Dressing Jaymee - Chapter 4 - Going Out - Sex Stories

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Dressing Jaymee - Chapter 4 - Going Out

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

the door of the suite. "After you, then," she said while holding the door open for Jaymee. And Jaymee stepped into the hallway. Jaymee stood in the hallway as Cate closed up the suite. Cate began to head for the elevator and noticed Jaymee wasn’t following her. The hallway was long and their room was located about halfway down. Another couple was entering a room at the very end of the hall. Jaymee watched as they fiddled with their key. The woman looked up and smiled, locking eyes with Jaymee. "I hate these things," the woman called out to him. Jaymee smiled in return but didn't respond. "Hey, get over here, girl," Cate called out. She smiled as Jaymee snapped out of it and made his way towards the elevator. He had just experienced his first exposure. The pair entered the elevator to head for the lobby. A few floors down the elevator stopped to pick up another passenger. A well-built middle aged, dark featured businessman wearing a jet-black suit and stark white collared shirt stepped in. He scrolled through his phone as he first entered and leaned up against the opposite railing in the elevator, not noticing Cate and Jaymee at first. As the elevator started moving, the businessman’s eyes fixated on Jaymee's high heels. He looked Jaymee up slowly and eventually made eye contact. He then turned to Cate who smiled at him confidently. He moved back to Jaymee and cracked a sexy smile in his direction. Jaymee blushed and added a hand to the railing as the elevator came to a stop ... in the lobby. The businessman's cologne was pungent in the air and followed him as he exited the elevator. As he was leaving, he smiled at the pair and said, "Have a good evening ladies." "Thanks," Cate responded as she smirked at Jaymee. The two watched as the businessman made his way into the hotel bar and took a seat alone near an inner window. They could feel his eyes follow them as they made their way through the turnstile leading outside. As Jaymee pushed his way outside the door, he caught eyes with the businessman one more time and flashed him a smile with a sexy little flirt. The businessman grinned and watched Jaymee follow Cate down the street. "Ok," Cate began, "where do you want to go?" "Let's just walk for a few minutes," Jaymee requested. It was a warm evening, just warm enough that you could get away without a jacket. As the two headed down the street, they passed the man selling newspapers on the corner that Jaymee had spotted from the window in the suite. He didn't bat an eye. They walked past a restaurant where people were eating and drinking while they looked out onto the street. As they walked past, Jaymee caught another glimpse of himself in the window. The juxtaposition of the figures in the restaurant and his own reflection made him realize that he was actually dressed in public. He couldn’t resist the smile that came across his face. They continued on their walk and with every step, Jaymee became more and more, Jaymee. Holding his handbag at his side, ...