My First Anal Experience – Anal – Free Sex Story

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This following is a true story, my story.

For those of you who have read “Billy and the Big Load”, welcome back. This is my second hookup with Billy, so please read it before you proceed with this story.

It was about a month after the “Billy and the Big Load”, that we met again. Just a reminder, I’m not using real names; Billy is just what I’m using to represent the other guy.

So during the period between our first and second meet, we continued to text on Grindr. We just exchanged flirty and dirty texts. He’d even sent me a picture of him fucking someone. And I immediately thought, “wow! I want him to take me”. Now here’s the thing, I wanted to have Sex. More precisely, I wanted to get fucked. And he was a nice guy, and I liked him. I felt comfortable and it didn’t hurt that he thought I was cute so I messaged him. I decided to Shower before I left for his house and thoroughly cleaned because hygiene, duh. And then I left for his place.

After walking 15 minutes, I reached his place, and he was waiting at the gate, with that smile, except this time, it looked more notorious. He was Horny for some Ass! We entered his house, and I slowly walked to his room. I was excited, and also nervous. It was a big step!

Before I realized what was happening, he came up behind me and began to feel me up. He helped me take off my jacket, and then my shirt, and then we fell onto his bed. We both stripped and I was completely naked, in his bed. He looked at me and smiled, and then slowly went down. He gripped my cock and began to jerk it slowly. As he continued to stroke me, I was getting harder and harder. He then wrapped his mouth around my cock and began to suck me. My eyes shut, my mouth opened, and I exhaled. Waves of pleasure ran up my body as Billy kept going. Then I got up and pushed him onto his back and leaned towards his cock and smiled, “It’s my turn”.

The familiar taste of his cock drove me wild and I kept blowing him with intent. After a while, I laid back and looked at him. He asked me, “You ready?” I looked him in the eye, my body trembling, I said, “go easy on me”.

He then turned me over and went down, and I felt his tongue between my cheeks. I don’t like the concept of rimming and so I wanted to stop him, but at this point I felt like I’d surrendered my body to him. Then he turned me over and I laid back, and he leaned over me, and held my legs, I willingly lifted my legs up, over his shoulder, maintaining eye contact the entire time. And then he leaned further and I felt a pain. His cock was trying to make its way through my hole. He knew it was my first Anal experience so he went easy.

He started to thrust gently, and with every thrust, I felt him go deeper and deeper. And then finally, he was inside me, and then he just held still, allowing me to take in the feeling, and get settled. I couldn’t open my eyes. I relaxed and focused on my breathing, allowing my muscles to relax. And just like that, the pain turned into waves of ecstasy. He began to thrust in me and I started to let out little bursts of laughter in pleasure, and then, I was moaning. He then leaned in and his lips touched mine. I tried but I just didn’t feel right kissing guys so I said no. He smiled and said that’s okay, and continued to fuck me. Then suddenly, I wasn’t feeling it anymore, and began to wonder, “what the hell is going on? Why am I suddenly not as excited as I was few seconds ago?” And I realized, he had music on. Full credit to him for trying to make my first Anal experience as lovely as possible, but the music just wasn’t doing it for me. So he got up and left to turn off the music. When he went, I just laid there in his bed thinking, “wow, this is really happening!” Then he came back, and just like that, he was fucking me again. He looked at me and said, “do you like it”? I said,”yess, fuck me harder…fuck me harder”. And so he did. He started to thrust faster and very soon, I asked him to slow down. I realized this is probably too much for my first time. But I just wanted more, so I let him go harder again. He kept varying the pace, and it was perfect. He then told me he was going to cum, and then he pulled out and this time, I had him cum on my body.

We then just laid there for a bit, allowing me to take in everything that just happened. Then we got dressed, and after a brief chat, I left.

I was so wet, so when I reached my house, I got into the Shower, and before I cleaned myself up, I closed my eyes, thought of what had just happened, and masturbated in the Shower. The was just the beginning 😉