My Girly Boy I

Recently, I was dating a fairly attractive woman. In the course of getting to know her, I also got to meet her son. The moment I saw him, I knew he and I would have to be lovers. He was the absolute picture-perfect, naturally happy girly boy. He had long brown hair, a nice, sun-kissed, brown tan, true brown eyes, and was thin and just perfectly proportional in every way.

He is easily the most attractive person I've ever seen. Just unparalleled, androgynous beauty. Also very intelligent and athletic.

When I first saw him, I very truly thought he was a flat-chested girl with cute braces, which was also very arousing. When I started talking to him, and realized he was a girly boy, it became even that much more hot. To add to his androgyny, he liked wearing girls' clothes and colors typically associated with girls. Even the backpack he wore was very girly. It made him divinely attractive.

Being who she was, his mother had no issue with he and I spending lots of time together. Slowly but surely, as I did with my ex's niece, I spoiled him and became his best friend. He wanted to be with me more than anyone and I even comforted him once when he was crying - holding him in my arms. He'd even get a little jealous when I'd talk to other people when we were together, which was incredibly adorable (he'd act sassy and just stare at me with his eyebrows raised).

When we were together, we'd have a lot of fun engaging in various activities, like gaming and as well, exercising. We had an instant connection and he immediately trusted me and began wanting to be physically more and more close. I was definitely his new Daddy.

With him wanting to be closer and closer to me physically, it became apparent that not only was he very naturally, beautifully girly in terms of his appearance, he also had a naturally beautiful girl personality, too. As he trusted me more and more, he began acting his true, girly self around me more and more.

One of the turning points was when he and I were done hanging out for the day, and as I was leaving and waving goodbye, he flicked his long and beautiful brown hair towards me, jutted his should in my direction, winked at me, and blew me a kiss. I blew him a kiss back and he got really excited with a big smile and went inside. This beautiful gesture of his made my dick leak a little precum, beyond the constantly hard dick I had when I was around him already. It was hard not to get out of my vehicle and just take him upstairs to make love then and there, but I had to be patient and wait for some really good alone time with him and his mom. Regardless, I know the first chance I had after driving home, I jacked off and produced a huge load while thinking of him. It was like this after every time I would hang out with him: My dick was basically stuck in an erection for him and I had to rub it out until I came for him.

He's still easily my number one fantasy material. It's very easy for me to cum just thinking of him, even without porno.

Anyway, the next time I was with him, things felt very different. I think at this point, we both were fully ready to escalate our little relationship. I sat down next to him, to play a board game with him, and slowly but surely, he kept scootching closer and closer to me, until my knees were pressing against his thighs. He also began placing his little hand on my shoulder when he wanted to tell me something in particular, just like a girl would. Needless to say, this was making me as hard as my dick could get, and leaking precum out of arousal. So, I moved in closer to him, in my first real advance on him. When I did, he raised his right leg and placed it on my thigh. I reached over and gently gripped and jerked my dick, then grabbed his leg and pulled it closer to me, so that my dick was pressing against his leg.

At this point, were were almost cuddling and I decided to test the waters with him a little further, so I gently guided his long, overhanging hair so that it was now resting over his ear. I wanted to see his beautiful, beautiful face. This made him smile as we were playing, and so I leant over and ever so gently kissed his cheek. When I did, he took a breath and grabbed my right arm, and so I kissed him gently two more times on the cheek. His hair smelled so good, like shampoo and sweat. He smiled very happily and again did his cute shoulder hair-flick at me, though just a little slower this time and let his eyes linger on me. I sat back and just watched him as he played. At one point, he rose his right arm and ran his fingers over my lips and I reached over and gently grabbed and slowly tugged on his little dick, which was clearly hard and visible through his tight capri pants. As I lovingly jerked his dick, he grew quiet and spread his legs wide and I leaned in and French-Kissed him very deeply. I could hear his mother coming and so things had to come to an end since we were going somewhere, but I knew then that we were both ready to be lovers. Needless to say, before going out with him and his mother, I went straight to the bathroom to jerk off and cum. I came immediately, and wished I could help him cum as well.

This intimacy escalated over the next couple times I saw him, where we became totally comfortable with each other. It also added a very sexy dynamic to the sex his mother and I would have. I began talking about him while I was fucking her, and this made me clearly even more excited. I'd mention he takes after her, in terms of feminine beauty (which was true, but just as a girly boy). I'd also tell her how beautiful and attractive he was to me, then even began telling her that I wanted him as a lover as well. She would just tell me that her son was lucky to have someone so caring as me, to want him.

One of the sweeter experiences I had with him was we were once sitting together and eating. His mother was with us. As he was chewing, some of the chips he was eating broke apart and some of it landed right in his lap, on his sweats, right on his dick area. When I saw this, I reached over and began picking up the broken chip pieces and made sure that my fingers rubbed against his dick. Without any hesitation, he allowed for me to put my hand in his crotch again. He just looked down at what I was doing, smiled, and kept eating. His mother also watched us and smiled. I ate the pieces that had fallen in his lap. He also began making a routine of resting his hand on my thigh when we'd sit next to each other, and as well, he'd rest his foot on top of mine. In these moments, I did notice his constant erections through his capri pants. Whenever I had the chance, I'd look for chances to touch his hard dick or move his hand so that he could touch mine. He grew to love resting his hand on my aching bulge, playing with it and feeling it. I could tell he loved it and little precum stains would be present on both our pants/shorts.

The best, first, most sweet sexual moment was when we were going to watch a little TV together. It was in the early evening. We all got on a couch and he rested his head in his mother's lap, and he put his feet (in sneakers) on my lap. Having a strong foot fetish, and fantasizing to no end about worshipping his feet, I began undoing his shoe laces.

Once they were undone, I pulled his little feet out of his cute sneakers and put his sneakers to my nose, and smelled deeply. He said something like "Ewww, that's gross!" and laughed and smiled at this, and playfully pushed his toes and feet against my face. I tickled his feet a little but then held them against my nose and mouth, and kissed on them gently. They were really stinky and sweaty...smelling like pure Heaven. I took his other shoe off and rested his other foot against my erection. He began playfully pushing his little foot against my dick, and I pulled his other sock off and began worshipping his foot. I smelled it, licked it, kissed it, and sucked on his toes. They tasted like pure Heaven, I still remember it vividly.

I briefly made eye contact with his mother - who had been running her hands through his hair - as I was overcome with lust, and she watched me as I ran my tongue between her son's toes and he played with my dick with his other foot. He had sloppily painted his toes an aqua color. As this was happening, she said she needed to go upstairs, leaving her son and I alone. Neither of us said anything to her, as we were completely enraptured by each other. Once she left, I turned off the TV and switched his feet out. I wanted to lick every drop of sweat off his other foot, and I rested his now cleaned one against my dick. As I began worshiping his other foot, I grabbed his little hand and helped him sit up. I told him to help me take off my pants and he did, so now I was just wearing underwear and my fully erect dick clearly visible through my briefs and inches away from his face. He couldn't take his eyes off my bulging cock.

Here, I grabbed him and gently sat him in my lap. I took the base of my dick and aimed the head to be right between his ass cheeks. I pressed him down against it and we sat like that for a few moments, just him in my lap and us smiling happy at each other. I leant over and kissed him on the neck, then gently licked his neck here and then, then asked him how he felt. He said he felt really happy, and that he felt really good. I leant over again and gently kissed his cheeks and his lips. I began kissing his soft lips again and again and gently began letting my tongue against his lips.

At this time, his mother returned and sat down again on the couch near us, and watched us intently.

After tonguing his lips, I I began to push my tongue into his mouth, parting his tender lips. He immediately put his tongue against mine, and we began French-Kissing for the second time as I started fondling his small, hard dick. I loved running my tongue over his braces. It was so exciting to really feel his dick and braces and I was happy to jerk it for him, finally. At this point, I began undressing him and he did the same for me. It was really sweet and at this point, on his own, he began gripping and playing, exploring my dick. It felt really good and tender, and I told him he could also suck on it like it was a straw. He did and he also began tonguing up all the precum that was oozing around my foreskin. He pressed my dick against his face, he loved it resting against his cheek and mouth.

Like me, he's uncut. Our dicks are similar, just mine much larger. But they're the same dark brown, with similar veins, and with a medium amount of foreskin. When our foreskins are pulled back, the heads of our dicks are the same color as well: a slight purple/red. While he played with my dick, I'd look over to his mother and would make eye contact, and she was gently massaging her pussy.

For a few moments, I enjoyed this but knew that I was going to end up cumming, and I really wanted him to enjoy his first time like a girl would, so I laid him on his back and began worshipping his body, just as I would a girl: I caressed his things, kissed his stomach, sucked on his nipples, and gently rested on top of him and licked and kissed on his neck again, and his ear. Without telling him, he put his arms around my neck and kissed me and we kissed for a little bit. We kissed as I put my dick against his and slowly rubbed and jerked our dicks together. After this sensuous playing, I went down on him and sucked on his dick a little bit and his balls. I then lifted his leg and began kissing and licking on his thigh and ass cheek, then his butthole.

I gently turned him over until he was on his stomach, and I began eating his ass. It tasted wonderful, like Heaven. I tongued his asshole and kept jerking on his dick. He loved this feeling, especially of getting his ass licked. I got it as wet as I could, with really gooey, thick spit, as I intended to now fuck him in the ass. I had considered lube or something, but I wanted his first time to be really natural and nice, like a girl's with her boyfriend. Here, I explained to him what I was going to do, and how exactly it was going to be, and he really wanted to try it.

So, I got him on all fours, hands and knees, as this was the position he said he wanted to experience. I got behind him and massaged and ate his ass some more with my tongue. I talked to him as I was doing all of this, and let him know I was going to start to push my dick into his butthole and he said he wanted to feel it. Bent over, his mother gently played with his hair and massaged him. It was incredibly sweet.

As slowly as possible, I began easing my dick into his tight, little asshole. Much to my delight, he took it as well as he could. It was a very slow-going process, but I finally popped the whole of my dick head into him and let it rest for a few seconds. We kept talking during it all, and he was really a natural and meant to be on the receiving end of dick. I gave him encouraging words and told him he was doing a good job. He was doing really well, and so I pushed myself a little farther into his asshole, and then back out, and began actually fucking him slowly. Once I started going in and out of him, he got very quiet and rested the side of his face against the sofa pillow. I stroked his hair and gently massaged his back as I fucked his asshole lovingly.

At one point, I reached down to feel his dick and it was rock hard and leaking precum. I felt so proud. Then another time, he said he felt like he was going to poop. I told him that's normal and it was okay if he did poop, that I would just keep going - so not to worry about anything. This seemed to make him happy and he even began moaning a little as I was buttfucking him. This moaning and his breathing really goaded me on and so I got a little more intense with him, fucking him deeper and faster.

It was just far too pleasurable to hold it, and my dick was as hard as it could possibly get, and I could feel my orgasm coming no matter what, so I decided to go a little faster again, to a medium fast pace, and I pushed a little deeper into his butt (but still not enough to make it bad or too much for him) - and I could tell he could feel by the sounds he was making it but didn't complain - and I pumped all my cum into his little asshole. It was probably the best orgasm I've ever had. It felt both like a dream and surreal, just beyond words. As soon as I was done pulsing and pumping cum into him, I hunched over him and jerked his little cock until he came and produced a little cum as well. He explained how cumming felt and I told him that the feeling will get better with time and the more often you do it, but he said he liked the feeling of my dick in his butt even more. It kind of made sense, with him being so girly.

At this moment, I just held him in my arms with his mom, nice and close, and played with his hair. He was very content and this experience set in motion a few more, very sweet lovemaking sessions before his mother reunited with her husband and they had to relocate.

Still, I'm optimistic that I'll be seeing him and his mother again.