Almost Lost It
One evening I was in the Club Baths doing my usual voyeurism with mild participation thing. Began a mild touching and masturbation scene with a pleasant young man named Ned -- a thin small guy with receding reddish hair and a quick smile. I liked him. Pretty soon he asked me to his room. Alone, our ministrations progressed from the mild caresses to deep kissing and sucking. In a while I found myself in a new position - flat on my back with my legs being lifted up by Ned's arms. As Ned's cock approached my ass, I realized what was happening and called a halt.
"Hey, hey wait. Wait. No, no. I don't get fucked. I've never been fucked man. Hey, no, I'm sorry."
"Oh, oh. Alright. Okay," he soothed.
But he kept lifting my legs and his dick kept coming closer and closer to my hole as he covered me with little kisses. After a while, I began to think, well, you know, maybe I should try this. If I'm ever gonna get fucked, this would be a good guy to try it with. He's nice. I'm turned on by him physically and things seem to be progressing slowly enough. Like I don't feel like I'm getting raped here or anything.
So, after a while, my protests grew quieter and quieter, and I was returning Ned's kisses with the silent understanding that it was okay for him to proceed. Ned was a very considerate lover. It took maybe a half hour for him to actually place the head of his cock in my asshole.
Oh, but when he did! That motherfucker hurt like a bastard!
"Hey, hey, hey. I can't do this." As I lowered my legs, and pushed him away.
"It's alright. It's going to be okay. I'll go slow. Don't worry. Going to be okay. Let me just keep going slow, real slow, and if it starts to hurt, you tell me and I'll stop right away.
"Well..." And the legs go up again.
More kisses. The glans of Ned's penis rubbing the outside of my anus. Feels fine.
Uh, oh. Here comes that thing into me again. I feel like a torpedo is being shoved up my ass. The head of his dick is in me now. I can't deal with this. No how. No way. I don't like this. I wasn't built to be fucked. Period.
"Umm, Ned. No, no. You gotta stop man. I can't stand this." I expel the head of his dick
with a single push.
The frustration and disappointment on Ned's face is painful to see.
But he recovers. A smile returns to his face and he stretches out on top of me, our sweaty bodies sticking together. We kiss.
"They say the small ones are the ones that tear up the upholstery the most," Ned declares enigmatically.
I smile agreement, not quite understanding what the fuck he means. I'm willing to agree to anything as long as he keeps that awful marauder out of my ass. Thinking about it later, I guess Ned was referring to the size of his penis, which was not huge, just about average. But does it make sense that a smaller dick would hurt more than a bigger one? Not to me, it doesn't. In later years, I think that if I had relaxed more maybe I would have adjusted better. Maybe I didn't really give getting fucked a fair chance. I've heard some guys say that it feels great. In fact, the bigger, the better. I'll take their word for it.