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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.

Sadistic Sharla

I’ve been seeing this woman professionally. I mean, since my wife died, I’ve been missing sex. Now my wife wasn’t all that wild, but what I miss, mostly because I never got it, is wild sex.

So I heard about Sharla. The first time, she greeted me at her door wearing a flowery dress, and after collecting her $120 cash, she led me into a large back bedrooom. It was an amazing place. Dark, but I could see literally hundreds of sex toys hung on the walls, on counter tops, and stacked in the corners.

Sharla, who is short and skinny with tightly cropped curly hair, and so black that one would think she’s first generation African, has a reputation. That is, one never knows what’s she’s going to do. What sex toys she might use on a person.

My first time was so fucked up that I swore I’d never come back. The second, third and fourth times, same thing. Yet here I was. This time, she greeted me at the door stark naked. You’d think she’d be worried about the neighbors glimpsing her in the doorway. She didn’t seem concerned at all. When I asked, she laughed saying half of her neighbors, male and female, are her clients. “The other half hate my guts, so it can’t get any worse,” she laughed.

I was embarrassed just going in her door fully clothed. Like, ‘What must the neighbors think of me, knowing what Sharla does for a living?’

It was very enjoyable just seeing her young naked body. She has small tits with big super-black nipples. To me, that’s a real turn on. She keeps her vaginal area totally hairless.

She led me to her ‘dungeon’ as she calls it, and had me immediately remove all my clothes. Even though I had done it several times before, I still felt a momentary pang of reluctance getting nude in front of her, even though she was stark naked. I wondered what she must think of me. Probably that I’m ridiculously white. I really should get out in the sun more.

She had me lay face up on her table, and tied my ankles and wrists with restraints. She told me today’s safeword was ‘carrot.’ I well-knew that I’d better remember that, because if things got too intense, as they very well might with Sharla, I’d better remember the word!

My penis was not hard. Too much fear. I was literally trembling in fear at what she might do. And that, believe it or not, was the biggest attraction. Knowing she might do anything, and there was nothing I could do about, made me terribly horny.

Today’s lesson started with some very light interaction with a feather duster. I wasn’t expecting that. She kept it so light, that at times I couldn’t quite tell if she was touching me with it or not. She started on my cheeks, then my nipples, and finally my penis. The fear was still there, but I was now as erect as a man can be. Every time she touched my with that feathery thing, my cock jumped an inch off my belly. Then it got even harder, and stayed off my belly, sticking straight up. I didn’t even know it could get that hard.

With my restrained left hand, I tried to cop a feel of her vagina. She backed away.

I wasn’t looking at most of what she was doing, even though my head was propped up so I could see if I wanted. But I had to look when I felt a light but cold and wet touch on the very tip of my dick. She was holding a tube of KY and rubbing it around my peehole. Then, surprise number one, she squeezed the tube right into my peehole. I felt my urethra expand with the KY jelly squirted inside.

She rummaged around in a drawer for a moment, then grabbed a little contraption. She also had a bottle of hydrogen peroxide, and was sterilizing it. Seeing what it was, my erection weakened immediately, and I started trembling again. It was a three-pronged affair some wingnuts. It was just the right size to fit into a guy’s peehole.

And that’s what she did with it. She slowly and gently inserted it into my peehole. It stung a bit, but not too much. She left it there for a moment for me to get used to. Then she started turning the screws. Wingnuts, actually. The prongs moved away from each other. At first, no problem. It felt kind of nice having my peehole opened up like that. I could even feel the cold air in there, in a place where no one ever feels cold air. My penis, with a mind entirely of it’s own, grew rock-hard again.

Sharla continued to turn the screws. Now, it was starting to sting a bit. She continued to turn the screws to the point where I was wincing and I was saying, “Too much!” She laughed maniacally and continued to turn the screws very slowly. Oh my God, it was starting to genuinely hurt. She reminded me that I knew the safeword. But, I also knew from previous experience if I actually said ‘carrot’ the session would end immediately. On top of everything else, I was thinking about my $120. I didn’t want to waste it.

Just when I thought I couldn’t take any more, she quit turning the screws, and just left it there. My peehole was so stretched open! The pain was still there, but subsiding. With the thing still firmly embedded in the end of my dick, she had me scrunch up, momentarily lifting my butt off the table, and put a bunch of towels under me. She left the room for a while. This peehole spreader thing of hers was very much on my mind. It was still making me very sore, but also very horny. If she hadn’t returned when she did, I probably would have had a hands-free orgasm. I was wondering what it would feel like to have the contractions of my urethra thwarted by the gadget.

What she brought back into the room was a WaterPik of all things. One of those deals for cleaning your teeth with little blasts of water. She turned it on, and started squirting high-pressure thin spurts of warm water on my scrotum, which hurt a bit, but was also delicious. Then she moved up the underside of my penis, and finally was squirting it on the underside of the head of my dick. She had regulated the pressure just right, so it felt wonderful, almost like a highly-focused tickle where the water was blasting against my frenulum, then the head of my penis.

Then, Sharla did the unthinkable. She squirted the warm water directly into my pried open peehole. She was spraying it against the inside surface of my urethra. I felt some of the very warm, almost hot water go deep into my penis, but not so far as into my bladder. Occasionally it stung so bad where it was hitting my inner urethra that I felt what seemed like electric shocks. At the same time, I felt over-the-top orgasmic. She turned off the WaterPik, and I was cumming. My penis was wide open, so the cum didn’t squirt out. Instead, it flowed up, filling the hole, and then out and over the top of my penis. I felt the contractions against those prongs which were stretching my urethra open so wide, and it had a surprising effect. The orgasm kept going. The sperm had ceased flowing, but the contractions were continuing. After a few more, they subsided. Then they started up again. I had a minor second orgasm.

Giving me a minute to recover, she started loosening the screws. Boy, did that hurt! The sting as she released the tension was at least twice as much as when she was stretching it open in the first place. I guess one’s penis gets used to the pain and shuts it out. But now it was back full force.

Finally all the tension was gone and she slipped it out of my penis, which was now quite slippery with a mix of cum, KY jelly, and water. The towels she had put under me were sopping wet, and not the most pleasant thing to lay on, but that was the least of my worries. That’s because she had grabbed the shaft of my still hard penis in one hand, and was starting to rub the palm of her other hand over the tip. Over my glans. It was the worst tickle of my life. I couldn’t stand it, and said “Carrot.” She acted as if she didn’t hear.

“Carrot! Carrot!” I screamed as I pulled so hard against my restraints that my wrists were starting to ache.

“Oh, that safeword has expired,” she replied as she continued to rub my glans with the palm of her hand.

I was starting to freak out. This was just too much. My penis was starting to soften. I figured if it went entirely soft, she might stop. But it didn’t soften fast enough, and she just kept rubbing.

After a minute, she quietly said, “The new safeward is ‘turtle.'”

“Turtle!” I yelled.

Sharla immediately stopped. Then she untied my wrists and ankles and left the room for a few minutes so I could collect myself. I couldn’t even move so I just stayed on the table for a bit, my ass still propped up on the wet towels. It was, without a doubt, the most intense thing that had ever happened to me. Finally, I got up, got my clothes back on, and drove home, convinced that I would never, ever subject myself to that again. And yet, I have made an appointment for Thursday and I can’t wait to see what Sharla is going to do next. I have masturbated to wonderful orgasms remembering that occasion several times.

Sliding Around on the Bisexual Scale

In late middle school I knew I had a problem. I knew I was quite attracted to boys my age, and not so much to the girls. Frankly, I wasn’t attracted to girls at all. They scared me because I didn’t know what to make of them.

I remember wearing sunglasses so that I could look at the boys swimming in the public pool without them knowing that I was looking at them. On the rare occasion when I saw some pornographic pictures, I’d like seeing the erections, but when I saw a woman’s vagina, it looked like a wound to me.

Once I learned to masturbate, which I figured out on my own, it was images of boys that turned me on. The first time I orgasmed, only one clear drip came out. I wasn’t very informed about sex, but I sort of knew what it was. I was also freaked. Like most kids in those times, I was under the impression that masturbating was a very bad thing. I didn’t quite know why, but I knew it was bad. Everyone said so. “Thanks parents, thanks society!” – I say cynically, now.

As “bad” as it was, it didn’t stop me from jerking off pretty much every day. That first time I came, I had done it by pressing the thumb and first finger against each hand against the sides of the shaft of my penis and moving up and down. For several months, I thought that this exact same grip was required, and did it that way every time.

Nothing happened with anyone but myself until high school. Then, I started jerking off with this very heavyset friend of mine. We took it to the point where we’d give each other handjobs. That’s all. I believe it was he who approached me about the idea of jerking off together. I wasn’t attracted to him, but he was a good friend. We did lots together, like talking endless about when we’d have cars someday and what kind they’d be. We both talked very authoritatively about girls, trying to insinuate we had experience, without actually saying anything.

Sometimes, while jerking the other guy off, we’d pretend his penis was a gearshift, and we were driving a car.

Diane came along. She was always talking about sex, and I know in retrospect she wanted to get into my pants. I was so oblivious that it never happened. But her brother, he was a late developer, he and I masturbated each other all the time. Soon he could get to the point where a drop of cum came out of him. By then, I had hairs around the base of my dick, and could cum in greater quantity. He and I would take the hollow pieces of a plastic chess set, and see how much semen we could pump into them. The last time I saw Benny, he was able to fill a pawn. I could almost fill a queen.

In my last year of high school, by now driving a beat-up old foreign car with a worn out transmission that required double-clutching, I met June. She was five years older. She was a small Asian chick who had the unlikely job of driving an 18-wheeler. I fantasized day and night about driving a big truck, and here she was actually doing it. I dreamed of trucking almost as much as of sex – still mostly with guys, however. That bit, about guys, was my big secret.

June looked a lot like Lucy Liu

One day, June said the company needed co-drivers, and the only thing required was a truck driving learners permit and being 18-years old, since there’d be a fully licensed driver in the truck. I was all over it, and got my permit the next day.

The first time out, we had a ten-wheeler with a ten-speed transmission. I was disappointed that it wasn’t an 18-wheeler, but so totally happy to be driving any sort of truck. June drove the first hundred miles. I was wondering if she’d let me drive at all. Then she pulled over and we switched seats. Because the old car I had, and because I had studied up on it, it didn’t take me long to figure out how to shift gears in that truck. June was very careful to instruct me in how to take corners so as not to run the back wheels over curbs, or worse. Still, I almost clobbered a stop sign while making a right turn. After that first 100 miles, she never drove again. She was delighted to have me do all the work.

They were two-day runs. We had to stay in a hotel overnight. All the first afternoon, I was trying to figure out how that was going to work, and assuming we’d rent two rooms. It turns out the company would only pay for one room. Interesting, eh?

By the way, I have to tell you, I was finding Junie rather attractive. She was more like a boy than a girl in many respects. She had short hair for a girl, and fairly small tits. I especially enjoyed her mouth. She could swear up a storm, which I found rather impressive at the time.

So that night, we were in our separate beds, and talking. She kept bringing the conversation around to sex, which I was fully on board with. I was too shy to do anything more, but not Junie. Suddenly she threw off her covers, and climbed into my bed. Awkwardly removing our clothing, we started rolling around and kissing. She totally wanted to fuck. So did I. However, I couldn’t get it up. I know now it’s called ‘performance anxiety.’ Plus, all my life up until then, thinking I had to keep my gay side secret, I was very careful not to spring boners at inappropriate times, like in the boys’ shower at school. So, I had accidentally taught myself not to get hard around other people, even when it’s OK. June was disappointed, even though I was able to bring her to orgasm with my fingertips. To say I was disappointed would be a huge understatement.

On the next drive, two weeks later, we had an 18-wheeler with a Spicer 13-speed transmission. I was delighted. It was larger and harder to manage than I imagined, but I loved learning to drive that thing. We stayed in a hotel again, and that night everything worked perfectly! To my surprise, I found Junie very attractive, and had a great time. That first time, I kind of thought of her hairy vagina as unattractive. Not this time! I was happy to lick it, and loved the taste. I fondled her breasts for a long time as well, which not only did she like, but I loved. I ejaculated inside a vagina for the first time in my life.

During the next few years, I still thought I was hopelessly gay. In those years, that would have been a bad thing, or so I believed. Homosexuality was not as accepted, at least in my circles, as it is today. To satisfy my desires, I had occasional experiences in bathhouses, and with the occasional guy. I met a gay plumber. Unlike me, he wasn’t keeping it a secret. I was surprised he could be so open about it and remain functional in society. Carl was very attractive to me. Slight of build, and blond-haired. He was rather feminine in build, but didn’t act that way. In all other respects, he was a ‘guy,’ drinking beer, following sports, swearing, working hard at manual labor, and so on. When we got into his bed, I was suddenly very uninterested in kissing or oral sex. All I wanted to do was handjobs. Fortunately, he was understanding. We got together a few more times, and then drifted apart.

Carl bore a resemblance to David Spade

In my late twenties, I had sold a business, bought a motorhome and traveled around the country. I met various guys, and the occasional girl. One was Amy, a very small, curly-blond haired woman, not unlike a young Meg Ryan.

Amy was a handjob expert. She liked sticking her skinny little finger into my peehole, which kind of hurt, but felt very exotic at the same time. One time, I ejaculated while her finger was in there. It scared me, because I thought the cum had to come out, or I’d burst something, but no, it was just fine. In fact, the orgasmic contractions lasted twice as long. She wanted me to put a finger in her ass, which I did reluctantly. When I pulled it out, I noticed a sweet odor, not at all what I would have expected. I put it back in, and felt her contractions when she orgasmed from the attention my other hand was giving her clit. From then on, I was a big fan of anal fingering.

I met a rather overweight Inuit (Eskimo) woman. She was great fun, but I thought I deserved better, so I cheated on her. She threw me out instantly, which I’ve always regretted, because she was great company. The best conversationist I had ever met. Also, a sexual monster. She loved having cucumbers shoved into her ass, and taught me to enjoy that as well.

I hadn’t been doing much of anything with guys, except for Larry. He was 18 years old, mostly heterosexual, although still a virgin. He and I started giving each other handjobs on a fairly regular basis.

Then I met Cindy. She was a true nymphomaniac. Every guy’s dream, right? Not so! She wore me out. She’d want to fuck at 11pm when I was sleepy, but I’d comply. At first it was fun. But then she’d wake me at 3am begging me for more sex. And then at 7am, she’d gently wake me again, and – you guessed it – wanting more. I tried to dump her several times, but the tears would come, and I would relent. I introduced her to Larry, figuring he’d get his first experience with a woman, and I’d get some relief.

The first time was a three-way. I probably should have held back so Larry could have a normal first experience, but I didn’t. I put my finger in her vagina while he was fucking her, which she loved. He probably wanted it simpler, but didn’t complain. I mean, after all, he was having a great time. Then, when he was about to cum, I stick my finger in his ass. He orgasmed so hugely that he was shaking all over, and practically fell off the bed, almost taking Cindy with him.

They hit it off big-time. I lost Larry as a wank buddy, but also got rid of Cindy who was becoming a big problem. As the two of them rode off into the sunset, I cooled down for a year or so, being happy just to jerk off once or twice a day.

Then I met Carol, who drove me fucking crazy. She was a perfectionist, and it overflowed into trying to control me. Like while having sex, she’d keep saying, ‘unh, uhh,’ or ‘yes,’ guiding me in exactly what she wanted. The prudent thing would have been to dump her early, because she was rather bothersome. But instead, I found myself more and more drawn to her. She was very intelligent as well as intuitive, and although she could get intense at times, she was a great and helpful companion. That was 26 years ago. Carol and I are still happily married with two beautiful grown children, who, due to Carol’s way of guidance, are already very successful adults.

A few years ago Carol went through menopause and lost interest in sex. She knows about my bisexual background, and has encouraged me to play with guys whenever I like. She absolutely doesn’t want me to get sexual with any women, however. I’m not sure why the double-standard line exists in her mind, but it does. So, every month or so, I hang out with Tom, who is a few years younger than me, built like a Greek god, and loves exchanging handjobs.


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.]

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.


“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.]

Odd Sports Physical

I went to my mom’s friend for my college entry physical. Perhaps I should have known better. She’s a nurse practitioner. Cheryl is her name. She’s a bit on the heavy side, has graying hair, and most of the time wears a no-nonsense expression.

She did the physical at her house, which I suppose is a bit weird, but at the time, I thought it would be better than waiting around in a doctor’s office. They always run late, and that bothers the heck out of me.

I got there and she instructed me to strip down to my underpants. Cheryl did all the usual stuff: blood sample, listen to heart and lungs, weigh on the scale. All the while, she was asking me questions, like why I joined the baseball team when I’m so good at football. (I didn’t get a football scholarship, but did get a partial baseball scholarship.) I thought this ongoing questioning was unusual from her. All the time she had known my mom, she barely paid any attention to me at all, and I came to think of her as a mostly non-talkative person.

My mind turned away from Cheryl and what she was doing. I was on the verge of buying an old Harley, and was really excited about that motorcycle. It was all I ever thought about lately.

She asked me to momentarily remove my underpants. That brought me crashing out of my daydreaming. Perhaps I shouldn’t have, but I asked “Why?” I mean all the medical exams I’ve ever had, either I would leave my underwear on, or at most, they’d swoop down the front for a moment for nothing other than the briefest of a glance at my balls or whatever.

“Because a young man needs to be checked for everything, testicular cancer, included.”

“Oh.” I felt really weird about letting Cheryl see my dick. My ass too, for that matter. But what could I do? This was a medical exam after all. No big deal, right?

So, I stepped out of my briefs. There I was stark naked in front of my mom’s friend. Now, nudity has always had an effect on me. Thank God that the showers in high school were all in separate stalls, because I’d often get at least partial wood in there. The other guys never knew. And of course I didn’t know what was happening with them in their showers. I kind of wondered. Anyway, the thing was I felt like my penis might rise up in front of Cheryl, and that would be weird, and embarrassing to the max.

First she did the turn my head and cough thing. I felt a stronger possibility of erection. In fact, I was becoming very afraid my penis was starting to puff up a bit.

“No hernia,” she quietly half-muttered. It’s not like I was relieved, because I was pretty sure there was nothing wrong with me, anyway.

She had me lay on her ‘examination table.’ It looked like a massage table to me, but whatever. She reached out, and started scrunching around on my sack.

To my horror, that fucked me up entirely. My dick rose of its own accord, and there was nothing, absolutely nothing I could do about it.

“Um, I’m sorry…” I started to blurt.

“Oh, it’s nothing. Just proves you’re a healthy boy.”

She continued to feel my balls for quite a while. Under other circumstances, it would have been wonderful. I’d like to have a girl, I mean, someone my age, do that. My mind drifted to Marie, a beautiful Mexican chick at school. She was a girl I always wanted to talk to, but never could. Oh well, now that high school was over, I’d probably never get the chance for the rest of my life. Somehow in my mind, I started imagining it was Marie squeezing my balls back and forth like that.

Suddenly my mind shot back to reality. What the fuck was happening? I was rock hard as Cheryl was continuing to massage my balls. And, why was she taking so long? I was starting to feel that pre-orgasmic feeling one gets. Oh no! But just before it was too late, she let go of my balls.

Whew, that was a close one! I realized this was as close as I had ever come to ejaculating, without actually ejaculating. I was sure I’d be rubbing one out later to finish the job.

She turned away to a little table, grabbed something, then returned. “The schools are insisting that we test for STDs these days. This may sting a bit.”

I didn’t really grasp what she was saying. I was vaguely thinking she was going to jab my arm for more blood or something.

Suddenly, I felt her grab my still rock-hard penis in her hand, wrapping her fingers firmly around it. There was that getting-ready-to-orgasm feeling again. It came on me suddenly. And then, as I looked to see what she was doing, she jabbed a Q-tip about an inch in my peehole. That did sting! She could have warned me. But then again, I guess she did.

Now, it would have been nice if she pulled it out right away. But no, she kind of pushed it in a bit more, and twirled it around. It stung big-time! Finally, she pulled it out, and if you can imagine it, that stung even worse.

“Owww, Holy fu…”

But then it was over. The pain ended as quickly as it had begun.

“I’m so sorry,” she said. It had to be done. Putting the Q-tip into some sort of little container, she immediately turned back to me and grabbed my penis again.

‘Now what?’ I was thinking. What torturous thing did she have in mind next? But that’s not what happened at all.

Cheryl apologized for that pain, and said, “This might help.”

She held my penis, looking at it intensely, and kind of shifting it to one side then the other. It was still as hard as a hammer. It felt nice for her to hold it that way. Then, she slid my foreskin all the way back. It was intense. Almost bordering on a different kind of pain. She held it that way for a good few seconds. Then she pushed it back over the head of my penis. Then she pulled it back again.

“Checking for proper functionality.” she said, in that same low, almost to herself voice.

She did that ever so slowly about five more times. That was it. I couldn’t hold back any more. I tried really, really hard, tightening up every muscle I had, but it was hopeless. Cum started shooting out of me, all over her hand and my stomach.

“Yes, all good!” she said, this time brightly, and with a smile on her face.

“You appear to be in perfect health young man.” With that, she left the room, so I could wipe up the mess, and put my clothes back on.

As I walked into her living room, I thanked her for the physical while feeling very strangely about what had just happened.

Cheryl asked me not to tell the details of what just happened to my mother. I assumed she felt guilty about going way beyond the rules for this sort of thing. I assured her I wouldn’t tell. I mean, I’ve never discussed anything sexual with my mom. There’s no way I could bring something like this up.

The next day, my mom and I were sitting around the dining room table, just talking about this and that, when she said, “Cheryl says you’re really healthy.”

I didn’t catch her meaning.

“I mean Cheryl says she ejaculated you during your exam.”

I must have turned ten shades of red.

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Aquarium Tubing

aquarium tubing used for urethral play

I went to an auto supply store, and bought 2-foot (60cm) lengths of clear flexible plastic tubing in the following outside diameters: 1/8-inch, 3/16-inch; 1/4-inch (approx 6mm), 5/16-inch, 3/8-inch, and 1/2-inch (approx 12.5mm). The 1/4-inch tubing is very similar to the plastic tubing used to pump air into aquariums.

I rounded and polished the ends, sterilized them, sterilized my hands and the end of my penis, and started playing.

I didn’t even bother with the 1/8-inch tubing, starting right out with 3/16-inch. It went in nicely, although it could have been a bit more flexible. It took a little while to push it through my prostate and urinary sphincters. What a remarkable feeling it is to have your prostate area invaded like that!

This was such an outlandish experiment for me that I was literally shaking. I was shivering as if it was cold in the room, but it was plenty warm.

I pulled it out, and went to the 1/4-inch. That went all the way in easily. I noticed that once it was in my bladder, I had a kind of shuddering effect. The pee would flow through the opening, then the tube would be pressed against the wall of my bladder, shutting off the flow. Then with the pressure off, the tube would float away, and once again pee would flow. This shuddering against the soft bladder wall happened at a rate I’d guess to be around 4 – 6 cycles per second.
Next came the 5/16 tubing. It was a big challenge getting it all the way into my bladder, but I managed it!

The 3/8 could only be put in about 7 inches, to about where my penis disappears into my body. It just would not go any further, and I wasn’t willing to risk injury.

All in all, the afternoon was tremendous fun. However, a few weeks later, playing with inflating my bladder with water, I gave myself a huge infection. I recovered after a week, but have decided none of that is worth the risk. I have found much better ways to have sexual pleasure and orgasms, such as described here: Advanced Male Masturbation

She Loves Peehole Tonguing

She loves peehole tonguing

I’m kind of a weird case, I suppose. I just love it when someone will get me all sexually excited, so my inner labia loosen up, and then they can try to stick their tongue into my peehole. Of course, they can only get in a few millimeters, but I love when they try. Within short order, I’ll orgasm. And not only that, I’ll cum over and over again, sometimes for like five minutes.

I have had a couple of mild infections from this, but they itch or sting a little bit for a couple of days, then they go away.

It doesn’t matter who does it. It can be a male or female, young or old, fat or thin. No matter what, I just love it!

For some of my friends with whom I’ve done this, I’ll reciprocate. It’s the men more than women who like their peeholes tongued. I love a hard penis just a little way in my mouth, and then there I am jamming my tongue into their peehole. Sometimes with men, I’ll feel sudden resistance, as my tongue is pushed out by the flow of cum.

For fun a couple of times, I tried blocking the cum in a man’s urethra with my tongue. The cum always gets out anyway, but the guys seem to particularly enjoy that.

Yes, I’ll swallow. I guess it doesn’t taste especially nice, but I rather enjoy it anyway. I’m sure you know this, but there’s quite a difference from one man to another. Some have cum that tastes bitter, some salty, some almost sweet.

I do enjoy putting my tongue in the occasional woman who will let me do that also. I have induced some to involuntarily pee. No, I don’t swallow that! I have brought many to orgasms. Here’s the interesting part: Most women will refuse to have their peeholes licked, but once they acquiesce, they want it every time after.

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