Three Shades of Fifty Ch 1 - The First Time

I have met someone. His name is Christian Grey, he's gorgeous, he's a billionaire. And he wants me.

Okay, breathe, Ana. BREATHE.

Any girl would be over the moon about this, but somehow I have reservations. I'm definitely attracted to him, but I find myself hesitating. I've never slept with anyone and I'm nervous. That must be it. Yet, part of me isn't sure that's the whole reason.

I'm standing there, running my fingers along the red satin sheets on the four-poster bed, letting my eyes wander over the whips, chains, and canes, and my mind starts making all sorts of unapproved side trips. I think about Christian's lips on mine in the elevator, about his hand on the inside of my thigh, about the lacy underwear I have on, and about Kate. I imagine her ridiculous grin when I tell her that I slept with Christian Grey. "Oh, Ana, that's so hot!" she would growl.

I turn around to face him. Maybe it's that last glass of wine giving me confidence. "Okay."

"Okay?" he asks. "Okay, what?"

I take a deep breath and steel myself. "Okay, I'll sign whatever you want."

A huge shit-eating grin spreads over his face. He walks slowly over to me until we're inches apart. My body seems attuned to his and I feel that spark once more.

"Really?" The grin is gone and all that's left is the sexiest stare I've ever seen on a man's face. Kate would know what to do in this situation. I just feel like I'm melting into a puddle on the floor.

I say meekly, so quiet even I can hardly hear myself, "Yes, sir."

I hear him growl — growl! — and he immediately takes my hand and leads me back to his study, where I can sign all the appropriate papers. I tell him I'm not really sure what fisting is but I'm pretty confident I wouldn't like it.

"We can work out the particulars of the hard and soft limits in the morning," he says. He looks incredibly edible with a lusty, dark expression. I bite my lip and he stands.

"You're biting your lip," he says.


"Don't apologize. It's just that I want to bite it too, hard," he murmurs and he sweeps every last item, including all the as-yet unsigned documents from his desk. He loosens his tie and walks around the desk slowly. His entire demeanor has changed. He's domineering almost and demanding. I feel a wetness between my legs and a quickening in my chest.

"Stand up." I do as I'm told immediately. As he passes behind me, he kicks the chair I was sitting on from underneath me, letting him slide right up against my backside. His hand rests on my right butt cheek softly and I moan softly. Before I realize what has happened, he's smacked me soundly on the ass. I let out a small shriek, but his hand is back on my butt, caressing it gently.

"Shh, Miss Steele. You must learn to mind your tongue," he says. He gives me another sharp smack on the ass but I keep completely silent. He presses his hardness against my left cheek as he caresses my right again with his hand. "Good girl."

His hand runs down my leg to the hem of Kate's dress and his fingers run along my bare thigh there, pulling the dress ever so slightly.

"Now, before we get ahead of ourselves, Miss Steele, are you on any form of birth control right now?" he asks. Oh god, should I be?

"No, sir." I squeak.

"Aha, I didn't think so." I feel him shift as he pulls a condom from his left pocket and tosses it onto the desk in front of me. "Better safe than sorry, Miss Steele." His left hand joins his right, playing with the slowly rising hem of my dress, Kate's dress. I idly wonder if she has ever had sex wearing this dress.

"Now bend over and grab the edge of the desk." I do as I'm told, bent just slightly at the waist. "Take a small step towards me, Miss Steele." Again, I follow orders, and I feel my ass press into Christian's stiffness, sending a current straight to my groin. I can't help my sharp intake of breath at the sensation.

"You do have a breath-taking posterior, Miss Steele," he says as both his hands rub over my entire ass until his fingers hook around my hips and he pulls me into him hard.Very hard. I smirk at my play on words. I'm now completely bent, at a right angle and can feel myself becoming wetter by the moment.

"Spread your legs for me."

I hesitate slightly, trying to figure out how to properly shift my weight so as not to fall over. Before I can react, his right hand leaves my backside and quickly returns, spanking me much harder than before, then again. I almost cry out, but manage to stop myself before more than a small "meep!" escapes my lips.

"Spread. Your. Legs," he says deliberately.

This time, I do as he commands, and quickly. My ass is throbbing now and I feel very exposed. Kate's dress is still covering me, but I have a feeling that won't last. My entire undercarriage, if you will, is facing him, and my head is dropped. All I can see are our four feet and the floor. He walks to my left side, continuing around the desk again.

"Wider." I shimmy, best I can, until my knees are about shoulder-width apart, straining against the skirt of the dress. I know my feet will start to hurt soon, the heels are too high for this to be comfortable for long.

"Good," I hear him say. I can tell he's on the other side of the desk, circling around.

"Now, Miss Steele," he begins. "I hope you're not particularly attached to your underthings."

I squirm slightly. "Well, they were a gift, sir."

He stops his slow progression around his desk. "From a man?"

"Yes, a man I like very much," I murmur, trying my best to sound sexy.

He snorts quietly. Oh shit, is he pissed?

He strides quickly over to me and lifts the skirt of my dress unceremoniously over my ass, revealing the lacy blue panties. He stills. I hold my breath.

Moments pass. I'm starting to get dizzy from holding my breath. He lets out a sigh and I immediately relax.

Sliding a finger under the string of elastic at my hip, he says, "Oh, Miss Steele, we're going to have to do something about that defiant streak." He punctuates this by snapping the elastic back to my skin, setting it ablaze.

"As much as I am touched that you like these," he says and he rips them with his bare hands, letting them drift into my line of vision on the floor between my ankles.

He continues his slow march around his desk again. "I'm going to spank you, Miss Steele, and I want you to stay completely still."

"Yes, sir."

"I'm was going to spank you seven times," he says, across from me. "But since you went and made me jealous, I'm doubling it." He's behind me again, his hands pulling my naked hips into his groin. I moan at the contact. "Hush," he says gently. "But remember," he slides a finger over my nub, nearly making my knees buckle. "I want you to count."

"Yes, sir."

I feel a shiver as he moves back and to the left, no longer keeping my naked backside warm.

It seems like eons pass and then suddenly I feel a crack across both cheeks. Holy shit! That fucking hurts! I scream and it somehow comes out as a vaguely intelligible, "One!" His hand rubs the spot he just struck sensually. I arch my back slightly, making my legs a little straighter, pressing my butt into his hand. And then it's gone.

Smack! Smack!

Once on each cheek, right in the middle. "Two, three!" I wail.

His hands caress the throbbing spots gently once more.

This time when he removes his hands, I hear metal clinking together lightly before I feel another hard slap, this time on the sensitive spot where my left thigh meets my ass.


He rubs it once more, then repeats the process on the right side.


And then I hear him walking around the desk once more. I realize I'm panting. My ass feels swollen, tender, and I'm so aroused despite myself. I'm scared as all hell, but what girl isn't the first time?

When he reaches his chair, directly opposite me, I hear him pull it out and sit down. I let my curiosity get the better of me and take a peek to see what he's doing. He's untying his shoes. I watch, mesmerized, as he removes first one then the other, then removes each sock and rolls it up, sticking it inside its shoe. He's completely engrossed in what he's doing and it's not until he's finished his task that he looks up at me. I immediately drop my head back down, knowing I've somehow misbehaved.

"Tut, tut, Miss Steele. I didn't say you could move," he says as he circles around once more. When he gets behind me, I see his naked feet. I don't know what it is about his bare feet, but I find them incredibly sexy, especially when standing between Kate's black patent leather high heels.

He wraps his hand around my pony tail and pulls back roughly. He presses his crotch into my ass and leans over my body so his mouth is right next to my ear, holding my thigh still with his free hand. "Miss Steele, I think you just earned yourself one more. And then I'm going to fuck you very hard." His hand that was on my thigh slides around until it begins to play with my nub once more. I moan but can't move at all, completely subdued by this man. "I thought I told you to hold your tongue, Miss Steele," he breathes, and slips two fingers inside of me. It's a good thing his arm is underneath me to keep me from falling when I lose all the strength in my legs for a moment.

"Oh, Miss Steele, you're so ready for me," he says, pumping his fingers in and out of me, agonizingly slow. "I do think you're enjoying your punishment."

"Yyyyes, sir," I stammer.

He releases my hair and stands, letting my head loll forward again. Still working his magic with his fingers, he smacks me hard with his other hand.

"S-s-six!" I scream out.

"Oh, Miss Steele, I'm not sure how much more of this you can take."

He smacks me hard on the other cheek.


"I'm not sure how much more I can take, either, Miss Steele."

He switches hands, now sliding his fingers in and out of me from behind. I can hear him licking the fingers of his unencumbered hand. "Mmm, Miss Steele, you taste divine."

I moan and buck my hips. How the hell is he making me feel so depraved and so sexy at the same time?

He slips a third finger into me and I feel strained, full, almost painfully so. I gasp and try to catch my breath, but I feel a quiver racing through my core.

"I don't want you to come yet, Miss Steele."

And how the hell am I supposed to stop from doing that?

"No, s-s-sir."

"Good girl," he says. Smack! Smack! One on each thigh.

"Eight, nine!"

Smack, smack, smack! He riddles my backside with spanks, distracting me, heightening the sensations.

"Ten, eleven, t-twelve!"

I hear the metal again and realize he's unbuckling his belt. I hear his zipper and watch as he steps out of his crumpled trousers.

"We're almost there, Miss Steele, the moment we've all been waiting for," he says seductively, like it's an order. An order to do what, I don't know, but an order nonetheless.

Smack! Smack! These slaps land almost on my hips, painfully. He takes his fingers away and reaches around me to the desk before I hear the rip of foil.

"Thirteen, Fourteen," I pant.

There's an interminable pause before the last slap, right between my cheeks, hitting my ripened sex, making every fiber of my being perk up and take notice.

"Fifteen!" I scream as he enters me from behind, grabbing my hips and thrusting violently into me, ripping my virginity to shreds. "Ah!"

He stops momentarily and I can feel his fingers trembling slightly.

"Ana?" He has lost all the confidence he had in his voice. He sounds like a small, lost boy, scared and confused.

"Don't stop," I whine, urging him to push through the pain. I can see the light at the end of the tunnel and I want to go there with him so much. "Please," I whisper. "Please don't stop."

That's all the encouragement he needs, and he resumes his ministrations, though much slower and more tenderly now. He reaches his hand around and teases my core. "Ana, come for me, baby," he groans, and, like a good sub, I obey.