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"She called Astrid, and I've been seeing her for about three weeks now."
"And you haven't told me?"
"Well, I wasn't sure that I would go out with her again after the first time, but I keep coming back to her. She's pretty wild."
"How so. Tell me."
"Well, its hard. I don't know if I can..."
"Come on now! We've been friends for how long? We tell each other *everything*. We've shared our most intimate thoughts and feelings with each other. How can it be too hard to tell me what this girl is like?"
I really was mad. I felt hurt that he was holding back from me. If he wasn't going to tell me about her, then there must be something very wrong. I wasn't going to just let this go, like I did last time I saw him. Something was up.
I had to push and prod him, make him feel guilty, and twist his arm. Only then did he start to tell me how show looked (hot blonde with big tits). But that still didn't explain anything.
Finally, I had to tell him how hurt I was, and cried a few fake tears, sobbing about how our relationship has been ruined if he doesn't trust me enough to tell me. He got a serious look on his face, looked down at the floor, then began to slowly talk.
"When we went out on our first real date, we made love that night. But it wasn't like anything I'd ever felt before. She was on top, and she kept tugging at my nipples, touching me in places I've never been touched before. And she whispered in my ear that I was a girl!"
"I was so scared, but when I climaxed, it was so amazing! It was the hardest I've ever come, by far. She told me that I was her girl now, and that she was going to make me become a woman. I wasn't going to ever see her again, but after what she did to me, I asked her out again."
"The second date, we showered together, and she shaved my legs. She told me it would be a reminder that I was her girl, and that I had to keep them like that. Again we made love, and again it was so amazing!"
"Every time I've seen her, the sex is better and better. And every time I see her, she does something else to me to turn me into a woman. She did my nails last time, and even painted them. She told me that I was allowed to take off the nail polish this time, but as I move further along, I will have to keep it on."
"I don't know why, but this turns me on so much! I want to run away and leave her, but I can't! I need her, and keep coming back for more. She said that she's buying me a dress, and next time I see her, she is going to let me wear it. I don't want to, but I can't wait either."
I listened quietly as he told me all this. I nodded my head, and said "uh-huh" from time to time to let him know I was listening. When he was done, there was a moment of silence.
"Do you want to be a girl?" I asked.
"I want to be hers" he said.
"How far will you let her go with this?"
"I don't know. Every time it gets better and better. Its really kinky, but I don't know what to say. I love it, and I don't want it to end."
"Does she dominate you?" I said. "Does she order you around?"
"She tells me what to do. She says that if I'm her girl, I need to do exactly what she says."
"Is this something you can get out of? Do you really want to continue down this path?"
"I don't know if I can stop. A couple of times I said to myself 'thats it!', but I keep coming back to her."
"It sounds like you're addicted to her."
"I might very well be. But this isn't a bad thing! I like it so much! I've never been this happy. I like it when she makes me feel like a girl."
I was stunned to say the least, but I decided that the best thing to do was to remain calm, and to be supportive. Perhaps this really was what he wanted. Perhaps he really was a girl inside. I would help him.
"Do you have a female name yet?" I asked.
"She calls me Jillian when we're together."
"And how far along are you?"
"Well, I shave off all my body hair now. And I wear panties most of the time. I have a couple of bras too, but I don't always have to wear them."
"Do you have one on now?" I asked.
"Yes" he said, pulling up his sweater to show me.
"Do you ever stuff the cups full?"
"When I'm with her."
"Do you like it?"
"Oh yes!" he said.
"Listen, will you become Jillian for me, right now? I have a whole closet full of clothes, and you're free to try on anything you'd like. I want to see you when you're a girl, so I can understand you better."
"Really, you'd do that for me?" he said.
"Of course. Come on now, I'll wait out here. You know where everything is. Knock yourself out."
I sat and sipped some more wine, while he almost ran into my bedroom. I didn't know if this was such a good idea, but I decided that I'd let him dress up, then press him to find out if he liked being a girl, or if he just liked the sex. If it was just the sex, that was one thing. If he liked being a girl, then it was something else.
It took a while, and I wasn't sure if it was because it took him time to change, or if he was shy at the last second, and was sitting there. So I walked over, and knocked on the door to check on him.
"I'm almost ready" he said. I went and poured us each another glass of wine.
A few minutes later, in he walked. Craig looked like a man wearing a dress, but wow, what a difference! His smooth legs were covered by pantyhose, and I had to admit that they looked pretty good. His choice of clothes wasn't the best though. He didn't seem to realize that you can't just mix any old skirt with any old top. But the effort wasn't half bad.
He also was wearing makeup, which I hadn't expected. And he had stuffed the bra with something, so his 'boobs' stuck out. Not all that bad of a job. His hair needed work, and there were lots of things about him that made him *not* look like a woman, but I could tell that he was very proud of himself.
"Well Jillian, very impressive" I said.
"Thank you Jaimie" he said in a different voice than his normal one. I guess he was trying to sound feminine, but it didn't quite work, at least for me.
"So Jillian, what do you do with Astrid once you're dressed up like that?"
"Oh, we do girlish things."
"Like what?"
"Like do each other's nails, watch a chick flick, gossip, things like that."
"I see. And what do you want to do now?"
"Talking is fine" he said. "Talk to me like I was a girlfriend of yours, not like I was a guy."
"I pretty much do that with you already" I said, shaking my head. About the only thing I do differently if its a girlfriend, is we might talk about guys. Do you want me to talk about some guys I know, and you can tell me if you think they're cute?"
He was silent. I had lied a little bit, but at least I was able to determine that he wasn't gay or anything. He didn't suddenly open up and want to go for guys once he wore a dress. So it was either the fact that he liked doing it, or that she was using it to control him. I decided to see if he would do something outside of his normal self, now that he was dressed up like that.
"Jillian, go get me a tampon. I think my period might be starting" I said.
He smiled, and walked off to the bathroom. Well, that was easy. What man would be willing to do something like that? I decided to discuss my period with him when he returned. And that didn't seem to phase him at all! I tried a couple of other things, but he didn't break character, or even flinch at all. And he never disobeyed me.
Very interesting. This Astrid had him wrapped around her little finger. She had convinced him that he enjoyed being a woman. How had she done this to him? What had he gotten himself into?
"Can I talk to Craig?" I said.
"I'll have to change" 'she' replied.
I waited fifteen minutes for Craig to emerge from the bedroom.
"Well, what do you think of me as a woman?" he asked.
"You have nice legs" I replied.
"Thank you!"
"Craig, I asked you to do several tasks for me when you were Jillian. Do you remember?"
"Sort of" he said.
"Sort of?"
"Yeah, it just kind of flew by. But I do remember that I enjoyed it so much!"
So something strange was going on. When he was Jillian, there was a major shift in his personality. And Craig didn't even remember all that he did as Jillian. Was this multiple personalities I was dealing with, or something? I wasn't a psychologist, but I had seen a few made for TV movies on Lifetime about people like that.
It was too much to think about, so I decided to just change the topic, and get back to the movie that we had been watching.
* * *
Two days later, I got a call from Craig.
"Astrid said to say thank you" he told me.
"For what?"
"You let me be Jillian for the first time when away from her house. She said that you've helped me move forward. And she rewarded me by letting me start taking her birth control pills, so I can start feeling what its like to have female hormones in my system."
"Craig! You should really think about this! Those could really harm you, or do things to you that you don't want. I think you should stop seeing her."
"Oh no, she assured me that its safe. And she wanted me to tell you one other thing."
"What's that?" I said, getting exasperated. She was starting to get on my nerves, the way she was twisting my friend.
"Astrid said to tell you that she wants to meet you."
"She wants to meet me?"
"Yes. She said that I should bring you with me tomorrow when I go over to her house."
"Hmmm." I said. Why would she want to have *me* there?
"Great! I'll pick you up at 6. Bye Jaimie"
He hung up on me! He didn't wait to hear my response, he just assumed that since Astrid wanted it, then I would want it too. What nerve!
But I also realized that this might be my chance to 'show her up', or to open his eyes as to what she really was, and how she was manipulating him. I would do this, but only to help out my good friend.
* * *
I dressed in a nice outfit for the big meeting, but not too nice that it looked formal. I wore my black skirt with knee high boots, and a white sleeveless top. I was fixing my makeup when Craig arrived to pick me up. I could see the outline of his bra under his white shirt.
"Don't you know that you can see that you're wearing a bra, when you wear a white shirt?"
"Yes" he replied. "Astrid told me to wear a white shirt today."
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