Ride or Die Pt. 01

She laughs at that. "Yeah. You did," she says before leaning back in and kissing me again.

She grabs my hand and leads me over to the bed. "I... I've never done anything like this before. I mean, I've had plenty of sex before, but, you know... Not like this."

She pulls back and looks me in the eye. "You're not having second thoughts, are you?"

"No. It's just that... I... I'm a bit nervous if I'm being honest."

"Relax, I'll be gentle. We'll take it slow."

"Does it hurt?" I ask as she puts her hand on my thigh.

"A little at first, but I'll make it so it hurts a lot less. It'll feel good, after you adjust. Really good."

"Okay, I trust you."

Her free hand ends up against my neck and she pulls me back into her kiss while her other hand slides up my thigh and starts to unbuckle my pants. Her lips are sweet like jam. Her hand slides below the hem of my shirt and up my bare chest, pulling it up over my head and toss it aside.

The music blaring in the background fades away and it's just the two of us. She pushes me down on the bed. She takes off my shoes and socks before pulling down my pants. She then rips off her jacket before taking off her top. Next comes off her bra, revealing two rather large breasts the shape of teardrops. After she gets her pants undone and off, she hooks her thumb under her white panties. Giving me a seductive smile, she slowly edges them down. As she slides them down, out pops a dick much bigger than mine.

Holy fuck! That must be at least 8 inches. She must've noticed my apprehension.

"Don't worry, I'm not going to stick it all in at once. I'll ease it in nice in slow after I get your tight little asshole nice as lubed up and stretched out."

I still can't believe her dick is bigger than mine by at least an inch...

She is taller than me, so I guess it makes sense. One thing's for sure, her body must've been sculpted by a god. Not only does she hardly have an ounce of fat, but she's somewhat lean. Not in a masculine kind of way, but very feminine. Wide hips with a bubble butt. A slim waist, but with abs. Thicc thighs, not chubby thighs, but massive thighs. Her underwear hits the floor before she crawls on top of me.

She leans down and kisses me. Those soft luscious lips feel warm against mine. I run my hands up her waist. Her skin is so smooth. Silk-like. "Turn over on your stomach, baby," She whispers before she gets off of me. I roll over on my stomach.

She pulls my legs off the side of the bed. She pulls down my boxers and tosses them aside. She then gets down on her knees. Her hands grab a hold of both of my ass cheeks. "Fuck, you have an amazing ass."

"Umm, thanks?" That's just what every guy wants to hear, not how big their dick is, but how nice their ass is.

Her hand comes down hard on my ass cheek. "Fuck!"

"Sorry! Couldn't resist."

Suddenly she dives face first into the crack of my ass. Her hot, wet tongue slides up and down my butt crack before finding the entrance to my backdoor.

A jolt of pleasure shocks my system as she circles her tongue around my rosebud. She squeezes my asscheeks as her tongue pushes at my backdoor.

Suddenly it slides in. "Ohhhh fuck."

The feeling of her hot, wet tongue sliding into my asshole is like having a massage and a hot bath, only in my butthole.

She starts to wiggle that tongue of hers in and out of my ass. It feels so good. It's making my dick hard.

All of a sudden, she pulls her tongue out. I look back at her, definitely wanting more. She gives me a smile before leaning down and giving me a hot and steamy kiss on the lips. "I'm just going to use my fingers to loosen you up some. Okay?" she says as she leans over and grabs a bottle of what I assume is lube from her bedside table.

"Yeah, that sounds good!" I'm practically panting now. She squirts some on her hand.

What kind of power does this woman hold over me? She's got me wrapped around her finger.

Uhhh, fuck! Literally, I'm wrapped around her finger, at least my ass is after she just worked it in my ass. I wasn't ready for that, but now that it's in, it feels kinda niiice! "Uuuhh."

Oh god, now she's working it in and out of me. Fuck that feels good. Oh shit! Did she just slide another finger in? I all of a sudden feel a little fuller.

"Do you like it? I've got two fingers in you now."

"Oh, don't stop. Please just... keep doing what you're doing," I moan out.

"I knew you'd like it." She lays a trail of kisses down in between my shoulder blades.

She really starts fucking me with her fingers. Hallelujah, that's fucking amazing. "Now I'm going to add a third finger, okay?"

"Yeah, go for it," I gasp. I'm actually panting for air. This girl has me panting like a girl as I grab onto her sheets. Oh shit, I feel like my ass is being stretched just a little further as she slides in another finger. God damn. It doesn't exactly hurt, but it doesn't feel comfortable. As she starts to ease her fingers in and out, it feels like my ass adjusts to them.

She leans in and kisses me on the shoulder. "Are you ready to try my cock?"

"Ahh... Fuck it. Let's do it."

"You're such a trooper." She pulls out her fingers. Fuck. I actually feel empty. It's weird. I want her fingers back in my asshole. I want to be filled up by her. I never in my wildest dreams would've thought I'd be in a situation like this. About to get my ass stuffed by a dick bigger than mine.

I'm not sure if it makes me gay or not, and honestly... I don't care. I've never felt this way about anyone before. I truly feel happy being around her.

I hear her squirt some more lube on her hand. I flinch as I suddenly feel her dick between my ass cheeks. She rubs it up and down the crack of my butt before the tip of her cock kisses my tied up balloon hole.

Oh shit. It hurts! Not as bad as I thought it would, but it still hurts. I clench a handful of sheets and bite into them. "Just breathe and relax. The more you tense up the more it's going to hurt."

I take in a lungful of air. In an instant, her dick pops into my asshole making my eyes go wide. I let out of a sigh of relief. Once it's in, it doesn't hurt as bad. "There, the hard part's over. Well, at least the painful part is over. The hard part is inside your ass."

"Ha haaaa!" She pushes more of her fat dick inside me without warning.

"Don't worry. We're just going to let your ass adjust as I ease my dick inside you. Just remember to keep breathing." God, I feel so full and yet, I think I actually love the feeling of it.

Ever so slowly, she slides more of her cock inside me. Gently easing it in. Inch by inch, she works her python inside my ass. Finally, I feel her hips slap into me. "Fuck, I'm all the way inside you. That wasn't so bad, was it?"

"Uhh, fuck. No," I gasp.

"Here, let's get more comfortable." She grabs onto my waist and hoists me up on the bed, keeping her dick still inside me. She pushes me down and my face lands on her pillow. I can feel her breast press up against my back as she leans down, sliding her arms underneath me and wrapping them around my torso. She kisses my neck as she starts to gently pull out her dick only to push it back in. She keeps rubbing up against a really sensitive spot inside my ass. Like a button that sends a riptide of pleasure through me every time it's hit.

Fuck, it feels almost too good to be true. I've had sex before, but nothing felt this good. The way her dick slowly pushes into my ass is almost better than the way you feel after winning a race. Almost.

Oh, fuck! She really went in hard that time. Okay, maybe it is equal to winning a race.

"I think you're ready, I'm going to start picking up the pace. Okay?" she whispers in my ear.

"Yeah! Oh. Please fuck me!" I moan out. She pulls her arms out from underneath me and leans up. She grabs my ass cheek and spreads it open with one hand while supporting herself with the other. Slowly, she starts bringing her hips back and forth, making that dick shuffle in and out of my ass. Each thrust a little faster than the last until my asshole has become her dick's punching bag.

"Ahhh fuck!" I shout out before biting into the pillow. It doesn't hurt, per se. Ehh, maybe it hurts a little. But holy fuck, it feels so good. Her dick battering against that sweet spot sends a tsunami of pleasure ripping through me. Every thrust rocks my very core from my toes to my fingertips.

"Oh, baby! I'm going to cum at this pace," she moans. My own dick is so hard it aches. I'm not too far from coming either. Especially when her cock hits that spot just right. Oh, fuck! It feels like someone stuck me in a sauna and kept flipping the temperature from extremely hot to extremely cold. My body doesn't know how to process all the stimulation.

I'm sure the sound of her hips slapping against my ass mixed with our heaving breathing, moaning, and shouting could be heard throughout the house, but I don't give a shit. Especially at this moment, when I'm on the edge of oblivion. One more thrust... "Urrrggghhh." She slams her cock, balls deep inside of me. My balls couldn't take anymore and churned out a load of cum all over the bed.

"Holy fuck!" I gasp as her dick continues to pulverize my ass. I'm clenching down hard on her cock as my own pecker spews out more cum. Such a bitter-sweet release. I felt like I was on the edge ever since she stuck her dick in my asshole.

Finally, she slams her hips forward, hilting her cock all the way inside my ass. Suddenly I feel a hot substance fill my bowels. "Oh fuck, I'm cumming!" she shouts out as she unloads inside my ass.

The steamy hot seed feels like my ass just got turned into a jacuzzi. Shit, that feels good!

She collapses on top of me, leaving her cock hilted inside of me as it starts to soften up. "God, that was amazing. It's been so long since I've had sex..." she says, barely able to catch her breath.

"Fuck... That was amazing!" I say. "I never knew taking it up the ass could feel that good."

"Well, it depends on the partner and preparation," she says as she finally pulls out of my ass and rolls onto her back. "Some people really don't take the time to prep the person receiving which will only make it hurt like hell."

"Well, that definitely was the best sex I've ever had." I roll over on my side and lean up over her and give a big kiss on the lips before collapsing back down.

"You're welcome, it's good to have a partner who is as open as you are," she says.

"Have you had a lot of partners?" I ask as I trace my fingers over the smooth skin of her forearm until they lock in between hers.

"I've had a few. Nothing deep."

"Yeah, me neither. Most girls only want me because of who I am. A rich kid."

"Life's so hard when you're wealthy..."

"It is! I tell you... Wait a sec, was that sarcasm?"

She laughs really hard. "Just a little bit."

"You think the sun's greener on my side of the fence? I mean, don't get me wrong, I'm not saying you've got it easy. And a lot of things in your life are much harder than mine. There's no doubt about it. It's just I wish I had my own life. My parents try to force their decisions on me. Like they have this life plan all laid out for me and if I don't follow it exactly, then I'm nothing to them."

I take a deep breath. "I feel so shallow complaining about my problems when they're so small compared to yours. I mean, you were homeless for god's sake. That must have been hard."

She rolls on her side, facing me. "It was extremely hard, but that doesn't mean the challenges you face are trivial. I completely understand how you feel. You feel trapped in a life that isn't yours. A prisoner to someone else's decisions and destiny. That's exactly how it felt for me, growing up pretending to be a boy. I was trapped in a body that didn't represent who I am. And now you're afraid that if you choose to disobey your parents and try to live your own life, they'll disown you."

"Yeah! That's exactly how I feel!"

"That's how I felt. But, I chose to do what I believe was best for me and unfortunately, I ended up losing my family."

"Was it worth it?"

"I think so. If people aren't willing to accept you for who you are then they don't deserve to be in your life regardless of whether they're family or not. You deserve to be happy."

"Wow, you're so... Wise."

"That's because I've been where you're at. Afraid to lose your family, but at the same time you're losing yourself. You try to make your parents proud, but it kills you inside. If you keep going that route, you'll break. It's not worth dying inside for other people's happiness. Be true to yourself. Yeah, you're going to lose people close to you. Family, friends, they'll exit your life. But you'll make new friends and get a new family that will love and support you for you."

"And here I thought you were some heartless thug. I still think you're a complete badass, but definitely not heartless."

She laughs. "I still think you're a rich kid, but you're definitely not the usual spoiled douche bags. But seriously, that hard ass, heartless thug you see on the streets wearing my face is all just an act. A front I have to put on so people won't mess with me or my friends. The streets can be a cruel place, you have to have thick skin and show a hard front in order to survive."

"So, if you're not really the hard-knock Ez that I stole my car, then who are you?"

"Okay, first of all, you lost your car. You should've realized betting against me is stupid. Anyways, my name or at least the name I chose when I transitioned is Esmeralda, but if you ever call me that on the streets, I'll kick your ass."

My eyes widen at her threat which makes her laugh. "I'm just kidding. But seriously, don't do that. If people see me vulnerable, they'll take it as an opportunity to take a shot against me. I can't have that. But, as far as who I am when I take off the Ez mask..."

She bites her bottom lip while she rolls on her back, tearing her gaze away from me. "This is going to sound lame, but deep down, I just want what any girl wants, to love and be loved. I want to find someone who'll love me for me. Underneath the thick skin, I'm really a girl who loves getting flowers, holding hands, going on dates, being told I'm beautiful. I just want to be treated like a woman. Or at least a human being."

"I get that, I mean... I'm not a woman or anything. But you are who you are."

"Exactly. By the way, if you tell anyone about this conversation, I'll..."

'Yeah, I know you'll kick my ass. Don't worry, your secret is safe with me."

She turns to me and gives me that beautiful smile that makes my stomach feel as if a bunch of ants are roaming around. "But for the record, you are beautiful."

I swear I saw a tear form in the corner of her eye before she attached her lips onto mine. God, her kiss is pure sugar. So delicious.

"You know, I find it so hot that you could probably kick my ass."

She lets out a chuckle. "Probably? I definitely can kick your ass. It wouldn't even be a fight, just a straight up beating."

"You don't have to be so blunt. I feel like I'd at least get a couple of hits in, not that I'd ever hit a lady."

"You'd probably break your hand if you tried to punch me."

"Well, it's a good thing I have no intentions of doing that."

She laughs and leans in once again for a kiss.

We continue to kiss until I fall asleep.

--

The Next Morning

I wake up to an empty bed. Slowly, I get out of bed. Ass is a little sore, not too bad. Looking around, Ez is nowhere to be found. I pull on my clothes and head out into the living room. That Hispanic girl is sipping coffee with the Asian she was making out with the last night.

"Hey, look who it is. How's that ass pretty boy?" The Hispanic girl snickers.

"Yeah, we could hear you moaning like a little girl, last night," The Asian says if I remember right, I think her name is Yuki.

I can feel my cheeks light up with heat, feeling totally embarrassed. Guess there's a first time for everything.

"Relax, nothing to be ashamed about. So what if you like it up the butt," the Hispanic girl says.

"Ez must really like you," Yuki says. "She rarely ever takes a boy home. Especially one we just hustled."

I hear a door open up and Ez walks out of the bathroom with a towel wrapped around her wet naked body and she uses another one to dry her hair. "Hope they're not giving you too hard of a time," she says. "James, that foul mouth latina is Octavia. Her Japanese girlfriend is Yukimuro. We just call her Yuki for short. Girls, meet James."

"Nice to meet the both of you," I say.

"Yeah, thanks for the car, I can't wait to crack her open."

"What?" I snap.

"Don't worry, she's just kidding," Ez gives her a glare.

"No, I'm not. I'm dying to see what's under the hood. That's gotta be modded the fuck out."

"Please, leave it all in one piece!" I beg. "I swear, I'll give you guys money. Whatever you want for it."

"Relax, she's just being cruel." Ez gives her another look. "We'll talk about it later. How about I get dressed and give you a ride to wherever you need to go."

"Okay."

She doesn't take long to change. Once she comes back out, we're in her truck and on the road. I tell her where I live and it doesn't take her long to get back to campus. She pulls up to the parking lot closest to my dorm room and puts it in park.

She turns to me and looks me in the eyes. "Listen, I don't just have sex with any random stranger I meet. I definitely don't do one night stands. But I understand if you're hesitant to continue where we left off. I mean, I did give your ass a pounding last night. I guess the point I'm trying to make is that I play for keeps. If you ever end up back in my bed, I will own your ass like I own your car. capeesh?"

*****

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