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 elusive sissygasm

Continued from: Sissy Slave Fucked and Diapered

I had Tiffany straddle my strap-on cock while he was still wearing his puffy diaper. I encouraged him to look to his right and watch himself in the mirror as he rubbed-off on the dildo. I calmly explained that since his little peenie is locked up, he needs to learn how to cum like a girl, through rubbing or through being penetrated in his sissy "pussy".

Tiffany tried to transfer some stimulation to his chaste penis, by riding the shaft of my dildo, all while I coached him along and told him he was a good little girl. Alas, it was no use. He only became more aroused and frustrated, with no sign of release. 

We eventually got him out of the pink crinkly diaper and I suggested we try some thinner, adult baby pull-ups, with little animal print patterns. 

I had Tiffany straddle the Sybian machine and turned it to a medium setting. 

"It's ok if you make some cummies into your pull-ups for Mommy. Squirt like a girl for me from your chastity cage". 

I encouraged poor Tiffany to try and have an orgasm, with his little dicklette still locked up.

I watched and recorded the show, as he moaned like a whore whilst riding the device. The stimulation was reverberating all around his penis and anus. 

"I think I'm also there Mommy!" He cried out, as he continued to ride the Sybian. 

"You must be so wet for Mommy. Show me you can cum like a girl!" I continued to encourage. 

I wanted Tiffany to mentally associate his pleasure with taking cock, so I approached him and had him take my dildo into his mouth, while he enjoyed the vibrations of the machine.  

 I took another photo for Summer, with the dildo in his mouth, before I turned off the Sybian machine. 

"No cummies huh?" I used a discouraged voice. 

I saw his bottom lip quivering and tears roll down his cheeks from the frustration and humiliation. 

"No Mommy"....There was a long pause. He crawled over to my seated position by his make-up station. With his eyes down he meekly asked me:

"Could we try penetration again Mommy? Then maybe I can cum?" 

Quite the eager little slut, I thought to myself. Three months in chastity has certainly turned this alpha male into exactly what I had hoped he would become, a cock-hungry, sissy slut. 

"Fluff my cock young lady", I purred to him.

He sat up on my knee like a little girl and began to stroke the cock with his ruffled, lace gloves. 

"Good girl! Moan like a slut for Mommy, show me how passionate you are for cock". I used my words to humiliate him further. 

"That's it Sweetness! Now down on your knees. You know what girls are expected to do now". 

"Yes Mommy", he whispered out, choking back tears. 

"Kiss the length of my shaft, good girl Tiffany! That's it. Worship that huge cock!" 

I continued my encouragement and emasculation of Andrew, listening to him gag on the penis and watching him kiss it with his painted lips.

We adjusted him up onto the chair, on his knees. He was good and ready to accept my cock into his sissy pussy. He was so desperate for release. I slipped him out of his little training pants and with a generous glob of lubrication, I entered Tiffany from behind. 

"Mommy, my clitty feels like it has to pee!", he mewed out in desperation. 

"That's the sissygasm building Tiffany, don't fight it! Let it happen". 

I got him onto the floor to try fucking him harder, hoping he would experience an orgasm this way. 

When the sissygasm continued to elude us, I took Tiffany over to the pink fucking bench, and secured his ankles in place. 

"Alright young lady", I spoke. 

"This is definitely going to work this time, with your legs in the air like a slut. I'll pet your balls and massage your cock cage while I fuck you ok?" 

I was determined to have Tiffany spurt for me. Just to qualify in her mind that it is actually possible. 

Forced to now stare at me, along with his precious Mary Jane heels and lace socks, I entered him deeply while massaging his swollen cock cage. 

Success!!

I watched Tiffany moan and whimper, as a few thick, powerful spurts of cum escaped his clitty cage and splashed down onto his stomach. I kept fucking him for a few moments longer, to milk out any remaining cum. Several more dribbles oozed from him cage and cascaded down by his balls.

"Good girl!" I praised him, as I removed my dildo from his "pussy". 

"You did it Tiffany! How do you feel?" I excitingly asked him. 

"That didn't really feel like an orgasm Mommy", he whimpered to me while pouting. 

I chose to ignore what he said completely and kept playing-up the fact that this was a huge step for him and a huge success in his transformation. 

"Look at all the cummies you made for Mommy! Open wide little one", I Mommy-voiced him. 

Andrew reluctantly opened his mouth and I scooped up all of his cum and fed it to him. I even flung some onto his face so he could wear like a badge of honour for me. 

"Swallow that down for Mommy. You need to get used to swallowing loads of cum Tiffany". 

His face twisted and looked disgusted as he swallowed his own sissy cream. I had him kneel for me in submissive pose. I wanted to take a photo of the cum on his face to send to Summer. 

I knew this was only a milking for him, a ruined orgasm, like a prostate milking. It was all very emasculating and humiliating but at least he felt something. 

My next plans for Andrew will be some cuckold scenes, first having to watch me with another girl. Then I'll escalate to me with a male slave while he watches. Finally I'll have him fluffing real cocks for me, and force him to watch me ride a dick he just sucked. He can be on cleanup detail too, if he ever wants his mouth to go near my pussy. 

These were the thoughts running through my mind, as I locked Tiffany into the cage in the sissy room. I gave her my final instructions of the session. 

"I want that cum to remain on your face Tiffany. You served Mommy well this weekend. I want you to spend a few hours in the cage to think about all we accomplished. When your time is up, I'll come release you and escort you to the locker room where your silly boy-clothes are. This will conclude your session, is that understood?"

"Yes Mommy, thank you Mommy", he recited, without hesitation or delay. 

Very sharp and well trained! I thought to myself as I left the room and went to fill the tub. 

I checked my phone to see that Summer had landed safely in Atlanta and had made it to her hotel room. 

I sent her the photo of "Tiffany" with cum all over her face.

There she is!! 

I sent her back a message, telling her that she looked yummy and cute. I'm going to allow her to masturbate for me, but I'm going to direct her exactly how to do so! This should be fun, I thought to myself, as I settled into the tub for a long soak.

Mistress Andrea

xoxo

Continued in: Bella's Daughter Cassandra

Sissy slave fucked and diapered

Continued from: Mommy's Sissy gets a new Name

"Well Tiffany, are you ready to show Mommy what a good little girl you are, or do you need to be taken over my knee again?"

I used my Mommy tone to torment the helpless sissy slave, while he was still gagged and bound to his princess bed. I had left him in this humiliating predicament and ridiculous outfit, following a warm-up spanking I gave him during: Mommy's Sissy gets a new name.

I had left him alone for twenty minutes, with his shame and embarrassment, the key to his chastity cage nowhere in sight. His predicament was disparaging, yet I always provided a glimmer of hope that I might unlock his penis for some edging, perhaps even a ruined orgasm, if he is obedient and feminine for me. 

But for now, it was MY cock he needed to focus on, if he knew what was good for him. 

After I removed Tiffany’s shackles and the ballgag, I ushered the sissy over to the windows and told him to kneel like a good sissy slut. 

He wasted no time in getting the dildo into his mouth and trying his hardest to please me. 

I stroked his wig, repeatedly calling him a "good girl" and reminding him that this was all being filmed for my pleasure. 

When it was time to fuck his ass, I made him ride me like a girl on his princess bed. Surrounded by mirrors so he could watch his own humiliation. 

Tiffany moaned like a whore, when my large dildo entered his tight, sissy hole. I told him that this is the way to please real men, by facing them and riding real cocks. 

I don't know what was more mortifying to Tiffany in this moment, having to face the windows in his sissy attire, riding my dildo, or having to face the video camera in reverse cowgirl. 

I was starting to feel that Tiffany had too much control over the depth and tempo of her fucking. Although very degrading, having to fuck herself on my cock, it was time to get her out of her dress and let Mommy take over.

I secured Tiffany into a floor pillory with a heavy metal collar, securing her neck to the bondage apparatus. I re-lubricated her and told her to be very vocal this time. I wanted her crying out that she loves being fucked and pleading with me to pound her harder. 

I eventually returned him to the princess bed to finish him off, with his legs in the air like a total slut. He was forced to look me in the face as he struggled through the deep fucking. His shame and humiliation was catastrophic at this point. He was so vulnerable yet still so aroused, it should be easy to get him into diapers and into the nursery after all of this. 

"I bet you want those diapers now sissy?" 

I taunted him, making him think about his original choice of wanting cock instead of a diaper. 

"Yes please Mommy. Please don't fuck me anymore", he whimpered, with tears in his eyes once again. 

"Alright my baby girl. Let's get you onto Mommy's change table and get your little bottom all wiped up". 

I reverted back to my soothing and caring Mommy tone. 

I put Tiffany on his back in diaper pose, with legs spread and in the air. I wiped and cleaned around his sissy pussy and applied baby powder to his locked up genitals. Next came a pink, crinkly diaper and a little baby girl top. 

With the additional padding that the diaper provides, it would be very difficult for him to feel any stimulation or sensation to his locked up little clitty. Exactly what I wanted, as I have some more devious plans for my naughty, baby girl. 

"Are you my little baby girl?" I cooed to him. 

I smacked the seat of his diaper, encouraging a quicker response. He nodded his head and whimpered out, "yes Mommy"...

Continued in: it was continued but Blogger deleted it.

Try this one: The elusive sissygasm

Mistress Andrea

xoxo