How Ray Became A Bottom Bitch - Chapter 1 - Popping My Cherry

A 14-year-old boy named Ray is raped by the school security guard who records it, blackmailing him into a sexual relationship while he questions his sexuality.

I was blocks away from the school gate when I heard the bell ring. My backpack thumped against my spine while I ran knowing that I was already late on my first day of high school. I skidded to a stop in front of a golf cart parked by the entrance. A large black man sat inside the cart, detention slips fanned out in one hand. Mr. Wilson was the school's campus security guard who would lock the gate, hand out detention slips, and direct any student who was late to the principal's office the second school had started.

"Running a little late there buddy?" His voice was deep and firm, similar to a military drill instructor, which made me immediately straighten up. He was a very intimidating 52-year-old man. His body was built like a football lineman who was long past his playing days. Tall, overweight, with a beer belly gut, and muscular arms that were larger than my thighs. His presence made me feel even smaller than I already did.

"I'm sorry," I stuttered as my eyes drifted to the detention slips he held. "My mom and I just moved here a few weeks ago. I don't really know my way around just yet which is why I was late."

At 14, I was innocent and pure. My mom had successfully shielded me from what she called the "very dirty things" of the world. While my body was going through puberty, my mind was still a child. I had no interest in exploring myself, no curiosity about sex, or masturbation. All I thought about was playing video games and watching my favorite shows on television.

Physically, I was a contradiction. I was a small Asian kid with a great head of hair, soft skin, and a baby face the girls at my old school loved. But, my body told a different story. The tight skinny jeans and the skater shirts that I wore did nothing to hide my figure that was more feminine than masculine. I was thin and fit, with a small waist, curvy hips, and an ass that was big and plump where I would struggle to find pants that even fit.

From behind, I've often experienced older men mistaking me for a girl. I could feel their stares which made my skin crawl. The attention made me very uncomfortable. I was straight, but I hated my body for betraying me, for looking like the total opposite of what I expected it to be.

Mr. Wilson looked me over with a slow smile spreading across his face. "New, huh? Alright, kid. Don’t worry about it. I’ll let you slide today. Hop in. I’ll give you a ride to your class.”

Every morning after that, he would be waiting by the gate where I'd get into his cart and he would take me to class. As he drove, we talked about video games, movies, music, or whatever topic was popular at the moment. Those small harmless chats made me break out of my shell and I found myself getting comfortable around him and enjoying his company. I still hadn’t made any friends, and on most days, Mr. Wilson was the only person I spoke to for more than a few words. He was the only one who made me feel like I actually belonged.

About a month later, he started driving me home too. I’d meet him in the staff parking lot after school, by his black Cadillac Escalade, excited to hang out. We were now on a first name basis, giving me permission to call him Derrick.

Our friendship began to shift a couple of months into my freshman year. The first signs were unexpected forceful slaps on my ass as I stepped out of his golf cart while he imitated how football players patted each other during games. Hugs became traps. His hands would clamp onto my ass cheeks over my jeans, holding on longer than he should. He grew more invasive as his hands found excuses to stick to my body. The worst was the most recent car ride home. He had started massaging my thighs as his fingers crept higher until they brushed so close to my crotch that I flinched while my entire body tensed up. As he pulled up to the curb, stopping in front of my home, he leaned in next to my ear and whispered, "Do you know how to thank me for all these rides, Ray? Give me a kiss," as he pointed to his cheek.

Before I got out of that car that day, I had swallowed my pride, leaned in, and pressed my lips to his cheek, feeling his stubble and the heat of his skin. I hated myself for not saying no and I knew deep down that everything that he did during that car ride was wrong. My mind screamed at me to push him away, but he was my only friend and the only person who seemed to care about me at school.

Then came the day he didn't immediately drive me home after school. Instead of turning towards my neighborhood, he steered his Escalade the opposite way, down a road lined with abandoned warehouses.

"Where are we?" I asked with a knot in my stomach.

"Just taking a little detour, baby," he said with an assertive tone. I was confused as to why he just called me baby. He has never called me that before.

He pulled the Escalade behind a crumbling building and turned off the engine. The sudden silence was deafening. "You know, Ray," he said, turning to me with an intense look. "The very first day I met you as you ran up to the gate and I saw that fat ass of yours in those tight jeans, I got so fucking hard."

A chill ran down my spine. "What are you talking about Derrick?"

"Take your clothes off now," he commanded, his voice leaving no room for argument.

I hesitated. My mind was screaming at me to get out of the car and run, but my body was frozen. I was shocked that Derrick was gay as he didn't portray himself as what a traditional gay man acts or looks like. I wasn't able to say to him that I wasn't gay with how frightened I was at that moment. He then slapped me hard across my face with an angry look in his eyes. "What the fuck are you waiting for faggot, take off your fucking clothes!"

My hands trembled as I pulled my t-shirt over my head then fumbled with the button on my jeans. Soon I was naked in the passenger seat of his SUV while I had goosebumps all over my skin. I've never been naked in front of anyone before and as I turned to look at him, he had an evil grin while he scanned my body.

I looked down at my dick which was small, thin, soft and hiding between my legs. It was a tiny nub that you could barely notice. He then pulled out his phone and started recording. "Damn, look at that little dick," he chuckled as he zoomed in. "Barely even there. You were built for taking dick, not for giving." He then zoomed out as he demanded, "Now turn around and shake that fat ass for me."

I felt so humiliated, but I obeyed because of a mixture of fear and a desperate need to please the only person who had befriended me. I swayed my hips from side to side making my ass cheeks clap as it jiggled wildly. He recorded it all as his breathing grew heavier.

He directed me like a doll, his commands sharp and specific. "Bend over. Stick it out. Wider. Let me see that hole. Open your legs. Turn around. Hold your dick and jack it off." He clicked picture after picture, the phone's flash continually covering the entirety of my body.

Then, he tossed the phone onto the dashboard. His hand shot out and grabbed a fistful of my hair, yanking my head down as I leaned over the center console. His other hand worked at his zipper and his thick, eight-inch cock sprang free, which was already hard. "Open your mouth," he grunted.

I didn't want to, but I continued to follow his directions, not wanting to be slapped again. He forced himself inside my mouth, stretching my lips wide. He was brutal when he face fucked me, his hips bucking as he forced his shaft deeper down my throat, making me gag. Tears streamed down my face as my nose was buried in his pubic hairs as I took the entirety of his meat. "Choke on it, you little faggot," he snarled. "This is what you are good for."

After what felt like an eternity, he pulled out. A string of saliva connected my lips to his tip. He leaned over me, as his big belly pushed my head down on top of his hard cock, and reached into the glove compartment to pull out a bottle of lube. He gave the bottle a couple squeezes into his hand and rubbed it all over the opening of my asshole. He pushed his large thick fingers into my hole, one, then another, coating my anal canal and stretching me open.

I was terrified as I begged, "Derrick, please stop. It fucking hurts really bad." I whimpered in pain every time his fingers were pushed inside me.

"Shut the fuck up," he snarled as he took his fingers out and grabbed the front of my throat, pulling me up so we were face to face. His other hand started molesting my body, pinching my nipples, caressing my flat stomach, and tugging at my tiny dick.

He then leaned in and gave me a kiss on the lips. I had sucked a dick for the first time, I had just been finger fucked for the first time, and now Derrick gave me my first kiss. His tongue separated my lips and forced itself deep in my mouth as we tongue wrestled and made out. His spit was mixed with mine and I felt such a rush. I couldn't believe I was actually enjoying what we were doing.

He physically flipped me around where I was on all fours over the center console but now my ass was where my head used to be and I was looking out the passenger side window. I could feel him lining his massive cock up to my hole and, without any warning, slammed into me balls deep.

I screamed in so much pain where it felt like I was being torn in two. "Stop! Please, stop!" I pleaded, my hands gripping hold of the seat.

He just laughed while saying, "Take it, you little faggot! Take every fucking inch! This is what you get for teasing me with this ass every single day!" He was relentless. Pounding into me with a powerful rhythm. Each thrust driving the air from my lungs. He was enjoying my pain, enjoying molesting my body, enjoying the brutal way his huge cock was destroying my tight hole.

His hand came down hard on my ass, the loud slap of skin meeting skin echoed in his Escalade. "You're hole feels so fucking good! Clamping down on my dick like you don't want to let it go. I knew you'd be a good fuck."

He spanked me again, and again, and again, sending a shockwave through my body. He loved watching my cheeks jiggle everytime he pistoned in and out of me, a sight that seemed to make his cock even harder. He kneaded and slapped my ass cheeks until they were glowing red and warm to the touch. "Fuck yeah, look at that ass bounce! A perfect fuck toy for my big black dick."

After a while of being brutally raped, the pain I felt began to lessen. As he grabbed my hair and pulled it back towards him, where my face was looking up at the ceiling, I noticed an overwhelming sensation where I started to feel good. A moan escaped my lips. A sound of pleasure that shocked me as much as it did him.

He noticed immediately. "Yeah, that's it," he grunted as he fucked my ass faster. "I knew you'd love it. I knew you were a little bottom bitch who loves to take dick. Your little cock is getting hard, isn't it? You love getting your ass raped, don't you?"

He drove into me harder where his ball sac slapped against mine as he continued to talk dirty and degrade me with his words. "You're going to be my personal cum dump. Whenever I need a hole to nut in, I'm going to call you."

Finally, with a loud roar, he buried himself deep in me and came, flooding my ass with his warm load. I could feel it filling me up. The sensation of him deep inside me with his throbbing cock was too much for me to handle. I started to moan loudly as my small dick, which had grown to its full three-inch hardness, twitched. I shot my own load all over the center console. This experience was all too new to me. I was scared at first but I started to enjoy it where by the end I wanted more.

Derrick then said, "God, you're so hot." As he pulled his cock from my bruised gaping hole, I felt a rush of his cum streaming down my leg. "For being such a good fuck, this is what you earned." He scooped up his thick white seed leaking from my hole and feed it to me. It tasted so bitter, but I couldn't get enough of it. I begged for him to feed me more which he gladly did.

He then grabbed his phone from the dashboard as he said, "Stay just like that." I heard the click of his camera phone. A final picture of me looking back, on all fours, my ass in the air, and his cum leaking from my used gaping hole.

"Look at you, my dirty fucking faggot," he sneered, his voice thick with satisfaction. "A perfect little filthy slut, just like I knew you'd be. You're fucking beautiful like this, Ray." He grabbed my hair, yanking my head up. "Now get over here and clean me off." His cock, slick with cum and lube, was right in front of my face. I hesitated for a second as he slapped my ass. "Now, bitch!" He grabbed the back of my head and forced me down, not letting me up. I opened my mouth and took his softening cock, tasting the bitterness of his seed. I licked and sucked him clean as he started the car and pulled onto the road.

He kept a firm grip on the back of my head, using my mouth to jack himself off to get him hard again as he drove. "That's it, keep my cock warm while I drive you home." He was rough, his thickening member was stretching my jaw, forcing my head up and down where his cockhead continued to hit the back of my throat.

"Your mouth feels so fucking good." We were a block from my house as he continued to moan. He then lifted himself up off the seat and said, "Get ready for your dessert." He grunted as he held my head down, his cock stuffed deep in my throat, and came again. He exploded, shooting a second load in my mouth. The consistency was thicker and it tasted more bitter and saltier than the first, but I swallowed it all. When he finally let go of my head, I was gasping for air with strings of cum and saliva dripping from my chin.

As he parked in front of my house, he threw my clothes at me, hitting my chest. "Get dressed," he ordered, his voice all business again. As I fumbled with my clothes, he described our new relationship, "You're going to be my very special friend now, Ray. And special friends help each other out. Anytime I feel like using one of your holes, you're going to be ready and you're going to let me. That's what special friends do. I'm going to teach you all you need to know on how to be a really good special friend."

He leaned in closer, his voice low in a menacing whisper. "And if you tell anyone about this or if you even think about saying no to me, I'll make sure every single person at school sees this video and pictures. I'll show them what a dirty filthy faggot you are and how much you love taking black cock and having cum shoot up your ass. Understood?" I submissively nodded my head slowly up and down while my body ached.

He then tossed a black plastic bag at me. "This is for tomorrow," he said with a smile. Inside the bag were girls clothing. A tiny denim booty shorts that looked like they wouldn't cover all of my ass. A thin tight black tube top that reminded me of what prostitutes would wear. A pair of black high heels and a handful of makeup. "There's a note in there for you. Follow it. You got that? Now get the fuck out!"

As I walked through the front door of my home, my mind was a complete mess. My body felt used, but I knew one thing was for sure, I wasn't a virgin anymore. As much as it hurt, as much as I hated Derrick for what he did, I couldn't deny the truth that I loved every second of it. I loved making out with him, I loved sucking his cock, I loved getting my asshole fucked by him, and I loved swallowing his cum. Did that mean I was gay? The thought terrified me. I didn't want to be gay. I wanted to make friends my own age and be a typical straight teen. If people at school saw the video and pictures that Derrick took of me, they would shun me. I was trying to figure out who I was, but I felt more confused and lost than ever.