I started at the age of 8, wearing my mother's panties, bras, stockings, shoes, dresses and night gowns. By the time I was 11 I was dressing completely wearing my moms wigs, wearing makeup, and walking around dressed like her. I was her height and her clothes fit just right. There was no sexual pleasure per say. I hadn't started to get pleasure from masturbation yet. The feel of the clothes was something I really enjoyed, seeing myself as a female felt normal. The first time I actually got off wearing her clothes was when I was 12. I was dressed up, the feeling was stronger then ever, when I felt this sensation coming from deep in my balls, then I shot my load to my surprise in the panties. After that the sexual side kicked in big time. Every chance I had I would wear women's clothes. By now any women's clothes got my attention and attraction. I would take clothes off the clothes line in backyards at night. I got to experience all kinds of clothes. If visiting some one I would find a way to nose around. And if the opportunity came up, I would try on their clothes. More then once my mother found her items moved or a stain in them but she never approached me about them directly. I remember once she found a long shinny silk night gown in my room. She just took it back. I never got caught until I was 14. I had one of mother's wigs and basic makeup with me. There was a house 2 blocks down from ours where this 50ish woman lived alone. I would cut her grass every 2 weeks. I knew her yard real well so I could walk into it at night. She always left her shoes outside the back door. She didn't wear shoes in her house. So I could count on finding something there always. I had grabbed a dress, panties, and bra from another yard off the clothes line. I used the extra panties to stuff the bra. Then went and got some shoes, I found some flat sandals. Wearing the wig & some makeup I went out walking around dressed up. It was about 2am, I had walked about 10 blocks from the house. Hadn't seen anyone since it was a weeknight. A car passed me, and kept going. I turned on to a side street to head back, when the car pulled next to me, the man offered me a ride. I just kept walking; he pulled ahead of me, and then got out. He walked up and grabbed my arm. He said you're a cutie baby. He tried to kiss me on the mouth. I resisted, but he was bigger then me by at least 10 inches, and 100lbs. As he manhandles me, he pushed me down on the grass in front of this house. He then said baby I want you. He opens his pants and flipped out his dick, it was good and hard, I froze. He got on top of me trying to get between my legs, I was able to roll over, and get on my stomach, but that only worked to his advantage, he pinned me down with his arm, and then pulled up the dress I was wearing to my waist, I was wearing only panties. He pulled the panties down exposing my cheeks. He said you are nice, love that ass. Then I felt his dick in my cheeks, he pushed in but nowhere to go, he then spread open my cheeks, drove it home into my ass, I cried out, but he had me. He proceed to pump, as he did he kissed my neck, he reached around and grabbed my boobs, which were panty specials that I had gotten off the clothes line, he smelled of cigarette and booze. After about what seemed forever he finally shot his load into me. I could feel every squirt as it went into me. I had tears running down my face, the little makeup I wore was smeared, and here I was full of a man's dick in my ass. He got out of me and rolled off to one side. I looked over at him and he just smiles back at me. I laid there not knowing what to do. He got up, told me I was really a good piece of ass.
As I rolled over to get up, he stood in front of me, and then told me to clean him up, I wasn't sure what he wanted, he slapped me hard, and said clean my cock bitch. He reached down and grabbed my hair, when he yanked, the wig came off, and he said what the hell!
He grabbed the bottom of the dress and pulled it up high exposing me, what the hell are you, I didn't answer. Well what ever you are suck my cock now. With that he pushed his dick into my mouth; I choked as he pushed in deep.
The taste was awful to me, but soon it got worst. He said now take this, and he let loose again filling my mouth with his cum. I swallowed some and the rest came out on my face and landed on the dress. Once he was done he pushed me down on the grass again, he zippered himself up and walk to his car and drove off leaving me there. I must have laid there 30 minutes before I got up and dressed myself again, replaced the wig and went towards home. I replaced the shoes, then went by the house where the clothes came from and return them to the clothes line, then went on home. I felt sick for about a week after that thinking what he had done to me. I was ashamed but couldn't tell anyone about it. It was about a month later that I told my aunt everything, including that I had worn her clothes. She listened and then hugged me. She advised me to let it go, and be careful, and not get runs in her stockings. Well i kept dressing up when I turned 16 I wanted more. I sneaked out around midnight and had my mother's wig and high heels. I grabbed panties and a bra and pantyhose off a clothesline like I had done so many times before. But this time I walked about a mile to a major street. I could walk like a woman moving my hips. A few cars went by it was around 2 am not many cars out. Finally after about 30 minutes this car pulled up. this older guy driving. he asked if I needed a ride? I said i could give him a ride. He said 10 for head I said sure. I climbed in he parked on a side street. I got busy. It didn't take long for him to reward me a nice mouthful. Once done I got out and waited for another car to pulled over. it was about 3 am by now and another man pulled up. made the same offer he said get in. he parked along the side street, he told me to get in the backseat, once he joined me he undid his pants and told me to get on my knees, he lifted the dress and pulled down my pantyhose and panties, in the darkness he couldn't see my dick, he grabbed my hips and got behind me moving his cock to find my hole, he found it and shoved it in hard, but in it went. It was feeling good and he said I am cumming just then a tap on the window. A city of Miami Police officer. The guy pulled out of me, and fixed himself, I pulled up my panties and pantyhose then fixed my dress. He said get out, he asked for ID. The guy showed his D.L I said don't have any. he told the guy to get lost which he did fast. the cop told me to come with him. He had me lean onto the trunk of his squad car he frisk me. He found the $30 I had in my bra. He told to me bring my hands back and he cuffed me saying I was being arrested for prostitution. He drove to the local office. he took me in and sat me a desk. Another cop came over and asked me a bunch of questions. That is when they figured out my age and sex. The second one grabbed my arm and took me home in cuffs. he knocked on the door, my mother answered, she was like what is going on. the cop explained where I was picked up and what I was doing. And how much money I had in my bra. She was flipping out. the cop left me with her. My dad wasn't home he was at a convention in Tampa. She dragged me to her bedroom and started yelling at me. Whose clothes I was wearing, those are my shoes and wig. So I told her about the clothesline. Then she wanted to know what i did for the money. She was crying you're a cheap whore. she lifted the dress and looked underneath. She saw the wet stain in the panties. She yanked the pantyhose down and then the panties followed. She stuck her hands between my cheeks, her fingers came up and she smelled them. This is a man's sperm. She said go to bed we will talk in the morning. i could have died right then. But morning awaited me. In the morning I was so embarrassed and shameful. When got up she asked me you want to be with men? You want to be a woman? Then she asked how many men have used me? I told her everything. She said no more whoring. She never said another word about it.