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Posted on April 8, 2018 by Sheery — 4 Comments

Sheery in Fogal Rapallo pantyhose

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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Posted on October 9, 2016 by Sheery — 9 Comments

DaisyDukes with Fogal Rapallo tights

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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Posted on June 5, 2016 by Sheery — 2 Comments

Selfie in Bustier and Pantyhose

It’s not often that I go on a date with another crossdresser but I too often question myself as to why not just have a little “fun” when I can. So I did and what a rush it was! So here is my little kiss-and-tell of that one very unforgettable date. Note that the name of my “significant other” has been changed to preserve her identity.

Read Part 1

Read Part 2

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.

In an excited rush, I grabbed a condom from the nightstand, ripped open the package and slipped it on as Sharon dabbed some lube on her hand then gave my rod a quick stroke to glisten it up. She then raised her ass, positioned my cock ready for the back door entry into her and began to let it slide in slowly.

I noticed the tightness of her sphincter which gave me a jolting rush from the incredible sensation on my cock. We both let out a loud moan in unison (girly voices of course) as she continued to ride my love rod with a very precise gyration of her ass. I actually admired for a second how Sharon could move her ass like that while the rest of her body remained stationary.

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Posted on April 19, 2016 by Sheery — 5 Comments

Oroblu Bustier and Thong

It’s not often that I go on a date with another crossdresser but I too often question myself as to why not just have a little “fun” when I can. So I did and what a rush it was! So here is my little kiss-and-tell of that one very unforgettable date. Note that the name of my “significant other” has been changed to preserve her identity.

Read Part 1

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.

“Am I really being fucked in the ass?” I thought for a moment. “Should I be doing this?”

It wasn’t my first time, though, so in that exact same moment, I consciously decided to calm the hell down and enjoy the experience. Otherwise, things can go south rather quick which I did not want to let happen.

“Yes, I should little bitch,” became my next thought. No going back then.

Sharon entered deeper, then deeper with her first few slow thrusts until finally making full penetration. There, she held her love rod in place while grabbing each of my straightened legs and pushing them back, using them for support. She flattered me by mentioning I have sexy, flexible legs which then gave her the green light to do whatever she wanted. I mean anything.

The real fun started, though, as she fucked with just more force than before which sent me through another wave of excitement, an exhilarating body high. I had always practiced anal penetration with a dildo a similar size to Sharon’s cock, however, the real thing was WAY different. There was no match of the sensation of hot flesh pounding me from the ass masturbation of a hard rubber dildo I was used to. This was definitely something I could easily get used to. Oh, and any guilt and second thoughts I had… turned into shame as to why I haven’t been doing this sooner.

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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 — 6 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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