Stories Of Moon 2 (A Moon Story)

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Being his assistant was more demanding than just being one of his lovers.

Setting aside the leather harness as she sat down on the bed again, he shook his head and walked over to his sex toy drawers. When he returned, he handed her a thick and squat black silicon dildo with deep grooving on the sides for her to look over. The rounded head and smooth surface of the material contrasted with the squared off edges of the shaft's furrows. When she was done rolling it back and forth between her hands, he offered her a second dildo. This one was long and fleshy, a pale skin tone shaft with a slightly pink glans, and it was clearly meant to be a man's cock despite the overt thickness and length. It bowed in her hand as she squeezed the two toys to compare their firmness. She set the shorter black dildo down and stroked the length of the phallus before swapping to explore their surfaces with her fingertips. The black silicon was blatantly rigid and inflexible, and it promised to be very demanding. The realistic cock was flexible enough to slightly crush in her hand, but it was clumsy and constantly moving due to its length and weight.

She was thinking through how they might feel against her lips when his persistent gaze interrupted her thoughts. She looked up to him, and he smiled with a nod. "Choose," he requested.

He usually wore his moods on his sleeve, but he'd been holding back something all day. She knew him well enough to be cautious of his request. "Why?" she asked slowly and deliberately while determining if it was something that she had done or just something that he needed.

Gesturing with upraised palms, he reiterated details that he'd been whispering to her for weeks while she was in the throes of orgasms. "For the next couple of months, we will train your pussy to perceive one of these as the cock it prefers and craves." He shrugged. "We'll keep going so when you handle a cock, when you feel a cock in your sex, when you see a cock... then you will compare it to the pleasure and sensations of the toy that you choose today." He was being completely logical which was never a good sign.

She took the time to examine the toys again, setting them side by side and noting the differences in their thickness and lengths. Her hands caressed the surface of their shafts, and she knew that it would be easy to immediately tell them apart even in the dark. Despite its more jagged shaft and thicker girth, she judged the black silicon sex toy to be much easier to start with than the long soft cock. Mostly decided, but pondering his state of mind, she looked up asked, "How?" He liked explaining things, and it was a good chance to uncover his motives and expose the emotions that he was suppressing.

He pointed toward the harness that they had been fitting to her pelvis and hips earlier. "The plan is to have you regularly fuck and wear the dildo you chose. With orgasms as rewards, frequently playing with your cock comes with great incentives. The harness will hold it in place so you can also enjoy it thoroughly and passively while you're home. We'll keep working on your double penetration training but with your cock in your pussy and me in your ass. We've made good progress and will keep pushing forward on hollowing out your vagina, but with your cock inserted before and after." He stepped closer and sighed while running a hand over her bare thigh. "Open, wet, and fucked, my lovely assistant. And using one of these will assure me that you are being fucked properly and often even when I'm traveling."

She suspected that he wasn't be honest about his intentions. Despite occasional requests to know what she was enjoying while he was working in other cities, he didn't really seem too concerned about her other male partners so long as it didn't interfere with his fun. "Do I have other options?" Sometimes he was very inflexible, and she wasn't always clear why. Maybe this was just a test of some sort.

His smile turned into an evil Cheshire grin. "Of course."

Something about his response provoked her. "What are they?" She set the toys aside and squared her shoulders. Despite her soft curves and heavy breasts, she wasn't a pushover and didn't play along with every whim and scheme that he came up with.

Studying her defensive posture, he relaxed and offered his answers. It wasn't implausible that she might go for one of them, but she had so many boundaries and rules that this was the only way to start clearing the logjam that blocked her from a more fulfilling sex life. "We can train your ass instead. Or we can go ahead and train your mouth for cock. Or we could prepare and maintain your ass for fisting. Or we could fit your sex with a collar to hold it open. Hmmm... I like those last two a lot." He could be honest. Her rejection was largely a given which is why they were having this discussion even though she wasn't self-aware enough to realize that.

Shuddering at the thought of more painful anal play, she pushed the longer realistic cock toward him and let it sink into the bed. He was angry about something, or possibly just grumpy, but his plans weren't something that he'd negotiate over without good reasons. He would let her bail, put things off, but then he'd be irritated until she decided what to do instead. Her hand reached out and pulled the black silicon cock closer, placing it in front of her legs, and she made her decision clear.

"That's the one?"

"Yes."

He seemed content with her answer. "Good. Let's start by lubing you and fitting it in." She supposed after all the work on the leather harness that his desire for a result was to be expected. He went to work, bringing over a soft towel and wet wipes as well as a pump bottle of Liquid Silk, and she just watched him in motion. Somewhere, deep inside, he was broken. With a sigh, she pulled some pillows together and beckoned for him to kiss her breasts and cuddle her

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Written by Cherish Desire
Uploaded October 29, 2020
Notes Lubed and ready are requirements that come with being his assistant. Ian needs to remind Moon that his expectations are as real as his arousal.

Themes: MF, Vaginal & Anal Sex, Fingering, Stretching, Dildo Play & Wearing, Vaginal Penetration
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