A Journey of Self-Discovery

Dressing Up For The First Time Part 2
Dressing in my sisters clothes became a regular thing after about 2 months of doing it, I would use her vibrator on my ass at least once a week. My family was gone more often so it gave me plenty of time to prefect doing my make up, hair and shaving my legs. One night when my family WAS home i was looking for a pen to write a card. I went to my parents room to look for one and on my step mom's dresser was a small blue key, i had no clue what it would go to and for some reason it seemed important. I put it back and continued on looking for a pen

Two days later my family was i out so imminently went to my sisters room to get dressed. I put on a hot pink mini skirt, a black tank top, a black bra with pink dots, and a pink and black thong. Then i put on some dark make up, and the blonde wig, i didn't shave cause i shaved the day before. i grabbed her vibrator and lube from her bedside table draw because i knew i was gonna use it that day.

After i was looking my best i went down stairs to get something to eat, i passed my parents room and started to think about the blue key. I went in and saw the blue key right where i left it, i had to know what it went to. I looked around until i checked their bottom dresser drawer and found a plastic fishing box with a blue lock on it, I opened it but i didn't expect what i found.

Sex toys and a lot of them. There was a lot of stuff that i didn't know what was or what they were called but one did catch my eye. It was a huge life like dildo, it looked about 12'' long and 2'' thick, with a life like balls and when i touched it i even felt real. I didn't have to think twice about taking it up to my room. I pulled off my thong got on all fours and lubed up my ass hole using my finger then stuck my sisters vibrator in. I had used it enough so i was able to get it in pretty quickly, i turned to the dildo and was so excited that i finally got to suck on the closest thing to a real cock there was.

I began to wrap my lips around the head and slowly began to take it in. i was in heaven, i had a 6'' vibrator in my ass and a foot long cock in my mouth dressed like a girl. The cock was way too big to fit in all in my mouth but that didn't stop me from trying, as i went down and came back up i started picking up speed and i tried to take more but i gagged at 7''.

I stopped for a second to catch my breath by licking down the shaft and to the balls, the balls felt so good in my mouth and it really felt like there was cum in their. I went back to suck the head and shaft and after a half hour of impaling my throat i was ready to get this thing in me so i started licking the head and rubbing the balls, i squeezed the fake balls in one last hard squeezed and something actually came out. Real actual salty sweet cum shot out of it and covered my face and filled my mouth, I sure it was my own Dad's cum that he filled himself for my step mom and that got me off. I sat their with my Dad's cum streams on my face and in my mouth, i swallowed it and rubbed the fake cock all over my face spreading it around.

I layed down on my back, spread my legs, took out the vibrator and set it aside, i then took the cock and got ready to put it in me. I positioned into place and slowly pushed it in, i felt like i was shoving a space shuttle up my ass, as i pushed it in even father i began to involuntarily moan and scream.

I pushed it deeper and deeper until it was 3/4 of the way in, then i slowly started to push and pull it in me but pushing it a little farther each time. After a lot of screaming, moaning and having that sweet cock in me i finally got the whole thing in me, it felt so intense. I gave up on being gentle and just started ramming the whole thing in and out of me probably tearing up my ass hole. I wished i could have kept in in longer but i couldn't help myself any more. I pulled my own dick out looking small compared to the cock and began shooting my cum at my own face, it covered my chest and got up to the bottom half of my face. The same time i came i squeezed the fake balls and shot more of my Dad's cum up in my ass.

I had never been more exhausted in my life, i layed there and for a little bit to get back my strength and eventually put everything back and cleaned my clothes and cleaned myself 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 sisters clothes. I went into my sisters 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 sisters 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, eye liner, lipstick, eye shadow, and mascara. I went back to my sisters 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 sisters 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.