There is a First Time for Everything

Rainbow slowly woke up from a deep slumber, the light from the bright morning sun shining through her bedroom window. She softly yawned and cracked her eyes open, her sight falling upon the beautiful mare sleeping contentedly in her embrace. Twilight looked so cute, her fur glistening in the morning sun. Her ears twitched and her chest rose and fell gently with each breath she took, her mane fluttering in the small breeze.

Usually, Rainbow would get up and go on her usual morning wake-up flight, but now she wanted nothing more than to spend the whole morning cuddling in bed with her marefriend. She smiled and snuggled closer to her, enjoying her marefriend’s warmth. She closed her eyes to drift back off to sleep, but it seemed her stomach had other plans, as it grumbled hungrily. She groaned, annoyed that her empty stomach had to ruin this perfect moment for her. As she started to feel the growing pangs of hunger in her belly, she knew she had to get up.

She glanced down at her marefriend, making sure that she was still asleep. She slowly pulled her foreleg from Twilight’s grasp, trying her hardest not to wake her up. She carefully peeled the sticky sheets off of her with a wing and she started to slide away, but Twilight twitched in her sleep, rolling on her side to face her. Rainbow froze as she stared at her marefriend, but she relaxed as Twilight settled back down into the pillows, her forelegs curling up to her soft chest.

Smiling to herself, Rainbow squirmed out of bed, carefully pulling the sheets back over her marefriend as she left. Quietly, she crept out of her bedroom, and with one last glance to make sure Twilight was still asleep, she closed the door behind her. Hopping over the railing overlooking the living room, she glided down to the kitchen, landing with a muffled thump. Pushing the swinging door open with a hoof, she grinned to herself as she planned out a romantic breakfast in bed with Twilight.

She never was much of a cook, but she was determined to impress Twilight. In the past, she never had the patience to take the time to make something, but today was different; she was going to cook breakfast for her marefriend or die trying. With that in mind, she confidently strode over to where her pots were and pulled the cabinet door open, spilling its contents onto the floor. She cringed as the metal banged against each other. Glancing upstairs, she prayed to Celestia that she didn’t wake her marefriend up.

Twilight slowly woke up, feeling all tingly. She arched her back and yawned, “Mmmm…Rainbow, last night was amazing…” She rolled over to face her marefriend and she felt around for her, but she felt nothing but the sheets. Confused as to why she couldn’t find her marefriend, she cracked one eye open, confirming that she was the only one in the bed. Opening her other eye, she sat up and looked around, only to find the white box full of toys laying on the floor.

Her curiosity growing, she forgot about Rainbow for a moment, using her magic to levitate the box to her. She popped the lid open with a hoof and peered inside, gasping in nervous excitement as she saw its contents. The toys from last night were inside there of course, but in addition to that, there were several more, including a fake stallion cock with a leather harness on the base, a couple double dildos, and a funny looking black box.

Her interest piqued, she pulled out the black box and opened it, and on the inside of the lid she read the words 'Anal Training Kit.' “Ohhh, so Dashie is the kinky type, huh? I think we’re gonna have some fun later on...”Twilight thought to herself as she inspected each toy.

There were three pink velvety toys in the kit, each bigger than the last. Each sex toy started off with a rounded tip and gradually widened until it narrowed down to a small stem with a flared base. Wondering how the toys would feel when in use, she placed them back in the box and pulled out the strap-on, inspecting it. It felt like it was at least a couple pounds, and it was nearly as wide as her foreleg. She could only imagine the sort of fun that they were going to have with it, making her tail start to twitch excitedly.

She put the toy back in the box and closed the lid. Setting the box down beside her, she looked around the room, trying to figure out where her marefriend had gone. “Sooo...where’s Dashie?” Twilight thought as she slid out of bed.

Walking over to the bedroom door, she lit up her horn and pushed it open. She walked down the short hallway and down the stairs, standing in the middle of the living room. As she looked at the bay window overlooking Ponyville, her nose was met with the familiar smell of burnt toast. She chuckled as she realized that Rainbow was trying to cook breakfast, and she trotted towards the kitchen door.

She pushed it open and saw Rainbow’s toned cyan flank sticking high up in the air, her head buried in a cabinet as she searched for something inside. With a sly grin, she crept up behind her and laid a gentle kiss on Rainbow’s exposed rear, eliciting a small “eep!” from the surprised mare.

“Hehe, morning Twilight,” Rainbow blushed, pulling her head from the cabinet.

“Morning, Dashie...” Twilight leaned in for a quick kiss. “Why weren’t you in bed?”

“Oh, uhh, I’m making breakfast...or at least I was trying to,” Rainbow said, grimacing as she saw a small plume of smoke rising out of the toaster.

“Have you ever used your toaster before?” Twilight asked as she cocked her head to the side, yanking the burnt bread out of the toaster with her magic. She tossed them out the open window and grabbed a couple new slices and placed them in the toaster. She turned the heat setting from maximum down to a regular setting and pushed the little lever down, pulling the bread down into the toaster.

“Not really, I usually just eat some berries and then I go on my morning flight,” Rainbow replied as she pulled some out of the fridge, pouring a generous amount of the succulent fruits onto each plate. As she tossed the empty container in the trash, the bread popped out of the toaster with a small ding.

Snatching them from the air in her telekinetic grasp, Twilight placed them on the plates and walked over to the table. She set the plates down on and sat down on one of the cushions, waiting for Rainbow to join her.

“Ummm... Twilight, I was kinda thinking...” Rainbow nervously trailed off as she sat down next to her marefriend.

“Yeah?” Twilight asked as they dug into their food, glancing at her the pegasus beside her.

“Well, since we’ve been together for some time now...” Rainbow took a deep breath to calm herself. Slightly afraid of what Twilight’s reaction would be, she hesitantly continued, her ears pinned back. “I... I think it’s time we stop hiding our relationship from our friends.”

“Rainbow, I really don’t know...” Twilight said slowly, her tail nervously flicking behind her. She hadn’t expected this at all. She waited a few moments to collect her thoughts and she continued. “What if they don’t like us being together? For being fillyfoolers?”

“Twi, what’s the worst that can happen?” Rainbow asked. “We’ve all gone through so much together, and something like this isn’t going to ruin our friendship with them.”

Twilight stared down at her empty plate, contemplating what Rainbow had said. On one hoof, it would be nice if they could stop keeping it a secret from their friends, and it would be nice to live without the worry of having somepony find out about your secret relationship. But on the other hoof, she really didn’t want her friends to think poorly of her. How would they even react? Twilight Sparkle, the element of magic, a fillyfooler? What would her family think of her? And what of Princess Celestia; what would she do? Disown her, take her element of harmony away, or send her away from Ponyville?

Twilight silently gasped as she thought of the worst possible outcome. ”What if she does all three?” She shuddered and turned her attention back towards Rainbow. “I’m still a little uneasy about telling them... Is it ok if we push that off for a little longer?”

Rainbow’s ears drooped a little bit; she really wanted to tell her friends about Twilight. "Oh well, I guess we can tell them later... That’s fine with me, I guess.” She picked up their plates and placed them in the sink on top of the other dirty dishes.

Sighing in relief, Twilight stood up and joined her marefriend, giving her a quick peck on the cheek in thanks. “So anyways... I took a look inside your box of toys...” She giggled as she sat down beside Rainbow, remembering each and every toy in vivid detail.

“Oh, really?” Rainbow’s ears suddenly perked up, a sly smile forming on her lips. “Anything in particular you want to try out?”

“Well, I’ve never experimented with anything anal before...” Twilight said sheepishly, wishing that Rainbow would pick up on the obvious hint.

“Really? Well then, I have a treat for you!” Rainbow said, giddy excitement apparent in her voice. As they made their way back upstairs, Rainbow tickled Twilight’s muzzle with her tail, teasing her. They walked back inside the bedroom and shut the door behind them, trotting over to where the white box of toys was laying on the floor. They sat down in front of it and opened the lid, revealing all of the toys within.

Rainbow pulled out the anal training kit and the bottle of lube and tossed them up on the bed. “Alright Twi, I want you to lay on the bed with your hind legs on the floor.” She smiled as her marefriend scrambled to assume the position she had just described. “Okay, we’re gonna start off easy with the smallest one.”

Rainbow pulled the smallest butt plug out of the kit beside her and poured a good amount of lube on it, spreading it all over the slim pink toy with her hoof. The toy itself was a nothing more than a slim rod about a half an inch thick with a very small bulge near the end; the perfect toy for beginners to anal play. She wiped the excess lube onto Twilight’s anus, spreading it all around the puckered hole. She pushed Twilight’s twitching tail out of the way, spread her cheeks with a hoof, and lined the toy up with her opening.

She slowly applied pressure on the toy, pushing just the tip inside her. She let Twilight get used to the new sensation of having something in her rear entrance for a few seconds, and then she pulled the toy back out. She let Twilight recover for a brief moment as she applied more lube to the toy. She placed the toy back at her entrance and pushed a little more inside of her, just over an inch.

Twilight clenched down on the toy, thoroughly enjoying the new sensations from her rear. She had heard that anal stimulation could be thoroughly enjoyable if it was done right, so she had read up on all sorts of tips on how to make the most out of your first time. The book that she had read had recommended a set of beginner butt plugs to start off with, but she had never been able to build up enough courage to go into a sex shop and buy something for herself. Just the thought of having something moving in and out of her ass really seemed to get her going, making her drip a little bit onto the floor, a few drops of her love juices landing on Rainbow’s hoof.

“Getting a little excited, eh Twi?” Rainbow said with a grin, licking Twilight’s juices off of her hoof. She bent down and licked Twilight’s slit, her tongue spreading her marefriend’s slightly engorged lips. She began to toy Twilight’s entrance with her tongue, feeling the heat radiate from it. She pulled the butt plug out until just the tip remained inside, and then gently worked it back inside, all the way to the small bump in the middle just before the narrow stem. She held the toy there for a few moments, letting Twilight get used to the size, and then pushed it all the way in up to the flared base. Twilight moaned and pushed back, trying to force the toy deeper inside her.

Sensing Twilight’s need, Rainbow started gently thrusting the toy in and out of Twilight’s back door, twisting it back and forth, slowly but surely stretching her marefriend. After a few minutes, she decided that it was time to move up to the next size, so she pulled the small butt plug from Twilight’s rear and said, “Ok, Twi, now that you’ve had a taste of the basics, we’re gonna move up to something a little bit...bigger.” She tossed the used toy on the floor and grabbed the next size up. This toy was a little bit larger than the first one, and was about an inch thick. She poured a good amount of lube on it and she placed the tip of the pink velvety toy up against Twilight’s opening, sliding the toy up and down her puckered entrance.

After several teasing strokes, she lined it back up and pushed it in a little bit, making Twilight gasp in pleasure as she felt her anus being stretched more than it ever had before. Hearing her marefriend gasp, Rainbow pulled the toy back out until only the tip remained inside her, and then she gently pushed it back in, going a little further this time.

She repeated this process for several minutes until Twilight could take the toy nearly all the way up to the bulge in the middle just before the narrow stem. “Ok Twi, just one more push and then it’ll be in...” Rainbow moaned softly, applying more and more pressure to the toy. With a sharp gasp from Twilight, the toy popped in, the flared base preventing the toy from disappearing inside her.

“You like this, don’t you, Twi? You like having something in you, filling you up...” Rainbow whispered sultrily, laying small kisses on Twilight’s rear, teasing her clit with a wing, lightly rubbing back and forth.

“Mhmmm...” Twilight moaned softly, clenching down on the narrow stem of the toy. She had heard that anal play was fun and exciting, but she didn’t know it would feel THIS good. Just the feeling of her puckered rear being stretched had started to slowly build up her orgasm, and Rainbow massaging her clit with her soft feathers only helped to push her along.

Wanting to get herself off, Twilight sent a hoof in between her legs, desperately trying to find her clit, but Rainbow quickly slapped it away. “No, Twi! No hooves, and definitely no magic! Now, push the toy out...” Rainbow instructed as she sat back on her haunches, folding her wings.

With a small groan of disappointment, Twilight tried pushing the toy out, but it wouldn’t budge; the thick part prevented it from coming back out. She relaxed for a few moments and tried again, pushing as hard as she could this time, and to Rainbow’s delight, the toy plopped out of her rear and onto the floor.

Quickly picking the toy back up, Rainbow squirted some lube inside of Twilight’s rear and on the butt plug. She quickly slid the toy back inside Twilight, watching as her marefriend took the whole toy in one push.

“Again, Twilight.” Rainbow commanded, idly playing with her own clit. Playing with her marefriend had gotten her extremely turned on, and she couldn’t help but play with herself.

Twilight groaned, her opening slightly sore from the sudden intrusion, but she shut out the small amount of pain and focused only the pleasure. She pushed on the toy again and felt it suddenly slide out of her, a little bit easier than before, only to be stopped by Rainbow’s hoof. Twilight glanced back at her marefriend in confusion, silently wondering why she stopped the toy from coming all the way out, but she soon found her answer.

Without wasting another moment, Rainbow pushed the pink toy all the way back inside Twilight, pushing it as far as it would go, the flared base spreading her cheeks wide. Like she did with the first butt plug, Rainbow twisted it inside of her marefriend, and then pulled it out to the widest point and pushed it all the way back in repeatedly.

“Alright, now let’s make things interesting...” Rainbow murmured, pushing the toy back in until it was fully seated inside her marefriend. She laid down on the bed in front of Twilight, giving her a short-lived but tender kiss. “If you can wear this plug in town for half an hour, I’ll let you do anything you want to me tonight...” she murmured, their muzzles mere inches apart.

“Ok...but I’ll only do it if you do it with me!” Twilight panted, already knowing exactly which toy she was going to pick; the strap-on. She slid off the bed and walked experimentally around the room, feeling how the butt plug moved within her with every step.

Rainbow’s eyes widened in excitement; she didn’t expect Twilight to be so receptive of her challenge. A smile quickly forming on her muzzle, she said, “You’re on!” She pulled the last and largest butt plug from the black box and poured a generous amount of lube on it. She squatted down on the bed and quickly lined the toy up with her rear entrance and sat down it, making the velvety toy disappear inside of her within seconds.

From the other side of the room, Twilight stared at Rainbow in amazement. “How did you do that? It’s taken me nearly twenty minutes to work up to this medium-sized one, and you just took the biggest one in a matter of seconds!”

“Uhhh, let’s just say I’ve had a lot of practice,” Rainbow said as she adjusted the plug’s position inside her, pushing it further into herself until it was all the way inside her. She hopped off the bed and trotted over to her marefriend, nuzzling her cheek as she walked by. “Now come on, let’s get going!”

“Al-alright...” Twilight said, feeling giddy as they made their way towards the front door.

“You know, if you don’t want to do this, I’m completely cool with that; I don’t want to pressure you into something you don’t wanna do,” Rainbow said as they reached the foyer. She watched in amusement as Twilight shifted her hind legs, trying to get the butt plug into a more comfortable position.

“No, Rainbow, it’s ok,” Twilight said, a slight strain in her voice. She stepped forward, pressing herself against her marefriend, and softly whispered into her ear, “And besides, I wantto do this with you...” She wrapped her hooves around her and they disappeared with a pop. A split-second later, they reappeared on the ground directly under Rainbow’s house, and they started cantering side by side towards Ponyville.

After the first few steps, Twilight got used to wearing the butt plug while walking, or as much as one could get used to walking around with something in their bum. As the outskirts of Ponyville came into sight further down the road, a sudden frightening thought burst into her mind.

“Hey, Rainbow? Can you hold on a minute?” Twilight nervously asked, stopping in the middle of the road, her tail covering her rear.

“Yeah Twi?” Seeing her marefriend acting a little skittish, she trotted back to her and asked in a slightly worried tone, “What’s wrong?”

“Ummm...what if somepony sees us wearing these?” Twilight shifted uncomfortably, the butt plug still firmly lodged inside her.

“Oh, you don’t have to worry about that; these plugs were designed specifically to be worn in public without anypony knowing but you.” Rainbow said with a grin. “To be honest, I’ve actually worn this plug a few times on some of the boring cloud-clearing days. It livens things up a bit, ya know?” She smiled reassuringly, draping a wing over Twilight. “Trust me, you don’t have anything to worry about.”

“Hehe, alright; I guess I’m just a little paranoid, is all...” Twilight said, her confidence slowly returning. They started walking down the path once more, and after a minute of silence, she asked, “Say, Rainbow, have you ever had any close calls before?”

Rainbow snickered as she remembered the only time that somepony had come close to discovering that she was doing something kinky in public. “Actually, yeah...” She glanced around to make sure nopony was around, and lowering her voice a bit, she continued. “Thunderlane and I were doing some cloud-bucking a few months ago trying to keep some storm from growing too big. To make a long story short, I was wrestling a cloud in front of him and a strong gust of wind blew my tail to the side, briefly showing that I had something extra back there.”

She blushed in embarrassment as she remembered what happened, her ears pinning back. “I thought for sure that he’d seen it, but when I glanced back to check, he had his head pushed up against the cloud, fighting with all his might. And besides, even if he did see it, he’d probably think it was just part of my awesome tail!” She grinned cockily as she flicked her tail from side to side, emphasizing her point. “Now come on; the half hour hasn’t started yet!”