The Most Difficult Olympic Sport

Some buddies and I got to talking after a pickup basketball game. A couple of us must have been horny, because the conversation turned to masturbatory things. I believe any of us who weren’t horny became so as the conversation became ever-more raunchy.

The discussion started with what might be the most difficult Olympic sport. I think we pretty much settled on Decathlon. Then someone said something like, “What if it wasn’t a sport?”

We were like “Huh?”

He went on, hesitantly, and slightly blushing to say, “What’s the most difficult sexual thing?”

Several of us had some suggestions, like “Reverse doggy style,” whatever that was, and “Anal intercourse.”

That one got some attention. Mel immediately asked, “Do you mean giving or receiving? With a man or a woman?”

Some of the guys admitted to bisexuality, and to my astonishment, some had even said they did it with other men.

This discussion was getting deep!

After a moment of silence, I, like an idiot, piped in with, “I think the most difficult thing is dry orgasming?”

Of course they wanted me to explain. I wished I hadn’t even brought it up, but since I did, I went on to explain in full detail. I told them that a man can learn to have full orgasms, with all the springs and chills feelings, even sometimes urethral contractions, but nothing comes out. When this happens, the man can stay erect and aroused and do it over and over again. It’s like having your cake and eating it too.

A couple of the guys thought I meant it in a theoretical way – that such a thing was not actually possible.

Being in so deep already, still the idiot, I explained that I had done it many times, that I found it extremely enjoyable, and that it’s something any man could learn.

One thing led to another and before long, all ten of us ended up agreeing to a meeting at Godfrey’s house. He has a large place and lives alone. The plan was that I would demonstrate the technique, and then those would would want to practice could give it a try. I mean, all of us getting naked and masturbating in each other’s presence. How crazy is that?

This was a Friday and the meeting was to be on Tuesday. The few days in between were hell for me. I was caught between a series of recurring emotions ranging from “What the fuck did I get myself into? I should cancel,” to “I can’t believe my buddies are so open-minded about this.” Basically, I was scared, like heart-racing scared at times, yet also so looking forward to it – like a kid knowing he’s going to Disneyland.

Tuesday evening finally came along. I was a wreck at work that day. Couldn’t think straight. Finally, by 7:15, nine of us had arrived. Carl called up and canceled. Wimp! But where it gets weird is that Sam brought is wife Sam. Truly, he’s Samuel, and she’s Samatha. But what was she doing there? I was trying to understand as we all stood around Godfrey’s dining table eating snacks and making small talk.

Samuel explained that he always tells Samantha everything. (I think most of the rest of us guys who were married may not have actually told their wives what we were up to.) She said ‘cool,’ as long as she could come also. Weirdly, the two Sams thought other women would be there also. But no, it was nine guys and just the one woman.

We were nervous enough about what was going to happen, without her being there. I think the evening almost failed. We spent way too long In Godfrey’s dining room just talking. Finally, Eric just asked me, “Well?”

I knew it was the point of no return. Still, I didn’t make any move to get things started. It was Jonny who got us moving in the right direction. Looking right at Sam (the woman), he quietly asked “Alright?” With his hands on his belt.

She was like, “Certainly. Dudes, I’m totally looking forward to this!”

I was thinking to myself, that although scary in some unclear way, it would also be exciting to share my skill with a woman – to have her watching. It’s just too bad she wouldn’t get naked – I assumed.

Jonny did remove his clothing, followed somewhat slowly by all the rest of us guys. Guess what? Samantha pulled her stuff off too. She’s fucking gorgeous. Curvy in just the right places, with light freckles on her face and most of the rest of her body. Oddly, her large, super-attractive tits and her tight, smooth ass were freckle-free.

All us guys, now naked, acted properly. No one went crazy in Sam’s presence. I was kind of worried one of the guys would start snickering, or making stupid cracks, piss Samantha off, and ruin the whole thing.

You may be surprised to know that none of the men, even though naked as the day they were born, were erect. We were all soft, squishy noodles.

More small talk ensued. It seems everyone was afraid to get things started. To my great fear – yes I was fearful once again, I knew it was up to me to get things started. I had been the fool to open my mouth three days ago, and say I could teach them this masturbatory technique.

With my voice almost shaking, I asked the group, “Who wants to go first?”

Ever the gregarious one, skinny, tall Lyle said, “Me, me!”

I instructed him to lay down on Godfrey’s couch. I sat next to him. With everyone watching intently, I touched his totally soft penis. Being evidently the expert in the group, I said “Watch this” and proceeded to extremely lightly run one fingertip over his frenulum. His soft penis jumped an inch at that first touch. Within 60 seconds the man was 100% fully erect.

I happened to glance around the room, and now, in solidarity I guess, half the men were similarly erect. A couple of them were idly touching themselves. Samantha was no prude. This girl already had one finger in her vagina.

Now it was time to start the lesson in earnest. I started wanking Lyle, telling him to let me know when he started to experience the ‘gonna cum’ feeling. That happened in about two minutes. I explained exactly how this dry orgasming thing is done – that it’s like edging where one stops just before the point of no return. But unlike edging, one doesn’t stop long enough for the feeling to subside. Instead, one resumes after only a second or two.

So that’s what I tried to do with Lyle, but it didn’t really work. He ejaculated within a few minutes.

I decided at that point, feeling that the men were starting to believe I was full of shit, that I should probably show how possible it really is.

So, I took Lyle’s place on the sofa and started wanking myself with everyone watching. By the way, if you’ve never wanked in the presence of a bunch of people watching you, it’s a super-amazing feeling! You’ve got to try it.

I spread my legs wide and told the men, and Samantha, to watch my perineum and the underside, urethral portion of my penis for contractions. To take it a step further, I asked for a volunteer to place a finger against my perineum to feel my contractions. That was Godfrey. He immediately admitted that this was the first time he had ever touched a man in a sexual way, and “It isn’t horrible.”

So, in front of everyone, I stroked and got close to ejaculating. It was difficult not to just immediately ejaculate with the excitement of everyone watching, and with Godfrey’s finger on me, but I managed a dry orgasm. First, before the bigger contractions came, Godfrey announced he could feel movement. Then, I had some stranger dry contractions, and everyone could see my perineum and penis pulsing. I stopped for a moment to regain my composure. A minute later, I had another dry orgasm. However, the time after that was beyond my control, and I ejaculated in front of everyone. How could I not? So far, this was already shaping up to be one of the best times of my life.

After my little demonstration, all the guy broke into groups, most laying on Godfrey’s carpet, and either doing themselves or each other. Of course Sam worked on Sam.

Most of the guys didn’t manage dry orgasming on this first experiment, but a couple of them did. A little later, pretty much everyone stopped what they were doing to see Samuel doing pretty much the same thing to Samantha.

She boldly, like a teacher, which she actually is, lectured the group on the fact that many women including her can have multiple orgasms anyway, but to specifically derive it and to try to extend it, excited her greatly. Sam brought Sam off several times. We were all so delighted to see that!

The evening was a smashing success. Over the past couple of years, the whole group has not gotten together again, but I have participated with several men, and sometimes groups of three or four, as we practice dry orgasming together. We have been discussing how some form of dry orgasming should become an Olympic sport.