What Happens in Vegas - Part 4 (Jennifer Love Hewitt and Ariana Richards)

[Cptnstrwrs]

(Crazy to think this is the fourth installment I've done for this story. Thanks to everyone who's left me feedback on the previous chapters)

Las Vegas


        My girlfriend Ariana Richards had gone with her friend Jennifer Love Hewitt to Vegas for the weekend. She told me they were going to be hiring a couple of male escorts to help break Jennifer out of her sexual shell. From the texts Ariana sent me, they made a little progress, but not enough. Next thing I know she's texting me, asking me to fly out to Vegas to meet them. Seeing how Vegas is so close to LA, I'm on a plane and halfway there a few hours later. A quick taxi ride from the airport and I find myself riding the elevator up to the hotel room that Ariana and Jennifer are staying in. I knock lightly on the door, seeing as how it's still early in the morning. Ariana opens the door for me, holding a finger to her lips, letting me know I need to be quiet as I enter the room. I enter the room, giving Ariana a quick kiss hello. "Jennifer's still asleep in the bedroom. I may have tired her out last night," Ariana says, smirking at me. "Let me guess. The two male escorts were too much for her?" I laugh. "Yeah, she did alright. But I think some time with the Captain will finally get her out of her sexual shell and bring out her kinky side," Ariana says, grinning at me. "Oh, I think we both know she won't be forgetting this encounter anytime soon," I say as Ariana leads me to the bedroom. "Let me have some alone time with Jennifer first. You can watch, and if you behave yourself, I MAY even let you join in," I laugh. "Oh gee, thanks!" Ariana sighes, rolling her eyes.

        Ariana and I head to the bedroom, walking inside. In the middle of bed Jennifer is laying on her back, still asleep, the sheets showing off the curves of her obviously naked body. I quickly take off all my clothes, climbing naked onto the bed. Crawling up to her, I straddle Jennifer's upper body. She starts to stir beneath me, and I stroke her cheek with one hand. "Wake up Beautiful," I say as Jennifer slowly opens her eyes. Her initial shock quickly fades and she smiles up at me. "Ariana told me you were coming for some quality time. I didn't think you'd be here so soon. You must really be eager to bring out my wild side," Jennifer says, smirking up at me. "You have no idea. Figured an early morning blowjob would be a good way to start. Now suck my cock!" I growl at her. I have to give her credit.

        If Jennifer is nervous or caught off guard it doesn't show as she leans forward, mouth open, wrapping her lips around my cock. As she goes to move her hands towards my cock, I grab her by the wrists. "Uh-uh. No hands, only your mouth and tongue," I say, grinning at her. Letting go of her hands, I put my hands on the back of her head, holding her in place as I feed her my cock, thrusting my cock in and out of her mouth. Sliding my cock into her mouth as deep as I can, I hold it there, watching as Jennifer's eyes start to water, the brunette gagging on my cock. I pull it out, Jennifer coughing and gasping for air. "You did good, Baby! I'm so proud of you! You deep throated the Captain Cock like a pro!" I laugh.

        As much fun as it was to cram my cock down Jennifer's throat, I know that if I'm going to bring out Jennifer's inner whore than I need to have her thinking she's in charge, that SHE'S the one deciding what dirty deed we do next. "As fun as that was, we're only just beginning. What wild and crazy stuff did you want to do now? I'm good with anything," I say, smiling at her. She stares at me for a few minutes, the wheels in her head turning. "And don't worry. There's nothing you can suggest that I probably haven't already done. And if you're worried about anyone else finding out what kind of freaky stuff you're into, well, I promise that me and Ariana won't tell anyone," I say, Ariana nodding in agreement from her seat in the chair next to the bed. "What if you sit on the edge of the bed and I rub my boobs all over your penis?" Jennifer asks. "You want to titfuck me? Ok," I say, trying not to grin at Ariana as I move to the edge of the bed. It's clear to me that Jennifer hasn't really had a ton of sexual experience, especially if she doesn't know the names of common foreplay techniques. As she tosses the bed sheet aside, giving me a glimpse of her amazing nude body, I'm more than eager to teach her everything I know when it comes to sex.

        She kneels in front of me, a hint of nervousness in her big, brown innocent eyes as she pushes her huge tits together, my cock almost completely disappearing between them. The warm, softness of Jennifer's tits on my cock feels amazing. It's clear she feels the same, her nipples harden as she rubs her tits up and down my hard cock. "Ugghh! Damn, Jen! You're as good at tit fucking as you are at sucking dick!" I groan. "T-thanks!" Jennifer replies softly, blushing with embarrassment. "Being good at sexual stuff isn't anything to be embarrassed about. Tell me something, and be honest with me. If you could do anything sexual with me that we haven't done yet, what would it be?" I ask. Her face turns an even darker shade of red before she finally answers me. "I guess I'd want you to bend me over on the bed and fuck me doggy style," Jennifer replies softly. "Alright then. Get up and get on the bed," I reply, grinning down at her as I stretch out my hand to help her up. Jennifer gets to the center of the bed, and gets on all fours. Getting into position behind her, I decide to stick a couple fingers inside her. To my surprise, they slide right in, her pussy already soaking wet. "How are you so wet already!?" I laugh. "What can I say? I really like your cock. And the way you crammed it down my throat was kind of hot," Jennifer giggles. "I like this girl!" I say, lining my cock up with her pussy.

        I give her one good thrust, and I slide balls deep inside of her. "Uggghhhh!" Jennifer and I groan as I enter her. Grabbing her by the hips I begin to fuck her, deciding to start slow so I can enjoy this as long as possible. "Fuck! Ugghhh! You're so deep inside me Captain! I can feel your cock stretching out my tight little pussy! Ugghhh!" Jennifer moans. "It won't be small OR tight by the time the Captain's done with you!" Ariana giggles from her nearby seat. "Hey! You just be quiet over there and keep playing with yourself!" I laugh, Ariana grinning back at me. There are few things hotter than fucking a hot woman with huge tits like Jennifer while your girlfriend watches while playing with herself. And luck for Ariana, I plan on giving her quite the show. It's clear that Jennifer wants to be less inhibited and we're definitely making progress, but I still feel like she's holding back. Luckily I know just the thing for situations like this: fucking the lucky lady as hard and fast as I can with the Captain Cock. "Hold on, Baby! I'm about to tear that pussy up!" I laugh. I fuck Jennifer with every ounce of strength I have, our bodies smacking together, the bed shaking as we fuck. She previous quiet moans of pleasure quickly change to deafening screams of pure ecstasy. How she keeps herself from cumming by the time I grab her tits and squeeze them hard is anyone's guess, but I'm just glad I'm one of the lucky few who have had a chance to play with her tits. "Ooh! Harder Captain! Harder! Ugghhhh!" Jennifer whines.

        I oblige, moving my hands back to her hips, holding her tight while I fuck her hard and fast. "Ugghh! Fuck me Captain! Fuck me! Uggghhhh! Just like that!" Jennifer squeals. Reaching around, I begin rubbing her clit, Jennifer writhing in pleasure beneath me. She grabs her tits, squeezing them hard as I continue fucking her doggy while rubbing her clit. Her lack of sexual experience is clear when she cums only minutes into our routine. "Oh God! Ugghhh! I'm going to cum! Captain, you're fucking me so good! I..Uggghhh!" Jennifer groans, cumming hard on my cock. As if releasing years of built up sexual tension, Jennifer cums hard, her body shaking violently as she lets out a ear piercing scream of pleasure before collapsing face down on the bed in front of me. "Oh fuck! She came harder now then she did last night. And it was two cocks last night!" Ariana giggles. "Well I DO often have that effect on women. You okay Baby?" I ask, stroking Jennifer's bare back as I pull out of her. A low groan and a nod are the only response I get from her, which is fine, considering how badly I gave it to her.

        As Jennifer lies there on the bed recovering from her orgasm, I walk to Ariana, sitting in the nearby chair. She's completely naked, legs spread wide as she rubs her clit with one hand while fingering herself with the other hand. Kneeling down, I grab each of her arms at the wrists, pulling her hands away. Leaning in, I start licking her clit, using my right hand to finger fuck her pussy. "Ugghhh! Fuck, Baby! I've missed you so much! Agghhh!" Ariana groans as I eat her out. I've gone down on Arians so many times since we've been together that I know every inch of her body like the back of my hand. It only takes me a few minutes and Ariana is screaming loudly, cumming hard. "Ugghhh! Oh my God! I'm cumming so hard! Don't stop, Baby!" Ariana shrieks, climaxing for me in her chair. Pulling my fingers from between her legs, I put my hand in front of the now exhausted Ariana, who sucks my fingers clean. Winking at her, I walk back towards the bed to find Jennifer in the center, laying on her back, grinning at me. "That was incredible Captain! I've never cum like that before!" Jennifer giggles. "Yeah! I could tell!" I laugh. "What are we doing now?" Jennifer asks, a sheepish grin on her face.

        To be honest, I wasn't expecting this. Here was Jennifer Love Hewitt, former 90s heartthrob, practically throwing herself at me. Though she's lacking in sexual experience, her question makes me think that she's more than willing to try almost anything I throw at her. The only problem is I've dreamed of this for years, but now that it's actually happening how can I choose from all the naughty things I've thought of over the years? Eventually I decide just to go with the simplest solution. "I know you're probably still a little tired from before. How about I get on top and do all the work? That way you can just lie there and enjoy yourself," I say. "Okay, that's fine with me," Jennifer replies, smiling at me. Slowly I get onto the bed and crawl towards her, carefully positioning myself above her. She opens her legs for me as my cock gets closer to her hips, giving me easy access. Her pussy is still wet enough that I slip right in, once again filling her completely as I stretch her walls to their max. I waste no time, pounding her pussy as hard as I can, the bed shaking beneath as we fuck. Her tits bounce wildly with my every thrust, making the whole thing that much hotter. "Ugghhh! Ooohhh! Fuck me Captain! Fuck my pussy! This time I want you to cum inside me!" Jennifer wails, Ariana and I exchanging smirks. "If that's what you want!" I grunt, pumping her pussy as hard and fast as I can.

        Between the sight of her huge tits bouncing around and Jennifer's face, contorted in a look that's a mix of pleasure and pain, I don't last too long. "Ugghhh! You wanted it, well here it comes!" I groan as my cock tense up. I blast my unusually large load deep inside my busty brunette friend, Jennifer's pussy quickly filling up with my cum. I've barely pulled out of her when some of it begins leaking out of her, running down her thighs. "Oooh! It's so warm! And there's so much of it!" Jennifer giggles, Ariana smirking at me as I just shrug my shoulders. "Well, today it's all for you," I laugh, smiling down at her. I give Ariana a quick glance and I start to feel a little bad. We've both been so busy lately that we haven't had any one on one time lately. "Hey Jen. Why don't you go take a quick shower and get cleaned up while I spend some time with my girl here?" I ask. "Okay! Be right back!" Jennifer says, hurrying to the bathroom. I turn to face Ariana, waving her over. We get on the bed, Ariana pushing me onto my back as she climbs onto me. She grabs my cock in her hand, the familiar touch making it rock hard once again. Ariana guides it to her pussy, lowering her hips onto mine, my cock disappearing inside her.

        Every time I fuck Ariana, it still feels as great and exciting as it did the first time, and today is no exception. Our bodies fit together perfectly, as though they were made for each other. She knows just how and when to move her hips, causing my cock to hit the most pleasurable spots in her pussy. If she saw her riding my cock, you'd think Ariana is miles away, as if in a daze as she fucks me, but that couldn't be further from the truth. This woman knows exactly what she's doing and will always be the best lay I've had in my lifetime. Unfortunately, even with all the sexual experience Ariana has under her belt, she usually ends up cumming before me. I don't ever make things easy for her either, playing with her tits as she rides me. Her body tenses up abruptly, almost going as rigid as my cock, and I know what's about to happen. "Ughhh! Oh Fuck Captain! I always cum so quick when I ride your cock!" Ariana whines as she cums, her body shaking hard on my cock. It takes her a few minutes to finish cumming, Ariana pulling herself off my cock and laying down next to me on her back. We cuddle for several minutes, lightly kissing each other as we wait for Jennifer to come back.

        When she does return, Jennifer is covered only by the towel wrapped around her body. "Hey! I'm back. Sorry it took so long. You really came hard inside me Captain! There was so much cum to clean up!" Jennifer giggles. "Sorry about that. I know you just got all nice and clean, but did you want to do some more dirty things?" I ask with a smirk, raising an eyebrow at her. "Oh, what the Hell? Sure, why not?" Jennifer laughs, climbing onto the bed. As she goes to climb onto my lap like Ariana did, I stop her. "What's wrong?" Jennifer asks, confused. "Nothing's wrong, I just think you should turn around so we can try the reverse cowgirl position," I explain. She stares at me for a moment. "Ooh! Okay! Sounds like fun! It's been awhile since I've done that one," Jennifer says eagerly, Ariana and I exchanging looks as Jennifer turns around. As her ass lowers towards my hips, I have to admit that Jen's ass is almost as awesome a sight as her big, famous tits. My cock slides right inside her, Jennifer letting out a soft groan as she slides down the length of my shaft. Once she's gotten me as deep inside as I can go, Jennifer begins slowly sliding her hips up and down on my cock, both of us moaning as she fucks my cock. "I'm tired of just watching!" Ariana says suddenly, popping up from her spot next to me and moving to face Jennifer. I see Ariana put a hand between Jennifer's legs, no doubt rubbing her friend's clit. "Oh shit that feels good! Please don't stop! Your fingers feel incredible on my clit!" Jennifer exclaims, confirming my suspicions.

       The three of us go at it for what feels like hours. I know it's only minutes, but when you're balls deep in Jennifer's pussy time just seems to slow down. Just as we start to get a good rhythm going, I feel Jennifer's body tense up on my cock, a sure sign she's about to have yet another orgasm. "Oh God! Oh my God! I'm cumming again!" Jennifer shrieks as she cums all over my cock. Her climax lasts for several long minutes, her pussy trembling all around my cock as she finishes cumming. Jennifer pulls herself off of my cock laying on the bed next to me, Ariana on the other side of me. My cock is aching by this point, and I know I need to cum soon.
"I've really enjoyed our time together, but we have a problem, ladies," I say. "I haven't cum in a while and I think it's only fair that Jennifer be the one who gets me off. Only problem is we don't want to make a mess when I cum again. We can't have Jennifer using all the hot water with another shower, but I don't know how we do this without making another mess," I say, giving a sideways smirk at Ariana. The room is quiet for a moment. Finally, Jennifer breaks the silence. "What if I swallow your load?" Jennifer asks softly, her face turning a light red. I pretend to think about it for a moment. "Yeah... I guess that could work. Are you sure you want to? I mean, it could be another huge load of cum. Can you swallow all of it?" I ask. "Well, I guess there's only one way to find out," Jennifer says, slowly moving so she's on all fours between my legs, looking up at me.

        Without having to say a word, Jennifer takes the initiative, diving mouth first onto my cock, her brunette head bobbing up and down as she sucks me off. It's definitely a better blowjob than the one from earlier, Jennifer filled with her newfound confidence in her own sexual abilities. She's come so far sexually from the first time I met her til now, and I can't help but feel like I had something to do with it. "Ughh! Damn Jen! You're a quicker learner! Show that cock who's boss! I want you to suck that cum right out of me!" I say, hoping to encourage her even more. The results are instant, Jennifer speeding up her movements, her cheeks hollowing out again and again as she sucks me off. Even Ariana gets in on the action. "I'm so proud of you sweetie! When we got here you were so afraid to let your inner freak out. And now you're a dirty little whore!" Ariana laughs. I swear I see a smile form on Jennifer's face, despite my cock being halfway down her throat. Spicing things up, she starts flicking her tongue all over the head of my cock, and I can't take it anymore. "Fuck Jen! I'm going to cum! Remember, every last drop!" I groan as my cock begins to quiver.

        As I start to cum, the force of it feels like a bomb going off between my legs. To her credit, I see  Jennifer's throat bulge over and over as she gulps down every shot of cum I give her. By the time I shoot the last bit of cum into Jennifer's mouth, I feel completely exhausted. As she lifts her head off my cock, Jennifer licks the head of my cock clean, a hint of disappointment on her face. "What's the matter? Did you not like the taste of it?" I ask. "It's not that. I'm just upset that you guys are leaving soon. Can we all do this back home in LA sometime? I'm sure my husband would be ok with that," Jennifer says. I already know what Ariana's answer would be, and I'd be stupid to turn down any opportunity to fuck Jennifer again, even if her husband's going to be involved. "Sounds good Jen! Just name the time and place!" I say, both women grinning at me....

The End