Waking Up to Your Cuckolding

I'm sure some of you have had the experience of going too hard at a party and waking up disoriented and out of sorts. This story is kind of like that, only it's after a Halloween party and you're not sure where your girlfriend is. And, since it's me writing it, I think we all know what your girlfriend is getting up to, don't we?

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Your head hurts. Your stomach is unsettled. The unfamiliar room you're in spins as you sit up. Your back aches from sleeping on the floor. You don't recognize the furniture. You don't recognize the curtains that cover the windows. Confusion reigns.

For a moment you fear you're going to vomit, but the sensation passes. You're wearing green pants and an odd, old-timey pair of shoes. Confusion reigns once more, though this time it quickly clears as you remember that you attended a Halloween party dressed as Robin Hood and that your girlfriend Jenna went dressed as Maid Marian.

"Jenna?" you ask.

No answer comes. You stand up and almost immediately topple over, falling into an empty bed. Again it feels as though your stomach is going to empty itself and again you fight off the urge. You push yourself up, grab the bed post for balance, and survey the room to discern that you're the only person in there. You search for your phone but it's nowhere to be found. The alarm clock on the nightstand says that it's just past 2 a.m., though.

You can't quite remember who hosted the Halloween party and it's entirely possible you ended up in a different house. You head for the door and open it slowly. You step out into a dark hallway. To your left are two more doors, both closed. To your right are one door and a staircase. You feel utterly lost, but you take a left and resolve to listen outside each door for any signs of life.

You tip toe down the hallway and press your ear against each door. You're greeted with silence, and while you're tempted to gingerly open each door and peer inside, you fear it would be a terrible mistake to barge in to find anyone other than your girlfriend inside.

You turn and head towards the staircase, stopping to listen outside the third closed door. You're greeted by silence once again. You head towards the staircase and stop to listen for any signs of life on the house's first floor. Silence is your only companion, though.

You take a deep breath, ensure that you have your balance, and descend the stairs while tightly gripping the banister. Each step feels dangerous given the state you're in, but you make it to the bottom of the stairs without incident.

The house remains unfamiliar to you, so you fumble your way through in search of Jenna. You pop your head into what looks like a home office to find two people sleeping on the floor. You find the kitchen and see leftover food and drinks strewn about the counters. Your stomach lurches at the thought of imbibing anything and you quickly move on.

An orange light draws you towards a doorway and you look into what turns out to be the living room. Several carved pumpkins sit on the fireplace and one has a candle still burning in it. A string of orange lights has been hung over the mantle, hence the glow that lured you to the doorway.

A moan lures your gaze from the fireplace to the couch. You see two people kissing. It's too dark to make out much detail, but it's clear that they're getting hot and heavy and it feels inappropriate to watch. You don't move, though, instead remaining in the shadows of the doorway.

"You're so fucking hot," the guy says before kissing her neck.

The girl moans and you see her hand come into view. It moves to his knee and towards his crotch. It disappears into darkness, but he moans in a manner that makes it obvious she's stroking his dick.

"I want to feel your mouth," he says.

The girl's head moves towards his lap. You've never had the balls to say that to a girl, to straight up ask for a blowjob. You're amazed that it worked. You suspect the guy is really good looking.

"Oh, fuck," he says. "That's it, girl. Suck that dick. Make me feel good and I'll fuck you hard."

Suddenly it's like you're watching porn, only you're doing so from the shadows. You should walk away. You should go find Jenna.

You remain, though. The sounds of the blowjob reach your ears, as do his moans. She even moans a little, too, and you feel your cock come alive. You stroke yourself through your green velvet pants. It feels good and you're not entirely in your right mind, so you feel almost no shame about spying on a couple and playing with yourself.

"Take it deeper," he says. "Swallow my fucking cock. Show me how badly you want it in your cunt."

To your surprise, she moans. She likes being talked to like that. It turns her on. You can't imagine a girl would ever want you to talk to her like that. You've tried a little with Jenna and she's never been into it.

"That's a good girl," he says as you listen to her struggle to take him deep. She's not quite gagging, but she's getting close. He seems to like it, though. "Let me feel your throat around my dick."

Now she's gagging. She keeps doing it, though. She's working to show him how badly she wants to get fucked. She's putting in the kind of effort a girl has never put in for you and for some reason it makes your dick hard to listen and think about how this guy is getting something you'll probably never get.

"I need you inside me," she says.

You freeze. You recognize the voice.

"I need you in my cunt."

It's Jenna's voice. You've been dating for four months. You know her voice.

"Yeah?" the guy asks. "What about Robin Hood? Isn't he the one that gets to enjoy your cunt?"

"I don't give a fuck about him."

Your legs tremble. Why does it turn you on to hear her say that? Why is your hand moving over the bulge in your pants at hearing your girlfriend utter those words to another man? The answers don't come, but they don't need to. You're awash in a kind of arousal - a deeper, purer kind - than you've ever felt before and you can't help but pursue it.

"I'm soaked. I need you to fuck me. I need you to fuck me hard."

You see his arm move in the darkness. You see her head move towards his lap. You hear her sucking his cock. You see her head bobbing up and down, though you still can't make out her face. You know it's Jenna, though. You know it's your girlfriend blowing some other guy.

A memory of stumbling into a bedroom with Jenna floods your mind. You were kissing. You were playing with her tits in that incredible costume. You lifted the bottom of her long skirt and slipped a hand into her panties to play with her wet pussy. She stroked you just as you're now stroking yourself. Then the memory fades and you suspect that you passed out long before you got a chance to fuck your girlfriend. You passed out and she went searching for satisfaction with someone else.

"That's a good girl," he says.

You hear the sound of flesh meeting flesh as he spanks her ass. Jenna unleashes a moan that's clearly muffled by the cock stretching her lips. Sounds of wetness fill the air. He's fingering her. She must be on her knees on the couch next to him. He must be fingering her pussy as she sucks his cock, as she proves to him how badly she wants his dick inside her.

"Get up," he says. "Dance a little for me. Seduce me."

She stands and you lean back to cloak yourself in shadow. The girl moves into the orange glow from the lights on the fireplace and any doubts you had about it being your girlfriend wash away. It's her. There's no question. She looks breathtaking in her Maid Marian costume. Her breasts are pushed up high and her waist is cinched in tight. She dances for the man on the couch, shifting her hips slowly and moving her hands over her body, grasping her tits and then running her fingers through her hair. She lifts her skirt and runs her fingers over her thighs. She spins around and bends over, shaking her ass in a remarkably alluring manner before looking over her shoulder to ensure she has his attention.

"You really want this dick, don't you?" he asks.

"It's been a long time since I got a proper fucking," Jenna replies.

A deep sense of inadequacy engulfs you as Jenna makes it clear that you've never given her a proper fucking. You were so certain the sex was good, but it seems that she's still dating you for reasons other than your skill with your cock.

"Robin Hood doesn't fuck you the way you need to be fucked?"

"I like him a lot and he's good at many things, but sex isn't one of them."

Your dick feels as hard as it's ever been. Your balls tingle. Your head swims. You should be heartbroken. You should be annoyed. You should be outraged. Perhaps those feelings will come later, but they're not present at the moment. Instead, you feel only desire.

"Luckily for you, I know how to satisfy a woman," he says.

He stands and comes towards her. You see his face, but you don't recognize him. He's shirtless so it's nearly impossible to tell what he came dressed as.

They kiss in the orange light. It's immediately clear that Jenna has never kissed you like that, though it's entirely possible you've never kissed her in the manner he's kissing her.

"Get on the couch. Take off your panties. Spread your legs for me."

You feel as though you're in a movie. A period piece where a woman dressed like Jenna gives herself to a forbidden man. It's the costume and the manner in which Jenna simply follows orders and completely surrenders to his desire, spreading her legs on the couch and offering herself for the taking.

"Do you have a condom?" she asks.

"No."

He moves on top of her. She makes no effort to stop him from taking his place between her legs.

"I'm not going to pull out, either," he says.

You stroke yourself faster.

"That's okay," Jenna replies. "Just fuck me. Fuck me hard."

She moans as he lies on top of her. He must be inside her. He must be inside your girlfriend's pussy.

"Oh my God," she says. "That feels so fucking good. Your cock feels so fucking good in my pussy. Fuck me hard. Please, fuck me hard."

The sex is only partially lit, but you can see Jenna's face. You can see him kissing her neck as he fucks her with wild abandon. You can hear it, too, and your mind fills in the blanks and offers you a picture of his hips moving as he thrusts in and out of her at a rapid, powerful pace.

"Oh fuck, oh fuck, oh fuck!" Jenna cries out.

She has an orgasm that looks and sounds unlike any you've given her. It's long and loud and she seems to lose control of herself as the climax rips through her beautiful body.

"Don't stop," she says. "Keep fucking me. Keep fucking my cunt!"

He gives Jenna what she craves. You watch and stroke yourself through your pants. Your cock is hard as a rock. You're leaking copious amounts of precum. You've made a mess in your underwear and you haven't even cum yet.

Jenna climaxes twice more before he holds her tight, buries his cock inside her, and cums. His orgasm is loud and his grunts and groans fill the room. You watch Jenna's face during his orgasm and you wonder if she's ever looked that satisfied when she's made you cum.

"That was incredible," she says as he pulls out.

"You're a damn good fuck," he replies.

She sits up on her elbows. "Yeah? Does that mean you'd want me again?"

"Maybe."

"Can I give you my number?"

He reaches for his pants and pulls out his phone. "Go ahead and put it in. I'll text you when I'm in the mood to have you again."

Not in a million years would a girl be okay with you uttering that sentence. Jenna happily gives him her number, though.

He takes his phone from her, gets dressed, and walks away. You watch Jenna and to your surprise she doesn't seem the slightest bit disappointed that he fucked her, came inside her, and left.

Instead, she smiles as she watches him go and then lies back on the couch and runs her hand between her legs. You can't see her fingers as they enter her, but you can hear it and there's no question she's fingering herself.

Compelled by desire and perhaps some form of insanity, you step into the living room and move towards your girlfriend.

Jenna sees you and pulls her fingers from her pussy as panic crosses her face. You stroke yourself through your pants as you move towards her.

You sink to your knees next to the couch. You smile at Jenna as you run your hands up her thighs and under her long skirt. Her chest heaves as she studies you with a nervous look on her face.

"My dearest Marian," you say with a smile, "it seems as though you've given your virtue to a man who was quite...vigorous with you."

Her nervousness washes away. "He was a bit rough, yes."

Your fingers near her pussy, but you stop short of penetrating her. "I wonder if I might soothe your bruised flesh."

You're not sure why, but it feels easier to play a character of sorts, to be the Robin Hood from the movies instead of yourself in that moment.

"And how would you do so, Robin?" she asks, playing right along with you.

Your heart is pounding as the words form in your mouth. "With my tongue, my dearest Marian."

She shifts her legs so her pussy is a great deal closer to your mouth. She pulls her skirt all the way up, too. It's the first time tonight you've seen the glorious place between her legs with any kind of lighting and it's exceptionally messy.

That's when the smell of sex hits your nose. It's potent, and yet you're drawn to her pussy. You lean closer. You purse your lips. You kiss her labia. She moans softly and then her hand moves to your head. Her fingers run through your hair and her touch is both soothing and massively arousing.

"Soothe me, Robin," she says softly.

Your tongue moves inside her. You lower your pants and stroke yourself as you taste him, as you taste her, as you taste the vigorous, wild, orgasmic sex she had with another man while you watched. You close your eyes and quickly find yourself awash in unmatched level of arousal.

"Your tongue feels so good," she whispers. Her hips began to move a little as if she's seeking to rub her clit against your lips.

"You taste magnificent, my dearest Marian."

She moans. Your tongue pushes deeper inside her. She slips a hand into her dress and grasps one of her breasts. Her eyelids flutter.

"Robin, my darling, I'm cumming!"

She has an orgasm as you lick his cum out of her pussy. You could easily do the same, but you stop yourself from climaxing, instead choosing to relish the pleasure of the moment and in particular Jenna's climax.

You lean back when she finishes cumming and her eyes open as her lips curl into a beautiful smile.

"That was...unexpected in the best way possible. Thank you."

"Oddly enough, it was my pleasure," you reply.

She sits up, leans forward, and kisses you softly, sharing in the taste of the cum you just cleaned out of her.

"Did you really give him your number?" you ask.

"I did."

"And will you really...will you really just go and fuck him if he texts you?"

"I will," she says. "The sex was that good. I...I mean, I guess you were watching so you must have seen that I came..."

"Harder than you've ever cum before?"

"That's right."

You kiss her. She leans back on the couch and you climb on top of her. She lowers your pants and guides your cock inside her. You fuck her knowing that you won't satisfy her like he did. She invited you into her pussy, though, so you take your pleasure while thinking of him, of the sex she had with him, of the way she moaned for him, of the way he seemed to make her feel.

You cum inside her as she moans for you. She holds you tight as you have an orgasm of unparalleled pleasure.

Your mind isn't exactly clear, but you're fairly certain that this is the best Halloween ever.