Cross-dressing double date goes as expected

Cross-dressing double date admittedly goes the way I expected it to. After all, ‘I’ am the one who got you ready for it.  You knew the risks when you agreed to be someone’s last-minute blind date.  And you were hardly dressed like a church girl.  What did you expect to happen?

But, let’s rewind.

You and I were just co-workers, and we talked reasonably often. Often enough, for me to confide in you one day about something. There was this guy I liked A LOT who wanted to go out with me, but he had a friend who just moved into town and was having a difficult time getting into the dating scene. Not wishing for his friend to feel left out and resentful, the guy chose to keep it in his pants for a while. Couple that with an already busy schedule and, I was in for some lonely lights.

But an opportunity arose.

He called me today and says that he has time TONIGHT to hang out, but will only do it if I can also find a date for his friend. This wouldn’t have been a problem if he’d thrown this at me days ago, but I only had a few hours.  ALL of my girlfriends said they’d already made plans. I know it seemed weird, but I was desperate.

“Could you…pretend to be a girl for one night? Just one!”

I mean, I wasn’t trying to insult you or anything, but you are pretty passable if you know what I mean. Your gentle features and slightly higher than normal voice for a guy would make you perfect. You need a little makeover.

“You will? AWESOME!”

I have to admit that I’m excited, even though you look incredibly nervous. Don’t worry, though. You’re in good hands. Just a little hair removal here, a little nail polish there, a pinch of lipstick, and a touch of blush. We’re going out dancing so of COURSE; you have to dress the part. This dress is admittedly a little…skanky…but we didn’t have time to go shopping. All we have to choose from is from my closet.

Fast forward a few hours

A car pulls up, and our guys greet us at my door. I gave my guy a huge hug and your guy…well..he’s at a loss for words. He wasn’t expecting his blind date to be so smoking hot! You blush as you feel his eyes practically assault your body and, as you timidly loop an arm through his, you feel a hand grab a healthy amount of one of your ass cheeks.

“Play it cool. It’s just one night. Crystal needs this,” you remind yourself as he sits next to you in the back seat. Like it or not, you know this is going to be a long night.

To be continued

Is a cross-dressing double date a secret fantasy of yours too? Call my phone sex line, and we can discuss what happens next!