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Chapter 18 by Schmugelflugel
How does the date go?
Good times all around
As you start driving, you can't help but sneak a few glances at the two of them as they sit in the back. Christys expression speaks volumes, as she is not only red from arousal and eagerness, she also turns over to James now and again, meeting his eyes and smiling at him. He is engaging with her as well, making several flirty remarks over the course of your drive. As you near your destination, he puts his hand on her upper thigh, elicitng a surprised moan from your girlfriend. Looking at you through the mirror yet again, he stares intently and asks:
"See how much your girl likes to be touched by me? What else should I do? Tell me!"
Your breath trembles as your chastity becomes even tighter. He's such a dominant stud, you're unsure what turns you on more: his assertiveness or Christys blatant arousal and submissive demeanour towards him. And if you're being honest with yourself, while these two factors are arousing as fuck, the biggest turn-on right now is the thought of actively choosing for Christy to be ravaged in your backseat.
"Please go on, grab her tits, touch her pussy until she's all messed up. I can take a detour so you'll have all the time you need."
James chuckles as he casually grabs one of Christys breasts, causing her to sharply suck in breath at the sensation. His other hand travels deeper under Christys dress, surely searching for her pussy, while he still looks at you. Now Christy butts in on the conversation as well.
"Ah yes, that feels so good. Baby, his hands feel so good, so manly. I love how he takes what he wants, without any hesitation." She shifts to part her legs even further, giving you a peek at his hand caressing her drenched pussy. "Do you see how assertive he is? Claiming my pussy as rightfully his? It feels so good, I might never want another man!"
Her teasing tone is broken up by wet noises as James increases the intensity of his caresses, but before things turn even hotter, he suddenly stops, much to Christys audible displeasure.
"That's enough for the tasting course, don't you think? We won't be needing that detour, after all I've heard you've booked us a very special menu. It'd be a shame to miss out on all the free food and drinks."
"Yes Master!" You answer while feeling a bit impatient and blue-balled from him stopping. Looking at your girlfriend, she seems to be on the same page. But at the same time, being denied now would only increase the pleasure later. Either way you were going to comply, leaning into your role of utter subservience almost as naturally as breathing.
Pulling in to the restaurant, you make a show of getting out of the car and getting the door for James and Christy. Your casual outfit and mid-budget car don't fit the whole chauffeur vibe, but it still serves to send an additional tingle of submissive pleasure through your body. As James emerges first, he holds out his hand towards Christy. As he stands quite close to you, you can't help but inhale his masculine scent. His entire presence dwarves yours while not really being much taller than you physically. As Christy takes his hand, gripping him tightly, a pang of guilt hits you. This is all your doing, giving her away freely and eagerly for this dominant man to have and enjoy. She takes great care to emphasize her exposed body as she disembarks and with a surprised yelp, she lighty trips and falls onto James. He of course catches her safely, the two of them embracing for a moment and as their eyes lock, you can see how his body reacts to the closeness of your girlfriends sexy body. Indeed the bulge you can make out in his grey dress pants looks promisingly huge. This in combination with the level of intimacy between the two of them keeps you in a state of hazy arousal. A mere touch would be enough to send you off right now.
"No worries, little one. I've got you." Jamess voice is deep and soothing, and as they move apart, he focuses on you, with Christy already clinging on to his arm, leaning into his side. Looking around, a few people are on the sidewalk, some clearly on the way to the fancy restaurant you've parked at. Your girlfriend's attire is more than sufficient to turn a few heads and the attention of several people seems to be focused on you. You're acutely aware of this as James holds out his hand and adresses you loudly and clearly.
"One last thing, slut. Considering the fact that you'll be paying for my date with your girlfriend, it would only be fair for you to supply the tip as well. After all, putting that on the check is just bad manners, don't you think?"
Your embarrasment is palpable and Christys expression is a mix of suprise and second-hand embarrasment as well. The nerve of this guy, exposing you like that to random ass strangers. And after all of your chatting, he's still kind of a stranger to you. Giving Christy away freely to this jerk could've been a serious mistake, no? But all these thoughts are washed away, as Christys expression suddenly hardens and her dominant "mistress-face" emerges.
"What are you waiting for, cucky? Pay my date to show your appreciation. After all, he's here to give me a better time than you ever could. You should be more appreciative of him!" Her demeanour draws out your inner submissive pet, and as eager to please as you are right now, there's no denying that you're in to deep to turn around now. With her twinkling eyes full of affection as your only reassurance, you take out your wallet and pull out a few bills.
"I'll be tipping double, so 100$ should be enough." He's teasing you now as well, joining Christy in some sort of twisted bullying dynamic. The onlookers stare at you, with mixed expressions of second-hand shame, mocking glares and even a few curiously aroused ones.
"Here you are M-Master." you mumble.
"What's that, I can't hear you. Speak up, Slut!"
"Here is the tip M-master. I've included 50$ for yourself, as my way of showing gratification for dating my girlfriend. I'll be waiting here to pick you up later. Take all the time you need, Master and Mistress!"
The words escape your mouth almost subconsciously as your body feels light from shame and arousal. The wet spot in your lacy panties has now soaked through your pants as well, betraying your innermost desires. You're feeling like you're about to pass out, barely able to make out Jamess cocky smile, Christys reassuring eyes and one onlookers approving grin of mockery as the two of them finally turn around and walk towards the restaurant. You stare at Christys swinging hips for a few moments, before finally fleeing into the safe confines of your car, even redder than before from your utter embarrasment.
You drive away, looking for a parking spot and for the next few hours, you sink in on yourself, trying to hide from the shame you've just experienced.
Two hours later, you've not only come to terms with what just happened, you realize that the extent of their humiliation has pushed your boundaries even further. Yes, their words had stung, but this sting only served to further your new role of a subservient pet for your girlfriend and any men she had any interest in by proxy. You're actually comfortable in this role and catch yourself planning for the next date, even mentally preparing outfits for yourself that would make your role clear right from the beginning. You use some of the time to browse several stores for fetishwear and without any restraint left, order a feminized and sluttified version of a chauffeurs uniform for yourself.
Finally, as you swim in a sea of denied arousal, aching for some form of release, your phone buzzes as your girlfriend and her date call for you to pick them up.
Hurrying over to the restaurant, you break more than one speeding limit bfore coming to a halt with screetching tires in front of the restaurant. Jumping out of the drivers seat, you again open the door for the two of them, this time loudly exclaiming:
"Hello Master, hello Mistress. I hope you had a good evening!" They both look actually surprised for once, taken aback by your enthusiasm. Christy is the first to recover, as she looks at you with sultry eyes.
"Yees, cucky. My date and I had a very good time with your money. Now it's time to go back home and get the real fun started, don't you think?"
She glances back at James who now shakes his confusion as well and helps her in again, mirroring the situation from before. Only this time, it's you who presses against his side and as he glances at you, you lean in and whisper in his ear.
"That's what I've been looking forward to this entire night. I's be honoured if you'd let me help you fuck my girlfriend. I'm almost as slutty as her, you know?" And with these words, you reach out to openly cop a feel of his impressive bulge. The hardness and thickness makes your mouth water and thinking of the dildo you've christened with his name, you're more than eager to try the real thing tonight, dead-set on making this a night to remember forever.
Now it's his turn to turn red as he seems taken aback again by your brazen sluttiness and utter subservience. Muttering some words of approval, he gets in, you close the door and within 10 agonizing minutes of you trying to focus on the road while the two of them make out in the back seat, you manage to finally pull in to your front porch.
How does the night progress in your home?
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Watching Girls You Know Get Fucked
A way for you to live out some cuckold fantasies
One day, you find yourself in a room tied to a chair. A strange masked figure instructs you to jack off as a woman/women you know get fucked by various guys. The relationship between you and the women getting fucked is entirely up to you, as are the people (or monsters) who are giving them some dick. Customize the names of both parties to make things more personal, whether it be the name of your girlfriend or a guy you knew in college. This story is meant to be very friendly to other writers out there, so please feel free to add if you have any ideas (27/6/2020: Story has been made public).
Updated on Jul 17, 2024
by lardasefyi
Created on May 17, 2020
by sharestories
You can customize this story. Simply enter the following details about the main characters.
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