Carpenter's Dilemma
You are Jesus Christ.
Well maybe you weren't exactly. You didn't have any Jesus-y powers like fish multiplication or fig-tree cursing. You also didn't have an amazing beard; though you were working on that point. You also didn't have a religion behind you but when you thought about it you always decided that it was for the best.
Jesus was known for a lot of things, mostly the whole ‘I am the son of God’ thing he had going on. There was one thing you beat him at though: carpentry. Even then you were more than just a carpenter, you did a lot of construction work and were almost through your architecture degree before you left home.
Oh yeah, that was also something that kept you different from the good ol' J-to-the-C. You don't live on Earth anymore. Well at least you didn't raise into the heavens after a brutal and pretty preventable death. All you can remember was that you were training a new guy on the site, someone yelled something and BAM! Equestria!
You can also recall that someone said something around the theme of “I like trains” followed by a train horn, then followed by “Who wants tacos?”
You. You wanted tacos. However that was pretty much an impossibility in this land filled with marshmallow technicolor equines known as ponies. You got to meet the princesses, you learned about the pony culture from a mare called Twilight Sparkle and you got a job from the Ponyville mayor named Mayor Mare.
You always wondered about her, was the fact that she was mayor literally because her parents named her Mayor from birth? Was it a name that you grew into like Captain Falcon? Things like this always confused you and you usually didn't want to think about it.
Either way, Mayor eventually hired you on to take on the construction and architectural aspects of the new town you were residing in. Apparently there was a pony who continually called down doomsday events on an almost weekly basis. That gave you a nice amount of work and you got to meet all the ponies in town. You fixing things that Twilight broke gave you pretty much an instant 'we are fine with an alien being here' card, and it usually came with free food from the mother mares.
Plus there were a few other benefits for working alone with mares who were mothers but that is best told by them. Being a male in Ponyville was pretty good.
Through boning plenty of mares throughout Ponyville, you got your second job and an unknown talent that wasn't fucking married ponies. Funny enough, it came from Rarity instead of actual mothers. After a particularly rough session with the fashionista she asked you a question that you weren't prepared for.
“How are you with foals?”
You laughed and told Rarity that Sparkle had proof that you can't knock ponies up. “That is one of the many reasons that I like you darling. However my sister is currently visiting and I have to go to the Crystal Empire with the girls. You know how it is.”
You did, everyone knew about the Elements of Harmony. You especially since you have to usually clean up after them in Ponyville.
“I need you look after Sweetie Belle for a few days. I'll definitely pay you quite well.” Rarity was practically begging at this point.
So in the end she was able to convince you with her mouth. On your dick.
So that weekend you looked after Sweetie Belle in your house, which was a decent one just within the limits of Ponyville. She actually was super well-behaved and you two had a blast. Sweetie asked if she could bring over her friends, Scootaloo and Apple Bloom, and you allowed it. Surprisingly enough the three of them were more interested in the stories of your human home instead of trying to destroy everything.
It was a good time and the foals didn't want to leave, so you told them they could come over whenever they wanted to provided that you were there. You didn't want them getting into any trouble inside your workshop.
The Cutie Mark Crusaders became attached to you pretty quickly after a few more visits. The ponies in town strangely enough didn't see many problems with an older male periodically looking after three foals. You figured it was an Equestrian thing because that wouldn't happen on Earth without people getting ideas.
The town also wondered how you could have the destructive trio around so many power tools and materials and not have your house flattened to the ground. It was pretty easy for you and you don't know why ponies didn't adapt it for their kids.
You taught them that the things in your garage were very dangerous and that only you had the training and education needed to use them. Then you showed them what a power saw did to a tree branch the size of their foreleg. Then you told them that if you could help them in any way, you'd cut stuff for them or teach them basic woodworking.
The main point is that you never said “no” straight out. You observed that both human and pony children did the same thing when told a straight “no”, they did it anyways. If you explained why you didn't want them to do something and came up with some kind of compromise or explained why it was so dangerous, they didn't try it.
Sawing that branch in half in less than a second scared them straight on never using anything saw-like.
So you did your best to help them out when needed. You taught them how to use basic tools properly and little different tricks for woodworking. It was little things that you would have taught your kids, if you had any. That was probably one of the reasons you spent so much time around the CMC and helping with their quests. Substitute children.
Each one showed some brilliance in their work as well. Apple Bloom was pretty talented on structural work, though mostly farm-related things were the best. Sweetie Belle was fantastic at decorative work and prettying up projects. Scootaloo was a daredevil and anything that she was really good at usually involved her scooter, such as ramps and rails.
In fact, Scootaloo started to come over by herself to work on her scooter jumps and tricks. Her once-a-week visits with the Crusaders started to become more frequent to the point where she would be visiting almost every day to learn more. She would ask you questions on what you were working on or have you check on different angles of her jumps. You also had to fix her scooter more than once, especially when she started grinding on rails.
You found that if you weren't working on a project or fucking somepony's wife, you were helping out Scootaloo. Just like you planned to today as soon as she was off school.
You could almost count down to Scootaloo knocking on your door.
Three. Two. O-
There was a quick series of knocks before the door to your workshop opened up. “Wow, almost a full second early, you must have cleared my picket fence easier this time.”
You turned around to see Scootaloo prop her scooter against the wall. “Yeah! I even got a bit more lift through my wings!”
“See? I told you that they weren't useless, you just have to know how to use them right. You are already surpassing pretty much most humans when it comes to distance and speed on jump of this size.”
The other main reason why Scootaloo liked you so much is that you made her wing problem a positive. Sure she couldn't fly but she could glide a bit. Plus you pointed out that her wings allowed her to balance grinding on rails without taking off. Seeing her wings as a gift to her scooter tricks always made her brighten up. It also made her more confident in her cutie mark, seeing as it had a wing and all in it.
“Yeah! I was even able to get some more tips from Rainbow Dash on gliding and taking off without my scooter. Check it out!” Scootaloo urged as she ran to an open space in the workshop.
She backed up a little and stretched a little before planting her hooves on the ground and spreading her wings. “First I gotta get in position like this.”
That was your only problem that you had looking after Scootaloo, she had no sense of modesty. As soon as her wings raised in preparation for take-off, her tail subconsciously raised as well. You don't know if Scootaloo knew, and you didn't want to ask her for obvious reasons, but she just put everything on display.
Time slowed down as you involuntarily started to scope her out. She had pretty much everything you wanted in an older mare, but smaller. Her flank was small but proportionate to her size, which you knew would feel great to grab. You could just imagine her tight little tailhole expanding and struggling to take your length. The texture of running your hand over her new cutie mark before giving it a nice, hard spanking. You could almost feel sweat drip down your neck at the thought of running your tongue over her tiny little slit and tasting her innoce-
“Then you take off like this!” You were snapped out of your thoughts and view as Scootaloo jumped up into the air and glided lazily through your workplace.
You sprung out of your chair in surprise as Scootaloo banked around a grandfather clock you were repairing. “Whoa Scoots watch out! Don't bump into anything!”
“Don't worry I got this! Catch me!” The orange filly laughed as she opened her forelegs for a hug.
Grabbing her just before she hit your chest you pulled her into a hug. “Scoots, what did I say about flying in the shop?”
She nuzzled your T-shirt before looking up at you with a slightly hurt expression. “I'm sorry, I know I am not allowed to, but everything was turned off and I thought I was safe. I just wanted to show you what I could do now.”
You thanked Celestia that the panic killed your half-chub or she could have probably felt it.
Your heart pretty much was able to handle the abuse it was taking from Scoots, but it still felt wrong. “Look sweetie, you can't fly in the shop because you might knock something over that needs to be fixed. I'm not mad I just want to make sure you don't get hurt.”
She looked at you with her sad eyes. “But… I'm not Sweetie!” She smiled then laughed before jumping out of your arms and onto your chair.
“Cheeky pegasus. Now get your cute flank off my chair and show me some designs, I know you spent half the class making them instead of listening to Cheerilee.”
She paused before she left your favourite seat. “How do you know that?”
“I do maintenance at the school and Cheerilee tells me things.” You said with a wink.
She did that little adorable nose scrunch thing that ponies did when annoyed so you booped her on the nose. “Hey no fair!”
“All is fair in love and war, now let's review those drawings.” You sat down and moved the schematics you were working on.
Scootaloo picked up the tube that was attached to her backpack that you made for her to roll up her drawings in. In between the art she did for class she had crude designs for ramps that you would look over and make actual measurements for her.
Then, taking the tube, she jumped up onto your lap. This usually wasn't a bad thing but you aren't quite over thinking of her in a sexual way from three minutes ago. You kept both your lust and embarrassment down however to make sure that Scootaloo didn't know that there was anything wrong.
“Alright so I was thinking of using a small ramp to jump up on a rail, then use the end of the rail to get a bit more air as I jump over Apple Bloom.” Scoots explained as she opened up her drawing.
It was a rough plan all right, but you knew you could make it work. Scoots settled in your lap as you took out a new sheet of paper and a few drawing tools. You then proceeded to both work on the drawing.
It was quite cute and fascinating on how easily Scootaloo picked up on the practicality of the math behind sports. You guessed that because she was so interested in stunts, things that related to them would be where she excelled at. You know that Rainbow Dash would have some sort of meteorology from all the weather work she did. Maybe it was something in relation to cutie marks.
You realized you were letting your mind wander again as you focused on the orange filly between your le- on your lap! She was on you lap, nothing more and this was a common occurrence. On your lap, not between your legs.
“Alright! Now we just gotta use the pertracter to make an angle right?” Scootaloo turned her head around to look at you.
You raised an eyebrow. “You mean protractor? Yeah it is on the top of the desk.”
She nodded in acknowledgment before placing her front hooves on the desk and standing on your legs. She leaned forward to see if she could find the protractor. Of course in doing so she left everything exposed again for your unwilling enjoyment.
It was like a well-made buffet right in front of you and you couldn't even have a taste.
With her tail partially raised, it was enough to send you reeling. Her perfect pony plot with a tight, small and lightly puffed ponut just begging to be fucked and stretched to gaping. Her tiny slit just waiting for a cock to be thr-
“Got it!” Scoots exclaimed before settling back into your lap again, and right against the lump in your jeans.
“Now we just gotta…” she started to say before she rolled her hips and accidentally moved her small ass against the straining bulge in your pants. “What is that? You got a measuring tape in your pocket again?”
You were absolutely too horrified and shocked to give any explanation. “You are sometimes so forgetful dude! Seriously you know I would have asked for it later and you would have forgot that it was in...”
Scootaloo turned around and looked down into your lap. “In… your jeans… right. That's your penis isn't it?”
You stuttered and stumbled on your words, only getting out half-replies before you settled on the good old stereotypical “I don't think you are even close to old enough to be talking about it. Guys have it happen all the time to them.”
“Was it… was it because of me?” Scoots asked as she hopped off your lap and onto the desk so she could look at you eye-to-eye.
You figured the situation was awkward enough that you could adjust your junk to make it less painful. “Yeah, it was with your butt in my face and your tail raised.”
Her smile faded for a second. “Oh really? I didn't mean anything by it, I wasn't thinking. I didn't mean to hurt you at all.”
You shifted a bit and took a few deep breaths to calm yourself down a little. “Well really, it didn’t hurt me, I just kinda needed… room to adjust. Hardening thing in small spaces.”
Her eyes seemed to brighten a bit at that. “You mean you are pretty big? I have never been able to see it. I’ve seen Big Mac a few times and a few other stallion when other mares go into estrus but never really… you know. Seen one. Up close.”
You groaned. “Holy shit this is turning into a bad porno and I am in it with an underaged filly. Please don’t ask if you can play with it all innocently like you don’t know what you are doing.”
“But I don’t know what I am doing. I just kinda…” she rolled her hoof around for you to finish the implication.”
“Don’t say ‘I wanna see your thing’ because then we are getting into bad porn territory.”
“You keep on saying porn like I know what that means.” Scoots grumpily said. “That a human thing?”
“Porn is either video or images of sex. We have tons of it on Earth and the acting is absolutely horrible. We are practically in a schoolgirl situation where you don’t know how things work and you just gotta ask me, the older man, how to have sex.”
Scootaloo tilted her head almost like a puppy. “I know how to have sex though. I’ve seen Rainbow Dash and Soarin’ do it all the time over the lake.”
All of your “wat”.
For some reason the orange filly took your silence to elaborate. “So then this isn’t one of your ‘porns’ since I already know a lot about sex from watching Rainbow Dash go at it. Plus they do teach us some stuff at school. Plus I know enough not to tell anypony anything you tell me, I don’t even tell them about Earth.”
You raised an eye at that. “You have never told anybody apart from Sweets and Bloom about Earth?”
“Well yeah, you told us that stuff when we were alone with you. All three of us assumed it was because you wanted us to keep it a secret.”
“Really? I never really thought of that, you were the only ones to really ask apart from Twilight.”
Scoots nodded her head. “Yeah well you know we are smart. I’m obviously not gonna tell anypony about this. Adults always never want us to talk about sex stuff but you aren’t like anypony else so let’s keep at it!”
You were having a moment but you had to draw the line sometimes. “No.”
“What do you mean no? You never say just no.” Scoots spoke with an unbelievably deadpan voice.
“I mean no. You are too young for me to be discussing this with you. If anybody was listening in on us I would be probably jailed, let alone seeing you or our friends again. Hell, I’d probably be jailed and stabbed or something if I was on Earth.”
Scootaloo moved forward and poked you in the forehead with her hoof. “You aren’t on Earth silly. Plus I am not gonna tell anypony. Seriously I wouldn’t even brag to Diamond Tiara even if we were still mortal enemies.”
“You are too smart for a filly.”
“You’ve been teaching me basic trigonometry for three months. We don’t do that for another three years according to Miss Cheerilee.”
Three years until basic trigonometry, that is what you have been doing. Then it clicked in your head why you are so against this and you really felt stupid for this. “I know you hate it when adults say this, but you are still just a filly and I really am uncomfortable with talking about sex with fillies. It is a big taboo to mix minors and sex in my world.”
Scootaloo placed her hoof under her chin for a moment. “Okay but when you first came here you said you didn’t find ponies sexy. I know from Sweetie Belle that you rut Rarity. What about that?”
Note to self: gag Rarity next time. She’d probably love it anyways, probably should choke her so she couldn’t moan as much.
“That is different! Mares like Rarity are of age and they know what they are getting into.”
“Yeah but I know what I am getting into! Beside you have to be somewhat attracted to me, you got hard!” Scoots pointed out. “Okay gimme a second I gotta think.”
“About what? I don’t see how you cou-”
“When you first came here you thought rutting ponies was wrong. Then you got over that eventually and started having sex with ponies but there had to be that first one. Now you think that having sex with younger ponies is wrong, but you are still attracted to me, so maybe I am that one pony who changes your mind?”
“I don’t think it would work out that way, I am just not attracted to fillies.” You tried to reason with her, but at this point she really was wearing you down on this.
“You do think I am cute and sexy though. Be perfectly honest, okay dude? You know that I am right. Maybe you are attracted to me only and not other fillies?”
Fuck. She had a point. Sure you didn’t want to stick your dick into Apple Bloom or Sweetie Belle, but something about Scootaloo really… well, got your motor going. Although she was absolutely adorable she also just had that spark of curiosity and ingenuity that you liked. You had to admit that if she was five years older maybe…
“Look you didn’t give me a ‘no’ so clearly you are thinking about it.”
Could it be possible to be pansexual towards pony fillies? That seemed too much of a special snowflake status anyways. So you like ponies, you didn’t like fillies, but you really, really liked Scootaloo. Plus that flank. Unf.
You raised your arms in defeat. “Alright. You got me. I think you are sexy, cute and I really like you. So what do we do from here?”
Again, Scoots did that cute little head tilt and she added a smirk. “Wanna show me your cock?”
“You’ve never had sex, we aren’t just jumping into the deep end like that.” You said as you loosened up from the stress you just got over.
The orange filly in front of you made one of the most cutest pouting faces you have ever seen. You booped her on the nose. “However, what happens when I show you something that could be potentially dangerous?”
She thought for a moment before smiling again, but this time it was one of those grins that made you know she was up to no good. “You make sure you show me every single step along the way so you know what we are doing. Safety first, right?”
You leaned in closer to her so that you could feel her breath on your face. “Safety first.”
Then you kissed her.
By all means it wasn’t a very good kiss at all. She was too tensed up and you pretty much were kissing flat lips. Plus there was a little bit of difference between human and pony mouths that you knew about. Her mouth was also smaller than the mares you have kissed as well.
“Whoa…” Scoots simply said with a dopey expression on her face.
“Yeah and that kiss sucked too. Okay follow what I do.” You motioned for her to jump onto your lap again, which she readily accepted. “Okay, now you know how your lips are when you say the letter ‘o’? Do that but hold it, then push out a tiny bit.”
She did the actions you told her to do. “Okay I’m coming in again, and this time relax. This is all about a bit of passion, so if something feels right to you, try it and I’ll guide you through it. Emotionless kissing is just plain wrong. Alright I’m coming in again.”
You pressed your lips against hers again, and it was certainly a monumental difference. Now it felt more right. Scootaloo’s lips were nice and soft, gently pressing against yours as you could feel her breath quicken through her nose. You moved your hand along her back and pushed her against you, gently stroking her mane.
Finally, you broke your kiss again. Scoots had her eyes closed and her mouth loosely open. She blinked a few times before looking up at you. “That was amazing! I don’t even know what to say. Wow…”
You smiled back at her, you knew exactly how to make her happy. “You say ‘holy fucking shit that was fantastic’.”
Scootaloo grinned almost in the same way that Rainbow Dash did when she was feeling competitive. Placing both of her hooves on your shoulders, her head was slightly higher than yours. She then spoke with words that you will always remember. “Holy fucking shit that was fantastic, and I want more.”
“Sure, but this time don’t break from the kiss until I let you, enjoy everything and if something feels right, do it, okay? You can’t hurt me.”
This time it was her leading the kiss, her hooves moving from your shoulders to wrap behind your neck. You followed her lead by wrapping your arms around her, forcing her legs to also spread out to your sides. You used your fingernails almost as a brush as you combed down her spine, stopping just above her tail.
Scootaloo moaned into your mouth as you felt heat against the straining member in your jeans. She felt that contact too, but didn’t break the kiss. After a few meticulous motions, she got used to the feeling of your clothed member pressing against her. She began to move away before you stopped her, placing your hand at the back of her head. You slowly flicked your tongue across her teeth before she got the idea and opened up her mouth. Her excitement grew as you both lightly flicked your tongues across one another, tasting each other for the first time.
Her groans only increased as she started to grind her tiny bottom against your erection, and you could easily feel her heating up even more. Your hands moved from the back of her head to the cute little flanks that she had. You caressed her cutie marks before moving your fingers over the small curve of her tiny tush until you were a little bit away from her filly slit. Instead of going further with your fingers, you gripped her so her lips would spread open slightly and you pushed yourself against her. You could feel how hot she was getting even under your rapidly-soaking jeans.
The filly broke the kiss and pressed her head against your chest as she rode your lap, the slightly rough fabric teasing her virgin sex. “Oh… oh wow this feels so good dude. You.... enjoying this?”
You chuckled a bit as you dry-humped a bit against her. “Seeing you about to cum is pretty sweet.”
“Cum?” Scoots asked in confusion.
“You feel that sensation slowly building inside you?”
“Yeah…”
“Keep going and you’ll see what happens.” You teased as you helped her grind against you.
She nodded as she moaned into your chest. Your hands on her rump seemed almost oversized as you kneaded her flanks, using a bit of effort to help push yourself against her. Her breathing started to become more erratic as you helped her get off on your lap. You weren’t really getting close at all, but it felt amazing to be giving this much pleasure to Scootaloo.
With a short cry, all four of her legs hugged you tight as a small amount of marecum splashed on your already soaked pants. You gave her some time to ride out first orgasm before you talked to her again.
Holding her in your arms like this sent mixed feeling through you. Sure, she was probably having the time of her life, and she had never felt this way before. However, you felt a pang of guilt when you again realized that you were making a filly climax in your lap.
Eventually she looked up at you again with a smile on her face. Seeing her happiness made all that guilt washed away. Scootaloo was genuinely happy that she was doing this with you, so why should you feel guilty about it? Things were different here, and she was different from everything else. You couldn’t have prepared to be so charmed and enamoured by this young mare.
“That was an orgasm.” You informed her.
She took a few more breaths to calm down. “So I did a cum?”
You snorted in a short laugh. “No what you did was have an ‘orgasm’, also known as ‘cumming’ in slang, ‘came’ in past tense..”
“So I had an orgasm by cumming on your cock?”
“Close enough, want to do more?” You asked hopefully.
She seemed to be recovered enough to excitedly bounce on your lap. “Yes! This is so much fun!”
You silently thanked the gods for your good fortune. Then you remembered that they were two pony princesses who might not like you fooling around with a filly.
“Alright, let’s get to my bedroom. Despite what Rainbow Dash might think about having sex in public, I prefer a comfy bed in private.” You told Scoots as she jumped off your lap.
“Best day ever,” you heard Scootaloo whispering to herself as you snuck out the back door of your shop.
Your luck was on your side again as nopony saw you sneak a filly into your house conspicuously. Less because you had Scoots behind you, more because she made you look like you pissed yourself.
Once you got inside your home you only saw an orange and purple blur rush past you. Seeing her run up your stairs you also caught a “firstonetoyourroomwins”!
You laughed at her childish manner and jogged up after her. Your house wasn’t too big, most of the furniture you made yourself. The kitchen was a bit small for you, but had a nice little dining area. Your living room had a couch with a few bookcases and a fireplace. Running up the set of stairs to your room was pretty fast. However the entire time you looked through your familiar rooms they were now filled with the possibilities of fucking Scootaloo in them.
Your second floor was entirely your room. You were the only one living here and to save on space and materials during construction you opted for an entire floor being your own bedroom. That gave the benefit of a good princess-sized bed. However your eyes weren’t concerned about the quality on your mattress.
It was on the adorable filly sitting on it with a smile to rival Pinkie Pie.
“Okay you are here first, what do you win?” You asked the energetic filly as you took off your shirt.
“How about another orgasm?” She sweetly suggested, but seemed a little down after she mentioned it. “Wait, I got to feel awesome, I want you too as well.”
Taking off your pants, you were left a little stunned by her desire to please you. “Really? I didn’t expect you to be so mature about it.”
She eyed your tented boxers with some apprehension and excitement. “Well, we are doing stuff that adults do right? I totally gotta think more like an adult then!”
You internally laughed at how she said that before you walked to her. “Wanna see it?” You asked, almost booping her on the nose with the tip of your clothed cock.
“Can I?”
“No, you can just sit there and I’ll continually boop you on the nose until I cum in my shorts.”
She didn’t look impressed with your sarcasm. “No kidding, but why you gotta wear all these clothes? It seems like it just takes away the fun of doing this often.”
“Well, for one, you know why I wear clothes. Two, I don’t do this often. Lastly, you seemed to like my jeans just fine.”
She blushed a bit at your comment before countering. “Well, if you didn’t wear so much we could do this more.”
That sent a shiver of excitement down your spine. “Don’t make me hold you to your word.”
“You always taught us that we always keep our word.” Your heart started beating faster as her front hooves were placed on your chest before trailing downwards.
“We will see how you fare after we are done. Go ahead and check me out, just be a bit careful. I am sure you know how guys are with being hit too hard.” You warn her.
You stood right beside your bed as her hooves started to pull down your boxer shorts slowly. Pretty much like in every single porn you see, your cock sprung out of them and almost hit her muzzle. “Ohh this is different. You don’t have that ringy thingy that stallions have.”
“Different species, I will also last longer than most stallion will too. So don’t feel like you are doing a bad job if I last longer than Soarin does with Dashie.” You informed Scoots as her hoof tentatively caressed your length.
“Okay, good, so should I use my mouth or something?”
You paused for a second as you thought out what is going to happen. You were pretty fucking aroused by now to say the least. You didn’t think you could resist for much longer without actually fucking the filly senseless. However you didn’t want to hurt the filly, and you still wanted her to have a good time. You got a brilliant idea to fix all of this.
“Okay Scoots, I got an idea. I’m going to lay down on the bed and you are going to go on top of me. You are also going to have your rump above my face alright? This way you can play with my dick all you want and I can prepare you for the next step.” You told her as you crawled onto the bed and laid down.
“Prepare me? Don’t you just slide yourself on in?” She asked as she trotted up beside you, about to turn around.
“Unless you and Sweetie Belle have been playing with her horn a bit, you are going to be really tight. If I just ‘stuck it in’ it could hurt a lot and I want to make sure you love this entire thing.”
Scoots jumped onto your chest before her legs drifted to your sides again. “Sweetie’s horn? What do you mean by… oh… that. No we haven’t, though that is a good idea. I’d rather play with your ‘horn’ though.”
You were too distracted by her cute rounded ass in your face to reply. Now you got a really good look at the filly’s soaked slit, more tucked in than a mare’s but still just as inviting. Her winking clit popped out ever once in awhile; but unfortunately too far away because of her small frame. you were definitely going to feast on her when you had the chance.
“Okay so I just suck on it?” Scoots asked as her warm breath made your length twitch.
“Almost, you suck on it while bobbing your head. Almost like a popsicle, but don’t hit the back of your throat.”
“Oh good, I was gonna ask about that, you are really, really big.” Relief was in her voice.
“Thanks, I’ll never be tired of hearing that.” You told her as you massaged her flanks.
Your breath hitched as her warm mouth enveloped your tip, her tongue lightly teasing you. You enjoyed the sensation of her lips on your erection as you gave her moans of approval. After a minute she got more confidence and was able to give you as much of a proper blowjob as a filly could. She was obviously sloppy and inexperienced, but you could only dream of how good she should get.
“Ohhh salty! A bit bitter though. That good so far?” Scootaloo asked.
“If you keep going I promise I’ll make sure you have at least three more orgasms today.”
You think she almost deepthroated your length as she went back to giving you oral. You would keep enjoying this with all your attention but you had other matters to attend to.
Using your left thumb, you pulled her lips apart slightly and you marvelled at how tight her pink flower looked. You used your right index finger to tease her a bit, lightly stroking her puffy lips as you gathered her arousal. You could feel her appreciative moans on your cock as you lubed your finger up. You lightly pushed the tip of your finger through, and gently penetrated her virgin sex.
She was tight as hell even with just one finger, there was absolutely no way she could fit your girth inside her like this. “Hey Scoots, I know this is gonna be hard with all these new sensations, but I need you to relax okay?”
“Mmmhmm”, was all you got due to her enjoying your finger and her new ‘toy’.
She did try her best though, and you could slowly snake your digit inside her. You were fully expecting a hymen, but you never came across it as your knuckle sank into her. Unfortunately, your finger also touched her cervix by the time it was fully inside her. She didn’t make much of a reaction, so you didn’t say anything. However considering how your dick was a few inches longer than your finger, there was going to be a length issue that you didn’t have with other mares. Sure you would still get another inch inside her, but she couldn’t take you fully.
Then you remembered that you were about to fuck a filly. Not only were you going to be in the tightest hole you’ve ever fucked, but if you continued this as she grew up, she was going to mould right to your shape. All the fucks about not being able to fuck her deeply were completely gone.
She was barely paying attention to sucking your cock, but being in her mouth felt awesome so you didn’t care. You started to finger fuck the filly for a little bit to get her used to the sensation of something inside her. When she could take your first finger easily, you used a your middle finger to open her up more.
By the time she could take your second finger she wasn’t even bobbing her head anymore, just drooling on your cock embedded in her muzzle. Her moans stimulated you well enough as you curled your fingers to rub against her inner walls. Another high pitched cry of passion later and you assumed you found her G-spot. She came almost instantly as you coaxed the orgasm out of her.
You ceased your ministrations momentarily waiting for her to calm down. She eventually relaxed enough and you used the opportunity to slip the tip of your ring finger in. Immediately she tensed up, her sex gripped your fingers almost as hard as when she was cumming. “Ow! Okay that hurts a little!”
You stopped immediately of course. “You okay though?”
“Yeah, it just stings a little bit.” She fidgeted before she realized that it moved your fingers and winced again.
You figured this would happen eventually, no filly could take you this easily even if it was Scootaloo.
“Okay, we have two options. We stop and you enjoy my fingers and we get me off with your mouth. The second option is for us to wait until you are used to this, then we have sex.”
“I uhh… oh… okay gimme a sec.” Scoots said as she wiggled her tush.
You started to take the little bit of your third finger out that you got in before Scoots spoke up. “No! Keep it in! It doesn’t hurt as much now, and I want us to do this all the way! If real sex is how mares do it with you then I want to as well!”
You gave her a little spank, which made her do the most adorable squeak you have ever heard from her. “Alright then my kinky cutie, let’s get you all loosened up. You take it at your pace, just squirm and press against my hand when you want to take more in, okay?”
She took a few deep breaths before she nodded. “Then the fun starts?”
You nodded in agreement. She nodded back and wiggled a bit, taking a little more of your triple digits. You decided to help her out a little by moving your already-buried fingers around, sending shivers of pleasure through her as she struggled to loosen up.
This went on for a few more minutes, and she was able to get your ring finger down halfway. You briefly regretted not turning your hand upside down to try and tease her tailhole a bit. You decided against her losing her progress so far and the fact you don’t know if she is into anal. Yet.
Soon though. Soon.
You heard Scoots take a deep breath and she relaxed a little before pushing back against you hard. You feared for her comfort as she sank down on your three fingers, right down to the knuckles. She squealed a little in pain and you were going to withdraw when she continued to press against you. “No! In! Keep it in! I can do this, I am tough! I need this!”
She rapidly took deep breaths as fast as she could, and you saw no blood so you figured she would be okay. You teased her clit with your thumb and soon she was a moaning mess on your chest. “Feeling better?” You asked.
“Ohhhh yeah. It doesn’t hurt as much now. Phew, I thought that would be like ripping off a bandage. You know, doing it all at once instead of taking it off slowly. Get the pain out of the way as quickly as possible.” Scootaloo said she clenched a little on your fingers.
“Yeah but it really hurt the first time you ripped one off though right?”
“Yeah… I got used to it. Am I good enough to have sex with now?”
You slowly pulled yourself out of the filly, fully enjoying the sight of her slightly gaping sex. You easily picked her up and spun her around. She had a few tear marks on her face which you wiped away with a clean finger. “Scoots you were always good enough to have sex with.”
“I swear this might not be worth it if you do all that sappy stuff.” Scoots joked.
“Yeah yeah. Okay how do you want to do this? You can be on my lap again or we can do it pony style. On my lap you have better control.” You suggested as you kissed her on the forehead..
“On your lap again. I really enjoyed it last time.”
You lightly tossed the filly off your lap as you moved further up the bed, resting your back on a pillow against the headboard. You motioned Scoots up on top of your lap again, and she followed you. Your erection was against your stomach, throbbing against the filly. You both noticed exactly how far up her body your length was. “That is all going to fit inside of me?” She sounded a bit scared.
You shook your head. “Not when you are this young. You’ll get about half in, but as you grow older you will be able to take more and more of me.”
She nodded. “Okay good, then we will keep doing this until I can fit all of you inside of me. Deal?”
“Deal, but that means I’ll probably have to become your special somepony. I don’t want you to do this with anyone else but me, and I don’t want to do it with anyone but you.”
“So you won’t rut any other mare?” She asked.
“I pinkie promise not to if you are my special somepony.” You swore to her.
You could almost hear a ‘squee’ coming out of her. “Alright then! What do you want me to do?”
You moved your hand down to the base of your cock before angling it slightly. “Just move yourself over it and slowly sink back down on it. Take your time too, okay?”
Scootaloo nodded as she aligned her prepubescent slit over your throbbing manhood. Grinding on your tip a little, you could feel just how hot and wet she was as she enjoyed the sensation. Slowly you felt her press against you, and soon her lips parted to take your pride inside of her.
“Wow, dude you feel so big.” The filly said as she stopped to get used to being penetrated.
“You are so fucking tight too, Scoots.”
She was too, even with you stretching her out she was unbelievably tight and you knew it was the right idea to loosen her up. You placed your hand on each side of her flanks to help her steady herself and to assist in taking you. Without speaking you each found a slow pace, where she would pull off slightly and you would inch your way into her a tiny bit at a time.
The underage and recently-virgin filly in your lap was leaning into you again, lightly pawing at your chest as you fucked her for the first time. She cried out a little as you hit her cervix. “Okay too much!”
You instantly pulled back a little to let Scootaloo rest exactly where she felt was “Deep enough”, which was just under two thirds of your length. “Wow, you took more than I expected, over half.”
All you got was a mumbled ‘yay’ before she started rocking on your lap again. You two didn’t say anything else and just enjoyed each other. Of course, true to Scootaloo’s nature, she got progressively louder and louder as you both fucked. You gripped her flanks a little bit harder and increased the pace of your thrusts. Scoots eventually lost control of her actions and just let you take over completely, allowing you to use her as you pleased.
“I’m gonna… fuck I’m gonna cum!” Scoots shouted her newly-acquired vocabulary as you violated her over and over again.
A few seconds later and you felt her tighten up as she cried your name out loud. Her pussy gripped your member for all it was worth and the feeling of a small amount of marecum soaking your thighs showed just how much she was enjoying this. You held your cock deep within the small filly as you let her ride out her orgasm.
Eventually her death-grip on your shaft lessened as she relaxed against your chest. Your hardness was still embedded deep within her still, and you swore she could feel your pulse. “Hey… you not done yet?” She sleepily asked you.
“Nah, got a good way to it though, you feel amazing.”
“Then keep going, don’t mind me, I can take it. I want you to cum too.” She shakily placed her hooves on your chest and pushed herself up. “If we are gonna do this more and more then I gotta keep up with you. I can be the best marefriend you have ever had!”
You didn’t correct her by saying you never had a marefriend, only ponies you’ve fucked. Your answer also got caught in your throat as her newly-slickened walls slid across your shaft. If she felt amazing before, Scootaloo’s pussy was heavenly, now that you got some extra lubrication from her orgasm. She must have felt the same way because her forelimbs were shakily trying to keep her upright.
Well, if she wanted you to cum inside her and keep going regardless of her keeping up with you, then you wouldn’t disappoint. You wrapped her up in your arms and placed your legs on the bed so you have some leverage.
Then you proceeded to make the filly in your arms into your own personal cocksock.
Looking down at Scootaloo as you fucked her you knew she was perfect for you. Apart from her amazing non-sexual qualities you loved, she was taking your cock like a champ! Sure it would be a year or so before she was large enough to take your cock fully. You didn’t think Scootaloo minded much, the amount you could fuck her with left her in a state of euphoria.
Scootaloo’s eyes were unfocused and half lidded. Her mouth was partially open and drool ran down her chin as she lazily moaned out. Her sounds of appreciation always hitched in pitch as you lightly tapped her cervix. She was enjoying the feeling of her cunny being filled.
All amazing things must come to an end though, and you felt your orgasm coming on rapidly as you penetrated the underage pony over and over again. “Hey Scoots, you ready to make me cum?”
“Yesh, totally just keep… keep going.” She mumbled out.
“You ready to become my mare?” You figured you could pretty much ask her anything at this point and she would agree.
She could barely speak as you increased your speed and simply replied with a ‘yes’ until she ran out of breath.
Then with one last thrust, your tip lined up with her immature cervix and you absolutely covered it in your human seed. You immediately kissed Scootaloo and you both cried in pleasure as you unloaded into the foal. Ropes of hot, sticky cum filled her to the brim and around your girth. You felt like you were completely emptied as you kept yourself inside the squirming orange filly.
You relaxed against the headboard of your bed as Scoots rested on your chest once more. The only thing you could hear was the soft sounds of both of you breathing in the afterglow of possibly some of the best sex you’ve ever had. Certainly, it was the most taboo so far.
“Feeling okay, hon?” You asked the filly on you.
“Yeah, it’s so warm inside my tummy right now.” Scoots giggled.
“Yeah well you get to have that whenever you want.”
She snuggled into your chest a bit more, nuzzling above your heart. “I wish I could just sleep over every day.”
“Well, it isn’t like anyone is stopping you from coming over here you know. Everypony in Ponyville trusts me with taking care of you and your friends while crusading.” You said as you ran your fingers through her mane.
“Yeah but I wanna be here everyday. I want to be with my cool coltfriend!” She complained in your arms as she leaned into your scratches.
“Well, special someponies don’t just move in with each other once they start dating. They go out for a while before they move in together.” You informed Scoots.
“Okay… but I kinda had a better idea. You know how I live at the orphanage right?” Scoots asked.
“Yeah, I had to get permission from them to let you sleep over.” You tell her.
It was really easy to get permission, too. You got a reference right off of Twilight and that was it. You didn’t also give much thought to Scoots being in an orphanage either. The care system in Equestria was pretty much the best you had ever seen or heard about. Scootaloo was in good hooves and everypony around town just accepted it. You just assumed it was the norm for this world and stopped comparing it to a human orphanage.
“Why are you bringing this up now?”
“Well, I’ve always dreamed… well… you know.” She rolled her hoof around for you to continue.
“You want me to adopt you for the sake of being here more often for sex?”
She panicked a little bit. “No, no! I want to be here anyways. You are literally cooler than Rainbow Dash at this point. Plus you help my friends and I whenever we need it. You also treat us like actual mares instead of just foals.”
You smiled, you knew all of this of course. “Really? Not the sex at all?”
A hoof hit your chest. “Yes the sex too, dude.”
“Alrighty, I’ll give it a thought okay? This is more than just a yes or no answer. Taking you in would be a pretty big thing, even if you weren’t planning on letting me fuck you all the time. I gotta be responsible about this. I will be thinking heavily on this alright?” You reassured her.
“Alright, I can totally deal with that. It makes sense too.”
You could feel yourself almost slipping out of your new special somepony. “You know what a super awesome special somepony would do for her new coltfriend, who may possibly be her new dad as well?”
“What?”
“Clean me off with your tongue.” You told her.
“Really?” Scoots said in surprise as she slid off your cock and watched your pearly-white seed drip onto your wilted member. “Well, it was just in my mouth before, and I did like the salty taste.”
You relaxed as your new fillyfriend and tentative daughter went down on you to clean your used cock off. You smiled as you felt her tongue lap at your manhood.
So now you had your own house, a good job, a decently solid sex life, a partner who you could pretty much train sexually, a filly you have fallen in love with, who you wanted to raise right, and a good future to look forward to. You gasped as you felt Scootaloo’s ministrations started up your drive again.
“Hey maybe-Dad?” Scoots asked while she bobbed on your tip.
“Whatcha need Scoots?”
“I left something out before. Soarin’ didn’t use that hole when I watched him have sex with Dash.” Scootaloo told you as she turned around to lift her tail. “He used this one instead, and if Rainbow Dash can take it up the butt then so can I! Wanna try out my tailhole?”
You simply grinned.
Author's Note
Scootaloo is best cocksleeve.
Write down them comments yo'. If you don't like how I wrote as story about you putting your dick inside of an underage Scootaloo, that's cool. If you think I should have aged Scoots up however, that is stupid. It takes away the whole point of nailing Scootaloo.
Again I am not a bad person because I am Canadian.
