Requested By: DominateDarkness
M Umbreon X M Sylveon

This interesting little encounter happened just yesterday. Just for a little backstory, I am an Umbreon, male, and live in a decently nice town. I also go to high school near the outskirts of my town that I just started about a week ago. This took place in that school with a certain Sylveon. I'll get into that soon. It was a Tuesday and around 7 in the morning as I started getting ready to go to school.

After getting ready, I walked to my front door and opened it, walking out and closing the door and began walking to school. When I reached school, I just walked into the front gates and sat down to wait for the school to open. While I was waiting around just on my phone, I looked up and noticed her. A Sylveon wearing a cute skirt. I kept my eyes on her and saw her walk behind the school.

"Huh… That Sylveon… I see her everyday. A great cheerleader and I can't keep my eyes off her." I said.

Slowly getting up I sighed.

"Eh, I am sure that Sylveon wouldn't even get to me. Oh well… I'll still watch her cheerleader sessions after school." I said, hearing the bell.

"Okay… Time for school." I told myself, grabbing my bag.

I made my way to the doors and walked in. Upon getting in, I did my morning stuff I always do after getting in school. After that, I walked into my homeroom and sat down at my desk, ready for another day of school.

The day ended up going well. Nothing much worthy to note but when lunch began, it somewhat changed. I walked in normally and like everyday, I noticed that Sylveon who already arrived and sitting with some friends. Letting out a sigh and walking by without eye contact, I got my food and sat away from them.

"I am fresh to this school. I am sure that Sylveon doesn't even know I exist here. For being here for just a week, I already attend her cheerleader sessions after school. Not really sure why. Could join the football team. Eh, oh well… I guess I'll just get more used to this school before doing anything with her." I shrugged softly.

I went back to my food but kept my eyes on her. When lunch was finished, I got up and walked to my next class but to my surprise I was stopped by the Sylveon.

"Hey." She simply said.

"Oh, um, hey..." I was confused.

She noticed my confusion and giggled softly.

"Just wanted to say hey. Well… I guess I'll be going now." She said, walking by me.

I looked back at her and tilted my head, extremely confused.

"Um, okay then… That was weird." I told myself and walked out to the hall.

As I walked out in the hall, I closed my eyes and shivered. I tried to continue the day and it went well enough until after school started. I walked to my locker and grabbed my stuff before walking out. I sighed softly and noticed Sylveon walking out with others down to the field. I sighed once more and looked down.

"She noticed me finally… But I froze up..." I closed my eyes.

"This sucks… I wish I can talk to her but it's hard..." I told myself and walked outside and around the school.

Upon reaching the corner, I noticed them beginning their session as I slowly walked to a bench and sat down. I tried not making myself known as I didn't want to appear as a weirdo to Sylveon so I covered myself with my backpack and hid my face to appear as I was looking at something or doing something. My eyes were just able to clear the top of my backpack as I watched them.

I sat there for 15 minutes before something happened. One messed up and everyone fell after trying to do a stunt or whatnot. I watched and looked at the Sylveon before I noticed something that made me freeze slightly. As she fell on her back, I got a look under her skirt for a moment but it was enough to notice a large bulge which clearly said she was actually a guy.

I was shocked as she noticed me. I didn't knew what to do so I quickly got up and just walked away, surprised with what I just saw.

I sat down near the exit of the school and after five minutes, I suddenly heard something. I looked back and instantly looked away, seeing Sylveon. He walked up to me and looked at me.

"Hey, uh..." He said.

Staying silent, he sighed softly.

"U- um… Can I ask you something?" He asked.

"Huh…?" I looked at him slowly.

"Um… Can you come by my place? I… Need to talk to you." He said.

I slowly nodded, not knowing what to do. He smiled softly and gave me his address. I took a note of it as he walked off. I stayed there for a bit before slowly getting up and going to his house. When I got to his house, I knocked on the door and he opened it.

"O- oh, come in." He said.

I nodded slowly and walked in. Before I was able to talk, he grabbed me and begged me instantly to not tell anyone. I was caught off guard but I agreed to not tell anyone since I don't mind it actually deep down. When he calmed down, he looked at me and told me if I was serious. I nodded and he smiled widely, hugging me. When he departed, he looked down slowly.

"W- well… Um… I'm very grateful. Um… I think I know how to repay you." He said.

"Huh?" I looked at him.

He leaned close to me and whispered in my ear.

"How about you fuck me?" He giggled softly.

My face lit up and looked at him in surprise but I slowly looked down and nodded. I accepted because it was an offer that would possibly never happen again and he was so sexy even as a male. Sylveon looked at me and giggled more and stroked my ear.

"I promise it'll be fun." He said, taking my paw.

He slowly walked me to a room and opened it with one of her feelers. The room we walked into was a bedroom as he looked at me and let go of my paw. He fell on the bed and giggled in a girl tone which made me blush harder. His skirt lifted up and soon his feelers reached down and pulled them off. My heart raced seeing him undress slowly as his feelers soon went back up and went into his panties, pulling them off too.

Upon him pulling them off, I finally saw his surprisingly large balls and thick penis. Sylveon giggled as he feelers gently massaged his balls, looking at him.

"Well? Come on, hehe." He giggled as his feelers wrapped around me, pulling me towards him.

He pulled me close where my own crotch pressed against his. I let out a shivery breath and stared at him who smiled and reached out, stroking my head.

"I'm ready for you, hehe." He said.

I nodded slowly as his feelers undressed the lower part of my body, soon leaving me naked. I was completely red in the face as he began rubbing our crotches together. I didn't know what to think at that moment. The feeling of him rubbing our dicks together felt oddly pleasurable.

My ears lowered slowly as he continued. This was when he let out a cute little moan and licked his lips.

"This is going to be so fun..." He quietly said, letting go of me.

The little rub session was enough to leave me rock hard already as Sylveon slowly got up and turned around and got on all fours, exposing his anus to me. He shook it side to side, his pink tail swaying with the movement.

"Please thrust it so deep into me, big brother." He said.

Hearing him say big brother to me made me feel weird inside but I did what he said and slowly got behind him. I grabbed my dick and pressed it against his ass as he cutely purred, his feelers waving around slowly. He looked back and me and let out a small giggle, telling me to do it and not to hold back.

Slowly nodded, I did what he wanted and pushed into him. He let out a very cute moan and wagged his tail as I began thrusting slowly in and out of him. It really felt weird at first as his ass was tight on my dick, but it started getting better as I kept it up, feeling his ass adjust to me size.

"O- ooo… So much better then I thought, heh..." Sylveon said softly.

"Huh…?" I looked at him.

He giggled and told me he wanted me to fuck him the moment he saw me. I blushed hearing this and just continued to thrust, surprised he wanted me to fuck him the moment I came to the school.

"Y- you are so big, heh..." He suddenly moaned.

He wasn't really joking, since I do have quite a large and thick dick. I was hit on girls quite a lot because of it, but I didn't expect to get together with a male. But for some reason, I liked it and I continued to pump into him.

"S- so big indeed, heh..." He said.

"And you like it…?" I panted softly.

"I love it…!" He moaned, his tail wagging heavily.

I smiled softly when I heard this, glad someone is enjoying my large cock. My paws gripped his side softly and started going harder into him. Sylveon moaned more and more as I continued going deeper and harder.

"P- please fill me more brother…!" He moaned out.

"You g- got it." I said.

My paws placed on his ass and spread his anus apart which made him cry in pleasure. After stretching his ass as far as it could possible go, I started truly digging into him, shoving my entire cock into his ass. I panted harder and closed my eyes. For my first time, it was already getting to me. My pleasure started reaching it's peak already which was a disappointment for me but I tried holding out for as long as I can.

My fur became quite shiny due to me sweating harder as my heart beat quicker, my breathing becoming uneasy as I started tensing up softly.

"I… Don't think I can hold it… D- dammit..." I moaned.

"It's okay, h- heh. Give me all of it…!" He said.

"O- oh, okay..." I moaned softly.

I continued to thrust deeper into him and soon I gasped, feeling myself shoot multiple strings of sticky cum inside her.

"S- syyyllllll!" Sylveon moaned loudly as I felt his ass tense up around my cock.

My first load was so powerful and large and it felt so amazing as I continued to squirt string after string of thick sticky cum inside his anus. This lasted for at least 30 seconds before I finally slowed and stopped, panting heavily and shaking softly, feeling the immense pleasure throbbing through my dick. Sylveon panted heavily as well and looked at him, giggling weakly.

"T- that felt s- so good..." He moaned.

"Y- yeah..." I replied.

Sylveon slowly let out a smirk.

"B- but we're not done yet." He said.

"Huh…?" I looked at him.

His smirk grew as he slowly removed my cock from his ass, seeing my cum leak from his anus.

"Not… D- done at all, heh..." He giggled and pushed me on my back.

I fell flat on my back on the bed and looked at him. He moved closely to my cock and suddenly licked it. I let out a small moan as it twitched softly, still full of pleasure.

"Looks so good..." He said, opening his mouth.

He then slowly inserted my cock inside his mouth and began sucking on it. I relaxed my body slowly as he kept sucking slowly, licking my shaft nice and slow.

"O- oh… So… Good..." I moaned softly.

He giggled through his sucking and suddenly it changed pace. Before I was able to get prepared, he thrust my cock down his throat. My legs stiffen as I looked at him, taking my entire and massive cock with ease and no gagging whatsoever. I was impressed honestly as my paw rubbed his head slowly. His tail wagged in delight as he kept deepthroating my dick.

The pleasure that was sent through my body caused my rings to glow faint yellow. The pleasure was just so intense already from ass fucking him that I already felt like cumming again, but I held out this time so he could enjoy my dick.

Sylveon clearly enjoyed it as he continued to just thrust it deep into his throat, not gagging or struggling once which made me wonder how he could do this with ease. I didn't really want to ask him however at the moment due to her mouth being full.

So we were just here for five minutes, Sylveon sucking me heavily and moaning cutely. This was at the point where I couldn't hold it anymore and looked at him. I shakenly told him that I was about to cum again. He nodded and smirked before consuming my entire cock. The warmness of his throat was too much and I came down his throat heavily. Sylveon kept my cock deep inside her throat, drinking every last drop I gave her. He did a good job as not a single drop fell from his mouth, drinking every last bit and I giggled softly.

I came for a bit longer before stopping as he removed my cock from his mouth, panting heavily and looked at me.

"T- taste so good." He giggled.

"Really…? Heh..." I rubbed her head.

He nodded and hugged me. I hugged back and gently rubbed his head. He giggled and stroked my back.

"That felt so good… But now I feel so tired..." He said.

"Y- yeah…" I replied.

"How about we get some sleep…?" He asked.

I nodded as we snuggled together.

"I think I found the perfect boyfriend, heh..." He said.

"S- same..." I smiled softly.

We kissed softly.

"Goodnight big brother, heh..." He said.

"G- goodnight..." I smiled and closed my eyes.

We then fell asleep...