Jack & Jill - his first time with a transexual

Jack and Jill meet

It was when I went to the patio to enjoy a cigar after dinner that we met.

On the road for business, I found a decent bar and grill near my hotel where I was welcome to enjoy a fine smoke. I had dinner and then moved outside for a relaxing smoke in the cool weather. I lighted a Churchill-sized stick and after a few minutes of solitude, an exotic looking brunette spoke from just behind and to the side of me.

“I love the smell of a fine cigar,” she said in a sultry voice that got my attention.

I turned to look as she moved forward into my view and was pleased to see a young woman dressed in a red formfitting top with a leather mid-thigh skirt, and more importantly, luxurious long dark hair as straight as if ironed.

“You’re welcome to enjoy one for yourself if you wish,” I said while politely standing to greet her. “I’m Jack,’ I added as I extended my hand to take hers lightly.

“Jill,” she said with a smile and laugh.

“No kidding, Jack and Jill?” I questioned.

We both had a short laugh and I motioned for her to sit across from me. When she sat down I got a great look at a long pair of tan legs and was impressed with the slight curve of her hips, slender torso, and just right sized breasts.

Now I was looking at her, face level with mine, and saw her dark eyes and lusciously thick lashes. She was exotic in that she was part Asian, possibly part Anglo and almost had a look of a Latina as well.

It is quite sexy to when a hot chick smokes a large sized cigar. Clearly it’s the oral phallus action but, there is also a sexy confidence to such a woman that I find attractive.

Jill allowed me to light the cigar as she expertly turned it, keeping it far off of the flame demonstrating that she was not new to the delights of a fine cigar. I was already hoping she was not new to other oral delights as well!

We visited for some time and she was obviously inserting and removing her cigar in as sexy a manner as you could imagine. It would have taken nothing more than her walking up to me to get me excited and thinking about sex with her. Add the sexy smoking, with the good conversation, and this became a pursuit I could not refuse.