CALL OF THE DAY: the Case of the Happy Cross-Dresser

Less broodiness, more bopping each other over the head with pillows!

Less broodiness, more bopping each other over the head with pillows!

I have only began talking to this caller this year, and although he did become something of a regular in the few months before I went off to tour the UK, we hadn’t been talking long enough for me to have missed him if he never called again. I mean, he didn’t even have a nickname, in my mental notes. And in the other direction, I just don’t expect most of my clients to give that much of a shit to try to find me after a 4.5-month absence.

But he called today, and when I read his index card in the five seconds before he said hello, I rejoiced inwardly. It’s my happy cross-dresser! (Okay, I guess he has a nickname now.)

We chatted for a bit, vague banter about “what have you been up to” and “did you get any new bits of lingerie over the summer?” His answer to that last one was kind of sad, actually. He said he went through and trimmed his collection down to four pairs of panties: “I worry that if anyone ever stumbles across anything, you know, four pairs can be explained away as girlfriends just leaving them, but anything more than that…”

(Gah. Sometimes I hate this world. Guys should be able to have as many frilly things in their drawers as they want!)

Anyway, he said he had a fantasy he wanted to share, about me catching him rummaging through my underwear drawer and taking blackmail photos of me, before dragging me off to a lingerie store that my friend owned. Together, she and I would make him try on different items and offer pungent but not mean-spirited critiques and compliments, and then…

But there he stopped. “Wait, I never ask what you want,” he said. “I want you to have fun, too. Do you enjoy what we do? Do you get off?” I thought about telling him a lie, and then I thought again. I could lie convincingly enough that he’d be fine, but there are a few callers with whom I prefer to keep things as real as possible. I don’t know why this category even exists in my head, but it does, and this caller is in it.

So I said, You know, don’t worry about that. I love the quality of our conversations, and I also really enjoy it when clients have fun with their own fantasies and invite me in to share and guide these encounters, even though it might feel vulnerable or risky. So, don’t you worry your pretty little head about me. I always have a great time with you!

That set him at ease, and we got on with his fantasy, with a few things I threw in, like the champagne that my girlfriend and I were going to have while we watched him strut his stuff.

I expect you to serve that to us, I said

“Oooh, can I wear a French maid’s outfit?”

I had to smile. I saw that coming. Of course you can, sweet heart. I’ll give you all the ruffles in the world, with silky sheer black thigh-highs and the perfect little white lace panties that let your cock and balls stick out. But you’re still going to have to crawl around your knees to clean up the drops of champagne you spilled on my thigh when you popped the bottle.

“Yes, oh god, yes, please, let me clean that up for you, I’m so sorry, I’ll get right down there and clean it up…”

I mean, how could I not enjoy creating experiences like this?

After he had come, we still had four minutes left in his time, and I remembered something that I had thought of at the beginning. I told him about this online store that sells frilly lingerie for men. While I was telling him about it, I quickly looked it up to remember to the name. Homme Mystere, that was the one, and clicked through to the site.

They’ve done a redesign recently, I think, and the new look made me want to get my caller over to them even more: All of the guys on there looked like they were having fun. Some were smiling and being playful, or just lounging around comfortably, looking at the camera with a clear, uncomplicated gaze. This is who I thought my caller was, or wanted to be. If he ever feels safe enough to get himself another pretty thing, I hope he tries there, instead of furtively picking out the easiest thing to hand in Victoria’s Secret.

The whole thing reminded me also of the Happy BDSM tumblr, which is full of kinksters all happy and smiling, sometimes laughing, having fun. There’s something so powerful about tangible joy in kink, both for those who receive and those who give. If I can share in that joy with this fancy dressed client of mine, then that is more than I normally get from doing a call, and that is enough for me.


Wanna help me share the joy?



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