Keyholder

Continued from: Bridesmaids

What must be running through the minds of these two, pathetic sissies I wonder, as they kneel here before Summer and I, clenching their bum cheeks so semen doesn't ooze from their bottom holes?

Each clench of their recently used sphincters', causing their cocks to twitch from within the metal bars of chastity cages. 

I have written of their journey into forced feminization before, so I won't waste anyone's time by going over it again. The Coles notes version is simply, these two hairless, heterosexual males are dressed like frilly bridesmaids and they were just bent over and fucked up their bums by a pair of "real" men. 

Summer and I were just coming down from the highs of consummating our marriage, still in our heels and still in our bridal lingerie, enjoying the way we tasted off each others' lips.

Bella and Vanessa had since left the hot tub and were now continuing to get to know each other, in the pool. After laying eyes on Vanessa for the first time, even MY mouth was watering, at the thought of what she must taste like. I'll have to ask Bella later, hehe. 

Our two pilots, after emptying their balls into the bowels of our two sissy slaves, headed out with the remainder of our reception guests. 

It was now time to treat the sissies to the gift I promised them, a rare but well deserved unlocking!

Since I first starting exploring and using enforced chastity with my silly males and sissies, much has changed on that front. There have been some significant advancements thanks to use of technology. Believe me when I tell you though, a chastity boy will do anything to cheat the system, escape the device and ultimately masturbate. Don't trust them! Take the use of chastity very seriously, if you go down this path, do it properly or don't do it, there is no half-assed or in between. 

Being a keyholder to many, I'll share with you my system of layering. I strongly believe that many things BDSM, are best complimented by layers of psychological captivity. Most submissives want and crave to feel "forced", captive and helpless at the hands of another. This is what fuels the submissive kink. 

A good example of this is the use of a bondage cage. I can put a naked submissive inside and padlock the cage. Under no circumstances can they escape without my intervention. However, I want this to be felt more deeply in their mind. I put the person in metal shackles first, wrists and ankles, then into the cage which I padlock shut. There's one more layer, plus a gag, but don't leave them unsupervised with something in their mouth. 

One more layer? Absolutely. Keep your bondage cage in a room with a cell door or lockable door. Let your slave see you shut the door and lock it, before you leave them in all these layers. It works great!

Chastity keyholding is no different. I want layers upon layers of security and control, so the silly male or sissy truly feels that there is no escape for their penis, without my intervention. 

I'll share with you my system, it works well. 

Most chastity devices either have an external padlock or these fancy new internal, brass locks. I prefer the internal, it's more sleek, less visible under clothing, which my silly males like and small padlocks can be easily clipped off with bolt cutters. 

Speaking of bolt cutters, I prefer metal bar chastity cages to plastic. I can't picture anyone with a penis, attempting to use bolt cutters on the bars of the device itself. Way too close to the little peenie to take a risk like that. Eeeeek! 

Lastly, most internal lock devices will come with two keys. My first step is to engrave my initials into both keys. For emergency and safety purposes, the chastity slave will get one key and I will keep the other. At my Facility, the key is kept in a coded lockbox that resembles a safe.

"But Mistress, they have the other key, at home, unsupervised. Do you trust them with that?"

Absolutely not! But safety is paramount and there should be a "break glass in case of emergency" option. 

Here's how I do it. 

This is a fun new item, recently on the market, in the kink community. It's great for distance domination and distance keyholding. Once paired uniquely with each device, I can use the app to Bluetooth unlock this little plastic key box. My slave, cannot defeat the app or open it by any other means short of taking a hammer to it.  

Their emergency key goes in here and the little coffin clicks shut and locks. I can open it remotely if they ask me to, providing a good reason of course. The app will track and record openings of the lockbox also, so if there is an unauthorized unlocking of the key box somehow, I'll know about it. 

Remember layering? I'm not done yet...

Adhesive, tamper proof bags, which all have a unique code on the face of the bag. 

The key box goes inside this bag, the strip that is removed to expose the adhesive for sealing the bag, has a code on it. The code on my "receipt" essentially, matches the code on the bag. I keep this with my version of the key, my slave keeps this sealed bag. 

When my slave attends for a session, they are required to produce the bag at reception, so Cassandra can confirm if the two codes match and the bag as not been tampered with.  

It seems like a lot of fuckin' around, but you only have to go through this once. It's well worth the extra effort. Once my silly males see the care and attention I put in to the security and cheat-proof keyholding, I can only describe their reaction as defeat...and despair. 

Like these two. So desperate for release that one of them has a penis up his bum and the other has a penis in his mouth. That kind of despair! 

A deal is a deal and I stuck to my word. 

I promised my two sissies that if they "entertained" the pilots, and boy did they ever, I would unlock their dicks and allow an orgasm. I didn't specify how, but I certainly had to make it humiliating. 

I accessed Kaylee's primary key from the safe I keep it in and unlocked his penis. Summer helped him out of his dress and panties and we kept him in his stockings and heels. 

His delicate and feminine satin glove, had his dick hard in no time flat. Tiffany listened from a position of timeout in the corner, in full view of the windows. He listened to Summer and I coach Kaylee on, encouraging to cum into his open mouth and onto his face. 

The ass fucking Kaylee just took probably helped to stimulate his prostate. The amount of sticky, hot cum that Kaylee fired at her open mouth was incredible. 

I took a picture while Kaylee was still grunting and cumming, being sure to capture some action shots of this gigantic facial. 

I took a page out of one of my reader's play books and sent Summer to the bathroom sink with Kaylee's panties. Summer was given instructions to run them under cold water then wring them out and return. 

I handed Kaylee the cold, wet panties and had him put them on. He gingerly crept them up his legs, dreading the moment they would come into contact with his still erect penis and balls. He gasped and winced, the moment the soaked panties finally caressed his genitals. 

 

"What a great idea for erections Mistress," Summer declared. 

"I can't take credit for this one Sweets, and it IS a great idea!" 

We put Kaylee in timeout, to suffer through the cold embrace of his panties and rapidly shrinking penis. 

Tiffany heard all this from his previous position in the corner. I wonder if he even wanted to cum anymore, knowing full-well how he was going to be cumming, the swallowing of his self-facial then sentenced to cold, wet panties. 

Who was I kidding, of course the little ape wanted to wank! 

Once Tiffany was cold, shriveled, humiliated and had the taste of cum in his mouth, we got both he and Kaylee locked back into their cock cages. 

Two tummies full of cum, two sissy bum holes full of cum and hours of hot sex with my wife beforehand. 

How did you consummate your marriage? Haha 

Cheers. 

Mistress Andrea

xoxo

Continued in: A New Dungeon Space