He was 34, I was 14, skinny, wearing my sisters undies, mini skirt and blouse
No one was around my house that weekend. Once it got dark I went out to walk around. I was free to me what I wanted. I was dressed in my sisters panties, thigh high stockings, a small training bra that she doesn’t use anymore. I put on over it one of her shortest mini skirts and a tight blouse that clung to my body. It really showed up my girlish body. I was 5ft. 7in tall, and weighed only 110lbs. I definitely had a girlie indent to my waist and nice hips. My make up was perfect, I really looked pretty. I spent time admiring myself in the mirror with a nice bow in my shoulder length black hair. I went walking around and liked when some boys, even men would notice and stare at me. I got a couple of whistles, and a young boy named John from the local diner, was talking to me, telling me how hot a girl i was. He wanted my name and number. I was flattered, and was convinced that I was passable and felt totally femme.
I wandered a bit further than I normally would go, or ever had gone before. I turned around mid block and started going the other way. Then I heard a voice “Wrong way?” I looked up and it was a big house, almost a mansion I guess, a man was on the porch. I affected the most femme voice I could and said I needed to get back. “Who’s the lucky man?” I asked what he meant. “Well, there must be some lucky guy to have you coming back to him. Hell, most of us would do anything to have a girl as pretty as you wanting to come to us” he said. I explained that I was just out walking and had gone too far and needed to get back. It would take a long time I told him. He said that he could take me back if I wanted. He was nice looking, about 6ft tall, in great shape, he was wearing a tee shirt and shorts with sandals on his feet. I stopped while talking to him, he had walked out to me on the sidewalk. As we talked I started flirting, using my newly felt “girl” powers. Without even noticing, he was holding my hand, we were walking to his porch. He promised to take me home. Eventually he found out I was alone at home for a week. He was alone too, he was single and asked if I was single too. I replied that I was. He brought me out a mixed drink, something very sweet, it tasted great and I had 3 of them. I stood up and could barely stand up. He got up and held me, close. His strong arms around my waist holding me up, I put my arms around his neck. His kiss was soft and full, it was my first kiss ever. I was melting. He walked me to the door and we went in.
Inside he picked me up and walked me to his bedroom. A big king sized bed and put me on it. I was scared for the first time. He laid next to me. Kissing me, caressing me I felt so good but was scared that he would find my secret. I had pushed my testes up into my body cavity, and pulled my small little cock between my legs. In the mirror when I put my legs together I looked like I had a hairy pussy. It was then that I realized I looked just like my sister. I’d seen her pussy many times and I looked just like her. I pulled up the panties and held myself positioned like that. The panties made it look like I had a pussy under them with my “pussy hair” showing with the see through material. I didn’t want John, the guy to find out. I was suddenly afraid that he’d find out and maybe hurt me for not being a girl. Besides it dawned on me that otherwise he might want sex and at 14 I wasn’t ready for sex yet, definitely not as this girlyboy. I stopped his hand, and held it to my face. I told him that I should leave, and he put his finger to my lips and I parted them. He put his finger in my mouth using my tongue and closing my lips he pushed it back and forth in my mouth. I held his hand and moved my mouth on it.
“I think it’s time you learn how to do it for real” he said and stood up, pulled off his shorts and teeshirt. Totally naked now he stood at the edge of the bed. “Come over here and get it, I want you baby, I want that hot mouth of yours”. I moved over, sucked on him a while, he told me what to do, then I pulled off, hid my face in the mattress in case he hit me and told him I was a boy. “I know baby, it’s OK” then I told him I’d never had sex before and didn’t want to do anything except with my mouth. “That’s great, do it then, let me make you a nice girlie cocksucker sweetie”. I returned and started moving back and forth on his 7 inch cock. It was perfect, straight, about an inch and a half wide, tapered head. I’d look up to him while sucking my first cock and I saw those muscles in his stomach, his chest, his arms and I was entranced. I wanted to suck this cock. I wanted to use my body to please a man. I pulled off and he asked what was wrong. I just said I’d never done anything before and wasn’t sure what was going on and if I wanted to. “Sweetheart, it’s going to happen” he said. “I know, I mean, I want to, I really want to please you, I like you a lot” then I blurted it out. “I love you” he just pulled me mouth to his cock and said “You will”. I took my first load of mancum in my mouth a few minutes later.
Staying naked, he kissed me after I swallowed, he wiped up the cum on my face and fed it to me. Then he pulled his hand up my skirt and I pushed it away. He pushed back and was rubbing on my boipussy over my panties. He pulled off the skirt and saw my see through panties and little training bra. He pulled up the bra, and was sucking on my nipples while he eased the panties down. “You’re so damn pretty, you’re perfect” he said. Then he moved down my belly, pinching my nipples and took my little 4 incher into his mouth. “You taste like a raindrop” he said. I blew in his mouth in minutes. Laying with him, I started to pull on my panties, and he stopped me. “Not yet baby, we have time together” I settled in his arms assuming he wanted me to blow him again. I went down on him and started sucking him. As soon as he was hard, he got something from the nightstand, and rolled me over onto my stomach. When I felt the lube on my ass I tried to move away. I told him I’d never done it and I couldn’t take his big one for my first time. He got very aggressive and held me down. He got on top of me and I could feel his cock at my hole. I was begging him not to, asking why he was doing this to me, I offered to suck him off, to do anything he wanted just not to force me to do this.
“Baby you dress that hot, and walk around like that, you come into my bed, what the fuck you think is happening. A girl needs to get fucked, and a man needs to fuck her. You’re my girl baby, and I’m gonna fuck my girl”
With that I felt it pushing in, I started crying, and begging him to please not hurt me. He had about 3 inches into me and I was telling him how much it hurt. He stopped. He made me do some stuff which did stop a lot of the pain. He continued. It was all the way in me, hi beautiful cock that I sucked on was now all the way inside my butt. I wanted a pussy, I was now getting fucked in what I had to use as a pussy now. He slowly started moving in me, I stopped crying and was resigned to just getting fucked and get out of there. It took over half an hour he was talking to me like a girlfriend the whole time. Half way through he pulled out, rolled me over, and was fucking me missionary. He was kissing me, using his hand on my cock which he called a big clit, and sucking on my nipples. With his tongue in my mouth his lips on mine, he moved rapidly pushing in all the way. He told me he was cumming inside me, making me his girl, his pussy, making me a woman. I was no longer a girl, I was made a woman.
He gently pulled out and laid holding me. I asked if I could leave now and he said I didn’t have to. I told him I did. He watched as I put on my panties, straightened my stockings, Pulled down my bra, put on the clingy blouse I was so proud of before. I loved how it made me look like a girl but now as he said, I was a woman. I’d had sex with a man. I’d satisfied a man with my body. His cum was in my stomach and up my boipussy. I took my purse and went to the bath and redid my makeup and brushed my hair, taking out the bow. That was for girls, I was a woman now. He drove me home, before I got out, in the dark of night, he brought me over and we kissed. He patted my butt and asked me for a date the next night. I agreed. He was my man and I was now his woman. I had a week alone, and intended to be the best woman he’d ever had during that time.
I spent most of those nights in his king bed, getting fucked over and over again, getting sucked, and sucking his cock. It was some time before we could have that much time together, I told him my real age, and we could only sneak around on a few evenings, or weekends, it couldn’t last too long. Though I do remember well the day I dressed like a girl, and the night I was forced to become a woman. I now live full time as a woman, I’ve been on hormones, my cock shriveled to about 3 inches, not very useful. I’m having my testes removed in a month, that will help to get rid of the male hormones. I guess it was rape, he forced me to get fucked, I liked it and after all I did drink with him, I did tease him, flirt with him I guess I deserved it. But it shaped the rest of my life.
