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36-Inch Flexible Dildo

36-inch dildo pressed into friend's anus

I have a friend that I play with from time to time. We usually just jerk each other off, but he does like anal play – a lot. I on the other hand, am not much into anal at all. Or, I should say I don’t like things stuck in me. But I do enjoy sticking things in my wife, and in my occasional male friends.

Usually, he likes ordinary dildos and things a few inches long. We have also experimented with fisting, and on a couple of occasions, I have gotten my whole hand into his rectum. He wants me to go farther, but I find he has a restriction about ten inches (25cm) in that I cannot get past.

One day, he showed me his new 36-inch (90cm) flexible rubber dildo. To give you some perspective, a typical man’s pants are only 31 inches in length.

He wanted me to put that in him. I was skeptical, and worried about physical injury. Still, he wanted it.

Se I lubed him and his dildo and went to work. He laid on his back with his knees up, and I started pushing it in. At about a third of the way, it was going nicely. At two-thirds, he had me stop a couple of times. He said it didn’t hurt, but he had to get used to the feeling. I resumed. It seemed stuck. I pulled back a little bit, then pushed forward again. It continued to enter him. There’s no doubt it was well into his transverse colon.

We kept playing, and finally, I was holding the last two inches (5cm). All the rest was in his large intestine.

He couldn’t see what I was doing, so he asked, and I told him how far it was in. That excited him. His penis, which had been semi-hard the whole time became like a flagpole. He wanted me to push in further. All the way in. I thought that was irresponsible. Like, what if he couldn’t push it back out? Something short in the rectum can be pushed out, but that long? I had my doubts. But I was willing to go another inch. I believe the far end was right up against his appendix, because that last inch was impossible.

He said he wasn’t feeling any pain, but his physiology told me otherwise. He was kind of wincing. So, ever so slowly, I pulled the whole thing out. As I was doing so, he rubbed his own penis to a fantastic orgasm.

In fairness to you, dear reader, I should point out that a year later this fellow was hospitalized for a serious intestinal problem having to do with an overzealous enema. So, it turns out there are limits to sexual play that should be regarded. Over the years, I have found many ways to have fantastic orgasms without taking any health risks.

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