I knew Timmy since he was 10 and I was 12. As we grew up we played together and hung out a bit. I was 16 and had fucked a girl 3 times and she moved away. I tried to get some other girls, but it was summer and none really from our neighborhood. I had fucked, and cum in the girls mouth twice and in her pussy once, and the other two fucks I pulled out and shot on her bald pussy. I was horny and now I knew what I was missing by not having someone to fuck or suck my dick. In the years Timmy had gotten chubby, and very insecure in his demeanor. He was kind of feminine really, not outwardly but around me I could see it.
He was 14, I was 16 and we were swimming in our pool, no one else was home, we went into my room. I pulled out of my trunks and started drying off. He kept his on. I reached over and pulled them down “No need to be shy, we’re both boys right?” I said. I reached to his very small microdick and flicked it a few times. “Does it get hard?” I asked and he said yes, and turned away from me. Both of us naked now, I pushed up against his ass with my hard cock, it went between his soft butt cheeks and was riding up the crack. I reached around with one hand and grabbed his microdick and the other was playing with his tits. Now his “pecs” were literally the size of almost B cup girls tits. I was playing with one and flicking the nipples, pinching it. He didn’t say anything. I started moving up and down in his crack. His soft round ass cheeks were feeling really good. I started jacking on him with only 1 finger and thumb, it didn’t need anything else. I think he probably got 3 inches hard, maybe! “Oh shit, it’s about to cum” I told him holding his hips with my hands while I pumped up and down in the crack of his ass globes. “Oh shit man, that feels so fucking good, fuck, fuck, yeah I’ll do you after I finish, man I can’t stand it, I have to do it” I told him as I was shooting a couple weeks load of cum all over his back and butt. I rubbed some of it on his ass crack more, then put the rest in his mouth. “No, don’t, I don’t want to do that” he told me. I made him take it in his mouth and swallow it. Then I sat him down and jacked his little one till he shot.
After that we were watching some porn, I purposely put on chubby girls and women getting anal sex from young guys. I got hard again, he was rubbing his micro. I started playing with his tits like the guys were doing to the women, I started sucking on them while fingering his little dickie. I laid him down and jacked on him. His cum shot on his stomach, and I took it all. I think he thought I’d swallow it like I made him do with mine. Instead I rolled him over and rubbed it all over and into his rear hole, and then the rest I used to lube my cock. He just held his breath not saying anything to me about not doing it. I gently and slowly inserted my 6inches into his ass. Holy shit if I knew how good fucking ass felt I’d have made that girl do it too. It was great. Since I’d already cum it took me about 25 minutes of fucking Timmy’s ass, reaching under him and playing with his titties before I came. I was moaning at getting fucked, and seemed to moan more when I’d pinch and roll his nipples. I shot as deep inside him as I could then kept my cock inside him and slumped over on top of him. I was whispering to him and telling him how good it made me feel. “I like letting you feel good” he told me. “You can do whatever you want with me, anytime. I’ll do it OK?” he said again. “What if I want you to suck on me and take my cum and swallow it?”. “I don’t like the taste but I’ll do it for you” he told me. I pulled out and told him to stay like he was and not move while I got dressed. Then I let him get dressed.
I just sat and watched him. “Did you mean it when you said you’d let me keep having sex with you?” I asked. He did, anytime, anyplace. After two weeks, twice a day minimum of getting my dick sucked, or fucking him in his ass, I even titty fucked him making him push them together with lotion and fucked him that way cumming into his open mouth. He was enjoying it. He really enjoyed being the “girl”. I would call him Tammy when we were naked. Then I snuck out and bought some big panties, and a bra in his size, then added thigh high stockings. He resisted but some sucking on his tits, and jacking his little cock turned him around. His mom thinks it’s great that I let him hang around me, my mom is glad that I am taking him “under my wing” as she called it.
Little do they know I’m just using him/her to fuck and get my nut. He likes it, I like it, and Tammy has grown to be an excellent cocksucker and a really good fuck with nice tits to play with when I fuck her missionary.
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