Massimo Monti

**Massimo Monti** is a possible match in Winked and the counterpart of Daniel Morales.

## Profile

**Profile picture Caption:**

I've got a summer mansion with your name on it 😉

**Profile bio:**

Having to spend my holidays alone is bothersome. I'm looking for someone to match my high... level of energy.

## Gallery

First DateSecond DateSecond Date (Premium Option)Third DateExtra Scene 1Bonus Scene 1CG1CG2CG3CG4CG5CG6Promo ImageDream Date summer '23 promo art
## Voice Messages

**Massimo's work**

Alright, since you asked so nicely, or should I say teased so nicely... I’m currently serving as a Chief Financial Officer for an international media corporation. I also happen to be a large shareholder for said corporation. See, I told you it’s boring! But if it matters to you to know what I do... I can work with that. I’ll take it even further... I’ll put on a suit for all our dates, if it pleases you. Then you can have the pleasure of undoing every cufflink, every button... If that’s your kinda thing... It can definitely be mine, too.

**Massimo's summer plans**

Correct me if I’m wrong, but... Our chemistry is off the charts, wouldn’t you agree? I feel really good about you, about us. I’d be a damn fool not to go for it...

You said you hadn’t had that much experience... well, I have. So believe me when I say... It’s not always like this between two people. This is different, and... I’d like to think you feel it too.

And if you need more reason... I think you’re gorgeous. And I admire what you do... You’re funny and clever... heh, like I said, I’d be a damn fool not to go for it.

**Massimo's accommodation choice**

I’d forward you the pictures, but I want it to be a surprise...

It’s a beautiful villa, and I think you’ll agree I definitely made the right choice. Among a sea of gaudy, modern mansions, it stands out, being all terracotta... Lots of flowers, lots of greenery... There’s a terrace where we could have coffee together, if coffee in the morning is your thing. The beach is a short drive away, but of course we have a pool of our own. We’ll need a way to cool off, right? I have a feeling it will get very hot this summer...

**Massimo's busy morning**

I couldn’t really sleep, probably because of jetlag, so I thought I’d go out jogging before it gets too hot for it. It... Wasn’t exactly my plan to leave you to fend for yourself... But I didn't want to wake you, and I had no idea whether you like jogging or not, and... Well, anyway! Jogging is actually a great way to get acquainted with an unfamiliar area. Maybe sometime we could... If you’re up for it... Go for a jog or take a walk together ? I get pretty competitive sometimes, but I promise I won’t leave you in the dust. Promise you won’t do it either?

**Massimo's driving around**

Since we rented the car, I thought I’d put it to good use... I pulled the top down and went for a ride, and let me tell you... The scenery here is stunning. I wish we could’ve gone together, and I think you’d really enjoy it, and who knows... Maybe some parts would... spark your imagination. Like this old-timey drive-in theater I stumbled upon. It’s pretty run down, I’m not even sure if it still works... but, on the off chance that it does, wouldn’t it be fun to check it out? Watch some old, foreign film we don’t understand a word of... Give up on trying to follow it... Make our own fun...?

**Massimo's list**

Hmm, let’s see... Sharing food is intimate, right? Long, sensual massages are intimate, too...

And I imagine showering together would be fun... Have you tried it? Sharing a shower, getting your partner all soaped up? The slippery feeling of skin on skin is incredible... I’m getting distracted just thinking about it! Shower sex... now, that gets a bad rep for not being the easiest, but I’m sure we could make it work...

But honestly... Most of all, I’m really glad you have no problems with me going down on you. It’s undeniably intimate, getting to experience someone like that... And believe me, you’d love the experience, too.

**On the plane with Massimo**

Come on, you know what I’m talking about... I believe they call it “joining the mile high club”? I mean, what else is there to do when a flight is only a couple of hours? Especially since you’ve been kind of insatiable recently... I’m not surprised you took the opportunity to try something new.

I loved that thing you did when you buried both of your hands in my hair while I was going down on you... You wanting more so badly was the hottest thing... And I’m glad you felt comfortable enough to not only ask for it but demand it. More of that, please...

**Massimo's "apology"**

Listen, I just have a lot on my plate today, and the last thing I thought I’d have to deal with was you being clingy. Or needy. Or possessive. Or however you want to call it. I know you disagree with this assessment, but what else am I supposed to think? It never bothered you before when I took some time for myself, and I was always ok with you doing the same. And not to mention it’s entirely immature to expect me to ignore obligations because you wanted to go to the beach or whatever! And...

Look... I’m not trying to have another fight... But can we just move on? Be done with this unpleasantness?

**Massimo's feelings**

Our plans haven’t changed. We set out to have fun this summer and... that’s what we’re doing, right?

I know throwing feelings into the mix surprised you... Hell, it surprised me too! But at the time, it felt like the right thing to do. It... it felt right to be honest about it. I don’t know, I guess I thought it would make our connection even stronger, make things even better than they already are... But that wasn’t necessary, right? I shouldn’t have tried to ask for more than what we agreed upon.

So don’t worry, nothing has changed. Once the trip is over, we’ll go our separate ways and... Think fondly of each other? I hope!

**Massimo's changing plans**

I can’t be alone in feeling like... Like it’s a mistake to never speak to you again. I mean... We have something good going on, don’t we?

I know our vacation was a far cry from real life. You have an incredibly stressful job ahead of you, I’m going back to my own hectic schedule, but... isn’t there something we could do? A couple of sexy, smart people like us could work something out, couldn’t we?

I don’t even know what I’m suggesting, to be honest, and I’m not even sure you feel the same way... But I’m betting that you do. And I’m betting on you wanting more of this.

**Massimo's dating troubles:**

Okay, I’ll admit it... I’ve only been on a couple of dates in the past few months... and you’ll perhaps be happy to know they’ve all gone horribly. I don’t mind admitting that perhaps I’ve been comparing those women to you, trying to get to that same level, get that same spark... Obviously it failed. Apparently, you can’t be replaced that easily.

I think a part of me knew this ever since our trip last summer... That there would be no one else I wanted to travel with, to... Unwind with...

**Massimo's future vacations:**

Alright, here’s what I’m thinking... An island in the Caribbean with our own private beach. Now, that would give us some much-needed peace and quiet! Then, to balance it out, an adventure someplace busy, like Seoul or Tokyo. A place where we can get lost in the crowd, become one with it. Now when I think about it, I’ve never been to Seoul... That’s definitely going on the list, yeah.

Hmm, what else could we do... Swim with turtles in Fiji? Eat pasta on Lake Como? Party on a rooftop in Dubai? It’s your turn to give me ideas.

## Aspirations

**Fantasies**

**Favorites**

**Impressions**

**Secrets**

## Trivia

* The name Massimo, means “Greatest”. It is of Italian origin.
* The character was likely inspired by the character Don Massimo Torricelli from the Polish movie *365 Days*.
* Middle name is Gray.