Date: Tue, 15 Sep 2009 16:56:07 -0700 (PDT) From: milo emit Subject: Boy in Mini Skirt A few years back I did delivery work for a friend while he recuperated from a serious accident. I delivered office supplies and on this occasion I was making a delivery to a house that had a small business in the back. I started to knock when I noticed a young boy in a mini skirt through the open door. He was standing in front of a full mirror with a pair of pink silk panties down to his knees. He was tucking his totally hairless dick back between his legs making him look like he had a vagina. I realized I knew this boy. I had seen him in school and heard about him from some of my teacher friends. He had also visited me a couple times. He was fourteen but very immature for his age. He was very feminine acting and had been sent home once when he wore a full length dress to school. He looked very young for his age. He wasn't fat or even pudgy but he had very little muscle tone. His body had the texture of a girl. His skin looked like it had never seen the light of day. His ass was toward me and look very inviting. Soft round with a wide crack. When he had finished positioning his dick, he did look like a young girl with a hairless pussy. He reached for his pink panties when I interrupted him. I said, hey little girl aren't you a pretty thing. He jerked up his pants and turned toward me. I could see he was about to cry when he recognized me. I said hi Jonathan you do make a very pretty girl. A smile came to his face and called me by name saying Hi. He said I had scared him. I said I was sorry then looked him all over. His mini skirt barely covered his pink panties. I said your are pretty I sure would like to see those pink panties again. With a big smile he lifted his skirt as high as it would go. The panties were at least a size to small and the way his dick was tucked he looked like he had a little pussy pushed against the silk panties. He turned around and his round bubbly ass pocked out tightly wrapped in the panties. He wiggled at me then said I bet you would like to feel my butt wouldn't you. I said you bet I would. Jonathan's Uncle allowed him to wear girl's cloths at home and he went to yard sales to purchase what he wanted. He lived with his bachelor Uncle. His dad and mom gave him up at a couple years earlier after he had been kicked out of school for wearing girl's cloths. His mom always kept him in girl's cloths wishing he had been born a girl. I had talked to Jonathan many times at school when I made deliveries. He even stopped by my house a couple time. Once he sat on my lap on the back deck and pulled his pants out so I could see his panties. He loved it when I commented how nice they looked and told him he could show me his panties any time he wanted. Seeing him with his mini skirt and pink panties was the first time I had seen him since he was twelve. Here I stood in his Uncles office with Jonathan showing me his pink panties. He said we could go to his bedroom and I could play with him. He led me to his bedroom and it was decorated like a little girls room. I ask where his Uncle was and he said he was away for the day. He stood in the middle of the room and slowly slipped his skirt down and off. Then he took off his halter top and stood in front of me with just his panties on. His body was thin and soft looking. He had a baby face and most people thought he was around 10 or 11. The only hair he had was the light brown hair on his head. His Uncle made him keep it short so his really looked like a little tom boy. His dick was outlined in the silk panties then he turned around and when he turned back he had tucked it back in between his legs. I said hey little girl that is sure a cute little pussy you have. Can I play with it? Jonathan went into his act acting shy. His voice was already high, but he made his voice sound more girly saying I don't know maybe. I said I would make it feel really good and he giggles in a girly way saying well ok if you want. My dick was about ready to rip out of my slacks and I'm sure he noticed. I walked up to him and ran my hand over the mound where his dick was tucked. I felt him shiver then giggle saying I was naughty. I hooked my fingers in his panties and tugged them down. They were a little hard to get down with his legs tightly holding his dick in place. I got them down and off his feet then went back fondling his little pussy. I could tell he was getting excited because his dick shaft started to fill with blood, but still it looked really cute how he kept it in place. He surprised me when he said you want to stick you big thing in my little pussy. I just nodded yes. Jonathan turned his back to me releasing his dick, but I couldn't see it as he got a tube of KY from his night stand then kneeled on the bed tucking himself back in and laying down on the bed on his back. I took my clothes off as he watched intently. He got a big smile on his face when my dick popped free from my underwear. I was hard and it stood straight out. I got on the bed kneeling over his legs. Jonathan squeezed a big glob of KY on my dick and smeared it around. He then said just put it in here and he pointed to the space just below where his dick was tucked. Jonathan had thick soft thighs and I laid over him and he guided me to the spot he wanted. When I pushed it was like pushing into a very tight hole and I forced my dick along his dick and between his thighs. I could feel his dick throbbing and it was hotter than his thighs. Jonathan had given up the pretense of being a girl as he was talking normally now just enjoying the feelings he was getting. He said no one has done this to me since my dad left. I pulled up like I was fucking him and he squeezed more KY on my dick. He stayed tight as I stroked a few time then said I know a better way to do this. Jonathan ask how so I pulled out and got up then pulled his legs straight up in the air. In this position I could see his dick head throbbing between his legs. It must have been painful being trapped like it was, but Jonathan kept his legs tightly closed even crossing his ankles. I got up close and rubbed my slick dick head against his little circumcised head and felt him shiver with pleasure. His dick was trapped so tight his head was swollen and purple. The opening was gaping open with a bubble of pre cum puddle just inside and wondered if this hairless pail little boy could cum yet. I pushed my throbbing meat up along his dick feeling the heat and stiffness of his dick then pushed between his thighs. When I was all the way in he said wow this is better then grabbed what he could of my dick. Every time I would push back into him he would rub his hand over my sensitive head. His legs were quivering every time I pushed into him. I pulled back till the head touched his purple head and moved it around some then moved it down till I found the tight little opening of his ass. I moved back to his dick then back to his ass hole. The third time I did this I applied a little pressure and my head slipped right into his ass. The heat and pressure around my dick was intense. Jonathan never made a sound or moved a muscle. He just went limp. His legs sprayed open and his dick sprang free. His dick was a respectable size for his size but small for his age. It bobbed up and down as I pushed all the way in. Jonathan's face was expressionless. He just laid there limply as I moved all the way in. I ask if he was all right but he didn't move. I said if I'm hurting you tell me and I will stop. Still nothing. I held my dick all the way in him for a few moments hoping he would say something. His eyes were wide open looking nowhere. The best response I got from him was when I took his dick in my hand and started to jack him off. He took in a sharp breath and his ass tightened even tighter around the base of my dick. The base of my dick is very sensitive and the pulsing of his opening around that area brought me to climax right away. His ass was very tight even in the relaxed state he was in. Jonathan's body shook a couple times and he shot one squirt of thin milky cum and then a few bubbles dribbled out over my hand. He breathed out and went totally limp again. I was shooting deep into him and when he felt my dick jerk around inside, he got a worried look on his face. I slowly recovered and pulled my aching dick out of him. His ass hole closed up tight as I came out. I got off the bed wiping the cum and KY off my dick with his silk panties. I said you better go clean up and get dressed. He got up and headed for the bath room holding his butt as he went. When I was ready to leave he came back into the bedroom dressed in boy's cloths. He still looked strange but I had to leave. He just stood there silently as I left him. Near the end of the summer I had to make a delivery to his house again. I knocked at the back door and Jonathan let me in. I sat the packages down and looked at Jonathan. He still had that baby face on him, but he had grown. He was taller and no longer soft looking. All he had on was a pair of levies. His chest was tight and his stomach was well tones. I said wow you've grown and he smiled and lowered his head. I guess he was taking track and working out over the summer. I ask where he little sister was. He said he didn't have a little sister. I said the last time I was here a little girl was here and let me play with her. Jonathan got a big smile on his face looked me in the eyes and said she don't live here anymore. I said that's too bad for I really had a lot of fun playing with her. He said well it's just me now. Then ask if I wanted to go back to his bed room. I followed and when I entered his room I noticed he locked the door behind me. His room was different. It was still a little feminine, but was more like a boy's room than before. There were no girl's cloths and it was not as neat as before. When he turned to face me I noticed his pants was unzipped and he had a hard on. It was barely visible through the opening of his pants. I walked up to him and cupped his dick saying I like playing with little boys as well as little girls. He got a big smile on his face and I unsnapped his pants and they fell to the floor. Next came his white briefs. He wiggled out of them and his dick popped out all five inches of it. He proceeded to undo my slacks as I took off my shirt. He assured me his Uncle was out for awhile and we had plenty of time to play around. I wrapped my hand around his thin dick as it throbbed and bobbed in the air. His dick was extremely hard. It filled my hand nicely. His head was flared over the shaft and tapered to a blunt end. The hole was a slit that opened wide when I pulled back. I could feel a little fuzz at the base of his dick but other than that he was hairless. His balls hung in a soft sack and moved up and down as I stroked him. When I was necked he wrapped his hand around my dick as well and we stood facing each other stroking each other. In almost a whisper he said you want to put it in me like you did last time. I said yes but I thought I might have hurt you last time. He said I hadn't but he was really embarrassed that I would want to touch him back there. He said it stung a little when it went in but felt really good afterward. He said he didn't know boys could do that to each other. He said he always wanted to know how it felt for a girl to get fucked and when I did it to him he figured he didn't have to be a girl anymore. I said OH you get fucked in the butt all the time now and he said no just by you. He pulled away and went into his bathroom coming back with some KY. He got on the bed and laid like he did last time but I got him to kneel next to the edge and pushed his tight little ass back and down to the level of my hard on. I coated my dick generously and when I got behind him he opened up his cheeks for me. He still had a deep crack and his opening was puckered in slightly. I put my head to his hole and when it touched Jonathan said oh yes. I started to push and he relaxed letting my head slip right in. He let out a little groan then said that feels really good. He made little whimpering sounds as I pushed all the way in. When I took hold of his skinny hips and pushed hard causing a grunt from him he released his cheeks and put his arms up over his head. As I pushed in I could feel is tight opening stretch around my shaft and slide down toward the base. His ass hole kept throbbing around the base of my dick. He would tighten up then relax then do it all over again. His body would quiver then relax. I reached around him finding a very hard slimy dick. He had coated himself with KY and as I smeared his precum over the head and shaft it made it even slicker. I stood behind him pushing my dick in him as deep as I could. Jonathan started to make little hunches back and forth till he was working a couple inches in and out. He said oh man I have never felt anything like this and started to push back and forth moving more in and out of his ass. I started to pump his dick realizing I couldn't last much longer. I felt him tense then he said I'm almost there. I started to move my dick in him and he stopped moving letting me do the work. I was coming fast. I felt his dick swell and spasm squirting out thick globs of cum. I couldn't hold back any longer. His ass throbbing around my dick causing a massive climax. I fell on top of him causing him to fall to the bed. I almost came out but was able to stay with him and jammed my dick hard into him as I fell on top of him. He let out and oh shit then started to laugh. I knew I hadn't hurt him and started to tell him in between gasps of air that he had the best ass I had ever fucked. He just said oh ya and wiggled his ass pushing up against me. I held him tight as I slipped out of him with a groan. We both went to the bathroom and he cleaned me up then himself. He hugged my necked body and didn't want me to go when I said I had to. Slowly he released me and we dressed. He gave me another hug as I went out the door. I didn't see much of Jonathan through the years. He is 18 now and stopped by the other day. He was tall and lean. His voice has deepened some and he had a nice tan. We sat on the deck and talked. He said he had a boy he liked a lot but didn't think he like him in the same way. I ask what he meant and he said he could fuck him any time but he wouldn't fuck back. He then in a soft tone he said you're the only one that has done it to me. I said would you like to do it now. He got a big grin on his face then in a teasing way said I though you only like little girls and boys. I said come on little boy lets have some fun. Fun we had. His dick was now six inches but not all that thick. He came in me twice then I got him on his knees and made it last as long as I could. He shot again as I came in him. Jonathan started collage this fall. He sent me a picture of his boy friend. He looks a little feminine but he assures me he is all boy. Milo