Under a Watchful Eye

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.”