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During Saturday, James and I went sightseeing around the Phoenix area in his Ford F-150 pickup with a bench seat. We had a blast but I could not get him to tell me what was this surprise he had in store for this evening.

After we ate dinner at a restaurant, we went back to James' apartment.

"James, what is this fucking surprise you have in store?" I curiously asked.

James looked at me and a smirk grew on his face. "Well, it involves you getting dressed up like a woman. You'll be my date tonight."

It took a few seconds for it to dawn on me what he was talking about.

"Cross-dressing?"

James nodded in agreement.

I thought about what he said for a few seconds. "I've always wanted to try that and nobody knows me here. What the fuck," I replied and actually started to get a little turned on thinking about dressing up like a woman.

"Great. We have some work to do," he said then grabbed my hand and ...

This story is part of the EroticStories.com FanClub archive. Therefore, you can only see the first few lines. If you want to see the rest, you can join the FanClub. All stories that have the small 'a' (this icon: ) behind the title are part of this archive and only available to members of the EroticStories FanClub. Stories that were posted in the last 60 days are NOT part of the fanclub, so you can fully read those. The easiest way to get to those stories is to check the new stories list or the top stories list.

stories in "first time"   |   all stories by "James Jenson"