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:

  • It’s exciting being a t-virgin and the only thing more exciting is to fulfill it with a “first time.”
  • I’ll finally be able to share my feminine persona with another. No one else knows (though some may suspect).
  • I’ll finally have the support from other transgendered people and the release of stress from having to keep myself bottled up all these years.
  • I get wet just thinking about being a slut.  Actually being one is making everything wet.

So here I am and I’ve decided that I want to get laid. No relationships. Maybe casual but secretive.

To counter any possible effect of weirdness, however, I’ve even gone as far as to prepare myself playing with a lovely phallic toy. Yes, sucking layers of plastic off the thing, testing the durability of my pseudo-vagina, even practicing putting the condom on with no hands and hungrily sucking that oily crap off of it.

Last thing, of course, is force feeding myself my wonderful love juice. A bit salty but not bad at all.

I found that throughout my “training”, the weirdness factor started to dissipate and I now I can’t get the thought of tranny to tranny action out of my head. A green light signal? I think so.

So I’ve update my lingerie closet and made a trip for some fine Italian pantyhose for an encounter bound to happen very soon. Not to mention, shaved. That’s probably important, right?

Keep you posted…

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Posted in Erotic Stories
8 comments on “Desperately Seeking Susan
  1. mightbe says:

    suppose it is too late but here I wonder if there is any others wondering and wanting…afraid but eager…. just wondering

  2. Sheery says:

    No need to rush hon but it does help to have a few other CDs for support whether online or in person.

  3. Charlie says:

    Oh my, we seem to think so alike! I have been a crossdresser since I was a little boy and the memories are so vivid. Like most I was raised hetero and took comfort in the broad statement “95% of all crossdressing males are hetero”. I call bs on that one! I got older and the dressing became more important and I noticed a desire to have a little fun. I couldn’t wait for my wife to go away at times so I could dress up and go out. I would flirt with men and finally after a few drinks I found myself realizing that I was enjoying it with the same arousal I used to have when I was intimate with a girl for my first time. I confess that I couldn’t resist the flirting and have given in many times, when I am dressed as Monica and have had a few drinks I get a little slutty!

  4. Sheery says:

    I’m raising my cocktail glass to cheer you. Ting.

  5. Rick says:

    Greetings all,

    I have been a crossdresser for over 30 years. I used to pride myself as a hetero and justified it by telling myself and others that I was fully committed to my wonderful wife. I realized that while I could be fully committed to my wife, that whenever I wore pantyhose and high heels, I would surf for any type of pantyhose photo: beit a male or female model. Over time, I realized that photos of men wearing pantyhose excited me as much as photos of women wearing pantyhose. Photos of nice, hard cocks spewing huge loads of cum through the pantyhose began to overtake the photos of women in hose.

    At that point, I determined that I was probably a pantyhose bi-sexual…..only interested in cocks when they were encased in pantyhose.

    Since then, I’ve had several pantyhose-related bisexual experiences, whereas I sucked a hosed cock in a gay bar in Norway, I went to a drag queen event at a club in London, UK, and I let a guy stroke my hosed cock to an awesome orgasm at an adult XXX cinema theatre here in Ottawa, Canada.

    It culminated last month with having a pantyhose-wearing guy join me in my hotel room while I also wore pantyhose. I took his hosed cock inside my mouth and enjoyed it far more than I would have expected. Meanwhile, after taking my hosed cock into his mouth for about ten minutes, he decided to pull down the waistband of my pantyhose and he took my cock directly into his mouth. As he was a seasoned cock-sucker, it took only a few minutes for me to announce my explosion. He told me to cum directly in his mouth so I did…..he swallowed my entire load, more proffessionly than any women I have ever been with.

    So now my question is…..should I repeat this bi-sexual experience or do I try to get my wife to join in next time???

    Your feedback is most welcome 🙂

  6. Charlie says:

    Once you tell your wife that’s a bell you can’t “un-ring” so unless you are certain you can handle what you see as the worst case scenario I’d recommend against it. Just my thoughts.

  7. Sheery says:

    It´s a tough call and depends on how open your wife/girlfriend is in general. Each case is different but I would recommend ringing the bell. If things don’t work out it may be for the better.

  8. Sheery says:

    I’d never recommend going behind your wife’s back to explore your fantasies (though it does sound exciting!) but maybe now would be a good time to SLOWLY introduce her to your love for pantyhose. For example, start by buying her a favorite brand of yours and telling her she would incredibly sexy in them.

    Once your wife feels more sexy to you, then things can get a little more interesting from there 😉

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