Stories Of Moon 2 (A Moon Story)
- 5 months ago
- 13 min read
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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?"
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 before he got too distracted by tools and toys and whatever was bothering him.
He managed to flop down on the bed, and they wrestled for a bit before he slipped between her thighs and began kneading her breasts while kissing her nipples. With lube and her Hitachi Magic Wand, he worked up to caressing and playing with her swollen lips and tender clitoris until she was moaning from the throbbing that started within her pussy and tingled all the way to her chest and toes. His fingers slipped into her moist sex, adding more lube with each thrust into her opening, and she clenched down while arching her back in response to his persistent urgency. Heavy breasts shuddering, gasping becoming panting, the firm silicon pressed into her pussy and the ridges grabbed at her labia is he pushed it deeper.
For a moment, she considered changing her mind as the tender folds of her lips were strained and tormented by the unyielding shaft. Then the dildo fit into place, the shaft lurching into her sex as the slightly wider circular base sealed her opening, and her legs kicked as the broad head of the Hitachi rumbled against the silicon and made the short shaft quiver and shake within her pussy. Her orgasm was almost immediate, and she had to push his hands away because she couldn't catch her breath while her abdomen was still seizing and clenching.
He seemed quite pleased when the black dildo didn't come out and used the wet wipes and towel to clean her pelvis and blot her dry. She would have complained about him pulling the harness on if she had the energy to do so. Instead, she was limp in his hands as he gently lifted and fit the straps around her waist and pelvis before cinching them tight enough to cradle her sex. When he stretched out next to her, he seemed happy with the progress only he kept track of while her fingers wrapped around his wrist and squeezed tight.
He had his plans, but she had other priorities. She let him bend her forward over the couch arm and enjoyed the feeling of his strength wrapped around her body while he ground his cock against the seat of her trousers. She reached down and undid her waist button and zipper as best she could while he continued to tug on her hips. Finally, her trousers were loose enough for him to push down, his thumbs hooking her panties as well, and his fingers pressed into the flesh of her round buttocks and thighs while undressing her.
"Are you ready?" he asked gently when he paused to adjust himself.
She moaned through her teeth. She knew that she hadn't done what he asked but suspected that it might be worse to admit procrastinating something so important to him. So, instead, she reached back and pulled her ass cheeks apart despite her lack of preparation.
He could tell from one look that her anus wasn't as lubed as it should be. Each evening that she visited, there were clear rules. She was to strip down, lube her pussy and do twenty strokes with her preferred cock toy to loosen herself up, and then inject enough lube to keep her ass moist for at least the night. Since sometimes Moon put the lube in her ass before coming over, he didn't double-check that part. At moments like this, she inadvertently made him doubt her interest and doubled down on the feelings of rejection that her behaviour inspired. He imagined that she couldn't help herself. She generally just drifted or avoided things that didn't immediately pay off with a tangible result, and her natural urge to rebel against anything pushed him away emotionally while she complained about his distance.
At least he could be proud that she didn't shirk her promises. He tried to focus on that, keep it top of mind, instead of being disappointed. As his assistant, she was supposed to be prepared to provide her ass and pussy for fucking and playing with at any time that he asked for it. The benefits of her status were not to be understated, but he knew that he asked for a lot in return. The right answer might have been to spread her ass cheeks and ask him to wet her first, but, by spreading her ass cheeks without resistance, she at least lived up to her commitments.
He didn't have any lube nearby so he wet his fingers in her pussy and stroked the slick juices over her puckered opening. His voice was quiet and calm as he whispered, "If you keep forgetting then I will be forced to start dry fucking your ass." He didn't like punishments, but there was a fine line between unprepared and taking advantage of the fact that he didn't check up on her promises.
She nodded. She could feel his lust diminishing as his urgency to fuck her cooled and he dealt with her state of unreadiness. She went out on a limb. "Then dry fuck my ass so I don't forget." She paused and added, "Please."
The condom unrolled over his cock with ease, though his shaft was sagging. He stroked her wetness over the latex sheathe and fitted the head of his cock to her ass. His glans would squeeze in, but it would be an effort to push through her tight sphincter. "If," he said as he began to test pressing his glans into her barely damp anus, "you insist on being dry fucked like this then we're going to have to open your ass more so it's an easier fit."
Her fingers turned white while she pulled hard on her buttocks while feeling her tender skin catch and the sudden ache and burning between her cheeks as his cock head pushed past her anus. "Yes," she said controlling her breath. "Yes, a bigger plug..."
He left his cock with just the head and an inch of the shaft inside of her clenching bottom. "How big of a plug?" She shivered when his cock pulsed while gripped by her tight pucker.
It was a tenuous balance, the pain and ache, the throbbing of his pulse and heat of his cock, the familiar longing and complaint of her openings. She willed herself to relax. "As big as you want." His cock twitched, and she enjoyed his arousal despite the seething burning where her sphincter was stretched without the lubrication needed to soothe the sensitive pucker. She could tell by his reaction, by knowing him, that he'd want a huge plug in her ass as often as possible. "How big would you want, Sir?" His cock double pulsed.
To her surprise, he slowly withdrew from her ass. Then he buried himself in her wet pussy. His strong hands ran up her sides and he ground his pelvis into her buttocks. He tipped upward with his pelvis, guiding the root of his cock to press against her tailbone, and his shaft throbbed alongside her spine while his scrotum rubbed against her wet lips and her clitoris. He sighed as he enjoyed the relaxed fit of her pussy around his cock and wished that she understood that her ass wouldn't suffer so much if she took the time to slowly open it for them to enjoy.
She pushed back onto his pelvis while working her vaginal muscles to milk and squeeze his cock. "This loose? A plug that would make my ass feel like my pussy? Or just the opening of my sex, all open and wet for you?" She knew what he wanted. It just wasn't as easy as getting up and masturbating on a whim. She preferred him there, his fingers inside of her, and his lust guiding her body to orgasm. On her own, it was just painful and boring.
He snorted and may have growled. He began pounding her pussy hard, and her thighs were grateful for the cushioning on the couch arm. His persistent hydraulic motion caused her juices to run out of her pussy, and she would have continued to egg him on if she could have caught her breath. Unable to form words, only grunting and panting as he hammered into her sex, she could only communicate with her pussy - alternating between suckling his cock and willing herself to open up and give him plenty of room to press deeper into the hollows of her vaginal passage.
His hands pressed into her long hair, and his fingertips dug into her back. He was fucking her hard enough to dully thump against her rounded buttocks and feel the shockwaves of his thrusts rebound against his thighs and abdomen. He sped up, increasing his pace, and planting his feet while gripping her hips for better leverage. Each stroke of his cock included a spanking as his firm pelvis slammed into her buttocks. His shaft was twitching, and his glans bobbed within her heated grip. One hand seized and pulled on her hip, and he was tugging her backward so her wet labia were crushed against the root of his cock while he continued to grind into her pussy hard enough to push her rounded buttocks apart. When he orgasmed, she was surprised - usually he was too reserved to shoot during an ad hoc fuck.
He smiled when he leaned over her and kissed her shoulders. "You say such wonderful things," he murmured. And then he slipped out and blotted her juices, tugged up her trousers, and turned her around so he could hug and caress and kiss her in his arms. She was left feeling her wetness pooling in her panties and craving more. He was left hoping that she understood exactly how big he wanted her anal plug to be.