What Could Have Been

Often when I make myself feminine, I think back to some decisions I made years ago, and how different my life might have been had I done things differently.

I had been sharing the rent on a house with a co-worker some years ago, and secretly prancing around in all sorts of lingerie and swimwear. He had no idea. Still, I felt frustrated by my lack of freedom to express my feminine side all throughout the house. When he was out of town, I would take advantage of the opportunity without any fear of discovery. When the time came to move out, I decided that I would get a one-bedroom apartment and live alone, just to allow me the pleasure of living in girlwear whenever I wanted. I imagined ordering lingerie for delivery to my front door on a regular basis, with hardly any risk of discovery.

Pretty much as soon as I moved in, I met a girl, and she was coming over all the time, and we were having sex so often that I could hardly keep up. This naturally left me with very few opportunities to dress up. This same girl is now my wife, and the mother of my child.

The sissy thing to have done would have been to either get rid of her or involve her in my fetish for women's swimwear and lingerie, rather than keeping it secret. She might have stuck around if I had told her or shown her, but it doesn't matter: the point would have been to choose femininity over masculinity.

My garter slip

Today, while she was out, I risked wearing my garter slip, stockings, and shoes, for the first time since she almost caught me. While I luxuriated in the tight, soft fabric, I fantasized about how if not for her, I could have chosen a very different path. I imagine myself wearing lingerie every day in that old apartment, expanding my collection of panties and bras and bikinis and shoes and skirts and dresses. I would have masturbated ecstatically in a garter slip like this one, only instead of quickly cleaning up, hiding my girlish garments, and immediately getting back into my male clothes, I would have cleaned up and immediately put on some simple satiny everyday panties and gone on with my day. I know that if I had no boundaries, I could happily wank myself to death, never tiring of the femininity of it all. Eventually, I would have come out of the closet, so to speak, and become proudly transsexual.

These thoughts brought me to a quick but satisfying climax. And it's not the first time. Even now, as I retell it, I'm getting horny again.

Alas, it was not to be. And yet, I still think I made the right choice. I wouldn't give up my "normal" life, with my loving wife and beautiful baby, even for that. But I can still have fun now and then, pondering how it might have been.