Well last night was my first pegging session. I talked with my FWB many times about her pegging me. Last night I actually did it. I prepped myself for a couple days. Stretching with plugs and used a dildo on myself a day before and before she pegged me. She has her own harness and when she put it on I was kind of shaking from excitement. It was actually happening. So I also put on my cock ring because why not add more fun to the pegging session. I went through my plug set ending on the biggest one before she stuck it in. I layed on my back got my legs in the air, put my ass in the proper position and she slid on in with ease. It was such a new sensation to have her in control and had been a year since I performed prostate play on myself. We took it easy at first and then I pulled up on her and she got the hint to go faster, and that ruined it. It started to burn a bit and I was uncomfortable. We added more lube but it was still burning a bit. Ended that pegging session on a not so good note. We did transfer into a wonderful face sitting session. She made such a mess on my face. Also she gave me a nice blowjob. Going forward I will plan on getting myself less sensitive to the dildo. Learning to relax and focus on the feeling of the prostate getting rubbed. It takes time.