Little Man Pretty Girl Ch. 01

I was shock at what I was thinking. Not only did I think I looked good in women's clothes but I was also thinking of ways to improve the look. What was wrong with me? A guy's not supposed to think this way. But then a guy never looked this good in a dress before.

My mind went from loving this look to hating it because the man inside me was telling me it was wrong. It wasn't until Janie came up behind me and slipped her arms around me that I finally made up my mind. "Well sweetie what do you think," Janie asked.

In that instant my whole life changed. "I can't see how I could ever go back to wearing men's clothes again. I'm sorry that probable sound pretty sick doesn't it?"

Janie kissed my neck and said, "Not really. I knew this was the real you the second I saw you in the club last night. I knew you hated what you were and I knew once I showed you how good you can look you would never go back. Now I want you to go and practice walking in those shoes. I also want to you to practice siting like a lady. I'm pretty sure you know what I mean. Meanwhile I'm going to shower and get dressed. I think we should go out for dinner and then to the club for some dancing."

I dragged my eyes off of the vision that was in the mirror and turned in Janie's arms. I reached up wrapped my arms around her head and said, "I don't know how you knew this was the real me but thank you for showing her to me."

Janie kissed me before saying, "I can show you a lot more that I know you will really love if you keep an open mind and allow yourself to experience them. Now go and practice so I can get dressed."

It only took me a few minutes to get use to the shoes and within fifteen minutes I was walking like I had been born in heels. All I had to do was think about all the women I saw walking down the street in heels and the rest was easy. Learning to sit and cross my legs came just as easily.

When Janie came out of her bedroom She was wearing a short dark blue dress and four-inch heels. She was caring two purses, one navy blue and one red. She handed me the red one and my wallet before saying. "Put in your credit card and your money. You can't use the credit card in stores but you can draw out cash from an ATM if you need it.

I knew she was right because my credit card had the name of Gerald on it and I was going to have to change it to Geraldine. I could still use the name Jerry but I'd have to change the spelling to Jeri. For anyone else this may be difficult but for me it was easy. All I needed was my computer and a little time.

Janie had called a cab to pick us up outside her apartment. We took the cab to a restaurant but before we went into the restaurant she pulled me into a jewelry store that was still open. She purchased a pair of starter earrings and had the jeweler pierce my ears with them. It was strange that she didn't ask me if I wanted them nor did I even balk at having them.

The restaurant was very nice and Janie and I drew a lot of attention as we walked though the restaurant to our booth. When I was dressed as a man I could barely get the waiter to notice me but tonight it seemed that he was hovering around our table.

Janie and I had vegetarian meals. I have been a vegetarian since birth and so was Janie. My mother wouldn't allow meat in the house and even Betty wouldn't eat it. I tried a burger a few times when I was a teenager but I didn't care for the taste so I stopped eating it. Janie told me she felt the same way and the low fat diet kept her waistline respectable.

Once we were in the cab going back to the club I remarked on the service we received and told Janie what I was use to receiving. Janie told me, "That because then you were an unimpressive man but tonight you are a sexy chick. Besides he received a very generous tip for the meal."

"Speaking about that what do I owe you for the meal," I asked.

"Don't worry about that you can pay for the drinks tonight and this cab ride," She told me which sounded good to me.

It wasn't until the cab stopped at the club and we got out that I realized I didn't have an ID to get in the club. I knew as a man no one ever believed I was twenty-one, now dressed as a girl I looked even younger.

I told Janie about my problem to which she said, "Just stand back and I'll take care of it. I have a lot of friends here and I'm sure I can get you in."

Janie went up to the doorman and spoke to him. I saw her hand the doorman a card, which he looked at before handing it back to Janie. The doorman stamped Janie's hand and then held out the stamp for me. He smiled at me and said dam before stamping my hand. Before he could say anything more Janie rushed us into the club.

The club was a lot busier then it was the night before. There were at least three times more people in the club tonight, but the women still outnumbered the men three to one. Janie and I got a glass of wine each before looking for a booth to sit in.

Just as we sat down two other girls came and sat down with us. One was a red head and the other one had brunette colored hair. The brunette looked slightly oriental and she was rather small. The red head was much taller and was very attractive.

"Well Jane were did you find this one, she's a real cutie." The red head asked.

Janie smirked and said, "Easy Lacey this ones all mine. I found her first."

"Meooow! You don't mind if I dance with her do you," Lacey asked.

"No as long as I can dance with Teddie," Janie told her.

"Okay we'll trade. Come on little one," Lacey told me as she held out her hand to me. I took a second to look over to Janie who simple nodded her head as she got up to take Teddie's hand.

Lacey and I danced through two songs. She asked me what my name was and how I met Janie. Since this was the first time I had to speak to someone other then Janie I had to do it carefully. Seeing my voice was never what any one would call deep to begin with I tried raising the pitch of my voice just a little but I also lowered my volume to a little above a whisper. What came out was a mix between a sultry alto and a breathy soprano. When I told her my name my voice sounded rather nice so I explained that I met her the day before at the club and we have been together the entire day.

When Lacey asked, "Is you name spelt J-e-r-r-y or J-e-r-r-I?" I thought she had found me out.

"It's spelt J-e-r-I like Jeri Ryan from the Voyager series," I told her.

Luckily the song ended and Lacey released me from her arms. Janie was right next to me and she took me in her arms when the next song started. We danced together for a minute or two before she asked, "Did Lacey say anything nasty to you?"

"No she just asked what my name was and how I met you." I told her as I rested my head on her warm breasts.

Before Janie could ask another question two men approached us. One was a little taller than Janie was and the other was about as tall as Janie when she wasn't wearing heels. The tall one asked if they could cut in to which Janie told them they could. I was surprised when Janie told them they could and easily flowed into the arms of the taller gentleman leaving me with the shorter one.

I wasn't very comfortable in his arms as you could imagine. I mean it was one thing to wear a dress and dance with a real woman, but it was something else entirely to be wearing a dress and dancing with a man. I was actually terrified that he would figure me out and slap me around for deceiving him. But I couldn't figure out how to get out of his arms with out drawing attention to us. I also wanted to know why Janie left me with him.

We danced for a minute or two till he said, "My name's Tim what's yours." I told him my name and he said, "This is a nice club are you a regular?"

"No this is my first time here," I told him. Even though it was my second it was still my first time dressed like a girl.

Tim looked sad and said. "I was hoping that you were one of the regular girls. I mean they are what I was looking for."

I could see a blush come to his face, which for some reason help me to relax so I asked, "So what are you looking for from one of the regular girls?"

Tim's face became even darker before he stuttered out an answer, "Well I guess seeing you're not one of the regulars maybe I shouldn't tell you. I mean if you are not one of them then that would be really embarrassing."

Before I could pursue the question any further the song ended and Tim left me standing on the dance floor alone. I shook my head at his complete rejection of me before leaving the dance floor.

Before I could make it back to my table Janie was at my side. As soon as we sat down Janie took my hand in hers and asked, "Are you okay, that guy wasn't fresh with you was he?"

"No he was pretty nice but I wasn't what he was looking for. Which to tell you the truth I'm kind of glad I wasn't," I told her.

"What was he looking for," Janie asked.

"He was looking for a girl that was a regular to this club. He seemed uninterested in me when he found out I wasn't one of them."

Janie laughed before saying, "Sweet heart you probable were one of them, but the poor thing didn't see it." I asked Janie what she meant so she said, "Honey this is a drag queen club and he was looking to hook up with one of them. You do know what a drag queen is don't you?"

Of cause I knew what one was. I had met a few during the gay pride events my mother took me to. It was at that instant I realized that I was now one of them. Well I would be if I kept dressing like a girl and I couldn't see changing that. I shyly said, "Yes they're girls like me."

Janie pulled me close kissed me and said, "Yes sweet heart they're girls like you. Now how does that make you feel? I mean to know that handsome man wanted a date with a girl like you. Do you think you would want to go out with him?"

If she had asked me the night before I would have told her I wouldn't want that. I mean I understand that people do that sort of thing and I never disrespected anyone for their sexual orientation but I never had those urges. But since I first saw myself dressed as a girl my whole outlook had changed. That doesn't mean I wanted to have sex with a man but I liked the attention they gave me. Where before no one paid me much attention but now it seemed everyone was looking at me and I really enjoyed it.

But I had to be truthful so I said, "Janie I can't say I wouldn't like the attention but I'm not sure I could do what they want I mean he would be looking for sex and I never did anything like that. I would have to put his penis in my mouth and in my backside. I'm not sure I can do that."

Janie kissed my forehead and said, "That's because you're a virgin. Don't you think every girl said the same thing before she tried it for the first time? I know I did and now I love it. For tonight don't worry about it because I'm not letting you out of my sight. Now lets go dance and have a good time."

We danced till two in the morning. Most of the time we danced together but once in a while a man would ask me to dance and Janie pushed me into doing it. By the end of the night I was really starting to enjoy dancing with men and I especially enjoy it when they held me close. Almost every man asked me if I was a regular or something like that. When I told them it was my first time most seem disappointed and they left me looking for more experienced girls.

At two in the morning Janie decided that it was time to go home. We walked the two blocks to her apartment with Janie's arm over my shoulder. We sat on the sofa and started kissing. We did this for about a half-hour till Janie said it was time for bed.

Janie found me a baby doll nightie to wear and told me to change while she went into the bathroom. When she came out she was wearing a red satin nightgown that went down to her knees. She came to me and we kissed before lying back on the bed.

We kissed for quite awhile then Janie open her nightgown and pulled out one of her breasts. She pulled my head toward her breast and told me what she wanted me to do with it. Instead of taking her nipple into my mouth she had me kiss her breast all over. Between kisses and licks with my tongue I covered her entire breast before she directed my head to the other breasts. It wasn't until I had covered both her breasts with kisses and licks that she would allow me to suck on one of the nipples.

While I was doing this Janie's hand was on my panty-covered cock. She massaged my penis though the panties for a long time. I loved the feel of what she was doing and the feel of the satin against my cock so much that I almost came in my panties. Seeing I was so close to cuming Janie stopped playing with me so I would calm down. When she released my cock she would pull me close and play with my ass. I learned that also felt good as she traced a finger along the crack of my ass.

When I felt like my balls were going to burst with the need to cum Janie took my right hand and placed it between her knees. I was sure she was telling me I could move up and feel her pussy. While I continued to suck on her nipple and with her hand on my cock I slowly moved my hand up her thigh.

I didn't want to rush this. I wanted to give her as much pleasure as she had given me. I also knew that my hands and mouth would have to give her pleasure seeing how small my cock was. I knew I would be very lucky if she allowed me to enter her with my tiny penis.

Instead of going straight to the V of her legs I rubbed her inner thighs with my hand. I also lightly scratched her thighs with my painted fingernails. Janie seemed to love what I was doing as she moaned sweetly every time my nails scratched her inner thighs as I got closer to her womanly mound.

When I finally reached her pelvis I could feel that Janie was as hairless as I was. Her pelvis region was as smooth as a baby's bottom and my mouth watered at the thought licking that special place with my tongue. After scratching her pelvis for a second or two my finger moved down to her slit. But when I got there I received the biggest surprise of my life.

When my fingers touched where I thought I would find her moist slit I found a lump of flesh instead. I could feel that it came out of her pelvis and bent back between her legs. Call me stupid but it took me a few second to figure out that what I was touching was a cock. Janie was a really a boy.

Once my fingers found Janie's cock I pulled my mouth from her nipple and stared down at her. Janie smiled up at me and said, "I told you I was full of surprises. Your not mad are you? I told you I wanted to make into a girl like me."

Janie pulled my head down and kissed me. Her kiss was warm and loving. When her lips left mine she laid my head on her chest and said, "Don't be afraid of it. I promise it won't bite. Just take it in your hand an feel it."

How could I refuse her? How could I refuse the one woman that showered me with attention? My hand moved down between her legs as Janie spread her thighs to give me access. Her cock was pushed back between her legs and I had to grasp the shaft to pull it out. As soon as I got it out Janie pulled up her nightgown so I could see what she had.

As soon as I got it out from between her legs it swell to full erection. I was surprised at how warm it felt in my hand, I was also surprised at how big it was. It was four or five inches longer then mine and at lease an inch and a half thick when fully erect. It was silky smooth yet it felt hard. With out thinking about it my hand stroked up and down the shaft to which Janie moaned sweetly as a drop of precum formed at the tip.

"See baby, see how excited I am that my little girl is touching my clit," Janie told me breathlessly.

I gave her clit another stroke and a second drop of precum forced the first one to dribble down the head and over my fingers. To tell you this didn't affect me would be a lie. Having that big cock in my small hand mesmerized me. I couldn't take my eyes off of it.

"Do you want to go down there and see it up close honey," Janie asked.

I wasn't sure if that was a question or what, but I knelt up to get a better look. Now that I was closer to it, it seemed bigger and I could make out the veiny texture better. Subconsciously my hand started to stoke the shaft as if it was the most natural thing to do.

I could feel Janie tense up and said, "Oh baby that's nice but squeeze it a little tighter."

I gripped it tighter and stroked it a little harder. Janie moaned and I saw her thighs tighten up. I loved when she moaned like that and I wanted to make her moan even more. When she told me to give her clit a kiss I didn't even think about it, I just leaned over and kissed the tip. When I pulled my lips away the tip of her clit had a red lipstick stain and my lips had a slick feel to them.

When I licked my lips I realized that they had some of her precum on them. I was surprised that the precum had no taste, but it did feel good on my tongue. With out thinking about it I leaned over again and kissed her cock.

But this time I did more then kiss it. This time I open my mouth and surrounded the head with my lips. I was surprised that having my lips around the head felt so familiar. It was like I had done this before. My tongue slid around the head like a swab and it came away coated in the precum.

When I pulled my lips off her cock I looked up at Janie and smacked my lips. Janie smiled and said, "You like that don't you? You like having my clit in your mouth. Don't be afraid baby you can suck it some more. Just lean over and take it in your mouth."

I knew what was expected of me. I dreamed about having it done to me for years. I turned around so I could get comfortable before pulling her cock back toward my mouth.

As soon as my lips surrounded Janie's cock she moaned deeply and I felt her give a little push with her hips. This slid her cock into my mouth a little more. At first this scared me and I thought she was going to ram it in my mouth. But she quickly settled down and allowed me to take my time.

It took me a while to get the hang of it but soon my mouth was moving up and down her cock like I had been doing it for years. I found that I enjoyed doing this and it felt good to have that cock in my mouth. But what I enjoyed even more was Janie telling me how good it felt to her.

"Oh that's my girl you sucking me so good. Take it a little deeper baby. Oh yea that's the way, mm god, your sucking me so well. Now a little deeper let me feel the back of your throat." I couldn't help myself I had to do what she wanted. I had to pleasure her the way she pleasured me all day.

I slid my mouth down till I felt it hit my throat Julie moaned and I felt the head of her cock get bigger in my mouth. I next pulled my lips back as I pulled a deep suction. This caused Janie to groan like she was in pain, but I could tell it was a sweet pain. When I slid my lips down again I went to far and the head pushed open my throat. I quickly felt a flood of nausea pass over me and I gagged violently.

When I pulled my lips back this time Janie said, "Oh baby girl I can't believe your trying to take in your throat all ready." I knew she liked this and I wanted to do it again.

I slid my lips down her cock once more and at the same time I tried to relax my throat. This time it slid in and even though I had to fight off the gag reflex I felt like I had just climbed Mount Everest. Janie squealed and I felt the head of her cock grow bigger. I felt her shaft pulse like it had it's own heart beat. I pulled back and did it again. This time my lips stopped at the bottom of her cock and I could feel her cum rush past my lips. The next thing I felt was a burning in my throat that I later learned was her first squirt of hot cum.