How two young teen boys became sissy cocksuckers

Spying on the neighbor boy as he jacked off turned me into a sissy.

When I was 14, I lived in a duplex with my father and stepmother. In the other side of the duplex lived a woman and her 13 year old son Danny. I had discovered the joys of masturbation at least a year ago and was constantly horny and regularly jacking off my little cock. I had also started spying on my stepmother in the tub. I had trimmed just enough plastic from the bottom of the bathroom curtains so that I could stand outside the duplex on a concrete block and see through the bathroom window. Several times I had watched my stepmother in the bathtub and had frantically jerked my cock to orgasm while viewing her delicious titties and pink nipples as well as her bushy pussy. She was, after all, only about 12 years older than me. One night I was taking out the trash for the following morning’s trash pick up, and in the dark I walked past a window at the back of the house. The light was on and there was no real curtain on the window, so I snuck up to the window hoping I might get a glimpse of the woman who lived there naked. Imagine my surprise when I saw instead her 13 year old son Danny sitting back in the recliner with his pants and underwear down to his ankles and his hard cock in his hand. It freaked me out a little to see another boy almost my age jacking off, but I couldn’t take my eyes off what he was doing. He had a jar of his mother’s hand cream for lubricant, and his hand was slipping up and down his rock hard cock (about the same size as mine). I watched until he orgasmed and the cum came spurting out onto his chest. I couldn’t get the image of Danny out of my mind, and I few nights later when his mother was gone, I again returned to the window to watch him. Sure enough, just as before, he had his dick out and was stroking in the same chair with the television going in the background. I suddenly realized that my own cock was throbbing in my pants, so I unzipped and slipped it out and began to stroke as I watched Danny stroke. In very short order a very intense orgasm overwhelmed me. I had to hold onto the brick wall to keep from falling. I spurted hot cum all over the back of the house, and it had to be the most pleasurable orgasm that I had ever experienced. My hips were still humping the air long after I had spurted every drop of cum. I looked back in the window just in time to see Danny’s cock throbbing and spurting his load.
Well, over several weeks I continued to spy on Danny’s jack off sessions and I completely forgot about spying on my naked stepmother. I discovered that his mother was gone for several hours on Mondays, Wednesdays, and Fridays, and that is when he would take advantage of her absence. I really became a little obsessed with watching him stroke his hard cock. Finally I determined to confront him. I had told my dad that I was going to a neighbor’s house to visit a friend, and I first slipped around back to check on Danny. His mother’s car had just pulled out of the driveway, and he was just pulling down his pants and underwear and getting in the recliner for his nightly jack off session. I went around the other side of the house to the front door, and just as I suspected the door was unlocked. Throwing caution to the winds, I entered the duplex and made my way down a long hallway to the back room where I knew that Danny was. When I walked into the room and spoke to him, he reacted just as you would expect. He jumped out of the recliner and was frantically trying to yank his pants and underwear back up. I just sat down on a couch, and told him in a calm voice that I had been watching him through the window, that I knew he liked to jack off when his mom was gone for the night, and I just wondered if I could join him. In other words, I proposed that we jack off together. I was only a year older but also in a school grade ahead of him, so maybe he looked at me as older or more experienced. I don’t exactly know why, but he agreed to my proposal. I pulled down my pants and underwear, sat down on the couch and began to tug on my cock. He did the same. For a while it became a regular routine for us. His mother would leave, and I would go over to jack off with him. Of course it was only a matter of time before we experimented with jacking each other off. I loved taking his hard dick in my hand and sliding it back and forth and making him hump against my hand. I also loved the feel of his hand on my weenie as he stroked me and stroked me. I especially loved the powerful feeling it gave me when I could make him cum and spurt hot cum halfway across the room. It wasn’t long before we started going farther. I was the first to take his cock in my mouth and suck on it. It tasted delicious to me, and before long, I simply couldn’t get enough of it. He, of course, sucked me too, but I’m not sure that he loved being a cocksucker as much as I did. We even started meeting up some mornings in an old storm shelter behind the house and I would suck him off before we walked to school. I learned to love the taste of Danny’s cum and I would swallow every drop hungrily. We started to experiment with crossdressing. I would try on some of his mother’s underwear. She was quite thin like me. Danny would try on my stepmother’s underwear, which I had taken from her dresser. She was a little plump like Danny. I’m sure that we were quite a spectacle all dressed up in panties and bras (and even panty girdles). It was a very sexual experience for us, and we would suck on each other’s dicks until we came. I don’t remember what prompted us to try anal sex, but I do remember the first time. We had read about it in a magazine that one of us had found. I remember that we used Vaseline as a lubricant. The very first time was a little painful for me, probably because I was tensed up and couldn’t relax, but I know that by my second time, I was hooked on sexual feelings that I had never felt before. It was like I was a girl being fucked by her boyfriend, and I absolutely loved the feeling of hot cum spurting into my boi-pussy. It wasn’t long before I was begging Danny to fuck me.
This is the story of how I became what I am. Less than a year later, Danny and I both seduced an older gay man into buying us girls’ clothes and wigs and turning us into sissy-bois. But that is a story for another time.

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