Chapter 4

I wiped a drop of his seed from the corner of my mouth and carefully licked over his penis, cleaning the little drops of his cum that I had missed. I looked up into his eyes and we smiled at each other.

“Thank you, Sara,” he said, “for everything.”

“You’re welcome, Jesse,” I said, smiling brightly at him. “Now let’s finish getting you dressed.”

I watched as he opened his legs and carefully tucked his scrotum back. I was mesmerized by how, in just a few seconds, his cock and balls appeared to have magically vanished. I’d never seen anything like that before. Then he pulled up the thong and slid the little skirt up his thighs. I handed him the black halter-top blouse and he put it on.

“You need some shoes,” I said, noticing that he was in his bare feet.

“I’ve always wanted to wear heels,” he said.

I thought for a moment. “Jesse, heels won’t go well with that outfit, they are much too formal and that outfit is way too casual.”

He gave me a disappointed look. “Can I at least try?”

“Yes, of course you can.” I looked into my closet and pulled out a pair of four-inch, rhinestone, t-strap sandals. His feet were a bit wider than mine and I knew he’d never fit into any of my pumps.

He put the heels on and I helped him lace them up. Once we had them on, he stood up, took a few steps, and immediately began to wobble and nearly fall. I reached out to steady him and then helped him get back to the chair where he could sit down. I tried not to laugh because I didn’t want to upset him.

“I think you need a bit more practice before you’ll be able to wear those,” I said, trying as best I could not to giggle. His face broke into a big smile.

“You may have a point.”

“Let me find you something easier to walk in that will go well with that outfit.”

I rummaged through my closet again and pulled out my new pair of Cocobelle gilded leather sandals. They were flat, so he’d have no trouble walking in them. I helped him put them on and secure the little straps around his ankles.

“That’s perfect, now let’s check how you look one more time,” I said.

He stood up and moved beside me as we looked at our reflection in the mirror. He truly looked stunning, and I was a bit envious. He had naturally dark tanned thighs that went perfectly with the faded jean skirt. I looked down and admired his round, heart-shaped ass that looked impeccable in the short little skirt. Guys always go crazy for an ass like that, I thought. The dark, long, flowing wig matched his skin tone and makeup perfectly, and the stuffed bra gave him the illusion of small 34B breasts. They were just big enough for him to get a little attention but small enough to go perfectly with his petite frame. I was utterly amazed, as it was virtually impossible to tell he hadn’t been born a woman.

We both stood awestruck in front of the mirror for at least five minutes. Dressed as a man, Jesse was average-looking at best. However, dressed as a woman, he was truly stunning.