I had loved wearing girly clothes from the age of 3. I was the second son in a group of 4 brothers. My mom and Dad always told friends that I was supposed to be a girl. That kind of remark really screwed me up. As i grew older, i was small, thin, and had big brown eyes.
In elementary school, the girls decided that i would look good in tights. I found it embarrassing but at the same time, exciting. I didnt do anything about it but one of my friends heard there comments. A few days later, he asked me if he could fuck me. I was frightened by that, but I was also turned on by it. His name was Greg and his sister was a cheerleader a couple of years older.
Greg kept pestering me about it and I kept thinking about it. Finally, I told him I would have sex with him if he would let me dress in his sister’s clothes. I was really excited about the possibility even though I had never had any sexual attraction with boys.
A week later, Greg invited me over to his house while his parents were away with his sister. When I got there, I went thru Greg’s sisters sexy stuff. I didnt plan on actually having sex with Greg but I wanted to wear real girls clothes.
I took a shower and suggested Greg do the same. While he was showering, I went to Kay’s room. I found a sexy nighty on her bed that she had worn the night before. It smelled so sexy that my cock got hard. I put on the panties and the babydoll top and didnt notice that Greg had got out of the shower and was standing, naked, in her doorway.
Greg said I was really pretty. I guess I blushed. He wanted to have sex immediately but I got him to calm down, since I didnt want to waste this opportunity.
I asked Greg if there were any other things that I might wear. Greg said his Mom, who was very sexy, had worn a really hot French maid costume for Halloween. We went to her bedroom and Greg helped me find the outfit. I sent Greg downstairs to wait.
I found some sexy crotchless panties, black thigh high nylons, garter belt, and frilly slips. I had tried my hand with my Mom’s makeup in the past, so it was nothing new to me. I put on makeup, probably a little too much but I liked it. I had found the sexy wig Greg’s Mom had worn and brushed it out. I put on the sexy black French maids dress, the wig and then a pair of black 4 inch high heels.
I checked myself out in the mirror. I could feel the fabric of the frilly slips against my hard cock. I walked out and down the stairs. Greg was sitting on the couch when he saw me. Greg stammered that I was beautiful and stood up to expose his hard cock.
I walked over in front of Greg and I took his hand and placed it on my ass. Greg tried to kiss me but I turned my head. It felt great to be a girl. Greg continued to stroke my ass and I found myself becoming aroused. I turned and Greg and I awkwardly kissed. Damn, it felt great.
We ended up hugging and kissing and as we both got turned on. Greg kept saying that he wished his friends could see me. I told him that wasnt a good idea. Finally, I felt Greg’s hands pushing me down on my knees. I complied and found Greg’s hard cock inches from my face. Greg told me to suck it. His cock was really pretty with a pronounced head.
I dont know how or why it happened but the next thing I knew was Greg’s hard cock was in my mouth and I liked it. He was moaning and holding my head and was gently fucking my mouth. Oh, I liked that, hearing his pleasure, knowing that I was pleasing him like a girl would. Suddenly, Greg shuddered and he pulled me close and began to cum. He pu.ped a huge load down my throat and I liked that too.
Greg pulled his cock out of my mouth and I kissed it, stroked it, and suddenly, it was hard again and I sucked him again. It was nice to be that young.
We spent the day playing around with Greg begging to put his cock in me. I told him I was a virgin and wasnt sure. Greg said his Mom had a bunch of sex toys if I wanted to try some. I said that it might be OK. He got her secret box of lotions and pens shaped toys. I layed across Greg’s lap and he applied lotion to my bottom. I must admit that it did feel great to have him fingering my ass. Then, he switched to one of the vibrators. I had never experienced this but as Greg slowly slid it in and out of my butt. Greg found a bigger dildo and fucked me with that, then back to an even bigger vibrator. He slid that monster into me and i dont know what he touched but i suddenly began to cum, unlike anytime in my life. I turned to Greg and just said, “Fuck me.”
Greg obliged and he fucked me 3 times, right thru my crotchless panties. This was turning out better than I had ever dreamed. Greg finally said he couldn’t fuck anymore but I wanted more. He asked if he should call his friends and I said, “Please.”
Our friends showed up, not knowing who i was. Greg said i gave fantastic head and had a super tight ass. Before i knew it, i had a nice hard cock on my mouth. I sucked until he came then took another. As the night went on I gave my body to these guys. About midnight, the front door opened and there were Greg’s parents and sister. Greg’s Mom was furious and told me to get out. I stammered that my clothes were upstairs, but she said to get out and I could wear my faggot clothes. She pushed me out the door, looking like a whore. I was frightened. It was a mile to my house. I began the long walk thru the darkness.
I was almost home, having ducked out of site several times. The last quarter mile, there was no place to hide, but I had to get home. As I was walking the last way, I heard a car come slowly and stop. A nice looking guy in his 30s asked if I needed a ride. He persisted and I climbed into the car with him. I was nervous but figured he was harmless.
As we sat there, he said, " you’re not a girl are you?" I started to cry and he said it was OK and he understood. He asked me if I wanted to tell him how I ended up dressed the way I was. We pulled into a little park across the road from my house and i told him my story. I felt better after sharing with him. He said he better let me off there, rather than pulling i to my driveway. We got out of the car and standing there in the dark with him, he gave me a nice hug. I found myself kissing him and he kissed back. He was much better than Greg, and I enjoyed making out with him. My hand found his hard cock in his pants. I stroked it, unzipped his pants and pulled his cock out. I knelt down and let him slide his cock into my mouth. I loved his cock, loved the feel of its head against the back of my throat. He suddenly came, pulling his cock out until it was resting on my tongue. My friend said he wanted to see me swallow his cum, which h I did. That obviously turned him on. He pulled me to my feet and kissed me again, his tongue probing to taste his own cum. As we were doing this, I felt his hand slide between my legs, over my cock and onto my ass. He moaned and said I was incredibly wet. I asked if he wanted to fuck me and he picked me up, holding me by my legs and his cock found my hot, wet, cum-filled ass and he fucked me. He bent me over the fender of the car and pounded my ass furiously. When I felt him cum, I also came.
I kissed him goodnight and walked to my house, sneaking in my bedroom window. This had been my introduction into gay sex, and I liked it. Being able to dress like a sexy girl made all the difference. I was a slut when dressed but not interested in guys unless i was dressed. My life changed after this.