It had been nearly a year since you arrived in Ponyville. You still had no idea how you got here, only that you arrived in pretty bad shape. Apparently you had fallen out of the sky. At first the little ponies were afraid of you, but they quickly warmed up to you. You’d even made some good friends, one of them being the quirky Pegasus named Derpy. Property was surprisingly cheap in Ponyville so it hadn’t taken long for you to save up enough money for a house. Working for Mayor Mare was rather lucrative and although she was a demanding taskmaster, your prior work on Earth as a paralegal made the transition to records officer quite smooth and easy.
Before getting your house, you had rented a room in Derpy’s house. She had been the one pony who truly showed you unconditional kindness and sympathy. That’s not to say that the other ponies weren’t kind as well, but they kept their distance. Derpy had rented the room to you for a mere fifty bits a week, much lower than the going rate for room rentals in Ponyville. You’d only lived in your new house for a week and you missed her quite a bit. You still spent time together after work, but it just wasn’t the same.
Groaning in frustration, you rolled over in bed. Ponies didn’t have much in the way of porn, and it had been a long time since you’d been with anypony or, err, anyONE. You had integrated yourself into pony culture quite well, but this was a big problem. It was around midday on the weekend and you were supposed to meet Derpy in an hour for lunch, but you had to take care of this problem first. You grunted in annoyance and slid your hand down your underwear, quickly jerking yourself. Masturbation used to be something that you enjoyed and looked forward to. Now however, it was about as enjoyable and necessary as using the bathroom. You focused on getting off as quickly as you could so you wouldn’t have to deal with these urges all day. You wanted to have fun with Derpy, not be distracted all day by all the attractive mares.
For some people, you’d imagine they’d have a problem looking at ponies sexually. But it didn’t take much for you to make the transition. Mares were sexy, and ponies in general were much nicer to be around than humans. That being said however, you knew almost nothing about courting a pony. The last thing you wanted to do was make things awkward or do something wrong, especially in such a small town. Nope. The only thing you could do was take care of your immediate needs then come up with a long-term solution later.
A loud knock on your door made you jump in surprise. Groaning in frustration you got out of bed and went to answer the door. Your frustration disappeared immediately as you opened the door and were greeted by the sight of Derpy. Seeing that clumsy, quirky Pegasus always immediately put you in a good mood. You quickly made a mental note to take care of yourself in a bathroom later as you smiled down at the Pegasus.
“Hi Derpy!” You said happily. “What brings you by?”
“Hi Matt.” She said, smiling back. “I know we were going to meet at the diner but I thought we could walk there together.”
You looked down at yourself, realizing you were dressed in nothing but your underwear. Ponies didn’t seem to care very much, but you certainly didn’t want to walk around town like this. You also realized that you had an erection, but thankfully Derpy didn’t seem to notice.
“Uhhh…I’ve gotta get dressed.” You said, turning around quickly. “Why don’t you come in and I’ll get ready real fast?”
“Sure!” Derpy exclaimed excitedly, stepping inside.
You shot up the stairs to your bedroom to find some clothes. You were able to find a shirt rather quickly, but you couldn’t seem to find any pants. How could you be so careless as to not have any pants washed and ready? You swore. Derpy looked up at you as you came down the stairs dressed in nothing but your underwear and a loose-fitting shirt.
“You okay Matt?” She asked, concerned.
“I’m fine, I just don’t have any pants…” You said, scratching your head.
“It’s okay Matt.” Derpy said. “I know you always want to wear all these clothes, but ponies don’t really care what you wear.”
“I know, but I care.” You said, looking at her in disappointment. “You mind if we push our lunch back a bit while I put some pants in the washer?”
“Okay.” She said. “I know how important this is to you.”
You quickly threw a few pairs of pants in the washing machine and came out to the living room to find the Pegasus lying on your couch.
“You know if you’re hungry you can always go without me.” You said, feeling sorry for making her wait. “We could have dinner together instead.”
“No, I’m fine.” She said. “I’m not that hungry.”
You plopped yourself down onto the couch, making her fly up into the air a bit. You both laughed.
“So Matt, can I ask you something?” She asked, sitting up and staring at you.
“Shoot.” You said simply.
“Although I still don’t understand why, I know you’re really uncomfortable if other ponies see you when you’re not fully clothed.” She observed. “Why are you so concerned with other ponies seeing you when you’re not fully clothed, but it’s okay if I see you like that?”
“You’re different.” You answer, not even needing a second to think. “In human culture, if you’re close to someone then it’s okay if they see you when you’re not fully clothed.”
“I see.” She said. “That’s very strange.”
You laughed and smiled at her, but your smile quickly faded.
“Matt, what’s wrong?” Derpy asked, concerned.
“Nothing.” You answer quickly.
“No, I know it’s something.” She said insistently. “You seem a bit….off today.”
“It’s nothing.” You reassure her. “I’ve just got some problems that I need to deal with.”
“What kind of problems?” She asked.
“Well, it’s kind of…personal.” You said, getting a bit uncomfortable with the conversation.
“But I’m your friend!” She exclaimed. “I want to hear about your problems! Maybe I can help!”
You smiled down at her and laughed happily.
“I love you Derpy.” You said, sighing. “You’re the best friend I’ve ever had. But there are some things that you have to figure out on your own.”
Derpy cocked her head cutely. “Please Matt, tell me…” She said quietly.
You sighed, defeated.
“Alright, I’ll tell you.” You said. “But remember, it was you that dragged it out of me. My problem is I haven’t…been with anypony in a long, long time.”
Derpy shot her head up excitedly.
“So you’re lonely and want a marefriend?” She asked.
“Well no, I’m not lonely.” You said. “I have a good job and a great friend like you. I just…well…I guess I’ll just say it. I need…sex…”
“Sex?” Derpy asked, her voice becoming higher in pitch.
You sighed. You knew that Derpy was an adult, but these little ponies were so innocent that you wouldn’t be surprised if Derpy hadn’t even had sex yet. It was probably a bad idea to bring it up.
“You have to understand Derpy that for guys, sex is a real biological need like eating and drinking.” You said, trying to explain. “I’ve been without it for so long, I’m going crazy.”
There was a long moment of silence between them before she spoke.
“W-well I could have sex with you…if you want…” She said softly.
“What?!” You exclaimed in surprise.
“I-I know you probably don’t want to because of my eyes, but I’ll…let you…use me…if you want.”
Your mouth was literally hanging open in shock. Derpy was turned partially away from you, blushing profusely.
It took a while, but you eventually got your voice back and could move your body again.
“D-Derpy…….I think that’s the nicest thing anyone’s ever offered me before.” You said truthfully. “But I can’t, and not because of your eyes. I care about you Derpy. You’re my best friend and I don’t want to ruin that.”
By then Derpy had gotten her nerve back and turned around to face you.
“We won’t ruin our friendship.” She said quickly. “I just…want to help you. I know what it’s like to want sex and not be able to get it. Because of my messed up eyes, no stallions even give me a second look. M-maybe we could help each other?”
You looked at Derpy in sympathy.
“Do you want to?” You asked.
“Y-yeah…” She said. “I haven’t had sex in years, but that doesn’t mean that I don’t want it…”
“Have you ever had sex before?” You ask.
“Y-yeah…” She said. “But not often. You?”
“There have been a few girls in the past.” You admitted. “But not as many as I’d like.”
“W-will you have sex with me Matt?” Derpy asked softly. “You don’t have to if you don’t want to, but I really want to.”
As much as your rational brain was screaming at you that this was a bad idea, you also knew that since you talked about this with her that your relationship would never be the same. All you could do was move forward.
“Sympathy sex, huh?” You said, your tone sour as you thought about it. “Okay, I’ll do it. But this is just sex, okay? We’re just a couple of friends helping each other out. We may or may not do it again, but we’re mainly friends, right?”
“Y-yeah.” Derpy said, breathing a sigh of relief.
“S-so I’ve never had sex with a pony before.” You said, nervousness creeping into your voice. “Where do we start?”
“Do you want me to suck you off?” Derpy offered.
“I’m already hard beyond belief.” You said. “How about I service you?”
Derpy pointed down between her legs and smiled widely. Your couch was already soaked. You made a mental note to call the cleaning service tomorrow.
“D-do you want to just…put it in?” She asked, looking down at your erection through your underwear.
“I’ve never just gone right to it before.” You admitted. “I always had to work the girl up to it, but you seem ready to go to me.”
You stood up and took off your underwear, letting them drop to the floor.
“But just to be safe-” You said, sitting down on the couch again. “-why don’t you be on top?”
Derpy awkwardly clamored over to you, stepping over you and sitting on your lap. You hugged her gently as she sat down on your crotch, her hot wet marehood grazing over your erection.”
You looked into her eyes as she wrapped her hooves around your neck, your pulsing erection pressed between you. Not wasting any time, you grabbed your erection and slid it along her marehood, popping the head into her with ease. She gasped at the sudden intrusion and you stopped immediately.
“You okay?” You asked in concern.
“Y-yeah…” She said. “It’s just…been a while…”
Seeing as her hooves were wrapped around your neck, you didn’t feel the need to hold her to keep her steady anymore. You slid your hands down her lithe form until they reached her rump. You squeezed her cutie marks and pulled her down onto your erection slowly. Her tight, quivering marehood gripped your cock as you slid yourself inside of her. She was so wet that you went in with ease, your erection pulsing as you felt each inch of her marehood engulf you. Sooner than you’d hoped you felt yourself fully sheathed inside of her, your sack pressed firmly against her rump as you pushed as far inside of her as you could go.
As soon as you were sure that you were completely inside of her, you looked her in the eyes.
“Well?” You asked. “How is it?”
“Y-you’re really big…” She said. “H-how about you?”
You thought for a moment, relishing in the feeling of being inside of her and feeling your erection pulse inside of her a few times in pure pleasure. It was then that you realized that hers was the best pussy you’d ever felt.
“You’re really tight.” You said. “Best I’ve felt so far.”
“Really?” She asked excitedly.
“Really.” You said. “I’ve only had sex a few times, but your pussy feels great.”
“P-pussy?” She asked, confused.
“Human word.” You said, not really wanting to explain it. “Now let’s not kill the mood.”
With that you slowly lifted her up and pulled her back down onto you. You almost lost it right there. You should have expected that. If just sliding inside her felt that good, then fucking her would feel even better. You’d have to take this slow.
You lifted her rump up and down, sliding her pussy up and down your shaft at a slow pace. She gripped you tightly as you fucked her slowly. She was breathing right in your ear, and you could tell that she was getting more excited because her breathing increased each time you pushed yourself inside of her.
“F-fuck…” She whispered.
This was the first time you’d ever heard her swear and you wondered why for a moment before you felt her clamping down on you. She was cumming. You had made her cum. The very thought that you could make her cum so soon filled you with pride, but it was a good thing you did because you weren’t that far behind her. You waited until she started to come off her high before you made your next move.
“Hold on.” You said, stopping momentarily.
You grabbed her flanks tighter and before she knew what you were doing you started to thrust into her with renewed vigor. She squealed as you fucked her roughly, focusing on one thing – release. You started pulling her down onto you as you thrust up into her, fucking her as fast as you could. It was mere moments after you got the rhythm right that you realized that you couldn’t hold on any longer. The thought of pulling out never even occurred to you and with a loud groan you thrust up into her as far as you could go and pulled her down onto you before you let yourself loose.
“Agh!” She exclaimed as you came. “I can feel it!”
This egged you on even more as your cock spasmed wildly inside of her, painting her insides with your cum.
“Ohhhhhhh…Derpy…” You moaned as you came inside of her. “You feel so good…”
Suddenly and without warning she kissed you and although you agreed that this was just sex, you couldn’t reject her as she pushed her tongue into your mouth as you came inside of her.
As your orgasm died down she broke the kiss abruptly.
“You felt good too…” She said, blushing.
As reality came crashing back you looked at her, then down between you. Then it hit you. You just had sex with Derpy. And as bad of an idea as it was, you really, really enjoyed it.
“Derpy, I…” You said, stirring.
“Shhhhh…” She said, putting her hoof to your lips. “We’ll figure it out later. For now, let’s cuddle.”
You couldn’t say no to that and without a second thought you turned and laid on the couch, taking her with you. You were still inside of her, but neither of you cared as you embraced each other and fell asleep in each other’s arms…