His Prisoner

by Jesse Jordan

  “What's that?” I ask, and Jessica stands on her tiptoes to whisper in my ear.

  “Please Master... I want you to fuck my ass. I'm begging you.”

  I grin, pulling her into an embrace and reaching down, grabbing the twin handfuls of her ass and kneading. “So... you're just giving me your ass cherry? You know I can't turn you down when you beg.”

  “I'm all yours Master,” Jessica moans, leaning her head back and showing me her collar as well as the enticing valley between her breasts. “And the shower would be cleaner... more relaxing.”

  “It'll still hurt,” I warn her as I lean down and suck on the curve of her neck, kissing along the hollow of her throat as I half squat to tug at her leggings. God bless yoga pants as the smooth skin of her ass is soon revealed to me, and I stand back, both of us breathing hard.

  “I know it'll hurt Master,” Jessica says, unknotting her shirt and peeling it the rest of the way off along with her bra before stripping her leggings off. “But with you, it always the good hurt.”

  Jessica gets in the shower and turns the water on while I strip, the water glistening off her skin like diamonds even when I open the door. She takes the handheld sprayer down and playfully squirts me with it, her eyes laughing before I take it from her and kiss her hard, our tongues immediately dueling around each other in twisting, writhing patterns even while I press her against the glass wall, squeezing her ass and making her moan deeply into my mouth again.

  “It'll hurt, but it'll feel good too the way I'm going to do it,” I promise her. “Turn around.”

  Jessica immediately obeys, bending over slightly and pushing her ass back towards me. If she weren't a virgin I'd want to take her asshole right now, but the first time... she deserves gentleness. I massage her instead, squeezing roughly on the outsides but more gently as my right hand moves towards the center. Jessica gasps when my fingers brush over her tight puckered hole and I rub. “Master.... oh that doesn't hurt at all....”

  “Take a deep breath and relax,” I command as I slip a finger inside, watching her face tighten before she remembers her training and opens up more, my finger slipping deeper. I finger fuck her asshole slowly, Jessica bending over more to loosen herself up more before I add a second finger. She whimpers in pain, but doesn't say anything as my fingers pump in and out of her tight asshole, the water helping to relax her ring. “Does it still hurt?”

  “A little Master... but it's good too,” Jessica gasps. “Can I rub my clit?”

  “I encourage it,” I chuckle, watching as Jessica reaches down and starts rubbing. She relaxes more as the dual sensations mix, the pain being carried away the way it's supposed to, and soon both of my fingers are plunging in and out of her ass easily. “Very good, my pet. Next is my cock.”

  “Master... yessss...” Jessica groans, her fingers still rubbing her pussy and clit while I line up. “Thank you Master.”

  Words jump to my mind but I don't let them out, and instead line my cock up with the winking pucker of her asshole. It's hard at first, but Jessica pushes back, opening her ass as best she can, and the sight of my cockhead disappearing into her ass is so erotic that I'm stunned at the gift this beautiful woman is giving me.

  Entering Jessica's ass for the first time is like nothing I've ever felt before. Around her ring she's almost painfully, impossibly tight, but as my cock breaches her most tender of inner secrets the rest of her is a warm softness that is better than any other ass I've ever felt. I go slow, short soft strokes that gently open this angel up to my total deflowerment, and when my hips touch the smooth globes of her asscheeks the pain's gone for her, leaving nothing but the pleasure of being taken totally and fully. “Master...”

  “Hold on,” I groan, pulling back before stroking in fully. We both gasp, I can't help it she's so amazing and the sensations running from my cock through my body are almost unbelievably good. We fall into a good pace, my hips taking their time guiding my cock in and out, filling my pet over and over. Jessica's lost, her nipples tight when I reach around and stroke them, nearly coming as I show her the deep, intimate pleasures of assfucking.

  “Oh fuck... fuck... fuck me... yes Master,” Jessica groans, her brain being overloaded with the sensations. I speed up, her eyes flying open at the feeling of my cock pounding her tender, precious ass, my hips smacking into her voluptuous curves. “Master! Oh fuck I love it!”

  “Take it all, that's it,” I encourage, getting rougher as her body relaxes and she can take it. Jessica's one of a kind body responds as we go faster and faster, my cock riding her tight ass and both of us finding total pleasure and abandonment in the feeling. I speed up more, my balls boiling to unleash within her tight bowels, and she grunts, both of us losing the ability to speak as we get closer and closer.

  Jessica comes first, her ass clamping around the base of my cock as she screams, the water spraying unfelt into her face as I plunge one more time before joining her, coming deep and hard into her ass. We freeze, both of us wanting this moment to last forever, and I make a decision that I know can change my life from this moment on. Actually, it's not even a decision, it's more like just knowing something, the knowledge exploding in my head as powerfully as my orgasm.

  Regardless of what it takes, no matter else... I have to have Jessica with me.

  Jessica

  “Master....” I half whisper, looking out at the turquoise blue water that laps at the brown sugar sand. “This is beautiful.”

  “Welcome to Cefalu,” Rodrigo says, looking amazingly dapper in the classic sport coat and cream colored slacks combination. He's even wearing an ascot, of all things, and I feel classy and pampered in my sleeveless blouse with pants and sandals next to him. “I thought you could use some time away from the villa, and today's a nice day to just enjoy some fresh air.”

  “Thank you,” I reply, looking out on the beach. There's a few bathers, Sicily is one of those islands where you can pretty much go some beaches all year around, but it's not crowded at this time of year yet. The Spring Break holidays are still a little ways off. “So what did you want to do?”

  “Oh, I don't know, just walk around for a little while, enjoy the town was my idea. Is there anything that you'd like to particularly do?” he asks. “There's some stuff I'd like to discuss with you, but for now, let's enjoy the morning.”

  “Can I take off my sandals and splash in the water some?” I ask, and he nods, smiling that Rodrigo smile that starts up the butterflies in my stomach even as I run gleefully down to the water's edge before stopping to take off my sandals. I turn to see Rodrigo close behind, his hand held out to take my footwear. I hand them to him, surprised after I roll up my pant legs that he's joined me, his slacks rolled almost to the knee and his docksiders in his hand. I splash and enjoy the feeling, fond memories coming over me as we walk in the wet, compacted sand.

  “You went to the beach a lot as a kid, didn't you?” Rodrigo asks warmly. Before I can answer, I see a couple walking along the other direction. I feel proud of being with Rodrigo, but something bothers me. With the couple, they're holding hands, the woman leaning on her lover's arm and for all the world looking 'lovey-dovey.' While I feel close to Rodrigo, I suspect that the couple we just passed wouldn't do nearly as much for each other as I would for him, there's a sense of public intimacy that we just don't have.

  Rodrigo notices, looking over. “What's wrong?”

  “Nothing, Master.”

  Rodrigo stops, reaching out and taking my hand. “You're lying, Jessica. Don't lie to me please.”

  I stop, turning to look at him. “I'm sorry Master. It's just... see that couple behind us?”

  Rodrigo glances, nodding. “Yeah, I noticed them. Why?”

  “I guess... this sounds so stupid,” I reply, sighing. “Master, I'd do anything for you. Probably more than that woman would do for her boyfriend. You know that, right?”

  “I know,” Rodrigo says. “And I've promised to keep you safe, to take care of you, to give you everything
you've ever dreamed of. Have I not?”

  “In some ways, you've given me more than I could ever dream of. But...,” I reply, then sigh. “I guess the girly side of me would like to hold your hand, to lean on you and be like they are in some ways.”

  Rodrigo smiles softly, looking at me with his dark eyes. “You know what the difference between them and us is, Jessica?”

  “No, Master. What?” I ask, and Rodrigo points towards the rocks up ahead. “The rocks?”

  “Those rocks, they're above a series of whirlpools, tidal pools that are very dangerous. There's signs all around the place that tell people not to go in them, and every summer, at least one or two people die because they either don't listen or fall in while trying to take pictures,” he says. “Jessica, the difference between us is that you would willingly leap into those pools with a rock in your arms if I ordered you to. At the same time, I would willingly leap into those pools if I saw you fall in without my orders. Those two wouldn't do the same for each other. That's better than any hand holding.”

  “I guess,” I sigh, still feeling sad for some reason on the inside. “I apologize, Master.”

  Rodrigo looks at me some more, then starts off again. For the rest of the morning until the sun is high in the sky we enjoy the beach, and as we walk, play, and just relax, my spirit lifts. After a lunch in a streetside cafe, we drive to Termini Imirese, where for the first time in months I get to walk around a mall, Rodrigo ditching his sportcoat and ascot before we go inside. We find a little gelateria, the Italian style ice cream shop that puts anything I had in New Jersey to shame, where he gets us a classic sundae to split.

  “Master, why did you bring me here today?” I ask as he passes me the single plastic spoon. Considering the amount of bodily fluids we swap on nearly a daily basis, a little bit of shared silverware is nothing. “Thank you, by the way.”

  Rodrigo takes a deep breath and shakes his head. “Not here. When we get back to the truck, I'll tell you on the way home. This isn't a conversation for public ears.”

  We continue shopping, Rodrigo letting me pick out a few items, and I'm shocked when he comes out of a lingerie store with a package under his arm. “A gift for both of us. We can open it at home.”

  We go out to the parking lot, where once inside, I look at him as he starts up the truck and pulls out into traffic. “Well?”

  Rodrigo glances over, his smirk faltering as he knows he's been keeping me waiting for hours, and even my patience is growing thin. “I thought about a few things in talking with Larissa, and since that bastard Leon threatened you,” Rodrigo says, his voice calm. “First, let me fill you in on a few things. For quite a while now, the man that you know as The Sultan and I have had a quiet rivalry. He's been the biggest hurdle to me getting promoted to capo. The other heads, they're worried about insulting such a major part of The Network, and for good reason, the Mideast arms and human trade is a big part of our income. Not the biggest, but a damn big part. Still, since I bought you, that rivalry has grown from quiet to just short of outright war.”

  “A civil war?” I ask, and Rodrigo laughs. “What?”

  “Wars within The Network are hardly civil, although I thought about it in the same terms. I was hoping to neutralize The Sultan through manipulation of the other capos, but The Sultan... well, Larissa says that The Sultan claims to have information that makes me look bad. She suspects that he's going to use that to either derail my promotion or worse. I'm pretty sure he'll be coming for my head, especially after what I did to Leon. If that happens, there's going to be blood on one side or another,” Rodrigo says softly as we come to a stop at a traffic light. “If that's the case Jessica, I need to know two things. One, that you can handle yourself. Second, that if shit does hit the fan and I buy the fucking farm, that you'll be able to keep yourself safe. Larissa likes you, she told me herself, but I can't be sure she'll be able to protect you if The Sultan kills me. I need to know that you'd be able to get out, to get to safety, even if it's just to the American consulate in Palermo.”

  The traffic light changes, and we turn right onto the road that heads back towards Caccamo. Rodrigo waits for me to respond, and it takes me a minute. “So today was just a test, not a day out together?”

  “It was both,” Rodrigo replies. “Jessica, I enjoyed walking on the sand with you, eating that sundae, and I'm looking forward to seeing you open up your present. But yes, I wanted to make sure that you can still get along in public if you need to. I couldn't be sure you hadn't turned into some sort of agoraphobe over the past few months. Keeping you cooped up makes you a liability, not an asset. And you can be the most valuable asset I have.”

  “Asset,” I whisper, looking down. Just an asset... nothing more. It hurts.

  Rodrigo glances over, saying nothing as we drive the twenty minutes back towards Caccamo, pulling off the paved road and heading back towards the villa. We left the villa gate open leaving this morning, and Rodrigo pulls in, hopping out and closing it behind us before getting in and clearing his throat. “There's something more I want to ask you.”

  “What?” I ask, looking over, my hands twisting in my lap.

  “I fully expect to win against The Sultan. I have a few aces in the hole that he won't expect or can prepare for,” Rodrigo says. “But if it doesn't, I might have to run. That could take me anywhere in the world. Jessica... if that happens, I want you with me.”

  “With you, Master?” I ask, confused. “You mean?”

  “I mean that I need to know if you want to come to America with me. Jessica, I know that I'm not the sort to be lovey-dovey like you mentioned, but I have never broken my word to you. I have taken care of you, and I swear I will always take care of you, but to continue to do so, I may have to ask you to do things that I didn't want to. Some of those skills that I said you'd never have to learn... I may have to ask you to learn.”

  “And if I say no?” I ask.

  Rodrigo looks disappointed, and looks at me with something in his eyes that I hope I'm not just imagining. “I'd be very deeply hurt. But if you insisted, I would free you, or if you want you'd stay here as my housekeeper. You'd be cared for either way. But you'd be better to me by my side.”

  I look into Rodrigo's dark eyes, and I wonder if I'm seeing something there that is just my imagination, or is there something more. Finally, I clear my throat and look at him. “Are you asking as Rodrigo, or as Master? Do I have a choice?”

  Rodrigo gives me a relieved smile, shaking his head. I think he was worried I'd demand my freedom. “Oh my beautiful Jessica, you've always had a choice. Each and every day, from the first time you called me Master, the choice has always been yours. Each day you've stayed since I didn't lock you in, you've made a choice. Since then, there's been a hundred times you could have slipped a kitchen knife between my ribs, and in the past week you could have shot me a dozen times over. So yes, you have a choice. You always have... and with me, you always will.”

  Rodrigo gets out of the truck, closing the door and heading towards the steps to the villa. My mind whirls, and suddenly I'm out of the passenger side of the truck, slamming the door and running up to him. “Master.... Rodrigo, wait!”

  Rodrigo stops, turning on the third step from the top, his face clear and bright and I make my choice. It's not that hard, when I think about it. “Yes, Jessica?”

  “I know my choice, but I need something from you,” I say, reaching up and taking his hand. “I need.... I need to know that I'm strong enough.”

  “And how would you like me to show you how strong you are?” he asks, turning the rest of the way around and sitting down on the steps so that we're eye to eye. “I know you are, but you have something else on your mind.”

  I nod, pointing towards the warehouse. “Master, I need to be pushed further than you've ever pushed me before. You told me, and I believe it. In my weakness, my submission, I've found strength that I never knew existed inside me. But I need more. I need to know... I want you to push me all the way
to the edge.”

  Rodrigo's face grows very grave, and he studies me. “You realize what that means, right? The risks can be very high. No limits, no safe words... I don't do edge 'play' like most people think of it. If we do this, we walk a very dangerous tightrope with no net.”

  I nod, squeezing his fingers. “I know Master. But that's something else that I've discovered in our time together, in our training. You said today that if you ordered me to, I'd have jumped into those tidal pools with a big rock in my arms. There's a reason why I would. Because I'm one hundred percent confident that if I step off, that somehow, some way, you'd catch me and save me before I drown. I trust you with my very life Master. So... let's walk that tightrope. I know you won't let me fall.”

  Rodrigo nods, reaching for and stroking my collar. “You are a one of a kind woman, Jessica. Let's go.”

  My fingers tremble as Master ties the silk rope around my left knee, bringing it to my neck, his eyes dark and dangerous. I'm sitting up now, but that won't be for long, once he rolls me back. I bend my head forward, and feel a moment of shock and loss when Master undoes my collar, and I whimper.

  “I don't want this damaged,” he explains as he sets it aside. “You'll get it back afterwards. Keep your head down.”

  I take a deep breath and lower my head, feeling the rope go behind my neck before Master draws it across my throat, wrapping me fully before tying my right knee. There's a little space, but not much, a quarter to half inch at most, and as Master rolls me onto my back, that space is eliminated. I pull on my knees with my hands to try and give myself some more help, but Master grabs my right hand and pulls it free, pinning it to the bed before tying it off with the scarf that he's already secured before doing the same with my left. I'm trapped, totally and completely helpless in a rig that can easily kill me, with no safe word.