Not long after I moved into my own apartment I found myself gravitating towards very "different" porn sites. I used the standard sites often enough, and I always enjoyed fantasizing about the sex that I watched on the computer screen. But there were nights that I felt a different pull. I felt ambivalent about straight up porn. I decided that there were only so many ways that ordinary porn could arouse me.
But at the same time, I'm aware that these...tastes...are not "normal." Yet early on when I read content about such sites, the writers bespoke of "normal" as a word being bullshit. Normal was whatever you wanted it to be. Was it normal for a cross-dresser to be dressed up in women's clothing complete with high heels? Was it normal for a gay man to want to orally pleasure another man's penis?
It started with a fetish-based "dating" site. My profile was admittedly weak. No pictures, only generic information. But I reached out anyway, and I guess through my words got one reply. Yet it was a generic reply, but at the time it was golden to me. I spent a wild, crazy night in the throes of "her command" by stroking my cock per her instructions and taking pictures as proof. I had a couple more correspondences with her but it faded away. Yet the seed had been planted, for her second instruction to me was related to wearing panties.
I had never before considered wearing women's clothing. I can recall once after sex with a college girlfriend I suggest that I wear her panties. It was a badly formed thought, blurted out without any planning. She was horrified and I quickly passed it off as a joke - something I'd seen in a movie, right?? I'd never exactly forgotten but had never really considered it either. Now, I was being forced to consider it and I was suddenly aroused. Her words were as generic as the first command, but I didn't care. It was the concept of being in panties that aroused me.
In a fit of terrified erotic pleasure, I went shopping. Yes, I literally went to the mall to Victoria's Secret and bought a pair of panties. I literally was sweating and shaking as I drove to the mall, yet my cock throbbed and felt alive with the taboo actions. How would I approach the store? I finally decided that I would just walk in and shop slowly, as if I was browsing for a sexy pair of panties for my (nonexistent) girlfriend. I did exactly that, and walked slowly through the store, getting suggestions from a young saleswoman. God, I almost got a full erection in the store when she began talking to me, thinking about the pleasures yet to come! But I maintained control, and left the store with a couple of pair of skimpy, sexy, satin panties. The bright red high-back panties and the light pink satin pair sat in the bag on the front seat of my car and again I had a huge erection. I had to stop the car at one point and force my erection to go down; my next stop would not look kindly upon me walking around with a boner!
I browsed slowly in the sex toy store, making three complete revolutions of the store. I paused in front of the dildos, looking at the huge variety of latex toys. I hesitated by the cock rings. An image formed in my mind. This black leather strap/metal loop cock ring on over my pair of panties, and the dildo in front of me maybe for me to suck? Or maybe to slip deliciously into my asshole? I left with a kinky leather cock ring, a realistic looking dildo and lube. I drove home fast - really fast.
I showered. Some of the sites I saw about feminization had the men showering and shaving. Well, my job didn't permit me to shave and get away with it, but then no one would see my pubic region. So I shaved that. The proximity of hand and cream and movement and the thoughts of what it would feel like gave me a huge boner. I avoided it while I shaved myself carefully, though when I was done I gave myself a couple of reward strokes. I groaned aloud in the shower.
I stepped out and dried off, and quickly seated myself in front of my computer. The panties, dildo and cockring were laid out in front of me as I began to do my first internet searches. "Men in panties" was the first. I saw a picture, the man was wearing stockings and a garter belt to hold them up, and his cock was encased in a black strap encircling the cock and balls. He was erect and he had a thick penis. I gasped; the picture felt deeply erotic. I reached for the cock ring. Sadly it took me a few moments to figure it out, but then before long I had a leather strap encircling the base of my cock and balls. I had another strap looped around by balls. Both loops were connected to the metal circle that was now snuggled down at the base of my cock. I stroked my cock slowly, and groaned. The pleasure! The sensations were so different and so powerfully erotic that I almost came right there. Instead I let go, and watched as my cock oozed clear pre-cum. I scooped it up on my index finger and slowly brought it to my mouth. Should I? I did, and was rewarded with the pleasant semi-salty taste of the fluid.
Then, I took the panties and slowly pulled them up my leg. They were small and ended up being very tight on my body, unable to fully encase my cock ring-aided erection. But the soft, smooth sensation of the material was sexy on my skin. I stroked myself savoring the new sensations. God I was so hard! I used the lube and slipped my hand easily up and down my shaft. Oh god the pleasure! It was amazing. I knew that this pleasure could last a long, LONG time with me in that ring, and it was going to be wonderful. My mouth watered as I stared at the dildo and the computer screen. Mouth or ass? Mouth or ass? Fuck it - mouth. I closed my eyes as I slipped the realistic dildo into my mouth. And yes, I fantasized that it was a real cock. A real man. I was sucking a real cock with my panties on and my cock encased in a ring! I stroked hard and fast, my hand flying, my body jerking slightly with the onrushing orgasm. I gasped around the cock as I almost gagged on it trying to deep throat it.
But then the orgasm came. I released the dildo and leaned back in my chair. I looked down at my body and stared at the head of my penis, eyeing the hole. My cock felt hugely engorged and was deeply purple, and my balls were churning up a monster cumload. I stroked and moaned, almost unable to keep my eyes open, but I did and watched as my orgasm finally hit and the cum erupted from my cock. I watched as a huge, hot stream of cum blasted from my cock and soar into the air, and it landed all over my lips, nose and one eye. I gasped as the second, third and fourth blasts all did the same, splattering huge amounts of cum on my own face. Inadvertently my mouth opened and I tasted the strong taste of my semen for the first time.
Later, after I had calmed down (but not yet cleaned up), I reflected on how completely satisfaction that orgasm had been. Was it the panties? The ring? Dildo? I decided that it didn't matter. It was all of it. Thought I didn't "name" myself until much later, that one night of masturbatory bliss was the night I "became" pantywriter.
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