Chapter 78
“That suit looks good on you Mr. Craig.”
Jason turned to the young woman standing next to him in the elevator. She was one of the company’s secretaries, not one of his though. She was in her early twenties and good-looking. Blonde, blue eyes, soft-looking lips and was dressed in a business suit.
“Thank you, Marie.”
She leaned closer, “don’t take this the wrong way, but you are so darn masculine. It might be the aftershave you are wearing.”
Before Jason had time to answer the elevator stopped and she walked out. He carried on for three more floors and when he got off, he was on the top floor. He walked over to his office and hung his jacket over his chair and sat down, getting ready for a new day. While he waited for the computer to boot up his thoughts drifted back to what Marie had said. Masculine? Shit, the day before he had been walking around Valerie’s place in heels dressed in a dress and wearing a garter belt. He closed his eyes and wondered what the heck he was doing. It all seemed so strange to him. Sure, he had fantasized about being Nina, but here at work, it all seemed like a different world. On the top floor, only three women were working, the rest men. His work world was men, and that’s who he spent his time with. The jokes and comments were all masculine and often highly sexual. Whenever one of the secretaries came up to deliver something all his co-workers ogled them and as soon as they had stepped into the elevator the comments began. “Would you fuck her? Does she suck cock? Do you think she takes it up the ass?”
He had always joined in and said his piece of mind. Over business lunches, the waitresses were often discussed and even offered money for a quickie in a limo parked outside. As Nina, would the men that he met, act the same or would they see that it was a man in drag? He had no idea, and it scared him. Maybe he should tell Valerie it was over and go back to being Jason full-time. On the other hand, it was only a game, wasn’t it? Valerie was helping him to become a woman, so he could get off on it in the privacy of his home, nothing else. He sighed and turned to the computer and began the day’s work.
Valerie was sitting in a diner across the street from the department store. She was deep in thought and very confused. What had begun as a game had turned into something where she questioned her sexuality. Sure, Jason was a cool guy, a good person and they had spent a summer together, but that was it. Then after he had returned from college, they had stayed friends, drinking, going out to dinner, or catching a movie together, as friends do. But the previous had brought an entirely new dimension to their relationship.
Finding out that Jason liked to fantasize about being a woman had made her laugh and him playing dress-up at her place had seemed like a fun thing to do. Then, in the middle of the night, when she had tossed and turned for hours without being able to sleep, she had turned on her bedside lamp and asked herself, “what the fuck is wrong?” It had taken most of the night to figure it out, but now she knew what it was. She had been turned on by seeing Jason dressed as a woman. It didn’t make sense at all. She didn’t find bisexual men interesting, she wasn’t a bisexual herself and she had only had one adventure with another woman, which had been fun and all, but not earth shattering. But seeing Jason in the doorway, looking like Bambi on his heels had made her go wet, and not a little bit. When she had undressed for bed, she was soaked. She had laid on her bed and fingered herself until she came in a drawn-out orgasm. What had made her understand what she was feeling was when she realized that she wanted to see Jason being fucked, like a little bitch. The thought about him taking a cock in his mouth or even up his ass, while she was watching made her wet again. Jason had always been emotional, and sometimes she had thought of him as a sissy, especially before he went on to college. It wasn’t until he had fucked her a few times, that she realized he was not gay, but the thought still lingered. He was a bit feminine, and maybe that’s why they were such good friends, he was more like a girlfriend than a guy friend to her. He could listen for hours about her failed relationships. He didn’t mind going shopping with her, and sometimes, he had agreed that a guy that was sitting close to them in a bar was good-looking.
She finished off her soft drink and asked for the bill. When she woke up that morning Jason had already left and she had asked the doorman to sign for a package that would arrive in the afternoon and keep it until she came home. When she walked out of the diner she decided that she would take Jason’s alter ego, Nina, as far as she was willing to go, and it would be very interesting to find out where that road ended.
When Jason walked into Valerie’s apartment that evening she wasn’t at home. He found a note on the floor, which said that she had gone for drinks with a girlfriend. But she had left him some homework. He was to put on the four-inch heels and practice walking.All content © N/.ôvel/Dr/ama.Org.
After changing into a pair of sweats and a T-shirt, Jason put on the heels and slowly walked out into the living room. He had decided it would be easier practicing in regular clothes than in a skirt or dress. He made it over to the sofa which he held onto while walking up and down its back. After ten times he felt he had it under control and ventured out onto the open floor. He got four steps before losing his balance and almost falling over. He swore under his breath and tried again.
Valerie came home an hour later and found Jason on the sofa watching TV.
“Hey, how did the practice go?” she asked.
Jason turned around and smiled. “Not too bad, I think I got it.”
Valerie walked into her room and changed clothes to shorts and a long T-shirt that kept on sliding over her shoulder exposing part of her left boob. She had picked up the box that the doorman had held on to and now she put it down on the coffee table in front of Jason.
“Let’s see what we got,” she said while using a nail to cut open the tape.
Jason moved closer and when she opened the box and took out a wig, he said, “Wow, that looks nice. Let me try it.”
“No, hang on, let’s do this right. We will make sure everything is here, and then I want to see you walk. After that, you can try these things.”
Reluctantly Jason agreed and the next item she took out was a pair of breast forms. When she opened the little plastic bag and gave one to Jason, he said, “this feels so real, but I guess I have to shave my chest a little, or it will hurt when I take them off.”
“If I remember right, you are not exactly a bear of a man, more like a few hairs, so you should be alright.”
Jason laughed and gave the breast back to her. “Ok, watch this,” he said and got up.