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Confessions in Daisy Dukes

OK, for starters, sorry about the long scroll down. I guess I could have made the image a little smaller but then I would have the misfortune of not letting you see the new love in my life for all its glory. I find it odd that I’m getting around now to try out these highly sexy denim shorts since they’ve been around, oh, since the 80’s. Better now than never as it goes.

Maybe it was a particular image that caught my eye or just the urge to wear something feminine but different, I can’t remember, but I went out and bought my very own pair of Daisy Duke shorts in my usual jean size (not revealing it, sorry). You should have seen my face when I ripped open that package and rushed to put them on.

They barely hung onto my ass meaning they were meant for a woman quite heftier than I. Fine, returned it and ordered another pair a couple sizes smaller. I was having my doubts if these would actually fit since I had never sized or worn womens jeans and the size ordered was WAY below my usual size for even a tight pair of jeans.

Received in the mail again. Ripped open the package, slipped them on with a bit of pessimism. Prepared for another return.

Yet the Hollister shorts fit, well, perfectly. They were tight but not constricting and no loose areas. I noticed on the tag, they have the slightest bit of spandex which allows them to stretch and cover my ass perfectly and comfortably. But now we have to get down to what I was really waiting for. The match made in heaven: wearing them over pantyhose.

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I Kissed a “Girl” and I Liked It, Part 3

Sharon was excitedly busy giving me the blowjob of her life when I suddenly had a moment of realization. There I was lying on the bed in my bustier and pantyhose and with a hole in the back that I could still feel wet from the lube Sharon had used to wet her cock that pounded me a good thousand times or so. The sexy crossdresser making me her toy and actually getting my silkies dirty had always been a fantasy of mine.

Yet this had turned into everything I imagined it would which struck me as odd. Does anything, especially a fantasy, ever end up being like you dreamed it would? “Maybe it would come close,” I thought as I watched Sharon’s head bob up and down and drowning in her sucking prowess. Nonetheless, I enjoyed the moment and the absolute “naughtiness” of our sexual encounter. I was at the peak of feeling feminine and sexy and never wanted that to end.

Sharon stopped her her vigorous blowjob all a sudden and climbed over me and into the cowgirl position with her ass just above my still-hard cock. She pulled down her black Oroblu pantyhose just enough so her bare ass was exposed then leaned over and gave me a soft kiss along with her sultry smile. As she reached for the lube nearby, I caressed the smooth, shiny nylon covering her legs and indulged in the feeling as they even rubbed against my own pantyhosed legs with every movement she made.

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I Kissed a “Girl” and I Liked It, Part 2

Sharon giggled for a second and made a humored attempt at an access hole through my pantyhose by poking her rock-hard cock into it several times while I’m on my back with my legs pulled as far as they go. As I anticipated her “entrance,” feeling her cock in and out and just barely teasing my ass was, in fact, a turn on. The tease made me so wild with anticipation, I start to tremble from the excitement.

Yet, realizing that the nylon and spandex was tough to break, Sharon ripped a small hole with her fingernails just below the crotch area and gently widened it exposing my asshole-turned-vagina. I even noted to myself, it would have been wet as possible if it weren’t for those damn gender differences. Oh well.

I grabbed a condom and lube, conveniently laid ready in place on the bed, and unrolled the condom onto her cock in a smooth, single stroke. Next, I squirted a little lube into my hand and softly stroked it over the condom-covered-cock while she let out a slow “Ooooh.”

Sharon was very gentle at first, easing her slicked love rod through my sphincter which penetrated with a little resistance but gave me a shock of excitement throughout my body. I remembered thinking “Oh my god, there is a dick inside me!” Even a wave of panic came across me.

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I Kissed a “Girl” and I Liked It

It’s not news that I’m willing to stray from my traditional vanilla hetero side and indulge in an escapade with another sexy crossdresser. It was my first time and it was a little awkward, sure, but not any different from that first time with a GG girlfriend many years back. The seed had been planted, though, and the next time would be a far better experience for certain, much like where the vanilla hetero experience took me.

Bisexuality is still something relatively new I’ve dabbled into after straying in and out of the bicurious phase more recently. To be quite honest, it excites me now more than ever before and will go out of my way to explore it when I have the chance. Then, of course, I have to spill it all here, not to brag about the conquest, but rather share the experience. So keep in mind the name here is changed to preserve the identity of that dear crosslover.

I have to admit that crossing that line I’ve always been taught was taboo or “wrong” isn’t easy. Also the experience doesn’t always go as planned (read the link above) but it can turn out an exciting fling which leaves you wanting more. So, whether or not you’re a relative newcomer, this could either make the bicurious in you think about that next step or possibly relive your tales of chicks with dicks.

So here goes my adventure (again)…

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Why Do I Always Write When I’m Horny?

There’s one thing I’ve come to realize is becoming a common theme as I write here. It was somewhat explained in my last post to the women readers (maybe all two of you). Yet, I’ve noticed a trend going way back to even the early days of filling up this website with page after page of endless dribble.

I’m almost always horny when I write and, if not, I try to get there somehow.

It’s funny how it has even grown through phases of turning the light on, if you will, before typing away on the keyboard. At first, it was just slipping into a pair of any old pantyhose and waiting for that erection to begin to kick in (see image above). Nowadays, it’s more complex. I slip into one of my few favorite pantyhose, a chosen piece of lingerie or even a camisole and mini and a select pair of heels. Then I finish it off with a wig and some makeup.

A little more time consuming now, yes, but I’m actually more into my female persona and, while I could just peek into a crossdresser chat room and get some filthy talk and camera exchanges going, I prefer to express my current “on” state in words that may get archived somewhere in digital land so the future crossdresser can look back and go “Huh?”

What’s different now, however, is that the more I do to become my woman self, not to mention the extra hour involved, the more I take pleasure in actually being that woman. Do I still get my seemingly required erection? Definitely, but I also get a deep body buzz of excitement from just looking in the mirror and knowing I’ve transformed to a woman. It is a sexual thrill still yet, equally, it is a sensual power trip that is completely intoxicating.

In fact, it is so overpowering, I nearly orgasm without having to polish up the bishop. Yes, really. I never imagined it would come to this but there’s just no going back to those days of getting my jollies from just a rag pair of pantyhose. No way.

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Who Would’ve Thought, The Right Heels Do Make the Woman

It’s no secret that succession of crossdressing phases goes something like this: slip into your mom’s pantyhose as a wee-tot, then try on a bra and heels and maybe her makeup a few years later. Then at point when you can pay for all this shit yourself, you buy them all for your very own. So shoes and in particular, high heels, would typically be a part of that equation. I’d say for most crossdressers in my opinion.

Well, somehow after all these years from the wee-tot stage, I still seem to have an aversion to high heels. I think they look sexy and I want to love wearing them since they are clearly the perfect accessory for gorgeous pantyhose over freshly shaven legs. I even splurged on some gorgeous leather clogs thinking that would spur my lust of the heels world. Sadly, those very lovely clogs have gotten few uses to grace my pantyhosed feet ever since.

“What gives?” I’ve been thinking to myself. I can’t go out with just pantyhose and regular shoes. My high heels just aren’t “doing it” either for me if you know what I mean. Then I finally realize the issue while browsing for heels one day: I never chose the right heels… duh.

Here’s a quick rundown of my collection of high heeled shoes…

  • Six inch clear plastic heels and, yes the stripper kind. Cheap, uncomfortable and painfully obvious what they are for. Seemed like a logical purchase at the time.
  • Six inch over-the-knee glittery boots. No, they are not made from leather or even faux leather but fish-scale shiny fabric. Bought with the heels above. Ditto on the logic.
  • Wedge sandals. Found in a steal of a deal on eBay. Had to glue a strap back in place not too long ago. They still haven’t made me feel quite like a supermodel.
  • Leather clogs. Definitely the most upscale high heels I’ve ever had but they are just not quite me and are, therefore, rarely used. I must not like heels then?
    • Yeah, I can see other crossdressers shaking their heads at me. Enough said.

      First, let me start out by saying that one telltale sign of a true woman is her ability to look through and pick out a pair for herself. I found this to be quite a journey through hell at first. There aren’t just a few high heels to chose from but THOUSANDS. I’m talking just high heeled sandals, too, not boots, flats, casual and whatever else to which there are millions more to browse through. OK, so this is what it is like for a woman when shopping for shoes… I almost call it a day. Almost.

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Pantyhose, The Root of All Evil

I can say without a doubt that my crossdressing has taken leaps and bounds since my first days experimenting in my sister’s tights as a sort of pre-pubescent indulgence in erotica or, as we all may know, the pantyhose fetish in it’s infancy.

Shaved legs, hell yeah. Whole body? Yep, that too.

Makeup… just now learning how to do up properly.

Wardrobe? Check, including the mandatory minis and fuck-me dress.

Heel collection: I realize how addicting that can get… and how much I drool over Louboutins.

Full public view, well, maybe that’s in the near future.

Despite my love of trying to bring out the inner woman in me, not to mention the sexual thrill it gives, I always seem to end up obsessing over my first real (non-human) true love: pantyhose. They are always my first item of attention when dressing and, even if being the only thing I have on, makes me feel more feminine than even the perfect makeup session (or those Louboutins). Well, OK, if I had those Louboutins over my pantyhosed feet, I think I would shoot my load on the ceiling.

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Covertly Expressing the Feminine Side

I said it before but I’ll say it once again. Yep, I’m still in the closet, safely locked away and with the key still hanging on a nail in the garage. So that part hasn’t changed from a while back. That doesn’t mean, however, that I wouldn’t find it exciting if I happened to be caught in my bra and pantyhose putting mascara on my lashes. It would just make me a bit uneasy to handle the consequences of such an occurrence, despite being in a sexy exhibitionist sort of way.

After all, I am famous and have paparazzi camped out outside of my headquarters. OK, maybe not but replace the pappo with my friends and family would be just the same anyway.

That doesn’t mean that I don’t display my femininity at all. I absolutely love doing so but in more covert terms. Actually, I like to make it more of a game of Can You Tell I’m a Crossdresser? If you correctly guess, I might give that fact away (if you’re, say, a cute crossdresser) or I may not (if you’re my sister). Maybe I’ll just keep you guessing like a sophisticated woman would which could’t be more feminine. Am I right?

But I’ll let you in on my little clues…

Shaved Legs

This has been a more recent thing for me but has now become an actual necessity. Silky smooth legs are oh so sexy and no more having bear witness to that gorilla hair visibly smushed up against my pantyhose. Ewww!

Luck has it that there’s nothing to really even hide by doing this since it has become (somewhat) mainstream being a practice by male athletes and especially bikers. I actually tell everyone that my runner’s legs are more aerodynamic and far cooler without leg hair. Then I jokingly tell them they are sexier too. Oh, if they only knew…

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Underappreciated Vices That Crossdressers Fancy (At least this one)

I seem to be doing a lot of thinking when it comes to slipping into my silken garments and looking at that bright shade of lipstick in the mirror. Oh, the philosophies of life as a crossdresser, way outside the norm, never boring and always making me question myself. Without regrets of course!

Since there is no official day of the crossdresser, that I’m aware of anyway, I’d like to dedicate this to the little things that are appreciated, solely by us and only by us. OK maybe not all, but if you ever donned panties for twenty years and don’t have a vagina, then you’ll know what I mean.

Favorite Color

Sure, your favorite color as He-Man you may be blue or black but the girly side craves another shade. Am I right or is it just me? Pinks, pastels and anything prefixed with “baby” all of a sudden become a part of your world (and maybe those twenty-year-old panties). Call it our society’s labels with masculine and feminine colors but I just happen to love fuscia on everything from nail polish to my lace teddy.

For some reason, pantyhose “suntan” seems to resonate with me as well. Not totally feminine but could be just a crossdresser thing?

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One Kid’s Cartoon is Another’s Favorite Bondage Porno

As a kid, I spent hours and hours in front of the TV, like all proper kids did. I’d say I would spend at least a minimum of eight hours a day watching the typical cartoons that showed up on cable which, coincidentally, was fairly new at the time. Yet during the thousands of hours stuck in front of the tube, there were several specific cartoon episodes that stuck out in my mind.

That is, when certain characters would get into trouble, then are erotically bound and gagged by some gargoyle waiting for someone to save them. I somehow never saw this as something those cartoon writers had intended or, really, how most kids probably innocently viewed it. You know, worry about the character then hope he/she gets saved. Or more so, hope the evil villain just kills them off.

No, I saw this as a version of pantyhose bondage porn, later shaping my future fetishes to come. Of course, we cannot forget that crossdressing era of my life that came about, largely in part to this.

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