A Date Night to Remember

Story Info
Date goes off script but full of fun.
3.5k words
4.17
9.6k
5

Part 1 of the 2 part series

Updated 06/11/2023
Created 11/27/2022
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You go over your dress one more time before you step out of the car. You smooth any wrinkles you find and double check in the car mirror. Your makeup is on point and you can't help but you blow a kiss at the mirror and hope this date goes well. It's been so long since your divorce that you've actually gotten all dolled up and it's exciting to say the least. As you slide out of your Jeep Wrangler you give yourself one last look over, your in a tight black dress that has a slit in the side going up to mid thigh. Your heels are nice and long, they perfectly show off your ass when you walk but aren't long enough to be regarded as "prostitute heels". Your dress comes up to your ample cleavage. It was definitely a feature you loved to show off and the low cut black dress was going to get them some attention. You decided to not wear any jewelry since you are meeting this man for the first physical time and you have heard all the stories about the horrors of what could happen. As you think of some of those stories you feel your breathing increase, its scary but also kind of exciting.

As you enter the very fancy restaurant you go to the hostess and before you can say anything she looks you up and down and says, "you must be Emilia". You are taken aback that she knew your name off hand and it must have shown on your face as she giggled, "I'm sorry ma'am. I was informed by your date what you'd be wearing. Please follow me, he's waiting". Well this is different. The typical date while you were married was picking up UberEats after work or getting fast food because your husband was 'to tired from his day off to cook anything'. You shudder and can't believe how long you put up with that nonsense.

The hostess brings you around to a more private area, dimly lit but with ample candles to see and there you see him, the dreamy man you've been talking to. His name is Angelo and he's nearly a picture of heaven. He's older then you but not by much. His five o'clock shadow looks like a permanent fixture on his face, and he's wearing a classy business casual suit but you can see his large hands bear the marks of a man who has done several years of hard labor. He strikes you as a lion contained within the suit. He gets up from his seat and helps you into yours. You lean your head back and smell his cologne, you feel something tingle inside of you. Tonight is already magical. You pass the time with small talk and catching up on life. You and Angelo have been talking for a while on the internet so you're not complete strangers. You also know that as far as bedroom activities go, he likes to give the orders, which you haven't tried before. But it always sounded fun.

As dinner begins to die down you slip a foot out of your shoe and begin to caress his leg. "Angelo, I had an incredible night. I wish I didn't have to go home tonight" You purr. He smirks back at you as his hand slips under the table, gently grabbing your outstretched foot. Slowly he begins to give you a foot massage right here in the restaurant. You shudder as he rubs your foot like a professional. He says something to you but you are caught up in the ecstasy of the moment and you bite your lip as you nod your head in agreement with whatever he said.

"I'm really happy to hear that. I was hoping you wouldn't have to go home tonight either". You realize you might have just agreed to go back to his place and the anticipation of what that could lead to has your groin feeling warmer and wetter.

As Angelo finishes with your first foot he politely asks for the other. Again you oblige him. His foot rubbing skills are second to none and you are positive you've never had this good of a foot rub, "do you accept these terms" he says dreamily. You are so lost in the moment and the feeling of your feet being rubbed after such an incredible date you languidly nod your head and say "mhhhmm".

"Wonderful. That makes me very happy. Now be a good girl and remove your panties". Did he just ask you to remove your panties? You look at him and cock an eyebrow, quizzically at him.

"Did I stutter?" He says again. Still calm but slightly more forceful. The heat between your thighs is definitely growing and the thought of taking off your underwear in the middle of a crowded restaurant is intoxicating. You look around sheepishly and see that Angelo's eyes haven't left you the entire time. Like a lion indeed you think. Slowly you reach one hand through the slit in your dress and tug your black lacy panties down around your ample ass and generous thighs. As it drops down around your ankles you pretend to have dropped your fork and go to pick it up. As you carefully grab your panties you can feel how damp they are. You are extremely wet and he is only making you wetter and wetter. With the panties now in your hands you place them in your lap and await what he has planned next.

"That's a good girl." As he says the compliment you feel an electric thrill go down your spine. "Now put them in your mouth. All the way in".

You've never done something like that before. Sure you've tasted your pussy when you've masterbated but you've never put your wet panties in your mouth. You look at him with your mouth half open trying to formulate a response then he says, "Put. Then. In. Your. Mouth." The total authority in his voice overrides your rational brain. Maybe it's the heat already so built up inside you, maybe it's the novelty of doing something explicit in a public setting.

Slowly you bring your hands to your mouth and insert the panties. You taste your sweet pussy immediately as you push the fabric into your mouth. The taste isn't unpleasant. Far from it. It furthers how incredibly aroused you are right now. Within a few seconds of you removing your hands and having the panties entirely In your mouth the waiter returns,

"Will you be paying together or separate?" He looks at Angelo expectantly. You see Angelo has a playful look on his face.

"What do you think Emilia?" He asks you. You know you can't respond without revealing your own panties are in your mouth and you slowly look up towards your waiter as he awaits your response. What feels like eternity passes between you and him before Angelo says,

"Never mind. I've got it". The waiter takes the card and leaves as you sag back in your chair and bring your hands up to remove the makeshift gag,

"wow now. I didn't give you permission to remove that. And I just bought you dinner. You are going to keep that in there until I tell you otherwise". You stare blankly at him and slowly nod. He shakes his head in response, "we are mostly alone. I want to hear you say that you'll listen".

"Ihll lishten" you say around your sweet tasting panties. Angelo pays and gets his card back. He helps you up and you can feel your thighs are soaked.

As you leave the restaurant your panties still in your mouth. The taste of your wet pussy on your tongue, your date keeps having a conversation with you and you can only respond with nodding your head and slight muffled grunts. He opens the door for you and as he helps you in he slides his hand up your dress and grabs a handful of your butt.

"I'm going to enjoy this" he says.

You patiently wait for him to come around and get in the car. As he sits down he looks at you, "it's dark out. I've got tinted windows and I'll buy you a new one", with that he produces a knife. At first fear shoots through you and you are to shocked to respond with anything but "mrph?!" And he carefully slices the front of your dress off revealing your nakedness. Now you are sitting in this man's car, your panties in your mouth, dress ripped in half, completely exposed and vulnerable.

"Much better. Don't you think?" It's hard to respond but he can definitely see the wet area between your thighs. As he finally starts the car he gently grabs your hands and places them slightly above your head and behind you. At some point he produced a pair of handcuffs and clips your hands together between the headrest keeping your hands behind your head. He says, "since I have you naked and vulnerable in my car. You are going to call me Sir for the night". As he says this he pinches your left nipple. Hard enough that you yelp. He then pinches the other and says, "well?" Through your soaked panties you respond, "yeshshuur".

"Good girl". He places his hand over your sopping wet pussy and prompts you to spread your legs. Gently as he drives away he begins to rub small circles around your slit. Never quiet touching it and getting dangerously close to your clit. You keep bucking your hips up to his hand and he keeps pulling away. You are breathing heavy and are burning with need.

"Do you want to cum" he says. You both know the answer, "ysh shuur" you say through the gag" he chuckles to himself and says, "be a good girl and beg". As he says that he takes the gag out of your mouth and expectantly waits to hear your response.

"I want to cum sir. I've been a good girl and I deserve it. Please sir, let me cum". You see a devilish smile cross his face, "I'm going to do whatever I want to you. You understand?"

"Yes sir you can use me however you want, Just please let me cum". This whole conversation he hasn't stopped teasing you and you cannot focus on anything else. He takes your panties, slips them inside your pussy and vigorously begins toying with your clit. flashes of pure ecstasy as you feel the electricity shooting out of your sweet wet hole all over your body. Your brain goes numb from the pleasure and he says, "are you my sex slave?"

Pleasure overcomes everything else and you automatically respond "yes sir I am your sex slave". You cum. Hard. Your whole body shudders and twitches as you come. But he doesn't stop rubbing you and you feel another orgasm crash through you like a tsunami. Your legs shake and buck as you squirt in his car. Slowly he stops rubbing you and brings his fingers to your face.

"well it looks like my slave made a mess. Didn't she?"

"Yes sir..." you meekly say and seeing his fingers close to your face, covered in your pussy juice, you instinctively open your mouth and wait for him to put them inside. Your new master obliges you, "that's a good girl. Clean up your mess. Do you enjoy the taste of your sweet pussy?" As his fingers work in your mouth all you can do is nod and moan again. He withdraws his fingers and slaps your face. Not hard enough to be very painful but hard enough to get your attention. "Bad girl". You're confused not understanding what you did wrong. Then you see him bring your panties up from where they were inside your pussy. They are beyond soaked. You've cum all over them several times. "Open up slave" he says as you immediately realize you hadn't said sir before.

"yes sir" and you open your mouth, he roughly stuffs them all the way in and your tastebuds are overrun with the taste of your post orgasm fluids.

As you try to focus you realize you've arrived somewhere. He parks and comes around to your side of the car. As he opens the door he uncuffs your hands and helps you out. You are standing in the open, completely naked and exposed with your panties in your mouth. He grabs your wrists and recuffs your hands behind your back. Then he places a collar with a small metal leash around your neck and begins guiding you with the leash. You are shuffling through a parking lot wearing nothing but the heels from dinner, a collar around your neck, hands cuffs, and your soiled panties in your mouth. It's cold outside and your nipples are hard enough to cut glass. Thankfully the walk isn't far and he guides you to a door into a nice looking house. When you enter he guides you to a room with a fireplace already on.

"Bend over at the waist, slave", he says commandingly. At this point you don't see much point in resisting. You are restrained and naked in his home. Your phone and ID are back in his car. You are totally helpless.

"Yshshr" you say through the gag and you bend over. He slips the gag out of your mouth and you feel him gently return them to your greedy pussy.

"Hold these for me." He says. With little effort the panties slide into you again and you see him walk to the front of you, "be a good girl". He releases his cock, it springs out and slaps your cheek, it's fully erect and your body immediately reacts. before he can even grab you to guide it into your mouth you are able to put your lips around it.

"Good job, slave. This is your place" he says as he slides his cock in and out of your mouth. Soon his cock is well lubed with your saliva and sliding all the way down your throat. Making sexy 'glugk glugk' sounds each time it fully enters inside you. As he slides it faster and faster in your throat he grunts, "im going to paint that slut face of yours" and withdraws leaving just the head in your mouth. As you feel the first string of his cum shoot down your throat, his cock pops out of your mouth and he grabs your hair and sprays all over your forehead and cheeks. Your face is thoroughly frosted and you pant after the vigorous throat fucking you received. His still hard cock slaps your face a few times, "now now, slave. What do we say?"

"Thank you sir for letting me suck your cock". He smiles down at you and grabs the dangling leash.

"Follow me slave". He guides you to another area of the house and you see what looks like a sawhorse facing a wall with a mirror on it. He brings you to the sawhorse and uncuffs your hands. Instinctively you bring them to your face to clean off his cream, but he quickly grabs your wrist, "now now slave. I didn't say you could clean up". You sheepishly look at the ground and realize there's leg and wrist cuffs attached to the sawhorse. He places you on your stomach, your breasts dangling and you feel your ankles locked in place and your wrists locked as well. You are yet again trapped. But this time, your entire body is on display. Your pussy and asshole are easily accessible if he should wish and all you can do is stare at yourself in the mirror ahead of you.

"Oh I'm going to enjoy you for a long long time". He slides your panties out of your pussy and you feel him press them into your tight asshole.

"wow. Wait what", you begin.

"I didn't give you permission to speak, slave" and he slaps your ass with a sting. The soaked panties slide past your sphincter and into your butt as you moan. He then comes around and you feel something on your nipples, its a set of nipple clamps. The clamps are connected by a chain and he brings the chain to your mouth.

"Hold this slut" he says. As you strain to look up and hold the chain to your nipple clamps you get a glance at your collar in the reflection. The collar says 'Fuck Slave'. With that he steps behind you, his large cock stroking your pussy lips up and down over and over again.

"Be a good little slut and beg" he says and slaps your ass a few times more. "Pweesh shtick yer cock inshide meeeee" you mewl.

He decides you've been good so he slides it inside of you, "don't drop that chain, slut", he says as he begins to really pump into you. As he pumps into you, you can see your breasts swinging back and forth and the chain is just torture as it pulls your rock hard nipples whenever your breasts swing.

As he fucks you he demands, "say you're my personal whore. Say it".

You struggle to make words come out during your vigorous pounding but finally you can talk as the chain slips out of your mouth, "I'm your personal whore Sir. I'm your slut. Fuck me please. Don't stop fucking me".

He abruptly stops. His cock slides out of you with a plop and he walks over to your face, cock glistening with your pussy. "You disobeyed me yet again, slut. I see you need more thorough training" He then wipes some of the cum off your forehead and grabs a sharpie. His cock is less than an inch from your mouth and instinctively you again take him inside. "There's a good slut. Know your place, whore". With your lips around his cock, he uses one hand to hold your hair and the other he writes something on your forehead. Next he reaches past you and pulls your panties out of your asshole. Withdrawing his cock he forces your panties roughly stuffed into your mouth. You try to spit them out but he grabs a small piece of cord and wraps it around your head to keep the panties lodged in your mouth.

"Do you like the taste of your ass, whore? Don't worry. You'll be tasting your ass a lot tonight", and he walks back behind you. You hear what sounds like a bottle of lube squirt on your butthole and you feel something rubbery press against your pussy. His cock presses against your now lubed asshole and he grabs your hair yet again. At the same time a buzzing starts and a vibrator attached to the sawhorse starts giving your pussy a good work over. His cock effortlessly slides into your awaiting asshole and he begins pumping in and out over and over again. While he vigorously fucks your ass he begins to say all sorts of degrading things to you and making you repeat them back to him through your gag.

"You like the taste of your asshole whore?"

"Yether I lov taste of mah ashole".

"Such a good whore with a cock in her ass".

"Yeshhir I'm a good whore. I luv cock in mah ashhole".

"Look in the mirror slut, look into your eyes and see what a whore you are" he says with absolute authority.

You look at yourself getting fucked in the ass, you see you are shackled to this sawhorse, vibrator on your clit making you cum every few minutes, a man you hardly know punishing your asshole, metal clamps on your nipples, cum all over your face. Your panties that have been in your pussy and asshole in your mouth and finally you see the words written on your forehead, 'IAM A DUMB BUTT SLUT'. You are both horrified and turned on even more.

He pulls your hair back and growls, "What are you?"

You feel another orgasm building and your mind goes blank.

He slaps your ass, "whore. What are you". You finally yell out, "I am a dum buttshlut shir". You feel his lot load shoot directly into your quivering ass. Painting your insides white. Finally his cock withdraws and you see him pull out a buttplug. He lubes it up on your soaked pussy and slides it effortlessly into your asshole.

"I want you to keep that inside right now". Then he walks over to the front of you, removes the panties, places them back inside your freshly orgasmed pussy and presents his semi hard cock to your face, "Well whore? Clean it".

Obediently you begin sucking his cock. The taste of lube, pussy, and asshole all complete the degradation you've been enjoying and you orgasm all over your panties yet again.

"That's a good whore. It's going to be a long weekend for you".

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AnonymousAnonymousover 1 year ago

very silly fantasy for girls who would in real life be horrified by any of this

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