tagTranssexuals & CrossdressersLittle Man Pretty Girl Ch. 01

Little Man Pretty Girl Ch. 01

byScribler©

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.

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byScribler© 11 comments/ 201791 views/ 29 favorites

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