UMD Stories

Two's Company, Three's a Mess
Story by WamSam1224
Posted 5/15/24     1445 views
You stand nervously outside the apartment building and double check the address. You can't believe you're actually doing this - meeting up with a girl from the internet! And not only that, she's promised a night you'll never forget. You had discussed so many fantasies with her, it's difficult to imagine which one might happen. Although you'd always been the one throwing pies and giving commands, some inner part of you tugged when you read her profile...something about letting her take control enticed you. How would it feel to submit to someone else? Besides, in the video chats, she was eager to discuss boundaries so as to not let it go too far. Still...something in her last few texts came off as weird. She was a little too concerned about the timing of your arrival; but perhaps that was just so the pies didn't melt. You shook your head to clear it and caught the door from someone on your way out. You texted Sam that you were in the lobby and she replied "4B".
In the elevator, your heart pounds. You had venmo'd Sam ahead of time so she could purchase supplies and stock them in her apartment without ruining any surprises. The doors open and you walk down the hallway until you come across a gray door with a brass 4B on it. You take a deep breath and knock, your heart threatening to explode out of your chest.
The door opens and there stands a 5'5 girl wearing a pencil skirt and low cut white blouse. Her red bra shows right through the thin material, outlining her 36Cs nicely. Her wavy dirty blonde hair is pinned up with a large clip. The blouse tucked into her skirt gives her a nice hourglass shape; her fishnet stockings capped by tall black heels makes her almost eye level with you. She looks like a sexy headmistress. Her blue eyes brighten at the sight of how tall and handsome you are, though you're too busy looking her up and down to notice. She snaps her fingers by her face. "Hey, my eyes are up here!"
"Uh, sorry, I just -" you stammer.

"Oh!" Her face breaks out into a smile. "Your accent!! I mean, I knew you were Irish, but like - *damn* dude!" She ushers you into her apartment.
To your left was a doorway leading to the kitchen, to the right a short hallway with closed doors. In front of you was what normally would be a cozy living room, but today all the furniture was pushed to the edges and plastic tarps covered everything. Sam leads you to the center of the room and gestures broadly. "So? What do you think? Pretty sure I got things covered on my end," she winks. "And I'm so glad you came on time! So - did you bring it?"
"Yeah, it was not as difficult as I thought to get one my size," you said, indicating your backpack.

"Wonderful! The bathroom is over here, go ahead and get changed," she replied with an enthusiastic clap. You nod and start heading towards the open bathroom door in the corner, but she puts out a hand to stop you. "What was that? I couldn't hear you," she insists while cupping her ear. Immediately you get the gist - "Yes ma'am." Sam smiles and bites her lip as she lets you go.

In the bathroom, you close the door and take another deep breath. You can already feel a tingle of anticipation as you change out of your street clothes and open the package in your backpack.

Inside was a white button-down, plaid shorts, black suspenders, fake chunky glasses, and a plaid bowtie. You put on the nerd costume and add a pair of long white socks as Sam had initially requested. Looking at yourself in the mirror, your arms looked good in the short sleeve shirt, and it was clear you were toned under the dorky outfit. 'Man, I must be the hottest nerd alive,' you think to yourself admiringly.

You step out of the bathroom to see Sam walking out of the kitchen holding two colorful pies. You freeze - 'What is she going to do with them? Are we starting already??' She smiles and looks you up and down, then smirks approvingly and exclaims "Perfect! You look absolutely stunning."

She brings the pies over and places them along the edges of her covered furniture, along with several other colorful sweets in tins and buckets. You glance around and realize that she had essentially created a pen with three sides of couches, chairs, and various tables; the fourth side opened towards the bathroom and had plastic sheeting up to the wall. You walk nervously to the center and grip your suspenders. Sam turns around to face you.

"Now then," she declares, "are you ready to get started?" You nod; she glares at you until you get it. "Uh, I mean, yes ma'am. Pardon me, mistress." She beams triumphantly. She had explicitly detailed how to address her during the scene. "Good. Remember, the safe word is 'Pineapple' just in case."

She walks to the bathroom, facing the door for a moment. She takes a deep breath, turns around, and confidently strides up to you. "Thank you for coming in today after school. I urgently need help with something, and thought you would be the perfect man for the job." She runs her finger lightly down your chest and across your crotch; you can feel another tingle.
A little louder, she says, " I need you to tutor another student in the theater department." 'Wait, what?' Suddenly you hear a doorway open from the hall to your left and the click of stilettos on a hard wooden floor. You spin around to face a scantily clad blonde with pigtails, a short plaid skirt, white knee-high socks, and a white button down tied under her voluptuous breasts. You can feel the blood rush downwards as she smiles and waves. "This is Erica," announces Sam. "Go on, give us a twirl!" Erica obeys, her ass clearly on display even without the skirt flouncing around.
"Now then," Sam says as she steps back, letting Erica stand in front of you, "I need you to show her how to be a stooge in a comedy. However, this will be an x-rated show, so I want her to get some practice on the acts she will have to perform in front of an audience." Erica twirls one of her pigtails and licks her lips as she eyes you up and down.

"Helloooo Erica," you say, a little deeper than usual. "Pleased to make your acquaintance."

She giggles, "You were right, Sam! He DOES have a sexy accent."

Sam grabs a pink fluffy pie - all the colorful pies were made like this, sitting in fragile crusts with no tins. She hands it to you, and you test the weight. Erica bites her lip sexily, then asked "So ...where should I start?" She kneels down and reaches for your pants, but you hold up your hand; she stops. "Get up," you command. She does so, her gaze never leaving yours. "Turn around." Hands on her knees, she looks over her shoulder as you stare at her gorgeous toned ass. Couldn't hurt to smack it a little, right?
So you do. You spank her with increasing force as she moans, until she loses her balance and falls forward onto her hands and knees. She flips over, legs wide, staring up at you with eagerness to please.

But you motion for her to turn back on all fours. You haven't even done what you wanted to with her in that position yet. You gently feel between her legs and find a little moist spot - she gasps. 'Oh good, she's enjoying this!'

Making sure her skirt was flipped across her back, you spank her with the pie; pink cream flies out in a circle across her back and thighs as she squeaks from the impact. You look up to Sam for approval, and she gestures for you to go on.

You turn around and grab orange and blue pies, line up your aim, and smash them on each of her butt cheeks. The colors look nice as they overlap each other, but you decide to play with color theory and mix them together. You sensually rub the mess into her skimpy thong and between her legs, listening to her little gasps for directions on where to focus. Your fingers find her opening and play with her lips, letting your middle finger explore. You tease her for a minute before turning around to pick up another blue pie.

This time, you hit her from the other direction; as you stand before her, she tilts her face up to meet your eyes. She slightly opens her mouth just before you splatter her face with blue, the creamy confection spraying over her hair and shoulders. You feel something move in your pants, then decide to grab a yellow pie. Meanwhile, she stands stock still on all fours with face still upturned, waiting for directions.

You slam the yellow into the blue, and it's difficult to make out her facial features, even when she spits out a glob. The cream sticks well to her skin, and her upturned face prevents it from falling too quickly. You decide to reward her with some more light fingering.

Next, you decide to move her legs apart and place a yellow pie between them. You walk around and push her shoulders so that she sits back onto the pie. You can feel her shiver of delight. You guide her hands to cup her breasts with her fingers outstretched and pick up pink and blue pies. You sandwich Erica's face, her mouth still agape as she lets out a quick "Mmph!"

Bits of crust with chunks of cream tumbled onto her34D breasts; their size act as a shelf, so most of it does not make it to the floor. You proceed to massage the mess into her chest as she lets her hands fall to her side. You slide yours under her bra and twist her nipples (to her delight!). She spits out more cream over her chin in order to let out a proper moan. It drips in the valley between her breasts and acts as more lubricant.

You can start to feel your member shift around, looking for a window to peek out of. 'Don't worry, you'll get your turn,' you chide.

When you can't take it anymore, you get up to get another pink pie and decided to unclip your cheap suspenders. Your pants fall to the floor as you hear a chuckle. You glance up, surprised, as you had forgotten Sam was even here. She dips her head towards your victim as if to say 'Go on, we both know what you want.' You carefully step out of the pants and walk back to Erica, one hand holding her pink prize and the other stroking your cock.

You place your member in Erica's warm mouth. She understands immediately, and starts to hungrily bob her head back and forth. 'Oh fuck...' You think to yourself as your eyes roll up to the ceiling; you could feel the cream from her face smearing against your clean skin rhythmically. 'There's only one way to make this better,' Your free hand grabs the back of her head and pulls it towards you; her nose bumps up against your abs as she gags on the full length of your cock. You hold it there, enjoying the choking sounds she was making, before finally letting her go and smashing the pink pie in her face. The cream and slobber mix together as she once again spits it out, clearing out her mouth to catch her breath.

You nudge her head forward again and this time she uses her hands for assistance. She goes to town, head bobbing enthusiastically, smearing more cream from her hands, forehead, nose, and chin on your skin. You bring her hands to your butt; she squeezes with excitement. She continues to gag on your cock as you feel yourself getting more and more stiff. She clearly had a lot of practice!

After a few minutes, you decide you're hard enough; you place a hand on top of Erica's head and she slows down, then pauses. You carefully take your dick out of her mouth as she licks her lips. "Stand up, and grab onto the edge of that chair," you instruct. She stands and wipes her eyes enough to see where you meant, then obediently bends over and grips the sides. You admire the little peaks of cream on her yellow ass before pulling her thong down and grabbing another green pie.

This one you smash upwards into her pussy, smearing it thoroughly. You stroke your cock in anticipation as you aim it towards her vagina; the cream feels wonderful on your wet, sensitive tip. She bends her knees to adjust her height and she gasps loudly as you thrust inside of her. 'Oh god, oh yes, oh fuck...,' goes through your head as you slide easily in and out of her. You can't tell if it's her or the cream that is lubricating your dick, but you don't care.
"Oh yeah, you like that, you dirty bitch?"
"Uh, uh, yes! Yes I like it. I'm a dirty whore, I'm a dirty slut!"

"You're my little pie slut," you grunt, increasing your speed.

"Uh, uh," she groans with each thrust, "yes I'm your little pie slut! Teach me to be a good little whore!"

You continue thrusting until you're close; but this isn't how you plan on finishing. You wrap your arm around her midsection and casually throw her to the ground; she lands in her original mess and squirms.

"On your knees," you command as you search for the perfect slime - the green one, yes, lumpy and thick. You hefted the bucket in your hands and sloshed it a little to test it's viscosity. 'Perfect.' You turn back to your slave as she obediently opens her mouth and closes her eyes. You take your cock and shove it in her mouth; she holds on, creating a suction with her luscious lips until you are...just...on....the...edge...!

You whip it out and cum on her face, trails melting from her forehead down her nose and obscuring one eye completely. 'Oh FUCK - I can't remember the last time I blew so much! Oh god, oh god, yes...shit, she looks like a good little whore with my cum all over her pretty face.' You pump until you're about empty, then you stick your tip in her mouth to let her lick it clean. Her mouth stays open, begging for more. You finish her off with a slow waterfall of the green slime pouring over her and filling every crack and crevice of her skimpy costume. You barely register that she's finger fucking herself as the lumps slide between her ample cleavage and over her belly button. You're too mesmerized by the sight of the leisurely moving river of gunge and the sound of her gurgling with delight.
Despite just releasing all over her face, you could feel your shaft start to rouse itself again. All you could feel was the bucket getting lighter, your dick twitching, and the slime pooling around your feet, morphing itself around your toes.

A loud clap startled you; you glanced behind you at Sam leaning against the wall. She continued to clap, slowly, methodically; what was that look on her face...that gleam in her eyes...?
"Oh, my darling pupil...that was good, very good. But not great."
The bucket ran empty, and you lowered it onto Erica's head as she continued to finger herself.
Sam strolled over to you, hands clasped behind her back. "Tsk, tsk. I had higher hopes for you." She got right up in your face and smiled maliciously. "I guess I'll have to show you how it's done." She walked towards the nearest chair and stood in front of it, fidgeting with her pencil skirt. You took a moment to appreciate how taut it was over her shapely butt, and how the heels accentuated her calves.
"There we go," she said, snapping your gaze back up at her holding a yellow cream pie with - oh god - a strap on pulled over the edge of her skirt. 'Has she been wearing that this whole time?? It's huge!' She strutted over to you, the 8" purple monstrosity wiggling to and fro; you couldn't take your eyes off it. 'Oh no, what is she going to make me do...?'

"Kneel," she commanded, and you obeyed. She paced back and forth in front of you as she said, "Now then, I want to show Erica how a good domme humiliates their slave. First of all, I want you to beg." Your eyes finally rose up to meet hers, a pout on your lips. "What?"
"You heard me. Beg."
"I...I... I want it?"
She snorted with laughter. "Oh come on, surely you can do better than that! Come on, my little pie slut, tell me how much you want it!"
She teased the pie in front of your face. You swallowed, your mouth suddenly dry. "I...I want that pie. Please."
She frowned; "Oh, so you just expect me to GIVE you my pie?"
You finally caught on, "Please mistress, I want that pie so bad, YOUR pie, please please please stick it in my face."
She smiled. "There we go, now that's more like it...you want this, my little pie slut?"
You could feel yourself throb. "Yes, mistress, please mistress!"
"Come on, a little more - or I'll have to give to Erica instead!"
Your eyes widened, "No, no, don't give it to her, she doesn't deserve it, please mistress, I wan-" *splat!*

Suddenly your vision disappeared and gunk forced itself up your nose. You pushed out the sweet cream that had landed in your mouth as you were talking. You sat there for a moment, stunned yet aroused, before slowly wiping your eyes.

Her pitch dropped to a husky pitch. "Alright, bitch - are you ready to squirm? Are you ready to be my little pie slut?" You nodded dumbly, ready to obey anything the headmistress orders you to do. She chuckled and grabbed two more pies - an orange and a pink. She walked back over and stood in front of your limp, kneeling body.
She bent over, cleavage leaning dangerously close to the edge of her white blouse. "Suck it."
You feel a drop in your stomach and a blush creep into your cheeks. You automatically open your mouth and taste the rubber of her dildo slide in with some of the sweet yellow whipped frosting. She pumps slowly, giving you a moment to adjust to the transfer of power. As you process what was happening, you start to suck more vivaciously.

"That's it, my little slut...suck it...take it all in..." She murmurs. You work up a rhythm until you feel the tip poking the back of your throat. Right when you finally start feeling satisfied with your performance, you heard a gasp before feeling both pies come down on either side of your head. They are smeared around the top and back of your head, followed by Sam pushing your head as far down her shaft as as it would go. You sputter, but do not struggle. 'This is my role now; I am her slut...' you remind yourself.
Sam releases you and steps back, letting you catch your breath as drool and cream dribble onto your chin. She grabs a bucket and walks back.
"You know you're not done, right?* she asked in a flat voice. You obediently take her dick into your mouth again and start pumping. This time, she moves her hips to the opposite rhythm, such that as your head moves forward, her hips thrust her dick forward to smack the back of your throat. You gag a little less each time, getting used to the feeling of having a full mouth.

Just as you find your rhythm, you feel a cold *plop* on the top of your head. It catches you off guard, and your rhythm falters. "Keep going," said the commander, and you obey. Another plop carefully lands on your head, then another on the bridge of your nose. You shudder as more clumps of gunge fall on your shoulders, ears, and eyes. This time you don't miss a beat: "Good boy..." she purrs.

Sam continues to let the gunge fall bit by bit, ruining your schoolboy uniform even more. The coolness dripping down the back of your shirt raises goosebumps along both arms. It doesn't taste too bad; rather bland, in fact. If it weren't for your position, you almost wouldn't mind tasting a bit more. As it were, you don't have a choice.

She laughs above you, clearly enjoying every minute. At this point, Erica has finished playing with herself and removed the bucket so she could crawl over. Her breast brushes against your arm as she starts rubbing your chest, unbuttoning your shirt to expose still-clean nipples. Sam takes an interest, and decides to mix it up a bit.

"Erica, do you wanna play too?" The submissive schoolgirl nods, still breathing heavily. Sam whips her cock out of your mouth and slaps your face with it. "Well Richard, since you clearly didn't satisfy her enough, I'll just have to show you how it's done!"

With that, Sam takes a step back and bends down to grab two different breasts. You wipe your eyes enough with one hand to see her bite her lip as she massages your left nipple. "Well, Erica certainly has you beat in the top-heavy department," she comments casually. "Erica, would you like to try your hand or rather, your mouth, at sucking?" Ever the obedient slut, Erica giggles and takes Sam's cock easily into her mouth. She starts enthusiastically sucking, her messy once-blonde locks bouncing ever so slightly. Your hands, as if possessed, reach out to fondle her.

Sam notices, but doesn't seem to mind. "Oh Richard, you really have some competition," she teases. "Seems like Erica's one-upped you again!"

You blush, for some reason a small sprout of jealousy blossoming in your chest; you have to win at SOME part of being a sub! You decide to consciously pull Erica's hair back and take over her dick-sucking duties. Erica sits back, astounded at the audacity. Sam's surprised expression quickly gives way to a smug look as Erica pulls your shoulders back, tongue searching for the cock that was rightfully hers. Sam decides to readjust herself such that each of you have a different side of the dick to lick while looking up at her with pleading eyes.

After some chortling, Sam finally steps back with "That's enough!" You both pause, panting. "Haha, since you both are so eager to please...both of you strip, flip - foreheads to the floor, asses in the air. NOW."
Your face flushes as you do as Sam commanded, staring straight at your sub-turned-competition, who winks at you and blows you a kiss. Then she gasps as you heard the first *SMACK!* The second one hits your bare ass, droplets of gunge that had dripped their way down splattering across your back. You could hear the tarp crunch as Sam steps away, then comes back to another smack; this time, on the other cheek.

"What do you say to someone who smacks your ass, Richard?" Sam demands.
Stumbling, you try to come up with the proper response, "Um, uh...thank you?"
She smacks you again, harder this time. "Try again," she teases.
"Uh, thank you, Mistress Headmistress! Thank you very much, Headmistress Sam," you grovel.
"There we go," approves Sam. "And as a treat..." *SMACK!* goes the pie, and you gasp as the frosting smushes its way into your butt-crack. You expected it to soothe like lotion, but it only makes the hand print sting.
Erica bites her lip, "Oh, please Headmistress, won't you give me one too?"
You hear more tarp crunching and another smack; Erica grimaces. "Thank you, Headmistress!"
"Good girl," Sam flatters, as fresh bits of blue fly onto her shoulders and hair.

Sam continues this game as you each try to one up the other for groveling. After three more pies each, your rainbow asses might have been a little bruised. Suddenly, you jerk as something flicks your dick.

"Oh? Is someone ready for round 2...?" asks Sam.
"Yes, headmistress..I-I mean, possibly..."
"Well, let's make sure we end with a bang, shall we? Richard, flip onto your back. Erica, go ahead and saddle him backwards. It's time to test your math!" Sam threw her head back and laughed, then bent down towards your face to sneer, "What do you get when you add one slut on top of another...?"

Before you could answer, Erica who clearly had been told the answer in advance shoves her messy pussy in your face and takes your cock in her mouth again. Spluttering, you manage to grab a breath before wrapping your hands around her slippery thighs. All the while you can hear slurping and laughing, which only stiffens your member more. Your hips instinctively push away from the floor to feel the back of Erica's throat, but it's difficult to focus on the sensation with the way she bounces her lower half on your face. All you can do is bury your face into the creamy crevice and lick whatever your tongue can find.

You don't even notice the tarp crunching again as Sam grabs a bucket and slowly pours bright pink slime along Erica's back. She makes muffled noises of delight but never stops sucking. 'Man, she is a trooper...' you thinnk to yourself. But you are certainly able to process the cold slime dripping from her body onto yours. By now, you're starting to feel a little overstimulated, but not in a bad way just in a way that you never had before. Coherent thoughts escape your grasp as you succumb to the slippery, creamy, delicious mess that was this gorgeous woman on top of you.

Sam circles the pair of you like a hungry shark. Every so often, she carefully adds a pie here, or an extra dash of leftover slime there. You can feel her smack Erica's ass, making her jiggle in your mouth. Between the lack of visual stimuli and your recent expulsion, it takes you a little longer to get close to cumming. As if reading your mind, Sam pulls Erica off and starts jerking you off. Taken by surprise, you lay there, eyes closed, and listen to her train of consciousness: "Oh yeah, cum for me slut, be a good little whore, c'mon Richard, be a good little messy sub for your Headmistress, you're my obedient slut, cum for me, cum for me..."

And then...you do.

It wasn't as much as before, but you feel another great release while Erica nibbles your ear. You groan into between panting.

Sam wipes her hand on your thigh (certainly to remove any cum, because there was no part of you clean enough to wipe off slime or cream). You open your eyes as she struts over to you with a pie in her hands. Despite your exhaustion, you can't help but vainly attempt to peek up her pencil skirt. Her evil grin looks upside down to you.

"So, how do you feel...?" she inquires genuinely, belying the look in her eyes. You grunt an affirmation that you're fine. "Good! Because I've been looking forward to this part." She bends down, teasing the pie in front of your face; a bit of pink swirl rises above the edge of the crust. Suddenly, you remember one of the final things you had agreed to, which seemed like an eternity ago. "On behalf of every woman you've ever done this to, you DESERVE this," she relishes before dropping the cum pie directly on your face. There was not enough frosting in your ears to block out the cackling of the two women.
You lay there, satisfied as hell, panting in your own mess. When the snickering dies down, you wipe your eyes with one hand as Sam's face hovers over you, smirking. "So, whaddaya say, my little wam whore? Up for round 3?" Your eyes widen before you catch on that she was joking. "Hahaha, don't worry, we're done why don't you be a gentleman and let Erica get cleaned up first?" With that, Sam helps Erica up and leads her to the bathroom, stripes of mess decorating her blouse as Erica leans in to whisper in her ear.

You hear the shower turn on and clothes drop to the floor. You hear Sam giggle and moan, but nothing from Erica except slurping. At this point, you're too tired to get up and watch; you just lay there, in the filth, smiling at the new-found discovery about yourself.
Tagged male+female
Comments:
geyemessy1:
5/15/24
  Report
Wow! Just wow! This is a dream come true! I wish I could make this a reality! Absolutely amazing work!
cmfan777:
5/15/24
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Really well done. A perfect amount of eroticism to go along with some great mess. I can't wait to read whatever else you have in store. Thank you!
PiedDCguy:
5/15/24
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Incredible work Sam! Such a great read and looking forward to more!
Chuck M:
5/17/24
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Ironic, I know a girl named Sam who I would love to something like this with..great story and very descriptive...totally love it!!
PieWriter:
7/11/24
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WOW! I loved this. Fun, elaborate, intense, "Pineapple!!" (Mine is 'Astro-physical-spatio-magentic-anomaly', but who's counting?).. loved this story! TY!
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