About 5'9", 175 lbs. smooth Chelsea gymboy jock. He was real horny. He said that he was usually a top, but was in the mood to be tied up and have a guy work him over. I was more than happy to oblige
He showed up here at my place at 2:00 p.m., and he was indeed a hot guy. He is so good-looking and muscular, that he can have any guy he wants. That makes him very cocky and rude to guys, which he admitted he always is (you know the type), so I proceeded to do some "attitude adjustment" on him. I slowly broke him down with some heavy bondage and some heavy work on his tits, cock and balls, and butt. He was fairly ticklish, and as the session went on, he got more and more ticklish.
After an hour of being tied standing spread-eagle to my bondage frame and having his body mercilessly teased and tickled, I moved him to a tight spread- eagle position on his back on the floor. It was then that he confided to me that he had always dreamed of having a guy tie him up and tease his dick for a long time, without letting him shoot. I looked him in the eye and said, "Boy, your dreams are about to come true." He really didn't realize what he was in for.
For the next several hours, I did nothing but tease and stimulate his hard dick, with some occasional work on his tits, feet, and butt. I would repeatedly get him close to shooting, then back off. At the times when he was not gagged, he would complain that his "Knob" as he referred to it, was getting painfully sensitive from all the attention it was receiving. Poor guy!
As you can imagine, for the rest of the time, I concentrated on the head of his dick, making his "knob" more and more sensitive.
Throughout the whole scene, I tied him into about six major bondage positions, with only three very short rest periods in between, always with his hands tied behind his back, so he couldn't play with himself. He was in such good shape that he could take some of my more extreme bondage for a lot longer than most guys usually can. Besides the bondage frame, and the tight spread-eagle on the floor, I had him on his knees, legs spread, ankles tied off, wrists tied and yanked way up his back, collar on, wrists and collar attached to a chain from the ceiling, forcing him into an awkward position, with his cock and balls very vulnerable.
One of the times I had him spread-eagled on his back on the floor, I decided to try my feather duster on his sensitive dickhead. I tied a wooden dowel across the tops of his upper thighs, and then tied his cock and balls to the center of the dowel. This forced his hard cock to stick straight up in the air, and to remain fairly motionless. I suspended my feather duster from a cord in the ceiling, and positioned it right over his "knob", and let it swing. The effect was pretty amazing. He was trying to buck away from it, moaning, and his dick was throbbing and leaking like crazy . Of course, this was not enough to make him cum, but it did the job of constantly stimulating him. It also gave me some much-needed down time, to relax, have a smoke and a beer, and to just sit back and enjoy the show. I have an electric fan in my room, and the breeze from the fan was just enough to keep the feather duster in some kind of motion. In a New York apartment, we use what we have available.
For another extended period, I had him on his belly on my bondage board, which I have told you about, with his cock and balls forced through the hole and tied off, his cock pointing straight down toward the floor. Lots of stop and go jerk off, plus a little surprise for his knob.
I had been using various implements on the head of his dick, including feathers, a toothbrush, a pot scrubber, and his least favorite, an old hairbrush with sharp, brittle bristles. While his dick was hard and straining, pointing down through the hole in the board, I placed a chair under the board and positioned the hairbrush on it so that the tip of his dick would just lightly poke into the stationary bristles when his dick was hard. He was howling and trying to thrash around, trying to avoid the unbearable stimulation of the bristles on the tip of his dick, but he was tied down real good (you know me, right?). His dick would then start to get a little soft, so all I had to do was to approach, stroke his dick a few times, with either my finger or a feather, it would get hard again, and the tip would once again touch the brush. This went on and on for nearly an hour, and the poor guy was going nuts. But I think he was learning his lesson about not being such a shithead to guys he'd meet in the future.
I took him through several more bondage ordeals, but he finally ended up spread-eagled on his back on the bed. I had told him that he was not gonna shoot his load until it got dark out, and it was about 8:00 p.m., almost an hour before dark.
As I had been playing with his dick for so long, it was obvious that the only way he was gonna shoot was to have both the shaft of his dick and especially the head masturbated continuously until he shot. I decided that his knob had received enough attention for a while, and knowing that he needed stimulation there in order to shoot, I proceeded to remove all stimulation to his cock head. I took two condoms, and unrolled them just over the head of his dick, then took a rubber band, tripled it, and slid it down just behind his glans, securing the condoms in place. This effectively deadened his knob to most stimulation. I then proceeded to just tease and stroke the shaft of his dick for over a half an hour, paying absolutely no attention to the covered head of his dick. This, mixed in with some pretty merciless tickling of his helpless bare feet, armpits and ribs. Man, he was going crazy. He was begging me to stroke the head of his cock and finally get him off. I, of course, just smiled. As it got darker and darker out, I was enjoying prolonging this.
Close to 9:00 p.m., I finally went for the kill. I removed the condoms from dick head, and immediately gave it the toothbrush treatment, which, after not being stimulated for so long, was even more sensitive, and it had him howling. I'm afraid I had to gag him again at this point, using one of my old jockstraps. I finally greased up his dick (and mine!) and taking about a half an hour of very slow, stop and go jerking, finally made him shoot.
It was a gut-wrenching load, and I know that he felt it through his entire body. Mine wasn't too shabby, either.
I then released him, and after he recovered for a while, he dressed and left. I called him once, but so far, no response. I'll probably never see him again, but man, what an excellent scene.
I would like to get into more scenes like that. It is fun to fantasize about them, but even more fun to do them in real life. Now, I know that seven hours does not seem like much to you, but with our busy New York schedules, that is actually a pretty good session.
So, guys, share your thoughts on this aspect of a tickling scene.