My Anal Cherry Got Popped

This is a true story of my first time having sex at 14-years-old.

This is a true story of my first time having sex at 14-years-old.

This was in 2002 where I dropped out of high school during of my Spring semester of my freshman year. 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. I dressed in baggy clothing, sagging my pants below my ass where my boxers were visible to all, smoking weed like I had no care in the world, and hitting on pretty girls.

That was my fake persona when I was in public. A wannabe bad boy who was a short 5’3 Filipino kid that had thick long flowing straight black hair just past my shoulders, which at times I styled into cornrows. 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 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 overseas.

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, communicate, socialize online. When 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. I get so hyperfocused 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 man.

One day I scrolled through the different MSN chat rooms and found a room that was geared for tops and bottoms. My curiosity sprung into action as I opened the room multiple times throughout the day, for the next couple of days, just lurking to see what the chatroom was all about. As people entered, they would type their age, position, and location, as some also added their ethnicity. This chat room was very active. It was a gathering spot for all tops and bottoms looking for sexual experiences. Requests for sex in the form of phone chat, camming, picture exchange, private chat, and in-person meet up were what I saw constantly as I read through the messages in the room.

I was still a virgin who has never been with a girl or a guy. When I watch straight porn, I don’t watch the scene because I’m sexually attracted to the girl that is getting fucked, I watch the scene to imagine myself replacing the girl in the scene. Watching gay porn was the same way. I know I’m a teen and my hormones were running rampant, but each instance that I entered the top and bottom chat room, I was craving an experience of being fucked as a bottom by a dominant top which I had been fantasizing about for quiet a while now.

I created a new MSN screen name, so I can be myself online without people I knew knowing what I was doing. I also completed portions of my new MSN profile with information of my location, sex, ethnicity, and position while adding a naked profile picture of me on all fours, spreading my big ass cheeks and showing my asshole while on my living room couch, without showing my face.

Sometime during that same week when I made my new screen name, I did what I typically do in the morning which was turning on my computer and entering the chat room. My horniness got the best of me during this day as I finally got the courage to type in the chat 18/Asian/bottom/San Diego. I added that I was looking for a local top to meet in-person. I of course lied about my age knowing that one of the rules that was enforced in the room was that I had to be at least 18-years-old to enter and participate in the chat.

I received many private messages from guys across the world complimenting my ass picture on my profile but it took quite a bit of time for a guy who lived in my city to respond. A private message with 41/blk top/SD popped up. He too commented that he loved my profile picture. I remember him asking if I could email him more naked pictures of myself but this time showing my face. At this point I was hesitant if I should go through with his request. I didn’t know anything about this man other than he was 41, black, and he lived in the same city as I do. I wanted to conceal this part of me from people I knew. I was also weary about sending him dirty pictures with my face as I didn’t know what he would do with them after.

After a few minutes trying to convince myself both why I should and shouldn’t do it, the guy I was chatting with sent me a couple “?” messages in the private chat. I remembered saying, “Fuck it” as I took my point and shoot digital camera and got naked. I set the camera on timer mode and placed it on my desk as it faced my bed. I took shots of myself in various compromising positions while I showed my face.

I emailed him three naked pictures. One of me standing, the other was of me sitting and jacking myself off, and the last was a shot of me on my back spreading my legs and asshole. He responded in the private chat something in the lines of “Fuck your hot!” He did question my age, but he let me know that he had no issue if I was younger than what I stated. I did ask to have him return the favor and send me some pictures of himself, as his MSN profile was empty, but he totally ignored my request.

We then continued to privately chat for a while as I answered all of his questions and provided him with more information about me than I should have provided a stranger. He on the other hand didn’t answer any of my questions. He didn’t even provide me with his name. I get it, he was chatting with jailbait and didn’t want to get caught. We planned for him to pick me up on the corner of my block at 11pm that night and drive to a nearby park to fuck in his car.

As nightfall came, I got ready putting on some black short running shorts with no underwear, a tight white tank top, and red high top Chuck Taylor Converses while quietly walking out of my home as my parents were already asleep. Standing at the corner of my block, I remembered the feeling of being both nervous and excited at the same time not knowing how the night will go. There was no traffic around my neighborhood at this time, especially during the weekdays, as I lived in the suburbs with blue-collar working families. I finally saw a car’s headlights driving up slowly towards me. He pulled up in his black Chevy Malibu, rolling his passenger window down, and greeting me by calling me a slut like he was picking up a prostitute.

I bent down to look at the driver. I saw a huge chubby middle-aged black man who looked to be triple my size with a shaved head and a huge beard. His muscular arms were something I could never forget because they were double the size of my thighs. Before he let me in his car, he told me that he didn’t believe that I was serious about having sex with him tonight. He wanted me take my shirt off, pull down my shorts to my knees, and show him my big bare-ass while I stood on the sidewalk to prove that I was down to fuck. I hesitated and felt pressured by the man, as he continued to say that this was a waste of his time, but I did eventually do what he requested of me as I frequently looked around my surroundings making sure that no one in my neighborhood saw what I was doing.

When he was satisfied, I quickly opened the door and sat in the passenger seat of his car. He then demanded that I take my shorts off completely and throw my clothes in the backseat. He wanted me naked with just my Converses on as I navigated him to the nearby park parking lot. I could vividly remember that he was a very dominant top and was really rough with me all night. He made me his submissive bottom as I let him do whatever he wanted with me.

This man didn’t even ask for my permission if he could touch me. His enormous hand immediately grabbed my small limp dick and started jacking me off as he continuously turned his head and stared at me and my naked body with his sex hungry eyes while he drove.

When we parked at the parking lot, he pushed his seat back and removed his shorts and boxers releasing his dick. This was literally the first time I saw a dick in-person that wasn’t mine. I stared at his dick in awe as it looked so big and thick like the BBC scenes that I have watched. His cock was massive, to my standards, which looked to be 6-inches but it wasn’t fully hard yet. In comparison, my dick was thin as popsicle stick and grows to just 4-inches when hard. I had thoughts of fear swirling around in my head assuming that his cock was too big to fit in my small tight virgin hole.

He continued being rough with me even though he knew it was my first time. I remember him pulling my head down towards his hairy cock and balls as he demanded that I open my mouth. The man started face fucking me hard and fast and at times held my head down to force his now 7-inch rock hard cock deep into my throat.

The man scared me with his dominant attitude as I continued choking me with his cock. He then directed me to continue sucking his dick as he reached to open the glove compartment and take out a bottle of lube. I copied the blowjob scenes that I’ve watched, bobbing my head up and down on his shaft and sucking on his balls. I remembered making out with his cockhead as I used my tongue to massage his huge mushroom and pushed the tip of my tongue in his head’s pisshole.

He poured lube on his hands and used two of his fingers to oil up the outside and inside of my asshole as I continued to give him a blowjob. He used his middle finger to finger fuck my hole, which was the first thing that has every penetrated my ass in the 16 years that I have been alive. I could still remember the feeling when the tip of his finger entered my hole. It was so painful that I screamed as his cock was still lodged inside my mouth. He finger fucked me until I could feel he was knuckles deep in my ass.

Once my hole was ready, he removed his cock from my mouth and started rubbing lube all over his cock. He then demanded I get on top of him as he reclined his seat back as flat as it could get. I got on top of his round stomach and slid myself down where I was now squatting my asshole over his cockhead. I was hesitant to sit on his cock as I thought about the pain as I was getting finger fucked. The man became inpatient as he lifted his pelvic area up and slammed his cockhead through my hole.

I was such in immense pain as I screamed while looking up at the car ceiling and grabbing a handful of the man’s shirt. He didn’t stop to give my asshole a break to get it use to his mushroom head being inside of me. I bit my bottom lip, placed my knees down onto the seat, and sat straight up while loudly moaning and screaming as he held onto my waist and continued to aggressively push his cock in my hole. It take long to get all of his cock in me. He paused for a minute as he told me to relax my hole and enjoy the fuck while he does all the work. He then grabbed my head and pulled my face down where our lips met. We were making out and tongue wrestling as he started to fuck me hard. In quick motions, he pulled his cock out of me until his cockhead was the only thing in my hole and immediately rammed his entire cock back inside of me.

He continued to increase his speed of his thrusts while the pain I was feeling had not yet gone away. Truthfully, I wasn’t enjoying myself as much as he was enjoying fucking the living daylights out of me. The man didn’t last long as he only fucked me for about 5-minutes before he moaned loudly, holding my ass down on his cock as I felt his ball sack touching my butt, and shooting warm streams of his cum up into my beat up hole.

Once he let go of my ass, I lifted myself off of his cock and moved myself back to the passenger seat as I could feel his cum rushing down my leg. He then made me do ass to mouth on him as I cleaned his cock before he drove me home. His cum tasted more bitter than when I masturbate and eat my own cum. There was a foul odor coming off his cock as I cleaned it off but I did notice that my ass was not dirty at all that night.

When I got home, I masterbated in my bathroom as I played with my cum drenched asshole. I then took a long hot shower and went to bed knowing I gave my virginity to a random stranger.

He became my first ever fuck buddy where we did meet and fuck raw again countless more times. He was the one who taught me how to be a bottom, fuck a cock right, and please a man well. To this day, I still don’t know the man’s name or anything about him other than his phone number, that was disconnected ages ago, and knowing he was a huge black man with a big thick cock that I loved playing with.

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