There I was, on the patio of a massive and very flash villa on the coast of an unbelievably beautiful (and bloody hot) Caribbean island. Not just any ...ld Caribbean island either, this place was a private island. Only people who owned one of the villas — or could afford to hire one for a week or so — their staff and guests were allowed to step foot on the hallowed soil. The sort of place that the likes of me shouldn’t even be allowed to dream about, let alone live in for a couple of months. I. " It occurred to me that I had just lost my virginity, wearing women's clothing, to a girl who was dressed as a guy. What was happening to me?"That was awesome," she said. She rolled off me and disappeared into the bathroom, leaving me to my confused thoughts. When she returned, she was holding her lipstick. "I've never had to wipe a guy's lipstick off before. Here, your face is a mess. Let's see what you can do with it."I stuffed my now limp penis between my legs, straightened my panties and. More

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