Ok, I will just go ahead and admit it! I have a thing for panty boys. But if you haven’t feasted your eyes upon the sight of a rock-hard eight-incher pressing against its Mistress-imposed satin prison, well, don’t knock it until you’ve tried it.

The first time a caller told me that he was wearing panties, I just about fell out of my chair. Eighteen years old and only slightly beyond virginity, I was new to the biz and quite naive. Not to mention the parochial education that had kept me running to confession every week, seeking redemption for my own guilty pleasures. (That is until I heard heavy breathing on the other side of the confessional after admitting to letting a boy touch my breasts.)

Then one night Theodore called.

I’m not going to dish on the nature of his fetishes and fantasies, because that’s not what I do. If you are looking for a prurient peek into the underbelly of phonesex, you won’t find it here.

What I will tell you about Theodore is that he was an honorable man. He touched my heart and opened my mind, and I will always be grateful for both. Although I haven’t spoken with Theodore since I graduated from college, there isn’t a week that goes by that I don’t think about him. In fact, if you visited my bedroom (dream on!), you would find a picture of Theodore dressed up in his sheer black lingerie on my bed stand…right next to a picture of my nephew and under the rosaries that hang from the lamp shade.

Not only was Theodore a man of honor, he was a good father, a hard worker, and possessed a generous spirit. A single parent to boys that had been abandoned by their mother, he spent many hours discussing with me his struggles, frustrations, dreams and triumphs as a parent. In between the creative kink and taboo naughtiness (of which there was plenty), I learned about the man behind the fetish.

It was kismet: Theodore became my friend and I became his teenage Mistress. And I can assure you, beloved ZenReader, that a very good time was had by all! I hope he thinks about me, too, once in a while. It would be my honor.

So what is it about panties and men? Why is it such a turn-on for so many? A person could spend a lifetime attempting to answer these types of questions, so let’s just leave the heavy thinking to the experts, of which I am not.

But the good news is that I happen to be quite the sexpert! So I will give you my two cents on sissification, cross-dressing, and sundries. Among other things:

1. For many cross-dressers, emasculation feels good because it is tiresome and demanding to be a big, hard-ass guy all the time.
2. Many submissives find that being forced to wear feminine clothing and do female-type things, reinforces their subordinate status in the power exchange.
3. The breaking of societal taboos heightens sexual arousal for most healthy human beings. Being feminized is one means to achieving this.
4. Some men adore and love and cherish femininity so much that they want to be a part of it. It is almost their prayer, their ode, their opus to womanhood.
5. Hey, I love being a girl! Why shouldn’t they?

I’ve come a long way in the few years since Theodore and I followed our separate paths. Sometimes I think that he would be the one just about falling out of the chair if he knew how deviously devilish I’ve become. But I think he might be a little proud, too.

I mean, after all, he started it!

This entry was posted on Monday, February 13th, 2006 at 9:04 pm and is filed under Kink-O-Phone, KinKergarten, Rhetorically Yours. You can follow any responses to this entry through the RSS 2.0 feed. You can leave a response, or trackback from your own site.