Dressing Jaymee - Chapter 1 - What do you like? - Sex Stories

Dressing Jaymee - Chapter 1 - What do you like?

... knew it. As their conversations grew in intimacy, Cate started to feel her pussy as they would text back and fourth. She then found herself sharing with Jeff that she was doing just that. Jeff shared the same as he would jerk himself through their conversations. Their texting became full on sexting. Soon they even started exchanging intimate photos of their bodies with one another, increasing the vulnerability and intensity of each self-given orgasm they had during their talks. Jeff and Cate were heavily into their secret world. They shared as much about themselves and their sex life as they could. They elaborated on what it would be like to fuck the other person, sharing every detail of every move that they wanted to make on one another. “What is your ultimate fantasy?” asked Jeff. “I… I guess it’s… It’s hard to say,” Cate responded, puzzled. She honestly wasn’t sure what it would be. Although her mind was open to experimentation, she couldn’t narrow it down. So Cate replied, “what about you?” Jeff responded with, “Well, I love girls. I love everything about them. Their hair, their clothes their shoes… I love them so much I like to feel and touch all of those things.” Cate paused and responded, “You like to feel and touch them on a girl?” “Ya, of course,” Jeff replied. “But sometimes I like them just for myself, too,” he continued, “lingerie, shoes, make-up, dresses, you name it. IT’S SO HOT! Those things make you girls so hot. It’s honestly all I think about, and sometimes ...

... I want some of that too, but just for me.” Cate entertained the notion with curiosity but was hesitant. She wasn't quite sure how to process it. Was he telling her what she thought he was telling her? On the other end, Jeff thought she understood but wasn’t convinced, so he came right out with it, “I dress-up in those things. I’ve bought women’s shoes, dresses, make-up, and I even have a wig. I wear them and it makes me feel sexy to do so.” Cate was dumbfounded. She didn’t see it coming and felt an immediate rush of emotion. Confusion mixed with curiosity, surprise, and desire, it all came at once. She stayed calm and felt it best to stick as close to curiosity as possible and ignore the confusion. She knew Jeff well and liked him a lot, plus he was her friend. She wanted to understand. “Okay,” Cate said, “so tell me about it, what do you do and how do you do it?” Jeff went on for days about his love of shoes, dresses, make-up, and a high-cut anything. He told her how he had been like that since he was a teen living at home. He explained how he would order items online and spend a day by himself wearing his collection around his home. One night he was even brave enough to sit in his yard and smoke cigarettes then walk through a parking lot, fully dressed. Soon he even shared photos of himself, fully dressed, with Cate. Cate listened with an open mind and eventually found her confusion and surprise morphing more into intrigue and deeper into desire. She was so impressed he was ...