I always loved girls clothes. I can remember being too little to realize that there would never come a day that I could wear them in public. I would watch my mom in her panties and bra, slip outlining her satin panty line and long to do just that. To stand in a makeup mirror, draped in satin, and applying lipstick to my lips was like a dream. I was thirteen when I first put on a pair of panties. My life has never been the same. I put them on and can feel my ass cheeks pucker. I feel my cock trying to strain out from between my legs because I'm so excited but I force it to remain hidden. I look at my smooth crotch, shimmering in satin, legs in pantyhose, bra clutching my chest, and just wish I could stay like that forever. Having said all that, here's what happened.
I always kept this a dark secret. I grew up in the south, and boys who liked panties and makeup weren't widely accepted in many circles. I was relegated to playing dress up at home, when no one else was there. My father was a traveling salesman and my mother worked long hours in her office. One brother was at college and the other was at boarding school. I played hookey from school one day because I knew no one else would be in the house, thus giving me full reign of my mother's clothes! I saw her off to work and no sooner than her tires left the driveway I was in her underwear drawer. I had a good looking mom. She had a tight bod, and so did I. I pulled out my favorite bra and panties, both shiny lime green shimmering satin, and a pair of black pantyhose. I loved the ritual of sliding the panties on, then putting on hose, then slipping into a slip. It was such a wonderful sensation on my legs and felt so good on my hips.
I stood in the mirror, just like my mother, putting on lipstick and mascara, and playing with my crotch. I had used some of my mom's shoulder pads to make my tits. After applying makeup for a solid hour I slipped into the closet to get a dress. I put on a tank dress made of a polyester/silk blend, then forced my self into a pair of heels. I would walk around the house, heart beating a million miles an hour, just imagining being a girl. I thought it was something I could do endlessly (still do!)
I laid down on my bed, spread my legs like a girl and began rubbing the satin crotch of my panties through the hose. I loved to lay back like a woman, caressing my own tits and feeling my own moist center, spreading and holding my legs open, imagining a man having his way with me. I did this all day long, jerking off, shooting my wad. I could cum 5 times in a day it made me so horny.
Enter Brad. My good friend since elementary school had come by after school to see if I wanted to go with him to the beach and go sailing. He let himself in my side door that was unlocked, unbeknownst to me. Brad rolled into my house as I lay on my bed in full drag and makeup, legs spread and rubbing my crotch. I guess he was going to try and surprise me because he did not alert me to his arrival until he was right on top of my room. I had nowhere to hide! I was in full drag, spread open on the bed, begging to be fucked like a girl.
"Yo, Johnny" Brad yelled. I jumped up hurriedly to hide but literally had nowhere to go. He immediately came around the corner in my room to see me standing there, fully dressed in girls apparel, breathing heavy like I'd run a marathon. I tried to blow him off and say come back later, I was just fooling around, but he wouldn't listen. I was ashamed. I wouldn't look at him. He asked a few times what I was doing and I wouldn't answer. I finally looked up at him, a tear running down my cheek, making my mascara run down my face a little as well. He walked toward me, and I glanced to his crotch to see him absolutely bulging. He came right up on me, put his hand right on my satin crotch rubbing it like it was a pussy, and kissed me deep and long. I was trembling I was so nervous, but kissed him back deeply, trying to get my tongue as far down his mouth as I could. He put his hands on my satin ass and slapped my cheeks while he french kissed me. I fell back on the bed like a woman and he got on top of me. My heart was pounding. I was nervous, yet probably the most excited I’d ever been in my life. His cock was so hard. It was much bigger than mine and was throbbing against the little patch of satin on my crotch. He pulled his cock from his tennis shorts and mounted my chest, sticking his rod into my red painted lips, force fucking my face like it was his own playground. I felt my mouth widen as it never had before and his cock was fully in my mouth, nuts resting on my chin. It almost gagged me it was so big, and I was amazed at my mouth being able to handle it. He thrust his cock into my face, all the while reaching behind and furiously rubbing my panty crotch. I wanted to be fucked. I wanted to be his girl so bad. He could sense it. He fucked my lips a little bit more before sliding down my body, feeling up my fake tits and rubbing my legs and ass furiously with his hands.
"Fuck me" I said, trembling and shaking.
"I want to fuck you so bad, baby" he said. "What's your name, girl?"
"Ashley" I said, breathing heavy, trembling.
"Do you want my cock, Ashley?" He said, kissing my chin and neck as his cock rubbed against my crotch.
"Please give me your cock" I said, "Please fuck me, Brad"
Brad pulled my panties down, spit on his hand a few times, each time lubing my asshole and kissing me simultaneously. I had a lucky rubber I was saving for that special someone, but I never imagined that special someone would be another guy. Brad wrapped and slid his cock into me after carefully poking it in and out, getting my manpussy ready for his rod. He finally got the head in, and slowly but steadily pushed his cock until he was fully in me. I screamed like a girl in ecstasy. I felt like a girl in ecstasy! All I could do was lay back, clutching my ass cheeks around his sweet cock, clutching his ass cheeks with my hands while he pumped me, kissing me all the while as he rubbed my fake tits. He fucked me missionary for about ten minutes before he pulled out. He fucked me so good that I came without touching myself. I came in my panties he had pushed off to the side to enter me. He pulled out and put his cock back up to my face, I licked and sucked at the head until it exploded in my mouth. I licked it all up and he rammed it down my throat. I took every last drop of it down and lay there, drenched in sweat and cum. He kissed me, and like a typical man, felt awkward and got up to leave. I lay there for at least an hour after that, just rubbing my flaccid cock through my soaking wet panties, already wishing it would happen again. I had to dispose of the bra and panties. They were drenched in cum and sweat, makeup smeared into the satin bra. My mother looked furiously for them, thinking she went crazy as she was the only woman in the house. Not anymore…………