Deep Undercover Ch. 05

Not twenty minutes later, Alex returns in a pair of forest green trousers and a black and white striped knit top, fit a little too well to hide much of his physique to the imagination. He reaches out his hand to me and says, "Come with me."

I put my glass down and take his hand. Without a word, he's leading me to the library. Butterflies fill my stomach in anticipation, as he opens the secret door. Down the stairs, the sun is streaming through the water of the pool, as he pulls me into his favorite room. He leads me over to the bed and says, "Take off your clothes, Madison."

Remembering his rules when we are in this room, I do as he says, "Yes, sir." It doesn't take me long to remove my blouse, skirt and silk and lace burgundy bra and panties. His breath catches as he ravages me with his eyes, up and down my body. Hands in pockets, he turns and walks to the wood table, examining the items, as if he's not quite sure what he's going to do with me. Finally he returns with a small, black, rubber cone-shaped toy in hand. He holds it up for me to view and asks, "Do you know what this is, Madison?"

"It's a plug, master," I'm confident in my answer.

"Very good. Have you ever used one?"

"No, master. I haven't."

"Have you ever had anal sex, Madison?"

I blush at the thought, "No. I haven't."

"Why not?'

"I don't know. It always seemed so...dirty to me. And I don't think I would enjoy it."

"I'll bet you $1,000 that you do enjoy it. In fact, I can guarantee it."

"Won't it hurt?"

He lowers the plug, his eyes sincere. Coming closer, he leans in and kisses me softly on the lips, "Trust me."

"I do."

"Good. Then come with me."

He sets the toy down behind me on the bed and, grabbing my hand, leads me to the leather-padded sawhorse near the glass wall. He moves behind me and nudges me forward, "Climb onto it intuitively, Madison. See those straps?" He points toward the leather straps attached at the base of the contraption, furthest away from us. "Those are for your hands and the others your feet."

I examine every inch of it. This is going to put me into an awkward position, but, like a good slut, I comply and climb on, adjusting myself so that my head is hanging over the furthest side. I feel Alex moving behind me, fastening my ankles. Then he comes around to the front and does the same with my wrists.

Inspecting his handiwork, he circles around me. I'm suddenly very self-conscious and struggle a bit with my bonds. Alex chuckles, "You're not going to get out of it, my beautiful little whore. Just make yourself comfortable." I hear him walk back toward the wall with the toys. Unfortunately, this thing is facing in such a way that I can't turn that far to see what he's doing.

He's coming back.I tremble, a bit nervous about what's next. I feel Alex's warm hand caressing my ass, "I quite like you like this, exposed like the little slut I knew you would be." His insult sends tantalizing shivers through my body.

He goes on, gently rubbing my ass, "Now relax. You're going to feel something a bit wet and cold in a moment. It's just lubricant." I can't help from tensing as I feel it drip onto my ass. I jump slightly as Alex's fingertip circles my virgin hole. I feel him walk away again. A few moments later, feeling him behind me again, he's pushing something against my asshole. I clench in hesitation.

"Now, Madison, it will certainly not feel good if you fight it. Relax, baby," he says, pushing his index finger into my wet pussy. I close my eyes and moan at the unexpected offer of pleasure. He continues sliding his finger in and out, teasing me.

I feel the slick rubbery tip on my unconquered hole again, gently pushing at the same rhythm as Alex's finger. I can feel it sliding in little by little. I relax more and more as he distracts me, fucking my used hole with his finger. "That's it, baby. Almost in," he assures me. I don't even care any more.Everything feels so good.

Finally, as I'm getting closer and closer to coming, I feel my asshole widen more and more, sucking the butt plug in like a welcome treat. Finally, it slides in and fits snugly. "Oh fuck, Alex! Don't stop!" I shout. I'm so close!

With that, Alex withdraws his finger and smacks my ass, hard. "I make the demands around here, Madison," his voice is very serious. He comes around to the front of the sawhorse. I can see his bare feet on the carpet and feel the proximity of his heat on the top of my head. Grabbing my hair forcefully, he lifts my head and kneels down, looking me in the eye.

"You're in such a perfect position to take my cock in. Do you want it, whore?" he asks.

Right now, I'll take anything he's willing to give, as I reply, "Yes please, master."

"Yes please, master, what?"

"Please give me your cock."

"Are you going to be a good little girl and take it all in?"

"Yes, master."

"We'll see..."

He drops my head and unzips his trousers. I can hear the elastic waistband of his boxer briefs snap as he pulls them down. Grabbing an entire fistful of hair, he lifts my head so that my gaze is fixed on his wanting manhood. It stares back at me, challenging me. Without a word, he pushes against my lips, forcing my mouth open, and thrusts inside, deeper than anyone has ever gone before.

I gag, but he doesn't remove it and instead says, "Just give it a second. Let your throat accept it. That's a good girl." He's right. A few seconds of gagging and my throat graciously accepts its welcome guest. He backs out and then thrusts in again, further and further each time, my gag reflex slowly giving up the fight. It's useless against this invader.

Soon he's thrust in to the hilt, his balls loudly smacking against my chin. "Oh fuck, Madison! I knew you'd be the perfect little cocksucker," he moans. He starts moving his hips faster and faster, careful not to slam against my face. My throat is happily accepting each entry as he moans in pleasure, his fist tightening its grip on my hair.

"Fuck! Your'e going to take all of my cum like a good little girl," he yells out, as his cock twitches in my throat. I can feel the warm cum streaming in, as Alex tilts my head back more so that it finds it way down. After he's satisfied that I've taken each drop, Alex gently lets my head down and releases my hair.

Staring at the floor again, I can hear his heavy breaths, as he pulls up his briefs and fastens his trousers. He kneels down and tilts his head. Pushing my hair from my face, his lips find mine and he kisses me hard, as he unbuckles my restraints. I let my arms dangle, as he stands and moves to the back, unbuckling those as well.But what about the butt plug?

Moving to my side, he reaches his hand under my stomach and helps me stand. He smiles, and, as if once again reading my thoughts, he says, "It stays in. Trust me." He winks. I can't help but smile in anticipation of what's to come.

As he picks up the lube and walks back toward the far wall he orders, "Get dressed. I'm taking you out for lunch."We just ate.I won't argue. I do as he says and dress quickly, smoothing down my now wild hair and adjusting my outfit carefully, conscious that with every single movement, I can feel the plug teasing the inside of my ass. He smiles and grabs my hand, pulling me out into the hall.

As we pass that last locked door, I can't help but wonder when I'll get a chance to get in.I have to get something to take with me to the agency.He leads me up the stairs and into the foyer. As he walks to the coat closet near the kitchen and pulls out a pair of all-black chucks, I realize I'm in my bare feet. "I'll be right back. I have to put on some shoes," I rush up the steps and to the walk-in closet, finding a pair of low-heeled brown ankle boots with buckles that cross the strings.Of course he picked shoes with straps too.

In the foyer, I find the front door open and can hear Alex talking to some people outside in Swedish, telling them that we will be back in a few hours. He's not to be followed by security. As I step out into the fresh air, my heart flutters when I see the beautiful black super bike at the bottom of the stepped path leading down to the drive. Alex turns just in time to see my eyes light up with excitement.

"I see you can enjoy beautiful things just as much as I can," he winks.

As I approach the bike, I can't help but admonish, "It's gorgeous!" I run my hand over the black leather grip, across the cold metal handle bars, down the spine of the body and over the warm leather seat. Handing me a fitted black leather jacket, Alex says, "Put this on. You'll get cold and it's safer." I won't bother arguing, despite the numerous times that I've done some very insane things on a bike in the name of my job.

I zip up the jacket, tugging the bottom down a bit. Alex hands me a black helmet, "I think you should drive."

"You want me to drive?" I'm shocked.

"You do know how, don't you?"

"Of course I know how. Why don't we race and I'll show you how good I am?"

"Maybe later. Seriously, though."

"Sure, but I don't know where we're going."

"I'll direct you."

I lift my leg over the seat and tilt the bike up, lifting the kickstand with my boot heel. Alex climbs on behind me, as I turn the key. As the engine comes to life and the bike starts to rumble, I can feel it sending exquisite vibrations through the end of the rubber plug and deep into me.That clever man.

"Let's go!" Alex shouts, as I rev the engine a few times. He wraps his arms around me, tight, as I release the clutch, shift into gear and twist the right grip.Here we go!We roar our way down the long, winding gravel driveway. Alex releases his left hand and gestures to turn to the left at the end of the driveway. Peering to each side and confirming that the coast is clear, we dart out onto the paved road.

Enormous trees are tight to each side as we wind our way up. It's all forest. We don't even pass any other vehicles on the road. The air is fresh and damp as we glide. Soon the trees open up a bit on the right, revealing a long drop down to more forest below.

"Keep going up the mountain," Alex shouts over the engine. I nod my head and give it more gas. Everything is so lush and green. The air is so crisp, but it's hard to think about anything other than the vibrations torturing my insides.

About fifteen minutes of zooming up the winding road Alex shouts again, "Slow down. We turn right up ahead. I'll signal when we're about to get to it." I acknowledge with another nod, easing off the gas and shifting gears. Not minutes later, Alex releases his right hand and motions to turn right at the next road. I see it up ahead. It's dirt and it looks like it's going to be bumpy.That fucker.

I lean into the turn, probably a little more than I should have with a passenger, but I know he's a trained rider as well. Alex places his hand back on me, but doesn't grip his left like before. Instead, he moves it down to my skirt, pushing it up as his fingertips find my soaking panties. "Oh fuck," I say into my helmet. He rubs me, hard, as the uneven dirt road pounds against the tires, sending shockwaves of pleasure through me.

Minutes later, I am forced slow down as we reach the end of this road at a fallen log. "This is it," Alex shouts, still tormenting me with his fingers. I halt the bike, kick down the kickstand and reach to turn off the ignition, but Alex's left hand intercepts. "Leave it for a minute. Take off your helmet," he says.

He removes his hands to do the same, tossing his helmet gently to the ground, I follow suite as Alex's left hand grips my throat. Pulling my head back, he ravages my mouth with his tongue, as his right hand finds its way back under my skirt. I moan into his mouth. I can't take it! The vibrations, the rubber plug in my ass, his fingers massaging my clit.I'm going to come!

Realizing I'm close, Alex's fingers and tongue retreat and he reaches around me and turns off the bike. "Not like this," he says. "I've got something better planned." Holding my waist, he climbs off the bike, unzips his jacket and tosses it over the bike. I follow suit, as he starts walking toward the forest, gesturing for me to follow.

He waits for me to catch up for him and takes my hand. With each step, the plug torments me, daring me not to enjoy it filling my ass.

As the density of the trees starts to thin, everything opens up to reveal a clearing at the edge of a cliffside with a stunning view of the valley below. Everything is green as far as the eye can see. There's a picnic set up with a blanket, two glasses, some wine, cheese, crackers. I flash Alex a smile and a questioning look. "I had one of my security team come ahead and set this up," he says. "But first we have some business to attend to." He reaches below a fallen log and pulls out a large bundle of climbing rope.

"I climb here often, so I always keep gear stashed away," he says, walking over to a tree and setting to work wrapping rope around it.

"I see," I swallow hard.I hope that rope is for me."And is that what we are doing?"

"No, Madison. No climbing today. Come here," he doesn't stop what he's doing to look at me. I approach him slowly, stopping just behind him, not wanting to interrupt whatever he's trying to accomplish.

He stops suddenly and turns, grabbing both of my arms hard and kisses me roughly. Turning me, he pushes my back against the trunk of the tree. His hands move down my arms, putting my palms flat against the cool bark. He untucks and slowly unbuttons my denim shirt, exposing my burgundy lace-covered breasts to the cool air and the entire valley. I don't even care that someone could see me right now.

He stops kissing me and works on tying my hands tight with the rope. With a hunger in his eyes, he then takes the end of the rope and disappears from view, circling the tree and wrapping the rope around me several times, carefully placing it just below and above my breasts and tight over my shoulders. He's gone for a few moments as I can feel him securing it behind me.

Back in front of me, he looks intently into my eyes as his hands lift my skirt and he slowly starts sliding dow my panties. He leans down, as I lift my feet so that he can take them off. His eyes are burning into mine again, "Open your mouth."

I do as I'm told and he shoves my panties into my mouth. They're soaked and taste of my sweet desire. Not taking his eyes from mine, he unzips his pants and pushes down his waistband so that it's out of the way of his massive erection.

Without a word, he grabs my thighs and lifts me up just enough so that he can slam his cock hard inside of me. I screech with pleasure through the panties. It's all too much, as I'm completely filled up, his dick and the plug competing inside of me.I'm going to come.

He grunts as he fucks me hard and fast. I can tell he's close already. "Ahhhh!" a muffled scream escapes me as I explode all around him. Not a moment later, I feel him spasming inside of me, as he starts to fill me with his seed, wailing my name, "Madison!"

Spent, he continues holding me for a few moments as he catches his breath. Finally he sets me back onto the solid ground, removing himself from within me. I can feel his cock sliding against the plug as he pulls out.Jesus the torment doesn't end.I already want him again. He smiles at me. He knows exactly what he's doing, as always.

He removes my panties from my mouth and chuckles, "Perhaps we should let these air out a bit. Did you enjoy tasting yourself, Madison?" He zips himself up and brushes my skirt into place.

I can't even speak. I can only nod that I did enjoy it. "Hmm..so you like tasting yourself. Have you ever been with a woman?" he asks, as he starts untying me.

I have to clear my throat after all of the screaming I've been doing over the past few days before I answer, "No. I haven't."

He unties me quickly, coiling the rope back up and putting it back under the log from which he retrieved it. "Let's have a snack and some wine," he motions for me to join him on the blanket.

As he pours me a glass of pinot noir and hands me a cracker with L'Explorateur spread onto it, he pries more, "Have you ever been curious about being with a woman?"

Nearly choking on my bite I act surprised by his question, "I'm not answering that!"

"Oh come on, Madison. I've already told you. I'll never judge you."

I take a sip of wine before I answer, "Fine. I am curious. I've fantasized about it and watched my share of girl on girl porn. But I've never had the courage to actually pursue it."

"I would be happy to arrange it for you."

"I'm sure you would, Alex."

"Well, whenever you're ready."

"Planning on keeping me prisoner forever then?"

"To be perfectly honest, I'm not sure I ever want to let you go."

We smile at each other and look out at the view as we continue to enjoy our picnic. "It's so beautiful here," I sigh looking over the trees all the way to the horizon. There's a slight chill in the air, but it's welcome as the sun beats down on us.

"It really is. Would be much more beautiful if we had some privacy," Alex mutters.

"What?" I'm a bit alarmed by his statement.

He turns his head and looks at me very seriously, "Don't let on that anything is wrong. Smile and act normally. But...we aren't alone."