Online Gender Switch

He realized that she had made a fool of him when he opened the drawer and found… a driver’s license that showed Sheila was actually named Simon.  He contacted Sheila on a dating site where she disguised herself as a female who was looking for intimacy with a male.  He figured that Simon or Sheila was experimenting with her identity, switching to see how the other half lives, and relying on the anonymity of cyberspace to express her feminine side, which he or she would otherwise normally hide.  When he confronted Sheila, she told him that at 18 months old, she began exhibiting very strong female characteristics and her parents thought that she would grow out of it, but by the time she turned 4, they realized that this was not a passing phase and they let him transition into a girl.

Sheila said that she knows that physically she is still a boy, but in her heart, she knew that she is a girl, and she has always been a girl.  Sheila told him, “Boys will be girls when their gender identity differs from the sex they were given at birth.  I’m in the right body now, and I feel good.  I began playing with princess dresses and dolls at a young age.  I wore skirts, first at home and then out, along with glittery shirts and skinny jeans, and eventually I grew my blond hair long.  I just started wearing a padded bra and taking hormone blockers to suppress male puberty.  Last year I had my name legally changed from Simon to Sheila, and that is my old driver’s license.  I am not out to trick you, and this is not a game for me and if you think that I deceived you, I understand, but I didn’t know you well enough to share all of my secrets with yet.  I was unsure about joining this dating site, especially since I am just looking for someone to treat me with respect.”

He said, “I was attracted to you because you’re a woman, and I think that you are a very hot looking woman.  I don’t feel that it would make me any less of a man, or any less straight, if I were to date you and there is no need to keep this a secret, as I am open to being in a relationship with you, if you will have me.  I see you as a beautiful butterfly and I want to get to know you for the woman that you really are.  Wanting to get romantically involved with anyone is difficult, as you are setting yourself up for rejection, humiliation, and disappointment, but I think this could work for us as you are a straight woman looking for a straight man.  I will always give you respect and offer you encouragement so you can flourish as a woman.”  Sheila said, “Next month, I am getting rid of my penis and having a vagina installed.”

Written for Fandango’s Story Starter #23.

12 thoughts on “Online Gender Switch

    1. It is a trick situation dating someone who has switched genders, as these people are more likely to attempt suicide, so you need to be very careful not to hurt their feelings.


  1. I’ve never actually met any transgender individuals, but I’ve known a few from on-line. Oddly it’s always the male to female gender too. I have never had any desire to be a man. I think it must be so complicated, and then that whole penis to vagina thing is pretty strange (IMO, but I’m not transgender either). I watched a documentary once about a couple who were both transgender. Now if you think getting the dick whacked and turned inside out is tricky, what about the other way ’round? The logistics of that make my tender parts hurt. 😬 I think those individuals who feel they were born ‘wrong’ have it tough. It is best to be non-judgmental and kind as possible.

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      1. 🤣 I hope the now man who was once a woman has plenty of athletic supporters. It could take getting used to, that’s for certain. When it’s done the other way ’round, the junk is getting tucked away, which minimizes the whole slightly unbalanced look.. do you suppose they call that one a “takeadickfromme-ectomy?”

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