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Posted on September 23, 2021 by Sheery — 1 Comment

Sheery pondering being a woman

At times, while being little miss me, I get an annoying thought that goes through my head… am I really just a wannabe girl? You know, doing my best impression to fool the unsuspecting but with none of the weight of being an actual GG (genetic girl). Now I’m not saying I’m a perfectly passing pretty girl prancing around town pretending every chance I get. Yet I can’t imagine myself taking on the real chores, shall we say, of womanhood. These would primarily be the social roles, sexualization and, oh, dealing with men just for starters.

To further explain, as I have gotten older, I’ve grown more to staying true to myself. I don’t lie or pretend to be who I’m not and I expect the same from others, AKA, being a good person or trying my best to be. You could chalk it up to maturity or maybe even being comfortable in my own skin (or both). When I’m all dolled up, however, I change to that other person in me, the feminine one, but still hold those values I have as regular male me underneath.

So the dilemma comes from ultimately trying my hardest to appear and act like a female when I go head to toe full gamut. Oh yeah, the posture, voice, walk in high heels, etc, you better believe I’m working on all of those. Well, if I make this much effort to trying to be female, not to mention have gotten quite far in that journey (and still progressing), then is it time to take on the more heavy duties in my female skin?

Or do I just conveniently transform back to male me when I get tired of playing little missy me, which pretty much is always the case?

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Posted on April 24, 2021 by Sheery — 5 Comments

Sheery, chilling on the bed

I’ve recently touched on the subject of my ever-evolving bisexuality and, looking back, even my past foray into bi-curiousness nearly a decade ago. Oh my how I was the curious kid exploring sexuality in all its many strange facets. It’s hard for me to believe that there was a time in my life where I had the hard-core, church-abiding belief that sex with women was the only road that lied ahead. Of course, I had that little “likes to wear women’s underwear problem” at that young age which I had naively assumed would pass as an adult.

Um, yeah, I really envisioned back then, too, worrying about how many days I can go without shaving my legs these days.

But here I am in a comfortable camisole, pantyhose with panties over them, a satin robe, wig and a swipe of lipstick and quick spray of perfume. Oh, I forgot the glass of wine too. I like to “get in the mood,” even a little bit horny, so when I write here my thoughts come through clearly as my female alter ego. I enjoy feeling like a woman even if it doesn’t lead to sex or masturbation although, admittedly, I could use both at the moment.

My first thoughts in these free-spirited effeminate moments usually turn to fantasies involving other crossdressers. You know… like rubbing our nyloned legs together, smudging our lipstick together, lipstick staining our pantyhose or, ahem, other body parts. Then, of course, getting jackhammered in the back door until I’m unable to sit on anything for at least a day. I would say I’m still attracted to genetic women, however, sex with crossdressers take me to a whole other level of excitement.

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Posted on January 7, 2021 by Sheery — 2 Comments

 

Can't you tell I'm a bisexual crossdresser

One of the reasons I enjoy writing this blog is that it serves as a diary of sorts. It is usually while slipping into my lady things and feeling the feminine vibes and then getting my inspiration into words. I also have a separate little black journal I write to although it is not quite as extensive in my (perverse) thoughts as it is here. The journal is also a lot harder to hide from people in case I’m dumb enough to leave it on the coffee table, which tends to happen on occasion.

(Note that you may have noticed a lapse in time last year. Just assume I was macho me the whole time, OK?)

Having this blog means I even like to go back and read my own writing to see what I was thinking about at some random point in time in the past, which tends to amuse me today. I ran across one entry in particular about my evolving bi-curious nature, though, which I felt the need to revisit since my sexuality has taken quite the detour from nearly ten years ago.

Back then I was coming to terms that I was wanting more than just “vanilla” hetero relationships and felt an urge to explore my sexuality. from the perspective of a woman, or kind of like one at least. I didn’t want to just dress up. I wanted to be the woman that gives the blowjob or takes a good pounding (albeit from the rear). It felt sexy and exciting to fantasize about it, plus it went everything against my rather conservative upbringing which just made it all the more exciting.

I asked, I received.

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Posted on December 29, 2020 by Sheery — 2 Comments

Sheery wearing an Oroblu bodysuit and Wolford Neon tights

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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Posted on March 18, 2020 by Sheery — No Comments

Sheery in teddy and tights

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

Sheery in denim mini and Wolford tights

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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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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