UMD Stories


Humiliation for Hire II
Story by Deeppan9x
Posted 4/13/22     2896 views
Glenn had loved his regular wet and messy sessions with Kiera however his work had taken a big hit a few months ago and money had become an issue. So, he'd been forced to cancel them much to his great disappointment. But then Kiera had contacted him a couple of days ago with a proposal; instead of paying her to mess him up she knew someone who would actually pay to mess him up.

He had been shocked at first by the suggestion but realised he could do with the money. And after talking further with Kiera he'd agreed to the idea especially when she offered to accompany him to the session and even drive him there. Which was why Gless was waiting nervously by the curb side as she pulled up in her smart city car.

"You ready?" Kiera called out.

"As I'll ever be" Glenn responded.

It turned out Kiera was a very fast driver and Glenn barely had time to register the scenery before they were pulling into a small gated community. Kiera punched in the access code and drove, more sedately than before, up to the driveway of the houses. Once parked they got out and made their way to the front door. Kiera knocked on it and they both waited for it to open.

The woman who answered was younger than Glenn had been expecting and was probably only a decade or so older than he was. She was elegantly dressed in a royal blue ball gown and had her hair up in a bun. He had to admit she looked quite attractive and was starting to look forward to the session now.

"Good to see you Victoria" Kiera said.

Victoria welcomed them both into her home and escorted them to dining room which held a table laden with a huge variety of desserts; everything from simple custard tarts to multilayer creamy gateaux. In addition to the desserts there were also a small number of jugs which held various sauces and more ominously there were three buckets of some unknown substance under the table.

"Wow, that's a lot of stuff" Glenn stated.

Whilst the two women dealt with the payment, Glenn was directed to another room to change. Kiera had explained some of her customers liked to add a little roleplay to the session. In Victoria's case she wanted him to play the part of her cheating husband. Glenn wasn't sure if this was based on real events or pure fantasy, but he guessed that really wasn't his business.

Glenn was surprised to discover the clothing that had been laid out for him. He'd assumed it would be a tuxedo based upon the elegant dress Victoria was wearing but instead it turned out to be golfing attire: a black polo shirt, plaid trousers, very embarrassing polka dot briefs, white socks and a navy-blue cap.

He quickly changed into the clothing provided including the pants and then made his way back in stockinged feet to the dining room. Kiera was sitting down at the far end of the room which implied she wouldn't be taking part unless Gleen called out the agreed safe word. As he entered the room Victoria turned to him and pointed a finger accusingly.

"Where the hell have you been?" she abruptly queried him.

Glenn was taken aback by the question and also Victoria's now hostile attitude. He looked over at Kiera how saw his confusion and rolled her arms indicating for him to play along. What's when he realised the session had started and he was meant to be playing the scumbag husband.

"Just playing eighteen holes" Glenn responded.

"I hear that's not the only holes you've been playing" Victoria stated.

Glenn did his best not to laugh at the witticism but luckily Victoria had turned away from him. She pulled out one of the chairs from the dining table and placing it directly behind Glenn forced him to sit down upon it. She then produced a set of furry handcuffs and taking hold of his arms, secured him to the back of the chair.

Victoria then went over to the table and started looking over the various desserts present. She picked up a couple of them up and after examining them closely put them down again. Eventually she settled on a simple custard tart and brought the pastry over to Glenn. She waved it threateningly in front of his face making her intentions crystal clear.

"You wouldn't dare" Glenn said.

Of course, it came as no surprise that she would and in fact did, especially after Glenn's little provocation. But what did shock Glenn was the force of the strike which was much harder than he had been anticipating. In fact, it also knocked the cap he was wearing off the top of his head. But the custard did lessen the impact somewhat.

As Victoria walked back to the table, she noticed the fallen cap and picked it up. She took a baked cheesecake, placed it in the hat before stepping back to Glenn and gently placing the cap back on top of his head. Then without warning she slammed her hand down hard on the cap smashing the cheesecake into his hair.

"My hair!" he exclaimed.

Kiera glanced over to check he was okay and wasn't actually objecting to the treatment. He waited until Victoria turned her back and returned to the table before giving Keira a reassuring wink. However, Victoria just happened to spin around at that moment and seeing "her husband" catching the eye of another women, hurled a chocolate pie directly into his face once again knocking the cap from his head.

Victoria followed up the thrown pie with a short barrage of pies which she brought over two at a time and covered Glenn from head to toe with. She then started with the sauces, coating him first with runny cream, then fruit coulis and finally custard.

Next Victoria produced a pair of fabric shears and started cutting away Glenn's clothing. First went the plaid trousers and then the polo shirt to leave him sitting there in just underwear. As his tormentor gazed upon his near naked body, he should have felt vulnerable but instead Glenn was completely turned on, a fact made evident by the tenting in the humiliating briefs he was wearing.

"Who's a naughty boy?" Victoria asked rhetorically.

Glenn didn't have time to reply as he received a pie to the crotch courtesy of Victoria who then took great delight in grinding it in. Then the shears made a re-appearance as his polka dot pants were sliced off. Glenn had a moment of two to imagine what would happen next as Victoria picked up the layered gateaux from the table and sashayed her way back to him.

Whilst carefully balancing the cake in one hand she hiked up her dress and began to straddled him. It was only then that Glenn realised that Victoria wasn't wearing any underwear as she lowered herself onto his erect member. Then as she rubbed the gateaux into his face, she enthusiastically rode him hard until he climaxed inside her.

"Oh god!" he exclaimed.

Getting off, Victoria retrieved one of the buckets that had been resting under the table. It was full of sticky black molasses which Glenn would have objected to if he wasn't so spent. Instead, Victoria tipped it over his head before offering the second bucket to Kiera, which she eagerly accepted, and using the third bucket to complete Glenn's humiliation by pushing it down over his head.

* * *

It took Glenn a good long soak in the bath and a couple of showers to get remove all the mess from his body. But the experience had been well worth it, and he'd even got paid for it. Victoria had requested a regular session with him and even suggested sharing him with some of her friends.

The end?
Tagged male
Comments:
madmalc:
4/20/22
  Report
I like it. You could really develop this theme with new characters(which I'm sure you're planning!)
Deeppan9:
4/21/22
  Report
Thanks for leaving the feedback Mac. I'm planning to do at least one more story in this series although it may be a little while until I get to write it
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