My Keyholder's Whims Ch. 02 by obionequixote,obionequixote

“OK folks — I guess we are done here! Who is ready to go to my house for an after-party?” asked Mistress Wilma. The whole crew responded with excited positive anticipation, and they gathered their things and I was allowed to come out from under the table. “Take care of the bill and leave a good tip, boi!” Mistress Wilma told me. I paid the tab and provided a generous tip to the waitress who seemed to have been aware of what was going on under the table.

I drove Mistress Wilma and Her cuck back to Her house and the rest of the party arrived a few minutes later. Once inside, Mistress Wilma told me to go give myself a warm water enema in the bathroom and then come upstairs. I gave myself a few washes until everything was clean and clear and then rejoined the group. Mistress Wilma’s cuck had an appointment with some other play partners and gathered his luggage to go see them.

The rest party all retired to the attic dungeon, and everyone got comfortable in the couches and chairs except for me and subbie cleo. Mistress Wilma and Domme Vickie instructed their subs to strip. The subs then sat naked at their Mistress’s feet, rubbing them and fetching drinks or whatever items they were directed to retrieve. One of the items that I was told to go fetch was the penis gag with the seven-inch phallus attached to the outside of it. Mistress Wilma had me put it on snuggly and lie on my back, with my feet away from the center of the room. Mistress Wilma then stood over my face facing the group and crouched over the phallus, raising Her skirt to allow Her to insert the phallus into Her pussy. She lowered Herself fully on to the dildo and rested Her butt on my face, all the while continuing to talk with Her friends as though nothing unusual were happening.

Every now and then Mistress Wilma would raise Herself up a few inches and then squirm down on the face mounted dildo and come to rest on my chin with my nose pressing up against Her clit. Whenever there was a lull in the conversation, She would reach back and swat my cage a few times just to get me to jerk and jostle, thus providing Her with some extra stimulation via the dildo mounted to my face. She would gasp a bit and push down harder on the dildo, eventually rendering a loud scream as She came all over my face. Domme Vickie was having Her legs and feet massaged by subbie cleo and was stroking Her consort’s cock through his pants. After the dinner had digested a bit, Mistress Wilma announced that it was time for some fun.

“Now, what should we do with him first?” Mistress Wilma asked the party, trolling for a vote on the next activity.

“Have you fucked his ass yet?” asked Domme Vickie excitedly. “Stretch his asshole!” She added. Mistress Wilma’s eyes lit up and she nodded Her assent to the suggestion.

Mistress Wilma pulled a wooden chair out into the middle of the room and had me go fetch an eight-inch dildo with a suction cup on its base. She had me lick the suction cup and smacked it onto the chair and gave it a swat to get it wobbling back and forth. “Go get me the coconut oil jar and come kneel on your hands and knees in front of me boi!” She commanded. I quickly crawled over to the toy chest and brought back the jar. “Face to the ground, ass up, boi!” She instructed. I readily complied and raised my ass as instructed. “Pull your cheeks apart for Me!” She continued.

With my ass cheeks spread wide and my face on the floor, She swooped out some oil and lubed my ass up. The feeling of intrusion by Her fingers into my hole caused my sphincter to tighten up. “Open that asshole up boi! Relax — take a deep breath!” She cajoled. I took in a deep breath as She inserted two, then three fingers inside of me, working them to stretch me out. “Now let’s see if your butt-plug training has been a success, boi.”

She pulled Her fingers out of me with a pop, and my asshole did a little gaping dance, constricting then gaping, then bouncing back to normal, then coming to rest somewhere in between. “Sit on that dildo, boi — NOW!” She barked. I positioned myself over the chair mounted dildo and fed the head of it into my awaiting asshole. The dildo was a bit longer and girthier than the butt-plug I had been practicing with, and it took a few tries to get it into my ass. Once the first third of the dildo was past the ring of my ass, the rest slid in easier. I managed to get it all the way in and was sitting on it completely.

“Now fuck it, boi! Ride that cock! Bounce on it!” Mistress Wilma ordered sternly. I commenced rising up, and then sliding back down on the rubber cock, and each time it slid back in, another small load of pre-cum would escape from the head of my dick and dribble out the little hole at the end of the chastity cage. I slowly built up to a faster pace and was bouncing up and down on the dildo in time with the music in the background. Everyone in the party was laughing and pointing at me as I provided them with their entertainment.

“What a tiny cock!” guffawed Domme Vickie, “Look at it bounce and drip! His face dildo is bouncing too!” Even subbie cleo was enjoying the display and chortled when she would glance up from her leg massaging duties.

My asshole was getting sore from the repeated intrusions, yet the feeling was erotic and the feedback from the group was somehow making it more exciting — to be put on display and to perform an act of self sodomization was humbling. Every time the dildo rubbed against my prostate, more semen would be released, and it was puddling on the chair in front of me. “Look at the mess you have made on my chair, boi!” Mistress Wilma shouted, “Get up off of that cock and clean that mess up with your tongue, bitch!”

I slowly rose off the chair and the dildo exited with a pop, my aggravated anus twitching. I knelt down in front of the chair and scooped up all the pre-cum on my tongue, licking the chair seat clean. The party whooped and cheered as I took care of my duty. Mistress Wilma had me come back and lay down on the floor face up and resumed Her seat on my face, this time with my legs pointed to the walls so She could nuzzle Her rosebud on my nose.

Domme Vickie was excited and was ready to provide the next act of the entertainment, leading Her subbie to the St. Andrew’s cross and chaining cleo’s wrists to the cross. Domme Vickie had cleo positioned face against the cross and put ankle cuffs on her and attached cleo’s spread legs to the bottom of the cross.

Domme Vickie went over to the rack on the wall and selected a few whips and floggers to use on Her subbie. When She had gathered the implements of pain that She wanted, She started by softening up Her subbie’s back with the flogger, laying into it with gusto. Subbie cleo’s back became increasingly pink, and then red as the flogger slapped her skin. Domme Vickie switched to the single tail whip and gave the subbie a few licks that left angry red stripes on Her sub’s back. Subbie cleo winced and let some muffled cries and squeals escape, but for the most part was taking the punishment well and was beginning to drift off into sub-space — that realm beyond pain where the body’s endorphins pump out to mask the pain and allow a subbie to float into a state of detachment and ecstasy. Domme Vickie was nearly orgasmic from Her effort and the responses that Her subbie was providing.

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