1. A Date For The Weekend Chapter 1


    Date: 11/6/2014, Categories: Crossdressing, Author: jill_on_her_knees, Rating: 5, Source: LushStories

    I've been crossdressing and living as a woman full time for years. I put a lot of time and work into transforming myself into an attractive woman that can accompany a man anywhere in public and never raise an eyebrow. I've long since moved on from having casual cheap hookups to expecting more elaborate playtimes, and generally only date men if we can plan a weekend or more together. I mean, if I spend all this time and effort I expect more payoff than ten minutes of action. I really provide a full girlfriend experience for the men I choose to date. I had been talking to a man named Dave online for awhile, and had talked on the phone several times recently and texted daily. We had many of the same interests and seemed to be very compatible. He had always been straight, but became interested in being with a girl like me. He had been thinking for awhile how he'd like to have a full time girlfriend with a secret, like mine. One that he could proudly show off to his friends and family and they'd never know I wasn't genuine. After I was convinced he really wanted this, we agreed to meet for a weekend long date as a trial run to see how the relationship developed. Dave owned a couple of businesses in Pensacola, but wasn't a suit type. He oversaw the operation of those businesses but led a leisurely life. He was absolutely loaded, lived in a nice beach area, and had plenty of time and money to enjoy life. If this worked out the way we with hoped, I would be moving there to be his ...
    full-time girlfriend. With eager anticipation, I flew down there to join him on a Friday afternoon. At the airport he had a car waiting for me, and following the GPS I drove out to his beach house in Pensacola Beach. He was busy that afternoon so I was to make myself comfortable and prepare for our date that night. He had another house in the city but we would be staying here this weekend. I'd be living here as his kept girlfriend if we decided to stay together, which was most likely to happen as we were already quite familiar with one another. We just had to be sure before committing. Of course I wanted to make the best impression possible, so I went all out on the makeup, spending over two hours getting it just right. I had my hair done early that morning, and the blonde curls looked stunning flowing over my shoulders and halfway down my back. It was casual dress, and he wanted me looking slutty. We were going to a bar just down the beach that had a tiny amphitheater next to where they would be playing live music. I choose all pink for my outfit, silky pink bikini style panties, a gorgeous pink bra with white lace trim, a swirly pink and white tight teeshirt with palm trees on it, and a very tiny pair of pink shorts that matched the teeshirt perfectly. To complete my slutty look I added a pair of black thigh high stockings, and a few unassuming pieces of jewelry. I squeezed my breasts together and checked to make sure there was in no way any kind of unseemly bulge. I had long ...
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