Continued from: Should we let the Sissy's Cum?
With our sissy "girls" idle and safely tucked-away in bondage, Katrina and I retired to my personal chambers to deal with our little arousal problem.
Watching our silly sissies suck each other off and cum into each other's mouths had us extremely horny!
Kat went down on me and skipped all stages of foreplay, she went right for my clit. Fuck me! Did I ever cum.
I pinned Katrina's wrists down and returned the favour. I soon had her beautiful sheen, cascading off my lips.
We chewed up around 45 minutes, going down on each other and waiting for our sissy's to "re-load". She even gave my asshole a nice, deep fucking with her tongue. Such a good girl!
We entered the sissy bedroom once again, to check on our idle girls. Andrew, who wasn't gagged but was locked in a cage, dropped his safeword of "yellow", as we entered the room. I knelt down to confirm it was in-fact a safeword moment.
We got him out of the cage immediately and Katrina took him out in the hallway to chat where he upgraded his status to "red" and done. She returned a short time later and told me she was taking Andrew home. Apparently he couldn't rebound back into role, after his orgasm. And I think he suspected we were going to peg the pair of them (yes that was the plan).
"See, these fuckin' male subs!" I said to Katrina. "It should be permanent chastity and anal only for these pathetic sissy bitches", I vented further.
"Ya no kidding", Katrina said. "I know you warned me this would happen Mistress. It makes me want to find a bull even more now and keep him locked up forever", Katrina frustratingly advised.
"Just remember Kat, no punishment for him safe-wording out. He has to know that there's no negative repercussions in doing that", I reminded her.
I kissed Katrina goodbye and saw the two of them out. Safe-wording doesn't mean Andrew's dick gets unlocked, it just means that his session ends. I kept the keys to his device as they left.
I returned to Kaylee to unlock his shackles and remove the dildo that was up his ass. I told him the session was over but had him lick my boots while we chatted.
"Kaylee, I need a secretary. A receptionist. You know, Cassandra's role, when she checks you in for appointments downstairs?" I said to him.
"I'd like this to be you, since you are almost completely passable as female", I added.
It was a sad truth. The leaves on the trees were starting to change colour, Autumn was upon us and with that, it meant Cassie had to return to school. We both had a little ugly-cry the other day, when we had to bid each other farewell, but Cassandra was adamant that she wished her maintenance spankings to continue.
Without fail, Cassie would make it home on the train every Sunday, to have dinner with her family. Sunday's became her maintenance days. She would come to my office for her spanking first, then go see her family for dinner afterwards.
I think her Mom Bella, caught on, watching Cassandra wince and squirm on a sore bottom throughout their Sunday dinners.
Occasionally Bella would be in the same boat, trying to keep a straight face and hold normal conversation with her husband, while nursing a sore bottom. It would be more efficient for me if I just spanked Bella and Cassie together! Maybe I'll suggest that to the pair of them.
Cassie was still given 20 minutes in the corner before her spanking and 20 minutes after. Since she wasn't doing any summer-school extra credit anymore, we eliminated the need for her to dress in proper school attire. Sometimes she was spanked bare naked, other times her jeans and panties would come down and every state of undress in between.
The conclusion of her maintenance appointments always ended in snuggles and kisses. If we had enough time before her dinner, she'd treat me to a little dance too. I think she missed my strip joint! Haha
As for Kaylee, he was predominately used to wearing frilly sissy clothes in baby pink and white, everything had bows and ruffles. I decided to take him shopping for some new bras and panties, options a little more "grown up". We also got him some professional, Secretarial outfits with hosiery and high heels in his size.
Of course I made him try things on in the stores and have the sales ladies help pick out his bra and panty sets while his face burned with embarrassment.
He wore little B-cup, falsey tits in his bras. With his make-up heavily applied and a high-quality wig in place, he was just about passable as female.
Of course he was dreadfully humiliated, being my feminized Receptionist, but with his little clitty locked in a chastity device, I still made the rules.
Sometimes he needed extra motivation over my knee and he was in no-way as proficient as Cassandra was, but at least I didn't have to pay him.
His payment was the occasional moments when I let him lick my bare asshole, or kiss my high heels.
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