I was just sitting at home when I got the call from Anna Kendrick. She said she needed some advice, that lately things hadn't been going well for her. Even without her saying anything I knew she was talking about her love life, having read all about her recent string of failed relationships. She was coming into town next week and so we set up a time and date for her to stop by. I felt a little bad for her so I made a few calls in the meantime, having thought of the perfect surprise for Anna. Sure she'd be a little hesitant at first, but I know that deep down she was going to love what I had planned for her.
The day finally came and Anna was right on time. We head right to my living room, Anna sitting down on one couch as I sit down on the one across from her. "So how is it I can help you Anna?" I ask. She's quiet for a moment, blushing. "Well Captain I'm not sure if you've heard but my last few relationships haven't really lasted that long. I'm not sure what I'm doing wrong and I thought you could help me with that," Anna says. "When you say 'what you're doing wrong'..." I begin. "Yeah, I mean in the bedroom," Anna replies, avoiding eye contact as her face becomes an even darker red. "Hey it's nothing to be embarrassed about. It happens to everyone at some point," I say softly, putting a hand on her shoulder. Her eyes start welling up and I can tell she's about to start crying. "I don't know what to do Captain! I'm not really a sexual person and now it's starting to affect my love life. I don't want to be alone the rest of my life!" Anna sobs. "You're not going to be alone," I say, hugging her. "Why don't you show me what you've got, and then I can give you some pointers," I suggest. Anna nods slowly. "At this point I'm willing to try anything," she says, her voice still a little shaky.
And just like that I've got my opening. Putting a hand under her chin I lift her head up so she's looking at me and I make my move. I kiss her hard on the lips, Anna's eyes going wide. I move my hands to her cheeks, holding her in place as I continue kissing her. Her initial shock melts away, Anna wrapping her arms around my head as I feel her kissing back. We make out for several minutes, Anna letting out a muffled gasp as I slip my tongue in her mouth the first time. She recovers quickly and as we continue kissing we take turns, slipping our tongue in the other's mouth. I pull away, staring at her. Anna gives me a big grin. I can tell she's still a little embarrassed but not nearly as much as she was before. "You're a good kisser," I say. "Thanks," she laughs. "If it's ok with you, though, I think it's time we do something a bit more intimate," I say.
Anna follows my eyes down to my lap, understanding. "Oh. Okay..." Anna says softly, blushing again. "If it's ok with you. I want to help you but I also don't want you to be uncomfortable," I say. "No, it's alright. I know it's something I need to work on and who better to practice with than you?" Anna replies. She stands, walking over to me. "Take off your clothes. It'll help turn the man on if you're just in your bra and panties," I explain. Anna is hesitant but slowly complies. She takes off her top and lets it fall to the ground. She does the same with her pants, leaving her in the most plain white matching bra and panties you've ever seen.
Kneeling down in front of me she unbuckles my belt. Slowly she unzips my pants and undoes the button. "Keep going," I say softly. Taking a deep breath Anna slides my pants down to my ankles before reaching into my boxers, producing my semi hard cock. She opens her mouth as she takes it in one hand, wrapping her mouth around the head. She flicks her tongue on the tip and it feels amazing. "Try getting more of it in your mouth. Guys want you to lick and suck the whole thing, not just the tip," I explain. Anna obeys, sliding her mouth up and down my length slowly, occasionally using her tongue on my shaft. "Good girl," I groan as she begins to speed up, encouraged by the compliment. I watch her head bob up and down on my cock and she looks like a natural, rather than the shy, inexperienced woman I know she is.
A beep from my phone interrupts my thoughts. I pick up the phone, a new text message letting me know it's time for Anna's surprise. "You're surprise is here. We need to finish this up so I'll help," I say. Gently grabbing the back of her head I begin moving my hips back and forth as she slides her mouth up and down my dick. I'm getting close to finishing and I know she's not going to be a fan of what I have in mind. As she speeds up the 'gwah, gwah, gwah' sound Anna's making is too much and I begin to cum. She begins to panic as I shoot my load, my cock still deep in her mouth, but I keep a firm grip on the back of her head. "Just let it happen Anna. Once you swallow your guy's load a few times you'll see how much your love life improves," I laugh, and to my surprise I feel her relax, Anna swallowing hard a few times before she starts sucking hard on my cock, desperately trying to get every last drop of cum in my body.
Anna finally stops, apparently satisfied that she's drained all the cum from my body. "I take it you don't normally swallow?" I ask as she stands up. "No, not usually," she replies, sitting down next to me on the couch. "Well if the next time you're with your a guy if you do what you just did I guarantee he'll leave happy. The way you sucked me off at the end there was incredible," I reply. "Good news. Your surprise is here," I tell her, replying to the message I received a moment ago. Anna looks a little concerned as my friend enters the room. "Anna, this is my friend Jason Luv. I invited him over to help us deal with your problem. You've probably never heard of him, but he's a famous porn star," I explain. She stares at him wide eyed, like she's never seen a big black man before. Finally she speaks, her voice shaky. "How's he going to help us?" Anna asks nervously. "Well, if you're up to it, you're going to fuck him while I watch and give you pointers," I explain.
Anna's eyes go even wider and for a second I'm sure her head is about to explode. "How long would that take?" Anna asks nervously. "You'd only have to fuck him until he cums," I explain. "But no one will make you do anything you're not comfortable with," I say. She looks from me to Jason and back to me again, slowly. Finally she speaks. "Ok. I'll do it. But he has to be gentle. I know how big black guys are," Anna says. As she walks over to Jason he's already in action, taking off his shirt and pants, sitting back down on the couch in only his boxers. I can tell Anna is more than a little nervous but she's all business as she kneels down in front of the first black man she's ever been with, sticking her hand into his boxers as she mentally prepares herself to suck the largest dick she's ever seen. Her eyes go wide as she pulls his dick out, surprised by how long Jason is, even though he's only semi hard right now. Anna quickly recovers though, opening her mouth as she lowers her head towards his cock.
As I watch her from my spot across the room it's hard to believe this is the same woman who nervously sucked my dick just moments ago. Something changed the moment she wrapped her lips around Jason's dick. All of her earlier fears and hesitation seemed to vanish, replaced by determination and maybe...desire? The speed her head bobs up and down seems to be ok with Jason as he groans his approval. He grabs the back of her head, pushing as much of his cock into her mouth as he can, Anna coughing and gagging as he does. As great as Anna is at sucking cock, Jason is more eager to move things along, motioning to her to stand up. He has Anna get on all fours facing me in the middle of the room. I jump in, undoing the clasp on her bra and sliding it off of her, finally exposing her breasts. For a minute it looks like she's about to say something, but she's caught off guard as Jason slides her panties down her legs. Jason lets out a whistle as he examines her pussy, Anna passing the surprise inspection. Using both hands to spread her ass cheeks Jason slowly moves his hips towards hers. He's so hard from Anna's blowjob that he doesn't even need his hands to guide his cock to her pussy.
Anna lets out a whimper as Jason pushes into her. "Oh god! It's so big!" Anna cries, her face a mix of both pain and pleasure. "Go slow! Please go slow! Shit! He's stretching my pussy!" Anna moans as Jason continues to slide inside her, inch by agonizing inch. Finally inside her as far as he can possibly go, Jason wastes no time as he starts pounding her pussy. "Oh fuck! That feels good!" Anna cries out, Jason grinning at me from his position behind her. "Give it to her Jay," I laugh. Grabbing Anna by the hips he begins to thrust into her even faster, fucking her as hard as he can.
The sound of their bodies slapping together is almost loud enough to drown out Anna's whimpering as Jason continues destroying her previously tight pussy. "Ugh! Oh my god! Uggghhh! I'm going to cum!" Anna groans. Seeing her face contorted in a mix of pain and pleasure is incredibly hot. I take my once-again hard cock in my hand and begin jerking it as I watch Anna getting drilled. She finally notices what I'm doing, her eyes going wide. "What are you doing?" Anna groans as she watches me. "Anna, you have no idea how hot it is seeing you on all fours getting destroyed by a big black dick," I reply, my voice a low growl. She gives me a little smirk before slipping one of her hands between her legs, furiously rubbing her clit as Jason continues going to town on her tight hole. He grabs her tits hard, rolling her stiff nipples between his fingers. That's all it takes to finally push Anna over the edge.
The brunette cums hard, Anna screaming loudly as she climaxes, her body shaking violently. If Jason notices he doesn't seem to care, thrusting as hard as he can until she finishes, Anna letting her upper body fall limply on the floor as she's plowed from behind. Jason pulls out of her, Anna's hips dropping to the floor. She slowly rolls over onto her back, gasping and panting as she recovers from her orgasm. Lowering his hips towards her, Jason spreads Anna's legs, sliding his dick back inside her. For a moment I think he's about to fuck her missionary position. But Jason has other plans, sliding his arms under Anna, right near the small of her back. "You might want to hold on baby," Jason laughs, Anna quickly wrapping her arms around his shoulders. He picks her up, cock still buried deep inside her, Anna wrapping her legs around his waist. The brunette squeals in pleasure as Jason slides her tiny body up and down his huge black dick.
"Ugh! Fuck me! Fuck me harder with your big black dick!" Anna wails as Jason speeds up, bouncing her up and down. It's too much for me to take, so I take my shot. "Hey Anna, I'm tired of watching. How would you feel about a little two on one action?" I ask. "Huh?!" Anna asks, voice a mix of surprise and panic. "Come on, there's nothing to be afraid of. You hadn't been with a black guy before today and now you clearly love it. The only thing better than one dick is two," I laugh. She hesitates, but finally answers. "That's fine. Let's do it. But only for a few minutes," Anna replies quietly. I walk over to them, Jason pulling out of her. I quickly slide into her pussy, letting her juices coat my cock. I pull out of her, Jason all too eager to get back inside her pussy. As the tip of my dick presses up against her puckered asshole I can feel Anna tense up. I push into her, Anna whimpering as I slowly slide into, inch by inch, until I'm balls deep in her ass.
I know that I'm the first guy to ever ass fuck her but I'm still surprised at how tight her asshole is. I shouldn't be though, considering how much of a prude Anna is. Jason and I beginning pumping her holes, Anna moaning as we bounce her up and down on our shafts. We start slow at first, but after a few minutes we decide to speed things up. "Ugh! I can't believe I have two dicks inside me! My holes are getting so stretched out!" Anna cries. I reach around her, grabbing her tits, playing with her nipples as I do. Apparently that's the last straw, Anna screaming as she starts to cum again. "Fuck. Fuck! FUCK! I'm cumming on two dicks!" Anna screams. Jason and I hold her as she climaxes, her body once again trembling hard. Once she finishes I pull out of her ass, Anna groaning as I do.
Jason, still inside her, carries her over to the couch, laying her on her back. He lays on top of her and begins drilling her pussy missionary position as hard and as fast as he can. Anna can't stop moaning and groaning with his every thrust. I stand a few feet away stroking myself as I watch him tear up her pussy. Jason turns, quickly grinning at me and I know he's about to be the first black guy to cum inside Anna Kendrick. Sure enough he is. With a grunt, Jason's body tense up seconds before his nearly foot long dick begins pumping Anna full of his semen.
Anna realizes too late what's about to happen. "Wait! Don't..." Anna gets out of her mouth but it's too late. All she can do is stare, wide eyed as the biggest dick she's ever fucked fills her with it's cum. "Oh god! He's not stopping," she whines. I finally reach my breaking point. "Anna I'm about to cum too," I say. She sighes, waving me over, opening her mouth. Taking full advantage of her unspoken invitation I stick my dick in her mouth, shooting my load down her throat. I finish, Anna giving my dick one final, hard suck to be sure all my cum is gone. Jason pulls out from between her legs, his cum slowly oozing out of Anna's pussy. She reaches down, catching as much as she can on her fingers before sticking them in her mouth, obviously wanting to taste Jason's cum.
"Next time you better warn me before you cum inside me," Anna says in a stern voice. Jason and I just grin at each other, catching her choice of words, both of us already thinking about our next encounter with Anna...
The End
Topic: The Captain Cuckolds Kendrick (An Anna Kendrick story) (Read 1532 times)