Jack & Jill - his first time with a transexual

I pulled her hand and started us walking across the parking area toward my hotel again.

“I’m sure I can deal with it Jill, whatever it is,” I said confidently while pulling her along.

“Just be gentle with me, please,” Jill said in a pleading sort of manner as we walked.

“I promise,” I told her, meaning it.

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We had held hands up the elevator and down the hallway to my room. Our body heat and flushing cheeks that told the entire story of our attraction.

After we entered my mini-suite and walked just as far as the small couch, I felt Jill’s hand on my ass and we turned into a passionate kiss. Our tongues lashed as each other and we were filled with the exhilaration of hot lust being fueled by tasting the first morsels of what would become a banquet of sex.

As we groped and rubbed our bodies together and began to explore with our hands, we fell lightly to the sofa without parting our mouths. I was enchanted with Jill’s olive, smooth skin and sensual looks and even more delighted to find her wearing high quality, lacy lingerie under her blouse.

Her small breasts were swollen and encased in a front-clasp bra through which her hard nipples could be seen as they pressed hard against the feminine fabric. I had much practice with this type of fastener and easily liberated her breasts in one quick, one-handed move.

As I kissed my way down her slender neck, Jill was moaning and breathing harder. When I brushed my hot tongue across her nipples, her back arched and she pressed her chest toward my mouth for more.

While I bathed her nipples with my tongue my hands began working around to her hips and lower back. I began to unbutton and unzip her leather skirt and she assisted by moving in just the right way.

“Jack,” she said breathlessly. “Please promise me again that you’ll be gentle.”

It sounded as if she was imploring me not to hurt her making me think that possible she could be a virgin. I didn’t mind and it wouldn’t be my first time but, I found it hard to believe given our ages and her overall sexual confidence.