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Posted on September 28, 2024 by Sheery — No Comments

Sheery's legs in pantyhose, not in public

If you’ve read here a while, it is not news that I still have not gone fully public with my crossdressing. I know, I know, I’ve been doing it for so long that everybody and their mom and sister should be able to tell there is a feminine side to me with just a millisecond glance at me as a “man.” I’ve actually gone out dressed in public once (at night) and, more recently, accidentally outed myself in public. Needless to say, I’m kind of getting “out there” at a pace where I’ll be fully out in public as miss me when I’m dead. Maybe I’m being optimistic here.

It is kind of funny how it went from a sexual thing, which it still is, to kind of a hobby… how far can I take it to looking like a woman then judging it by how people around me react (or not). Then again, I’m pretty sick of being “macho” man and maybe an effeminate approach might be in store. Either way, I’ve been questioning why not just dress and go? It’s not like I’ll be running around in the streets in my trademark lingerie and pantyhose.

It should also be said, I think I’m over donning those girly garments underneath my normal clothes knowing others don’t know my little secret going on there. Keep in mind that I have been dressed around other guy ladies like myself several times but in more controlled situations where there are only us crossers and others who don’t mind our company. I do want out in the wide open though and do want that side of me to be expressed someway, somehow.

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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 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 February 5, 2017 by Sheery — 3 Comments

Sheery in Bustier and Pantyhose

Ah yes, the dilemma many of us crossdressers will face in our feminine journeys (or unless we’re being blackmailed): to stay in the proverbial closet or come out to the world. Admitedly, it is a tough decision so maybe realizing why we are in there in the first place may help us to dip our pantyhosed toes in the pool.

10. Your dog has been threatening to out you.

9. The crossdresser in me has no problem, but the gay side, well…

8. Might as well, your parents have caught you inside already.

7. Still hiding from those pantyhose monsters your mom told you about after she caught you wearing hers.

6. Still figuring out what that pansexuality thing is. May come out as that instead.

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Posted on June 9, 2013 by Sheery — 2 Comments
Catherine Bach
Image: MySpace

Ah, it’s that time of year again. The weather heats up and we all come crawling out of our solitary caves, out for whatever piece of life that exists beyond our abodes. For us closeted crossdressers, that means skipping all those layers over your pantyhose and bra and getting out there to flash some femininity in public.

One image I can’t get stuck out of my head this time of year is Catherine Bach (you know, Daisy Duke) in her tight little shorts and pantyhose covering her so very long legs. In fact, it even inspired me this time around to try out my own leg show just the other day.

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Posted on May 4, 2013 by Sheery — 3 Comments
Sexy Heels
Image: Wikimedia

As a closet crossdresser (i.e. scaredy-cat), probably the one scenario that scares the absolute shit out of me is hopping into the bathroom, taking a shower, throwing on my feminine attire and then walking out of the bathroom only to find all my friends and family waiting outside. Happy Birthday!

In other words, there is no way I am ready to come out as tranny me. Not yet, anyway. Though the thought of it has continually crossed my mind only to be shot down again and again. What a total pussy I am.

Today, though, I came across a post from the I Love Wearing Tights blog that gave me a bright idea. To sum it up, a crossdresser recalls an episode of his life where, as a teenager, he went out to a riverside park, then got dressed in full drag behind the bushes and took a quick walk in the park. All of this done at night.

Then the dusty light bulb fluttered on and off in my head.

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