Chapter 77
She giggled. “I was thinking about that earlier, I couldn’t see the bulge, and I know you have a good size cock. Anyway, it looks like you have a pussy right now, so I guess being a bit uncomfortable is worth it. Go and put on a dress.”
He chose the blue one with the shoulder straps, but when he put it on it just hung on him. It took a few seconds before he realized what was missing. Boobs, he had no tits. He pulled off the dress and put on the black bra, and after putting on the dress again, it looked a bit better. He grabbed his socks and rolled them up and stuck them into the bra to fill it out. After taking another look in the mirror, he was pleased. The dress was snug around his waist and hips. The rolled-up socks and the bra made the illusion of boobs, overall he looked good.
Valerie smiled when she saw him. “Oh my god, you look great. What did you do to make the boobs?”
“Socks in the bra.”
“Wow, turn around.”
When he did she was astonished at what she saw. Apart from the short hair, Jason could be a young woman.
“Bend over, like if you were picking something up,” she said.
When he did the dress slid up along his legs to about half way up his thigh.
“Look at me, and smile,” she said.”
“You are so bossy, you know?”
“Shut up Nina, and do what you are told.”
There was a long silence, during which neither of them spoke. Then Jason slowly stood up straight and turned towards Valerie. “That was amazing.”
“What?”
“What you just said, for a second I felt like a woman, like Nina.”
Valerie drank from her wine and after putting down the glass she said, “Cool, put on the heels, and make sure to use the shorter. I don’t want you to fall over.”
When Jason was gone, Valerie closed her eyes. What had just happened, she thought? When Jason had looked at her, she had had a vision of her walking over to him and pulling up his skirt. And then slap his ass. What was going on with her? She had never ever been into S&M, but for some reason seeing Jason dressed like a little slut had turned her on. She wanted to tell him to do things, small things, and maybe even dirty things. She finished her wine and then went to refill her glass. This dress-up game had taken a completely new turn.Published by Nôv'elD/rama.Org.
Jason held on to the wall and tried to keep his balance. He slowly opened the door and stepped out. He stopped and swayed a little before holding on to the door frame.
“This shit is hard. How the hell do you walk on these,” he said.
When Valerie saw him she couldn’t help laughing. He looked like Bambi on ice. “Put one foot in front of the other and then slowly walk towards me.”
She watched as Jason made his way across the floor to where she was sitting. When he got there he grabbed the edge of the sofa and then walked around and sat down. “That’s not an easy thing to do, walk in heels.”
“I’m sorry to tell you, but you looked like John Wayne, Nina needs to practice. Anyway, here is your prize,” she gave him a glass of wine which he finished in two long drinks.
“That was good. So, how do I look?”
Valerie began with his feet and then slowly let her eyes move up until they ended at his eyes.
“Like a guy in girl’s clothes. You are a long way from being Nina.”
Jason felt a bit disappointed. “I see, so basically I look like a freak?”
“Let’s see, you need makeup, real boobs, and you have to learn to walk on those heels and you need a wig.”
“Fuck!”
Valerie laughed. “Not to worry.” She reached for her laptop that lay on the coffee table and opened it up. After searching Google she said, “look, here is a site for crossdressers. Give me your wallet.”
“It’s in my pants. Jason took off the heels and went to get it. He still had a hard-on and when he had stood up, his cock had moved and a bulge had formed in front. When he came back to the living room, he stood in front of Valerie and gave her his card. When she looked up, her face was only inches from him and she saw his erection.
“Wow, I guess wearing those clothes has turned you on.”
Jason looked down, “oh shit, I am so sorry.”
He quickly sat down again and adjusted his cock. Valerie glanced at him and smiled. “It’s OK, don’t worry about it. We already know Nina is a horny little thing.”
She began scrolling down the list on the site and then clicked on boob forms. “Look at these, which ones do you like?”
Jason leaned in and pointed, “what about those?”
“OK, and you are a C cup.” She clicked on the item and added it to the shopping basket. Then she went to the wig department and chose a dark brown with long curls, a little bit like her own hair.
“I have makeup you can borrow so we don’t need that. Anything else?”
“I guess that’s it.”
“Good, I think it’s worth getting this sent overnight.” She clicked a few times and then gave the credit card back to Jason and closed the computer.
“That’s it, tomorrow we will finish off Nina.”
Jason sighed and lay back against the sofa. He looked down at himself and pulled up the dress until his panties and garter belt were visible. Then he let his hand slide in between his legs.
“Hey, if you are going to jerk off, do that in your room.”
He blushed and said, “calm down. This is amazing; it feels like if I had a pussy, I can hardly notice the outline of my cock.”
Valerie leaned forward. He was right, just the slightest rise was all she could see. Suddenly she had an urge to touch him.
“May I?” she said and let her fingers hover above his crotch.
Jason swallowed, “yeah, I guess.”
Gently she lowered her hand and then she let her fingers slide down between his thighs and pressed down her palm. She felt the outline of his cock, but it was the overall sensation was that of a hot pussy.
“Jason, you have a man pussy,” she laughed.
“Fuck you.”
She doubled over laughing almost spilling her wine. When she got herself under control she said, “sorry, I didn’t want to hurt your feelings. I have to agree, the illusion of you having a cunt is fantastic, but as soon as you touch it, you feel the cock.”
“Mm, well, there is nothing to it. I’m not cutting it off.”
Valerie giggled. “I don’t want you to, I like your cock, it’s beautiful and I am sure many women also think so.”
“Thanks.”
She got up and took their glasses to the kitchen and when she came back she said. “Go to bed, Nina, tomorrow I will teach you how to walk in heels.”
Jason got up and walked in front of her and when she turned to go into her bedroom she smacked his ass. “Mm, I love that firm ass, Nina.”
Before Jason had time to answer she had closed the door. He realized his erection was back and he walked into his room where he began to undress, carefully placing the clothes in the paper bags.