The Life of a Sissy Slave

Continued from: Rise and Reign

There was much to clean-up, after Summer and I enjoyed a night and then a morning of lust together. My sissy slave, Tiffany, had his first opportunity ever, to see me with another girl. All while his little pennie remained locked in a chastity cage. 

Sissy did a good job, holding our toys and lubricant for us. I put a butt plug up Summer's ass and spanked her, while Tiffany watched. He must have been so tormented and desperate for release. 

And what of the huge mess? Well that's where Tiffany comes in.

I fully assume that Tiffany sneaks a little sniff, or a quick taste of the gusset of my worn panties. His desperation level is so intense that I actually don't blame him. I fully assume he smells and feels the delicate nylon feet of my stockings. Most male sissies have deep fetishes toward hosiery and high heels, so naturally, I make him hand-wash my delicates and polish my high heels when in slave-maid mode.

This weekend he gets the added bonus of seeing to Summer's delicates and footwear also. I’m quite certain he had a little Flight Attendant fantasy, crush on her. Her whole work universe is hosiery and heels! 

All of Andrew's elaborate sissy dresses come from Amazon or Etsy, or a lovely online store called the Sissy Boutique. At the back of the neckline zippers, there are rings to attach a padlock. His waist aprons with bows have a second padlock, and all of his ankle cuffs have a stirrup which runs under the base of his high heels, locking the shoes onto his feet. 

I enjoy that he has the autonomy to just mince around the house in his locked heels, seeing to his list of chores. It's just like white noise in the background, watching him work away, cooking and cleaning like a 1950's housewife .

With the lockable clothing in place, I can even leave the house for hours on-end while chores are being completed, content in knowing that he cannot escape the layers upon layers of satin and ruffles. 

I suppose if he wanted to escape my facility he could simply walk out the front door, but he'd then have to walk home in his maid dress and heels. Psychological bondage is so lovely!

I do make him go outside, while crossdressed, but he typically does this very quickly out of fear the neighbours might see him.

Out on the back deck there is a little more privacy, but people still have windows. Five or ten minutes serving Summer and I while we sun ourselves, is usually all he can take before he's begging us to punish or beat him, if it means he can scurry back inside to hide from the humiliation. 

We sent him back inside to clean and sanitize our sex toys. I love making him handle and clean the realistic dildos and strap on cocks, knowing he's been forced to suck them and having to reflect on the last time I fucked him like a girl.

So there you have it, the life of a BDSM sissy slave. I don't have to cook, I don't clean. My high heels and boots are always polished and sparkling, and my lingerie and hosiery is hand-washed in rose-scented water and hung to dry.

 Life is good! 

I've been asked by a few people, Summer and Cassandra in particular, how I go about "making a sissy slave". 

The answer is simple. The sissy was always there. Like a gifted sculptor, I just chipped away at the rough edges. 

I typically would not go and seek-out a sissy slave, they seem to appear naturally, you just need the all the right ingredients. And what are those ingredients you might ask? Take Tiffany for instance, nee: Andrew.

It requires a couple tablespoons of Financial District, corporate douchiness, a pinch of misogynism, and a yellow or red sports car. (a tell-tale sign of a small penis, which in the case of Andrew, I confirmed was accurate). *giggle*

Then go and cheat on your girlfriend with the local office tart.

That is how you go from this:

To this:

Andrew's girlfriend is Katrina, quite a pretty and a sexy little thing. Who doesn't like a fiery redhead?  

When she first brought Andrew to me her inner-fire was raging alright. She was out for revenge. It was all about his infidelity and wanting him punished and humiliated et cetera. We did all of that, but it wasn't until I suggested a chastity device that we really started making progress. Orgasm denial does wonders to silly, male pets. 

His process was long and required much commitment on the part of both of them. Shaving became waxing, waxing became electrolysis and with the help of Summer's fitness routine, Andrew began to develop more feminine curves and a rounded butt. He is now completely hair-free from the neck down and smooth like a girl, with more of an hourglass figure. 

Upon my request, Katrina disposed of all his male underwear and replaced them with the most delicate, feminine panties. The keys to his chastity cage are kept with me. Even if she wanted to unlock him to enjoy his tiny cock for an evening, it is literally impossible without my intervention. 

The next time you're surrounded by these presumed, alpha males, in their skinny-legged suits and outrageously colourful dress socks, see if you can pick out the one who is hiding a little secret under their façade. 

Which of them is being forced to wear panties, even stockings and garters under their suit? Which girlfriend, wife or Mistress, has their dicklette locked up in a chastity cage?

So this is how my sissy slave came to be. Monday to Friday, 9-5, he's Andrew, 24/7 kept in panties and a chastity device. 

On weekends he's sentenced to my facility as "Tiffany", where he sleeps in his frilly pink bedroom, nursing a sore bottom and weeping into his princess sheets.

Mistress Andrea

xoxo

Continued in: The Receptionist

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

Train the Trainer

 Mistress Andrea certainly keeps herself in top physical condition, it is a bit of a requirement for her unique work as a Dominatrix. However, she was noticing that some of the husbands and boyfriends of Willow Creek were a bit doughy. They definitely will not be able to fit into the feminine and frilly clothing she has planned for these silly, sissy boys. That being said, Mistress went and found herself a 25-year old, ex-figure skater with Mommy issues, the cute and bubbly Summer Holiday!

Look at this little sniper!

Before Mistress could unleash Summer on some of her clients, she thought a familiarization session should be in order. This was Mistress' home gym yes, but it had some special features. It was no ordinary gym when you look closely. 

Summer certainly had the aggression level for her new role. She just wasn't 100% sure about the new types of motivation Mistress was telling her about. Whipping, spanking, cock and ball torture, feet and ass worship...this was all new to her. 

Summer went on to try some of the other equipment, all while glancing around the room and noting that some parts of the equipment had been sexualized, or bondage implements added. 

When she saw the electo-sex prod and the single-tail whip, she started to understand what would be required of her but didn't know where to start. 

Summer, using her most cute and submissive tone, politely asked Mistress if she would run her through a workout session using some of the new "stations". She said it would help her understand what the sissy male slaves would endure. 

"Of course sweetheart", Mistress happily obliged. "Let's start with the deepthroat trainer. You would use this station to humiliate the silly boys and giggle at them while they struggle to please you. Remember to rate them on their cocksucking abilities and belittle them about how much they love sucking cock”.

"If their nose can dab the pressure plate at the base of the training dick, the device will record this. You may wish to reward a slave for a high score", Mistress went on to describe. "If their nose can't reach the plate, you may need to ah-hem...motivate them. Would you like to try Summer?"

"Ooooo yes please Mistress!"

Summer eagerly got down on her knees, like she's done this before, and took the training cock into her hand and guided it into her mouth. 

"It looks like you could use some more intensive training also Summer", Mistress snipped. "Your nose needs to hit the counter to record a successful suck". 

Summer gagged and wretched loudly. "Mistress I can't reach it", she panted, with slobber cascading off her lips.

"Perhaps YOU need some motivation? Go kneel by the mirror and get those pants off. Hold the riding crop in your palms for me", Mistress commanded. 

"That's a good girl!" 

Summer could feel those words electrify and caress her pussy. Ohhh how she loved being called a good girl. 

Mistress gave Summer twelve lashes of the riding crop on each bare bottom cheek, which she made her count aloud. 

"Is this how you want me to motivate your clients Mistress?" Summer yelped out as her whipping concluded. 

"Absolutely!" Mistress Andrea replied. "Now lets try the exercise ball. I can see your pussy has started to provide the lubricant already". 

Summer blushed deeply but Mistress was right, something about the vulnerability of this situation, the embarrassment, giving up control and the pain...it was making her so aroused! Summer slipped easily onto the exercise ball and groaned out loud when the dildo entered her. 

Mistress helped to press on Summer's shoulders so the bouncing action provided her with a good fucking.

"Now remember Summer, when you're doing this with the sissy boys, the training cock will be right up their ass. Be prepared for a lot of whining and crying", Mistress coached her. 

Summer moaned out and gasped, "Yes Mistress, my gawd I'm so turned on!!" 

"Can we start back up in the morning Mistress? I need you to FUCK ME so bad right now!"

"With pleasure sweetheart". Mistress purred, as she reached for her strap-on. 

Mistress took Summer around to every piece of workout furniture available, and fucked her on them.  Summer was ravenous, high energy and had cum three times so far. 

The two of them were actually breaking a full sweat now, Summer was quite the little handful. 

After Summer's fourth orgasm Mistress pulled out. They were both out of breath, painted in sweat and smiling from ear to ear.

"I think I'm gonna like it here Mistress", Summer said, still breathing heavily. 

"Time to hit the shower huni?" 

"Yes Ma'am, just don't forget the strap-on". 

Mistress shook her head in disbelief. "What a little wildcat!” 

Until tomorrow...

Continued in: Summer Stays the Night