Dressing Up For The First Time

I was always interested in women’s clothing. I don’t know what it was but it just made me wonder what it was like to be a girl. I finally gave into my curiosity and wanted to browse my sisters clothes. I went into my sister’s room when the house was empty and opened up her closet. I saw all of her nice shirts, blouses and dresses, i looked around pulling some stuff out and eventually made my way to her dresser and saw all the panties and bras. I wanted so badly to try on a whole outfit but i was terrified of getting caught. Then i got an idea. I picked out the clothes i wanted to try on (a purple tank top with short shorts and a padded purple bra with a lacy thong) and went to my room, locked the door then striped down and started to put on the thong and bra. It felt so good to be wearing them, it just felt right but something was off, i needed boobs. I stuffed the bra with socks and then it looked right. Then i put on the shorts which were even shorter on me and the tank top. I looked in the mirror. My body looked good and my face need some work. I went back to my sister’s room and grabbed her razor, shaving gel, and her makeup bag. I went to my bathroom and took off everything and shaved off all hair below my neck. I never realized how good my legs and ass looked now that all the hair was gone. I put back on all the clothes which felt even better now that my skin was silky smooth, then went to my mirror to apply the blush, eyeliner, lipstick, eye shadow, and mascara. I went back to my sister’s room and got her blonde wig and came back and put it on. I looked amazing, no one would be able to tell that i was a boy. I spent the rest of the day in the clothes. I started doing my nails, looking at clothes online and taking cute pictures of myself in the mirror. When it started to get near the time my parents got home i went back to my sister’s room to put everything back. I was heartbroken that i had to take off everything, but i did and i put everything in the room back to the way it was. At least once a week i would dress up in different clothes, but the time after this was when i really discovered how fun it was to cross dress.

After the first time i crossdressed in my sisters clothes, i just had to do it again. It was a week until i had the house to myself for a couple hours. Right when my family left i went to my sisters room and picked out some clothes different than the ones i wore last time. I chose my sisters dark purple prom dress that goes down to my upper thighs. I also got her black strapless bra, her cute black thong, the blonde wig and makeup bag from last time, I went back to my room and locked the door to re shaved everything again, I slowly put on the thong because i love the feeling, then put on and stuffed the bra. It took me a little bit to get the dress on but when i finally did it was worth it. After i applied the make up and put the wig on i look beautiful. The dress looked really good on me with my thin feminine figure, and i filled it in pretty well. i went back to my sisters room for a braid to tie back my hair, As i went to her bed side table and opened up the drawer, i saw the braid but i also found something else. Inside the draw was a big hot pink vibrator. It was about 8 or 9 inches, was completely smooth and was plastic. I suddenly got a very naughty idea, i was scared because i had never done anything like this before but so horny i didn’t care. So i grabbed the vibrator and the bottle of lube in the back or her drawer and went back to my room.

I sat on my bed trying to think of what i should do with it, When i finally thought of what i should do, i got on my knees and put my elbows on my bed with the vibrator in hand and started to suck it, bobbing my head, and licking its shaft. It didn’t have any taste but the feeling of it in my mouth felt unbelievable. After about 10 minutes of this i was so damn horny i had to get it in me. I started to slide off the thong but left on the dress, i took the lube and began to applied it to my asshole. After i thought i had enough, i put some on the vibrator and laid back on my bed and spread my legs and started to insert the vibrator in my ass. I tried to relax as much as possible which helped because it slid in without much pain, there was a little pain but that just added to the pleasure. i finally got the whole thing in my ass and started to thrust it a little harder at a time. When it finally wasn’t a tight as hell i turn on the vibration setting to 100% and immediately moaned loud enough that it filled the whole house. It was easily the best feeling i’d ever felt at that time. After a half hour of making that vibrator fuck my ass in various positions i was about to cum, so i rammed it in me at full force as fast as i could. With one loud scream i came in my dress. It took me a minute to calm down after that orgasm, i realized that i didn’t even touch my cock the whole time i was using the vibrator. I then took off the dress and cleaned my cum out of the inside, cleaned off the vibrator and put the dress and everything else back in her room.

After that day any time i dressed up i always used her vibrator even after i made my next big discovery…

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