For content filtering software, click here

A Big Sissy, Her Love of Femininity, and Her Humiliations

The Catch-22 of Being a SissySissy Phone Sex Mistress EmmaJane 800-601-6975

Even for the sissy who has fully, wholeheartedly, and passionately embraced her precious girlishness, there are times when reminders of the reality of her situation appear like a slap in the pretty powdered face, underscoring that cold hard fact that (a) no sissy is ever going to be a real Woman and (b) no sissy is a real man. Masculinity has left the building and is long gone. That fact, on top of sissy’s trying to so hard to look, act, and feel as feminine as possible in the presence of a real woman, can be a constant source of humiliation and even conflict, despite the joy in the feminization process.

Here is a perfect example of the utter delight yet sheer humiliation in being a sissy, that an exceptionally well-trained and behaved sissy girl of mine, who is committed to submission to real Women, experienced when she was left in the care of a very feminine, attractive, and strong young woman (who just so happened to be decades younger than Sissy):

“My Lady friend went out … and hired a 19-year-old cheerleader to watch me… I had to wear a pretty taffeta dress with petticoats in front of her, and to make it more humiliating, this cheerleader decided what time I had to go to bed. She made me put a nightie on, tucked me in, and gave me a little kiss on my forehead. All this and the lass is 40 years younger than me! Why did I submit? Because non-compliance would have caused the young girl to tell my powerful Lady, who herself is 18 years my junior. Then I would have been either caned or paddled, and that stings so much!”

Poor thing! *giggles* How humiliating such a display of femininity was for her in front of her sitter!

Embracing Femininity AND Humiliation

The aforementioned girly girl is a very special sissy who is fully in touch with her sense of femininity and dedicated to being the best, prettiest, and most well-behaved sissy possible. However, this big taffeta-wearing sissy readily admits to still “feeling like a man” in that she is very physically attracted to Women. Yes. She admires women and finds their feminine trapping to be attractive in the sense that she may feel a bit jealous of their hair, dresses or heels, BUT… Her attraction extends beyond that to genuine sexual attraction. (As if a real woman is going to think of a sissy in a sexual way!) This lust for Women only contributes to the particular brand of humiliation she experiences and enjoys.

“You are so sweet, so precious to me. I consider you my mentoress in the wonderful world of Womanhood. It’s a privilege just to be able to talk to you. I love talking about dresses and skirts with you, but I really want to kiss and hug you, too. Yes, there’s still a guy underneath the crinolines.”

“I truly adore talking to such a refined and beautiful Southern lady like you. It is a delicious embarrassment wearing a pretty dress and petticoat in front of you; one that makes me tremble with both shame and a desire to be close to you.”

Clarifying the Mistress-Sissy Dynamic

Of course, we have discussed proper sissy obedience and manners, as well as respecting boundaries, so Miss Thing accepts that my teasing her about these attractions is merely part of that titillating balance of heightening her feminine feelings while humiliating that part of her that longs to have interactions with a Woman that only a real man would. She knows that  feminization phone sex is as close to sexual interaction as she will ever get when it comes to her Mistress.

“EmmaJane, I love telling you about this stuff because your questions always heighten the nuances of my humiliations.”

…And I love evoking that rush of conflicting feelings that only makes my girl feel even more submissive and feminine as ever.  After all, I adore my sissy girl, and there is no place in our particular relationship for any remnants of anything masculine, be it in appearance or behavior. Ours is a Mistress-sissy intimacy that is founded on mutual affection and a deeper connection, not raw lust and sexual yearning, and it all centers around the joys of femininity.

  • What is it that brings you those feelings of embarrassment that only serve to fan your flames of feminine submission?
  • Do you prefer any humiliation you experience to be subtle or blatant?
  • More sensual or hardcore?
  • Playful or harsh?
Ms. EmmaJane: fetishphonesexcalls.com Ms. Olivia: experiencedmistress.com

Ms. EmmaJane: fetishphonesexcalls.com
Ms. Olivia: experiencedmistress.com

Ms Olivia do you think I’m gay or bi

Olivia 1-800-601-6975

Does being a crossdresser mean you’re gay or bi?

In my considerable experience with crossdressers, sissies and transgender individuals I’ve found that there is no ‘set’ anything when it comes to gender, sexuality and erotic fantasy.

So called studies say that the majority of crossdressers are heterosexual men.  Remember there are . . . → Read More: Ms Olivia do you think I’m gay or bi

Rockin’ Around the Feminine Christmas Tree With Two Mistresses

*Listen to Emmajane talk about doubling your feminization fun while you read.* Early Christmas Present for Sissies, Crossdressers, and Transgender Ladies

Ms. Olivia + Ms. EmmaJane = Happy Femme Holidays!

As you have surely heard by now, here at the Crossdressers Phone Sex blog, I am now joining the ever-amazing, sexy, blonde, and . . . → Read More: Rockin’ Around the Feminine Christmas Tree With Two Mistresses

New Mistress comes to crossdressers phone sex

 (( ** Ms Olivia audio of crossdressers phone sex blog ** )) Have you seen the new banner and some of the changes?

I absolutely adore Ms Emma Jane because she’s smart, hot and she really knows about femme girls, feminization, sissification and gender issues.  Can you handle a double dose of your . . . → Read More: New Mistress comes to crossdressers phone sex

Sissy training school

Ms Olivia 1-800-601-6975

 (( Ms Olivia audio of this sissy training school blog post ** ))

This Experienced Mistress loves to train a slutty sissy! You can tell I have lots of sissification training ideas … here’s just one example, a Ms Olivia audio of a sissy in training. I think your sissy . . . → Read More: Sissy training school

reactions to phone sex Mistress Olivia tumblr photos

Olivia 1-800-601-6975

 (( ** Listen to this post in the Ms Olivia audio **)) Phone sex Mistress Olivia on tumblr

Have you seen phone sex Mistress Olivia on tumblr?  If you haven’t you’re missing out on some fabulous photos and you’ll see some great ideas for your next crossdressing fantasy.  I do love . . . → Read More: reactions to phone sex Mistress Olivia tumblr photos

Ms Olivia and the sissy slut

Ms Olivia 1-800-601-6975

( ** Listen to this blog post in a free Ms Olivia audio **) What makes you think about being a sissy slut?

What turns you into a slut?  ~laughs~  This is a nature versus nurture kind of question.  Are you born to be a sissy slut or are . . . → Read More: Ms Olivia and the sissy slut

sissy thinks about men all the time now

Ms Olivia 1-800-601-6975

 ** Listen to the blog post here in this Ms Olivia audio** coerced sissy

Sometimes a really intense sexual fantasy involves a bit (or more than a bit) of coercion.  Mistress knows that you secretly yearn to experience your full feminization and I set out to seduce, tease, trick and . . . → Read More: sissy thinks about men all the time now

funny story shopping while dressed en femme

Ms Olivia 1-800-601-6975

**NEW:   listen to this blog as a Ms Olivia audio ** Have you ever been shopping dressed en femme?

Some of you are able to go out while fully feminized.  Some of you keep your crossdressing totally private.  As an aside, if you need some tips of for how to . . . → Read More: funny story shopping while dressed en femme

Feminized crossdresser on our phone sex honeymoon

Ms Olivia 1-800-601-6975

Feminized and about to be taken like a woman

First, the honeymoon.  Since you’ve been in chastity, you have had lots of pent up energy to fully focus on being the best feminized crossdresser — getting more and more in touch (literally) with your feminine side.

My Mistress bridesmaids and . . . → Read More: Feminized crossdresser on our phone sex honeymoon