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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 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 November 15, 2015 by Sheery — 2 Comments

Fuscia Dim slippers and black pantyhose

I said it before but I’ll say it once again. Yep, I’m still in the closet, safely locked away and with the key still hanging on a nail in the garage. So that part hasn’t changed from a while back. That doesn’t mean, however, that I wouldn’t find it exciting if I happened to be caught in my bra and pantyhose putting mascara on my lashes. It would just make me a bit uneasy to handle the consequences of such an occurrence, despite being in a sexy exhibitionist sort of way.

After all, I am famous and have paparazzi camped out outside of my headquarters. OK, maybe not but replace the pappo with my friends and family would be just the same anyway.

That doesn’t mean that I don’t display my femininity at all. I absolutely love doing so but in more covert terms. Actually, I like to make it more of a game of Can You Tell I’m a Crossdresser? If you correctly guess, I might give that fact away (if you’re, say, a cute crossdresser) or I may not (if you’re my sister). Maybe I’ll just keep you guessing like a sophisticated woman would which could’t be more feminine. Am I right?

But I’ll let you in on my little clues…

Shaved Legs

This has been a more recent thing for me but has now become an actual necessity. Silky smooth legs are oh so sexy and no more having bear witness to that gorilla hair visibly smushed up against my pantyhose. Ewww!

Luck has it that there’s nothing to really even hide by doing this since it has become (somewhat) mainstream being a practice by male athletes and especially bikers. I actually tell everyone that my runner’s legs are more aerodynamic and far cooler without leg hair. Then I jokingly tell them they are sexier too. Oh, if they only knew…

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Posted on January 23, 2012 by Sheery — 1 Comment
My 2nd favorite heels, Danskins
My 2nd favorite heels, Danskins

In case you haven’t guessed already, I get my jollys off of slipping on pantyhose and lingerie. Aw, hell, I go all out with makeup, wigs, heels, the whole bit. Nothing too suprising.

But apparently you must too if you’re sitting there reading this. Great! Nice to meet other crossdressers, tv’s, tgirls or just that girly boy with a pair of hose waiting for him underneath his pillow.

As for myself, I can trace back my infancy years of feminine crossover to stealing my sister’s knee high socks and happily masturbating (while, amusingly, not really knowing what “masturbation” meant at the time). Then it slowly progressed in my wee teens to actually buying Leggs pantyhose myself under the guise that “it was for my mom.”

By fifteen, my inner Sheery really came through and I actually bought my first camisole and panty set from JC Penney (I know, don’t laugh) which was the most nerve wracking, yet insanely exciting, experience I had ever had. I threw in some of the “premium” Hanes pantyhose while I was at it because, hey, if you are going to appear like a teeny bopper CD, then you might as well do it right.

Then came the best part later that evening. Putting on the pantyhose (no tighty whities on this time) then slipping on that turquoise camisole and panties. The climax I had shortly after was no where near the ones I would have with intercourse in my later years. Not that the future intercourse was average but I think I came on the ceiling that night.

From then on, I’ve never looked back.

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