Jimmy's Pillow - Patreon Exclusive Preview

[Elfy]

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Jimmy is a young man with an unhealthy attachment to his pillow. His parents have tried everything to wean him off the infantile obsession before he goes to college but it has been to no avail. With desperation they turn to a very third party with a very unconventional method of altering behaviour.

This is a 37,500 word story that is sexual in nature and full of humiliation!

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“Can… Can I have my pillow now?” Jimmy practically whispered. He wanted it not only for his mental wellbeing but also because it would cover him up.

“Of course.” Nanny Jade smiled as much as her stern face seemed to allow, “You just have to get in the crib for me.”

“But… why?” Jimmy couldn’t keep the whine out of his voice.

“Because I said so.” Nanny Jade raised her eyebrows, “Do you need another reminder?”

Jimmy could feel the stinging in his rear end suddenly rise at the recent memory of his punishment. He looked to the door and wondered if he could run away, even if he could he knew he had nowhere to go. He was now naked and he was still without his pillow. He knew he couldn’t leave the house without his emotional crutch.

“Could you turn around?” Jimmy asked the Nanny. His eyes flicked down to his crotch as an explanation. He didn’t know what reaction he was expecting but he had hoped the Nanny wouldn’t bark out a laugh like she did.

“You don’t have anything I haven’t seen many times.” Nanny Jade chuckled.

Jimmy turned around and awkwardly tried to keep his genitals covered as he clambered over the edge of the crib to lay down on the mattress. He put his head on the pillow and immediately saw Nanny Jade walk over. She looked down at him and Jimmy was reminded of a shark looking at their prey.

“Now I’m just going to strap you down.” Nanny Jade said almost conversationally, “There’s no need to worry.”

“What’s happening?” Jimmy asked. He was still covering his genitals as one of his ankles was taken and put through a leather strap, “Why are you here? Do my parents know what you’re doing?”

“I’m here…” Nanny Jade grunted as she tightened the leather strap around Jimmy’s ankle and started repeating the process with the other ankle, “Because your parents are worried about your behaviour and have hired me to change it.”

“My behaviour?” Jimmy frowned and looked down as his second ankle was cuffed to the corner of the crib.

“The pillow.” Nanny Jade, “They think you need to grow past it. If it helps, I’m of the same opinion. You’ll thrive without it and I look forward to helping you on your journey.”

Jimmy couldn’t believe any of this was happening to him. His parents had hired this crazy woman to wean him from the pillow and then left him with her. They said they would be gone for a week and Jimmy had no reason to suppose that Nanny Jade wouldn’t be here the whole time. He could see his pillow lying on the edge of the changing table, even now he wanted to be reunited with it more than anything in the world.

Jimmy’s left wrist was taken and moved above his head and towards the corner of the mattress. It was put through another leather loop which was swiftly tightened. It left Jimmy with just one hand to cover his modesty.

“Please, you don’t have to…” Jimmy started but his voice choked to a stop when the Nanny grabbed his second wrist.

Jimmy whimpered as his right hand was pulled away from his dick. It was lifted above his head leaving Jimmy completely exposed. He could feel his face flushing an even darker shade of red and he felt so embarrassed his heartbeat was pounding in his ears. Jimmy was now tied to the bed in a star position with each of his limbs pointing at a different corner. This was not how he imagined his first time naked in front of a woman would go.

“Now I did promise you your pillow.” Nanny Jade said as she turned and walked across the room.

Jimmy watched her walk away and despite everything he noticed how her hips swayed to and fro in her heels. He saw the authoritarian woman pick up his beloved pillow and bring it over to the bed. Jimmy nearly gasped from relief when the pillow was laid out on top of him.

“So Jimmy, I want you to yell me what sort of person walks around carrying a pillow or a blanket or a teddy bear as a security item.” Nanny Jade said as she placed her hands on the edge of the crib and loomed over the helpless man.

Jimmy couldn’t have blushed anymore which was probably a good thing since he thought his skin might permanently stay red if he could. He knew what Nanny Jade wanted him to say because it was the same taunt he had heard all of his life. He still found it impossible to give her the answer though, he simply averted his eyes and focused on feeling the smooth pillow against his body. It was the only comfort he had at that moment.

“Maybe I’m asking too much of you.” Nanny Jade finally said after an uncomfortably long silence, “But I’m sure I’ll get the answer out of you sooner or later.”

Jimmy’s attention was brought back to the Nanny as she took the pillow from his body and slipped it underneath his head as if he was going to sleep. He was embarrassed that his penis had swelled up a little from feeling the pillow against his naked body. He knew it was just a physical reaction to feeling the pleasant smoothness against his sensitive body parts but he hated it. His pillow was an innocent talisman of safety, even feeling himself getting a little hard felt like a defilement of it.

“Until you can tell me which group of people carry around pillows I will give you some clues.” Nanny Jade said as she walked away to somewhere behind the headboard of the crib.

Jimmy pulled on the straps searching for a weakness. All four of the restraints seemed incredibly secure and he had very little room to move. He could hear noises behind the solid headboard and wondered what was happening. The pillow under his head provided some comfort but the extremely unusual situation made him feel very uneasy.

“Here you go…” Nanny Jade said as she walked back to the side of the crib.

Jimmy just had time to turn his head and look at the Nanny when something rubbery was thrust towards his face. He reacted with a gasp and found the amber material pushed past his lips. As he felt a cool sweetness drop on to his tongue he realised what was happening.

“Ungh!” Jimmy tried twisting his head away from the Nanny.

“Be a good boy and drink your milk.” Nanny Jade said with her patented smile that didn’t reach her eyes.

It wasn’t like Jimmy had a choice in the matter. His limbs were tied down and the latex teat of what he now realised was a baby bottle was pressed firmly between his lips. He couldn’t even turn his head to the side with Nanny Jade holding him in place. He tried to resist as the milk dripped out on to his tongue but as his mouth filled he was forced to swallow. As his mouth cleared of milk he squeezed the latex with his lips squirting more liquid into his mouth.

With a moan of frustration Jimmy sucked on the bottle to empty it of milk. He knew this stubborn Nanny was going to stand there until he finished so he wanted it to be over as soon as possible. He sucked down the milk and tried to avoid Nanny Jade’s piercing eyes.

“There’s a good boy.” Nanny Jade said encouragingly, “Is this giving you a clue as to my question?  Who carries pillows or blankets around with them everywhere?”

Jimmy refused to communicate. He didn’t want to give the Nanny the satisfaction of getting what she wanted. His face was still burning red as he finished the bottle. The sound of air coming through the nipple caused Nanny Jade to pull it back out and place it behind the headboard.

“What are you going to do to me?” Jimmy asked hesitantly. He wasn’t sure if he wanted to know the answer to that.

“I’ve told you, silly boy.” Nanny Jaded shook her head, “I’m here to break a bad habit. I have one week to do it.”

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“Looks like you’re ready to go again.” Nanny Jade said softly as she continued to use the edge of the pillow to stimulate Jimmy.

Jimmy was too embarrassed to talk. He couldn’t see his crotch with the pillow in the way but he could feel his organ straining to get hard again. He didn’t know what was causing this reaction. Was it just the physical sensation of the pillow on his naked body? Was it because he was being dominated? Was it because his love of the pillow went far further than he ever thought? Was it simply because Nanny Jade was hot?

“Such an excitable little boy.” Nanny Jade whispered throatily.

Jimmy was not a very sexual person and yet he found himself clamouring to be touched again. He was extremely confused and torn between wanting to hold his pillow and wanting the Nanny to play with him. There was a battle raging in his head because he already knew that the Nanny would almost certainly incorporate the pillow and he didn’t want to end up spurting on it again.

Jimmy jumped as he suddenly felt a hand on his dick. He looked up at the Nanny in shock, she was just looking back at him and smiling. Jimmy blushed as Nanny Jade gently rubbed on his engorged organ. His penis ached slightly after being stimulated not long before but any miniscule pain was swallowed by the waves of pleasure that Jimmy just couldn’t deny.

Nanny Jade turned the pillow so the face of the cartoon bunny printed on it was pressed against the tip of Jimmy’s dick. As she slowly tickled her hand up and down Jimmy’s shaft the other brushed the top of the penis with the soft pillow. She could see she was having the desired effect on the young man. Jade knew how men’s minds worked. She knew that Jimmy was fighting a losing battle with his hormones.

Jimmy moaned through gritted teeth as he felt pre-cum starting to smear across the pretty picture on the pillow. He was still thinking about the first time he had stained the pillow, now he was doing it again. The innocence of the pillow was being shattered. With the loss of innocence a new feeling was filling Jimmy’s mind, an almost sadistic thought clouded his mind and came down like a fog. The pillow’s innocence was gone forever and now Jimmy was expressing his devotion in a very different way.

“Tell me who carries pillows around all the time.” Nanny Jade said.

Jimmy couldn’t bring himself to give the answer the Nanny wanted and as long as the domineering woman continued touching him he wasn’t going to say anything that might stop things. The Nanny was picking up speed and Jimmy was soon moving his hips again. Pillow or no pillow he was lost to the pleasure running through him.

The pillow that had been rubbing the head of Jimmy’s cock now tilted downwards. It was wrapped around Jimmy’s member as Nanny Jade used it as a makeshift fleshlight. The sensitive nerves covering Jimmy’s genitals were now excited on all sides by the gentle caress of the pillow. Excitement was practically pouring out of Jimmy now, the clear sticky fluid soaking into the headrest.

As the last of Jimmy’s rational thought was subsumed by his need he no longer saw his childhood pillow, all he saw was a bunch of cloth to soak in his orgasm. The bunny picture he had snuggled against all his life was now just a target. In the throes of passion Jimmy let go of his childhood love to enjoy the pillow in a much more adult way.

Jimmy’s hips started bucking as his fingers and toes curled. His eyes were tightly closed as he writhed. He was reaching the edge, he was about to jump off a cliff into a sea of pleasure…

“Not just yet.” Nanny Jade quite suddenly stopped. She pulled the pillow away and stood back from the crib.

Jimmy’s eyes shot open as all the sensation suddenly left his dick. He looked up pleadingly at the Nanny as he thrust his hips into the air begging for friction that didn’t exist. His dignity had deserted him, he just really needed to be finished off. He could feel his tool twitching and throbbing. To be so close to finishing and then denied felt beyond cruel.

“Please…” Jimmy pleaded in a desperate whimper.

“You seem very keen to cum on your beloved pillow.” Nanny Jade taunted as she held the pillow up.

Jimmy whimpered. He could see the snail-trail on the surface, the remnants of his natural lubrication smearing the happy bunny. His face burned red as he realised how he was acting. He couldn’t stop himself, he needed more stimulation!

Jimmy felt so conflicted but as Nanny Jade wrapped the pillow around his dick any thought of preserving the sanctity of the object disappeared. He was sure he had never been this hard before and even feeling the smooth surface of the pillow was nearly enough to make him finally climax.

“Doesn’t this feel like a better way to enjoy your pillow?” Nanny Jade asked as gently clenched one finger after another. The variable places of pressure caused Jimmy to jerk about in his restraints.

Jimmy was thankful that the Nanny didn’t seem to expect an answer because at this moment of desperation he wasn’t sure how he’d answer. He gingerly pushed his hips up forcing the pillow to rub against him, he bashfully looked at Nanny Jade hoping she would continue to pleasure him.

Looking down at the pillow that now obscured his crotch Jimmy saw Nanny Jade’s hand starting to move and he immediately let out a moan. His inhibitions and embarrassments were now completely eclipsed and he moaned brazenly. He let Nanny Jade know loudly how much he was enjoying things. From the way Nanny Jade’s hand moved he knew she was going to keep going until he came.

Jimmy’s pillow fleshlight rubbed insistently on his dick. His moaning and thrusting became stronger and stronger, it wasn’t long until Jimmy knew he was on the way to an orgasm and his breathing became shallow.

Nanny Jade watched Jimmy’s face intently and then right at the last second she pulled the pillow away. For the second time Jimmy was denied the orgasm his body craved. He looked down in disbelief that he would be teased this away. His tool throbbed in the air, clear liquid running down it’s length. He threw his head back against the pillow in frustration. It was as if his penis was a beacon now, all Jimmy could sense seemed to come from his dick whilst every other nerve faded into the background.

“Not yet.” Nanny Jade said with a knowing smile and a sing-song voice.

In that moment Jimmy hated the Nanny more than he had hated anyone. His frustration at being trapped on the bed, played with and left blue-balled was clouding every sense. As his horniness receded a little he started thinking more about what he had almost done with his pillow and felt shame. He couldn’t believe the object that had grown to mean more to him than anything else became just something to hump against that easily.

“Now then…” Nanny Jade looked at the pillow and it’s increasing number of stains, “Let’s get you ready for the night.”

“What do you mean?” Jimmy asked, “You can’t just leave me like… this.”

Jimmy pointedly looked down at his crotch. His penis, engorged with blood, was still standing proud and waiting to be finished off. He felt so sensitive that even small breezes caused by the Nanny moving the pillow threatened to send him over the edge.

“Of course I won’t leave you like that.” Nanny Jade chuckled.

Jimmy smiled and put his head back. He was endlessly thankful he would get some relief from his sexual frustration. He let out a deep breath and waited to be finished off. He didn’t pay any attention to what the Nanny was doing and didn’t even find it immediately suspicious when he had to lift his backside so the pillow could be slipped underneath him.

“Wait!” Jimmy only belatedly realised the pillow was being pulled up between his legs again.

“You don’t want to make a mess of your sheets.” Nanny Jade said as she reached for the tape.

“My sheets?” Jimmy was shaking his head, “What do you-”

“Come on, sweetie. You’re going to need the potty sooner or later.” Nanny jade was wrapping the tape around the diaper to hold it in place again.

Jimmy could feel the head of his penis poking up beyond the pillow’s frilly edge. It was still swollen as it was pressed against his belly and as the soft pillow was placed against him he felt his excitement rising again. It was like the presence of the pillow alone was enough to get him excited. He felt so close to the edge as he lifted his hips to create movement against the soft pillow.

“I imagine that if I just do this…” Nanny Jade reached forwards with a hand, “We’ll have some interesting results.”

Jimmy was squirming as the Nanny reached out a couple of fingers and tapped gently on the underside of the head of Jimmy’s dick. She was right, it was just the push Jimmy needed.

Jimmy gasped as the sudden touch combined with Jimmy’s pillow humping caused him to suddenly spray his milk over his belly. He grunted as Nanny Jade’s fingers quickly withdrew leaving him writhing and desperately trying to continue his orgasm. His cum landed in splotches over his tummy. His mostly ruined orgasm serving to leave him almost immediately more frustrated.

[diaper24/7]

Will this be posted on here to?

[Elfy]

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