Caught By My Sister and Her Friend

My sister , which we are going to call Rhonda, has always had a real naughty personality. She was 12 and I was a boy at 10, Mom had put sis in charge since she had to go to work early. My mom and Rhonda had caught me wearing their clothes a few times and my mom made the remark one day after catching me again. She said, “the next time, I’m going to dress you up all the way”, “you’ll see what it feels like to be a girl.”



Sis had caught me a few times wearing her clothes after that. And each time I would beg her not to tell mom .And of course sis would always come up with a compromise. She told me If I would help her with some things around the house, she would keep it our little secret. She gave me a drawer in her chest with some of her panties, bras and slips to use and not to wear anymore of hers.

Time went on and I was still sneaking and trying on her dresses when she wasn’t home. I always tried to put everything back so she would not notice. And I thot I was getting good at this too. Neither mom or sis had said anything about my dressing for a few months.



Then one day after school I came home and Rhonda was already home. As I opened the door, she ask me to come to her room. As I entered, I saw on her bed was some underwear, a slip and a dress. I ask in a very timid voice, “what’s..a what's going on?” She said she knew I was still messing with her clothes, but she didn’t say anything. She didn't want to upset mom. So, today she went to a department store after school and purchased some clothes in my size and wanted me to try them on.

Rhonda said, in a stern voice,” take off your school uniform!, and put these panties on, come on!, pull them up, you wanted to wear them so bad!” I was shaking and was so nervous, I said I didn’t want to. “I won’t do it again, sis!” Sis said, “ Your "not doing it again luck" has just run out and now your going to get dressed up like a girl, just like mom said she would do if she was to find out!”



Rhonda said, “Here’s your very own bra, so put it on and shut up! Now, get over here and get this dress on. Put your arms up and I'll pull it over your head. Now, I know you saw the petticoat on my bed when you came in. It's short and fluffy just like mine, Come on!, step into it and pull it up under your dress. “Well now, I think you're starting to look like the girl you want to be. Come over here to the vanity and lets fix up that face of yours. A little mascara, blush and some pretty red lip stick will brighten up anyone's face. Let’s fix your hair a little. Now were going to go into the living room, sit down and wait till mom gets home to see what a nice sweet girl you turned out to be."



I pleaded and begged Rhonda not to tell mom, I’ll do anything for you, please sis”. "Sis said anything?". Hmmmm... sis thot for a moment and said “everyday after school I want you to put on this outfit and do all of my chores. And if I ever catch you not dressed up, then mom and all your friends will know all about it.



Everything was going great, I would get home from school and put everything on with my dress. Then I'd walk down to the community boxes and get our mail. When sis came home, she would inspect me to make sure I was dressed right. She would always giggle a little and shake her head at me. She'd say," I just can't believe you actually enjoy wearing that stuff!"



Sis said I'm going to have to teach you how to walk in my dresses and heels. And also how to fluff my dress up before sitting down like a girl. She took a few minutes everyday to show me something. She did sit me down one Saturday and showed me how to apply my make up a little better. And she would always remark how I have become a wonderful sister to her.



She would check to see if her work was done like she ask. Sis didn't want mom to be dissatisfied at all. Since she was supposed to be doing it anyways.



One day after school, I got dressed and started washing the clothes. I heard the door open. I yelled out, “Sis, I’m in the laundry room”, The door opened slowly, I spun around and there was my mom. I could see she was shocked and her smile on her face went to an confused look, then she shook her head and said in a giggling voice, “well!, I guess you've been busy dressing up again, haven't you now!. "And that dress!, that not your sister's!"



I explained that Rhonda caught me a few times again in her things and made me dress this way.

She looked me over, but didn't say anything for a few minutes. Then said, "Well, Rhonda is in-charge of you, so you better do as she says or you will have to answer to me as well. Mom said, "Hurry and get finished up in there and go to your room. I will talk to sis when she comes home.



Later in my room, I heard mom and sis in the kitchen talking and giggling. Sometimes they would let out a loud laugh, but I couldn't make out what they were saying.



Finally they called me for supper. As I came in, mom handed me an red apron with white lace on it and said "put this on and get over there and start serving the food. "I did as she said and brought everything over to the table. I went to sit down.



Mom said in a stern voice, "Oh! No!, you don't sit here with us. This table is for regular people, When your finished serving us, you can take your plate to the back porch and eat. We don't want to look at a sissy while we eat. Rhonda said "look she's starting to cry, Mom looked up and said "no wonder you want to wear a dress. Take those sissy tears outside please!"



When they finished, they called for me and told me to clean up everything in the kitchen, then come into the living room.

As I walked in mom and sis giggled an told me to sit down. Mom watched as I put my hands under my rear and smoothed out my dress as I sit down. She said, "OMG! I guess someone has been practicing haven't we!" With that said, they both started laughing again.



Mom said, "We have decided to replace all your clothes with girls. And for now on you will wear panties, a bra or camisole under all your clothes. And when your home you will wear pretty dresses and petticoats like you always wanted too. "Rhonda added, Yes, your gonna get to be my new sister" Mom said, " Rhonda is still in charge of you and I will leave a list of things for you to do around the house. I want you up at 5am. "you'll cook me breakfast, clean up and start your chores . There will be no more sleeping in for you this summer. And if you don't get up, Rhonda has my permission to paddle you and I will too when I get home."



Mom said " when Rhonda gets home from summer school tomorrow she will take you shopping for some summer dresses and more lingerie. your going to learn how a to act like a girl for the next few months of summer. I hope you enjoy yourself."



More later as Bobby grows up:

Did you ever do cfnm for sister or any of her friends

You are truly a fortunate guy to have a sister in possession of such facts about you and for her to keep them a secret. Neither of my sisters would do so.... I am sure that before night fall all of thier freinds would have the complet and detailed story of the event. But, then this may not be so bad as I then may have an opening to give them the show my sister was privileged to witness.

Great story, and it reminded me of getting caught by my sister.



I was out back mowing the lawn on a hot, sweaty summer afternoon. I was 14 I think, and only wearing a pair of thin nylon shorts. With all my sweating my shorts were soaked, and thin nylon sticks to your skin when wet. There was no liner in these shorts - I hated liners and always cut them out.

Anyway, I was pushing the lawn mower back and forth with my wiener clealy visible under the thin, wet, material. I noticed it, and then became fixated on it, as I was just into puberty, and it's increasing sized was facinating to me. Then I started getting a *****, as happened at the drop of a hat for me, and it was sticking straight out of the shorts. It must have been quite a sight.

I couldn't stand it any longer, and stopped the mower and went over to the house, under the small porch that led to the back door. There was plenty of room to stand up there. I started rubbing myself through the nylon, watching erection push tightly against the nylon. It was a real turn-on, and my climax was coming quickly.

(Now there was a basement window near where I was. The window had a thin curtain over it, plus the basement was dark, so I was sure no one was down there; But I was wrong.)

Just before I "Came', I took my **** out from inside my shorts so I didn't shoot in them. I came good, and squirted a lot of times. When it was finished squirting, I leaned back against the house, my hand slowly stroking, as 'It' calmed down and I caught my breath.

As I became concsious of myself again, I looked down at my hand and my early puberty **** shiny-wet with my own *****, and saw my sister looking out the basement window, maybe 3 feet away. She gave a small wave, and a big smile.

I instantly turned away and put my **** back in my shorts. The basement window slid open, and she said, "That was a great show Bobby. I only wish I had friends over to have seen it with me, but at lease I can tell them all about it - in great detail." And she left the window.

I was frozen with embarrassment, and could say nothing. I couldn't move either, and just stood there, looking down at the ground where I had shot my load. There was a good amount running down my arm too.

A few moments latter my sister came back to the open window and reached out with box of tissues in her hand. "Looks like you could use these." she said with a giggle. "But seriously, I swear I won't ever tell anyone. Some things between a sister and her brother, stay between her and her brother."

With that I fell back against the house and looked at her for the first time and said, "Thank you." My arms hanging at my sides, and my wet nylon shorts clinging like a second skin to my still throbing penis, for her to see. But it didn't seem to matter now - she saw me do it all, right in front of her. I thought I was going to die.

"You still have the lawn to finish, big guy." and she closed the window.

"Hummmmm," I murmered, she has, never, ever, called, me big guy, because I was only 115 pounds. Even more confusing, if she was making some reference to my weiner, it wasn't very big either.

I walked back to the lawn mower, started it up and resumed pushing. My half erect weiner pushing from side to side with each step under my shorts.

I like your story but give us more detail next time :)