My Hairless Monkey: Break-up is Tragic

by OneUppington

Rating: teen
Tags: Comedy, Sex, My Little Pony: Friendship is Magic, Romance, Original Character
Length: 2134

Heartsleeve thought it was over between him and Cheataboo, but then she just had to turn into some two-legged creature. The lengths she goes to try and win him b… Wait, what?

Heartsleeve has a problem.
Well, technically not his problem. His Ex’s problem. But knowing this type of problem, I can’t blame Cheataboo for roping him into it. After all, if someone turned you into some practically hairless ape-like creature, you’d call somepony about it, right? Even your previous partner?

Not your previous partner?
… Yeah, me neither. But she did. To him. So now it’s his problem.

Published 2014-11-14 18:30:06 UTC
Last updated 2014-11-14 18:30:06 UTC

I Left My Heart in San Fransicolt

“…So that’s One year, two months, Three weeks and four days of staying the hell out of each-other…” I conclude. “Broken by an apology and a plea for help.”

“Wow,” exclaims Pocket Star. “That’s freaky just by itself. But why now?”

I could only shrug as he puts his front legs around me.

“Well, we’re going to find out, aren’t we?” Pocket asks.

“Yeah, we are. Or at least, I am,” I reply. “She sounded like she was in a bit of a mess last night, so maybe you should...”

“Should what? Leave you there with her? No chance in Tartarus! Heartsleeve, you know how mischievous she can get. I want to be there so she pulls out none of her tricks! And besides,” He says as he holds my hoof. “Don’t you want me to be there?”

I smile… because he’s right. I do want him to be there.

We kiss in the Centigrade, our favourite café in San Fransiscolt.

Pocket Star was my best friend back in our school days. We never really thought back then of where it escalated now. We both even snickered through the sexual education class when our teacher talked about homosexuality. Yet here we are. In a café. Kissing.

Pocket was the first of the two of us who came out of the closet. About a month after that class, if I recall. He found some magazines at a newspaper stand and realised that the Playfilly was a little more interesting than the Playcolt. The teacher from that class caught him there, flicking through to the centrefold of Soarin the Wonderbolt and he just panicked. A little heart to heart with her later, he decided to open to himself… then to his parents… and then to me.

Not an ‘I’m in love with you’ opening, of course. More of a ‘just to let you know and to make sure this doesn’t affect our friendship’ opening. Which it didn’t. We continued to hang out, discuss our future plans to open a clothes repair shop, and… well, actually opened the clothes repair shop. Pocket’s always been there for me.

Especially when I decided to leave Cheataboo.

Now, you’d think with a name like that, I should be wary of the pegasus filly known as Cheataboo and her cheating ways. I should also have been wary as it turned out she started to go out with me because she just didn’t want to tell her coltfriend at the time that it was over between them. And that the way she pays for the rent was by asking me for money so she can con the casinos at Las Pegasus for even more money. And that her cutie mark is five playing cards that are all aces.

Upon reflection, either I was such a bucking idiot for not assuming that she’s a trickster, or she is that good at being a trickster.

One weekend, Pocket and I decided to close the shop and see Las Pegasus for ourselves. I mean, why not, right? Two unicorn stallions, using a cloud-walker spell to hit the floating strip, go to some stand-up gigs, hit the roulette tables; generally, the mission was to have a good time. We didn’t tell Cheataboo about this little trip, nor that we were using the same hotel I know she goes to everytime she’s there, nor slip the receptionist a few bits to take us to her room. I wanted to surprise her. But… she surprised me instead. I mean… Sweet Sparkle, it’s still a little painful. Seeing her there… giving… this pegasus…

“Sleeve, you’re thinking about that moment again, aren’t you?”

I nod.

Pocket decided to hug me a little bit tighter than he usually does. It helps immensely.

So, after we caught them by her door, Pocket and I took a picture of them, headed back home, packed my bags, drop the picture on the table with the note saying if she wanted to explain herself, I’m going to be at Pocket’s place. She never really got into contact with me since…

… until last night… One year, two months, three weeks and four days later.

That was quite a fun year, two months, three weeks and four days. Really feel like a different pony. I am a different pony, let’s be honest; A little under a year and a quarter I was a spikey green haired straight pony that was crying his eyes out over his cheating ex-girlfriend. Now, I grew out the mane to put it in a mane-tail, really happy about this point in my life, and now getting hugged and kissed by another stallion, my former best-friend no-less, in a café as we wait for our…

“Two soy caramel lotta-choca-on-a-mochaccino with two sweeteners and extra foam for Pocket Star?”

Huh… That was quicker than Old Bean usually makes them. Wait, that doesn’t sound like him at all. For starters, he sounds younger. And from Trottingham. And a filly.

Oh Celestia, it finally happened. Old Bean said that this day would come, but I never believed it to be this day. The day he retired and a new barista came in. Fair enough, of course. Old bean was behind the counter since I was five and bored out of my mind waiting for my mom’s latte. I wonder where he’ll go… More importantly, I wonder who would dare to replace somepony like Old Bean?

As Pocket Star lets go of me and walks to this barista, I turn to see her. A very little, very brown-mained, very browner coated earth pony which stands out immensely from the mostly unicorn staff behind the counter. San Fransicolt is deeply rooted with unicornial lineage; just as much as Trottingham, of which I can tell she’s from by that accent, has with our hornless brethren. Her smile is… how can I put this…? It seems like she’s perplexed of something… Still fairly warming, though. And she, like Old Bean before her, has a label on the machine she’s using. For Old Bean it was just his name, so with that in mind, I assume her name is… Cuppaday. Aw, that’s a cute n… Is that a My Hairless Monkey doll?

That is a My Hairless Monkey doll. She’s got a My Hairless Monkey doll on top of the machine.

Technology’s taken quite a leap since Princess Twilight Sparkle put a bit more funding into schooling. It didn’t take long for animation to be discovered and to be as good as it is now. It didn’t take long before they became foal cartoons. One of these said cartoons is My Hairless Monkey, what’s usually called a filly show… but it somehow seems to get a demographic of older ponies. Even Stallions; even stallions who claim to be straight. Not me and Pocket Star, though. Don’t get us wrong, we tried to watch it, but we can only laugh at the fact that it reminds us of some certain renowned ponies from Ponyville. It’s clearly just the tale of Princess Twilight and the Elements of Harmony but they all are these things called humans. I mean, seriously. Why can’t it just be her as she is? Not some pink-skinned, short-muzzled, creatures with no wings or horns! And the names, Oh the names…

“Do you see the My Hairless Human doll she put on the coffee machine?” Pocket giggles as he returns back to our table with our coffee. “A little good luck charm on her first day, I bet.”

I smile. “Which one is it, actually? The one based on the princess?”

“Yeah! What was that name, now…?” My companion ponders until the answer came to him. “Tara Strong!”

I giggle a little bit. It’s the same initials, they aren’t even hiding it! “Hey, Do you remember what Rarity was?”

He’s shaking his head.

“Tabitha Saint Germaine.”

We both laugh. “Oh my goddess…” My partner sighs. “The sad thing is how well it fits her! Okay, Okay. What was Pinkie Pie, again? Andrea Libman?”

“Was it? I thought it was Fluttershy…”

“… You know what? It could be. Anyway!” Pocket Star pulls out a piece of paper. “She asked me to give this to you.”

Huh? Okay. I get hoofed over the paper… “This is a fully fledged letter…” I say, as I read it out so that my Star can hear.

Dear Heartsleeve,

Your mother earlier this morning has told me how you have came out of the closet after a horrible end of your old relationship. (Congratulations to you and your new lover, by the way. You both look fantastic together.)

This made Pocket blush a little… and me a lot. Thanks mom, for telling a total stranger about the current changes to my life.

Though, I got to admit, I am thankful about how well she took the news. Apparently, I have an Aunt in Ponyville which the two were as thick as thieves back when they were young. Sadly, Aunt Heartstring ran away there with a candy maker due to a spat with grandma. Thankfully for me, I don’t have to wonder what grandma thinks of me now. Still miss you though, Granny Heartbreak.

The reason I am writing about this, is because I was thinking of planning the same thing. You see, one of the reasons I left Trottingham is that my ex-coltfriend was playing around with every filly in the area.

“Oh Goddess!” Pocket Star proclaims. “The poor thing!”

I nod, as I continue the letter.

I wrote this to get this relation between us to ask you to assist me in living in San Fransicolt. See the sights and sounds and maybe… a filly to help me get started. Probably a big ask, but I would be grateful.

Hope you reply by writing on the back of the page.

Sincerely, Cuppaday.

We both are pretty silent for a while.

“So… should I write back?” I ask, interrupting this silence.

“I feel like you should, Sleevie.” Pocket says. “At least… correct her.”

Hmm… Yeah…

“Alright. You got a pen?”

“Got one fresh from the pen and sofa store.” He smiles as he pulls out the ball-point… Hey, I did tell you technology changed a lot since Princess Twilight came to be. He hovers it over to me, and I start to write.

Hey Cuppaday,

We would love to help you out with anything you want. However, I wish to correct you on something. I can’t blame you for believing it is the case, but I didn’t turn gay because of the break-up. I turned gay because I found something I never did with my ex-fillyfriend, or in any other filly I tried to have a first date with. A… feeling. Kind of hard to put in words exactly, but I think you understand.

Really, what I’m trying to say is don’t try to filly-fool if you’re doing it to just piss off your ex-coltfriend. If anything, it proves that his actions got to you and that he got to you. Just be true to yourself, and maybe the right pony will come along… No matter who they are.

I look at Pocket to ask him a question. “Should we tell her about Dream Weaver’s bar?”

Our favourite hangout. It’s kind of fantastic really, that a retired film producer made a LGBT friendly bar here. Maybe because his films are… well, if the title ‘Rarity Takes Manehattan to Her Bedroom’ is considered eye-catching for you, then you are probably are his demographic. Great guy, though.

Star looks at the Trottingham pony and then back to me. “I think she might like it, whether or not she is gay. Go for it.”

I nod to symbolise okay.

If you still want to give it a try, we know a bar with a few singles. On the corner of Rainbow Dash and Pinkie Pie Street, under the name ‘Moneyshot.’ It’s nicer than it sounds, trust me. Just head on in, find a purple unicorn with pink and blue hair and tell him that we sent you and your story. If there was anyone who would help you pick up, it’s Dream Weaver.

Our phone number is 575-7848 if you ever want to call us.

Welcome to San Fransiciolt,

Heartsleeve.

Pocket looks at the finished letter. “Looks good.”

I smile. “Let’s go see what Cheataboo got herself into.”

We both nod as we leave the letter under her tip jar.

… And of course, A few Celestias inside it. San Fransicolts always tips.

Author's Note

So, this is the new thing. I hope you guys love it.