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Posted on May 15, 2013 by Sheery — 1 Comment

SOH Charmeuse teddy (with Wolfords)

As I sit here painting my toenails today, like a good little girl, and anxiously await my outfit for my night “out,” I finally receive that long awaited ring at the buzzer. Yes, it’s a package! I’m a bit nervous since that means I’ll finally out myself as girly me for a few moments in the next day or two. I’m eager to try on my first fem outfit however.

Hold on a second. I think this package is smaller than expected and begin to wonder if the club shorts and dressy top are skimpier than I had thought they would be. Then I rip the package open to find a gorgeous charmeuse teddy (Shirley of Hollywood). Oh, right, I forgot that I ordered lingerie about a month ago after coming home after a night of drinking with the chums.

Well, I can’t throw this on and take this out on a stroll around the block. At least not yet 😉

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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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Posted on April 17, 2013 by Sheery — 2 Comments

Wearing a Teddy with Danskin TIghts

I woke up refreshed but feeling unusually horny this morning. Enough so to make slide into some shiny Danskin tights, throw on a cute black teddy then into my usual bathrobe. I can’t remember what I dreamed about last night but it really has me in a feel sexy mood today.

After my morning coffee, I skip reading the news and head directly back to my bed and pull out the vibrator from a drawer nearby. It’s nice and slim, smooth and about six inches long which is perfect for some womanish masturbation.

I unsnap the crotch on my teddy, turn my little toy on and, remembering an idea from somewhere online, begin to penetrate my ass but through the pantyhose. The stretch on the tights limited penetration to just a few inches but it was all that was needed. Oh, did it feel nice and incredibly kinky at the same time!

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Posted on February 28, 2013 by Sheery — 41 Comments
This teen's favorite hangout (Flickr: sshb)
This teen’s favorite hangout (Flickr: sshb)

From my perspective, one of my biggest fears as a in-closet crossdresser is being caught by someone who notices the tiny speck of nail polish remaining on my finger which I thought was completely clean. That or she notices the strap of my teddy just barely bulging through the sweatshirt I wear over it.

Those were two separate incidents, with me out and about in the city, where I didn’t know the other person. I initially try to avoid, at all costs, any revelation of my feminine attire since it makes me extremely embarrassed. Yet I notice that, as soon as the “shame” subsides, I am left with a gratifying feeling.

Is this how an exhibitionist feels, I wonder? Yep, I think it does.

Actually I can recall one of my most unforgettable moments, exposed as a crossdresser, starting out as an embarrassing situation and leading to a rush of sexual tension.

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Posted on February 15, 2012 by Sheery — 19 Comments
Transgender symbol
Credit: Wikipedia

For as long as I can remember, crossdressing has given me a feminine side that I truly couldn’t live without. Also, as long as I can remember, I’ve always been what they would call “hetero” with typical vanilla relationships with women.

Being the coward I am, I’ve never been able to share my alter ego with any of my past girlfriends. God forbid their reactions or, gasp, laughter if they reject my inner woman. Worse, what if one of them let the cat out of the bag to one of my friends? I’d have some explaining to do.

In that time, though, the inner woman grows up and wants more out of herself, to look more passable, be more sexy.

Not to mention feel more like a woman would too.

Ok, that is somewhat difficult since there is that matter of male genitalia getting in the way even though it’s used to enhance the “female” pleasure. Let’s not lie though. Wanking it is about as male as it gets and, after years of rinse and repeat, is about as vanilla as the hetero relationships too.

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Posted on February 12, 2012 by Sheery — 3 Comments
Sexy Lingerie
Around the corner (Flickr: LaggedOnUser)

I guess I’ve talked about pantyhose enough thus far and, what can I say, it’s an integral part of me being Sheery the crossdresser. It’s my favorite “partner” turning me on anytime, anywhere she wants.

Once in a while, I wear only pantyhose when I feel like it but they are an absolute requirement anytime I change en femme. When I get in my real girly mood, though, the “look” just doesn’t seem quite complete without its complementary pieces.

Namely, fine lingerie.

For some reason I have an odd relationship with lingerie. Sure, there are the favorite items, some of which, I paid quite a price to get (but look so good in). When you think about it, too, lingerie should make you feel more intimately feminine than anything else you could slip on.

Shall I say, even more so than pantyhose.

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Posted on February 9, 2012 by Sheery — 17 Comments
Pantyhose Collection
The Best of The Best

It shouldn’t be news to anyone. Yes, I love to slip on one of my hundred or so pairs of pantyhose and change into my feminine side. Sometimes I’m left wondering, though, why am I left massively horny even after the ten thousandth or so time this happens?

When you think about it, a pair of pantyhose is just inanimate garment of nylon and spandex with a little color thrown in. Not exactly in porno flick or blow up doll territory. Fairly innocent to say the least.

Of course, I could go into the soft clingy feel on my legs and body or how I love checking out in the mirror the shine they leave on my legs. Yet, I sure as hell don’t feel the same way when putting on a tight pair of jeans. Shine alone isn’t exactly something I have a severe fetish over either. I’m not a moth.

Then the answer dawned on me. Let’s just say, hypothetically, that pantyhose were acceptable in society to be worn, not strictly by women, but equally by both sexes.

So we have…

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Posted on February 1, 2012 by Sheery — 7 Comments
My first memories were blue
My first memories were blue (Flickr: Sumlin)

I’ll be so kind to admit it right now. I’m in my late thirties and, using my sharp math skills, have spent the better part of thirty years as a crossdresser. Even as a lot of time has passed since my first days across the border, I’ve always found myself trying to recall those first moments that would bend my gender the rest of the way.

No, I didn’t raid my mother’s drawer of bras and pantyhose. No, no one decided they would have some cruel fun, dress me all girly and proceed to laugh at me.

It actually can be traced back to first grade in grammar school and my beloved teacher, Mrs Rainwater. I can vaguely remember what she looked like. Things like her youthful face and short curly hair.

I remember one detail about her rather vividly and something that bonded me to her back then. She always wore blue knee-high socks on some days and on other days, blue pantyhose.

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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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