Thank you Guv for such a creative, challenging and painful dare!
I started this at 12pm today, as I don't have any thongs, a quick trip to the local H&M and I felt like a pervert (that I am) bringing the pack of white lacy thongs clearly my size to the till. Thankfully the retail worker didn't say anything. It was hard to contain my nerves and arousal going commando, I then found a cafe nearby and put my thong on.
Getting home was increasingly uncomfortable as the thong pressed into my asshole. Once I got home I gave myself a quick clean in the butt, and set up one dildo on on the cupboards in the kitchen and another on a stool. I used a smaller dildo in my ass to start warming up because I knew I had to use my larger one to cum from anal. What I didn't anticipate was the pain my nipples were going to be in - attaching a pair of chained clover clamps with a weight in the middle made every single thrust a punishment, as it kept swinging and pulling on them. This made me so much hornier but also desperate to cum, because I wasn't sure how much I could take. I fucked myself for about 3 minutes using the smaller dildo and replaced it with the larger one, which hurt to put in but quickly became okay and pressed on my prostate nicely. After about 15 minutes of fucking I felt my cock starting to leak, it had filled with some cum.
At this point I was desperate to complete the dare because my nipples were on fire. I tied my balls up and taped them as far back as I could with duct tape, and started sucking on the dildo I first used in my ass with the condom on, sucking out cum. I realised though that a lot of it leaked onto the shaft, so I took off the condom and sucked it clean. By now I was quite eager to piss and I peed through my white thongs, making a mess on the floor. I took them off and realised that the back had been soiled with so much lube and my ass from fucking, it had yellowed already... soaked in piss I closed my eyes and put it in my mouth, the mixture of the piss, ass and lube was NOT pleasant... but it made me feel so pathetic and turned on. I put the large dildo back in my ass and jerked my little cock off until I came - a mostly dry orgasm.
I took off my nipple clamps, and they had made clear marks on them - four little dots pressed onto them, flattened out. I imagine I'll feel that for a while!
Thank you again for the custom dare