I've written about my later experiences here, but have never told the store of my firts time on the receiving end.


I’d already crossed several lines that summer, beginning with mutual masturbation, then oral sex, and I’d even managed to get my penis up my cousin’s butt a few times. I’d enjoyed it all, but each new step left me questioning my sexuality again. And each time I’d found a way to rationalize this new transgression away. We were just horny boys, I told myself. All boys do it. We’d quit as soon as we had girlfriends. It wasn’t really gay, I told myself. And even when he crossed the biggest line, letting me have anal intercourse with him, I told myself he’d been the one that crossed the line, not me. I was playing the insertive role, not me. He was the girl, I was the boy.

But over the weeks he’d began to tire of always being the girl. He knew how much I was enjoying penetrating him, climaxing inside each time, and I’d even confessed that I could not imagine sex with a real girl feeling any better (or different.) So, naturally, he was itching to swap positions, and he began to also complain that I was too big for him.

I’d played with my butt for years, and I had no physical fear of him penetrating me. It was the mental side that scared me. A penis inside me would not something I could rationalize away, that would be crossing the final line. And, to boot, I feared I’d like it.

So, on this Sunday afternoon, with my family visiting kin down the road, we snuck back to my house ostensibly to play video games. But, instead, we went immediately to my bedroom and began to strip for sex. As expected, he demanded that this time I let him be the boy. Afterwards, he promised, he’d be the girl for me. I knew it was only fair to let him try.

Unlike our first few experiences with him being the girl, we now knew how important lubrication was. Accordingly I’d managed to squirrel away a half-empty bottle of Vaseline in my nightstand, and the supply got smaller each weekend he visited. But there was plenty, and I scooped up a bit and rubbed it into my butthole. I handed the jar to him, and had him smear a bit onto his tip and shaft. I still remember how cool the gel felt on my butt.

Because of our height difference, I’d guessed doggy-style or standing would be near impossible, so I decided to try a position I’d imagined but we had not attempted. Remember these were our early days, when our erections were rigid and not so flexible as they have become after the years. I lay on my back on my own twin bed, completely naked except for my socks, while as usual he merely let his shorts drop to his ankles. I slid to the edge of the bed, lay back, and spread my legs.

He stepped forward and guided his skinny little penis directly to my ass. In this position and in the daylight, there was none of the fumbling from the first time I fucked him. He pushed directly into me, and the lube and his small size facilitated a relative smooth entry. After an inch, though, the warmth was interrupted by a sudden and unexpected pain, and I had him pause for a moment for it to pass. It did, and quickly, and I told him to continue. Because of the copious lube, his small girth, and most importantly his short length, he bottomed out in a single push. I felt his little balls nestle against me and I knew his was all the way in me. And that is when the reality hit me full force.

Despite the growing pleasure, I was suddenly overwhelmed by the realization that I’d crossed the final frontier, and was deep in the middle of the queerest of acts. There was no more rationalizing, no more excuses, for I was doing the queerest thing available: I was being the girl, and another boy had his entire dick up my butt. And I liked it.

That’s what shocked me the most, I liked it. I knew I liked penetration my things like brush handles, tampon tubes, and the likes, but this was different This thing was alive. It was warm and it was alive and attached to a boy. And that boy’s body was responding to my body as if I was a real girl, his body was on autopilot and he was starting to build up to a respectable fucking pace, even slamming a bit. And I liked it. I really liked it. And after a few more minutes I began to really like it. I even imagined I was our female cousin lying there, with his dick in my cunt, slamming his little balls against me.

I started to feel feminine, and fantasizing about wearing some of her clothes the next time, maybe some hose or her little training bra…and then suddenly, just as I grabbed my own hard cock and started to pump in unison with his strokes, it was over. I felt him push in and stay deep, and I knew what was next, so I began stroking myself hard to try to catch up with him. As I took the bold step of crossing my bare ankles behind his back to pull him deeper in me, I felt the inevitable twitching and knew his little cock was spurting its bright white ropey semen deep into me.

He immediately was shy, embarassed, and quickly disengaged even as I was still cumming. He left for the bathroom, while I pinched my head and held my thighs together and waddled to the other bathroom. I was leakign from both ends, and as soon as i sat on the toilet i felt a lat of his semen spurting from my rear as i release my own. I knew however, that some of his semen was left inside me, and it for some reason excited me further. This was going to be fun, I thought, and I began thinking of how I'd fetch and stash some of my female cousin's underwear to use next weekend. I was already hooked.