UMD Stories


Guilty Pleasure: The Final Session
Story by Deeppan9x
Posted 11/9/22     2978 views
Peter arrived far too early for his final session with Dr Olivia. Rather than go straight in and sitting in the waiting room staring at the therapist's impressive qualifications, he decided instead to stay in his car and listen to some music until it was time for his appointment. So, he was ideally placed to see the catering van pull up outside of the offices.

The caterer got out, opened the loading door and pulled down a small ramp. They then carefully wheeled out a catering trolley that was almost a tall as they were and bearing half a dozen laden trays. Peter noticed that the trays contained a variety of cream pies, gooey cakes and jugs of assorted sauces. He could guess where the desserts would soon end up especially when the rear doors to the offices opened and his therapist stepped out.

Suddenly feeling shy and not wanting to be seen by Dr Olivia, Peter slumped down in his car. But after a moment or two his curiosity got the better of him and he peeked over the dashboard. The caterer wheeled the trolley into the offices before returning to the van and driving off. Dr Olivia waved the caterer goodbye then turned towards Peter's car and cupped her hands around her mouth.

"I'm ready when you are" she yelled.

Sheepishly Peter got out of his car and made his way into the building. He quickly passed through the empty waiting room and stepped into the therapist's office. Dr Olivia was removing the final desserts from the catering trolley and placing them on her desk as he entered. She gave Peter a welcoming smile and indicated for him to take a seat on the chair in front of her desk. Before sitting down, he checked there wasn't a pie or cake already resting upon it.

The therapist then took her seat behind the desk and quickly consulted her notes before returning her focus to her client. Peter was trying to reflex but that was proving to be more difficult than expected especially with all the messy ammunition laying around him just waiting to be used. Dr Olivia began the session with a straightforward question.

"So how are things between you and your girlfriend?" the therapist asked.

Peter took a few seconds to collect his thoughts before responding. He confirmed that things were going very well with his girlfriend, and he was very optimistic about their future together. They had even engaged in some messy sessions which she had seemed to enjoy. But up until now the mess had all been one way, with him on the receiving end. But that would change this coming weekend which was both his ultimate fantasy and worst nightmare.

It had been his fantasy ever since he'd hit puberty. He didn't know where it had come from, but he'd always thought the idea of pieing a woman incredibly exciting. It was something he'd read online fiction about, downloaded videos on and joined websites to explore well before he'd ever had a chance to enact it for real with a woman.

But it had become Peter's nightmare when he'd actually attempted to experience it of real with his girlfriend. She'd been willing and he'd stocked up with plenty of messy goodies but when it came time to start dishing them out, he couldn't. Something had held him back and it had taken him a session with Dr Olivia realise that it was guilt. And so now he attended regular sessions with the therapist to help address his guilty feelings.

"Well let's get on with it then" Dr Olivia said.

Peter watched as the therapist stood up and selected one of the cream pies from off her desk. It looked to be frenched silk with chocolate filling topped with fresh cream all in a pastry case. The therapist carefully balanced the pie in the palm of her hand before slowly making her way over to Peter, swaying her hips provocatively as she did so.

The grin she gave Peter might have been friendly but there was more than a hint of menace about it, and he knew there would be no mercy given. But before she deposited the pie into his face, she teased him with it by almost driving it into his face before stopping, taking a moment for him to contemplate his fate before taking the pie away. She did this three times before finally smashing it into his face.

"A promising start" the therapist declared.

Whilst Peter sat there with chocolatey cream dropping from his face, Dr Olivia picked up a pair of identical cream pies from off the desk and sandwiched his head between them. Next the therapist quickly grabbed another two pies, one of which she thrust into his face before taking the second one and depositing it on top of his head.

With pie filling dripping down the inside collar of his shirt, Peter realised that he was in for a somewhat messier session than he'd previously experienced. He'd already been on the receiving end of five rapidly delivered pies and that had barely dented the number of desserts that the caterer had delivered. But that didn't alarm him, in fact it excited him, and he was looking forward to seeing how Dr Olivia intended to use the remaining supplies.

The therapist had picked up a large cake which seemed to be completely covered in an inch or more of white icing. She then walked over to Peter and to his complete astonishment held it out for him to take. He carefully took it off her expecting for her to change her mind at any second and instead thrust the cake into his face. But she clearly had something else in mind.

"You know what to do with that" Dr Olivia stated.

Peter knew what was expected of him but hesitated which earned him a sharp look from the doctor. So, after taking a deep breath he propelled the cake upwards whilst at the same time ducking downwards with his head. This had the effect of burying his face deep into the cake, breaking through the icing and penetrating into the creamy filling beneath. After a few moments he pulled his head out of the cake and attempted to clear some of the filling from his face so he could see again.

It turned out that Dr Olivia was standing right beside him and was holding a jug above his head. As Peter glanced up, curious to see what the container held, the therapist tipped it over to send a stream of cold custard down on top of him. The yellowy substance coated his facial features before running down his shirt and pooling at his lap.

"Let's tidy that up, shall we?" the therapist asked rhetorically.

Peter was pretty certain that Dr Olivia didn't have cleaning in mind, which was proven to be correct shortly thereafter as she picked up a key lime pie and thrust it against his crotch. Shockingly the therapist didn't then immediately withdraw her hand as she continued to grind the pie firmly against his groin. So, she quickly discovered exactly how excited Peter was by the treatment she was dishing out, much to his embarrassment.

That didn't appear to bother Dr Olivia, in fact she seemed to take great delight in teasing him. And as such she continued to rub her hand up and down the inside of his leg which had the effect of hardening his already erect member. Peter closed his eyes to better enjoy the sensation, so was somewhat surprised a few seconds later when it came to a sudden stop.

Opening his eyes, he discovered the therapist standing a couple of steps away from him. Oddly rather than holding a pie in her hands as he would have expected, she instead held her notepad. Peter took a moment to relax as Dr Olivia consulted and added to her notes which meant that his erection began to abate. Putting down her pad, the therapist picked up another pie from off her desk and turned to face her patient with a smile upon her face.

"You're making incredible progress" Dr Oliver asserted

And with that she let fly with the pie which struck Peter dead centre in the middle of his face. More pies followed as the therapist bombarded Peter with the majority of the remaining desserts. Pies impacted all over his body including his torso, arms, legs and of course his head and face. Sometimes they were hurled at distance and other times pressed against him at close range.

After the pies came to an end Dr Olivia moved on to the other desserts. A trifle was dumped over his head, jugs of sauce were emptied all over his clothes and cheesecakes were screwed into his face. There was even a huge multicoloured sheet cake which the therapist struggled to lift and almost dropped a couple of times on her way over to Peter before smashing the entirety of it against him to leave him thoroughly covered in vibrant icing.

"How are those guilty feelings?" the therapist asked.

Peter thought about it and realised that indeed his feelings of guilt about messing up a woman were certainly greatly reduced if not completely gone. He began to think about the upcoming weekend with his girlfriend and what he might do to her, it was exciting to plan for. Of course, he still had this session with Dr Olivia to get through first.

The therapist was having to look around to identity the few desserts that remained. She gathered together the few remaining pies and a final jug of custard. Most of the pies soon found their way to Peter's face as Dr Olivia hit him again and again. As for the jug of custard, the good doctor took it in one hand and with the other hand pulled out the waistband of Peter's trousers. She then poured the cold liquid down into his pants, coating his erect member.

The once again the therapist began to massage Peter's cock whilst reaching out for the penultimate cream pie. She started slowly and built-up a pace gradually, all the time bringing pie she held ever closer to his face. Peter thought he was going to get pied at the moment of his climax but instead the therapist struck before his moment of release.

"So, do you think you'll be able to mess up your girlfriend now?" Dr Olivia questioned.

Peter was dismayed at his lack of an orgasm, especially as this was the second time, and looked up at the therapist. However, rather than standing right beside him as he'd expected she was now sitting back behind her large desk with pen and notepad in hand. She jotted down a few notes before returning her attention to Peter, looking at him expectantly. It then dawned on him that he hadn't answered her question yet.

He spotted an unused pie and without a second thought threw it at the therapist. Peter's aim was true, and it struck Dr Olivia directly in the face much to her surprise. And you know what, Peter realised that he didn't feel guilty for doing it. In fact, he was now very much looking forward to the weekend with his girlfriend.

The End.
Tagged male+female
Comments:
newpieguy09:
11/12/22
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Bravo!
Deeppan9:
11/13/22
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Thanks newpieguy09
madmalc:
11/16/22
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It had to end this way. Great stuff, I think k I need to find a therapist!!
Deeppan9:
11/16/22
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Thanks for the feedback Malc. And yes I think there was only one way to conclude this series.
Aero__:
12/6/22
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Nice conclusion Thanks for sharing these. Are you going to cross polinate any of these? Sofia (From Anyone's Stooge) could be a fun one to meet up with another one of your characters.
Deeppan9:
12/6/22
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Thanks Aero__. I have considered "cross pollinating" my Humiliation for Hire series with an older standalone story and might do so next year. In the meantime I am working on a sequel to Anyone's Stooge so there will certainly be more of Sofia
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