LONG but I get to the point eventually.

I was bullied in high school. A lot. At one point when I was about 16 I was cornered by one of the guys responsible. Now, he would never admit it in those words, but the only reason he was harassing me was apparently because he was attracted to me. I guess that it was easier for him to choose me because well, I'm often mistaken for a girl. I'm kind of skinny and short, I prefer to have long hair, what little body and facial hair I had grew in really thin so it was barely visible.

He cornered me alone behind the school on a friday. I was scared, I had no idea what he planned to do, I thought he was going to kill me or something. He told me not to talk, then he kissed me. He pinned me there against a wall, exploring my mouth with his tongue. I didn't want it, I had never kissed a man before, I didn't know how to feel. He pulled away. He told me to meet him back there at night.

After he left I went home, got in the shower. After washing I just sat there worrying about what was going to happen. I figured he wouldn't kill me at the very least. Given what he did earlier I felt maybe he just wanted to talk. Maybe he was confused. Whatever it was, I was worried more what he would do if I didn't show up. So I got dressed, something simple. Had dinner, brushed my teeth, and headed back over to the school. He was already there when I showed up, holding a duffle bag. Again he told me not to say anything. He said that he was very confused about a lot. He lead me to his car and we drove to his house. His parents were out, for how long I didn't know. We went up to his room where he handed me the bag, and he told me that what he wanted me to do would be a huge deal. He said that whether I did it for him or not he would stay off my back and keep everyone else from picking on me for as long as he was in school.

He had me open the bag. It was filled with women's clothes. Another pocket was full of different kinds of makeup, nail polish. He said whether I was even into that or whether I accepted his offer I could keep the bag and everything in it. I thought it over. Being raised the youngest child with 3 sisters obviously they had convinced me to play dress up with them often before including makeup. I knew I could DO IT, but this was far removed from that and I didn't even know how far he wanted to take it.

But I figured it would be okay. He wasn't lying to me, I could see from how he was acting and just from his face he wasn't planning anything else. So I nodded, accepting his offer. He looked surprised, a bit happier. I grabbed my phone out of my pocket and showed it to him, then stepped outside to call home. I told them I would be staying over at a friend's house for the weekend. That way, if I ended up staying longer I wouldn't have to explain it again and if I left early I could just say the plans changed.

I went back in and he left the bedroom. His was the second bedroom in the house with a bathroom attached, the other being his parents room. I dug through the clothes, all of it was about the right size, but mostly skimpy stuff. Not the kinds of things I felt comfortable wearing at the time, I didn't want to assume there was going to be anything expressly sexual about this. Eventually I found something nice. A skirt that actually went past my fingertips, a long sleeved top... The shoes couldn't much be helped, all he grabbed were heels. I found ones that went with the rest of it well enough though. Same with the underwear, there were literally no simple pairs of underwear in there. I settled on a thong though, a frilled one, I figured if he actually got to see my underwear there wasn't much of a point in being boring about it.

I took another shower, made sure to scrub everything and put my nails in order, condition my hair, take care of rough spots on my hands and feet. I got out, dried off, and spent another long while taking care of makeup. I didn't have to do a whole lot, my features aren't exactly masculine to begin with which was part of the problem I guess. But, it took me a while to remember exactly what it was I needed to do, I hadn't done it in years. I got dressed, I put my hair in a simple ponytail at first since it was the only hairstyle I could think of at the time. Then I decided it would be better to drape it over my shoulder instead, that looked better.

Finally I was finished, I let him back in. He sat on the bed and looked at me, had me walk around a little. Then I sat on the bed. He leaned over to kiss me again and I let him, it felt better this time. He pulled me closer and I didn't resist. He stopped for a second. He asked me if I would use my hand. I was already theoretically prepared for whatever he had planned, but I still had to take a minute to seriously decide if I was prepared to go through with it. After it became more than a kiss, it would be easier to make the next leap.

I nodded, and we went back to kissing. He guided my hand to his zipper and I opened it, then pulled out his cock. For some reason I imagined it feeling different in my hand. His was bigger than mine, but it still felt similar. He was already hard, throbbing in my hand. I stroked him slowly at first, then faster. He started running his hands over my body, up and down my back. I gasped when he squeezed my ass, I wasn't expecting it nor was I used to it.

I felt one of his fingers exploring too far and pushed his hand away. I wasn't paying attention, I knew what I was feeling but for some reason I was surprised when I noticed that I had tented my skirt. Eventually he came, managing to avoid getting it on anything but my hand and his pants. I guess I found out then that I liked men, as well, because otherwise that would have been it. I would have left. I still wasn't sure what was going on with me but I was horny then so I decided to stick around.

He went into the bathroom. I heard him pee and flush, wash his hands. I don't know what he was thinking or what else he was doing in there but when he came out he was hard again already. I tried to get him to do something about mine, but without talking it wasn't getting me anywhere. He put his hand on the back of my head, and I looked up at him. I knew what he wanted. I leaned down from sitting beside him and put my face near it slowly while I gripped the base with my hand. As I was about to put my mouth around the head it pulsed, turning the darkest purple I could imagine possible right then.

I closed my lips around the head, keeping my teeth out of the way, and licked around the head for a while. It tasted bitter, but not as bad as I expected. I could feel him lightly pushing on the back of my head, so I started trying to fit it in my mouth. I got it down a couple of inches before I felt like I was going to gag, and just bobbed from that point. He seemed fine with this, he moved his hand away and grabbed my ass again instead, that was starting to feel good.

I felt a twitch, and he grabbed the back of my head and held my head down without any warning. I gagged as he came in my mouth. He relaxed and let go. I should have been a bit angry or something, but right then I felt like I needed to clean up the mess. I swallowed what was in my mouth, same bitter taste, I licked what leaked out off of my hand. While I was doing this, he asked me if I wanted to stay the night and I nodded without really thinking.

I probably should have been a bit let down, but I figured he was about as inexperienced as I was and probably still not sure if he was prepared to touch another penis. I went into his bathroom to wash up and I rubbed off, thinking about what just happened. Used the toilet, changed into something else I'd found in the bag that was more comfortable to sleep in, and went back out. I assumed we were going to sleep in the same bed so I laid down while he went to use the restroom. I didn't expect when he came back out and crawled into bed that he would put his arm around me. It felt nice. Warm, and surprisingly safe given our past.

The next day after I woke up, his parents still weren't there. He was making breakfast, I took another shower and put on anything I could find in the bag that actually covered things. After breakfast I took a step out back to take a call. Parents checking up, I reassured them I was fine. I went back in and we headed upstairs. I actually wanted to continue, and so did he. I wasn't, however, too thrilled with what was logically the next step. I'd never tried any form of anal before, I just knew it was going to hurt. I managed to relay that I wanted him to to rub me off. This time he understood and he said he would do it if I let him fuck me.