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Cuckold feminization by Ms Olivia

crossdressers phone sex

Olivia 1-800-601-6975

First the cuckold

When he first started calling me, we talked about cuckolding.  That’s a hot scene and so many ways to do it.  We’ve talked now for years and like most long term phone sex callers, he has become more comfortable telling me his sex secrets and erotic fantasy scenes that he wants to explore.  He was curious about the thrill of erotic humiliation from being a cuckold so I suggested cuckold feminization.

Slowly adding to the cuckold feminization

At first, he was just a cuckold in panties.  The little extra zing of being put in panties while watching a man … a real man … an Alpha man … fuck his woman is HOT!  We both liked that.  A LOT.  Then I said, you look so cute in those panties, let’s put you in a bra.  Well a bra and panty set is very hot and simply begs for silky stockings.

Full feminization and transformation

Now, he is talking about getting boobs.  He’s thinking small but I think he should get nice big breasts, say, something along a D cup size tits.  We talked about this today and he agrees that a feminized cuckold really would look best with nice BIG BREASTS — because for a crossdresser, it’s all about the boobs!  I’m so glad we agree!  ~smiles~  Of course, I knew he would eventually agree because I had this all planned out almost from day one of talking with him.

One example of cuckold feminization by Ms Olivia

I am the Experienced Mistress and I love to plan what I will do with a long term caller.  Feminization is one of my favorite things and making a man a cuckold and then turning him into my feminized playtoy is FUN!  What should I do with you?

Your Experienced Mistress,

Ms Olivia

Learning Southern Speak of Sensual Sissy Humiliation (Part Three)

Sissy Mistress EmmaJane800-601-6975

Before beginning, I would like to extend a special “Thank you” to Sissy Lynn, who has offered her own observations and inquiries about Southern Mistress speak translations. I am including one of those here. Thank you, pig-tailed Sissy Lynn!

“Don’t You Think I Should Only Be Allowed To Touch Myself . . . → Read More: Learning Southern Speak of Sensual Sissy Humiliation (Part Three)

Learning Southern Speak of Sensual Sissy Humiliation (Part Two)

Some Clarification On Sensual Sissy Humiliation Sensual Humiliation Southern-Style:  Soft AND Hard…

Let me preface this second segment of Southern Mistress speak with an important note: Just because I say something that might be superficially “tame,” as it were, this does not take away from or negate the intended sting of sissy humiliation in . . . → Read More: Learning Southern Speak of Sensual Sissy Humiliation (Part Two)

communication with Mistress

Ms Olivia 1-800-601-6975

How to talk to a Mistress

Do you ever get tongue tied when you try to talk to a Mistress?  I know there are many people who are shy or unsure about communication with a Mistress.  ** Listen to the Ms Olivia audio of this blog post **

Topping from . . . → Read More: communication with Mistress

Learning Southern Speak of Sensual Sissy Humiliation (Part One)

Southern Sissy Humiliation Talk

Sissy Mistress EmmaJane800-601-6975

People just love to snicker about and take delight in the way we speak here in the South, finding our particular vernacular to be novel, cute, and amusing. It’s often joked that a Southern Woman -or Southern Mistress, as in this case- can cut you off . . . → Read More: Learning Southern Speak of Sensual Sissy Humiliation (Part One)

FREE phone sex

Free phone sex info and dates

Here’s a quick post for the girls to make sure you know about the FREE PHONE SEX available this Thursday and Friday.  Mark your calendars in slutty red lipstick or pretty in pink lip gloss … this is a really wonderful deal for you.  And …. what girl . . . → Read More: FREE phone sex

In a Perfect Sissy World, What Would YOU Want?

When a Sissy Imagines More

Wondering how things could be, speculating as to what might be different, and pondering whether the proverbial grass is greener on the other side of the fence are all part of the human condition, especially for those -like sissies- who are restricted in expressing a vibrant, colorful, and very . . . → Read More: In a Perfect Sissy World, What Would YOU Want?

Gender question for en femme crossdresser or sissy

Olivia 1-800-601-6975

Gender question from a crossdresser

** Listen to the Ms Olivia audio of this blog post **

I love getting emails because I get inspired by your comments, questions and ideas.  Sometimes I will post excerpts of the email here on the blog and then add my thoughts.

I’m always curious . . . → Read More: Gender question for en femme crossdresser or sissy

Crossdresser engagement

Ms Olivia 1-800-601-6975

** Listen to the Ms Olivia audio ** If you are a crossdresser

… then you have a wedding fantasy.  At least that’s true for the majority of crossdressers simply because there’s something so uniquely feminine about the whole bridal/wedding experience.  And crossdresser wedding lingerie is sexy to me!  I . . . → Read More: Crossdresser engagement

Ms Olivia asks about your sissy name

 ** Listen to the Ms Olivia sissy name audio ** Femme names are important

The name you choose to express your feminine side is important to any crossdresser or sissy!  I think this is particularly important with the power exchange fetish play that goes on between a Mistress and a sissy.  Often Mistress . . . → Read More: Ms Olivia asks about your sissy name