2000-06-02 - 00:07:13
"It's Going To Hurt When I Pull Out"
"It's Going To Hurt When I Pull Out"
Unless there are any fabulous developments in my life--in which case I'll break in with current updates--I am going to regale you with funny sex stories this weekend. Sexuality can be so hilarious. At least mine.
Ten or eleven years ago, when I lived in this city before, I was deeply attracted to a guy named Mark who was dating my friend Pat. After they broke up, Mark started dating Pat's ex, also a good friend of mine, Jon. I bided my time. A few months later, after Mark and Jon were no more, I made my move and Mark and I became an item.
The sad part was Mark tortured himself with not wanting to be gay, and so in between in all these relationships he would disappear back into the closet for weeks or months and then surface again, sexually frustrated.
A decade and hundreds of sexual partners later, I look back on our brief, on-again, off-again imbroglio as some of the best sex I've ever had. Fuck. Once we got started--once he worked his way through the group of friends to moi--we just couldn't keep our hands off each other.
And Mark had the sweetest butt imaginable. Those buns shaped the jeans, not the other way around. We're talking rock-hard, smooth, mouthwatering.
He'd never been fucked before, and I wanted to fuck him. But that would mean he was gay, you see, so Mark wasn't into that.
Well, there is a sure-fire way to get a reluctant guy interested in that particular activity and so one night I rimmed the living daylights out of him. I think it was his first time; I was still pretty new at it myself, but I was so aroused I turned a different color.
As was Mark. Sure enough, he said he was ready to have me inside him. In his darkened bedroom, I donned the condom I'd brought with me just in case, lubed up Tab A and Slot B, asked him if he was sure about this. He was sure. I said, "Well it will probably hurt at first, but just tell me to stop anytime."
He lay there on his back, his smooth tanned legs propped up on my shoulders. I began to ease into him. He yelped. I pulled right back out. In the dark I could see his contorted face. He still wanted to try again. We tried again. Again, too painful. We paused, kissed some more.
For our third try he grabbed onto my hard-on, said he would feel more comfortable guiding me in with his hand. That was fine by me. We got back into position. I could feel myself prodding up against his butthole. Mark started to moan, like he had when I'd rimmed him. Okay, maybe we were getting somewhere. I felt myself push in a ways, up to that point where he'd cried out twice before. He kept moaning. My dick stiffened all the more in anticipation. Slowly, I prodded in further, egged on by Mark's ecstatic cries. Soon I was all the way inside, and he obviously loved it. I began to thrust, at first slowly, then like a crazy man. Mark was jerking his dick as we grunted and sweated and writhed and eventually came at the same time.
Sweat dripped off my chin onto his cummy belly as I gazed down at him, my dick still tucked inside. No words, just two boys glowing in the dark.
Finally, I said, "Okay, now comes the fun part. It's going to hurt when I pull out."
"What?" he said, laughing: "Pull out? You were never in!"
He'd been aroused by my dick rubbing up against his asshole, and I had just fucked his lubricated, clenched hand.
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