Sissy Sucks Cock and I get a Spanking

This summary is not available. Please click here to view the post.

I lost the bet!

This summary is not available. Please click here to view the post.

The Predicament of Chastity

Continued from: Time for a Recap

I don't operate a rub n' tug. You don't just roll in here for a blowie or a handie...silly boys!

If you are male and a client of my Facility it means you are in a 24/7 chastity device with no access to the keys. You better believe you're going to pay for your orgasms, when they're permitted! Both financially and psychologically. 

"Aww, is someone crying little chastity tears? Would you like Mommy to unlock you?"

As described in the post called: Remember, be girly, I began to offer a service at my Facility where chaste males who had just been spanked and had finished their 20-30 minutes of cornertime, could be jerked-off to orgasm. 

To be eligible for this service, the silly male would have to be in their cock cage for 30 days minimum and pay an additional fee of twenty dollars, on top of their overall session fee (which is quite a bit more than that).

The other dreadful condition, is that my sissy Secretary, Kaylee, would perform the handjob. Yes, Kaylee is almost 100% passable as female, but my male clients still know Kaylee is a dude and that they're being jerked-off by a dude. 

They usually hold-out beyond the 30-day mark, trying to fight their desperation with their own machismo and homophobic ideologies. But by day 38-ish, they're calling the Facility, sniveling and whining to be unlocked, begging for a spanking session with handjob ending. 

In comes Kaylee, I personally remove the cock cage from the client and my sissy works the cock until there are ropes of hot cum all over their stomach, all over Kaylee's face or both. 

I mentioned in a previous post that I keep an elegant, feminine pair of leather gloves in the refrigerator. Immediately after the client cums, these gloves get handed to Kaylee to be put on. He will continue to handle and fiddle with the client's cock until it's dreadfully cold, shrunken and limp. The chastity cage is locked back on, I retain the keys and the client's session is over.

Time to fuck with their minds just a little more! 

We began to advertise and offer a blowjob program, BUT! Here are the conditions as it was written in our feature-sheet we sent out to the clients:

My caged boys who have been locked for 30 days or more, know they may ask for a handjob to orgasm at the end of their session, for an additional cost of $20.00.  However, if you can hold out just a little longer for Mistress, you'll have a soft, delicate, warm mouth...to cum into!

That's right my little pets, any client who has been locked for 60 days or more, may ask for a blowjob!

Wouldn't that feel nice, can you make it 60 days for me?

It's only an extra $50.00, added to your original session rate. 

Mistress Andrea xoxo

What a mind fuck huh? Hehe

Do they hold out for 60 days, can they hold out, just to get a blowie? Or do they jump the gun and just take a handie by day 30? 

They all know it's going to be Kaylee doing it, so they have that mental hurdle to deal with too. I've said it before, chastity and denial does wonderous things to silly boys.

Or...they safeword out of this mental torment completely, their chastity keys are returned to them and they are no longer clients.

This was fun! So enjoyable that Summer and I put a bet on who would break first. Not who actually...but when. Closest to the number of days without going over was our terms. 

Our wager...which I still can't believe I suggested, was a bare naked, very real, hairbrush spanking for the person who loses the bet, administered by the person who wins. 

Summer has never ever spanked me and never Domme'd me before, but it didn't matter. I wasn't loosing this one. I know my clients better than she does.

I had someone in mind, my winning horse! We weren't picking names of people, just the time it takes them to break, but I had a specific person in mind. I took the cocky route and chose 60 days, exactly. 

Summer knows a few of my clients but not all of them. I think she just randomly picked a number. She settled on 67 days, we both smiled and shook on it. 

To make things a little more real, we both agreed on the brutally severe, antique, ebony hairbrush.

Even I started to feel a few butterflies, questioning my cavalier selection of 60 days. This is gonna fuckin' suck for whomever loses this bet!

Just to rub some salt in it, we deliberately displayed the vicious brush on the fireplace mantle of our room, where it would stay, as a reminder, until the bet is "settled". We wrote down

Andrea: 60

Summer: 67

on a little piece of paper and slid this note under the backside of the hairbrush. I guess if she really wanted to be a bee-otch, she would have just picked 61 days, and cock-blocked me. A client could hold out for 200 days and Summer would still win, as she didn't go over and is closest to 200. Remember those losers on the Price is Right? That first bid thing and some jackass would fuck everyone and just bet a dollar. I'm glad my darling Summer is too young to remember that show, I doubt she's ever seen it. 

Haha! 

I loved how poor Kaylee didn't even know he and his mouth are now being wagered on for sport! The end result of all this shenanigans will be a 60+ day, pent-up river of ejaculate, being blasted into his mouth from an erect cock. Poor poor sissy! 

We decided to bring Kaylee upstairs to break the news to him. He knew that client cocksucking was now being offered but I wanted to explain my expectations. 

We didn't mention our bet but I touched on the 60-day minimum and a few of the other rules. 

I explained that after the clients had finished their full session, whether it be spanking or dungeon domination, they would be taken to a small blowjob room. In this room they would be bare naked, bound, gaged and blindfolded. Only then does their cock cage get removed. 

"I'll come and get you Kaylee, to lead you into this room and you will suck the client's penis until they cum into your mouth ok?" I said cheerfully. 

"Then it's cold-glove time, the cage goes back on and they can go collect their things from the locker room".

Kaylee lowered his head in shame and groaned in defeat. 

"No spitting. You will swallow every drop of cum!" Summer added. 

Hehe, that's my girl! She beat me to it. 

Speaking of Summer beating me...lets fast forward shall we? 

This little twerp in my waiting room is named Edward, he was the horse I bet on. When our notice about blowjobs went out he was at the 23-day mark, since his last unlocking, not even eligible for the handjob program.

37 days later, on day 60, I was waiting by the phone for the call to come in. That day came and went with no sign of the desperate Edward. 

 

This little fucker went 71 days, before calling to book a session and asked for a blowjob ending! 

Summer won the goddamn bet, because of this little puke. Now what? I'll tell you now what. 

Kaylee is about to suck his first cock for money...

And I have to go see Summer, to "settle" this bet she just won. 

*sigh*

Mistress Andrea

xoxo

 

Continued in: I lost the bet

 

 

 

 

Time for a Recap

Continued from: "Big Girl" Clothing

I am embarrassed to admit that I did not know what the term "recap", actually stood for. Thanks Google. Nor would I have pronounced it the way the Google lady did when I hit the little audio button.

re·ca·pit·u·late: to summarize and state again, the main points

Similar to SPAM? You know that stuff? The grotesquely coloured, gelatinous mold of meat. Google didn't get this one right, it actually stands for "spiced ham".

Arby's is another fun one. Arby's is a popular fast-food chain in the States. Raise your hand if you were today years old, when you learned Arby's is pronounced RB's, and R.B. - simply stands for Roast Beef.

Enough of my nonsensical rambling. I thought I would provide a RECAP post, just to ensure everyone is caught up on who's who and where everyone is. 

Summer officially moved in with me after we spent a magical few days in New Orleans. We foodie-explored, drank and fell in love with each other, over and over again. She is still a Flight Attendant for a major airline and I still manage a devious little side-business for her, where she sells her cabin-crew nylons and high heels to salivating foot fetishists.  

She and I have actually been house shopping. We're looking to move and create a new "Facility" for our clients, with exciting new fantasy spaces and more vanilla living space for Summer and I. To follow our beautiful journey together, these posts will help.  

Summer first comes into my life: Train the Trainer

Our sexual relationship begins to blossom: Summer's first time in the Dungeon

Fight Attendant Nylons: Selling used hosiery

I begin to fall in love with her: Can't say goodbye

My very first client, Bella, has officially become a collared slave. She has signed a contract turning ownership of herself over to me and thus far, she has been a spectacular little playmate. Summer really enjoys playing with her too, both in a Domme role and even as a submissive alongside Bella. 

I'm not sure what she does about her husband, when she comes home with welts on her body, her bare bum bruised a crimson red and striations on her wrists and ankles from braided rope. Or those times I send her home in a chastity belt and I keep the keys! lol 

Oh well...not my concern. She serves Summer and I very well, without complaint and she absolutely loves her role and the therapeutic BDSM that comes with it! With the following posts, you can follow Bella's transformation from an affluent, snooty housewife, to a drooling and collared anal slut. 

Her very first spanking as an adult: Bella Goth spanked to tears

 

She masturbated after being spanked: Shameful Arousal

She likes age regression: Bella and MDLG / ABDL

She likes anal and pony play: Bella's Pony Session

Bella finally gets collared: I own Bella as a sex slave

Bella also has an adult daughter if you remember? The tight-bod, juicy-arsed little dancer, Cassandra Goth. She almost got kicked out of her swanky performing arts school, until I took her in hand and gave her the spanking she greatly needed. She took a job as the receptionist to my BDSM studio that we refer to as "The Facility". Cassandra then turned into my personal stripper on the side, when she discovered that I had a special room, specifically for that purpose. 

We began a strict regiment of maintenance spankings with her, once a week in my office while I helped her to focus on her studies. Her new found discipline got her back on track and she was not kicked out of school. The double-edged sword to that story though, is that she had to leave both me and her part-time job behind to return to school in the fall. Every Sunday however, she takes the train home to have dinner with her family. Prior to going home she stops by my house, religiously, every Sunday, just to receive her maintenance spankings. 

She should be done her second year within a month or two and has expressed an interest to return to The Facility and resume her secretarial job. She also misses stripping for me and giving me lap dances, so she is more than welcome to come back! Cassie has been a bi-curious little plaything of mine before too, she has the confidence of youth, a chip on her shoulder and a bit of a potty mouth. More or less, she's an absolute weapon! Haha. You can read more about her escapades here:

First time meeting Cassie: Bella's Daughter Cassandra

Her punishment spanking: Cassie spanked severely

She's my Receptionist: Cassandra checks her Mom into my Facility

Summer school: Cassandra finds the strip joint

To cover Cassandra's receptionist role, her replacement has been a male, heterosexual slave of mine named Kyle. Or at least he used to go by Kyle. 

Inescapable chastity and orgasm denial soon led to him willingly wearing panties under his boy clothes for me. Hair removal came next, anal bleaching, full female outfits, sissy outfits and now he goes by Kaylee. With full hair and makeup done and in high heels, he performs the role of my slutty Secretary at The Facility. 

I've taken him as far as performing handjobs on male clients who qualify for this service, and he has sucked the cock of another sissy and swallowed his cum. He still has a long road ahead, to become my perfect little, sissy cock-whore, but we'll get there. 

When Cassie returns to her summer Secretary job, Kaylee will be demoted to a sissy maid. If you're interested in how a heterosexual, male submissive ended up in frilly pink dresses and high heels, you can follow Kaylee's journey here: 

Kaylee still identified as a male here, in Summer's Domina Debut

Long-term chastity started to change him: Darwinist Domination

Desperate to cum, two sissies jerk each other off: What would you do for the keys?

They finally suck each other's dicks: Should we let the sissy's cum?

Who's the other sissy that Kaylee performed a 69 with? Remember Andrew? Boyfriend of the fiery redhead, Katrina. Andrew was also a heterosexual, once alpha male, laced with a personality featuring toxic masculinity. Well his name is Tiffany now and he's laced in something else these days, literally, along with bows and satin and nylon.

His journey was an interesting one, which started with strict spanking, a personal trainer (Summer) and 24/7 chastity. Now, he knows what it's like to suck a cock and knows what it's like to have cum breath. Katrina has recently taken on a bull as her new boyfriend and the two of them cuckold and humiliate Tiffany frequently. 

This is Katrina's tattooed and hipster-bearded bull named Cole. Can you picture Tiffany kneeling before Cole and undoing his belt, his hands beginning to tremble, knowing that belt has been used on his own ass before, at the hands of Cole. Then unzipping his pants and taking his alpha cock into his sissy mouth, just to fluff Cole hard, so he can fuck Katrina right in front of him. 

Incredibly humiliating and emasculating isn't it? They have an awesome throuple dynamic. 

Let me see if I can get this right, Katrina told me the other day what the official "pronoun" is. Tiffany now identifies as a pussy-free, sissy cuckold. This means he's required to fluff Cole, possibly even be fucked by Cole. The only time Tiffany can taste pussy is from Cole's dick, after it's been inside Katrina. Other than that, from what I understand, Tiffany only gets to lick Katrina's ass, panties, feet and footwear, and pleasure for him means pegging, actually being fucked by a real cock, or sucking dick. 

You can catch up on the pussy-free, sissy cuckold below and how "Tiffany" came to be:

Summer meets Andrew for the first time: Train the Trainer

Andrew officially becomes "Tiffany": Mommy's sissy gets a new name

His first sissygasm: The elusive sissygasm

Katrina considers a bull: Sissy Maid

As for "The Facility" itself, business has been steady and the constant flow of money is an added bonus. If you love what you do for work, you'll never work a day in your life right? 

Most of the clients to my Facility are still predominately seeking adult discipline and spanking, for a multitude of reasons. With Summer living with me, we now offer a dual Dominatrix rate for the dungeon or a dual Disciplinarian rate for spankings. A handjob eligibility program started, with Kaylee jerking off the male clients after they've been spanked. This added perk has been wildly popular and another new revenue stream, pun intended ;)

I have been thinking about a male client, blowjob program, for after their spankings. It would be Kaylee's sissy mouth of course, not fuckin' mine! 

I hope this RECAP helped and you're all caught-up now. I'm about to go tell Kaylee that she's going to be sucking the client's dicks for money soon. Eeeee! *squeal* of excitement. 

Mistress Andrea

xoxo

Continued in: The Predicament of Chastity

 

"Big girl" clothing.

Continued from: Slumber Party Subs

When you're dressed in "big girl" clothing, Mistress lets you do big girl things! 

Both Summer and Bella knew this, when I originally offered a change of attire. From the lens of all three of us, this would officially bring an end to the MDLG scene we had been exploring and officially start a new scene. Where this scene would take us, I didn't know yet. But what I did know is that I wanted to watch!

Who wouldn't want to watch this!? 

Patent stilettos with ankle straps, glowing from the light of the fireplace. Delicate stockings on their toned legs, creating an airbrushed silhouette. God damn these two are sexy as fuck! Whatever shall I make them do?

Taking turns manually masturbating each other in front of the fire is what I went with first. Just enough to bring each other to edge a few times. Neither was permitted to cum yet, even though they both began to beg me for an orgasm. 

As they were finger-blasting each other's pussies, I peeled myself out of a few layers and got extra comfortable on the couch. Having just denied them orgasm, I wanted to tease and torment by showing them how wet and aroused it made me, to watch them in action. 

They knelt in place before me, with their heads down and cunts throbbing, and were forced to watch me masturbate to orgasm. Summer whimpered a little, playfully. Bella remained silent, likely fearing a whipping. She knows she is the slave in this dynamic, required to adhere to more strict rules, while Summer is the submissive and is granted a little more latitude to act out. 

I gave her a treat, and told her to hover her asshole over Bella's lips, then face-sit her. 

I orchestrated a transition into 69, where I granted both of them permission to cum. Due to the build-up and the edging, their pussies were like a hair triggers. One wisp of breath, the grazing of a tongue and some moaning, had my girls cumming instantly.

I was overjoyed to watch them cum at the same time too! So friggen hot. 

Ok...now it was my turn!

I knew exactly what I wanted, but I had to tip the scales in my favour first. I'll explain to you what that means, because I have often been asked by Dommes who I've mentored, about this exact subject:

"But Mistress, isn't sucking cock or being doggystyle fucked an act of submission?" They would ask me.

It can be...depending on the setting. If my pleasure and amusement is paramount above all else, I'm going to do and get, whatever the fuck I want. 

I told the aspiring Dommes to never sacrifice their own pleasure, simply because you think a certain sex act is more submissive than dominant. Just make some adjustments to the scene, so the person doing the fucking does not feel dominant at all! 

With silly males it's easy. They can fuck me doggystle all they like, or I can kneel and suck while they remain standing, but I'll be fucking and sucking this: 

Suddenly it's not such a dominant act for them anymore, is it?

Sissy slaves, this isn't even a conversation so I'll skip them completely. 

As for a silly male, who actually gets to use their unlocked penis with me, which is extremely rare, accessorize them! The last time I let a male slave fuck me doggystyle, he was collared, ball gagged, blindfolded, had nipple clamps on, two condoms on his dick and a decent-sized butt plug up his ass. 

Now who's pleasure is this fucking suppose to be for? Certainly not his! 

All this being said, I applied the same theory to my girls. I plugged both their bum holes with girthy anal plugs, then gagged the pair of them. I blindfolded Bella but left Summer with her sight. I needed her to help guide Bella around. 

There! All set. The scales of dominance were now tipped in my direction. I could get these two into strap-ons and take all the dick I wanted. 

Bella provided some good submissive support and although she would have been able to hear some gagging and sputtering on a cock, she probably couldn't tell if it was me or Summer. 

Summer couldn't say anything and I remained as quiet as possible, as I draped myself over Bella's back and gestured for Summer to enter me from behind. 

She gave me a nice, sensual fucking while Bella drooled beneath us. 

I loved all the attention I was getting, I felt Goddess-like, slutty and in complete control! I wanted more. Would a spit-roast be taking it too far? Is that WAY too submissive?

Nah...look at these two lovely sluts of mine. Recently age regressed, spanked, and sent to the timeout corner. Now plugged, gagged and one of them blindfolded. I don't think they feel dominant right now, I'm gonna go for it! 

Jesus fuck, did I ever cum! 

I love getting anything I want, any way I want. Remember Dommey girls, don't deprive yourself of something you want just because you're a Domme. Tip the scales in your favour and carry on. 

I removed all of their accessories and they nuzzled at my feet for the next little while. What a lovely slumber party this has been. 

 

Mistress Andrea

xoxo

Continued in: Time for a Recap