Lost Boy

by Jennifer White

  

Craig was over at my place talking to me when I first noticed that he had shaved his legs. But I had better explain a few things first. You see, he had been a close friend of mine since college, but we were just friends, and nothing more. Even when he was dating other girls and I had a boyfriend, we still hung out together.

I always felt that at least a couple of his girlfriends felt jealous of his relationship with me, and didn't want him hanging out with any woman but them. But hey, that's how it was, and our relationships with others weren't going to tear us apart.

Even more than my girlfriends, I felt like I could tell him anything, and he was the same with me. When I needed a shoulder to cry on, I could rely on him to be there. Or when he was in a rocky patch with a girlfriend, and needed a woman's perspective on what to do, I was there for him.

Oh yes, and we both like wine and old romance movies. So we were perfect for each other, except for the fact that we had no interest in dating each other.

 

So anyway, one day he came over with a rented movie and a bottle of chardonay. I made a plate of veggies with dip, along with cheese and crackers. We sat down to talk, then watch the show.

As we watched, I noticed a few times that he was squirming around, as if not quite comfortable. I couldn't help but to see him itch his legs again and again. Then he pulled up the leg of his slacks to scratch the skin directly.

It was then that I noticed that his leg was hairless and smooth. Given that he seemed so itchy, I concluded that he had just shaved them.

"Are your legs bugging you?" I said. "I can't help but notice that you keep itching them."

"Shh Jaimie, I can't hear the dialog."

I pressed 'pause' on the remote.

"And I can't watch the screen with you squirming and itching like you've been bit by a zillion mosquitos. Now tell me, what's going on?"

He was hiding something from me, which was very unusual for him. I didn't like it, but he must have a good reason if he didn't want to tell me.

"I just itch, that's all" he said, looking away from me. Now I knew that something was up.

"I have some cream I use on my legs. They sometimes itch after I shave them, and the cream soothes them for me. Do you want me to get it for you?"

"Um, uh, no, its not that, but yeah, I guess I'll give it a try."

I went to get my cream, and knew that I had hit home with my remark. So he was shaving his legs, but he wasn't about to tell me why. I decided not to push him on it, but to just let him tell me when the time was right for him.

* * *

 

A few weeks later when I saw Craig again, there was something else that struck me as funny. Girls notice things that guys might overlook, so he seemed very surprised when I asked him if he just had a manicure.

"Um, no, I just cut my nails" he said.

"Oh, because they look so evenly shaped, and your cuticles look so good, I thought that perhaps someone did your nails. Your new *girlfriend*?"

I was taking a wild guess. He hadn't told me about a new girlfriend, but what else would cause him to be acting so weird?

"How did you know?" he asked, stunned that I had figured it out.

"Feminine intuition" I replied. Or in other words: using your eyes and your brain.

"So tell me about her!" I said. "What's her name?"

"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."

"Oh" I said, shaking my head. I was going to have to deal with this woman.

 

We rode in the car over to her house, and I worked myself up into a good fit of rage. I was ready to take her head off, as soon as the did something to set me off.

We walked up, rang the doorbell, and waited for her. When she finally opened the door, I gasped. This Astrid was a real knockout. She had short blonde hair, and it was slicked back. She wore all black leather, hugging her womanly curves. She did have big tits, as Craig had said. Her leather top had a hole in the middle so that you could really get a good look at them.

"You must be Jaimie" she said. "Won't you come in?"

She led us to the living room, and motioned for us to sit on the couch. Before I sat, I gave her the once-over with my eyes. When I reached the top, my eyes locked on to hers, and we had a bit of a stare-down for a moment.

But then something strange happened. I felt a stronger and stronger urge to sit, like my knees were getting weak.

"Sit Jaimie" she said, and I sat right down. She turned to Craig, and looked deeply into his eyes.

"Go change my love, and return to me as Jillian."

He got up and left for a room in the back.

"Lets get into something a little more comfortable" she said to me. I stood up, and found myself putting my hand into hers. We walked holding hands into her room.

Once inside, she opened the closet door, and looked through her clothes. She pulled out two negligees, one in red and one in powder blue. She handed me the blue one.

"Put it on Jaimie" she said, as she looked into my eyes. To my surprise, I found myself stripping naked, as she did the same. We each put on our negligées, and stared at each other.

Astrid had a wicked smile on her face. She licked her lips, and suddenly I felt myself getting wet! I had never been attracted to a woman before in all my life. But somehow, she got me going.

"Jillian, get in here now!" she yelled. Seconds later, Craig ran in as fast as he could in the high heel shoes he was now wearing. He was dressed up in a slutty outfit, with a miniskirt and a tiny top. He was wearing fake breasts that were hanging out of the pushup bra. And he wore quite a bit more makeup than he had at my house.

"Now watch" said Astrid, "watch closely to see how a woman pleases another woman."

She laid down on the edge of the bed, and spread her legs wide open.

"On your knees Jaimie!" she ordered, and I fell to my knees before her. She wanted me to go down on her! I wanted no part in this, but slowly, even against my will, I felt my head move lower and lower until she was right there in front of me.

I stuck out my tongue, and went to work. I did her as I would have wished it done to me. I caressed her nipples with my hands, or touched her in all the right places as I kept going at it. I lost track of all time. Was it ten minutes, or an hour? All I knew was that I was *enjoying* this, and I was getting incredibly wet myself.

"Now your turn Jillian" she said.

I stood up, and went to the night stand to get a Kleenex to wipe off my mouth, as Jillian assumed the position.

"You saw how a *real* woman does it" said Astrid. "Do like she did. Be like a real woman."

I watched 'Jillian' do her for ten minutes, and I now felt incredibly horny. When Astrid made Jillian stop, because she was getting too tender, she sat up and looked at me.

"Your turn" she said. I found myself almost running to the bed, lying down, and pulling up my garment to reveal my crotch. In all the time I had known Craig, he had never seen it before.

"Take it all the way off Jaimie" said Astrid, so I did. I was now naked.

"Jillian, suck her nipple" said Astrid. Craig would never touch me sexually, but Jillian hurried over to start sucking me. And meanwhile, Astrid went down on me. I almost immediately started exploding with pleasure, as orgasm followed orgasm.

Astrid pulled up, and put two of her fingers up inside me. She explored the wall of my vagina, until she found just the right spot. She started massaging it, and I was engulfed in a warm glow that started in my center, and radiated out. She had found my G-spot, and was bringing me in a way I had never come before.

Then she moved her thumb onto my clitoris. Between the G-spot getting it, my clitoris getting it, and Craig sucking away at my nipples, I was just overwhelmed with orgasms.

Finally, I had to push her away, as my privates got so sensitive that it tickled to have her keep touching me. I was unable to speak, because of the aftershocks from all the orgasms. I must have felt more orgasms in that half hour, than I had in the past year combined!

"You will never want to be with a man again" said Astrid. I knew that it was true. *This* was what I wanted now. I was hooked. How could a mere man ever do that to me?

"Jillian, you want to be Jaimie, don't you?"

"Yes! With all my heart, I wish I was her!"

"Good. Jaimie, you are a close friend of Craig's. You will do everything in your power to help him become a woman."

"Yes" I said. "I would be glad to help you."

"Good. Now massage my feet, both of you."

We eagerly started on Astrid's feet.

* * *

 

When Craig took me home when we were done for the night, I tried to reflect back on what had just happened. I had remembered arriving, and talking to her. But the next thing I remembered, the three of us were in bed together.

It was the first time I had ever done a three-way, and all I can say is that when it was done, I was in love with Astrid. I wanted her so much! I had given her the longest kiss when we parted. She had put her tongue into my mouth, and that got me wet again.

"I'm going to help you become a girl" I said to Craig. "Come over tomorrow, so we can start."

"Thanks Jaimie. You know, I wish I was you. You're so lucky to be a girl."

* * *

 

When Craig arrived after work the next day, all we could talk about was Astrid.

"So, what do you think of her?" he asked.

"I love her!" I said, which was certainly true. Very true. I hadn't been able to get her out of my mind since she made me explode in pleasure.

"I knew you would" said Craig. My true meaning was completely lost on him. Oh well, that was men for you. I don't know why I had ever bothered to date them, when I should have been going out with women all this time. I couldn't wait to be with Astrid again.

 

I had promised Astrid that I would help make Craig into a woman. So I had him dress up, and started calling him Jillian. I spent an hour with Jillian, teaching her how to put on makeup, how to put together an outfit, and lots of things that we women knew, but men were clueless on. Another reason not to date them!

Then I did a role playing game with Jillian, where she had to pretend to be a young girl on her first date, and I pretended to be a guy. I did all of the things guys had done to me, and tried to show her how it felt.

For example, I talked and talked to her, but didn't take my eyes off of her boobs. After a while, she started to get annoyed.

"Why are you looking down when you're talking to me? My eyes are up here."

"Bingo!!" I said. "Do you know how many times I've been with a guy, and he keeps staring at my boobs when he talks? Or even if he isn't talking, he keeps staring at them? I just hate it!"

"I can see why" said Jillian. "Did I ever...."

"No, *Craig* wasn't that way usually, although I did see him ogling other girls sometimes. But he wasn't bad, for a guy."

"What else can you teach me? This is fun!"

I taught Jillian about women's nutritional needs. I showed her the soy based products I used, because soy has natural chemicals within it that are very similar to estrogen. Some women claim that soy helps with symptoms of their periods, or even with menopause. So I told Jillian to start taking it right away, just in case.

I also gave her a list of books to read, which many young girls would have read, but not boys!

"These give us some common ground with each other. Like a shared experience. Read them all, at least twice, until you know the stories inside and out."

"I promise I will" she said.

We watched a romance movie, then it was time for her to go for the night.

"I'll see you tomorrow at Astrid's" she said as she prepared to leave.

"Good night. I'll see you there."

As Jillian drove away, I realized that she had forgotten to change back into being Craig again. Oh well, perhaps she was getting more comfortable with being a girl now.

* * *

 

The next day at work, I thought about all that had gone on the night with Astrid. I wondered how she had done those things to us. Somehow, she made Craig want to become a girl, in order to receive pleasure from her. And then there was what she did to me.

I had always been 'normal' when it came to dating and romance. But she somehow made me feel something towards *her*. And now as I scanned the people in my office, I wasn't looking at the men and wondering what they looked like naked. No, I was checking out the women! I was looking at the pretty secretaries and the administrative assistants, and wondering what sort of bras they were wearing, and how wonderful they would look naked. I even got wet as I imagined being with this cute young blonde.

How could Astrid have changed me over like this? In just one night, my entire world had shifted 180 degrees. My preferences had been turned, and now I was only interested in *women*.

And I so much wanted to please this Astrid, that I was willing to help turn my best friend into a girl, because that was what she wanted. How could she have so much of a hold on me? How could she have changed something deeply rooted within me? I didn't understand how she had done this.

I had always considered myself to be a very strong person. But I felt like a little girl again, meek and intimidated because of her. And the more I thought about her, the more I felt like I was falling in love with her!

I knew that if I was to go with Craig to visit her that night as we had planned, that I would never look back. I would be so head over heels for her that I would never break loose.

Part of me wanted to stay home, keep Craig away from her, and try to go back to how things were. But I knew that I was only kidding myself, like when I'd say to myself "that's it, tomorrow I go on the diet" or "I'm giving up smoking for *real* this time". You say it to yourself, but you know that you don't really mean it.

Tonight would be the turning point in my life. More than getting married would be (if I ever wanted to be with a man again), or having a baby (I could still do that if I was with Astrid...we'd just need a donor), or anything else I could think of.

Tonight was the night.

* * *

 

When we arrived at the door, I was going to tell her off right away. But one look into those eyes of hers, and I was speechless.

"What have you done to me?" was all I could say.

She just smiled in response, and invited us in.

"Tonight, I will tell you everything darling" she said. "But first, we make love."

I cannot begin to tell you all that we did together that night. Just suffice it to say that when we were through, there was little doubt in my mind that I loved this woman.

"Jillian, go prepare us some supper" ordered Astrid, and Craig sprang up to do it.

"Now my dear, you asked me what I did to you. It is rather simple, really. First, you were placed into a state of hypnosis, just as I had done with your precious Craig. You don't even remember, because I told you that you were not allowed to. Then I administered a drug, one that makes you even more open and vulnerable to suggestion and manipulation. I gave you additional instructions, and now you are hopelessly in love with me, aren't you?"

"Yes" I had to admit. "I never thought I would love a woman, but I *am* deeply in love with you."

"Excellent!" she said. "And now for the next stage. Previously, you cared about Craig, but just as a friend. But that is going to change. Now you desire only women, so Craig has no place in your life. But Jillian does. It is your goal in life to do *everything* you can, to make Jillian into a real woman. Because once she is a real woman, then you can love her with all your heart. *You* will complete my work, and finish her."

"Why do you think I will do this?" I said defensively. I wanted no further part in this.

"Because dear Jaimie, you are under hypnosis right now! As soon as I give you some additional instructions, you will obey me by forgetting this conversation, but starting with your mission to truly turn Craig into Jillian. He is very accepting now, and actually *wants* to be a woman. So all you have to do is to keep pushing him. Make him dress up, and go out in public. Get him on hormones full time. Use a strap-on, and penetrate him. Make him your slave. He wants to *be* you, so he will be willing to do *anything* you tell him. Turn him into a woman. Have him take a second job as a maid or a secretary, to save up enough money for his operation. Then you will have the woman of your dreams, who you can love."

"No..." I whispered.

"Jaimie: listen to me. You will now forget this conversation ever happened. You will only care about your mission. The love you feel for me you will transfer onto the woman that Craig will become. With all your heart, your only goal in life is to turn him into Jillian, so you can have the ideal love of your dreams. Now!"

 

"Weren't you going to tell me what's going on?" I said.

"Later" said Astrid "For now, let us go eat with Jillian. Supper should be ready."

I followed her downstairs, and to the kitchen where Jillian had set up a nice dinner at the table. I looked at Jillian, in her pretty dress, and my heart just melted. I knew that underneath, I was looking at Craig. But more than anything, I wanted to help him truly *become* Jillian. It was at that moment that I realized that the more feminine he became, the more I loved him. I wanted him, but as a girl. I needed to turn him into a girl completely, so we could have our true love.

I glanced over to Astrid, and hoped that she didn't guess as to my true plan. I needed to get us out of there, so there would be no chance of Jillian falling for Astrid. She was very sexy and alluring, and I needed to keep *my* love away from her clutches.

As soon as possible, I made an excuse of not feeling well, so of course Jillian offered to take me home. Perfect!

 

As we drove away, I knew that I would never see Astrid again. But it didn't matter. Every day I would move Jillian closer and closer to true womanhood, until one day she would be completely female, and I would have my true love that I had wished for all my life. I was undressing her with my eyes. Oh how I wished she already had a pussy, so I could make love to her tonight. That would have to wait. Until then, I had much work to do, to make her into a woman....

  

  

  

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