Reaching the Peak

Continued from: Farewell Julie

[F/m] [FF/m] [sissy] [spanking] [humiliation] [forced feminization]

What does one do after you've climbed Mount Everest and reached the summit? What does one do, in the kink / spanko community, when you have reached that same level of achievement?

Do all of you remember Sissy Alice? 

Well, through my guidance, dominance and mentorship, he literally just reached the peak!

If you'd like to go back and read about this sissy's beginnings and the first time I sent him to a professional disciplinarian, his series of tales can be found here: 

Spanked by Lady Jose

Alice's journey continued to escalate as he tumbled further down the rabbit hole, ultimately leading him to a kink event in Europe, where he was spanked in front of an audience. That story can be found here: 

Alice in Wonderland

I sent him back to Lady Jose in early May, for discipline and correction, similar to his very first session over her knee. Lady Jose and I were able to commiserate behind the scenes and thought it was time to send Alice back to school.

I guess she made him write out and recite Dutch words that she was trying to teach him, with failure resulting in the dreaded school cane, an implement poor Alice was not yet familiar with. 

Such skill and precision, look at those lines. Well done, Lady Jose! 

Back for another lesson at the blackboard...as the school strap and school paddles sit menacingly close-by to Alice's left. 

I guess he wasn't absorbing the lesson to the satisfaction of the teacher, so his bare bum did the absorbing. 

I sent Lady Jose a nice email after the session, once again thanking her for taking the time to "look after" this naughty young "lady" for me.

And to my surprise, she sends me this: 

Another thing, Sarah Gregory is visiting me in Holland in June and we do offer double sessions, she's only here for a few days and probably only once.

Do you think Alice might be ready for a double session?

Best Jose

OMG! 

First of all...Sarah Gregory is MY spanko girl crush!! I can't even...

We wrote an entire series on this blog called Tara Gregory! For cripes sakes (I hope she doesn't mind). A series of tales about a young, college-aged brat who has some mommy and daddy issues. She drops out of school and becomes a stripper, ultimately leading to her still needing to be spanked at home, even at her age. I think there is about 11 stories in that character's series. It starts here: 

Tara Gregory: Beginnings

I had butterflies on behalf of Alice I think. Could you imagine? Disciplined by the elegant Lady Jose AND the lovely Sarah Gregory...at the same time?! 

Naturally, how could Alice resist such an offer. He was almost at the top of Mount Everest and I was already up there, extending my hand to grab hold of his, and pull him onto the peak.

Alice booked a session with the two women in mid-May.

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Young Malcom stays with his Auntie from time to time, to help around the house while his older cousin Sarah is away at college.

He knows he's not suppose to have naughty feelings about his older cousin, but she’s  so attractive and alluring. 

Auntie Jose was out to the market one afternoon, when Malcom finally summoned the courage to sneak into Sarah's room. It was cutely decorated and tidy, with the exception of some laundry on the floor that immediately caught his attention. 

His thumb and forefinger, slowly rubbed the gentle fabric of her discarded panties, the delicate lace was adorable. Then a black satin pair, he nicked from the hamper and brought to his nose, as blood drained from his rational mind and pumped into his stiffening cock. 

Next he was right into her underwear drawer, rummaging through the treasure trove of Sarah's most adorable and sexy panties. To his own shock and surprise, he slipped into a pair of pretty pink ones, allowing the delicate feminine materials to cradle and caress his tenting penis. 

"What the HELL are you doing, young man!" 

Aunt Jose's voice shot out through the room, causing Malcom to jump and lurch backward in complete terror. 

"You'll be spending the afternoon draped over my knee young man...or should I say, young lady? If you're already wearing your cousin's panties, perhaps we should find some other clothing of hers to wear?" 

"Please, no! Don't dress me up like a little girl, Auntie...please no!" 

This is actually how Alice's session began. Caught with his older cousin's panties and forcibly feminized by his strict Aunt Jose. 

And they were filming this, as a production. Can you believe it?! 

"There...much more suitable young man...since you're about to be over my knee and sobbing like a little girl you may as well look like one, now come with me! It's time for your spanking." 

I'm sure there was an earlobe tug at this point, as Malcom is marched out of his cousin's room, wobbling in his ridiculous high heels and placed in timeout in the living room. 

And as he stood, facing the wall, dressed like a little girl and armed with the knowledge that he was about to be severely spanked, he hears the front door creak open. 

"Auntie..." Sarah sings out through the quiet of the home. "The teachers just went on strike, I'm home for a bit!" 

"Oh my god, M-Malcom...is that you? And are those my old clothes?!" 

Obviously you can tell where this scene is heading. Sarah is furious that he was going through her panty drawer and agrees with the frilly feminized lesson he is currently being taught. But she also wants in on the action and the opportunity to throttle her silly cousin. 

The ladies were nice enough to share some of the scene with me, while it was happening! 

Yikes! Ebony hairbrush. 

Alice would later report that Lady Jose had him by the chin, forcing him to look her in the eyes as Miss Gregory spanked him OTK. 

Auntie administered a really sound strapping after her sissy nephew was good and warmed up. 

Uncle's belt by the looks of it maybe? 

When they sent me this next one below, do you know the first thing that came to my mind? 

Sarah Gregory hasn't aged! Like at all. Maybe it’s spankings that keep her so youthful? The secret fountain of youth is having her own bottom reddened. Hehe. 

I've been following her work for years, a decade or more and she looks exactly the same! I don't know what's more exciting to me, picturing her hot little body over my knee while she calls me Mommy, or picturing MY hot little body over her lap, while saying, "yes, Miss Gregory."  

Apparently in this household, panty thieves get the cane. He was required to count each stroke and thank her for it. 

A job well done, ladies! Back in timeout with the hourglass doing its thing. 

Again, from what I understand, this was all filmed for either one or both of their production companies. I can assume that very shortly, this lovely video will be available for all of you to watch.

Simply Googling "Miss Sarah Gregory spanking" or "Lady Jose spanking" will put you within reach of volumes upon volumes of their wonderful content. 

For a direct link to Lady Jose's work, try her loyal fans link: Lady Jose Spanks 

Miss Gregory's site: Miss Gregory Spanking

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So what do we think, everyone? Did Sissy Alice reach the top of the mountain? I'd say so! 

Or so I thought. He has left the peak and is well into the stratosphere now. You'll never believe what he just did and yes, it was once again filmed! 

Another double-Domme session but this time, with Lady Jose and the infamous Mistress Baton, a woman known for the most severe judicial canings and prison-style punishments. 

And I'll leave you with a little teaser...both women packed their strap-ons for this one! 

Poor Alice! Look where this rabbit hole has lead you, and I know that you cannot thank me enough.  

You're welcome. 

Mistress Andrea

xoxo

Continued in: Suburban Moms