Gracie Answers Her Mail

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Crossdressers & anal sex are discussed.

"Dear Gracie

My boyfriend is interested in anal play. I'm nervouse, hell, I'm even grossed out at the idea of rimming, but I don't want to flat our say 'no' (as I have to him playing with my ass!) Any suggestions?

Just call me Ass Play Virgin"

Dear Ass Play Virgin,

I can understand your reluctance. It's an area that is taboo to many ~ & what's more terrifying is that it is 'new.'

While it is kind of you to consider making him sexually happy, never, ever consent to things you just don't want to do. However, if this is one of those 'Well, maybe...' moments, here's what I suggest:

Instead of using your fingers or mouth, get a toy.

There are many, *many* anal sex toys ~ from beads & dildos to vibrating gizmos. Starting with an object other than your own skin may be an easier way to start.

With toys you can please him, yet avoid many other fears (common ones for women include injuring a partner with their long fingernails, keeping clean & fear of partner's 'reactions.')

Toys can be eased in with little contact of your own skin, they are without sharp points, and toys can be cleaned well (as well as reserved for 'that area only').

Once you need not worry about tasting forbidden fruit & can just enjoy his pleasure, you may become more interested in venturing further down (up?) this dark passage.

Oh, & don't forget the lube!

Until next time, I remain,
Your Gracie

"Dear Sex Kittens, I've been contacted at an online dating site by a man who says he is a crossdresser. He says he's straight, but I don't know what to think. I consider myself an open person, & don't want to dismiss a person out of hand, but I don't know much about this at all, & I don't want to end up dating & caring for some guy who is really gay or who is confused about his sexuality. So tell me, what is the deal with cross dressing? Cyndi"

Dear Cyndi, None of us here has any personal knowledge or experience with dating a crossdresser ~ we only know what we've read, which includes an excellent book, but typically we women prefer real stories from women we know & trust. So we put the call out in our large network of friends, and we were blown away by the responses!

Due to the incredible amount of replies from crossdressers themselves, their partners, and others who have relationships with those in the world of CD, we are still wading through it all. Seriously.

It seems that while it is true that male crossdressers can be straight, there is plenty of evidence that shows that these men can also be gay or bi-sexual.

Since we do not wish to do a disservice to this topic, we are going to present the replies in several parts ~ beginning with Janet's Story, a woman who meets a male CD & is intrigued...

While there is no easy or fast answer, we hope the series will help you (& others) come to see the issue in a full sense, and see what makes sense for you.

With much affection,


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Gracie's Room

Come inside my boudoir... As a former pro & a general wild one, I'll discuss all sorts of naughty business. For more, read my bio.

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