I Want to be Beautiful

Description

Let’s talk about the clothing issue. You initially asked if a guy wearing women’s clothes would be considered gay. The simple answer is no, but this isn’t a simple situation we are talking about. I’m sure you have a few choice pieces hidden around here? I mean you said you wear something most days, even if it’s just around the apartment.” He nodded and stood. She watched as he went down the hall silently. He returned with a box.

Melinda looked in the box and saw a wide variety of women’s undergarments. Some were nicer than others, some had more lace or more satin. She was glad to see that he didn’t possess any plain old cotton granny panties. For some reason, she thought that would have been weird. “Have you worn any of these out?”

“Yeah. I wear the panties sometimes, well more often than not, really.”

“And how does it make you feel?”

“Good. I mean it turns me on, of course, but it seems to be more than that. It makes me feel good. It makes me wish I could actually dress up completely.”

“Why haven’t you?”

He looked incredulous at the idea. It had been a desire of his for a long time, but he didn’t think he would ever have the courage to actually do it. Plus, he was sure he would look ridiculous as a woman. He noticed that she stared at him, even studied him.

“I think you could make an attractive woman.”

He laughed.

“No, I’m serious. With the right makeup and outfit, you would be way better than passable. Do you want to try it? I could teach you how to do your face, so you didn’t look like a caricature of a woman, and I have an idea how to deal with you not having much of a wardrobe.”

His pulse raced. He could feel the pounding in his chest as he nodded to his friend.

“Great! Now first things first, go take a shower. It’s always easier to make up a clean face. Oh, and you might want to jerk off while you are in there. If not, you might become distracted.”

That elicited another bright blush. While it may have been an odd thing to hear from his friend, it didn’t make it less true. He got up and went down the hall. A minute later the bedroom door opened. He wasn’t in the shower yet, and she took him completely by surprise. He froze. Melinda looked him up and down. He only wore a pair of light blue satin panties.

“I just wanted to tell you that I’m going to run over to my apartment and get some makeup and stuff. I’ll be right back.” She smiled and turned away. He listened for the front door to close before letting out the long-held breath and headed into the bathroom.

She paused on the other side of the front door and held that image in her head for just a moment. James was a handsome, if not a little bit skinny, man. Seeing him standing there almost naked, a state she never managed to get him in before, was exciting. The added fact that he was wearing panties that were straining to hold in a rather substantial erection was a great and sexy bonus.