Date: Tue, 10 May 2005 06:11:05 -0700 (PDT) From: milo emit Subject: Jessie bi adult youth Jessie moved into the neighborhood when he was 8. Tall skinny kid almost too skinny. He had short spiked dark brown hair. Brown eyes, little turned up nose on a round face. He had a high squeaky voice whenever I got him to talk. He seemed very shy and would never talk to me. In fact most of the time he would turn away from me as I walked by on my morning walks. I time my walks to the times he got on the school bus. He was in a lot of my wet dreams. When his dad was around he would be very talkative. Once while talking I ask him if he had any girlfriends. He said man that's gay. I was really confused by that statement till about a year later I was talking to his mom and she started talking about Jessica. I though that was the name of their newly adopted child till I realized they adopted a boy. All at once it hit me Jessie was a girl. The new adopted child was 4. Two years later they gave birth to a little boy of their own. I soon realized they wanted boys. Though they loved Jessie and didn't mistreat her, her parents lavished most of their time on the boys, especially the youngest. The children are now 11, 6, and 4. About this time Jessie's hair started to grow long and she started dressing like a girl. She's still was a tall skinny thing with a high squeaky voice. It was hard to start treating her as a girl. I acquired a Golden Retriever about thee months ago and he goes with me on my morning walks. The first time Jessie saw him she fell in love with him. She is now my best friend. She talks me to death till the bus comes and so does her little brother Josh. Josh is very husky for his age with a cute round face and fat cheeks. He's not fat in any way for his body is tight as a board. He has large hands and very long fingers. They look a little out of place on him. Once last fall he was playing in the sprinkler in my back yard. He had a tight little bikini swim shorts on. Once when he bent over I pulled his pants down off his round little ass. He grabbed his ankles and looked between his legs back at me. He was giggling. His butt cheeks were clenched so tight I don't think I could pry them open. A second later he relaxed and ask if I was going to spank him or pull his pants back up. I could see his little ass hole. It was the same color as the rest of his bottom and barely wrinkled. I said I'll do more than spank you if you keep showing me that little hole. Josh giggled and pulled up his pants running saying you'll have to catch me first. When he turned around I noticed his little dick was hard and seemed large for his age. He seemed disappointed that I didn't chase him and went back playing. About that time his mother showed up. He gave me a little smile saying maybe next time and left with his mom. Jessie spends a lot of time with me when I'm playing with the dog in the back yard. I have a glass door to the deck from my bedroom. I had just finished my shower when Jessie walked. I was pulling my underwear up. I had my back to her and didn't realize she was coming in. It startled me and I turned around. with my underwear just below my balls I said Jessie! do you always come in a man's bedroom when he's getting dressed. Nonchalantly she said sure all the time when my grandfather visits. He say's it's alright as long as I don't tell my parents. I noticed she gave my privates a good look then sat on the edge of my bed and started her never ending talk. I finished dressing and she acted like it was an every day thing. I was a little flushed. Later that day her mom showed up and we had coffee and talked. I had become good friends with Jessie's parents, but her dad wasn't home much. During our talk Jessie interrupted us asking if she could spend the night with me since Josh was staying with a friend. I didn't have a clue but her mom said that's fine with me, then looked at me saying if it's alright with you. I threw up my hands and said sure I have an extra room and bed. Jessie's mom had confided in me once that her dad really wanted the first to be a son and treated Jessie like a boy till the boys came alone. I think they jumped at any opportunity to have her out of their hair. Jessie left with her mom only to show up after supper with her night things in a little pink suitcase. We watched TV and during commercials Jessie never stopped talking. She told me about her grandfather and how she would sleep with him sometimes when he visited. I said with a twinkle in my eye your mom don't care you sleeping with a man. She said he's not a man he's my grandfather then giggled and said you know what I mean. I laughed. She said my parents are always gone when I sleep with him. I promised him I wouldn't tell. About 10 o'clock Jessie said isn't it about time for bed. I had to agree so she went to the bathroom to shower. I turned down her covers and went to my bedroom, undressed and put on my robe. I waited till she was done so I could tuck her in. She came out of the shower with a big towel around her. She went to her bedroom turned out the light and came back to my room with her night things. She said I'm sleeping in here tonight. She pulled her towel off facing me as if it was the natural thing to do. From the waist up she looked like an young skinny boy. No hint of tits yet. From the waist down she was all girl. She had a fairly big puffy pussy that was just starting into puberty. Not even any fuzz yet. Long skinny but strong looking legs. She threw the towel in the corner and pulled a short night dress on without any panties. She jumped in the bed and under the covers. She laid on her side facing my side. I turned out the light removed my robe. I had skimpy underwear on and it wasn't dark enough to hide the fact that I had a hard on with the head peaking out the top. I crawled in bed and laid on my back. Jessie scooted next to me still on her side and put her head on my shoulder. I had my hands behind my head and removed my left hand and laid it down her smooth innocent back. I pulled her night shirt up and she removed it. She was so soft. I lightly touched her from her shoulders to the crack of her ass. I knew she was mine to do what I wanted, but I decided to be very careful just incase this was all innocence. Jessie whispered in my ear. You know what I do to my grandfather? I said no what. She placed her hand on my chest and rubbed from my neck to my navel. She said wow you don't have any hair on your chest like grandfather. I said I'm sorry. She said no that's ok I like it better this way. Jessie got quite for a moment still rubbing my chest and stomach then said you know what else I do? I said no what? Jessie put her head under the cover and in one swift move her hand slid down my body snagging my bikini underwear. As my hard dick came free from the material her mouth was sucking the top third of my dick. I about passed out. Just as fast as she started sucking me she stopped, came from under the covers and ask, you like that? I said yes I about died. Did your grandpa teach you that. She said yes and sometimes he shoots in my mouth, but I don't like that much. I ask, does he ever do anything else to you? She said yes all the time. As I rolled toward her, Jessie laid on her back and opened her legs. I though that was an invitation so I laid on top of her. My dick was pressing along her young innocent pussy. I gave a couple gentle pumps and felt her lips spread along my shaft. She was really wet. Her slick gooey fluid coated the length of my dick. Jessie said your just like my grandfather. My dick and heart was throbbing with excitement. With every throb of my dick I could feel my pre cum mix with hers. Jessie's arms were around my neck. Her knees came up and clamped against the sides of my thighs. I reached between us and pushed my head hard against her extended clit and Jessie pushed hard against my throbbing member. While holding my dick head tightly between the crack of her pussy I pulled back till the head pushed passed her young opening. Jessie gasped as I opened her up slightly. I took this as and invitation to penetrate her and on the next pass I hesitated as she once again gasped. Instead of pushing back up her slit, I applied a little more pressure at her little opening. My swollen dick head slipped into the tight opening enough to trap it in place. I removed my hand and pushed a little more. I felt the head start to gain entry just as Jessie tightened up and pushed up against my chest with her hands. She went rigid and it felt like her little pussy was trying to expel the large object trying to invade her body. By doing this she caused my blood engorged head to slip past her tight entrance. I felt her opening close around the back of my flared head wrapping tightly around the smaller part of my shaft. My dick was throbbing with pleasure. I kept getting the sensation of cum being forced out of my dick and realized I was so hot with pleasure that what I was feeling was pre cum forcing it's way past the opening I was trapped in. Jessie got a frightened sound in her voice as she pushed up against me. I came up off her body but she kept her knees tightly against me then her legs went around my back. With a shaky voice Jessie said, Grandfather said I can't do this yet. He said I was to small. I said he never put his peter in you? She was still shaking and her eyes were like large saucers. She said he just puts his finger in there. I said I won't put anymore in, but you have to relax. Does it hurt?. In a squeaky voice she quietly said no. I said if I pull out now it will hurt so just relax and I'll pull it out in a minute. I know I lied but I had to have and excuse to stay in this young innocent child as long as possible. I think she started to breath again and I felt her body relax, but she kept her legs around me. I laid back over her keeping my dick in place. I giggled and said you are so tight what are we going to do if I'm trapped in this position then tickled her in the ribs. Jessie jerked and laughed and I was half way in her. I though the top of my head was going to explode. My dick throbbed and swelled to max. Jessie stopped in mid laugh and went tense again. Her breathing was a little quicker. She said you went in all the way. I said not quite. She reached between us and felt the exposed part of my dick. She said it feel like your all the way in. I said does it hurt. She seemed to think about if for a moment and said no. A moment later she said it kind of feels real good. I said if it feels good why don't I leave it in you. Jessie said it's making my body feel good and tingly all over. Her breathing was becoming very heavy now. I said I'm going to slowly put the rest in and if it don't feel good I'll stop. Jessie just sort of held her breath and I started to feed her the last few inches of my 6 1/2 inches. I was delighted when I was all the way in, but knew her little body couldn't take another millimeter. My dick was swollen to the max as I pushed in her. I could feel my engorged head push her hot tight tissue open as I went deeper. Now that I had gained complete access to her innocent sex I relaxed and my dick deflated some. Jessie took a breath. I ask how does it feel? Jessie said are you all the way in? I said you got it all and kissed her forehead. She said it feels like it's a long way in me. She paused then said it really feels good. I said it will get better. Hang on I'm going to move around some. She wrapped her legs tighter around me and put her arms around my neck. I slid my legs off the bed bringing her to the edge. I said let loose with you arms and as she did I stood up. I reached over and turned on the lamp next to the bed. Jessie pushed up on her elbows to see where we were joined together. She said wow you really look big in me. I said it is big in you. I'm glad it didn't hurt. She said it didn't hurt at all. I said loosen up you legs some. She let her legs go and her knees came away from me. Her knees came back toward the bed and gaped open. I placed my hands around her thin thighs just above where we were joined and took a long slow stroke. Jessie took in a long deep whinny breath. Her head flopped back on the bed and her hands griped the sheet under her. I ask did that hurt. She gasped out no! no, it was the best feeling I have ever had. With my dick in this young innocent child feeling her tight sleeve massaging it's length causing it to swell and relax at the rate of my heart beat. I knew I couldn't last much longer and I didn't want to cum just standing still. I wanted to be moving in her feeling her wet tightness sliding along the length of my dick. I wanted to watch the passion in her face as I moved in her. I gripped her thighs tightly and took a long gentle stroke. I was shaking so much I almost came dislodged. I pushed back in just as my head came free. The head started to push up pass her opening then popped back in with squishy sucking noise. For an instant I though I might have hurt her. Jessie's head tilted back and her chest came up off the bed some. As I took a couple more stokes she grabbed her breast like she had some tits and massaged them. Her breath was fast and raspy. I was plunging in faster now. Pushing in and up bringing her little ass off the bed slightly then instantly pulling back out. It was like knocking the breath out of her with each plunge and pulling air back into her body as I instantly pulled back out. I lost count how many times I pushed in and out of this little girl under me. I was mesmerized at the look of pleasure displayed on her face. I watched her body react to the movement of my dick invading her body. Her hands working over her little nipples and watch them get larger from her touch. I didn't think the pleasure could get any more intense as I was about to climax. I was wrong. Jessie climaxed. It was intense. She arched her back. Her breathing became more urgent. Her squeaky voice became more of a shrill. Her velvety sleeve became so tight it almost trapped me in place. I had to apply more force to move in her. Just as I climaxed I felt her pussy start to throb like my dick does when it ejaculates. It felt like a wonderful milking machine on my dick sucking me dry. I pushed and relaxed with each throb of my climax. Then I just pushed deep and road the final throbs of my pleasure. Her pussy was hot and throbbing as she slowly came down from her climax. My dick was also throbbing. It was so hard it hurt. It felt like my dick head was twice it size. I held still panting like I had ran a marathon. I noticed Jessie was panting just as much. Her face was flushed and sweaty like mine must be. Finely she opened her eyes and we made eye contact. She smiled and ask, does it always feel that good? I said yes if done right. Slowly the throb in my dick eased and started to deflate. Jessie also relaxed. We stayed joined until I became to soft. Jessie was up on her elbows again watching between us. She tightened up and it looked like a big long soft sausage slip out of her. Even though I was soft, she felt tight. We giggled at the sight. We cleaned up and she watched the cum flow from her as she stood in the bathroom. We slept good that night. I held her smooth young body against me till I fell asleep. The next morning I was rock hard and spooned up against her. We would had joined again. she said she didn't hurt but her pussy felt really tired. I'm sure it did. We just played with each other. When I came it was in her mouth. I tried to stop her knowing she didn't like her grandfather cumin in her mouth. She did it any way saying she liked it better from me. She looked different after that. She doesn't talk so much. She likes to cuddle when we are alone and soon we hope we can sleep together again. Milo