tagTransgender & CrossdressersLittle Man Pretty Girl Ch. 02

Little Man Pretty Girl Ch. 02


I walked down the stairs and out onto the street. Seeing it was Sunday morning the street was deserted. There weren't any cars moving and no one was out and about. I knew finding a cab was going to be difficult this early so I started walking. Once I crossed the street I looked up to where I was sure Janie's apartment was and saw a drape flutter closed in one of her windows. I knew she had been watching me, but why, did she think I wouldn't leave.

I started walking to where I knew there would be a subway station. I thought I could take a subway the forty or so blocks to my apartment. But in the end I walked all the way home.

I barely remembered the walk as my mind went over what had taken place over the last three days. I remembered everything Janie said to me and everything we did. I remembered every feeling I had and every kiss she gave me. I also remembered how much I loved it and how much I wanted it to continue.

When I reached my apartment I knew I was going to do what she wanted and I also knew I had to set things in motion for when she called me back. If she didn't call me I would do it on my own. I'd change myself into what Janie had made me.

When I reached my apartment I found I had an email from my boss. He had a company that was being hit almost nightly by hackers and he wanted me to find their mouse holes and close them for good. I also had to back tract the hackers to see if I could find out who was behind this. He also wanted results by Wednesday. This wasn't that big of a problem and I went right to work.

While I worked my mind went over everything that Janie had said this morning. I had to understand how this would affect my life. As far as friends were concerned I didn't have any. Work was another problem entirely.

My boss, the owner of the company was a straight male that believed that gay men where a waist on society. God knows he told me that on more than one occasion. He knew my mother was a lesbian and every time she was brought up in a conversation I could see the disgust in his face. I was sure he would let me go once he found out what I was going to turn myself into.

Money wasn't much of a problem as I had a nice tidy trust fund from the settlement of my father's death. My mother had invested most of the money and there was a tidy nest egg. I also had done quite well in the working world seeing I was paid quite well and I had invested over half of it. But I would need a job to sustain my life.

As far as my mother and Betty was concerned I felt that they would understand. Well I felt that they would except it. I'm sure it's hard for any mother no matter how opened minded she was to understand why her son wanted to be a girl. That I would leave for later.

By two in the morning I had all the mouse holes closed up and I installed a sentinel program to catch any hacker in the future. I felt I had done enough for one day and I needed some sleep. But sleep wouldn't come and when it did it was fitful.

By Wednesday not only did I have the case that my boss wanted done but I also closed out ten other cases I had been working on. I also went into the states birth registry and established a birth record for Geraldine Adams. She also had a driver license record and a credit rating. Now as far as any one was concerned Geraldine Adams was a real person.

Wednesday was the day where I would go into the office to hand in my time sheet and any cases I had closed since the week before. My boss Jake was always happy to see me as he knew my work was my life. It was not unusual for me to hand in time sheets for a hundred or more hours in a week. Seeing I was a salary employee I would still only receive my base salary but that salary was substantial.

I walked into the office at three thirty in the afternoon. As usual there was only one or two employees in the office, as most did their work from home. I waited outside Jake's office for a few minutes before I was able to go in.

As soon as Jake saw me he shook my hand and slapped me on the back while saying. "Come in Jerry have a seat. American Label called me and told me they could see the difference in their access logs. They haven't had an attack since early Monday morning."

"I'm glad they're happy. " I told him as I handed over my closed cases and my time sheet.

"Happy, they're as ecstatic as I am. You are my best investigator I hope you realize that." He always told me that, but today I wondered what he would say when he finds out what I wanted to do. Jake looked at the stack of closed cases I gave him and said. "Dam Jerry you really worked your tail off this week. Come on this calls for a few drinks to celebrate. Maybe if we're lucky we can find us a couple of sluts to nail before we go home."

This was not uncommon, as Jake and I would go out once a month or so for a drink or two before he went home to his wife. As far as the sluts were concerned we both knew that would never happen. Jake loved his wife and kids too much to risk getting caught. And as far I finding one we both knew that would never happen.

I woke up late Thursday morning with a pounding headache. My stomach felt like I had been punched numerous times and my mouth tasted like aged cheese. At first I couldn't remember why I felt this way then I remember going out drinking with Jake. Jake was in the mood to celebrate and before either of us realized it we were well into our cups so to speak.

It took a while for me to remember that I had open up to Jake. He had nonchalantly told me I needed to find a woman to take care of me because lately I looked like hell. Seeing I was quite drunk at the time I told him I had found a woman. When he asked for more details, I gave every detail I could think of right down to the size of her penis. I also went on to tell him exactly what we did and how much I loved it. It wasn't long after that I was in a cab on my way home and so was Jake.

When I turned on my computer I found an instant message from Jake telling me to be in his office at four this afternoon or else. I had no idea what or else meant but I was sure it had something to do with my confession of the night before. I knew I screwed up royally and I was going to have to start looking for a new job.

By ten to four I walked into Jake's outer office. Jake's secretary said. "Back so soon Jerry?"

"Yea, he IM'd me and told me to be here at four." I told her.

She sighed and said. "Good luck he's been in a foul mood all day. He's chewed me out twice for something he was suppose to do." She picked up the phone and told Jake I was waiting. When she hung up she picked up her purse and said. "You can go in now and I'm leaving while I have the chance." By the time I opened the door to Jake's office his secretary was already out the door.

When I walked into Jake's office he was on the phone and I heard him say to the caller. "He just came in this shouldn't take long so I'll see you at the restaurant."

Jake put down the phone and said. "Good afternoon Jerry have a seat." I thought I should remain standing. I figured that if he became violent I could try to run but when he growled for me to sit the second time I dropped into a chair.

Jake straightened out some paper on his desk before he said. "You know Jerry you really pissed me off yesterday. I've never been as mad at any one as I am at you."

In a timid voice I said. "I'm sorry Jake it not like I planed it. It's just how I feel."

"Well I'm sorry you feel that way. I always thought of you as a friend and then to hear you tell me you have no friends really pissed me off."

Okay this was not going the way I had thought it would so I said. "I'm sorry Jake I never thought you felt that way I just thought you were being a boss. A good boss but a boss non-the less."

Jake growled and said. "I don't usually invite my employees out for drinks or to my home for dinner. I only do that with friends. But of cause you wouldn't know that since you never bother to accept one of my invitations."

I felt bad about that so I said. "I'm sorry I thought it you were just making an idle gesture. I didn't think you wanted me to come. A lot of people say they want you over for dinner but they don't really mean it."

Jake laughed and said. "I guess they do, but I meant it. I want my wife to know who I talked about all the time. I keep telling her how smart you are."

I didn't know what to say to that and I didn't thing Jake did either. We didn't speak for a few seconds then Jake said. "About that other thing you talked about last night were you serious?"

I looked down at my feet, the same feet that still had red nail polish on them. Jake couldn't see them because of my shoes but I knew that were there. Finally I said. "I know you hate gays but yes I'm going to do it. It just felt so right."

Jake chuckled and said. "Like you said some people say things they don't really mean. That's not to say I want to go that route. It just means I really don't care one way or the other. I know I said some things, but I just thought that's what two guys say to each other. That's why I was always embarrassed when you mother was brought up. I kept forgetting she's that way. Now if that's really the way you want to go then it's okay with me as far as your job is concerned. You don't have to go looking for a new one like you said last night."

I was shocked that he said this so I said. "Are you sure, don't you think that could cause problem with the other employees?"

"If you have problems with the other employees we'll work them out. Jerry I don't want to lose you. You're the best investigator I have. Besides who do you really see here beside my secretary and me. I'm not sure how she'll feel about it but that's her problem. I can replace a secretary easier than I can replace you. Now if this is what you want then go for it. God knows you need some happiness in your life. Just do me one favor.

I couldn't believe my luck so I said. "Anything Jake what is it."

Jake laughed and said. "From now on don't tell me about the sex you and this Janie have. That was more information than I really needed." We both laughed about that. Jake handed me a few cases and told me he would see me the following week.

We walked outside together he went uptown to meet his wife and I went down town to go home. I was half way home when my cell phone went off. When I looked at it I saw it was a number I didn't know.

When I turned it on and said hello I heard a sweet sultry voice say. "Hi there baby girl would you like to meet me for dinner." I knew instantly it was Janie.

"Of cause I do where and when." I told her excitedly.

Janie told me to meet her in a restaurant near the business district. I told her it would take me an hour to get there. She told me she would be waiting breathlessly and that I should hurry.

I knew taxis' were going to be stuck in traffic and the subways would be crowded, but the subway was my best bet. Luck was with me, as the five o'clock rush had not let out as yet. It took me only forty five minutes till I was walking into the restaurant.

Janie stood up as I came into the restaurant so I could see her but I spotted her the instant I walked in. She was wearing a navy blue blazer with a white silk blouse underneath, matching knee length skirt and white two-inch pumps. Her smile lit up her face as she watch me stumble my way over to her.

She hugged me to her and kissed me on the cheek before she whispered in my ear. "I missed you baby girl. I hope you missed me too."

"I missed you terribly." I told her.

We sat down next to each other just as the waiter brought over our menus. With out looking at the menu Janie ordered a salad with vinaigrette dressing and a bottle of wine. I ordered a salad as well.

After the waiter left Janie asked. "Did you do what I asked." I told her about getting Geraldine Adams an Identity. "Well you are resource full. What about your job, you know once you become girl you can't switch back and forth."

I told her what took place just before she called me. I also told her about the night before and what I told Jake. "My you were lucky most girls like us have to give up good paying jobs and take junk work when they make the switch. You must be really good at what you do. Now what about your mothers."

"I haven't told them yet but I will. I just didn't want to do it over the phone." I told her.

Janie smiled and said. "I understand and I agree you should tell them in person. Now would you like to move in with me I have plenty of room."

Of cause I said I did. Janie told me that she normally worked Monday through Thursday unless she had a job that needed her at a different time. "Now if you really want to do this then tomorrow I have a hair appointment for you and your nails will be done at the same time. Since you have a credit card in Geraldine's name we can do some shopping after. Of cause we'll have to get you a drivers license in case someone asks for an ID."

We ate dinner and then went to Janie's apartment where she had me put on my make up and change into female clothes. But just after getting my makeup on my cell phone went off. Jamie quickly grabbed it and answered it.

It was my mother. I heard Janie's half of the conversation. "Oh hello Mrs. Adams. Yes your son is here but he can't come to the phone right now. Oh my name is Jane Michaels, his girlfriend. He hasn't told you about me yet well maybe he just forgot. No he didn't tell me about his coming for dinner on Sunday, Oh I would love to come, he's told me a lot about you. Oh wonderful we'll see you on Sunday." Janie hung up the phone and said. "There now you can tell her on Sunday. You can still get your hair styled but we'll leave the nails till Monday."

Once I was made up and we were dressed in nightgowns Janie and I went in to watch some TV. Half way through one of the sitcoms Janie said. "I guess I should tell you this now. We can't have an exclusive relationship." When Janie saw the question in my face she said. "You know how much you loved having my clit inside you. Well I love it just as much and though I love you little clit in me I'm going to need more. I also like men, big men and from time to time I will date men. You can too."

"I don't need any one else." I told her. She could hear the disappointment in my voice.

Janie pulled me into her arms and said. "Please baby girl don't be that way. I know it's disappointing to you and you probably think it's because of you little clit but it's not. Even if you had a big clit like mine I would still want to date men. I like how a man makes me feel and like giving myself to them. When I'm with a big man I feel more like a woman."

"Will you be bring them here?" I asked hoping that she wouldn't.

"Not if you don't want me too. I would rather bring them here because all my stuff is here but if you don't want me to I won't." She told me.

I knew that would be asking a lot of Janie seeing that this was her home and not mine. I told her she could bring them here and while they're here I'll stay in the spare bedroom.

Janie thanked me before saying. "You know you're going to have to try a man once, just to see if you like it too. You can't say you don't like men if you never had one." I didn't like that either but I knew that Janie wouldn't let me rest until I slept with one man.

That night Janie and I made love with me on my back and my legs up near my breast. This time she didn't use any dildoes to open me up in stead she used her fingers to get me lubed then eased her clit into me. At first the pain was almost unbearable and I almost asked her to stop. But then the pain slowly started to diminish. After a few minutes of slow shallow fucking the pain was gone and I was begging to be fucked harder.

Once Janie came in me and I came on my nightie she asked. "Are you okay baby girl."

"Now I am. It hurt a lot when we first started but it got better." I told her.

Janie kissed my cheek and said. "I know baby girl but it's something you have to get use to. Your boyfriends aren't going to use dildoes on you before they fuck you. Men aren't that considerate. Lets go clean up so we can get some sleep."

On Friday Janie and I went to the Drivers license office and I got a new drivers license with my girl picture. It looked horrible but most driver license pictures do. We then went to the beauty salon that Janie had made my appointment.

I was quite surprised when I went in and found Lacey was the stylist. All pretence of me being a real girl stopped when Janie said. "She wants a do that's easy to take care of but she also has to appear male one more time. She still hasn't told her mother yet."

"Well I'll be, she had me fooled even with this nasty hair style." Lacey told Janie before she said to me. "Come on little one when I get done with you your own mother won't know she had a boy."

I was soon in a chair bent way back so I could have my hair washed. While she was wetting down my hair Lacey reached under the short skirt I was wearing and felt my clit. "Talk about little one." She said as she played with my clit. This caused me to redden with embarrassment. Lacey saw my red face and said. "Don't be embarrassed little one. At lease you can wear jeans and slacks with out reveling what you are. Isn't that right Teddie?"

I looked over to where she was looking and I saw Teddie standing close by thankfully there was no one else in the shop. "You'll never hear me complain." Teddie told her, to me she said. "My boyfriend's glad I don't have a big one. He said it would make him gay if my clit was bigger than it is." Both girls laughed about this. "Besides I can wear anything I want without worry. My clit's only two inches long when hard."

When Lacey was finished with my hair it was a lot shorter then it had been and it was cut uneven. At first I thought it was a joke, then I realized how well it looked and how feminine it looked. I couldn't imagine how it could be combed to look like a man's. The way it flipped up on top could be flatten down, but the uneven sides didn't look manly at all.

Lacey saw what I was looking at and said. "All you have to do is wet it and comb everything back then hit it with some hair spray." I paid for the hair cut and Lacey said. "Remember Monday eight AM is your appointment to get your nails done. You will probably be here till noon." I thanked her and Janie and I left the shop.

"Now lets go to your place to get your computer and whatever else you need. While were up there we can stop at a dress shop I know to see if we can find something." Janie told me. When I asked if she had anything special in mind she said. "No silly I shop just to shop. Don't worry you'll get the hang of it.

We took a cab up town to the area where I lived. We stopped in three different dress stores as well as Macys and Gimbals. By the time we were done we were loaded down with boxes and bags. Most of the clothes were for me but Janie bought herself a few things as well.

When we reached my apartment Janie said. "Well I'm glad we decide to buy some clothes you've worn just about everything that Samantha left behind. By the way beside being exhausted how do you feel about shopping?"

"Well it's a challenge just keeping up with you but it was fun and I love all the clothes we bought. I'm sorry that it's over."

Janie laughed and said. "Over, no dear girl you've only just begun. You have enough pretty things to wear but you still need the basics. We'll get those tomorrow now what do you need here beside the computer."

I wanted to bring everything but in the end we only had room in the cab for my computer equipment. I would have to arrange for movers to come and take what else I needed. Janie hailed a cab on the street and paid the driver to carry down the computer equipment. She told me girls shouldn't carry heavy things. When we got to her apartment I paid him an extra twenty to carry it up.

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