The Leaves are Changing

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. 

I even got him a little desk name-plate, with pink hearts on either side of the name: 

💕Kaylee💕

Mistress Andrea

xoxo

Continued in: Summer requests a MDLG weekend

Should we let the Sissy's Cum?

Continued from: What would you do for the keys?

When we left off, our poor, humiliated sissy slaves were giving each other hand jobs, on a frilly pink loveseat in a sissy bedroom. We took it one step further and "forced" them to kiss, while continuing to play with each other's penises. They were both in girly attire and high heels, they both had their make-up done and wore wigs for us.  

Their humiliation was devastating by this point, yet we hadn't heard a safeword spoken. I think they were both too desperate to cum. 

Katrina and I were both aware of what will happen if our two "girls" are permitted to have full-blown orgasms. Like all male submissives, sissies especially, they will both fall into that post-orgasmic slump, where they want nothing to do with us, the outfits they are in or the room they are in.

It doesn't last all that long, maybe 45 minutes tops, but Katrina and I had to be strategic about our next steps. 

They were already begging us to cum from their skillful edging, we decided to push our luck and see if they'd go further down the rabbit hole for us. A sissy who's been edged will pretty much agree to anything, if they think an orgasm is in their future.  

I had the two of them kneel and look at the floor, before I presented their next, horrible predicament option. 

"Kaylee huni, you've been locked up the longest, would you like to cum for me?" I laid out the bait for him. 

"Yes please Ma'am", he quickly responded in a wispy voice. 

"Tiffany, would you like to orgasm for me also?" I asked. 

He responded the same, and instantly. 

"Katrina and I are going to allow it girls, provided you cum into each other's mouths, after sucking some cock, does this sound fair?"

They both whimpered and protested. Shaking their heads and panicking. 

"It's ok if you don't want to, we'll just lock up your limp little clitties again". I declared as Katrina giggled out loud. 

"Have you ever sucked a dick before Kaylee?" I asked, in an uplifting tone.

He shook his head no and began to softly cry. 

"Would you like Katrina to help you with the cock?" I asked. 

He nodded his head in the affirmative and squeaked out a, "yes please Ma'am". 

HAHA! Success! We've got him in our web now! 

Katrina knelt and began to jerk-off Tiffany's cock, inches from Kaylee's mouth. She coached and guided Kaylee who was dying from humiliation at this point. 

"See huni, work the cock with your hands just a little, like this. Not too much though, you want to feel it grow the rest of the way in your mouth". Katrina said. 

Wow, Kat is a pro! So embarrassing for both of them...growing in his mouth, she said! My gawd that was hot to hear.  

I watched as she guided Kaylee's mouth onto the semi-erect dick. She began to push on his back and shoulder, encouraging a good head-bob. 

"It's ok if you gag a bit Kaylee, your future boyfriends will like that", Katrina said to him. 

Jesus, she was on a roll! "Future boyfriends!!", OMG. 

Tiffany was overwhelmed with shameful arousal and a desire to cum. He started pleading out loud for permission to orgasm. 

"Not so fast my little cock-slut, it's your turn. Ask your girlfriend nicely, for her permission to suck cock". I ordered Tiffany. 

Katrina stopped Kaylee before there were any accidents. Katrina remained in a crouch and looked up at her "boyfriend", Tiffany. 

"Well?" She barked. 

"Please Ma'am, please may I suck cock for you", he whispered out, a sickening look on his face. 

Katrina once again helped, by guiding the cock into Tiffany's mouth and stating her reminder once again. 

"Remember Tiffany huni, let it grow in your mouth!" She cooed. 

God damn! I was embarrassed FOR them, at this point. How humiliating.

Before long, our little cum-slut Kaylee was desperately begging to cum. Katrina stopped her boyfriend's sucking and looked back at me with a wink. 

It was time for our two sissies to experience a final humiliation, and yes, we were going to let them cum. 

"Ok girls", I spoke. 

"If you get into 69 position for us you may continue to suck cock and cum, provided you cum directly into each other's mouths, understood?" 

There was surprisingly no more reluctance on the part of these two sluts. They got on the floor and maneuvered into position, sticking their firm cocks in each other's faces. 

Kat and I took a seat and watched the lovely show before us. She confessed to me that this was actually really hot and she was super horny right now. Kaylee's spanked bum would have been transferring warmth, right onto Tiffany's cheeks. 

"Try to cum at the exact same time girls! And make sure everything gets swallowed down into your tummies", I reminded them. 

There was lots of slurping, the unmistakable *guck, *guck, *guck sounds, and a few deep retches. 

Before long, our two sissies were twitching and grunting their way through powerful orgasms. After so much time pent up, the volume of ejaculate must have been exceptional! Katrina and I could only imagine, rope after rope of hot cum, squirting down each other's throats. How shameful for these two straight men.  

With the help of a pair of leather gloves, I kept in the refrigerator, I had their two little clits back to limp, useless and shrunken in a matter of seconds. Kat and I wanted to get those little dicklettes locked back up instantly, before their post-orgasm slumps began. 

With the taste of cum still in their mouths, we then put them into idle bondage positions to give them time to "re-load", so to speak. This will allow for their sissy desires to return to somewhat normal levels. 

Tiffany was placed into a locked cage with an anal plug up his ass, while Kaylee was bound and gagged on the floor, with a pink dildo filling and stretching him too. 

An hour idle should do it. Then we'll return and see if they want to be fucked. 

Or perhaps fuck each other?...hmmm...

*eyebrow raise 

Mistress Andrea

xoxo

Continued in: The Leaves are Changing

What would you do for the Key?

Continued from: I just became a foot pimp

Katrina called me from across town, asking if we were still on for today...

"Yes huni, I'm just doing his make-up now", I said cheerfully.

"Excellent. I'm excited Mistress!" She replied. 

"Tiffany is all ready to go. She's just patiently, ummm...waiting". Katrina added. 

In a previous post referenced above, I had given Katrina a few ideas about her boyfriend and his sissy slavery. This is the same post where we cuckolded him in my bedroom and he was forced to watch me fuck his girlfriend. 

I had suggested that the next logical step in his transformation, could include interacting and possibly playing with another sissy slave. 

Well...that session is going down today. 

Katrina's boyfriend, a heterosexual male named Andrew, will be referred to as Tiffany throughout this post and during his sissification. 

One of my own personal sex slaves, also a heterosexual male whose name is Kyle, will be referred to as Kaylee throughout this post and during the session. 

Both of these silly boys have been made-up and dressed up. It was time to get them together to see what happens. Katrina and I thought that it would be extra humiliating for them if we were to do something vanilla first. 

We decided to all have lunch together. 

Katrina and I chatted about our "girls" during lunch and how well mannered they were becoming. We spoke of their clit cages and orgasm denial. We purposely would throw-in little injects like a "sit up straight Kaylee" or "wipe your mouth Tiffany", amidst this seemingly vanilla environment. 

The girls both had huge pouts on, with their stomachs sickened from butterflies of humiliation. They didn't eat much. 

"How would you like to start things off Kat?" I asked her. 

"Well, I think both of our girls need spankings Mistress", she declared right at the dining table. 

"I would agree. Take them up to my room and prepare them Kat, I'll tidy this all up", I said. 

Katrina first positioned my loveseat closer to the sofa, so we could spank the girls in close proximity to one another. Then she went to slip into her lingerie and heels. 

Katrina sat and addressed them both. 

"Tiffany, do you know how many days you've been in that clit cage?" She asked. 

"94 days Ma'am", Tiffany said without hesitation. 

"And you Kaylee, how long have you been locked up?" Katrina asked. 

"212 days Ma'am", his voice cracking with embarrassment as he spoke.

"Oh my. You must be dying to have your clits freed and stroked to a little spurt no? I just wonder what you'll do for us, to earn the keys?" Katrina spoke in rhetorical questions. The girls didn't answer, they just kept their eyes lowered. 

I entered the room with the chastity keys dangling around my necklace. I made sure our two sissies saw them hanging there.

"Are you spanking your own girl Kat?" I asked.

"Sure why not", she stated matter-of-factly. 

The two girls got their hairless, smooth little bubble butts, roasted over our laps. We continued until they started making little yelps and wispy-sissy noises, all while struggling over our knees. 

They looked so dreadfully humiliated and embarrassed. 

I spoke to them while they stood in the naughty corner. I offered them a horrible predicament to choose from. 

"Girls, your options are simple today. Ask us nicely to take you to the dungeon space to use and abuse you and we will. Your clit cages however, will remain locked in place".

"Ask us nicely, to take both of you to the sissy bedroom, and I will unlock your little clits". 

The two ridiculous sissies stood there in silence for a moment, then I think they started whispering about what to choose. 

Kaylee must have been elected as the spokesperson, she asked permission to turn around. 

Kaylee pathetically whimpered out, "may we please go to the pink bedroom Mistress?" 

Katrina started laughing. 

"A good choice sissy girl", I replied. "Leave your skirts here girls, you won't need them".

We sat our two girls on the pink ottoman cubes, then Katrina and I got a little more comfortable, making out and kissing each other. We told the two girls to look away, but the passionate sounds we were making, soon had their little clits straining against the chastity cages. 

"Would you two like to come sit on the loveseat together? I'll take the chastity key off from around my neck. One step closer girls", I urged them. 

I watched their horror, as I moved the video camera and mast-lighting into place. 

"Alright girls, do you both wish to be unlocked?" I asked. 

They were too humiliated to answer, they just nodded their heads in shame. I reminded them that they both had a safeword to use, if needed. 

When I unlocked their clits, they engorged and sprang to life. 212 days with not even a full erection! That's a long time. 

"Katrina and I won't be touching your clits girls. You're also well aware that you're not permitted to touch your own. You know you'd be punished for this. 

"But...we'll allow you to touch each other's clitties if you want". I laid down an awful choice for them. 

"Go ahead sweet girls, get each other hard", Katrina added. 

"Maybe we'll let you make some cummies", she cooed to them in a baby voice. 

Kaylee at least had the added barrier of a satin glove. Poor Tiffany knew she was skin on skin only. They very cutely, just started out by holding each other's cocks. I think Kaylee, with the barrier of her satin glove, was the first to start stroking and getting Tiffany erect. 

The camera's were rolling, our girls looked fantastic! Katrina and I stood back and watched the show.

Wouldn't it be cruel if we gave them this glimmer of hope, only to lock them back up again, without a release? 

I wonder what they'll do with each other, to prevent that from happening? 

Stay tuned!

Mistress Andrea

xoxo

Continued in: Should we let the Sissy's Cum?

  

I just became a foot-pimp!

Continued from: Crying is not a Safeword and the storylines involving: Cabin Crew Nylons 

"There, there sweetheart, you can stay 'little' for as long as you like ok? Mommy will take good care of you", I softly swooned to her. 

This is the manner in which I was speaking to Summer, after her punishment session with me and we had her in the tub for a nice soak. 

Her spanking experience and punishment session, administered for something naughty she had actually done in her life, brought her emotions to a deeper level of vulnerability. 

I guess the only thing that made sense to her in the moments after, was to ask me if she could be a 'little', for the rest of our time together. I happily indulged her. 

She soon found herself in an adult-baby onesie, a delicate lace choker and fuzzy pink socks that went over her knees, with little sheep prints on them. 

Summer slipped my hosed-feet, out of my high heels that I had been in for the past few hours. It was a welcome relief. She sat on her bum in front of me. 

"So this must be what the gentleman who buy your pantyhose fantasize about huh? That first moment when your hot and sweaty heels come off. They picture you running your hands over the damp musk of your nylons?" I said to her.

"I guess so Mommy. That last post I made, the one that got me punished, those nylons sold about three minutes after I posted them, and for two times the price I was asking", Summer explained. 

"Show me what you think the gentlemen wish they were doing Summer", and I extended a foot to her. 

She closed her eyes slightly, then ran her nose along the sole of my foot, tracing a line up and down the seam that ran through the middle of the sole. She was inhaling deeply, while brushing her lips against my arch. 

"Are my nylons smelly Summer?" I bluntly asked her. 

"No Mommy, not at all. They smell like feet...that have just been in hot, high heels. I smell beautiful, feminine lotion and strict leather. Your soles are very warm and damp against my nose Mommy". 

I leaned back into a more comfortable position. 

"Massage both of my feet Summer, using only your lips and tongue", I commanded. 

"Yes Mommy, right away", she replied. 

Look at her poor, spanked ass cheeks, peeking out of her little 3-snap onesie. How adorable!

I began to speak to her about this whole cabin-crew tights fetish, as she continued to cradle my hosed foot and suckle on my toes. 

"Perhaps little one, Cassandra and I could help you market and legitimize you little side hustle? Rather than sneaking a quick sale after a long flight, we could normalize your business, so to speak?"

"But Mommy, isn't it a dirty and naughty thing to do?" She innocently asked. 

"No sweetheart, you're simply providing a service to people, bringing them happiness". 

"So I wouldn't be punished for posting my hosed-feet online and selling my nylons, Mommy?" 

"No Summer, you might be punished for not producing enough content for me. You'd become my little feet hooker", I giggled. 

"We'll talk some more about this, after you make Mommy cum", I ordered. 

I slipped out of my dress and rode Summer's tongue to an amazing orgasm. She was still in a very submissive state and insatiable, she wanted more! 

I gladly indulged her. She ended up licking my pussy, feet and asshole for probably the next two hours. She had so much sexual energy!

Look at her magical little tongue, fucking my tight bottom hole. 

"That's it my baby girl! Make Mommy cum onto your lips", I continued to encourage her until my clit was too sensitive to continue. 

I threw on a satin robe and we went downstairs. I made Summer a hot chocolate with mini marshmallows floating in it, while we talked more about her side hustle. 

"We'll get you some professional photos done, of your feet Summer, as a first step. Cassandra is 19 so she knows all about the social medias, the hype, followers and smashing like buttons and so on". I reassured her. 

"Then we'll make sure you're well stocked-up with Ziploc bags and we'll start to sell your hosiery after every flight and build your little foot-slave empire." I explained. 

Summer giggled in delight. 

"You're like my foot-pimp Mommy! Are you going to smack me around if I'm underperforming?" She asked, holding back laughter. 

"Absolutely young lady. Ten toes on the curb!" I jokingly declared. 

"And I still get to be your 'little' sometimes, Mommy?" She asked me, looking all adorable and pouty. 

"Of course little one", I assured her, as I kissed her pouty lips. 

About a week later, Cassandra had a full website up and running with about 15.5K followers. She named it "Arrivals and Departures". 

There were plenty of Flight Attendant references and hotel-room pictures. Neck scarfs and high heels were in abundance. Most images of Summer looked exactly like this: 

Finally her professional cover photo that we had done.

Summer's feet:

I think in the first week, Summer had about 42 people, pre-ordering her worn pantyhose from flights. Starting deposits to even get a chance to bid, were set at $45.00 USD. 

I take half the profits of this business, Summer gets a controlled portion, like an allowance. This was her idea, she said it would make her feel more little and cared for. I set up the same arrangement with Cassie, who also received an allowance from this side-hustle. 

Yes it's official, I'm her foot-pimp now! 

After a month or so, maybe Summer can just buy her own airline, with her new-found revenue stream?  We'll have a "stable" of Flight Attendants, all working for us and selling their hosiery like an assembly line! Haha!

World Domination via fetishists. 

Mistress Andrea

xoxo

Continued in: What would you do for the key?