Peeking Outside the Closet, I Like the View! (Part 2)

Lacey camisole, shiny pantyhose

Lacey camisole, shiny pantyhose

This is part 2 of the tale of my first romp with a transvestite. Read part 1 for the prelude.

Just to recap, I was on the verge of taking a major life turn by venturing out of the lingerie closet and into the transgendered world. Just some mingling with the gurls.

In other words, I was starved for a girly hookup. So why not just do it? Mosey on down to the nearest gay bar or, even better, a gay-friendly neighborhood and everything will probably take care of itself. That was the plan anyway.

Time to prepare. Shower, shave (everything of course), clean out my ass and slip on my favorite silky fuscia babydoll and some Woldford pantyhose. OK, I’m an absolute little bitch when it comes to going out in any kind of en femmme, so a disguise of jeans and a t-shirt went over these.

Alright, take a deep breath. Time to head on down to the gay district, toward the evening time, like a lamb sacrificing itself to the wolves.

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Desperately Seeking Susan

Oh Susan, where art thou? (Flickr: Tractorpirate)

Not too long ago, after a failed attempt at seducing a (real) woman, I came to a sudden conclusion.

A little background first. It has always been a deep, dark fantasy of mine to hook up with another transvestite counterpart but living it out in real life carries some issues, especially for a crossdresser that has been hetero all her life.

  • I’ll be crossing into the bisexual barrier with no turning back. I have nothing but respect for being gay or bisexual, but it’s a major decision for someone who has has only known being hetero, you know.
  • What if I don’t like the experience? Will I feel “weird” and require therapy? Ok, maybe the therapy is a stretch but they are plausible questions.
  • Will I find myself transforming from a closet crossdresser to a full time transvestite? Again, it’s a major decision and requires a major life change.
  • Will my friends, oblivious to my crossdressing, eventually find out? I live in two distinct worlds that haven’t collided yet.

Of course, with the cons come the pros:

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Crossdressing to Bi-Curious, Did I Miss Something?

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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This Crossdresser’s Other Vice, Sort Of

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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So Really, What Makes Pantyhose So Arousing?

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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I Might Have to Check This Out, Now

I found this the other day while browsing The Gender Center website (Australia)

http://gendercentre.org.au/index1.htm

Really, though, I have to respect the service they are providing:

The Gender Centre is also committed to educating the public and providers about the needs of people with gender issues. We offer a wide range of services to people with gender issues, their partners, families and friends in New South Wales. We also act as an education, support, training and referral / resource Centre to other Organizations and Service Providers. We specifically aim to provide a high quality service which acknowledges human rights and ensures respect and confidentiality.

I believe that is suppose to be spelled “Hosiery” in their description. I let them know, don’t worry.

Now where do I sign up?

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All En Femme and Horny, Now What?

The lovely transvestite, Lauren Close

Credit: Lauren Close (Flickr)

As is customary, we as crossdressers or transvestites find those moments where we can’t resist entering our inner woman and bask in the satisfaction that immediately results. For me, that means stripping naked, shaving (not just the face honey), a shower and choosing some silky little things that I’m in the mood for.

Let’s see, some Wolford tights and heels making my legs unbelievably sexy, check. I’ll go with the nude today.

Hmmm, a black teddy, see-through in the bust area. Check.

Long black gloves, brown wig and lipstick. Check.

A little perfume to top things off (you really have to try this). Done.

It’s incredible the intensity it brings admiring that “model” in the mirror, turning around for the butt view and making yourself more “wet” by the moment. Now that I’ve successfully seduced my better half, time to take it further.

Auto-erotic time since no one else around? Check.

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An Ode To My First Grade Teacher

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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Ok, A Little Bit About Me Before We Go Forward

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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Welcome To The Confessions!

Me and my black Danskins

Me and my black Danskins

Hello and thanks for paying a visit to the Confessions!

As for me, I’m Sheery, a still-in-the-closet crossdresser who is tired of keeping this life long secret forever. What’s the fun in that? Despite my extreme timidness of exposing my alter ego, I’ve slowly been trying to incorporate my feminine ass into the world we like to refer as transgenedered.

Long story short, I’ve been a crossdresser for, oh, as long as I can remember. I guess you can say I’ve progressed from just slipping on a pair of hose to trying out a bra with it to now going the full cover of a women. And loving it too!

Sadly, there is only so much fun that can be had when there is only yourself to look at and admire in the mirror.

So now, I find there is a whole world out there of sexy crossdressers and TV’s that I want to reach out to, not to mention, maybe one day give in to my “lesbian” side and explore the boundaries of my femininity that’s never before been crossed.

So slip on your favorite tights, maybe a lacey babydoll, prop yourself up in those stilletos, then add a little lipstick and stay tuned. You’ll see nothing here but erotic thoughts, news and other interesting stuff happening in TV land. Though with a primary focus on the erotic thoughts 😉

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