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Posted on July 23, 2022 by Sheery — 7 Comments

Me in a Wolford Bodysuit and Neon 40 pantyhose

Like countless times before, I find myself sitting down with a cup of coffee in hand and legs draped in my favorite black Wolford Neon 40 pantyhose. I notice a little wear on the heel but, no problem, I have more (yes, more than one) of the same colored Wolford in case of a quick need to replace them. Or maybe a special night out on the town. Yeah right, I’ll be staying in tonight.

Anyway, while I scroll through the news on my mobile, I wiggle my toes and admire that ever-present shine, something I’ve also done a million times. I figure I should be bored of this by now but I’m not. I feel great wearing my most prized garment. Actually not just great but really comforted over my lower half, like a cross between silky tactile pleasure and a nice warm hug from a good friend.

Of course I’m also wearing a bodysuit like in the image above (not the same one though) and a short silky robe to round out my household look. Yet I kind of look at them as adornments to how killer I think my legs look in Wolford pantyhose. I mention Wolford since they are my favorite pantyhose at the moment but these could very well be one my other Oroblu, Pierre Mantoux or even Danskin tights I’ll slip into every once in a while.

Now, to say I have a pantyhose fetish makes me laugh and cry out loud. Of course I use to download those JPEG images and watch any kind of videos where pantyhose was the star (yes porn too, OK?). Not to mention gaze at lovely women wearing those shiny tights from behind my sunglasses. I’ve jerked off plenty of times with nothing more than the closest pair of tights and a hand and, if I do a hard search, I’m pretty sure I can come up with a pair of cum-stained hose that I could try on again for a quick chuckle.

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Posted on July 17, 2022 by Sheery — 4 Comments

Posing in Victorias Secret teddy and Wolford tights

I may give an impression that I’m quite the out-of-the-closet crossdresser that you may have seen down the street but the truth is I am still quite private in my life as a crossdresser. Although I have been out in public a few times, it is still kind of a rare thing for me. I guess you can say I still have a foot outside of that proverbial closet at the moment. I am definitely not ready to reveal my feminine self to friends and family. It may never even get to that point but who knows what the future holds?

Now that said, I know that there is that desire to tell my story to someone… anyone please! In particular, that person would not judge me but, at worst, may get a little surprise at my taste in women’s undies or possibly doing a double take looking at one of my female “poser” photos. Keep in mind I’m not talking about those semi-anonymous online friends who I may have had a dirty conversation with here or there.

I mean an actual live person that I could admit all my secrets to, a non-friend and non-family member and definitely someone that does not know any of my friends or family. Hey, sometimes I have to go all out CIA to make sure those rumors don’t get around to the wrong people if you know what I mean.

I would have thought this person would be another crossdresser but, in my case, I happened to be in a crowded bar having a casual conversation with another male who mentioned he was gay, naturally as though he were out of the closet (which he was). I can’t really remember the entire conversation but I do remember saying something to the effect that looks aren’t always what they seem, referring to myself.

“Oh really?” he asked (that I do remember). “Um Yeah, I’m a crossdresser,” I said a bit surprised that I actually did say it. Yet we still finished our conversation as if none of it really mattered. However the topic of my secret crossdressing life did come back to the forefront of the conversation and, meanwhile, I’m wondering why the hell I just told him that.

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Posted on April 3, 2022 by Sheery — 12 Comments

My leg in Wolford Neon 40 pantyhose

Just moments ago I happened to find myself slipping into a pair of Capezio shiny dance tights that I found in a box tucked away in the back of a cabinet a little bit earlier. Of course I didn’t stop there adding a bustier, some tight-ass daisy dukes, heels, wig and some fucsia lipstick to round it all out. I pranced and posed in front of the mirror admiring what I see, and getting very much in the mood if you know what I mean.

So I had to do what any pantyhosed freak in a similar mood would do in that moment. A little self-loving and some frosting for the cake. Oh yes, I did have a taste in case you were wondering.

In the past (like decades ago), after these typical pantyhose-donning episodes, I usually came out of them in a rush to take off my pantyhose, feeling like I committed a serious sin and swearing I will never do this again (albeit fun at that moment). I always knew I would get these urges to “wrongly” wear silky pantyhose and lingerie in the future but I wouldn’t be able to sustain this forever. Or would I? I figured I would quit my experimental phase of crossdressing eventually and maybe have a normal married life.

If you have read around this blog, you would obviously find this is not true. And I have nothing but pantyhose to blame for turning my life upside down. Oh, why did you have to come into my life way back when I was a kid and give me that little “kink” of pleasure that I couldn’t stop thereafter? I didn’t even like women’s underwear or even looking like a woman way back then. Why why why?

Maybe you are into your own little fix of pantyhose and a wank, probably with a pair of panties thrown in (I don’t judge). However, take my warning, because pantyhose may become the gateway to the following…

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Posted on December 12, 2021 by Sheery — 1 Comment

Sheery posing in Wolford pantyhose

As I sit here right in my living room, I have just slipped on a pair of black Wolford Neon 40’s and then had thought that really made me stop and wonder. This beautifully sexy, silky garment is pretty much the basis for my entire life. Obviously it is something you know (I know you too!) but it is quite surprising to think of how it made me who I am.

I can remember vividly how it all started at five years old by falling in love with Mrs Rainwater and her navy blue pantyhose that she would wear with sandals. I think the real life shaping event, however, happened when my sister actually had a pair of navy blue knee highs at the time, which I stole from her that first time then eagerly wore them dreaming of “being” Mrs Rainwater. Little did I know the seed that this planted growing up!

Funny, though, I actually never really got into pantyhose until I was around 11 years old having worn knee highs up until then. But one day, I don’t know what got into me, but I was in a Circle K market and saw the rack of Legg’s pantyhose and just grabbed a pair of Sheer Energy in an Off Black color (yes, I do remember that first pair well) then brought it to the counter to buy. I remember the cashier saying “Don’t you hate it when your mom makes you buy these?” and I nodded in agreement (and reflief). Then I rushed home to get these on my legs. That would be the point where I never looked back.

My teenage years took a slight deviation, having to try out lingerie to accompany my legwear. This was probably the time where my crossdressing was in its infancy since I needed something more than pantyhose to satisfy me, yet while still enjoying them. I suppose there was a growing need to feel more girly and lingerie made me feel “better.” However, I only found it more as a compliment to pantyhose since I would never wore bras, pantys or other lingerie alone. In fact I exclusively wore lingerie with pantyhose but then I would wear pantyhose at any time, under pants or whenever and get myself off without anyone noticing.

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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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