Sissy Cucks and Sucks

Continued from: Bella's Pony Play

This is the lockable cage that sissy Tiffany (aka Andrew), will be spending some time in while I fuck his girlfriend Katrina. As described in the previous post, Katrina wanted to evolve her boyfriend's humiliation by not only continuing his forced feminization and chastity, but also to begin cuckolding him. 

The cage is located directly beside my bed and due to it's small size, Tiffany will likely be forced into a crouch position for the majority of my session with Katrina. Who knows, my receptionist Cassandra might even stop by and join in. 

The three of us were all sitting at the dining room table and working through the details of the session. 

Katrina brought Tiffany to the session, already dressed like a little girl and made-up for us. Cassandra, although she was not working at reception today, put him into the usual "waiting-room predicament" so the three of us could chat. 

It must have been dreadfully humiliating for the poor sissy, having to listen to us whisper and giggle from the dining room. We learned that Katrina didn't tell him why she booked him a session today. For all he knew, he was there to be spanked.

Cassie and I had the foundations of a plan for what we wanted to do with Katrina. We just needed her to fill in the blanks. She told us that she wanted to be poorly treated, called names, degraded and dominated sexually throughout this session. She wanted the illusion for her sissy to be, that she was just some "free-fuck" in a high-end hotel room, posting herself all over the internet for casual hook-ups. 

I nodded at Cassandra in agreement. The foundations of our original plan would track with this very well actually. I explained to Katrina that I would have a difficult time calling her degrading names like she wanted me to, but I understood how arousing it will be for her. 

"Just remember I'm playing a role Kat. I would never ever speak to you in a manner like this", I reassured her.  

"Ya, ditto." Cassie chimed in like a teenager, with that nugget of reassurance. 

I told Katrina that we're going to play around with gender roles a bit too, and told her to treat Cassie and I as though we are male. 

She looked excited. Her face and neck were flushing with arousal. 

"Alright Kat, take Tiffany upstairs and lock her in the cage while you get yourself dressed and ready. I'll text you when Cassie and I are good-to-go, then I want you to kneel and face the wall near the cage." 

"Simply tell Tiffany":

"My Master likes me to dress in lingerie and slutty heels, and wait for him like this on date nights." 

We all giggled together. This is gonna be hot!

Katrina had her sissy in shackles and stowed away while she got ready, then knelt down to likely tell him for the first time, that he's about to watch her get fucked. 

Cassie and I were ready, I text Katrina, who got herself into the requested position to wait for me. 

"There's my little hotel slut! Hello slut. Turn and face me, keep your hands on your head and stay on your knees". I ordered.

"Yes Master", she said right away. 

I had taken my hair extensions out and dressed up like a man. Tiffany could hear my voice and knew it was me, but what she couldn't see, was the giant bulge in my dress pants. 

I kept ordering Katrina around, while she continued to call me Master. I had her turn and face the wall again, while I sat and spoke to Tiffany in the cage. 

"So this is your girlfriend I understand? Isn't she everyone's girlfriend?" 

"Yes Mistress", Tiffany said, in a knee-jerk reaction. 

"It's yes Sir, sissy". I scolded. 

"I'm sorry Sir, yes Sir", he said. 

"Tonight, Katrina exists in this room for my pleasure, and anyone else who might pop by for a drink, isn't that right slut?" 

"Yes Master", Katrina instantly responded. 

"Hell, maybe I'll even post her juicy ass on some escort sites, she can make me some dough tonight". I followed up. 

Tiffany whimpered from the cage, as he now understood the overall "just" of the session that was about to occur.  

I pulled Katrina by her hair, over to the side of the cage. I claimed her pussy as mine, by grabbing it and rubbing her over her panties. 

"From what I understand, you don't get to have this do you sissy?" I asked Tiffany. 

"No Sir", he peeped. 

"It’s mine now isn't it?" I said as I continued to rub Katrina, while she moaned like a whore. 

"Yes Sir it is", he peeped-out again. 

"I'll tell you what else is mine, this whorish mouth! Get on your knees slut", I barked at her, while gearing my pants off. 

Tiffany's only vantage point was now my men's style dress socks and shoes, and his girlfriend's stockings while she knelt. A perfect illusion for him to see. 

"Get my dick hard, bitch!" And with that, I slapped her face. 

For the benefit of Tiffany listening, Katrina cried out with an "ouch", then she winked at me before proceeding with my cock. 

"That's my good little cock-whore, now into your mouth with it. Show Master how much you love sucking cock!" 

I kept the narrative going. I was saying as much as possible to remind poor Tiffany that his little cocklette is in an inescapable chastity device.

I took things over to the couch and began fucking Katrina, in full view of the cage. 

Katrina was definitely being extra vocal, for the benefit of sissy Tiffany. 

"Head down, ass up bitch!" I hissed, as I pinned her head down with my shoe and continued to pound her.

I grunted and moaned and simulated the sounds of cumming inside her pussy, then ordered her to get in a "down" position on the floor. 

I pulled out my phone, this was all scripted in advance of course, and called Cassandra who was downstairs. I created the illusion that I was calling some buddy. 

Here's what Tiffany would have heard from the cage and Katrina from her down position. 

"Hey Man, what you sayin'?"

"No just chillin tonight, I've got some random piece over".

"No not her, a different one". 

"Serious bro, I just busted right in her cunt, no condom". 

"Ya she wouldn't mind a DP. Seriously, you comin' over?"

"Alright see you shortly then".

"...yes I'll loosen up her ass". 

"ATM?...no that's cool, she'd totally be into that bro".

"Ya, ya...ya, just let yourself in". 

*bleep*

"Did you hear that slut? You get to take two cocks tonight!" 

"Thank you Master", Katrina spoke into the floor. 

"Come clean my dick off. I guess I need to use it again", I said to her.

Katrina sucked and gagged on my dildo for a bit, all while Tiffany watched on in desperation and humiliation. 

Cassandra gave us a few minutes, then rolled in, dressed like a dude. She gave me a "hey Man", as she approached. 

"Don't be shy bro, this bitch can't wait to get two cocks in her!" 

Cassandra got out of her pants and took a seat on the couch. Katrina silently mouthed the words, "I'm loving this", to me, while she once again knelt. 

She started sucking my dildo, while stroking Cassandra's. She was gagging and retching loudly, likely for the benefit once again, of her poor, caged sissy. 

Between laboured breaths, Katrina gasped out to Cassie, "I want your big, black cock Sir! Please fuck me."

"Up your ass?" Cassandra asked her, playing into her role.

"Anywhere you wish Sir", Katrina responded. 

During our initial planning meeting in the dining room, we hadn't planned on Katrina taking it up the ass tonight. She told us she has limited experience with anal and would need some training and stretching first. 

But we can certainly let Tiffany hear us pretending to fuck his girlfriend in the ass...

As Cassie entered her, Katrina cried out, "Ohhh gawd your cock is so huge Sir!" I think it turned her on, trying to speak coherently while my dildo was in her mouth. She was ready for her first of several orgasms that would follow.

Cassandra and I continued to spit-roast her, eventually moving to the floor to create a better view for Tiffany. His poor cock must be straining against the confines of his chastity cage by now. 

"Is Tiffany looking forward to being spit-roasted by two dudes, slut?" I asked Katrina. She didn't respond as my cock was down her throat. 

I yelled over to the floor cage. "Sissy, do you want to trade places with your girlfriend?" 

"No Sir", conflicted and embarrassed, he whispered out in shame. 

"I'm gonna let you taste her filthy cunt, sissy. But you'll be tasting it off my dick once I finish inside her again", I called out. 

"Thank you Sir", Tiffany replied. 

We eventually got Tiffany out of the cage and a little closer to the action. Katrina had orgasmed again, onto Cassandra's cock and another onto mine. We had fucked her all over that bedroom in a variety of positions, while Tiffany was bound and gagged, being forced to watch the ravaging of his girlfriend. 

I put my suit jacket back on to look more dude-ish, before we untied Tiffany for his final act of degrading humiliation. 

Katrina, now well spent and satisfied, relaxed on the bed and watched her boyfriend clean her pussy juices from my cock. 

All the while I was pestering him about being a pussy-free sissy. 

"This is the only way you get her pussy isn't it Tiffany? From sucking a cock that just finished inside your girlfriend?" I tormented. 

He held my dildo in his little satin glove and cleaned every inch of my dick, while Katrina watched on in vengeful delight. 

"Cassie huni, can you take this pathetic sissy down to the stage and put her in timeout. She can reflect on this session while I debrief with Kat", I said. 

"Yes Sir", Cassandra responded, as switched on as ever. She never misses a beat that girl! She maintained our fantasy roles perfectly. 

Katrina and I embraced on the bed and she thanked me for the wonderful session. She said it was an amazing experience. 

"Where did you find that Cassie girl?! My god she is a handful!" Katrina giggled. 

"My personal little stripper! Yes she's something else alright", I replied. 

"If we're slowly escalating with my sissy Ma'am, where should I take things next", Katrina asked me. 

I suggested that the next logical step might be to try Tiffany with a second sissy slave, to see what they'll do with each other, if it means their dicks will be unlocked. 

"But Andrew isn't gay, Mistress", Katrina injected. 

"You'd be surprised huni", I cooed to her. "Orgasm denial does amazing things to silly boys".

She giggled out loud in delight. 

I then suggested to her that a boyfriend or "bull" could be introduced to their dynamic, so she is not depraved of real cock and being fucked when she wants. 

"That sounds hot Mistress. Does my bull get to use Tiffany too?" She asked. 

"Time will tell sweetheart. We'll take it slowly and I'll help you, if that's your ultimate goal", I coached her. 

"Thank you Mistress. May I go down on you before I take Tiffany home Ma'am?"

"Of course you may!" I purred. 

Mistress Andrea

xoxo

Continued in: Summer gets caught

 

Bella's Pony Play

Continued from: The BDSM Spectrum

I have an amazing pony play session all lined up for Bella, do you think I can find my fuckin' beige riding breeches? The ones that look amazing with black boots. The ones that are so tight across my gorgeous ass, that they look like they're painted on?

F**k!

I had to take things in a different direction with my attire. I decided on a mixture of formal equestrian wear, combined with Yellowstone, slutty and crazy barrel racer. I'll still look hot, Bella will be a puddle for me regardless. 

I wasn't able to find an actual barn, play space. They were all either dirty or smelly, so I decided to renovate my dungeon space for this session.

Bella was booked. I sent her some online porn homework, to explore and report back to me on. She had never seen pony play in BDSM before. I set her up with some material and videos to review. 

She was absolutely horrified at what was to come, and excited, embarrassed, aroused and soon to be humiliated. The contradictory cocktail of emotions she must have been experiencing, leading up to this day, I couldn't even imagine the butterflies she must have.

I told her to dress "country-slutty" for me. There would be no check-in with Cassandra this time, no anticipation or waiting. Bella knew she was getting a spanking first, then taken right to the "barn" next. If she fussed, the spanking would quickly become a woodshed strapping.  

I hiked her little ripped jeans down, her panties next, and started-in on her bare bum. A steady and meaningful hand-spanking. 

When I got her jeans and heels off, it turns out she wore nude stockings under her jeans, so the nylon pops through the jean-rips, to give her legs a flawless appearance. Cute idea, I thought. 

Bella received a nice, long warm up, before I asked her to kneel in the pose she is familiar with, we call it "open". 

"No timeouts in the corner today young lady, remain in "open" for me while I change. Get your hair into a high pony, you're not to move and you're to keep your legs spread and cunt displayed. 

"Yes Ma'am", she obeyed and blushed at my crass choice of words. 

I returned to find her in the same pose, trembling with anticipation and soaking with arousal. I clicked closer to her in my boots, inspecting her positioning and her ponytail. 

She knelt deeper, to kiss the smooth leather of my boots as I invitingly outstretched a foot. 

"Mmmm, good girl", I purred. 

I put Bella in a head-harness, mouth gag and leather collar. I led her to the dungeon and into her new pony stall. 

The setting was perfect. I could see Bella's eyes darting around the space. Likely mortified that she had been placed in a make-shift, horse stall with a straw floor. 

"I have to get all your tack on slave girl". I said to her. 

"But first, I need to calm that pussy down a bit. You are WAY to aroused right now", and I shook my head at her. 

She groaned into her gag, utterly ashamed over her soaked pussy, reacting to this environment. 

We got her into stockings and pony boots, which buckled and padlocked to her feet and knees. 

I helped her up onto a wooden pony, torture device and watched as she lowered her weight onto the unforgiving spine. The next little while will be spent watching her shift and adjust, trying to keep the painful pressure off her pussy lips, clit and asshole. 

After a solid 15 minutes on the wooden horse while I sat on a straw bale and watched, I asked if she was ready for her pony plug. The alternative option I gave her, was to just stay on the wooden torture horse. 

She cried and nodded her head. Bubbling spit from her harness gag in an attempt to say, "plug please, plug please Ma'am". 

I re-bound her in strappado, so her creamy little asshole was pointed directly at me. I chose a lovely and sleek, black-haired butt plug to match her actual pony tail. It looked beautiful on her. Or in her, rather. 

Next came a stainless chastity belt, to keep her pussy locked down and out of play. Her plug tail cascaded nicely from the anal opening in the chastity belt. Another head harness with some padlocks, an arm binder and finally, a nipple chain with some bells, she was all set. But my gawd was she ever humiliated! Her eyes were bloodshot from the stinging of her tears. 

I penned her up in her stall and locked the gate. Then I just sat back to watch her attempts to balance on the awkward heels, squeeze and contract on her plug, and jingle about from her loose and flopping tits. 

As some time passed and her struggles intensified, I asked if she was ready to go outside for some trot and prance training. 

Her eyes widened from behind her face harness. She shook her head violently in protest. 

I led her from her stall by her harness reins and whipped her in a crouch position. 

Eventually I returned her to her stall and calmly spoke. 

"Do you need to safeword out, Bella?"

She shook her head no. 

"Then it's time to go out the back for some prancing", I replied. 

She groaned and cried, but eventually lowered her head and allowed herself to be led outside by her reins. I could only imagine what was going on under the metal shrouds of that chastity belt. I bet there was an absolute frenzy in the works. 

I told her how I wanted her to lift her knees high and prance. Very controlled, very dainty. She practiced on the spot for me, while scanning the horizon and windows for any peeping neighbours. 

She did a quick trot for me, then a prance. All while I whipped her bare butt and flanks, encouraging her to keep her knees up and move slowly and under control. 

I saved her from any further embarrassment and led her back to her stall inside. I'm sure her humiliation levels were at the critical point, yet when I bent her over her stall to remove her tail-plug, I saw what success looked like! 

The poor, poor thing! She just can't help it! Little spider-silk strands of cum, dripped from the metal screening housing her pussy. 

I kept her in her head harness and gag and entered her bottom hole with my strap-on, through the little opening that the chastity belt provides. 

Before long she was screaming and making sounds through her gag that I hadn't heard her make before. I slowed right down and stopped. I thought I was hurting her.

She began to violently shake her head no and started to buck her ass and hips back into my harness, fucking her own butt with the dildo. I held her reins to control her bucking and to pull back on her gag, but she only got more frantic. Her tits continued to bob and jingle with abandon, perfectly framed and presented by her armbinder. 

She didn't want me to slow down at all, she wanted me to....

OMG! She was cumming from anal only! 

She was screaming "NOOOO" and "FUUUUUCK" at the top of her lungs while her legs shook and liquid squirted from the screening of her metal chastity.  

I've never heard Bella swear before, not even during the most severe spanking over my knee... 

While we were debriefing this pony session and doing aftercare, she pinned me down all cute-like, wearing my hat too, which made her even more cute. 

"Mistress, what the fuck was that?! What did you do to me!!?" 

She gritted her teeth and pinned my hands down, trying to act serious. 

I indulged her passionate cuteness and fought her off, up into a sit. I kissed her deeply. 

"I think someone likes being a pony slave, that's what happened”, I purred. 

"Oh Gawd! Thank you Mistress!", she sighed and groaned in embarrassment.

"Did I actually cum and squirt from being assfucked, Mistress", she asked me innocently. 

"Why yes you did, pony slave", I cooed.   

Mistress Andrea

xoxo

Continued in: Sissy sucks and cucks

 

 

The BDSM Spectrum - According to Mistress Andrea

Continued from: I let Katrina Domme me, sort of

I have never found an image on the interwebs, that more accurately depicts my take on the BDSM spectrum, than this one:

I see naughty vs. nice here, I see ying and yang, fire and ice, the need for both pleasure and pain, name your cliché. I see the balance required, for BDSM dynamics to work. The need to be whipped on the left, and the cuddles of aftercare on the right. 

It's a beautiful image. A close second place, of similar concept would be:

Yet, this is MY style and MY interpretation of BDSM, according to Mistress Andrea. It's not backed by any empirical evidence or research of any kind. This is merely my opinion, based on my own experiences. 

I rely heavily on outfits and settings in my scenes. I find that the participants have a much deeper and more rich experience, when attention to detail is closely adhered to. Submissives can immerse themselves into their role much easier, and achieve that escape they are craving. Dominants can get into their groove much easier too, pushing the limits of their subs with less inhibitions. 

I have a difficult time picturing a kink couple, floating around in the vanilla world, wearing their Levi 501's and deciding to bust out the flogger and ball gags on a whim, in their current attire in their vanilla bedroom.

Perhaps that's what spontaneity is? I don't know. I need more of a plan, more of a script and a need to know where I am playing within the spectrum. 

Once again, this spectrum I speak of is according to me. 

Bella Goth, during her recent session, experienced one of these poles for the first time. She's an adult woman, mother and executive and I had her dressed like a little girl, spanked her and later put her in an adult diaper. The beginnings of that 3-part story can be found here: Bella's Age Regression Kink

This was so humiliating for the poor thing. So much so that she was soaked and had an orgasm, figure that one out.

Let's call this kink of hers, the extreme right. It's ddlg, mdlg, adbl, diaper use, age play, humiliation and for males, sissy slavery and forced feminization. 

On the other end of the spectrum, the extreme left we'll call it, I associate with pony play. Have you ever come across it on the interwebs? 

Elaborate leather body-harnesses, high-heeled boots, gags and plugs. The slaves' look so sharp and well trained, that it makes me think it's the absolute apex you can achieve, as a submissive. 

Their movements and behaviour is almost cocky and proud. That's how switched on they are. Something for a new submissive to aspire to be? Who knows. This is just my take on things, I find pony slavery to be elegantly beautiful and artistic. Your slave has "made it to the show", if they are at this level, and they should be extremely proud of it. 

However, therein lies the horrible and wonderful predicament of a submissive. Both ends of my spectrum are degrading, embarrassing and dreadfully humiliating. Yet we all know what humiliation does to a submissive. It traps them in the vicious cycle I want them in. 

So we have polar left, and polar right, as described above, lets not forget all the goodness in between those poles. This is where you find the rope bondage, the schoolgirl attire, nurses uniforms and enemas. This is where all the other uniforms and fantasies and BDSM activities reside. 

I enjoy playing on both poles of the spectrum and everything in between.

Why is all of this important right now? 

I thought I would explain it first, as I am going to take Bella to the polar left, on her next session. She's going to be a prancing pony slave for me! My goal with her was to show her one extreme, then show her the other, before we do everything else, in between.

Now I just need to find a BDSM barn / country setting. 

Stay tuned. 

Mistress Andrea

xoxo 

Continued in: Bella's Pony Play  

 

I let Katrina Domme me, sort of.

Continued from: Katrina wants to cuck Andrew

Sometimes it's fun to be on the bottom, with the right person. Katrina won that lottery today, as we were in the midst of cooking up a devious little scheme for her sissy boyfriend.

Plus, I haven't had any phallic objects in me, in quite some time. I've been on a bit of a lezzie tear lately and I rarely unlock my male pets and never unlock my sissy pets. 

I figured..."what the hey". Let's see what this little firecracker can do.

We basically agreed to a dress rehearsal together. She was going to use my strap-on and play out on me...what she wants me to do to HER, in front of her helpless and feminized boyfriend.

Still following? Confusing I know... 

She got right down to business, telling me that he never gets her pussy, only her bumhole. She wanted me to start with her throbbing puss puss.

I reminded her to be nice and vocal, as I will be with her, on the day of. Making sure her sissy boyfriend can hear everything that he is never offered. 

She was a little shy at first, before she finally told me to lick her pussy from behind and make her cum. 

Boy, did she ever cum! I was impressed with myself. She was shaking and trembling in no time flat. I got to enjoy the lovely view of her little bum hole, squeezing and contracting as she shuddered through her orgasm. 

I helped her into one of my strap-on harnesses and showed her where we should probably stand, to create a good vantage point for sissy Tiffany. 

"Stroke the full length of the cock Kat. His little dicklette should start to throb inside the metal bars of his chastity cage", I told her. 

"Oh I intend to!" She replied. 

I laid down on the bed and let my head drop off the side. A perfect throat fucking position for Katrina. She did not disappoint. 

She even made a point of slapping the dick off my cheeks and telling me to do this to her also, on the day of the session. 

She wanted him to see me beating her up and degrading her, with the turgid dildo. 

She pulled the dick out of my mouth so I could answer a question. 

"Mistress, do you have a realistic, big, black cock?"

"I think I do huni", I responded. Panting and drooling from having my throat fucked. 

"Can you use that on me Mistress?" She said in excitement. 

"Anything you wish Kat", I managed to get out, before she plunged the cock back in my mouth to shut me up. 

When she was done with my mouth, I was invited up to ride her, and ride her I did! It felt amazing and Katrina was super sexy. I didn't mind being on the receiving end of this one. 

Our passion was mounting, I was definitely getting ready to cum! She was pounding the shit outta me at this point!

We finished up our dress rehearsal with a lovely orgasm for me. She was a bit insatiable at this point, participating in her first lezzie experience. She wanted to try going down on me. 

No complaints here, by all means. 

Girls just know how to do it better. My pussy was all puffy and hot from the vigorous fucking. I came right onto her lips and tongue almost immediately.

"That was so fuckin' hot Mistress", she said, both of us out of breath and sweaty. 

We hit the showers. 

I redeemed my role, by grabbing her by the pussy lips and pinning her against the shower stall. 

"So you want me to own this, right in front of Tiffany huh?"

"Mmmm, yes please Mistress, I want him whimpering. What should I wear?"

"Slutty lingerie, sky-high heels. Dress ultra slutty for me". I said. 

"And Tiffany?" She asked. 

We both paused, then said "like a little girl", at the same time. We laughed and tickled each other under the hot water. 

My hair was wet and disheveled, I was barefoot, as we came back down to find Cassandra in the kitchen. Apparently she heard everything. 

"So that was a ‘consultation’, huh?" Cassandra said. 

Katrina and I both giggled and blushed. 

"Sheesh! Where was MY invite?" Cassandra huffed out. 

My brazen and bold receptionist, stood right up, walked over to Katrina and French kissed her right in front of me. 

"Umm, Kat huni", I said. 

"Do you want to be spit-roasted in front of Tiffany? I think we just found another willing participant for you". I asked her...

Mistress Andrea

xoxo 

Continued in: BDSM according to me