(18M) First time anal - giving and receiving (PT 1)

There was history between me and my best friend. 

He was staying the night at my place again. It was easier for us to have fun when he came to my house. My parents were older than his and loved to travel the world. I was left at home alone frequently for long stretches when they traveled. He would come over and it was just us. I would literally almost shiver with excitement when I knew he was spending the night. One of my favorite things was sucking his cock.

It would happen the same way every time. I would ask him if he wanted to “do it” and he knew what I meant. I always thought it was kind of funny… He never let me touch him unless his cock was hard already. So he would tell me to wait while he touched himself and got it nice and stiff. We had of course proven on more than one occasion that it was no problem for me to take him from soft to raging in minutes with my mouth. Still though, he almost always wanted to be hard first.

We always went to bed wearing nothing but our boxer briefs. He would strip them off and I would climb between his legs. He always came over freshly showered and used the same soap for as long as I could remember. The scent was intoxicating to me as I lowered my head down and inhaled the fresh soapy smell, grabbed his stiff young cock in my hand and popped it immediately into my mouth. We were young and inexperienced. Never thought to mix it up doing things like licking or sucking on his sack, tonguing his smooth young ass, or even licking or stroking his shaft. I just knew to put it in my mouth and bob my head up and down until his cum filled my mouth. The way I would do it, it pretty much constantly rubbed the head of his cock on the roof of my mouth. Apparently that worked well because he never lasted long.

It was always the same, but I loved it. The feel of his stiff cock in my mouth. I would touch his tight sack. I loved the feel and look of it. He was one that had that very pronounced line that ran from his pink little asshole, across his taint and up to his sack. Always thought that was hot, still do. I would be bobbing my head up and down, the head of his cock rubbing rhythmically on the roof of my mouth. It was strange… We had the whole house to ourselves but always did this in my bedroom, in my bed, lights out. It was dark and silent and I loved to hear his breathing while I sucked him. He would lay still at first, but eventually his hips would begin to pump lightly and involuntarily I think. It was so fucking hot feel him get thicker, stiffer as he got close… His breathing louder, ragged and hitching. Lots of precum leaking out of him, more sweet than salty back then. He tasted amazing always. Those last few breaths always told me he was cumming for sure. His hips would come off the bed, locked upward, his raging cock thrust deeper in my mouth and then his dick would convulse like crazy. I loved that feeling. It was so hot to have him spasming in my mouth, hot waves of his sweet cum spilling into my mouth with each one… I would swallow every drop eagerly. We never talked about it. Just once we had cum, we rolled over like nothing and crashed out asleep.

It might surprise you to know we both had girlfriends and were sexually active with them. But again, long history between he and I, and we each seemed to enjoy continuing things. Somehow we never found it weird that we were “swinging both ways.”

So, now you have the history of what we typically did. Tonight was different. This time he asked me if I had heard of having sex “up the butt.” Of course I had and as soon as he mentioned it, I knew where this was going. I was literally shivering with excitement as we talked about it. And I’ll tell exactly what happened in part 2.