1. Dressing Jaymee - Chapter 4 - Going Out


    Date: 4/27/2016, Categories: Crossdressing, Author: Elise_xo, Rating: 2, Source: LushStories

    Cate walked out of the bathroom and into the suite. She poured them each another glass of wine and headed over to the window. It was dark out but the city was busy and full of lights. The hotel was on a main road and looked over a series of bars, restaurants, and clubs. There were several large apartment buildings behind the bars and Cate started to scan the lit windows. She watched as people prepared for dinner; a woman exercised in her living room, a couple fought, and some kid was sneaking a smoke on a balcony. "What are you looking at?" Jaymee asked from behind her. Cate paused, turned around, and then responded, "Are you ready to let others see you dressed?" "Others like who?" Jaymee questioned. "Anyone. Strangers. People you've never seen before and will probably never see again. Come here," Cate gestured towards the window. Jaymee smiled and moved towards her, stopping about two feet from Cate. "No, I said here," Cate grabbed and pulled Jaymee’s arm so he was standing in front of the window. Cate set Jaymee's drink down. "Stay there," she said. Cate walked around the suite and turned off all the lights in the room except one. She made her way back to Jaymee who was quietly gazing out the window. Cate could sense a bit of the uncertainty he was feeling. Cate put her hands on Jaymee’s waist and whispered from behind his shoulder, "Look around outside, who do you see?" Jaymee responded, "I see a woman in her apartment, she's talking on her phone and looking out the ...
    window." "Who else do you see?" Cate demanded softly. "I see a group of guys walking down the street. They're dressed for a club and laughing. I see an older woman making her dinner, a guy selling newspapers on the corner. There's a lot of traffic, it's moving slowly down the street." Jaymee said. "So what do you think, Jaymee? If you can see these people, they can probably see you?" Cate asked. "Well they must, I guess," Jaymee responded. "How does that make you feel, knowing they can likely see you dressed," Cate whispered as she set her chest closer to his back. "Do you want them to know? Do you want them to see?" she asked. Jaymee's body was heating up as his mind built the emotions of any implications or reactions he could potentially receive from strangers who saw him dressed. As he pondered the question further, he could feel Cate rubbing the fabric of his dress at his sides. The slinky material created just enough of a breeze to keep him conscious through the erection growing in his panties as the thought of public exposure became more erotic. Jaymee had allowed the emotions of the last few hours to come together and create the confidence he needed to consider such an exercise. "Jaymee, I think the world should meet you. Come out with me," Cate said as she continued to grind his back. Jaymee turned around, smiled at Cate and took a few steps over to the desk. He grabbed a small handbag out of his luggage and said, "OK, let's do it". Cate grabbed her purse and walked over to ...
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