First Time Anal

My buddy and I had planned a night to hang out at his apartment. He had moved to a new place and we had hung out a few times. We would watch t.v and eventually get naked and start sucking each others cocks. This night was no different. The expectation was we would chill, get naked and suck each other until we both came and then I would go home. 

This night was a little different. As we were sucking on each other, I just started to feel that I needed a little bit more than what we usually do. We had always stuck to the same thing but I was curious if he was up for trying something new. We had always joked about fucking each others ass before we had ever done anything so I figured it might be a stretch but maybe he would want to put his cock between my ass and slide it up and down my crack. I wanted to feel someone on top of me so I figured this would be a good way. In the middle of sucking his cock on the couch, I said to him " I need something more". Then I stood up, wiped my mouth and told him to follow me to the bedroom.

I climbed up on his bed and laid down on my stomach. I told him that I wanted him to put his cock in between my ass. He climbed up and straddled my legs so his dripping cock was on my ass. I was planning on him sliding his cock in my crack and sliding it up and down my crack until he came on my back. He placed his cock on me then as I was anticipating his cock to slide up my crack I felt him stop. His legs were on both sides of mine and he proceeded to slide his cock up to my hole! This was unexpected! I never had a cock go into my hole. He pushed his cock at my entrance and it started to go in. It got just a little bit in and then this incredible pain hit me and I clenched up. Wow, it was painful. He pulled back and said “let me get something to help out". He came back with some lotion and lubed up his cock. He started to ease his cock back in my hole. I told him to go really slow. He did and as he slid in, it started getting easier and without pain. He got to the bottom and just stayed there for a bit. He asked if "I was ok” and I told him “yes”. He then proceeded to start to slide his cock out of my ass and before he slipped out he pushed back into me. Then he started to slide his cock in and out at a nice slow pace. I started to really enjoy it after the little bit of pain went away. After about five minutes of going in and out slowly he started to pick up his pace. I could feel his body pushing on mine and I was fairly helpless in this position. I just relaxed and his thrusting got harder and faster. Now he was just going fully in and out at a fast speed. He then moved up and grabbed both sides of my hips. He started to really pump me fast while holding and pulling my hips into him. This made him go in deeper. This lasted for a few minutes and then he said that he was going to cum. I was not sure if I wanted him to bury it deep in my ass and fill me with cum or pull it out and cum all over my ass and back. In a moment of panic, I told him to pull out when he is ready to cum. He made some more hard deep thrusts and then he abruptly pulled out and came all over my back shooting half way up my back and dribbled cum all over my ass.

      He unstraddled my legs and went to clean himself up. He came back with a towel and wiped his cum from my back. I rolled over and just laid there thinking about my first anal experience. I got dressed and went home. I thought about how awesome it was and how the next time I want him to cum inside me. Can’t wait till we do it again!