Sisterhood of Sin -- 12 --The Caged Cock - Sex Stories

Sisterhood of Sin -- 12 --The Caged Cock

... process, so I ask, "How does that feel?" "Weird. A little cold, but not bad." "Good. Now try to relax." I push my finger in with a slight twisting motion. It slips in past the first knuckle, but it feels like he's got a death grip on it. "It's in, Dan, now just relax." I work it, fucking his ass with just the one finger until I suddenly feel it relax and the second knuckle slips easily in. I keep fucking it, adding more lubricant before he has a chance to complain. When the time seems right, I slip the second lubed finger in. "Hey!" "Relax, Dan. I did this to myself to help the plug go in easier. If I can take it..." He's a sucker for challenging his toughness. He relaxes more and I curl the two fingers down toward the base of his cock and feel his prostate. I know that if I stroke it too much, he will come, but I don't want him to yet. I stroke it twice, just to see if I can get away with it. He doesn't complain. "How does that feel?" "Not as bad as I expected." "Maybe even kind of good?" "Well, weird still, but I guess kinda good?" I slip my fingers out and push the butt plug in without difficulty. "Okay, close on that now, but don't push it out." I review my progress to this point and decide that it was too easy. He's offered only token resistance since I ordered him into the shower. This tells me that he's possibly wanted me to cross these barriers with him; telling me the story of his CFNM experience, agreeing to punishment so easily when I know that cold water on his ...

... cock and balls isn't all that upsetting to a guy from Northern Minnesota, and letting me fuck his ass with my fingers seems like a major turning point in our relationship to me. Maybe he doesn't see it that way, but I'm excited by what it could mean for us, especially when I reach beneath him and discover how hard his cock is. I quickly release it. I don't want him to come before the spanking. I choose not to mention it, not wanting to openly humiliate him for enjoying anal play. That test will come later. "This will be an over the knee spanking, Dan. You may get the chair." "Yes, Sister Cate." I'm pleased that he's still playing the submissive role. He brings the chair in and places it where he spanked me last week. I place a towel on it and pull the hem of my habit way up before I sit. When he goes over my knee, I grip his hard cock between my nylon-encased thighs. I wiggle my legs a little, making sure I can feel his cock. The situation is a bit bizarre, such a tall man bent over a much smaller woman's lap, presenting an ass that has a plug stuck in it. I feel my nipples stiffen as I deliver the first smack very hard. "Ow!" "Now don't be a baby, Dan. You know that my hand is stinging, too. Count after each one, or I'll add one to the count you'll receive." "One!" I rub his cheek and feel him squirm, trying to get more stimulation on his cock. I smack the other side. My pussy feels much more awake now. I alternate cheeks with each swat, rubbing each right after I hit, but I ...