Captain's Orders

It only took about ten minutes for Aileron and Cross to get back to their hotel room, but by the time they were halfway there, Aileron was getting a bad feeling from his future team partner. Considering she had ignored his presence the entire way back, he wasn't sure if she was just trying to act like he didn't exist or didn't even care that he was there.

"So..." he asked, trying to break the thick layer of ice that had formed between them on the flight down to the city, "how was practice for you?"

"Fine," Cross replied coldly, not bothering to look at Aileron when she said it.

Aileron returned to staring ahead and didn't try to talk to her again for the rest of the trip. As such, the silence between them increased with every step until he couldn't stand it anymore.

Eventually, it became too much to take. "What's your problem with me?" Aileron asked Cross, stepping in front of her to make her stop. "Seriously, you've been ignoring me this entire time."

Cross glared at Aileron and practically growled, "You've just been waiting for this, haven't you? Well I can work through this, and you're not getting any, you pervert."

"You've got to be kidding me," Aileron sighed, finally understanding where things had gone wrong between them. "So you think I'm just the stereotypical stallion that's only after a plot view and some action?"

"I caught you staring at my plot earlier today, so yeah, pretty much."

Aileron couldn't help but shake his head at her assumptions based on what he'd done early in the morning. Had she known him better, she would have realized that he didn't completely wake up until after being up for at least fifteen minutes. "Will you just forget about that already?"

"Why should I? You're just like all the other stallions that try to flirt with me..."

"Look, it was still early for me, and you had your plot up in the air in my general direction. What else could I have done?"

"You could have at least not looked!" When she realized she had been yelling, she cupped a hoof over her mouth and muttered something incoherent. "I swear I didn't mean to yell there," she stated, backing away slowly as if she were afraid. "I don't know what came over me."

Aileron wrapped his foreleg around her and told her, "It's fine. I think I know the problem."

Cross' mind raced with theories of what Aileron may have come up with based on her reactions to what he'd done. For a second, she almost thought that he had discovered her secret, but then she realized that the truth was so far out in left field that he would never think of it.

"You're not into stallions, are you?"

"What?!" Cross exclaimed, shocked that he would ever accuse her of that. "Why would I be a fillyfooler?"

"Well... you were acting like you hated stallions. What else was I supposed to think?"

On the inside, Cross was only half angry at Aileron for his idea. How was he supposed to know what was really going on? Nevertheless, she threw his foreleg off of her and stepped around him, heading in the direction of the hotel.

"I'm sorry, okay?" Aileron apologized, running after her. "I totally didn't mean that."

Cross turned around to face Aileron and offered, "Look, can we just agree to get this over with as soon as possible? That's the only thing I want."

"Sure."

With the issue settled, the two of them continued down the street until they reached their hotel- a rather large, three story marble building toward the edge of town. Luckily, Cross' room was on the first floor, meaning that they had less time to argue with each other on their way there.

When Cross flung the door to her hotel room open, she seemed to be moving slower than before, almost as if she was thinking a bit too deeply about what she had agreed to.

"Are you sure you want to go through with this?" Aileron asked, earnestly considering not forcing her into anything she didn't want. After all, he didn't want to ruin his image anymore than he already had from earlier. That would only make this night even more awkward.

"Not really, but I guess I can if you want to."

While Cross flopped onto the bed, Aileron checked the small icebox in corner, having realized just seconds before that he hadn't eaten since lunch. Surprisingly, there wasn't much in her refrigerator; he would have expected there to be more for her filled out form.

Though she wasn't exactly fat, there was definitely a tiny layer of pudge around her flanks, even as a stallion. It really only added to the amazing view from behind. All it did was bolster the feelings that Aileron had for her.

"Sorry I don't have anything in there," Cross apologized, sitting up from where she had been lying on the bed. "I haven't had time to get anything."

"It's fine," Aileron replied, heading over to the bed. He flopped over onto the surprisingly comfortable mattress and turned over so that he was facing Cross directly. "So what do you want to do?"

"I don't know... how do you usually start?"

She had just trapped him in a corner; if he admitted that he'd never done it before, she wouldn't trust anything he said afterwards. If he acted like he did and screwed up, she would probably kick him out. "Well, I usually start off with a kiss, I suppose. If you w-"

He was cut off as Cross' lips forcefully locked against his.  Though Aileron could tell she was a novice, it was still one of the better kisses he had received compared to the various marefriends from his past.

When he realized she had pulled away, he blushed and brought his head back. Their eyes locked, and something seemed to pass between them.

This time, Aileron pulled her into a tight kiss, and as her tongue slipped between his lips, he realized that she was much better than he had thought she would be. His own tongue wrestled with hers for dominance, and soon he felt a strangely warm feeling coming from between his hind legs.

As her leg brushed against the warm spot that cropped up, Aileron couldn't help but shudder. Whatever she had just done, it had felt amazing, and he only wanted more of it.

However, when he glanced down between Cross' legs, he noticed that nothing had happened. Her member was still fully inside the sheath and didn't show any signs of coming out. For some reason, he felt almost guilty at getting pleasure without Cross feeling it.

Before she could react, Aileron slid down to the sheath and gave the end a lick, finally feeling where the tip was deep inside. Though it seemed a bit strange that she wasn't getting aroused at all, he set out to make her get there.

Using the knowledge he had gained from watching his older sister and her coltfriend, Aileron used his wings to massage the two orbs hanging beneath the sheath, causing the tip to pop out. Though he knew it would feel weird, he took the tip of her cock into his mouth and slowly caressed it with his tongue, causing it to become even  more erect than it was before.

As more and more of it was revealed, Aileron took each extra bit into his mouth, bobbing up and down on her surprisingly large erection. Each time it seemed to get even longer, and by the time it was almost at the back of his mouth, he was worried about it growing any larger.

After it became too thick to breathe consistently, Aileron pulled back and took in the sight of Cross' incredible girth. Though it wasn't as long as he figured it would be, her member made up for its lack of length by being incredibly thick.

Aileron gulped as he thought about the idea of it penetrating him. However, if the wet feeling between his legs was anything to go by, the idea of having her new stallionhood thrust inside his moist petals was more arousing than frightening.

Those feelings almost disappeared when he looked up at Cross and saw her wincing. "What's wrong?" he asked, afraid that he had done something wrong.

"Nothing..." Cross answered, finally opening her eyes and looking down at her full erection. Though she brushed away the tear that formed at the edge of her eye, Aileron managed to notice it.

"Something's wrong; I can feel it. Just tell me."

"Let's just get on with it, okay?"

Though he wanted to see what her problem was, he had to deal with the carnal desires nagging at his mind first. If he didn't do that, he would be more interested in the mass of stallion-flesh beneath him than what she was saying.

"Alright, but you're on top," he said, turning around and raising his tail so that his marehood was fully visible. Slowly, Cross switched from laying down to standing behind him and clambered on top of him, her erection dangling just beneath Aileron's dripping vagina.

As Cross bucked her hips forward multiple times, missing her target, she eventually hit the crease between his hip and leg, and he faltered to the side, falling sideways onto the mattress. "If you need help, just tell me," Aileron offered, getting back up into a standing position and raising his plot into the air in front of her. "It's harder than it looks."

This time, when she mounted him, Aileron could feel the tip of her member at his soaked entrance. As she thrust forward, he felt as if she was going to rip him apart from the inside out. Her incredible width spread him apart like nothing he ever could have imagined, making him feel as if he'd just taken an entire tree into his new genitalia.

As she continued to push forward, Aileron whimpered into the mattress as his entire upper body was pressed against the downy surface. With each consecutive inch that entered, he felt even more of his body spread out, leaving an increasingly full feeling behind- one that wasn't entirely painless, but not exactly painful either.

Eventually, after what seemed like forever to the stallion-turned-mare, Cross stopped pushing and pulled back, allowing the walls of Aileron's new marehood to relax. However, before he could compose himself, Cross thrust back inside, making his eyes widen as his insides stretched out again.

Aileron moaned into the pillow as Cross began to develop a rhythm, pumping in and out of his moist slit, forcibly stronger with each push inwards. By the time he felt a strange pressure rising deep within his loins, each successive thrust was mostly painless, having faded into pure bliss minutes before.

He gasped loudly when Cross bucked her hips forward harder than usual, hitting something deep inside him that felt amazing. Without warning, Aileron found himself on the brink of climax.

He cried out louder than he ever had as his insides exploded in a feeling of passion, and fireworks filled his vision. "Oh my Celestia..." he murmured, as Cross continued to pump in and out of his convulsing love tunnel.

However, Cross showed no signs of stopping, even as her stallionhood spewed strands of hot cum all over his insides. Aileron only knew one way to get her to stop, but it was dangerous to do.

When Cross had pulled back for a powerful push forward, he quickly slipped off and fell to the bed, allowing a few droplets of her cum to dribble out of his wider opening. As if proving his worry right, Cross fell forward when she realized that he had moved, unable to stop the force she had put into her movement.

As the two of them disentangled themselves from each other, Cross glared at Aileron with a look that could have killed. "Why the hay did you do that?" she asked, scowling at him.

Aileron leaned away before answering, "Well, you didn't seem like you were stopping."

"Of course I wouldn't have stopped! Do you have any idea how good that felt?"

When she said that, something was triggered in his mind. It was almost as if she had never gone through it before. Maybe he would be able to admit that he had been a virgin before they had done it.

"Well, I was a virgin too... That was just a little much."

Cross shook her head in disappointment and exasperatedly explained, "That's not even close. I've done it before, I just-" At that point, her words dwindled off into incomprehensible muttering.

"What is it?"

"I didn't have any feeling down there until now, okay?" Cross said, as if trying to rush her words fast enough that he wouldn't understand them.

Aileron's jaw dropped faster than anypony else's ever had. "Wow..." he whispered, taking in all of the effects that would have on a mare who had obviously gone through the act of intercourse before. To not be able to feel any of it would be a horror beyond anything ever experienced. "I'm really sorry about that. If it helps, you can do it as long as you want."

Unfortunately for him, Cross was still fully erect, and she told him, "You'd better be serious."

As much as he was sure he'd be sore by the end of the night, he had to go along with the deal he'd made. So Aileron raised his plot in the air again and prepared to take in her larger-than-usual erection for the next few hours until one of them fell asleep.

"You know... I might want to try something first," Cross admitted, setting Aileron on edge. With how much she had enjoyed rutting him senseless, he had no idea what she was going to try.

However, when he felt her hot breath on his still-sensitive slit, another shudder passed through his body. On the outside, Aileron may have appeared collected, but on the inside, he was practically screaming for Cross to get on with it so he could be done with the whole ordeal.

Those feelings vanished as Cross took her first lick, catching Aileron's engorged clitoris with the tip of her tongue.

His whole body tensed up as she kept lapping at his soaked pussy, only increasing his already high levels of arousal. With each subtle lick, Aileron felt himself slipping closer and closer to climax.

When Cross pulled away, Aileron almost felt deprived. As such, he whirled around to her and told her, "You're not doing that to me."

"I'm sorry," Cross apologized, being as sincere as possible. "I just can't keep going on. It feels too weird."

Though he was still mad, Aileron could see her point. Taking her new stallionhood into his mouth had been strange at first as well, though he had obviously adapted to it better than she had.

"It's fine, I guess," Aileron comforted, wrapping his foreleg around Cross' barrel. As she melted under his touch, he glanced down at her somehow still mostly erect member. It would only take a little to get her aroused enough to give him the feeling of it pumping back and forth inside his dripping marehood again.

Without giving her any warning, Aileron slipped his hoof down between her legs, rubbing it gently up and down the shaft that she was still sporting with pride. If her guttural grunts and moans were anything to go by, she seemed to be enjoying the feeling of his hoof stroking her most private of parts.

While Cross pulled him into a passionate kiss, Aileron kept working on her erection, until he noticed that she was lightly bucking her hips forward, trying to add a whole new level of feeling to what he was doing. At that point, he decided that he had tortured her enough, and aligned her love rod with his soaked slit.

In one quick movement, he impaled himself on her member, creating the same full feeling that had sparked so much enjoyment from his first time. He couldn't help but gasp loudly and moan into her mouth as her erection reached places he hadn't imagined being stimulated.

Aileron somehow pulled himself up off her shaft, against the feeling of euphoria causing him to become weak with pleasure. However, when he reached the tip, his leg collapsed and he fell back down, filling himself to the point of absolute bliss.

After that failed attempt, he quit trying to get up and simply let Cross lie beneath him with her erection shoved deep into his love tunnel. And yet, as if she was conspiring against him, she kept bucking her hips forward slightly, hitting something that made his entire body shudder.

"Could you flip over?" Cross asked, brushing her lips up next to Aileron's ear before nibbling on the very tip. He silently complied, though something that sounded like a whimper escaped from between his lips as her girthy stallionhood shifted from side to side inside him.

Cross almost came then and there because of the way that the walls of Aileron's marehood gently massaged the entire length of her erect cock. Still, she could tell that he was nowhere close, and had to resist before she came inside and ruined the feeling for him.

In a last ditch attempt to distract herself from the way her new equipment was feeling, she bit down on her foreleg. Just as she wanted, the pain from her self-inflicted wound took over for a second, allowing Aileron to lie back with both of them in the perfect position for a hard rutting.

But before she got to that, she had to do something to thank him for flipping over. If his hardened grimace was anything to go by, it had hurt more him for than her, and he had to be rewarded for persevering.

From her new position, she could easily penetrate again if she had to, and the thought of toying with his body had run through her mind just seconds before. Then she realized that doing that would amount to nothing better than torture for him instead of a gift. If she couldn't do that, she was having trouble thinking of what would make a fitting present for taking it like the stallion he should have been.