What He Wanted and What I Wanted

He wanted someone to fist him. I've never done that fully, and especially not with a man. Years ago, I got four fingers into my girlfriend's butt. but that's as far as we could go. We both had fun. And a few months ago, I put my entire fist into a woman's vagina, while her husband watched. I felt around for her cervix and couldn't find it. When I asked, she told me she had a hysterectomy. Oh! That's why I couldn't find it! Later, she put a fingertip into my urethra, which was delicious, but that's another story. Anyway, this fellow wanted to be fisted, and fisted deep. I, on the other hand, wanted a good, firm testicle massage. My wife will massage my balls, and frequently, but by gosh, she just won't squeeze hard enough. She says her wrists get sore, but I think she is just afraid of hurting me. So, we communicated by email a few times, and made arrangements to meet at his house. When I arrived, he answered the door fully nude. He was a good looking guy. About twenty years younger than me at around 40. He was not tall or short, quite trim, and had a wonderful smooth butt. Quite athletic, but he was walking kind of funny. He told me he had run a marathon (26 miles) yesterday, and so had a sore foot. Funny thing, I had a sore foot too, from too much tennis. We introduced ourselves, and I came in and took off my shoes, and of course everything else, too. He appreciated my shaved cock and balls. I'm quite hairy everywhere else. If it were up to me, I would be smooth as a billiard ball, but I'm not, so I just shave what makes sense. He seemed to appreciate the older, hairy kind of person I am. His dick was just a bit on the small side, which I particularly like. But what I especially like, which we had both determined in our emails, is that he is not an all-gropey person, and neither am I. In other words, I like handjobs and related activities, but don't enjoy kissing, frotting, hugging, blowjobs or anal sex with men. I'm pretty sure I'm fully bi-sexual, but for some reason, I only enjoy those activities with women. Go figure! Within a couple of minutes, he had spread a sheet over his sofa and had laid sideways on it, on his back, and pulled his feet up so I had clear access to his butt. I started very slowly by simply touching his penis and scrotum with very light touches. He became only slightly erect. He seemed embarrassed that he didn't get fully hard, but I told him I often don't get hard the first time with a guy either. After a minute or two, I ever so slightly started slowly stroking around his anus, but not quite directly on it. Finally, I touched his actual butthole every so lightly. He shuddered. He did seem to be enjoying my slow, anticipatory approach. Next up, I lubricated one finger with the lube he provided, and slowly inserted it into his butt. Considering that he was interested in fisting, I was surprised to find his butt quite tight. I had to twist a bit, and really take my time getting that one finger in. When it was time for two fingers, I had to move even slower. He was very tight. Now, I have put my fingers (not fists) into many male and female butts, so I know tight when I see, er, feel, it, and he was tight. So, I took my time, watching his face and physiology for signs of pain. He was enjoying, so I pushed on. Finally, I had four fingers in, and he was in heaven. He was also stretching nicely. Before I even arrived, I was resigned to the idea that I might not actually be able to fist him, even though I was hoping to fully fist someone's ass for the first time. But he might have been just too tight, like my girlfriend was. But no. In time, I had all five fingers and the bulk of my hand in his butt. The worst of the stretching was over. I turned it back and forth a bit to make sure he wasn't in pain or too close to the limit, but no, he was fine. So, ever so slowly, I went all the way in, and felt his sphincter constrict around my wrist. Very nifty! In time, ever several minutes, I pushed on. He wanted me to go as deep as I could. Now, I was a bit concerned about rupturing his intestine, but he said that just doesn't happen. Still I was concerned, because he said he had never actually been fully fisted before, so he was new to this also. Well, I pushed on, and I can now tell you that there is another constriction about six inches in. I think this is where the rectum meets the large intestine proper. If you look at anatomical drawings, there is quite a bend there, but it automatically straightened out for me. I uncurled my hand before pressing further, so with two fingers, I could feel where the opening led. First a little to the left, and then to the right, and pushed in more. His bowel was straightening out, to allow me clear, but tight passage. I took a moment to feel for my fingertips with my other hand through his belly. Sure enough, I could feel my hand in there. Then I wiggled my hand back and forth inside him. He loved it! All told, I think I went in about ten inches. But I sensed it was enough, and ever so slowly, I pulled out. Perhaps next time, we'll go even further! By the way, during the whole time, his penis remained small and soft. Personally, I would have loved to see his totally hard erect penis waving around while I fisted him, but I was still quite satisfied anyway. I washed up. Surprisingly, there was nothing disgusting on my hand or arm. He must have had an enema or something prior to my arrival. Now, it was my turn. He had me lay on the sofa, and started with a slow and gentle touching of my genitals. I erected only slightly. As I said, I often have trouble getting hard at first with someone new. Then he squeezed my balls gently. He started all sorts of variations of massaging my balls. Squeezing until they popped into different positions in my scrotum, pulsing them, even slapping them, which I didn't realize I enjoyed, but now I do! He slowly, ever so slowly increased the pressure. Somehow, he know exactly how much pressure was right, because it never hurt, but felt absolutely wonderful. All that wonderful ball massage did the trick. I became fully rock-hard. After a while, he asked what else I like, and so I told him. I love it when people hold the shaft of my penis in one hand, and rub the palm of their other hand over the glans (tip of penis). So, he started doing that. If you've never had it done, let me tell you: At first, it is unbearably pleasurable. Yes, that's right. It is like a sort of intense tickle that you feel like you can't stand. You squirm tremendously, and want to get away from it. That's why you can't really do it to yourself, or at least not properly. You won't put up with it. But when someone else is sitting on your chest, and rubbing your glans like that, it is delicious torture. Oh, not real torture. It doesn't hurt. It only makes you squirm. After a while, something else sets in. It is a new feeling, unlike other sexual activities. It is like a combination of the feeling that you have to pee, and are going to cum. But you don't pee, and you don't cum. You can just keep going and going. The need to squirm subsides. Now, the good practitioner of this palming technique will watch the recipient, and either squeeze harder or less hard with the holding hand, and will vary the angle and pressure of the rubbing, to keep the recipient squirming. And that's just what he did. Even though he had (probably) never done this before, he had a natural feel for it. After a long while, I volunteered to 'do' him. I gave him a lighter version of the same palming treatment and he loved it. I massaged his balls, and unlike most men whose balls I have massaged, he was OK with a fairly firm massage. A man after my own taste! We traded back and forth a couple of times. He never put a finger in my ass, which was fine with me. Oh, i enjoy that from time to time, but this evening was mostly about his ass. When I was near orgasm, I went to work on him. When he was nearing orgasm, he went back to me. When I worked on him, he did become fully erect, but never ejaculated. I did ejaculate near the end of the evening. Oddly, after all that wonderful experience with a sexy man, I didn't cum hard, but rather a small orgasm with little output. I worked on him after that, mostly doing an ordinary handjob. He was quite hard, and it lasted quite a long time. He apologized for not 'being able to cum.' I told him cumming wasn't the goal - to just lay back and enjoy whatever happens. Finally, he says he had a dry orgasm. I didn't feel any contractions even though I had one finger in his anus and was massaging his prostate at that point. So maybe, he had just had enough. Sometimes it happens that way. If you are young, you might think orgasm and a huge ejaculation is always the goal. But not, let me tell you that the play itself is the goal, and ejaculation and all that is just a side effect, really. I believe we'll get together again in the next couple of days. The second time, in my experience, is always much calmer, smoother, and we'll both be erect almost the whole time. We'll probably both also ejaculate good and powerfully. Although, another possibility is some serious edging. That's where the participants get very close to orgasm repeatedly, but then stop stimulation momentarily before resuming. With practice, you can actually have orgasms, with contractions and everything, but without cumming. This way, you can stay hard and play all night long.