Derpy's Confession

by Oldtakufanboy

Rating: mature
Tags: Derpy Hooves, Slice of Life, Human, Anthro, My Little Pony: Friendship is Magic, Original Character, Sex
Length: 3103

Derpy tells me that she has feelings for me

My name is Jake and everyday I get mail from this hot mare named Derpy who is such a klutz at times. However, I do notice that she has been acting…weird every time she gives me the mail. Today however, was rather unexpected when she tells me that she likes me.

8/16/16 update: audio read

Published 2016-06-09 05:00:01 UTC
Last updated 2016-06-09 05:00:01 UTC

Derpy's Confession

I was sitting in the living room reading the book of When Marnie Was There; a book that I liked back in my younger years before I was transported here in Equestria because of some sort of experiment that went wrong. I was lucky that I had it in my hands to remember what humans look like, since there's no way I could go back home to the normal world. I may be homesick, but I actually like it here in Equestria. Sure, it's weird that I live in a place with anthro creatures, but I got used to it. I met many of them who were nice, including the princesses. I began to learn of the society and of the past. Three years ago after living with the princesses for quite some time, I decided to move out and find a place in society. I got a job of construction and it fitted me perfectly. I was paid handsomely and continued to do so. However, starting this week is my day off. My boss is quite a nice mare and she says that I earned this week off after working a lot on this bridge near Manehattan.

As I flipped to page seventy-six, I heard a knock at the door.

"I bet I know who that could be," I said, as I bookmarked my page before getting up.

I walk over to the door and there she was: Derpy. Now I don't know much about her, either than the fact that she's kind of a klutz, but she seems to come to give me my mail a lot and she's always flustered. Her cheeks flush and her tail swishes to and fro when she tries to talk to me. Now that I think of it, I think she has a crush on me. I do have to admit, I always find clumsiness in a woman rather sexy. And speaking of sexy, I do find Derpy rather sexy; she has D-cupped sized breasts that could make any stallion go nuts for her and her clumsiness is sexy.

Derpy looks up at me with a blush and hands me my mail.

"U-um, here's the mail, J-Jake," stuttered Derpy, as I take the mail from her hands.

"Thanks, Derpy," I said with a smile.

Her face gets redder, as I notice at the corner of my eye that she was looking at my abs.

"Y-y-your w-welcome," she says, as she fidgets with her fingers, "how's your morning?"

"It was rather nice," I replied, "it was cold this morning, but I decided to make myself some pancakes. How was yours?"

"M-m-my morning was rather…um…"

"Fine?"

"Y-yes."

"Would you like to come in for a drink of coffee?"

"Wha?!" shouts Derpy, as her satchel slips of her arm and falls to the ground, dropping a lot of mail on my patio, "Oh no!"

Derpy bends down and grabs pieces of mail one-by-one.

"Here," I said, as I went to my knees and helped her out, "let me help you out with that."

"T-thanks," said Derpy, as she and I picked up pieces of mail together.

As we did, there was one left and unexpectedly, as I reached for it, I felt Derpy's hand touch above my own before she could catch it. She and I flinched and looked away from one another.

"Sorry, you take it," I said, as I could feel my cheeks get warm.

As she reached for it, I looked back at her and could see her furry breasts, which made my mind wander. I shook my head and stood up.

"I-uh- I'm sorry for shocking you like that, Derpy," I said, as I scratched the back of my head.

"It's okay," said Derpy, as she stood up and places her satchel over her arm, "but I would love s-some coffee."

"Come right in," I said, as I held the door open for her to enter.

She walks in and looks around the kitchen and living room. She was rather impressed, but then my book caught her attention. She picks it up and looks at it, as though she never seen a book before. I also bet she's never seen a book that dealt with humans in it.

"I see that book caught your attention," I asked, as I walked in the kitchen.

"Y-yes," she said, as she places it back down on the coffee table, "never heard of a book that had humans in it."

"Back where I'm from, most books are made by humans," I said, as I began putting in coffee mix in the coffee maker.

"Really?"

"Yep. There are all sorts of books like fantasy, historical, fiction, science-fiction, etc."

"S-s-sounds interesting," she said, as she walks up near the kitchen and sits in the stool, "your house is quite…unique."

"Why thank you, Derpy," I said, as the coffee maker beeps, allowing me to pour our coffees in.

I handed over a mug to Derpy, which made her flinch and fall off the stool. I ran out of the kitchen to help her up.

"Derpy," I said, as I sat her back on the stool, "are you okay?"

"M-my head hurts," she said, as she rubs her head.

"Sit right there," I said, as I rushed to the freezer and pulled out an icepack.

I came back to her and placed it softly on her head, making her flinch.

"Th-thank you," she said, as her face goes red, as a cherry.

She places her hand on the icepack, as I walk back into the kitchen and take a sip of my coffee. As Derpy sat there quietly sipping her coffee, she clenches her right fist and slams it down.

"Jake," said Derpy with a blush, "do you have a special somepony you like?"

"Huh?"

"D-d-do you have somepony…special?"

"Like a partner? Not really. Why?"

Derpy gulps and places her coffee aside. She places her icepack down and gives out an exhale.

"J-Jake," she said, as her face gets ever so red, "I…l-l-like you."

Whoa! I did not see this coming. Looks I was right: she does have a crush on me.

"You do?"

"I think you are a really handsome human, you are far more attractive than most stallions that try to hit on me and you are the first guy who's treated me kindly and not act like a horny stallion."

"Well…that explains why I'm noticing you blush and act flustered around me."

"Jake…would you mind if I come back after my shift? I get off at seven."

"You are always welcome," I said, as I ruffle her hair, "I have to also admit…you are pretty cute when you're clumsy."

Derpy blushes and looks away from me. She then gets up and straightens out her wings.

"Time for me to get going," she said, as she walks away from the kitchen and towards the door, "see you later. I'll be back here to hang out with you."

"What do you have in mind?"

"Something," she said with a wink, before flying away.

I close the door and sat down on my reading chair, wondering on what Derpy has in store tonight for whatever she calls fun.

"I guess I should go back to reading," I said, as I picked up When Marnie Was There, "that'll make time fly fast."

It was seven O'clock, as I walk over to the door. As I opened it, it was Derpy wearing something I didn't expect for her to wear for tonight: her usual uniform. However, she was holding onto a small package that had a sweet smell coming from it. The weirdest part was that her breasts were on top of the package, which made me flush.

"Hiya," she says in a cutesy voice, "I'm here."

"Um…"

"What?"

"Are you allowed to wear that when you're off work?"

"I just like wearing it for tonight. I'll get it cleaned."

She then hands over the package to me.

"I also got you something as a thank you from this morning," she said, as I grabbed ahold of it, "you can open it if you like."

I look down at the small package and pulled off the top. Inside were small cookies that had the color of Derpy's fur and one that had her cutie mark.

"I asked the baker to make me cookies that had my color and have one of them with my cutie mark. Like it?"

"Derpy, this is very sweet."

She blushes and places a hand on her cheek.

"Anyway, would you like to come in," I said, as I opened the door for her, "it's cold out here."

"Sure," she said, as I began to notice her shivering.

The two of us walked in and sat down on the couch. She continued to shiver, as she held onto my arm. She may be cold, but her fur felt very soft against my arm.

"Would you like me to start a fire?"

"C-c-c-could y-y-you?"

"Anything for a cute mare like you," I said, as I stood up and walked over to pick up a log of wood.

I place it gently in the fireplace and then got the fire going by lighting a pice of paper beneath to get it started. I walk back to Derpy, who still continued to shiver.

"It'll get warmer in a bit," I said, as I ruffled her hair, "care to tell me about yourself?"

"Oh! Sure. Well you know me as Derpy and I'm the klutz of Equestria. Sometimes, I feel as though people hate my clumsiness and think that I should not get a job. Sometimes, I feel as though I can't do anything right because of my clumsiness and that my eyes are crooked."

"Derpy, don't ever think like that," I said, making her look up at me, "you are special and don't let those ponies ever bring you down. You are perfect no matter how you think of yourself. I don't mind your clumsiness or that your eyes are crooked…I find your clumsiness…sexy."

"Huh," said Derpy, as her face went red.

"Yes, I like clumsiness in a girl. I think it makes them look cute. Derpy, I think that's one trait I like about you."

Derpy couldn't answer me; I think I made her feel tongue-tied.

"My favorite trait about you is that you are very kind and that you make me feel like a special mare."

"You're too kind," I said, as I could feel my face warm up.

Speaking of warming up, I began to feel the heat coming from the fire and Derpy's body beginning to feel warmer.

"Jake?"

"Yes?"

"Can I…be your special somepony?"

I smiled and held onto her head. I slowly and gently place our foreheads together and gave out an exhale.

"Yes…I'll be your special somepony."

I reeled my head back, as I look into Derpy's eyes. She then puckers her lips and plants a kiss upon my lips. I didn't retreat; instead, I kiss back. I then felt her tongue poking into my mouth, as our tongues began fighting one another for dominance. The both of us reel our heads back, giving us some air.

"You're a good kisser," I said, as I gave her a kiss on her cheek.

"You are too," she said, as she kisses my cheek.

She then looks down at her uniforms and begins to unbutton her buttons one-by-one. Her shirt was unbuttoned and she tosses it aside, revealing to me her black bra, which did show off her gray fur from her body.

"W-w-would you like to touch them," she asks, as she squeezes her breasts together.

"Yes, please," I said, as she begins to unclip her bra, making it fall to the floor.

Her breasts her perky and her pink nipples were hard.

"Touch me," she asks.

I take my right hand and place it gently onto her left breast, making her give out a light moan. Her breast felt soft and squishy, as I gave it a few light squeezes. I then brought my mouth to her nipple and gave it a lick.

"Ah," she moans, "do that again with your tongue."

I gave her nipple a few more flicks, as I grabbed ahold of her other breast and did the same. As I continued to do so, I then began to suckle on her left breast.

"Suck it," she moans, as she places her hands on top of my head.

I continued to do so, as she moans a little louder. I then began to have a creamy taste in my mouth; I pulled my mouth away from her breast and notice milk pouring out.

"Don't worry," she says, "drink it. It actually tastes good."

I suckled more and more of her milk, but I only get a dribble. My couch was a bit soaked from her milk, but I'll deal with that later.

"Was it good?"

"It tastes delicious," I said, as I wiped my mouth, "like ordinary milk. Are you sure you're not a milking mare? With breasts and milk like yours, you could sell milk."

"No silly," she said with a giggle, "I'm not a fan of getting milked, but I do like it when you do it though."

Derpy then looks down and gasps. I look down to where she was looking and noticed a tent in my pants.

"Sorry," I said, "that was inappropriate of me."

"Actually," said Derpy, as she fidgets with her fingers, "can I…see it?"

"You would?"

"I'd like to milk you, as well."

"I must warn you, that it's…different then a stallions."

"I don't care, because it's you."

I blush and began unbuckling my belt, making my pants fall to the floor. I then pulled down my boxers, making my four-inch member pop out. Her wings flare up, but then went down.

"My," she says, as she inspects, "you weren't kidding. It does look different."

"I told you."

"Can we do this next to the fireplace? I'd like to do this where there's room for us to lie down."

"Of course," I said, as I kick my pants, buckle and boxers away.

We walk over to the fireplace, as I began to feel a lot warmer. I then began taking off my shirt, revealing to Derpy my abs that made her squeal like a fangirl.

"Your muscles look so cool," she says.

"Thanks," I said, "I do contraction and do a lot of heavy lifting."

She then places her hands on my chest and pushes me down to the floor. I was on the ground, as Derpy crawls up to me and places her breasts between my member. My God, they felt amazing. It felt like two marshmallows squishing against my member.

"Does this feel good," she asks, as she squeezes her breasts against my member.

"Y-yes," I said before giving out a light moan.

"That's good to hear," she says, as she rubs her breasts up and down my member.

I moaned, as she picked up the pace and began feeling her tongue reach down to the head and giving it light licks.

"Derpy," I moaned, "this feels amazing. Your breasts are the best."

"Thank you," she said before stopping her titfuck and began sucking on the head.

Her mouth felt warm and moist, as she starts bobbing her head up and down.

"Derpy," I moaned, as I gripped onto the carpet, "I! I'm about to cum!"

I yelled, as Derpy reels her head back and allowing my load to spray against her face. Her face was covered with my seed and she licked her lips.

"It tastes delicious," she said in a sultry voice, "almost as good as my milk."

"That's good to know," I said, as I reeled my head up to look at her.

"By sucking your cock, made me wet," she said, as she stood up to reveal to me her pants looking wet.

She unzips her pants, as it falls to the ground. She then sticks her fingers in her dripping pussy, as though she were putting on a private show for me. Her tongue sticks out, as she tries to stick her fingers deep inside with drips of her juices falling down onto my legs.

"Can you lick it for me," she asks, as she pulls her fingers out and shows me her sticky fingers.

"Can't keep a lady waiting," I said, as I went on my knees and sticked my tongue out.

I began licking around her vagina, making her coo before I licked at her clit. She moaned loudly, as my tongue licked within her.

"Sweet Celestia," moaned Derpy, "you know how to use your tongue."

I continued to do so, until Derpy gives out a yelp with her juices squirting onto my face. She lays on the floor panting, as I could smell her juices seeping into my nose; it smelled like cranberries.

"Jake," panted Derpy, "I want you to put your cock in my muffin."

I grab my member ad slowly stick it in, making her gasp.

"What? Are you okay?" I asked.

"It's okay," she said, "just be gentle."

"For you, I will."

I slowly thrust into her, sending her pleasure like no other stallion could do. Her tongue sticks out, as I continued giving her more thrusts. I began to pick up the pace, as she sits up and wraps her arms around my neck.

"I love you," she shouts, "I love you, Jake!"

"I love you too, Derpy!"

In the living room were the sounds of slapping flesh, the crackling the fire and the sound of panting loudly.

"I! I'm! About! To Cum!" shouts Derpy between thrusts.

"Me! Too!"

I thrusted as quick as I could, before the both of us released out juices within one another. The two of us lay on the floor panting, as the fire crackled beside us. I reached over to Derpy's left and pulled out a blanket from under the coffee table. I place it over us and snuggled against one another.

"That was amazing," said Derpy, "you are just amazing."

"You are a sexy mare," I said before we both nuzzled noses.

"Well, shall we get some sleep?"

"Good night, my mailmare," I said, giving her a kiss.

"Good night, you handsome human," she said, as her eyes closed.

"In the morning, I'll make us some muffins with berries."

The two of us fell asleep, as the fire began to flicker out, making the room pitch black.

Author's Note

"Clumsy is sexy"
- Konata From Lucky Star