The Greatest Joys of Being a Crossdresser

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

Sheery in Wolford Iris bodysuit and Neon 40 tights

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 ↓

Sheery in Wolford Tights and Sonia Body

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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Top Ten Dead Giveaways of Your Pantyhose Fetish

Posted on March 26, 2023 by Sheery — 2 Comments ↓

Obviously a Pantyhose Fetish

Sure, long gone are the days of secretly hiding your pantyhose stash out of view from your parents. Maybe on occasion they caught on to it. These days, however, likely it’s still not ideal if the general public catches wind of your secret hobbies. No worries, yet you may want to pay attention to those little details you may have forgotten that are just about to out you…

And so we have the top ten dead giveaways of your pantyhose fetish activities, you weirdo.

10. You no longer have socks in your drawer.

9. People are suspicious of you describing everything as silky and shiny.

8. All you ever complain about are runs, and you never ran a day in your life.

7. Old pantyhose litter your house like old war trophies. Guilty here.

6. You hang around the Hooters in sunglasses a bit too much.

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Coming Soon… Me on OnlyFans (No, Really)

Posted on February 23, 2023 by Sheery — No Comments ↓

Sheery in a DKNY bustier and Wolford tights

It’s not news that I have my own erotic fantasies whenever I’m dressed and (almost always) in the mood. Yes, there is that vision of hot crossdresser sex with that beautiful crossdressed lover having her way with me or even tying me up helpless as I am wrestling around in my pantyhose. Yet there is always that one little fantasy that I’ve had for as long as I can remember… getting hot and horny in front of the camera (and maybe with that beautiful crossdresser).

I’ve actually seriously considered this and have looked into creating a CAM website or a live feed of me all dolled up and ready to go… well wherever, whatever. My motivation is pretty much directly proportional to the level of how turned-on I am which, unfortunately, is not 100% of the time. I still pick at that itch from time to time browsing for that perfect web camera, or something I would look oh-so gorgeous in while on camera. Hell, I even thought of adding it as a part of this website. Maybe a little blinking red button to enter my private room for a little show if you know what I mean 😉

However, more recently I’ve been hearing about OnlyFans where pretty much anyone gets in on the sexy camera action and, not to mention, have a little side gig or even a primary income source while doing it. It seemed really intriguing to me, especially not having to deal with website development costs and, in return, leaving around 20% of earnings for the OnlyFans take. And if it does not work out or is not suited for me, no real time or effort (or money) is wasted. Sounds like a deal a bit hard to pass up.

Now there may be some work in drawing fans to watch me, which I’m well aware of, but that might actually work in my favor. I would probably need some camera time under my (garter) belt to make me less nervous as I do my thing in front of the camera for the one or two peepers getting off on it. But, honestly, I can’t really think of anything more exciting than getting into femme mode, slipping into some sexy lingerie and pantyhose and finishing it off with hot miniskirt, heels and makeup. Then I would get to do my little striptease and… hmmm let’s see.

So what would I do exactly on camera and all hot and excited? I’m thinking one or more of these…

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You Guys Really Creep Me out

Posted on January 15, 2023 by Sheery — 2 Comments ↓

Sheery in the shadows

As a crossdresser, it is always nice to meet other crossdressers, especially given that other non-crossdressers you may end up hanging out with might not be fully into your thing if you know what I mean. Generally this would happen meeting someone online, establishing a little rapport about our tights and favorite girly items we like to wear and then may even end up exchanging numbers. Nothing really out of the ordinary unless you count that crossdressing thing.

Now, if things get a little flirty or (I dare say) romantic, then I can get into that too. However, I would also note that this is in the perspective of female me and not my usual male self. An important distinction because they are in fact quite different.

First of all, there is that whole establishing a “connection” thing. Sure we are crossdressers and obviously have that in common. Maybe we have fallen in love from that avatar picture in the profile and think the other is the hottest thing on earth since… actual women. OK, these are really men, dressed as women who no longer have that traditional male/female division to overcome in order to interact and maybe hook up if that is desired.

Well, it doesn’t quite work that way.

I’m not ashamed to admit that I did learn that the hard way with actual women a long time ago. Reversing that role though makes it all the more apparent. For miss me, it is downright scary some of the creepy crossdressers I have stumbled upon online. One in particular complained I never responded to her online, so I said sorry and gave her my number (side note… not a good idea). Then the messages started pouring in…

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The Only Heels I’ll Ever Need From Now On

Posted on December 18, 2022 by Sheery — No Comments ↓

Yves Saint Laurent with Wolford tights

Surely you know by now that I love slipping into a pair of Wolford tights, then maybe sipping a glass of wine while enjoying that silky softness on my legs. If you can’t tell, I’m doing just that as I type here. I also just got on my bed and propped my legs in the air to snap a quick photo (ahem, no dirty thoughts now). It’s actually what you see right above. That shade of Neon 40 is called Sodalite Blue and is quite gorgeous if I say so myself.

Normally my Wolfords are at the center of my attention, however, I just happened to receive a package in the mail the other day with some new footwear, ahem, also in the photo above. This is also one of the first times that I can remember where I am actually turned on wearing heels. Seriously, I had one of those OMG orgasmic moments trying these on, posing in the mirror, then prancing around on the carpet.

They are actually Yves Saint Laurent Tribute platforms that I got for a steal practically new on Vinted. Brand new, I wouldn’t even think about buying heels this pricey which I’ve checked online that are between 500€ – 1500€. By chance, I happened to see these in a listing that caught my eye for more like 200€ which I snapped up. I took from my budget for male clothes (zero) and splurged on something that the female in me would more likely enjoy.

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Dressed, Sipping Wine and, Oh, Some Lovely Thoughts Cross(dress)ing In My Head

Posted on November 27, 2022 by Sheery — No Comments ↓

Sheery in DKNY bodysuit and pantyhose

As usual, I like to write here when I’m in the mood. That is, fully crossdressed and feeling like miss me. Over the years though, (and it has been quite a lot of years writing here) I’ve gone from slipping on some pantyhose and maybe lingerie to full-on shaving, makeup, wig, perfume and paying attention to those little details to transform myself into a more feminine persona. Oh yeah, and a spray of Chanel No. 5 really does help with that.

I know I’ve dived into this before but the more I’m transformed into a woman and see more of a woman in the mirror, I can’t help but to convince myself I just might actually pass for one. It’s definitely a feeling of empowerment and, not to mention, quite a high that I get off of. I don’t know, I would say kind of like an adrenaline rush I’m having even though I’m not actually out in public strutting my stuff if you know what I mean.

Of course all of this makes me incredibly horny yet in a way that truly distinct from my usual male self. It is just something about smelling that perfume or noticing that flavor from my lipstick or even noticing that warm silky feel of the pantyhose draping my legs. Or is it the wine? It is as if it is an experience of being an actual woman who feels turned on which, in itself, I can say is truly a pleasure I crave.

Then it’s moments like these that I occasionally break out the Fleshlight (with that little thing so I can mount it on my refrigerador) and desire nothing more than to be rammed in my backdoor, ironically, while standing in my heels and fucking my little toy. I have natural female-like boobs, too, (weird genetics) so I also like to pull down my bra and push my breasts together wishing a cock would squeeze right between and come right in the middle of them. Oh, and then I like to give a soft rub on my nipples which gives me mini-orgasms.

You can say my masturbation has evolved over the years.

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Ok, So Now What Do I Do Here?

Posted on September 25, 2022 by Sheery — No Comments ↓
Wolford Vegan Leather Body

Image: wolfordshop.com

Ever see something that on first glance you just have to have it? Yeah, like I really have to ask a crossdresser such a question with an obvious answer? Well, several months back, my eyes glanced on this vegan leather bodysuit from Wolford that made me nearly come in my tights. Aside from that, it is a collaboration with Amina Muaddi and (YIKES) has quite a hefty price tag, $665 in the US and £409 in the UK. OK, I would have waited until the end of season sale for this one I guess.

Yet this thing was so gorgeous I debated selling my car, plasma… my body just to be able to slip into this sexy, kind of fetichy garment. Alright, no I didn’t but you could see what I mean. I really did have to have it.

Then it turned out that miracle happened and I found this very same Wolford bodysuit on Vinted for $100 in perfect condition. It was in a size small which, normally with Wolford bodysuits, I can fit into snugly. So of course I would also like a (vegan) leather bodysuit to look like it were painted on. At a fraction of the price, I rushed to buy it and eagerly awaited that delivery truck like the ice cream man.

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Top Ten Ways To Quit Your Crossdressing

Posted on September 3, 2022 by Sheery — 2 Comments ↓

There were many a day in the past where I’ve had that same conversation with myself, then repeatedly came to the same conclusion: So when am I going to quit my crossdressing once and for all? I remember that time when I moved out of my parent’s house to go to college when I knew for sure I’d ditch that, ahem, filthy (but fun) habit. That went well. Or maybe it was that time when I was in pantyhose looking at the mirror at the hair on my legs all squished up, again I thought why keep doing this? Since then I’ve shaved my legs periodically.

So maybe you’ll have better luck and to give you a little nudge, here are the top ten ways you can quit your dirty, filthy (but maybe fun?) habit of yours.

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So I Slipped Into Pantyhose Today, Again …

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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