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Things I Really HATE About Crossdressing

Posted on July 30, 2023 by Sheery — No Comments ↓

A while back I told of my absolute joys of being a crossdresser, so why not get all dolled up and let out all my frustrations today? Don’t get me wrong though. If you came here looking for reasons to really hate crossdressing and give it up, you would be out of luck. I LOVE my crossdressing life and the way my new bra hugs the natural curves of my chest. Like anything in life, however, it does have its pet peeves and annoyances from time to time.

Sometimes those pesky problems can get the best of me. Most times I brush them off. Well, now it gives me a little writing material.

So, as I sit here in my black Wolford bodysuit, Neon 40 tights (black) and a black miniskirt (plus my favorite heels), time to begin the tales of things I really HATE about crossdressing…

The Guilt

This use to be an issue in the past but not so much over the last decade or so. Nonetheless, it’s worth a mention… getting that urge to slip into some pantyhose, throw on some lingerie and get a quick wank out of the way. Then the post-climax being the need to stop doing this from now on.

I can safely say this was due to me not being comfortable in my own skin. Hey, once I realized this crossdressing thing won’t go away at all then there was no choice but to embrace it, pervertedness and all.

Shaving

Smooth legs are awesome. Smoothness everywhere else is nice. Shaving sucks. So do those little nicks and cuts from shaving. Why do I have to make an appointment in my calendar every week or ten days to do it? My god, shaving sucks.

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The Greatest Joys of Being a Crossdresser

Posted on May 30, 2023 by Sheery — No Comments ↓

I’ve noticed over the years that the more involved I am in my crossdressing, that is getting all the little woman-like details sorted out, the more I’ve come to appreciate it even more. There use to be a point in my life where I thought it was a curse (well, many points actually) but when I came upon the realization it will never go away, I guess I thought, What the hell, I might as well enjoy it while I’m alive.

The truth is I actually feel like it’s WAY more fun immersing myself in my own feminine world. Trying that new lipstick color, searching for those perfect heels (still), finding out my perfect wig color is dirty blonde or just enjoying that feeling of being all dolled up. I haven’t even gotten into the sexual kink out of it all either which, I might add, is also pretty awesome at this stage of the game.

Anyway, here is my list of things that enjoy most about crossdressing (in no particular order)…

Sensuality

It’s difficult to describe that feeling when I’m completely transformed into miss me. It is kind of a warmth all over sexiness knowing this could be dangerous. Maybe it is the combination of noticing the tightness of that miniskirt or that sweet smell of Chanel that also heightens and arouses the senses to an unbelievable degree. In any case, I like this and don’t want it to stop.

Escape

I hear and read about it all the time how crossdressing is used an escape from your real self and I can say that it is true. Life is hard and we all have our ups and downs, especially me, but getting into our alter-selves does really separate myself from the real world, even if just for a moment. It is honestly the only thing to make me forget about those Zoom meetings at work coming up in the next couple of hours. Um, yeah sorry, it looks like I’m having trouble with my camera here…

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The Pantyhose Diaries

Posted on April 17, 2023 by Sheery — 1 Comment ↓

If you’ve been here long enough then you may already know pantyhose is definitely a passion but not the so-called fetish it always use to be. Don’t get me wrong, I love and wear them as always (like right now even) and they never lost their erotic appeal, not for a second. Way back, however, there was a time where they were the only focus… slip some on, have a quick wank and go on with my day. Or I’d just wear them under my jeans and take notice of that swishy noise and silky feel as I’m walking in public. Alright, I still do that from time to time.

What I’m getting at is that the days of the panty(hose)-boy with the “fetish” are long over in favor of doing this whole look like a girl thing. It’s funny, too, that I never understood how this possible evolution could even happen. I even quite stupidly thought that eventually I would grow out of that kink. Maybe I would just have to take a few minutes to get away from the family, sneak out in the woods, slip on my Wolford tights and come on a pine tree every now and then.

Let’s just say it didn’t quite work out that way.

Not that I’m unhappy being a (way) more girly me. I just never thought it would come to this, no pun intended. Over the years, I’ve read many crossdressing blogs and also have met others online that started with the typical pantyhose fetish which eventually led to full on transformation and, in some cases, changing gender completely (aka Caitlyn and, yes, she did have a pantyhose fetish in her past). What was really strange to me, however, was that it seemed like in many cases the whole thrill we seek by wearing pantyhose in the first place seems to have disappeared in the process.

I mean once you are hooked, how could you want to leave your love of pantyhose?

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So I Slipped Into Pantyhose Today, Again …

Posted on July 23, 2022 by Sheery — 7 Comments ↓

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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Time to Spill All Your Dirty Little Crossdressing Secrets

Posted on July 17, 2022 by Sheery — 4 Comments ↓

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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WARNING: Pantyhose May Cause Permanent Life-Altering Changes

Posted on April 3, 2022 by Sheery — 12 Comments ↓

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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It’s Crazy to Think How Much Pantyhose Has Shaped My Life

Posted on December 12, 2021 by Sheery — 1 Comment ↓

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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Do I Really Want to Be a Woman… Or Just Act Like one?

Posted on September 23, 2021 by Sheery — 1 Comment ↓

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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Let’s Revisit My Attraction to Other Crossdressers, Shall We?

Posted on April 24, 2021 by Sheery — 5 Comments ↓

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. Don’t get me wrong, I’m still attracted to genetic women, however, crossdressers take me to a whole other level of excitement.

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Hetero to Bisexual Crossdresser, How Did That Happen?

Posted on January 7, 2021 by Sheery — 2 Comments ↓

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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