Under a Watchful Eye

by darthshadow25

Rating: mature
Tags: Sex, Slice of Life, My Little Pony: Friendship is Magic, Romance, Original Character
Length: 5224

In Ponyville there lives a mare with a keen eye and a slightly voyeuristic proclivity. She appreciates the pony society's lack of clothing.

Rainy Day is a mare who just can't get enough. She loves looking at stallions and what they have to offer the mares of the town, and she doesn't let the the norm of being nude mitigate her enjoyment of the male form.

In this story I will explore the concept of constant nudity in relationship to its affect of a voyeur through the eyes and experiences of Rainy Day.

Published 2017-03-04 06:30:01 UTC
Last updated 2017-03-10 17:14:30 UTC

Chapter 1: Sunny days and reveries

As a mare in Equestria, you see countless beautiful sights throughout your life. From the picturesque vistas of Rainbow Falls to the charming simplicity of Ponyville. You are never short on wonderful things to look at. This, of course, includes stallions.

There are many ways a stallion can pique a mare’s interest, but none quite as profound or inherent as their appearance, as first impressions are everything, and how a pony looks contributes largely to their attractiveness.

A myriad of factors goes into the sex appeal of a stallion. Ranging from things in their control like geniality, cleanliness, physique, and swagger, to things wholly outside of their control like palette, personality, height, and, arguably the most important, package.

Oh yes, the package.

While many, or even most, mares will marvel at stallion’s...well, stallionhood, they will most certainly deny it. They believe it to be uncouth or inappropriate to gaze at a pony in such a way, but that doesn’t stop them from taking in the sights.

Though true that we don’t often wear clothes, pompous places like Canterlot notwithstanding, and we have been desensitized to seeing stallions and colts sheepishly struggle to conceal a poorly timed and uncontrollable bout of arousal, we still can get some thrill from gazing and marveling at what Celestia gave us. It is in our nature.

But of course we are better than that and should never ogle other ponies like some piece of meat, no matter how juicy or tender that meat may look. This, however, stops virtually nopony from doing it. I know it doesn’t stop me.

In fact, it is my favorite pastime.

Now this is not to say I’m a whorse, I don’t touch...usually. I just like to take in the sights and appreciate the wonderful and bountiful garden of fertility cultivated in my little town of Ponyville, and what a harvest it brings during the summer when most mares, including myself, go into heat. Like I said, I usually don’t touch.

When I’m not touching (them at least), I’m watching, enjoying the sights and sometimes smells. I admit, I’m a very needy mare, I’m horny all the time, but I have self control and have enough brains to realize that I don’t feel like paying to have an STD some swarthy stallion gave me after a night of passionate rutting zapped away by our neighborhood physician. His horn is multi talented.

So, in the interest of my modest stockpile of bits and the little bit of shame I do have, I stay away from most suitors, opting instead to just gazing at them or even having a nice, flirtatious conversation before going home and hoofing myself silly. I’ve gotten very good at hoofing myself, getting myself to erupt in pleasure and sometimes bodily fluids, fueled by nothing but my thoughts of those I had seen and my skillful hoof. Sometimes watching stallions gets me so worked up I have to run home and-

“Excuse me, miss?”

“Hmm….? Oh! Did you say something? I’m sorry, I was lost in thought.”

The friendly pony that had approached her smiled a kind but knowing smile. “I see, and what good thoughts they must have been.” After a brief chuckle he continued. “I just happened to notice that you were staring at me for a while and I just wanted to make sure everything was alright, but it might just be a misunderstanding. I know I’ve been lost in thought many times staring nowhere in particular.”

By the time he finished his explanation on why he had interrupted her reverie, she had taken note of a few things about this stallion. The first being his beautiful alabaster coat and kind blue eyes. She didn’t think those eyes could hold any animosity towards anypony. The second thing she noticed was what she always notices. Between his loins he sported heavy orbs just barely visible from her perspective. She instantly became jealous of any mare who had the serendipity to walk behind him. While all she could see were those two balls, like twin moons just barely peaking over the horizon, it was impressive she could see them at all at this angle. By the time this realization came over her she could hear him speaking again.

“I’m sorry, could you repeat that? She said with a sheepish smile.

With a small chuckle he introduced himself as Sky Bright and explained that he was concerned about her. Ponies don’t often space out back to back.

“Oh I’m more than fine, just an active mind is all. My name is Rainy Day, hehe, I guess we are a bit of opposites.” she said, laughing a bit too hard.

As it turns out, they weren’t quite opposites. His beautiful White coat contrasted with her clean grey one, but both of their eyes were a powerful blue. His the color of a blue sky and hers the deep blue of a pure ocean. His mane was a short cropped mess of silver and hers was an elegant, yet practical, grey mane a few shades darker than her coat.

“I guess we are.” With a genial smile he cast a glance at a cafe across the way. “I’m sorry to have bothered you, how about I treat you to some food. We can talk all about our differences over lunch.”

His eyes beamed warmth, but were slightly shaky as if he were nervous. His smile holding as he waited for the reply. Taking her time, she sized him up and down, trying not to linger between his legs for too long. After assessing his offer, she lifted her hoof and offered it to him.

“Lead the way.”

And so he did. After taking her hoof into his and gently nudging her along his path, he led her to the cafe that he knew to sell delicious daffodil salads. He trotted along happy with himself and his generosity toward the nice mare, completely unaware that Rainy's eyes were fixated on the delicious looking meal right in front of her. She realized then that she was right to be jealous of those mares.

Author's Note

This is just an idea that I had that I wanted to get down. At some point in the story It will get explicit, but I'm not going to rush to that (and by that I mean I'm not going to make the escalation to sex feel inorganic).
Let me know what you think and how I can improve my writing. I'd love to get some feedback and make the content I make even better.

Chapter 2: A salad in the ranch

The cafe was a short trot away, and while it didn’t seem to take long in Sky’s eyes, Rainy would have sworn the journey took forever. While Sky walked ahead of her and told her some story that she paid no attention to, Rainy was transfixed by those two large, heavy orbs nestled between his hindlegs. They playfully bounced around in rhythm with his trotting and made Rainy’s mind wander to filthy but oh so fun places. Sky’s tail, which hid this beautiful sight from Rainy frequently, was swishing back and forth every few seconds, accompanied by an increased enthusiasm in his voice. Apparently the story he was telling her was exciting.

As they approached the cafe, Sky briskly turned around and made a grand sweeping gesture directed behind him.

“And with that we have reached our destination. So, where would you like to sit?” His grin faltered for a second when he noticed that she had spaced out again, but she quickly regained her composure and he forgot about it just as fast.

“Ummmm...anywhere is fine, as long as there is a good view” she said as she surveyed the cafe. It was a quaint place with multiple tables set up outside and a few ponies milling about searching for the optimal table to take up residence.

“Well,” he said motioning to a table toward the building where the cafe operated out of and where you could place a to-go order. “I always sit there when I can, is that table alright?”

With a quick glance at the table in question, Rainy gave a nod and started heading toward it.
As she took the lead, Sky happily got up and trotted behind her briefly. She was a really cute mare, not a very athletic build, but she still maintained a healthy and attractive figure. Her flanks had a curve to them that made Sky wish he had the courage to ask her out. It took all the willpower he could muster to simply get this far, but his good-hearted nature made this situation easier to handle.

As his eyes wandered across her plot he thought he saw a sliver of wet fur between her thighs, but surely it was just a few errant hairs or a trick of the light. Regardless of its cause, that mental image brought a stirring to his loins. Picking up the pace and coming alongside Rainy, Sky asked her if she had eaten here before. The purpose of his question being more to distract himself rather than actually ascertaining that knowledge.

She glanced over at him and said, “Not that I can remember, but it looks like a nice enough place” then took her seat at the table across from him.

Calling it a seat was a bit of an overstatement. Really they just sat around the table in the short trimmed grass that had a few patches missing here and there from hungry customers who were made to wait a bit too long.

On each table there was a nice pale yellow tablecloth with a vase sitting on top with sunflowers in it. Rainy took note of the establishment's name, “Sun-kissed Café” which was emblazoned in bright yellow letters above the threshold to the building. Each letter elegantly stylized and the dot on the I being a replica of our sun goddess’ cutie mark. It really was a nice place, as long as you were a fan of Celestia, but then again, who wasn't?

“So have you been here many times before?” Rainy asked with a pleasant smile.

“Oh, loads of times. Back when I was in school, my mom would take me here every Sunday. It was a little tradition of ours, and the food was good and reasonably priced. We haven't eaten here together in a few years though…” Trailing off, Sky looked sad for a moment, but quickly brought his smile back and looked at the mare across from him. “All things have to end sometime, I enjoyed it while it lasted.”

“Your mother sounds like a nice pony” Rainy said while hailing down a waiter.

“She is. Nicest pony I've ever met,” he said. “Present company excluded of course,” he added quickly before looked away with an awkward laugh.

Rainy’s wings fluttered lightly and she fixed him with a challenging stare. “Oh, is that so? You hardly know me. All you know is that I'm beautiful, aloof, and willing to accept free food.”

“I never said you were beautiful!”

“I thought you thought I was pretty,” she said with a little pout while feigning being hurt. “I guess I'm just an ugly mare you took pity on. And here I thought you liked me.” Her onslaught of teasing was having the desired effect.

“W-well I meant to say...that is...I do think you are pretty, but─”

“But I'm not your type, I understand,” she said, cutting him off with a slight smirk.

“No!” He said a bit too loudly, drawing the attention of multiple other guests. “Sorry,” he said to those around them before directing his attention back to her.

“Hello and welc- oh hey there Sky!” A chipper pale blue unicorn in an apron and levitating a clipboard and a few menus said as she approached. “Who's your friend?” She added with a wiggle of her eyebrows.

“H-hey Moonbeam. Uhh....R-rainy Day, meet Moonbeam. Moonbeam meet Rainy Day.” he glanced away from the waitress, avoiding eye contact at all costs. He nervously started counting the petals on the sunflower.

“You know Sky? He said he used to come here all the time” Rainy said, enjoying how cutely nervous Sky was being.

“Oh I know him very well. He has been coming here for a long time, and we dated briefly, but we work better as just friends.” She projected a genuine smile as Sky, who sheepishly returned one. “Wow, he must really like you, he's usually not this nervous. Well, I'll leave you be. I'm sure Sky is just dying to be alone with you again.” She grinned at him playfully, knowing that she was only serving to make a hard situation for him even harder.

As Moonbeam trotted away, Rainy cast a predatory glance at Sky who was too busy counting to notice. “So you do like me. Ha! I knew it. But should I give you a chance after calling me ugly?”

“I never called you ugly! I just─”

“Calm down. I'm only teasing.” she said with a giggle. “ So, how did you and Moony over there become an item?”

“I wouldn't say we were an item. We kinda just tried it out. We both hadn't been with anypony before and we trusted each other.” he retold, glancing back at the direction Moonbeam left. “She's really nice and a wonderful pony, but we are better being friends.”

“That's a nice story and all, but that doesn't really answer my question. There has to be more of a reason than just trust and being lonely. Come on, you can tell me. I bet I already know what it was,” she finished teasingly while she rubbed her hoof in little circles on the table.

“I don't think you do...it's, kinda personal,” he said, blushing and praying that the food would arrive soon.

“Mmmmmm, I bet it's very personal. I'd love to find out w─”

“Here we are,” Moonbeam interrupted, having returned with their meals. “A daffodil salad with extra extra ranch for the handsome stallion, and a daffodil salad with a sane amount of dressing for his lovely date.”

“She's not my date!” He said defensively with a betraying blush. “I mean, kinda...I'm just trying to be nice and─”

“Oh I think you are very nice.” Rainy interrupted, giving him a hungry look. “And other than calling me ugly, you have been a perfect gentlecolt.”

“But...I didn't...aughh!” A head slamming to a table could be heard all around the cafe as Sky gave up being right.

Moonbeam giggled and gently told Rainy to enjoy her meal before turning around and trotting to another table to take somepony’s order. Rainy glanced at her flanks as she walked away. She could certainly understand why Sky had wanted to rut that. She had full, attractive, and needy lips hidden behind her silky tail. Had Rainy been into mares she would have gotten very worked up thinking about them.

Finally, Sky raised his head and started eating his ranch soup quietly while Rainy ignored him. He gave a quiet sigh and cast his eyes into his plate.

“What's wrong?”

“Huhh…” Sky looked up to see Rainy looking slightly worried, her head cocked to the side and ears lowered.

“Is something wrong?” She asked genuinely.

Letting out a much louder sigh than before, Sky muttered something and went back to eating. Rainy couldn't hear what he said, so she got up and slowly made her way over to him, sitting down and draping a wing over his back. “I'm sorry I teased you so much. I often forget that some ponies don't take it well.”

As soon as he felt her pinions brush against his back he tensed up, but after a second or two he managed to relax, enjoying the softness of her feathers. “It's not so much that. I'm just tired of messing up. It seems like no matter how hard I try, I fuck up any chance with a nice mare I get.” He lamented as he stared at his half finished bowl of food.

Frowning, she hugged him closer. “I don't think you messed anything up. I think you have done great. Just look at what you managed to get before,” she said directing his attention to Moonbeam who was deftly balancing three plates on her back. “She's a real catch, but it's not your fault that you are better as friends.”

“It is my fault...like I said. I always fuck something up,” he said while running his hoof along the edge of his bowl dourly.

“Listen mopey, I think you have done an amazing job today. How about we go to your house so we can have a nice private conversation. We can talk some things out and get to know each other better. How does that sound.” Giving him a kind and warm smile, she really hoped he would say yes.

Author's Note

So Rainy Day's cutie mark is a watering can shaped like a cloud what has 3 raindrops coming out of it's spout. Sorry I can't draw, so in the story image she is a dirty blank flank.

Chapter 3: Coffee and Couches

Rainy sat on a plaid couch looking around the room with mild interest. After she had asked Sky to take her to his house for a third time he finally relented. He told her he just wanted to be alone and that he had a nice time, but she was having none of that. She cajoled him until he conceded that he would like to spend more time with her, but not right now. To that she implored that no time is better than the present, which, being a phrase he uses often, he had to concede to for the sake of integrity.

The whole way to his house she had remained some contact with him, whether that be her wing hugging him to her or her hoof patting him reassuringly. He couldn't deny that Rainy’s attention was nice and, eventually, it made him feel a bit better.

Rainy spotted a few stallions on their way who would have been a delight to rut, but her focus was on Sky. Unlike those other stallions, he needed her right now.
But that doesn't mean she can't enjoy the view, right?

When they arrived at his house, he told her to take a seat in the living room while he made coffee. She nodded primly and took her seat. The room she was sitting in was quaint and utilitarian. Much like the rest of his house. It was very neat with not a single errant object in sight. The color pallette he seemed to prefer was simple with muted colors, which contrasted sharply with the lively and obnoxious orange, red, and yellow couch.

Rainy thought the room─ and most likely the rest of the house ─was pretty boring, but everypony has their own taste, so who was she to judge. Hell, she spent most of her free time either watching stallions or masturbating while thinking about stallions she has watched. She had no room to talk.

Around the time Rainy was about to get up and go see if he needed help, she smelled the wafting aroma of coffee. An unmistakable and satisfying smell, even if you aren't a fan of coffee yourself, like Rainy.

She didn't have the heart to tell him.

“How do you like your coffee?” Sky called from the other room. “Black, or with sugar and cream?”

“As far away from black as possible if you don't mind.” Rainy called back. She shifted awkwardly in her seat. Her arousal from earlier had dried up shortly after Sky became melancholy and now matted the fur around her vagina.

Sky rounded the corner as she found a comfortable position where she wouldn't be bothered by her sticky thighs. “I hope this is ok.” He said as he offered her a mug of coffee from a plate on his rump.

“I'm sure it will be. Thank you.”

As Rainy delicately grabbed the cup in both hoofs, Sky set the plate on the table and took his seat. “You could have at least waited until I set the saucer down first.” He said with a small chuckle, momentarily forgetting his insecurities.

“But then I wouldn't have had an excuse to get close to your flank,” she said before taking a sip of coffee, her eyes shooting wide as the contents of the cup entered her mouth. “Holy crap this is sweet.”

“I'm sorry, I knew I put too much─”

“Don't be sorry. It's delicious, thank you very much,” she said with a flutter of her eyes and a slightly sultry smile.

“If you say so…” With a small sigh he sipped from his own steaming cup and sat it down. “So what were you wanting to talk about?”

“How a stud like you thinks he can't do anything right, when in reality he could get any mare he wants.”

“I'm not a stud and I can't get any mare I want. I'd be lucky to get A mare.” He seemed very convinced of this, like he had turned this fact over in his mind and examined it from every angle, but really he probably just accepted his own point of view as fact, and continued to do so until no other options could coexist.

“Oh I beg to differ.” As she said this she looked him up and down again, taking in the sight of Sky in all his glory. Well most of his glory. The way he was positioned gave Rainy a clear line of sight on his sack and sheath. His large, balls being pushed up by the couch and slightly overlapping his sheath. His sheath was wide and thick, indicating with fairly high accuracy that he was packing a monster. Well, maybe not a monster, but certainly something that would make any mare in her position soaked. Which it was currently doing.

After her quick glance over his body, Sky casually and instinctively placed his hoof between his legs, helping to both support him and conceal his goods. The latter of which disappointed Rainy as she felt the stickiness get slightly worse.

“Sky?”

“Yes?” He looked into her concerned eyes and took a deep breath, knowing things were about to get uncomfortably real for him.

“Why do you have such a poor self image, at least when it comes to mares?” She asked, placing her hoof on top of his. She cocked her head inquisitively.

After letting out a sigh and looking away from Rainy, Sky started slowly explaining. “I...I haven't had the best experience with mares.” Each word came out slowly, like he was trying to choose just the right words.

“Yes, you told me that at the cafe, or at least inferred it. Tell me, what makes your experience so bad? I promise I'm not going to laugh.” She squeezed his hoof reassuringly.

“Well...Moonbeam, as you know, was my first marefriend. We were already late to the party when it came to dating, so that was my first clue that my romantic life was going to be less than subpar. When she asked me out, and yes, she made the first move. Well I was really excited. I had a nice mare whom I could call my own. We would kiss and cuddle, normal stuff like that. It was really nice…” He trailed off as he seemed to recollect some nice memories, it bringing a smile to his face.

“It sounds nice. So what went wrong?”

“We tried getting more serious,” Sky said succinctly, his smile falling away. “After a month or so, we were out by a lake relaxing near the water. She rolled on top of me and started kissing me, which I was more than happy to return. Then things went south when she started going south. She began kissing me lower and lower until she came to...well you know,” he finished awkwardly.

“Oh I'm well aware,” she said, rubbing the hoof that she was holding onto, the same one concealing the new subject of the situation.

After flushing a bit, he continued with a stammer. “A-as I w-was saying. She made it to my…”

“Dick.”

“Yes...my dick. After she reached that she started kissing it up and down. Before long I was harder than I ever─ this isn't right! I shouldn't be telling you this!” He said, getting up and starting to pace. “I just met you, I shouldn't be regaling you with my sexual escapades.”

“Sky, we all do stuff like this. There is no need to be embarrassed,” Rainy said as she got up along with him. “Please calm down,” she said, trying to put her hooves on him to stop his pacing. Once she found purchase, she turned him face to face with herself. “I was really enjoying your story. We are both fully grown ponies who have sexual needs and desires. There is no reason to be ashamed or embarrassed by them. Want to know a secret?” She didn't wait for him to respond. “I'm a voyeur. Nothing gets me wetter than seeing other ponies pleasuring themselves or each other.” With his information Sky’s face became scarlet and he tried avoiding eye contact.

“My point being that you don't need to hide anything from me, or be ashamed and embarrassed about it. So please, continue your story.” She motioned to the couch and after a few seconds he nodded and made his way back to his seat along with Rainy.

They sat in silence for about a minute, Rainy maintaining an implacable smile all the while. Eventually, Sky’s muscles relaxed and his breathing became normal again, although the blush had not left his face. “You really are a voyeur?” He asked, his blush deepening and his now exposed sheath twitching.

“Mmmhmm. I love it, but right now we are focused on you. So please, continue.”

After another second of casting his eyes over her body, taking in the sight of the beautiful mare in front of him who wanted to hear such an embarrassing and sexual story, he began speaking. “Well, uhh, where was I?

“You were telling me how Moony was kissing your rock hard dick all over.” She said with a slight biting of her bottom lip. After she reminded him of where he was, Rainy could see his sheath swell, a clear sign his hopefully huge member would make an appearance with a little more stimulation.

“Yeah, that. She was doing that and she began to suck it. I can't even put into words how good it felt.”

“Oh I can imagine…” Rainy purred.

“I bet.” He said with a smile, finally being able to relax mostly about the situation. “Well, even though she didn't have any experience, she did an amazing job. I started to feel funny, but at the time I didn't know that I was about to ejaculate. She kept it up and the pleasure kept increasing until…” His forlorn expression returned. “I came all over her, partially inside of her mouth, all over her face and...just everywhere. She stared at me for a long time. Probably in shock after what I just did to her. Once the shock faded she gagged and yelled ‘eww, eww, eww’ as she ran for the lake. I just sat there, partially covered in my own semen and sitting right next to the small puddle that formed beneath her before she ran.” Sky’s head drooped slowly as he explained the situation. Some of his past disgust bubbling up to the surface.

Meanwhile, the whole time Sky had been telling her the story, Rainy kept getting hornier and hotter. She knew she needed to be serious and strong right now for him. But imagining her in Moon’s position at the time made her hungry. It got her soaked.

Through force of will, she managed to shake off the cloak of arousal that the story had draped over her. “I think you might be overreacting. I'm sure you didn't cum that much.”

She was fishing. After seeing his magnificent sack she suspected that he was telling the truth, but she wanted confirmation before they proceeded.

“Unfortunately I'm not. I always make a huge mess, and 9 times out of 10 it has scared or even scarred the mares I've been with. Some react better than others, one even said she liked it. But I've never gotten another date after it happened, so who knows.” He finished lamely, looking at his forehooves.

“So...this is what you mean by you fuck everything up? You cum too much, Something that you can't control?” She asked, incredulously.

“I guess. It might not seem like much, but how would you feel knowing that every single pony you have ever dated wanted nothing to do with you after you fuck? It's not a good feeling.” Sky’s voice had risen now, but his anger seemed to be directed at himself rather than Rainy.

“Moonbeam still wants to be your friend.” She pointed out.

“But she doesn't want to date me anymore. I'm just not good enough and I never will be…” His voice died off. His eyes were puffy and he had lost all will to maintain eye contact. He simply sat there, ruminating on his failings.

“I think you are good enough.” Rainy muttered, but she didn't think he heard. “Sky, I'm not going to sit here and let you beat yourself up over something that isn't your fault at all.” Standing up from her seat on the couch, leaving a noticeable wet mark behind. “Lay back.” She commanded.

Sky looked up at her with his eyebrows creased. “What?”

“I said lay back. You are in more dire need of a blow job than any stallion in history.” She said, looking dead serious. “Don't make me tell you again.”

At the mention of a blow job Sky's ears perked and his eyes filled with trepidation laced with excitement. “But I just told you what happens every time.” He said, trying to convince her to stay her tongue.

“And I want to see it for myself and make you feel happier, because this mopey Sky just isn't going to cut it, so unless you are going to kick me out or do it yourself, lay back.” She stated with finality.

Unable to believe that this was actually happening he acted on his first impulse and started to lay back, but before he could get into a suitable position, he seemed to change his mind and sat up.

“You said you are a voyeur?”

“Uhh, I believe we established this.” She said with a slight chuckle, but the question made one of her eyebrows raise.

“Then I'll do it.”

“Ok, now lay ba─”

“No, I mean, I’ll do it. To myself. You said you like that kind of thing, and I would be more comfortable doing it to myself than having a mare I just met blow me.”

“Ok, but on one condition.” She said with a smirk.

“And what's that?” Sky asked, looking worried about what the condition might be.

“I get to join you.”