Many ponies underestimated the power of checklists, but Twilight Sparkle wasn’t one of them. Almost any problem she faced could be solved with a checklist, just so long as she had time to compile one. They brought comfort and order to her life - they were precious to her. She still had her mammoth ’First Day At School’ checklist in safe keeping, alongside the even longer ’First Date (Mare)’ checklist (every item neatly ticked, some lines multiple times), ’First Date (Stallion)’ checklist (currently untouched) and the truly massive ’Moving to Ponyville’ checklist that took up half the box she kept them in (it had been a trying time for her).

One checklist, though, was special. It was written by her own hoof as she did not dare dictate it to Spike. Longer than any other, it laid down a complex plan of breathtaking audacity. She had started it shortly after moving to Ponyville, slowly plotting a course to a goal that she decided would be the ultimate achievement of her life. It was titled ’Seduction (Princess Luna)’. The thought of anypony actually finding it in its secret hiding place kept her awake at nights.

The Plan was years in the making, with seemingly insurmountable barriers halting progress for months until they fell before her great intellect. Twilight's biggest problem was that this Plan could not be allowed to fail. She needed a safeguard and after weeks of effort, modifying the time magics she found in the Starswirl the Bearded in of the Canterlot library provided the key.

With long and painstaking labour, she developed a spell that would allow her to 'save' and 'reload' her life, keeping all her memories between saves. With this spell, she could relive each day until it was perfectly spent getting closer and closer to Luna’s heart (and bedroom).

Twilight had listed all the problems that would need to be overcome with the powers of foreknowledge that the spell would grant her. Finding how to get close to Luna, finding the weaknesses of her terrifying guards, learning her likes and dislikes. All the knowledge thus gained was to be used for maximum effectiveness towards the triumphal day when she brought all the elements together to seduce the mare of her dreams. It would take years of subjective time to do, but Luna would be hers!

Creating the necessary spells and drawing up the Plan was a massive effort, but the memories from the fateful day of the one thousandth Summer Sun celebration kept her focused. That long night she saw Luna’s beauty and vulnerability that she so wanted to protect and cherish, but she also saw the power and glory of Nightmare Moon, the merest thought of whom sent delightful shivers down her spine. Luna combined in her graceful form the dichotomy of sweet vulnerability and commanding power that overwhelmed Twilight’s thoughts.

She could barely contain her excitement on the night that she finally triple-checked the checklist and found that it was complete. She was ready. Not willing to wait a moment longer than necessary, she rose at the crack of dawn on the first day of the great endeavour and cast the first of the complex spells she had crafted for the undertaking.

As the plan could take subjective years to fulfil, she ran the risk of coming back having forgotten the day-to-day affairs of Ponyville. The spell she cast captured her state of mind, sealing it in the strange bust in the centre of the library. When she came back and faced the bust, her memories of Ponyville and her friends would be returned to her. Satisfied that the spell was cast, she departed leaving a note to Spike informing him that he was in charge until she got back.

The train journey was nerve-wracking as she came ever closer to her love, her destiny. She spent the time quadruple checking the appendices in section three of the tertiary portion of the checklist (conversational gambits to determine Luna's favourite foods).

Disembarking from the train, she headed quickly to the palace. The place guards knew her, and would let her through without hesitation. She sneaked in anyway - she was worried that if they were to casually greet her she would break under the pressure and admit everything - it’s useful to know one’s own weaknesses.

With ninjistic stealth, vulpine cunning and the obligatory black catsuit, she slipped into the palace grounds. With ghostlike grace, she glided through the corridors unobserved by anypony who would raise the alarm (she was observed by a number of ponies who would not raise an alarm, because they had lived in the palace for years and knew Twilight Sparkle by now).

Twilight’s courage stayed with her until she reached the corridor that lead to Luna’s personal chambers. Here came the first test - the Lunar guards.

She had drawn up a number of plans for getting past them - the first one was to use the 'need it, want it' spell to ’persuade’ one guard to start making out with the other and slipping past while they were distracted. Despite having a ridiculously low projected success rate (2.3%), it had for some reason remained at the top of the checklist, ahead of several more practical options such as ’teleporting the guards to another part of the palace’ (87.9%) and ’asking nicely to see if she could speak with Luna’ (74.5%).

She read the checklist one last time. She quickly made a save point and reloaded to make sure it worked. She was ready. Satisfied, she squared her shoulders and haunches, held her head high and with a deep breath, rounded the corner to face the first great obstacle.

Luna’s bedchamber door was unguarded.

Years of meditation and training under the immortal Celestia had given Twilight superpony powers of control - she didn’t knock herself out with a face-hoof, just bruised herself slightly. When she recovered from her chagrin, she reloaded to lose the bruise and trotted up to the door nervously.

There was no immediate answer to her timid knock, so she steeled herself and did it again more forcefully. After a moment a beautiful yet sleepy voice called out “Enter”.

Twilight hesitantly opened the great doors and found herself facing complete nothingness. Her eyes strained but could not make out anything past the portal. Luna’s bedchamber lay shrouded in magical darkness - clearly the princess liked to sleep in the dark. With a gulp, she squared her shoulders and with one last glance at the empty corridor, she stepped into the abyssal void.

Testing the unknown with awkward hooves placed carefully on the unseen floor she entered the room. She turned, eyes aching for light, and reached with her magic for the door that she knew was there behind her, pushing it closed with a soft click. The faint and distant sounds of palace life were immediately cut off; all Twilight could hear was the hammering of her heart. She stood still, breathing deeply, until her heartbeat calmed and breathing slowed. Senses straining in the void, she became aware of slow breathing, some strides ahead of her.

“Luna?”

“Hmm? Twilight? Prithee, tell me what doest thou here?” The sound of a yawn followed the words in the darkness.

This was going to be he hardest, and longest, part of her campaign - the verbal seduction of Luna. This would be a slow game of cat and mouse, mapping out the perfect things to say to overcome Princess Luna’s defences and win her heart. She would save and reload, going through each conversation time and again with playwrights and poets until everything she said and did was perfect.

The first step was simple - establish a baseline. By having the most awkward conversation first, she could learn how Luna would react when things went wrong and she could start inuring herself against being shot down by the goddess (something that was bound to happen often).

She had even drawn up a recovery plan for dealing with the inevitable rejection (1. Eat as much ice cream as physically possible, 2. Reload, 3. Repeat as necessary). In previous visits she had reconnoitred the Canterlot ice cream parlours and identified the best one for emotional recovery. She had even drawn up a sliding scale listing which ice creams were to be consumed, based on the severity of her emotional distress - she would save the chocolate and dandelion for when things looked really bad.

Bracing herself for the divine retribution that was sure to follow, Twilight made her first move. The worst pick-up line she could think of.

“Hi Luna - I'm sorry to wake you. It’s just that I’m feeling really horny and was hoping that you were too...”

The silence that followed dragged on for what like hours until suddenly a sultry voice whispered into her ear “Why Twilight, we thought you’d never ask!”

----------------------------------------------------

Twilight, startled, leapt and spun to face the voice but could see nothing. The chuckle at her antics sounded <hungry> and her heartbeat raced with excitement and fear.

“Princess? I can’t see you...”

Twilight was desperately turning her head left and right, straining for any sight or sound of the alicorn. Complete silence was her only reward until she heard the faint whisper of a falling cloth in one direction. She sprung to face the noise, motionless, until Luna, satisfied that her distraction had worked, nipped at Twilight’s ear from behind.

“Aaaah!” Twilight shouted with a surprised shriek.

“Twilight Sparkle, thou hast disturbed the sleep of a Princess, and made lewd suggestions to our person! Thou shalt be punished!” The delight in Luna’s voice made her intentions clear, and Twilight gulped as heat started to gather in her hindquarters in anticipation. She instinctively backed away from where she thought the princess stood, only for her rear to collide with the hoof of Luna’s bed. She fell backward onto her haunches with a yelp. A silken muzzle stole a quick kiss from her lips and then darted away.

“Hmmm - it’s been so long... We don’t recall the correct punishment for thy crimes. We shall have to... improvise”

Before Twilight had a chance to respond with more than an intake of breath, she felt silken movement around her fore hooves. Her hooves were drawn tightly together as they were lifted inexorably above her head. With her weight on her haunches, she found herself with her belly, and her rapidly dampening marehood, fully exposed.

“Is this is alright, Twilight?” Luna asked, dropping her faux haughty air, “I mean it’s been so long. Am I going too fast? Is this too rough? Do you want this? We can do something else...”

“Oh goddess, please don’t stop!” Twilight exclaimed. “I mean, *ahem*, ’Oh no! I have insulted the princess of the night! I must be punished!’”

“Hehehe. We are greatly angered by thy villainous ways. Prepare to be it tickled!”

“Eeek!”

Luna set to tickling the helpless mare with both hooves, giggling along with her captive. Electric sparks danced up Twilight's spine as Luna's hooves brushed over her cutie mark. The tickles soon changed to caresses, the giggles to moans, and Luna started licking the purple fur in front of her. She slowly worked her way down from Twilight’s slender neck, across her teats, which were teased mercilessly, down her belly and finally to Twilight’s very damp and ready pussy.

Teasing Twilight’s slit and swollen nub with considerable skill, Luna delighted in the pants and moans coming from her captive. Normally she would have held back and prolonged both their pleasure, but no-one had shared her bed in centuries and she was too eager for her own satisfaction. She carefully and ruthlessly drove Twilight to a screaming climax.

Twilight lay gasping on the floor. The mysterious bindings slipped away from her hooves as she slowly recovered her breath and mind. Taking the hint, she struggled to her hooves.

“Now is the time to demonstrate your worth to your goddess, supplicant!” Luna declared, making little attempt to hide her desires behind her mock-arrogant tones.

Twilight would have liked nothing better but, “I can’t see you...” She said desperately. No sooner had she spoken than she felt a waft of air pass her face, carrying a captivating musk.

“The night is to be experienced with all your senses, Twilight.” Luna’s voice suddenly turned deep and seductive, “Feel your way.”

Twilight breathed in deeply and reached ahead with her hooves, to where the voice was coming from. A silvery laugh rang out when a hoof brushed a luxuriously soft flank that danced out of the way. Twilight stumbled, but when she rose, she found her muzzle scant inches away from the delectable odour he had smelt before. She eagerly leaned up and in to taste the night. Luna gasped with joy as Twilight’s tongue began to explore her nether regions, lapping up the juices now freely flowing from her. Her nervousness flowed away as she relished the experience. Her long exile and strong urges had, however, left her in even more desperate need than Twilight, and she barely lasted minutes before the pressure became unbearable and orgasms took her.

Twilight continued to lap at Luna’s lower lips until Luna pulled away with a gasping laugh, leaving her in the darkness. This time, though, Twilight thought she could see a distant spot of light. Eyes straining, she peered ahead at the distant spark that had caught her eye.

The spark was swiftly joined by a twin and then yet more motes of light, all dancing back and forth. The lights, (stars! Twilight thought) rushed to her until she was surrounded by he majesty of the night. Her eyes wide with wonder, the mare tried to take it all in as they flowed around and behind her. She span around to see their destination when normal lamp light came to her peripheral vision. The starfield moved away, revealing more of the bedchamber of the princess of the night. The star-studded darkness was still captivating her vision, until what she was seeing clicked in her mind - it was Luna’s tail.

Luna was reclining seductively on her queen-sized bed, her cosmic tail settling on the covers, still drifting in some aethereal wind. Her long, slender legs were clothed in long, purple and white striped stockings that drew the eye to her perfect flank. Twilight gaped at the beauty of the sight and then took a step forward towards the lovely vision. She paused a moment when a fore-hoof touched something soft - she glanced down and saw a single, long, midnight-blue stocking. It was creased strangely and Twilight blushed when she realised that it had recently done service binding her hooves.

Luna beckoned Twilight to the bed and the young mare gladly moved to her side, reverentially stepping onto the bed. Luna’s tail drifted to cover Twilight's haunches, her wings to blanket her back. Twilight snuggled up to the alicorn, feeling a immensely satisfied as she nuzzled Luna’s neck.

“Thank you, Twilight” Luna said, “I'm sorry that was so fast - after a thousand years of draught, I was getting a little tense.” Luna stretched delightedly on the silken covers, before turning back to face Twilight “That felt so good. I understand if you're too tired, but if you’re up for more...”

She was interrupted by Twilight’s nuzzling moving up her neck to her muzzle and their lips met in a kiss. Luna’s passion grew and the kiss became deep and hungry, tongues dancing with each other. Still kissing, Twilight rolled Luna onto her back and Luna gave way until the smaller mare was astride Luna, trapping her in her embrace. After a heavenly eternity, Twilight broke off from the kiss for air. She then started peppering Luna’s muzzle with little kisses. When she reached Luna’s neck the kisses started including little nips as well and Luna’s closed her eyes and started to hum with joy. Twilight mentallly noted Luna’s reaction and filed it in her mind for later as she worked her way back down Luna’s body to her marehood. Licking carefully around the sides of her slit, she boldly teased the goddess.

Luna quivered with delight under Twilight’s ministrations, her hips grinding the air furiously. She gasped and moaned as the pressure built and found to her embarrassment that the centuries of enforced celibacy had left her weak and her resistance to pleasure was still almost non-existent. Despite having only recently come, she could feel the pressure building and was helpless against it.

Twilight was loving every one of the squeaks, moans and gasps coming from the princess - The Princess! Having her at her mercy, unable to resist the pleasure she was giving her, made her feel empowered. Luna’s grinding hips were loosing coordination, her breaths coming in quick, short pants and her hooves weakly pressing Twilight’s head into her marehood.

Twilight redoubled her efforts, sensing that Luna was close and when her mouth pulled away from her slit to suck on Luna’s swollen clitoris, Luna’s feeble resistance gave way and she fell to the bed, spasming and crying out with joy.

Twilight awaited smugly for Luna to recover. She was already planning a fresh assault, to see if she could make her come even more swiftly. Toying with with ideas in her head and scanning the room for props, she became lost in her thoughts. She didn’t notice Luna’s breathing deepen and slow; she didn’t notice the set of the proud goddess’s jaw. Luna was not going to be humbled by this mare who was millennia her junior - she was going to turn the tables and would not stop until Twilight begged for mercy!

Silently sliding off the bedsheets behind Twilight, she gathered her power with a grin. She was a goddess and she had more tricks at her disposal than mere magic.

Twilight didn’t notice when her thoughts and ideas morphed into daydreams. The cunning plans to have Luna powerless at her hooves, writhing with pleasure, took on extra texture. She became lost in the thought as a hoof drifted down to her rapidly dampening pussy. A lazy grin formed on her face as the hoof began to slide back and forth and her eyes took on a distant cast. The dream Luna was bound in chains, looking up at her mistress with begging eyes. Twilight’s heat grew stronger and a second hoof drifted down to tease her teats. A moan broke from her lips and she was completely distracted by the vision in her head.

This was what the real Luna was waiting for. The blue silken sheets were suddenly seized with Luna’s magic and wrapped themselves around Twilight, trapping her hooves under her.

Breaking free from the daydream that Luna had trapped her in, Twilight found herself suspended several feet above the bed, tightly bound with the bedspread. She struggled, but her fore legs were trapped under her body and her rear legs kicked at the air, finding no purchase. Luna waited until Twilight was fully aware of her situation, her struggles achieving nothing, and then slowly started spinning her round, wrapping even more layers of sheet around the helpless mare.

As the room gracefully span around her, Twilight cast around in desperation. Her eyes caught on a pillow and she flung it with her magic at where she thought Luna stood. The long shot was awarded with a grunt, and the spinning stopped, but she was still helpless. Looking around for more ammunition, she saw with dismay as a blue aura seized all the remaining cushions and floated them from sight. She watched powerlessly as one pillow drifted with aching slowness into her face with the softest of blows before falling away behind her. She growled with annoyance, but was answered with a giggle.

“Now now, Twilight. You are clearly not showing me the respect that I am due as your princess. You must be taught the error of your ways. The punishment will continue until you apologise!” There was the sound of a drawer opening, and closing.

“Hah..,” Twilight huffed with mock defiance, “Never! I shall not bow to a tyrant!”

Luna giggled again, and finished wrapping Twilight in the sheets. Twilight, for her part, suddenly realised that whilst she was wrapped up snug like a pig in a blanket, her hindquarters were fully exposed and the princess had an excellent view, standing behind her. There was silence and then something cold, hard and wet touched her inside leg and she kicked reflexively and yelped. It slowly moved up her leg until her tail was magically moved aside and it reached her pussy where it held steady, only just touching her.

Everything was still for a tense moment. She then felt herself starting to slowly slide backwards, onto the object. She struggled and squirmed in vain as she was slowly impaled on it. It was a dildo, Twilight realised, as it worked its way in to her tight pussy. She instinctively clamped down on it, trying to halt the movement, but it was no good. The disconcerting experience made it impossible for her to gather her thoughts - without focus, all she could think was that she was equally grateful that it was well lubricated and that it was not divinely proportioned as it slid inexorably inside her.

The sliding stopped when the toy could go in no further. She moaned, unable to move the dong in or out, and tried to grind her hips in search of relief. After an eternity of stillness, she found herself moving forwards again as at the same time the phallus moved back, until it had nearly left her. Groaning with frustration, Twilight fought to overcome Luna’s magic with her own, but without focus it was no contest. The dildo started to slide back in, but at Luna’s pace, not Twilight’s.

“Aahhh... Please, princess... I...” Twilight begged

“Well, since you asked so nicely,” replied Luna with a smirk and she slowed the pace.

“Ah! I didn’t mean...”

“Oh, I'm sorry.”

The movement suddenly stopped entirely.

“Nooo! Don’t stop..”

“Make up your mind, little Twilight,” said Luna mockingly.

Happy that both Twilight and the toy were well lubricated, Luna started moving them both in counterpoint with steady vigour, filling the mare with powerful thrusts that Twilight was powerless to prevent. Twilight was gasping and grunting in time with the thrusts from the dildo and sweating from the heat of her cocoon and the frenzy of the action. She tried again to grasp the dildo with a purple aura, but the pleasure broke her thoughts entirely and her magic abandoned her.

Tensing and twitching, grunting and gasping, Twilight found herself on the precipice of orgasm. Luna saw this and didn’t hesitate to push over with a flurry of sudden, powerful thrusts. Twilight let out a hoarse scream of joy.

“Well, Twilight?” Asked Luna, “Are you ready to apologise for your rudeness?”

It took Twilight a while to recover enough breath to speak.

“Princess...” Twilight gasped, “I... haah, I... apologise. I am sorry that I threw a pillow at you.”

Luna was all smiles as she withdrew the dildo (eliciting further gasps and twitches from Twilight) and unwrapped the mare from the silken clutch of the bed sheets. “You are forgiven,” said Luna magnanimously.

Twilight was gently lowered to the bedroom floor where she lay panting for a while. Humming happily to herself, Luna settled down beside her, flank to flank, pulling over a blanket that had miraculously survived the encounter to cover them both and keep in their warmth.

“Thank you, Luna,” whispered Twilight, who found herself now exhausted and struggling to stay awake. “Sleepy...,” she murmured.

“Sleep well, my dear Twilight Sparkle.”

Luna, feeling better than she done for a millennia, lowered her head to her hooves. As she drifted back to sleep, a sly thought crossed her mind and she laughed softly.

“Hmmm - are you ready for round two, little one?”

With that Luna let herself fall asleep, to join Twilight in dreams.

Author's Notes:

Okay, in case it wasn't painfully obvious, this is my first clopfic and indeed first fanfic of any kind. Please do feedback - I need to improve.