Testing the waters

The truth was, I wasn't really sure what I wanted. I liked how my softer, hairless body felt but I had never really thought about actively becoming more girly. Having said that, as I browsed women's underwear online my cock seemed to decide for me, my erection painfully hard as I thought about the soft fabric of some of the garments sliding over my skin.

It took a few sessions of browsing before I finally took the plunge and ordered. I selected a three pack of cute, girly hipster style underpants. They didn't look that different from guy's briefs really, and I figured I could probably get away with wearing them to school without anyone noticing. I also picked out a simple black thong, the hours of looking at female models proudly displaying them, and their butts making me eager to see how my own compared. Finally I added a pack of simple nylon stockings, curious about how it would feel to slide them up my hairless legs.

It took a few days for the order to arrive and to my surprise I found myself getting more and more impatient for it as time wore on. When it did finally arrive I eagerly tore it open and inspected my haul. The briefs were far skimpier than I had envisaged, the front of them so tight that they mashed my cock and balls up into me such that it looked like I barely had a bulge. They also didn't quite cover all of my butt cheeks, leaving about a third of them exposed at the bottom. Despite this they were actually quite comfortable once I got used to them and after walking around in them for a while, my balls stopped aching altogether. I was particularly pleased with how they looked in the mirror. When I posed, no matter which angle I took they looked amazing and my butt looked just as cute as any of the models I had seen online, except maybe mine was a little chubbier. I was definitely pleased with the purchase.

Next I tried on the thong which was even tighter at the front. It felt as if my cock and balls were actually being pushed back inside my body by the tight fitting garment. What's more is any attempt to stretch some more space into the front for my package only served to pull the thong deeper and harder into my ass crack, something I soon discovered, I didn't really mind. In fact, once I started to walk around in it I found myself enjoying the sensation more and more. The constant pressure on my hole was intoxicating, as was the feeling of my nude cheeks rubbing together. Soon I found myself sashaying about my apartment, swinging my hips wide to fully experience the new sensations the thong was giving me. Again I was thrilled at how my butt looked in them, unable to see a noticeable difference between my own ass and that of a sexy young woman's.

Finally, I tried the stockings. I was not ready for how utterly amazing they felt, as if my entire lower half had been swallowed up by something soft, smooth and sexy that just made me want to wriggle and squirm. Again I paraded about in them, relishing how they made me feel and when I bent before the mirror on my hands and knees and looked back over my shoulder I thought I looked so fuckable I almost came on the spot, soiling them.

I hastily took off the stockings and packed everything away, the rest of the night taken with thoughts of what I would try out first, at school and what the reaction of my team mates would be.