Date Night 175

It was our monthly date night, and it was my turn to organise. I had special plans, and I was going to make sure it was unforgettable.

Dinner was booked for 7:30, and I rolled up to your house at 5. Enough time for you to get ready, and go for a drink beforehand. It was a fancy dinner, so we were to dress for the occasion, me in a pressed white shirt, slacks and newly polished boots, and you... well, I had brought something special planned for that.

You opened the door, standing there in your silk dressing gown, and wet hair from your fresh shower. I presented you with your favourite flowers. A kiss hello, and you started to ask questions. "Where are we going?", "What am I going to wear?", and "Wait... what's in that box?"

Not giving any answers yet, we walked into the kitchen and you placed the flowers in a vase, taking a deep breath of their fresh smell, and smiled. God I love your smile.

I opened the lid of the box, towards me so you couldn't see, and pulled out a nice bottle of wine. "This is to get us started, the rest of this is for you tonight"

You opened the wine, and poured us a glass each.

I left, with the box, and headed to your bedroom. Placing the box on your bed, then walked back out. I picked up the glass of wine, and we cheered. Kissing you passionately, I pushed you up against the kitchen counter. I bit your neck and nibbled on your ear, then slid my hand up your leg, under your gown, and over your freshly shaved pussy as you moaned softly. Quickly stopping and pulling away, so as not to get you too excited, I looked at you and said.

"Tonight, beautiful, you are all mine. Is that clear?"

You just nodded, a small grin on your face, as you sipped your wine.

"The box is in your room. I want you to follow the instructions inside very carefully. Do not disappoint me.

Now go get ready"

You took your wine with you, headed to your bedroom, and started to get ready.

I let you be, as I heard the sound of your curated bedroom foreplay playlist start, while I went back to my car and brought in my bag.

In your bedroom, you curiously opened the box. On top, was a hand written note.

"I want you to wear everything in side this box"

The word "everything" was underlined.

Putting the note aside, you pulled out the first item, a black strapless mini dress. It was your size, but it was short, just above halfway up your thighs.

You laid it aside and looked in the box, and pulled out some shiny black stiletto high heels, with a small platform, again in your size.

Two items remained.

Pulling out a small Victoria's Secret shopping bag, you opened it to find a lacy red g-string. Nearly see-through, it wasn't going to cover much.

The last was a small brown box, written on it were the words "choose one". Opening it up and tipping it onto the bed, spilled out three silicone butt plugs. "Was he expecting me to wear this out tonight?" You wondered. Picking one up, it was smooth, flexible and had a T-shaped base. The thought of being out at dinner wearing the plug excited you, you were already starting to get wet at the thought. No one but you two would know. You chose one, and continued to get ready.

When you came out of the bedroom, my jaw nearly dropped to the floor. You looked stunning.

You had quickly curled your hair, put on makeup, thin winged eyeliner, and bright red lipstick. Your new dress hugged your athletic body tightly, pushing your tits up and out, your ass hugged tightly. But your legs, with the dress so short, and the platform stilettos, your legs went for days. Standing there, holding your clutch, you were a sight to be seen. It was hard to not take you right then and there.

I walked up to you, grabbed you and held you tight. Not wanting to smear your lipstick already, I only gave you a light peck on the lips, then moved to bite your neck. My hands traced down your back, gripping your ass, and my fingers slid down until they felt the base of the plug between your cheeks. I grinned.

"Good girl. Which one did you choose?"

"The middle sized one" you replied, smirking.

I was impressed, my cock twitched, picturing it.

Finishing off our glasses of wine, we left and walked into town.

Our first stop, was the local wine bar. Cozy and comfortable, we drank a great glass of Shiraz, before needing to head off. Another drink, this time a cocktail, at another bar, before heading across the road to the best restaurant in town.

Dinner was, as expected, exquisite. Plied with wine and a delicious set menu, we laughed and talked the night away. We both nearly forgot about the secret hiding under your dress.

We left, and headed back down to the bottom of town, to the whisky bar. It was dark, loud, and had board games to occupy us. Before we entered, I took your clutch off you, and pulled something out of my pocket, slipping it inside your bag. Handing it back to you with a knowing look, you waited until we were inside with a booth to check. I went to the bar and ordered us drinks, and sent you a text.

"Take your bag to the bathroom and come back wearing it". As I got back to the table, you looked at me, biting your lip, got up and left.

In the bathroom, you pulled out the surprise. A Lovense remote controlled egg vibrator. Already wet from the nights events, and especially from this new surprise, it slid in with ease.

Walking back, you sat down and picked up your drink before saying anything.

"So what's your plan then?"

I looked at you and grinned. "This."

Pressing a button on my phone, the egg burst into life. The sensation nearly making you drop your drink. The vibrations railed hard up against your gspot, and reverberated into the plug in your ass. The tail vibrated onto your clit too, but not as much as you would like.

Everything felt amazing, and you knew it wasn't going to take long to get you off.

And then it suddenly stopped.

You looked at me, pleadingly. And I relented, but turned it back on to its lowest setting. Much to your disappointment

We started playing cards, and with each round, I would turn the setting up one notch, with you doing your best to ignore it. I got up to order another drink, and leaving, turned it up to full blast.

The powerful vibrations sending waves through your nerves. You squirmed in your seat, hoping no one would notice you writhing in pleasure. Trying desperately to maintain composure. Coming back with more drinks, you begged me to turn it off.

I shook my head. "I want to watch you cum"

I looked straight into your eyes as you wriggled, panting, letting out soft moans. Hoping no one would notice.

"Cum for me", I demanded, and you were sent over the edge. I let you ride it out, softly moaning, eyes closed, your hands digging tightly into mine. You almost forgot you were in a bar. A couple of glances in your direction, you wonder if they knew what was happening.

Turning the vibrations down, but not entirely off, I say it's time to head home. I have more in store for you, but you're going to have to wait.

The walk home is made slightly uncomfortable by the persistent soft buzzing of the egg, and fullness of the plug, constantly reminding you of their presence.

We got home, and walked in side. Pouring a glass of wine each, I grabbed my bag and we walked into your bedroom. Taking your glass off you, I spun you around and pushed you up against the wall. Kissing you hard. Tonguing you. Probing your mouth.

I turned you around, and told you to stand facing the wall, as I reached into my bag.

Pulling out a set of soft cuffs, I undid your dress and slid it off, down to the floor. Cuffs tied to your wrists, I pulled your arms behind you and clipped them together. Next, a blind fold placed over your eyes. Good luck getting out of my control now.

I left you standing up against the wall, as I went to my bag to pull out the rest of the toys I had brought, and laid the on the bed. Walking back over to you, I stood behind you and pulled your head back, with a hand around your neck.

"Are you going to submit to me?" I ask.

"Yes" you say, in almost a moan.

"Are you going to do everything I tell you?"

"Yes Sir" you say, falling into line.

"Your safe word is 'Red'. Do you understand?"

A simple nod suffices.

A thick collar is placed around your neck, and a thin leather leash holding you to my will.

I drop to my knees behind you, and slide your g-string off. A rough bite on one ass cheek, a soft kiss on the other. I run a hand up your thigh, and begin to take out the still vibrating egg inside of you - until it's almost out, and push it back in side. I slowly fuck you with it for a minute or two, as you moan - until it comes out completely. I hold it up to your clit, and turn the vibrations on to maximum - but only for 30 seconds, before it's turned off and put away. You moan in frustration.

I look at you standing there, handcuffed, legs spread, ass plugged, dripping wet. Tonight was going to be good.

Holding your leash, I pull you over to the carpet next to your bed, and place you on your knees. You instinctively open your mouth - ready for me.

I walk behind you, picking up my bag and pouring all the contents out, laying them onto the bed. I place into your cuffed hands a soft g-spot vibrator, and whisper in your ear "I want you to cum for me". You knew this was going to be a struggle, you could barely move, your hands were behind your back. Even with the toy, you could barely reach enough to play. But that didn't matter, you were going to have to try.

I sit back on the bed, and watch you get started. Fumbling for the controls, and the correct orientation of the g-spot massager, you hold it awkwardly in your fingers, struggling to use it the way you want.

Sitting on the bed, I sip the wine, enjoying the view.

The vibrator sliding up against your gspot. The vibrations reverberating through the plug in your ass.

Struggling to fuck yourself. Moaning. Desperately trying to cum.

I stand up, and take my clothes off, already rock hard watching you play with yourself. Walking in-front of you, I place the tip of my hard dick at your lips, as you open up.

You being to lick and suck on my dick, but I stop and pull out.

"I want you to cum. Don't worry about me. I will use your mouth however I want."

"Yes Sir" you say in a soft moan, the vibrator slowly working in and out of your dripping pussy.

I grab your ponytail and hold your head in place.

You open up, holding your lips into an O, as I begin to slowly fuck your mouth.

You pull the vibrator out, and hold it to your clit. Fumbling to turn the vibrations up. You feel the pressure build. You're close. My hard cock sliding in and out of your mouth, over your tongue, as I use you. Your eyes closed, unable to see anything anyway - you can only feel. You're right on the edge, ready to explode.

Noticing this, I say. "If you cum now, it will be your only one for the night. If you stop, I will fuck you over and over until you scream." I'm still using your mouth.

Desperate for release. So close to the edge. You struggle to think clearly. The vibrator feels so good on your clit, sending shockwaves through to your core. Your ass, full. You don't want it to stop. But the thought of this being your only orgasm for the night makes you reconsider.

Reluctantly, with a whimper, you lower the vibrator off your clit, and drop it to the floor.

I pull out of your mouth, my dick now soaked.

"Good girl." I say

"Thankyou Sir" - already regretting not continuing, as you hear the sound of the vibrator buzzing away on the floor.

I pick it up, and put it aside. "I want you on the bed. Now. Ready for me."

I help you up, and bend you over on the mattress. Your knees spread, your face pressed into the mattress, your hands still cuffed behind your back, your ass high.

Your pussy looks so inviting, so wet, I just want to fuck you right then and there. I come close behind you, place a hand on your back and push you down, as I place the tip of my cock ok your clit. Working over it, swirling it around, tracing the outside of your lips, as you moan. I trace it up, parting your lips, placing the tip right at the entrance and begin to slowly push forward. You moan even louder.

I'm slow, teasing you, only letting the tip of my cock enter you. It's not enough, and you softly beg "please...", in a muffled voice.

I pull out and away, gently smacking your ass, as you moan in frustration. "Not just yet babe"

You hear me shuffle things around on the bed, picking up something, but you're not sure what.

You feel me begin to play with the plug in your ass, pulling on it gently, as you relax and let me take it out and set it aside. An odd sense of mixed relief and emptiness, after wearing it all night.

From my other hand, you feel something else slide directly into your soaking pussy with ease, as you realise it's the next sized up plug.

I leave it there inside of you, as I head back to the bed and pick something up.

A hard smack hits your ass and you jump, as you feel the sting of the riding crop.

"Count to ten for me" I command in a stern, sexy voice, making you desperate to see please me (and yourself). L

"One" you say, in a soft voice.

Smack! The other ass cheek stings.

"Two"

Smack! "Three"

Smack! "Four"

Smack! "Five"

Smack! "Six"

Your thoughts wondering if it was a little harder than before.

Smack "Seven"

Smack! "Eight"

They definitely were.

Smack! "Nine"

Not wanting to break. You can handle this.

Smack! "Ten"

Your ass now red and sore.

"Good girl. Let's give you a reward" I say, as I tap the base of the plug sticking out of your pussy with a light tap of the crop.

I grab the plug and fuck you with it gently. Smaller than the vibrator you were fucking before, and not long enough to tease your gspot, you moan desperately.

Next, you feel copious amounts of lube on your ass, and a finger, as I slowly finger your tight ass and fuck you, readying you for the next plug. I slide the plug out of you, it nearly dripping in your wetness, and place it slowly at your ass. You feel me push, pushing the plug inside you, and slowly stretching you. Just before it gets to its widest point, I stop, and pull back. I slowly fuck you with the plug for a few minutes, stretching your ass to the widest point of the plug. Until I push it in further, and you feel your ass tighten up around the new plug, holding it in place.

From all the sensations of the night, you so badly want to be fucked, and to cum again.

I pick up the vibrating wand, turning it on low, and place it onto your clit.

Maybe this is your chance.

I slowly move it around, rubbing your clit with the wan, and gradually turn up the vibrations as you grind into it.

Then I slide it upwards, over your wet pussy, and onto the new plug, sending vibrations deep into your ass.

I pick up the other vibrator, and hold it against your clit. The sensation of two power vibrations nearly sends you over the edge.

"You're not allowed to cum until I say so"

I turn the vibrator on your clit to high, and rub it over and around your clit in circles. I slide it up and down between your lips, making it nice and wet, before pushing it inside your pussy.

I begin to fuck you with it, slowly, pushing it all the way in, deep and vibrating over your gspot, before pulling it nearly all the way out. Over and over, as you feel an orgasm building up.

Faster and faster, you don't want me to stop.

I don't.

"Hold it. Not yet" as I continue to fuck you.

The wand still resting on the plug in your ass, and the vibrator fucking you, pushing against the plug with every stroke. The vibrations grinding on your gspot, as the toy slides in and out. You're so close, and could cum any second, but try to hold onto it until I say so.

I fuck you like this for a few more minutes, until you hear the words you're desperate for: "Cum for me slut"

You nearly explode at the word alone. Shaking violently, grunting, screaming into the mattress, clenching your bound fists. Shockwaves sent through every nerve in your body as you tense, riding a wave of orgasmic pleasure, as everything still vibrates inside you.

As you come down from the high, back to earth, take take the vibrators away and turn them off.

"It's my turn" I say, standing behind you, stroking my dick at the sight of you.

I press my rock hard dick up against you, holding it there, as you wait.

I push hard, entering you completely, filling you up, as you gasp. Fuck me you feel good. You're so wet. So tight. The I feel the plug pushing against my dick. I wasn't going to last long.

I begin to fuck you slowly, trying to savour the feeling. My hands grip tightly into your ass cheeks as I hold you in place. I begin to fuck you hard. Pumping in and out of you. The plug grinding over the tip of my cock. You gripping my cock tight. I'm only going to last 10 minutes at best.

You ask me to undo your hands so you can play with you clit, but I say no.

You're mine. You will cum when and how I let you.

I continue to slide in and out, picking up speed. Grunting. Taking what's mine.

Until you feel me explode. Filling your pussy with over a weeks worth of cum. Continuing to fuck you until I can't any longer.

I pull out, leaving you in place, and walk infront of you. "Clean my dick and I will let you cum again"

You don't need to be told twice. You open up and swallow my dick. Coated in a mixture of cum and your pussy juices. I grab your hair and you tongue around my dick, lapping everything up. Trying to catch every drop of cum.

"I'm going to hold the wand onto your clit, on high, until you cum again. You can cum whenever you want". You nod and moan, your mouth still full of my cock.

I walk back behind you, and pick up the wand, turn it on high, and hold it against your clit. Not moving it. Letting you grind up against it.

You feel the vibrator slide into your dripping pussy. Fucking you as you're filled with my cum. Cum dripping down your pussy, onto the bed, over you clit.

I fuck you with the vibrator for a bit, then stop. Leaving it in place.

You feel me grab the plug in your ass, and slowly pull it out, you ass not wanting to let it go.

I throw it aside, and reach forward. Undoing your cuffs.

"I want you to hold the wand" I say, and you grab it, holding it where you want it, grinding into it.

I begin fucking you with the vibrator again. Getting it nice and coated in the mixture of cum and juice. Then I pull it out, and begin to push it into your ass. Stretching you wider than the plug. Slowly pushing deeper.

You continue to grind the wand on your clit, as I fuck slowly your ass with the vibrator. Your pussy now feeling empty and desperate.

Your orgasm begins to build. You're getting close.

I pull the vibrator out, and you feel something else push into the entrance of your ass. It's my cock, hard again. I've been stroking it this whole time, and I'm ready to cum again.

You're not sure if your ass can stretch any more, I'm a lot bigger than the vibrator, but you're too focused on the wand on your clit.

I don't push any further, just slowly fucking the entrance, and still stroking my cock. You feel my hand slapping your ass on each stroke. Harder and faster my strokes become. And you build up, so close to cumming again.

I grunt, "I'm going to cum", and it tips you over the edge.

Your ass clamps down over the tip of my dick as you begin to cum, and it sends me off. I cum, unleashing another large load, directly into your ass. I pull out for the last few, and cum over your ass cheeks and back.

You're still cumming. Holding the wand onto your clit. Not letting go. Moaning, screaming, shaking.

Fuck me you're so god damn hot.

You finally drop the wand, unable to take any more, and collapse.