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I Am A Boy Why Cant I Wear Dresses Like My sister

Watching My sister With Her Boyfriend In The Livingroom…
When I was young around 8 or so. I began to notice the difference between me and my four older sisters. They all have wonderful cloths, I had dull drab cloths. I had come across a “Sears Catalog” and hid behind a chair in the living room. As I was just engrossed in all the fine women’s under things and wonderful dresses, my next oldest sister (4 years older) looked over the chair top! I didn’t see for sometime until she made a noise.

I looked up and she had a look of wonderment. She asked “Just what are you up to there, mister?” I knew what I was up to was not on the up and up. Hence me hiding behind the chair. My My! she said, “you should not be doing that!” and ran off to tell mom. She got into trouble for tattling on me and nothing was said to me. I think my mom thought if she didn’t make a fuss that I would grow out of it.

But it has just emboldened me. And every chance I got I was into that catalog. I moved onto my sister’s old magazines. I had found an old box of my sister’s dresses in the attic and started wearing them on the sly. I loved it! My sister started dating at 15 and my mom worked afternoons, she was to watch me. She hated that but I promised to stay down stairs and out of her way.

She started to bring her boyfriends home. (I must say she had quite a few!) I would sneak a peek from the kitchen behind the sliding door between the kitchen and living room. I didn’t understand what they were doing at first but realized that the boys all loved it! Then after watching them for a few weeks, (some boys would just zip up and leave) she caught me because I couldn’t get back down stairs fast enough.

We agreed I was not to say anything about her boyfriends and she would let me dress as a girl! And on this coming Halloween, and if I wanted every Halloween from now on, she would dress me as a girl. I said deal. She said it was ok for me to watch her with her boyfriends, and if I had any questions I was free to ask. She told me boys really liked to have their penises sucked on.

I said I see what you mean. That when she was sucking, the looks on their faces was pure pleasure. She had about ten different boyfriends and said she liked them all. She said some boys do like to suck other boy’s penises too. She asked if I have ever thought about doing that? We were getting closer all the time and I said yes. She said “I see”. Then, I confessed that I was seeing “George” the boy next door and had sucked his penis like she had done to many of her boyfriends.

She asked did I enjoy it? I did, very much! She asked did I sallow his cum? I said of course and said I like the taste. Mmm she said. I asked” ” Should I not swallow?” Oh no, she said “you should always swallow!” Good because I like to swallow. Halloween was fast approaching was I going out as a girl? I said are you kidding? Ah yes! and I wished that I could be dressed as a girl 24-7! She laughed and said she new that, but liked to hear it.

I told her that George was going to take me around too. She asked if I was going to reward him for his e****t? I will after we get finished. She asked if he like me dressed as a girl? I told yes, and that I did dress for him a lot. She said great! This year she was going to pull all the stops, That I was going to be the girl of my dreams! That she bets George won’t be able to wait and will get me to reward him before we get finished.

I said yea I always cave and give him what he wants. She said she too was like that. We laughed, and hugged! I loved my sister. That Halloween she was right “I was the girl of my dreams!” She also was right about George, I had to give him a blow job half way into the evening, behind the school. When my sister got back from her date I was waiting up for her.

I was stilled dressed as that great looking girl. She asked did I have a good Halloween? OMG! it was great! And I didn’t want to change to for bed. She asked if George got his reward? I said she was right and he begged me to give him relief half way through. She asked if I made him wait? I said I couldn’t so I sucked his cock behind the school. She laughed and said she had done that many times, and always caved in to boys too.

I said I ended up sucking him three times before we kissed and said good night. She said some boys can go and go. I agreed that George must be one. Because he seems to need it more and more. (He is three years older than me) I confessed to my sister that I didn’t want to change out of my dress. She said that she was sorry but I can’t go to bed with makeup on.

I went up stairs and showered and went to my bed room and found that she had laid out a nightie and pink panties. Oh my! She stopped by and asked if I was in the nightie, I said and all so the panties. Our secret she said. I slept so soundly. The next day after mom left for work, I got into my short black skirt and makeup and a white top.

sis asked did I have a date? I right at the moment but had hoped George was going to call me. She had a better idea. One of her boyfriends was coming over tonight and she wanted to play a trick on him. And was I up to the task? I said sure what did I have to do. She was going to blind fold him and wanted me to give him a blow job.

I asked, what if he catches me? She would tell him that I was her cousin and that I wanted to learn how to suck cock. But I’m a guy! I said. She said that iI wasn’t much of a guy and was more of a girl. I agreed and said I would do it. That night she had her boyfriend’s cock out and hard. And waved me on over. I crept in and took his cock in my mouth while my sister watched.

It was a lot better than Georges and it took a lot longer for him to cum. But He did and I must say it was a lot more than George too. I slipped out and watched my sister take off his blindfold. She asked him he he liked it. I wanted to hear his answer. And moved the sliding door, shit he jumped up zipped up and sister came over to the door.

I was standing there caught. My sister said come in and meet her friend. I shook my head no, but she grabbed my hand and pulled me in. He said “Who is this?” My sister said my cousin from Canada. He held out his hand And I put my hand out and we shook hands. He squeezed my hand and pulled me close. What is that on your cheek? I reached up and moved my hand across my cheek and then looked it was his cum.

Shit again, he smiled thats better he said. Said good night and left. My sister and I sat down and talked about what had happened and if I had fun. I said it was great! And I really like his cock. And my god was there a lot of cum. She said that there is good cock and there is great cock but never has she seen a bad cock. We both laughed! She asked was it better than Georges? I said way better and that I was going to have trouble going back to Georges cock , that she had ruined me.

We laughed again. She said that we could maybe do a threesome. that she saw I was really into cock and she liked watching me suck cock. I said that I couldn’t wait. and yes I would love to. She said then she will plan it soon. She asked if I liked being a girl? And she never understood why “Boys can’t wear dresses” I hoped you like the story and leave some comments.

Kisses to all, love tammy.


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