“I'm just nervous, you know?” Scootaloo looks up at me with her big, round eyes, and I imagine that as a filly, she probably got a lot of adults to do what she wanted just by flashing those babies.
I put a comforting hoof on her shoulder. “I know, Scoots, and you've got every right to be. It's a big step, sex.”
She goes on as if I haven't said anything. “I mean, what if I do something wrong? What's he gonna think of me then? What if he doesn't like it? What if-”
This time, my hoof in her muzzle makes sure she'll pay attention. “Listen, kid, sitting here worrying about that kinda stuff isn't gonna solve anything. Got it?” She nods. “Good. Now, Rumble's a great guy, and I've seen you two together enough to know that nothing – and I mean nothing – is gonna come between you two. If he seriously decides to dump you because you were a bad lay during your first time, well, then I'll eat my flight suit.”
She chuckles, and I think she's lightening up a little bit. Her next words tell me otherwise. “I know you're telling the truth, Auntie Spitfire, but it's still scary.”
I try to disarm the situation with a smirk. “Scoots, would you believe I was a nervous wreck before my first time too?”
“You?” she says with a disbelieving face. “But you're the second most fearless pony there is!”
“Second most?”
“Behind Rainbow Dash.”
I laugh, but not at her. Scootaloo's hero worship of the newest member of the Wonderbolts was how I met her in the first place; she was practically beside herself to meet the pony that her idol admired almost as much as she did Dash. What struck me most about her was her wings. At her age, most fillies would have developed longer, sleeker wings, and they'd probably be doing at least a little bit of flying. Hers were still small and stubby, and the best she could pull off was a little hover. It was a birth defect, but the kid was all smiles all the time. I saw why the first time I watched her hop on that scooter of hers and go tearing down the road. While her wings couldn't generate enough lift for her to really fly, there was a lot of power there, and she could pilot that little machine like nobody's business.
I got to know her through Dash, but she's taken a liking to me too. I made sure to say hey to her after our shows when she could come along, and I'd always ask about her when Dash came back from a trip to Ponyville. The kid has a lot of spirit, and I have a lot of fun hanging out with her. If I could have figured out the logistics of including a scooter in some Wonderbolt shows, I totally would have tried to bring her in so she could show off her stuff, but I don't think she would like that as much as just talking and laughing and chatting with me and Dash. We're like three generations of crazy daredevil mares, each with our own war stories to share.
When she started going out with Rumble, I could tell right away that it was gonna be something special. Since I'd been around the block a few times myself, I started giving Scoots advice to help her along. She listened to what I said (probably against her better judgment), and I got to watch her grow up right before my very eyes. Love was a very new thing for that rough-and-tumble youngster. No matter what she wanted to talk about, she knew she could go to either me or Dash for a little encouragement and a few jokes.
It started to be a pretty regular thing; on days when I didn't have a rehearsal or a show, I'd meet up with Scoots and we'd discuss the latest developments in her relationship over lunch or coffee. As much as I can't stand kids sometimes, this filly was different. She wasn't trying to constantly crack jokes in order to win me over, and she was willing to sit and listen to me, even though compared to her, I'm pretty much an old-timer. I really felt that way when she started calling me “Auntie Spitfire.” I guess there are worse nicknames I could have ended up with. In spite of the whole “Auntie” thing, though, I gotta say that I respect the kid a lot.
Some things have led up to tonight, however. You see, last week, we met up for our usual lunch date, but I'd never seen a smile that wide on Scoots' face before. I didn't even get a chance to ask her what was up before she did a backflip – catching an impressive amount of air – and told me all about how Rumble had finally gotten around to popping the question. Of course she said yes, and I congratulated her, but as our conversation went on, she started to act less like somepony that had just been told the most wonderful news in her life and more like her nerves were completely shot.
As it turns out, Scoots had agreed to save herself for Rumble. I was real proud of both of them; took a lot of courage and patience to make that kind of commitment. Scoots, on the other hoof, was way more nervous than she needed to be about doing it. Sure, the three of us had talked about sex when she was a little older; like I said before, war stories, right? Anyway, while she knew what to do, she was still driving herself right up the wall worrying about whether or not she was gonna be any good in the sack. That's why she came over to my house tonight, so she could have a frank discussion with her Auntie Spitfire.
Now, when I look at her, I can see that the fear is still there in her eyes, so I share my story. “It's true, kid. I had no idea what I was doing, so I just winged it...um, no pun intended. He and I took it slow, figured out all the details. Eventually, we had ourselves a grand old time, but it took work and practice. It's the same way Dash got into the Bolts, and how you learned all those sweet moves on your scooter. Hard work and practice. And don't worry if your first time isn't all sunshine and rainbows and crap like that; he's probably just as nervous as you are about the whole thing, so it'll be a learning experience for the both of you.”
She's still frowning, but I can see the gears turning. What she says next, though, certainly isn't what I expected. “Could you...teach me?”
I freeze, and my mouth hangs open for a second before I sputter out, “Huh?”
She stares at me with those big, innocent eyes. I can already feel my walls crumbling down. “I know it's not gonna be perfect, but I still want to know what I'm doing the first time. That's one of the reasons I came to you and not Dash. I know you could teach me, probably better than she could.” She giggles. “Well, that and the fact that she's out in Fillydelphia all week.” What she's suggesting is a little absurd, but unbelievably (even to myself), I'm already starting to consider it. Damn those eyes. She goes on, “I love Rumble, and I want him to have a good time with me; I think the only way that can happen is if I have a little practice, like you said.”
“That's not exactly what I meant, kid,” I say.
“I know,” she says with a little smile that melts me even more. I always thought she was cute, but I've never looked at her like that. Now, I see what an attractive young mare she's grown up into, and I know that Rumble is going to be one lucky pegasus to have her. She goes on: “If you don't want to, that's fine too, but I really would appreciate your help. So will you teach me, Auntie Spitfire?”
Seriously, damn those eyes...and that nickname. A hundred doubts race through my mind. Don't get me wrong, I love this kid as a friend, maybe even like a little sister, and I'd do anything in my power to help her out. But this? I think that might be a little far, even for me, and I've had a few mares in my day. There's something in her face, though; I feel like if I don't do this for her, she might look elsewhere. I'm not saying she's gonna sleep around or anything, but I can tell this isn't something I can just explain away. If there's one thing Scoots picked up from me and Rainbow Dash that I didn't want her to, it's a tendency to be stubborn as a mule.
“Scoots, listen close, all right?” She nods. “What you're asking is...well, a little unusual.” Her face falls, and I quickly go on. “I didn't say I wouldn't do it, okay? I get the feeling that this is an itch you're gonna keep on scratching if I say no, and I'd rather you get a lesson from somepony you trust. Scoots, it's really sweet that you want to make a good impression, and I'm willing to help you, but that's it, got it?”
She beams. “Oh, thank you, thank you!” She throws her forelegs around me in a tight hug, and I give her a soft, awkward one in return. “You don't know how much this means to me, Auntie Spitfire.”
“Y'know, kid, I think I just might.”
***
Several minutes later, I'm in a position I never thought I would be. There's a strap-on hooked up around my hips (Want to know why I have it? All I have to say about that is “war stories.”), and I've got my front hooves on Scootaloo's back, just above her tail. She's lying down on the bed beneath me, her stubby wings flapping erraticly. This will be her first time experiencing penetration from another pony, and I'm just as much of a nervous wreck as she is. This is for her and Rumble, I remind myself, and I stroke her back lightly. “Scoots, you doing all right?”
Her voice is breathy. “Yeah, I'm okay.”
“Okay, now listen up, if it hurts or anything, you just feel free to tell me to stop, and I'll stop. Got it?”
“Yeah,” she says in a faraway tone. That probably has something to do with the teasing I've already done; after all, I'm not just gonna go in there dry. Her little pink slit is already moist, both from my light tongue work and her own building arousal. I can smell it, and it's starting to turn me on.
Right now, though, I need her to focus. “Scoots!” She tenses up beneath my hooves. “This is important. I don't want to do anything that's gonna cause damage or hurt you, all right? And it's gonna be the same way with Rumble. If you're uncomfortable, don't just grin and bear it; say something, or you might end up in bad shape. Do you understand?”
She looks back at me, her eyes not quite as glazed-over as they were before. “Yes,” she says intensely, and I know she's serious. It was weird for me to use that motherly tone, but I care about this kid. Now, I'm sure that she's ready.
“All right,” I say with a soft smile, dropping the disciplinarian voice. “I'm gonna put it in now, okay?”
“Okay,” she whispers, facing back towards the front. I look down toward her cute little orange rump, focusing on her aroused marehood and the thick black strap-on that's slathered with lube and aimed directly for her. Take it slow. With an easy, steady motion, I push my hips forward, and the fake stallionhood goes along with me. I make contact with her lower lips.
She gasps at the first sensation of touch, and I rub and pat her back gently as I ease myself forward. Her lips part fairly easily for the slick instrument, and as I descend deeper into her body, a throaty moan builds up from the other side of the bed, growing in intensity as I sink inside. Several inches of my accessory vanish into her. “Doing okay, Scoots?”
She attempts to talk between breaths. “Ah...oh wow...I feel...amazing...”
“Trust me, kid, this isn't near as good as the real thing.” I pat her twice on the rump. “Want me to go in any further?”
“A little...hah...more...”
Going along with her wishes, I push in until she gasps out for me to stop. The poor thing is quivering beneath my hooves; her body definitely isn't used to the innumerable sensations ripping through her right about now. I continue to stroke her softly to provide a little bit of comfort while she conforms to the presence of something long and hard buried in her love tunnel. For nearly a minute, I don't move my hips, instead allowing Scootaloo some time to breathe.
Finally, she turns to look back at me again. “You can...start moving, if you want.”
I smile back. “If you're sure, then okay.” Slowly, almost agonizingly so, I start to pull out, and a new round of moaning pours out of her mouth. I swear, it's like her inner walls are clinging tenaciously to the strap-on, so much so that it's providing a fair amount of resistance. I look down and see that the fake member is now stained with her juices in addition to the lube. “Enjoying yourself, kid?”
Her moans have words interspersed between them. “It's...mmm...incredible...thank you...”
I lean down to whisper the next words in her ear. “Just think, it's gonna be even better when it's you and Rumble.” I start to slide back into her, and she gives a little cry of surprise and joy. “He's gonna stick his big, fat cock right up in you, and his mind is just gonna be blown by how tight you are.” She gasps and groans as I push the strap-on further in. “He's gonna love every single, solitary second, and he's gonna want to rut you until he can't even think straight any more.”
I roll my hips forward the last little bit, then start a slow pattern of back and forth. My head stays by Scootaloo's ear, where I can hear all of her moans of pleasure and feed her more words of encouragement. “He'll tell you that you're so warm, and so wet, and so absolutely wonderful.” She bites her lip and clenches her eyes shut as I pick up speed little by little. “Or maybe he won't talk at all; maybe he'll be too busy staring at your amazing body and feeling you clench down around his cock.”
As if on cue, her inner walls constrict, but I continue to grind against her. I'm not pushing in all the way, but I know I'm getting deep. I move faster. “He'll grunt, and he'll groan, and he'll ride you like there's no tomorrow, because he loves you more than anypony in the whole world and he wants you to feel it.” I shove in the strap-on hard, and Scootaloo screams out. I wait to see if she'll say anything, but all I hear is hard breathing. Taking that as a signal to go on, I start to pound harder, working my hips like a machine to drive the false stallionhood deep, oh-so-deep into her. Suddenly, her own hips join in on the action, pushing back to meet mine as I thrust forward and pulling away as I withdraw. Her cries increase in volume and frequency.
I know she's close. “He'll feel the pressure start to mount, and he'll hold on for dear life while his body goes absolutely crazy, begging for release.” I'm going at a very high speed now, and each plunge into Scootaloo draws out another shriek of bliss from the young mare. The strap-on is quite soaked at this point, and our hips slap together lewdly as I bury the entire length inside her with every thrust. “He'll call out your name, and with a voice filled with strain, he'll shout out, 'Scootaloo! I'm gonna cum!'”
Her screams are guttural, almost primal. “Oh Rumble! Cum inside me, sweet Celestia, cum insi-i-ah!” She somehow manages to growl and moan at the same time just before I feel her convulse and twitch, crying out wordless sounds in a quavering voice as an orgasm tears through her body. I give one final thrust and leave the strap-on buried deep inside her as her body spasms and her wings buzz with excitement. I smile as I watch her ride out the throes of passion. Her eyes roll back in her head and her tongue lolls out of her panting mouth.
Once she's settled down, I slowly pull my hips back and look down. The strap-on is absolutely drenched, as are the sheets below, but that's just fine. When I make my exit, Scoots' rump drops to the bed, and even more of her juices leak out and add to the moist stain beneath her. I lay down on the bed next to Scootaloo; even though her eyes are pointed in my direction, I know she can't see me at all. Visions of her future husband are surely dancing about in her head, and I smile gently. “You did great, Scoots. Rumble's gonna love it.”
Even in her post-orgasm fog, she still manages to comprehend my words. In the midst of long, even breaths, she says, “Thank you...Auntie Spitfire...”
I ruffle her mane. “No problem, kid. Glad I could help.” I plant a little kiss on her forehead and pat her on the shoulder. “I think you two are gonna be just fine.”
