Slightly awkward first times
Twilight sat in her room, nervous yet excited for the proposal that Cadence had given her a few days ago. The proposal had come in the form of a letter, requesting that the young alicorn visit her in the Crystal Empire for a new type of lesson.
Dear Twilight,
It has come to my attention that your twenty-third birthday is coming up and that you haven’t enjoyed the company of a special somepony in your adult years yet, or even when you were growing up in Canterlot. I’ve talked to Celestia herself about this and she even agrees that it’s time for you to take on a new kind of friendship lesson that you’ll attempt on you own, for the most part. Please visit me in the Empire at a date of your choosing.. I await your earliest response.
With love,
Cadence
Though the letter was brief, Twilight knew what her old foal sitter was talking about. It was also something that Twilight had a hard time dealing with when she was back in Celestia’s school for gifted unicorns. While most of the class had small relationships with others, Twilight was one of the few that took companionship in books rather than ponies. Celestia had brought up the topic plenty of times, but Twilight would always say she wanted to be great with magic and always focused on studying. When she graduated from her school, Celestia was certain that Twilight would have dropped the books and found herself a pony to spend some special time with daily.
Sadly that didn’t happen, and that was part of the reason why Twilight was relocated to the town of Ponyville. Yet, even with her living on her own, Twilight never ventured into the sensual relationship parts of friendship like Celestia had planned for her on the side. Thankfully, after her adventure into the mirror portal, Cadence herself saw a glimmer of hope in the young alicorn as she showed some interest in the new guard. With a few pulled strings, Cadence was able to keep the two close to each other in order for a proper relationship to grow.
Despite their closeness, the two never evolved into true lovers. Despite that Cadence, Celestia, and even Shining Armor thought it was best for Twilight to enjoy the throes of passion in bed with another. While it was always Celestia’s intention to lead her student towards a mate, Shining was pretty adamant about his little sister not spending her whole life stuck in a library. For Cadence, it was all about letting Twilight understand why she married Twilight’s brother in the first place; secretly hoping Twilight would marry one day as well. While they all pushed both ponies together, it was Twilight and Flash that agreed to the night of their own accord. They knew it would happen eventually, but all they needed was a small push from family in order to try and break the ice.
“This is so nerve racking,” Twilight said softly to herself as she waited for Flash Sentry to visit her room. On top of the large bed, Twilight fidgeted anxiously wondering how much longer he was going to take. Her eyes would scan the room, trying to find something that she would distract herself with but after a few seconds of looking around, her ears perked up at a sound coming from behind her door.
Twilight stared at the large doors and listened intently as she started to hear the sound of Flash’s hoof plates echo down the crystal keep. Eventually every step that got closer, Twilight’s heart raced more and more. The more she stared at the door, the longer it seemed for Flash to get to it; Without warning, the sound of a second set of hooves greeted her ears. The steps were quick, yet delicate; Twilight knew it was probably Cadence checking up on her. Both visitors stopped at the door and exchanged a few words with each other. Curious to hear them, Twilight moved herself close to the bed’s edge in order to listen in. Sadly, before she could, the doors opened out and Flash walked in with a nervous look on his face. Looking up, Twilight saw Cadence staring at her with a soft, reassuring look on her face before she turned around and walked down the hallway.
“Hello, Princess,” Flash said quietly as he closed the door behind him and removed his helmet and armor.
“Hi, Flash. I take it you’re as ready as I am?” Twilight answered back. She tried desperately to avoid sounding as nervous as she felt, and failed.
“As… ready as I’ll ever be,” Flash said with an awkward smile on his face as he slowly trotted towards her.
Even though both were nervous for their first time, they were also very excited. In fact, Flash took it upon himself to learn proper ways to please Twilight when the time actually came for him. Flash was sure he was well read enough to pleasure his princess.
“Shall we get right to it then?” Flash asked as he came to a stop at the foot of the bed.
Twilight hesitated, not sure on how the act of lovemaking was properly done. Even with the books she read to help her; her mind was going blank with instructions. Seeing that she was unsure of what to do, Flash made the first move and craned his neck up to kiss her on the lips. In her distracted state, Twilight didn’t register his movement until his lips were on hers. Feeling the somewhat dry lips connect, Twilight’s wings fluttered slightly and her eyes went wide. Kissing was something they had done plenty of times, but it felt more passionate this time around. Relaxing herself, she closed her eyes and moved her tongue around his mouth, letting them dance around for a few long seconds.
Wanting to impress her a bit more, Flash pulled himself up onto the bed, causing her to fall back and rest against it. The kiss broke briefly but Flash quickly dove back into her lips.
Oh Celestia, he’s so eager, Twilight thought as her cheeks blushed more.
Her thoughts were confirmed when he finally broke his kiss and started on her neck. As eager as he was, Flash was nervous he was taking things too quickly in his mind. From what he read, taking it slow for the first time was something that wasn’t recommended, yet he was still unsure thanks to the book being horribly outdated. Yet so far his eagerness was paying off for him. Flash was able to pick up soft and gentle sighs coming from Twilight, and he relaxed slightly; he was clearly doing something right, at least. The book said to start with a long kiss, then slowly he moved kisses down her body and he eventually came to the first major part of pleasuring a mare. Still kissing, Flash moved from her neck to her chest and eventually found his way between her legs. The more he moved down, the faster his heart beat, knowing her pussy would soon be in sight.
For Twilight, the feeling of his lips caressing parts of her body was greater than any book could possibly describe. Though her mind was blank, her body moved on it’s own accord; her legs slowly parted for him to have perfect access to her nethers. Looking down at his mane, Twilight watched him continue his way down until he came to a sudden halt.
Oh man, this is where that book said to be… adventurous with my tongue. Flash’s mind raced as he stared blankly at the dry pussy in front of him. Though he had seen it plenty of times through shifty eyes whilst on duty, seeing it up close made him nervous. Flash slid part of his body off the bed while keeping his head between her legs. Feeling him stare at it without saying anything made Twilight feel nervous.
Oh gosh, does it look unfitting? Maybe I should have trimmed that little patch of hair that’s growing there… Twilight’s nerves didn’t slow down at all; her mind continued to process ideas as to why he was still staring. Her body started to ache and her wings started to flutter open as well. Her body wanted, needed – almost craved – to be touch by him, yet her mind said otherwise. By the time she had processed a fair amount of thoughts, she wondered if she needed to guide him, telling him she was truly ready for him.
Still a bit nervous, Twilight slowly placed her hooves on both sides of the Flash’s head, which caused him to lean forward into her. As his head got closer, her scent got so strong it felt like all the oxygen had left the area. While she was dry, it almost looked like it was trembling and screaming to be pleasured. Flash slowed his breathing and Twilight shivered as the hot air brushed against her pussy. Twilight almost felt embarrassed by the way he was looking at it; his eyes were wide, yet focused on what he was told to do for her. While he was the newest guard, assigned to protect Twilight’s room by Cadence herself, he was eager to be one of the few that got the pleasure of helping a new princess.
Before he could push his face right into her, she pushed his cheek away ever so lightly, showing she was a bit hesitant for the act to come. He looked up at her and gave her a soft smile, which comforted her slightly. Flash waited patiently, even though his tongue almost felt like it was going to melt in his mouth. He wanted to dive in and just devour her, but he wasn’t an experienced lover. He was told to go at her pace and he never disobeyed orders. With a deep sigh, he spoke up to her.
“Whenever you feel ready, Twilight,” he said quietly as he stared into her eyes.
Twilight remained silent, but took a deep breath and nodded her head. She was still unsure, but she knew she wouldn’t last the night without a male.
Twilight waited as he got ready to pleasure her and closed her eyes. Flash leaned his head ever so slowly into her. The uncultured and restless stallion inside of him was screaming at him to lurch forward and make her moan in wild passion; he wanted to hear her beg for it to never end and just enjoy the small princess for himself. Yet the proper gentlecolt in him just wanted to enjoy the mare’s body in all its beauty. The way her curves looked with their elegant shape, and just how soft she felt when he rubbed his hooves against her sides and slowly moved towards her tender ass. Twilight let out a few more deep, relaxed breaths as she felt his nose brush ever so slightly against her wetness.
“Please,” she whimpered.
That was all he needed to hear. Without wasting another second, he moved his tongue out and let the tip of it trace around the outside of her folds, taking in the taste of flesh and her arousal. She let out a soft gasp as she felt his tongue gently lick at her nethers; her already aching wings were now to the point of throbbing, and she almost wished she didn’t have them in the first place. She was well informed on how sensitive wings are when pegasi get aroused, and now had to deal with it herself.
Refusing to give her a moment’s rest, the eager stallion did his job tracing the tip of his tongue along the outside of her folds, his vision spinning from the overpowering fragrance of her sex. Letting her scent guide his actions, he started to press his tongue harder into her while slowly moving up to her clit. As his tongue hit the mark, Twilight let a soft moan which almost made the aching penis underneath Flash’s stomach cum prematurely.
Wanting to hear her get a bit louder, he put more eagerness into his licks, tracing circles around her clit. Every lick made her body tremble and made her hips start to slowly rock back and forth in time with his actions. She may have been a princess, but now she felt like Flash was taking control of her in his own way.
“Mhm, I thought you s-said this was your f-f-first t-time,” Twilight stammered out, barely able to form words.
“Beginners luck, Princess. Or maybe I’m just that skilled,” Flash replied with a chuckle as he pulled away for a second, until he came back in.
Though he spoke, it was like his motions never stopped. Going back to licking her clit, Flash put more movement into his tongue. Twilight could only continue to moan as she found his tongue moving up and down her vagina, circling around her clit before pressing down on it. The movements of his tongue seemed so effortless that she refused to believe it was his first time.
"I think you’re bluffing,” Twilight said quickly, spewing her words before a moan escaped.
“Oh? A–mmph!” Flash started to say but was stopped by Twilight pushing his face back in to keep going.
Though her push felt stronger than it should have been, Flash resumed his tongue work as he felt her hooves move against his cranium in slow circles. Though he was still eager to keep lapping, Flash was finding it harder to maintain a proper composure. His erection twitched and started to hurt from not being touched, and he wanted to stick it so badly into her. Not able to take the torment anymore, Flash stopped licking and rested his head against her body until she broke from her allured state.
“What’s wrong? Why did you stop?” Twilight asked, her voice on the border of concern and frustration.
Instead of speaking, Flash pulled his body away and stepped back. Twilight wondered what was up until she gasped as she saw his erection come into view. In her pleasure, she completely forgot that he had to get off as well, and she knew it was going to end up in her very soon. Twilight said nothing for a few seconds, wondering on how a real cock differed from a fake one. No doubt it wouldn’t feel like the plastic she was used to, and actually move without her guiding it, yet the realness of it scared her more. The way it twitched underneath him made it look like it had a life of its own; her mind wondered if he would be considerate enough to go at a slow place rather than just rolling her on her stomach and rutting her senseless. The thought of it piqued her interest slightly, but noticing his sad expression, she finally spoke up.
“I take it… that you want to put it inside of me?” Twilight asked, the words almost sounding like a nervous pornstar reading straight from the script.
The expression left his face and quickly got turned into a smile as Flash nodded his head feverishly. He was ready to hop on the bed and get right to it, but seeing her worried expression, Flash moved closer.
“You looked worried, Twilight. You don’t have to worry about being hurt, I’ll go as slow as you want,” Flash said as he pulled his body onto the bed and nuzzled her cheek.
Twilight sighed deeply, her eyes closing as she tried to calm herself down. Sure, it looked big, intimidating and scary, but she was just over-thinking it as usual. As soon as she felt his rock hard cock inside her, she was sure she’d enjoy it to its fullest qualifications and length.
“F-fine, just… just be gentle, okay?” she asked, her arousal down in her nethers begging to be pleased by something. Flash’s dick would definitely do.
Nodding, Flash reached for her sides, ready to flip her over to the crux of a first time lover’s position: doggy style. But Twilight caught his hoof and shook her head. “I’d much rather do missionary position, if you don’t mind. It’s just that I’d like to… to… to look at your face while we’re doing it,” she said with an embarrassed blush appearing on her cheeks.
Flash smiled fondly and nodded his head, helping her to relax on her back and spread her throbbing wings to relieve tension there. On her back now with Flash above her, Twilight awkwardly spread her legs, unsure if any formality was involved in asking a stallion to fuck her silly.
Still smiling, Flash played along with her cute, nervousness. He helped spread her legs wider, giving him a grand and glamorous view of her dripping cunt. Smacking his lips at the reminiscent taste he last had of it, Flash’s dick throbbed to be enveloped by those lips right away.
“Okay now, easy does it…” Flash muttered, grabbing a hold of Twilight’s lower hooves as he leaned a bit lower to position the tip of the dick over her vagina. His head brushed her clit ever-so-slightly, eliciting a moan of approval from Twilight. The mare was hugging herself hard, afraid she would burst at how much she wanted to be penetrated. The gentle treatment she asked for earlier was replaced by a need; a desire that couldn’t be quelled until that huge package Flash toted around was deep inside her. But unfortunately for her, all he was pulling off was light prodding at her pussy, never going more than an inch inside her.
“Mmhmm… ngh, just stick it into me already!” Twilight begged, biting her lower lip hard at his teasing. Normally she wouldn’t make such an outburst, but normally she wouldn’t be drooling uncontrollably either.
Blinking at her sudden demand, Flash complied to his princess’ orders. Grunting, he pushed forward, entering her inch by painfully slow inch. Twilight was in a frenzy as he penetrated her, legs shaking uncontrollably and eyes closed tight.
Giving his erection a hard push, Flash planted the full length inside of her, causing her to give off a slight whimper of discomfort.
“You okay? I didn’t mean to hurt you,” Flash said.
“It’s alright, it just hurt for a second,” Twilight replied as she looked at his face.
“Are you sure you want me to continue?” Flash asked, still unsure if it would be right to rut her if it was hurting her.
“Yes, you’ve got me pretty aroused right now, and I don’t think you want a sexually frustrated mare, now do you?” Twilight answered back as she put a small smile on her face before she gave his nose a small lick.
Flash smiled back, happy to see she was still good to go. Seeing her smile, Flash refocused his attention on moving his hips accordingly. His thrusts were short, just fast enough to give Twilight the pleasure she was craving. Not wanting to disappoint her lover, she raised her hooves and wrapped them around his muscular neck before pulling him even closer to her. She closed the distance by wrapping her legs around his midsection, making sure the feeling of being stretched to the limit never left her.
“Can’t have that now, can I?” Flash said with a smirk on his face as he gave her a particular hard, yet satisfying thrust. “Hope I’m able to please you enough.”
Twilight responded by resting her head into his shoulder and closing her eyes in order to focus more on his moments. Feeling her warm breath caress his neck, Flash grunted and pulled his cock out of her quivering pussy a good few inches before he rammed it back in and started to repeat the deep, thrusting motion. Twilight loved the feeling, and though she continuously bit her lower lip, she wouldn’t have traded it for anything. She felt wrong for enjoying so much, yet the continuous motion of his dick grinding against her walls offset that feeling completely.
Every motion pushed the once-virgin mare into a higher state of bliss. Her moans were slowly picking up and Flash’s thrusting started to quicken its pace. Twilight, knowing she was starting to get close, dug her hooves into his back, whispering sweet nothings into his ear. Every word she spoke only made him push that much harder, and the sturdy bed started to creak from the power of his thrusting. Her words continued and were accompanied by the feeling of warm lips pressing into her neck.
“Flash… I’m so close. Just a bit more,” Twilight spoke softly, feeling her body tighten and tense up. Her legs quivered in anticipation for the big pay-off she knew would accompany the rising feeling of needed release in her nether. “Fill me up when you finish.”
Flash silently nodded, knowing no words were needed for a moment such as this. His actions spoke louder, after all, and Twilight’s moans evolved into screams of ecstasy. Grunting with another deep thrust as he pushed Twilight’s walls to their newfound limits, he knew he didn’t have much more endurance to hold out.
Wanting so desperately to finish at the same time as Flash, Twilight held out the best she could manage, but her inexperience handicapped her endurance. With a final shrill shriek, Twilight’s legs convulsed as she thrust her hips upward, her orgasm rocking her body with hormones and a need to unload herself.
Luckily for Twilight, Flash didn’t have much fuel left in himself either, so now was as good as ever to pump his load in her. Thrusting just as she did, Flash managed to reach the full length of his cock inside her tight pussy, releasing an incoherent groan as he came.
For the first time ever, Twilight knew what it was like to be filled by a stallion’s seed. It felt like hot chocolate was being poured into her vagina, so warm and gooey that she couldn’t decide whether she enjoyed it or not. But Flash’s continuation of his thrusting to empty his dick of all his semen made her change her mind quickly, and she enjoyed the sensation of the sticky mess inside her.
“O-oh Flash, this is… wonderful,” Twilight sighed, still holding onto her lover as he finally stopped pounding her pussy. Both ponies were covered in a light sheen of sweat, their combined sexual juices dripping on the bed. With an exhausted sigh, Flash slowly pulled his deflating erection from her winded body. With a soft squishing sound, he left her body and rested against the bed before it slowly made its way back into his sheathe.
“I’m glad I can please you, Twilight,” Flash said quietly, nuzzling her cheek with affection before he gave it a kiss. “So, when can we do this again?”
Twilight chuckled at him before she closed her eyes and pressed her lips against his. Both held their lips against each other, slowly letting their tongues connect and dance around in a small act of trying to dominate the other. Finally they broke their kiss; a single strand of saliva connecting them for a second before it broke and fell onto Twilight’s fur.
“Oh, we’ll be doing this a lot,” Twilight said as she wrapped her hooves around his neck and gave him one last kiss. You can be sure of that.