Where Do We Go From Here?

Sheery in Fogal Rapallo pantyhose

I recently had an epiphany about my whole crossdressing life up until now. Primarily, I’m no longer a little teenie-bopper sneaking around with my stash of girly goodies waiting eagerly for a chance to slip into some pantyhose in my room with the door locked. Those days are LONG past. Yet, given how long it was ago, I can still remember my dress sessions rather vividly, as if it were my first time driving.

I’m not afraid to admit it to myself that crossdressing is deeply rooted part of my personality. I love it, have an inredible passion in it and, well, I just happen to like throwing on a pair of pantyhose and getting off on it… for the last few decades. Is there really any harm in it? Ok, so maybe getting a snag in the nylons but that’s another story.

I find it of interest in my self-assessment, however, that crossdressing is obviously ingrained in my own sexuality. Before you go all Captain Obvious here, think about it. Man throws on pantyhose, some lingerie and maybe a wig and a little makeup. Then dot some perfume on for good measure before stepping into those heels. Typical crossdresser duties and was actually what I did just an hour ago.

Yet that’s where the silky things end and crossdresser me takes the stage. All five senses are heightened (yes, I can taste the “fruit” from my lipstick), arousal is taking it’s shape and I NEED, right then and there, to be missy me. No longer am I the weird dude with the feminine tendencies but rather a transformed me with feminine desires and feelings. And those desires now have to be met.

For most of my life, this has been done in the confines of being by myself to handle those raging sexual urges by… you name it, toys, positions, movies or even just grinding on the bed. It usually led to an orgasm ranging from drip drop to full on explosion. Afterwards, though, a certain shame and guilt was felt which would eventually pass (the taboo monster making a visit?). Then the cycle repeats. Sound familiar?

These days, though, I don’t have that shame. Ever. Not that it’s an OMG realization. I’m glad I’m comfortable with myself and killed off the taboo monster.

I think it’s pretty clear that I’ve accepted myself as the diehard crossdresser pantyhose freak but my sudden realization is that this will be a part of me until I die whether I like it or not. Now, duh, I’ve always known that this happens with crossdressers, anyway, yet I’ve always been in denial about it personally. I never would see my future self at 69 years old and wrinkly posing in my Wolford tights and ready to try on a new teddy.

That’s the reality though and now I’m ready for it. So what now?

Well, I’m just going to keep on living, day by day. I’ve become more open to sharing with others willing to share my passion and feminity as a crossdresser and have done so to wonderful experiences. That was the next step needed to get out of the wank myself on a Saturday night phase. A very satisfying step indeed.

Now, I have no idea where this will lead which begs the questions. Will I come out? Or steer toward being transsexual?

I can say, at the moment, neither of those is under consideration. Given my lengthy process of self-acceptance, however, the possibilities are very real. Tomorrow is another day.

(Shhh, I secretly always wanted boobs though)

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Posted in CD Diary
4 comments on “Where Do We Go From Here?
  1. Glossy says:

    WOW!!! Looking very sexy. Crossing dressing is engrained in my psyche as well it is part of who I am and what I enjoy doing. As I am writing this, am suntan pantyhose and 7″ stilettos wearing a purple, pink, and red dress feeling very feminine. Although, I am not much into wigs, breast forms and make-up.

    When I go out I dress like you in the picture with heels, pantyhose, short shorts and a blouse or some other woman’s top. By the way what pantyhose are you wearing, I definitely got to get a pair. The heels look good on you and I have shorts similar to what you are wearing, but I don’t have a top like that. You’re rocking the look, so hot!

    I am glad you killed the taboo monster. Taboos only hold people back. You can feel confident expressing yourself any way you wish. That is the philosophy that I apply to everyday life.

  2. Sheery says:

    @Glossy Thank you for your kind words! And you’re a mighty brave woman to be rockin’ the 7″ heels. Don’t injure yourself! Sheery

  3. Gigi says:

    Looking astounding here! I really enjoy reading about your journey…helps me deal with the guilt you speak off ans cheers me up. I ordered an Aneros massager for my birthday next month and started to keep myself smooth and clean everywhere. I still fancy girls, not “macho” men, but the more I think about it…I dunno what I would do if I met an elegant CD….

    Heck, I already chosen my girly name and I am starting to care less and less about checking in a box…so who knows!

  4. Sheery says:

    @Gigi A good girl always keeps herself pretty 😉

    It’s nice you have a good attitude about being a CD, that is caring less about “checking in a box.” Taking it day by day and becoming more comfortable in yourself makes the CD life get a lot better.

    X Sheery

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