Part two of our little incursion with Nathanael, look into the comments for the previous parts.

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Opening up the cabinet, Nathanael saw Nicole take out two black latex gloves, and put them on. Remembering what happened last time disposable gloves were in play, he tried to escape from the bench, almost instinctively, before another quick smack brought him back into line. Parts of his mind were screaming at him to run, to hide, to do anything but lay here and take it. Another, more and more growing part was looking forward to this, looking forward to having h9is ass played with and maybe even wanting to please his handler.

He wasn’t a sissy, right? He just did not want to get spanked anymore, right? Shit, why did the cage seemingly shrink and become so much smaller, so much more restrictive. He saw the evil smile on Nicole's face in the mirror, as she lubed up first her fingers, and then two other items carefully kept out of view from his perspective. What was that? His mind raced with the possibilities, but came to a screeching hold as he felt her fingers push into his ass. She did not warm him up with one, she pushed them both in, insistently forcing them in as he tried to keep his muscle tight, tried to keep her from doing like she wanted with him, but the pain split through his conviction.

“Relax it, and it won’t hurt as much. You will feel like a good sissy and understand why it feels so good to obey. Now, open up!” The command at the end, with the pain in his cheeks and the splitting pain from fighting against the fingers triggered something in Nathanaels mind, and he relaxed his ass.

Smiling, knowing she has him now, Nicole started to push deeper, as Nathanael felt her hit that spot with her fingers. That beautiful spot, that had started all of it and got him into this position, he felt pleasure radiating from his ass and felt the shiver run up and down his spine. The thoughts melted under the pressure, it became so much harder to think straight and with every moment, every move and curl of NAdine’s fingers, he was more unsure, if he wanted to.

The world seemed to swirl around his head, and without truly realizing it, Nathanael opened his mouth and began panting, his tongue out from his mouth. Nadine always loved those glazed over eyes in the mirror, the heat and insecurity of a femboy not knowing how much pleasure his ass holds for him. Oj, how much she looked forward to having that tongue lap obediently at her cunt, but for today she had other plans for it.

She intensified her efforts, and Nathanael started to lose all sense of things around him, getting turned on by whomever was looking so damn in pleasure right there in front of him. His mind was just so foggy, and his ass felt so good. His cock-sage felt as if it was shrinking by the second, pulsing against his cock. As Nicole withdrew her fingers, he started to mewl, wanting more, needing more! He felt his ass stretch, as Nicole took the prepared dildo and shoved it deep into his ass.

Nathanael saw her lift up the rubber cock for a moment, saw it in the mirror, but he was beyond caring. If it would hit that spot, fill him up and make him feel good, he wanted it! Not able to really form any words anymore, he just let out a deep moan, as the cock pushed his ass wide open, doing his best to relax and get it deeper, needing it deeper, just a little bit more!

There it was! As the rubber cock hit that magical spot, stretching him and filling him, Nathanael panted, moaned, spit running from his mouth as he fought against the shackles, not to escape but because his body wanted more, needed more, could not handle this pleasure laying down. He felt like a puppet with his strings cut, shaking in the wind, quivering and shaking but at the same time feeling like he could not control any of his limbs.

Nicole started to push and pull the rubber dildo, fucking Nathanaels ass with it. Soon, it moved freely in and out, and his moans now came in the rhythm of her movements. “I think you need something with a little more force behind it!” Unbeknownst to him, with her other hand she had put the second item she had lubed upü onto her hips: An Even bigger strapon. “Now, be a good boy and open wide for me!”

Nathanael barely registered the words, all his mind could comprehend when the dildo was pulled from his ass was that it wasn’t over. Not, that he wanted it to be. His cock was leaking precum all over the side of the bench, his cum slowly being milked from him. He moaned hard, eyes wide as Nicole in one smooth motion pushed the full 8 inches of her strapon into his ass, stars exploding in front of his eyes, as he felt his ass stretch beyond anything he had imagined so far, as his cock made the cage jump with joy.

He moaned and panted, never having felt so good in his life. As the strapon had fully sunk into his ass, Nicole's hips hit his cheeks, the sensitive skin reacting to getting slapped again with a burning pain, but Nathanael was too far gone to care. It only made the situation more horny, the pain underlying his helplessness. Without fully realizing it in the moment, all he wanted to do right now was to please, to be made to feel helpless and to get fucked!

Nicole gave him all three, fucking his ass hard and holding two fingers to his mouth. She smiled has he obediently began to suck on them. She oh so loved branking her wards, and this one had passed the point of no return, whether he himself knew that yet or not. She took the dildo she had used on his ass and pushed it into his mouth! She could watch him choke and try to lick the cock in the mirror, and it send shivers down her spine and into her pussy, as she started to fuck him harder and faster, slamming her rubber cock into his ass and her hips against his tortured cheeks.

“Now, cum for me!” With a few more fast strokes, she grabbed a hold of his balls and squeezed, the cry of pain and pleasure from Nathanael somewhat muted by the cock in his mouth, as he came, filling his cage with cum and shooting it all over the leather side of the spanking bench. Nicole did not stop though, and continued roughly fucking Nathanael, who screamed into his gag,, loving every second of his, as pure carnal pleasure coursed through him, as his mind was as split open as his ass, as he felt himself getting stretched and the big, fat cock pushed on his prostate, forcing him to moan into the cock in his mouth, tasting his own ass on it while helplessly strapped down to the spanking bench.

He did not care in that moment, cared about nothing but the pleasure and pain, about getting fucked and leaking his cum all over until he would pass out! He already felt his balls clenching, a second orgasm in the mix. With his cock, he had never experienced such pleasure, never been able to reach the heights she forced him onto. The hard fucking of his ass brought him soon to the edge!

Nicole was also enjoying the rubbing of the rubber strapon on her clit, the gagging and gurgling noises from Nathanael, his cum leaking down the bench, as he lay there helplessly in front of her. And above all: Those glazed over eyes, speaking to his lust, telling her how much he wanted and enjoyed it. Pushing the cocks deep into his mouth and ass, she moaned and cried: “Cum with meeeee!”

The command hit Nathanaels brain, and he came came out all the cum in his balls, screaming into the gagging rubber dildo with his muscles quivering against his bounds. The last thing he noticed, before the world went dark around him, was the screams of his new mistress behind him.

As he awoke, it slowly dawned on him, what had happened. He had been fucked, fucked in the ass, and it had felt soo good. He could no longer deny it: He wanted this! He wanted to be fucked like this every day from now on. He looked around and saw that he was lying on the pink bed. As he moved, he noticed there was a dildo gag still in his mouth, forcing him to suck on it, and he felt a plug deep in his ass.

He tried for a moment, if he could take them off, but found the plug was sitting tight in him, without any way seemingly to decrease its size, and the gag was locked around his mouth. Giving up, he opened the door to his closet, to see pink and frills all over the clothing. The true closet of a sissy!

Taken aback for a moment, he felt the plug press on the very special spot in his ass as he moved and moaned into the cock in his mouth. Well, maybe it wasn’t too bad he thought.

As Nicole saw him through the secret video feed give in, saw the look in his eyes as he grabbed the clothes and making the decision to accept his fate, she paused the video, pressing a button on the remote on her lap she knew would give her ward a nice little vibrating reward in his ass for a moment for being such a good boy.

She pushed her hand into her panties, as she studied the image of him on the screen, memorizing it. She would have so much fun with this one!

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I hope you enjoyed this next part in the journey of Nathanael, finally resolving that mean cliffhanger. I might get onto a different story next for a bit, but don't worry, updates for this are still to come! As always, feedback is appreciated, if you want to give it. I hope you have a lovely day ;)