Hi, my name is Max, this is a story from when I was 12.
"Hey Max" my friend Caleb said, Caleb is 16 and I've known him since we were both little. Our moms are good friends so naturally we became good friends to. "I can't wait to go to your house tonight dude, your parents are gone all weekend arnt they?" I asked Caleb. "yeah bro this will be fun, what time you comin over?". "Bout 6:30 il bike over, my mom wants me to have diner before I go" I told my friend. "alright peace, see you later tonight" Caleb said and then he hung up. After dinner I said bye to my mom and told her I'd be home tomoror afternoon. "hey dude I'm here" I said as I walked into Caleb's house. His parents had already left for the weekend, "hey max!" Caleb called from his room, he was most likely playing ps3, which would be what we would do for a good while during this sleep over, good fun I thought to myself. For a couple hours we played ps3 fighting each other and fighting as a team, video games were always fun I thought. "Hey max, let's play a game not on ps3" said Caleb. "alright" I thought I could use a break anyways it's 9:00 we've been gaming for 2 hours straight. "what are we gunna play?" I asked. Caleb responded with checkers. "How about we make it more interesting though?" asked Caleb slyly. I asked "how would we do that?" I asked, interested. "well, the loser has to wear girls cloths for the rest of the night!" Caleb stated. I pondered this for a bit, then thought why not it will be a good few laughs if I can win, "challenge accepted bro" I said ready to beat him in this game. 20 minutes later Caleb said "king me" as he defeated my last pice and took it for himself. "damnit" I said. "haha okay max go get dressed the outfit is in the guest room, and put ALL of it on." he said giggling. In the room I found a dark purple tight girly shirt, black tights and a matching, very shorty skirt, how odd I thought for 16 year old boy to own these, they obviously weren't his mothers. Uhg this is going to be embarrassing I thought as I started to take my shirt off i noticed another article of clothing, tight pink panties. I guess this is what he meant by ALL of them I thought, still very weird. Reluctenly I got naked revealing myskinny figure, plump little ass and my soft dick, i had begun to think about girls because of the panties and then there was a twinge in my dick, I thought no I cannot get hard right now, I have to go and be near Caleb in this outfit. I picked up he panties and slipped them on, very tight I thought, then again most of girls cloths are. After the panties I got into the black tights then put my new purple shirt on after all that there was still my skirt to put on, prolly good I thought, my dick feels revealed in these thin tights the skirt was jus clipped on and the shirt slide over the clip part perfectly. The skirt is was very short I felt like one of the girls I see in anime porn when I'm searching online. I walked out of the room fully changed and presented myself to Caleb. Much to my surprise he didn't burst out laughing, instead he was just staring at my body. Finally he said "did you put your panties on?" he asked "yeah dude, they feel weird" I said. "show me" he demanded, turning so my side was facing him as to not show the perfect outline of my dick, even soft in these tights is easily. Noticed with my skirt up I pulled up my skirt and pulled down my tights just enough to a show a bit of pink. "Very good" he said "you look very cute" I thought this was wierd. "now what?" I asked. Caleb got up from the table and walked over to me and lifted up my skirt directly in front. I pushed his hand way and tried to hide my junk as best as possible with this tiny skirt, "what the hell dude, u can see me perfectly though this without my skirt". "I know slut" I was very confused, he took out his phone and showed me a picture of myself in this outfit. "tonight your going to be my slut or I'm going to show his to everyone" with that he pulled up my skirt once more and then began to message my dick and balls, I backed up and tried to push him. "alight max il just post this in Facebook.."he threatened "no..." I said realizing u had no choice "il be your slut". " good because you look amazing in that outfit" he said rubbing my plump 12 year old ass. "okay let's go back to my room" reluctantly I followed him "okay max la down on my bed, I'm going to turn on some porn for you to get hard to, I know what you like" he turned on his tv and what I saw was a video of an anime girl in an outfit not far from my own fingering herself. This was humiliation at its worst, I couldn't not get hard. "good" Caleb said as he lifted my skirt up and saw a bulg forming. He pulled my tights down just enough to reveal my hardening dick in pink panties he mAssaged it a bit and then pulled my panties down just enough so that my dick and balls were exposed, I had no hair around my dick and he could see everything, I felt so weird. "jack off" Caleb demanded. "what??" I said surprised. "do it or il post this" I felt humiliated but I would feel worse if that picture got out, so I started to jack off to the porn as Caleb watched me. I pumped my dick and soon I came all over my hand he told me to wipe it on the inside of my panties. I did then Caleb came over and slid my panties back up, now my soft dick and balls were covered with my cum. He massaged my chest and dick and said "good slut, now turn over". Still laying on his bed I turned over my ass barely covered by my skirt. He came over and lifted my skirt and once again pulled down my tights to reveal my panties then he began to massage my ass. He pulled down his Pants and took some lotion and put it in his dick, which was very hard by now, I thought he was going to jack off on me. After he covered his dick in lotion he walked over to me and rubbed my ass again then he pulled my panties down and spread my legs then the sharpest pain I've ever felt. "AHHH" screamed as Caleb slid into my virgin ass. "shut up slut" he said, I did as I was told. After a few painful minutes I heard " I'm cumminnggg" he yelled then I felt a flow of warm cum go into me. After a few seconds Caleb's dick began to soften and he pulled out of me pulled my panties back up, while his cum was still slowly sliding out of my ass. "good slut" he said as he sat down and began to play games.