Milly's Date Part 2

Milly had to admit Dante was being far more reasonable than she was expecting. Despite knowing she was very much against being married period he maintained a level head and wasn't taking it personal. Her previous would be suitors were all so easily riled up in comparison if she so much as breathed in a way that didn't suit a noble.

Maybe it was because he'd been going to Ashford for a year with her? The Disciplinary Committee weren't exempt from the events and at least had to dress according to them. So maybe he'd grown used to her antics back then?

Sadly from his words he made it clear that he also wanted this courtship to work out in favor of their eventual union. When he mentioned pride and duty Milly was hard pressed to disagree. Personally she didn't put much stock in her pride as a noble. She wasn't ashamed of it per se but she honestly cared very little for it.

Hell she pretty much used and abused the pride of her past suitors to get out of the arrangements scott free. The thought of admitting they couldn't handle a 'brat not even out of college' was anethema to those old geezers. Going after her and her family would be an admission that she'd gotten the better of them. So with all the dignity they could muster they broke off citing they simply weren't compatible due to her age.

Duty on the other hand was another thing. She did feel rather strongly about that. It was the duty of House Ashford to assisst the Vi Brittania line to the best of their ability. It was her duty as Student Council President to ensure the student body had an enjoyable stay at Ashford (even if a certain _sour puss _of a Vice President called her insane or said she was going over board). It was duty that had her hold her tounge when Claudia arranged these meetings.

Her mood dimmed at the reminder. In the past she really had let her own emotions get the better of her. She'd pratically been spitting in her mothers' face everytime she'd sabotaged these dates. Claudia was certainly strict and a bit of a control freak but she'd never been unfair to Milly. In her own way she'd always shown that she treasured and loved her daughter dearly. She should probably apologize when she got home tonight. Maybe they could take a spa day sometime soon.

So her own personal feelings had no place here. If the courtship broke off it would have to be by mutual choice. That said maybe this wouldn't be such a bad thing. Summer break had just started and classes wouldn't start again until September. Like Dante said it'd be perfectly normal to find herself more attracted to him the more they were around each other. He certainly wasn't lacking confidence if he felt she'd fall for him by the end of August.

At the very least she was enjoying herself around him more than her previous suitors. The pompous windbags treated her like either a child that didn't know anything or some piece of jewelry to go on their arm. He'd even called her 'Milly' instead of 'Miss Ashford'. The casual address was honestly a breath of fresh air from the old fuddy duddy way those old men spoke to her. It was nice that while he may be doing his best to see this courtship to success he wasn't taking things too seriously.

When their orders came and he casually placed her in his lap she was surprised for just a second.

Then she settled against him and became surprised for an entirely different reason.

There was a lot going on in Dante Jackson's lap.

His thighs were firm beneath her legs, his arm was steady around her waist, and his chest was warm at her side. That was all very nice. Expected, even. What was less expected was the thick, soft lump trapped at the front of his suit pants, pressed under her ass in a way that made it quite difficult to pretend she had not noticed.

Milly shifted once to get comfortable.

That only made her notice more.

It was not just a little bump or some vague masculine presence. There was a long, heavy lump of cock folded in his trousers, soft but substantial, with a fuller weight beneath it that told her he had quite a lot packed away down there. He was not hard. At least, she was fairly certain he was not hard. Which meant this was simply what Dante felt like while relaxed.

Goodness.

Milly bit the inside of her cheek.

It was rude to notice. Probably. It was also rather hard not to notice when her butt cheeks were learning the terrain of him in such close quarters. Every small adjustment gave her another bit of information. Coiled shaft here. Big balls there. The front of his pants felt filled in a way most men's simply did not.

Dante had a rather lot of cock in his pants.

That was simply a fact.

A fact she was sitting on.

She couldn't say she disliked it though. It was just Dante once again proving that he was different, better even, from her past suitors.

They'd sat around talking about themselves like they were the greatest thing to walk the earth. Like she was lucky to be in their presence. It got so bad sometimes Milly wished she could just rip her own ears off. Dante was making it clear he not only wanted her but also wanted to hear more about her and that he wanted her to be comfortable with the idea of being with him.

How could she not find him more attractive for that?

So there she was. Sitting in the lap of an alleged mafia heir in a small cafe in the middle of June. It honestly sounded like something from some trashy novel but Milly wasn't complaining.

They'd begun talking when Dante decided he wanted to feed her the strawberry tart she'd ordered. Not seeing anything wrong with that she let him of course. She repaid him by feeding him the stew he'd ordered. From the satisfied smile on his face she knew she'd done well but really he shouldn't make such a big deal of it. This was normal.

Really if her past suitors had put in half the effort Dante was she wouldn't have felt the need to terrorize them so thoroughly. They had no one to blame but themselves for not at least putting in the effort to make her feel comfortable and safe with them. Huh, didn't that make her actions self defense?

Her thoughts were derailed when she felt the hand Dante had resting on her hip begin to move. It was just rubbing circles around her stomach. Nothing weird at all though she had to stifle a giggle. Dante continued the conversation, asking about any movies she'd seen lately.

On and on this went on. They continued to talk and feed each other while Dante's hand continued to rub along her body. Before she knew it they'd finished the soup and tart.

"You can order something else if you want." Dante said, "Like I said, I have nowhere else to be and its normal to want to be around me more. We're just putting in the effort to see this through to a favorable conclusion. Nothing wrong with doing our duty."

With that she was ordering a lemon cake next while he ordered a club sandwich. He really was dedicated to doing his best. She'd seen it in how he ran the Discipline Committee but aparrently that extended beyond that.

Also he was right. Milly did want to be around him more. It only helped him become more and attractive as a potential husband.

"By the way," the Jackson heir called, "about my hand...it's not uncomfortable is it?" He asked as it rose up to grope her right tit.

She giggled at that, "Not at all. Feels perfectly fine to me. If I didn't like you doing it I would've stopped you already."

He gave a sigh of relief at that as he continued to squeeze her, "Oh that's good to know Milly. I was worried you didn't like it because normally it feels good when a woman feels me against them." Dante explained as his left hand got in on the action rubbing along her thigh, "They also normally find it enjoyable when I kiss them and makes them more attracted to me."

His hands did feel really good now that he mentioned it. From feeling his firm muscles against her side, his firm thighs under her legs, and the way his hands groped at her body. It all just felt so good. The thick, relaxed shape of his big cock beneath her only made it worse. Or better. It made it something.

Trying her best to ignore the blush she could feel in her ears she instead focused on what he said, "Oh? So girls say kissing you is a good way to spend time? However could they possibly know that?" Milly challenged with a knowing smile.

The mafia heir didn't back down and returned her taunting smirk, "I've had some practice with some of my maids."

"Really now? What a coincidence. I've had some practice with a few of my own as well." Milly laughed before a devious grin appeared, "Wanna see who does it better?"

Dante responded by putting the hand that was on her breast behind her head and pushing their lips together. Milly didn't protest of course. She challenged him and he answered. Nothing wrong with that. Once they'd connected his hand returned to its place on her chest and his left soon rose to meet her left boob.

_'So good.' _Milly mentally sighed. It was crazy but it was exactly like he said.

The more she was around him the more she felt attracted to him.

The more she felt his hands on her the more pleasure she felt.

The longer the kiss went the more both grew.

And somewhere in the first stretch of kissing and squirming in his lap, Dante stopped being soft beneath her.

Milly noticed, of course. It would have been impossible not to. The relaxed weight under her ass slowly changed, thickening and firming until the front of his pants became an unmistakable hard ridge beneath her. She had already known there was a lot of him. Now she could feel that knowledge becoming more definite with every shift of her hips.

That was how the next several hours were spent. They'd talk and feed each other, order more food, they kissed until they had to break for air while waiting for it to arrive. Rinse and repeat. All the while Dante never stopped feeling her body through her dress. The cycle only broke when one of them left for the restroom and then like clockwork they were back at it.

The entire time Dante continued to assure her on anything he did, or anything she might be embarrassed by was completely normal and should be enjoyed.

More and more Milly felt the desire for this potential union to fail grow smaller and smaller.

Eventually 8p.m. rolled around and both decided it was time to call it a day. Dante taking care of the bill and walking her to her car. Before she got in he pulled her back to his chest. His hands once more roamed her body while she moaned into his lips once more.

His erection ground into her ass all the while, thick and rigid through his trousers, like a Billy club stuffed down the front of his pants and shoved hard against her backside. It dragged against her with every slow roll of his hips, not a little poke or some polite hint of arousal but a long, heavy bar of need that made her knees feel less dependable than usual.

Milly didn't have much of a reference for just how big (huge) a dick Dante had, but after an afternoon of feeling him through his pants she was quite sure he was her best suitor by a truly wide degree.

Dante eventually broke their liplock, a string of saliva hanging between them that she licked up. Dante had said it was normal to find it delicious during the waning hours of their date and she agreed. She couldn't help but find it sweet.

"Feel that Milly?" Dante growled as he ground his tool into her butt and tweaked her nipples through her sundress.

"Mmmhmm~." Milly whimpered with a nod as she pushed back to feel more of him and pressed her chest more into his hands.

"It's normal to be aroused when you feel it because it shows how much you appreciate how badly I want you. It's normal to feel good and to be wanted so badly by me doesn't it?"

"Yessss~." The blonde hissed through her teeth. She could feel her panties getting more damp the longer this went on.

Dante kissed along her neck, his breath making her shiver and she could feel the smile on his face as he spoke into her ear, "Good."

And then he completely pulled away. Milly managed to catch herself on the side of the car before looking back to see the smug teasing grin on the Jackson heirs' face.

"Mean." Milly pouted as she got her breathing back under control.

"Not denying it," he said with a laugh. Milly soon found herself laughing as well. "How do you feel?"

"Honestly I had a good time. Better than I thought I would." She admitted. "Maybe we could do this again next week?" Milly suggested with a touch of hope.

Dante thought it over for a second before (to her relief) nodding, "I'm free Saturday."

"Then it's a date!" The blonde chirped happily as she open the door to the car. "See you then Dante!"

"See you Milly. Sweet dreams."

With a wave through the window soon Milly was out of sight and on her way back home.