Chapter 1: With GIFs
Chapter Text
Maggie Livingston hasn’t been home for a winter break in three years since she transferred to an out-of-state college. Only summers, and even then, it’s dwindled down since she started working during breaks and weekends. But now she’s set to graduate in the summer and work full time, so she’s decided to surprise her parents by coming home for Christmas. She requested the entire week off months ahead of time and conspired with her aunt to make sure her parents weren’t leaving town or anything.
She drove for seven hours, getting to her hometown and driving up the street to the house by seven-thirty. Her parents’ cars weren’t there. But she knew they were out to dinner and still wanted to surprise them, so she parked around the corner and carried her suitcase in with her.
If only she had looked around. She would have noticed the lube dispensers on the tables and condoms in the toffee bowl on the coffee table. If she’d gone into the kitchen, she would have seen how many smart waters and bottles of wine were in the fridge—along with way too many cans of whipped cream. Or seen the snack bowls set up on the dining room table with yet-to-be-opened bags of chips, pretzels, energy bars, dark chocolate, mixed nuts, and a watermelon.
All of this would have clued her in that her parents had something planned tonight. But she bypasses it all, dragging her suitcase up to her room, stripping to her camisole and panties, and crawling into her childhood bed for a nap after plugging in her phone and setting an alarm for thirty minutes. But she doesn’t press the save button to actually set the alarm and doesn’t plug in her charger completely. Within the hour, her phone will die. All while she sleeps like the dead, exhausted from her long drive.
Simon and Tanya are new to Crimson Oaks and swinging. They’ve been to a club in their old city, but when they moved, they were at a loss for how to find the scene and break into it without coming off as perverts. Luckily, Tanya joined a neighborhood book club where she met Erica Livingston, who practically runs the swinging scene with her husband, Michael.
They’re fifteen years older, but the scene is evenly mixed age-wise, and everyone gets along. They started attending their parties within weeks of moving in and became engrained in the scene in their new home. Erika and Michael don’t always host, but their parties are the best. Attendees have use of the entire house except for one locked door upstairs, including the pool, jacuzzi, she-shed, and garage. They clear most of the living room and family room for dancing and have plenty of supplies, food, and drink.
Simon and Tanya like to roam separately after doing some dancing and getting a few drinks in them. They like to stumble onto the other with different people on accident, and either watch or join in.
Simon once walked in on Tanya getting spit roasted over the wall of the jacuzzi and just slipped into the hot water in front of one of the jets and told her how hot she looked. She once caught him licking ice cubes out of another woman’s pussy, and she just waltzed over and sat on the other woman’s face. A lot of the women in this scene like to nap in the bedrooms upstairs and get ‘woken up’ by whomever opens the door and finds them. The Livingstons have their bedroom up for grabs, along with a guest room, and Michael’s personal gym. Tanya and Simon once woke Erika herself by teaming up on her in her own bed with his cock and Tanya’s strap-on.
Tonight is the first party in a month, and the couple is more than excited. Neither has had sex or even touched themselves for the last three days in pure anticipation.
As they walk into the Livingston house, the lights are low, only red and purple lightbulbs on, and music is weaving through the first floor. Erika greets them in an ivory negligee, her large breasts still perky, nipples poking through the fabric encasing them. Simon boldly eyes her cleavage as she tells them where they can find snacks, drinks, whipped cream, condoms, and lube.
“Make yourselves at home. It’s lovely to see you again,” Erika says. She sees Tanya at book club once a month but only sees Simon at these parties and a few neighborhood BBQs.
They like the music in the living room, so they go there to dance for a song or two after grabbing a batch cocktail from Michael’s new built-in bar in the corner. Once they’re sufficiently loose and happy, they split up. Simon stays on the dance floor, dancing with a few new partners. Tanya wanders to the pool. She likes to skinny dip and fuck in the water.
A few drinks in, Simon is a little buzzed and has to use the bathroom. The downstairs one is taken, and he doesn’t like using the pool house, so he wanders upstairs, passing a promising scene in the guest bedroom. He uses the bathroom, and he’s on his way back down when he sees the door that’s usually locked is ajar.
Curiously, he pushes it open and grins when he sees a young woman sleeping in the full-sized bed. He likes this game. There’s something taboo about stumbling on a defenseless woman and doing things to her until she wakes up. There’s always a moment where he wonders if she will scream, like she’s not literally attending a sex party, but when it passes and she gets into it with him, it’s still hot as fuck.
He steps into the room, leaving the door half-open behind him. He can hear music and light moans and groans downstairs, giving a heady atmosphere to the scene he’s playing out in his head. Walking to the bed, he goes to the side with her back. She’s sleeping peacefully, the blanket around her waist, exposing her camisole that’s sort of see-through. Enough that he can see her large breasts and hard nipples poking through the fabric.
She’s in the center of the bed, so there’s enough room for him to slip in behind her. He pulls the blanket up, ducking his head to get a look at her innocent white panties. He bites his lip, holding back a groan. So far, she’s still asleep, not having detected his presence at all.
Lust building in his veins, he plants his hand on her soft ass and squeezes lightly. She’s warm and toned, her flesh supple and attractive. He moves his fingers to her center, brushing them over her pussy in her panties and rubbing. She’s hot there and gets easily wet as he touches her.
And she doesn’t even know yet.
Simon groans. He’s glad he kept a strip of condoms in his pocket. Pulling his hand away, he quickly takes off his clothes and jerks his cock as he stares at the sleeping woman. She’s beautiful. She has big, perky tits that he bets look hot as fuck when they bounce while she’d getting fucked. Her hair is a pretty auburn color, spread on the pillow. Her face is lovely, full lips parted as she breathes deeply.
He doesn’t recognize her, but a lot of people cycle through these parties. Some people move in or move away. Some people are just visiting. Some people take breaks and then come back. Not knowing who this woman means nothing. She’s still here at a swinging party. And everyone knows the Livingston’s rules.
Fishing out a few condoms and a mini bottle of lube from his jeans, he sets them on the nightstand. For later.
Cock throbbing, Simon squeezes the base and leans over the bed, hooking his fingers in the waistband of the woman’s panties and pulling them down her smooth, toned legs. He also pushes the camisole up and over her breasts, licking his lips as he gets a good look at her tight, dark pink nipples.
Getting back into the bed, he slides in and spoons her. He flattens his thick cock against her pussy, nestling the shaft into her slit. He wraps his arm around her, gently groping her breasts. But he has to be careful. He’s always loved the idea of getting his cock inside a woman’s pussy before they wake up. He and Tanya tried it with Erika that one time, but Tanya got too aggressive with sucking her tits and Erika woke up just as Simon was getting the condom on.
Now’s his chance.
Shifting to grab a condom and the lube, Simon quickly slides the latex down his cock and squirts some lube on his fingers, spreading it over his length before pressing his fingers to her pussy.
The woman shifts when his fingers slide over her clit. He strokes it lightly, listening to her breathing and noises. She’s still asleep, but he’s definitely making her feel good. She is sighing and wiggling, and her pussy is getting soaked the more he touches her. Maybe he could make her cum. But he doesn’t want to wake her up yet.
Pulling his hand away, he spoons her more completely and pokes his cock against her pussy from behind. He pushes her knees forward and spreads her ass, giving him all the opening he needs to slide half his cock into her tight pussy.
He swallows his groan at the feeling of her pussy squeezing his cock. She’s so tight, she almost feels like a virgin. He wonders who her partner is. He’s a lucky bastard to get this pussy to himself outside of the scene. Simon grunts as he thrusts shallowly, slowly working his entire cock into her cunt.
Shuddering with his full body, he works his cock in and out of her with slow, easy thrusts. Her pussy clings to his shaft, replacing the small amount of lube he’d used with her own natural wetness.
Their lower halves are still covered by the blanket, the shroud making the taboo somno-fucking even hotter. Simon shuffles closer to her back, fucking her open nice and slow.
Maggie’s had sex dreams before, but this one is out of this world. She can’t remember the details, or who it’s about, as she slowly comes to. But the horniness remains. The heat in her cunt; clench in her core. The arousal courses through her body. She wakes up sluggishly, moaning as her pussy squeezes around something. It’s like her dream followed her into reality, and she’s actually being fucked.
Her body rocks on her bed, up and down. The fabric of her pillow shifts under her ear. She feels the distinct heat of a body behind her now. And as her right leg stretches up, she can definitely feel something moving inside her pussy, sliding through her wet lips and filling her cunt with measured movements.
“What?” she whispers, the word coming out more like a confused moan as she wakes up and her brain clears slowly. She rubs her eyes, peering down. Her camisole is bunched up over her breasts, exposing them to the cold air of her bedroom. Her lower half is under the blanket, but she can see and feel movement under the fabric. She finally twists her head back, and sees a man in his late-thirties, naked, spooning her. As she finally realizes that the thing moving inside her cunt is his cock.
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She stops breathing, fear spiking through her arousal. “Who are you?” she gasps.
The man grins crookedly. He’s handsome, even though he is much older. Full head of hair, kind brown eyes, and nice teeth. “Simon, nice to meet you. What’s your name?”
She opens her mouth to yell, scream, cry. Whatever. But his cock pierces her right over her G-spot, making her gasp and jerk and cry out, “Mag—gie.”
“Well Maggie, you’ve got one of the best pussies I’ve ever fucked,” he says so casually. “Your partner is a lucky guy. Is this your first party?”
“What? No.” She finally notices the music filtering into the room from downstairs. Were her parents throwing a party?
The man, Simon, bands his arm across her body, pinning her to his chest as he starts moving faster inside her pussy. “My wife and I are new to the Crimson Oaks swinging scene, but I’d definitely remember seeing you. We can exchange pleasantries after though.”
Did he say swinging scene? Like sex parties?
Maggie opens her mouth to argue or scream. She wants to kick or fight. But as his cock pushes into her faster, the arousal interrupts her fight-or-flight instincts. She moans, digging her hands in the pillow in front of her face as he starts pounding her pussy under the covers.
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Maggie squeals as his cock hammers into her pussy, making her core clench and pussy gush. How long had he been fucking her before she woke up? She already feels like she’s going to cum.
“Oh my God.”
“That’s it, baby, take it,” Simon says. “You’ve got the perfect pussy, so fucking tight, squeezing me, taking my cock so well. You’re perfect. So perfect.”
Maggie can’t take it anymore. She seizes with an orgasm that makes her scream her head off and squirt all over the stranger’s cock.
Simon groans loudly, cock throbbing as her cunt ripples around it. He yanks himself out of her, not ready to cum and for this encounter to end. He wants to dominate her, and her holes. He throws the blanket off their naked bodies and slips two fingers into her winking, soaked pussy, coating them in her wetness and then teasing the bud of her asshole with his middle finger.
Maggie is still reeling from how hard she came. She heaves and pants heavily, trying to catch her breath. When she feels a finger invading her ass, she bucks and mewls. She’s always been a little ashamed of how much she enjoys anal play. Some guys haven’t been as into it once they see that she is. They want to talk a girl into it.
But she can’t find it in herself to resist now. She’s horrified to realize she’s accidentally walked in on some swinging orgy party her parents are throwing. And it’s emboldened some stranger to walk into her room, find her sleeping, and start fucking her. She should just be feeling horrified and tell him to get the fuck away from her.
But she can’t. She’s still hazy with lust and endorphins from her orgasm, and his finger feels good in her ass. It’s a misunderstanding, not an attack. He’s being nice and complimentary and making her feel so good.
“Fuck!” she curses when Simon fits two fingers inside her ass and starts scissoring them, stretching her out. He’s for sure going to fuck her ass. Her pussy clenches at the thought.
“You like this?” he asks, teasing and turned on. “You like my fingers in your ass, Maggie? What if it was my cock?”
“Yes!” she shouts, face burning red in embarrassment at her outburst.
“Fuck, so hot,” he says. He shifts her onto her back, dragging his fingers out of her. He uses some wipes from the to-go packet on her nightstand to wipe his fingers before grabbing the lube. Turning back to her, he lies on his side next to her. He pours lube liberally onto his condom-covered cock. Pressing the head of his cock against her ass, he tells her, “Breathe easy for me, Maggie. I’m coming in.”
Her ass fights his initial penetration, but once the tip pops in, it’s easier for him to slowly stretch her ass around his cock. She sighs in ecstasy, even as the stretch makes her wince.
Simon suddenly shoves her right leg up and over his right shoulder next to his head, spreading her out for him, and pushes his fingers—now cleaned—into her pussy. He hooks his fingers against her G-spot and thrusts while he saws his cock into her ass.
“What’s going on here?”
Fear and shame make Maggie freeze and gasp. Both she and Simon look at her open door and see Nathan Carmichael standing there, watching them with a dubiously blank expression.
Simon doesn’t stop fucking her ass, giving the other man an easy grin. They’ve seen each other around. He’s a little older than him and Tanya; teaches at the local high school. He and his wife, Sasha, are fixtures at these parties, just like Erika and Michael Livingston. And tonight, he noticed Nate in the gym with two lovely ladies. “Hey Nate. Did we distract you away from your own little group?”
“I heard screaming,” Nate says.
Maggie’s eyes are wide and frightened. Her heart pounds as her high school physics teacher walks into her childhood bedroom, casually talking with the stranger currently fucking her ass while fingering her pussy. Her whole body is on display, but she can’t stop it. The older man’s eyes walk up and down her spread-out body, pausing on her bouncing tits and pulsing pussy.
“Nice to see you again, Maggie,” Mr. Carmichael says with a deep, erotic tone. He walks up to the bed, standing right over her. He’s wearing the same horn-rimmed glasses he’s worn since she was a freshman in high school. Plenty of girls had crushes on him. She always just admired him. But even she has to admit that he has a certain appeal. His mature dignity and intelligence go well with his square jaw and salt and pepper hair.
This guy used to be her teacher and volleyball coach, and now he’s greeting her while she gets ass-fucked during her parents’ swingers’ party.
What the fuck is her life?
“Hi—hi, Mr. Car—Mr. Carmichael,” she stammers through mewls while Simon’s cock repeatedly plunges into her ass.
“You two know each other?” Simon asks through grunts. “Wanna join us, Nate?”
Mr. Carmichael eyes Maggie darkly. This is his former student. But she’s almost twenty-four now and so fucking pliant and sexy, taking a cock up her ass like a champ. His cock is rock hard, and he has to press the heel of his hand against it in his slacks. His shirt is still at Michael’s home gym. He steps closer to Maggie, reaching down to cup her jaw with his hand. “Do you want me to?”
The shame swirling inside her dictates that she should say no. But the excitement thrumming in her core begs to say yes. So she does. “Yes.”
Mr. Carmichael hums, pressing his thumb over her lips until they part, allowing him to slip the digit into her mouth. She sucks on it. He groans, his cock twitching in his pants.
“Yes? You want me to fuck that wet cunt while he fucks your ass?” he asks her.
Maggie moans are his thumb, nodding vehemently. She’s never done double penetration before, or a threesome for that matter, but the sex in the air and promise of more is too intoxicating to end it now. She wants more. Wants it all.
“Say red if you want to stop,” he says. “Nod if you understand.”
She nods.
Mr. Carmichael turns his eyes to Simon, who has paused in his ass fucking, keeping himself lodged inside Maggie. “Scoot over, but don’t pull out. I want her pussy on top.”
Simon wraps his arms around Maggie and shuffles backwards while Mr. Carmichael fishes a condom and bottle of lube from his pants while shoving them done. His hard cock bounces up, hard, thick, and curved upwards at the tip. He slips the condom on and sets the lube on the table on the other side of her bed before lying on his back as close to the middle of the bed as he can get.
Without pulling out of her ass, Simon turns them over Nate’s body, the teacher helping her straddle his lap, dripping pussy hovering over his cock. Without ceremony, he plants his hands on her ass and pulls her onto his cock.
Maggie’s mouth drops open as she moans loudly. She’s never been so full before. His cock slides right in, and suddenly she’s stuffed with two cocks and can’t move. She’s paralyzed with pleasure and pressure.
Nate groans as her pussy swallows his cock, squeezing down as her clit brushes on his pelvis. He squeezes her ass while Simon pushes her onto his chest with his hands on the small of her back and begins thrusting in her ass again. Nate yanks Maggie down, kissing her slavishly, spearing his tongue into her mouth while he shallowly thrusts up into her pulsing pussy.
“Fuck, so tight on my cock,” Nate rasps. “Is this what you wanted? Two men to just walk into your room and stick their cocks in your holes and fuck you hard?”
Maggie moans brokenly against her ex-teacher’s mouth. She kisses him desperately as her body bounces helplessly between their bodies. Her clit glides in small circles on Mr. Carmichael’s pelvis, her core clenching as their cocks fuck her with only the small membrane separating her pussy and ass between them.
“Oh fuck, oh fuck, oh fuck!” she cries out, body tensing as it threatens to go over a cliff. “I’m gonna cum, oh fuck! Faster, harder!”
The men obey, thrusting their cocks into her holes rapidly. Simon pulls out when Nate thrusts in, and visa versa.
“FUCK!” Maggie screams when she cums, both holes closing around their cocks. Her body vibrates between them, her eyelids fluttering and mouth open wide.
Nate grits his teeth as he feels her pussy squeeze him. Simon gives a choked-off groan as he suddenly pulls out of her ass when she gets too tight. He takes a deep breath, eyes watching Maggie rest her pussy on Nate’s cock.
He licks his lips. “Wonder if I could fit in there with you?”
Maggie shivers violently at the suggestion. Two cocks in her pussy? Why does that turn her on? It would hurt! It would be impossible!
But she wants it.
“Yes, yes!” she begs. “Fuck my pussy, please!”
Mr. Carmichael cups her face and says, “The condoms would tear.”
“Take them off,” Maggie snaps.
Mr. Carmichael’s eyes flick to her desperate ones. “There are rules.”
She shakes her head. “I don’t care. I’m clean and on birth control. I want it. Please.”
They’re men. They’re weak.
Sharing a look over her, they share a nod. Simon pulls his condom off and gets the lube while Mr. Carmichael lifts Maggie to pull his condom off. She’s quick to sink down onto his bare cock. They both moan loudly as they feel each other without barriers. Her pussy is so hot around him. He knows he’s going to blow soon.
“You want both our cocks in your tight little pussy, huh?” he speaks to her with a dark voice, eyes blown with arousal as he bucks into her. “You want us to stretch you out, use you, cum inside you, fill you up?”
“Please!” Maggie whines, bucking on top of Mr. Carmichael as Simon squirts more lube over his cock and her pussy lips. Her hands squeeze Mr. Carmichael’s shoulders and arms as Simon shuffles behind her and notches his cock against Mr. Carmichael’s already inside her pussy. He shallowly works the head of his cock in, pouring more lube into the mess. Once his head is in, his cock is stable enough that he doesn’t have to hold it, slowly working it inside her, rubbing it alongside Mr. Carmichael’s shaft.
It’s a stretch, and for a minute, she doesn’t like it. But she doesn’t use the safe word or complain as she twitches on top of her ex-coach’s chest. He rubs her back soothingly, murmuring to her, “Don’t forget to say red if you want to stop.”
“Uh huh,” she mewls, nodding against his chest. Her breasts flatten against him as Simon finally gets balls deep inside her pussy. It feels like she can’t breathe, like there’s no room in her body for air. She feels like a stuck pig on a spike as two cocks throb in her cunt.
“You okay?” Simon whispers against the back of her neck.
Her pussy is stretched beyond belief, and she’s still gasping for breath, but there’s a hint of euphoria in the pain that makes her body shake with pleasure. “Yes! Please move!”
“Fuck, I’m not gonna last long like this,” Simon grunts, thrusting his cock into her, sliding it against Nate’s. With all the extra lube he’d applied, they all move easily together.
Nate groans, squeezing Maggie to his chest. He fists his hand in her hair and pulls her head to the side, craning his head forward to bite and suck on her neck.
Simon bends his leg forward, planting his foot on the bed for an anchoring balance as he thrusts into her from behind. The combination of her tight pussy and rubbing against another cock drives him close to cumming.
Nate is in similar straits. He lifts Maggie’s body so he can kiss her and fit his hands between their sweat-soaked bodies to pinch her nipples and flick her clit. She shakes on top of him, screaming against his lips and bucking wildly. Her pussy gushes, squirting on their cocks and getting so tight, they can’t move or else they’ll be forced out.
Her orgasm pulls them in, and both men cum, one after the other. Their cum shoots inside her, straight for her womb, filling her cunt until it overflows and drips out of her and onto Nate’s thigh.
Maggie is limp and sleepy as Simon pulls out of her to take care of the empty lube bottles and condom wrappers. Nate slowly pulls out of her and lays her down. He grabs several wipes before returning to her, propping her legs up so he can clean her up. As he does, more of their combined cum seeps out of her stretched out pussy. He wants to smash his face against her pussy and clean her up with his tongue. But he thinks she’s had enough. Her face is blissed out and dazed.
After wiping her clean and tucking her back into bed, he turns to see Simon pulling a water bottle out of the side pocket of a suitcase. He brings it over and guides Maggie to drink.
Maggie mewls tiredly when Nate cups her chin after she takes a few sips of water.
“Welcome home, Maggie,” he says.
Chapter 2: No GIFs
Chapter Text
Maggie Livingston hasn’t been home for a winter break in three years since she transferred to an out-of-state college. Only summers, and even then, it’s dwindled down since she started working during breaks and weekends. But now she’s set to graduate in the summer and work full time, so she’s decided to surprise her parents by coming home for Christmas. She requested the entire week off months ahead of time and conspired with her aunt to make sure her parents weren’t leaving town or anything.
She drove for seven hours, getting to her hometown and driving up the street to the house by seven-thirty. Her parents’ cars weren’t there. But she knew they were out to dinner and still wanted to surprise them, so she parked around the corner and carried her suitcase in with her.
If only she had looked around. She would have noticed the lube dispensers on the tables and condoms in the toffee bowl on the coffee table. If she’d gone into the kitchen, she would have seen how many smart waters and bottles of wine were in the fridge—along with way too many cans of whipped cream. Or seen the snack bowls set up on the dining room table with yet-to-be-opened bags of chips, pretzels, energy bars, dark chocolate, mixed nuts, and a watermelon.
All of this would have clued her in that her parents had something planned tonight. But she bypasses it all, dragging her suitcase up to her room, stripping to her camisole and panties, and crawling into her childhood bed for a nap after plugging in her phone and setting an alarm for thirty minutes. But she doesn’t press the save button to actually set the alarm and doesn’t plug in her charger completely. Within the hour, her phone will die. All while she sleeps like the dead, exhausted from her long drive.
Simon and Tanya are new to Crimson Oaks and swinging. They’ve been to a club in their old city, but when they moved, they were at a loss for how to find the scene and break into it without coming off as perverts. Luckily, Tanya joined a neighborhood book club where she met Erica Livingston, who practically runs the swinging scene with her husband, Michael.
They’re fifteen years older, but the scene is evenly mixed age-wise, and everyone gets along. They started attending their parties within weeks of moving in and became engrained in the scene in their new home. Erika and Michael don’t always host, but their parties are the best. Attendees have use of the entire house except for one locked door upstairs, including the pool, jacuzzi, she-shed, and garage. They clear most of the living room and family room for dancing and have plenty of supplies, food, and drink.
Simon and Tanya like to roam separately after doing some dancing and getting a few drinks in them. They like to stumble onto the other with different people on accident, and either watch or join in.
Simon once walked in on Tanya getting spit roasted over the wall of the jacuzzi and just slipped into the hot water in front of one of the jets and told her how hot she looked. She once caught him licking ice cubes out of another woman’s pussy, and she just waltzed over and sat on the other woman’s face. A lot of the women in this scene like to nap in the bedrooms upstairs and get ‘woken up’ by whomever opens the door and finds them. The Livingstons have their bedroom up for grabs, along with a guest room, and Michael’s personal gym. Tanya and Simon once woke Erika herself by teaming up on her in her own bed with his cock and Tanya’s strap-on.
Tonight is the first party in a month, and the couple is more than excited. Neither has had sex or even touched themselves for the last three days in pure anticipation.
As they walk into the Livingston house, the lights are low, only red and purple lightbulbs on, and music is weaving through the first floor. Erika greets them in an ivory negligee, her large breasts still perky, nipples poking through the fabric encasing them. Simon boldly eyes her cleavage as she tells them where they can find snacks, drinks, whipped cream, condoms, and lube.
“Make yourselves at home. It’s lovely to see you again,” Erika says. She sees Tanya at book club once a month but only sees Simon at these parties and a few neighborhood BBQs.
They like the music in the living room, so they go there to dance for a song or two after grabbing a batch cocktail from Michael’s new built-in bar in the corner. Once they’re sufficiently loose and happy, they split up. Simon stays on the dance floor, dancing with a few new partners. Tanya wanders to the pool. She likes to skinny dip and fuck in the water.
A few drinks in, Simon is a little buzzed and has to use the bathroom. The downstairs one is taken, and he doesn’t like using the pool house, so he wanders upstairs, passing a promising scene in the guest bedroom. He uses the bathroom, and he’s on his way back down when he sees the door that’s usually locked is ajar.
Curiously, he pushes it open and grins when he sees a young woman sleeping in the full-sized bed. He likes this game. There’s something taboo about stumbling on a defenseless woman and doing things to her until she wakes up. There’s always a moment where he wonders if she will scream, like she’s not literally attending a sex party, but when it passes and she gets into it with him, it’s still hot as fuck.
He steps into the room, leaving the door half-open behind him. He can hear music and light moans and groans downstairs, giving a heady atmosphere to the scene he’s playing out in his head. Walking to the bed, he goes to the side with her back. She’s sleeping peacefully, the blanket around her waist, exposing her camisole that’s sort of see-through. Enough that he can see her large breasts and hard nipples poking through the fabric.
She’s in the center of the bed, so there’s enough room for him to slip in behind her. He pulls the blanket up, ducking his head to get a look at her innocent white panties. He bites his lip, holding back a groan. So far, she’s still asleep, not having detected his presence at all.
Lust building in his veins, he plants his hand on her soft ass and squeezes lightly. She’s warm and toned, her flesh supple and attractive. He moves his fingers to her center, brushing them over her pussy in her panties and rubbing. She’s hot there and gets easily wet as he touches her.
And she doesn’t even know yet.
Simon groans. He’s glad he kept a strip of condoms in his pocket. Pulling his hand away, he quickly takes off his clothes and jerks his cock as he stares at the sleeping woman. She’s beautiful. She has big, perky tits that he bets look hot as fuck when they bounce while she’d getting fucked. Her hair is a pretty auburn color, spread on the pillow. Her face is lovely, full lips parted as she breathes deeply.
He doesn’t recognize her, but a lot of people cycle through these parties. Some people move in or move away. Some people are just visiting. Some people take breaks and then come back. Not knowing who this woman means nothing. She’s still here at a swinging party. And everyone knows the Livingston’s rules.
Fishing out a few condoms and a mini bottle of lube from his jeans, he sets them on the nightstand. For later.
Cock throbbing, Simon squeezes the base and leans over the bed, hooking his fingers in the waistband of the woman’s panties and pulling them down her smooth, toned legs. He also pushes the camisole up and over her breasts, licking his lips as he gets a good look at her tight, dark pink nipples.
Getting back into the bed, he slides in and spoons her. He flattens his thick cock against her pussy, nestling the shaft into her slit. He wraps his arm around her, gently groping her breasts. But he has to be careful. He’s always loved the idea of getting his cock inside a woman’s pussy before they wake up. He and Tanya tried it with Erika that one time, but Tanya got too aggressive with sucking her tits and Erika woke up just as Simon was getting the condom on.
Now’s his chance.
Shifting to grab a condom and the lube, Simon quickly slides the latex down his cock and squirts some lube on his fingers, spreading it over his length before pressing his fingers to her pussy.
The woman shifts when his fingers slide over her clit. He strokes it lightly, listening to her breathing and noises. She’s still asleep, but he’s definitely making her feel good. She is sighing and wiggling, and her pussy is getting soaked the more he touches her. Maybe he could make her cum. But he doesn’t want to wake her up yet.
Pulling his hand away, he spoons her more completely and pokes his cock against her pussy from behind. He pushes her knees forward and spreads her ass, giving him all the opening he needs to slide half his cock into her tight pussy.
He swallows his groan at the feeling of her pussy squeezing his cock. She’s so tight, she almost feels like a virgin. He wonders who her partner is. He’s a lucky bastard to get this pussy to himself outside of the scene. Simon grunts as he thrusts shallowly, slowly working his entire cock into her cunt.
Shuddering with his full body, he works his cock in and out of her with slow, easy thrusts. Her pussy clings to his shaft, replacing the small amount of lube he’d used with her own natural wetness.
Their lower halves are still covered by the blanket, the shroud making the taboo somno-fucking even hotter. Simon shuffles closer to her back, fucking her open nice and slow.
Maggie’s had sex dreams before, but this one is out of this world. She can’t remember the details, or who it’s about, as she slowly comes to. But the horniness remains. The heat in her cunt; clench in her core. The arousal courses through her body. She wakes up sluggishly, moaning as her pussy squeezes around something. It’s like her dream followed her into reality, and she’s actually being fucked.
Her body rocks on her bed, up and down. The fabric of her pillow shifts under her ear. She feels the distinct heat of a body behind her now. And as her right leg stretches up, she can definitely feel something moving inside her pussy, sliding through her wet lips and filling her cunt with measured movements.
“What?” she whispers, the word coming out more like a confused moan as she wakes up and her brain clears slowly. She rubs her eyes, peering down. Her camisole is bunched up over her breasts, exposing them to the cold air of her bedroom. Her lower half is under the blanket, but she can see and feel movement under the fabric. She finally twists her head back, and sees a man in his late-thirties, naked, spooning her. As she finally realizes that the thing moving inside her cunt is his cock.
She stops breathing, fear spiking through her arousal. “Who are you?” she gasps.
The man grins crookedly. He’s handsome, even though he is much older. Full head of hair, kind brown eyes, and nice teeth. “Simon, nice to meet you. What’s your name?”
She opens her mouth to yell, scream, cry. Whatever. But his cock pierces her right over her G-spot, making her gasp and jerk and cry out, “Mag—gie.”
“Well Maggie, you’ve got one of the best pussies I’ve ever fucked,” he says so casually. “Your partner is a lucky guy. Is this your first party?”
“What? No.” She finally notices the music filtering into the room from downstairs. Were her parents throwing a party?
The man, Simon, bands his arm across her body, pinning her to his chest as he starts moving faster inside her pussy. “My wife and I are new to the Crimson Oaks swinging scene, but I’d definitely remember seeing you. We can exchange pleasantries after though.”
Did he say swinging scene? Like sex parties?
Maggie opens her mouth to argue or scream. She wants to kick or fight. But as his cock pushes into her faster, the arousal interrupts her fight-or-flight instincts. She moans, digging her hands in the pillow in front of her face as he starts pounding her pussy under the covers.
Maggie squeals as his cock hammers into her pussy, making her core clench and pussy gush. How long had he been fucking her before she woke up? She already feels like she’s going to cum.
“Oh my God.”
“That’s it, baby, take it,” Simon says. “You’ve got the perfect pussy, so fucking tight, squeezing me, taking my cock so well. You’re perfect. So perfect.”
Maggie can’t take it anymore. She seizes with an orgasm that makes her scream her head off and squirt all over the stranger’s cock.
Simon groans loudly, cock throbbing as her cunt ripples around it. He yanks himself out of her, not ready to cum and for this encounter to end. He wants to dominate her, and her holes. He throws the blanket off their naked bodies and slips two fingers into her winking, soaked pussy, coating them in her wetness and then teasing the bud of her asshole with his middle finger.
Maggie is still reeling from how hard she came. She heaves and pants heavily, trying to catch her breath. When she feels a finger invading her ass, she bucks and mewls. She’s always been a little ashamed of how much she enjoys anal play. Some guys haven’t been as into it once they see that she is. They want to talk a girl into it.
But she can’t find it in herself to resist now. She’s horrified to realize she’s accidentally walked in on some swinging orgy party her parents are throwing. And it’s emboldened some stranger to walk into her room, find her sleeping, and start fucking her. She should just be feeling horrified and tell him to get the fuck away from her.
But she can’t. She’s still hazy with lust and endorphins from her orgasm, and his finger feels good in her ass. It’s a misunderstanding, not an attack. He’s being nice and complimentary and making her feel so good.
“Fuck!” she curses when Simon fits two fingers inside her ass and starts scissoring them, stretching her out. He’s for sure going to fuck her ass. Her pussy clenches at the thought.
“You like this?” he asks, teasing and turned on. “You like my fingers in your ass, Maggie? What if it was my cock?”
“Yes!” she shouts, face burning red in embarrassment at her outburst.
“Fuck, so hot,” he says. He shifts her onto her back, dragging his fingers out of her. He uses some wipes from the to-go packet on her nightstand to wipe his fingers before grabbing the lube. Turning back to her, he lies on his side next to her. He pours lube liberally onto his condom-covered cock. Pressing the head of his cock against her ass, he tells her, “Breathe easy for me, Maggie. I’m coming in.”
Her ass fights his initial penetration, but once the tip pops in, it’s easier for him to slowly stretch her ass around his cock. She sighs in ecstasy, even as the stretch makes her wince.
Simon suddenly shoves her right leg up and over his right shoulder next to his head, spreading her out for him, and pushes his fingers—now cleaned—into her pussy. He hooks his fingers against her G-spot and thrusts while he saws his cock into her ass.
“What’s going on here?”
Fear and shame make Maggie freeze and gasp. Both she and Simon look at her open door and see Nathan Carmichael standing there, watching them with a dubiously blank expression.
Simon doesn’t stop fucking her ass, giving the other man an easy grin. They’ve seen each other around. He’s a little older than him and Tanya; teaches at the local high school. He and his wife, Sasha, are fixtures at these parties, just like Erika and Michael Livingston. And tonight, he noticed Nate in the gym with two lovely ladies. “Hey Nate. Did we distract you away from your own little group?”
“I heard screaming,” Nate says.
Maggie’s eyes are wide and frightened. Her heart pounds as her high school physics teacher walks into her childhood bedroom, casually talking with the stranger currently fucking her ass while fingering her pussy. Her whole body is on display, but she can’t stop it. The older man’s eyes walk up and down her spread-out body, pausing on her bouncing tits and pulsing pussy.
“Nice to see you again, Maggie,” Mr. Carmichael says with a deep, erotic tone. He walks up to the bed, standing right over her. He’s wearing the same horn-rimmed glasses he’s worn since she was a freshman in high school. Plenty of girls had crushes on him. She always just admired him. But even she has to admit that he has a certain appeal. His mature dignity and intelligence go well with his square jaw and salt and pepper hair.
This guy used to be her teacher and volleyball coach, and now he’s greeting her while she gets ass-fucked during her parents’ swingers’ party.
What the fuck is her life?
“Hi—hi, Mr. Car—Mr. Carmichael,” she stammers through mewls while Simon’s cock repeatedly plunges into her ass.
“You two know each other?” Simon asks through grunts. “Wanna join us, Nate?”
Mr. Carmichael eyes Maggie darkly. This is his former student. But she’s almost twenty-four now and so fucking pliant and sexy, taking a cock up her ass like a champ. His cock is rock hard, and he has to press the heel of his hand against it in his slacks. His shirt is still at Michael’s home gym. He steps closer to Maggie, reaching down to cup her jaw with his hand. “Do you want me to?”
The shame swirling inside her dictates that she should say no. But the excitement thrumming in her core begs to say yes. So she does. “Yes.”
Mr. Carmichael hums, pressing his thumb over her lips until they part, allowing him to slip the digit into her mouth. She sucks on it. He groans, his cock twitching in his pants.
“Yes? You want me to fuck that wet cunt while he fucks your ass?” he asks her.
Maggie moans are his thumb, nodding vehemently. She’s never done double penetration before, or a threesome for that matter, but the sex in the air and promise of more is too intoxicating to end it now. She wants more. Wants it all.
“Say red if you want to stop,” he says. “Nod if you understand.”
She nods.
Mr. Carmichael turns his eyes to Simon, who has paused in his ass fucking, keeping himself lodged inside Maggie. “Scoot over, but don’t pull out. I want her pussy on top.”
Simon wraps his arms around Maggie and shuffles backwards while Mr. Carmichael fishes a condom and bottle of lube from his pants while shoving them done. His hard cock bounces up, hard, thick, and curved upwards at the tip. He slips the condom on and sets the lube on the table on the other side of her bed before lying on his back as close to the middle of the bed as he can get.
Without pulling out of her ass, Simon turns them over Nate’s body, the teacher helping her straddle his lap, dripping pussy hovering over his cock. Without ceremony, he plants his hands on her ass and pulls her onto his cock.
Maggie’s mouth drops open as she moans loudly. She’s never been so full before. His cock slides right in, and suddenly she’s stuffed with two cocks and can’t move. She’s paralyzed with pleasure and pressure.
Nate groans as her pussy swallows his cock, squeezing down as her clit brushes on his pelvis. He squeezes her ass while Simon pushes her onto his chest with his hands on the small of her back and begins thrusting in her ass again. Nate yanks Maggie down, kissing her slavishly, spearing his tongue into her mouth while he shallowly thrusts up into her pulsing pussy.
“Fuck, so tight on my cock,” Nate rasps. “Is this what you wanted? Two men to just walk into your room and stick their cocks in your holes and fuck you hard?”
Maggie moans brokenly against her ex-teacher’s mouth. She kisses him desperately as her body bounces helplessly between their bodies. Her clit glides in small circles on Mr. Carmichael’s pelvis, her core clenching as their cocks fuck her with only the small membrane separating her pussy and ass between them.
“Oh fuck, oh fuck, oh fuck!” she cries out, body tensing as it threatens to go over a cliff. “I’m gonna cum, oh fuck! Faster, harder!”
The men obey, thrusting their cocks into her holes rapidly. Simon pulls out when Nate thrusts in, and visa versa.
“FUCK!” Maggie screams when she cums, both holes closing around their cocks. Her body vibrates between them, her eyelids fluttering and mouth open wide.
Nate grits his teeth as he feels her pussy squeeze him. Simon gives a choked-off groan as he suddenly pulls out of her ass when she gets too tight. He takes a deep breath, eyes watching Maggie rest her pussy on Nate’s cock.
He licks his lips. “Wonder if I could fit in there with you?”
Maggie shivers violently at the suggestion. Two cocks in her pussy? Why does that turn her on? It would hurt! It would be impossible!
But she wants it.
“Yes, yes!” she begs. “Fuck my pussy, please!”
Mr. Carmichael cups her face and says, “The condoms would tear.”
“Take them off,” Maggie snaps.
Mr. Carmichael’s eyes flick to her desperate ones. “There are rules.”
She shakes her head. “I don’t care. I’m clean and on birth control. I want it. Please.”
They’re men. They’re weak.
Sharing a look over her, they share a nod. Simon pulls his condom off and gets the lube while Mr. Carmichael lifts Maggie to pull his condom off. She’s quick to sink down onto his bare cock. They both moan loudly as they feel each other without barriers. Her pussy is so hot around him. He knows he’s going to blow soon.
“You want both our cocks in your tight little pussy, huh?” he speaks to her with a dark voice, eyes blown with arousal as he bucks into her. “You want us to stretch you out, use you, cum inside you, fill you up?”
“Please!” Maggie whines, bucking on top of Mr. Carmichael as Simon squirts more lube over his cock and her pussy lips. Her hands squeeze Mr. Carmichael’s shoulders and arms as Simon shuffles behind her and notches his cock against Mr. Carmichael’s already inside her pussy. He shallowly works the head of his cock in, pouring more lube into the mess. Once his head is in, his cock is stable enough that he doesn’t have to hold it, slowly working it inside her, rubbing it alongside Mr. Carmichael’s shaft.
It’s a stretch, and for a minute, she doesn’t like it. But she doesn’t use the safe word or complain as she twitches on top of her ex-coach’s chest. He rubs her back soothingly, murmuring to her, “Don’t forget to say red if you want to stop.”
“Uh huh,” she mewls, nodding against his chest. Her breasts flatten against him as Simon finally gets balls deep inside her pussy. It feels like she can’t breathe, like there’s no room in her body for air. She feels like a stuck pig on a spike as two cocks throb in her cunt.
“You okay?” Simon whispers against the back of her neck.
Her pussy is stretched beyond belief, and she’s still gasping for breath, but there’s a hint of euphoria in the pain that makes her body shake with pleasure. “Yes! Please move!”
“Fuck, I’m not gonna last long like this,” Simon grunts, thrusting his cock into her, sliding it against Nate’s. With all the extra lube he’d applied, they all move easily together.
Nate groans, squeezing Maggie to his chest. He fists his hand in her hair and pulls her head to the side, craning his head forward to bite and suck on her neck.
Simon bends his leg forward, planting his foot on the bed for an anchoring balance as he thrusts into her from behind. The combination of her tight pussy and rubbing against another cock drives him close to cumming.
Nate is in similar straits. He lifts Maggie’s body so he can kiss her and fit his hands between their sweat-soaked bodies to pinch her nipples and flick her clit. She shakes on top of him, screaming against his lips and bucking wildly. Her pussy gushes, squirting on their cocks and getting so tight, they can’t move or else they’ll be forced out.
Her orgasm pulls them in, and both men cum, one after the other. Their cum shoots inside her, straight for her womb, filling her cunt until it overflows and drips out of her and onto Nate’s thigh.
Maggie is limp and sleepy as Simon pulls out of her to take care of the empty lube bottles and condom wrappers. Nate slowly pulls out of her and lays her down. He grabs several wipes before returning to her, propping her legs up so he can clean her up. As he does, more of their combined cum seeps out of her stretched out pussy. He wants to smash his face against her pussy and clean her up with his tongue. But he thinks she’s had enough. Her face is blissed out and dazed.
After wiping her clean and tucking her back into bed, he turns to see Simon pulling a water bottle out of the side pocket of a suitcase. He brings it over and guides Maggie to drink.
Maggie mewls tiredly when Nate cups her chin after she takes a few sips of water.
“Welcome home, Maggie,” he says.