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Little Man Pretty Girl Ch. 01

By: Scribler



Why I went to the club I didn't know. I guess it was for something to do. I had been alone for so long that I needed the company of others. Even if they did treat me with disdain I still needed to socialize with other humans. 

You see I live alone and I work from home. I do security consultant work for companies that are having trouble with hackers. Recently my work revolted around Identify theft. 

I used to work in an office but that was even worse than working alone. Each day I would watch as the women in the office coyly flirted with any man that was around, any man but me. It wasn't because I was homely or because I had a disfigurement. 

It didn't have anything to do with my physical looks as much as my size. You see my growth had came to a sudden stop when I was thirteen years old. At the time I stood five foot two inches tall and thirteen years later my height had not changed. What was even worse I couldn't put on anymore weight than the eighty-nine pounds I weighed then. 

I always wished I had looked more like my father. He stood well over six feet tall and weighed an impressive two hundred and fifty pounds of rock hard solid muscle. Well at lease that was what my mother told me. I never knew my father he was killed by a drunk driver when I was only two years old. I know my mother loved him very much and she stayed faithful to him for five years after his death. That was when my Aunt Betty came into the picture. 

As far back as I could remember my mother was a fitness fanatic. I later learned that she would constantly exercise so when she went to bed at night she was exhausted. This caused her to sleep through the night and not wake up crying at the loss of her beloved husband. 

When I was able to go to school my mother thought it was time that she did something with her life as well. Not that she needed to work as my father had been very responsible before he died and took out several life insurance polices. When all the insurance polices were paid off my mother received well over three million dollars. My mother had a degree in business management and took an offer as manager of a local health club. 

Six months after my mother took the job at the heath club Aunt Betty moved into our guestroom. I'm sure that in the beginning they're relationship was purely platonic but with in a few months they were sleeping in the same bed. 

At the age of seven years old this did not effect me. My beautiful mother doted on me, as did my equally beautiful Aunt. What more could a boy want. My mother of cause treated me like her son but so did Aunt Betty and I treated them both like they gave birth to me. 

But here in lies one of my problems. You see most boys, whether they like to admit it or not are physically attracted to women that resemble their own mother. I unfortunately am attracted to women that look like my Aunt Betty. My life might be better if I was attracted to women that resemble my real mother. 

You see my real mother and I look very similar to each other in fact once we were asked if we were sisters. I have the same fair skin as my mother. We are also the same height. We weight nearly the same the last time we checked and our hair and eye color is the same. I've been told by some that I am the spiting image of my mother. 

Aunt Betty on the other hand is very different. She is almost six feet tall and very slim. She has large breasts that overflow her D cup bras. Her legs are very long and well muscled. She is what men think of when they refer to women as amazons. I know in my heart that women that look like my Aunt are unattainable to men like me but I still crave them. 

I have tried dating women that were smaller then me, but those women are hard to find and they seek men that are taller and look manlier than I do. Even when I have found a shorter woman that would go out with me my other problem rears its ugly head. 

You see being a small man has also had an affect on my manhood. My penis when hard is only three inches long and as thick as a quarter. When the few dates I have been able to get in my bed saw it several of them laughed outright while others told me that they needed a bigger penis to satisfy them. Only one or two were kind enough to not mention my size as a reason to break up with me. But I knew why they broke up with me. 

As you could imagine this left me quite jaded when it came to women though I could never turn to men for sex. Not that I had anything against gay men, As my mother was quite active in the lesbian community and I would be brought to many of the gay pride events as a youngster. I found most gay men fun to be around but I never found them to be sexually attractive at all. 

Seeing any possibility of having an active sex life as more or less a joke I retreated into my computer at a very young age. I found computers to be my forte. I was enthralled with their workings and spent hour after hour in front of one. When the Internet came along I was instantly hooked on it, as it didn't matter how big you were as long as you could punch keys on the keyboard you could get around quite nicely. 

At first I tried out the chat rooms like everyone else but they left me feeling empty. It was in one of these chat rooms that I got my first taste at hacking. I found that I was quite good at it and I could get into any system I chose to. I didn't do any damage or steal any thing of value. I just loved the challenge of getting in. I was careful not to leave any thing that could lead the authorities to me so I never got caught. That's how I got my first job but instead of hacking into a company I developed safeguards so others couldn't hack into them. 

This was why I came to this club. It had been several months since I was out amongst other people in a social setting and once again I craved other people around me. I needed their closeness and their smells as if to say to me that there were other people out there looking for the same thing I was. 

The club was in an old warehouse district that at one time, a long time ago was filled with crates filled with everything a big city needed to survive. Once the transportation system grew and the city could be supplied from the outside. Areas like these highly expensive and highly taxed warehouses were no longer needed. They were bought up by enterprising entrepreneurs and turned into night clubs and loft apartments for the young and wealthy. 

It was my first time to this club, as I very rarely went to the same one twice. As usual I had to show my ID as I entered seeing I never looked my age. Once inside I looked around and saw that for it's size there were very few people in the club. There were only twenty or so people of which most of them were women. Seeing this was a Thursday night I thought it was unusual. You would think there would be more men around with this many free women. 

As my eyes surveyed the room I saw standing just inside the door what could only be my image of my perfect woman. She was tall almost six foot in height. She had long shapely athletic legs encased in shear hose atop four-inch high-heeled shoes. Her upper legs were wrapped in her electric blue Lycra mini-skirt that left half her thighs exposed. Her flat hard tummy was bared so one could see the diamond pendant that was pierced though her navel. Her matching top was tight around her large breasts and her nipples were poking though the material. Her face was beautiful and her makeup accented her features perfectly. On top of her head was a mane of golden blond hair that cascaded down to mid back. 

She was everything I wanted in a woman and everything I knew I could never have. Even as she stared back at me I turned and walked away toward the bar. I wanted one drink before I went back to my apartment in despair. 

I climbed up on to a barstool and ordered a double scotch on the rocks. I waited for the bar tender to ask for my ID but she didn't ask. I'm sure she knew I was carded when I came into the club. As my drink was poured I placed a twenty on the bar to cover the cost. 

From behind me I heard a sweet sultry voice say, "Nancy that one's on me and I'll take my usual." When I turned to see who just bought me a drink I saw my Amazon beauty smiling down at me as she asked, "You don't mind if I pay for that do you?" 

What could I say, well really I couldn't say anything as my tongue was tied in knots. I barely shook my head no as I watched her slip onto the barstool next to mine. Her smile never left her face as she held out her hand and said, "My names Janie Michaels."

I took her hand gently and said in a horse whisper, "Jerry Adams." 

Janie smiled and asked, "Is this your first time here? I don't think I ever seen you here before. I'm sure I would remember someone as cute as you." 

Cute! I hated the word cute when some one was using it to describe me. But for some reason I didn't mind that Janie was using it. But then again I could care less if she called me a pig as long as she kept smiling at me. 

Janie and I talked for a few minutes at the bar before moving to a secluded booth. We continued to talk for the next three hours on every subject you could think of. She was very intelligent and we had a lot in common, from losing our fathers at an early age to working in the computer industry. 

Janie was a system analyst but instead of working for a company she was a freelancer who did work for several smaller companies when they needed her. Apparently she did quite well as she had several other analysts working for her and they all did pretty well monetarily. 

At two in the morning Janie leaned over and kissed me on the lips before asking, "Would you like to come and see my apartment? It's just a few blocks away." 

Her kiss was so sweet it made my head spin and my toes curl. There was no way I was going to say no. The fact that I was ill equipped to satisfied this lovely creature wouldn't have stopped me, though at the time my short comings was the furthest thing from my mind. 

When I agreed to go with her she kissed me once more and this time she slid her tongue into my mouth. Again I was left dizzy by her kiss before she said, "Finish your drink before we go." 

I downed what was left in my glass as Janie finished off the last of her wine. She then stood up and held out her hand to me. I took it and we walked out of the club hand in hand. 

Janie's apartment was two blocks from the club in fact it was in another of the renovated warehouses. By the time I was less then a block from the club I was finding it difficult to walk in a straight line. I was sure it was because of all the drinks I had and seeing I wasn't use to drinking so much. By the time we reached her apartment we were laughing at just about anything. 

When we finally made it to her apartment Janie pushed me on to one of her couches and started kissing me. Her mouth seemed to be every where and her hands were every where her mouth wasn't. I'm not sure how it happen but Janie's top came off and I was sucking on her nipples like a baby while she started rubbing my cock though my pants. It had been so long since anyone other then myself had touched my cock that with in seconds I was dumping a load of cum straight into my pants. Once I came I think I passed out as the next thing I remember was opening my eyes and to a blinding bright light. 

When I became accustom to the light I realized that it was the sun streaming in though a large window that went from the middle of the wall up ten feet to the ceiling. I was lying in a bed that was three times bigger then the full size bed that I normally sleep in and the room I was in was at lease thirty foot by forty foot. The bed I was in had satin sheets and a silk lined comforter all in pink. The walls were done in white and there were paintings hanging on three of the four walls. 

I knew instantly that this wasn't my bedroom but it took me a few moments to realize whose bedroom it was. Then I remembered Janie from the night before and I also remembered that I had passed out on her sofa. 

My head hurt like some one had hit me with a baseball bat and the rest of my body hurt as well. In fact every muscle in my body hurt so much it reminded me of the last marathon my mother talked me into running with her and Betty. Even my throat and my backside were hurting. 

When I pulled the sheet back to get out of bed I saw that I was completely naked. I had no idea where my clothes went, as I didn't see them anywhere in the room. The only thing I did find was a white satin robe lying at the foot of the bed. With nothing else to wear I slipped into the robe and went in search of a bathroom. 

After going to the bathroom I looked in the mirror. My face was slightly puffy and my eyes were blood shot. Other than that I seemed okay except for my head pounding and my muscle aches. I figured I should go look for my clothes and see if Janie was at home. 

I looked every where for my clothes until I found Janie working at her computer. Thankfully I didn't have to punch a clock and no one would notice I wasn't at my computer at home. When I saw her I cleared my throat and said, "Um can you tell me where my clothes are. I don't remember getting undressed and I guess I should leave." 

Janie turned at the sound of my voice and smiled. She looked even better than she did the night before. She was wearing a crop top tank top and a pair of baggy shorts. She didn't look hung over and from what I could see she seemed pleased to see me. She stood and came over to me and kissed me lightly on the lips before saying, "Well just like a man. Get his jollies off passes out and when he does wake all he want's to do is leave." 

I couldn't tell if she was joking or if she was upset with me so I quickly said I a bit of a whine, "No it's not like that I just though you would want me to leave seeing you have work to do." 

Janie gestured to her computer and said, "Oh I'm just answering some emails. It's no big deal. Besides you can't leave yet I put your clothes into the washer. You made a bit of a mess in them last night and I thought you would want them cleaned before you put them back on." 

When she mentioned that I had came in my pants a wave of embarrassment swept over me. I instantly could feel my face start to heat up. Janie giggled and said, "Don't worry lover you're not the first man to do that and I'm sure you won't be the last. Now how about I make you some breakfast." 

Just the thought of food turned my stomach and Janie saw it in my face. "Well how about some coffee orange juice and a couple of aspirins." 

Just the though of something to drink reminded me of how thirsty I was. "That sound really good and if you don't mind do you think I could take a shower too," I asked. 

"Of cause love. I have a new toothbrush you can use and I'll see what I can find for you to wear, though I doubt I have much that would fit you." Janie told me as she took my hand and showed me to her bathroom. 

Once she gave me the new toothbrush she left the bathroom. I quickly found the toothpaste and started to brush my teeth. When I pushed the toothbrush into my mouth I saw a picture in my mind of something being pushed into my mouth. At first I wasn't sure what it was then the vision became clearer and I realized that it was a penis and a large one at that. I quickly shook my head and the vision disappeared. 

I wasn't sure why I thought of that, as I never had any thoughts like that before. But the vision kept coming back and after a few times I could see that the cock was jutting from Janie's crotch. The vision stopped coming but I could now see it in my mind quite clearly as if it really happen and I had enjoyed it when it did happen. 

When I finished brushing my teeth I stepped into the shower and started to wash up. When I washed my bottom I had another vision of Janie fucking my ass with her cock. This vision was even more vivid than the one I had of sucking her cock. I could almost hear her telling me that I was her girl and she was going to do this every night. I shook my head to clear the vision and quickly washed up and got out of the shower. 

The thought of gay sex never bother me but to have these day dreams about a girl like Janie it wasn't right and I was shaken to my core that I was having them. I stood in front of the sink with my arm braced as if to hold me up while my body shook at what my mind was telling me.

That was how Janie found me when she came back into the bathroom. She wrapped a towel around me and asked, "Are you okay sweetie your shaking like a leaf?" 

She held me to her and that simple gesture seemed to relax me. But to cover the real reason why I was shaking I said, "I guess I'm hung over worse than I thought." 

Janie patted my body off with the towel to dry me as she said, "I think you're dehydrated too. You did have a lot of alcohol last night and that can dehydrate you. Let's get you dried and into some clothes and I'll get that orange juice for you." 

Janie started to rub the towel along my back and bottom and before I knew it I was hard. I told her that I could dry myself but before I could get it out Janie reached around me and cupped my package in her hand. She massaged my cock and balls for a second or two before she said sweetly, "Are you going to take care of this too, or are going to let me handle it." 

Before I could say anything Jane turned me around and dropped to her knees. She then bent over and sucked my cock into her mouth. I never had any one do this before and god it felt so good. Her warm wet mouth felt wonderful and the way her tongue played with my cock was nothing I ever felt before. God I didn't want her to stop, but I couldn't last that long as I felt a strong urge to cum. 

When I knew I couldn't hold out any longer I said, "Janie I think you should stop. I can't take that anymore." 

But Janie didn't stop in fact she sucked even harder and her tongue whipped at my cock inside her mouth. In less than a second I groaned deeply as the first jet of cum fired out of my cock and into Janie's mouth. I heard Janie moan and she moaned as each squirt of cum was pumped into her mouth. 

Once Janie sucked me dry she leaned back open her mouth so I could see the load of cum I had just pumped into her mouth. Once I saw it Janie closed her mouth and made a big show of swallowing my cum. 

When she was done she licked her lips and said, "Mmm that was yummy. You must be a vegetarian. I hope you'll let me do that again I really liked the way your cum tastes. The only thing I didn't like was all this hair. It tickled my nose." 

I helped Janie to her feet and told her that she could do it any time she like and I would be glad to return the favor. Janie stroked my hair and kissed my forehead before saying in a far away voice, "You will my sweet you will. But for now lets get you dressed so we can get some fluids into you. I hope you don't mind but I didn't have anything that I thought would fit you except for a few things and old girlfriend left behind." 

Janie walked me into the bedroom and showed me the clothes that she had found. First was a pair of pink satin and lace panties. I thought to myself that I really didn't need them until Janie said rather forcefully "I tried to find you a pair of plain white cotton ones but none of my girl friends wear anything like that. I knew you had to wear something under your cloths so I picked out those. The Capri pants are the closet thing I have to pants that I thought would fit you and the tank top isn't gender specific. As for the sandals they were all I had and I knew you had to wear some thing on your feet. I'm sorry but that was the best I could do." 

I told her that it was okay and I appreciated her efforts. Janie kissed me lightly on the lips and left me to make a pot of coffee. I picked up the panties and once again thought to myself that they really weren't necessary but Janie made it clear that she thought I needed them so I put them on to make her happy. It's the lease I could do seeing that wonderful blowjob she just gave me. Beside if she decided that she wanted to give me another one I really should be wearing them. 


Little Man Pretty Girl Ch. 01



Next I pulled on the Capri pants, they were tight in the butt as well as my legs but there was some stretch to them and once I had them on they seem to fit rather nicely though they didn't come up above my hips. The tank was also tight and it too only reached about half way down my stomach. This left a large gap that exposed my belly for anyone to see. 

After sliding the sandals onto my feet I walked over to the full length mirror that hunk on one of the walls. What I saw looking back at me was a younger version of my mother. Except for my hair and the lack of make up I looked like a girl in these clothes. I almost took them off but in the end I decided that Janie went to too much work getting them together. I decided to let Janie see them and ask her what she thought. 

I found my way back to the kitchen where Janie was cutting up some fresh fruit. I cleared my throat and asked, "Do you think this looks to feminine on me." 

Janie looked up and smiled then looked closely at me before asking me to turn around for her. Finally she said, "Well there no mistaken those as girl's clothes but you carry them off pretty well. I'm sure you already knew that what exactly are you asking me?" 

I felt myself blush deeply before I said, "I was just wondering if I looked too much like a girl in them." 

Janie smiled and came over to me before saying, "You look like a boy who is wearing girl's clothes. But if you want to look like a girl I think we can do it. If we combed your hair a different way and put some make up on you. I think you would make a very pretty girl. Of cause we would have to put a bra on you and something in the cups to give you a shape but I think we can do that if that was what you want." 

"No, no I don't want look like a girl. I mean I don't want to ruin what we have. You are the first girl to have anything to do with me in a long time and I don't want to ruin that," I told her in a rush that sounded rather desperate. 

Janie took me in her arms and said in a voice that sounded like she was talking to a child, "Sweetie that won't ruin what we have. I like you just as you are. But I'll let you know right now that I like girls more than I do boys. I like how they smell and how they feel in my arms. So don't get too attached to me because sooner than later I'll be out looking for another girl to fill my bed." 

I didn't like what she was saying and I'm sure it showed on my face. Janie moved me over to the table and sat me down. She then got me a large glass of orange juice four aspirins and a cup of coffee. She went back to cutting up the fruit while I drank my juice. When she was done cutting up the fruit she brought over plates for both of us. She sat across from me and started to eat. 

All the while she ate she kept staring at me finally I asked, "Is there something wrong with me?" 

Janie shook her head as if to clear it before saying, "No Sweetie I was just day dreaming that was all." When I asked her was she was day dreaming about she said. "You probably won't like my answer, but I was just thinking that if you were a girl I would really fall for you. I mean you would be everything I would be looking for in a female lover. You very sweet and you're tiny like the girls I usually go for. I know this sounds silly but I think I could really fall for you if you were a girl like me." 

Janie giggled at the thought before turning back to her food. When she finished her breakfast she turned to me and said, "Your clothes should be ready to go in the dryer. I'll check them so you can get going as soon as possible." 

I felt that she was dismissing me and I dread that this would be the last time I would see her. I wanted to let her know I'd do anything so I could keep seeing her but I wasn't sure what I could offer her. 

I had just finished my breakfast when Janie came back into the kitchen. She sat next to me and said. "Your clothes should be done in a half-hour." She then brushed her hand over me cheek before saying, "Do you think I could ask you a big favor." I told her yes. She then said, "This maybe to big of a favor for you to grant and it may sound a little freaky. I don't want you thinking I a freak." 

"I would never think that. Go ahead and ask," I told her quickly. I saw this as a possible opening to some sort of relationship with her. 

Janie giggled and said, "I better not, the more I think this through in my head the stranger it sounds and I don't want you thinking I'm some weirdo. No maybe you should just go home an let me get over this." 

I felt the rejection in her voice and I knew that my fun with this beautiful woman was coming to a quick end. So in desperation I said, "Please tell me what you want. I promise I won't think you're strange." 

Janie giggled once more and said, "Okay but I warned you. I was just thinking that I would like to dress you up like a girl. Not like you are now, but fully dress you up. I mean make up and restyling your hair. I want to put polish on your nails and even reshape your eyebrows. That's really weird isn't it?" 

Okay this was weird and my mind rushed over the implications of what it would mean. I knew she would think of me as less of a man if I did this, but lets face it I really wasn't much of a man anyway. Besides what could she do that I couldn't change back. Even if she reshaped my eyebrows all I had to do was wait and the hair would grow back. I also saw this as a way to show her I wanted to be around her. I finally told her she could do it if she wanted as long as she didn't do anything that was irreversible. 

Janie's smile lit up her face and she before she said, "Are you sure. I don't want to force you into anything you don't want to do. But I do think you would make a really pretty girl." 

I knew she was right about that. Hell I was told several time by several women that I should have been born a girl. I even saw it for myself an hour ago when I looked in the mirror. So after swallowing what little manhood I had left I told her I was sure. 

Janie jumped to her feet pulled me into her arms and kissed me deeply. My head spun once more as I stood on my tiptoes so I could reach her lips. Once she was done kissing me she said, "First we should shave your arm pits and your legs. After that I want to shave you pretty little cock and those cute little balls of yours." 

It kind of hurt my feelings when she said my cock was little but at lease she wasn't laughing at it. Janie pulled me down the hall and into her bedroom where she quickly stripped off all my clothes. She then moved me into the bathroom where she got out a razor. She shaved off the sparse hairs on my face, which had been growing for the last month then she went to work on my armpits. 

Once my armpits were done Janie stepped back and looked me over before saying, "Maybe we should use hair remover instead of the razor. It will take less time and in the end your skin will feel a lot smother and more like a girls." 

Janie took out a blue and white bottle from under her sink and gave it a few shakes. She then dropped to her knees in front of me and started coating my legs with the thick blue-green liquid. She worked up my legs and all over my crotch before tuning me around. She covered me ass in the liquid and also my back before turning me once more to cover my chest and stomach. She even coated my arms with the liquid. 

When she was done she said, "We need to let that work for ten minutes before you can wash it off. Meanwhile I'll go see what I have that I can dress you in. Thankfully Samantha left a lot of her old clothes here when she moved out and I'm sure you two are the same size. Those were her Capri pants you were wearing earlier." 

At first my skin started to tingle and it itched around my cock and balls but after a few minutes the tingle faded. The only bad part so far was the smell coming off the hair remover. So far it really wasn't that bad except the time seem to drag, as I couldn't do anything except for standing and waiting.

Janie came back and told me to stand in the tub. She turned on the water before taking a washcloth. She then proceeded to wipe the liquid off of me with the wash cloth and rinse the washcloth with water. 

When she had the foul smelling liquid off of me she told me to get out of the tub. Once out she plugged the drain so the tub started to fill. When the tub was half full she poured in three handfuls of white crystals into the water directly under the spout. Bubbles started to form immediately and the room filled with the scent of flowers. 

Once the tub was filled Janie told me to get in. As I got in I asked if this was necessary. "Of cause it is. The scent will stay with you so you'll smell like a girl and it will also soften your skin so you feel like a girl. Besides a nice hot bubble bath will relax you and make you feel so feminine. Now you relax while I get everything else ready. I'll be back in a few minutes to work on your eyebrows and give you a pedicure." 

Janie was gone about twenty minutes before she returned carrying a small tray. She knelt by the side of the tub and started plucking my eyebrows with a pair of tweezers. At first I felt a sharp pain as she started pulling out each hair. After a few minutes I got use to the pain and Janie could go faster. It still took her over twenty minutes to get my eyebrows shaped the way she wanted them. 

By the time she had my eyebrows done and given me a pedicure the water in the tub had started to turn cold. Janie held a towel open for me and said, "Okay honey out of the tub and let me dry you off. But you have to promise me that you won't look in the mirror until I'm done putting on your makeup and you're dressed." 

Janie started patting the towel on me to dry me. She started from my neck and slowly worked her way down my body. Between the gentle patting and the sensitivity of me skin I had an erection very quickly. When Janie noticed it she knelt down in front of me and said, "I see my little girl's clit is all excited. Do you want me to lick your clit until you cum." 

At first I wasn't sure why she was referring to my cock as a clit but it struck me that she was really treating me like a girl and wanted me to go along with it. If it meant I was going to get another blowjob from her I would be willing to call it anything she wanted. Janie knelt in front of me waiting for my answer. So I said, "Would you please suck my clit Janie, Please." 

Janie smiled her wonderful smile before sticking out her tongue and licking my cock. I didn't think removing the hair that covered my balls and around my cock would make her tongue feel any different but the difference made me squeal like a girl. The wet warmth of her tongue shocked me and I could feel the roughness of her tasted buds. 

Janie took my balls into her mouth and lovingly mouth them till they were dripping with her saliva. She then took my cock into her mouth and sucked lightly at first before building to a strong suction as her mouth moved up and down my tiny shaft. It didn't take her long before she had me moaning as she tried to pull the cum from my balls. All too soon I was pumping another load into her hot mouth, which had Janie moaning on each squirt. 

When I finished cuming I expected Janie to show me the load she had in her mouth like she did earlier but instead she stood up. She pulled me into her arms and kissed me on the mouth. I kissed her back to let her know I appreciated what she did. When I felt her open her mouth I open mine as well. 

What followed next first surprised me then shocked me. When Janie slide her tongue into my mouth I noticed that it was slimy. With out thinking about it I started to suck on her tongue and I cleaned off what was on it. I then felt something flow from her mouth and into mine. It was thick and silky smooth and it had a slightly salty taste to it. I wasn't sure what it was at first but then it became clear that it was my cum. Janie was feeding me my own cum. 

I was going to pull away but Janie held my head tightly and her lips stayed firmly on mine. I couldn't pull away and soon more of my spunk flowed into my mouth. I tried to keep my tongue away from it but Janie's tongue started to play with the spunk and she pushed it onto my tongue. 

I couldn't help but taste it. Surprisingly it wasn't that bad. In fact except for the slightly salty taste of it, it didn't taste like anything. When I got over my shock I like the feel of it in my mouth and I even tried to give a little of it back to Janie. 

After we kissed for a few more minutes Janie pulled her mouth from mine. With out thinking about it I swallowed the cum that was in my mouth. It then hit me not only was Janie turning me into a girl by dressing me like one but she also had me swallowing cum like a girl. 

When I looked up at Janie I saw her smiling down at me. It wasn't a mocking smile but one that told me she was pleased with me. When she saw me looking up she brushed my cheek with her finger and said, "I'm sorry I surprised you like that. I just wanted you to know what a girl has to do when she sucks off a man. I didn't think you would want to suck off a man to find out so I gave you a little of yours." 

I realized that I couldn't be angry with Janie so I said, "I'm not angry you just surprised me was all." 

Janie laughed and said, "I'm full of surprises now come on and let get you dressed. I want to see what my little girl looks like." 

When we walked into the bedroom I noticed that Janie had covered the full-length mirror with a blanket and the mirror on her makeup table was also cover. She walked me over to the bed that had several articles of clothing. She picked up what looked like two beasts and said, "You're in luck, I didn't know Samantha left these when she moved out." 

I asked her what they were and she said, "These are breast forms. Samantha was as flat as you are. The poor girl looked like a boy when she pulled off her top. She wore these to give her some shape so every one would stop asking her if she was a boy or a girl. After working for me for a few months she was able to save enough money so she could get breast implants. Here let me glue these on you before I start to do your make up." 

Janie picked up a tube of surgical glue and smeared it all over the back of one of the breast forms. She then placed it on my chest and after positioning it just so she had me hold it in place while she applied the glue to the other. 

Once the glue was dried Janie showed me how to put on a bra. Once my bra was holding my breast in place Janie went to work on my fingernails. She started by applying nail extensions to my nails. Once the glue was dry she sanded then till it looked like they were my own nails. She applied a coat of red base to each nail. While my fingernails dried she applied a coat to my toenails before going to work on my face. 

Janie told me what she was using and how she was applying it. She told me this so some day I could do it on my own. First she used an eyebrow pencil to darken my eyebrows so they stood out. Once that was done she applied mascara to each eye. This was the hardest part, as I wanted to blink each time she touched my eye. The eyelid liner was also difficult but not as bad as the mascara. Before she put on the eye shadow she applied a second coat of red to my fingernails and toes. 

While the second coat dried Janie put on my eye shadow before applying a liquid cover coat to my face. This would give my face a slight tan look. With a sponge she spread it evenly all over my face and even on my neck. She then added blush to high light my cheeks and an even coat of lip-gloss to my lips that made my lips glisten. Once my makeup was done Janie applied a topcoat to my nails before going to work on my hair. 

My hair was rather long, as I never seem to have time to get it cut. Actually it was because of my mother that I kept it long. She liked it when my hair was long. In fact it wasn't until the day before I started school that I got my first hair cut. She used to have me sit on her lap and she would brush my hair for hours when I was small. 

Janie seemed to like my hair too as she started brushing it and blowing it with a hair dryer. When she couldn't get it to do what she wanted the she wet it with a spray bottle then rolled it up in hot curlers. While she was waiting for the curlers to do they're magic she rolled a pair of stockings up my legs before putting a garter belt around my waist. Once the stockings were secured to the garters she helped me put on a satin thong panty that matched the bra I was already wearing. 

Janie once more started on my hair. It took her about thirty minutes to finally get it to do what she wanted or at the very lease to look presentable. Finally she said, "If we're going to do this sort of thing on a regular basis you are going to have to see my stylist. This is too much work to do this every day." 

I just about laughed before I said, "You expect me to go into a salon and tell someone that I want a style that would make me look good in a dress?" 

"No I expect you to go in to my stylist and she would do your hair with out knowing you're a boy under your clothes." I laughed at her statement till she said, "I'm serious sweetie. When you see what I'm looking at you'll think the same thing. I think you could go out right now and no one would know that you aren't a real girl. Of cause you'll have to put on a dress first." Janie looked quite serious when she said this. 

Before I stood up Janie slipped a pair of three-inch high-heeled sandals on my feet. When I looked down at my feet I marveled at how pretty my feet looked in the heels. I could see my painted toenails though the suntan stocking and my toes were sticking out of the toe of the shoe. There was a strap that went around my ankle and several that went around my instep. The shoes were almost the same color red as my toes. 

Janie helped me to my feet and helped me maintain my balance till I grew accustom to the high heels. Once I was able to stand on my own Janie said. "God I can't believe how sexy you look right now. The only thing that gives you away right now is the breast form were they stick out beyond the bra and your hard little pecker that's pushing out the front of your panties." 

I looked down but I couldn't see it as my breasts were in the way. Janie came over slid her hand into my panties and pushed my cock down and between my legs. It was quite painful to have it pushed back that way but it seemed to do the trick. 

Janie next held a red dress open for me to step into. I had a little problem standing on one foot while trying to get the other foot inside the dress. Janie giggled at my attempts before saying. "This would have been easier to put it on over you head put I'm not taking any chances now that I finally got your hair to hold it's shape." 

We finally got the dress on and zipped up, For accents Janie put a gold chain around my waist and a red velvet choker around my neck. She spritzed me with perfume and pronounced me done. 

"Well what do you think, do I look as pretty as you thought I would," I asked dying to know what she thought. 

Janie looked me over and said, "No definitely not. You look better than I could have hoped. I really mean it. Before you were cute but now you're a stone fox. I'd better watch it or someone will try to take you away from me." 

For some reason I was excited by her words and I wanted to see what I looked like. Janie moved me over to the full-length mirror and pulled down the blanket. I couldn't believe my eyes, what stood before me in the mirror was a very beautiful girl. I was slightly taller then my normal five foot two thanks to the three-inch heels I was wearing. I had a nice rack on top thanks to the breast forms that were glued in place. The dress was quite short leaving five inches of thigh showing. My legs looked really sexy in their stockings and the shoes I was wearing really seemed made for me. Janie had really done a wonderful job on the makeup and my face looked perfect but I wasn't happy about my hair. It looked okay but definitely need a better style. 




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. 




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. 




Little Man Pretty Girl Ch. 02



Once the driver had all the equipment up in Janie's apartment Janie told me I should give the driver a blowjob in lieu of a tip. I was shocked that she would say such a thing right in front of the driver. Before I could react to that the driver said, "Look girls that really sounds fantastic but I could really use the money. Besides if my wife finds lipstick on my joint once more she's going to cut it off." 

Janie walked over to the driver grabbed his package and said. "We wouldn't want that now would we. Here's and extra twenty to make up for it," Janie took the twenty and stuffed it down inside his pants before releasing her grip on his manhood. The driver said thanks and bolted for the door. 

Once he was gone Janie laughed hysterically. I on the other hand was a little miff by what just happen. When Janie calmed down I asked, "Don't you think that was dangerous offering him sex without knowing whether I would do it or not?" 

Janie saw how serious I was. She came to me and took me in her arms before saying. "No I don't he would have gotten the blowjob even if you refused. I would have gladly taken your place. Now before you get your panties in a knot lets go put away your clothes. After that we can take a nice long bubble bath together." 

Once we cleared out the remainder of Samantha's things from the second dresser we started putting in my things. Nothing we put in remotely resembled anything a man would wear. There were twelve panty and bra sets a dozen pairs of stockings ten garter belts five busters and a corset. In the closet we hung three dresses, one of which was so short it was embarrassing. Beside the dresses there were three skirts four blouses, two jackets and six pair of shoes. 

Once all my things were put away I said. "I don't see that we have to do anymore shopping I have more clothes now then I ever own as a man." 

Janie laughed and said. "That's probable true. I remember before I changed that I owned six pair of jeans and ten shirts and that was about it. You'll find that as a girl wearing the same thing every day isn't much fun. Beside you don't want to be seen wearing the same thing every day. And you can't wear evening clothes during the day and vise-a-versa." 

Janie and I went into the bathroom and started filling the tub. While the big tub was filling we each filled our own enema bags and filled ourselves with the cleansing solution. After the tub was filled and a thick layer of bubbles filled the surface we voided our enemas and sunk into the tub together. 

As we lay in the tub together we kissed and ran our hands over each other's body. I played with Janie's breasts, which had her moaning sweetly. She played with my flat chest seeing we agreed not to glue on the breast forms until after our visit to my mother's. 

After Janie had me moaning almost constantly with her nipple play she asked. "Baby girl have you thought about getting breast implants any time soon?" 

"No not really. Are they expensive and how hard will it be to get them." I asked with closed eyes. 

"Not very expensive. If you don't have the money I'll lend it to you. Besides you wouldn't have to worry about taking off you breast forms every few days so your skin has a chance to breathe. I know you'll be a lot happier when you don't have those bags glued to your chest all the time." Janie told me while she rolled one of my nipples between her thumb and forefinger. 

"I think I would like that. I'll have to look in to it." I told her as I took her hard clit into my hand. 

Janie let me play with her clit for a few minutes then she had me knee up and lay my chest over the end of the tub. After lubing up my hole with her fingers she pushed her clit into me. The pain was almost as bad as it was the night before. But once she was in me it quickly faded to a dull ache before I started feeling that blissful feeling of being reamed. 

Janie fucked me for ten or fifteen minutes as water sloshed out of the tub and onto the floor. When she came, it felt like she open a fire hose inside me and I could feel her cum drip out around her clit. I didn't cum this time but I really didn't mind, as I loved the feeling of being ridden. After her orgasm Janie and I lay back in the tub quite content. 

Once the water had cooled we got out of the tub and dried off. After one more enema to purge Janie's cum from my rectum we put on panties and robes before going into the living room. In the living room Janie had me put on a pair of four-inch stiletto heels and coached me on how to walk in them. They were a lot more difficult to walk in then the shorter heels but I did like the way they made my leg muscles flex. Besides they made me feel a lot taller. After the walking lessons she gave me standing lessons and sitting lesson but most of all she gave me flirting lessons. 

I was taught how to flirt with the way I stood the way I walked and the way I sat. She taught me how each position I took could be a suggestion of seduction or a suggestion of rejection. She then went on to hand movement, which was a whole different language in it's own. She also taught me how to eat like a girl. It didn't seem that difficult until she started correcting me. I never realized women ate differently than men do. 

The lessons continued till ten o'clock when Janie said it was time for bed. We changed into nighties before we slipped into bed. Once in bed we started kissing. I worked my way down Janie's body till I took her clit into my mouth. After sucking on her clit for a few minutes Janie asked me to lick her pussy. 

I licked her pussy for long time before she asked me to stick my clit into her. After sticking my tiny clit into her I started fucking her slowly while Janie started stroking her own clit to the same rhythm I was using. I tried lasting long enough till Janie came but I couldn't last that long. 

After cuming in Janie's bottom I knew I had to do something to bring her off. I reached into the nightstand and pulled out the bottle of lubricant and the second dildo she used on me. As quickly as I could I lube up the dildo and slid the head into Janie's bottom. 

She gasped at the unexpected intrusion but quickly said, "Oh god yes baby girl give it to me. Fill me with it." I started fucking Janie with the dildo till she had every inch of it deep in her pussy. 

Janie was beside herself with pleasure as she tried to speak and only gibberish came out. When I had the dildo sliding in and out at a fast rate Jane fell over onto her side as she continued to stoke her clit. A flash of an idea came to me and in a second I laid along side her and took the head of her clit into my mouth. 

Janie felt my mouth instantly, she grabbed my head with her hands and started fucking my mouth. I could barely keep the dildo moving but that didn't bother Janie as her own movements kept the dildo sliding in and out her. She didn't last that long after that as I felt the first of what would be the biggest load I ever had in my mouth. I swallowed three times just to keep up with her. 

When Janie's orgasm subsided I eased the dildo out of her and slid up the bed to lay along side her. Janie pulled me into her arms covered my face with kisses while saying. "Oh baby girl that was wonderful you really made me cum hard that time." 

Janie fell asleep almost instantly but I didn't fall asleep so quickly. That orgasm told me that Janie needed more than I could give her. I could never fuck her like that with my own clit. Dildoes are nice but I knew from first hand experience that the real thing is so much better. This experience also taught me that if I tried to keep Janie away from other men or acted like a brat and didn't support her she would leave me or force me to leave. I had to let her do what she wanted and with whom she wanted for both our sake. 

I woke up to Janie kissing my face. Once she seen my eyes open she said. "Good morning lover are you ready to shop to you drop?" 

"I guess so. I need to talk to you about dating men." I told her but she stopped me with a finger over my lips. 

"Not another word about that. We'll cross that bridge when we come to it. Now eat your breakfast and then into the shower with you." Janie placed a tray in front of me before she got up and started going through my closet for something for me to wear. 

Janie was already dressed in a tan skirt white blouse and two-inch heels. Her figure looked a little different today. She looked slimmer and her hour glass figure was more pronounced. 

After I finished my breakfast I when into the bathroom. Janie followed me in and while I was filling myself with the enema. Janie kissed my shoulder glided her hands over me before saying. "I think it's time to use the hair remover again, I'm starting to feel a little stubble. I'll have to remember to get a few bottles while we're out." 

When I came out of the bathroom Janie was waiting for me. In her hand was the white corset that we had bought the day before. She wrapped it around me and did up all the hook and eyes that went from the bottom to the top on the front side of the corset. Jane then went around to the back and started pulling the drawstrings tight. 

When Janie started to push the air out of me with the corset I asked. "Is this really necessary?" 

"Of cause it's not necessary, but it really improves your figure. Can't you tell that I'm wearing one? Now be quiet and breathe out." I guess that was why Janie looked different this morning. 

I expelled all my breath and Janie pulled the strings tighter. Once she was done I tried to take a deep breath in but I could only take in about half of what I needed. When I complained Janie said. "Such is the price of beauty. Now look at yourself in the mirror and tell me it isn't worth the trouble." 

I turned and looked at the mirror and I was shocked by what I saw. Not only was I thinner, but I had hips and a waistline. Except for the fact I didn't have any breasts and I had a tiny little penis I looked like a girl. Janie saw the look in my eyes and giggled, she knew she had me hooked. 

After I stared at myself for a minute or two she handed me a pair of stockings and told me put them on. The one problem with a corset was bending over. Due to the constriction it was very difficult to bend over and get something on you feet. It took several tries but I was finally able to get both stockings on and adjusted properly. 

Once both stocking were attached to the garters Janie handed me a white pair of panties while saying. "You know I can't be here to dress you all the time. You are going to have to do this yourself someday." 

"I know, I may need some help knowing what goes with what. Like this corset when do I wear it and with what." I told her. 

"You could wear the corset with just about anything. For the next couple of months you should wear one most of the time. It will train your body so you look more feminine with out it. You can wear shorts around the house but I think you should wear dresses and skirts for a while. It'll remind you of what you are. Also you will act more feminine in a skirt than shorts. You could wear pantyhose but I hate them. I think stockings are more ladylike. It'll be easier if I tell you where you could wear something as we look at it." 

While I was doing my makeup Janie took the starter rings out of my ears and put in hoop earrings. They weren't that big of a hoop, but they definitely looked better than the gold balls I was wearing. Once my makeup was done and my hair was brushed out we grabbed our purses and headed out the door. 

We walked two blocks to a parking garage and got into Janie's SUV. I was surprised that she had a car at all seeing most people that lived in the city didn't have one. But Janie told me that she needed one because she did a lot of work in the suburbs. Once we were out of the parking garage we headed for the suburbs. Janie told me that the stores in the city were okay but it took too long to get from one to the other. For marathon shopping the malls out in the suburbs where the way to go. 

We hit the first Mall at ten in the morning just when they were opening up for business. We started at one end of the mall and hit every store that had anything that a girl could wear. We walked our way down one side of the mall and back on the other side before going to the next mall. 

We hit three different malls that day and I swear we stopped in every store. I think I tried on over fifty dresses and as many skirts and blouses, and I bought over half of them. They came in all different colors and lengths. There was mini skirts mid-thigh, knee length and calf length. I also bought a ton of sweaters from open V-neck to turtle neck. Short sleeved long sleeved, crop top, waist length and full length. 

Also there was the underwear. I bought panties busters garter belts bras and of cause corsets. Fifteen corsets all told. I bought slips chemises and camisoles, all of them in different styles and colors. 

Lets not forget the shoes I bought, over thirty pair of heels from two inch mules to four and half inch stilettos. I especially liked the taller ones as they made me look taller. Not to mention how pretty they looked on my feet. 

Janie tried to caution me on not spending too much but I didn't listen. That day I wound up putting over five thousand on the credit card. I really didn't care as I had a ton of fun and I had the money to spend. Janie just laughed and told me. "Just remember baby girl. There is always tomorrow and the stores will always be here." 

By the time we got home it was near eleven. We brought everything up to the apartment before Janie and I took the truck back to the parking garage. By the time we had unpacked everything and put it all away it was almost one in the morning. Janie and I barely took showers before getting into bed. With a single kiss we fell deeply asleep. 

We slept until nine the next morning where we slid in to a bubble bath for an hour. By eleven I was setting up my computer with Janie's help directly in front of hers so we could see each other as we worked. At noon Janie decided that we should change for the drive to my mother's 

I changed into a pair of jeans and a polo shirt. I had to take my earrings out and put in the starter posts once more. I really hated wearing my male clothes once again and I hoped it would be the last time. Janie changed into a yellow sundress with two-inch sandal heels. She of cause wore stockings and garters. When I saw her dressed I wished I could have worn the same thing. 

On the drive to my mother's house I asked Janie about Samantha. "Was Samantha like me?" I asked 

Janie smiled and said. "If you mean was she born a boy then yes she was like you. She looked a lot like you about the same height and size. Between her legs she was a little bigger but not much. When Sam came to me she had already changed herself somewhat. She had already started wearing girls cloths but that was about it. When she applied for a job I had posted she gave me her resume but there was something about her that looked wrong. I couldn't put my finger on it but I knew something wasn't right. At first I thought it was her resume because she looked so scared when she gave it to me.

"When I looked it over it was pretty impressive. So I asked her a bunch of questions which she knew the answers to. I was ready to hire her but I said I needed to check her schooling first. The poor thing broke down and told me every thing. Her family rejected her and she was living in a shelter. I still checked her schooling but I checked under Samuel not Samantha. I hired her and she moved in the next day. I helped her change into one of us and now she's living in the suburbs with a rich boyfriend. They are quite happy together." 

By the time Janie finished her story we here pulling into my mother's drive way. We were just stepping on to the porch when my mother came out and took me into her arms. Betty was right behind her as usual. 

My mother was still a very attractive woman even though she was forty-five years old. I swear she didn't look a day over thirty. She was still the same height and weight she always was. A size two if that. There was a wrinkle or two around her eyes but with the right makeup no one would see it. She was still a beautiful woman that any man would want to catch. 

But the reason no man had caught her was standing behind her. Betty was still a tall beautiful woman, though she tried to hide it. As long as I've known her she's never worn makeup. She always wore slacks and never a dress. But to say she was unfeminine would be a mistake. 

When my mother pulled away from me she said. "Jer you smell wonderful what are you wearing?" 

I heard Janie giggle from behind me before she said. "That would be the bubble bathe we shared this morning."

My mother looked over my shoulder and I could see a look of surprise on her face. She covered it quickly before walking around me while saying. "I guess you would be Jane?" 

Jane took my mother's hand and said "Yes Jane Michaels. I'm glad to meet you." 

I quickly made introductions. "Janie this is my mother Sally Adams and Betty Daniels her um." 

"He still has a problem with the word partner." Betty told Janie before she said. "Please come in." 

We went into the living room where Janie had to tell my mother and Betty all about herself. During the conversation my mother kept looking at me and when I looked back she would pull her eyes away. For a while I thought she knew or some how suspected but I couldn't figure out how. 

When Janie was done my mother turned to me and said. "What's new with you Jerry?" 

I knew I should have said something at that point but it didn't feel right. I just couldn't come right out and tell my mother that her boy was now a girl. I saw in Janie's face that she was upset with me but she wasn't going to be the one that told them. 

After I told them nothing was new my mother said, "Jer could you be a dear and go look at my computer. I think I have a virus on it." 

Knowing that this was an out I grabbed for it. "Sure mom I'll be right back." 

Janie went to get up as she said. "I can look at it. It is what I do." 

My mother grabbed her Janie's hand and said. "No Jer can look at it besides while he's gone Betty and I can tell you embarrassing stories about him." I groaned at that because I knew my mother would. 

I looked at my mother's computer for over an hour but I couldn't find a thing wrong with it. By that point I realized that my mother had sent me out of the room so she could speak to Janie. I dreaded what they were saying but I really had no control over it. As I walked back toward the living room I heard giggling coming from the living room so I knew the talk was about me. 

When I entered the room all conversation stopped then my mother jumped up and said. "Dinner should be ready Betty do you want to help me." 

As soon as they left the room Janie said. "You're a coward you know that. You had the perfect opportunity and you chicken out." 

I looked down at the floor and said. "I know I just couldn't do it." Janie turned her face from me and didn't say a word.

Dinner went well and the conversation was bright. Janie didn't hold it against my mother or Betty but she didn't so much as look at me. After dinner we sat for an another hour and talked before Janie and I left for home. 

All the way back to the city Janie didn't say a word to me. If I asked a question she didn't answer. The only thing I heard from her was the word coward every so often. 

When we got home Jane went into the bedroom and changed for bed. She then sat at her computer for an hour or so before she went to bed. I changed too and worked at my computer till one in the morning. By that time I figured Janie was sound asleep. I crawled into bed and cuddled up to her but She pushed me away. I guess I was lucky she let me stay in the bed at all. 




Little Man Pretty Girl Ch. 02



The next morning Janie's attitude changed completely. She came into the shower and said, "I'm sorry I was such a bitch last night." 

"I'm sorry I didn't tell my mother when I had the chance. I will next time," I told her as she started scrubbing my back. 

"I know you will baby girl. I know you'll tell her the next time you see her," She told me. 

After the shower I asked Janie to help me with the corset I was going to wear that day. Janie was very helpful on what I was to wear to the beauty salon to get my nails done. I wore a pale green sundress and two-inch pumps. 

I arrived just in time for my appointment and Teddie took me right back. The nails that Teddie used were a lot more involved then the ones that Janie used on me. It took her over an hour to get the nails on and that was before she started applying the color. She told me that these nails were harder then my real nails and they should never break. 

By the time she was done I knew all about her last three boyfriends and her present one including all the sex they had together. I was also told about Lacey the size of her organ and the fact that Teddie could swallow the whole thing with out choking. I wasn't sure if I ever wanted to go back but one look at my nails told me I wouldn't go anywhere else. 

When I arrived back at the apartment Janie was busy at her computer but she did stop long enough to look at my nails. With out changing clothes I went to work at my computer seeing I had spent so little time working in the past week. I didn't change because I was comfortable and Janie said I should stay dressed as feminine as possible while I worked. I felt I couldn't get more feminine then I was at that point. 

We worked together until five o'clock when Janie got up and took a shower. I was at a critical juncture and I couldn't stop to join her. By the time I worked through the problem Jane was standing in front of me in a black mid thigh length dress that revealed her cleavage. 

"Are you going out tonight?" I asked. 

"No I thought since you were dressed up all day I should dress up too. In fact why don't you take a shower and change into that purple sweater dress that I thought you looked so good in. You know the off the shoulder one. I'll be right in to tighten up your corset." 

I really didn't want to break my train of thought but I really wanted Janie to be happy especially after yesterday. So I saved my work and after a good cleansing I was in the shower. I even covered myself with hair remover to get any stubble off of me. 

As soon as I was out of the shower and dried Janie was wrapping me in the corset. Once the corset was on Janie left the room telling me to hurry. I slipped on my hose and panties then sat down to do my makeup. Once my makeup was done and my hair was brushed I put on the dress. 

Janie was right the dress looked perfect on me. The skirt was a little short and it tended to ride up but it looked super on me. After putting on a matching choker, tennis bracelet and a pair of purple four-inch stiletto heels I was ready. When I looked at myself in the mirror I thought what a shame we weren't going out. 

I walked from the bedroom into the kitchen to find Janie but she wasn't there. I saw by the wrappers that she had gotten a take out meal and I could smell something in the oven There was a bottle of wine on the counter and four glasses standing next to it. The four glasses frighten me just a little but I got over it quickly thinking the Janie had invited over a few friends. Then I wondered if they were guys. 

Before I went any further I called out for Janie. In an instant she was standing in the kitchen. As soon as I saw her I asked in hush tone, "Do we have company?" 

"We will shortly. I invited a couple over." She told me. 

"Are they a couple of guys." I asked and I could hear the nervousness in my voice. 

"No sweetheart I would never do that to you. They're both girls so calm down." She told me after taking my hand. 

Janie poured two glasses of wine and handed me a glass as she took the other. After taking my first drink she said. "Look at the way your hands look with that glass your nails seem to sparkle." 

She was right they did seem to sparkle and for some reason that seemed to calm me. Janie went on to tell me how beautiful I looked. I thanked her and told her she looked beautiful too and so sexy. 

We finished off the glass of wine and Janie filled my glass when the doorbell rang. "You stay here and I'll get the door. I'll come and get you in a minute." 

I could feel the butterflies in my stomach return so I drank deeply of the glass and had half of it gone when Janie came back into the kitchen. She took the glass from my hand and placed it on the counter then steered me into the living room. 

When we reached the living room I received the shock of my life. Standing in front of me was my mother and Betty. My mouth fell open and I stood gapping as the heat of embarrassment filled me to the core. I tried to say something to apologize but nothing would come out of my mouth. Finally Janie said, "Sally Betty I would like you to meet your new daughter Geraldine Adams." 

When I looked at my mother's face I was sure I would see shock or surprise maybe even hate but that was not what I saw. What I saw was love, amazement and even joy. But there were also a few tears. Betty just smiled her warm soothing smile that always told me I could do no wrong. 

My mother came to me hugged me tight and said, "You're beautiful I can't believe how beautiful you are. Betty isn't she beautiful." 

Betty came over to me and said, "You're as beautiful as your mother. The resemblance is uncanny." 

"They do look alike don't they," Janie told Betty. "You three sit I'll check on dinner and get us all some wine." 

As soon as Janie left the room I said stutter, "I'm sorry I don't know why Janie did this. I really should have told you about this yesterday. I guess she was madder than I thought," 

My mother took my hand pulled me down onto the sofa with her and said, "This wasn't Janie's idea. Well I mean she didn't tell us about you wearing girl's clothes. I spotted the earrings yesterday and that in of it self doesn't mean much, but take the way you smelt the fact that your hair was so different and your eyebrows were plucked told me there was something up. When I took a closer look at Janie I realized that she was a male at one time too. Her Adams apple shows a little and her hands are too big. Taking all those things into account I asked Janie point blank if she was born a male. She never tried to deny it, in fact she was proud of it, so I asked if you were changing too. She admitted that you were and that you were supposed to tell us yesterday."

"I was supposed to tell you and I was going too but when it came time I just couldn't. I didn't want to hurt you or Betty," I told her in a slightly whiny voice.

My mother pulled me into her arms and said sadly, "Jer what hurt me and Betty was how unhappy you always were. We knew as a little boy how you use to get picked on at school. And how many times were you embarrassed when someone would ask if you were my daughter or sister. Though I took pride in that fact that they could see the resemblance it hurt me to know that you were embarrassed by it." 

"So you two are okay with this. I mean you're not hurt that I'm strange," I asked. 

"Well I don't think you're strange and neither does Betty. We both understand that you have this urge to be thought of as a girl and we'll support you as much as we can. Besides what is so strange about this. If you're comfortable dressing like this you should do it after all. It never bothered you that Betty was a cross dresser." 

"Betty is not a cross dresser," I told my mother with a giggle in my voice. 

Betty and my mother laughed before my mother said, "Sure she is. When have you ever seen Betty in a dress? You know as well as I do that she wears jeans almost all the time. She wears men's socks and men's shoes. If she isn't wearing a T-shirt it must be winter and she's in a flannel shirt. Betty has be a cross dresser all her life. But for a girl it's expectable where as for a man it's not." 

I looked at Betty who nodded her head before I asked, "You're both alright with the fact I won't be your son any more." 

Betty laughed and said. "You're still be my little Jerry though now I'll have to spell it with a I instead of a Y. As for your mother she always wanted a daughter now she will have both. She had a son for twenty-five years and hopeful she'll have a daughter for that long." 

I looked at my mother to see if she agreed. She smiled kissed me on the cheek and said, "I would be proud to call you my daughter. Beside who wouldn't, you are gorgeous and where did you get your nails done. They simply take my breath away. 

I told my mother about the salon that I went to and she asked for the name and number. Janie came in with four glasses of wine and asked, "Well is everything alright?" 

"Just perfect thanks to you." My mother told me. 

"I didn't do much. And Jeri no matter what they say, they made me do it. Your mother saw right through me and made me arrange this. I wouldn't have done it on my own." 

"Oh you have Janie," My mother told her. "You've taken my very unhappy son and made him in to a beautiful and happy girl." 

"I didn't make her into anything. I just open a door and she walked through. Well it was more like she ran through." Janie told her with a laugh. 

My mother went to Janie kissed her on the cheek and said. "Whatever you did I thank you." 

Janie held out her hand to me and said. "Dinner is ready. If you would all follow me to the dining room." 

After dinner my mother and Betty left telling us that they would like us to come by in a few weeks. After they left I wanted to get back to work but Janie pleaded saying. "Come on baby girl we haven't made love in three days. I promise I won't bother you all day tomorrow. In fact I won't be here." I relented and allowed Janie to pull me into the bedroom. 

Janie did make love to me. She kissed me all over and licked my clit until I almost came. She then licked my pussy before rolling me onto my back and slid her clit into me. For some reason it didn't hurt when she entered me. It was the most sensuous thing I ever felt. I even sighed like a girl would. When she flooded my bowels with jizum I painted both our bodies with cream. 

After we rested we got up to use the shower while in there I asked Janie, "Do you know where I can get implants done?" 

Janie hugged me to her and asked "Are you sure there will be no turning back after that?" 

"I'm sure I don't want to turn back I like what I am. Everyone I know is okay with me the way I am and I can see how much you like what I do to your breasts," I told her. 

Janie thought for a second and said, "The doctor I used isn't doing breast implants any more. The doctor that Samantha used was an ass and he treated Samantha like dirt. We'll have to look around and see what we can find. Maybe you should ask your mother she may know some one that doesn't care about what sex you started life as." 

Janie went to bed and I went back to my computer for a couple of hours. By three in the morning I closed two cases and decided to call it a night. As soon as I crawled into bed Janie woke and reached out to me. I fell asleep in her arms. 

I woke up the next morning just as Janie was heading out the door. It was the first morning I had to dress myself. I chose a pleated nave blue skirt, knee length, a white silk blouse and three-inch heels. I couldn't put on a corset as they all needed to be tighten for the first time. Instead I chose a white bustier as it did almost the same job though it wasn't near as tight. 

After getting dressed and my makeup on I looked around the room I noticed all the dirty laundry lying around. I have been doing laundry since I was twelve seeing my mother worked every day and she didn't have time except on weekends. Weekends were when her and I would do things together. After several weekends were spoiled by her having to do laundry I decided to learn how to do it so I could take care of it after school. 

When I'm working on a case I would normally install a search program that I developed. I would let the search program run while I sat and watched it. It's pretty boring, as I can't do anything until the program has run its course. Today I decided that while I was waiting I'd start cleaning up around the apartment. 

When Janie returned home she quickly noticed that I had the kitchen spotless the den dusted and vacuumed. Several loads of laundry done and the bathroom cleaned. She came into the den kissed me on the cheek and said, "You're a little Susie homemaker aren't you. Did you make dinner too?" 

"I thought about it but you don't have anything here. Tomorrow after I see Jake I'll do some grocery shopping. If that's okay with you," I asked her. 

"That's great to me if you want I can go with you. I don't have anything to do tomorrow." When I told her I'd like that she asked. "Do you want me to call for a pizza or do you want to go to a restaurant?"

"I'd love to go to a restaurant but I really can't leave right now. If I do I'll have to start all over again." Just as I said this I hit a critical juncture and I stopped paying attention to Janie. 

"I'll call for pizza and Friday we can go out for some dinner and dancing with a couple of guys I know." Janie told me. I didn't quite hear her but I told her that sounded good to me.  It was about fifteen minutes later when Janie came back in the room. I now had my problem under control and I was able to pay more attention to her. "Bill and Joel will be here at eight Friday night. We'll go eat then to the club for some dancing." 

"Wait, who is Bill and Joel," I asked as her statement started to set in. 

"Bill and Joel are two friends that I date once in a while with. Bill will be my date he's a real looker. He's six four and two hundred and fifty pound of rock hard muscle. But he is as gentle as a lamb. Joel will be your date he's only six foot tall and thinner than Bill by a lot. But he can make a girl's toes curl in bed. They're both great dancers and I always have a great time with them." Janie knew I had not paid attention to her when she told me about Friday earlier. 

When I could get a word in edge wise I said nervously, "I didn't agree to that." 

Janie smiled and said, "Yes you did, you said it sounded like a good Idea to you." 

"Well I didn't mean it you caught me at a bad time. I can't go out with them." I whined. 

I could see frustration in Janie face and she said slightly irritated, "Why on earth can't you. It's a date no one said anything about having sex with him. We're just going out to dinner and later some dancing nothing more. Well nothing more that concerns you. Unless of cause you want invite Joel back here." 

I was about to tell her I wouldn't, but she held up her hand and said, "Don't close your mind to anything remember me telling you that. Now don't close your mind to this. You may not want to invite him back, but you may want to. I'm not forcing you in an direction but Friday night if you don't sleep with Joel you will be sleeping alone." Once that was said Janie stormed out of the room. 

While I watched the computer in front of me I thought about what she said and I remembered how I felt last Friday night. I understand she need a man but why did she trick me into this date. I realized if she hadn't, I'd probably come up with a reason why I couldn't go and this was the only way to get me to agree. I was pretty sure she was doing it for me so I would get over my fears and become comfortable. Besides she might feel guilty about leaving me home while she was out. I wanted to go to her and tell her I thought it over and I was okay with it but I couldn't, I couldn't leave the computer.

About an hour later Janie came back with the pizza and two cans of soda. She put the pizza on the desk sat down next to me and said apologetically, "If you think I tricked you I'm sorry. I don't want you thinking I'm forcing you into something I'm really not. If you think your not ready for this then I'll call the guys tomorrow and tell them something came up and we have to cancel." 

Even though I couldn't see her face I knew Janie was sincere. My only problem was I couldn't take my eyes off the screen as I searched for the open hole. Then as if by chance the hole appeared and I quickly typed in a line of code to fill the gap. Now I could sit back and talk to Janie. 

Janie looked at the screen and asked, "What are you doing?" 

"Filling mouse holes," I told her. I could see the confusion in her face so I explained myself. "A mouse hole, that's what Jake and I call them, is a gap in the security program that hackers use to get in. Once I find the gap I fill the gap with the right code and the hole is filed."

"Where do the holes come from," Janie asked. 

"Almost always it's left by the programmer. It's just things they missed. Look about Friday I think it's a good idea. I mean it can't hurt and it might be fun. Joel knows what I am right and he's okay with that." I asked her. 

Janie laughed and said. "Okay with it, he prefers it. He likes girls with small clits like yours. I mean he likes girl like us regardless of the size but he prefers the smaller ones. He knows from the start that you are new and you may say no. He's okay with that as long as you're nice about it. I mean you can't act like a bitch or get him all hot and bothered to leave him hanging." 

"Like I said it sounds like fun, as far as you and Bill, I understand that you need what I can't give you and I can also understand your need for a real man," I told her. 

Janie hugged me and said, "Do you really understand my need?" 

"Of cause I do. I know what it's like to need some one. God knows I've needed someone for a long time until you came into my life," I told her. 

Janie kissed me and said, "Thank you baby girl. I know you will need a man some day because you're just like I am. You crave attention and when you realize just how much attention a horny man will give you, you'll love being around them too." 

"I hope you're right, but all I know is being close to a man scares me," I told her. 

"Don't worry sweetie. Joel won't do anything I haven't already done. The only difference will be he won't have any breasts for you to play with, but of cause that's if you decide to go to bed with him. Now lets eat." 

Janie and I ate while I continued with the case I had been working. She watched what I was doing and she asked several question which I answered when I had the time. Through most of the evening she couldn't keep her hands off of me and by ten o'clock she had talked me into leaving my work and coming with her to the bedroom. 

Janie and I made love for several hours with her cuming in my mouth and twice in my bottom before we fell into an exhausted sleep about two in the morning. I came several times also though mostly it was into open air. 

Seeing we went to sleep at a late hour I was surprised when I woke at seven in the morning. Though I tried I couldn't fall back to sleep. I knew it was because I was excited yet fearful that today was the first day Jake would see my female persona. 

I knew he said he didn't care and he wanted me to be happy, but I feared that once he saw me, he wouldn't understand what I was doing. And even if he lived up to his agreement not to fire me I didn't want him to reject me as a freak. 

When I couldn't get back to sleep I eased out of the bed as gently as I could. I didn't want to wake Janie as she didn't have anything to do today and I wanted her to sleep as long as she could. Once out of the bed I went into the bathroom for a cleaning and a quick shower. After the shower I simply slipped on a pair of panties and a sating robe before moving into the kitchen.