My name is... Eh, I’ll decide what my alter ego will be later. Haven’t gotten that far yet. I am currently 28 years old and for the last eleven years, I have experimented with my sexuality. My first time having sex with a guy was when I was 15. Before then, I experimented with anal pleasures when I was a lot younger. For some reason, anal sex always fascinated me. I never saw it as a bad thing and when I first watched porn, it made me wonder why people did it. So I tried on myself. It felt strange but it wasn’t a bad strange (but it was messy!). Soon as I got older, I experimented more and more with it. Shoving things in my ass and getting intense orgasms from it. When my first time happened, it was unexpected. It was a guy from my math class who was deemed as one of the “popular guys” in my school. He was a very good looking white guy too. Imagine my shock as someone who was very reserved and quiet in school and kind of a social outcast being lusted by someone who girls had crushes on and were heartbroken that their dream guy was actually gay. To me, I felt a little more excited about this. But the idea of having sex with a guy was still nerve-wracking to me. But he didn’t let up, he kept hitting on me in class and on the school bus. I openly objected him but secretly liked it and I think he knew that too. One day, I got off the bus and he was there with his shirt off and muscles showing. He was the one who gave me my first cigarette so he was there to give me one that day. He walked home with me and invited myself into my home. He knew my parents were at work and my sisters were in school until 4pm. He sat on my couch and we talked and watched music videos on MTV (when that was still a thing!)

Since he had a habit of hitting on me, I got used to the usual flirting he did but today was the day he actually succeeded. He always pointed out when he got an erection in his pants and would show me his bulge. I saw it and laughed at first but then I got something in my head to poke it... and I did. Then after doing that, he pulled down his pants and showed his beautiful dick to me. Instantly, I got up and... I walked into the next room with my heart racing. Next thing I knew, the phone rang and startled me. It was my mother calling from work and asking me if I was okay. As I was telling my mom that I was fine, the guy (who we can call Tim) wandered in with his pants down and dick swinging. I stared at it as I was on the phone. When I finally got off the phone with my mom, I just looked at him and he was smiling. He knew I wanted it. That I wanted him. I told him to wait there in my dining room. I went upstairs to my room and grabbed a bottle of lube that I stole from my parents room. It was one of those self warming lines (that I didn’t really care for but it was all I had at the time). I went back downstairs and handed him the bottle... and dropped my pants... and bent myself over a chair... while Tim lubed himself up, rub his huge dick between my ass cheeks... and put himself in me.

This was the first time I ever felt something like this. It was smooth and went in easier than anything else that I used that was phallus shaped. It hurt a little bit but it went away and the pleasure kicked him. It was in that moment all my nervousness evaporated away and I felt myself feel lightheaded. I felt his dick in my ass and he was slowly thrusting himself. He was very good at understanding it was my first time. He put his right hand around my waist and grabbed my dick and jerked my slowly as he kept fucking my virgin ass. We then agreed that we needed a change of scenery so we went to my room. I was on the edge of my bed on all fours while he kept fucking and jerking me off. It felt incredible, I couldn’t even think about anything else except how amazing it felt to have sex like this. In some ways, it felt better than sex with a girl (I had sex with two girls up until this point). Eventually, he kept hitting my o-spot and I eventually came. I had cummed so hard like I had never came before in my life. Sadly, I felt bad that he didn’t cum but he didn’t mind. My sheets were covered in my cum and I laid on my bed just motionless and still. It was like I was coming down from being high (I assume that’s what it feels like. I’ve never done drugs before so I wouldn’t know). When I finally got up, I looked at him. I asked him one question: “Did I feel good?”

“Yeah you did” he said with a cool smile.

Afterwards, we left my house and he walked with me to get my sister from school. We talked as if nothing happened but he made a joke about how hairy I was (I’m half Arab so by default, I’m naturally hairy. Can’t help it. I do shave myself from time to time though). I felt a little embarrassed and ashamed but I guess he knew that because he followed it up with “but I like it though”

After that day, I didn’t see Tim for a while until the beginning of my sophomore year in high school. Tim and I had this relationship where he was tease me in his own sense and I would brush him off and tease him back. But we both knew it was different now just like we both knew that when my parents weren’t home, he was coming back to my place.

And that is the story of how I lost my (anal) virginity! Hope you enjoyed it and feel free to share your stories in my DMs. To this day, no one knows about my secret life except those who I shared it with. Not even my parents know. It’s my life and I decide how open I want to be and who to expose my identity to. Until next time!