This would be his first experience with anal play and penetration, so it was a process working up to his relaxation and ultimate comfort. Lubrication was needed as well.
Before attempting the initial insertion, we gave him an enema and basically douched his asshole. Then, I asked him to find his most comfortable position which turned out to be on his back missionary. I advised him to relax and not to clinch is cheeks.
Once he reached relaxation, I put on some latex gloves and applied the lube to his rectum area. I wrapped the cock ring around his lightly erect penis, and pulled the probe to enter into his hole. Little by little, I pushed in the probe and pulled it out. The idea is to open the hole slowly and stretch it little bit at a time.
Eventually, the probe would be fully inside his rectum and his penis rock hard. From there, I began to play with it and did so until he couldn't take it anymore.
I asked him how it felt, and of course he admitted it was strange at first but eventually began to slightly enjoy the penetration but more so was impressed with the cock ring and how it extended his erection. He also mentioned how the pulling from the anal insertion and play.
Although he didn't seem to eager to do it again anytime soon, he did say that the feel of the toy was very comfortable with the silicone material. Gentle touchy, sturdy material and all around quality product.