Insatiable

While writing that last post, I mentioned knowing that if I had no boundaries, I would wank myself to death. I thought I had written about this before, but searched for it throughout my writings, to no avail. I wanted to link to the article I thought I had written, as a case in point. But there is no such article. Therefore, here's a little story about my insatiability when it comes to feminizing myself.

One evening, with my wife out of town for a bachelorette party or some such, I had decided to make full use of her absence to engage in as much girlish debauchery as I could handle. There was so much that I wanted to wear, and in only one night, that I hardly knew where to start. I have limited ability to recuperate at my age, so every wank must count.

Usually, when she's not far away, I have limited time to enjoy my femininity. I browse around the web for things that interest me for a while, which normally feeds some specific fantasy. I then fulfill it by wearing whichever girlie item fits the fantasy best. Sometimes, I'm already obsessed with some specific garment, and develop an elaborate fantasy around it. In any case, it's over after one wank, so I prefer my fantasy to match what I'm wearing, to maximize my pleasure. At times, this isn't enough to satisfy me, for various reasons. I actually keep a diary of every "incident", including what I wore, how much I enjoyed it on a scale of 1 to 10, and a brief description of the circumstances. Merely documenting this after the fact often launches me into another fantasy, so I find myself wanking again in another garment. This second orgasm is usually much harder to achieve. Interestingly, when making love to my wife, I can never muster the lust to come twice.

On this particular evening, I knew that I had all night. I was ravenous for femininity. I had a plan. Since I had no fear of interference, and total privacy for many, many hours, I decided that I would spend the evening wearing nothing but women's clothes, and sleep in my wife's little slip dress that she left behind under her pillow. I had fantasized many times about doing this, but inevitably my playtime would end after succumbing to the temptation of orgasm. This time, I was determined to at least see how long I could go, and try to avoid masturbating.

I whet my appetite browsing the web for the usual: pictures, stories, captions, videos, and so on. I probably wore swimwear while doing so (my records are sketchy, so I'm not sure). I tried to hold out, but probably lasted only an hour or so. In spite of my ambitions, I achieved my first climax quite quickly after all that preparation. In fact, it was too quick to be fully satisfactory. Thinking of my original plan, rather than giving up right then and there, I changed into a bikini. The thought of actually executing on my plan was so arousing that I couldn't resist coming again, soon after putting it on.

By now, I was already tired. My penis was sore from having climaxed twice. With resignation, I cleaned up the mess, and thought my valiant attempt had no hope of continuing. But there again was that thought: now that I've gotten it out of my system, I can surely wear women's clothes without having to masturbate. This would be somewhat less fun, but satisfying nonetheless, on an entirely different level. I slipped into my corset, stockings and high black boots, figuring that if I was going to do this, I might as well challenge myself.

I settled onto the sofa in my lingerie to watch a movie. I spoke to my wife on the phone. The whole time, I counted my blessings that I could wear such an outfit. I lounged happily in my feminine attire, fondling the lace of my panties and the smooth nylon of my stockings, snapping my garters, and adjusting my bodice. Before long, and much to my delight, I gave in to temptation yet again.

At this point, I would normally start feeling a little ill from all the strain, and more than a little over-satiated. And so it was then. But I had a seed in my head. I felt like I could go no further, but by now I was wondering if I even could cum if I tried. I struggled a bit to think of what I'd want to wear, but the very idea of being such a sissy that I could still climax after everything I had already done, spurred me on. I chose my favorite swimsuit, and carried on, knowing that I still had to somehow sleep wearing panties and a nightie.

It was less difficult than I had thought. It was somewhat painful, as with an overworked muscle, and it hurt to even have an erection, but the overload of femininity was too much to keep me from succeeding. I came again!

It was late by now, and I was exhausted. I felt like there was no amount of masturbation that would cure me of this fetish. All I had to do was allow myself to fantasize, and I could keep cumming over and over again. The idea that this dirty little fetish was impossible to satisfy made me want to come yet again! Somewhat unnerved, I slipped into the nightie and panties as planned, brushed my teeth, and went to bed, excited about sleeping en femme. I was drifting off to sleep, and just wanted to enjoy some sweet girlish dreams. I tried not to think about what I was doing.

It was no use. I woke up in the middle of the night with a massive erection, throbbing with the dull pain of muscular fatigue. I would not be able to sleep until I wanked it out, so I once again satisfied my urges.

By now there was no longer any doubt. I had discovered that there is no practical limit to my arousal when indulging my feminine fantasies. I could literally wank myself to death if I allowed myself to. It was also both arousing and disconcerting to confirm that my ample appetite for straight heterosexual intercourse was far smaller than that for feminization. This was not surprising. That the latter was limitless, was.

By morning, I was so worn out and so sore that I couldn't imagine how I would explain to my wife why I wasn't eager to fuck her when she returned. I schlepped around all day in a fog from my exertions of the night before. I had only now, after all these years, discovered the magnitude of my problem.

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.