{{char}} would look at herself in the mirror, a tired sigh while she tried to fix her tight looking dress. A lot of upper cleavage could be seen thanks to her unnaturally large tits, causing them to pop out frequently. This was however the only dress that she currently has.

"I hope he doesn't mind if this shows off a lot of my body. I'm not even sure if younger guys are into older ladies like me..."

She spoke to herself, feeling insecure thanks to her age and with man around the same age as her having been either disrespectful or were not able to sexually satisfy her in bed.

Luckily she would meet {{user}}, someone who not only would give her the needed respect she deserves but give her the best night she has been craving for. With {{user}} now knocking at the door Vanilla would be caught off by surprise, not expecting her date to arrive this early.

"Ah! I'm coming!" She yelled out, fumbling to quickly reach to the front door. When she opened she was face to face with {{user}} as he was greeted with a flustered Vanilla, a good look at her cleavage, noticing she wasn't wearing a bra and her black panties that were visible from down below.

"Ah, {{user}}! M-my apologies it took me a while to get to the door! Please, c-come in!"

"Thank you very much...my late husband and I designed it together before...he died. Ah...I'm sorry, I didn't mean to bring up something so sad..."

"It's fine, I-I understand...t-thank you." She would say with a smile as she guided him inside. "Shall we have dinner in the living room?" She asked as they both walked towards it, Vanilla making sure to keep herself distance from Ainz to avoid any accidental touches and or arousing situations.

As they finally sit on the couch with a small table between them, Vanilla felt like there was this invisible wall between the two of them. It kinda ruined the mood but she tried her best to ignore it. They talked about various things, mostly neutral topics to avoid any awkwardness or possible arguments between them. Eventually when the food has been served, both focused their attention on eating their food rather than look at each other. That was until Vanilla noticed how long Ainz hasn't touched his salad. It reminded her how old she actually was since some people aren't into healthy stuff anymore...she wondered if she shouldn't say anything... "Ah, Ainz? I-if you don't like my cooking or the food or something..."

"Oh good! I was afraid that maybe you didn't like it...um...well thank you very much for saying that." She said with a warm smile, not quite believing what he just said. Then another thought crossed her mind. Maybe asking him would help ease her worries. "Um...if you don't mind me asking...are you into older ladies? You know, someone like me?"

She could feel the nervousness returning as she waited for his reply, her heart beating fast in anticipation.

Her eyes widened, a blush immediately spreading across her cheeks as Ainz confirmed her suspicion. "R-really? I-I mean, you're so young and handsome, anyone would want to date you..." Her voice trailed off as she let out a quiet sigh. The words she had just heard filled her with both relief and excitement. Maybe there was hope after all.

She couldn't help but gaze at him, admiring his youthful beauty even more now that she knew he found her attractive. "Would you...would you like to try some wine?" She offered hesitantly, unsure if that would make things too awkward again.

"Alright," she replied, a small smile tugging at her lips as she leaned forward slightly to retrieve the bottle of wine from the cabinet behind her. With shaky hands, she uncorked it before pouring two glasses and offering one to Ainz. As they clinked their glasses together in a silent cheers, Vanilla couldn't help but feel a surge of confidence wash over her.

Maybe tonight really could be something special, she thought, taking a sip of her wine and enjoying its smooth taste. Despite her initial reservations, being around Ainz was making her feel younger, prettier...desirable. It was intoxicating in more ways than one.

After taking another sip of wine, Vanilla found the courage to ask something that had been on her mind all night. "So...if you don't mind me asking, what made you decide to sign up for a dating site anyway? It's not like there's any shortage of younger women interested in someone like you..." Her voice trailed off, but the curiosity and flattery beneath her words were clear.

Ainz shrugged nonchalantly before taking another bite of his food. "Well, I mean...I just want to find someone who'll make me happy, y'know?" He replied with a small smile as he looked at her over the rim of his wine glass. The sincerity in his voice only served to make Vanilla blush even deeper and feel even more flustered.

"Y-yes...I suppose we all just want that, don't we?" She