Anal Fun

Ready to have that little item in your ass?" "Oh NO! Nope, no!" she said realizing too late what I intended, not that it would have mattered of course. "Barri, not now, not yet, please!" "Look IW" I growled, "stop arguing with me. It's time to stretch that asshole the next step unless you want to get split open with my cock. And if you don't start behaving a little better, I'm going to use that crop on your ass now. In fact I might just anyway, so stop angering me." I placed the lube and plug on the dresser. I firmly grasped the base of the plug in my right hand and told her to relax and grip the dresser firmly. She did as instructed, relaxing as best she could. I took the tube of lubricant and using my fingers worked some in and around her tight asshole. Then I actually squirted some up her rectum. Lastly I lathered the plug with it until it was literally dripping. This was going to be an effort to insert and I wanted it to go as smoothly as possible. I marveled at the size of the thing, but it wasn't as big as me and I knew she could handle it. I waited for her to really relax."Take a couple of deep breaths and relax as much as you can, I'll be a gentle as possible, honest."She did exactly that, and I did as promised. I exerted a steady firm pressure on the base of the thing, but pushed it in very slowly. It was pretty erotic watching the black cone stretch her sphincter muscle wider and wider. By the time it was about 3/4 of the way in she was grunting and gasping, still doing her best to relax. I pushed a little harder."Almost there, just a little bit more" I encouraged as the thing stretched her wider still. "OH, OW, OH FUCK!" she started to pant. It was nearly there and then with a final extra push the widest part was at her opening and it popped the rest of the way in. She gave a loud grunt. "Fuck! God it hurts!" "You'll get used to it in a minute. Just think what it would have been like if I have tried to fuck your ass without doing this!"She just grunted and panted some more, still bent over, trying to adjust to the hugeness she was feeling. "Stand up when you're ready" I said and leaving her to decide on her own. She stood on place until I figured that the plug had loosened her up as much as possible. I was hard at the thought of sodomizing her ass. "Okay IW, it's time." She knew what I meant, but didn't say anything or move, just looked at me waiting for instructions."Over the chair!" She delicately got back in position and didn't realize I had a couple of surprises in store. First I took some stretchy Velcro straps and fastened her ankles to the chair legs, this spread her legs nice and wide and made sure she wouldn't be able to move much. Next I attached the wrist cuffs and bent her over so her ass was the perfect height and well exposed. I stretched her forward and attached the cuffs via a piece of rope to the front legs.She was complete exposed and vulnerable and her torso was hanging over the chair seat. I wasn't done. I went and got the ball gag and without letting her see them, the adjustable nipple clamps and a couple of the heavier weights for them.The first thing I did was gag her. Then I stopped and standing behind her I started to finger her pussy, playing frequently with her clit. Almost immediately she was flooding my hand with her juices. Even knowing what was coming she was an insatiable little slut. She was squirming and moaning into the gag and wiggling around trying to maximize the stimulation. I let her build very close to cumming before I stopped. I could tell she was groaning into the gag and probably begging for more.I went in front of the chair and finally let her see the clamps. Her eyes went wide and she started to violently shake her head from side to side. I knew her nipples would be extremely sore and sensitive, so I didn't tighten the clamps as much as before, but plenty tight enough to be felt, especially after I hung the weights on them, which I did. As soon as the weights were in place she tried to hold as still as possible because as much as they hurt just hanging there if she moved the tore sadistically at her tender flesh. I knew she wouldn't be able to hold still long however. By now I was rock hard. Now normally a cock is going to give some and make anal a little easier than a plug or dildo does, but I swear that to me at least, my cock felt like steel. I stripped off my clothes and stood in front of her."Take a good look at what you're about to feel bitch" I mocked. I moved back behind her again and though impatient, took the time to finger her some more. Again I pushed her right to the edge, though it took longer because as she started to squirm her nipples were feeling exquisite pain. Still, when I stopped I could tell she was groaning in frustration.At last it was time. I really had to pull hard to get the plug out, but out it came. I just stared for a moment at her obscenely gapping hole. Much to my pleasure it didn't close up, but looked like a small tunnel. I squirted some lube inside and much as I had with the plug I covered my massive cock with it too. As I place the head against the opening I could hear her muffled screams of anticipation. "Quiet IW, I haven't even started yet!"I couldn't resist. I slapped her ass hard with my right hand, catching the end of a welt. The scream that came out even through the gag was unbelievable.