Ponies Meet New York

by Caddy Finz


Chapter 1: The Big Five-O

"Hey, how yah doin', boss?" I greeted as Mr. and Mrs. Cake entered Sugarcube Corner for their weekly visit.

"Just swell, Vinnie!" Mr. Cake replied. "It's always good to see the guy who helped us get into the fortune five hun-"

"Uncle Vinnie!" The cake twins beamed in unison as they each latched on to my front legs.

"Pumkin! Pound!" I greeted. "How are my favorite kids? You two being good?"

"We sure are, Uncle Vinnie." Pound replied.

"Atta boy! How about you, Pumpkin? Did you ever make friends with that other filly at pre-school?"

"No, I didn't." Pumpkin huffed. "She wouldn't talk to me so I pushed her into a mud puddle and tore up her books."

"Well that's not very nic-"

"Pumpkin!" Mrs. Cake scolded. "I'm disappointed in you! When we're all done here, I'm marching you right over to their house and you'll be sincerely apologizing!"

"But I don't wan-"

"That's not negotiable, donchya know!"

"Anyway, Vinnie." Mr. Cake cut in. "I wanted to wish you a happy birthday! I know it's still a few days away but tonight, I'd like you to join me and the fellas down at the bar for drinks on us. It's not every day that somepony turns fifty. What do you say?"

"Wow Uncle Vinnie, you're old!" Pound blurted out as he climbed onto my back.

"Pound!" Mr. Cake scolded. "I swear, you two are gonna be the death of me."

What a beautiful thing, such innocence. I was always one to try to look tough but I always had a soft spot for the youngsters. Over the few years I've been here, I've been a guy that the kids around here look up to. The Cake Twins aren't the only ones in Ponyville who call me "Uncle Vinnie" and it just warms my heart to have such an honor. *Sigh* I wish I had some foals of my own.

It was true though. I am getting a bit up there, or at least over the hill. Luckily for me and others Earth ponies like me, at this age, I haven't even lived half of my life yet. Like I mentioned before, the average is one hundred and twelve, key word average. Heck, I don't even know how old Jackie's granny is but I bet she's still got a few more decades left in her. Real feisty for her age.

I have the events of three years ago to thank for this though. Some kind of higher being was looking favorably upon me and gave me a chance to start anew. I'll never forget that. I'll never forget how truly blessed I was to get such a life changing opportunity. I'm happier, healthier, friendlier and I plan on sticking around for a lot longer than I had originally planned.

There's just one thing that I simply haven't been able to stop thinking about though. One fact that stands above all the others. The fact that I was anything but deserving of this. If you recall what got me here in the first place, I wasn't exactly a saint. No, scratch that. I was a monster. I was a mean, nasty, bitter, cynical, miserable criminal. For somepony like me to have been blessed with the chance to turn my life around like this is just incredible.

Though I couldn't be happier with how things played out, I can't help but feel kinda bad sometimes. Surely there are others who were more kind and did great things to positively contribute to society who were less fortunate. It seems really unfair. I bet it sounds odd coming from a guy who had a bunch of great things happen to him but I'm telling you what, not a day goes by without me feeling gratitude. I will never take this for granted.

"Well thanks a million, Carrot." I said to the stallion whom I saw as a brother. "It's been a while since I got to have a nice cold brewskie."

"No problem!" Mr. Cake replied. "How about you and Pinkie close up shop and come meet me and the guys down at Berry's Tavern."

"Alright pal, see yah there! Hey yo Pinkster! Let's clean up and blow this joint! Wait-no no no no NO NO NO NOT THE CANNON!"


"Hey Pinkster, I'll catch up with yah!" I called over to my friend as I trotted towards my home. "I'ma go clean up real quick and I'll meet yah down there, capiche?"

"Okie dokie lokie!" Pinkie replied. "See you in a jiffy, spiffy!"

That girl hasn't changed a bit. It's her bubbly, upbeat attitude that makes me feel like a million bits and I hope she never does change. Of all the friends I have made, it's her and the other five who have really made me what I am today. Twilight was the one who encouraged me to open up and pour my heart out to the rest and set the foundation for my new life here. Rainbow Dash reminds me a lot of myself minus the past crimes and whatnot. Applejack completely changed my outlook on the types of people I once despised and she even donated her blood to help save my life. If that doesn't touch your heart, I don't know what will. Rarity was the one who took me on my first trip to Manehatten for my forty-seventh birthday and showed me the true generosity of the ponies of Equestria as a whole. And Fluttershy...my dear sweet friend Fluttershy is the main reason I have started the long path of self forgiveness. It's gonna take some time but I'm on the right track to being truly happy with who I am now and forgiving myself for who I once was.

It was a long, hot day and the heat in the kitchen at work made me sweat a lot so I hurried home to take a quick shower, fix up my hair and douse myself in unnecessary amounts of cologne. Hey, once an Italian always an Italian. There are some habits that you just can't kick. It's a lot like how I wave my hooves around in the air when I rant and rave because I can't remember where I put my pretty lavender soap. I don't really think about it while I'm doing it, it's simply here to stay.

It wasn't a very long trot over to the tavern and with my equine stamina and lack of smoking, I made quick work of the distance between me and where I was to meet some friends for the night. We actually did this quite often. Nearly every Friday evening like this one, it would be just me and some guy friends of mine and a lot of the time, Pinkster would be there too. It's nice to have other guys I can relate to and talk about hoofball with. Big Mac, Carrot Cake and Shining Armor are the fellas I've made close friends with and we hang out every weekend that we have the free time.

Seeming how this was just another Friday night like many before, I expected there to be just me, the gang and Pinkster. I failed to notice that half the townsponies were nowhere in sight so I got quite the surprise when I trotted through the door of my favorite hangout.

"SURPRISE!"

It was a set up! The good kind I mean. All of my closest friends were waiting for me to show up and greeted me as soon as I trotted in. The place was decorated with balloons, streamers and a big banner that read "Happy Birthday, Vinnie!" hanging up in the middle of the room. This was gonna be fun.

"Surprise, Vinnie!" Pinkster beamed. "Check it out! Just about everypony showed up! There's me and Twilight and Rarity and Fluttershy and Rainbow Dash and Applejack and Big Mac and Shining Armor and Cadence and Thunderlane and Cheerilee and Lyra and Bon Bon and Spike and *Gasp!* Apple Bloom and Scootaloo and Sweetie Belle and Babs and-"

"Okay we get it, Pinkie!" Twilight shouted. "Now let's party already!"

"Hey everypony!" I yelled at the top of my lungs. "We're all gonna get wasted!"

And that we did. In a few days, I would be fifty years old but that wasn't about to stop me from enjoying my time with those closest to me. Still though...sometimes I just couldn't help but feel that something was missing. Friends have been quick to encourage me to find that missing thing though. Wow, doesn't that sound selfish? I mean look at me, I'm the luckiest stallion around! I've got a great home, my dream job, friends who love me and...

"Vinnie, I'm tellng you, getting out there and finding a date would be good for you." Cadence said as I polished off a mug of cider. "Just give it a try. What could it hurt?"

For quite some time, my friends, who all care for me very deeply I may add have been trying to get me to come out of my shell and get out into the dating world. They all mean well and Celestia bless them and everything about them but remember, I was once a different species. Right now, to date a mare just wouldn't feel right to me yet. I mean, It's not wrong or sick or anything. I'm one of them now. The only issue is the simple fact that I'm just not ready to take such a step yet.

"Cadence, I really appreciate you and I know you mean well, dear." I replied. "Really I do, but at this point, I think it would still feel kinda weird."

"What do you mean?" She asked. "You've been a pony for three years now. If you end up meeting a nice mare and you two decide to be each other's special somepony, there's nothing wrong with that."

"I know that, hon. The only thing is that I myself still don't feel ready to do that yet."

"And there's nothing wrong with that either, Vinnie. Still though, my offer stands. If you ever decide to give it a try, I'd be happy to help you find a special somepony."

"With the princess of love helping you out..." Shining Armor began. "You'd be sure to nail yourself a hot piece of-oof!"

"Shining!" Cadence scolded as she elbowed her buzzed husband in the stomach. "Watch your mouth! I'm not going to hook him up with a cheap fling! I'm going to help him find something meaningful!"

In all honesty, she was right. I was kind of lonely at times when all of my friends were busy with their own lives and I've had my fair share of cheap flings. Those of which I didn't miss a whole lot. I used to go to clubs and bag myself a broad, take her home for the night, get intimate with her and never see her again. They all played out the same way. Meet, hook up and gone all in that order and after a while, it made me feel very empty. They were all the same...except one. I did once have a very serious relationship with a the only woman I fell in love with. She loved me as well and we even talked about getting married. That all went down the tubes when I could no longer hide my true line of work from her. I just couldn't lie to her and get seriously involved with her without telling her the truth. I confessed to her my ties with the mob.

Her name was Jennifer Sachentov and she rightfully left me after I came clean. I dated her when I was in my late twenties and I have since moved on and continued my fruitless attempts to fill in the void with cheap hookups. No more of that. I was beginning to really consider my friend Cadence's advice. All I had to do was simply try. What do I have to lose?"

"Hahahah! You guys are adorable!" I laughed. "I'll think about that, Cadence, but for now, I just wanna enjoy hanging out with everypony. Yo, Rainbow! How about a drink off? I bet I'll beat you this time!"