UMD Stories

Dean's Dream Come True
Story by WamSam1224
Posted 10/26/23     1600 views
You walk up to the hotel room, sweating bullets. Julia promised that everything was set and all you had to do was show up, but you couldn't help but second guess it. 'Could this really be happening?' You thought to yourself. 'Is this really it...?'
You knock on the door, hesitantly but loudly. You wipe your sweaty palm on your pants as the door cracks open to see who dares to interrupt her. "Oh good, it's you! A bit early, but no worries." She closes the door, unlatches the chain, and opens it so you can see her fully.

Beaming at you, brimming with excitement, is a early-30s woman just a touch shorter than you (thanks to her heels) wearing a light pink satin bathrobe. Her straight black hair shone even in the dim sconce lights of the hallway, flowing just past her shoulders. Her brown eyes were outlined with smoky makeup, and her pouty dark red lips suggested you come in.
You cautiously stepped in, still stunned that you weren't being catfished.The bathrobe was loose, but you could still make out a slim hourglass shape. Plus, those heels really accentuated her slim calves; they weren't too tall, about 3 inches, but they were strappy and sexy.
Once you tore your eyes off of your host, you looked ahead to see tarps covering half of the hotel room, with all the furniture pushed to the right of the door. The overhead light was joined by a large ring light aimed at the middle of the opposite wall where the tarps were. There were pies on either side of the tarped wall on the floor along with several buckets of gunge. The closed door on your left was likely the bathroom.

"Now then, are you ready? Aren't you so excited?? Oh my gosh, I almost thought you wouldn't show!!" Julia giggled and you couldn't help but notice how the bathrobe slid against her smooth skin. "Come on, I've got your outfit right over here. I hope you got your measurements right when you sent them to me!" She walked over to a chair and picked up a plastic bag. "There's too much crap in the bathroom,since I was getting ready in there, so I can turn my back and you can change in the corner."
You removed your shoes by the door and gingerly stepped onto the tarp where she indicated. You slowly started to strip, still in shock at how well prepared everything seemed. 'Is all this stuff really going to be covering me??'
Before removing your pants, you glanced back and saw that Julia stayed true to her word and had her back to you. You appreciated how much you've come to trust her during this whole process.
With the clear plastic tarp under your feet crinkling with every step, you removed all your clothing before opening the plastic bag. You beheld the black and white indignity in your hands: a maid outfit. You gulped. You laid it down gently before fishing around for the other parts that had been previously agreed upon. You removed a red lacy thong and boxer briefs. You layered on the underwear as best you could with your growing excitement, then stretched the maid outfit over your head. It was tight, had a deep square neck, and came down to the same length as the briefs on your hairy thighs.The capped shoulders stretched a little, not quite as puffy as they could have been. It fit, and was decently comfortable save for the thong already riding up your crack.

"Alright... I'm ready," you said, glancing down at your new outfit.

Julia turned around and squealed "Oh my gosh!! Look at you, hahahaha, oh that's perfect! I'm so glad it fits!" She clapped her hands. "Here, I wanted to add the finishing touches myself," she added after walking over to a duffel bag you had ignored earlier.She picked up a headband and apron. She giggled while walking over to you, stepping carefully on the tarp.
"Arms up!" She briskly commanded, and you obliged; what else could you do? You were already here...

She popped the headband on your head and tied the apron around your waist, pressing her body up against yours as she purred in your ear, "Are you ready...? Are you ready to be my little slut? You make SUCH a cute maid. You're going to look sooo good plastered with pies..." You blushed.
She stepped back and you put your arms down. "Woah, did I say you could put them down?" Julia asked accusingly. You put them back up."What, are you not even going to apologize for stepping out of place...?"

You blushed deeper and stuttered "S-sorry."
"Sorry...? And who are you apologizing to...?" Julia placed her hands on her belt.
"Um...Mistress. Sorry, I'm sorry, Mistress Julia."

"There you go," she smiled and dropped her robe. You were shocked at her 32Bs in a bright red underwire bikini with a bow sitting perfectly between her breasts. She posed with hands on her hips, and your gaze flowed over her body.The bottom was a small red triangle, with ties on both hips.
She giggled, and the underwire, though supportive, couldn't contain the bouncing.You were mesmerized, and she giggled more.
"Oh come on, close your mouth! You'll start to drool," she said, clearly enjoying the attention. You hadn't even realized your mouth was agape.

"Alright, back to business! You remember the safe word, correct?"

"Yes, 'Amazon'," you reply.

She cocks an eyebrow.
"Erm, yes, Mistress."
She smiles. "Good. Now then...since you've been SUCH a terrible maid, I don't think you deserve a tip."

You recognize the thin foreplay for the scenario; it was her idea, but you figured it couldn't hurt. "Oh, what? No, I think I did a great job Mistress! I deserve a tip."

She smirks. "Oh, do you? Do you really think you deserve a tip..? Do you want it?"
You can't help but grin, your arms starting to get tired. "Yes, I want it."

She turns around and bends over at the waist, showing off her best asset. "Alright, if you say so...in that case, get on your knees and put your arms behind your back."
You comply and she returns fastening an 8" purple strap on around her waist. It sways side to side with every step of her strut.Julia grabs a thick blue frosting pie (like in Chega Mais) with her right hand as she reaches for the back of your head with her left. You open your mouth willingly, ready to submit to her.
"That's right," she murmurs as she slowly slides her extension into your mouth. "There's a good little slut." It's thick enough to take up most of your mouth, and tastes vaguely rubbery.

Your lips wrap around it and Julia pumps slowly, giving you a chance to warm up to your new role. You quickly feel saliva pooling in your mouth as she starts to move a little faster. "Tell me how much you want your tip," she commands.
You try to speak around the dildo, "Ay-wan-eh!"
She laughs at your attempt and pushes it deeper, hitting the back of your throat. "Oh yeah? You want it? You're such a little whore, aren't you? Yeah, you're my whore. You ~deserve~ this tip."
She whips it out completely, letting you gasp for air as drool dribbles over your chin, before sticking it as far back as it will go. Julia holds the back of your head so you can't escape as she moans with delight.
"Oh, but of course, we need to add some makeup to our little whore, don't we?" She pulls out again. "Come on, beg me for some 'makeup', my little whore!"
You breathlessy beg for what you know is coming. "Yes, Mistress, I want the makeup, please, Mistress, I want it!"

She chuckles and grabs the back of your head again, pumping fast, saliva spilling out around your lips. Just when it's becoming difficult to breath again, she pulls your head back and *SPLAT* goes the blue frosting pie in your face.

You sit there, mouth open, catching your breath as Julia laughs hysterically at the sight of you, on your knees, in a maid costume - with pie in your face!!

When she catches *her* breath, she commands you to sit still. You comply and listen to her crunchy tarp footsteps as she moves around the room, then grabs your left hand. She ties some kind of rope around each of your wrists, and you start imagining what she's going to do.

You wait for more instructions as you feel her tying rope around your ankles as well, then walking to opposite corners of the room. The anticipation gives you goosebumps. The blue frosting is so thick that it stays smeared on your face, your mouth slightly open so you can still breathe.

"Stand up, and back up against the wall," she instructed in a deeper pitch than before. You could feel her hands guiding you blindly backwards, then you felt the ropes tighten until they were almost taut. You could feel Julia's gentle fingers wipe away enough frosting to see, and you blink cautiously, happy to see red instead of blue.
Julia's smiling face steps back and admires her handiwork. She smirks with her hands on her hips. "You know, for a maid, you are surprisingly bad at staying clean. And even worse at cleaning! For every hotel room you claimed to have taken care of, it looks even messier than when you came in! Tsk, tsk... I mean, really. It's a shame this hotel doesn't have a complaint desk..."
She crosses her arms.
"So we've had to make our own!" And snaps her fingers.
'We? Wait, wha-' and before you can fully process what's going on, three giggling women in tiny triangle bikinis pour out of the bathroom. You blush as you realize that the surprise Julia had vaguely referred to in the emails was not her wearing a bikini, but rather bring some friends. The three ladies were a brunette in a blue bikini, blonde in a green, and a redhead wearing yellow triangles.The busty blonde nearly nip-slipped as she bent over, pointing and spitting out "Oh my god, he looks ridiculous! I can't believe you got him in that!" The slightly smaller and more perky brown haired beauty sneered and declared, "Well he should! He did a HORRIBLE job cleaning our rooms! I'd say it's time for a little payback." The petite redhead giggled as her long curly locks nodded in agreement.
They proceeded to take up multiple pies and surround you as your previously twitching member woke up fully.
"Look girls," exclaimed Julia. "He's pitching a tent, just for us! Hahaha." And with that, she cocked back her right arm and you felt a pie slam into your chest to the chorus of cheering from the other girls.
You could feel some of the cream splatter on your collarbone and try to seep its way into your cleavage. You blushed even harder as you realized one of your greatest fantasies will actually come true.

*SPLAT!* came another pie, just off your right shoulder. *WHOOSH!* went another just clipping the top of your head, your little headband almost falling off. You could feel chunks of cream plop from the wall onto your shoulders. With a *SMOOSH!* a bakery pie hit its mark, and you felt the pressure on your member as it stood erect upon impact. The girls cheered, "Good one!" and "Nice shot!" ringing through your ears. You could feel yourself throb at their laughter.

"C'mon girls, don't hold back! Let the maid really have it!" Julia encouraged, and set an example by smacking you straight in the face followed by more whooping laughter. Now that you were blind again, you couldn't see what was going to hit you.
You flinched as your stomach was hit, then your chin, and again as an off center pie just caught the tip of your tent.
You heard a *Flop* followed by annoyed twitters. 'Funny, I don't feel anything...well, besides embarrassed.'
"Go on Stacy, don't waste the pie! At least put it on his head or somethin!" Julia said exasperatedly.
'Wait, what?' And then you heard a soft scraping noise, sensed a presence in front of you, and subsequently felt a *plop* of pie chunks on top of your head. The girls cheered, and Stacy elicited even more cheers by poking at the pole in your tent. You quivered at the light touch, then gasped as she gently grasped you before running back to the pack.
Before you could recover from having been touched by one of the scantily clad goddesses throwing pies at you, you feel a *SMACK* on your forehead as your face is covered with a fresh layer of cream. You try to shake some of it out of your eyes, but to no avail. You feel another *SPLAT!* on your thigh, just missing your tent by centimeters, and another straight onto your neck. You can feel cream dripping into the front and back of the dress, cool against your hot skin.
Another dozen or so pies hit you in various places, but four more are able to smack you right in the face. Every time it happened, the girls cheered and you throbbed. Finally, you heard the voice of respite.
"Alright girls, looks like we covered him pretty good! That will show him what we do to bad service around here!"
Another voice piped up, "But, we didn't really get ALL of him, did we?"

A slightly deeper one snickered, "I don't know, does he LOOK covered to you? Because I have never seen anyone absolutely smothered in pie before."
"Ladies, ladies, you both have a point. So, let's draw a fresh canvas, shall we? First, Stacy, go ahead and clear his eyes," Julia ordered. Giggling approached you as you felt thick layers of cream and frosting wiped off your eyes; blinking, you found yourself blushing as deeply as Stacy's hair as she licked some of the cream off her fingers.
"Good. Now, Macy, Tracy, grab those two blue buckets over there," Julia pointed as she directed. She walked up to you; you could feel globs of cream pattering onto the floor beneath you as you twitched in anticipation. "How does it feel so far, pie slut?" She purred, enunciating your new nickname. You pulsed yet again, wishing she would untie your hands long enough to stroke it. "Are you enjoying this as much as we are? Hehehehehe, don't worry, we're not finished yet," she giggled as she began to tear off the maid outfit to reveal the boxers and hairy belly underneath.

Julia stepped back, and the blonde and black haired beauties tossed their buckets of - 'oh shit!' - ice water! You gasped at the temperature change as your manhood faltered from the shock. Julia and Stacy grabbed towels and roughly wiped you off, making sure to poke, tickle, and squeeze you in every way they could think of. 'But why would they bother cleaning me off...? Isn't this humiliating enough??'

The answer soon became apparent as the girls complimented each other's colors. 'Colors? What colors?? Oh no...' You couldn't help but think as you felt a resurgence at the sight of four beautiful women holding dark red, bright red, fuchsia, and dark pink lipsticks aimed at you. You felt a tingle run through you like electricity up and down your spine from your groin. They crowded around you as they went to work, carefully spelling out each insult loudly in a cacophony of embarrassment.

"F-O-O-L with a BIG arrow..." on your right leg, pointing up your thigh.
"P-I-E ...M-E..." on your chest in big letters.
"S-U-C-K-E-R..." along your clavicle.
"M-E-S-S-Y T-R-A-M-P..." on your left leg.
"P-I-E S-L-U-T..." on your left arm.
"C-U-M W-H-O-R-E..." on your abdomen.
"J-U-L-I-A'-S B-I-T-C-H..." on your forehead.

The lipsticks were new and tickled sharply against your still-slick skin. You couldn't help flinching and gasping at some of the letters, or at the little licks and kisses the girls showered you with. Julia especially enjoyed teasing your nipples with her tongue. You let out soft breathy moans as she bites gently down.

They finally pull back, admiring their work, complimenting each other on word choice and handwriting. You shiver and throb as your biggest fantasy comes true.
"So, my little slut, shall we show the girls how true those names are? Y'know, he already showed off one of them. Macy, Stacy, go ahead and loosen the ropes a bit so he can show you his skills..." Julia smirked. Your arms rested against your sides as you slid to the floor, grateful for some respite from the standing. You hadn't even noticed that your legs were getting tired because of all the excitement - which wasn't about to end anytime soon!
You perked up as she stepped closer, stroking her strap on. You opened your mouth willingly as the other girls crowded closer to snicker at your enthusiasm. You took Julia back into your mouth and found a stronger rhythm than before. 'Oh god, I have an audience now - I need to impress them! Wait, did I really just think that? Oh, but, look at the bouncing...oh..yep, gotta suck, need to make them jiggle more...'
You drooled happily as the girls flicked your ears and shoved your face deeper on Julia's cock. She cheered and high fived Macy, then gestured towards something you couldn't see, but you didn't care - you were the center of attention, and the reason they were laughing so sexily.
Julia put her hand over your eyes in a signal to close them, and you complied. You could feel a hand tweaking your nipple here, twirling a strand of your hair there, and, wait, was that a hand near your underwear...?
Out of nowhere, a cold splash of something sweet and sticky landed in the back of your opened boxers, and you yelped with the dick in your mouth. As you processed what just happened, you felt a cold slap on your nose and cheeks - 'wait, is that the same substance??'
The girls giggled maniacally as one of them hiked up your boxers into a wedgie. 'Ye-ouch!' Julia kept her hands on the back of your head, strap on in your mouth, as the others took turns splashing more icy sweetness into your underwear and giving you wedgies. Some of it finally trickled onto your lips and you finally tasted your torture mechanism: custard!

Julia finally let you go and ordered the girls to tighten the restraints again. You stood back up, and they wrapped zip ties snugly around the bottom of your boxers. 'Oh? What's this...?'

Julia picked up another bucket, and gestured for Stacey to do the same. She timidly giggled, her auburn waves bouncing around her face. Tracy confidently opened the front of your boxers with both hands, and all the girls snuck a peek at the inside of the tent. On the count of 3, Julia and the redhead tipped green and blue lumpy gunge into your boxier briefs; you gasped at the sudden coolness, but was surprised it was warmer than the custard. Now you understood the zip ties: without an exit, this gunge would keep your stiff member trapped in a floating bulge of green and blue, with every crack and crevice flooded with the thick sludge. Even with the zip ties, you felt a trickle or two escape down your thighs, sending a shiver up your spine.

Whistling, Julia rallied the girls to pick up pies. "Alright girls, we know the target. Have at it! Pie our little wam whore!!"
*WHAM!*
*SPLAT!*
*SMOOSH!*

You felt pies hit your face, chest, and hip. Seems like Julia had the best aim of them, followed by Tracy. You could hear them laughing, "Oh my god, his underwear looks like a diaper! Bwahahaha!"

You shook your hips back and forth to more laughter; you couldn't see it anymore, but you supposed it felt like a diaper at this point, with how it sloshed around. "Oh look, our little pie slut is dancing for us! C'mon sexy slut, dance!" one of the girls said. Despite it not being Julia, you obeyed, and continued shaking your hips as a pie smashed directly into your crotch, making you gasp. Suddenly enough pie dripped from your face that you could blink one eye open to see the four smiling faces - or rather, three grins, and the top of Julia's head as her dark waves bounced in time with her laughter. 'Is she...is she bent over laughing? At ME??' You throbbed in your makeshift diaper.

The girls grabbed more pies while Julia continued to try and catch her breath. Her face was starting to turn a little red around the edges, but your world went white a moment later. Three more pies flew through the air, one right in your face, one just catching the top of your head, and the third on your right shoulder.

You waited for the next volley when you heard your commander's voice gasp, "Alright, wait, wait, hold up - phew - alright, there's an idea I wanted to try." You could hear her steps on the tarp as she walked over to the pies, then to you. You could sense her imposing presence in front of you, and you twitched with anticipation.

"Alright Dean," she said in a deep tone. "I want you to show my girls how much of a pie slut you are. Do you want these pies I'm holding in my hand....?"
You nodded.
"I can't HEAR you, slut!"
You hurriedly licked enough cream around your lips to respond, "Yes Mistress."
"Tsk, tsk...my full title, pie slut! Otherwise you won't get your treat."
"Sorry! Sorry, Mistress Julia. I meant to say, yes Mistress, please Mistress, I would very much like those pies you're holding..." You whimpered.
"That's much better! But, since you made a mistake before..." You could hear a crunch further away from you. "I don't think you deserve them," she said in a softer, more whispery tone.
"No! Mistress, please, I'm a dirty little pie slut and I deserve a treat! Please, Mistress Julia!" You begged with a smile, with more than a hint of desperation in your voice. But it was met with a moment of silence...well, except for the girls' giggling. Your smile faltered.
"Please Mistress! I'm a dirty little slut! I'm a messy whore! Please give me what I deserve!!"
...nothing but giggles...

You waited with baited breath. Suddenly, you felt the edge of Julia's breast press against your left nipple as she purred directly in your ear, "You're MY dirty little slut, and don't you forget it!" Then, she slammed two gooey pies on either side of your head, encasing it in cream completely, before yanking down your boxers revealing the red lacy thong underneath. Covered in blue and green slime, the thrill of the surprise pie sandwich caused your manhood to move it aside and expose yourself completely. You could tell the girls were full on laughing, despite the cream now in your ears.
'Was she standing in front of me the whole time?? Oh shit, I must look like a total fool, begging for something right in front of me...'

The slime, having cascaded down your legs, was still trickling down your thighs when a creamy pie hit you right in the dick. You gasped.
"Haha! Nice shot," said Julia. "Quick, somebody hand me a pie!" Someone must have complied, because the next sensation was Julia mushing a bakery pie into your crotch, stroking your member. She sucked on your right nipple as she stroked, and you squirmed under her touch. Shock waves of ecstasy flowed through your body - the touching, the sucking, the humiliation - you were so hard it stuck straight out, despite the thong. She stopped playing with your nipple to wipe your eyes so you could appreciate her creamy goatee and mischievous smile. There was also some cream on her bikini. You throbbed.

"Now, my little pie slut...are you ready for the finishing touch...?" She asked, winking. "Stacey!" She barked, and the redhead meekly obeyed. Julia pointed at your crotch, and Stacey understood immediately. She started flicking her tongue around your tip while Julia wiped off her face with a paper towel and grabbed another two pies. She stood by, gently urging Stacey on, while the other two girls cheered. Her head started bobbing on your cock, the sensation of the slime lubricating her mouth insanely erotic. You never thought such a thing would be possible, but you were just about ready to explode.
"Oh...oh... Mistress Julia, please, may I cum?" you gasped.
"I don't know...do you want to?" She asked coyly.
"Yes, - ah - Mistress, please, oh, I do, I do!"
"Hm...let me see...what do we think, girls? Should we let him cum?" She looked back at the others who laughed and gave thumbs' up.

Julia also laughed and bent her knee against the back of Stacy's head, gently forcing her to deep throat your dick. You could feel your tip pressed against the back of her throat, but she didn't choke. It felt like pure ecstasy, with a single continuous lightning bolt shooting up your spine from your loins, saying that it's time. You gasped, eyes rolling up towards the ceiling, and begged, "Please please please please please..*whine* ...pleeeeease Mistress Julia, I'm such a whore, I'm YOUR whore,I'm your little slut, please may I cum...?!"

Julia released Stacy and lowered the pies before commanding in a low tone, "C'mon, cum slut!" You couldn't hold it in anyone, and finally let yourself spray the largest load you've ever had. Your whole body spasmed, muscles in your legs, chest, abdomen, and even arms clenching as the tension slowly left your body in a white arc. Julia kept pace with the stream, ensuring that no drop didn't land on either of the creamy torture devices.

Finally, when you felt empty and more satisfied than you ever had in your life, Julia stood up and looked you in the eye. You smiled weakly at this beautiful, bikini-clad Mistress who had ridiculed you, humiliated you, and taught you how to find the deepest pleasure life can offer. "Th-thank you..." You muttered, the effort of speaking revealing just how exhausted you suddenly felt.

Julia smiled back: "Well I had to make sure my favorite maid got what he deserved."
*BLAM!* went the pies to either side of your head, both types of cream oozing all over your head and shoulders. You shuddered in delight, your cock twitching despite its previous exertion, and felt utter delight at having been used as a target and a toy for the pleasure of these four beautiful women.
You blinked just enough to open one eye to see Julia walking away, laughing so hard her butt jiggled in her triangle bikini bottoms. You admired her one more time before you registered what she had said to the girls.

'Wait, what?!'

The girls picked up bathrobes from the bathroom, tied them on, laughing and discussing their favorite moments, and walked out of the room. You tugged on the restraints, but they stayed firm.
'But...but...she wouldn't really leave me here, would she?! I thought I could trust her...' You wriggled in vain, wondering how the hell you were going to get free, then wondering who was going to find you like this...when the door opened.
You breathed a sigh of relied as Julia walked back in alone. "Sorry about that, I wanted to walk the girls back to their room. They can't stay here tonight, not with the mess you made!" She winked and walked over to the furniture pushed to the side. "Besides, I could never leave my camera equipment behind." She pulled out a nice looking camcorder that had been hidden behind a pillow. Then she walked directly in front of you and pulled another camcorder out, this time looking through the lens and walking up to you. "Now, here is the final result! What a messy maid you are...goodness, that thong didn't even pretend to hold you in! Hahaha, what a cute little slut you are, Dean..."

She cut the recording and placed the cameras to the side before untying you. You crumpled to the floor in disbelief..."You were...recording me? And this? All of this??" You blushed but started to feel turned on again.

"Well, duh! What did you think the ring light was for? There's also a mic on the ceiling you didn't notice haha. But I'll grab that later - for now, how do you feel?" She asked with genuine concern.

You smiled dumbly and looked up at Julia. "Amazing, Mistress. Thank you."

She grinned. "Good! I was hoping you'd enjoy yourself. I'll make a copy of the video for you, but otherwise I was just going to keep it to myself. After all," she bent over, hands on her knees, pushing her cleavage out, "I never want to forget the time that Messy Mistress Julia turned Dean into her precious little pie slut!"
Labeled male+female
Comments:
dick4pies:
10/30/23
  Report
What an exhilarating story
Chuck M:
5/30/24
  Report
wow! great story!
harvey428:
5/30/24
  Report
If only I could find someone to do this to me . . .
jpierce:
6/4/25
  Report
Love this story.
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