I was the only friend Leo trusted enough for this.
These past few weeks, he had been given me some signs, and then we both had gotten drunk enough for him to ask me outright. He had convinced me. We were roommates in college, both adults, and we trusted each other.
Now he was laying down on his back, pulling over his legs and exposing his wrinkled pink hole. I helped him keep his balance.
"Go slow, alright?" He said.
I nodded. We avoided eye contact. My heart was racing, but at least neither of us were hard. We were both doing this out of curiosity.
Leo's ass was as hairy as the rest of him. I tried not to stare, but it was hard since Leo was blinking. I cleared my throat.
"Dude, are you sure?" I asked.
"If you're not, please say it now..." Leo said.
"No, no, I'm good."
"I'm probably gonna hate it," Leo said with certainty.
"Yeah, me too," I said, sounding way less sure. "Me too."
We chose to do this late at night so nothing could go wrong. It would be annoying to have one of our friends knocking in our dorm while we were fucking... It sounded so wrong, but it was just experimentation.
"Should- should I... use my finger first?"
Leo handed me the lube.
"I think so..."
I put some lube on my fingers.
"Alright, here we go."
The moment my finger rubbed on his entrance, it started to blink, and Leo trembled softly, then shivered. I avoided his eyes, and kept massaging, then pushed just the tip.
He was trying as much as me to stay silent, although he let out some sighs once in a while.
Leo's hole hugged my finger, and tried to fight me, to push me away. Weirdly, I was aroused by that. I insisted, massaging the ring of muscles, until he relaxed. That's when his cock got hard.
And once it started to grow, it got really big, really fast. He had a full hard-on when I stared at his eyes, and his cheeks were a deep red. He was biting his lip.
I almost asked him if he was enjoying it, but it was obvious. The question would've sounded too... indulging.
I got hard too. Our cocks, we were bros even in size.
"Okay, hm. I'm going all in..." I said, and Leo nodded with eagerness.
I didn't think he was gonna enjoy so much.
When I inserted my whole finger, Leo grunted, then a moan escaped him.
"Is it too much?"
"No, no. Keep going."
Leo had his eyes closed. I removed my finger and pushed all the way again, then I fingered him properly. His face was contorted in pleasure... It made my cock jump.
It didn't take long for Leo's hole to be as welcoming as any pussy. It felt weird to think about my bro's ass like that...
I wanted to put my dick inside, if only to be done with it.
I warned him.
"Alright... Slowly..." Leo scratched his beard, trying to sound calm.
"Relax," I said, rubbing my cock on the tight hole. "Here we go."
I pressed my pink head and his butthole gave way.
Leo took it like the champ he was. His hole was so warm and tight, I could feel the throbbing in my cock. I had to concentrate for my body to relax, before keep going.
"Wait, wait... alright... go on." Leo didn't know how vulnerable he sounded.
He was talking in whispers. I watched his lip twitch, his eyes closed tight.
I was doing that to him..
He never complained, allowing me to go balls deep, and when I got there, I wanted to stay.
His walls were closed tight around my shaft, making me go crazy. I could feel every inch, and every vein pulsing with fervent blood.
I opened my eyes and looked at Leo, he was staring right back at me, his face all melted. His lips were trembling.
"Shit," he whined.
"Is it good?"
"Don't move... please."
It made me want to move.
With only one stroke, Leo grunted. I looked down and saw his cock starting to spill his cream all over his belly.
He shot five hot juicy loads.
I watched my friend crumble in front of me, and I knew we had crossed a line, but all it did was turn me into a beast. It was the best fuck of my life.