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Posted on December 10, 2013 by Sheery — 3 Comments

Black Body Slip with Black Pantyhose

After going through my treasure trove (read: massive suitcase full of lingerie, pantyhose, tights and other womanly things) one recent evening, I came across an item that I have had for over twenty years now. What better way to bring back the old memories of this lovely charm than to slip in on for old times sake and see if I still “have it.”

I remember buying this body slip, when I was sixteen, at a JC Penney after seeing an ad from the Sunday paper. I recall thinking that I absolutely had to have this while, at the time, I was experimenting with wearing lingerie for the first time. Lingerie, along with my teenage pantyhose fix, made me horny like nothing ever before during my youth in those days. Even more so than girls.

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Posted on November 28, 2013 by Sheery — 2 Comments

Leg Warmers with my Tights

If you haven’t lived through the 80’s like I have then, unfortunately, you were unable to experience the era of leotards and tights in the crazy Jane Fonda inspired workout days. What always accompanied those shiny multi-colored tights of those days was a pair of leg warmers scrunched up and beautifully worn on the lower legs.

Oh, the love in remembering those days is always recalled every time I see them worn, usually over thick tights on a cold winter day. While probably not the “it” thing in fashion at the moment (though in my book, all the rage), you can still spot them around here or there on lovely women whose legs get a bit chilly in the cool air.

Of course, sitting at home in my own pair of thick, shiny suntan colored JC Penney tights, my legs also get a bit cold. That’s when I grab my pair of matching tan colored leg warmers, sitting dormant for the last six months and slip them over my tights. A much better alternative to pants, wouldn’t you think?

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Posted on November 4, 2013 by Sheery — 1 Comment
Daring Teddy with Pantyhose
Image: Pantyhose Swish

A little over a year ago, while on ebay, I stumbled upon a gorgeous red teddy that I couldn’t take my eye off of. It was made of a beautiful red lace with a bikini-tie back and a lace halter at the neck that tied up as well. I remember shelling out quite a sum for it and being only mildly satisfied once I received it.

I have always had my pantyhose fetish, of course, but when I find a piece of lingerie I like I have to have it. You can call it my other prized fetish if you will. Yet this one basically became just another item in my lingerie drawer collection. Kind of fetish-worthy.

Even when paired with some sexy Silvia Grandi pantyhose, it looked great on me I thought, but it didn’t just have that spark of sexiness that I look for while wearing my lingerie. Maybe it would be something saved for a special date around Christmas time. In other words, forgotten.

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Posted on September 15, 2013 by Sheery — 2 Comments

Men's Shop

I have to admit, I’ve had a little trouble coming up with something for you to glance over then move on to your sports, porn or whatever. Maybe it’s something to do with with the fact that my ability to write here is directly proportional to how “in the mood” I feel, usually when I’m all glammed up.

And for a while, the last few weeks at least, it’s been no glam at all. 100% Pure unadulterated masculine me (almost masculine anyway). Yeah, yuck.

I bought a sexy new string body that I’m dying to try on. At the moment, it’s still in the packaging.

I have new vintage aerobics wear (and plenty of matching tights) for my indoor workouts. They’ve gone unused so far.

Just for kicks I counted all the pairs of pantyhose I had some time ago. Eighty pairs, all unworn in the last few weeks too.

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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 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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