Sexy MILFs Range From 18 to 80


MILF Mistress Vivian 1-800-356-6169

What’s Your Pleasure Young or Mature MILFs?

When I say Sexy MILFs, what comes to your mind, youth or experience? MILFs aren’t always mature and experienced, they can also be as young as springtime. A fine example is the lovely Helen Mirren, pictured here in 1969!

Do sexy MILFs have to be older? Not always.

Many of the gents I speak to always request an older Erotic Entertainer. What I have found most interesting is that the callers’ ages range from 18 to 80, also. Young men seem to be searching for both the guidance of a maternal woman and someone he can show off his youth to.

Sexy MILFs at a Mature Age

The Dame @ 64

When older men call for a Mature MILF, he knows he will be speaking to a contemporary, someone closer to his age. He is looking for the person he can confide in and who shares a common history. More than likely, he’s always dated women older than himself.

Grow older gracefully.

One of my favorite quotes about aging is,  “Grow old with me! The best is yet to be.”
In just two sentences, Robert Browning imparts the excitement of a relationship when one grows older.

I can’t think of another woman who is the very picture of growing older gracefully than Dame Helen Mirren.  She is full of life, in demand on both sides of the pond, and exceptionally beautiful. I can only imagine what a Ladies’ Lunch with her would be like.

What about you, dear readers? Youth or Experience?  Go on and take the POLL!


Guiding Mature Cross-dressers in Search of Style

Mature Cross-dressers & MILF Mistress Vivian 1-800-356-6169

Mature Cross-dressers Just Want to Have Fun

Mature Cross-dressers might think that as they get older, it is more difficult to present themselves as a beautiful woman. I have to disagree, those who have been dressing for decades, might just need a new perspective of what looks the best on a changing body. There comes a time in every gal’s life, she has to step back – further from the mirror, and see the whole picture.

Mature Cross-dressers What is in Your Closet?

If yours is anything like mine, you can see the passage of time throughout my wardrobe. The years I had to dress for sales, simple and classic, but now the hem looks a few inches too short. You’d see several skirts and blouses from the 70’s, when I went through my gypsy phase, and of course a few pair of well-worn bell-bottoms.

Yes, everything still fits, with few exceptions – but that doesn’t mean I should wear them, unless it’s a Disco retro party. Sure it’s been said, that everything old, is new again – but that doesn’t include my more mature body. One must adjust, if one wants to fit in. Would you agree?

Just One of The Girls

It is such a delight when I get to connect with a cross-dressing male, who is near my age and in need of advice. I’ve had to change styles to fit the worlds I’ve worked in, and my closet has everything from pretty cocktail dresses, to leather corsets.

What I have learned from the years of speaking with every type of cross dresser, is at some age, they would just like to meld in, and be just one of the girls. For the mature ladies, that might mean putting aside the sissy slut wear for a kinky weekend party, and take a harder look at your casual pieces.

Tossing Out the Glitter

Presenting yourself as your genuine age, could also mean it is time to go through your cosmetics too. Using frosted make-up, heavy black eye-liner or too bright blush, will only add years to your pretty face – when at our age, less really is more.

Have you been searching for an older Fem Dom who understand how to grow old gracefully? Would you like an honest assessment of your clothing style, or tips on cosmetic choices and application? Your MILF Mistress Vivian is here to be your fashion guide and sexy confidant.

Not Just a “MILF,” But an Older Teacher

There are definitely a significant portion of you younger guys who are not into the typical MILF experience, but are really looking for a teacher that is older than you, an experienced woman to guide your way into sexual ecstasy.

What An Older Teacher Offers

older teacher

Are you like the others who knew from a young age that you desired older women? Did you admire a specific older teacher? More than the others described how they felt?

By the time you were older yourself, all your masturbatory fantasies and images became “seeing” these older women as they taught you “lessons” you knew younger women would never be able to share in any skilled way. Is that right?

Oh, how I love being a teacher for younger men like you. It is delicious to talk you through, point by point, how to take care of a woman sexually, how to really court a real life woman.

I especially love sharing the major differences between what real life is like compared to the crazy not-real world of porn. Sure, you might not want your bubble burst, but c’mon, you hunger for us for a reason, right? To teach you right from wrong!

Being a Good Student

How do you please an older teacher Mistress? By being a good student, of course!

I love when my boys take my homework seriously and turn in their assignments on-time and done neatly. Of course, the homework includes watching MILF porn, stroking instructions and telling me the details of their fantasies as they orgasm. Not the typical theme assignment like in college, right?

Come let me teach you, sweet boy. I am quite the older teacher!

Pursuing a Mature Mistress

We older women, especially a  mature Mistress, can absolutely see you when you are checking us out, thinking you are being slick looking us up and down at the grocery store or the restaurant.

Wrinkles of a Mature Mistress

mature mistress

I can feel your eyes on my face, nearly counting the crinkles I carry around my eyes, the “laugh lines” I have from a lifetime of roaring howls… snickers and giggles. (If you have not spoken to me on the phone, I, most definitely, am one who thinks many things are hilarious and bust up laughing lots.)

Even as your eyes follow the gentle creases in my face, you avoid my eyes this early on, wanting to make sure I am the woman you would want to pursue as a cub. Your hunger grows for a mature Mistress. The longer you linger on my appearance, the more desire you feel.

A Mature Mistress Knows What You Are Thinking

I feel your view shift to my hands. Do they demonstrate experiences you have yet to imagine? Wiping the tears of our children, decades of holding our lovers’ hands… years and years in the workforce… traversing places that continue unfolding with each of your young footsteps.

Mature Mistress Daphne 1-800-356-6169

Look Into My Eyes

Once you have evaluated us and determined we are, indeed, worthy of your cubby desires, you then… not gaze… but intently stare into our eyes. Even if I am in another animated conversation, my face flushes feeling your attention… and I, discreetly, look around to see from whence that energy came.

I do find you. Over there.

Our breath syncs and the inhaling/exhaling rhythm becomes the vehicle to our inevitable meeting. You move first, walking towards me, ignoring my friends, stepping up boldly, telling me how beautiful I am. I blush furiously. You take that as a positive sign to move forward.

“May I buy you a drink?”

“I would like that. Very much.”

You think you made the first move.


You turn to go to the bar for a drink to serve to the woman you’re keenly attracted to. How funny, that he thinks he was the one who charmed his way to your side. I smile to myself knowing that in reality, it was I who tempted you, drew you in like willing prey, into a delicious web-ish, world.

Watching you move away, I click the latch on your new training collar.


Admiring Your MILF Mistress

You’ve been watching one the MILF Mistresses for awhile, admiring Her words, maybe even speaking to Her on the phone… where do you go from here?

Express Yourself

Mistresses love hearing from those who are watching, either closely or from afar.

Ideas of how to tell your MILF Mistress you are there, observing Her special gifts of tending to the boys in her midst include:

Any of these examples of expression are welcome and wonderful to receive.


I believe the most wondrous way to show your admiration is your devotion to the MILF Mistress you connect with most, the One who makes you weak in the knees… or drives your cock crazy with desire. Regular contact with Her demonstrates your hunger and your need for guidance as a young acolyte.

Does your Mistress-of-Choice offer ideas of ways to remember Her when you are not on the phone or texting? Does She ask you to do something in particular to think of Her during your day? Perhaps drawing tiny dots on your palm at certain times of the day (one of my favorite things to do)? Or touching yourself thrice at specific times, and later, let Her know you obeyed Her instructions?

Together, you can come up with a myriad of ways to please your MILF Mistress.

She deserves your care and attention. Doesn’t She?

milf mistress

From Slut in Training to Precious Pet

Guiding a submissive in training, to his ultimate goal can be a very long journey. The road to the title of precious pet, can be a bumpy one – even for the most eager and willing. It takes a special person to put their ego aside, to serve Mistress – as she directs, . . . → Read More: From Slut in Training to Precious Pet

A MILF & Her Virgin Cub

It’s just delicious being a MILF sometimes. Younger men treat me really well, even those who don’t identify as submissives love to serve me my iced tea (unsweetened with lots of ice) and rub my feet when they’re tired.

Virgin Cubs

There are many avenues to being a MILF cub… memories of your mom’s best . . . → Read More: A MILF & Her Virgin Cub

Two MILFs In a Pod

Two MILFs Are Better Than One

It has been some time since there were two MILFs here on YMM, so I lured in one of my favorite kinky gals, Ms Daphne. Oh she’s a dirty girl she is, and just what we have needed over here – a super, duper, uber – cougar.

. . . → Read More: Two MILFs In a Pod

Enchantrix Daphne Stops By YMM

Meet MILF Daphne

So many in our culture find growing old difficult, so difficult they will endure any number of medications and surgeries to try and bypass the “ravages of time.”

I, on the other hand, see walking towards being older as a gift, a privilege… moving forward in a new role as . . . → Read More: Enchantrix Daphne Stops By YMM

The Joys of Jerkin’ Your Gherkin for Masturbation May

Pull Out Your Pickles! Its Masturbation May

It has cum at last, the one month a year, when you have better odds that your LDW Mistress, will allow you to finish what She started.

Masturbation May 2017

Since I am The Empress of Happy Endings, #MM 2017 is going to all about quantity, not . . . → Read More: The Joys of Jerkin’ Your Gherkin for Masturbation May