The thought had, of course, crossed my mind before. It's not a huge stretch of the imagination. It's a bit of a joke, really. Masculinity is too fragile: the femininity of women's underwear must inevitably corrupt it. Women laugh and chide their men about how cute they would look in a bra. Then the men joke right back, playing along, intending to show how confident they are of their manhood. Both of them, however, fear what would happen if he actually did wear women's underwear. Subconsciously, both know how fragile masculinity is.
It came as a challenge at first. She dared me to put on her panties, and I did. No problem there. It was stupid. I felt ridiculous, but not even embarrassed. They didn't seem to fit quite right. They looked grotesque against my muscular ass and the bulge in front. Not a pretty picture at all. "See?" I said. "Nothing to it."
The trick is in not letting it get into your head.
As I said, this was a pointless exercise in courage. I showed off my machismo, my male fearlessness, by- ironically- wearing women's underwear. Clearly, she looks better in her panties than I do. In fact, she looks better in my underwear than I do. But that's because she's a girl, and I like the way she looks. As far as I could tell then, I passed with flying colours. The seed, however, had been planted.
I had practically forgotten about the incident, until it crept back into my thoughts a few weeks later. My mind drifted into an erotic fantasy as I worked. This happens to everyone. Only it abruptly stopped when I remembered that I wore __'s panties. For some reason, this suddenly brought me intense worry. I had, I imagined, compromised my virility. Thank God I hadn't liked it! I thought to myself.
As the day wore on, I agonized over my blunder. I worried that __ would think me less of a man. I tried to convince myself that I was being foolish. But it didn't work. The thought that there would be consequences to wearing women's underwear consumed me.
Eventually, __ assuaged my fears by fucking me passionately. She even initiated it all. She made me feel desirable as a man again. I forgot about it again for a little while. But it came back to me. Soon I became fascinated with __'s panty drawer. I considered myself fortunate that I hadn't worn a bra, too. Or a garter belt. Or that sexy little nightgown. Any of those would have made me doubt even more my manhood.
I had to prove to myself that I wasn't afraid, that I was still as manly as before. The only way to do that, I rationalized, would be to wear women's underwear again. I might even wear a bra and panties this time, just to prove it all the more forcefully.
I knew all along that I was lying to myself. In truth, I was curious. I wanted to experience __'s undies again.
I waited until I knew I could be alone for a long while, and stole into her dresser for a panty and bra set I had given her one Valentine's day. My heart pounded. My cock stiffened. I touched myself all over, overcome with horniness. I became frightened and took off __'s lingerie and put it back exactly as I had found it in her dresser. Oh my God! I liked it! My heart raced with both excitement and fear. I had compromised my manhood -- but worse, I loved it! I was still excited, but I couldn't bear the thought of wearing those panties again. I couldn't allow myself to capitulate. I had looked over the edge of the cliff, and survived. I couldn't go any closer. But it was so exhilarating! Naked, I came all over myself, fantasizing about the horrible, wonderful consequences of my gender-bending: that I would succumb to wearing all sorts of sexy girlie garments and eventually become a real girl! I never came so hard in all my life. I never felt such shame as when I cleaned it up. This would be the last time. I had momentarily lost my manhood, but now everything was alright as long as I didn't let it happen again.
How could I not agonize over this little discovery? The more I worried about my manhood's erosion, the more I fantasized about its inevitable result. My hands shook with anticipation as I rifled guiltily through __'s dresser for something horrifyingly effeminate to wear. I stumbled upon her one-piece swimsuit, and rapidly became fixated on it. There was no mistaking it for something a man would wear. My knees buckled as I thought of how it would squeeze my waist inwards and give me a gorgeous, feminine, hourglass figure. Still, I couldn't allow myself to feel this, no matter how badly I wanted to. I put it on over my own underwear, clinging desperately to my last shred of manhood. I had to resist. But there I stood, fondling myself, with a woman's bathing suit on me, on top of my underwear. If I don't let it touch my dick, it won't corrupt my manhood, I hoped. It was strange: feeling the spandex all over me except for my mundane, protected penis. It brought me momentarily to my senses. I took off the swimsuit in a pang of guilty sobriety, and put it back where I found it. I sighed with relief. That was close! Imagine how overcome with effeminacy I would have become had I dared to let it touch the essence of my manhood!
The very thought of giving up my manhood gripped me with intense, perverse delight. No sooner had I closed the dresser drawer than I doffed my underwear and wiggled into the same swimsuit, giddily confident about my new-found femininity. I gamboled around like a horny schoolgirl, rubbing myself all over, basking in the ecstasy of my new identity. I was so glad that I had done away with my feeble masculine protection. The realization that I was unprotected from such inescapable femininity filled me with great satisfaction. I came all over __'s bathing suit, relishing my girlhood.
Then, I was ashamed again. I had succumbed, and I wasn't excited about it anymore. I had failed to contain my urges. I secretly berated myself for months after that. __ never found out, because I washed the swimsuit before she came back.
It wasn't long until I caved in again. This was all part of my initiation. I had to renounce my manhood more and more often. Over a long period of time, I tried everything on. I knew that it was wrong, that it was abnormal, that it was dangerous, that it was eroding my manhood. I just didn't care. It was so much fun! Each time, I became possessed with the desire to feel feminine. I longed to feel something beautifully girlish on my body. I unleashed my pent-up womanhood by wrapping my body in lingerie. It was so. . . naughty. No heterosexual man, I reasoned, should ever be so familiar with women's underwear. I discovered things about women's underwear that most men would never be aware of. I no longer feared becoming effeminate: I hoped for it. I wanted to look as good in __'s underwear as she did. I wanted to be a girl.