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!