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This is a place for me to jot down things that I have done as dares/as a direct result of dares.
I've been doing a lot more naked stuff, outside at night. It's fun.
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The Peg Race

Posted 05-08-2022 at 10:50 PM by tyragon123

I finally got some much needed time to myself at home, and did not put it to waste. A few days ago I saw this roulette, Peg Race, and it captured my imagination. Originally I planned to use six of my dildos. After I got going, I decided to skip one (the red dildo with a slight bend) that was too similar in circumference and length to the previous one.

I found a long video to have on in the background while I completed my task and set off. Dildo one was no challenge at all, and I had taken it “balls deep” (despite it not actually having balls) almost immediately. The roulette then requires you to reroll for a task to do with said dildo, which also wasn’t a problem. I then moved on to the next dildo (orange with the knot). A great transition dildo as the shaft is equivalent to the first dildo and the knot is equivalent to the next dildo.

This is a great roulette as the time spent mastering one dildo is good preparation for taking the next. Next up was the pink dildo, and I was able to get into a great rhythm with it. In my previous anal adventures I have had to go really slowly on dildos this size and up, or else it gets painful. Especially this one with the moulded head and veins. This time I was able to get up to 80+bpm for five or so minutes. From here everything kept going smoothly with the fourth dildo. Slightly wider, but smooth and basically the same length. This hurdle was conquered pretty quickly, and before long I was on to “The Big One”.

A thick, 12 inch purple dildo that has always been a real challenge. I have managed to take it almost balls deep before but I’m pretty sure it was a little painful. Right from the get go I was able to take ~8 inches. I went very slowly and eventually managed to comfortably fit all 12 inches. I picked one of the easier tasks from the roulette for this dildo as I didn’t want to push it.

After this I did a couple of other small things:
Some fingering, all the way up to four fingers partially/mostly inserted
Put in one of my bigger buttplugs while I cleaned up a bit
Some spit roasting with the pink dildo in my ass & blue dildo in my mouth

I had a lot of fun with this roulette. No sissygasm unfortunately, but there was a very large puddle of precum by the end of the task. It really showed me that, provided you do it the right way, anal can be pleasurable, pain free and rewarding. Even at large lengths, circumferences and high speeds.

I was in some kind of cowgirl position the whole time (either kneeling or squatting) and, despite consuming food and liquid before and during, was just exhausted by the end. (Thirsty and low blood sugar) Staying in that position for extended periods really wears you out.

Next time I get some time alone I would love to do some anal on a barstool, because that seems like a really interesting position.
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