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I Love My Crossdressing Evolution, But Where Will It End Up?

Posted on December 29, 2020 by Sheery — 2 Comments ↓

I often times think about how my crossdressing has evolved over the years. Well, maybe even my whole life. More than two thirds of it, I’d say, I desperately tried all I could to keep it a secret. It was something I would do every now and then in private just to get my kicks and then get on with my day. I guess I thought of it back then as just some of my “weird” tendencies.

Yet back then, it was only about slipping into pantyhose which eventually led to slipping on lingerie along with it. I knew that only made me a male in women’s underwear since I surely didn’t look the part of anything female. It was enjoyable and satisfying nonetheless. Those “taboo” articles of clothing made it oh so alluring to drape it on my body and pretend I was female in some perverted sort of way. At least that was how I thought of it back then.

Today, however, my own crossdressing has evolved to a point where I couldn’t have imagined even ten years ago. No more am I the male pantyboy (or more like the resident pantyhoseboy). Instead I have incorporated more “girlyness” into my everyday lifestyle. For example, I shave all body hair (even my face!) and keep my fingernails and toenails perfectly trimmed with my toenails nearly almost always painted. Then there is that subtle dot of perfume that I like to put right over my deodorant in the morning.

I don’t exactly give myself away entirely as little miss me but I do absolutely enjoy giving away a hint of my feminine side whenever I can. And each day it is a little bit more than the last.

I am always left thinking, though, what will I be like ten years from now if I keep going in this direction?

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That One Little Piece of Lingerie…

Posted on March 18, 2020 by Sheery — No Comments ↓

If you’re like me (of course you are), then after all those years of slipping into your favorite pantyhose and lingerie, you have those few items that you have and will always love forever. By the way, I estimate I have worn approximately 500 pairs of pantyhose and around 200 pieces of lingerie in my lifetime. Yet there are only a few items that I still have that are very dear to my heart.

Note that I’m not talking pantyhose here. Don’t get me wrong, they are my first love and I still even have my very first pair of Wolford Neon 40 on display in my bedroom (now too worn to wear). Lingerie, however the complement to my beloved  legwear they may be, is still a valued treasure in my book though.

So back to that lingerie, to the day there is that one very piece I continue to wear, a black Victoria’s Secret teddy, purchased five years ago on a whim. It was one of those rare purchases that is actually much better when you have and hold it than what you see in pictures before buying. And what a beautiful teddy it was.

I usually have issues with wearing teddies being they are too constrictive and/or the fit is off or, worse, it just plain looks bad. I get it, they are not made for men or an effeminate one at that. However, this one, while coming out of the package looking very teeny weeny tiny, actually fit to perfection. Not only that, but there were no restrictions in movement whatsoever. In other words, it was nice and comfortable. Up until now, a comfortable teddy was practically a paradox.

But comfort is just a small part of the equation. How it looks, at least to yourself, is what really counts doesn’t it?

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How About Now, Do I Look Like a Woman

Posted on June 17, 2018 by Sheery — 6 Comments ↓

While I can’t speak for all crossdressers out there, I firmly believe that eventually a line gets crossed where one goes from the occasional pantyhose-under-the-jeans to the full-on appearing (more) like a woman. Or, at least hoping to appear like one.

Calling it growing up or hitting puberty if you will. Really, there are those little things you do just like a little teeny-bopper girl. Shave your legs and armpits (and beard A LOT more), exfoliate and lotion all over, manicures, pedicures, etc, etc. They not only make you look more feminine but FEEL more feminine as well. And feeling more feminine makes you act more feminine, too, which is kind of the end goal of this whole crossdressing thing. Well, in my book anyway.

One way I found to validate myself as a crossdresser was to have at least have a decent photo. That is definitely the hardest thing to do since you either have to hire a friend or photographer to do the deed or learn how to use the auto feature on your own camera. Then, of course, the most important part: the pose.

There is always the easy way out… taking a selfie or a mirror-selfie. How lame is that, though, since the selfie is so ubiquitous that they are really hardly even noticed. Maybe one here or there is OK, but if a portrait collection consists of only selfie photos,  then why even bother?

I know I’m being a bit snotty but, coming from a crossdresser who has taken many a bad photo and has quite the collection to prove it, having a good photo of yourself where someone viewing it has to ask, “Man or woman?” is the ultimate joy of growing into my own feminine self.

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Where Do We Go From Here?

Posted on April 8, 2018 by Sheery — 4 Comments ↓

I recently had an epiphany about my whole crossdressing life up until now. Primarily, I’m no longer a little teenie-bopper sneaking around with my stash of girly goodies waiting eagerly for a chance to slip into some pantyhose in my room with the door locked. Those days are LONG past. Yet, given how long it was ago, I can still remember my dress sessions rather vividly, as if it were my first time driving.

I’m not afraid to admit it to myself that crossdressing is deeply rooted part of my personality. I love it, have an inredible passion in it and, well, I just happen to like throwing on a pair of pantyhose and getting off on it… for the last few decades. Is there really any harm in it? Ok, so maybe getting a snag in the nylons but that’s another story.

I find it of interest in my self-assessment, however, that crossdressing is obviously ingrained in my own sexuality. Before you go all Captain Obvious here, think about it. Man throws on pantyhose, some lingerie and maybe a wig and a little makeup. Then dot some perfume on for good measure before stepping into those heels. Typical crossdresser duties and was actually what I did just an hour ago.

Yet that’s where the silky things end and crossdresser me takes the stage. All five senses are heightened (yes, I can taste the “fruit” from my lipstick), arousal is taking it’s shape and I NEED, right then and there, to be missy me. No longer am I the weird dude with the feminine tendencies but rather a transformed me with feminine desires and feelings. And those desires now have to be met.

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Confessions in Daisy Dukes

Posted on October 9, 2016 by Sheery — 9 Comments ↓

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

Posted on June 5, 2016 by Sheery — 2 Comments ↓

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

Posted on April 19, 2016 by Sheery — 5 Comments ↓

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

Posted on April 5, 2016 by Sheery — 4 Comments ↓

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?

Posted on February 21, 2016 by Sheery — 6 Comments ↓

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

Posted on February 7, 2016 by Sheery — 5 Comments ↓

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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