I'm not ALWAYS a mean Domme! I really do enjoy giving my boyfriend pleasure. I usually reserve giving the ultimate forms of pleasure to my bulls (blowjobs, fucking my pussy, etc), but I still like to make my sissy bf feel good in the ways that he deserves (cumming while being pegged and in chastity). It was the last day of Locktober and I decided to roll the camera to record our play session. I had told him to get dressed up like a sissy for me and he looked so cute in his girly lingerie! He gets sooooo desperate whenever he's locked in chastity and hasn't cum in a long time, so he was eager to get going! I started warming his ass up by using my hand and his favourite paddle. I teased him a little before I put my cock in, reminding him what little attention his dick has had this month while it's been locked up. I started in on his ass from behind and he immediately started moaning. I could tell he was loving it. I pushed him down on the bed so that he was lying on his stomach and I was grinding on him while fucking his ass - my favourite pegging position! He gets so subby when he's getting his ass fucked so I took advantage of that and made him say embarrassing things. I flipped him over so I could have a better view of his locked up cock. It was so cute bouncing around as I pounded him! I've never allowed him to cum while being pegged and in chastity at the same time, so I thought what better way to end Locktober than putting those two humiliating things together! It's so fun now that my bf is a total sissy because he loves cumming like a girl with a vibrator on his little clit! I knew he was so desperate for the vibrator so I pulled it out. He was in heaven! It didn't take long for him to start begging to cum. I almost forgot to say yes because for the last month I've been saying no! lol. He came like a pathetic sissy, and I made him eat his cum, obviously!