UMD Stories

Your Payment
Story by SethJamba
Posted 2/17/21     1068 views
1
Edward sat an in elegant posture, awaiting for his "master" to appear. He was currently roleplaying for his friend. And Edward was used to cosplaying... not crossdressing. So when his friend Eli asked him if he was up for it... Edward, begrudgingly, agreed in roleplaying for friend for the time.

Edward is a handsome Japanese-Hispanic male with black hair and eyes. As mentioned before, he loved to cosplay. He would usually make various videos with the help of his friends dressed in various superheroes, anime, etc. He was very eager when to dress up with others who shared the same passion.

But this current scenario was anything but enjoyable right now. He was currently dressed in a maid outfit. The maid outfit in question is a black dress at knee length with a white bib with two black bows at his neck and a white apron at the bottom. He had on white knee high nylons and wore on of his two shoe options: black slip on low heel dress shoes. And he wore a black bow tie around his neck for a small add on.

Edward perked hearing the clicks of heels against the wooden floor. He saw his friend. For their little roleplaying, he dressed as a smartly dressed man, Edward's "master," with a classic black suit jacket, covering white dress shirt and black tie was covered with a black vest. He had on black slacks and patent leather dress shoes for hiding the black dress socks he had on.

They were roleplaying as a maid who has done a great job of cleaning and wanted to be paid. How? Well, that's what Edward didn't know.

Edward awaited the arrival of his "master" with his legs crossed and hands in his lap, looking ever so innocent.

"Did you clean everything?" His friend said in a regal tone.

"Yes sir," Edward replied in his best feminine and polite tone he could muster.

"The stairs?"

"Yes sir."

"The furniture?"

"Yes sir."

The fellow role player rambled on about everything he could think off for the crossdresser could have cleaned and Edward was very polite with the responses as they continued.

"Well done then, maid. Now for your payment for your cooperation..."

"Of course sir." And with that Edward rose up and followed Eli...

To another chair in the marble dining room?

Edward mentally gained confusion upon walking into the room, but did not question his friend's roleplaying so he sat down in the chair with retaining his professional posture, leaving him to ponder what he was planning on doing.

The smartly dressed man returned with a trolley of pies, mostly banana and chocolate cream pies from what Edward could decipher and saw about two dozen. The master picked one up and strode over to Edward, who was slightly shifting at the approach and wondering why he was approaching him... in a seductive manner.

"What is my payment for today, sir?"

Edward did get a answer... in a messy -yet soon to be arousing- way.

His friend took one of the pies -a chocolate cream pie- and smashed into his "maid's" chest, immersing the top of his costume in a brown paste that was very gooey. Some of the cream exploding upon contact and splattering onto the crossdresser's neck and bow tie while some instantly ran down his outfit after the impact and the crust stayed for a bit before falling itself. Landing in his lap, Edward had a face of surprise at the action, letting out a gasp like a woman who just had her favorite dress trashed. It didn't stop there though...

The thrower went back to the trolley and grabbed a few more pies, enough to tarnish the "maid's" appearance. He would either throw them at Edward or smash them in his handsome face or adorable costume. Two more pies landed against his costume and about three hit his face, leaving crust and cream all up on his body. Four more pies came crashing onto him, each ruining a certain portion of the costume. The "maid" took each impact that covered and smothered the poor crossdresser in the gooey and crusty dessert. Although, Edward was rather slightly aroused by each impact and letting out small moans from each.

The role player made sure the maid was quite comfortable during the onslaught and the pies were just the start. He squirted him with Hershey's chocolate syrup, getting Edward's face, dress, stockings and heels with brown. The "master" even made his "maid" take off his heels, fill them with whipped cream and placed them back on, letting the cream "exploded" as Edward placed them on.

After the "payment," Edward was a dessert maid. The roleplaying crossdresser had been covered in all on his body with the various substances. His handsome face and black hair were smothered in pie cream, crust and the chocolate syrup. The chocolate syrup stains were very visible along his outfit in a various directional forms. The black knee length dress, white bib, and apron had been smothered from the master's onslaught, splotches of the pies' crust and cream littered among it. His bow tie had taken some impacts "face first" so the end result made it crooked. His white nylons were longer white, now brown and yellow from the substances, and his black heels -as before- were creamy white from the whipped cream on the inside and crust covered on the outside. Needless to say...

Edward had enjoyed his payment.

The friend approached the victim, having a smirk of his own. "How's that for your payment?"

"Very good sir."

"Perhaps you should also receive a good review on my behalf."

"I would enjoy that."

"Yes you would, now... clean up this mess."

"Of course, sir."

His friend walked away and left Edward to it. The "maid," though had a bulge from his session. If he role played and got paid more like this...

He would so crossdress some more in this outfit, minus the desserts on he is currently wearing.
Tagged male
Comments:
gungebrah:
2/17/21
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Very good story (I wish it was me)
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