tagTranssexuals & CrossdressersSissy Prodigy Ch. 01

Sissy Prodigy Ch. 01


If you are offended by sexual content please leave now. This is a work of fiction. Everyone in this story is above the age of 18. Thanks for your comments and ideas for future content.


"I have no idea what you are doing, and I don't want to know Kel. All I know is that something is going on while I am not here and I ought to call the school to have his ass fired right now. You probably have been scheming behind my back for longer than I have a clue. If I catch him on the street I may run his ass over with my car. I will let you know what we are gonna do when I get home from work and your little ass better be here and awake when I get home!" mom screamed at me before heading out to work. She slammed the door on her way out of the house. I should have been more careful to cover my tracks better to keep her from finding anything to make her suspicious. I had left my laptop open with chats from Mr. Lee for anyone to see and mom read way too much. Not to mention some of the pictures we were sharing with each other in photo share.

Mr. Lee is the Physical Education teacher at my high school and we had been seeing each other for a couple of months. I enjoyed his class since he was one of those fresh out of college teachers and still young. Not to mention how damn good looking he was in class everyday. He was living near us while he was waiting on a house across town to come open. I had on a pair of Soffe shorts and a tee shirt one day while mom was at work. They may have been a little too short but it was the weekend and he stopped by as I was going to my car in the driveway. The fact that I had my hair up in a rubber band and my toenails were painted pink was my business.

"Why is it that I never saw this look in gym class Kel? I must say that it is mighty different and I also must say very hot. There are alot of cheerleaders that would love to have a cute little ass like that one" he says with a really devious look on his face. "And I may need to take another look at that pulled muscle you had in your leg the other day at school. I surely wouldn't want it to flare up again. If you would be so nice to invite me inside I could take a closer look" Mr. Lee suggested.

I had actually complained of a leg problem one day to him after running in our fitness test. While he was glaring up my legs to my ass I saw that he also noticed my toenails.

"Sure you can come inside, mom won't be home for hours and I don't see any harm in having some company for a while. Come on inside!" I say as I open the door and steps into our house. As I stood in the kitchen I felt Mr. Lee's hands touch my hips lightly and pressing his chest against me. On my bare neck I felt his breath as he began placing kisses and nibbling with his teeth. I couldn't do anything thing but enjoy the attention.

"You certainly do have a pretty little ass there little miss Kel. I don't see any reason why you should be hiding it in those skin tight shorts." he moaned into my ear.

And it didn't take him long to try to get me out of them. I felt a hand slip under the tight edge of my shorts gripping my ass cheeks. Knowing he found my panties and there was nothing else to hide and I didn't want too. Reaching back I pushed the shorts off to the floor letting him see the red thong panties. Two thumbs spread my little ass cheeks wide open so he could lick the entrance to my honey hole. His thick tongue lapped my little boi pussy up and down. Probing around he pushed that tongue inside of me and I lost all control. I let out a squeal that was deafening when that tongue began wiggling deeper inside. My legs started trembling about the time my little boi clit exploded with a few shots of sissy cum.

I lay on the edge of the counter having been pleasured greatly my tiny body was still recovering. Mr. Lee was quickly getting his shorts off and his cock popped out rock hard. Mr. Lee placed his cock between my cheeks and started humping me from behind. I begged him not to put it in me because I was too scared. But that cock surely did feel good sliding back and forth between my cheeks. Pressed against the kitchen counter with his cock against my body, we quickly found our way to the living room. He sat down on the sofa with me beside him on my knees. I lowered my head to his hard cock and sucked him slowly. The feel of a hard cock in my mouth was so sweet. I never knew how much fun it could be to pleasure a cock with my lips and tongue. My ass was up in the air, so he used that chance to play with my pussy. He was able to get one finger in me and used it very well. It just added to the heat of me sucking his dick. Using my tiny hands I jerked and stroked him slowly letting him know how much I enjoyed his sweet cock. He grabbed my head placing it in his lap and relieved his full balls into my young mouth. He short stroked it with quick thrusts in my lips when I felt the shots of hot thick cock juice. Moaning and loving the gift from my favorite teacher. I swallowed it gladly and savored the taste. We made out after that and pledged to see each other again.

A deliver boy showed the next day with a package in a brown paper wrapper. I took it inside to see what it was and who sent it to me. There were directions to a lake house not far from town, a note from the sender, a really cute pink outfit and a pink vibrator. Not wasting any time playing detective I got naked and tried out my new toy. Before mom got home from work I frenzied myself into two huge orgasms. That next Saturday we met at his parents' lake house spending most of the day in nothing much more than a pair of panties or boxers. He gave me two more outfits and I gave him what he had wanted for a while. Straddling me over the back of a huge leather sofa and licking my pussy wet like before he pumped that hard cock in and out of me most of the day. We probably used every flat surface in that house, from the bathroom to the kitchen and back. I am sure mom didn't want to know anymore than she read from my chat with him because we had said some pretty wild stuff. I sent him a text message to let him know that I was going to be busy with my mom for a few days. I just didn't add any details to tip him off that we had been caught. I spent the day cleaning and trying not to think about what mom was going to do when she cooled down. I hoped she didn't do anything too drastic that would cause trouble for any of us. I wiped any and everything from my computer that she could use against me as evidence. When mom got home from work she told me that she had called her brother Jake and I was going to live with him and his daughter Sarah for a while. She said that she didn't give him any details of what may or may not have gone on. "This is the last of what has gone on that I want to hear about so get your stuff ready this week and we are going there this weekend" mom says and leaves the room and gets ready for bed. I just sat there with all those kinds of thoughts running through my head and how I was going to tell Mr. Lee. As I saw it we had gotten pretty tight and it was gonna hurt to lose all that.As a young teen I had spent some summers with my Uncle Jake and his daughter Sarah. She was my favorite cousin because she was so popular and always seemed to have people over to hang out. Me and Sarah were also about the same size physically. Being older than me and my idol she had a way of getting me to do about anything she wanted. Summers before this one we would play dress up and I was always her little project. I never minded being put in some of her stuff and playing since she was the one asking me too.Growing up I might be Britney, a Spice Girl or some other female star. Those games were really fun and the clothes made me feel more like Sarah, which is what I wanted. I wanted to be her "BFF" as she called it. The outfits were miniskirts, thigh high hose, heels, dresses and most of times makeup too. There were lots of pictures taken during play times and she taught me how to act like my character.Sarah is a good-looking brunette with a very physical looking body. When she was 16 and we would go out to eat or shop there were more husbands hitting on her than one can imagine. I always loved how good she reacted when that happened, how she could sweetly brush them off. Watching her work guys like that could give me hope that it was genetics at work and not a learned thing.

On Sunday morning we drove to Uncle Jake's getting there about six o'clock. Sarah was with some friends so I didn't see her til later, just before mom headed home. I could not believe how much Sarah had grown and matured in a year. She was now about to start her third year of college and she was beautiful. Wearing a pair of cutoff blue jean shorts and a real pretty top, I was in awe of how hot she looked. At home I would have only dreamed of looking that good when I did my own playtime. We all hung out for a while, then mom left and I waved goodbye.After Uncle Jake went to bed me and Sarah talked and I told her how good she looked. I wanted to hear how college was going and what she had been doing kept my interest for a long time. I felt like her best friend again hearing all her stories. And then Sarah started asking about me and what I had been doing this summer. She pulled off my baseball hat and wanted to see how long my hair had gotten. I smiled as it fell down to just short of my shoulders. Sarah loved it and used her hands to flip it up teasing me laughing. Kel your hair looks cool as hell and I cant wait to see what I can do with it while you are here.

"You look really cute cousin. Have you been doing any dressing or prettying up that little body" Sarah asks.

I smiled and told her it was her fault that I enjoyed wearing girls clothes. I opened my bag showing her some of the things that Mr. Lee had bought me and I put on a pair of pink panties and matching top. As we sat around I used this time to borrow some of her nail polish. Painting my hands and toes in a bright pink color. We kept talking late that night staying up til about one, discussing just about everything. Reminiscing about the fun we had in summers past, she pulled up pictures on her laptop of me in some of the stuff I had played in.

"I hope no one else has seen these Sarah!" I say to her kind of shocked to see those pictures.

"No Kel no ne else has seen these but I am happy to see that you enjoy wearing this stuff. So if you want I can plan for you to have a little fun. I guess you have become quite the little sexpot while you were away from me. I know girls whose body doesn't look as hot as you do in an outfit." she tells me. "So what would you do if the chance ever came up? What do you think you would do if a man wanted to touch you or want you to touch him Kel? I think you make a very pretty girl and I don't think you would have a problem getting a chance to test your courage if that's what you want." Sarah told me looking for a reaction. She was surely my biggest fan and I loved hearing her say that.

"Well everything until now is just between me and you. You are the only person on planet Earth that knows my secret" I exclaim. After that we both rolled over and tried to go to sleep.

I woke up early that morning with an awful headache and could not go back to sleep no matter how hard I tried. Not wanting to risk Uncle Jake catching me I really needed something to get rid of my headache. I got up and grabbed a short white robe hanging in Sarah's bathroom. The house was very dark and I made it to the kitchen and to the medicine cabinet. Grabbing a couple of aspirin and some water I heard footsteps come into the kitchen.

"I am sorry Uncle Jake if I woke you up, I just needed something for a headache. I want to thank you for letting me stay with you guys for a little while and I just hope it isn't too much trouble. Anything I can do around here I will to make it up to you." I tell him.

"Kel it is gonna be great having you around here with us and if you need anything just let me know sweetie!" he says. Uncle Jake is a very good looking fortyish man with a few grey hairs and has always been very fit. He owns a succesful Accounting practice that lets him do and buy about anything he wants. I was very surprised at the term sweetie but I just passed it off initially.

"I was about to get up and go to the gym before work this morning, so this is a welcomed chance for me to see you. We have not seen you in a while and I hope your head gets to feeling better. Why don't you come here for a minute and let me show you something that I have been admiring for quite some time." Uncle Jake says. Grabbing me by the hand leading me to his bedroom nearby, I saw his computer was on. He opened a folder and there were some of the same pictures that I had seen on Sarah's laptop. Some of them a little more explicit with my tiny ass showing in a thong or lace panty.

I felt Uncle Jake's hand sliding up the inside of my leg to my crotch and I could not move. His hand pushed my panties up into the cheeks of my ass as he began massaging and caressing me slowly. He put a finger to my lips and whispered to me to be very quiet. I felt my panties being tugged off my ass and down my legs. I placed both hands on the desk and leaned forward, not believing this was happening. Uncle Jake's thumb pressed against my little ass pussy and it felt so good it turned my toes inward. I moaned as that thumb teased my little pussy. His other hand played with my clit and balls as he spread my legs open.

"Kel I have waited months to get to touch you like this. You have such a pretty little body sweetie. I hope Uncle Jake can make you feel as sexy as you looked in those pictures. You are prettier than alot of your cousins' friends I have seen around here. I would love nothing more that to have me a pretty litte niece running around here while Sarah is out running the roads." Uncle Jake whispers to me. Still using his thumb to massage my little hole, I moaned and panted heavily. I saw one of his desk drawers open as he pulled out a small tube of something I believed to be lube. Then I felt the cold moist feeling around my boy pussy, as he rubbed it on slowly. A finger was the next thing to follow as he slipped it inside my rear end.

I winced and grimaced slightly when that finger opened me a knuckle at a time. Wiggling my little ass, the finger was a snug fit but moved in and out easily. Rotating and pumping with his big hand Uncle Jake pleasured both of us alot. Kisses and his tongue on my under parts had me breathing like a dog in heat. He knew I was enjoying myself too. That finger was a welcomed gift as I thought of Mr. Lee's cock pumping my pussy.

"Yes, yes, yes Uncle Jake I love your finger inside of me. Please don't stop!" I begged. He knew I was hot for something and glad to be in position to give it to me. Working that finger in and out of me Uncle Jake massaged the walls of my pussy. He was very talented too!

When he grabbed my hand and placed it on his cock I was amazed how much thicker it was than Mr. Lee's. It felt so good in my hand I slid my hand up and down the shaft. The finger slid from my pussy and he turned me towards him pushing me to my knees between his legs.

"You want to taste my cock Kel? I would love for you to wrap those sweet lips around it for me sweetie." Uncle Jake said.

My hand still holding it I kissed the head and wrapped my lips around him and sucked it into my mouth. It was so nice as he allowed me to go as slow as I wanted too. Tasting a wet cock was so awesome, even if it was my Uncle's. Slurping his cock like an ice cream cone making him very wet. He must have thought of me as some little cock slut the way I went to his dick that way. But it was all I could do to control myself. Mr. Lee has spoiled me for cock since we started seeing each other.

"That's a mighty sweet mouth you have their Kel" Uncle Jake moaned. Directing me off the head to lick up and down the shaft to his balls. I used my tongue to tease each one of those nuts looking up to him in that desk chair. His hand in my hair he moved me back to the head of his cock. The way he handled me was so sweet and hot too. Never forcing his cock to me he allowed me to have fun as he got a very good blow job.

I felt Uncle Jake's hands under my armpits as he lifted me up and led me over to his bed. He told me to get up on my hands and knees which I did quickly. He pulled me to the edge of the bed with my ass pointing to him. Massaging my pussy again with his fingers I moaned before feeling the tip of his cock to my ass. Pressing that stiff cock hard it popped into me and let out a little short squeal. I didn't really know how bad I missed that feeling of a cock inside of me. Pushing with his hips and pulling back on me Uncle Jake's cock went deep with one thrust. It was definitely his way of slowly enjoying his first taste of my pussy.

"Damn that is some of the sweetest pussy I have ever felt Kel. You are a fucking natural for this baby. I am gonna love having you around here" Uncle Jake says moaning and grunting.

He used my little ass pussy very well and even with power just a few times. Slamming his cock into me, popping against my ass cheeks. My legs spread farther open and my little body being pressed down flat to the bed. I begged Uncle Jake to fuck me as good as he could. Pulling back to the entrance of my pussy many times and jamming it deep then deeper.

"I am gonna cum inside of you Kel. It is going to be huge too sweetie. Get ready baby!" he says as his cock dumps a massive load of cum in my pussy. Short slow pumps of his dick just before he leaned over against my backside to relax after a good fuck. His cock still inside of me when my little clit juiced the covers on his bed as I finished too.

Uncle Jake crawled back on top of his bed to rest and I got up on my hands and knees moving to exit his bedroom. I didn't say a word as I picked up my panties and robe to head for the master bath. Using a hot washcloth I cleaned up before going back upstairs to Sarah's room.


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