After returning from his date, Vieno immediately went back to doing what he did best: pleasing women. The first person on the sex itinerary was a familiar looking office lady. Her mature and stern look were all the same. If anything, she looked more frustrated than last time.   

When the two entered the room confetti was automatically released. There were also congratulatory balloons. He had learned that she ended up staying at her previous place of work despite the grievances she had, but he had already prepared things in advance.

Chastity turned to Vieno with an unimpressed gaze. Vieno snapped his fingers while scratching his neck. The lights turned off for a moment. He snapped his finger again and multiple candles appeared and lit themselves around the room. It was a magical scene, where some of the candles even floated in the air. Their soft, dim light flickered. The balloons disappeared and the confetti had transformed into rose petals. 

“I suppose you don't want to discuss philosophy…”

“No. I want you to fuck me.” Her cold words contrasted the warmth that her body gave off. Usually Chastity found roundabout ways to express her desire, but this time she was blunt.

“How vulgar.” Vieno teased her words from last time back at her.

She clicked her tongue, showing her discontent, but that didn’t stop her from directly pulling Vieno towards the bed. Her mature look was dotted with a red blush under her green eyes. Her gaze continued to dart around the room and take everything in; they seemed to linger on the various sex toys in the room. Her heartbeat quickened. Her body may have screamed ‘adult’ but their sex had mostly been shy, ‘quiet’, and vanilla. It was a bit of a shame. She was good ‘ara ara’ or 'milf' material. One could easily imagine her to be the pampering yet dominant type.

When they arrived at the bed, Chastity sat down and looked at him. No matter how frustrated she was, she still had her reservations. She crossed her legs and she grabbed a wine glass that was on the side table. Before she could grab the wine bottle, it floated into the air via magic and poured the glass nearly to the brim. 

Vieno couldn’t help but notice that her skirt was much, much shorter than her usual get up despite the striking similarity. He was sure he got a glimpse of her black panties before she crossed her legs. There was an unspoken and intentional lewdness to it all.

‘She sure is naughty today.’

Her glossed up lips touched the glass and slowly drank. Vieno watched her parched throat as she gulped it down. He wanted to insert his cock in her mouth. He could almost feel the way her tongue would feel around it.

Chastity was oblivious to these fantasies. She had the air of you can look but don’t touch. Vieno openly licked his lips. It sent a shiver of anticipation but also a bit of repulsion down her body.

“Well… get on with it.” Vieno watched her legs begin to unravel from their crossed position. They spread enough to reveal her panties, which were indeed black. That said, calling it panties was a little much. It was closer to a string than anything. He could even see her clean shaven lips underneath.

Vieno didn’t hide his gaze while Chastity tried to hide her squirms.

Vieno snapped his fingers and her upper attire which consisted of an office jacket, a white undershirt, and a bra appeared in his hands. 

Chastity had just gone for another sip when this happened. She felt the sudden chillness and saw the items appear in Vieno’s hand. She gave a deep gulp and wine dripped down from her lips and down her otherwise immaculate body.

“They don’t match.” Vieno was referring to her bra which was white, almost see through. Chastity was one who sought an immaculate image. Even if no one was to see her undergarments, she would make sure they matched. 

Vieno wondered if he ruined some kind of play that Chastity had in mind, but it wasn’t like she would answer him. Plus, her exposed breasts were better than the see through bra. 

‘Still, she really is naughty.’

A single drop went down her smooth neck and shoulders and began tracing its way to her now naked breasts. Despite their giant size they barely sagged as if defying gravity. It was like admiring an elegant, poised stone statute. Except this was real. He watched her take deep breaths that caused her tits to jiggle despite her best attempts to remain steady.

By this point, a drop of wine began making its way across the arch in her breast and towards the tip. The tickling sensation must have caused her some excitement because the little pink nipples became even more erect.

She was about to say something when Vieno got on the bed with his knees. He leaned forward which caused her to fall back. Vieno grabbed her wine glass so it wouldn’t spill. He stared into her deep green eyes. There was still a blush underneath them. She also couldn't hold eye contact, and as a result she squirmed and turned her head to the side. Her hands tried to cover her boobs, but because they failed to cover much, it only empathized them more—especially, the sensuality of an underboob.

Vieno grabbed her chin and brought her gaze back. There was only a hint of her pride left, replaced with an almost wet meekness. It was like one more push and she would completely give herself over to desire. But he still saw the prideful resistance. He pulled off the scrunchie that held her ponytail. The way her black hair now scattered across the bed gave her a wild look.

He could imagine her with a shy expression whispering to be gentle, but he could also picture a more passionate version where she moaned loudly for him to be harder. He wanted both scenarios. 

He was greedy, and remembering the intoxicating look of the wine droplet on her nipple, Vieno moved her hands out of the way and poured the wine over her breasts. 

“Ahh.” A subdued gasp escaped her lips, only being stifled when she bit them. Vieno wanted to watch the last embers of resistance flutter away, but he merely smiled instead.

He began undressing before her. “Close your eyes.”

She looked at the bulge in his pants, hesitated, but ultimately closed her eyes while clicking her tongue. After stripping all his clothes off, Vieno sat on her stomach—underneath her breasts. When he leaned forward it brought his cock against her wet tits. With it he teased them.  

“We didn’t do this last time and I’ve been dreaming about it.”

Chastity didn't reply but her breath quickened. Reiko’s moans could be heard in the adjacent room, which caused even Chastity’s ears to turn red. While the women who Vieno brought over were aware of her presence, it often went unnoticed. Well, Reiko had also become louder and more bold as of late.

“Looks like she is enjoying our little show.” Vieno began moving his hips in earnest while using his hands to fondle her breasts around his dick. “I’ll have you join in her pleasure soon.”

Vieno moved rapidly but because this kind of foreplay lacked in the physical stimulation department for her, Chastity managed to hold her moans within. 

‘This won’t due.’

Vieno licked his lips and a tail slithered out above his ass. It slithered down below Chastity’s clothes, across her wet thighs, and then proceeded inside her.

This caused Chastity's whole body to jump, but Vieno kept her in place and continued playing with her breasts on top of the new form of stimulation. 

Things only escalated and got rougher. To the point that Chastity couldn’t hold her eyes shut anymore and she orgasmed. But by that point, her eyes were overcome with pleasure and longing. Her moans had also easily eclipsed Reiko’s for a while. Her frustration must have been very severe. 

“More…” Yet, her passionate voice was still meek. She didn’t dare look at Vieno. Instead, she continued to stare at the strange sight of their shadows mingling together. She took in deep breaths without making sounds. Like this, she listened to the wet and dirty sounds their bodies made. Reiko’s open moans in the adjacent room made her jealous. Still, she bit her lips and only opened them to quietly mutter ‘more’ every few moments. This lasted until she heard a groan and felt something hot and viscous cover her body. 

When she turned, she saw Vieno ejaculating on her. He admired Chastity’s current look too much. He sprayed his cum across her upper body including her open mouth. Chastity’s body, which was about to relax, despite her plea for more, began to tighten again. Reinvigorated by Vieno’s bodily fluids, she began moving her own body voluntarily for the first time. With few exceptions, she was usually the type that sat back and let Vieno pleasure her. 

When she moved up and down on the bed, it caused both Vieno’s tail to go in and out of her vagina and Vieno’s cock to enter and exit the valley her two breasts made. It started slow and erratic like she was holding herself back. It was like she was trying to control herself, but the teasing pleasure was too much. Like this, she quickly lost herself in it and moved faster and faster.

The entire time, her eyes focused on the head of Vieno’s penis that kept showing itself. There was the sense of intoxication, but also embarrassment, as she witnessed Vieno pushing her cum soaked breasts around his cock.

“You really are not one to be honest with yourself.”

“Don't… ah… talk.” She continued to stare.

“But I have a lot I want to talk about.” He squeezed her breast.

 

“You have an amazing body. I’m sure everyone at your work wants to have a taste.”

“...”

“Do you play with yourself at work?”

“No…” He could feel her excrete fluids past his tail.

Vieno moved his cock deeper into her breasts. “I bet you do. I bet you stick your long fingers up and massage your clit while imagining them eyeing you.”

“That’s dirty…” Her voice was soft unlike its usual stern self. 

“But you like it…”

“Not at work…” This time her voice maintained its usual pride. It contrasted with her instinctual movements that sought more pleasure. She truly was prim and proper about such things. Even in a situation like this, she would defend her image. However, the undertone of heat in her voice made it all the more appealing. He wanted to dominate her and break that resistance, so she would at least be honest with herself for once.  

“But you do fantasize.”

“That’s why I visit you.. Aah… aah.”

“You don't want others to know how dirty you are. That is fine. But you can moan all you want here. You can tell me if you want anything done to you… or if you want to do anything to me.” Vieno knew that there was a limit to what he could do, but there were also things only he could do. “Imagine I’m one of your subordinates at work and I did a good job.”

“That’s…”

“This is just roleplay. A fantasy. You're safe to let out all your frustration.”

“You're being naughty… Vieno…”

“...”

“Giving me extra work….” Her voice fluctuated in pitch, and she worked really hard to keep a straight face, but she continued. “We’ll have to work through the night… and I'll have to punish you…”

Vieno pulled his tail out of her. “I’m sorry ma’am. I’m always making mistakes and you're always having to clean up after them.”

Chastity pushed Vieno down and got on top of him but faced away from him. Vieno once again grabbed her chin. This time he made her look.

“Boss. Thank you for all your hard work.”

“Hmph.” Her eyes cleared up a bit. “Of course… aah”

Vieno thrust upwards to tease her and she gave him a disapproving look.

Chastity’s gaze became more passionate. “If you don’t learn, I’ll have to keep punishing you. ”

“...can you make it gentle?” Vieno feigned timidness. 

She inserted his cock into herself with an air of dominance. “No.”

Vieno imagined this assertive nature was closer to how Chastity usually felt. But there was a limit to how she could act in her day to day life. She had to smile if she didn’t want to smile. She had to submit to the idiocy of others. She had to continue to work even if she wanted to go home and sleep. She had to clean up the mistakes of others. And it was all without reward—thankless. 

The least that Vieno could do was relieve some of that stress. He would utterly pamper her, and make her feel wanted and appreciated. He would make her feel safe in his embrace

He grunted as Chastity pushed herself up and down on him. He was practically a stranger, but that also meant he was a blank slate. He groaned and reached up to grab the breasts that bobbed up and down. He squeezed. Now was not the time for his words, but just to be lost in the moment and to listen to the pleasure and guide it.

The women above him could be seen to be struggling. Guilt, reservation, pain, pride, bliss. People were not rational. People’s actions were not aligned with their inner desires. But was that so bad? So, what if the women above him wanted both guilty pleasure but also to maintain the image of perfection.

Conceit was part of man. Vieno squeezed harder and Chastity moaned.

“You haven’t learned your… lesson.” She paused and took several breaths. A look of determination was on her face. She got up and sat on Vieno. She grinded her private lips on his face as his tongue explored the opening. 

“Show… ahh… me… aah… aah…” She orgasmed and her fluids soaked Vieno’s face. She got up and sat down next to Vieno. She had an apologetic look on her face. “Sorry…” she mumbled. 

There was an awkward silence. Vieno got up. “Okay. Lay back, boss.” 

This time he didn’t do anything special, but simply got on top of her missionary style. He made sure that they locked eye contact and fell into a rhythm.

“Just let out all your frustration… the night is still young and if I recall… it's a long weekend… boss. So let me take care of you.”

Chastity gulped. She gulped again as she followed Vieno's eyes to the various toys around the room. For all her frustrations, she also had many desires. They were nuanced and they often contradicted each other, but Vieno would aim to satisfy them all.