Nobody knows this - writing this took 2 months on and off as I remembered stuff. Some years back, when I was 14 and my best friend was 15, I pretended I was a girl (by my best friends encouragement) and we hooked up a few times.
It started when we were hanging out in my garage. My mom had a small clothing business she operated from our house. We were looking at some stuff and making fun of it as young boys do, when we stumbled onto some panties and bras. We both got quiet as we pulled out more and more stuff. My friend jokingly said, “these look like they will fit you” and we both laughed. It was getting late so we called it a night.
That weekend, we had a sleepover. We were talking about girls and stuff and he confessed that he was so horny that he would fuck anything wearing panties like the ones we had looked at in my garage. I laughed and said, “even me?” He pulled down the blanket and showed me the bulge in his shorts. “That’s just from thinking about those panties.” I said, “Let me see your dick and I’ll put on some panties.” He thought about it for a bit and said, “Go get some panties first.” I immediately left the room and headed for the garage. My heart was beating so fast. I was horny too but had never though about doing this. I liked girls. I grabbed 4 or 5 panties, shoved them under my shirt and headed back to my room.
When I got back to my room, I locked the door, turned off the light (only the light coming in my window lit the room.) I dropped my shorts and quickly put on a bikini bottom. It was too small and barely covered my cock. I turned around to see if he was watching. He had his cock in his hand and was stroking. He said, “You should go grab a skirt or dress or something. Be my girl.” I put my shorts on over the panties and went back to the garage. It took some rummaging but I found a box with some sort of dresses, the one piece ones with the top and bottom together. The top was like a tank top and the bottom was a miniskirt. I put it in an old bag and rushed back to my room. The light was still off and he was pretending to be asleep. I dropped my shorts again and put on the dress. It was pretty tight. I had to stretch it quite a bit to fit into it. “You look hot.” is all he said. He was on one of the twin beds in my room, naked with no covers on. I went over and stood next to the bed. I turned around slowly so he could see me. With my back towards him, I bent over and grabbed the other bed. I felt his hand on my butt. He squeezed it a little. My dick was pretty hard now and really tugging at the panties I was wearing. I wanted to take them off but I knew he was pretending that I was a girl. I let him take the lead.
After playing with my butt for a while, he said, “sit on your bed.” I turned and sat down. He quickly got up and presented his cock to me. It was a little longer than mine and wider. I naturally reached out for it and stroked it a little. He put his hand on the back of my head and pulled me towards it. I opened my mouth and slowly learned how to suck a cock. It took some time but I figured out how. My biggest fear was a big load of cum in my mouth - that I didn’t want. Every now and then I would taste a little cum at the tip. I sheepishly would say “don’t cum in my mouth” trying to sound like a girl. He kept saying, “I won’t. I want to cum inside you.” At some point, he grabbed my hand, pulled me to my feet, spun me around, and pushed me over onto the bed. My feet were still on the floor and I felt him pulling up the skirt. I climbed up on the bed so I was bent over, on my knees, with my head down and ass up. I must have been a sight, trying to act like a girl. I felt him pull the panties to the side and run his finger up and down my ass crack.
(This is where I have to add a confession inside my confession. I had already played with my ass by this time in my life. I had fingered it while I jerked off and had managed to work in two fingers from time to time. I had never considered being fucked by a guy though. This was thoroughly new and exciting (and a bit scary, I knew what the pain would feel like at first.))
I heard him spit on his fingers and felt him rub the spit on my ass. He then tried to finger it but it wasn’t wet enough. He then bend over and actually dribbled some spit right onto my ass hole. It felt weird and good at the same time. It must have felt good enough to relax me so when he tried his finger again, it slipped right in. He worked it in and out for a bit and then tried a second finger, it went right in also. This was tight for me. It felt good, and then not so good. I knew he was going to try his cock any minute. He then climbed up onto the bed and fed me his dick saying, “get it really wet. Spit all over it. Its going in your ass.” I eagerly sucked it again. I liked it at the time. I did what I could and he stood back up behind me and lined himself up.
I felt his dick head at my ass. It almost felt wider that my ass crack. I could feel it on the inside of both of my cheeks. I tried to help position it and push back on it. It wouldn’t go. He tried more spit on both his cock and my ass, but it wouldn’t go in. I finally said, in my soft girlish voice (in my head at least) “let me get on top.” This is how I would finger myself. He laid down and I quickly put his dick back in my mouth. I really slopped it up. I then spit in my hand and rubbed it into my ass, fingering with two fingers. I climbed up on top of him and immediately took his entire cock into my ass, first try. It felt really good and painful at the same time. I rode it for what seemed like just seconds when I heard him moan and felt him cum . I could feel the spasm of his cock. I kept riding. I didn’t even care but I had my cock in my hand for the first time since we started and was stroking while riding him. I didn’t know if he wanted to see me cum at this point so I stopped and slowly climbed off of him. He said, “get back on your bed like you were before.” I quickly got up on the bed, ass up again. He slid right back in without a hitch. This time he was in control. He fucked me raw. I had my cock in my hand the whole time and shot a huge load onto my blanket. He pounded me for a while and came again inside me. This time, after he came, he crawled back onto his bed, pulled up the blankets and went to sleep. I had been used and loved it.
I took off the panties and dress, shoved them under my mattress, crawled into my bed and jerked out another load as I tried to rub my sore ass a little. I came really hard the second time and fell asleep. The next morning he woke up and said he had to go home. I thought we would never speak of it again. We ended up doing this a lot. Always in the dark, always pretending to be a girl, and always got a little better. I still think about the only cock that has ever been in my mouth or my ass.