Chapter 3

I watched as his eyes opened and it was as if his jaw had hit the floor while I stood beside him in my old torn t-shirt and ratty sweatpants. There was only one beautiful woman looking back at us in the mirror, and it wasn’t me.

It wouldn’t be exaggerating to say that in this newly transformed state Jesse looked like a model. Obviously not as tall as a model, because he was only 5’4”. However, because of his high cheekbones, soft feminine features, and the jet-black flowing wig, combined with my makeup job, I would have sworn Jesse was born a woman had I not known the truth.

It took him a full two minutes to speak. He just stood there staring into the mirror and I watched as his eyes went up and down his reflection as he studied every detail of the transformation.

“Sara, I ... I ... thank you,” he said simply. I could tell that he was ecstatic with what I’d done so far.

Now the last step. “What do you want to wear?” I asked.

“Honestly, I have no idea,” he said hesitantly. “Why don’t you just pick something out for me.”

Jesse and I were nearly the same size, so I figured he could just wear something of mine. I paused for a moment, trying to come up with something simple for him to wear. I rummaged through my closet for a couple of minutes and finally found a short, faded blue-jean skirt and a tiny black cowl-neck halter top. I desperately needed to do laundry so I didn’t have a large selection of lingerie to choose from, but after what felt like an exhaustive search I finally found a clean matching white lace thong and bra set.

I turned around and faced him and showed him the clothes I’d picked out. His eyes immediately lit up and I could tell he was happy with my choices. He stripped off the tank top and dropped his shorts to the floor. In an instant he was standing naked in front of me, his small erection standing up proudly. I now felt bad concerning the earlier remark I’d made about how small my ex was because Jesse appeared to be about the same size.

That didn’t seem to bother him, though, as he reached for the lace bra in my hand and began to put it on. He turned away from me so I could help fasten the little hooks in the back. He turned again to face me and I realized how ridiculous the bra looked over his flat chest. I thought for a moment and then grabbed some of my gym socks; I rolled them up into small balls and stuffed them into the cups of the bra, giving him the illusion of breasts.

He started to slide the thong up his thighs and then stopped; a perplexed look broke over his face and I could tell something wasn’t right.

“What’s wrong?” I asked. “If you don’t like that thong I can try to find another one, but I don’t have a big selection right now because I need to do laundry.”