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.

The moment I saw this $47 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 it's 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 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.]