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Peehole Stretcher

I have jerked off with a friend from time to time. He’s a guy I met at church. He’s four years younger than me, and like me he’s married with a handful of kids. I have two girls and a boy. He has two children. Both of us are happily married, In both cases, our wives don’t enjoy sex as much as we’d like. The wives kind of know what’s going on with Keith and I, but we don’t talk about it. I think they are secretly relieved that Keith and I have an outlet for our sexual energy, so the women are off the hook.

I went over to Keith’s office a couple of weeks ago where we meet up every now and then to jerk each other off. It’s a nice private psychiatrist’s office with various furniture. He even has a sort of back room with a massage table in it. Why, I don’t know exactly, but that’s where we play.

On this occasion, he said he had a new toy, but wouldn’t tell me what it was until arrived. The back room was warm, we had removed our clothes, me, with an erection right from the start, and him still soft, as was usual. It takes a bit to get him erect.

Anyway, he finally brought out the thing. It didn’t look like much. I don’t know what I was expecting, maybe one of those battery powered massagers or something. This was a small stainless steel rig. Essentially a ring with two one-and-a-half inch long prongs. Each prong was attached by a screw and wingnut assembly. The prongs were thin, like the tines on a fork, but round and smooth. They were bunched together.

Keith's urethral peehole stretcher
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I figured out what it was right away. A peehole stretcher. I wasn’t sure I liked the idea. It worried me, and made me especially horny at the same time. Strange reaction I know, but that’s what was going through my mind. I thought I’d probably decline, going for a regular handjob instead, but if he wanted, I could use it on him.

Yet, I was somehow quite excited by the thing, so I guess it’s no surprise that five minutes later, I was laid out on Keith’s massage table, with my six-inch dick fully erect and sticking straight up in the air. Usually it lays against my belly, unless I’m especially aroused. I was also nervous.

Keith was busy liberally washing the thing in rubbing alcohol. He got the alcohol all over his hands too. He said sterility is important in the urethra. Then, he took his time drying it off, which caused my feelings to intensify. I was becoming remarkably aroused. At the same time, I was becoming scared. He was going to put that thing in my dick!

Finally the contraption and his hands had dried. He put some oil on it, and a bit on the tip of my glistening penis. It glistens when the skin of the glans is stretched tight with super-erectness.

The first touch of his oily fingertip right on the end of my peehole was wonderful. I’m sure you know what I mean. The first touch, wherever it is on your genitals, is always so delicious. I craned my head up to watch as he placed the bunched-together prongs against my peehole. Slowly, ever so slowly, he slid them into my dick.

So far, so good. It didn’t feel like much. I did feel a sense of penetration in a place a guy is never penetrated, and maybe a very slight sting. But here’s the crazy thing. I was getting all jittery. I don’t know if it was the fear or what, but my legs, especially my thighs were sort of jumping with all sorts of little involuntary contractions. Shivers, really.

Once it was fully inserted, he just left it there for a minute. With his eyes, he asked whether I wanted him to continue. I knew it might hurt, but I absolutely wanted to go on with this experiment. Oddly, I already was feeling a hint of that ‘gonna-cum’ feeling.

He started cranking the little wingnuts. The prongs started to separate. No problem. It felt kind of nice. The slight sting when he first inserted it went away.

He continued to turn them, and I started to feel some tightness. It was a rather delicious feeling. He turned them some more, and now, I could feel a sort of pinching sensation. I asked him to stop for a minute. I raised my head and looked at the thing stuck into the tip of my dick. He saw me look, and tilted my dick toward my eyes, so I could see the opening. It was stretched surprisingly large in a tight oval shape. I could see way down into my urethra. My dick pulsed in some sort of anticipation. Almost the kind of pulse that happens when you start to ejaculate.

After a moment, he continued moving the prongs apart, ever so slowly. There was no mistaking it now, the thing was starting to hurt. My legs were still shivering, but now, even more so. My heart was racing. I wasn’t sure this was good for me, but then again, I figure no real harm could come from it. Still, I was scared, and super aroused at the same time. I know it doesn’t make any sense, but that’s what was happening.

I lifted my head again and watched as he slowly, gingerly turned the wingnuts some more. It was really stinging now. I wasn’t sure I could take any more. I told Keith to stop for a moment. Instead, he turned one of the wingnuts one more quarter turn. Damn, that hurt! And suddenly, cum was bubbling up into my wide open urethra, between the prongs, and up over the top of my urethra. As I was cumming, the sting was strong and was actually throbbing with every ejaculatory contraction.

As soon as I settled down, Keith started loosening the wingnuts. Damn if that didn’t sting more than when they were stretching me wide open, but only momentarily. Finally, the prongs were bunched back together again and the thing was removed from my peehole.

It had been one of the strongest orgasms of my life. And certainly the strangest.

Keith was just dying for me to try the thing on him. Even though he had owned it for several days, he had refrained from trying it on himself, since he wanted to save it for this very occasion.

His penis was already as hard as I had ever seen it in anticipation. I got him on the table, and to my surprise, I was very interested in applying the thing to him. Who knew that I had sadistic tendencies?

I got it all sterilized with the alcohol and went to work. His legs didn’t become all jitterly like mine had been. In fact, I was still having some trouble standing there next to the massage table. My legs now felt rubbery. He loved it right from the start.

As I was working the wingnuts, opening his dick ever wider, he was screaming for me to stop, then a second later, screaming for me to keep going. Evidently, this was giving him lots of exciting pain, and I understood how he was enjoying it. A half-hour ago, I wouldn’t have understood that interest in pain at all. Just like me, after a couple of minutes, he came involuntarily. The cum flowed up through his widely stretched urethra over the spreader and my fingers as I held his throbbing penis. After it was over, I slowly released the wingnuts, and again just like me, I could see that the pain of releasing it exceed the pain of being held stretched open. He was wincing and jerking reflexively as I loosened it.

Finally, it was fully out. I had become hard again as I was working on him. He wanted to give me a regular handjob, and I was all for it, although I figured it wouldn’t amount to much. But no, after a short while, I came again. There was a very slight pinkish tint to part of my cum, so I guess the thing had injured me slightly. After I came again, it was time to put Keith on the table for his second ejaculation, but he was soft, and couldn’t cum again, despite me spending five minutes trying.

And that was the craziest session of my life. The next day, it stung to pee a little bit. After that, I was back to normal. Keith reported that he was fine, too. Still, the thing kind of scares us, so we both decided we don’t need to do that any more.

Today, Keith just texted me that he has purchased a ball press, whatever that is. I can’t wait to play with it.

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