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A Dating Mistress: My "New" Italian boi Friend

Updated: Sep 12, 2023


"I've always been the Mistress & now it's time for Me to take the lead role!" -Ms. Monday Jones


Every morning I wake up to a text message from My Italian boi friend. "Good Morning Bellissima" with a red rose emoji from the iPhone collection. He lives in New York, so the text always arrives 3 hours before My usual wake-up time in Portland, Oregon. If I'm in the mood to respond, I reply with something clever and sign it with "good morning My boi."

My Italian boi friend likes to talk. He can talk all day long if I let him. He even has Italian filler words he uses in between words when he speaks. I'm personally not use to all the talking. He wants to connect on a daily basis, too. I'm also not used to this.

My Italian boi friend drinks a lot of coffee. AND wine. He dines out a lot too. Not because he wants to eat out all the time, but his work calls for it. Big business dinner meetings and such. He's a boss, and when he talks about work, he gives off a mob vibe. Like maybe he owns a piece of the world and is a financial dictator or something of that nature.

My Italian boi friend is 5 years older than Me. He was born in Rome, Italy. He's an Aquarius sun (like Me). He has a common birth name (like Me). His is super Italian, too: Tony.

Okay, if I keep going at this rate, My blog entry is going to resemble a high school senior's essay about their new foreign pen pal/crush from Italy.

:When did I first meet My new Italian boi friend?," you ask. Mmmmmm, I met him in the flesh in January 2022. I met him online in November 2021, when he messaged Me on Instagram. However, I started manifesting him years ago. To be transparent, Our/our first date sucked. He was abrupt and aggressive. I had to be more assertive than desired.

It felt a little like unpaid work...

There was a pause in Our/our communication after the first date, but not without Me explaining My perspective about why the first date went sour. He broke the silence on April 6 (4/6) with a DM on My Instagram and a profound mature apology. He also asked if he could call Me later that day. I'm glad I said yes.

Let Me backup a bit.

As I wrote above, I started manifesting this guy years ago. However, I'm not going to go through My check list of wishes with all of you right now. Let's just say this fucking dude checks a lot of mother fucking boxes. It has thrown Me for a moment or two in the "get to know you" phase of Our/our dating story. I even would insert the word "check" in conversations when he would mark another box.

My Italian boi friend entered My inbox on My Instagram while I was boarding a flight from New York to Portland in November of 2021. He introduced himself. His introduction was rather simple. BUT it caught My eye.

Come to find out later, he found Me through the #HunterBoots that I had posted on My story right before boarding the plane that November day. Then he went to My profile (@Mondayjones420), when I still had it public. Then he recognized Me from a Manhattan venue that I had attended 3 or 4 years prior. He was the doorman of the club. He took money and checked IDs.

SIDE NOTE: My Italian boi friend has a thing for rubber. He loves rubber boots, to be exact and follows the hashtag Hunter Boots. He mainly follows that hashtag because he was part of the company's design team in Italy back in the day. He happened to be on the team that designed the Hunter boots I was wearing in the post I put on My IG. Small world or star alignment?

We didn't share phone conversations or FaceTime right away. I took a moment and held back to watch him on Instagram. What I could see was that he's an artist. A damn good one, too. My "new" Italian boi friend is talented in many different mediums: paint, clay, tattooing, latex, charcoal, sex, etc. He's wicked smart, too. I am in awe of his craft.

I saw that he has a ton of interests and a fair amount of them lined up with mine: sex, guns, style (in design), food, travel, sports, motorcycles, art, tattoos, dogs, kink, Hunter boots, etc. When the phone calls began is when I really started to ask Myself, "Did I find My match?" Our phone calls and FaceTime dates were vulnerable and intimate right out the gate. It was as if the topics were limitless AND all subjects were on the table.

I found out that My "new" Italian boi friend is into BDSM and very familiar with D/s & M/s relationships. His mother is a Pro Domme and still working today in Italy. His sister also is a Pro Domme that is currently working out of London. He grew up in a dungeon as his mom's office.

You won't believe how happy this makes Me. Not only does this guy understand My lifestyle, he lives it, too. I love the fact that he is so comfortable in his sexuality and not afraid of his perverted ways. My Italian boi friend is bisexual and switches in the Dom/sub dynamic. However, he made it very clear to Me that he submits to women and dominates men. It's like he's continuing his mother's work. I FUCKING LOVE IT!

I'm sure I will share stories of Our/our sexual adventures as they unfold but at this current moment, writing this blog post, My Italian boi friend and I have not had sexual intercourse. I'm honestly not sure when or if We/we will get there. It feels like We/we have too many kinky desires in the way of conventional vanilla penetrative penis-vaginal sex to explore in Our/our Femdom D/s dynamic.

From the sounds of it, My new Italian boi friend has plenty of vanilla sex opportunities. I do, too, and he seems as if he would prefer Me to be his Female Lead, his Mistress, his Domme, his full-time Goddess.

I'm game to try...

When I do think about having sex with My Italian boi friend, I think of him at My feet, locked in a cock cage while I masturbate telling him he's worthless to Me. I am telling him that he doesn't know how to please Me and therefore I have to do it Myself. Sometimes I think about him being locked in the cage under My bed in chastity while I'm fucking another man above him. Or him being My bent-over boi while I fucking own his man-pussy. These fantasies really get Me off. *I understand this style of sex isn't for everyone. However, no need to yuck My yum.

I don't feel bad about these fantasies. Not only has My new Italian boi friend willing signed up for this, he's given consent to this dynamic style in Our/our relationship. Plus he himself is a sexual narcissist, and I'm happily helping him by breaking his ego. We/we truly are well matched.

FUN FACT: During the summer of 2021, My sub violet and I were doing some research on buying residential property in Italy. The last place I looked at was Cinque Terra outside of Alassio Italy. Guess where My Italian boi friend owns property in Italy? That's right, Cinque Terra.

I'm one lucky Cunt.

Anyways, My new Italian boi friend speaks My love language of Money really well. He even has shared some work endeavors he would like Me to be involved in as Our/our partnership evolves. AND, I'm already looking forward to filming Our/our shenanigans through the Femdom porn We/we plan to create together. He's already asking if he could help with designing My space in Portland Oregon when it turns into My full-time studio/dungeon later this year.

Oh yeah, AND he wants to take Me home to Italy to meet his mother. We/we are just waiting on his green card approval before moving the relationship outside of New York State so We/we can indulge in some much-needed travel together.

Well fuck! I may have gotten what I was looking for in a personal D/s relationship.

Fuck finally! AND I've learned: be ready for what you manifest because it will show up.

SIDE NOTE: The number combo 4 & 6 meaning in the book Messages in the Numbers The Universe Is Talking to You by Alana Fairchild is "divine intervention in your love life and your financial affairs."


SONG: Me and Mrs. Jones by Billy Paul (Listen HERE)

Photos taken November 2020

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