500 strokes - Wet Canings with Jack

By Steve W. February 2000

This session lasted from 13:00 until about 20:30. Plenty of time to play and rest between short sessions. Plenty of time to build up to some serious C.P.! Plenty of time to build up for some serious piss fun too!

I'd been told to wear only a particular pair of shorts when opening the front door to Jack when he arrived. These are red satin running shorts but they have no lining so it's impossible to prevent my cock from peeping out of the right leg of the shorts. Good thing my front door is not visible from the street but I still feel pretty foolish wearing the shorts, which I guess is why he tells me to!. I'd also been instructed to drink half a litre (slightly under a pint) of liquid in each hour since 12:00, so I knew this was going to be a wet session again. By 13:00 I'd drank over a litre of squash and I managed to stick to the half litre per hour rule for the whole session.

After we'd chatted and drank for a while, and Jack had taken a shower, he told me to stand up and then gave me a hand-spanking, gradually taking my shorts down between each group of six spanks. Once the shorts were off, he got me to lean over my stool and gave me six strokes with almost every implement I'd laid out. This amounted to a total of 102 strokes in all, plus a few hand spanks thrown in from time to time. By the time he'd done that I was bursting for a piss but I knew from previous sessions with Jack that this would not be allowed. As it turns out, he was bursting too and got me to kneel on the floor (suitably prepared with waterproof sheet and towels) and then proceeded to piss all over my chest, cock and legs, followed by my back. Being soaked I began to get cold so I was allowed to take a warm shower and then dry off ready for the next activity.

Jack said that he wanted to set a target of 500 strokes of the cane by the end of the day. I wasn't too sure about this and was hoping that the 100 or so I'd already had would count towards our previously agreed target of 500. Anyway, I said we could give it a try, knowing that Jack is not the type to break the skin. He suggested that I put some tight jeans on for the first hundred strokes. I have a pair of very tight stretch grey Wrangers so I quickly went and put them on and got back over the stool. Jack liked the jeans a lot, they do make my butt look cute. The cane was given quite hard in groups of ten. After each ten Jack changed sides so half were given back-hand. Not as accurate as the fore-hand strokes but much better than most guys' back-hand cane! At the end of the hundred my butt was really hot and tingling in spite of the protection offered by the jeans. But Jack had a way of cooling it down, he stood directly behind me pissed all over my butt, soaking the jeans and causing me to get hard again. Knowing it was permissible, I used the time to relieve myself too, even though I was hard. I love the feel of piss-soaked jeans clinging to my butt and legs! I was then getting a bit cold again so was allowed to remove the jeans and dry off. Jack then attached some clover-leaf tit-clamps to my tits. Not having had any tit-work for a long time they were agony right from the start, especially when he hung a ten-ounce weight from the chain connecting the clamps together. My tits have always been very sensitive but rarely fail to raise an erection when played with! Anyway, once the clamps and weight were on, it was back to the stool for the second hundred strokes with the cane. Same pattern as before but this time without the protection of the jeans. OK they stung more, but they didn't seem much more challenging than with the jeans on. Maybe Jack had adjusted the weight to take account for the lack of protection. My butt was certainly stinging at the end of the hundred. I was told to stay in position. Then I felt a well-lubricated dildo touch my butt-ring! I hardly had time to enjoy the feeling when it was inside me and I was enjoying that feeling instead! After he's fucked me with the dildo for a while he took it out and, as he hadn't told me to stay in position I stood up. As I did so the tit-weight fell off the chain and then Jack took the clamps off. Wow, that hurts! Nice hurt though! Then Jack reached for a condom so I knew I had to get back over the stool and I got a nice slow screw for about ten minutes.

200 strokes done, 300 to go. Time for a rest, a drink, watch a video and generally re-compose. After half an hour Jack said he was needing to piss but, as I was eating a snack at the time, said he would wait for a while. When I'd finished eating he got me to put on another pair of skin-tight and very faded blue Wrangers and a thin, skin tight, grey tee-shirt. He got me to lie on the floor, face down, and he really soaked the jeans and the tee-shirt with his piss. Then I had to kneel so that he could piss into my mouth. I let his piss pour out of my mouth onto the front of the tee-shirt and jeans. Plus I was pissing into the jeans myself I'd got so full. Those jeans were getting really, really soaked! Even so, I wasn't feeling too cold so it was fine when Jack told me to lie face down again for the next 100 strokes of the cane. I discovered that taking the cane on wet jeans is worse than taking it on naked butt! But the feel of the piss-soaked jeans clinging to me was so sexy that I stayed hard for the whole hundred - in fact I was getting so turned on that I raised my butt off the floor to meet the strokes. Jack took the hint and the last twenty were delivered really hard. He told me to strip off and dry myself because he wanted to fuck me again - in fact he'd decided to fuck me after each hundred strokes from now on. I stripped, dried myself off and assumed the position. This time it was faster, and deeper, than before and lasted longer!

Then we took quite a long break. We'd agreed in advance that one of the things we wanted to do was to use a catheter and I needed to get all the bits and pieces for this into sterilising solution for half an hour. We also needed time out to rest and to tank up for the final session of the day. So, almost an hour later the kit was sterile and dry and we were both rested and full of piss!

Jack got me to kneel in the floor. He pissed over me and told me to open my mouth and drink his piss. I did and it got me really horny drinking his piss like that! When he'd finished I wanted to go too and so, as previously instructed, I filled a glass with my piss and drank it. Then he told me to get over the stool - another 100 strokes of the cane coming. As expected these strokes were harder again than the previous set and they were delivered at a slower pace. Towards the end my knees kind of went from time to time but he always waited until I was back in position before carrying on. 400 done, just the last 100 to go. I stayed in position and soon felt Jack's cock inside me again for what became a really hard fuck. How he stops himself cumming I just don't know - I nearly did! By now I needed to piss again and Jack told me to piss into a thin plastic bottle. I knew what was coming later! The bottle would hold a litre so it would take several goes over the next half hour or so to fill it. Jack needed to go too so I was back kneeling on the floor, getting soaked once again and also drinking Jack's piss as he pissed into my mouth. Dried off again I was able to put some more piss into the bottle. We watched some naughty video while we tanked up again.

About twenty minutes on I put some more piss in the bottle, almost filling it. Jack told me to prepare to be catheterized. I washed my hands and cock thoroughly using a fresh towel to dry (it's important to maintain high levels of hygiene when playing with catheters) and then fetched the sterilised kit into the room we were playing in. I unwrapped the sterile (new) catheter and put a stopper in it. I also drew up some water into a syringe so the securing balloon could be quicky inflated once the tube was in place. The feeling of a well lubed catheter being pushed up my cock is an amazing feeling which rarely fails to get me really horny. Yes, it hurts - it's supposed to! But it's a kind of pain, a bit like tit pain, that I find incredibly erotic and I only get to experience it a very few times a year. Once the tube is fully in, the feeling then is not painful - it just feels like I'm constantly pissing, a great feeling for a guy who is into piss fun! Once the catheter was in and secured I was able to use it to finally fill the bottle of piss. A long thin plastic tube was attached to the bottle and it was hung from a hook near the ceiling. The other end of the tube was, of course, attached to the catheter. Only a clamp on the tube stopped the contents of the bottle flowing back into me.

When the clamp was released I didn't feel anything at first but soon began to feel that I could use a piss. Very soon I was feeling really full and the clamp was closed again to give me time to adjust to feeling that full. Soon it was re-opened and this time I could feel the piss flowing into me. However hard you drink, your bladder never fills that quickly! Soon I was feeling really full and, looking down, I could even see that I was really full. It was beginning to get painful. Jack closed the clamp again but this time I didn't relax 'cos this was hurting. He patted the new bulge gently with his hand. Instant hard on! He continued like this for a few minutes - opening the clamp for a few seconds, closing it, patting me, opening it again. This until I had to say I really couldn't take any more. Jack agreed. I grabbed the syringe and deflated the securing balloon and slowly pulled the catheter out. This bit isn't much fun which is why I do it myself and I was relieved when it was out. But now I was still feeling very full of course. I needed, badly, to piss. So I was told to lie on the floor face up and let it go. Wow, it felt like gallons gushing up all over me! I was told to piss into my mouth so I raised my head off the floor to do so, getting a face full of piss into the bargain. When I'd finished I was told to kneel and Jack emptied himself over my chest and into my mouth again. Then I dried myself, removed the soaked towels off the floor and assumed the position for the last hundred strokes of the cane.

The final set were taken very slow and very hard. Jack eased up a bit between sixty and eighty but used full force for the final twenty. I got really horny again towards the end and when his cock was inside my butt again he told me to play with my cock. I thought I was going to shoot instantly but tried to hold back. I rather over did the holding back bit and didn't shoot until long after Jack had shot his load.

I've had 500 strokes in a session before but they've usually been a mix of implements and not all on the butt. So this was a first for me and even now, two days later, my butt is bright red and I can feel slight ridges. It seems Jack had timed the session exactly right, my skin would have broken if even just a few more cane strokes had been applied. As it is - I'll be OK for meeting at the Club in eight days time!

Warning: Please don't play with catheters unless you know what you're doing. I was taught by a urologist. If you get it wrong it can very rapidly go comprehensively wrong and lead to damage to or infection of your balls!

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