A Ten-Day Feminine Getaway in Florida with a Date Night

My girlfriend participated in a paid photoshoot for an online magazine out in Florida. I drove down with her and spent ten days dressed entirely as a woman. We stayed at Cape Coral, inside the private home of the e-zine’s owner/publisher, known to everyone as “Parrothead” (PH). GF had mentioned us to PH before, and it turns out he is well-connected in the local “Lifestyle” scene. He arranged for me to go on a blind date with This T-girl Admirer, someone he knew personally. I was completely unaware that they had set this up behind my back.

We got there just before sunset on the 22nd. PH, his wife (Kat), and another girl from the shoot (Deb) invited us three out to a Chinese restaurant so we could relax after two days of driving down. That is when I found out about my date. So, GF did my makeup while I put on a white skirt, a violet blouse, stockings, and champagne-colored sandal heels with four-inch lifts.

Cliff was ten years younger than me but looked ten years older. He was quite large, standing nearly two inches taller than I am even in my 4-inch heels. He had slightly thinning sandy hair and steel-gray eyes. He sported that Don Johnson/Miami Vice style: a white sports coat over a crew-neck pocket T-shirt with crisp cuffed dress slacks. I gave him a quick hug and a peck on the cheek. PH, Kat, Deb, and my friend Ed headed off in PH’s car, while GF rode along with Cliff and me.

Cliff treated me like a proper lady throughout dinner—opening doors for both of us, holding out my chair at the table, all those little gentlemanly gestures you expect on a date. The food was excellent. We laughed and chatted away. After eating, we drove back to the house and dropped GF off. She had packed an overnight bag for me, so I spent the night at Cliff’s place.

We stopped by a beach shop in a strip mall where he bought me a string bikini—black with white polka dots. His home was just within walking distance of the shore. I walked there wearing nothing but my black flip-flops and that new bikini. He carried a small cooler containing a cold six-pack (even though I don’t drink) along with a couple of towels. We played in the gentle waves until midnight, making out on the sand, kissing and fondling each other. I was so turned on that I had to give him a blowjob right there on public beach, even if nobody could really see us out in the dark. I LOVED feeling his throbbing cock as my throat caressed it, pressing my lips against his pubic mound. He held the back of my head firmly, pushing himself deep into my mouth while he came. Being the Cum Whore that I am, I milked his dick dry, swallowing every drop.

When we returned to his house, I cleaned up and slipped into a sheer black nightie without even bothering with panties. He got hard again, cuddled up behind me, and I drifted off to sleep in his arms with his large, hard cock inside me. I just LOVE sleeping like that.

The next morning, I woke early on my stomach as he was pounding the hell out of my ass. I clenched my sphincter muscles tightly when he finished. As he lay atop me afterward, I talked him into giving me a urine douche. It felt fantastic having him pee inside me. Still holding all that liquid within, he laid me across his lap and delivered a good, hard bare-handed spanking. The arousal was so intense it felt almost as pleasant to empty my bowels as it did receiving the spankings.

Since we were running behind schedule, I simply slipped on thong panties and flip-flops, stuffed everything else into my overnight bag, and he drove me home wearing that outfit. My task for the day was helping with the setup—positioning props, setting up backdrops, etc., which I did in my nightie first before changing into the new bikini to work through the rest of the day. That made it easy to lounge by the pool between takes.:mrgreen: