New Orleans, Louisiana
So there I was in the Big Easy, the day after Mardi Gras, heading back to my hotel after a long night of wild partying. I get off the elevator and head to my room. As I turn the corner I nearly trip and fall over something on the floor. I look down, seeing a small brunette woman sleeping on the floor. Bending down I gently shake her. "Hey are you alright?" I ask. She looks familiar but I can't quite place the face. "Huh? Yeah. I'm ok. My friends and I went out partying last night. I forgot my room key and when I got back they weren't here. So I just crashed out here," she answers, still half asleep.
The fact I can't recognize her is driving me crazy, but I'm more concerned with someone seeing me with a half conscious woman in the hallway and getting the wrong idea. "Hey how about you wait for your friends in my room? It's just a few doors down," I say. "That's probably a good idea," she says, slowly standing up. "If someone saw me passed out on the floor like that Netflix wouldn't like that. They'd probably cancel my show. My name's Jenna by the way," she yawns, reaching out to shake my hand. That's when it hits me. The young woman in the hall is Jenna Ortega. "I knew I recognized you from somewhere," I exclaim. "Yeah, and that fake that I was drinking last night wouldn't help either since I'm legally able to drink yet," she laughs. "How old are you?" I ask. "I'm only twenty right now," she replies. "Well I won't tell anyone if you don't," I laugh, opening the door to my hotel room.
Jenna flies past me, hurrying into the room, turning on the lights. "You never told me your name," she says. "Sorry about that. You can call me Cptnstrwrs," I reply. She stops dead in her tracks. "You're Cptnstrwrs?! I've heard of you before, but I never thought I'd ever get to meet you," she says, her face turning a light shade of red. As she stands there staring at me, I slowly realize that she must have some kind of crush on me. I take a shot, wanting to see if I'm right. "Between your partying last night and sleeping on the floor out there you must need to clean up. How about taking a shower while you wait for your friends?" I ask. Her eyes widen for a split second. "Y-you mean for us or just me?" Jenna stammers nervously. I decide to take my shit, the worst possibility being that she says no. "Well I really just meant for you. I could use a shower too. I could wait til your done or..." I reply, watching the wheels turn in her head. "I mean... I don't see why not... I... Sure. Let's do it. We can save time and water by showering together," Jenna replies, her face turning an even darker red as she blushes more.
We walk into the bathroom, closing the door behind us. "Here's what we'll do. We both face the door and get undressed. Then you hop in the shower first and then I'll do the same. But no peeking," Jenna says, staring deep into my eyes. "I mean it!" she says, pointing a finger st my chest. "Okay! Okay. I won't peek," I laugh. "Alright, let's get started then," she says, turning on the water. She faces the door and I quickly get undressed and hop in the shower. I jump back, feeling how cold the water is. "Jenna wait!" I shout as she starts to step into the shower, her back to me. It's too late, my mind distracted by the little toned ass in front of me. The freezing water blasts the front of her tiny naked body. "Shit!" Jenna cries out, turning quickly as she jumps back, wrapping her arms tightly around me. I can feel her thin, toned body shivering against mine. Slowly she looks up at me, a goofy smile on her face. "Sorry. I didn't realize it was that cold," she says. I try to ignore her little rock hard nipples pressing against my chest but it's no use. My dick starts to get hard, poking her in the thigh. For a moment I hope that she doesn't notice but I quickly realize that's not happening. "What? Ohhh!" Jenna says, eyes going wide as she stares at my cock. "It's so big, but it's not even totally hard yet," she says in a soft voice.
I realize my chance has come. Putting my hand under her chin, I tilt her head up, staring her in the eyes. "Go on. Touch it. It's ok. And I know you want to..." I say in the most seductive voice I can manage. Her hand moves in slow motion, stopping centimeters from my dick. I hear her take a deep breath as she gently wraps her fingers around my shaft. "Mmm. That feels good baby. But why don't you stroke it a little?" I suggest. Jenna obeys, slowly moving her hand up and down my shaft, my cock growing longer and harder as she does. "You're doing great baby, keep it up," I groan. She speeds up just a little, the look on her face letting me know some of her earlier nervousness has faded.
Jenna does such a good job stroking my cock that I decide to reward her. Slipping a hand between her legs I begin to rub her clit, Jenna moaning as I do. "Oh shit! That feels so good Captain. Please don't stop," she whines. I speed up my hand, sticking a few fingers inside her twenty year old twat. "Fuck!" Jenna cries as I enter her. "Damn! I can't believe how wet you already are!" I exclaim. Her hand cranks into overdrive as I pull my fingers out of her. I stick my hand in front of her, Jenna sucking her juices off my fingers, flashing me a seductive smile. I nod at her, letting her know I'm ready for more.
She takes my hand, leading me out of the bathroom and to the nearest of the two beds in the room. I sit down on the foot of the bed, Jenna kneeling in front of me. Opening her mouth wide she lowers her head onto my cock as she begins to blow me. I watch her head bob up and down on my cock, turned on by the sound of her gagging on my dick as she slobbers on my entire length. Her eyes water each time she deep throats my cock, the tears causing her makeup to run down her cheeks. She ignores all that, forcing herself to continue blowing me. Jenna gives my dick a few more licks, before deciding that's enough. "Back up on the bed and lay down," she says playfully. I do as instructed, surprised by the tiny brunette's speed as she climbs onto me, straddling my body. Lowering her hips, Jenna pushes my cock towards her lower lips, sliding my dick inside her as far as she possibly can.
"Damn! Your pussy is so tight!" I grunt as she begins riding my dick. It's a tight fit, even with Jenna's pussy being as wet as she was moments ago. She moans and groans as she bounces up and down on my erect cock. "Fuck Captain! Your dick is stretching my tight hole," Jenna cries with each downward thrust of her hips. And she's right. There's almost no give in her muscular walls. She speeds up, whimpering and whining as she implies herself on my dick. "I want to cum! I'm so close Captain! Any second now!" Jenna cries. She begins rocking her hips even harder, her eyes closed tightly, as she groans in pleasure. "Uggghhhh! I'm cumming! I'm cumming all over the Captain's cock!" Jenna cries loudly. Her body falls forward on top of mine, Jenna laying there limply, panting hard. I give her a few minutes to rest, the poor girl clearly exhausted from her wild ride.
Deciding she's had enough time to recover I grab her lightly by the hips, pulling my dick out of her. I gently roll her off of me and onto her back on the bed, right next to me. As we lay there in silence I can't help but keep thinking about the sight of her little, toned ass when she got into the shower with me. I know it's probably a long shot but I take my chances. "That was amazing baby. But I think we need to step it up. You want to try something a little more...kinky?" I ask, turning to look at her. She's quiet for a few seconds before she turns and looks back at me. "How kinky are you talking?" Jenna says softly. Standing up I walk to the foot of the bed. Slipping my hands under her I squeeze her ass cheeks. "I want to fuck that hot little ass of yours," I say, smirking at her. Jenna is silent for a moment, deep in thought. Finally I get my answer. "Alright. But you have to be gentle. I've never done anal before," she says nervously. "Don't worry sweetie. We can stop any time if you don't like it," I say, stroking her inner thighs.
Jenna forces herself to sit up, her mouth drawn to my cock once again. She slobbers and drools all over my dick before stopping. "Ok. Let's do this before I change my mind," Jenna sighs, dropping back on the bed to her previous position. She puts a hand under each of her legs, spreading herself wide open. I take my cock in my hand, not an easy task thanks to Jenna's spit that now coats my dick. Walking over to her I place the head of my cock against her asshole, Jenna tensing up at the sensation. "I'll count to three then slide inside," I say. "Okay," Jenna says, voice shaking. "One!" I exclaim, pushing inside her. Jenna lets out a yelp as I penetrate her cute little ass. If I thought her pussy was tight, the tightness of her ass is unlike anything I've ever experienced. I enter her slowly, inch by inch. "You okay?" I ask after getting the first three or four inches of my cock inside her ass. She nods quickly, her eyes tightly shut.
Grabbing her by the hips I lean in and begin pumping in and out of her tight asshole. I'm careful not to pull completely out of her, unsure if Jenna could handle me constantly re-entering her asshole over and over. The tiny brunette whimpers as I pound her previously virgin asshole, stretching it with every move I make. "Ugggghhhh! Ahhhhh! H-how much longer is this going to take Captain? I'm not sure if my ass can take much more of this," Jenna whines, her face flush. "Not too much longer, especially since you're asshole is a lot tighter than I thought it would be. You're doing great so far baby," I reply as I lean in and gently stroke her face. I speed up my thrusting, Jenna not a fan of the choice, as her moans and groans of pleasure and pain become louder. Reaching up her body I cup her tiny breasts in my hands, rolling her still hard nipples between my fingers as I fuck her hard. "Fuuuuuuucccckkkkkk!" Jenna wails, her noisy outburst too much for me to take.
I feel my cock tense up seconds before it happens. I cum hard, spraying buckets of cum into Jenna's aching asshole, filling her with my load. "Oh shit! It feels like you filled me up Captain!" she moans, arching her back as my cock still spasms, pumping her full of my cum. Jenna lays there motionless, aside from panting hard as I finish cumming. I slowly, carefully pull out of her asshole, Jenna groaning as I do. I try not to laugh as she lays there completely exhausted, the hard and heavy ass fucking taking a bigger toll on her than me. As I watch her begin to slowly start moving again, I catch sight of a thin stream of my cum as it begins to leak from her asshole. "I guess that was more cum than your hot little ass can handle," I laugh. Jenna's only response is a tired weak smile.
We both jump as a loud beep comes from the other side of the room. Pulling herself off of the bed Jenna walks to where she threw her clothes, digging into the pocket. "My friends just texted me. They're back at the hotel. I should probably go," she says, gathering her clothes. "Ok. I had a fun time. We should meet up again sometime," I reply. We quickly exchange phone numbers. "Definitely. But maybe without the anal sex. I think I'm going to need some time before I do that again," she says, smiling weakly. "Fine by me," I say, smiling back at her as she heads to the door. She walks with a slight limp, no doubt from her first ass fuck, and I can't help but smile, knowing that Jenna won't soon forget our wild night together...
The End
Topic: Ass Wednesday (A Jenna Ortega story) (Read 11672 times)