the waistband of her skirt. She shook her head tsking "Oh Twilight, denim? Is that really the proper look for a student of your caliber? Is teacher going to have to instruct you like you were a little filly again?"
Twilight cupped her hands together behind her back and bit her bottom lip. It had been some time since she had been scolded by a teacher. Celestia was fairly giving with what Twilight wore to class but she had had some stricter teachers. She shivered, feeling her cock twitch inside her panties hearing Cheerilee talk to her like this… “I’m sorry I’ve been a bad girl Miss Cheerilee…”
Cheerilee lifted an eyebrow. So that’s how you want to play it hmm? “We’ve had this discussion before, Miss Sparkle, I warned you what would happen next time. Go bend over the arm of that sofa young lady!”
Twilight’s eyes widened and licked her lips before walking over and bending herself over the arm of the couch. She closed her eyes, bit into bottom lip and waited. After a few moments of no sound she opened a single eye to see Cheerilee smiling down at her. Twilight blinked as Cheerilee ran a single fingertip down her spine, causing her to shiver.
smack
Twilight yiped, feeling Cheerilee’s firm palm smack onto her skirt. She wiggled a bit as Cheerilee moved to stand behind her pushing Twilight's face onto the cushions.
spank!
“Youch!” Twilight cried out. Cheerilee was a lot stronger than she looked. Twilight hadn’t been spanked like this since… she couldn’t even remember.
smack smack spank
“Alright, that’s enough over your skirt you naughty naughty filly.” Cheerilee pulled Twilight’s skirt off and tossed across the room where it landed by the entrance to the library proper. She then patted Twilight’s panties-covered butt, moving her tail to the right side. “After this I don’t think I’ll need to worry about you being out of uniform again will I?”
“N-no Miss Cheerilee! I’ll be a good filly I promise.” A tear fell down Twilight’s cheek even as her ass twitched in anticipation of what was to come.
“We’ll just to make sure you will not forget again!” Cheerilee ran a fingertip on the seam of her panties. “Now I’ll give you a choice shall I? Would you prefer twenty swats over your panties or five stinging swats on your bare bottom?”
Twilight hesitated a few moments as she felt her cock throbbing where it was shoved into the arm of the sofa. five swats and I’ll be up faster… “Five swats, please Miss Cheerilee.”
“Very well, I want you to ask me very nicely to pull off your panties and spank your little bottom red.” Cheerilee gave a small warning swat as Twilight squirmed.
“Y-yes Teacher! Would you please take off my panties and spank my naughty bare bottom? It’ll help me be a good girl.” Twilight closed her eyes, trying not to think about her painful position
“Of course I will Twilight! I’d be happy to help you be a good girl.” Cheerilee tugged Twilight’s panties down her legs. She snorted at the sight of Princess Celestia’s cutie mark on the front of Twilight’s panties, filing it away as something to tease her little love about at a later time. I wonder if she has a pair of Princess Luna’s as well. She licked her lips as she watched Twilight’s firm bottom tense and release and ran a fingertip over her soft fur before lifting her hand and bringing it down hard on Twilight’s bottom.
“Yipe!” Twilight was not expecting it to hurt that much! And that was only one?
SpankSpankSpankSpank
After the final swat had landed on Twilight’s now-red bottom, Cheerilee moved back allowing, Twilight to jump up. Her hands moved to her bottom as she tried to rub the heat from her cheeks. Her dick bounced up and down as she rubbed.
Cheerilee licked her lips watching Twilight’s small dick. Mmm, just the perfect size… “I see that you’ve been working on a gift to thank me for helping you to be a good girl hmm? Is it ready?”
Twilight paused in her rubbing as she tried to figure out what Cheerilee was talking about until she slowly followed the direction in which she was looking and swallowed. “Y-yes it is! Do you like it?”
Cheerilee smiled, walking closer before she got down on her knees and licked her lips. “Oh yes, it’s wonderful.” She brushed a fingertip over the shaft before softly kissing the tip. She could hear Twilight above her moaning and felt Twilight’s hands come down on her shoulders. After a few more kisses she licked the head of Twilight’s cock, her fingers massaging into Twilight’s ball sack. Cheerilee pulled back and licked her lips. The salty taste of Twilight’s precum was like ambrosia. I need more… Without another thought Cheerilee took Twilight’s small cock in her mouth, suckling gently and closing her eyes. It was nice being able to take all of Twilight in just one mouthful, far easier on her throat than her last coltfriend had been.
Twilight shivered, her toes curling as she felt Cheerilee suckling at her cock. The entire shaft felt electrified. Twilight moaned and began thrusting her hips hard, trying to force her cock farther into Cheerilee’s mouth even if it wasn’t possible.Cheerilee hummed while encircling Twilight’s cock with her tongue and then pulling back until Twilight’s cock head was the only part left in her mouth, before quickly thrusting her lips around the shaft again, causing Twilight’s eyes to roll back and her hand to curl into a fist as she trembled. Her mouth opened and silent pants escaped her as she took her other hand and put it onto the back of Cheerilee’s head. She pulled her to her crotch before thrusting one final time.
Cheerilee’s tongue happily lapped at the drops of precum dribbling from Twilight’s cock until a full stream filled her mouth, causing her cheeks to bulge. Shit I forgot, small cock or not unicorns always cum a lot. Determined not to allow a single drop to escape she began swallowing down the salty cum as even more filled her mouth. Finally, after a few more spurts Twilight’s cock stopped twitching and Cheerilee let it slide from her mouth before cleaning it with her tongue. She moaned. The fur between her thighs was covered in her own juices and so soaked it was even dripping onto the floor but after that… She blinked and her eyes widened to see Twilight was still fully erect and smiling.
“Didn’t you know? unicorns normally have to ejaculate twice per session… I mean, if you are up for it?” Twilight smiled, a light blush covering her cheeks as her fingers began undoing the buttons of her blouse.
“Fuck me, Twilight Sparkle… I want you in me!” Cheerilee laid back on the floor, her legs spread to reveal her swollen and soaked sex. She stretched back her arms over her head and stared up at Twilight, who had stopped messing with her buttons. Her eyes glazed over as she ripped the remaining buttons off and let the ruined blouse fall to the floor.
Twilight licked her lips and got down on the floor. She kissed Cheerilee’s lips, snaking her tongue into her mouth and tasting herself. She pulled back a strand of saliva connecting them as Twilight aligned herself. “How could I say no after you asked so nicely.” With that said she thrust her cock into Cheerilee’s pussy and groaned.. It felt so good she almost came right then. No, this is my first time with the mare I love, I have to last at least until she is relieved. Twilight pulled out until just the tip was in before slowly thrusting back in. As she thrust in and out of Cheerilee’s pussy Cheerilee reached up and grabbed hold of one of Twilight’s large breasts, wrapping her lips around her nipple and suckling.
Twilight’s eyes widened as her nipple was suckled and began to thrust harder and faster, determined to bring Cheerilee to climax. She closed her eyes tight as sweat rolled down her forehead. She grunted, thrusting as fast and hard as she could, feeling Cheerilee’s pussy walls squeeze against her cock as her lips let go of Twilight’s nipple.
“Oh Twilight! Yes!”
Twilight bottomed herself as deeply into Cheerilee as she was able to as her cock began to spurt. She collapsed on top of Cheerilee, her bangs plastered to her forehead. She panted, trying to get her breath back. She felt her cock finally shrinking down but didn’t care as Cheerilee kissed her forehead. Finally, after catching her breath, Twilight looked into Cheerilee’s eyes and smiled. “So, h-how did I do?”
Cheerilee wrapped her arms around Twilight’s back and hummed happily. “Twilight Sparkle, as in all of your studies. You’re a natural.”
