(This story takes place shortly before Captain's Log - Britney Spears)
Los Angeles, California
Hi everyone, it's Ariana Richards again. You may have heard that a few weeks back I accidentally broke some high tech sex simulators that billionaire Landen Long owned. Rather than have me pay him back for the broken equipment he decided to have me...work off my debt in...other ways. Which is exactly why I'm on his private jet, headed for New York City. Landon has a penthouse there and he called me the other day, telling me he has a new job for me and that if I just spend the weekend in New York, he'll knock off some more of my debt.
There's a car already waiting for us when I land, one of Landen's many assistants bringing my bags to the car. We drive non-stop, finally reaching the penthouse, located deep in the heart of the city. I'm more than a little anxious as I ride the elevator up, dreading whatever Landen has planned for me. Knowing him it will most likely be something humiliating, maybe even a little degrading but at least no one will see any of it. His assistant carries my bags behind me, opening the penthouse door and motioning for me to enter. For a penthouse, it's huge, bigger than most houses I've seen. We come to the living room and I see Landen sitting on one of the couches, talking to an older man who's sitting across from him. They both stop and stare at me as I approach, the older man letting out a whistle. He looks familiar to me but I can't place him.
Landen stands, walking over to me. "Hello Miss Richards, a pleasure to see you again," Landen says, his tone suggesting otherwise. "I'm not going to waste any of our time with this, so I'll get right to it. This is porn legend Randy West. He's had a long and successful career, breaking in dozens of young women to the porn industry, many of them going on to become huge stars. And for roughly the next day and a half, I'm paying him to absolutely ravage you," Landen says with a smirk. "Randy was one of my favorite male porn stars when I was a young man. I watched him turn so many innocent young girls into cheap whores and soon he'll do the same to you. Tell me, is he the oldest man you've ever slept with?" Landen asks. "How old is he?" I ask softly. "I'm seventy six, but trust me baby, I can go like a man half my age," Randy replies, smirking back at me. "How old are YOU?" Randy laughs. "I just turned forty five a few days ago," I reply. "Ha! That's funny. I've always worked with women a lot younger than me, but this time it's two for one: younger woman and a MILF at the same time," Randy says. "Trust me baby, I'll treat you right," Randy adds, smirking at me.
As much as I don't necessarily want to sleep with a man that old, I have to admit there's something drawing me to him. Randy is in much better shape than most men his age, and probably a lot of younger men too. And I am more than a little...curious to see how much experience he has, having broken in so many famous porn stars. "Well, I know Randy is ready to begin, Ariana, well, I know she's eager to get this over with as quickly as possible. If you'd both follow me," Landen says, standing. Randy and I follow him to the master bedroom, a huge king sized bed in the center of the room. "Oh, before I forget, I'll be sitting right over there watching the two of you go at it," Landen says, grinning at me. "Now don't be shy you two! Clothes off! Let's not drag this out, shall we?" Landen laughs. Randy wastes no time undressing and I find myself unable to look away. Seeing the older man naked for the first time my earlier suspicions were definitely correct. He's still in great shape, muscular despite the fact he's in his seventies. I begin to think this might not be so bad after all... "Hey! What are you waiting for?! Take your clothes off before I decide to starting adding to what you owe me!" Landen growls. Seconds later I'm completely naked, both men's eyes looking me up and down. The look in Randy's eyes makes the last bit of my earlier resistance melt away, while the sinister look in Landen's eyes makes me glad that he probably won't be fucking me this weekend.
"Holy shit my man! You weren't kidding! She DOES have a smoking body," Randy exclaims, climbing onto the bed, laying face up on his back in the center of the bed. "Come on over here and sit on my face Beautiful! I want to get a taste of that pretty little pussy," Randy says, the lust in his voice compelling me to obey. I lower my hips slowly, not wanting to smother him, stopping only once I feel his tongue run up and down my pussy lips. "Ugh! That feels so good!" I exclaim. "Heh! If you thought that was good then just wait," Randy says, his tongue focusing in on my clit. "Oh fuck! That feels amazing! Please don't stop! Right there! That's the spot!" I cry, grabbing the bedsheets tightly. Now, I'm no stranger to having random guys eat my pussy, but Randy has a technique that's far better than anything I've seen before, besides Cptnstrwrs, that is. It feels so good that I could cum any second...but of course, Landen has other ideas. "That's enough Randy. Can't have our friend here finish too soon. Tonight she has to earn it," Landen laughs. I climb off of Randy, the older man moving to the edge of the bed, sitting there. As I look at both Landen and Randy, their faces tell me exactly what's expected of me.
I get off the bed, walking in front of Randy. Kneeling in front of him, I can see the anticipation in his eyes, and no lie, it turns me on a little, knowing that someone is this excited to have me blow them. "Alright Baby. Let's see what the sexy milf mouth of yours can do," Randy laughs. Wrapping my fingers around the base of his cock, I open wide and slide his cock into my mouth. I go as fast as I can, my tongue moving like a whirlwind around his cock as I slobber all over it. Randy is rock hard within seconds. "Damn! I didn't even need that Viagra before! Why didn't you tell me you were bringing me a cock sucking connoisseur?" Randy laughs. He puts a hand on either side of my head, holding me in place as he stands up, still ball deep in my mouth. Still holding my head in place, Randy begins moving his hips back and forth, face fucking me with his cock. GWAH! GWAH! GWAH! He deep throats me over and over with his cock, tears running down my face as I gag on his big, beautiful cock. The older man gives it to me for several minutes before abruptly pulling his cock out of my mouth. I cough hard, gasping for air. "That was one of the best blowjobs I've had in years. Get back on the bed Baby. After that you deserve a little reward and I know just the thing," Randy says with a smirk.
I do as I'm told, Randy climbing onto the bed seconds after me. He climbs on top of me, cock in his hand. "Ugh! Please don't tease me," I say, surprising myself, as Randy rubs the head of his cock up and down my pussy lips. "Suit yourself Baby. I can't lie, since we started I couldn't wait to shove my cock in your pretty, little pussy," Randy laughs, sliding inside me. "Damn! That's tighter than I was expecting! No offense Babe," Randy grunts as he starts thrusting in and out of my pussy. "Ugh! Agghhh! Oh my God! None taken Randy. Please don't stop! You feel so fucking good inside me!" I moan, watching his cock disappearing over and over between my legs. Randy, apparently taking my comments as an open invitation, speeds up, the bed shaking hard with his every thrust. Between the length of his cock and it's hardness, no thanks to the Viagra, I know my pussy is going to be sore tomorrow but try as I might, I could care less. "Oh yeah! Give it to me! Fuck me as hard as you can Randy! I can fucking take it!" I growl, wrapping my legs around his waist, as if trying in vain to get him even deeper inside me. He puts his hands on my upper arms, pressing me into the bed even more as he hammers my pussy into next week. It feels incredible. Sure, I've been in a few porn films before this, but Randy is different from all the other guys. His technique, the feel of his body, the way he talks to me. He moves his hands to my chest, squeezing my tits a few times before pulling on my rock hard nipples. "Someone's enjoying herself!" Randy laughs before tilting my head back and nipping at my neck.
It's all too much, my body unable to contain all the pleasure I'm feeling right now. "Cum for me Baby! I know you're close! It's ok! Cum all over my cock!" Randy growls in my ear. "Ugghhhh! Oh fuck! Ugghhhh! I'm going cum Randy! Uggggghhhhhh!" I shriek, overwhelmed by my orgasm. I'd probably rank it as one of the top ten orgasms I've ever had, pleasure radiating throughout my whole body, Randy still pumping away as if he's oblivious to what's happening right now. As if he's trying to prove my point, Randy gives me a few last thrusts and pulls out of me. "Well I think it's safe to say you enjoyed your reward!" Randy laughs. "Whew! I-I guess you could say that!" I gasp, still trying to catch my breath as I recover from my climax. He lies down next to me, stroking my body softly, kissing me all over as I regain my strength. "I got to admit Sweetheart, you lasted longer than I thought you would," Randy says, grinning at me. "Gee thanks!" I reply sarcastically.
"It's great you two are getting along so well, but I think it's time for Ariana to start doing more of the work. Especially since she's SUPPOSED to be working off more of her debt," Landen says. "Well, I guess he has a point. Come here Babe. Let's see what you've got," Randy says, slapping his thighs. I pull myself up off the bed, swinging a leg over his body. Randy uses one hand to aim his cock towards me as I lower my hips towards his, using one hand to spread my pussy lips open. Inch by inch, he slides inside me and I feel every last bit of it. "Oh yeah! Your big, porn star cock is stretching my tight, little pussy out! That cock is so deep inside me!" I whine as I start wriggling my hips around on his cock, trying to work his cock further inside me with no luck. Based on Randy's moans and groans I know I'm on the right track. "Yeah Baby! That's it! Wiggle that sexy little ass around! Show that cock who's boss!" Randy laughs as I ride him as hard as I can. I feel myself getting even more turned on as he starts smacking my ass as I bounce up and down on his cock. He catches me off guard when he grabs my tits, holding on to them tightly as I slide up and down on his shaft. At this point it's a toss up as to who's going to cum first. Or...it would have been if Landen didn't get involved again.
"Stop! Stop it right now!" Landen shouts and I stop dead in my tracks, Randy and I exchanging confused looks. "I invited Ariana here to pleasure my hero Randy and so far she's failed miserably as far as I'm concerned. She's not only cum, but, after riding him like that you still couldn't make him cum in return? I find that type of behavior very bitchy and I think Ariana must be punished," Landen says in a condescending tone, smug grin on his face. "And I just happen to have the perfect punishment. If Ariana is determined to act like a bitch then Randy will have to fuck her like one too. Get on all fours bitch!" Landen snaps. I climb off of Randy, getting on all fours as commanded. Landen comes up behind me, spreading my ass cheeks with his hands, and spits on my asshole. "She's all yours. I think you know what to do," he says to Randy. "Well Baby, it looks like I'm going to have to fuck that sexy little ass of yours," Randy says, spreading my ass cheeks. "Go for it," I reply, feeling the head of his cock brush up against my asshole.
He pushes into my ass with little resistance, not stopping until he's fully inside me. Grabbing an ass cheek in each hand, Randy slowly begins pumping in and out of my ass."Damn girl! I knew you're ass would be tighter than your pussy, but this is crazy!" Randy grunts as he goes to town on my ass, smacking it with every thrust. After a few minutes he speeds up, moving his hands from my ass to under my body, cupping a breast in each hand and squeezing tightly. It all feels so good that I can't help myself. "Oh fuck! I'm cumming again! You're fucking my ass so good! Don't stop baby!" I cry, my newest climax more intense than the first one. My whole body shakes as I cum, Randy continuing to fuck my ass the whole time. "Are you kidding me?!" Landen exclaims. "Here's what's going to happen. The two of you are switching positions and Ariana is going to fuck Randy until she passes out from exhaustion!" Landen exclaims.
Randy pulls out of my ass and lies down on his back on the bed next to me. As I go to climb onto him, Randy puts his hands on my hips, trying to turn me around. I understand, and I turn around so we can try the reverse cowgirl position. His cock slides right into my still wet pussy and I begin sliding up and down his length. Sometimes I feel like reverse cowgirl is an awkward position to be in, but it's one of the only ones we HAVEN'T done yet so what the Hell? "Faster!" Landen snaps and I do as I'm told, moving my hips as fast as I can. Randy grabs my hips as tightly as he can, holding on for dear life as I ride his still hard cock. The only sound louder than either of our moans and groans of pleasure is the sound of my ass repeatedly slapping against his hips. He runs his hands up the sides of my body, stopping when he reaches my chest. Randy once again grabs my tits, squeezing one in each hand as he tugs and rubs my hard nipples between his fingers. It all feels so good that if I hadn't just cum minutes ago, I'd be doing it right now. "I said go faster! I know you can do better than this!" Landen shouts angrily. Forcing myself to speed up, I fuck Randy as hard and fast as I can. I think Randy can tell how exhausted I am, releasing my tits as he moves his hands back to my hips to help me stay upright. My pussy is aching, but I go on, hoping to God that Randy cums soon.
"Hey man! She's totally exhausted up here. Ariana's no good to anyone if she passes out. I'm close to cumming, but if we change positions I can cum before she's too tired to go on," Randy says, a hint of concern in his voice. "Fine! Just be quick about it!" Landen sighes. Still holding me by my hips, Randy slowly pulls his cock out of me. He gently lowers me onto the bed, face up. Climbing on top of me, he pushes his cock against my aching pussy lips. "Sorry Baby. I can tell your exhausted. We're almost done but it's going to get worse before it gets better," Randy whispers as he slides inside of me. He begins to fuck me missionary position, harder and faster than before. The familiar sound of the bed shaking fill the room. "Ughh! Agghhhh! Right there! Fuck me Randy! Fuck me until you cum!" I hear myself shout. "Argh! I'm close! I'm so close Baby!" Randy grunts, giving his all as he fucks me without mercy. "I want you to cum inside that dirty little whore!" Landen growls. "Ugh! Aahhhh! Ugghhhh!" Randy cries as his cock tenses up inside me. "Cum for baby! Give it to me!" I cry. And he does, pumping his huge load deep inside me, that familiar warmth of a cum filled pussy radiating between my legs. Even with him still inside me, I can feel some of his cum leaking out of me, running down my thighs.
As I lie there, I can't believe how things have changed. When the night began, I was horrified at the thought of sleeping with an seventy something man, but now I can't believe how great it was. Randy took care of me the whole way through and it wasn't nearly as humiliating as I thought it would be... That is until I feel the first cumshot hit my face. "Don't you move! Don't you fucking move!" Landen growls. More and more cum splatters on my face, Landen jerking himself as he shoots his load all over my face. My face is practically covered in his cum by the time he's finally done, but at least it's over. I've worked off my debt to this creepy young billionaire... Or so I thought. "Go clean yourself off in the bathroom. You look like a cheap little whore with all that cum! When you're done, hurry up and get dressed," Landen snaps. I run to the bathroom as quickly as I can, not wanting any of Randy's cum to drip out of my pussy and onto the floor. I clean the cum from between my legs first. As I finally see myself in the mirror I almost want to cry. My cum covered face does make me look like a dirty whore, just like Landen says. Wiping myself clean I hurry back to the bedroom silently. Gathering my clothes I quickly get dressed. "There's a car downstairs waiting for you. I'll be in touch," Landen says with a grin. All my hopes of being done with Landen are shattered, knowing that this is far from the end. If there's any consolation it's that in a few hours I'll be back home with my man Cptnstrwrs...
The End...For Now
Topic: Debts to Pay - Part 2 (Ariana Richards) (Read 1024 times)