Posted on March 2, 2012 by Sheery — 2 Comments
Lovely tranny in teddy and some shiny pantyhose
What I recommend to a date (Flickr: The Poss)

This is part 3 of the tale of my first romp with a transvestite. Read part 1 for the prelude and part 2, the hookup.

Action time! I break out of my “disguise” of jeans and t-shirt to reveal my silky fuscia babydoll and Wolford pantyhose to the lovely Racquel. What a feeling of finally sharing my sexy girly side with another.

My girly cock was thinking the same thing too.

I lied down on her bed and caressed her black stockings with my hosed legs as she approached me. Then the unthinkable happened. She begins to strip down the Wolfords. Uh-oh, instant turn-off.

I don’t think Racquel particularly minded the lingerie and pantyhose (I believe she even called it “cute”) but only saw it as an obstacle to her real desire: get right to the cock.

Ok, so I know we’re not exactly two lesbians going at it but thoughts of manly gay sex began going through my head enough to cause a panic. I always envisioned myself a woman going at it with another hot woman, not two men who put aside their femininity to fuck.

In other words, the Wolfords and the babydoll had to stay on to preserve the “womanly” nature of the fucking.

Fortunately, Racquel played along, began to make fun of me (nicely) and pulled out a pink lace babydoll from her closet, then asked if I like it as she slipped it on. Actually she said, “Will this do, honey?”

Yes it will.

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Posted on February 27, 2012 by Sheery — No Comments
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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Posted on February 20, 2012 by Sheery — 8 Comments
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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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 6, 2012 by Sheery — No Comments

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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Posted on February 3, 2012 by Sheery — 4 Comments
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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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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