February Contest – Image 17
I tug at the hem of my skirt while nervously glancing around me, hoping no one I know will be in there. The bar is pretty popular but it is also far away from where I normally go out, so I think I’ll be okay.
The bouncer looks me up and down before handing back my ID.
“Go ahead.” He smiles as his eyes linger on me a bit too long.
“Thanks.” I take a deep breath and push through the curtains into the bar.
Bathroom first.
The sudden reappearance of her voice in my ear practically makes me jump. At the beginning of the cab ride over she was non-stop talking through the airpod in my left ear, going on about rules and what is expected of me. Since then, there has only been silence.
I don’t respond or disobey. I know that will only make things tougher for me, though I do feel drawn to be my normal bratty self. Instead I head directly to the bathroom, walking past the mostly filled bar area without even a glance toward the patrons sitting there.
There are three single bathrooms lining the hallway beyond the bar, all occupied. I wait patiently but the waiting allows my mind to wander into anxiety triggering thoughts. Part of me wants to run, but all that will come of it is regret. I know I want this. There’s a reason I agreed.
The door in the middle pops open and a girl of a similar age steps out, smiling briefly to me before leaving. Without acknowledgement, I dart in and lock the door.
Good girl. You’re following the rules well.
I look into the mirror to give her a view of me.
I like the outfit, especially that top. I’ll have to ask where you got that later.
I have to admit, I do like the look. A short black skirt with a white top, all under a grey peacoat. There are only a few constraints on what to wear, so I took the opportunity to add a few pieces to my wardrobe on her dime. The thing she truly cares about is the collar around my neck. It’s a fashionable piece, with a link and charm off the bottom, and could easily pass as a normal choker. At least I hope it does. Judging by the look from the bouncer it may be more obvious than I thought.
Regardless, the collar is an important part of the deal. It certainly acts as a consistent reminder of my role in this dynamic. More importantly though, is the camera in the front of the collar, feeding live video back to her.
You remember what you need to do before we proceed, correct?
My heart flutters but I do it anyway. While still facing the mirror, I lean forward and pull down my top, low enough for the camera to see down my chest in the mirror.
Wow, I knew it. They’re absolutely adorable.
“Satisfied now?” I instantly regret letting my brattiness come out.
Careful with that attitude. Remember who is in charge. Insolence will only make it worse for you.
My cheeks turn red in the reflection. I need to be better going forward.
Keep going. Now the other end.
I lift the top back up and then reach down to pull up the skirt. My uncovered pussy slowly appears in the mirror.
Good. Now turn.
I turn around, my ass now facing the mirror, and then turn the collar so she can get a good view.
Bend. I can’t see it.
I obey, bending over enough so the red gem center of the plug becomes fully visible.
Good girl. Turn back around. You will touch yourself while I go over what happens next.
A spike of anxiety sets in but I again obey. I turn and pull the collar back around, once again facing the mirror head on. I then reach down and begin to touch myself, my fingers gliding effortlessly across my already soaking pussy. Between the anticipation of tonight and my obedient responses to her commands, it’s no surprise I’m turned on already.
Looks like you’ve followed every direction so far. We can proceed. When I tell you, leave the bathroom and walk to the bar. He is in the third seat from the end of the bar closest to you. You will sit in the seat next to him.
The voice pauses, drawing out my torturous self teasing.
Go now.
I obey, removing my damp fingers and straightening my clothes out before exiting the bathroom. There are two people waiting outside but I ignore them and briskly walk past.
As I walk back into the bar area, I take a better look around. It certainly fits the speakeasy mold. A long, wooden bar with gold accents scattered throughout on my left. On my right is the lounge area, filled with chairs and small couches set up in small circles. Even most of the attire being worn fits a fancier, old school vibe.
The first two seats of the bar are filled with what looks like a young couple, the man in a full suit and the woman in a gorgeous, one-strap maroon dress. I can’t help but feel out of place next to her. She looks like a Hollywood starlet.
Beyond those two is the man, as expected. He too is wearing a suit, although the jacket has been tossed around the back of the chair. His focus is down to his phone, so he doesn’t initially react as I approach. I quickly position myself on the chair, letting the camera linger in his direction before facing forward. From the front I see that his tie has been loosened and his sleeves have been rolled up to his elbows. The drink clutched in his right hand is almost empty, basically just a chunk of ice remaining. I suspect he’s been here for a while.
I snoop a glance down to his phone, which is open to his message app. As he finishes typing something out, a new message pops up, something only one line long. His head immediately lifts up, catching my snooping in action. He first glances at the airpod and collar, and then smirks while setting down the phone.
“You must be Lilly.”
His voice is calm and confident, with a hint of refrained excitement. A stark contrast to me, futilely attempting to hide how much of a shaky mess I am. He even looks more handsome than his picture. It’s a little intimidating.
“I am,” I respond after a long pause. “You must be Scott.”
“Yes, nice to meet you. Can I get you anything?”
Cranberry vodka.
The voice startles me again. I didn’t expect her to chime in for something so trivial.
“Cranberry vodka,” I reply.
From there, our date presses on like any regular date would. We each have a couple drinks, asking questions back and forth while covering a litany of topics. The only topic that isn’t covered, or even mentioned, is her. He must have his own set of rules as well.
After her input on my drink choice she is mostly quiet. Her only salacious command while at the bar is for me to casually open my legs and flash him. Unfortunately, he doesn’t seem to catch it.
Most of her commands occur during my trips to the bathroom. Nothing too crazy, most likely just testing my obedience and reminding me of my place. But every time I come back to the bar a little more riled up and antsy.
Mercifully, the moment I’ve been waiting for finally comes as the bartender brings over the bill.
“So,” Scott says as he lays his credit card down, “Would you like to keep this night going? We can head back to my place.”
The choice is yours, but if you say yes, that is the last choice you get to make tonight.
“That sounds great!” I try to hide my eagerness but I’m sure it’s obvious how excited I am. It’s been a fun date, but I’m ready for the main event.
Good girl. I’m proud of you. Now comes the real fun. Be a good slut and you will be rewarded. Disobey any of my commands and you will be punished.
When the cab pulls up, he reaches in and opens the door behind the driver for me.
“What a gentleman!” I tease with a wink as I duck into the car. He laughs, closes the door, and makes his way around the car.
Skirt up. Spread your legs. Let him see what he missed earlier.
Fuck, already?
I hold back my instinct to protest and roll back the skirt until my pussy is in plain sight. She’s trying to bait me into breaking the rules. I can’t make it that easy for her.
The door opens and he jumps in. As he turns to face me he freezes like a deer in headlights, his eyes immediately drawn down between my legs. The world is mostly dark around us and there are no lights on in the car, but the ambient light from the street is just enough for him to see clearly.
“Ready?” the driver asks while starting the navigation.
“I…ugh,” he mumbles back, still completely caught off guard. He looks up to me, seemingly still trying to process if this is real.
“Yes, thank you,” I say to the driver. Scott breaks free from his trance but still alternates glances between my pussy and my face.
See what you do to him? Just the sight of that pretty little pussy is breaking him. Take his hand. Let him feel how horny you are.
I reach out and reposition his left hand on my thigh. His eyes grow even wide as I slowly slide it up until I feel his fingers make contact.
He takes over from there, teasing around my lips and clit as I lean back and suppress the moans I feel bubbling up.
Pull the top down. Give him a show.
I glance up to the rear view mirror to confirm I am out of sight from the driver’s view. Then I reach up and tug the top down, exposing my right breast.
He shifts in his seat, repositioning himself as I catch a glimpse of a bulge by his thigh. The sight inspires me and I begin my show, alternating between massaging my breast and teasing my nipple.
Apparently my performance inspires him as well. His fingers slide slowly inside of me, curling up as they fill me. I tense my body to suppress the gasp trying to burst through me. He then begins a massaging pattern while the palm of his hand rubs on top of my clit.
Good girl. At this rate he may fuck you right in this car.
The driver seems oblivious, but even the slightest of glances back would catch my struggle to maintain composure. My left hand clenches the handle on the door so tightly I feel like it might break it.
No cumming in this car. Save it for later.
This time a slight moan escapes me. I close my eyes, delaying the feeling as best I can, but everything about this moment could send me over any second. Exposed in public while getting fingered and the verge of cumming near a stranger. It’s a fantasy playing out live.
Then, mercifully, his fingers stop and remove themselves. I look at him, both in pleading desire and confusion. The cab pulls off on the side of the road and I understand.
We have arrived.
The elevator dings closed and my first thought is to jump him right here. Before I get the chance, her voice returns.
Drop something and bend to pick it up. Show him what you’ve been concealing.
More teasing is not what I want right now, but I concede. I reach into my pocket, fake fumbling around, and then let my keys fall out to the floor.
“Shit,” I swear as I turn and bend to pick them up. The peacoat is short enough that with a little help I lift it high enough to completely moon him.
“Oh my God. Have you had that in the whole time?”
“Oh sorry!” I feign embarrassment back, but he sees right through it, so I opt for an overly dramatized flirtiness instead. “Wanted to be prepared for anything, ya know, just in case.”
Before he answers, the elevator opens and I walk into the hallway. It takes him a second, but he gathers himself enough to follow and lead me to the apartment.
As he opens the door, I move to walk in, only to be stopped in my tracks.
No clothes in his apartment. Strip now.
“What? I can’t-”
I stop myself but it’s too late.
Oh Lilly. You were doing so well.
“Can’t what?” He asks but my focus isn’t on him.
Now you have to crawl while in his apartment. Only he can give you permission to stand or be clothed. Don’t screw up again.
I exhale as Scott looks toward me, puzzled and waiting for a response. Without a word, I begin to strip right there in the hallway.
“W-what are you-” He trails off as I toss the coat and top into the apartment. As I begin to lower the skirt, a noise comes from somewhere down the hall. Whether it was from inside an apartment or a door opening didn’t matter, it’s enough to spark urgency. I toss the skirt in, fall to my knees, and crawl into the apartment hastily. Once inside, I stay on all fours, facing him.
“I…wow. I was not expecting this.” He tosses his own coat down but his eyes stay glued to me, the naked woman on all fours for him.
“I have to crawl and be naked in your apartment unless you say so.”
Add sir.
“Sir.”
His face betrays how completely dumbfounded he is by my actions the past few seconds. He knows what the deal is for tonight, but I don’t think he realized just how far she is willing to go.
Ask to suck his dick. He’s been hard since the cab. I think you owe him.
“Can I go down on you sir?”
“Uhh yes, of course Lilly.”
Tell him to call you “slut.”
“Thank you sir, but you can call me slut instead. I prefer that.”
“Uhhh okay…good slut.” He still seems unsettled. Hopefully this will help. I crawl over to him and sit back up on my knees. My eyes stay fixed on his skeptical face as I fumble with the belt buckle and then rip it off.
Use his belt as a leash. Give him the end.
This one takes me a second to act on but I manage to suppress the insolent reaction brewing. To be fair, it is within my limits. With shaky hands I feather the belt though the buckle and then slide the loop over my head. After snugging it around my neck I hand him the other end.
“Holy shit,” he mutters, grasping the end of the belt in disbelief. Before he can say anything else I resume the process of getting his pants off. At least he is enjoying this so far, his dick looks like it might tear through his pants any second.
He’s too nervous. Ease his concern.
“Don’t go easy on me sir. This slut needs to be handled properly.” I allow a slight teasing smirk.
His dick springs free as I drop his pants and boxers to the floor. As I reach up to grasp him a tug on the leash chokes me slightly. I look up and see a devilish, ear to ear grin. I think his nervousness is gone.
“No hands,” he commands.
I nod and drop my arms. The next thing I know, my mouth is as deep as it can go onto his dick, gagging and drooling as I continue to refrain from using my hands. With the leash he holds me tight to him and his hips begin to buck. I’ve given a good amount of blowjobs in my life, but I’ve never been face fucked while pulled on a leash like a little plaything. This type of situation has only even been a fantasy.
Now that I’m living it though, I want even more.
I must be dripping on the floor right now. I lift my gaze up, just enough to lock eyes with him, and see that animalistic hunger I’ve been waiting for all night. The sight of that along with my meek stature under him makes me feral. I would let him do anything to me right now.
He tugs the leash back, prying my head away from him. I gasp and inhale deeply, not realizing how out of breath I actually was.
“Bedroom,” is all he barks out as he begins to walk away, tugging me by the leash. I stay close, frantically crawling in order to keep the leash from choking me.
It’s been a while since I’ve heard her voice in my ear, though I swear I can hear the light sounds of a whimper coming through. I wonder if she can actually see what’s happening, or if she’s just imagining it.
We reach the bedroom but stop right at the base of the bed.
“Stand,” he demands, pulling up on the leash. Ungracefully, I stumble my way up.
For a second, nothing happens. He just stares lustfully into my eyes, pondering something. Then, he releases the leash and reaches around my neck.
“I know this is supposed to stay on,” he says as he unclasps the collar. “But she won’t be able to see you getting fucked like the slut shes turned you into deserves. She needs to see her hard work pay off.”
He walks around the bed and sets the collar on the dresser, facing the whole bed.
Oh fuck yes! This is going to be great!
“She likes that sir,” I whimper out, still swooning from his last line. There is even a little shakiness in her voice now.
“I figured she would. Now,” he turns back to me, “Onto the bed, on all fours.”
I climb on and watch as he slides off the last of his clothes. He then walks around the bed to my backside, leaving me completely at his disposal. My imagination immediately runs wild in anticipation.
“Let’s take a closer look at you,” I feel his hands tease around my lips, circling up and around a few times before settling around the base of the plug. My cheeks burn red, not only from the humiliation of him inspecting me but also the fact that someone is watching it happen.
“I have to admit, this was a nice, unexpected surprise. But I think it served its purpose.”
The pressure of the plug pushes back against me as he twists and slides it out. It stretches and stretches, taking me to the limit, until finally there is relief.
“Mmm!” I moan out at the sudden absence of it. The relief feeling doesn’t last long though. Suddenly the leash is pulled back and the sting of a spank makes me yelp.
“Now,” he growls. “Let’s give her a good show!”
“Yes sir!”
Good slut! Make me proud.
Most of the building windows are dark, which makes sense at 1AM, except for one apartment at the corner. My apartment. She is still awake.
The cab drives away as I make my way inside, still wobbly from the night’s events. Quite frankly, it’s impressive I can even walk at all right now. I’m not entirely sure how disheveled I look but I bet I don’t want to run into anyone.
The elevator opens to my floor and I make my way to the door at the end. The warm glow of light emits through the bottom. I take a deep breath and open it.
“There you are! Fun night?”
I roll my eyes and walk in. She sits on the couch opposite the door, only wearing a T-shirt and watching TV. The evidence of her own fun night still sits on the table in front of her.
“So how many times did you cum watching all that play out? ” I ask, looking at the vibrator next to her still open laptop.
“Oh, quite a few. Can you blame me? I nearly fell off the couch when he slammed your face into the pillow and fucked your ass. And then when you screamed ‘I’m cumming!’ while looking at the camera? Oh mama! That one’s burned into my memory. That looked like the most intense orgasm I’ve ever seen!” She mockingly fans herself.
I laugh and turn away for a second to hide my embarrassment. It’s not surprising she enjoyed everything. I even threw that look into the camera just for her benefit.
“You were sadistic tonight!” I turn back toward her and toss my coat onto a chair close by. “I was ready to curse you out several times. Touching me in the cab? Naked in the hallway? Devious.”
She sticks her tongue out. “I can’t take all the credit. Scott played his part well.”
“That’s an understatement. Where did you find him?”
“I have my ways. If you are looking for a second date, I’m sure I can arrange that.”
I have to admit a second “date” is very much in play. But that can wait. I walk toward the couch, her eyes fixed on me, and unclasp the collar.
“Maybe, but my focus is on you.” As I reach her I toss it into her lap. “Your date is next weekend. And after tonight, you’ve raised the bar. I’m feeling inspired to make it a night you never forget.”
She shivers slightly. I lean in and cusp her cheek.
“If you think tonight was rough, just wait.”
The smallest of whimpers escapes her. I smile and turn to walk away, eager to begin my planning.
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