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Sword Swallower

I went to a vaudeville revival convention a few years ago. Dancers, musicians, jugglers, mimes, clowns, ventriloquists, comedians, and others attended. I fancied myself a bit of a magician, but it was more a hobby than a profession.

I didn’t know anyone, and I wasn’t even sure they’d let me in, but they welcomed me with open arms. Four days in, and I felt very accepted. I was becoming one of them, seemingly a big, happy, if somewhat weird international family. Most of the people knew each other from years and years back. They grew up in the business together. They’d meet at various theaters and so on. I noticed they were a very horny, sexual lot. There was frequent innuendo and outright sexual discussion. I gathered a lot of intercourse and other activities went on in the hotel rooms among these people.

So one night, a sword swallower, a guy named Jeremy Blue, was going to do a private show. I was invited, along with like a hundred other people. Everyone was saying that it was going to be a very unusual show, with something more than sword swallowing.

So, we’re all chit-chatting in the audience, when the curtain opens, and out comes Jeremy with a tray of various sword-like things.

True to form, he did some real geeky sword swallowing. Now, I’m not really a fan of such things. It’s not a magic trick. It’s real. Sword swallowers have trained their throats to accept foreign objects, and they really do stick metal things down through their esophagus right into the stomach. The thing that was cool, is this guy had a great onstage personality. He was truly funny. You didn’t have to like sword swallowing to enjoy his show.

Next, he did some things with fire. Putting out balls of fire in his mouth. Spitting flames, juggling three flaming balls.

Then, a hush came over the audience. Many of them evidently knew something I didn’t.

Jeremy started doing a striptease on the stage. I thought it was a joke, but he kept going until he had not a stitch on. Not only that, he was more naked than most, explaining that he didn’t have any hair except on the top of his head because it would interfere with his fire show tricks.

He proceeded to rub fire wands over his stomach, chest, and even his face. I couldn’t help noticing that he was growing an erection during this process. He seemed totally unabashed, like an erection on a stage in front of a hundred cheering performers was normal, an everyday occurrence. I was shocked, but somehow fascinated, maybe even delighted also. Now, I’m not gay, but I do appreciate the human body, whether male or female.

He stopped, lit what looked like a wad of cloth on fire, and held the flames under his balls for a very long time. I don’t know why that didn’t burn him. He put that out, and seemed to be done with fire.

Now, he grabbed one last implement from his tray. It looked like a miniature sword. He handed it to someone in the front row, and it was passed around. I got to touch it for a moment. It was indeed a miniature sword, about fifteen inches long, with an additional six inches of a small handle. The edges were not at all sharp. In fact, it was highly polished stainless steel in a sort of oval shape. Somewhat like the handle of a fork, but tapered toward a dull but pointy end.

The small sword came back to the stage, where Jeremy rubbed it with something. In a moment, the smell wafted from the stage down to us in the audience. It was rubbing alcohol. Then he rubbed it with something else, oil I assume. All the while, it never occurred to me what he might do with such a thing. I was too focused on his ongoing erection, which he had continued to ignore during this whole thing with the little sword. He continued to tell funny jokes. Then, he sat in a chair, and the whole crowd leaned forward to see better. A big TV screen lit up behind him, so we didn’t have to strain to see what he was going to do next.

And what he did, sent me into a masturbation frenzy back in my hotel room right after the show. He slowly stuck that sword into his peehole. Eventually all fifteen inches disappeared into his penis, while he was explaining how it felt going past his two sphincters. Did you know there are two urinary sphincters? I didn’t. One is voluntary, the other involuntary, he explained. He left it in a moment, then started masturbating with it buried all the way to the handle. He announced ‘I’m now orgasming.’ We could all see his muscles throughout his body tensing and we could see his penis and perineal area pulsing on the monitor, but nothing came out. He stayed stationary for a couple of minutes. It seemed to take quite a while for his orgasm to end. Then he slowly withdrew the little sword. When the tip came out of his peehole, it was followed by a couple drops of semen. He put on a robe, accepted his very enthusiastic applause with a big smile, and the curtain closed.

I’m no sword swallower, and I value my life, so I’m not going to experiment with Jeremy’s urethral trick, even though the thought has occurred to me. But I hear the urethra is very prone to infection, as well as physical damage, so I’ll stick with ordinary masturbation – while I replay in my mind what Jeremy did, thank you very much!

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.

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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.

Sister Takes Me Beyond Orgasm

How my sister learned this stuff, I don’t know. I’ll probably get around to asking her one of these days.

What’s she’s been doing lately drives me crazy. After every time, I swear I won’t ever let her do it again, but then between sessions, I really start to crave it once more.

Here’s what she does, with minor variations every time:

She gets me entirely naked. Sometimes she remains clothed, sometimes she becomes totally naked also.

She has me lay on her massage table. I’m usually already erect. It used to embarrass me to have her see me erect, but that was long ago.

She has tied up some short ropes to the table legs ending in four bandanas that she ties around my wrists and ankles, explaining that the treatment will be so severe, she wants to make sure I don’t thrash and fall off the table.

She’ll dangle the corner of a sheet of toilet paper over my penis. She lowers it slowly, waving it back and forth. My penis twitches in anticipation. Finally the corner of the toilet paper just brushes over my frenulum ever so lightly. My oh my, what a feeling, as my penis jumps an inch. If I wasn’t hard already, I certainly become hard during this procedure.

Kayla then abandons the toilet paper, and starts massaging my balls. She starts out lightly, but then adds more and more pressure. She squeezes them between her thumbs and first two fingers, making them pop back and forth in my scrotum like wet bars of soap. Yes, it hurts, but not very much. I love it. I once ejaculated just from this treatment. She hadn’t even touched my dick.

Next, after some gentle fondling, she jerks me off in earnest. I cum. I cum hard, squirming all over the table. But, as she explains it, that’s only a side effect.

She keeps jerking me off after the pleasure subsides. It becomes agony. I am indeed thrashing, yelling, but laughing too. I would fall off the table if I wasn’t tied down. I’d stop her if I could, but I simply can’t do anything about it.

The treatment gets worse. She starts rubbing the palm of her hand over the tip of my penis. I’m screaming. I can’t stand it. I so want her to stop. But, as she has told me several times, there’s no safe word, because there’s no way I can get hurt. It’s not like some BDSM practices in which one could be injured.

That’s not entirely true. One time, she rubbed my glans like that, but without oil on her hand. The next day, I had a sort of burn, or chaffing on my glans that took a few days to heel.

She keeps going. I’m screaming. I’m laughing. I’m writhing out of control. My wrists hurt where I’ve pulled hard against the bondage. I know the drill. She’ll stop when my penis becomes soft. Not before. The damn erection won’t go down. I guess it’s because of the continuing stimulation. She keeps going.

One time, I ejaculated a second time during this part of the process. But most of the time, it’s just torment. I hate it but I love it. Go figure!

Q-Tips

My wife got a Covid test, and it gave her an idea.

We have tried some crazy things, but this has to take the cake.

Her idea was so weird that I just shut her down right away. I said “No fucking way,” with a laugh.

But the idea was gnawing at her. She started pestering me about it, the same way I’ve pestered her about some of my ideas.

Finally she talked me into it.

Her idea is that we should shove Q-tips into each other’s peeholes.

Since it was her idea, she went first.

After getting her all wet and slippery with my tongue, I spread her inner labia with the fingers of one hand, and tried inserting the Q-tip into her peehole. It went in less than a half-centimeter, and she said it was too scratchy. I dipped it into some of her ample pussy juice and tried again.

She was kind of wincing, which made me really want to stop, but she insisted that I press on. I got it into her about three or four centimeters, and she reported that it gave her a strong ‘gotta-pee-like’ feeling. We left it there, and I focused some attention on her clit, by rubbing it lightly with another Q-tip. She went into immediate orgasmic convulsions. Knowing her as I do, I kept up the rubbing with the other Q-tip, and she orgasmed again. It was fun watching the Q-tip sticking out of her peehole bob back and forth as she came.

After she calmed down, I pulled it out, perhaps a little too quickly. She kind of squeaked, telling me that pulling it out like that stung. Oops.

Now, it was my turn. She had me lay down. It didn’t take any convincing to get me erect. I was already hard in anticipation.

Have you ever had sex that’s so good, or maybe freaky, that you start shivering? That’s what happened to me. The thought of having a Q-tip jammed in my peehole simultaneously excited me, and scared me, and my body started involuntarily shaking. My lovely wife found that particularly exciting.

She grabbed another sterile Q-tip, and introduced a half-centimeter into my peehole. It was immediately ouchy. I told her, and she responded by pulling it out, coating it with her left-over pussy juice, and pushing it very slowly back in. It stung a little bit, but not very much. She tried twisting it, which caused me to yell. That hurt! Finally, with no more pain, she got it half-way in. I took a look down at my penis with that Q-tip sticking out, and it sent me over the moon. Or more specifically, I just started pumping out cum with one of the strongest orgasms I’ve had in a while. Mind you, she had never even stroked my cock.

I was scared to death that the Q-tip would block my cum. I have no idea what might have happened if it did, but the semen simply oozed out around the Q-tip.

She pulled it out. Ouch! Ouch! Ouch! That really stung, even though she did it slowly and gently.

The next day, peeing was very difficult. My urethra was stinging like crazy. She reported the same thing. A couple of days later, we were back to normal. We have decided not to try that experiment again!

[Note to you, dear reader: If you absolutely must try anything like this, be very careful about infection. Keep everything sterile. Avoid even the tiniest sharp edges to prevent tearing the very delicate urethral lining. While some people find they can go years with untroubled urethral play, those who have had infections will tell you it can be very, very severe. It’s like Russian roulette. You never know if or when it could be you in the hospital emergency room trying to explain how you got such a severe infection.]

Pussy Slapping

All you people here in California are crazy! Especially my younger cousin. I only get to see her every couple of years, but when I get out here, she always has some nutty idea to try out.

This time she wanted me to get naked again. We’ve done things before, you know, mutual masturbation, licking each other’s pussies, and so on. I’m so glad she instigates such things, because if it were up to me, – well I would have been too shy to suggest such things.

So this time, I was in her room, and she suggested we get naked. I didn’t know what she had planned, but I was all for it.

She was as beautiful as ever. Me, I don’t know, people tell me I’m ‘hot,’ whatever that means, but I think I’m average at best.

Then the fun began. She announced she wanted to play with vagina slapping. She had this theory that a girl could get off that way. I was kind of nervous about it. Might it just hurt and not be fun at all?

She was willing to go first. After trying a couple of ways to lay on the bed to give me maximum access to her pussy, we found that laying on her back, right at the edge of the bed, with her feet on the very edge and her knees up high was best.

I figured it would be a good idea to lick her clit first to get her ready. She did not object. I enjoyed the taste of her girl juice. It’s the only girl juice I ever get. Or, have ever gotten, so far. I could feel an orgasm building in her, and was all set to stop. She said “Stop” first, and put her hand between my tongue and her puss. We must have gone just a bit far, because I could see she was making all kinds of faces, and I felt her legs jittering. I believe she almost had an orgasm, or had a sort of mini-orgasm.

I let her settle down a moment. I was concerned she might not want the slapping now. You know how a person’s mood can change after orgasm, right? I know some women can have orgasm after orgasm. For me It’s happened a couple of times, but for the most part, me and my cousin are one-time-cum girls.

Quietly, she said, “Slap me.”

I started very gently. She said, “Harder.”

I built up the pressure, and she seemed to be enjoying it. I was still hitting her vagina light enough that I don’t think I was hurting her. I modified the way I was hitting so that my middle finger was banging right against her clit. She said, “Mmmm.”

I switched my hand position so now my middle finger was hitting right on her asshole. Bang! That did it. She was orgasming so hard I felt I had to wrap my arms around her to keep her from falling off the bed.

After she settled down, she told me that it was a particularly exquisite orgasm because it was what she called a ‘ruined orgasm.’ She explained that she really wanted me to keep hitting her pussy and asshole when I quit to hold her legs so she wouldn’t fall. Somehow, an orgasm that is finished without ongoing stimulation is stronger or better, she explained.

Now, it was my turn. She started slapping, and it was hurting a little bit. But there was some sexiness in it too. As she was doing it, I found myself staring at her pretty breasts that were shaking slightly with her slaps. Who knew I had a lesbian streak in me? My vagina started to sort of tingle, almost an itch under her slaps. Then she got me one time directly on my clit. That fucking hurt! But not really. Or I should say, only for a moment. Because the next moment, I started feeling my legs shaking. Really shaking. Like jittering, shivering, or kind of convulsing. That’s never happened to me before. Oh I guess they shake a little when I orgasm, but not like this. Was it out of fear? Pain? Or just some kind of sexual energy? I have no idea, but I do know what happened next: I had the biggest orgasm of my life. My cousin kept slapping as I was cumming. My big orgasm turned into a sort of double-orgasm. Just as it was ending, it started up again. There may have even been a mild third wave.

After a long recovery period in which we both stayed naked, laid in each others arm on her bed, and talked about everything in the world for an hour or so, we showered – together – dressed, and spent the rest of the day with family.

She promises that the next time we get together she’ll give me a ruined orgasm. I’m so looking forward to that!

Peehole Temperature

I don’t know whether my sister believed me, or just wanted to go along with it. Furthermore, I doubt she was really worried about having COVID-19. We’ve both been careful, knowing that at our age, we’re relatively safe, but could infect more vulnerable people.

So any way, I told her that we should take each other’s temperature.

Now, I’ve been interested in urethral play lately, so I proposed that the best way to take temperatures is to insert thermometers in each other’s peeholes. She said “Sure,” so I knew immediately she was onboard with it.

We took our clothes off. Or, because it’s more celebratory, she took my clothes off while I took hers off. I was immediately erect, and as I found out a minute later as she laid down on the bed, she was immediately wet.

Now, one doesn’t just jam an old-fashioned glass thermometer into one’s sister’s peehole. I could imagine that would be uncomfortable. So, I took considerable time noticing her inner labia by fondling them as best as I could considering how slippery they had become. Finally, I spread her labia far aport, got a good look at her little tiny peehole, and slowly introduced the thermometer.

She reported that it stung a bit. When I started to pull it slowly back out, she said, “No, keep going.” I pushed it in a full two inches, feeling the resistance as it passed her urinary sphincters. She started orgasming right away, with the thermometer bobbing back and forth a bit with her internal contractions.

Next it was my turn. She got me good and hard, almost going too far to where I would have ejaculated. Then she greased up the thermometer with her pussy juice, and pushed it slowly deep into my erect dick. I came. What else could I do? The pumping just started up automatically. I was glad it was an anal thermometer, the kind with an enlarged bulb at the end because it blocked the semen in my urethra as my body was trying desperately hard to eject it. But it was locked in, and that caused my contractions to be twice as strong and last twice as long. I wasn’t expecting that, but it didn’t hurt a bit, and was absolutely fascinating. I was kind of afraid that the internal pressure would hurt my body, but no, all was fine.

It did sting slightly when I peed for the next day or so, but otherwise it was a wonderful time for a shelter-in-place brother and sister.

Peehole Play with Katie

I had fantasized about this for a while, and now it was happening.

My friend Katie has had a fascination with peeholes for a long while. So have I. That’s not how we met, but it bonds us. Well, other things bond us as well, but we’re both peehole freaks, and we know it!

We’ll find good pictures on the internet of peeholes – both male and female. We’ll text them to each other. We’ve examined the outer surfaces and first couple of millimeters of each others’ peeholes in detail. However, until now, we’ve never really played with them.

What with COVID and all, we had the whole afternoon to ourselves, and nothing to do. It was time to break out the toys.

She had found a Sharpie marker. You probably know the kind. They’re about a half-inch (13mm) in diameter, and taper to a smooth blunt point at the back end.

I had ordered a thing on the Internet that frankly scared me. It was called a “peehole stretcher.” It was three blunt prongs about two inches (50mm) long fastened into a circular frame about 1.5 inches (35mm) in diameter. The prongs are attached to thumbscrews, so initially, they’re bunched together in a little two-inch long bundle about 3/16 of an inch (5mm) in diameter. With the thumbscrews, they can be cranked so that they become further and further apart.

Using three-prong urethral (peehole) stretcher

The moment I saw this $62 item online, I knew I had to have it. Now, I’m not much into pain, but the thought of my urethra being spread open was so amazing that I masturbated and came a moment after seeing the listing. I bought it.

It arrived a couple of weeks ago, but until now, It just sat in its plastic bag, never used.

Katie and I were going to have a very special peehole celebration. First we ate a nice lunch, drinking lots of tea. We knew that urethras are subject to infection, so we figured peeing afterward would be a final step in our health protocol.

She and I turned down the air conditioning so it would be warm enough. We took off all our clothes. She did a little dance, making a point of showing me her little pencil-eraser nipples, all hard, with little goosebumps around them. She lifted her breasts in her hands in an inviting way. I was immediately erect. Katie wasn’t done. She made a point of wagging her ass in my face, and spreading her butt so I could get a close up view of her puckered pink asshole. I caught a whiff of her sweet anal gland fragrance. Until meeting her, I never realized an anus had such an inviting scent. Katie momentarily placed a fingertip against her anus. I can’t explain why, but seeing that really turns me on, as if I wasn’t turned on 100% already.

Now, it was time to get down to business. We used both hydrogen peroxide and rubbing alcohol thoroughly soaking our toys, our fingers, and our outer peehole areas.

It seemed interminable waiting for the alcohol to dry.

We decided we’d ‘do’ Katie first. She got on the bed and spread her legs. I figured a little foreplay would be a good way to start, so I ran my fingertips ever so lightly over her cheeks, her forehead, then her ample breasts, and finally her little nipples, receiving an exclamation of delight. I then proceeded down her body, ever so lightly brushing my fingertips over her sides, her stomach, then jumping to her upper legs, and finally gave her inner labia some attention. She opened her legs wider, and in a moment, her clit became visible. I only gave that a little attention. She orgasms easily. Like most men, and some women, once she orgasms, she’s kind of done – usually. So then I ever so gently fingered her anus, just brushing my fingertip around the opening, but not in it. Finally, I pressed a finger in, but only a quarter-inch (6mm) or so. She loves that, but I think I love doing it even more.

Unfortunately, that meant I had to go through the whole alcohol-on-the-hands procedure again. As it was drying, she fondled my balls gently within my scrotum, which is yet another thing that I truly love.

Finally, we were ready. She got back down on the bed, and I coated the Sharpie with a liberal amount of coconut oil. I had some difficulty holding her inner labia open due to all her wetness. They kept slipping away from my fingertips. After quite a lot of messing around, trying to gain access to her peehole, I finally had good access.

I pressed the back end of the Sharpie against her opening. Moving very slowly, I finally slipped it a very slight amount. She kept making squinting faces like maybe it was hurting, so I kept stopping, asking “Is it OK?”

“Yes, wonderful. Keep going – but slowly.”

Stopping to put more coconut oil on the Sharpie, I then had to struggle to get her inner labia open again with one hand, so I could reintroduce the marker. It slid in with moderate resistance. I think I finally got it in about an inch, maybe two (25-50cm).

“Ah, OK, that’s starting to… well, not quite hurt. I think you’re pressing right against my sphincter. It feels interesting. Like I’ve gotta pee, but nicer.”

I started to pull it out.

“No! Wait. Let me fully experience this.”

For a while, I held it still within her urethra. Then, I thought maybe a little vibration would be nice. Gently, I started a little push-pull motion.

Katie immediately went into a crashing orgasm. I could feel the pulsations on the end of the Sharpie in my fingertips, which almost triggered a spontaneous orgasm in me.

After she settled down, I asked if she was still gung-ho. I though maybe she’d have a mood shift after orgasm, like us men do.

“Oh, no, you’re not getting off the hook that easy, Buster,” she announced.

I was delighted, but also scared. My penis, which had been hard the whole time I was working on Katie, went soft.

After another coating of alcohol on the end of my penis and on her hands dried, she started putting some coconut oil on my penis and then working it in with a good overall stroking. I was still scared about what was to come, but I did become erect again under her ministrations.

Once I was fully erect, she put some of the oil on the three prongs, and brought the contraption to my peehole. She wiggled it a little this way and that, and it slid a quarter-inch (6mm) into my penis. It didn’t hurt or anything. It felt interesting. Rather nice. But it was scaring me more than I would have admitted. However, there was no hiding it from Katie. My legs started involuntarily shaking.

She asked if I wanted to continue.

“Hell, yes!”

It was scaring me, but also intriguing and delighting me. Slowly, ever so slowly, she got the thing all the way 50mm (two inches) down into my dick. I felt a slight sting, but so slight I could barely notice it.

“OK?” she asked.

“Totally,” I said with a shaky voice.

She started working the thumbscrews. Ever so slowly, the prongs were moving away from each other. At first I didn’t feel much of anything. My penis was still rock-hard. My legs were still shaking.

She continued to unscrew the thumbscrews. Now, I could feel a little pressure as it was expanding my urinary opening. Not pain, just pressure. And it was wonderful. I’ve never felt anything like it. I wanted more pressure.

“Keep going.”

She did. Now, the pressure was turning into pain. I didn’t say anything to Katie, and worked at not letting it show on my face.

Now, normally, I’m not much of one for pain. I mean, I even trim my toenails carefully, in case it might hurt. But on this occasion, the stinging that was going on with my penis was positively erotic. Yes, it was pain, but by gosh, it was something else too.

I think Katie knew I was at some sort of limit, so she stopped turning the screws, and just studied my face. I lifted my head up, so I could see the end of my dick. There it was, with my peehole propped wide open. What an interesting and erotic sight!

“More, please.”

She turned a thumbscrew another half turn. I screamed! The pain went on the scale from one to ten! What a fucking sting!

She immediately undid the thumbscrew, and then the others. As she was loosening the device cum just started pouring out of me. It was the weirdest orgasm of my life. I don’t think there was the usual pulsing, yet it was a very, very strong orgasm.

With relief, I felt her slip the stretcher out of my penis.

Something was different. I had just ejaculated, but I wanted more. This had never happened to me before. I asked Katie to jerk me off.

“Really?”

“Yes, oh yes, please,” I practically begged.

So, putting more coconut oil on her hand, she wrapped it around my dick, and started jerking me off with an ordinary although oily handjob. Within fifteen seconds, I ejaculated again, and it was as strong as the previous orgasm, although this time, the pulsing was strong and seemingly continuous for a good several seconds.

I calmed down and then she asked if I could do her again. I was delighted, and reintroduced the Sharpie, giving her a good long urethral fucking, resulting in a second orgasm.

Katie and I compared notes the next day. We both discovered that urethral play results in a stinging sensation while pissing the next day. Still, we plan to do some more. She wants me to modify the stretcher so I can try it on her, and we’re going to buy some more online urethral toys. I think I’d enjoy having a catheter stuck all the way into my bladder. We’re looking at some little tiny vibrators on cords that can be pushed deep into one’s urethra. How exciting is that?

[Note: This memoir is presented for your entertainment. You do not need to engage in urethral play. There are a million ways to have good orgasms without ever introducing anything into your peehole. It is totally not medically advisable and truly dangerous. Some urethral infections can last a very long time. They can cause strictures or incontinence, requiring surgery to correct. Some people have died from urethral infections.]

Getting the Cum Out To Get To the Good Stuff

After the cum is out - ejaculation

My girlfriend Emily and I have been together for ages, but never married. We have a massage table in the den. Initially we used in the usual way, to give each other massages. Of course they were happy ending massages – for both of us.

Over time, what we do with that table has evolved. Lately, there are a couple of things we do which you might consider highly unusual. Now, don’t judge, OK?

Emily likes anal massage. Using a lot of coconut oil, I’ll put my finger slowly in her ass, and massage all around inside. It gives her orgasms. Not just one usually, but two or three. They are kind of connected together. Mind you, I don’t touch her vagina at all, at least not while we’re doing this, yet she orgasms big time. I know exactly what’s going on, because I can feel her contractions as she’s orgasming. Her ass actually squeezes my finger quite firmly.

Then it’s my turn. For this, she needs to tie me to the massage table. She has some bandanas that she uses so my wrists and ankles are tied to the corners, and I can’t get away.

By the time I’m all tied down, my cock is totally hard, and usually sticking straight up. When I masturbate or whatever, my dick mostly lays against my belly, but Emily has me so excited, it must be one notch harder than normal, and literally sticks up in the air like a six-inch flagpole.

She grabs it and jerks me off. I always cum way too soon. You’d think this is where the fun would be over, but it’s just beginning. Emily says she has to get the ‘cum out’ or ‘get the cumming out of the way,’ so her real work can start.

She doesn’t clean the cum up. It’s all over my cock and balls, and belly, and her hand. Here’s the thing: She just keeps going, as if I hadn’t cum at all.

It’s horrible. It’s the worst tickle-like thing in the world, as any guy who has had post-ejaculation stimulation can attest. I really want it to be done. I squirm. I yell. I laugh. But no, she just keeps going. For some reason, maybe it’s the ongoing stimulation, my cock stays hard. After awhile, it’s not quite so terrible any more. I can almost stand the ongoing attention. She knows it’s dying down, so then she kicks things into high gear.

She puts more coconut oil on the palm of her right hand. Then, while holding the shaft of my cock in her left hand, she starts rubbing that oiled palm over my cockhead. I’m immediately in fucking agony! She’s laughing sardonically. Sadistically. Like a crazy woman. I’m laughing too, between my screaming, squirming, and yes, even convulsing. This is the most unbearable thing a man can feel. And yet, it’s enjoyable in its own way.

Not only does it have that miserable tickle-like, almost pain-like effect, but I also feel like I might cum again, so there’s some pre-orgasmic sensation mixed in. And one more thing: I’ve really got to pee. I can’t hold it in. I just can’t. I end up peeing all over the place. Emily is of course prepared. We have plastic sheeting on the table and on the floor. She knows to move her face away, and makes sure her palm is still rubbing over my peehole, so the squirting is diverted. She just keeps going. Most of the time the involuntary urination is just a squirt or two, but sometimes I let out with a real soaker. Sometimes, I ejaculate a second time. Every now and then, I literally can’t tell if I’m cumming again or pissing. The intensity of the rubbing is just that extreme. I wish I had a safeword I could say to make her stop, but since there’s no physical harm that can be done, other than perhaps a bit of chafing if we hadn’t used enough oil, we have agreed not to have a safeword.

Like all good things, it can’t last forever. Emily has decided the session is over when my cock goes soft. This can never be soon enough for me. But unfortunately, with all that stimulation, my penis stays hard an extra long time.

I swear I’ll never let her do that to me again. Then, about a week later, I can’t wait for our next session.

How I Attained Peegasm

So far, I’ve attained ‘peegasm‘ also known as ‘pissgasm’ only twice. Every now and then, I’ll try it again.

The goal is simple, to emit urine and semen at the same time. In practice, it’s so nearly impossible that it’s exactly the kind of challenge I like.

The male body is specifically designed to block the flow of urine while ejaculating. The urinary sphincters clamp down tight. My job is to thwart that. So, after trying a few different things, I finally settled on the following technique:

1. I wait until my bladder is uncomfortably full. One time I went too far with this and found out the body will start leaking out spurts of urine despite all efforts to keep it in. As I went running to the bathroom, urine spilled out on the floor leaving a trail behind me.

2. Then I start jerking off. As the ‘gonna cum’ feeling starts to build up, I try to maintain that feeling, but also try to let go and pee. Almost always one of four things happens:

a. The orgasm that’s starting to build subsides.

b. The urge to urinate subsides.

c. The piss starts flowing but I don’t cum.

d. I have an ejaculation, but didn’t pee.

Of course the last variation is the worst, because then the fun is over.

3. I go through a few cycles of building up to orgasm while really feeling the urge to pee, hopefully avoiding ejaculation until I’m actually urinating. Quite often, I’ll start to urinate, but the orgasm doesn’t happen, or the orgasm will shut off the flow of urine.

I’ve tried letting the orgasm happen, then opening the pee valves. That doesn’t work.

I’ve tried stimulating my cock really vigorously while peeing, hoping to instigate an orgasm. That mostly doesn’t work, but sometimes the orgasm will happen. Unfortunately, that shuts off the flow of urine.

The magic seems to be mental. You want to just let go. To really relax the urinary sphincters.

The first time it worked, my wife was asleep inside the house. I was outside on a hill in a cherimoya (a rare edible semi-tropical fruit that tastes like vanilla ice cream) orchard late at night at the edge of my front yard. There was traffic on the road nearby, but unless someone shined a spotlight sideways right at me, they would not see me from their cars. I think this semi-exhibitionism heightened my experience and may have made the peegasm possible.

I was standing, jerking off vigorously, and really, really had to pee. And then it happened. The pee was flowing, and then, it switched from a steady stream to orgasmic and very fluid spurts. I couldn’t see clearly in the dark, but I’m certain I was ejaculating while still peeing.

The other time, I was sitting on the edge of the bathtub. The tub was dry. The light was on, so I could watch clearly. Again it started with urine flow. That smooth flow was interrupted by spurts of white cum. ‘Interrupted’ isn’t quite the right word. The urine flow never shut off. The flow became chunky as the output was the mixed thin yellow fluid of urine interspersed with white sections of cum. Very exciting! It was a super-strong orgasm. Oddly, when it was over, I still had quite a bit of piss in my bladder, yet I couldn’t continue peeing for a minute. Finally, the muscle tension let go, and I was able to finish the urination.

That’s it for now. I’ve gotta keep practicing. In fact, I have a male friend who I think I’d like to practice this with. I’m not sure exactly what we’d do or how we’d accomplish it, but I can imagine it might start with us both sitting on the edge of the tub, but holding huge amounts of urine in our bladders, and maybe wanking each other, with a lot of feedback, like “Hey, wait a second…” and “OK, go on…” and so on.

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