Karyn's mom had opened the door and was now talking to her daughter, who she thought was Jon. She was just making polite small talk. As Jon came down the stairs he took a good look at Karyn. She was dressed in a shirt and tie and a pair of slacks. Her hair was slicked back. He thought she looked funny but didn't dwell on it. If he thought she looked funny then she must think he looked even funnier wearing one of her dresses. He didn't want to allow himself to feel embarrassed. He was proud of the effort that he and Susan had gone to. To everyone else he looked like a very attractive girl, well made up and wearing a nice dress. The only problem was that Karyn saw him for who he really was. But he hoped she'd hold up her part of the deal and act the part of a gentleman and treat him like a lady, even just for tonight.
Jon rescued Karyn from the small talk and said a quick goodbye to Karyn's mom. The pair headed out the door together, with Karyn's mom looking on lovingly. Once they were out of sight Karyn stopped and turned to face Jon. She spoke first, "Wow Jon. I don't think I've ever put in as much effort as you have but I'm glad you did. You look good, all things considered." Jon replied in his soft spoken voice saying, "Thanks Karyn. You look good too. I've been wearing your clothes long enough now that this feels kind of normal. Your underwear is still a bit tight on me but the soft dress feels nice on my skin." Karyn once again noticed Jon's changed voice and the feminine way his hands moved as he spoke but she didn't comment on it. She just waited for Jon to finish speaking and then leaned in for a kiss. Jon was a bit surprised at first but soon went along with it, opening his mouth to allow Karyn's tongue to explore his mouth. His new natural instincts were to low Karyn to control the situation, feeling much less aggressive than he normally would. Karyn reached her arms around Jon's back and started to rub his butt through his dress and the satin material of the panties he was wearing. Jon's arousal grew and soon the front of his dress was tenting out slightly. Karyn gave his crotch a quick run and then released her embrace. She told Jon she had booked a restaurant and then they were going to see a movie afterwards. Jon was happy with the sound of that plan and held Karyn's hand as they walked down the street.
It didn't take long to arrive at the restaurant and Karyn took charge and gave the name, "Jon Gibson, table for two. " The waiter said"right this was sir," and showed them to a quiet table in the corner.
Karyn remembered her promise to play her part tonight and so she pulled Jon's chair out for him and guided him in to his seat, gently running his back and feeling the straps of his bra beneath his dress. Jon politely thanked her and waited for her to take her seat opposite him. They sat silently for a while, browsing the menu.
