50 shades of gray

By ShoopDaWho

172K 1.7K 105

This is the story of a 21-year-old college student, Anastasia, who begins a relationship with a 27-year-old... More

Chapter 1 -The First Time
Chapter 2 - If At First You Don't Succeed
Chapter 3- A short lesson in Limits
Chapter 4 - initial Negotiations
Chapter 5 - Briefly....
Chapter 6 - Upkeep
Chapter 7οΏΌ- Long and Awaited
Chapter 8- MorningοΏΌ
Chapter 9- The Email
Chapter 10-Her Collection
Chapter 11-A Skype How-To
Chapter 12-Smooth Moves
Chapter 13-Signature Dish
Chapter 15- Benefits of Submission
Ch 16-The Name of the Game
Ch 17- Be Careful What You Wish For
Chapter 18-The Dressing Part
Chapter 19- Graduation
Chapter 20- Mine
Chapter 21- The Laying-Out of Cards
Chapter 22- Two Kisses
Chapter 23- Stare Down
Chapter 24- Trapped
Chapter 25 - A Graceful Exit?
Chapter 26- Ready or Not...

Ch 14-For Your First Challenge

6K 61 7
By ShoopDaWho


My eyes shoot up to his. I had no idea I was biting my lip. I guess I just do it unconsciously.

Christian stands up from his seat, dropping his napkin on the table and walks slowly toward me. He positions himself directly behind my chair. I can feel my pulse quickening at our proximity. He leans over me, his cheek almost touching mine, and takes the pen from my hand. He signs his name on the line below my signature on both copies.

Christian Grey.

He tosses the pen on top of the documents and leans both hands on the edge of the table. His hot breath against my ear sends shivers down my spine.

"You're all mine now, Miss Steele," he growls softly then bites my earlobe. Hard. I gasp at the pain and the pleasure of it.

He bites into my neck and down to my shoulder, leaving behind a trail of fire. I moan softly and lean my head away, giving him purchase.

"Miss Steele, I don't suppose you've ever been restrained during sex before, hm?" I think he knows the answer to that one.

In a moment, he's wrapped my hair around his wrist and has pulled it back almost painfully. "Answer me," he seethes. I can see a complete change in his demeanor. He's serious. He's Dom Christian.

"No, I haven't, sir."

He relaxes his grip and smoothes my hair down my back gently.

"Stand up."

I stand up and place my napkin on the table.

He hands me a room keycard. "Suite 1001. I want you sitting on the leather couch in ten minutes." And like that he leaves the room.

I'm left standing panting and dripping wet alone in the dining room. Before I even have time to panic, our waiter returns with a note for me. He busies himself cleaning up the table while I open it. It only has one line of text in Christian's neat hand:

Wear only the shoes.

It's all I can do to keep from moaning out loud. I check my watch quickly. I'm guessing I only have about eight minutes left. Quick as I can in these heels, I scurry out of the room.

Christian is nowhere to be found, but that's not really surprising. What is surprising is that I feel his eyes on me. Somewhere. He's somewhere. I don't have time to focus on that. I carefully descend the stairs back into the main bar area and head for the lobby.

Once I'm back on the marble floor, I have to watch my step more carefully. The upstairs and the bar are both old hard wood so I didn't have to worry as much about slipping. I'm worried I'm going to lose my footing and break a bone in these heels. I finally reach the elevators and press the "up" button, checking my watch. I have just five minutes. Shit.

The elevator is not nearly as fast as I'd like it to be. This will give me no prep time once I'm in the suite. Finally, finally, the doors open on the tenth floor. I see Suite 1001 at the end of the hall and practically run to it. Two minutes. I of course fumble with the keycard but finally manage to get the door open.

Thankfully I've been in this suite before. Otherwise, I'd be losing time ogling at the size of it. Hell, I didn't realize it had a second bathroom when I was here last time! Jeez.

I disrobe as I walk, peeling my dress off and folding it neatly before leaving it on a chair in the corner. If our phone sex session the other night was any indication, Christian does not take kindly to clothes being strewn about. After taking off my necklace and putting it on the desk, I seat myself on the leather couch and check my watch. Less than a minute left. I cross my legs and and put my hands on my knees.

The couch faces the bed, so the door is behind me. Now I get to play the waiting game.

I suck at the waiting game.

I check my watch again. It's only been a couple minutes.

I put my hand back on my knee and look straight forward. I'm sure this is how Christian wants me to sit. Eyes straight ahead, a demure look on my face, legs crossed.

Or maybe knees together?

I shift.

Maybe knees apart.

I shift again. Hm, I don't think I can sit with my crotch on display until he arrives. I try knees together again. I put my hands on my lap but decide it's too much like I'm trying to hide myself and put them back on my knees.

Looking straight ahead, I really don't have much to look at. Just the bed. It's a huge California King with a big corona of a sun for the headboard and restraining points on each of the corners.

Wait, restraining points? Those weren't there last time.

I hear the door open and my pulse quickens. I'd just caught my breath from hurrying up here and like that it's labored again. Even though the temptation to turn around and look at him is so great, I stay completely still and stare at the bed.

And the bedside table. Which has a vibrator on it. It's the same exact one as Kate gave me. Billie. Or, as Christian calls it, Little Katie.

There's that familiar tug deep down in my groin and I feel a wetness spreading on the leather. It feels sinful just sitting like this.

I hear Christian moving around, opening drawers, shifting things around. Then music. It's some classical piece that sounds familiar but I can't identify. It's mixed with a techno beat underneath. With the music blasting, I can't even hear him moving around anymore. It's driving me crazy this anticipation. I shift slightly in my seat, sitting up a little straighter so the firm edge of the couch touches me just so.

"Ah, Miss Steele, remember the rule about self-pleasure?" His voice sounds right behind me and I nearly jump. I blush and scooch back on the couch slightly.

He appears in front of me wearing a pair of worn-in jeans with the top button open. He's shirtless and shoeless and I feel everything in me tighten at the sight.

"Although I am disappointed you did not follow my instructions fully, Miss Steele, you pleased me by getting here on time."

My eyes dart up to his questioningly. What didn't I do correctly? I'm sitting on the couch, I conducted myself in a modest manner on my way up, I was here on time...

"You're wearing a watch, Miss Steele."

Shit. He's right. He said only the shoes. I drop my gaze and chastise myself. I was trying so hard, too. It takes all I have to not immediately apologize, but I know I shouldn't speak.

"Give me your wrist," he commands.

I oblige, holding out my left hand so he can remove the offending watch. Stupid, stupid, stupid Ana. Deftly, his fingers turn my hand so my palm faces up then unbuckles my watch strap, letting his fingers linger on the inside of my wrist. It sends goosebumps up my arm.

Pulling me gently by the hand, he leads me to the desk in the corner, where he sets my watch down next to the keycard and my necklace. Then he leads me to the foot of the bed and has me sit on the edge.

"I know you tried, Anastasia. That pleases me."

I smile slightly, staring at my hands in his. His are so much bigger.

"Look at me, Ana."

I lift my eyes to his and feel that spark immediately. I let a small sigh escape my lips and I see a smile pulling the corners of his mouth.

"Do you remember your safe words?"

I nod slowly.

"You may speak."

"Yellow and red, sir."

"Very good. You'll tell me if it's too much?"

"Yes, Mr. Grey."

There's a quiet rumble in his chest. "Good." He drops my hand and stands back slightly. "Stand up and face the bed."

I do as I'm told and he takes my hand again. I look over but he grumbles incomprehensibly and I lower my eyes again. I feel a leather strap wrap around my wrist and tighten to near-painfulness. "Is that too tight, Miss Steele?"

"No, Mr. Grey."

"Good," he says as he moves to the other side. "Put your face down on the bed, Anastasia." The restraints are low, about hip height, and once I've laid my head on the bed, I can just stretch far enough for him to secure the other restraint. There's no moving from this position. I'm bent over further than I was when he spanked and fucked me the first time — my head is a few inches lower than my hips.

There's a long moment where nothing happens then he slides in behind me. I feel the heat of him against my legs and his hardness, rough in his jeans, against my ass. "You look edible, Miss Steele."

I whimper slightly. It's all I can do. My vagina is pulsating. He slides a hand between up and spreads my ass cheeks apart, examining me. I feel more naked than I ever have in my life right in this moment.

"Miss Kavanagh really did a phenomenal job, Miss Steele." I feel his fingers pulling and pulling me apart, I'm starting to worry I might split in two. The feeling is heady. "I am so looking forward to claiming your ass."

I can't help it, my knees buckle for a moment, but Christian hooks his fingers under my hips and pulls me back up almost immediately. "Careful you don't fall over, Miss Steele. We couldn't have that, now could we?" Slowly he starts stroking me along my ass now that I'm more stable. He presses his crotch into mine and a jagged moan escapes my lips.

"I am torn, Miss Steele." I feel a slight chill as he steps back from me, but almost immediately a hand is playing with my clit, his thumb sliding into my opening just barely and pressing down in a dizzying way. "On the one hand, I want to reward you. You are trying very hard to be an excellent sub, which pleases me. And you signed the contract, which pleases me immensely." His hand's movements quicken and I begin panting loudly.

"On the other hand," he says, pulling his hand away. I almost whine but manage to control myself. Barely. "You made me compromise greatly on this Katherine Kavanagh issue and should be punished."

Smack smack smack smack! In quick succession I feel the shock of four quick hard slaps on the ass. I muffle my screams, turning my face into the comforter of the bed.

His hands are back, the one soothing my ass, the other resuming its ministrations on my sex.

"I think I'll go ahead with my original plan and save your reprimand for later," he says finally and pulls both hands away. This time I can't rein in my whine before it escapes my lips, not even muffled by the bedspread. There's a soft chuckle from Christian.

"Now I know you've never received oral sex and that is really a crime. I want to know before we continue if you are ready for some anal play?"

I think for a moment, terrified. Am I ready for this? What in god's name have I gotten myself into?

"You may speak."

"Whatever sir wants." That's the closest thing to non-committal I could come up with. Maybe he'll take the hint that I'm not really ready.

"Good," he says, and I feel him spread my cheeks once again. He kneels down behind me and I hear him breathe in deeply, smelling me. I shift slightly on my feet, self-conscious.

"Anastasia," he says softly. I feel the soft, hot wetness of his tongue lick just next to my pussy and I moan. "This is a time," he says, licking the other side. "That I want you to be," he pauses to lick me very slowly right down the center, letting his tongue penetrate me just slightly. A long groan escapes me and my eyes roll back in my skull. Jesus, that feels incredible. "Very vocal."

His mouth closes around my clit and sucks gently, letting the flat of his tongue press gently against my core. I can't think, I can hardly stand, and the sounds I'm making are ridiculous. I sound like a dying horse.

He hums and my body convulses. I don't think I'm quite at an orgasm yet, but it's like I just had a mini one. I can barely catch my breath as his nose pushes against my opening and his tongue flicks my clit over and over again.

Instinctively, I arch my back slightly and start rocking my hips, riding his face. He swats my backside sharply with one hand and I stop. Still with his lips on me, he says, "You must stay still, Anastasia, or I will change my well-laid plans and punish you." The movement and his breath make me scream. Maybe it's gibberish, maybe it's swear words. I have no idea. "God, you are so responsive."

Slowly he runs the tip of his tongue from my mound, around my clit twice, up my vagina, dipping inside twice, and then keeps going. When he reaches the backside of my vagina, he nibbles gently on the little bit of flesh there between it and my ass.

"Holy shit!"

With it in his teeth, he laughs softly. Fuck fuck fuck. Why does that feel so good? He lets his fingers play with my clit as he repeats the process, starting low and working his way up, this time with little flicks of his tongue playfully along the way. His thumb enters me again, pressing forward on that rough spot I discovered during our cybersex session last night. He fucks me with his thumb and his tongue, one pushing at the front and the other pulling at the back. I feel full and empty at the same time, when another of those mini-orgasms washes over me. I'm pulling against my restraints, which seems to intensify everything. There's something glorious about handing over all the control to this man that I trust inherently.

"Sir, please," I moan. I am so close to a full release. I just need something. Him to speed up or slow down or...

He slides his mouth up further and licks my asshole, flicking it before plunging his tongue inside.

Everything becomes sensation as I orgasm over and over again, bucking and spasming wildly, pulling my restraints over and over again. I call his name loudly, "Mister Grey!"

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