First time dressing up

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. When i was 15 i finally gave into my curiosity and wanted to browse my s****rs clothes. I went into my s****rs 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 witch 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 s****rs room and grabbed her razor, shaving gel, and her make up 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 witch felt even better now that my skin was silky smooth, then went to my mirror to apply the blush, eye liner, lipstick, eye shadow, and mascara. I went back to my s****rs 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 s****rs 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 s****rs 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 f****y left i went to my s****rs room and picked out some clothes different then the ones i wore last time. I chose my s****rs 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 make up 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 in 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 s****rs 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 vary 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 had 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 witch helped because it slid in with out much pain, their 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 id 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 f***e as fast as i could. With one loud scream i came in my dress. It toke 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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Posted by Badassgirl123
6 months ago    Views: 1,698
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1 month ago
Love this story...reminds me of my first couple of times trying on my sisters panties and playing
1 month ago
Great story
4 months ago
I love how you had to clean the cum out of her dress!
4 months ago
I loved reading your story, very well written
Brought back memories , i would do the same thing when i was home alone
6 months ago
I love this :)
6 months ago
Pretty much the same way u started with my sis's sexy clothes! Loved it.
6 months ago
Mmmmm, Sexy Story Jess! I Bet You're a Hot Little Rider! ;-)
6 months ago
starting out real good now for part two
6 months ago
love it
6 months ago
wow the best I read your today made me remember my younger days
6 months ago
great story thanks for sharing!
6 months ago
Great story.