Summer gets a Babysitter

Continued from: Summer gets put on the nipple

Summer ended up staying in her role the entire day and into the evening. I assigned her a specific bedtime where she was diapered, given a bottle while cradled in my lap, then put down into her crib. I had her wrists and ankles loosely shackled to the crib bars with padlocks. She had the freedom to move about and stir but was not able to leave the crib or reach her princess parts to masturbate. 

I checked on her a few hours after I put her down and she was actually asleep. I turned on a baby monitor in the room for safety, in the event she needed me through the night.

I retired to my room to text Cassie. It was her maintenance spanking day tomorrow and I had just come up with a devious little plan...

I was in new "Mommy" attire by morning, which consisted of Cuban-heel stockings, a lovely dress and of course my trusty pearls. I picked out a ridiculously little sissy dress for Summer, in pastel yellow. I had her in matching ankle socks and shoes to complete the look. 

Before I got her into her dress for the day, I did some simulated potty training with her.

"Try to use the toilet for Mommy, like a big girl", I sang to her. 

She shook her head in bratty defiance, pointing at her little pink potty in the corner. 

"You want to use your pink, princess potty?" I asked. 

She nodded her head and said, "yes Mommy". 

When Summer finished up on the potty I got her into her dress for the day. She was extremely embarrassed over her attire but didn't put up too much of fuss. She knew I was standing dangerously close to the wooden hairbrushes attempt acting out. 

"Sweetie, Mommy has to head into town for a few hours and you're too little and silly to be left alone. I booked you a sitter". I told her. 

Summer's real identity poked through the layers of ruffle and satin and she giggled out loud at the thought of needing a babysitter.  

"Ok Mommy", she blushed deeply. 

It was Sunday after all, Cassandra was due to arrive for her maintenance spanking this afternoon. I figured I'd buy her a first-class train ticket and get her here a few hours earlier. She can be a "prop" for Summer's overall experience, then I'll address her maintenance. 

Cassie dressed like a bitchy teen girl for us. A style that screams: "TikTok and emojis are the only important things in my life".

"This is your babysitter, Cassie", I said to Summer. Even though the two have met numerous times before.  

Summer was drowning in humiliation, being dressed so little and now in the presence of Cassandra, who's about 10 years younger than her.

"Hi Cassie", she squeaked out with her eyes lowered. 

I continued on with my role, spelling out an itinerary for Cassandra, right in front of my embarrassed Summer. 

"Ok Cassie, her bottles are in the fridge and she's just been changed. She had a little trouble with potty training this morning and didn't want to use the toilet like a big girl, so I want you to give her a spanking before her afternoon nap". 

Cassie giggled while Summer buried her face in her hands. 

"A spanking Cassie, a timeout in the naughty corner, then a new diaper, a bottle and put down for a nap, ok?" 

I reiterated as Summer listened on in shameful horror. 

I had Cassandra repeat it all back to me in the correct order, which literally made Summer moan out loud. Deeply humiliated yes, but I could tell her pussy was aching like crazy!

Summer regained her composure and jumped into my arms to kiss me goodbye. She snuck a little grind of her pussy into my waist. Such a bad girl!

"Start the nap-time process at noon please Cassie", I said as I left the room. 

As I was leaving, Cassandra settled onto the bed and asked Summer to show her some toys. They played for awhile together, Cassie read her a children's book and they both coloured at the table. 

I think I should have put one of them, if not both of them in a chastity belt. Those two vixens are at very high risk of fooling around if left alone. 

I found out later they actually didn't. Cassie stuck to her role and Summer, despite being extremely aroused, managed to behave herself. 

As noon-hour approached, Cassandra declared it was nap time. Summer blushed and looked down at her shoes and socks. 

"How does your Mommy usually spank you Summer", Cassandra bluntly asked. 

"Umm, I have to lay across her lap with my bum bare", Summer whispered out, her face burning with embarrassment. 

Cassandra thought for a moment, then responded. 

"I'm not your Mommy so I'm not going to bare your bum for this Summer. I don't think this little onesie portion is going offer much protection anyway. Come with me to the bathroom." Cassie ordered. 

Cassie draped Summer over her lap while sitting on the toilet and gave her a long, hard spanking with her hand. 

I wonder if Cassandra was awash with butterflies, knowing she's on deck for a spanking today too? 

She then gave Summer a 20-minute timeout in the corner with her hands on her head and nose touching the wall. Just like I told her and in the correct order, she diapered Summer, gave her a bottle and put her down for a nap. 

The timing was exceptional. I had just arrived back home as Cassandra crept down to the kitchen to advise me that Summer was down and in-fact sleeping. 

I brought Cassandra into my office to ask her how it all went. 

"Thank you for doing that for me Cassie", I said. "Summer really needed an escape this weekend. We appreciate you helping her get there". 

"No problem Ma'am, it was fun and cute...

"Ummm..."

"Is it my turn now Ma'am?" Cassandra nervously asked. 

"I'm afraid so young lady, you know what day it is." My tone became serious with her. 

"Everything off Cassie, fully nude", I commanded.

"Mistress nooooo!" She pleaded. "Can I please keep my panties on?"

This was an odd thing for her to say. She's literally given me a naked lap dance before and my tongue has explored every inch of her pussy and ass. Suddenly she's shy?!...

"Ahhh, I see young lady", I hissed to her as she finally stripped her panties off. 

"We'll be talking about this further when I'm done. Now over my knee young lady", I barked.  

Cassandra was softly crying as she stripped herself naked. She usually cries before her spanking even begins, then goes a little quiet when the first few slaps start. By the time I get to my leather belt or the wooden bathbrush, she's openly sobbing again, releasing all her tension and pent-up emotion. 

She hates it in the moment, but knows it's for her own good. 

Hopefully Summer was actually asleep, for Cassandra's sake, because oh boy there was quite a bit of racket that came from this office!

As customary during her weekly maintenance, Cassandra spent 20 minutes in the corner when her spanking concluded. She uses this time to finish up the last of her tears and breathe deeply for me, surrounded by her thoughts of quiet reflection.

When her time was up I had her kneel and turn and face me while her hands were still on her head. She was dreading this moment, to be so exposed and shamed. She knew a good scolding was coming. 

"Cassandra Leigh Goth!" I lashed out. "Is this how you're required to keep your pussy hair?"

She began crying again, not from the stinging in her bottom but from the unbearable shame and embarrassment. 

"Well young lady?" I continued. 

"No Ma'am", she blubbered out. 

"No Ma'am, what?" I snipped. 

"My pussy is required to be shaved bald for you Ma'am", she stuttered out amidst her tears. 

"This is correct young lady", I calmed my tone. "And you better hope Summer stays asleep, because you're going to be punished for the next few hours". 

"I'm sorry Ma'am", she pleaded with me. 

I left poor Cassie in my office, naked and vulnerable while I went to fetch a razor and some lotion. She watched on in complete humiliation, as I dragged her by the bicep to my desk and shaved her pussy right on the spot. 

"Now young lady, what will be a suitable punishment for you? You've already been spanked so we're not going that route"...

Decisions, decisions...

Mistress Andrea

xoxo

Continued in: White Noise

Summer gets put on the Nipple

Continued from: Summer requests a MDLG Weekend

When we left off, I had Summer in an adult-sized highchair and I just finished feeding her some instant oats for breakfast. She had asked me for a weekend of deep, therapeutic age regression, wanting to be a "little" and wanting me to play the role of a "Mommy" figure. 

She had already received a spanking for being too silly with the bathtub and now, after her feeding, she just appeared extremely happy and content. 

I cooed to her in my Mommy tone, asking her to clean up her toys like a big girl. She put duckie back where it belonged, then she wanted to do some colouring. 

I showed her the little work station I had set up and the coloured pencils and markers. 

"Oh Mommy! Can I draw you a pretty picture?!" She asked excitedly. 

"Actually baby girl, it's a colouring book with pictures already in it. You just have to colour them in huni". I explained to her. 

"Ohhhh, even better Mommy!" She said. 

Little did she know, it wasn't any ordinary colouring book. *evil grin* 😈

I watched her quickly flip through the first few pages. She was giggling all the while but managed to get back into character.  

"Mommy this book is for grown ups!" She cried out in a baby voice, as she started some bratting. 

Summer took her bratting one step further, by standing up, stomping her feet and acting out a little tantrum that I can only describe as adorable. Adorable, yet I had to pretend I was cross with her and definitely mete out strict consequences. 

It pretty much looked like this: 

Wooden spoon time? Absolutely! I clicked down to the kitchen with haste and grabbed the time-honoured, traditional implement of Mommy correction. 

She was sitting on her bed with a huge pout on when I returned to her. I stripped her out of her onesie and blistered her naughty butt with that spoon until she was kicking her feet and sobbing out loud. 

Her left butt cheek was starting to look a little angry so I finished up with my hand and declared her punishment was over. 

"I think someone needs a little nap", I whispered to her. 

"Yes please Mommy", she said as she sniffled some snot up her nose and wiped her face. 

I removed my dress and bra so Summer could embrace my naked chest. I guided her head toward my tits until she latched onto my nipple. 

I shhhhushed her and soothed her, while she simulated a breast-feed with me. Her lips were soft and her suction was just right, the perfect amount of stimulation and pinch. It was making my clit jump!

After Summer spent some time rotating between each of my nipples, I got her into the crib and massaged some lubricant up her bumhole with my finger. Next came a nice big plug for her ass. I used one that is in the shape of a realistic penis. I bobbed it in and out of her mouth a few times, before her little pucker gobbled it right up and it seated in place. 

A little baby powder onto her wet pussy, followed by a pink crinkly diaper that I fastened in place and she was all set for her nap. 

I pulled her up off her feet for a kiss. 

"Thank you Mommy", she sighed into my lips. 

I carried her over to her little bunk bed. 

"You're ok to sleep in your ruffled sockies huni?" I asked her. 

"Yes Mommy, it won't be a problem. They're too cute to take off", she replied. 

"If you need to go number one you can pee into your diaper sweetie. I plugged your bum so there's no number two'ing", I said. 

"Thank you Mommy", she giggled. 

I rocked her for a bit, until I saw her eyes starting to get heavy. Then I kissed her forehead and told her to nap for Mommy. 

Even with the throbbing of her sore, spanked cheeks and pressure of the penis plug, she told me she has never felt more comforted and cared for. 

Mistress Andrea

xoxo 

Continued in: Summer gets a babysitter

 

Summer requests a MDLG Weekend

Continued from: The leaves are changing

If you've been following the news lately, I am sure you've noticed some of the struggles that airports have been having. Long lines, baggage staffing issues, lost luggage et cetera. Of course, in concert with having the worst traffic gridlock in the world, I think YYZ just earned the accolade as being one of the worst airports in the world too. 

I'll qualify that by saying worst for lines, wait times and recent baggage issues. Apart from that it's clean, safe, has good food and everyone in Canada are generally pleasant. The 1% however, the loud-mouthed, selfish and disrespectful, greasy travelers, who make everyone's experience poor; guess who takes the brunt of their horseshit? My little angel Summer!

How could you give her a hard time?! She's so cute I wanna bite her bare butt!

Well, she called me, almost in tears, from outside of her hotel near LaGuardia. Let me tell you, Mama Bear's claws were coming out as she vented to me.

The poor thing. She ended up telling me that she had a shitty couple of days. Apparently her flights were full of entitled passengers, trying to get to their cruise ports so they can spend the next seven days filling their gobs with buffet food.

I let her vent away, then I did what any loving Dominatrix would do. I floated out an invitation to spend the entire weekend together, doing anything she wants! 

I asked if she wanted to leather-up and take out her frustrations on some pathetic, male slave in my dungeon. I asked if she needed a spanking with cornertime, to press her reset button and even asked if she wanted to be ravaged and pillaged, Viking style, as she experienced with me before: Rise and Reign

Her response was freakin' adorable! It went a little something like:

"Mommy...I want to spend the weekend as a little, would that be alright?" She squeaked out in a baby voice...

Awwww, my heart! 💖

Of course I agreed. 

I had the added pleasure of getting to tell her that I renovated a space in my facility, exactly for moments like this. A space that is slightly different than the sissy bedroom, where she can escape to a world of cuddles, colouring, being fed in a highchair and put down for naps in a crinkly diaper. I think she'll love it! 

When Summer landed back in Toronto on the Friday night, I had a limo waiting for her at he airport to bring her to my facility. 

As usual, when she and I have been apart for a bit, we couldn't keep our hands off one another. 

I told her that we wouldn't be "starting" until tomorrow morning and that we had a freebie night before her regression begins. 

That being said, we spent most of the evening on the furs in front of the fire, cumming onto each other's lips repeatedly. Her pussy still tastes like friggen gummy bears. My gawd!

In the morning I slinked my way out of bed and left Summer sleeping, while I went to shower and put together my "Mommy" look for her. I think I nailed the 50's housewife quite well! Clicking around the kitchen, constantly baking something with a wooden spoon in-hand. That’s the look I was going for. I wonder if June Cleaver, in her pearls and elegance, ever took the wooden spoon to Ward? 

Look at my precious little sleepyhead! I woke her up gently and took her to the new space to give her a bath. It was quite the sight, to see my bare naked Summer, using the potty on the left while I filled the tub for her. 

While she was in the tub I picked out an adult, three-snap onesie for her and some thin white knee socks with ruffles and bows at the top. 

I had her do a diaper position in the crib for me while I got her into her socks and onesie. She looked absolutely adorable!

I asked her to go empty her potty into the toilet and drain the tub, which one would think, should take about 30 seconds. After five minutes, Summer had not returned...

I entered the bathroom to find Summer splashing water all over the place while playing with a yellow duckie.

"My word young lady! Look at the mess you're making!" I shouted. 

She had managed to turn the tub faucet into a decorative fountain / waterside somehow. 

"I was just letting duckie go down the water slide Mommy". She explained.

"You're so little and silly Summer, and now there's water all over the floor. Get over here this minute missy!" I scolded. 

I bent her over the counter so she could see the vicious hairbrushes that rested there. I spanked her butt until she was yelping out loud. 

I then took her across my knee and continued to tan her little arse, right over her onesie. 

I carried on until she was crying out, "I'm sorry Mommy". I didn't need to escalate to my hairbrush, my hand did the trick just fine. 

Summer was made to mop up her little mess, all while nursing a sore bum. 

While she dealt with this, I made her some instant oats and told her it was time for breakfast. She blushed when I showed her the highchair I was going to use and how I was going to spoon-feed her.

Little airplane noises while I feed her maybe?...Too soon? 

lol

Mistress Andrea

xoxo 

Continued in: Summer gets put on my nipple

  

    

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