I invited Kelly over to examine her daughter's ass. Kelly was visibly excited. She ran her hand over Cassie's ass and bent down to have a close look.
"Very nice," Mommy Kelly said. She was obviously enjoying watching her daughter get beaten.
I moved to the other side. I wanted to cane her from both sides; otherwise, the marks were always greater on the far side from where I was caning. I use a backhand stroke from my dominant hand. I don't like switching hands, and I find that it's not the force of the blow that causes the damage, but the speed with which I flick my wrist. I can cause as much of a reaction with a sharp flick of the wrist as I can from a hard strike.
I continued to leisurely cane Cassie's ass. By now she had stopped crying aloud and was simply gulping ragged breaths as the strikes multiplied on her tender ass. Her ass was now crisscrossed with angry red welts. Black and blue patches had also appeared. I was delighted with the sight of her shredded ass. I paused at 25 as I ran my hand over her damaged bottom.
"25. Thank you, Mistress. May I have another?" Cassie moaned.
"Halfway there, you worthless whore. How much did you enjoy that pathetic fuck now?" I taunted her. "I bet you wish you had never sucked that cock now. You see what trouble men get you into? Maybe next time your pussy tingles, you'll think twice before you let a cock inside it."
I continued beating her shredded bum. Tap, tap, whack. I was really warmed up now and my strokes were even and very hard. Her ass was totally black and blue now and the strokes continued to shower down. I paused again at 40 and allowed Cassie to catch her breath. I invited Kelly over to closely examine her daughter's ass again. Kelly ran her hand over her daughter's ass. Kelly was so turned on by now that a wet spot showed on the back of her dress. Kelly's hand strayed from her daughter's ravaged ass and she let a finger trace the outline of Cassie's pussy crack.
I told Kelly to sit back down and I finished administering the last ten strokes.
"How do you feel now, slut? Have you learned a lesson? Do you want to suck cocks now?" I asked the poor girl.
"No, Mistress. I'll never fuck or suck a man again."
"Good girl," I told her. I unclipped Cassie's hands and she immediately began rubbing her ass. I ordered her to stop and took the belt off her waist. Finally, I released her legs from the stocks. I ordered her to go over to the wall and place her nose against it with her hands on her head. I told her not to touch her ass unless I gave her permission.
I knew that Mommy Kelly was a switch and that she would enjoy being dominated by me, as well. I moved the punishment bench around so that she would be facing her daughter's ass and could watch it while she was bent over the bench. I ordered Kelly to strip.
I went to my chest of toys and extracted some nipple clamps and a medium-large strap-on.
Kelly's body was middle aged, not at all tight and pert like her daughter's. Kelly was a little over weight and had a tummy role. Her ass was saggy and not tight. Overall, however, she was a reasonably attractive woman for her age.
I began tugging on Kelly's nipples, rolling them with my fingers and pulling them sharply out from her body. Kelly was clearly enjoying the attention to her tits, although she winced when I tugged sharply on them. When her nipples were rock hard from the attention, I applied the clamps. They were the screw-down type. I tightened them sufficiently so that they wouldn't fall off, but not so tight as to cause great pain.
I ordered Kelly to bend forward over the bench onto her elbows, and to spread her legs apart. I stepped into the strap-on. I pulled Kelly's ass cheeks apart and examined her butt hole. As I suspected, it had been penetrated many times, giving a natural gape. Her shaved cunt was dripping wet, as I suspected. Her pussy lips were swollen and hung down, not tight like her daughter's, but typical of a woman her age.
I squirted some lube on my rubber cock. I didn't need to lubricate Kelly's snatch; it was wet enough. I slowly inserted my cock into her cunt from behind. It slid in easily, even given its rather large size. Kelly groaned in pleasure and I began to slowly move in and out. Gradually I built up a rhythm, going all the way in and then pulling back, almost all the way out.
I told Kelly she could touch herself and her fingers immediately went to her clit, rubbing furiously. I warned Kelly that she couldn't cum without my permission.
I continued to fuck her that way for several more minutes. I could tell Kelly was close to orgasm, so I ordered her to stop touching her clit.
I pulled out of Kelly's cunt. I could hear her disappointment. I squirted lube on my index and middle fingers and slowly inserted them in Kelly's asshole. She groaned with pleasure and thrust her hips back to push my fingers all the way up her ass. I continued to lube Kelly's ass with my fingers and added a third finger.
I lubed my cock up again and slowly introduced it into Kelly's ass. I pushed the tip and left it there for about ten seconds, then withdrew it, allowing her ass to rest for a few moments. I again pushed it in a little ways. I continued to toy with her ass like this, each time pushing my cock a little deeper. Finally, I sensed her sphincter give way and I pushed all the way inside her. I paused with my cock all the way in her ass for about 15 seconds. Then I slowly started moving in and out.
Kelly groaned with obvious pleasure and excitement. I began a steady rhythm in and out. The ass has many more nerve endings than the vagina, so an anal orgasm is much more powerful than a vaginal one. Most women cannot orgasm from a purely vaginal fuck, but they can when being fucked in the ass. I told Kelly she could touch herself again. She began frigging her clit as I fucked her ass.
"Please, Mistress," she begged, "can I cum?"
"Yes, my pet," I told her. "Cum for your mistress."
Kelly's whole body shook as she experienced an earth-shattering orgasm. Between watching Cassie's ass getting shredded and being bent over and ass fucked, Kelly experienced one of the best orgasms of her life.
I left my cock in her ass until her orgasm subsided, then I slowly removed my strap-on from her ass. I told her to sit on the chair with her legs spread apart. I then ordered Cassie to come kneel in front of her mother and clean her cunt and asshole. Cassie knelt before her mommy and began to expertly lick her pussy and ream her ass.
Kelly became aroused again and grabbed Cassie's head with both hands, grinding her hips into Cassie's face. I ordered Cassie to continue licking Kelly's cunt and ass until Kelly began bucking her hips into Cassie's face.
"Please, Mistress," Kelly moaned, "may I cum?"
"Yes, you may," I replied. Kelly cried out as her orgasm wracked her body. She held Cassie's face to her cunt until the waves subsided. Then she released her daughter.
I ordered Cassie back to the wall with her hands on her head. I told Kelly to come and stand before me and to also put her hands on her head. I examined Kelly's cunt, and thrust my fingers inside her. I pulled them out and sniffed them and then licked them. I told Kelly to turn around and I repeated it with her asshole. I thrust three fingers inside her and then smelled them. I had Kelly lick them clean.
I told Kelly to get dressed but I left Cassie against the wall where I could admire her damaged ass. I told Kelly that when she got home, she was to rub lotion on Cassie's ass and to repeat it at least twice a day, morning and night, for the next week. I said that Cassie may have to ride home in the back seat of the car on all fours, since sitting on the front seat would be too painful.
I have a sideline selling sex toys to my clients, and I sold Kelly some nipple clamps, a medium sized dildo, and a medium-small butt plug, along with some lube. I told Kelly she was to plug Cassie's ass for at least an hour a day. She was also to clamp her own nipples at least once a day. She could use the dildo on Cassie's pussy whenever they played.
I told Cassie to get dressed. I asked her if she had learned her lesson. Cassie thanked me for punishing her and said she would be a good girl and listen to her mother from now on.
I saw them out the door and told Kelly she could bring back Cassie any time for further training or if she needed to be punished again. I knew they would be back. As painful as the caning had been, I knew Cassie would fantasize about being caned by me and would masturbate many times reliving the experience. That's the way I train my subs.