A Tale of Two Ass Chees

Benedict had spanked me on Monday, neither of us had expected it to bruise as it wasn't a particularly rough session. A few hours later, I realized I had a polka dot pattern of bruises on the right side of my ass. See I'm a little OCD about some things and symmetry is definitely one of them. The spanking itself had been bad enough to be unbalanced, but the bruises were a harsh reminder. All week long I'd been begging him to come back over and even out. Finally at 3 am on Thursday morning (we're both chronic insomniacs,) I got a beautiful text. "Tomorrow at lunch I'm going to come take care of your ass. I've been neglecting it, both in terms of fucking it and disciplining you. Be prepared for me. I'm going to make sure you start your weekend off right, with an ass full of cum and a nice set of bruises." This got me wet on the spot, it was a mere 9 hours away.

I woke up the next morning and headed for the shower. I wanted to be absolutely spotless for the anal torment that was to follow. What seemed like gallons of water up my colon later, I was dried, ready and in position. I was face down, ass up on my chaise, with a Cat-O-Nine Tails next to me, so that would be the first thing Benedict say when he walked in the door.

This particular Cat-O-Nine Tails was an Icicles No 38. The handle doubled as a thick glass dildo and the tail was seemingly soft leather. I heard the door open and I tensed up. Not as word was said as he started spanking me gently with his hand. I was grateful for the warm up as I knew I'd get much more. The smacks gradually increased in both frequency and intensity. I could feel my cunt getting wetter with each smack. My ass was turning a rosy shade of pink as I moaned gratefully. My enema had left me clean and what I thought was pretty opened up, so I hadn't prelubricated intentionally. I wanted to feel the soreness of his hard cock but I wasn't prepared for the glass handle which was thrust rudely into my rejuvenated asshole. Normally a 1.5 diameter doesn't faze me in the slightest, but the round, hard, untapered, glass was leaving quite an impression on my sphincter and rectum.

Benedict resumed his spanking, harder now. This was especially cruel as I'm prone to tensing up in anticipation of a blow, and all that did was making the glass more apparent. Every now and then he'd reach between my lips and feel my wetness. It didn't matter that my mind knew this was humiliating and painful, my cunt betrayed my masochistic submission. I spread my legs to allow him deeper access as well as lessen the tension on my asshole. He began fucking my ass with the crude glass phallus. I tried to relax, knowing resistant muscles would be worse off for the abuse. He continued spanking me with his free hand and despite my discomfort, I was moaning and grinding like a bitch in heat. He didn't allow me to cum, but kept me on the edge, I would have done anything he'd asked for relief. With one vicious tug, Benedict relieved my asshole of the transparent intruder. I tensed for the sting of the tails but instead the manual smacks continued paired with the mace like blows of the glass handle. They weren't overly hard, but I knew they'd likely bruise, which was most certainly his goal. Just to ensure my asshole didn't become too tight, he'd occasionally dip a finger or two in and stretch them out.

I had my legs spread just about as wide as was possible and was taken by surprise by the first square blow from the Cat. I jumped a little, but I screamed bloody murder and closed up when the second blow fell squarely on my exposed lips. I knew it had been unintentional, after all a new toy takes some getting used to, but that had left me smarting and I chose to protect my most sensitive parts. The Cat could have been very painful, the leather was in extremely narrow strips, the ends of which cut the worse, but lucky for me this was an introductory session. Now that Benedict has become acquainted with the Cat, I suspect next time won't be won't be so gentle. Now of course, gentle is a relative term when it comes to my spankings. In this case my ass was read and I was moaning. The blows kept falling as I buried my face in the sofa, biting the pillows on the harder blows. I love the warm feeling from a thorough spanking and right then, I was positively glowing. If only my anus self lubricated as well as my cunt did.

The Cat was laid down and Benedict walked around the chaise to play his cock at my mouth. It took no time at all for me to suck him to hardness. The sound of me gagging and site of my eyes widening in panic as I lose the ability to breath never fails to elicit an erection that Michelangelo would be proud of. As soon as he was ready, he grabbed my by my hair and jerked my body around so that my asshole was readily presented. He plunged in dry which hurt like hell. I'd underestimated the effect that the glass had on my tight muscles. At this point, I knew that my pleasure and my comfort were irrelevant. I bit my lip and put my head down, determined to take this violation.

This hurt, I was wishing I'd lubed up, I was wishing I hadn't laid that flogger out, but it was too late for regrets. I had nothing to focus on right now but the right hard cock pumping me. It felt like my asshole was being invaded by group of Lilliputians with a battery ram. Normally I'll loosen up after the first few thrusts, but no such luck this time. If Benedict knew how much pain I was in, he didn't let it deter him, if anything, it just aroused him further. Before I knew it, he was pulling out and coating my ass with a hot, soothing load of cum. I could feel it dripping down my cunt and legs. He used his finger like a squeegee, guiding his cum into my gaping asshole, once he'd pushed it all in, I was treated to one final smack to seal it all in.

He laid down next to me and I crawled into his arms, grateful for the pain to be over and very happy that I hadn't let him down. The aftercare is always my favorite part. No matter how far Benedict pushes me, he always brings me back to safety and warmth. I couldn't ask for more from a man.