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Posted on April 5, 2016 by Sheery — 4 Comments

Sheery in lingerie, tights and heels

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)…

Me and Sharon had met online several months ago. After the usual hellos, flirty exchanges (a pic or two included) and chat room sessions, it was time for the meetup. In a hotel. So it wasn’t as if we were in the dark about what we were going to end up partaking in. Yet the anticipation of slipping into my silky lingerie and pantyhose in front of another crossdresser doing the same was enough to make me cum just at the faintest thought of it. Finally, came that magical day.

And there I met Sharon at the bar in our hotel who was a little bit older and a little taller than I was and fully dressed in a black sleeveless dress and long brown hair that wasn’t a wig. She was strikingly beautiful which intimidated me for a second since I was in public-male-mode (I still didn’t dress in public). Yet she fully understood this and we casually had a drink and chatted. We hit it off right away with the usual bullshit “What do you do?” which eventually led to conversations about our crossdressing lives to which we could hardly find an end to. As well, it was always a relief to share that side which is hardly discussed among others.

There is, also, nothing like casual crossdresser talk to get in the mood and we eventually made our way up the hotel elevator to room 505, a little tipsy and very horny by then. Feeling a mutual attraction, we even grabbed and gently held hands on the way from the elevator to the room. I felt very comfortable and  immediately attracted to Sharon after revealing that femme side of me dying to get out. Of course Sharon wore it on her sleeve which I admired and made her even more desirable.

We enter the room and my first course of action was to open my suitcase and pull out…

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Posted on February 21, 2016 by Sheery — 7 Comments

Nude in Oroblu Pantyhose and Clogs

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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Posted on February 7, 2016 by Sheery — 5 Comments

Guess Geary Sandals

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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Posted on December 28, 2015 by Sheery — 2 Comments

Pantyhose and painted toes

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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Posted on November 15, 2015 by Sheery — 2 Comments

Fuscia Dim slippers and black pantyhose

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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Posted on September 13, 2015 by Sheery — 9 Comments

Victorias Secret camisole and Wolford tights

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 vices 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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Posted on April 12, 2014 by Sheery — 2 Comments
Daphne Bound and Gagged
Image: Wikia

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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Posted on March 26, 2014 by Sheery — 6 Comments

Sheery the Crossdresser

Ever think about that wacky weird path of your own crossdressing days from the very beginning up until now? While, personally, I can’t recall every single time I slipped on a pair of pantyhose and wanked in them, I can recall some of the major points through my own journey into feminine bliss (or is it abyss).

For instance, when I was in my pre-pube days, I had no clue what a crossdresser was or what the hell was going on with me. All I knew at the time was that I was harboring an arousing love of pantyhose and I was the only one in the world who had this freaky side to him.  Being a young teenager, that put me in a bit of isolation carrying around a secret that was not really understood but sucked me in with a compulsion I couldn’t resist.

Yet one day on the couch watching an episode of Cheers years back, I can vividly remember a piece of dialog that changed my whole perception of my growing fetish (also an unfamiliar word at the time)…

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Posted on March 8, 2014 by Sheery — No Comments
Glow Wresting Girl in Sexy Tights
Image: 1941

Oh my, how I love reminiscing about the 80’s in one of those frequent moments I’m caught daydreaming through random crap that flies through my head. Usually it’s the music that brings me back to the days of my childhood. Once in a while, however, surfin’ the net sometimes does it just as well.

That’s when I usually come across images, not created from digital cameras, but scanned from photos or magazines and and portraying beautiful women wearing shiny tights. You know they are from the 80’s either from the graininess of the image or the poofy hairstyles you see. It is then the memories of my developing pantyhose fetish reignite causing me to look on and on for more like the 80’s legs junkie that I am.

And then, there they were, the GLOW Girls. For those out of the loop, GLOW was sort of a spin-off of WWF wresting but for women, created sometime in the mid-eighties I believe. I remember catching them on cable TV a few times absolutely falling in love after watching them (sort of) pounding the shit out of each other while clad in their sexy costumes consisting more or less of leotards (or sometimes lingerie!) and tights.

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Posted on February 4, 2014 by Sheery — 1 Comment

Legs Crossed in Black Pantyhose

Unfortunately, I’ve been a bit under the weather this past week. Nothing, however, beats the day that you wake up, sickness gone, and go about doing the things you had planned to do before the illness began.

Take today for example. I feel so good that the first thing on my mind is throwing on some of my girly wear to capture that silky feeling I love so much. But then I thought, “Why stop there?” Since I feel like this is a day that I can dedicate purely to crossdressing, I might as well document it all, right?

Of course it may reveal how absolutely boring I am but I don’t give a shit. I’ll have my fun (alone), then write…

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