My Anal Teen Cherry Got Popped - Sex Stories

My Anal Teen Cherry Got Popped

This is a true story of my first time having sex at 16-years-old.

This was in 2002 where I dropped out of high school in the beginning of my fall semester of my junior year. I was placed in an alternative school within the school district where other students who dropped out can make up their credits at their own pace. During this time, I was still in the closet with my family and friends as I acted like a typical teenage boy trying to fit in and be cool. I tried looking tough, dressing in baggy clothing, sagging my pants, smoking weed, and was hitting on girls.

That was my fake persona when I was in public. A wannabe bad boy who was a short 5'5 Filipino kid that had long flowing straight black hair just past my shoulders, which at times I styled into corn rolls. I also had light brown eyes, large lips, cute face that the girls loved, caramel skin, skinny physique with a flat chest and flat stomach, no facial or body hair other than my pubes that I usually shaved off, and an abnormally large peach shaped ass which was always covered by my baggy pants. I was such a poser trying to replicate how gangster rapper's acted and what they wore from the music videos that I have watched.

When I was at home, you would find me in my bedroom, that I locked at all times, so my parents couldn't barge in and see what I was up to. I loved being on my desktop computer because I could be the total opposite of who I portrayed to others. I had an unhealthy obsession with porn as a teen ...

... where I would masturbate multiple times a day as I enjoyed watching scenes of blowjobs to deep throating, threesomes to gangbangs, cum play to creampies, and anal fucking to gape scenes. I watched it all from straight to gay porn. I do remember that I was obsessed with BBC and teen/old men type porn during this time. I truly thought I had daddy issues back then because I didn't really have a relationship with my dad who was in the navy and constantly out on deployments at sea.

Back in the early 2000's there wasn't any type of social media like we have today. Chat rooms, message boards, and instant messaging were all the craze for people to meet and communicate online. When I wasn't at school and my parents were at work, I would be online in MSN chat rooms finding people to talk to, on AOL instant messenger chatting with my friends, or downloading porn to watch.

I have always been a curious person. When curiosity hits me, I get so hyperfocus with whatever I am curios about that nothing else really matters at that moment. I was already so heavily into watching porn when the curiosity bug hit. I wanted to see if I could take it a step further and actually do some of the things I've watched with a real person.

One day I scrolled through the different MSN chat rooms and found a room that was for tops and bottoms. My curiosity sprung into action as I opened the room multiple times throughout the day and night for the next couple of days just lurking to see what the chatroom ...